# US 4,394,070 A · Helichromic compounds and displays > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 4,394,070 A - Document ID: US4394070A - Status: Granted - Kind: A - Application number: 06/274,184 - Filed: 1981-06-22 - Granted: 1983-07-19 - Earliest claimed: 1980-07-16 - Assignees: Minnesota Mining and Manufacturing Company - Inventors: Harvey A. Brown; William A. Huffman - Web page: https://patentgrep.com/patent/US4394070A ## CPC - C09K 19/60: Pleochroic dyes - C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE ## Abstract A composition for use in liquid crystal display devices, consisting essentially of a nematic liquid crystal material and a helichromic compound possessing both a chromophoric moiety and a helical ordering moiety. The helical ordering moiety is capable of helically ordering the mixture of liquid crystal material and helichromic compound. The helichromic compound can be utilized in conventional "guest-host" and "twist nematic" displays as well as in unique helichromic displays. When used in helichromic displays, the helichromic compounds eliminate after-image scattering and enable the display to be operated at reduced voltages. ## Claims ### Claim 1 A composition consisting essentially of a nematic liquid crystal material and, in admixture therewith, an organic, nonionic, nonliquid-crystalline helichromic compound, said helichromic compound being soluble in said nematic liquid crystal material, and said helichromic compound being a dichroic dye and having the general formula Q--Z).sub.n wherein: Q is a radical selected from the group consisting of azo, azo-stilbene, benzothiazolyl polyazo, methine, azo-methine, merocyanine and methine arylidene radicals; Z is an organic group capable of imparting helical ordering characteristics to said mixture of nematic liquid crystal and helichromic compound; and n is an integer having a value of 1 or greater. ### Claim 2 A composition consisting essentially of a nematic liquid crystal material and, in admixture therewith, an organic, nonionic, nonliquid-crystalline helichromic compound, said helichromic compound being soluble in said nematic liquid crystal material, and said helichromic compound being a dichroic dye and having the general formula Q--Z).sub.n wherein: Q is an anthraquinone radical; n is 1 and Z is an organic group capable of imparting helical ordering characteristics to said mixture of nematic liquid crystal material and helichromic compound, and Z is substituted in the 1, 4, 5, position of Q. ### Claim 3 A composition consisting essentially of a nematic liquid crystal material and, in admixture therewith, an organic, nonionic, nonliquid-crystalline helichromic compound, said helichromic compound being soluble in said nematic liquid cyrstal material, and said helichromic compound being a dichroic dye and having the general formula Q--Z).sub.n wherein: Q is an anthraquinone radical; n is 2; and Z is an organic group capable of imparting helical ordering characteristics to said mixture of nematic liquid crystal material and helichromic compound, and Z is substituted in the 1 and 4, or 1 and 8 positions of Q. ### Claim 4 A composition consisting essentially of a nematic liquid crystal material and, in admixture therewith, an organic, nonionic, nonliquid-crystalline helichromic compound, said helichromic compound being soluble in said nematic liquid crystal material, and said helichromic compound being a dichroic dye and having the general formula Q--Z).sub.n wherein: Q is an anthraquinone radical; Z is an organic group capable of imparting helical ordering characteristics to said mixture of nematic liquid crystal and helichromic compound, and Z includes a linking group linking it to said Q, wherein said linking group is selected from the group consisting of --CH.dbd.N--, --CH.dbd.CH--, --N.dbd.N--, --O--, --CH.sub.2).sub.p, --O--CH.sub.2).sub.p, --C--CH.sub.3).sub.2 --, ##STR96## --C.sub.6 H.sub.10 --, phenyl groups, naphthyl groups and combinations thereof, wherein p is 1, 2, 3, 4 or 5, and Z is substituted in the 1, 4, 5 or 8 position of Q or any combination thereof; and n is an integer having a value of 1 or greater. ### Claim 5 A composition consisting essentially of a nematic liquid crystal material and, in admixture therewith, an organic, nonionic, nonliquid-crystalline, helichromic compound, said helichromic compound being soluble in said nematic liquid crystal material, and said helichromic compound being a dichroic dye having the general formula Q--Z).sub.n wherein: Q is an anthraquinone heterocyclic dicarboximide radical; n is an integer equal to 1; and Z is an organic group capable of imparting helical ordering characteristics to said mixture of nematic liquid crystal and helichromic compound, and Z is substituted on the nitrogen of said heterocyclic dicarboximide radical. ### Claim 6 (depends on 1) The composition of claim 1 wherein n is an integer having a value of 1 or 2. ### Claim 7 (depends on 1, 2, 3, 4, 5) The composition of claims 1, 2, 3, 4 or 5 wherein Z comprises an asymmetric carbon atom. ### Claim 8 (depends on 1, 2, 3, 4, 5) The composition of claims 1, 2, 3, 4 or 5 wherein Z is selected from the group consisting of a (+)-2-methylalkyl group, a (+)-3-methylalkyl group, a (+)-citronellyl group, a (+)camphanyl group, a (+)-3-methylcyclohexyl group, and a (+)-.alpha.-methylbenzyl group. ### Claim 9 (depends on 1) The composition of claim 1 wherein said helichromic compound is selected from the group consisting of ##STR97## ### Claim 10 (depends on 3) The composition of claim 3 wherein said helichromic compound is selected from the group consisting of ##STR98## ### Claim 11 (depends on 4) The composition of claim 4 wherein said helichromic compound is selected from the group consisting of ##STR99## ### Claim 12 (depends on 5) The composition of claim 5 wherein said helichromic compound is selected from the group consisting of ##STR100## ### Claim 13 (depends on 1, 2, 3, 4, 5) A liquid crystal display device which is responsive to the absence or presence of an electric field, said device comprising one auxiliary polarizer, a layer of nematic liquid crystal composition, and two conductive electrodes positioned, respectively, adjacent opposing surfaces of said layer, said nematic liquid crystal composition being the composition of claim 1, 2, 3, 4 or 5, and said helichromic compound being present in an amount ineffective to allow said mixture to substantially absorb unpolarized light incident thereon in the absence of an electric field, but effective to provide said mixture with the ability to substantially absorb polarized light incident thereon in the absence of an electric field, and to substantially transmit said polarized light incident thereon in the presence of an electric field. ### Claim 14 (depends on 13) The liquid crystal display device of claim 13 wherein said helichromic compound is present in a concentration of between about 0.5% and 2% by weight of said liquid crystal composition. ### Claim 15 (depends on 1, 2, 3, 4, 5) A liquid crystal display device which is responsive to the absence or presence of an electric field, said device comprising two auxiliary polarizers, a layer of nematic liquid crystal composition, and two conductive electrodes positioned, respectively, adjacent opposing surfaces of said layer, said nematic liquid crystal composition being the composition of claim 1, 2, 3, 4 or 5, and said helichromic compound being present in an amount ineffective to allow said mixture to substantially absorb unpolarized or polarized light incident thereon in the absence of an electric field, but effective to eliminate the hydrodynamic effect of optical bounce and reduce decay time. ### Claim 16 (depends on 15) The liquid crystal display device of claim 15 wherein said helichromic compound is present in a concentration between about 0.1 and 1.0 percent by weight of said liquid crystal composition. ### Claim 17 A liquid crystal display device which is responsive to the absence or presence of an electric field, said device having no auxiliary polarizers and comprising a layer of a nematic liquid crystal composition and two conductive electrodes positioned, respectively, adjacent opposing surfaces of said layer, said nematic liquid crystal composition consisting essentially of a nematic liquid crystal material and, in admixture therewith, an organic, nonionic, nonliquid-crystalline helichromic compound, said helichromic compound being soluble in said nematic liquid crystal material, said helichromic compound being a dichroic dye, said helichromic compound comprising at least one helical ordering moiety capable of imparting helical ordering characteristics to said mixture of nematic liquid crystal and helichromic compound, and said helichromic compound being present in said mixture in an amount effective to allow said mixture to substantially absorb unpolarized light incident thereon in the absence of an electric field and to substantially transmit unpolarized light incident thereon in the presence of an electric field. ### Claim 18 (depends on 17) The liquid crystal display device of claim 17 wherein said helichromic compound is present in a concentration of between about 1 and 5 percent by weight of said liquid crystal composition. ### Claim 19 (depends on 13, 15, 17) A display device according to claim 13, 15 or 17 wherein said device includes a means for applying an electric field across said electrodes. ### Claim 20 (depends on 17) The liquid crystal display device of claim 17 wherein said helical ordering moiety comprises an asymmetric carbon atom. ### Claim 21 (depends on 17) The liquid crystal display device of claim 17 wherein said helichromic compound has the general formula Q--Z).sub.n wherein: Q is an organic group having a chomophoric character; Z is an organic group having a helical ordering character capable of imparting helical ordering characteristics to a mixture of nematic liquid crystal material and said helichromic compound; and n is an integer having a value of 1 or greater. ### Claim 22 (depends on 21) The liquid crystal display device of claim 21 wherein n is an integer having a value between 1 and 4. ### Claim 23 (depends on 21) The liquid crystal display device of claim 21 wherein Z is an organic group having an asymmetric carbon atom. ### Claim 24 (depends on 23) The liquid crystal display device of claim 23 wherein Z is selected from the group consisting of a (+)-2-methylalkyl group, a (+)-3-methylalkyl group, a (+)-citronellyl group, a (+)-camphanyl group, a (+)-3-methylcyclohexyl group, and a (+)-.alpha.-methylbenzyl group. ### Claim 25 (depends on 21) The liquid crystal display device of claim 21 wherein Q is a radical selected from the group consisting of azo, azo-stilbene, benzothiazolyl polyazo, methine, azo-methine, merocyanine and methine arylidene radicals. ### Claim 26 (depends on 31) The liquid crystal display device of claim 31 wherein Q is an anthraquinone radical and Z is substituted in the 1, 4, 5 or 8 position of Q, or any combination thereof. ### Claim 27 (depends on 21) The liquid crystal display device of claim 21 wherein Q is an anthraquinone heterocyclic dicarboximide radical and Z is substituted on the nitrogen of said heterocyclic dicarboximide radical. ### Claim 28 (depends on 26) The liquid crystal display device of claims 26 wherein Z additionally comprises a linking group linking said Z organic group group to said Q, wherein said linking group is selected from the group consisting of --CH.dbd.N--, --CH.dbd.CH--, --N.dbd.N--, --NH--, --N(alk)--, --O--, --S--, CH.sub.2 --.sub.p, --O--CH.sub.2 --.sub.p, --C(CH.sub.3).sub.2 --, ##STR101## --C.sub.6 H.sub.10 --, phenyl groups and naphthyl groups and combinations thereof, wherein p is 1, 2, 3, 4 or 5. ### Claim 29 (depends on 21) The liquid crystal display device of claim 21 wherein Q additionally comprises one or more ballasting groups selected from the group consisting of NH.sub.2, --CH.sub.2 --.sub.p CH.sub.3, --O--(CH.sub.2 --.sub.p CH.sub.3, --CH(CH.sub.3).sub.2, ##STR102## C.sub.6 H.sub.11, phenyl groups, naphthyl groups and combinations thereof, wherein p is 0, 1, 2, 3 or 4. ### Claim 30 (depends on 21) The liquid crystal display device of claim 21 wherein Q comprises at least one aromatic ring having one or more substituents independently selected from the group consisting of lower alkyl, lower alkoxy, F, Cl, Br, NO.sub.2, NH(alk), N(alk).sub.2, OH, CN, CF.sub.3, and CH.sub.3, substituted thereon. ### Claim 31 (depends on 17) The liquid crystal display device of claim 17 wherein said helichromic compound is selected from the group consisting of ##STR103## ### Claim 32 A composition consisting essentially of a nematic liquid crystal material and, in admixture therewith, an organic, nonionic, nonliquid-crystalline helichromic compound, said helichromic compound being soluble in said nematic liquid crystal material, and said helichromic compound being a dichroic dye and having the general formula Q(Z).sub.n wherein: Q is an anthraquinone radical; n is 3; and Z is an organic group capable of imparting helical ordering characteristics to said mixture of nematic liquid crystal material and helichromic compound, and Z is substituted in the 1, 4 and 5 positions of Q. ### Claim 33 A composition consisting essentially of a nematic liquid crystal material and, in admixture therewith, an organic, nonionic, nonliquid-crystalline helichromic compound, said helichromic compound being soluble in said nematic liquid crystal material, and said helichromic compound being a dichroic dye and having the general formula Q(Z).sub.n wherein: Q is an anthraquinone radical; n is 4; and Z is an organic group capable of imparting helical ordering characteristics to said mixture of nematic liquid crystal material andhelichromic compound, and Z is substituted in the 1, 4, 5 and 8 positions of Q.