US 7,732,022 B2 · Stilbene derivatives, liquid-crystal mixtures and electro-optical displays

Abstract

Disclosed are fluorostilbene compounds of formula I, liquid-crystal media which comprise these compounds, the use of the media in electro-optical displays, in particular in VAN LCDs, and a process for the preparation of these compounds.

Claims25

Dependent claims

A compound of formula I

in which
R11 and R12 each, independently of one another, denote H, halogen, —CN, —SCN, —SF5, —CF3, —CHF2, —CH2F, —OCF3, —OCHF2, an alkyl group having 1 to 15 C atoms which is monosubstituted by CN or CF3 or at least monosubstituted by halogen, in which optionally, one or more CH2 groups, in each case independently of one another, are replaced by —O—, —S—, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—,
—CO—, —CO—O—, —O—CO— or —O—CO—O— in such a way that neither O nor S atoms are linked directly to one another,
and
each, independently of one another and, if present more than once, also these independently of one another, denote
(a) a trans-1,4-cyclohexylene radical, in which optionally, one or two non-adjacent CH2 groups are replaced by —O— and/or —S—,
(b) a 1,4-cyclohexenylene radical,
(c) a 1,4-phenylene radical, in which optionally, one or two non-adjacent CH groups are replaced by N,
(d) naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, or
(e) 1,4-bicyclo[2.2.2]octylene, 1,3-bicyclo[1.1.1]pentylene or spiro[3.3]heptane-2,6-diyl,
where in
(a) and (b), one or more —CH2— groups, independently of one another, are optionally replaced by a —CHF— or —CF2— group, and in
(c) and (d), one or more —CH═ groups, independently of one another, are optionally replaced by —C(F)═, —C(Cl)═, —C(Br)═, —C(CN)═, —C(CH3)═, —C(CH2F)═, —C(CHF2)═, —C(OCH3)═, —C(OCHF2)═ or —C(OCF3)═,
Z11 and Z12 each, independently of one another and, if present more than once, also these independently of one another, denote a single bond, —CH2—CH2—, —CF2—CH2—, —CH2—CF2—, —CF2—CF2—, —CH═CH—, —CF═CF—, —CF═CH—, —CH═CF—, —C≡C—, —COO—, —OCO—, —CH2O—, —OCH2—, —CF2O—, or —OCF2—, or a combination of two of these groups, where no two O atoms are bonded to one another, and
m and n each independently denote 0, 1 or 2, and
(m+n) denotes 1 or 2.

13 more elements

A compound which is one of the compounds 1 to 149 or 226 to 299

No.
R11
R12
wherein
1
n-C3H7
C2H5O
2
CH3
CH3
3
CH3
C2H5
4
CH3
n-C3H7
5
CH3
n-C4H9
6
CH3
n-C5H11
7
CH3
n-C7H15
8
CH3
CH3O
9
CH3
C2H5O
10
CH3
n-C3H7O
11
CH3
n-C4H9O
12
CH3
CH2═CH
13
CH3
E-CH3—CH═CH
15
CH3
CH2═OH—O
16
CH3
CH2═CH—CH2O
17
C2H5
CH3
18
C2H5
C2H5
19
C2H5
n-C3H7
20
C2H5
n-C4H9
21
C2H5
n-C5H11
22
C2H5
n-C6H13
23
C2H5
n-C7H15
24
C2H5
CH3O
25
C2H5
C2H5O
26
C2H5
n-C3H7O
27
C2H5
n-C4H9O
28
C2H5
CH2═CH
29
C2H5
E-CH3—CH═CH
30
C2H5
CH2═CH—O
31
C2H5
CH2═CH—CH2O
32
n-C3H7
CH3
33
n-C3H7
C2H5
34
n-C3H7
n-C3H7
35
n-C3H7
n-C4H9
36
n-C3H7
n-C5H11
37
n-C3H7
n-C6H13
38
n-C3H7
n-C7H15
39
n-C3H7
CH3O
40
n-C3H7
n-C3H7O
41
n-C3H7
n-C4H9O
42
n-C3H7
CH2═CH
43
n-C3H7
E-CH3—CH═CH
44
n-C3H7
CH2═CH—O
45
n-C3H7
CH2═CH—CH2O
46
n-C4H9
CH3
47
n-C4H9
C2H5
48
n-C4H9
n-C3H7
49
n-C4H9
n-C4H9
50
n-C4H9
n-C5H11
51
n-C4H9
n-C6H13
52
n-C4H9
n-C7H15
53
n-C4H9
CH3O
54
n-C4H9
C2H5O
55
n-C4H9
n-C3H7O
56
n-C4H9
n-C4H9O
57
n-C4H9
CH2═CH
58
n-C4H9
E-CH3—CH═CH
59
n-C4H9
CH2═CH—O
60
n-C4H9
CH2═CH—CH2O
61
n-C5H9
CH3
62
n-C5H11
C2H5
63
n-C5H11
n-C3H7
64
n-C5H11
n-C4H9
65
n-C5H11
n-C5H11
66
n-C5H11
n-C6H13
67
n-C5H11
n-C7H15
68
n-C5H11
CH3O
69
n-C5H11
C2H5O
70
n-C5H11
n-C3H7O
71
n-C5H11
n-C4H9O
72
n-C5H11
CH2═CH
73
n-C5H11
E-CH3—CH═CH
74
n-C5H11
CH2═CH—O
75
n-C5H11
CH2═CH—CH2O
or
wherein
76
CH3
CH3
77
CH3
C2H5
78
CH3
n-C3H7
79
CH3
n-C4H9
80
CH3
n-C5H11
81
CH3
n-C7H15
82
CH3
CH3O
83
CH3
C2H5O
84
CH3
n-C3H7O
85
CH3
n-C4H9O
86
CH3
CH2═CH
87
CH3
E-CH3—CH═CH
88
CH3
CH2═CH—O
89
CH3
CH2═CH—CH2O
90
C2H5
CH3
91
C2H5
C2H5
92
C2H5
n-C3H7
93
C2H5
n-C4H9
94
C2H5
n-C5H11
95
C2H5
n-C6H13
96
C2H5
n-C7H15
97
C2H5
CH3O
98
C2H5
C2H5O
99
C2H5
n-C3H7O
100
C2H5
n-C4H9O
101
C2H5
CH2═CH
102
C2H5
E-CH3—CH═CH
103
C2H5
CH2═CH—O
104
C2H5
CH2═CH—CH2O
105
n-C3H7
CH3
106
n-C3H7
C2H5
107
n-C3H7
n-C3H7
108
n-C3H7
n-C4H9
109
n-C3H7
n-C5H11
110
n-C3H7
n-C6H13
111
n-C3H7
n-C7H15
112
n-C3H7
CH3O
113
n-C3H7
C2H5O
114
n-C3H7
n-C3H7O
115
n-C3H7
n-C4H9O
116
n-C3H7
CH2═CH
117
n-C3H7
E-CH3—CH═CH
118
n-C3H7
CH2═CH—O
119
n-C3H7
CH2═CH—CH2O
120
n-C4H9
CH3
121
n-C4H9
C2H5
122
n-C4H9
n-C3H7
123
n-C4H9
n-C4H9
124
n-C4H9
n-C5H11
125
n-C4H9
n-C6H13
126
n-C4H9
n-C7H15
127
n-C4H9
CH3O
128
n-C4H9
C2H5O
129
n-C4H9
n-C3H7O
130
n-C4H9
n-C4H9O
131
n-C4H9
CH2═CH
132
n-C4H9
E-CH3—CH═CH
133
n-C4H9
CH2═CH—O
134
n-C4H9
CH2═CH—CH2O
135
n-C5H9
CH3
136
n-C5H11
C2H5
137
n-C5H11
n-C3H7
138
n-C5H11
n-C4H9
139
n-C5H11
n-C5H11
140
n-C5H11
n-C6H13
141
n-C5H11
n-C7H15
142
n-C5H11
CH3O
143
n-C5H11
C2H5O
144
n-C5H11
n-C3H7O
145
n-C5H11
n-C4H9O
146
n-C5H11
CH2═CH
147
n-C5H11
E-CH3—CH═CH
148
n-C5H11
CH2═CH—O
149
n-C5H11
CH2═CH—CH2O
or
wherein
226
CH3
CH3
227
CH3
C2H5
228
CH3
n-C3H7
229
CH3
n-C4H9
230
CH3
n-C5H11
231
CH3
n-C7H15
232
CH3
CH3O
233
CH3
C2H5O
234
CH3
n-C3H7O
235
CH3
n-C4H9O
236
CH3
CH2═CH
237
CH3
E-CH3—CH═CH
238
CH3
CH2═CH—O
239
CH3
CH2═CH—CH2O
240
C2H5
CH3
241
C2H5
C2H5
242
C2H5
n-C3H7
243
C2H5
n-C4H9
244
C2H5
n-C5H11
245
C2H5
n-C6H13
246
C2H5
n-C7H15
247
C2H5
CH3O
248
C2H5
C2H5O
249
C2H5
n-C3H7O
250
C2H5
n-C4H9O
251
C2H5
CH2═CH
252
C2H5
E-CH3—CH═CH
253
C2H5
CH2═CH—O
254
C2H5
CH2═CH—CH2O
255
n-C3H7
CH3
256
n-C3H7
C2H5
257
n-C3H7
n-C3H7
258
n-C3H7
n-C4H9
259
n-C3H7
n-C5H11
260
n-C3H7
n-C6H13
261
n-C3H7
n-C7H15
262
n-C3H7
CH3O
263
n-C3H7
C2H5O
264
n-C3H7
n-C3H7O
265
n-C3H7
n-C4H9O
266
n-C3H7
CH2═CH
267
n-C3H7
E-CH3—CH═CH
268
n-C3H7
CH2═CH—O
269
n-C3H7
CH2═CH—CH2O
270
n-C4H9
CH3
271
n-C4H9
C2H5
272
n-C4H9
n-C3H7
273
n-C4H9
n-C4H9
274
n-C4H9
n-C5H11
275
n-C4H9
n-C6H13
276
n-C4H9
n-C7H15
277
n-C4H9
CH3O
278
n-C4H9
C2H5O
279
n-C4H9
n-C3H7O
280
n-C4H9
n-C4H9O
281
n-C4H9
CH2═CH
282
n-C4H9
E-CH3—CH═CH
283
n-C4H9
CH2═CH—O
284
n-C4H9
CH2═CH—CH2O
285
n-C5H9
CH3
286
n-C5H11
C2H5
287
n-C5H11
n-C3H7
288
n-C5H11
n-C4H9
289
n-C5H11
n-C5H11
290
n-C5H11
n-C6H13
291
n-C5H11
n-C7H15
292
n-C5H11
CH3O
293
n-C5H11
C2H5O
294
n-C5H11
n-C3H7O
295
n-C5H11
n-C4H9O
296
n-C5H11
CH2═CH
297
n-C5H11
E-CH3—CH═CH
298
n-C5H11
CH2═CH—O
299
n-C5H11
CH2═CH—CH2O.

671 more elements

Dependencies are inferred from the claim text.

Facts

Application

11/953,497Filed 10 Dec 2007

Priority

DE 10 2006 058 60811 Dec 2006

Published

US 2008/0149891 A126 Jun 2008

Granted

8 Jun 2010

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

C09K 19/16
Linked by a carbon chain: the chain containing carbon-to-carbon double bonds, e.g. stilbenes
C09K 19/3048
Cyclohexane rings: in which at least two rings are linked by a carbon chain containing carbon to carbon double bonds
C09K 19/42
Characterised by the chemical structure of the liquid crystal components , e.g. by a specific unit: mixtures of liquid crystal compounds covered…
C09K 2019/0407
The structure containing one or more specific, optionally substituted ring or ring systems: containing a carbocyclic ring, e.g. dicyano-benzene,…

Stilbene derivatives, liquid-crystal mixtures and electro-optical displays

Life of this patent

Abstract

Claims25

Stilbene derivatives, liquid-crystal mixtures and electro-optical displays

Life of this patent

Abstract

Claims25