GB2188048A - Liquid crystalline esters - Google Patents

Liquid crystalline esters Download PDF

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GB2188048A
GB2188048A GB08704421A GB8704421A GB2188048A GB 2188048 A GB2188048 A GB 2188048A GB 08704421 A GB08704421 A GB 08704421A GB 8704421 A GB8704421 A GB 8704421A GB 2188048 A GB2188048 A GB 2188048A
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glass
substituted
ocnh2n
cnh2n
liquid
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Prof Dr Dietrich Demus
Wolfgang Wedler
Dr Wofgang Weissflog
Dr Siegmar Diele
Dr Gerhard Pelzl
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Werk fuer Fernsehelektronik im VEB Kombinat Mikroelektronik VEB
Werk fuer Fernsehelektronik GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/39—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups
    • C07C205/42—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by esterified hydroxy groups having nitro groups or esterified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
    • C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
    • C09K19/2014—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups containing additionally a linking group other than -COO- or -OCO-, e.g. -CH2-CH2-, -CH=CH-, -C=C-; containing at least one additional carbon atom in the chain containing -COO- or -OCO- groups, e.g. -(CH2)m-COO-(CH2)n-
    • C—CHEMISTRY; METALLURGY
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/22—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and nitrogen atoms as chain links, e.g. Schiff bases
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
    • C09K19/3001—Cyclohexane rings
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
    • C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0477—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by the positioning of substituents on phenylene
    • C09K2019/0481—Phenylene substituted in meta position
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    • C09K2019/0477—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by the positioning of substituents on phenylene
    • C09K2019/0485—Phenylene substituted in ortho position

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Liquid Crystal Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Pyridine Compounds (AREA)

Abstract

Glass-like liquid crystalline esters have the general formula I <IMAGE> R<1>=CnH2n+1 or OCnH2n+1 (n=H2); R<2>=R<1>, (CH2)mCN (m=0-4), NO2, Br, H or <IMAGE> R<3> and R<4>=H, CnH2n+1, OCnH2n+1, NO2 or CN; or R<2> and R<3> together =OCH2O; <IMAGE> or <IMAGE> B=as A or <IMAGE> X=CO, C(R<5>)=N-OOC (R<5>=CnH2n+1, n=0-4) or COY (Y=Z<1)<CH2)2Z<2> in which Z<1> and Z<2>= O, S, NR<5>, CHR<5>, CO, CH=CH or -N-CR<5>- and n=0-10 or Z<2>=a single bond or OOC).

Description

SPECIFICATION Glass-like crystalline liquid 2-substituted-I ,4-bis-(4-substituted-benzoyloxy)-benzene The invention relates to glass-like liquid crystals which are used as anisotropic solid optical media for producing optical components such as, for example, compensators, prisms, plates with optical rotation, polarisers and also for thermo-electro-optical memory displays.
Glass-like liquid crystals have already been described (H. Kelker, R. Hatz: Handbook of Liquid Crystals, Verlag Chemie, Weinheim 1980; N. Kirov, M. P. Fontana, N. Afanasieva: Mol. Cryst.
Liq. Cryst. 89, 193 (1982)). The glass temperatures are very low and lie typically far below 0 C, e.g. for N-(o-hydroxy-p-methoxybenzylidene)-p-butylanilin) M. Sorai, S. Seki: Bull. Chem. Soc.
Japan 44, 2887 (1971): G. P. Johari: Phil. Magaz. Vol. 46, 549 (1982)): around --65"C.
Substances with such low glass temperatures are at room temperature in an ordinary crystalline liquid (e.g. nematic) state or are crystalline solid because they cannot be cooled down sufficiently far below their melting temperature. Consequently, they cannot be used as anisotropic solid media nor for memory displays.It has already been proposed to use 3,3'-sulphonyl or 3,3'sulphonyl-di-(4-acyloxy-benzoic acid ester), 4-[4-(4-substituted benzylidene amino)-naphthyl-(1)- azo]-benzoic acid ethyl ester, biphenyl-4,4'-bis-(4-carbonyloxy benzylidene-malonic acid-di-n-alkyl ester) or 4-4(4-alkyl cyclohexanoyloxy)-2-methyl benzoic acid-(4-substituted-phenyl ester) alone in mixtures with one another or with other crystalline liquid or non-crystalline liquid substances as anisotropic solid optical media and also for thermo-electro-optical memory displays at room temperature. For further improvement of the properties of the mixtrues to be used, however, further and new components are urgently needed.
The object of the invention is to find glass-like crystalline liquid substances of which the glass temperature is above room temperature.
According to the invention, as such crystalline liquid 2-substituted-1,4-bis(4-substituted-benzoy- loxy)-benzenes to the general formula
in which R1:CnH2n+i OCnH2n+1 s iii n=4-12, R2=R1, (CH2)m CN with m= 0-4, NO2, Br, H
R3,R4=H, CnH2n4l OCnH2n+1 NO2, CN N02,CN R2+ R3=-0-CH2-O
CO=Y with Y = Z1---(CH2)n---Z2 (Z1, 22= O, S, NR5, CHR5 , CO, CH= CH, N = CR5-) n= 0-10 and in addition Z2=a single bond, OOC were found to be suitable.
The substances can be used alone, in mixtures with one another or with other crystalline liquid or non-crystalline liquid substances as glass-like nematic liquid crystals with glass temperatures above room temperature, as anisotropic solid optical media for producing optical components such as compensators, prisms, plates with optical rotation, polarisers and also for thermoelectro-optical memory displays.
By producing correspondingly orientated layers, it is possible to produce from this optical medium and with an homogeneous orientation, optical compensators, prisms and, if dichroitic dyes are added, polarisers, or with a twisted orientation, to produce plates with an optical rotation and also, if corresponding cells are used, to produce theremo-electro-optical memory displays.
Synthesis of substances to formula I takes place by acylation of suitable intermediate products. In this respect, the molecule segments with ring systems A and B can be introduced one after another in various sequences but also simultaneously. A multiplicity of compounds can be obtained by esterifying derivatives for formula II (with Z'=0, S, NR5)
with acid chlorides III.
Acylation of the hydroquinone derivatives IV
with the acid chlorides V
takes place by known methods.
Also the acylation of trifunctional derivative VI leads to compounds to the general formula I.
(Z2 inY=O,S,NR5) Examples of embodiment Examples for production Example 1: 0.01 mol of a derivative for formula 11 is taken up in 100 ml absolute toluene. 0.01 mol of acid chloride Ill are added at room temperature, dissolved in 50 ml of toluene. Then, accompanied by agitation, the result is blended with 0.015 mol triethyl amine, left for 20 hours to stand and then heated for 30 minutes to 80"C. After cooling, the product is extracted from the precipitated hydrochloride by suction, the toluene drawn off in a vacuum and the remaining residue is recrystallised. Suitable solvents are, for example, ethanol, n-amyl alcohol, dioxane, dimethyl formamide.
Yields: 43 to 68%.
Example 2: 0.01 mol hydroquinone to formula IV is reacted with 0.02 mol of an acid chloride V in the presence of 0.03 triethyl amine and processed as described under Example 1. Yields: 51-74%.
Example 3: 0.01 mol of a trifunctional derivative to formula VI is reacted with 0.03 mol of an acid chloride VI in the presence of 0.045 mol triethyl amine and processed similarly to Example 1.
Yields: 39-57%.
Table 1 shows the conversion temperatures ( C) of a few of the substances according to the invention. In the table: K=crystalline-solid S = smectic N = nematic is = isotropic-liquid Numbers in brackets relate to monotropic conversions.
Table 1
R n K S N is COO ( CH2)O 0 O .91 - . (65) 1 .98 - 80 2 .73 - . 80 3 .68 - . 96 A 4 .80 - . (76) -coo O (CH2)n CN 0 .107- . (SO) 1 .91 - . (47) 2 2 .112 - . (39) -COO-CH2O OCnH2n n 1 .85 - 120 2 .92 - . 117 3 .82 - . 111 4 .79 - . 109 5 .75 - . 105 6 .84 - . 105 7 .80 - . 105 8 .84 - . 104 9 93 . 104 10 .92 - . 104 Table 1 cont'd.
R n K S N is -coo-cH2OOco C11H 2n +1 4 121 - . 152 5 120 - . 153 6 110 - . 153 7 103 - . 152 8 99 - . 151 9 99 - . 149 10 103 - 148 --COOO-N = C 74 - 74 - (.22) I C5H11 CH3 C=NOOC+}c5H11 58 - - (.17) CH3 CH CH = N-ooc 3C5H11 75 - - (.70) -COO-N: cH{+}0c5H13 87 - - .92 C00-N=CH cN 110 - - (,65) COO N = CH < N 77 - - .99 COO CH -CH2 108 - - (.80) N02 COO---CH, 80 . 96 .112 N02 -COO-CH2-CH = CHNO2 164. 195 - -C00-CH2-CH: ----CH = CH 107 - - 130 -COQ-CH2-CH2CN 88 (.80) .91 Table 1 cont'd.
R K S N is C CH2 CH2O+}CN 75 . 164 - - C00-CH2-CH2-O 76 16 -- . 109 --- CO --NHH- C H2 121 - - ( . 112 ) .
CO---S-CH,- 70 - - . 80 134 134. - CH2 134 . 151 - CH3 -C00-CH2-CH -N 0 60 - 70 C2H5 COOCH2{+Br 95 95 (.( 61) . 121 CH3 82 - - 113 CO0 CH eCH ( CH 3 )2 75 - - 95 t-o .99 - - 112 0CH2 COO CH X OC8H17 .78 - - 80 OCH3 -CO0-CH2 .75 - - . 86 co .85 - - (. 58) Table 2
Rl K S N is CH3O .219 - - (.151) C2H5O . 185 - - ( . 166) C3H70 .140 - - . 148 C4H90 .134 (108) . 155 C5H11O .134 . 136 . 149,5 C6Hl3O .110 151,5 . 154 C7H150 .110 . 158,5 - -.
C8H170 96 . 163 - C9H190 .93 166 - C10H21O .87 . 168 - C7H15 .100 130 - Tabte 3
R1 K N is C4H90 . 133 ( 122) C8H17O 96 .103 Examples of application Example 1 The substance to the formula
has a melting point of 70"C and a clarification point of 94"C. It is heated to about 100"C, into the isotropic-liquid range. Afterwards, it is allowed slowly to cool to temperatures around 80"C.
In this nematic condition, the molecular structure can be orientated by wall effects as well as by electric or nagnetic fields. Rapid cooling to temperatures of O to 5CC allows the nematic phase to rigidify in glass-like fashion. By fresh heating and cooling in the manner already described above, it is possible to vary the orientation. The structure of the nematic phase fixed in the glass state is stable for several months.
Example II The substance from Example I is mixed with the substance
(conversion temperatures of this substance: K 95 N 187 Is; can be cooled down to about 65cm.
The proportions in the mix were so chosen that the substance from Example I has a molar fraction of 0.72 in this binary mixture. The mixture fuses in the temperature range between 50" and 70"C to produce a nematic phase. The clarification point is around 11 iCC. Subsequent rapid cooling with a cooling table results in the formation of a clouded glass-like body which, under the polarisation microscope, shows the typical textural image of a nematic phase. This glass-like body softens under increasing temperatures in a temperature range between 20"C and 35"C.
Crystallising-out was observed after about 2 to 3 days.
Example 111 By the addition of 1 % of the dichroitic dyestuff
to the substances according to Example 1 and 2 and with an homogeneous orientation of the substance between two glass plates or other transparent material, it is possible to produce coloured polarisers which can produce linearly polarised red light and which, in a perpendicular attitude, absorb linearly polarised red light.
Example Vl By filling the substances according to Example 1, 2, 3 into an electro-optical cell which consists of glass sheets provided with an electrically conductive transparent and fittingly textured coating, and spaced apart by 5 to 30 ,'lem, a thermo-electro-optical memory display is created in which individual dots or relatively large areas of surface are heated by a laser or an electrical heater out of the glass-like state into the usual nematic state and switched over and also subsequently, while retaining the switched-over state, are cooled back to the glass state so that the input data is stored.

Claims (3)

1. Glass-like crystalline liquid 2-substituted-i ,4-bis-(4-substituted-benzoyloxy)-benzene to the general formula
in which R CnH2n+1; OCnH2n+1 ; with n=1 - 12, R2=R1, (CH2)m CN with m=O to 4, NO2, Br, H
R3,R4=H, CnH2n41 ; OCnH2n+1 NO2, CN R2+ R3=-O-CH2-O-
X= CO,
R5= CnH2n+ with n=O to 4; CO=Y with Y = Z1---(CH2)n---Z2 (Z1,Z2: O,S,NR5,CHR5, CO, CH:CH,-N=CR5-) n 0-10 in addition Z2=single bond, OOC.
2. Glass-like crystalline liquid 2-substituted-1,4-bis-(4-substituted benzoyloxy)-benzene according to Claim 1, characterised in that they are used alone, in mixtures with one another or with other crystalline liquid or non-crystalline liquid substances as anisotropic solid optical media as well as for thermo-electro-optical memory displays.
3. Glass-like Christalline liquid crystal as claimed in Claim 1, substantially as described in any of the examples herein before disclosed.
GB8704421A 1986-03-05 1987-02-25 An anisotropic solid optical medium comprising a glass-like crystalline liquid 2-substituted-1,4-bis-(4-substituted-acyloxy)-benzene Expired - Lifetime GB2188048B (en)

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DD28759386A DD247227A1 (en) 1986-03-05 1986-03-05 GLASSY NEMATIC LIQUID CRYSTALS

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Cited By (5)

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GB2222158A (en) * 1988-08-02 1990-02-28 Werk Fernsehelektronik Veb Glass forming polycyclic compounds
EP0504660A2 (en) * 1991-03-16 1992-09-23 BASF Aktiengesellschaft Liquid crystal compounds
EP0583605A1 (en) * 1992-07-22 1994-02-23 BASF Aktiengesellschaft Defined oligomeric liquid crystalline compounds with smectic liquid crystalline phases
EP3106478A4 (en) * 2014-02-14 2017-10-04 Zeon Corporation Polymerizable compound, polymerizable composition, polymer, and optically anisotropic body
US10071949B2 (en) 2015-12-29 2018-09-11 Samsung Electronics Co., Ltd. Polymerizable liquid crystal compound, composition for optical film, and optical film, compensation film, antireflective film, and display device including the same

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DE4332733A1 (en) * 1993-09-25 1995-03-30 Basf Ag Liquid crystalline compounds
JP2006347893A (en) * 2005-06-13 2006-12-28 Hirosaki Univ New t type compound and liquid crystal composition containing the same compound

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CHEMICAL ABSTRACTS 105(8):70528P *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2222158A (en) * 1988-08-02 1990-02-28 Werk Fernsehelektronik Veb Glass forming polycyclic compounds
GB2222158B (en) * 1988-08-02 1992-06-03 Werk Fernsehelektronik Veb Glass forming polycyclic compounds
EP0504660A2 (en) * 1991-03-16 1992-09-23 BASF Aktiengesellschaft Liquid crystal compounds
EP0504660A3 (en) * 1991-03-16 1994-03-23 Basf Ag
US5417882A (en) * 1991-03-16 1995-05-23 Basf Aktiengesellschaft Liquid-crystalline compounds
EP0583605A1 (en) * 1992-07-22 1994-02-23 BASF Aktiengesellschaft Defined oligomeric liquid crystalline compounds with smectic liquid crystalline phases
US5417884A (en) * 1992-07-22 1995-05-23 Basf Aktiengesellschaft Defined oligomeric liquid-crystalline compounds having smectic liquid-crystalline phases
EP3106478A4 (en) * 2014-02-14 2017-10-04 Zeon Corporation Polymerizable compound, polymerizable composition, polymer, and optically anisotropic body
US10400170B2 (en) 2014-02-14 2019-09-03 Zeon Corporation Polymerizable compound, polymerizable composition, polymer, and optically anisotropic product
US10954443B2 (en) 2014-02-14 2021-03-23 Zeon Corporation Polymerizable compound, polymerizable composition, polymer, and optically anisotropic product
US10071949B2 (en) 2015-12-29 2018-09-11 Samsung Electronics Co., Ltd. Polymerizable liquid crystal compound, composition for optical film, and optical film, compensation film, antireflective film, and display device including the same

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DE3703640A1 (en) 1987-09-10
JPS62212349A (en) 1987-09-18
GB8704421D0 (en) 1987-04-01
DD247227A1 (en) 1987-07-01
GB2188048B (en) 1990-09-12
CH671233A5 (en) 1989-08-15

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