Patent US627665A successfully refreshed from Google Patents.
Patent US3568933A successfully refreshed from Google Patents.
Patent US5380460A successfully refreshed from Google Patents.
← Back to Patent Explorer
US5380460A Expired / Lapsed US ⏱️ 0.0 years remaining

Ferroelectric liquid crystal compounds containing chiral haloalkoxy tail units and compositions containing them

Assignee: Micron Technology Inc
•
Filing: 1991-09-20
•
Granted: 1995-01-10
•
Expires: 2011-09-20
📄 Original PDF 🌐 Google Patents 🔄 Sync Now

Abstract

Abstract Chiral, nonracemic compounds of the general formula: ##STR1## wherein m and n are either both zero, both equal one or n is equal to one and m is equal to zero, X and Y and Z are halogens, R' is an alkyl, alkoxyl, alkenyl, thioalkyl, thioether, ether, or alkylsilyl group containing three to fifteen carbon atoms, and R is an alkyl group having one to fifteen carbon atoms and where Ar is: --A.sub.a --(E).sub.e --B.sub.b --(F).sub.f --D.sub.d -- where A, B and D independently of one another are aromatic rings which are selected from the group consisting of a phenyl, a pyridine ring, a pyrimidine ring, a pyridizine ring, a pyrazine ring and a thiadiazole ring, wherein a, b and d are integers from 0-3 such that a+b+d=2-3, where E and F independently of one another are linking groups selected from the group consisting of a --CH 2 --CH 2 --, --CH 2 --O--, --CH 2 --S--, --O--CH 2 --, --S--CH 2 , --OOC-- or --COO-- wherein e and f can be 1 or 0, when e and/or f is 0, the adjacent aromatic rings are linked by a carbon-carbon single bond, preferably e and f are both 0 or one of e or f is 1, and wherein * indicates a chiral center, which are useful as ferroelectric liquid crystal components having high polarization are described.

Inventors

  • 👤 Michael D. Wand
  • 👤 William N. Thurmes
  • 👤 David M. Walba

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-10 02:14
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/24; C07D213/28; C07D213/30; C07C; C07C69/00; C07C69/76; C07C69/84; C07C69/92; C07D213/60; C07D213/62; C07D213/63; C07D213/64; C07D213/65; C07D239/00; C07D239/02; C07D239/24; C07D239/26; C07D239/28; C07D239/32; C07D239/34; C07D239/38; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/24; C07D405/00; C07D405/02; C07D405/12; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3441; C09K19/52; C09K19/58; C09K19/586; C09K19/588

Claims Analysis

Total Claims: 30
Claim 1
Independent Claim 215 words
A chiral nonracemic compound having the formula: ##STR116## and enantiomers thereof, wherein: Ar is a core unit containing at least two aromatic rings having the formula: --A a --(E) e --B b --(F) f --D d --, where A, B and D, independently of one another, are selected from the group of aromatic rings consisting of phenyl, pyrimidine, pyridine, pyrazine, pyridizine, and thiadiazole, where a, b, and d, independently of one another, can be 0-3 and a+b+d=2 or 3, where E and F, independently of one another, are selected from the group --OOC--, --COO--, --CH 2--CH 2 --, --O--CH 2 --, --CH 2 --O--, --S--CH 2 --, and --CH 2 --S--, where e and f independently of one another are 0 or 1; R' is an alkyl, alkenyl, alkoxy, thioalkyl, thioether, ether or silylalkyl group having three to fifteen carbon atoms; X and Y are halogens; and R is an alkyl or alkenyl group having from one to fifteen carbon atoms, provided that when R' is an alkyl group containing from three to fifteen carbon atoms, Ar is not 5,4'-substituted 2-phenylpyrimidine, 4,4'-substituted phenylbenzoate, 4,4,-substituted biphenylbenzoate or 4,4'-substituted biphenyl; and provided that when R' is an alkoxy group containing from three to fifteen carbon atoms, that Ar is not 4,4'-substituted phenylbenzoate, 4,4'-substituted biphenylbenzoate, or 4,4'-substituted biphenyl.
Claim 2
Dependent Claim 215 words
A chiral nonracemic compound having the formula: ##STR116## and enantiomers thereof, wherein: Ar is a core unit containing at least two aromatic rings having the formula: --A a --(E) e --B b --(F) f --D d --, where A, B and D, independently of one another, are selected from the group of aromatic rings consisting of phenyl, pyrimidine, pyridine, pyrazine, pyridizine, and thiadiazole, where a, b, and d, independently of one another, can be 0-3 and a+b+d=2 or 3, where E and F, independently of one another, are selected from the group --OOC--, --COO--, --CH 2--CH 2 --, --O--CH 2 --, --CH 2 --O--, --S--CH 2 --, and --CH 2 --S--, where e and f independently of one another are 0 or 1; R' is an alkyl, alkenyl, alkoxy, thioalkyl, thioether, ether or silylalkyl group having three to fifteen carbon atoms; X and Y are halogens; and R is an alkyl or alkenyl group having from one to fifteen carbon atoms, provided that when R' is an alkyl group containing from three to fifteen carbon atoms, Ar is not 5,4'-substituted 2-phenylpyrimidine, 4,4'-substituted phenylbenzoate, 4,4,-substituted biphenylbenzoate or 4,4'-substituted biphenyl; and provided that when R' is an alkoxy group containing from three to fifteen carbon atoms, that Ar is not 4,4'-substituted phenylbenzoate, 4,4'-substituted biphenylbenzoate, or 4,4'-substituted biphenyl.
Claim 3
Dependent Claim 29 words
The chiral nonracemic compound of claim 1 wherein A, B and D, independently of one another, are selected from the group consisting of phenyl, pyridine, pyrimidine, pyridizine and pyrazine.
Claim 4
Dependent Claim 39 words
The chiral nonracemic compound of claim 1, wherein A, B and D are selected from the group phenyl, pyridine, pyrimidine, pyrazine, and pyridizine and wherein at least one of A, B or D is a nitrogen containing aromatic ring.
Claim 5
Dependent Claim 31 words
The chiral nonracemic compound of claim 1 wherein E and F are --OOC-- or --COO-- and e+f=1 and at least one of A, B or D is a nitrogen containing ring.
Claim 6
Dependent Claim 28 words
The chiral nonracemic compound of claim 1 wherein e and f are both 0 and at least one of A, B or D is a nitrogen containing ring.
Claim 7
Dependent Claim 30 words
The chiral nonracemic compound of claim 1 wherein Ar is selected from the group consisting of a 2-phenylpyridine, a 5-phenylpyridine, a 3-phenylpyridizine, 6phenylpyridizine, a 2-phenylpyrazine, a 3-phenylpyrazine, and a 5-phenylpyrimidine.
Claim 8
Dependent Claim 19 words
The chiral nonracemic compound of claim 1 wherein one or two of A, B or D are phenyl rings.
Claim 9
Dependent Claim 29 words
The chiral nonracemic compound of claim 1 wherein two of A, B, and D are phenyl rings and one of A, B, and D is a nitrogen containing aromatic.
Claim 10
Dependent Claim 14 words
The chiral nonracemic compound of claim 8 wherein e and f are both 0.
Claim 11
Dependent Claim 40 words
The chiral nonracemic compound of claim 1 wherein a, b, and d are all 1, A is a 2,5-disubstituted pyrimidine, B is a para-substituted phenyl, D is a para-substituted phenyl, e is 0, f is 1 and F is --COO--.
Claim 12
Dependent Claim 31 words
The chiral nonracemic compound of claim 1 wherein d, e and f are zero, a and b are 1 and A is a 2,5-disubstituted pyridine and B is a para-substituted phenyl.
Claim 13
Dependent Claim 31 words
The chiral nonracemic compound of claim 1 wherein d, e and f are zero, a and b are 1 and B is a 2,5-disubstituted pyridine and A is a para-substituted phenyl.
Claim 14
Dependent Claim 43 words
The chiral nonracemic compound of claim 1 wherein e and f are zero, a, b and d are 1 and A and D are phenyls and B is selected from the group consisting of 2,5-disubstituted pyridine, 2,5-disubstituted pyrimidine, 3,6-disubstituted pyridizine and 2,5-disubstituted pyrazine.
Claim 15
Dependent Claim 31 words
The chiral nonracemic compound of claim 1 wherein e and f are zero, a, b and d are 1 and A and D are phenyls and B is a 2,5-disubstituted pyrimidine.
Claim 16
Dependent Claim 39 words
The chiral nonracemic compound of claim 1 wherein E and F are selected from the group consisting of --CH 2 --CH 2 --, --O--CH 2 --, --CH 2 --O--, --S--CH 2 --, and --CH 2 --S--, and where e+f=1.
Claim 17
Dependent Claim 18 words
The chiral nonracemic compound of claim 15 wherein each of A, B and D is a phenyl ring.
Claim 18
Dependent Claim 13 words
The chiral nonracemic compound of claim 15 wherein Ar has two aromatic rings.
Claim 19
Dependent Claim 19 words
The chiral nonracemic compound of claim 15 wherein a+b+d is two and both rings of Ar are phenyl rings.
Claim 20
Dependent Claim 24 words
The chiral nonracemic compound of claim 1 wherein R' is an alkyl, alkenyl, alkoxy or thioalkyl group having from three to fifteen carbon atoms.
Claim 21
Dependent Claim 23 words
The chiral nonracemic compound of claim 1 wherein R' is an alkyl, e-alkenyl or alkoxy group having from three to fifteen carbon atoms.
Claim 22
Dependent Claim 20 words
The chiral nonracemic compound of claim 1 wherein R' is an alkyl group having from three to fifteen carbon atoms.
Claim 23
Dependent Claim 20 words
The chiral nonracemic compound of claim 1 wherein R' is a thioalkyl group having from three to fifteen carbon atoms.
Claim 24
Dependent Claim 20 words
The chiral nonracemic compound of claim 1 wherein R' is an e-alkenyl group having from three to fifteen carbon atoms.
Claim 25
Dependent Claim 15 words
The chiral nonracemic compounds of claim 1 wherein X, and Y are fluorines or chlorines.
Claim 26
Dependent Claim 13 words
The chiral nonracemic compounds of claim 1 wherein X, and Y are fluorines.
Claim 27
Dependent Claim 20 words
The chiral nonracemic compound of claim 1 wherein R is an alkyl group having from two to eight carbon atoms.
Claim 28
Dependent Claim 13 words
The chiral nonracemic compound of claim 1 wherein Ar is a 2,5-diphenylthiadiazole ring.
Claim 29
Dependent Claim 15 words
The chiral nonracemic compound of claim 11 wherein one of E or F is --COO--.
Claim 30
Dependent Claim 53 words
The chiral nonracemic compound of claim 11 wherein Ar is a core unit selected from the group consisting of: ##STR117## and wherein R' is an alkoxy group having three to fifteen carbon atoms; X and Y are fluorines; and R is an alkyl or alkenyl group having from one to fifteen carbon atoms.

References Cited (Backward Citations)

US4911861A Cited
US5100579A Cited
JPS62111939A Cited
WO1987005018A2 Cited
US5064569A Cited
EP0278665A2 Cited
US4954600A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1998-01-09 1998-07-11 1999-01-10 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2002-01-09 2002-07-11 2003-01-10 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2006-01-09 2006-07-11 2007-01-10 $7700.00 Window Closed / Lapsed

Assigned Categories & Tags

No categories assigned to this patent yet.

Assign Category Tag