DE19732158A1 - Chip card with bistable display - Google Patents

Abstract

A chip card containing a ferroelectric liquid crystal display with a ferroelectric liquid crystal layer is characterised in that the liquid crystal layer consists of a low-molecular liquid crystal with a higher-order, inclined smectic phase in the working temperature range. The display used according to the invention can be switched at voltages </=15 V, in general </=5 V, can be written in a wide temperature range and withstands everyday stresses such as pressure, bending, deformation or extreme temperatures.

Description

A chip card is a card, usually made of plastic and in Credit card format, provided with an integrated circuit, which Can store and / or edit information electronically, and means for Information transfer between the card and an electronic reading and / or writing system.

A smart card is a chip card that also provides means for Review / control of access to the card. For example, this means an integrated one Circuit that controls who has the stored information what purpose used. This can increase data security.

Chip or smart cards are, for example, as telephone and credit cards "Medicards", "Cashcards" and as ID cards for access control, already in diverse use.

These technologies are expected to advance further in the near future Areas such as the "electronic wallet", i.e. H. Replacement of cash, tickets and pay TV.

Desirable and already proposed for chip cards is a permanent, visible electronic display (display) on the card, the information, for example about fill level, remaining amount or dates.

Such a display should also work without applying electrical voltage be readable, since neither the thickness nor the manufacturing costs of a card make the installation allow a battery. The display must therefore have an optical storage capacity have.

For reasons of optical bistability, such applications have so far been used surface stabilized-ferroelectric-liquid crystal displays (Surface Stabilized  Ferroelectric Liquid Crystal Displays, SSFLCD) and bistable nematic displays (see E. Lüder et al. 1997 International Symposium, Seminar & Exhibition, Society of Information Display, Boston, Massachusetts, Article 9.4, SID 97 DIGEST, pp. 109-112) as well as surface or polymer-stabilized cholesteric textures (SSCT or PSCT).

SSFLCD's are already in use as computer displays, the use in Chip cards, however, require a considerably different property profile, that for example, in accordance with ISO 7816 in addition to the optical storage capacity of printing and Shock resistance, flexibility, a low addressing voltage, readability Daylight and particularly low thickness and weight includes.

There is therefore a high demand for SSFLC displays or for ferroelectric ones Liquid crystal mixtures (FLC) for such displays, which specifically the Requirements for chip or smart cards have grown.

The task of finding a mechanically and thermally stable optically bistable display for use in chip cards, which can be operated at voltages below 15 volts, preferably below 5 volts, has a high contrast and a high brightness or reflectivity Surprisingly, solved by using higher order, inclined smectic liquid crystal phases, such as S _I *, S _F *, or inclined smectic crystals, such as S _J *, S _G *, S _K *, S _H *.

An object of the invention is therefore a chip card containing one Ferroelectric liquid crystal display, characterized in that the Liquid crystal layer consists of a ferroelectric liquid crystal which in Working temperature range has a highly ordered inclined smectic phase.

The display used according to the invention can at voltages ≦ 15 V, in general ≦ 5 V, can be switched is in a wide temperature range writable and robust against everyday loads such as pressure, Bending, deformation or thermal stress.  

For the purposes of the invention, higher order means higher order than smectic C phase.

The working temperature range preferably covers the range from 0 to 60 ° C, particularly preferably 10 to 50 ° C, very particularly preferably 15 to 40 ° C.

The chip card according to the invention is preferably a smart card.

The highly ordered inclined smectic, optically active (ferroelectric) Liquid crystal (FLC) can consist of a mixture of low molecular weight Connections consist of a single substance as well.

Working phases are preferably S _I *, S _F *, S _J * or S _G * phases, preferably S _I * or S _F * phases.

In the case of mixtures, it is preferred that the mixture be non-optical active base mixture, preferably in a proportion of <50%, and one or there are several optically active compounds (dopants). If the If liquid crystal is a single compound, then it must itself be optically active be.

The FLC generally has a spontaneous polarization of 0.1 to 100 nC / cm ^-2 , preferably 1 to 60 nC / cm ^-2 , particularly preferably 2 to 40 nC / cm ² .

Suitable compounds for FLC are known to the person skilled in the art.

Generally suitable connections can e.g. B. by the general formula (I),

R ¹ (-A ¹ -M ¹ ) _a (-A ² -M ² ) _b (-A ³ -M ³ ) _c (-A ⁴ ) -R ² (I)

where the symbols and indices have the following meanings:
R ¹ , R ² are the same or different

• a) hydrogen, -F, -Cl, -CF ₃ , -OCF ₃ or -CN,
• b) a straight-chain or branched alkyl radical (with or without asymmetrical carbon atom) with 1 to 20 carbon atoms, where
  • b1) one or more non-adjacent and non-terminal CH ₂ groups by -O-, -S-, -CO-O-, -O-CO-, -CS-O-, -O-CS-, -CS- S-, -S-CS-, -CO-S-, -S-CO-, -O-CO-O- or -Si (CH ₃ ) ₂ - can be replaced and / or
  • b2) one or more CH ₂ groups can be replaced by -CH = CH-, -C∼C-, cyclopropane-1,2-diyl, 1,4-phenylene, 1,4-cyclohexylene or 1,3-cyclopentylene and or
  • b3) one or more H atoms can be replaced by F and / or Cl and / or CN and / or
  • b4) the terminal CH ₃ group can be replaced by one of the following chiral groups (optically active or racemic):
    

with the proviso that at most one of the radicals R ¹

, R ²

Hydrogen, -F, -Cl, -CF ₃

, -OCF ₃

or can be -CN;
R ³

, R ⁴

, R ⁵

, R ⁶

, R ⁷

are the same or different

• a) hydrogen
• b) a straight-chain or branched alkyl radical (with or without asymmetric carbon atom) with 1 to 16 carbon atoms, where
  • b1) one or more non-adjacent and non-terminal CH ₂ groups can be replaced by -O- and / or
  • b2) one or two CH ₂ groups can be replaced by -CH = CH-,
• c) R ⁴ and R ⁵ together also - (CH ₂ ) ₄ - or - (CH ₂ ) ₅ - if they are bonded to an oxirane, dioxolane, tetrahydrofuran, tetrahydropyran, butyrolactone or valerolactone system;

M ¹

, M ²

, M ³

, are the same or different -CO-O-, -O-CO-, -CO-S-, -S-CO-, -CS-O-, -O-CS-, -CS-S-, -S- CS-, -CH ₂

-O-, -O-CH ₂

-, -CH ₂

-S-, -S-CH ₂

-, -CH = CH-, -C∼C-, -CH ₂

-CH ₂

-CO-O-, -O-CO-CH ₂

-CH ₂

-, -CH = N- or a single bond;
A ¹

, A ²

, A ³

, A ⁴

are identical or different 1,4-phenylene, where one or more H atoms are represented by F, Cl, OCH ₃

, CH ₃

, C ₂

H ₅

, CF ₃

, OCF ₃

and / or CN can be replaced, 1,3-phenylene, where one or two CH groups can be replaced by N, pyridazine-3,6-diyl, where one or two H atoms can be replaced by F, Cl and / or CN may be replaced, pyridine-2,5-diyl, where one or more H atoms may be replaced by F, Cl and / or CN, pyrimidine-2,5-diyl, where one or two H atoms may be replaced by F, Cl and / or CN can be replaced, 1-alkyl-1-silacyclohexylene-1,4-diyl, where one or two H atoms can be replaced by F and / or CN,
1,4-cyclohexylene, where one or two H atoms by CN and / or CH ₃

and / or F can be replaced, (1,3,4) -thiadiazole-2,5-diyl, 1,3-dioxane-2,5-diyl, 1,3-dithiane-2,5-diyl, 1, 3-thiazole-2,4-diyl, where one H atom can be replaced by F, Cl and / or CN, 1,3-thiazole-2,5-diyl, one H atom by F, Cl and / or CN can be replaced, thiophene-2,4-diyl, where an H atom can be replaced by F, Cl and / or CN, thiophene-2,5-diyl, where one or two H atoms can be replaced by F, Cl and / or CN can be replaced, naphthalene-2,6-diyl, where one or more H atoms can be replaced by F, Cl and / or CN, naphthalene-1,4-diyl where one or more H atoms can be replaced by F, Cl and / or CN can be replaced, naphthalene-1,5-diyl, where one or more H atoms can be replaced by F, Cl and / or CN, phenanthrene-2,7-diyl or 5,10- Dihydrophenanthrene-2,7-diyl, where one, two or more H atoms can be replaced by F and one or two CH groups can be replaced by N, indan-2,5-diyl, indan-1-one 2,5-diyl, benzothiazole-2,6-diyl, benzothiazo l-2,5-diyl, benzoxazole-2,6-diyl, benzoxazole-2,5-diyl, benzofuran-2,5-diyl, benzofuran-2,6-diyl, 2,3-dihydrobenzofuran-2,5- diyl, piperazine-1,4-diyl, piperazine-2,5-diyl or 1,3-dioxaborinane-2,5-diyl;
a, b, c, are 0 or 1, with the proviso that the compound of formula (I) may not contain more than four five or more-membered ring systems.

The liquid crystal generally contains 2 to 35, preferably 2 to 25, particularly preferably 2 to 20 components.

The components of the liquid crystal are preferably selected from the known compounds with smectic and / or nematic and / or cholesteric phases, for example of the formula (I). These include e.g. B .:

• - Derivatives of phenylpyrimidine, such as in WO 86/06401 and USA 874 542,
• - Meta-substituted six-ring aromatics, such as, for example, in EP-A 0 578 054 described
• Silicon compounds, as described for example in EP-A 0 355 008,
• - Mesogenic compounds with only one side chain, such as in EP-A 0 541 081,
• Hydroquinone derivatives, as described for example in EP-A 0 603 786,
• Phenylbenzoates and biphenylbenzoates, such as those from P. Keller, Ferroelectrics 1984, 58, 3; Liq. Cryst. 1987, 2, 63; Liq. Cryst. 1989, 5, 153 and J. W. Goodby et al., Liquid Crystals and Ordered Fluids, Vol. 4, New York Described in 1984,  
• Thiadiazoles, as described, for example, in EP-A 0 309 514,
• Biphenyls such as, for example, in EP-A 0 207 712 or Adv. Liq. Cryst. Res. Appl. (Ed. Bata, L.) 3 (1980),
• - Phenylpyridines such as in Ferroelectrics 1996, 180, 269 or Liq. Cryst. 1993, 14, 1169,
• - Benzanilides such as in Liq. Cryst. 1987, 2, 757 or Ferroelectrics 1984, 58, 81,
• Terphenyls such as in Mol. Cryst. Liq. Cryst. 1991, 195, 221; WO-A 89 / 02.425 or Ferroelectrics 1991, 114, 207,
• - 4-Cyanocyclohexyls such as in a Freiburg conference Liquid crystals 1986, 16, V8 described,
• 5-alkylthiophenecarboxylic acid esters, for example in Butcher, J.L., Dissertation, Nottingham 1991,
• - 1,2-diphenylethanes such as in Liq. Cryst. 1991, 9, 253 described.

Examples of chiral, non-racemic dopants are:

• optically active phenylbenzoates, such as, for example, P. Keller, Ferroelectrics 1984, 58, 3 and J.W. Goodby et al., Liquid Crystals and Ordered Fluids, Vol. 4, New York 1984,
• - Optically active oxirane ethers, such as, for example, in EP-A 0 263 437 and WO-A 93/13093,
• - Optically active oxirane esters, as for example in EP-A 0 292 954 described
• optically active dioxolane ethers, such as, for example, in EP-A 0 351 746 described
• - Optically active dioxolane esters, such as, for example, in EP-A 0 361 272 described
• - Optically active tetrahydrofuran-2-carboxylic acid esters, as for example in EP-A 0 355 561 described, and
• - Optically active 2-fluoroalkyl ethers, such as in EP-A 0 237 007 and US 5,051,506.

Particularly preferred components of the liquid crystal are those from groups A to P:

• A. phenylazaaryl derivatives of the formula (II),
  R ¹ -A ¹ -A ² -R ² (II)
  wherein
  R ¹ and R ² each alkyl with 1-15 C atoms, in which also one or two non-adjacent and non-terminal CH ₂ groups by -O-, -S-, -CO-, -O-CO-, -CO -O-, -O-CO-O-, -CO-S-, -S-CO-, -CH-halogen, -CHCN- and / or -CH = CH- can be replaced and in which one, several or all H atoms can be replaced by F,
  A ^{1 represents} 1,4-phenylene, trans-1,4-cyclohexylene or a single bond, and A ²
  and Z denotes -O-CO-, -CO-O-, -S-CO-, -CO-S-, -CH ₂ O-, -OCH ₂ - or -CH ₂ CH ₂ -.
• B. 5-alkylthiophenecarboxylic acid esters of the formula (III),
  in which mean:
  R ¹ , R ² straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or more non-adjacent -CH ₂ groups being replaced by -O-, -O-CO- or -CO-O- can,
  A ¹ , A ² , A ³ , are the same or different, 1,4-phenylene, where one or two H atoms can be replaced by F, pyridine-2,5-diyl, one or two H atoms being replaced by F may be replaced, pyrimidine-2,5-diyl, where one or two H atoms may be replaced by F, trans-1,4-cyclohexylene, where one or two H atoms may be replaced by -CN and / or -CH ₃ can be (1,3,4) -Thiadiazol-2,5-diyl,
  M ¹ , M ² identical or different, -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH ₂ -CH ₂ -, -CH = N-,
  a, b, c, d, e zero or one.
• C. Schiff bases of the formula (IV),
  R ¹ (-A) _a (-M ¹ ) _b (-A) _c (-M ² ) _d (-A) _e -R ² (IV)
  in which mean:
  R ¹ , R ^{2 are} identical or different, a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH ₂ groups also being represented by -O-, -CO-, -CO-O-, -O-CO- or -O-CO-O- can be replaced,
  A 1,4-phenylene,
  M ¹ , M ² identical or different, -CO-O-, -O-CO-, -CH = N-, with the proviso that at least one of the groups is -CH = N-,
  a, b, c, d, e zero or one, provided that a + c + e = 2 or 3 and b + d = 1 or 2.
• D. 4-cyanocyclohexyls of the formula (V),
  in which mean:
  R ¹ , R ^{2 are} identical or different, straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, with one or two non-adjacent and non-terminal CH2 groups by -O-, -CO -, - CO -O-, -O-CO- or -O-CO-O- can be replaced, and in which one or more H atoms can be replaced by F,
  A ¹ , A ² , A ³ , are the same or different, 1,4-phenylene, where one or two H atoms can be replaced by F, pyridine-2,5-diyl, one or two H atoms being replaced by F may be replaced, pyrimidine-2,5-diyl, where one or two H atoms may be replaced by F, trans-1,4-cyclohexylene, where one or two H atoms may be replaced by -CN and / or -CH ₃ can be (1,3,4) -Thiadiazol-2,5-diyl,
  M ¹ , M ² identical or different, -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH ₂ -CH ₂ -, -CH = N-,
  a, b, c, d, e zero or one.
• E. Compounds with only one side chain of the formula (VI),
  R ¹ (-A ¹ ) _a (-M ¹ ) _b (-A ² ) _c (-M ² ) _d (-A ³ ) _e (-M ³ ) _f (-A ⁴ ) -H (VI)
  in which mean:
  R ¹ : straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH ₂ groups also being represented by -O-, -CO-, -CO-O-, - O-CO-, -O-CO-O- or -Si (CH ₃ ) ₂ - can be replaced,
  A ¹ , A ² , A ³ , A ⁴ identical or different, 1,4-phenylene, where one or two H atoms can be replaced by F or CN, pyridine-2,5-diyl, one or two H- Atoms can be replaced by F, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, trans-1,4-cyclohexylene, (1,3,4) -Thiadiazol-2,5- diyl or naphthalene-2,6-diyl,
  M ¹ , M ² , M ^{3 the} same or different, -CO-O-, -O-CO-, -CH ₂ -O-, -CH = N-, -O-CH ₂ -, -CH ₂ -CH ₂ -,
  a, b, c, d, e, f zero or one, provided that the sum of a + c + e is 0, 1, 2 or 3;
• F. metasubstituted compounds of formula (VII),
  in which mean:
  R ¹ , R ^{2 are} identical or different, a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, one or two non-adjacent and non-terminal CH2 groups also being represented by -O-, -CO-, - CO-O-, -O-CO-, -O-CO-O- or -Si (CH ₃ ) ₂ - can be replaced,
  A ¹ , A ² , A ^{3, the} same or different, 1,4-phenylene, where one or two H atoms can be replaced by F, pyridine-2,5-diyl, where one or two H atoms can be replaced by F. can, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, trans-1,4-cyclohexylene, where one or two H atoms can be replaced by -CN and / or -CH ₃ , (1,3,4) -Thiadiazol-2,5-diyl,
  and A ¹ too
  M ¹ , M ² , M ^{3 the} same or different, -O-, -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH ₂ -CH ₂ -, -CH = N-,
  X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ , X ⁸ CH or N, where the number of N atoms in a six-membered ring is 0, 1 or 2,
  a, b, c, d, e, f are zero or one, provided that the sum of a + c + e is 0, 1, 2 or 3.
• G. silicon compounds of the formula (VIII),
  R ¹ (-A ¹ ) _i (-M ¹ ) _k (-A ² ) _l (-M ² ) _m (-A ³ ) _n -R ² (VIII)
  in which mean:
  R ¹ straight-chain or branched alkyl having 1 to 22 or 3 to 22 carbon atoms, with one or two non-adjacent and non-terminal CH ₂ groups by -O-, -CO-, -CO-O-, -O -CO- or -O-CO-O- can be replaced,
  R ² straight-chain or branched alkyl having 1 to 22 or 3 to 22 carbon atoms, where also one or two non-adjacent CH2 groups by -O-, -CO-, -CO-O-, -O-CO- or -O-CO-O- can be replaced, with the proviso that a non-oxygen-bound CH ₂ group is replaced by -Si (CH ₃ ) ₂ -,
  A ¹ , A ² , A ^{3, the} same or different, 1,4-phenylene, where one or two H atoms can be replaced by F, trans-1,4-cyclohexylene, pyridine-2,5-diyl, one or two H atoms can be replaced by F, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, (1,3,4) thiadiazole-2,5-diyl,
  M ¹ , M ² identical or different -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH = N-,
  i, k, l, m, n zero or 1, with the proviso that i + l + n = 2 or 3.
• H. hydroquinone derivatives of the formula (IX),
  in which mean:
  R ¹ , R ² : the same or different straight-chain or branched alkyl radical having 1 or 3 to 16, preferably 1 or 3 to 10, carbon atoms, one or two non-adjacent and non-terminal CH2 groups also passing through
  -O-, -CO-, -O-CO-, -CO-O-, -O-CO-O-, preferably -O-, -O-CO-, -CO-O-, can be replaced,
  R ³ -CH ₃ , CF ₃ or -C ₂ H ₅ , preferably -CH ₃ , CF ₃ ,
  A ¹ , A ^{2 the} same or different, 1,4-phenylene, trans-1,4-cyclohexylene, preferably 1,4-phenylene.
• I. pyridylpyrimidines of the formula (X),
  in which mean:
  A is N and B is CH or A is CH and B is N, C is N and D is CH or C is CH and D is N, it being possible for one or two CH groups to be replaced by CF groups,
  R ¹ , R ^{2 are} identical or different, a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, one or two non-adjacent and non-terminal CH2 groups also being represented by -O-, -CO-, - CO-O-, -O-CO- or -O-CO-O- can be replaced and wherein one, more or all H atoms can be replaced by F.
• J. phenylbenzoates of the formula (XI),
  R ¹ (-A) _a (-M ¹ ) _b (-A) _c (-M ² ) _d (-A) _e -R ² (XI)
  in which mean:
  R ¹ , R ^{2 are} identical or different, a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, one or two non-adjacent and non-terminal CH2 groups also being represented by -O-, -CO -, - CO-O-, -O-CO- or -O-CO-O- can be replaced,
  A 1,4-phenylene,
  M ¹ , M ^{2 the} same or different, -CO-O-, -O-CO-,
  a, b, c, d, e zero or one, provided that a + c + e = 2 or 3 and b + d = 1 or 2.
• K. Optically active phenylbenzoates of the formula (XII),
  R ¹ (-A) _a (-M ¹ ) _b (-A) _c (-M ² ) _d (-A) _e -R ² (XII)
  in which mean:
  R ¹ , R ^{2 are} identical or different, a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, one or two non-adjacent and non-terminal CH2 groups also being represented by -O-, -CO-, - CO-O-, -O-CO- or -O-CO-O- can be replaced, and wherein at least one of the radicals R ¹ , R ^{2 is} a branched, optically active alkyl group,
  A 1,4-phenylene,
  M ¹ , M ² identical or different, -CO-O-, -O-CO- or a single bond,
  a, b, c, d, e zero or one, provided that the sum of a + c + e is 2 or 3 and b + d = 1 or 2.
• L. Optically active oxirane ethers of the formula (XIII),
  where the symbols and indices have the following meaning:
  * a chiral center,
  R ^{1 is} a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, with one or two non-adjacent and non-terminal CH2 groups by -O-, -CO-, -CO-O-, -O -CO-, -O-CO-O- or -Si (CH ₃ ) ₂ - can be replaced,
  or the following, optically active group,
  R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ^{7, the} same or different, H or a straight-chain or branched alkyl radical having 1 to 16 carbon atoms,
  P -CH ₂ - or -CO-,
  A ¹ , A ² , A ³ are the same or different, 1,4-phenylene, where one or two H atoms can be replaced by F, pyridine-2,5-diyl, one or two H atoms each having F may be replaced, pyrimidine-2,5-diyl, where one or two H atoms may be replaced by F, trans-1,4-cyclohexylene, where one or two H atoms may be replaced by -CN and / or -CH ₃ can be (1,3,4) -Thiadiazol-2,5-diyl,
  M ¹ , M ² identical or different, -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH ₂ -CH ₂ -, -CH = N-,
  a, b, c, d, e zero or one.

The asymmetric carbon atoms of the oxirane ring or rings can have the same or different R or S configuration.

• M. Optically active oxirane esters of the formula (XIV),
  where the symbols and indices have the following meaning:
  * a chiral center,
  R ^{1 is} a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, with one or two non-adjacent and non-terminal CH2 groups by -O-, -CO-, -CO-O-, -O -CO-, -O-CO-O- or -Si (CH ₃ ) ₂ - can be replaced,
  R ² , R ³ , R ^{4 are the} same or different, H or a straight-chain or branched alkyl radical with 1 to 16 carbon atoms,
  A ¹ , A ² , A ^{3, the} same or different, 1,4-phenylene, where one or two H atoms can be replaced by F, pyridine-2,5-diyl, one or two H atoms being replaced by F. may be pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, trans-1,4-cyclohexylene, where one or two H atoms can be replaced by -CN and / or -CH ₃ can, (1,3,4) -Thiadiazol-2,5-diyl,
  M ¹ , M ² identical or different, -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH ₂ -CH ₂ -, -CH = N-,
  a, b, c, d, e zero or one.

The asymmetric carbon atoms of the oxirane ring can be configured in the same or different R or S configuration.

• N. Optically active dioxolane ethers of the formula (XV),
  where the symbols and indices have the following meaning:
  * a chiral center,
  R ^{1 is} a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, with one or two non-adjacent and non-terminal CH2 groups by -O-, -CO-, -CO-O-, -O -CO-, -O-CO-O- or -Si (CH ₃ ) ₂ - can be replaced,
  R ² , R ³ , R ^{4 are} identical or different H, a straight-chain or branched alkyl radical with 1 to 16 or 3 to 10 C atoms or an alkenyl radical with 2 to 16 C atoms, where R ² and R ³ together also - (CH ₂ ) ₅ - can be
  A ¹ , A ² , A ^{3, the} same or different, 1,4-phenylene, where one or two H atoms can be replaced by F, pyridine-2,5-diyl, where one or two H atoms can be replaced by F. can, pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, trans-1,4-cyclohexylene, where one or two H atoms can be replaced by -CN and / or -CH ₃ , (1,3,4) -Thiadiazol-2,5-diyl,
  M ¹ , M ² identical or different, -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH ₂ -CH ₂ -, -CH = N-,
  a, b, c, d, e zero or one.

Asymmetric carbon atoms of the dioxolane ring can be configured the same or differently, R or S.

• O. optically active dioxolane esters of the formula (XVI),
  in which mean:
  * a chiral center
  R ¹ straight-chain or branched alkyl radical having 1 to 16 or 3 to 16 carbon atoms, where one or more non-adjacent and non-terminal CH ₂ groups by -O-, -CO-, -O-CO- or -CO-O - can be replaced,
  R ² , R ³ , R ^{4 are the} same or different, H or an alkyl or alkenyl radical having 1 to 10 or 2 to 10 C atoms, where R ² and R ³ together can also be - (CH ₂ ) ₅ -,
  A ¹ , A ² , A ³ , identical or different, 1,4-phenylene, where one or two H atoms can be replaced by F, pyridine-2,5-diyl, one or two H atoms being replaced by F. can be pyrimidine-2,5-diyl, where one or two H atoms can be replaced by F, trans-1,4-cyclohexylene, where one or two H atoms can be replaced by -CN and / or -CH ₃ can, (1,3,4) -Thiadiazol-2,5-diyl,
  M ¹ , M ² identical or different, -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH ₂ -CH ₂ -, -CH = N-,
  a, b, c, d, e zero or one.

Asymmetric carbon atoms of the dioxolane ring can have the same or different R or S configuration.

• P. macrocyclic compounds of formula (XVII),
  in which mean:
  n: 0.1
  Y: -CO- (t-butyl), -CO- (adamantyl)
  Q: O, NY.

The liquid crystal components are produced in accordance with the known Methods familiar to those skilled in the art, such as, for example, in Houben Weyl, Methods of organic chemistry. Georg Thieme Verlag Stuttgart or the quoted Writings are described.

The mixture is prepared by methods known per se.

Mixtures which contain at least one component from groups A are preferred to D included.

Mixtures containing one or more, preferably two, are particularly preferred to eleven, components from group A and one or more components the groups B, C and / or D, preferably one to seven components from the Groups B, C and / or D included.

The mixtures preferably contain 0.1 to 79% by weight of one or more Group A components and 0.1 to 67% by weight of one or more Components from groups B, C and / or D.

The mixtures particularly preferably contain 3 to 67% by weight of one or several components of group A and 1 to 57 wt .-% of one or more Components from groups B, C and / or D.

The mixtures very particularly preferably contain 5 to 53% by weight of two to nine components of group a and 1 to 43% by weight of one to five Components from groups B, C and / or D.

The ferroelectric liquid crystal (FLC) display used according to the invention contains two carrier plates, these can be made of glass or, because of the flexibility preferably, plastic or one each made of glass, the other of Plastic. Suitable plastics are, for example, known plastics such as Polyarylates, polyether sulfones, cycloolefin copolymers, polyetherimides, Polycarbonate, polystyrene, polyester, polymethyl methacrylates, and their Copolymers or blends. The inside of these carrier plates are also conductive  transparent layers, as well as orientation layers and possibly further auxiliary layers, such as insulation layers.

The orientation layer (s), e.g. B. Polyimides such as 6,6-nylon are common rubbed films made of organic polymers or obliquely evaporated Silicon dioxide.

Crucial for the electro-optical properties and storage properties of the display is the approx. 1-3 µm thick FLC layer, the layer thickness, is preferably determined by spacers. These spacers can mixed particles, such as spheres, or structured columns in the Be inside the display.

The entire cell, usually sealed with an adhesive frame, can electrically, for example by soldering, bonding, pressing or the like. The display is powered by a voltage or voltage pulses suitable electronic circuit controlled. The control takes place in the generally directly or as a multiplex control (see e.g. Jean Dijon in Liquid Crystals, Application and Uses (Ed. B. Bahadur) Vol. 1, 1990, Chapter 13, pp. 305-360) or T. Harada, M. Taguchi, K. Iwasa, M. Kai SID 85 Digest, 131 (1985).

The electro-optical effect, which is based on the birefringence of the FLC material or on based on the anisotropic absorption of a mixed dichroic dye, is visible between two crossed polarizers (polarizing foils).

The electrode spacing is generally 0.5 to 4 μm, preferably at least 1.2 µm, particularly preferably at least 1.5 µm.

The FLC display for the chip card according to the invention can thus be manufactured fundamentally known methods follow, as described, for example, in E. Lüder et al. 1997 International Symposium, Seminar & Exhibition, Society of Information Display, Boston, Massachusetts, article 9.4, SID 97 DIGEST, pp. 109-112.  

To produce a chip card, the FLC display is placed in or on one with a or several electronic microchips provided plastic card embedded or applied.

The microchips contain the program and / or memory functions that the Ensure the desired function of the chip card. Such chips and theirs Production are known to the person skilled in the art.

The card also contains means for data exchange with an external one Writing and / or reading system, for example electrically conductive contacts or an "antenna" in the form of flat coils.

The card body is generally made of plastic, preferably Polyvinyl chloride (PVC) or acrylic-butadiene-styrene copolymers (ABS) or Biopol® (a biodegradable plastic, from renewable resources, the company Monsanto, USA).

The plastic cards used are known and for the most part commercial available (e.g. Gemplus, http://www.gemplus.fr).

Usual technical specifications for chip or smart cards according to the invention can be found, for example, in:
ICC-Card Specification for Payment Systems (Version 2 (1996)) and the literature cited therein, in particular:

• - Europay, MasterCard, and Visa (EMV): June 30, 1996
  Integrated Circuit Card Application Specification for Payment Systems
• - ISO / IEC 7813: 1990
  Identification cards - Financial transaction cards
• - ISO 7816: 1987
  Identification cards - Integrated circuit (s) cards with contacts
• - Part 1: Physical characteristics
• - ISO 7816-2: 1988
  Identification cards - Integrated circuit (s) cards with contacts
• - Part 2: Dimensions and location of contacts
• - ISO / IEC 7816-3: 1989
  Identification cards - Integrated circuit (s) cards with contacts
• - Part 3: Electronic signals and transmission protocols
• - ISO / IEC 7816-3: 1992
  Identification cards - Integrated circuit (s) cards with contacts
• - Part 3, Amendment 1: Protocol type T = 1, asynchronous half duplex block transmission protocol
• - ISO / IEC 7816-3: 1994
  Identification cards - Integrated circuit (s) cards with contacts
• - Part 3, Amendment 2: Protocol type selection (Draft International Standard)
• - ISO / IEC 7816-4: 1995
  Identification cards - Integrated circuit (s) cards with contacts
• - Part 4, Inter-industry commands for interchange
• - ISO / IEC 7816-5: 1994
  Identification cards - Integrated circuit (s) cards with contacts
• - Part 5: Numbering system and registration procedure for application identifiers
• - ISO / IEC 7816-6: 1995
  Identification cards - Integrated circuit (s) cards with contacts
• - Part 6: Inter-industry data elements (Draft International Standard).

The chip card according to the invention is suitable, for example, for access control, as check card, electronic ticket, telephone card, parking garage card, "electronic wallet" or for pay TV.

Reference is expressly made to the references cited in this application taken; through quotation they are part of the description.

Claims (10)

1. Chip card containing a ferroelectric liquid crystal display, characterized in that the liquid crystal layer consists of a ferroelectric liquid crystal which has a highly ordered inclined smectic phase in the working temperature range. 2. Chip card according to claim 1, characterized in that the highly ordered inclined smectic phase is an S _I *, S _F *, S _J * or S _G * phase. 3. Chip card according to claim 2, characterized in that the highly ordered inclined smectic phase is an S _I * or S _F * phase. 4. Chip card according to claim 1 or 2, characterized in that the liquid crystal layer contains one or more compounds from groups A to D:

• A. phenylazaaryl derivatives of the formula (II),
  R ¹ -A ¹ -A ² -R ² (II)
  wherein
  R ¹ and R ² each alkyl with 1-15 C atoms, in which also one or two non-adjacent and non-terminal CH ₂ groups by -O-, -S-, -CO-, -O-CO-, -CO -O-, -O-CO-O-, -CO-S-, -S-CO-, -CHHalogen, -CHCN- and / or -CH = CH- can be replaced and in which one, several or all H- Atoms can be replaced by F,
  A ^{1 represents} 1,4-phenylene, trans-1,4-cyclohexylene or a single bond, and A ²
  and Z represents -O-CO-, -CO-O-, -S-CO-, -CO-S-, -CH ₂ O-, -OCH ₂ - or -CH ₂ CH ₂ ;
• B. 5-alkylthiophenecarboxylic acid esters of the formula (III),
  in which mean:
  R ¹ , R ² straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or more non-adjacent -CH ₂ groups being replaced by -O-, -O-CO- or -CO-O- can
  A ¹ , A ² , A ³ , are the same or different, 1,4-phenylene, where one or two H atoms can be replaced by F, pyridine-2,5-diyl, one or two H atoms being replaced by F may be replaced, pyrimidine-2,5-diyl, where one or two H atoms may be replaced by F, trans-1,4-cyclohexylene, where one or two H atoms may be replaced by -CN and / or -CH ₃ can be (1,3,4) -Thiadiazol-2,5-diyl,
  M ¹ , M ² identical or different, -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH ₂ -CH ₂ -, -CH = N-,
  a, b, c, d, e zero or one;
• C. Schiff bases of the formula (IV),
  R ¹ (-A) _a (-M ¹ ) _b (-A) _c (-M ² ) _d (-A) _e -R ² (IV)
  in which mean:
  R ¹ , R ^{2 are} identical or different, a straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 C atoms, one or two non-adjacent and non-terminal CH ₂ groups also being represented by -O-, -CO-, -CO-O-, -O-CO- or -O-CO-O- can be replaced,
  A 1,4-phenylene,
  M ¹ , M ² identical or different, -CO-O-, -O-CO-, -CH = N-, with the proviso that at least one of the groups is -CH = N-,
  a, b, c, d, e zero or one, provided that a + c + e = 2 or 3 and b + d = 1 or 2;
• D. 4-cyanocylohexyls of the formula (V),
  in which mean:
  R ¹ , R ^{2 are the} same or different, straight-chain or branched alkyl radical having 1 to 22 or 3 to 22 carbon atoms, one or two non-adjacent and non-terminal CH2 groups by -O-, -CO -, - CO -O-, -O-CO- or -O-CO-O- can be replaced, and in which one or more H atoms can be replaced by F,
  A ¹ , A ² , A ³ , are the same or different, 1,4-phenylene, where one or two H atoms can be replaced by F, pyridine-2,5-diyl, one or two H atoms being replaced by F may be replaced, pyrimidine-2,5-diyl, where one or two H atoms may be replaced by F, trans-1,4-cyclohexylene, where one or two H atoms may be replaced by -CN and / or -CH ₃ can be (1,3,4) -Thiadiazol-2, 5-diyl,
  M ¹ , M ^{2 the} same or different, -CO-O-, -O-CO-, -CH ₂ -O-, -O-CH ₂ -, -CH ₂ -CH ₂ -, -CH = N-,
  a, b, c, d, e zero or one.

5. Chip card according to claim 4, characterized in that the liquid crystal one or more components from group A and one or more Contains components from groups B and / or C and / or D. 6. Chip card according to claim 4, characterized in that the liquid crystal two to eleven components from group A and one to seven components contains the groups B and / or C and / or D. 7. Method for producing a chip card according to one or more of the Claims 1 to 6, characterized in that a ferroelectric Liquid crystal display with a ferroelectric liquid crystal layer, which in the Working temperature range has a highly ordered inclined smectic phase, embeds or applies in or on a plastic card, the plastic edge an integrated circuit that stores information electronically and / or edit, and means for information transfer between the Card and an electronic reading and / or writing system contains. 8. Using a ferroelectric liquid crystal display with a ferroelectric liquid crystal layer, which in the working temperature range has highly ordered inclined smectic phase for the production of Chip cards with permanent bistable display. 9. Method to improve the flexural strength of smart cards with permanent bistable display, characterized in that one is a display Ferroelectric liquid crystal display used, the liquid crystal layer in the Working temperature range a highly ordered inclined smectic phase trains. 10. Use of a chip card according to one or more of claims 1 up to 6 for access control, as check card, electronic ticket, telephone card, Parking garage card, "electronic wallet" or for pay TV.