CN111448291A - Liquid crystal composition - Google Patents
Liquid crystal composition Download PDFInfo
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- CN111448291A CN111448291A CN201880078182.0A CN201880078182A CN111448291A CN 111448291 A CN111448291 A CN 111448291A CN 201880078182 A CN201880078182 A CN 201880078182A CN 111448291 A CN111448291 A CN 111448291A
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- liquid crystal
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- 239000000203 mixture Substances 0.000 title claims abstract description 224
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 169
- 150000001875 compounds Chemical class 0.000 claims abstract description 570
- 125000004432 carbon atom Chemical group C* 0.000 claims description 276
- 125000000217 alkyl group Chemical group 0.000 claims description 137
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 87
- 125000002947 alkylene group Chemical group 0.000 claims description 80
- -1 naphthalene-2, 6-diyl Chemical group 0.000 claims description 71
- 125000003342 alkenyl group Chemical group 0.000 claims description 66
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- 238000001179 sorption measurement Methods 0.000 claims description 41
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 25
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 25
- 125000006850 spacer group Chemical group 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 18
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 239000011159 matrix material Substances 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- 230000004044 response Effects 0.000 abstract description 14
- 230000007547 defect Effects 0.000 abstract description 10
- 239000000758 substrate Substances 0.000 description 65
- 125000004122 cyclic group Chemical group 0.000 description 46
- 230000000694 effects Effects 0.000 description 42
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- 238000000034 method Methods 0.000 description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
- 125000004450 alkenylene group Chemical group 0.000 description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 229910052799 carbon Inorganic materials 0.000 description 17
- 239000010408 film Substances 0.000 description 17
- 230000000274 adsorptive effect Effects 0.000 description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 125000000962 organic group Chemical group 0.000 description 14
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 12
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 229910052796 boron Inorganic materials 0.000 description 9
- 230000001965 increasing effect Effects 0.000 description 9
- 229910052710 silicon Inorganic materials 0.000 description 9
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 150000001721 carbon Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 239000011593 sulfur Substances 0.000 description 7
- 239000002156 adsorbate Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000004642 Polyimide Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 230000001678 irradiating effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 229920001721 polyimide Polymers 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 3
- 125000006017 1-propenyl group Chemical group 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000005725 cyclohexenylene group Chemical group 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000002834 transmittance Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 description 2
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- 125000005450 2,3-difluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C(F)=C(F)C([*:1])=C1[H] 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229910004205 SiNX Inorganic materials 0.000 description 1
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 1
- AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- NWAIGJYBQQYSPW-UHFFFAOYSA-N azanylidyneindigane Chemical compound [In]#N NWAIGJYBQQYSPW-UHFFFAOYSA-N 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DKQVJMREABFYNT-UHFFFAOYSA-N ethene Chemical compound C=C.C=C DKQVJMREABFYNT-UHFFFAOYSA-N 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 238000004375 physisorption Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000626 sulfinic acid group Chemical group 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical group S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- 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
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/16—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon double bonds, e.g. stilbenes
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
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Abstract
The invention provides a polymerizable liquid crystal composition, which has negative dielectric anisotropy (delta), meets the requirements of general liquid crystal compositions for display in a wide temperature range, high-speed response and low-voltage driving performance, and has no display defect or few display defects when forming a liquid crystal display element; the invention provides a liquid crystal display element using the liquid crystal composition. A liquid crystal composition having a negative dielectric anisotropy (Delta), which contains 1 or 2 or more compounds selected from the group consisting of compounds represented by the general formulae (N-1), (N-2) and (N-3), and 1 or 2 or more polymerizable compounds.
Description
Technical Field
The present invention relates to a liquid crystal composition.
Background
In a liquid crystal display device, a voltage is applied to a liquid crystal composition held between 2 substrates to control the alignment of the liquid crystal composition, thereby changing the optical characteristics of the liquid crystal composition to perform display. The liquid crystal composition changes from an initial alignment state by application of a voltage. The initial alignment state is controlled by an alignment film using rubbed polyimide, but the rubbed polyimide is difficult to split the alignment state, and therefore, a method of controlling the pretilt angle using a polymerizable compound has been developed and put into practical use. In recent years, a method of controlling the initial alignment state by a self-aligning compound without using an alignment film itself has been studied. However, in these methods, a polymer of a polymerizable compound is used in order to control the alignment of the liquid crystal composition.
These liquid crystal display elements polymerize a polymerizable compound by irradiating ultraviolet light in a state of "dropping a polymerizable liquid crystal composition containing the polymerizable compound in a liquid crystal composition on a substrate and sandwiching the composition between substrates". In this case, although the polymerizable compound and the liquid crystal composition are selected so that the liquid crystal composition is in a specific alignment state, the conventional polymerizable liquid crystal composition has a problem that the initial alignment state is insufficient or changes with time. If these problems occur, a display failure occurs in the liquid crystal display element. Therefore, development of a polymerizable liquid crystal composition capable of achieving a specific alignment state is desired.
Background of the invention
Patent document
Patent document 1: japanese Kokai publication No. 2014-524951
Disclosure of Invention
Problems to be solved by the invention
The invention provides a polymerizable liquid crystal composition, which has negative dielectric anisotropy (delta), meets the requirements of general liquid crystal compositions for display in a wide temperature range, high-speed response and low-voltage driving performance, and has no display defect or few display defects when forming a liquid crystal display element; the invention provides a liquid crystal display element using the liquid crystal composition.
Means for solving the problems
The invention provides a liquid crystal composition which has negative dielectric anisotropy (Delta) and contains 1 or 2 or more compounds selected from the compounds represented by general formulas (N-1), (N-2) and (N-3) and 1 or 2 or more polymerizable compounds, and a liquid crystal display element using the polymerizable liquid crystal composition,
(in the formula, RN11、RN12、RN21、RN22、RN31And RN32Each independently represents an alkyl group having 1 to 8 carbon atoms, and 1 of the alkyl groupsOr non-adjacent 2 or more-CH2-may also be each independently substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-,
AN11、AN12、AN21、AN22、AN31and AN32Each independently represents a group selected from the group consisting of the following (a), (b), (c), and (d):
(a)1, 4-cyclohexylene (1-CH present in this radical)2Or 2 or more-CH not adjacent2-may be substituted by-O-)
(b)1, 4-phenylene (1-CH or more nonadjacent-CH-present in this radical may be substituted by-N)
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ or nonadjacent 2 or more-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by-N)
(d)1, 4-cyclohexenylene (cyclohexenylene),
the above-mentioned group (a), group (b), group (c) and group (d) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
ZN11、ZN12、ZN21、ZN22、ZN31and ZN32Each independently represents a single bond, -CH2CH2－、－(CH2)4－、－OCH2－、－CH2O－、－COO－、－OCO－、－OCF2－、－CF2O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,
XN21represents a hydrogen atom or a fluorine atom,
TN31represents-CH2-or an oxygen atom,
nN11、nN12、nN21、nN22、nN31and nN32Each independently represents an integer of 0 to 3, nN11+nN12、nN21+nN22And nN31+nN32Each independently is 1,2 or 3, when AN11～AN32、ZN11～ZN32When a plurality of them exist, they may be the same or may be different).
The polymerizable liquid crystal of the present application is particularly useful for forming a liquid crystal display element for active matrix driving.
ADVANTAGEOUS EFFECTS OF INVENTION
By using the polymerizable liquid crystal composition of the present invention, a VA-type, IPS-type, FFS-type, PSA-type, or PSVA-type liquid crystal display element can be provided, in which the alignment of the liquid crystal composition after the production of the liquid crystal display element can be brought into a desired state, and in which display defects caused by alignment defects of the liquid crystal composition are not present or are suppressed.
Drawings
Fig. 1 is a diagram schematically showing an embodiment of a liquid crystal display device.
Fig. 2 is an enlarged plan view of the region surrounded by the I-line in fig. 1.
Detailed Description
The liquid crystal composition of the present invention has negative dielectric anisotropy, has a nematic phase-isotropic liquid transition temperature of 60 ℃ or higher, has an absolute value of dielectric anisotropy of 1.5 or higher, and contains 1 or 2 or more compounds selected from the group of compounds represented by the following general formulae (N-1), (N-2), and (N-3).
The compounds represented by the general formulae (N-1), (N-2) and (N-3) correspond to compounds having negative dielectric properties (Δ has a negative sign and an absolute value of more than 2).
The compounds represented by the general formulae (N-1), (N-2) and (N-3) are preferably compounds in which Δ is negative and the absolute value is greater than 3.
In the general formulae (N-1), (N-2) and (N-3), RN11、RN12、RN21、RN22、RN31And RN32Preferably independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms or an alkenyloxy group having 2 to 8 carbon atoms, and is preferablyThe alkyl group has 1 to 5 carbon atoms, an alkoxy group has 1 to 5 carbon atoms, an alkenyl group has 2 to 5 carbon atoms, or an alkenyloxy group has 2 to 5 carbon atoms, more preferably an alkyl group has 1 to 5 carbon atoms or an alkenyl group has 2 to 5 carbon atoms, still more preferably an alkyl group has 2 to 5 carbon atoms or an alkenyl group has 2 to 3 carbon atoms, and yet more preferably an alkenyl group (propenyl group) has 3 carbon atoms.
When the ring structure to which the compound is bonded is a phenyl group (aromatic group), a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and an alkenyl group having 4 to 5 carbon atoms are preferable, and when the ring structure to which the compound is bonded is a saturated ring structure such as cyclohexane, pyran, dioxane, or the like, a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, and a linear alkenyl group having 2 to 5 carbon atoms are preferable. In order to stabilize the nematic phase, the total number of oxygen atoms is preferably 5 or less when carbon atoms are present, and is preferably linear.
The alkenyl group is preferably selected from groups represented by any one of the formulae (R1) to (R5) (the black dot in each formula represents a carbon atom in the ring structure).
In the case of a request for increasing Δ n, AN11、AN12、AN21、AN22、AN31And AN32Preferably each independently aromatic, and preferably aliphatic, in order to improve the response speed, preferably represents trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 2, 3-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2 ] phenylene]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably having the following structure,
more preferably, it represents trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene.
ZN11、ZN12、ZN21、ZN22、ZN31And ZN32Preferably each independently represents-CH2O－、－CF2O－、－CH2CH2－、－CF2CF2-or a single bond, more preferably-CH2O－、－CH2CH2-or a single bond, more preferably-CH2O-or a single bond.
XN21Preferably a fluorine atom.
TN31Preferably an oxygen atom.
nN11+nN12、nN21+nN22And nN31+nN32Preferably 1 or 2, preferably nN11Is 1, nN12A combination of 0; n isN11Is 2, nN12A combination of 0; n isN11Is 1, nN12Is a combination of 1; n isN11Is 2, nN12Is a combination of 1; n isN21Is 1, nN22A combination of 0; n isN21Is 2, nN22A combination of 0; n isN31Is 1, nN32A combination of 0; n isN31Is 2, nN32Is a combination of 0.
In the present application,% represents mass% unless otherwise specified.
The lower limit of the preferable content of the compound represented by the formula (N-1) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%.
The lower limit of the preferable content of the compound represented by the formula (N-2) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%.
The lower limit of the preferable content of the compound represented by the formula (N-3) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%, 20%.
When the viscosity of the composition of the present invention is kept low and a composition having a high response speed is required, the lower limit value and the upper limit value are preferably low. And, in the composition of the present invention, TNIWhen the retention is high and a composition having good temperature stability is required, the lower limit value and the upper limit value are preferably low. In order to increase the dielectric anisotropy while keeping the driving voltage low, it is preferable that the lower limit is increased and the upper limit is increased.
The compounds represented by the general formula (N-1) include compounds represented by the following general formulae (N-1 a) to (N-1 g).
(in the formula, RN11And RN12R in the general formula (N-1)N11And RN12In the same sense, nNa11Represents 0 or 1, nNb11Represents 1 or 2, nNc11Represents 0 or 1, nNd11Represents 1 or 2, nNe11Represents 1 or 2, nNf12Represents 1 or 2, nNg11Represents 1 or 2, ANe11Represents trans-1, 4-cyclohexylene or 1, 4-phenylene, ANg11Represents trans-1, 4-cyclohexylene, 1, 4-cyclohexenylene or 1, 4-phenylene, but at least 1ANg11Represents 1, 4-cyclohexenylene, ZNe11Represents a single bond or ethylene (ethylene) but at least 1Z present in the moleculeNe11Denotes an ethylene group, a plurality of A's being present in the moleculeNe11、ZNe11And/or ANg11Which may be the same or different)
More specifically, the compound represented by the general formula (N-1) is preferably a compound selected from the group of compounds represented by the general formulae (N-1-1) to (N-1-21).
The compound represented by the general formula (N-1-1) is the following compound.
(in the formula, RN111And RN112Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN111Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably a propyl group, a pentyl group or a vinyl group. RN112Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group or a butoxy group.
The compounds represented by the general formula (N-1-1) may be used alone or in combination of 2 or more compounds. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be low, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-1) is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-1) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-1.1) to (N-1-1.23), preferably a compound represented by the formulae (N-1-1.1) to (N-1-1.4), preferably a compound represented by the formulae (N-1-1.1) and (N-1-1.3).
The compounds represented by the formulae (N-1-1.1) to (N-1-1.22) may be used alone or in combination, and the lower limit of the preferable content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-2) is the following compound.
(in the formula, RN121And RN122Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN121Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group, a butyl group or a pentyl group. RN122Preferably an alkyl group having 1 to 5 carbon atoms, a carbon atomThe alkenyl group having 4 to 5 subgroups or the alkoxy group having 1 to 4 carbon atoms is preferably a methyl group, a propyl group, a methoxy group, an ethoxy group or a propoxy group.
The compounds represented by the general formula (N-1-2) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, it is preferable to set the content higher, when importance is placed on solubility at low temperature, the effect is high when the content is set lower, and when importance is placed on TNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-2) is 5%, 7%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 37%, 40%, 42% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 48%, 45%, 43%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-2) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-2.1) to (N-1-2.22), preferably a compound represented by the formulae (N-1-2.3) to (N-1-2.7), (N-1-2.10), (N-1-2.11), (N-1-2.13) or (N-1-2.20), preferably a compound represented by the formulae (N-1-2.3) to (N-1-2.7) when the improvement of Delta is important, or T-1 when the improvement of T is importantNIIn the case of (2), the preferred are the formulae (N-1-2.10) and (N-1-2.11) and the formula (N-1-2.13), the compound represented by the formula (N-1-2.20) is preferable when the improvement of the response speed is important.
The compounds represented by the formulae (N-1-2.1) to (N-1-2.22) may be used alone or in combination, and the lower limit of the preferred content of these compounds alone or in relation to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35%. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, 3% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-3) is the following compound.
(in the formula, RN131And RN132Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN131Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN132Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 3 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, preferably a 1-propenyl group, an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-3) may be used alone or in combination of 2 or more compounds. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be much larger, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-3) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-3) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-3.1) to (N-1-3.21), preferably a compound represented by the formulae (N-1-3.1) to (N-1-3.7) or (N-1-3.21), and preferably a compound represented by the formulae (N-1-3.1), (N-1-3.2), (N-1-3.3), (N-1-3.4) or (N-1-3.6).
The compounds represented by the formulae (N-1-3.1) to (N-1-3.4), (N-1-3.6) and (N-1-3.21) may be used alone or in combination, and preferably are a combination of the formulae (N-1-3.1) and (N-1-3.2) or a combination of 2 or 3 selected from the formulae (N-1-3.3), (N-1-3.4) and (N-1-3.6). The lower limit of the preferred content of these compounds alone or in relation to the total amount of the composition according to the invention is 5%, 10%, 13%, 15%, 17%, 20%. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-4) is the following compound.
(in the formula, RN141And RN142Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN141And RN142Preferably, each independently is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably a methyl group, a propyl group, an ethoxy group or a butoxy group.
The compounds represented by the general formula (N-1-4) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be low, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-4) is 3%, 5%, 7%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 11%, 10%, 8% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-4) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-4.1) to (N-1-4.14), preferably a compound represented by the formulae (N-1-4.1) to (N-1-4.4), preferably a compound represented by the formulae (N-1-4.1), (N-1-4.2) and (N-1-4.4).
The compounds represented by the formulae (N-1-4.1) to (N-1-4.14) may be used alone or in combination, and the lower limit of the preferable content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 3%, 5%, 7%, 10%, 13%, 15%, 17%, 20%. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 11%, 10%, 8% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-5) is the following compound.
(in the formula, RN151And RN152Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN151And RN152Preferably, each independently is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-5) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is attached to the improvement of Δ, the content is preferably set to be higher, and the weight is moreIn the case of solubility at low temperature, if the content is set to be low, the effect is high, and T is regarded as importantNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-5) is 5%, 8%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-5) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-5.1) to (N-1-5.6), and is preferably a compound represented by the formulae (N-1-5.1), (N-1-5.2) or (N-1-5.4).
The compounds represented by the formulae (N-1-5.1), (N-1-5.2) and (N-1-5.4) may be used alone or in combination, and the lower limit of the preferred content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 5%, 8%, 10%, 13%, 15%, 17%, 20%. The upper limit of the content is preferably 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-10) is the following compound.
(in the formula, RN1101And RN1102Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1101Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. RN1102Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-10) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be low, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-10) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-10) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-10.1) to (N-1-10.14), preferably a compound represented by the formulae (N-1-10.1) to (N-1-10.5), preferably a compound represented by the formulae (N-1-10.1) and (N-1-10.2).
The compounds represented by the formulae (N-1 to 10.1) and (N-1 to 10.2) may be used alone or in combination, and the lower limit of the preferred content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20%. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-11) is the following compound.
(in the formula, RN1111And RN1112Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1111Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group, a butyl group, a vinyl group or a 1-propenyl group. RN1112Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-11) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, it is preferable to set the content higher, when importance is placed on solubility at low temperature, the effect is high when the content is set lower, and when importance is placed on TNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-11) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-11) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-11.1) to (N-1-11.14), preferably a compound represented by the formulae (N-1-11.2) and (N-1-11.4).
The compounds represented by the formulae (N-1-11.2) and (N-1-11.4) may be used alone or in combination, and the lower limit of the preferred content of these compounds alone or in combination with respect to the total amount of the composition of the present invention is 5%, 10%, 13%, 15%, 17%, 20%. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-12) is the following compound.
(in the formula, RN1121And RN1122Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1121Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1122Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-12) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be low, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-12) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-13) is the following compound.
(in the formula, RN1131And RN1132Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1131Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1132Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-13) may be used alone or in combination of 2 or more compounds. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-13) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-14) is the following compound.
(in the formula, RN1141And RN1142Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1141Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1142Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-14) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be low, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-14) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-15) is the following compound.
(in the formula, RN1151And RN1152Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1151Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1152Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-15) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-15) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compounds represented by the general formula (N-1-16) are the following compounds.
(in the formula, RN1161And RN1162Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1161Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1162Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-16) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-16) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compounds represented by the general formula (N-1-17) are the following compounds.
(in the formula, RN1171And RN1172Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1171Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably an ethyl group, a propyl group or a butyl group. RN1172Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-17) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is attached to the improvement of Δ, the content is preferably set to be higher, and the weight is moreIn the case of solubility at low temperature, if the content is set to be high, the effect is high, and T is regarded as importantNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-17) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compounds represented by the general formula (N-1-18) are the following compounds.
(in the formula, RN1181And RN1182Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1181Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably a methyl group, an ethyl group, a propyl group or a butyl group. RN1182Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, and preferably an ethoxy group, a propoxy group or a butoxy group.
The compounds represented by the general formula (N-1-18) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, and when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on improvement of ΔTNIIn the case of (3), if the content is set to be much larger, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-18) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-18) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-18.1) to (N-1-18.5), preferably a compound represented by the formulae (N-1-18.1) to (N-1-18.3), preferably a compound represented by the formulae (N-1-18.2) and (N-1-18.3).
The compound represented by the general formula (N-1-20) is the following compound.
(in the formula, RN1201And RN1202Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1201And RN1202Preferably, each independently is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-20) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-20) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-21) is the following compound.
(in the formula, RN1211And RN1212Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1211And RN1212Preferably, each independently is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-21) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is attached to the improvement of Δ, it is preferable to set the content to be higher, and when importance is attached to the solubility at low temperature, the content is set to be higherThe effect is high when T is regarded as importantNIIn the case of (3), if the content is set to be much larger, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-21) is 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-22) is the following compound.
(in the formula, RN1221And RN1222Each independently represents R in the general formula (N-1)N11And RN12Same meaning)
RN1221And RN1222Preferably, each independently is an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably an ethyl group, a propyl group or a butyl group.
The compounds represented by the general formula (N-1-22) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is placed on improvement of Δ, the content is preferably set to be higher, when importance is placed on solubility at low temperature, the effect is high when the content is set to be higher, and when importance is placed on TNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-1-22) is 1%, 5%, 10%, 13%, 15%, 17%, 20% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 35%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 5% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-1-22) is preferably a compound selected from the group consisting of the compounds represented by the formulae (N-1-22.1) to (N-1-22.12), preferably a compound represented by the formulae (N-1-22.1) to (N-1-22.5), and preferably a compound represented by the formulae (N-1-22.1) to (N-1-22.4).
The compound represented by the general formula (N-3) is preferably a compound selected from the group of compounds represented by the general formula (N-3-2).
(in the formula, RN321And RN322Each independently represents R in the general formula (N-3)N11And RN12Same meaning)
RN321And RN322Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, and preferably a propyl group or a pentyl group.
The compounds represented by the general formula (N-3-2) may be used alone, but 2 or more compounds may be used in combination. The type of the combinable compound is not particularly limited, and it can be suitably used in combination according to the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like. The kind of the compound to be used is, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is attached to the improvement of Δ, it is preferable to set the content higherWhen importance is attached to solubility at low temperature, the effect is high when the content is set to be high, and when importance is attached to TNIIn the case of (3), if the content is set to be higher, the effect is high. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (N-3-2) is 3%, 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 33%, 35% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, 7%, 6%, 5% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (N-3-2) is preferably a compound selected from the group consisting of compounds represented by the formulae (N-3-2.1) to (N-3-2.3).
Z in the compounds represented by the general formulae (N-1), (N-2) and (N-3) contained in the liquid crystal compositionN11、ZN12、ZN21、ZN22、ZN31And ZN32The total content of the compounds of the formula (N-1) is preferably 5 to 50% by mass relative to the total content of the compounds of the formula (N-1), (N-2) and (N-3), and Z is a group selected from the group consisting of the compounds of the formula (N-1) contained in the liquid crystal compositionN11、ZN12、ZN21、ZN22、ZN31And ZN32The total content of the compounds that are single bonds is preferably 5 to 50% by mass relative to the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3).
As ZN11And ZN12The compound represented by the general formula (N-1) which is a single bond is preferably a compound represented by the general formulae (N-1 a), (N-1 b), (N-1 c) and (N)The compound represented by (1 g) is preferably a compound represented by (N-1 a), (N-1 b) or (N-1 c).
Further, preferred are compounds represented by the general formulae (N-1-1), (N-1-2), (N-1-3), (N-1-4), (N-1-5) and (N-1-22), and preferred are compounds represented by the general formulae (N-1-1), (N-1-2), (N-1-3), (N-1-4) and (N-1-5).
The total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3) in the total content of the compounds having negative dielectric anisotropy is preferably 80% or more, preferably 85% or more, preferably 87% or more, preferably 90% or more, preferably 93% or more, preferably 96% or more, preferably 98% or more, and preferably substantially 100% or more. By "substantially" is meant: except for compounds such as impurities which are not intentionally contained at the time of production.
Z in the compounds represented by the general formulae (N-1), (N-2) and (N-3) contained in the liquid crystal compositionN11、ZN12、ZN21、ZN22、ZN31And ZN32The total content of the compounds that are single bonds is preferably 50 to 100%, preferably 60 to 100%, preferably 65 to 95%, preferably 70 to 90%, based on the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3).
Z in the compound represented by the general formula (N-1) contained in the liquid crystal compositionN11And ZN12The total content of the compounds that are single bonds is preferably 50 to 100%, preferably 60 to 100%, preferably 65 to 95%, preferably 70 to 90%, based on the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3).
The total content of the compounds represented by the general formulae (N-1 a), (N-1 b), (N-1 c) and (N-1 g) contained in the liquid crystal composition is preferably 50 to 100%, preferably 60 to 100%, preferably 65 to 95%, preferably 70 to 90%, based on the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3).
The total content of the compounds represented by the general formulae (N-1-1), (N-1-2), (N-1-3) and (N-1-4) contained in the liquid crystal composition is preferably 50 to 100%, preferably 60 to 100%, preferably 65 to 95%, preferably 70 to 90%, based on the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3).
"Z in the compounds represented by the general formulae (N-1), (N-2) and (N-3)N11、ZN12、ZN21、ZN22、ZN31And ZN32The content of the compound having a single bond "with respect to" the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3) "and" Z in the compound represented by the general formula (N-1)N11And ZN12The preferable lower limit of the content of the compound having a single bond "relative to" the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3) "," the content of the compounds represented by the general formulae (N-1 a), (N-1 b), (N-1 c) and (N-1 g) "relative to" the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3) ", and" the content of the compounds represented by the general formulae (N-1-1), (N-1-2), (N-1-3) and (N-1-4) "relative to" the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3) "is 50%, 60%, 65% and 70%. Similarly, the upper limit is preferably 100%, 98%, 95%, 93%, 91%, or 90%.
When a liquid crystal display element is produced using the liquid crystal composition of the present invention by adjusting the content, the liquid crystal composition of the present invention preferably contains 1 or 2 or more compounds represented by general formula (L) because the compound represented by general formula (L) corresponds to a compound having a substantially neutral dielectric property (Δ has a value of-2 to 2), the number of polar groups such as halogen contained in the molecule is preferably 2 or less, preferably 1 or less, and more preferably none.
(in the formula, RL1And RL2Each independently represents an alkyl group having 1 to 8 carbon atoms, 1 or none of the alkyl groups being adjacent2 or more of-CH2-may also be each independently substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-,
nL1represents 0, 1,2 or 3,
AL1、AL2and AL3Each independently represents a group selected from the group consisting of the following (a), (b), and (c):
(a)1, 4-cyclohexylene (1-CH present in this radical)2Or 2 or more-CH not adjacent2-may be substituted by-O-)
(b)1, 4-phenylene (1-CH or more nonadjacent-CH-present in this radical may be substituted by-N)
(c) Naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl (1-CH ═ or nonadjacent 2 or more-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by — N ═ may be substituted),
the above-mentioned group (a), group (b) and group (c) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
ZL1and ZL2Each independently represents a single bond, -CH2CH2－、－(CH2)4－、－OCH2－、－CH2O－、－COO－、－OCO－、－OCF2－、－CF2O-, -CH-N-CH-, -CH-, -CF-or-C ≡ C-,
when n isL1A plurality of A's being present for 2 or 3L2In the case where n is the same or different, when n isL1A plurality of Z s being 2 or 3L3In the case where they may be the same or different, compounds represented by the general formulae (N-1), (N-2) and (N-3) are excluded
The types of the compounds represented by the general formula (L) are not particularly limited, and may be appropriately combined and used depending on desired properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, etc. the types of the compounds used are, for example, 1 in one embodiment of the present invention, or 2,3,4, 5, 6, 7, 8, 9, or 10 or more in other embodiments of the present invention.
In the composition of the present invention, the content of the compound represented by the general formula (L) must be appropriately adjusted depending on the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, process compatibility, drop marks, afterimages, and dielectric anisotropy.
The lower limit of the preferable content of the compound represented by formula (L) is 1%, 10%, 20%, 30%, 40%, 50%, 55%, 60%, 65%, 70%, 75%, 80% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 95%, 85%, 75%, 65%, 55%, 45%, 35%, 25%.
When a composition having a low viscosity and a high response speed is required for the composition of the present invention, the lower limit value is preferably high and the upper limit value is preferably high. When Tni of the composition of the present invention is kept high and a composition having excellent temperature stability is required, the lower limit value is preferably high and the upper limit value is preferably high. In order to increase the dielectric anisotropy while keeping the driving voltage low, it is preferable to lower the lower limit and lower the upper limit.
When reliability is important, RL1And RL2Preferably, all alkyl groups are used, and when importance is attached to reduction in volatility of the compound, alkoxy groups are preferred, and when importance is attached to reduction in viscosity, at least one is preferably an alkenyl group.
The number of halogen atoms present in the molecule is preferably 0, 1,2 or 3, preferably 0 or 1, and when importance is attached to compatibility with other liquid crystal molecules, 1 is preferred.
With respect to RL1And RL2When the ring structure to which the compound is bonded is a phenyl group (aromatic group), the compound is preferably independently a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atomsWhen the ring structure to which the group and the alkenyl group having 4 to 5 carbon atoms are bonded is a saturated ring structure such as cyclohexane, pyran, dioxane, or the like, the group and the alkenyl group each independently preferably have a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms. In order to stabilize the nematic phase, the total number of oxygen atoms is preferably 5 or less when carbon atoms are present, and is preferably linear.
The alkenyl group is preferably selected from groups represented by any one of formulae (R1) to (R5) (the black dot in each formula represents a carbon atom in the ring structure).
When n isL1When importance is attached to the response speed, 0 is preferable, 2 or 3 is preferable for improving the upper limit temperature of the nematic phase, and 1 is preferable for achieving a balance between these. In order to satisfy the required characteristics, it is preferable to combine compounds having different values as a composition.
In the case of a request for increasing Δ n, AL1、AL2And AL3Preferably aromatic, and preferably aliphatic, in order to improve the response speed, each independently represents preferably trans-1, 4-cyclohexylene, 1, 4-phenylene, 2-fluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, 1, 4-cyclohexenylene, 1, 4-bicyclo [2.2.2 ] 2]Octylene, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, more preferably having the following structure,
more preferably, it represents trans-1, 4-cyclohexylene or 1, 4-phenylene.
When Z isL1And ZL2When importance is attached to the response speed, a single bond is preferable.
The number of halogen atoms in the compound represented by general formula (L) is preferably 0 or 1.
The compound represented by the general formula (L) is preferably a compound selected from the group of compounds represented by the general formulae (L-1) to (L-7).
The compound represented by the general formula (L-1) is the following compound.
(in the formula, RL11And RL12Each independently represents R in the general formula (L)L1And RL2Same meaning)
RL11And RL12Preferably, the alkyl group has a straight chain of 1 to 5 carbon atoms, the alkoxy group has a straight chain of 1 to 4 carbon atoms, and the alkenyl group has a straight chain of 2 to 5 carbon atoms.
The compounds represented by the general formula (L-1) may be used alone or in combination with 2 or more compounds, and the types of the combinable compounds are not particularly limited, and may be suitably combined and used in accordance with the required performances such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like.
The lower limit of the content is preferably 1%, 2%, 3%, 5%, 7%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55% with respect to the total amount of the composition of the present invention. The upper limit of the content is preferably 95%, 90%, 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30%, 25% with respect to the total amount of the composition of the present invention.
When a composition having a low viscosity and a high response speed is required for the composition of the present invention, the lower limit value is preferably high and the upper limit value is preferably high. When Tni of the composition of the present invention is kept high and a composition having excellent temperature stability is required, the lower limit value is preferably an intermediate value and the upper limit value is preferably an intermediate value. In addition, when the dielectric anisotropy is to be increased in order to keep the driving voltage low, the lower limit value and the upper limit value are preferably low.
The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-1).
(in the formula, RL12Represents the same meaning as in the general formula (L-1)
The compound represented by the general formula (L-1-1) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-1.1) to (L-1-1.3), preferably a compound represented by the formula (L-1-1.2) or the formula (L-1-1.3), and particularly preferably a compound represented by the formula (L-1-1.3).
The lower limit of the preferable content of the compound represented by the formula (L-1 to 1.3) is 1%, 2%, 3%, 5%, 7%, and 10% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, and 3% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formula (L-1-2).
(in the formula, RL12Represents the same meaning as in the general formula (L-1)
The lower limit of the preferable content of the compound represented by the formula (L-1-2) is 1%, 5%, 10%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 35% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 60%, 55%, 50%, 45%, 42%, 40%, 38%, 35%, 33%, 30% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-1-2) is preferably a compound selected from the group consisting of the compounds represented by the formulae (L-1-2.1) to (L-1-2.4), more preferably a compound represented by the formulae (L-1-2.2) to (L-1-2.4). especially, the compound represented by the formula (L-1-2.2) is preferably a compound represented by the formula (L-1-2.3) or (L-1-2.4), and the content of the compound represented by the formulae (L-1-2.3) and (L-1-2.4) is preferably not less than 30% in order to improve the solubility at low temperatures, because the compound represented by the formula (L-1-2.2) is particularly effective in improving the response speed of the composition of the present invention.
The lower limit of the preferable content of the compound represented by the formula (L-1-2.2) is 10%, 15%, 18%, 20%, 23%, 25%, 27%, 30%, 33%, 35%, 38%, 40% with respect to the total amount of the composition of the present invention, and the upper limit thereof is 60%, 55%, 50%, 45%, 43%, 40%, 38%, 35%, 32%, 30%, 27%, 25%, 22% with respect to the total amount of the composition of the present invention.
The lower limit of the preferable content of the total of the compound represented by the formula (L-1-1.3) and the compound represented by the formula (L-1-2.2) is 10%, 15%, 20%, 25%, 27%, 30%, 35%, and 40% relative to the total amount of the composition of the present invention, and the upper limit of the preferable content is 60%, 55%, 50%, 45%, 43%, 40%, 38%, 35%, 32%, 30%, 27%, and 25%, and 22% relative to the total amount of the composition of the present invention.
The compound represented by the general formula (L-1) is preferably a compound selected from the group consisting of compounds represented by the general formula (L-1-3).
(in the formula, RL13And RL14Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms)
RL13And RL14Preferably, the alkyl group has a straight chain of 1 to 5 carbon atoms, the alkoxy group has a straight chain of 1 to 4 carbon atoms, and the alkenyl group has a straight chain of 2 to 5 carbon atoms.
The lower limit of the preferable content of the compound represented by the formula (L-1-3) is 1%, 5%, 10%, 13%, 15%, 17%, 20%, 23%, 25%, and 30% relative to the total amount of the composition of the present invention, and the upper limit of the preferable content is 60%, 55%, 50%, 45%, 40%, 37%, 35%, 33%, 30%, 27%, 25%, 23%, 20%, 17%, 15%, 13%, and 10% relative to the total amount of the composition of the present invention.
Further, the compound represented by the general formula (L-1-3), preferably a compound selected from the group of compounds represented by the formulae (L-1-3.1) to (L-1-3.13), more preferably a compound represented by the formula (L-1-3.1), the formula (L-1-3.3) or the formula (L-1-3.4), particularly a compound represented by the formula (L-1-3.1), is preferably used in order to improve the response speed of the composition of the present invention, and further preferably a compound represented by the formulae (L-1-3.3), the formula (L-1-3.4), the formula (L-1-3.11) or the formula (L-1-3.12) is used in order to prevent the compound represented by the formulae (L-1-3.3), the formula (3-1-3.7374), the formula (L-1-3.11) or the formula (L-1-3.12) from being dissolved at a temperature of 20% or more.
The lower limit of the preferable content of the compound represented by the formula (L-1 to 3.1) is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, and 20% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 20%, 17%, 15%, 13%, 10%, 8%, 7%, and 6% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-1) is preferably a compound selected from the group of compounds represented by the general formulae (L-1-4) and/or (L-1-5).
(in the formula, RL15And RL16Each independently represents an alkyl group having 1 to 8 carbon atoms or an alkoxy group having 1 to 8 carbon atoms)
RL15And RL16Preferably, the alkyl group has a straight chain of 1 to 5 carbon atoms, the alkoxy group has a straight chain of 1 to 4 carbon atoms, and the alkenyl group has a straight chain of 2 to 5 carbon atoms.
The lower limit of the preferable content of the compound represented by the formula (L-1-4) is 1%, 5%, 10%, 13%, 15%, 17%, and 20% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 25%, 23%, 20%, 17%, 15%, 13%, and 10% with respect to the total amount of the composition of the present invention.
The lower limit of the preferable content of the compound represented by the formula (L-1-5) is 1%, 5%, 10%, 13%, 15%, 17%, and 20% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 25%, 23%, 20%, 17%, 15%, 13%, and 10% with respect to the total amount of the composition of the present invention.
The compounds represented by the general formulae (L-1-4) and (L-1-5) are preferably compounds selected from the group of compounds represented by the formulae (L-1-4.1) to (L-1-5.3), and are preferably compounds represented by the formulae (L-1-4.2) or (L-1-5.2).
The lower limit of the preferable content of the compound represented by the formula (L-1 to 4.2) is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18%, and 20% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 20%, 17%, 15%, 13%, 10%, 8%, 7%, and 6% with respect to the total amount of the composition of the present invention.
Preferably, 2 or more compounds selected from the compounds represented by formula (L-1-1.3), formula (L-1-2.2), formula (L-1-3.1), formula (L-1-3.3), formula (L2-1-3.4), formula (L-1-3.11) and formula (L-1-3.12) are combined, preferably 2 or more compounds selected from the compounds represented by formula (L-1-1.3), formula (L-1-2.2), formula (L-1-3.1), formula (L-1-3.3), formula (L-1-3.4) and formula (L-1-4.2), and the lower limit of the total content of these compounds is 2%, 3%, 5%, 10%, 13%, 23%, 30% or more, 3-1%, 3-30%, 3-1-3-1%, 3-4.2%, 3-30%, 3-1%, 3-1%, 3-4%, 3, and 3-30%, 3-4%, 25%, 3-.
The compound represented by the general formula (L-1) is preferably a compound selected from the group consisting of compounds represented by the general formula (L-1-6).
(in the formula, RL17And RL18Each independently represents a methyl group or a hydrogen atom)
The lower limit of the preferable content of the compound represented by the formula (L-1-6) is 1%, 5%, 10%, 15%, 17%, 20%, 23%, 25%, 27%, 30%, 35% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 60%, 55%, 50%, 45%, 42%, 40%, 38%, 35%, 33%, 30% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-1-6) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-1-6.1) to (L-1-6.3).
The compound represented by the general formula (L-2) is the following compound.
(in the formula, RL21And RL22Each independently represents R in the general formula (L)L1And RL2Same meaning)
RL21Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, RL22Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
The compounds represented by the general formula (L-2) can be used alone or in combination of 2 or more compounds, and the types of the combinable compounds are not particularly limited, and can be suitably combined and used in accordance with the required performances such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like, and the types of the compounds used are, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
When importance is attached to solubility at low temperatures, the effect is high if the content is set to be high, and conversely, when importance is attached to response speed, the effect is high if the content is set to be low. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The lower limit of the preferable content of the compound represented by the formula (L-2) is 1%, 2%, 3%, 5%, 7%, and 10% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, and 3% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-2) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-2.1) to (L-2.6), and is preferably a compound represented by the formula (L-2.1), the formula (L-2.3), the formula (L-2.4), or the formula (L-2.6).
The compound represented by the general formula (L-3) is the following compound.
(in the formula, RL31And RL32Each independently represents R in the general formula (L)L1And RL2Same meaning)
RL31And RL32Preferably, each independently is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
The compounds represented by the general formula (L-3) can be used alone or in combination with 2 or more compounds, and the types of the combinable compounds are not particularly limited, and can be suitably combined and used in accordance with the required performances such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like, and the types of the compounds used are, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
The lower limit of the preferable content of the compound represented by formula (L-3) is 1%, 2%, 3%, 5%, 7%, and 10% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content is 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5%, and 3% with respect to the total amount of the composition of the present invention.
When a high birefringence is obtained, the effect is high if the content is set to be high, and conversely, when high Tni is emphasized, the effect is high if the content is set to be low. In addition, when the drop mark or the afterimage characteristics are improved, the content range is preferably set to the middle.
The compound represented by the general formula (L-3) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-3.1) to (L-3.7), and is preferably a compound represented by the formulae (L-3.2) to (L-3.5).
The compound represented by the general formula (L-4) is the following compound.
(in the formula, RL41And RL42Each independently represents R in the general formula (L)L1And RL2Same meaning)
RL41Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, RL42Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
The compounds represented by the general formula (L-4) can be used alone, but 2 or more compounds can be used in combination, and the types of the combinable compounds are not particularly limited, and can be suitably used in combination according to the required performances such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like, and the types of the compounds used are, for example, 1,2,3,4, or 5 or more as one embodiment of the present invention.
In the composition of the present invention, the content of the compound represented by the general formula (L-4) must be appropriately adjusted depending on the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, process compatibility, drop marks, afterimages, and dielectric anisotropy.
The lower limit of the preferable content of the compound represented by formula (L-4) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content of the compound represented by formula (L-4) is 50%, 40%, 35%, 30%, 20%, 15%, 10%, 5% with respect to the total amount of the composition of the present invention.
The compounds represented by the general formula (L-4) are preferably, for example, compounds represented by the formulae (L-4.1) to (L-4.3).
The compound represented by the formula (L-4.1), or the compound represented by the formula (L-4.2), or both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2), or all of the compounds represented by the formulae (L-4.1) to (L-4.3) may be contained depending on the required performance such as solubility at low temperature, transition temperature, electrical reliability, birefringence, etc. the lower limit of the preferable content of the compound represented by the formula (L-4.1) or the formula (L-4.2) is 3%, 5%, 7%, 9%, 11%, 12%, 13%, 18%, 21%, the upper limit thereof is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, relative to the total amount of the composition of the present invention.
When both the compound represented by the formula (L-4.1) and the compound represented by the formula (L-4.2) are contained, the lower limit of the preferable content of the compounds is 15%, 19%, 24%, 30%, the upper limit is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-4) is preferably a compound represented by, for example, formulae (L-4.4) to (L-4.6), and preferably a compound represented by formula (L-4.4).
The compound represented by the formula (L-4.4), the compound represented by the formula (L-4.5), or both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) may be contained depending on the required performance such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like.
The lower limit of the content of the compound represented by the formula (L-4.4) or the formula (L-4.5) is preferably 3%, 5%, 7%, 9%, 11%, 12%, 13%, 18%, 21%, and the upper limit thereof is preferably 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10%, 8%, relative to the total amount of the composition of the present invention.
When both the compound represented by the formula (L-4.4) and the compound represented by the formula (L-4.5) are contained, the lower limit of the preferable content of the compounds is 15%, 19%, 24%, 30%, the upper limit is 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13% with respect to the total amount of the composition of the present invention.
The compounds represented by the general formula (L-4) are preferably compounds represented by the formulae (L-4.7) to (L-4.10), and particularly preferably compounds represented by the formulae (L-4.9).
The compound represented by the general formula (L-5) is the following compound.
(in the formula, RL51And RL52Each independently represents R in the general formula (L)L1And RL2Same meaning)
RL51Preferably an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, RL52Preferably an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 4 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms.
The compounds represented by the general formula (L-5) can be used alone or in combination with 2 or more compounds, and the types of the combinable compounds are not particularly limited, and can be suitably combined and used in accordance with the required performances such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like.
In the composition of the present invention, the content of the compound represented by the general formula (L-5) must be appropriately adjusted depending on the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, process compatibility, drop marks, afterimages, and dielectric anisotropy.
The lower limit of the preferable content of the compound represented by formula (L-5) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, 40% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content of the compound represented by formula (L-5) is 50%, 40%, 35%, 30%, 20%, 15%, 10%, 5% with respect to the total amount of the composition of the present invention.
The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.1) or the formula (L-5.2), and particularly preferably a compound represented by the formula (L-5.1).
The lower limit of the preferred content of these compounds relative to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, 9%.
The compound represented by the general formula (L-5) is preferably a compound represented by the formula (L-5.3) or the formula (L-5.4).
The lower limit of the preferred content of these compounds relative to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, 9%.
The compound represented by the general formula (L-5) is preferably a compound selected from the group consisting of compounds represented by the formulae (L-5.5) to (L-5.7), and particularly preferably a compound represented by the formula (L-5.7).
The lower limit of the preferred content of these compounds relative to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, 9%.
The compound represented by the general formula (L-6) is the following compound.
(in the formula, RL61And RL62Each independently represents R in the general formula (L)L1And RL2In the same sense, XL61And XL62Each independently represents a hydrogen atom or a fluorine atom)
RL61And RL62Preferably each independently an alkyl group having 1 to 5 carbon atoms or an alkenyl group having 2 to 5 carbon atoms, preferably XL61And XL62One of them is a fluorine atom and the other is a hydrogen atom.
The compounds represented by the general formula (L-6) can be used alone or in combination with 2 or more compounds, and the types of the combinable compounds are not particularly limited, and can be suitably combined and used in accordance with the required performances such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, and the like.
The lower limit of the preferred content of the compound represented by formula (L-6) relative to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35%, and 40%, the upper limit of the preferred content of the compound represented by formula (L-6) relative to the total amount of the composition of the present invention is 50%, 40%, 35%, 30%, 20%, 15%, and 10%, the preferred content is preferably increased when Δ n is increased, and the preferred content is decreased when precipitation at a low temperature is emphasized.
The compounds represented by the general formula (L-6) are preferably compounds represented by the formulae (L-6.1) to (L-6.9).
The types of the combinable compounds are not particularly limited, and 1 to 3, more preferably 1 to 4, are preferably contained among these compounds, and since the molecular weight distribution of the selected compounds is wide and effective for solubility, it is preferable to select 1 compound from the compounds represented by the formula (L-6.1) or (L-6.2), 1 compound from the compounds represented by the formula (L0-6.4) or (L1-6.5), 1 compound from the compounds represented by the formula (L2-6.6) or (L-6.7), 1 compound from the compounds represented by the formula (L-6.8) or (L-6.9), and appropriately combine these compounds, among which the compounds represented by the formula (L-6.1), the formula (L-6.3), the formula (L-6.4), the formula (L-6.6) and the formula (L-6.9) are preferably contained.
The compounds represented by the general formula (L-6) are preferably, for example, compounds represented by the formulae (L-6.10) to (L-6.17), and among them, compounds represented by the formula (L-6.11) are preferred.
The lower limit of the preferred content of these compounds relative to the total amount of the composition of the present invention is 1%, 2%, 3%, 5%, 7%. The upper limit of the preferable content of these compounds is 20%, 15%, 13%, 10%, 9%.
The compound represented by the general formula (L-7) is the following compound.
(in the formula, RL71And RL72Each independently represents R in the general formula (L)L1And RL2In the same sense, AL71And AL72Each independently represents a group represented by the general formula (L)L2And AL3In the same sense, AL71And AL72May also be substituted independently of one another by fluorine atoms, ZL71Z in general formula (L)L2In the same sense, XL71And XL72Each independently represents a fluorine atom or a hydrogen atom)
In the formula, RL71And RL72Preferably, each independently is an alkyl group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkoxy group having 1 to 4 carbon atoms, AL71And AL72Preferably each independently of the other 1, 4-cyclohexylene or 1, 4-phenylene, AL71And AL72May also be independently substituted by fluorine atoms, ZL71Preferably a single bond or-COO-, preferably a single bond, XL71And XL72Preferably a hydrogen atom.
The kind of the combinable compound is not particularly limited, and may be combined according to the required properties of solubility at low temperature, transition temperature, electrical reliability, birefringence, and the like. The types of the compounds used are, for example, 1,2,3, and 4 in one embodiment of the present invention.
In the composition of the present invention, the content of the compound represented by the general formula (L-7) must be appropriately adjusted depending on the required properties such as solubility at low temperatures, transition temperature, electrical reliability, birefringence, process compatibility, drop marks, afterimages, and dielectric anisotropy.
The lower limit of the preferable content of the compound represented by formula (L-7) is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, and 20% with respect to the total amount of the composition of the present invention, and the upper limit of the preferable content of the compound represented by formula (L-7) is 30%, 25%, 23%, 20%, 18%, 15%, 10%, and 5% with respect to the total amount of the composition of the present invention.
When the composition of the present invention is intended to be an embodiment having a high Tni, the content of the compound represented by formula (L-7) is preferably increased a little, and when an embodiment having a low viscosity is intended, the content is preferably decreased a little.
The compounds represented by the general formula (L-7) are preferably compounds represented by the formulae (L-7.1) to (L-7.4), and preferably compounds represented by the formula (L-7.2).
The compounds represented by the general formula (L-7) are preferably compounds represented by the formulae (L-7.11) to (L-7.13), and preferably compounds represented by the formulae (L-7.11).
The compounds represented by the general formula (L-7) are represented by the formulae (L-7.21) to (L-7.23), and preferably the compounds represented by the formulae (L-7.21).
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.31) to (L-7.34), and is preferably a compound represented by the formula (L-7.31) or/and (L-7.32).
The compound represented by the general formula (L-7) is preferably a compound represented by the formulae (L-7.41) to (L-7.44), and is preferably a compound represented by the formula (L-7.41) or/and (L-7.42).
The compounds represented by the general formula (L-7) are preferably compounds represented by the formulae (L-7.51) to (L-7.53).
The lower limit of the total content of the compounds represented by the general formulae (i), (ii), (L) and (N) is 80%, 85%, 88%, 90%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99% relative to the total amount of the composition of the present invention, and the upper limit of the content is 100%, 99%, 98%, 95%.
The lower limit of the preferable content of the total of the compounds represented by the general formulae (i), the general formula (ii), the general formulae (L-1) to (L-7), and the compounds represented by the general formulae (M-1) to (M-8) is 80%, 85%, 88%, 90%, 92%, 93%, 94%, 95%, 96%, 97%, 98%, 99%, and 100%, relative to the total amount of the composition of the present invention, and the upper limit of the preferable content is 100%, 99%, 98%, and 95%.
The composition of the present invention preferably does not contain a compound having a structure in which oxygen atoms are bonded to each other, such as a peroxy (-CO-OO-) structure, in the molecule.
When importance is attached to the reliability and long-term stability of the composition, the content of the compound having a carbonyl group is preferably 5% or less, more preferably 3% or less, still more preferably 1% or less, and most preferably substantially none, based on the total mass of the composition.
When importance is attached to stability by UV irradiation, the content of the compound substituted with a chlorine atom is preferably 15% or less, preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and further preferably substantially not contained, with respect to the total mass of the composition.
The content of the compound having all six-membered ring structures in the molecule is preferably large, and the content of the compound having all six-membered ring structures in the molecule is preferably 80% or more, more preferably 90% or more, further preferably 95% or more, and most preferably the composition is substantially composed of only the compound having all six-membered ring structures in the molecule.
In order to suppress deterioration due to oxidation of the composition, the content of the compound having a cyclohexenylene group as a ring structure is preferably small, and the content of the compound having a cyclohexenylene group is preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and further preferably substantially not contained, with respect to the total mass of the composition.
When importance is attached to the improvement of viscosity and the improvement of Tni, the content of the compound having 2-methylbenzene-1, 4-diyl in which a hydrogen atom may be substituted with halogen in a molecule is preferably small, and the content of the compound having 2-methylbenzene-1, 4-diyl in a molecule is preferably 10% or less, preferably 8% or less, more preferably 5% or less, preferably 3% or less, and further preferably substantially none, with respect to the total mass of the composition.
The term "substantially free" as used herein means that the term does not include any substance except those intentionally contained.
In the case where the compound contained in the composition of the first embodiment of the present invention has an alkenyl group as a side chain, the number of carbon atoms of the alkenyl group is preferably 2 to 5 in the case where the alkenyl group is bonded to cyclohexane, the number of carbon atoms of the alkenyl group is preferably 4 to 5 in the case where the alkenyl group is bonded to benzene, and it is preferable that the unsaturated bond of the alkenyl group is not directly bonded to benzene.
Average elastic constant (K) of liquid crystal composition used in the present inventionAVG) Preferably 10 to 25, as the lower limit thereof, preferably 10, preferably 10.5, preferably 11, preferably 11.5, preferably 12, preferably 12.3, preferably 12.5, preferably 12.8, preferably 13, preferably 13.3, preferably 13.5, preferably 13.8, preferably 14, preferably 14.3, preferably 14.5, preferably 14.8, preferably 15, preferably 15.3, preferably 15.5, preferably 15.8, preferably 16, preferably 16.3, preferably 16.5, preferably 16.8, preferably 17, preferably 17.3, preferably 17.5, preferably 17.8, preferably 18; as its upper limit, it is preferably 25, preferably 24.5, preferably 24, preferably 23.5, preferably 23, preferably 22.8, preferably 22.5, preferably 22.3, preferably 22, preferably 21.8, preferably 21.5, preferably 21.3, preferably 21, preferably 20.8, preferably 20.5, preferably 20.3, preferably 20, preferably 19.8, preferably 19.5, preferably 19.3, preferably 19, preferably 18.8, preferably 18.5, preferably 18.3, preferably 18, preferably 17.8, preferably 17.5, preferably 17.3, preferably 17. When it is important to reduce power consumption, it is effective to suppress the amount of backlight light, and since the liquid crystal display element preferably has a high light transmittance, K is preferably set toAVGThe value of (d) is set lower. In thatWhen importance is attached to improvement of response speed, K is preferably set toAVGThe value of (d) is set higher.
The polymerizable compound of the present invention is preferably a compound represented by the following general formula (P).
(in the above general formula (P), Rp1Represents a hydrogen atom, a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms wherein the hydrogen atom may be substituted with a halogen atom, an alkoxy group having 1 to 15 carbon atoms wherein the hydrogen atom may be substituted with a halogen atom, an alkenyl group having 1 to 15 carbon atoms wherein the hydrogen atom may be substituted with a halogen atom, an alkenyloxy group having 1 to 15 carbon atoms wherein the hydrogen atom may be substituted with a halogen atom, or-Spp2－Pp2，
Pp1And Pp2Each independently represents formula (P)p1-1) to formula (P)p1-any one of the above-mentioned-9),
(in the formula, Rp11And Rp12Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, Wp11Represents a single bond, -O-, -COO-or methylene, tp11Represents 0, 1 or 2, and a plurality of R exist in the moleculep11、Rp12、Wp11And/or tp11In the case of (2), they may be the same or different)
Spp1And Spp2Each independently represents a single bond or a spacer,
Zp1and Zp2Each independently represents a single bond, -O-, -S-, -CH2－、－OCH2－、－CH2O－、－CO－、－C2H4－、－COO－、－OCO－、－OCOOCH2－、－CH2OCOO－、－OCH2CH2O－、－CO－NRZP1－、－NRZP1－CO－、－SCH2－、－CH2S－、－CH＝CRZP1－COO－、－CH＝CRZP1－OCO－、－COO－CRZP1＝CH－、－OCO－CRZP1＝CH－、－COO－CRZP1＝CH－COO－、－COO－CRZP1＝CH－OCO－、－OCO－CRZP1＝CH－COO－、－OCO－CRZP1＝CH－OCO－、－(CH2)z－COO－、－(CH2)2－OCO－、－OCO－(CH2)2－、－(C＝O)－O－(CH2)2－、－CH＝CH－、－CF＝CF－、－CF＝CH－、－CH＝CF－、－CF2－、－CF2O－、－OCF2－、－CF2CH2－、－CH2CF2－、－CF2CF2-or-C ≡ C- (wherein, R isZP1Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a plurality of R's are present in the moleculeZP1In the case of (2), they may be the same or different)
Ap2Represents 1, 4-phenylene, 1, 4-cyclohexylene, anthracene-2, 6-diyl, phenanthrene-2, 7-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, naphthalene-2, 6-diyl, indan-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 1, 3-dioxane-2, 5-diyl, Ap2Unsubstituted or substituted by an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or-Spp2－Pp2The substitution is carried out by the following steps,
Ap1is represented by (A)p1－11)～(Ap1-19) a group represented by (a),
(wherein, at ★, Sp is reacted withp1Or Zp1Bonded to Z at ★★p1Bonding, wherein 1 or more than 2 hydrogen atoms in the structure can be replaced by alkyl with 1-12 carbon atomsA haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group, or-Spp2－Pp2Substituted)
Ap3Is represented by (A)p3－11)～(Ap3-19) a group represented by (a),
(wherein, at ★, with Zp2Bonded at ★★ with Rp1Or Zp2Bonding, wherein 1 or more than 2 hydrogen atoms in the structure can also be replaced by alkyl with 1-12 carbon atoms, halogenated alkyl with 1-12 carbon atoms, alkoxy with 1-12 carbon atoms, halogenated alkoxy with 1-12 carbon atoms, halogen atom, cyano, nitro or-Spp2－Pp2Substituted)
mp2And mp3Each independently represents 0, 1,2 or 3, mp1And mp4Each independently represents 1,2 or 3, and a plurality of P's are present in the moleculep1、Spp1、Ap1、Zp1、Zp2、Ap3And/or Rp1In which case they may be the same or may also be different). It is preferable that 1 or 2 or more of the polymerizable monomers are contained.
In the general formula (P) of the present invention, Rp1Is preferably-Spp2－Pp2。
Preferably Pp1And Pp2Each independently of the other is of formula (P)p1-1) to formula (P)p1-3), preferably (P)p1－1)。
Preferably Rp11And Rp12Each independently is a hydrogen atom or a methyl group.
Preferably mp1+mp4Is 2 or more, preferably 2 or 3.
Zp1And Zp2Preferably each independently a single bond, -OCH2－、－CH2O－、－CO－、－C2H4－、－COO－、－OCO－、－COOC2H4－、－OCOC2H4－、－C2H4OCO－、－C2H4COO－、－CH＝CH－、－CF2－、－CF2O－、－(CH2)2－COO－、－(CH2)2－OCO－、－OCO－(CH2)2－、－CH＝CH－COO－、－COO－CH＝CH－、－OCOCH＝CH－、－COO－(CH2)2－、－OCF2-or-C ≡ C-, preferably a single bond, -OCH2－、－CH2O－、－C2H4－、－COO－、－OCO－、－COOC2H4－、－OCOC2H4－、－C2H4OCO－、－C2H4COO－、－CH＝CH－、－(CH2)2－COO－、－(CH2)2－OCO－、－OCO－(CH2)2－、－CH＝CH－COO－、－COO－CH＝CH－、－OCOCH＝CH－、－COO－(CH2)2-or-C.ident.C-, preferably only one present in the molecule is-OCH2－、－CH2O－、－C2H4－、－COO－、－OCO－、－COOC2H4－、－OCOC2H4－、－C2H4OCO－、－C2H4COO－、－CH＝CH－、－(CH2)2－COO－、－(CH2)2－OCO－、－OCO－(CH2)2－、－CH＝CH－COO－、－COO－CH＝CH－、－OCOCH＝CH－、－COO－(CH2)2-or-C.ident.C-, all others being single bonds, preferably only one present in the molecule is-OCH2－、－CH2O－、－C2H4-, -COO-or-OCO-, the others all being single bonds, preferably all being single bonds.
In addition, it is preferable that only Z is present in the moleculep1And Zp2One of them is selected from the group consisting of-CH-COO-, -COO-CH-, - (CH)2)2－COO－、－(CH2)2－OCO－、－O－CO－(CH2)2－、－COO－(CH2)2-linking groups in the group, others being single bonds.
Spp1And Spp2Each independently represents a single bond or an alkylene group having 1 to 30 carbon atoms, wherein-CH in the alkylene group2The alkylene group may be substituted with-O-, -CO-, -COO-, -OCO-, -CH-or-C.ident.C-, and a hydrogen atom in the alkylene group may be substituted with a halogen atom, and is preferably a linear alkylene group having 1 to 10 carbon atoms or a single bond, as long as oxygen atoms are not directly bonded to each other.
Ap2Preferably 1, 4-phenylene, 1, 4-cyclohexylene, anthracene-2, 6-diyl, phenanthrene-2, 7-diyl or naphthalene-2, 6-diyl, preferably 1, 4-phenylene, 1, 4-cyclohexylene, phenanthrene-2, 7-diyl or naphthalene-2, 6-diyl, in mp2+mp3At 0, phenanthrene-2, 7-diyl is preferred, based on mp2+m p31,2 or 3, it is preferably 1, 4-phenylene or 1, 4-cyclohexylene. To improve the compatibility with liquid-crystalline compounds, Ap21 or more than 2 hydrogen atoms in the structure can be replaced by methyl, ethyl, methoxy, ethoxy or fluorine atoms.
Ap1Preferably of the formula (A)p1－15)、(Ap1－16)、(Ap1-17) or (A)p1-18). To improve the compatibility with liquid-crystalline compounds, Ap11 or more than 2 hydrogen atoms in the structure may also be substituted by methyl, ethyl, methoxy, ethoxy or fluorine atoms.
Ap3Preferably of the formula (A)p1－14)、(Ap1－15)、(Ap1－16)、(Ap1-17) or (A)p1-18). To improve the compatibility with liquid-crystalline compounds, Ap31 or more than 2 hydrogen atoms in the structure can be replaced by methyl, ethyl, methoxy, ethoxy or fluorine atoms.
mp2+mp3Preferably 0, 1,2 or 3, preferably 1 or 2.
The total content of the compounds represented by the general formula (P) is preferably 0.05 to 10%, preferably 0.1 to 8%, preferably 0.1 to 5%, preferably 0.1 to 3%, preferably 0.2 to 2%, preferably 0.2 to 1.3%, preferably 0.2 to 1%, preferably 0.2 to 0.56% of the composition containing the compounds represented by the general formula (P) of the present application.
The preferable lower limit of the total content of the compounds represented by the general formula (P) is 0.01%, 0.03%, 0.05%, 0.08%, 0.1%, 0.15%, 0.2%, 0.25%, 0.3% with respect to the composition containing the compound represented by the general formula (P) of the present application.
The preferable upper limit of the total content of the compounds represented by the general formula (P) is 10%, 8%, 5%, 3%, 1.5%, 1.2%, 1%, 0.8%, 0.5% with respect to the composition containing the compounds represented by the general formula (P) of the present application.
If the content is small, the effect of adding the compound represented by the general formula (P) is difficult to be exhibited, and problems such as a weak alignment controlling force of the liquid crystal composition or a weak alignment controlling force with the passage of time occur, and if it is too large, the amount remaining after curing increases, the curing takes time, and the reliability of the liquid crystal deteriorates. Therefore, the content is set in consideration of their balance.
The compound represented by the general formula (P) is preferably a compound represented by the general formula (P-1), the general formula (P-2), the general formula (P-3) or the general formula (P-4).
Pp31-Spp31-Ap32-Spp32-Pp32(P-3)
(in the formula, Pp11、Pp12、Pp21、Pp22、Pp31、Pp32、Pp41And Pp42Each independently represents a group represented by the formula (P)p1In the same sense, the term "a", "an", "the" or "the" is used,
Spp11、Spp12、Spp21、Spp22、Spp31、Spp32、SPp41and SPp42Each independently represents the same as Sp in the general formula (P)p1In the same sense, the term "a", "an", "the" or "the" is used,
Ap11、Ap12、Ap13、Ap21、Ap22、Ap23、Ap32and Ap42Each independently represents 1, 4-phenylene, 1, 4-cyclohexylene, anthracene-2, 6-diyl, phenanthrene-2, 7-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, naphthalene-2, 6-diyl, indan-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 1, 3-dioxane-2, 5-diyl, Ap11、Ap12、Ap13、Ap21、Ap22、Ap23、Ap32And Ap42Each independently unsubstituted or substituted with an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a haloalkoxy group having 1 to 12 carbon atoms, a halogen atom, a cyano group, a nitro group or-Sp in the general formula (P)p2－Pp2The substitution is carried out by the following steps,
Ap41a is represented by the general formula (P)p1In the same sense, the term "a", "an", "the" or "the" is used,
Ap43represents a in the general formula (P)p3In the same sense, the term "a", "an", "the" or "the" is used,
Zp21、Zp22、Zp41and Zp42Represents a single bond, -O-, -S-, -CH2－、－OCH2－、－CH2O－、－CO－、－C2H4－、－COO－、－OCO－、－OCOOCH2－、－CH2OCOO－、－OCH2CH2O－、－CO－NRZP1－、－NRZP1－CO－、－SCH2－、－CH2S－、－CH＝CRZP1－COO－、－CH＝CRZP1－OCO－、－COO－CRZP1＝CH－、－OCO－CRZP1＝CH－、－COO－CRZP1＝CH－COO－、－COO－CRZP1＝CH－OCO－、－OCO－CRZP1＝CH－COO－、－OCO－CRZP1＝CH－OCO－、－(CH2)z－COO－、－(CH2)2－OCO－、－OCO－(CH2)2－、－(C＝O)－O－(CH2)2－、－CH＝CH－、－CF＝CF－、－CF＝CH－、－CH＝CF－、－CF2－、－CF2O－、－OCF2－、－CF2CH2－、－CH2CF2－、－CF2CF2-or-C ≡ C- (wherein, R isZP1Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a plurality of R's are present in the moleculeZP1In the case where they may be the same or different), but Z present in the moleculep21And Zp22At least one other than a single bond)
Pp11、Pp12、Pp21、Pp22、Pp31、Pp32、Pp41And Pp42Preferably each independently of P in the formula (P)p1Are identically of formula (P)p1-1) to formula (P)p1-3), preferably (P)p1－1)，Rp11And Rp12Preferably each independently a hydrogen atom or a methyl group.
Spp11、Spp12、Spp21、Spp22、Spp31、Spp32、Spp41And Spp42Each independently represents a single bond or an alkylene group having 1 to 30 carbon atoms, wherein-CH in the alkylene group2The alkylene group may be substituted with-O-, -CO-, -COO-, -OCO-, -CH-or-C.ident.C-, and a hydrogen atom in the alkylene group may be substituted with a halogen atom, and is preferably a linear alkylene group having 1 to 10 carbon atoms or a single bond, as long as oxygen atoms are not directly bonded to each other.
Ap11、Ap12、Ap13、Ap21、Ap22、Ap23、Ap32And Ap42Preferably each independently of the other 1, 4-phenylene, 1, 4-cyclohexyleneAnthracene-2, 6-diyl, phenanthrene-2, 7-diyl or naphthalene-2, 6-diyl, preferably 1, 4-phenylene, 1, 4-cyclohexylene, phenanthrene-2, 7-diyl or naphthalene-2, 6-diyl. In the general formulae (P-1) and (P-2), each independently is preferably a 1, 4-phenylene group or a 1, 4-cyclohexylene group, and 1 or 2 or more hydrogen atoms in the structure may be substituted with a methyl group, an ethyl group, a methoxy group, an ethoxy group or a fluorine atom for the purpose of improving the compatibility with the liquid crystal compound. In the general formula (P-3), phenanthrene-2, 7-diyl group is preferable, and 1 or 2 or more hydrogen atoms in the structure thereof may be substituted with a methyl group, an ethyl group, a methoxy group, an ethoxy group or a fluorine atom in order to improve compatibility with the liquid crystal compound.
Zp21Preferably a single bond, -OCH2－、－CH2O－、－CO－、－C2H4－、－COO－、－OCO－、－COOC2H4－、－OCOC2H4－、－C2H4OCO－、－C2H4COO－、－CH＝CH－、－CF2－、－CF2O－、－(CH2)2－COO－、－(CH2)2－OCO－、－OCO－(CH2)2－、－CH＝CH－COO－、－COO－CH＝CH－、－OCOCH＝CH－、－COO－(CH2)2－、－OCF2-or-C ≡ C-, preferably a single bond, -OCH2－、－CH2O－、－C2H4－、－COO－、－OCO－、－COOC2H4－、－OCOC2H4－、－C2H4OCO－、－C2H4COO－、－CH＝CH－、－(CH2)2－COO－、－(CH2)2－OCO－、－OCO－(CH2)2－、－CH＝CH－COO－、－COO－CH＝CH－、－OCOCH＝CH－、－COO－(CH2)2-or-C.ident.C-, preferably only one present in the molecule is-OCH2－、－CH2O－、－C2H4－、－COO－、－OCO－、－COOC2H4－、－OCOC2H4－、－C2H4OCO－、－C2H4COO－、－CH＝CH－、－(CH2)2－COO－、－(CH2)2－OCO－、－OCO－(CH2)2－、－CH＝CH－COO－、－COO－CH＝CH－、－OCOCH＝CH－、－COO－(CH2)2-or-C.ident.C-, all others being single bonds, preferably only one present in the molecule is-OCH2－、－CH2O－、－C2H4-, -COO-or-OCO-, the others all being single bonds, preferably all being single bonds.
In addition, it is preferable that only Z is present in the moleculep21One of (A) is selected from the group consisting of- (CH)2)2－COO－、－(CH2)2－OCO－、－O－CO－(CH2)2－、－COO－(CH2)2-linking groups in the group, others being single bonds.
Preferred examples of the compound represented by the general formula (P-1) of the present invention include polymerizable compounds represented by the following formulae (P-1-1) to (P-1-46).
(in the formula, Pp11、Pp12、Spp11And Spp12Represents P in the general formula (P-1)p11、Pp12、Spp11And Spp12Same meaning)
Preferable examples of the compound represented by the general formula (P-2) of the present invention include polymerizable compounds represented by the following formulae (P-2-1) to (P-2-12).
(in the formula, Pp21、Pp22、Spp21And Spp22Represents P in the general formula (P-2)p21、Pp22、Spp21And Spp22Same meaning)
Preferable examples of the compound represented by the general formula (P-3) of the present invention include polymerizable compounds represented by the following formulae (P-3-1) to (P-3-15).
(in the formula, Pp31、Pp32、Spp31And Spp32Represents P in the general formula (P-3)p31、Pp32、Spp31And Spp32Same meaning)
Preferable examples of the compound represented by the general formula (P-4) of the present invention include polymerizable compounds represented by the following formulae (P-4-1) to (P-4-15).
(in the formula, Pp41、Pp42、Spp41And Spp42Represents P in the general formula (P-4)p41、Pp42、Spp41And Spp42Same meaning)
The composition of the present invention preferably contains a self-aligning compound in order to further impart vertical alignment. The self-alignment compound is a compound that controls the alignment of a liquid crystal composition without using a conventional liquid crystal alignment film such as polyimide for one or both substrates.
The self-alignment compound is mainly used for being added into a liquid crystal composition and has the following functions: and a member (an electrode (e.g., ITO), a substrate (e.g., a glass substrate, an acrylic substrate, a transparent substrate, a flexible substrate, or the like), a resin layer (e.g., a color filter, an alignment film, a protective layer, or the like), an insulating film (e.g., an inorganic material film, SiNx, or the like)) which is in direct contact with a liquid crystal layer containing the liquid crystal composition, thereby inducing vertical alignment or homeotropic alignment of liquid crystal molecules of the liquid crystal layer. Further, a compound capable of aligning the liquid crystal composition perpendicularly or substantially perpendicularly to the substrate is preferable.
The self-aligning compound preferably has: a polymerizable group for polymerization, an adsorptive group in which a mesogenic group similar to liquid crystal molecules can interact with a member directly contacting the liquid crystal layer, and a flexible group for inducing alignment of the liquid crystal molecules.
The self-aligning compound is preferably a compound represented by the following general formula (SA L).
(in the above formula, PalRepresents a group represented by the general formula (P-I) to the general formula (P-IX),
(in the formula, Rp11And Rp12Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, Wp11Represents a single bond, -O-, -COO-or methylene, tp11Represents 0, 1 or 2)
SpalPresentation sheetA bond or a linear or branched alkylene group having 1 to 20 carbon atoms, 1 or not adjacent 2 or more-CH in the alkylene group2-may each be independently substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,
t represents an adsorption group, and T represents an adsorption group,
MG represents a mesogenic group,
cg represents a hydrogen atom, the adsorption group, or the-Sp groupal－PalOr a linear or branched alkylene group having 1 to 20 carbon atoms, 1 or 2 or more-CH groups not adjacent to each other in the alkylene group2Each independently of the others-CH-CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-, and all of Cg, MG and T may be substituted as described above for the polymerizable group-Sp-al－Pal－，
nsal1、nsal2And nsal3Each independently represents a natural number of 1 to 5)
The polymerizable group of the present invention is PalThe group represented is bonded to other structures directly or via a spacer as required. The polymerizable group is preferably represented by Pal－Spal-represents.
PalPreferably, the group is selected from the group represented by the following general formulae (P-I) to (P-IX).
(in the formula, Rp11And Rp12Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, Wp11Represents a single bond, -O-, -COO-or methylene, tp11Represents 0, 1 or 2)
P is abovea1The group is preferably selected from the group represented by the following general formulae (P-I) to (P-IX), and is preferably the general formula (P-I).
In the self-aligning compound of the present invention, Pal－SpalOptionally mesogenic, adsorptive and/or flexibilizing groupsAnd (4) bonding.
In the self-aligning compound of the present invention, the polymerizable group is preferably bonded to the mesogen group, the adsorbing group or the flexible group directly or via a spacer, and more preferably bonded to the mesogen group or the adsorbing group directly or via a spacer.
The above spacer group (Sp)al) Preferably represents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, more preferably represents a single bond or a linear alkylene group having 1 to 20 carbon atoms, and still more preferably represents a single bond or a linear alkylene group having 2 to 10 carbon atoms. In addition, in the above spacer group (Sp)al) In the (b), 1 or 2 or more-CH not adjacent to each other in the alkylene group2-may also be substituted independently of each other by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-.
In the self-aligning compound of the present invention, the polymerizable group (P)al－Spal-) is preferably 1 or more and 5 or less, more preferably 1 or more and 4 or less, further more preferably 2 or 3, and further more preferably 2.
Pal－SpalThe hydrogen atom in (E-O) -may be substituted with a polymerizable group, an adsorptive group and/or a flexible group.
The mesogenic group in the present invention means a group having a rigid portion, for example, a group having one or more cyclic groups, preferably 2 to 4 cyclic groups, more preferably 3 to 4 cyclic groups, and the cyclic groups may be connected by a connecting group as necessary. The mesogenic group is preferably a skeleton similar to the liquid crystal compound used in the liquid crystal layer.
The "cyclic group" in the present specification means an atomic group in which constituent atoms are bonded to form a ring, and includes a carbon ring, a heterocyclic ring, a saturated or unsaturated cyclic structure, a monocyclic ring, a 2-ring structure, a polycyclic structure, an aromatic group, a non-aromatic group, and the like. The cyclic group may contain at least one hetero atom, and may be substituted with at least one substituent (e.g., a halogen atom, a reactive functional group, or an organic group (e.g., an alkyl group or an aryl group)). When the cyclic group is a monocyclic ring, the mesogenic group preferably contains 2 or more monocyclic rings.
The mesogenic group is preferably represented by, for example, general formula (a L).
(in the formula, ZALRepresents a single bond, -CH-, -CF-, -C.ident.C-, -COO-, -OCO-, -OCOO-, -CF2O－、－OCF2－、－CH＝CHCOO－、－OCOCH＝CH－、－CH2－CH2COO－、－OCOCH2―CH2－、－CH＝C(CH3)COO－、－OCOC(CH3)＝CH－、－CH2－CH(CH3)COO－、－OCOCH(CH3)－CH2－、－OCH2CH2O-or C1-20 alkylene, 1 or 2 or more-CH not adjacent to each other2May also be substituted by-O-, -COO-or-OCO-,
AALrepresents a cyclic group having a valence of 2,
ZALand AALWherein 1 or 2 or more hydrogen atoms are independently replaced by a halogen atom, an adsorbate group, or Pa1－Spa1-or a 1-valent organic radical,
when Z isALAnd AALWhen a plurality of each of them are present, they may be the same or different from each other, and mALRepresents an integer of 1 to 5, wherein ＊ at the left end and ＊ at the right end in the above formula represent a bond)
In the general formula (A L), ZALPreferably a single bond or an alkylene group having 2 to 20 carbon atoms, more preferably a single bond or an alkylene group having 2 to 10 carbon atoms. 1 or 2 or more-CH not adjacent to each other in the above alkylene group2-may also be substituted by-O-, -COO-or-OCO-. When linearity of the rod-like molecule is desired, a single bond in which the ring is directly connected to the ring or an even number of atoms directly connecting the ring to the ring is preferable. For example, when-CH2－CH2In the case of COO-, the reaction mixture,the number of atoms directly linking the ring to the ring is 4.
In the general formula (A L), the cyclic group is preferably selected from the group consisting of 1, 4-phenylene, 1, 4-cyclohexylene, 1, 4-cyclohexenyl, tetrahydropyran-2, 5-diyl, 1, 3-dioxane-2, 5-diyl, tetrahydrothiopyran-2, 5-diyl, thiophene-2, 5-diyl, 1, 4-bicyclo (2,2,2) octylene, decahydronaphthalene-2, 6-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, pyrazine-2, 5-diyl, thiophene-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, 2, 6-naphthylene, phenanthrene-2, 7-diyl, 9, 10-dihydrophenanthrene-2, 7-diyl, 1,2,3,4,4a,9,10 a-octahydrophenanthrene-2, 7-diyl, 1, 4-naphthylene-1, 4,4 b [1, 4a ] octahydrophenanthrene-2, 7-diyl, 1, 5-b, 4,5, b, and 1, 5, 4']Dithiophene-2, 6-diyl, benzo [1, 2-b: 4, 5-b']Diselenophene-2, 6-diyl, [ 1]]Benzothieno [3, 2-b ]]Thiophene-2, 7-diyl, [ 1]]Benzoselenopheno [3, 2-b ] phenophenopeno]Selenophene-2, 7-diyl and fluorene-2, 7-diyl, which may be unsubstituted or substituted, more preferably 1, 4-phenylene, 1, 4-cyclohexylene, 2, 6-naphthylene or phenanthrene-2, 7-diyl, preferably 1, 4-phenylene or 1, 4-cyclohexylene. Further, 1 or 2 or more hydrogen atoms in the cyclic group may be replaced by a halogen atom, an adsorbing group, or Pa1－Spa1-or 1-valent organic group.
In the general formula (A L), the term "monovalent organic group" means a group having a chemical structure formed by forming an organic compound into a 1-valent group, and refers to an atomic group obtained by removing 1 hydrogen atom from an organic compound, and examples thereof include an alkyl group having 1 to 15 carbon atoms, an alkenyl group having 2 to 15 carbon atoms, an alkoxy group having 1 to 14 carbon atoms, an alkenyloxy group having 2 to 15 carbon atoms, and the like, preferably an alkyl group having 1 to 15 carbon atoms or an alkoxy group having 1 to 14 carbon atoms, and 1 or not adjacent 2 or more-CH groups out of the alkyl group, alkenyl group, alkoxy group, and alkenyloxy group2-may also be substituted by-O-, -COO-or-OCO-. The monovalent organic group may also have a function as a flexible group described later.
In the above general formula (A L), mALPreferably an integer of 2 to 4.
Among the mesogenic groups, a more preferred form is represented by the following general formula (A L-1) or (A L-2), and more preferably by the following formula (A L-1).
(in the above formula, Xal1～Xal18Each independently represents a hydrogen atom, a halogen atom, Pa1－Spa1-, an adsorption group or a flexible group, ring A and ring B each independently represent a cyclohexane ring or a benzene ring,
Xal1～Xal18any 1 or 2 or more of them are substituted with the above-mentioned adsorptive group,
Xal1～Xal18any 1 or 2 or more of them are substituted with the above-mentioned flexible group,
the above-mentioned adsorptive group and the above-mentioned flexible group may be substituted with the above-mentioned Pa1－Spa1－，
The general formula (A L-1) or the general formula (A L-2) each has 1 or 2 or more of the above-mentioned Pa1－Spa1－)
In the above formula (A L-1), X is preferably Xa11Or Xa18～Xa112Is substituted with at least 1 or 2 or more of an adsorbing group, more preferably Xa11Or Xa110At least 1 or 2 or more of them are substituted with an adsorption group. In this case, the above-mentioned adsorptive group may be substituted with Pa1－Spa1-. Particularly when ring A is a cyclohexane ring, X is preferably Xa110Substituted into an adsorption group.
In the above formula (A L-1), X is preferably Xa16～Xa114At least 1 or 2 or more species of (a) are substituted with a polymerizable group, more preferably Xal9Or Xa111Is substituted with Pa1－Spa1－。
In the above formula (A L-1), X is preferably Xa11～Xa13、Xa6～Xa114、Xa117～Xa118At least 1 or 2 or more of them are substituted with a flexible group, preferably Xa11～Xa13、Xa6～Xa19、Xa111～Xa114Or Xa117～Xa118At least 1 or 2 or more of them are substituted with a flexible group. More preferably Xa11Is substituted by a flexible group, and Xa6～Xa19Or Xa111～Xa114Any 1 of (a) is substituted with a flexible group. In this case, the former X is more preferablea11The flexible group (2) has a larger number of carbon atoms than the latter. The flexible group may also be substituted with Pa1－Spa1－。
In the above formula (A L-2), X is preferably Xa11Or Xa16～Xa110Is substituted with at least 1 or 2 or more of an adsorbing group, more preferably Xa11Or Xa18Substituted into an adsorption group. In this case, the adsorptive group may be substituted with Pa1－Spa1-. Particularly when ring A is a cyclohexane ring, X is preferably Xa18Substituted into an adsorption group.
In the above formula (A L-2), X is preferably Xal6～Xa110Is substituted by P for 1 or 2 or morea1－Spa1-, more preferably Xal7Or Xa19Is substituted with Pa1－Spa1－。
In the above formula (A L-2), X is preferably Xa16～Xa110At least 1 or 2 or more of them being substituted by Pa1－Spa1-, more preferably Xa17Or Xa14Is substituted with Pa1－Spa1－。
In the above formula (A L-2), X is preferably Xa11～Xa17Or Xa9～Xa114At least 1 or 2 or more of them are substituted with a flexible group, preferably Xa11、Xa4～Xa17Or Xa19～Xa112At least 1 or 2 or more of them are substituted with a flexible group. More preferably Xa11Is substituted by a flexible group, and Xal4～Xa17Or Xa19～Xa112Any 1 of (a) is substituted with a flexible group. In this case, the former is more preferableXa11The flexible group in (1) has more carbon atoms than the latter. The flexible group may also be substituted with Pa1－Spa1－。
Preferred forms of the mesogenic group include those represented by the following formulas (A L-1-1) to (A L-2-3) — general formula (A L) in which 2 hydrogen atoms are eliminated from the structure.
One or more hydrogen atoms in the cyclohexane ring, benzene ring, pyran ring or dioxane ring of the general formulae (A L-1-1) to (A L-2-3) may be replaced by a halogen atom or a P atoma1－Spa1A 1-valent organic group (e.g., an alkyl group having 1 to 15 carbon atoms or an alkoxy group having 1 to 14 carbon atoms), an adsorbing group, or a bending group.
Preferred forms among the mesogenic groups are structures represented by the general formula (A L-1-1), the general formula (A L-1-4), the general formula (A L-1-7), the general formula (A L-2-1) or the general formula (A L-2-3), structures represented by the general formula (A L-1-4), the general formula (A L-1-7) or the general formula (A L-2-3), and structures represented by the general formula (A L-1-4) or the general formula (A L-1-7).
The adsorption group of the present invention is a group having a function of adsorbing an adsorption medium such as a substrate, a film, or an electrode. The adsorption is generally classified into chemisorption in which a chemical bond (a covalent bond, an ionic bond, or a metallic bond) is formed and the adsorption medium and the adsorbate are adsorbed, or physisorption other than the chemisorption. Therefore, the adsorbing group of the present invention is preferably a group capable of physical adsorption to the adsorbing medium, and more preferably the adsorbing group binds to the adsorbing medium by intermolecular forces. The mode of binding to the adsorption medium by the intermolecular force may be binding to the adsorption medium by interaction such as permanent dipole, permanent quadrupole, dispersion force, charge transfer force, or hydrogen bond. Preferred embodiments of the adsorbent group of the present invention include those capable of binding to the adsorbent medium by hydrogen bonding. In this case, the adsorbate group of the present invention may be a donor or an acceptor of a proton via a hydrogen bond, or both.
The adsorption group of the present invention is preferably a group containing a polar element having an atomic group in which a carbon atom is bonded to a heteroatom. The polar element referred to in the present specification means an atomic group in which a carbon atom and a hetero atom are directly bonded to each other. The heteroatom is preferably at least 1 selected from the group consisting of N, O, S, P, B and Si, preferably at least 1 selected from the group consisting of N, O and S, preferably at least 1 selected from the group consisting of N and O, and preferably O.
In the self-aligning compound of the present invention, the valence of the polar element in the present invention is not particularly limited, such as monovalent, divalent, or trivalent, and the number of polar elements in the adsorption group is not particularly limited.
In the self-orienting compound of the present invention, the number of the adsorption groups in one molecule is preferably 1 to 8, more preferably 1 to 4, and still more preferably 1 to 3.
In addition, the adsorption group of the present invention does not contain Pa1－Spa1-and a flexible base.
The adsorption group of the present invention contains 1 or 2 or more polar elements, and the adsorption group can be roughly classified into a cyclic base type and a chain base type. The cyclic base type is a form containing a cyclic group having a cyclic structure containing a polar element in its structure, and the chain base type is a form containing no cyclic group (having a cyclic structure containing a polar element) in its structure. The chain group is a form having a polar element in a linear or branched chain group, and may have a cyclic structure containing no polar element in a part thereof.
The adsorption group of the present invention is a form containing a cyclic group, and means a form containing at least 1 polar element in a cyclic atomic arrangement. The cyclic group in the present specification is as described above. Therefore, when the adsorption group of the present invention is in a form containing a cyclic group, the adsorption group may be branched or linear as long as it contains a cyclic group having a polar element.
The form of the adsorption group of the present invention as a chain group means the following form: the molecule does not contain a cyclic atomic arrangement containing polar elements, and contains at least 1 polar element in a linear atomic arrangement (which may be branched). The chain group in the present specification means an atomic group in which atoms constituting the chain group are bonded in a linear (branched) form without arranging cyclic atoms in the structural formula, and means an acyclic group. In other words, the following concept is used: the term "linear or branched aliphatic group" means an aliphatic group which may have a saturated bond or an unsaturated bond, and includes, for example, an alkyl group, an alkenyl group, an alkoxy group, an ester group, an ether group, a ketone group, etc., and may be substituted with at least 1 substituent (a reactive functional group (e.g., a vinyl group, an acryloyl group, a methacryloyl group), etc.), a chain organic group (e.g., an alkyl group, a cyano group, etc.)). The chain group of the present invention may be either linear or branched.
The adsorption group of the present invention preferably has a chain group or a cyclic group, and when importance is attached to the adsorption ability, a chain group is preferable, and from the viewpoint of stability to the liquid crystal composition, a cyclic group is preferable.
When the adsorption group of the present invention is a cyclic group, it is more preferably a heteroaromatic group (including a condensed ring) having 3 to 20 carbon atoms or a heteroaliphatic group (including a condensed ring) having 3 to 20 carbon atoms, still more preferably a heteroaromatic group (including a condensed ring) having 3 to 12 carbon atoms or a heteroaliphatic group (including a condensed ring) having 3 to 12 carbon atoms, and yet still more preferably a five-membered heteroaromatic group, a five-membered heteroaliphatic group, a six-membered heteroaromatic group or a six-membered heteroaromatic adipoyl group, and a hydrogen atom in these ring structures may be substituted by a halogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms or an alkyloxy group.
When the adsorption group of the present invention is a chain group, it is preferably a hydrogen atom or-CH in a linear or branched alkyl group having 1 to 20 carbon atoms2-CH substituted by a polar element, 1 or more than 2 not adjacent of said alkyl group2May also be substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO--COO-or-OCO-substituted. When the adsorption group of the present invention is a chain group, it preferably contains a polar element or 2 or more polar elements at the end.
The hydrogen atom of the adsorbing group of the present invention may be substituted with a polymerizable group.
Specifically, the type of the polar element of the present invention is preferably a partial structure represented by a polar element containing an oxygen atom (hereinafter, referred to as an oxygen-containing polar element), a polar element containing a nitrogen atom (hereinafter, referred to as a nitrogen-containing polar element), a polar element containing a phosphorus atom (hereinafter, referred to as a phosphorus-containing polar element), a polar element containing a boron atom (hereinafter, referred to as a boron-containing polar element), a polar element containing a silicon atom (hereinafter, referred to as a silicon-containing polar element), or a polar element containing a sulfur atom (hereinafter, referred to as a sulfur-containing polar element).
The oxygen-containing polar element is preferably selected from the group consisting of a hydroxyl group (-OH), an alkanol group (-R), and a mixture thereoft－OH；RtIs alkylene), alkoxy (-OR; wherein R is alkyl group, formyl group (-CHO), carboxyl group (-COOH), ether group (-R)tORt' -; wherein R ist、Rt’Is alkylene or alkenylene), carbonyl (-R)t－C(＝O)－Rt’-; wherein R ist、Rt’Alkylene or alkenylene), carbonate (-O-C (-O) -O-) and ester (-COOR)t’-; wherein R ist’Alkylene or alkenylene) or a group having such a group bonded to a carbon atom.
The nitrogen-containing polar element is preferably selected from the group consisting of a cyano group (-CN), and a 1-stage amino group (-NH)2) 2-amino (-NH-), 3-amino (-NRR'; wherein R, R' is alkyl), pyridyl, carbamoyl (-CONH)2) And ureido (-NHCONH)2) At least 1 group of the group or a group having the group bonded to a carbon atom.
The phosphorus-containing polar element is preferablySelected from the group consisting of phosphino (-CX)2－P(＝O)H2) And phosphoric acid group (-CX)2－OP(＝O)(OH)2) At least 1 group of the group or a group having the group bonded to a carbon atom.
The boron-containing polar element is preferably a boron acid group (-B (OH))2) A group of (1).
The silicon-containing polar element is preferably-Si (OH)3A group OR a group in which-Si (OR) (OR ') (wherein R, R ' and R ' are alkyl groups) is bonded to a carbon atom.
The sulfur-containing polar element is preferably selected from the group consisting of a mercapto group (-SH), a thio group (-S-), an oxysulfide group (-S (═ O) -), and a sulfonyl group (-SO) -2-) sulfonamido (-SO)2NH2) Sulfonic acid group (-SO)3H) And a sulfinic acid group (-S (═ O) OH), or a group in which the groups are bonded to carbon atoms.
Therefore, the adsorption group of the present invention is preferably selected from a group consisting of a group having a cyclic group with an oxygen-containing polar element (hereinafter, referred to as an oxygen-containing cyclic group), a group having a cyclic group with a nitrogen-atom polar element (hereinafter, referred to as a nitrogen-containing cyclic group), a group having a cyclic group with a phosphorus-containing polar element (hereinafter, referred to as a phosphorus-containing cyclic group), a group having a cyclic group with a boron-containing polar element (hereinafter, referred to as a boron-containing cyclic group), a group having a cyclic group with a silicon-containing polar element (hereinafter, referred to as a silicon-containing cyclic group), a group having a cyclic group with a sulfur-containing polar element (hereinafter, referred to as a sulfur-containing cyclic group), a group having a chain group with an oxygen-containing polar element (hereinafter, referred to as an oxygen-containing chain group), a group having a nitrogen-atom polar element (hereinafter, referred to as a nitrogen-containing chain group, referred to as a phosphorus-containing chain group), a chain group having a boron-containing polar element (hereinafter referred to as a boron-containing chain group), a chain group having a silicon-containing polar element (hereinafter referred to as a silicon-containing chain group), and a chain group having a sulfur-containing polar element (hereinafter referred to as a sulfur-containing chain group), and 1 or 2 or more groups per se or containing the group are contained, and from the viewpoint of adsorption capacity, 1 or 2 or more groups selected from the group consisting of an oxygen-containing cyclic group, a sulfur-containing cyclic group, an oxygen-containing chain group, and a nitrogen-containing chain group are more preferably contained.
The adsorption group of the present invention is preferably a group represented by the following general formula (T).
(in the above general formula (T), Xt1Represents a linear or branched alkyl group having 1 to 18 carbon atoms or-NH2The hydrogen atom in the above alkyl group may be substituted by cyano or Pa1－Spa1-, or-CH of the above-mentioned alkyl group2-may be substituted by-O-, -COO-, -C (═ O) -, -OCO-, -CH ═ CH-,
r is as defined abovet1Represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or Zt1A linear or branched alkylene group having 1 to 8 carbon atoms bonded thereto or Zt1A linear or branched alkenylene group having 2 to 8 carbon atoms bonded thereto, wherein Z ist2Represents a single bond, -CH of a linear or branched alkylene group having 1 to 18 carbon atoms or a linear or branched alkenylene group having 2 to 18 carbon atoms2-may be substituted by-O-, -COO-, -C (═ O) -, -OCO-,
Zt1represents a single bond, -CH of a straight-chain or branched alkylene group having 1 to 18 carbon atoms or a straight-chain or branched alkenylene group having 2 to 18 carbon atoms2-may be substituted by-O-, -COO-, -C (═ O) -, -OCO-, in such a way that the oxygen atoms are not directly adjacent to each other, and, in addition, when X is presentt1is-Zt2－O－RatAnd R isatIn the case of alkylene or alkenylene, Z may bet1With Rt1Bonding is carried out on the raw materials,
Wt0represents a carbon number of 1 to 18Straight-chain or branched alkylene of (A) or (B), or-CH of the alkylene2May be substituted by-O-, -CH-, -COO-, -C- (O) -, -OCO-in such a manner that oxygen atoms are not directly adjacent to each other, and furthermore, the hydrogen atoms of the above alkylene groups may be substituted by the general formula (T),
Wt1represents a single bond, a straight-chain or branched alkylene group, -CH of the alkylene group2-may be substituted by-O-, -COO-, -C (═ O) -, -OCO-,
nt1represents an integer of 0 to 4 inclusive,
the hydrogen atom in the molecule may be substituted with the polymerizable group Pa1－Spa1-, ＊ represents a bond to a mesogenic group, a polymerizable group, a flexible group or a spacer group)
Among the above general formula (T), X is preferablet1Represents a linear or branched alkyl group having 1 to 17 carbon atoms, -NH2or-Zt2－O－Rt1A hydrogen atom in the alkyl group may be substituted by a cyano group or Pa1－Spa1-, the above-mentioned Rt1Represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or Zt1A linear or branched alkylene group having 1 to 8 carbon atoms bonded thereto or Zt1A linear or branched alkenylene group having 2 to 8 carbon atoms bonded thereto, wherein Z ist2Represents a single bond, -CH of a linear or branched alkylene group having 1 to 18 carbon atoms or a linear or branched alkenylene group having 2 to 18 carbon atoms2-may be substituted by-O-, -COO-, -C (═ O) -, -OCO-in such a way that the oxygen atoms are not directly adjacent.
Examples of the form in which the adsorbing group (general formula (T)) in the general formula (T) may be substituted with an adsorbing group (general formula (T)) include a group represented by the general formula (T).
(in the above general formula (t), Xt1、Zt1、Wt1And nt1The same as the symbols in the above general formula (T),
Wt2represents a single bond or an organic group having a valence of 2 to 4,
mt1represents an integer of 1 to 3 inclusive, and hydrogen atoms in the molecule may be substituted with the polymerizable group Pa1－Spa1-, ＊ represents a bond to a mesogenic group, a polymerizable group, a flexible group or a spacer group)
-W in the above general formula (t)t2-Any "represents: wt2Represents a single bond to a polyvalent group, and the bond is a valence of 1 to a polyvalent (Any).
In the general formula (t), the 2 to 4 valent organic group means: an atomic group in which 2 to 4 hydrogen atoms are removed from an organic compound, wherein the organic compound is a group having a 2 to 4-valent form and has a chemical structure.
In the general formula (t), the organic group has a valence of 2 to 4t2Any is preferably a chain organic group, and examples thereof include: a linear or branched alkylene group having 1 to 10 carbon atoms (the alkylene group having-CH)2The alkylene group may be substituted by-O-, -COO-, -C (. quadrature.O) -, -OCO-) such that oxygen atoms are not directly adjacent to each other, or a linear or branched alkylene polyvalent group having 1 to 10 carbon atoms (the alkylene group has-CH-)2The "O" group may be substituted with an oxygen atom not directly adjacent to the "O", "COO", "C (═ O) -, -OCO-), -PH-, -POH-, -NH-, a nitrogen atom, a phosphorus atom, or the like. The alkylene polyvalent group is a group having a valence of 3 or 4, which is obtained by removing 1 to 2 hydrogen atoms from an alkylene group, and is a group having a valence of 3 to 4, which has a free valence in a so-called hydrocarbon chain.
The group represented by the above general formula (T) is W in the general formula (T)t0That is, in the case where the adsorptive group (general formula (T)) may be substituted with the adsorptive group (general formula (T)), the preferred form of the group represented by the above general formula (T) is, for example, Wt2In the case of an organic radical having a valence of 3, i.e. mt1’Is 2, Wt2Examples of the nitrogen atom or the alkylene polyvalent group include the following general formula (t-a) or (t-b).
(in the above formulae (t-a) and (t-b), RtcA hydrogen atom, a linear or branched alkyl group having 1 to 10 carbon atoms or a polymerizable group Pa1－Spa1-represents a group of atoms represented by,
Zt1and Zt1’Each independently represents Z in the general formula (T)t1In the same sense, the term "a", "an", "the" or "the" is used,
Xt1and Xt1’Each independently represents Z in the general formula (T)t1In the same sense, the term "a", "an", "the" or "the" is used,
Wt1represents W in the general formula (T)t1In the same sense, the term "a", "an", "the" or "the" is used,
nt1and nt1’Each independently represents n in the general formula (T)t1In the same sense, the term "a", "an", "the" or "the" is used,
the hydrogen atom in the molecule may be substituted with the polymerizable group Pa1－Spa1-, ＊ represents a bond to a mesogenic group, a polymerizable group, a flexible group or a spacer group)
In the formula (t), for example when-Wt2In the case where Any is a 4-valent organic group, that is, mt1’Is 3, -Wt2when-Any is an alkylene polyvalent group, for example, the following general formula (t-c) may be mentioned.
(in the above formula (t-c), Zt1、Zt1’And Zt1”Each independently represents Z in the general formula (T)t1In the same sense, the term "a", "an", "the" or "the" is used,
Xt1、Xt1’and Xt1”Each independently represents X in the general formula (T)t1In the same sense, the term "a", "an", "the" or "the" is used,
Wt1is represented by the general formula (T)W of (2)t1In the same sense, the term "a", "an", "the" or "the" is used,
nt1、nt1’and nt1”Each independently represents n in the general formula (T)t1In the same sense, hydrogen atoms in the molecule may be substituted with the polymerizable group Pa1－Spa1-, ＊ represents a bond to a mesogenic group, a polymerizable group, a flexible group or a spacer group)
In the above general formula (t), mt1’Preferably 1 or 2, mt1’More preferably 1. Among the forms represented by the above general formulae (t-a), (t-b) and (t-c), the form represented by the above general formula (t-a) is preferable.
In the above general formula (t), -Wt2Any is preferably a single bond or a 2-to 3-valent organic group, more preferably a single bond, a straight-chain or branched alkylene group having 1 to 8 carbon atoms (the alkylene group has-CH2A linear or branched alkanetriyl group (having 1 to 8 carbon atoms) which may be substituted by-O-so that oxygen atoms are not directly adjacent to each other (the alkanetriyl group may have a-CH group)2An alkyl-subunit which may be substituted by-O-so as not to be directly adjacent to an oxygen atom or may be linear or branched (the alkyl-subunit having-CH)2-may be substituted by-O-in such a way that the oxygen atoms are not directly adjacent. For example, the following groups can be mentioned.
(in the above formula, RtcRepresents an alkyl group having 1 to 8 carbon atoms or a polymerizable group (P)a1－Spa1－)，nt0Represents an integer of 1 to 7, ＊ represents a bond) and W may bet2Is substituted with a polymerizable group (P)a1－Spa1－)。
In the above general formula (t), mt1Preferably represents 1 or 2.
In the above general formula (T) or general formula (T), Wt1Preferably represents a single bond, or a linear or branched alkylene group having 1 to 8 carbon atoms (represents a single bond orStraight-chain or branched alkylene group, -CH of said alkylene group2The alkylene group may be substituted by-O-, -COO-, -C (. quadrature.O) -, -OCO-) so that oxygen atoms are not directly adjacent to each other, and more preferably represents a single bond or a linear or branched alkylene group having 1 to 7 carbon atoms (represents a single bond or a linear or branched alkylene group, and-CH-of the alkylene group2-may be substituted by-O-in such a way that the oxygen atoms are not directly adjacent. In addition, Wt1May be bonded in place of the hydrogen atom of the mesogenic group, the polymerizable group or the flexible group.
In the above general formula (T) or general formula (T), X is containedt1Is not in contact with Zt1Form of linkage (chain radical) and Xt1And Zt1The bond forms a ring form (cyclic group).
In the former form, the alkyl group is preferably a linear or branched alkyl group having 1 to 8 carbon atoms or a-NH group2、－Zt2－O－Rt1A C1-7 linear or branched alkyl group substituted with a group or a cyano group, more preferably a C1-7 linear or branched alkyl group, a-Z-substituted alkyl groupt2－O－Rt1A cyano-substituted straight-chain or branched alkyl group having 1 to 7 carbon atoms. In the former form, R is as defined abovet1Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, and Z ist2Preferably a single bond, a linear or branched alkylene group having 1 to 10 carbon atoms, or a linear or branched alkenylene group having 2 to 10 carbon atoms (the alkylene group or-CH group of the alkenylene group)2-may be substituted by-O-, -COO-, -C (═ O) -, -OCO-in such a way that the oxygen atoms are not directly adjacent.
In the latter form, n is preferablyt1Is 1 or more, Xt1is-Zt2－O－Rt1，Rt1Is a linear or branched alkylene group having 1 to 7 carbon atoms or a linear or branched alkenylene group having 2 to 7 carbon atoms, and Z ist1With Rt1The linkage is preferably represented by the following general formula (T'), for example.
(in the above formula (T'), Rt1’Each independently represents a linear or branched alkylene group having 1 to 8 carbon atoms or a linear or branched alkenylene group having 2 to 8 carbon atoms,
Zt2’each independently represents a single bond, a linear or branched alkylene group having 1 to 10 carbon atoms, or a linear or branched alkenylene group having 2 to 10 carbon atoms, -CH2-may be substituted by-O-, -COO-, -C (═ O) -, -OCO-,
Zt1’represents a linear or branched alkylene 3-valent group having 1 to 18 carbon atoms or a linear or branched alkenylene 3-valent group having 1 to 18 carbon atoms, -CH of the alkylene 3-valent group or alkenylene 3-valent group2-may be substituted by-O-, -COO-, -C (═ O) -or OCO-in such a way that the oxygen atoms are not directly adjacent,
Wt2represents a single bond or an organic group having a valence of 2 to 4,
－Wt1-CH represents a single bond, a linear or branched alkylene group, or a-CH group of the alkylene group2-may be substituted by-O-, -COO-, -C (═ O) -, -OCO-,
nt1’represents an integer of 1 to 4 inclusive,
mt1’represents an integer of 1 to 3 inclusive, and hydrogen atoms in the molecule may be substituted with the polymerizable group Pa1－Spa1-, ＊ represents a bond to a mesogenic group, a polymerizable group, a flexible group or a spacer group)
The alkylene group having a valence of 3 means a group having a valence of 3 resulting from further removing 1 hydrogen atom from an alkylene group. The 3-valent alkenylene group refers to a group having a valence of 3 resulting from further removing 1 hydrogen atom from the alkenylene group, and includes a so-called 3-valent group having a free valence in a hydrocarbon chain, such as an alkanetriyl group or an alkyl-ylidene group.
In the above formula (T), when X ist1Is not in contact with Zt1In the form of a linkage (chain radical), Zt1Represents a single bond, a linear or branched alkylene group having 1 to 12 carbon atoms, or a linear or branched alkenylene group having 2 to 12 carbon atoms, — CH of the alkylene group2-may also be substituted by-O-, -COO-, -C (═ O) -, -OCO-.
In the above general formula (T), when X ist1Is a reaction with Zt1In the case of the form of the bond (cyclic group), it is represented by the above general formula (T').
In the above general formula (T), nt1Preferably represents an integer of 0 to 3, nt1More preferably, it represents an integer of 0 to 2.
The general formula (T) is preferably at least 1 selected from the group consisting of cyclic groups represented by general formulas (T-1-1) to (T-4-1) and chain groups represented by general formula (T-5-1). When the cyclic group is selected as the adsorption group represented by the general formula (T) in the present invention, the cyclic group is preferably represented by the general formula (T-1-1) or the general formula (T-2-1) from the viewpoints of adsorption ability and compatibility with a liquid crystal composition. On the other hand, when the chain group is selected as the adsorbing group represented by the general formula (T) of the present invention, the general formula (T-5-1) is preferable from the viewpoints of adsorption ability and stability to a liquid crystal composition.
(in the formula, XtaAnd XtbEach independently represents-O-, -S-or-CH2－，
Rt5Represents a linear or branched alkyl group having 1 to 8 carbon atoms, a cyanolated alkyl group or a linear or branched alkoxy group having 1 to 8 carbon atoms, at least 2 or more of these alkyl groups being represented by-CH2-may be substituted by-CH ═ CH-, -C.ident.C-, -O-or-NH-in such a way that the oxygen atoms are not directly adjacent,
Zt3presentation sheetA bond, a linear or branched alkylene group having 1 to 18 carbon atoms or a linear or branched alkenylene group having 2 to 18 carbon atoms, -CH of the alkylene group or the alkenylene group2-may be substituted by-O-, -COO-, -C (═ O) -, -OCO-,
Wt2represents a single bond or an organic group having a valence of 1 to 4,
Wt1represents a single bond, or a linear or branched alkylene group,
nt1represents an integer of 0 to 4 inclusive,
mt1represents an integer of 1 to 3 inclusive, and hydrogen atoms in the molecule may be substituted with the polymerizable group Pa1－Spa1-, ＊ represents a bond to a mesogenic group, a polymerizable group, a flexible group or a spacer group)
In the above general formulae (T-1-1) to (T-4-1), X is preferably XtaOr XtbAny of them is-O-, more preferably XtaAnd Xtbis-O-.
Specific examples of the above general formulae (T-1-1) to (T-4-1) include the following groups.
(in the above formula, RtcWith a hydrogen atom, an alkyl group having 1 to 7 carbon atoms or a polymerizable group Pa1－Spa1-, hydrogen atoms in the molecule may be substituted with the polymerizable group Pa1－Spa1-, ＊ represents a bond to a mesogenic group, a polymerizable group, a flexible group or a spacer group)
The above-mentioned general formula (T-5-1) preferably represents the general formula (T-5-2).
(in the above general formula (T-5-2), Wt1Represents W in the above general formula (T-5)t1Are identical to each otherIn the sense of (1), Rt51And Rt52Each independently represents a linear or branched alkyl group or a cyanoalkyl group having 1 to 8 carbon atoms, and at least 2 or more of these alkyl groups are-CH groups2-may be substituted by-CH ═ CH-, -C ≡ C-, -O-or-NH-in such a way that the oxygen atoms are not directly adjacent, RtcWith a hydrogen atom, an alkyl group having 1 to 7 carbon atoms or a polymerizable group Pa1－Spa1-represents, nt1、nt2And nt3Each independently represents 0 or 1, and hydrogen atoms in the molecule may be substituted by Pa1－Spa1－)
Specific examples of the above general formula (T-5-1) include the following groups.
(in the above formula, RtcWith a hydrogen atom, an alkyl group having 1 to 7 carbon atoms or a polymerizable group Pa1－Spa1-represents that hydrogen atoms in the molecule may be substituted with the polymerizable group Pa1－Spa1-, ＊ represents a bond to a mesogenic group, a polymerizable group, a flexible group or a spacer group)
(in the above formula, RtcWith a hydrogen atom, an alkyl group having 1 to 7 carbon atoms or a polymerizable group Pa1－Spa1-represents that hydrogen atoms in the molecule may be substituted with the polymerizable group Pa1－Spa1- (＊) represents a bond with a mesogenic group, a polymerizable group, a flexible group or a spacer group)
The polar group of the self-aligning compound of the present invention is preferably not a hydroxyl group (alcoholic, phenolic, -COOH, -SO)2(OH), etc.).
In the self-aligning compound of the present invention, it is preferable that the polar element contained in the adsorptive group or the polar element contained in the polymerizable group is localized. The adsorptive group is an important structure for vertically aligning the liquid crystal composition, and the adsorptive group is adjacent to the polymerizable group, whereby more favorable alignment properties can be obtained and favorable solubility in the liquid crystal composition can be exhibited. Specifically, the mesogenic group is preferably in the form of having a polymerizable group and an adsorptive group on the same ring. In this case, the term "a form in which 1 or more polymerizable groups and 1 or more adsorbate groups are bonded to the same ring" and "a form in which one of 1 or more polymerizable groups or at least one of 1 or more adsorbate groups is bonded to another, and the polymerizable group and the adsorbate group are present on the same ring" are included. In this case, the hydrogen atom of the spacer of the polymerizable group may be substituted with the adsorbing group, and the hydrogen atom of the molecule of the adsorbing group may be substituted with the spacer of the polymerizable group.
In the self-aligning compound of the present invention, 1 or more hydrogen atoms of the polymerizable group may be substituted with the adsorptive group. In this case, a preferable embodiment includes a polymer group Pa1Or if desired an SP attached to the polymeric groupa1The form in which 1 or more hydrogen atoms are substituted with an adsorption group is more preferable, and a polymerizable group (P) is mentioneda1－Spa1-) wherein 1 or more hydrogen atoms are substituted with an adsorption group represented by the general formula (T).
Examples of suitable forms of linkage of the adsorptive group and the polymerizable group include the following formulae (T-1-1.1), (T-6-1.1) and (T-5-1.1).
(in the above formula, Rt11a、Rt16aAnd Rt151aEach independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, Rt151bAnd Rt151cEach independently of the otherAn alkyl group having 1 to 3 carbon atoms, a cyanoalkyl group having 1 to 3 carbon atoms,
Xaand Xbrepresents-O-, -S-or-CH2－，
Lt151aAnd Lt151bEach independently represents a methylene group, an ethylene group, a propylene group, an ethylene group, an isopropenyl group or an ethylene group,
nt11c，nt151c、nt16c、nt151d、nt151e、nt151fand nt151gEach independently represents 0 or 1, nt11a、nt11b、nt16a、nt16b、nt151aAnd nt151bEach independently represents an integer of 1 to 11, and ＊ represents an inverted or inverted addition to the mesogenic group
In the above formula (T-1-1.1), X is preferablyaOr XbAny of them is-O-, more preferably XtaAnd Xtbis-O-.
Preferably, in the above formula (T-5-1.1), Lt151aAnd Lt151bEach independently is methylene, ethylene, vinylene, isopropenyl, or ethylene.
In the above formulae (T-1-1.1), (T-6-1.1) and (T-5-1.1), nt11a、nt11b、nt16a、nt16b、nt151aAnd nt151bPreferably, each independently is an integer of 1 to 8, more preferably an integer of 1 to 5.
The flexible group of the present invention has a function of inducing the alignment of liquid crystal molecules, and preferably represents a linear or branched alkylene group having 1 to 20 carbon atoms, more preferably a linear alkylene group having 1 to 20 carbon atoms, and still more preferably a linear alkylene group having 2 to 15 carbon atoms. 1 or 2 or more-CH not adjacent to each other in the alkylene group2-may each be independently substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-, or-OCO-.
The flexible group is preferably bonded to the mesogenic group from the viewpoint that the self-alignment compound has a so-called amphiphilic property with respect to the liquid crystal layer.
In the self-orienting compound of the present invention, the number of the flexible groups is preferably 1 to 6, more preferably 1 to 4, and still more preferably 1 to 3.
In the above-mentioned self-aligning compound, it is preferable that a polar portion such as an adsorbing group or a polymerizable group which is not easily fused with the liquid crystal layer and a non-polar portion such as a mesogen group or a flexible group which is easily fused with the liquid crystal layer are present unevenly within the molecule, and an amphiphilic property is exhibited to a so-called liquid crystal layer. Therefore, the self-aligning compound of the present invention is preferably of the following structure: the mesogenic group has a flexible group for aligning liquid crystal molecules at one end thereof, and a polymerizable group and an adsorptive group at the other end thereof. It is considered that since the interface free energy is increased in the vicinity of the interface between the liquid crystal layer and the substrate, a substance having a nonpolar portion having affinity for the liquid crystal layer and a polar portion having low affinity for the liquid crystal layer in one molecule is arranged on the interface, and the interface free energy is lowered.
The lower limit of the content of the self-aligning compound in the liquid crystal composition of the present invention is preferably 0.02 mass%, preferably 0.03 mass%, preferably 0.04 mass%, preferably 0.05 mass%, preferably 0.06 mass%, preferably 0.07 mass%, preferably 0.08 mass%, preferably 0.09 mass%, preferably 0.1 mass%, preferably 0.12 mass%, preferably 0.15 mass%, preferably 0.17 mass%, preferably 0.2 mass%, preferably 0.22 mass%, preferably 0.25 mass%, preferably 0.27 mass%, preferably 0.3 mass%, preferably 0.32 mass%, preferably 0.35 mass%, preferably 0.37 mass%, preferably 0.4 mass%, preferably 0.42 mass%, preferably 0.45 mass%, preferably 0.5 mass%, preferably 0.55 mass%. The upper limit of the content of the polymerizable compound represented by the general formula (I) in the liquid crystal composition of the present invention is preferably 2.5% by mass, preferably 2.3% by mass, preferably 2.1% by mass, preferably 2% by mass, preferably 1.8% by mass, preferably 1.6% by mass, preferably 1.5% by mass, preferably 1% by mass, preferably 0.95% by mass, preferably 0.9% by mass, preferably 0.85% by mass, preferably 0.8% by mass, preferably 0.75% by mass, preferably 0.7% by mass, preferably 0.65% by mass, preferably 0.6% by mass, preferably 0.55% by mass, preferably 0.5% by mass, preferably 0.45% by mass, preferably 0.4% by mass.
A particularly suitable specific example of the self-aligning compound of the present invention is a compound represented by the following general formula (al-1-1).
(in the above general formula (al-1-1), Ral3Represents a linear alkyl group having 1 to 12 carbon atoms, wherein 1 or 2 or more-CH groups not adjacent to each other are present in the alkyl group2-may also be substituted by-O-or-CH ═ CH-,
Lal5、Lal6、Lal7and Lal8Each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a halogen atom or Pa1－Spa1-, 1 or 2 or more-CH groups not adjacent to each other in the alkyl group2-may also be substituted by-O-or-CH ═ CH-,
ring Aal3Represents 1, 4-cyclohexylene or 1, 4-phenylene,
Ralaor RalbEach independently represents an hydro-atom or P as defined abovea1－Spa1－，RalaOr RalbAt least one of (A) represents the above Pa1－Spa1－，
Zal3Represents a single bond, -CH2－CH2－、－CH2-O-or O-CH2－，
Ral4Represents an adsorbing group represented by the general formula (T),
pa13and pa14Each independently represents 0 or 1)
Preferably, L in the above general formula (al-1-1)al7And Lal8One of them represents an alkyl group having 1 to 5 carbon atoms.
In the above general formula (al-1-1), RalaAnd RalbPreferably represents the above-mentioned Pa1－Spa1－。
In the above general formula (al-1-1), Ral4Preferred are the above-mentioned general formulae (T-1-1) to (T-7-1), or the formulae (T-1-1.1) or (T-5-1.1).
Preferred examples of the compound include compounds represented by the following formulae (A L-2.1) to (A L-2.60).
The composition of the present invention may further contain 1 or 2 or more compounds (Q) as additives for improving reliability. The compound (Q) preferably has the following structure.
(in the formula, RQRepresents a hydroxyl group, a hydrogen atom, a straight-chain or branched-chain alkyl group having 1 to 22 carbon atoms, one or two or more CH groups in the alkyl group2The radicals may be interrupted by-O-, -CH ═ CH-, -CO-, -OCO-, -COO-, -C.ident.C-, -CF-in such a way that the oxygen atoms are not directly adjacent to one another2O－、－OCF2-substitution, bonding at star with other structures)
RQRepresents a straight-chain or branched alkyl group having 1 to 22 carbon atoms, one or two or more CH groups in the alkyl group2The radicals may be substituted by-O-, -CH ═ CH-, -CO-, -OCO-, -COO-, -C.ident.C-, -CF-in such a way that oxygen atoms are not directly adjacent to one another2O－、－OCF2-substituted, preferably linear alkyl, linear alkoxy, one CH with 1 to 10 carbon atoms2Straight-chain alkyl, branched-chain alkoxy, one CH substituted by-OCO-or-COO-radical2A branched alkyl group substituted with-OCO-or-COO-, more preferably a straight-chain alkyl group having 1 to 20 carbon atoms, one CH2Straight-chain alkyl, branched-chain alkoxy, one CH substituted by-OCO-or-COO-radical2Branched alkyl groups substituted with-OCO-or-COO-. MQRepresents trans-1, 4-cyclohexylene, 1, 4-phenylene or a single bond, preferably trans-1, 4-cyclohexylene or 1, 4-phenylene.
More specifically, the compound (Q) is preferably a compound represented by the following general formula (Q-a) to general formula (Q-d).
In the formula, RQ1Preferably a linear or branched alkyl group of 1 to 10 carbon atoms, RQ2Preferably a linear or branched alkyl group of 1 to 20 carbon atoms, RQ3Preferably a straight-chain alkyl group, a branched-chain alkyl group, a straight-chain alkoxy group or a branched-chain alkoxy group having 1 to 8 carbon atoms, LQPreferably a linear alkylene group or a branched alkylene group having 1 to 8 carbon atoms. Of the compounds represented by the general formulae (Q-a) to (Q-d), the compounds represented by the general formulae (Q-c) and (Q-d) are more preferable.
The composition of the present invention preferably contains 1 or 2 compounds represented by the general formula (Q), more preferably 1 to 5 compounds, and the content thereof is preferably 0.001 to 1%, more preferably 0.001 to 0.1%, and further preferably 0.001 to 0.05%.
Specifically, the antioxidants and light stabilizers usable in the present invention are preferably compounds represented by the following (Q-1) to (Q-44).
(wherein n represents an integer of 0 to 20.)
The liquid crystal composition of the present embodiment is applied to a liquid crystal display element. Hereinafter, an example of the liquid crystal display device of the present embodiment will be described with reference to fig. 1 and 2 as appropriate.
Fig. 1 is a diagram schematically showing the structure of a liquid crystal display element. In fig. 1, the respective components are shown as being separated from each other for convenience of explanation. As shown in fig. 1, the liquid crystal display element 1 of the present embodiment includes a first substrate 2 and a second substrate 3 disposed to face each other, and a liquid crystal layer 4 provided between the first substrate 2 and the second substrate 3, and the liquid crystal layer 4 is formed of the liquid crystal composition of the present embodiment.
The first substrate 2 has a pixel electrode layer 5 formed on a surface thereof on the liquid crystal layer 4 side. In the second substrate 3, a common electrode layer 6 is formed on the liquid crystal layer 4 side. The first substrate 2 and the second substrate 3 may be sandwiched by a pair of polarizing plates 7 and 8. A color filter 9 may be further provided on the liquid crystal layer 4 side of the second substrate 3.
That is, the liquid crystal display element 1 of one embodiment has a structure in which a first polarizing plate 7, a first substrate 2, a pixel electrode layer 5, a liquid crystal layer 4 containing a liquid crystal composition, a common electrode layer 6, a color filter 9, a second substrate 3, and a second polarizing plate 8 are sequentially stacked.
The first substrate 2 and the second substrate 3 are made of a material having flexibility, such as glass or plastic. At least one of the first substrate 2 and the second substrate 3 is made of a transparent material, and the other is made of a transparent material, or an opaque material such as metal or silicon. The first substrate 2 and the second substrate 3 are bonded to each other with a sealing material such as an epoxy thermosetting composition and a sealing material disposed in the peripheral region, and a spacer composed of a resin formed by photolithography or a granular spacer such as glass particles, plastic particles, or alumina particles may be disposed therebetween in order to maintain the distance between the substrates.
The first polarizing plate 7 and the second polarizing plate 8 can be adjusted so that the polarization axes of the respective polarizing plates are adjusted to improve the viewing angle and the contrast, and preferably have transmission axes orthogonal to each other so that their transmission axes operate in the normally black mode. More preferably, either one of the first polarizing plate 7 and the second polarizing plate 8 is arranged to have a transmission axis parallel to the alignment direction of the liquid crystal molecules when no voltage is applied.
From the viewpoint of preventing light leakage, the color filter 9 is preferably formed into a black matrix, and a black matrix (not shown) is preferably formed in a portion corresponding to the thin film transistor.
The black matrix may be provided on the substrate opposite to the array substrate together with the color filter, may be provided on the array substrate side together with the color filter, or may be separately provided, that is, the black matrix is provided on the array substrate and the color filter is provided on the other substrate. The black matrix may be provided separately from the color filters, or may be formed by overlapping the respective colors of the color filters to reduce the transmittance.
Fig. 2 is an enlarged plan view of a region surrounded by an I-line, which is a part of the pixel electrode layer 5 formed on the first substrate 2 in fig. 1. As shown in fig. 2, in the pixel electrode layer 5 including thin film transistors formed on the surface of the first substrate 2, a plurality of gate bus lines 11 for supplying scanning signals and a plurality of data bus lines 12 for supplying display signals are arranged in a matrix shape while being crossed with each other. Fig. 2 shows only a pair of gate bus lines 11 and a pair of data bus lines 12 and 12.
A unit pixel of the liquid crystal display element is formed by a region surrounded by the plurality of gate bus lines 11 and the plurality of data bus lines 12, and a pixel electrode 13 is formed in the unit pixel. The pixel electrode 13 has a so-called fishbone structure including two trunk portions that are orthogonal to each other and form a cross shape, and a plurality of branch portions extending from the trunk portions. Further, a Cs electrode 14 is provided between the pair of gate bus lines 11, 11 substantially in parallel with the gate bus line 11. In addition, a thin film transistor including a source electrode 15 and a drain electrode 16 is provided near an intersection where the gate bus line 11 and the data bus line 12 intersect with each other. The drain electrode 16 is provided with a contact hole 17.
The gate bus lines 11 and the data bus lines 12 are preferably formed of metal films, more preferably of Al, Cu, Au, Ag, Cr, Ta, Ti, Mo, W, Ni, or an alloy thereof, and still more preferably of Mo, Al, or an alloy thereof.
The pixel electrode 13 is preferably a transparent electrode in order to improve transmittance. The transparent electrode is formed by sputtering or the like of an oxide semiconductor (ZnO, InGaZnO, SiGe, GaAs, IZO (indium nitride), ito (indium tin oxide), SnO, TiO, AZTO (AlZnSnO), or the like). In this case, the thickness of the transparent electrode may be 10 to 200 nm. In addition, in order to reduce the resistance, the transparent electrode may be formed as a polycrystalline ITO film by firing an amorphous ITO film.
In the liquid crystal display device of the present embodiment, for example, a metal material such as Al or an alloy thereof is sputtered to form wirings on the first substrate 2 and the second substrate 3, and the pixel electrode layer 5 and the common electrode layer 6 are formed, respectively. The color filter 9 can be produced by, for example, a pigment dispersion method, a printing method, an electrodeposition method, a dyeing method, or the like. In the case of a method for producing a color filter by the pigment dispersion method, a curable coloring composition for a color filter is applied to the transparent substrate, subjected to patterning treatment, and then cured by heating or light irradiation. This procedure is performed for 3 colors of red, green, and blue, respectively, whereby a pixel portion for a color filter can be manufactured. In addition, the color filter 9 may be provided on the substrate side having the TFT or the like.
The first substrate 2 and the second substrate 3 are opposed to each other so that the pixel electrode layer 5 and the common electrode layer 6 are located inside, and in this case, the distance between the first substrate 2 and the second substrate 3 may be adjusted by a spacer. In this case, the thickness of the liquid crystal layer 4 is preferably adjusted to be, for example, 1 to 100 μm.
When the polarizing plates 7 and 8 are used, the product of the refractive index anisotropy Δ n of the liquid crystal layer 4 and the thickness of the liquid crystal layer 4 is preferably adjusted so that the contrast becomes maximum. In the case of two polarizing plates 7 and 8, the polarization axes of the respective polarizing plates may be adjusted so that the viewing angle and the contrast are improved. Further, a retardation film for enlarging the viewing angle may be used. Thereafter, a sealant such as an epoxy thermosetting composition is screen-printed on the substrates so as to provide a liquid crystal injection port, and the substrates are bonded to each other and heated to thermally cure the sealant.
As a method for holding the composition between the 2 substrates 2 and 3, a general vacuum injection method or a dropping injection (ODF: OneDropFill) method can be used, and although no drop mark is generated in the vacuum injection method, there is a problem that an injection mark remains. In the liquid crystal display element production step of the ODF method, an epoxy-based photo-thermal curable sealant is drawn in a closed bank shape using a dispenser on either a base plate or a front plate, a specific amount of a composition is dropped under degassing, and then the front plate and the base plate are joined to each other, whereby a liquid crystal display element can be produced. In the present embodiment, the ODF method can suppress the occurrence of dropping marks when the liquid crystal composition is dropped onto the substrate. The term "drop mark" is defined as a phenomenon in which white appears on the trace of a liquid crystal composition when black is displayed.
In addition, in the manufacturing process of the liquid crystal display element by the ODF method, it is necessary to drop the most preferable liquid crystal injection amount depending on the size of the liquid crystal display element, and the liquid crystal composition of the present embodiment has little influence on, for example, a sudden pressure change or impact in the dropping device generated at the time of dropping the liquid crystal, and can stably continue dropping the liquid crystal for a long time, and therefore, the yield of the liquid crystal display element can be kept high. In particular, since the most preferable liquid crystal injection amount is small, it is difficult to control the deviation from the most preferable value within a certain range, and a stable discharge amount of the liquid crystal material can be realized in the small liquid crystal display device by using the liquid crystal composition of the present embodiment.
When the liquid crystal composition of the present embodiment contains a polymerizable compound, a suitable polymerization rate is preferable as a method for polymerizing the polymerizable compound in order to obtain good alignment performance of the liquid crystal, and therefore, a method of polymerizing by irradiating active energy rays such as a single ultraviolet ray or an electron beam, or by irradiating them together or sequentially is preferable. In the case of using ultraviolet rays, a polarized light source may be used, and an unpolarized light source may be used. In addition, in the case of polymerizing a composition containing a polymerizable compound in a state of being held between 2 substrates, at least the substrate on the irradiation surface side must be provided with transparency suitable for an active energy ray. In addition, the following means may be used: in the case of light irradiation, only a specific portion is polymerized by using a mask, and then the orientation state of the unpolymerized portion is changed by changing the conditions such as an electric field, a magnetic field, or temperature, and further irradiated with an active energy ray to be polymerized. In particular, when ultraviolet exposure is performed, it is preferable to perform ultraviolet exposure while applying an alternating-current electric field to the composition containing the polymerizable compound. The applied alternating electric field is preferably alternating at a frequency of 10Hz to 10kHz, more preferably at a frequency of 60Hz to 10kHz, the voltage being selected depending on the desired pretilt angle of the liquid crystal display element. That is, the pretilt angle of the liquid crystal display element can be controlled by the applied voltage. In the liquid crystal display element of the transverse electric field MVA mode, it is preferable to control the pretilt angle to 80 degrees to 89.9 degrees from the viewpoint of alignment stability and contrast.
The temperature during irradiation is preferably within a temperature range in which the liquid crystal state of the composition of the present embodiment is maintained. The polymerization is preferably carried out at a temperature close to room temperature, that is, typically at a temperature of 15 to 35 ℃. As the lamp for generating ultraviolet rays, a metal halide lamp, a high-pressure mercury lamp, an ultra-high-pressure mercury lamp, or the like can be used. The wavelength of the ultraviolet light to be irradiated is preferably ultraviolet light in a wavelength region other than the absorption wavelength region of the composition, and the ultraviolet light is preferably intercepted and used as necessary. The intensity of the ultraviolet ray to be irradiated is preferably 0.1mW/cm2～100W/cm2More preferably 2mW/cm2～50W/cm2. The energy of the ultraviolet rays to be irradiated may be appropriately adjusted, and is preferably 10mJ/cm2～500J/cm2More preferably 100mJ/cm2～200J/cm2. The intensity may be changed by irradiating ultraviolet rays. The time for irradiating ultraviolet rays is appropriately selected depending on the intensity of the ultraviolet rays to be irradiated, and is preferably 10 seconds to 3600 seconds,more preferably 10 seconds to 600 seconds.
In the liquid crystal composition of the present embodiment, since the compound (i) does not inhibit the polymerization reaction of the polymerizable compound, the polymerizable compounds are polymerized appropriately, and the remaining of the unreacted polymerizable compound in the liquid crystal composition can be suppressed.
When the compound (ii) is used as the polymerizable compound, for example, the obtained liquid crystal display element 1 includes two substrates 2 and 3, and a liquid crystal layer 4 containing a liquid crystal composition and a polymer of the compound represented by the general formula (ii) and provided between the two substrates 2 and 3. In this case, it is considered that the polymer of the compound represented by the general formula (ii) is present in the liquid crystal layer 4 toward the substrates 2 and 3.
The liquid crystal display element 1 may be an active matrix driving liquid crystal display element. The liquid crystal display device 1 may be a PSA type, PSVA type, VA type, IPS type, FFS type, or ECB type liquid crystal display device, and is preferably a PSA type liquid crystal display device.
In the liquid crystal display device of the present embodiment, since the liquid crystal composition containing the compound (i) is used, it is not necessary to provide alignment films such as polyimide alignment films on the liquid crystal layer 4 sides of the first substrate 2 and the second substrate 3. That is, the liquid crystal display element of the present embodiment may be configured such that at least one of the two substrates does not have an alignment film such as a polyimide alignment film.
Examples
The present invention will be described in more detail with reference to the following examples, but the present invention is not limited to these examples. In the compositions of the following examples and comparative examples, "%" means "% by mass".
In the examples, the following symbols were used to describe the liquid crystal compounds.
(Ring structure)
(side chain structure and connecting structure)
[ Table 1]
| Description of the formula | The substituents and the linking groups |
| 1－ | CH3－ |
| 2－ | C2H5－ |
| 3－ | n－C3H7－ |
| 4－ | n－C4H9－ |
| 5－ | n－C5H11－ |
| V－ | CH2＝CH－ |
| V2－ | CH2＝CH－CH2－CH2－ |
| 1V2－ | CH3－CH＝CH－CH2－CH2－ |
| －1 | －CH3 |
| －2 | －C2H5 |
| －3 | －n－C3H7 |
| －4 | －n－C4H9 |
| －5 | －n－C5H11 |
| －O1 | －O－CH3 |
| －O2 | －O－C2H5 |
| －O3 | －O－n－C3H7 |
| －O4 | －O－n－C4H9 |
| －O5 | －O－n－C5H11 |
| －V | －CH＝CH2 |
| －V1 | －CH＝CH－CH3 |
| －2V | －CH2－CH2－CH＝CH2 |
| －F | －F |
| －OCF3 | －OCF3 |
| －CN | －CN |
| － | Single bond |
| －E－ | －COO－ |
| －1－ | －CH2CH2－ |
| －CFFO－ | －CF2O－ |
| －T－ | －C≡C－ |
| －O1－ | －OCH2－ |
| －1O－ | －CH2O－ |
In the examples, the measured characteristics are as follows. Unless otherwise specified, the measurement was carried out according to the method defined in JEITA ED-2521B.
Tni: nematic phase-isotropic liquid phase transition temperature (. degree.C.)
Δ n: refractive index anisotropy at 25 DEG C
Δ: dielectric anisotropy at 25 DEG C
K11: elastic constant K11(pN) at 25 DEG C
K33: elastic constant K33(pN) at 25 DEG C
γ 1: rotational tack (mPa. multidot.s) at 25 DEG C
Evaluation test of Low temperature storage Property: the liquid crystal composition was filtered, and the dissolved air was removed under vacuum and reduced pressure. Adding into a fully cleaned container, and standing at-20 deg.C for 240 hr. Then, the presence or absence of precipitation was visually observed, and the following 2 ranks were used for the determination.
○ No precipitation could be confirmed
× precipitation was confirmed
Evaluation test of vertical alignment property: "a first substrate (common electrode substrate) including a transparent electrode layer including a transparent common electrode and a color filter layer but not including an alignment film" and "a second substrate (pixel electrode substrate) including a pixel electrode layer including a transparent pixel electrode driven by an active device but not including an alignment film" are prepared. The liquid crystal composition was dropped onto the first substrate, and the sealant was cured by sandwiching the liquid crystal composition with the second substrate, thereby obtaining a liquid crystal cell. The vertical alignment properties at this time were observed using a polarization microscope and evaluated on the following 4 scales.
◎ uniform vertical orientation
○ very few orientation defects, but of tolerable grade
△ containing orientation defects at an unacceptable level
× poor orientation is very poor
Evaluation test of pretilt Angle stability: the liquid crystal cell used in the above (evaluation test of vertical alignment) was subjected to a rectangular alternating current of 10V and 100HzThe wave side was irradiated with a high-pressure mercury lamp at 365nm with an illuminance of 100m/cm2200 seconds of UV light. Thereafter, physical external force was applied to the cell while applying a rectangular alternating current wave of 10V and 100Hz, and the stability of white display was evaluated on the following 4 scales.
◎ uniform orientation
○ very few orientation defects, but of tolerable grade
△ containing orientation defects at an unacceptable level
× poor orientation is very poor
(examples 1 to 24, comparative example 1)
Liquid crystal compositions of L C-1 to L C-14 and L C-R1 shown in the following table were prepared, and their physical properties and physical properties are shown in tables 2 to 4.
[ Table 2]
| LC－1 | LC－2 | LC－3 | LC－4 | LC－5 | LC－6 | |
| 3－Cy－Cy－2 | 21 | 21 | 21.5 | |||
| 3－Cy－Cy－4 | 6.5 | 6.5 | 6.5 | |||
| 3－Cy－Cy－5 | ||||||
| 3－Cy－Cy－V | 32 | 31.5 | 32 | |||
| 3－Cy－Cy－V1 | ||||||
| 3－Cy－Ph－01 | ||||||
| 3－Ph－Ph－1 | 12 | 10 | 12 | 10 | 12 | 10 |
| 3－C－C－Ph－1 | 7.5 | 5 | 6 | 4 | 2 | |
| 3－C－C－Ph－3 | ||||||
| 3－C－Ph－Ph－2 | ||||||
| 3－Ph－Ph5－02 | ||||||
| 3－Cy－Ph5－02 | 10 | 10 | 10 | 10 | 10 | 10 |
| 5－Cy－Ph5－02 | 5 | 5 | 5 | 5 | 5 | 5 |
| 3－Cy－1O－Ph5－02 | ||||||
| 3－Cy－Cy－Ph5－02 | 7.5 | 7.5 | 10 | 10 | ||
| 3－Cy－Cy－Ph5－04 | 9 | 9 | ||||
| 4－Cy－Cy－Ph5－02 | ||||||
| 3－Cy－Cy－1O－Ph5－02 | 14 | 14 | 8 | 8 | ||
| 2－Cy－Ph－Ph5－02 | 7 | 7 | 7 | 7 | 7 | 7 |
| 3－Cy－Ph－Ph5－02 | 8 | 8 | 8 | 8 | 8 | 8 |
| 3－Cy－Ph－Ph5－03 | ||||||
| 3－Cy－Ph－Ph5－04 | 9 | 9 | 9 | 9 | 9 | 9 |
| TNI[℃] | 75.3 | 74.3 | 74.9 | 75.5 | 75.4 | 74.7 |
| Δn | 0.103 | 0.103 | 0.103 | 0.103 | 0.104 | 0.103 |
| γ1[mPa·s] | 88 | 77 | 90 | 79 | 91 | 80 |
| Δε | －2.8 | －2.8 | －2.8 | －2.9 | －2.8 | －2.8 |
| K11[pN] | 14.4 | 13.4 | 14.4 | 13.4 | 14.5 | 13.3 |
| K33[pN] | 13.5 | 14.0 | 13.3 | 13.8 | 13.0 | 13.6 |
| γ1/K33 | 6.5 | 5.5 | 6.8 | 5.7 | 7.0 | 5.9 |
[ Table 3]
| LC－7 | LC－8 | LC－9 | LC－10 | LC－11 | LC－12 | |
| 3－Cy－Cy－2 | 21.5 | 21 | 12 | |||
| 3－Cy－Cy－4 | 8.5 | 9.5 | 8 | |||
| 3－Cy－Cy－5 | 7 | |||||
| 3－Cy－Cy－V | 31 | 32 | 31.5 | |||
| 3－Cy－Cy－V1 | ||||||
| 3－Cy－Ph－01 | 12 | 4.5 | ||||
| 3－Ph－Ph－1 | 13 | 2.5 | 2 | |||
| 3－C－C－Ph－1 | 8 | 10 | 5 | 5 | ||
| 3－C－C－Ph－3 | ||||||
| 3－C－Ph－Ph－2 | 3 | 2.5 | 2.5 | |||
| 3－Ph－Ph5－02 | 15 | 15 | 10 | 10 | ||
| 3－Cy－Ph5－02 | 10 | 10 | 8 | 8 | ||
| 5－Cy－Ph5－02 | 5 | 5 | ||||
| 3－Cy－1O－Ph5－02 | ||||||
| 3－Cy－Cy－Ph5－02 | 10 | 10 | 7 | 7 | 12 | 12 |
| 3－Cy－Cy－Ph5－04 | 9 | 12 | 12 | 12 | ||
| 4－Cy－Cy－Ph5－02 | 10 | 10 | ||||
| 3－Cy－Cy－1O－Ph5－02 | ||||||
| 2－Cy－Ph－Ph5－02 | 7 | 7 | 7 | 7 | 5 | 5 |
| 3－Cy－Ph－Ph5－02 | 8 | 8 | 8 | 8 | 5 | 5 |
| 3－Cy－Ph－Ph5－03 | 5 | 5 | ||||
| 3－Cy－Ph－Ph5－04 | 9 | 4 | 9 | 9 | 4 | 4 |
| TNI[℃] | 76.2 | 73.8 | 75.3 | 74.2 | 110.8 | 108.8 |
| Δn | 0.103 | 0.102 | 0.103 | 0.103 | 0.098 | 0.098 |
| γ1[mPa·s] | 92 | 78 | 87 | 76 | 153 | 122 |
| Δε | －3.0 | －3.0 | －2.8 | －2.8 | －3.2 | －3.1 |
| K11[pN] | 13.7 | 13.0 | 13.8 | 13.3 | 19.5 | 17.4 |
| K33[pN] | 13.3 | 13.4 | 12.7 | 13.6 | 17.5 | 18.1 |
| γ1/K33 | 6.9 | 5.8 | 6.9 | 5.6 | 8.7 | 6.7 |
[ Table 4]
| LC－13 | LC－14 | LC－15 | LC－16 | LC－R1 | |
| 3－Cy－Cy－2 | 12 | 21.5 | |||
| 3－Cy－Cy－4 | 8 | 9.5 | |||
| 3－Cy－Cy－5 | 7 | ||||
| 3－Cy－Cy－V | 29 | 17 | 19 | ||
| 3－Cy－Cy－V1 | 10 | 10 | |||
| 3－Cy－Ph－01 | 3 | ||||
| 3－Ph－Ph－1 | 2 | 13.5 | |||
| 3－C－C－Ph－1 | 7 | 7 | 6 | ||
| 3－C－C－Ph－3 | 4 | 4 | |||
| 3－C－Ph－Ph－2 | 2 | 2 | |||
| 3－Ph－Ph5－02 | 10 | 10 | 5 | ||
| 3－Cy－Ph5－02 | 15 | 15 | |||
| 5－Cy－Ph5－02 | 10 | 6 | |||
| 3－Cy－1O－Ph5－02 | 11.5 | ||||
| 3－Cy－Cy－Ph5－02 | 15 | 15 | 15 | 15 | |
| 3－Cy－Cy－Ph5－04 | 15 | 15 | 6 | 5 | |
| 4－Cy－Cy－Ph5－02 | 10 | 13 | |||
| 3－Cy－Cy－1O－Ph5－02 | 14 | ||||
| 2－Cy－Ph－Ph5－02 | 5 | 5 | 7 | 7 | 7 |
| 3－Cy－Ph－Ph5－02 | 4 | 2 | 7 | 7 | 8 |
| 3－Cy－Ph－Ph5－03 | |||||
| 3－Cy－Ph－Ph5－04 | 9 | 9 | 9 | ||
| TNI[℃] | 111.2 | 110.2 | 85.6 | 84.5 | 74.7 |
| Δn | 0.098 | 0.098 | 0.103 | 0.105 | 0.103 |
| γ1[mPa·s] | 154 | 135 | 113 | 108 | 84 |
| Δε | －3.1 | －3.1 | －3.9 | －3.9 | －2.8 |
| K11[pN] | 20.6 | 18.3 | 15.1 | 15.0 | 14.9 |
| K33[pN] | 18.3 | 18.7 | 16.0 | 15.7 | 13.5 |
| γ1/K33 | 8.4 | 7.2 | 7.1 | 6.9 | 6.2 |
Liquid crystal compositions containing polymerizable compounds were prepared by adding the polymerizable compounds to 100 parts by mass of each of the liquid crystal compositions in the amounts shown in the tables, and low-temperature storage stability, vertical alignment property, and pretilt angle stability were confirmed. The characteristics are shown in tables 5 to 9. Confirming that: the polymerizable liquid crystal composition of the present invention has excellent characteristics.
[ Table 5]
[ Table 6]
[ Table 7]
[ Table 8]
[ Table 9]
Description of the reference numerals
1. Liquid crystal display element
2. First substrate
3. Second substrate
4. Liquid crystal layer
5. Pixel electrode layer
6. Common electrode layer
7. A first polarizing plate
8. A second polarizing plate
9. Color filter
11. Grid bus line
12. Data bus line
13. Pixel electrode
Cs electrode
15. Source electrode
16. Drain electrode
17. Contact hole
Claims (9)
1. A liquid crystal composition having a negative dielectric anisotropy Delta and containing 1 or 2 or more kinds of compounds selected from the group consisting of compounds represented by general formulae (N-1), (N-2) and (N-3) and 1 or 2 or more kinds of polymerizable compounds,
in the formula, RN11、RN12、RN21、RN22、RN31And RN32Each independently represents an alkyl group having 1 to 8 carbon atoms, 1 of the alkyl groups or 2 or more-CH groups not adjacent to each other2-may also be each independently substituted by-CH- ═ CH-, -C.ident.C-, -O-, -CO-, -COO-or-OCO-,
AN11、AN12、AN21、AN22、AN31and AN32Each independently represents a group selected from the group consisting of the following (a), (b), (c), and (d):
(a)1, 4-cyclohexylene radical, 1-CH present in this radical2Or 2 or more-CH not adjacent2-may be substituted by-O-,
(b)1, 4-phenylene, 1-CH or nonadjacent 2 or more-CH present in this radical may be substituted by-N-,
(c) naphthalene-2, 6-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or decahydronaphthalene-2, 6-diyl, 1-CH ═ or nonadjacent 2 or more-CH ═ present in naphthalene-2, 6-diyl or 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl may be substituted by — N ═ s,
(d) a 1, 4-cyclohexenylene group,
the above-mentioned group (a), group (b), group (c) and group (d) may be each independently substituted with a cyano group, a fluorine atom or a chlorine atom,
ZN11、ZN12、ZN21、ZN22、ZN31and ZN32Each independently represents a single bond, -CH2CH2－、－(CH2)4－、－OCH2－、－CH2O－、－COO－、－OCO－、－OCF2－、－CF2O－、－CH＝N－N＝CH－、-CH-, -CF-or-C ≡ C-,
XN21represents a hydrogen atom or a fluorine atom,
TN31represents-CH2-or an oxygen atom,
nN11、nN12、nN21、nN22、nN31and nN32Each independently represents an integer of 0 to 3, nN11+nN12、nN21+nN22And nN31+nN32Each independently is 1,2 or 3, when AN11～AN32、ZN11～ZN32When a plurality of them are present, they may be the same or different.
2. The liquid crystal composition according to claim 1, wherein Z in the compounds represented by the general formulae (N-1), (N-2) and (N-3) contained in the liquid crystal compositionN11、ZN12、ZN21、ZN22、ZN31And ZN32The total content of the compounds which are single bonds is 50 to 100% by mass relative to the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3).
3. The liquid crystal composition according to claim 1, wherein the total content of the following compounds contained in the liquid crystal composition is 5 to 50% by mass relative to the total content of the compounds represented by the general formulae (N-1), (N-2) and (N-3);
the compound is Z in the compounds represented by general formulas (N-1), (N-2) and (N-3)N11And ZN12At least one of which is a linking group other than a single bond, ZN21And ZN22At least one of which is a linking group other than a single bond, ZN31And ZN32At least one of the above-mentioned compounds is a linking group other than a single bond.
4. A liquid crystal composition according to any one of claims 1 to 3, which contains 1 or 2 or more compounds represented by the general formula (P) as the polymerizable compound,
in the above general formula (P), Rp1Represents a hydrogen atom, a fluorine atom, a cyano group, a hydrogen atom, an alkyl group having 1 to 15 carbon atoms wherein the hydrogen atom may be substituted with a halogen atom, an alkoxy group having 1 to 15 carbon atoms wherein the hydrogen atom may be substituted with a halogen atom, an alkenyl group having 1 to 15 carbon atoms wherein the hydrogen atom may be substituted with a halogen atom, an alkenyloxy group having 1 to 15 carbon atoms wherein the hydrogen atom may be substituted with a halogen atom, or-Spp2－Pp2，
Pp1And Pp2Each independently represents formula (P)p1-1) to formula (P)p1-any one of the above-mentioned-9),
in the formula, Rp11And Rp12Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, Wp11Represents a single bond, -O-, -COO-or methylene, tp11Represents 0, 1 or 2, and a plurality of R exist in the moleculep11、Rp12、Wp11And/or tp11Which may be the same or different,
Spp1and Spp2Each independently represents a single bond or a spacer,
Zp1and Zp2Each independently represents a single bond, -O-, -S-, -CH2－、－OCH2－、－CH2O－、－CO－、－C2H4－、－COO－、－OCO－、－OCOOCH2－、－CH2OCOO－、－OCH2CH2O－、－CO－NRZP1－、－NRZP1－CO－、－SCH2－、－CH2S－、－CH＝CRZP1－COO－、－CH＝CRZP1－OCO－、－COO－CRZP1＝CH－、－OCO－CRZP1＝CH－、－COO－CRZP1＝CH－COO－、－COO－CRZP1＝CH－OCO－、－OCO－CRZP1＝CH－COO－、－OCO－CRZP1＝CH－OCO－、－(CH2)z－COO－、－(CH2)2－OCO－、－OCO－(CH2)2－、－(C＝O)－O－(CH2)2－、－CH＝CH－、－CF＝CF－、－CF＝CH－、－CH＝CF－、－CF2－、－CF2O－、－OCF2－、－CF2CH2－、－CH2CF2－、－CF2CF2-or-C ≡ C-in which R isZP1Each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and a plurality of R's are present in the moleculeZP1Which may be the same or different,
Ap2represents 1, 4-phenylene, 1, 4-cyclohexylene, anthracene-2, 6-diyl, phenanthrene-2, 7-diyl, pyridine-2, 5-diyl, pyrimidine-2, 5-diyl, naphthalene-2, 6-diyl, indan-2, 5-diyl, 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl or 1, 3-dioxane-2, 5-diyl, Ap2Is unsubstituted or substituted by alkyl having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, haloalkoxy having 1 to 12 carbon atoms, halogen atom, cyano, nitro or-Spp2－Pp2The substitution is carried out by the following steps,
Ap1is represented by (A)p1－11)～(Ap1-19) a group represented by (a),
wherein at ★ is reacted with Spp1Or Zp1Bonded to Z at ★★p1Bonded, wherein 1 or more than 2 hydrogen atoms in the structure can be replaced by alkyl with 1-12 carbon atoms, halogenated alkyl with 1-12 carbon atoms, alkoxy with 1-12 carbon atoms, halogenated alkoxy with 1-12 carbon atoms, halogen atom, cyano, nitro or-Spp2－Pp2The substitution is carried out by the following steps,
Ap3is represented by (A)p3－11)～(Ap3-19) a group represented by (a),
wherein, at ★, is reacted with Zp2Bonded at ★★ with Rp1Or Zp2Bonding, wherein 1 or more than 2 hydrogen atoms in the structure can also be replaced by alkyl with 1-12 carbon atoms, halogenated alkyl with 1-12 carbon atoms, alkoxy with 1-12 carbon atoms, halogenated alkoxy with 1-12 carbon atoms, halogen atom, cyano, nitro or-Spp2－Pp2The substitution is carried out by the following steps,
mp2and mp3Each independently represents 0, 1,2 or 3, mp1And mp4Each independently represents 1,2 or 3, and a plurality of P's are present in the moleculep1、Spp1、Ap1、Zp1、Zp2、Ap3And/or Rp1In this case, they may be the same or may be different.
5. The liquid crystal composition according to any one of claims 1 to 4, which comprises 1 or 2 or more compounds represented by the general formula (SA L) as the polymerizable compound,
in the above formula, PalRepresents a group represented by the general formula (P-I) to the general formula (P-IX),
in the formula, Rp11And Rp12Each independently represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms or a haloalkyl group having 1 to 5 carbon atoms, Wp11Represents a single bond, -O-, -COO-or methylene, tp11Represents 0, 1 or2，
SpalRepresents a single bond or a linear or branched alkylene group having 1 to 20 carbon atoms, 1 or not adjacent 2 or more-CH in the alkylene group2-may each be independently substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-,
t represents an adsorption group, and T represents an adsorption group,
MG represents a mesogenic group,
cg represents a hydrogen atom, the adsorption group, or the-Sp groupal－PalOr a linear or branched alkylene group having 1 to 20 carbon atoms, 1 or 2 or more-CH groups not adjacent to each other in the alkylene group2Each independently of the others, -CH ═ CH-, -C ≡ C-, -O-, -CO-, -COO-or-OCO-, and all of Cg, MG and T may be substituted with the polymerizable group-Spal－Pal－，
nsal1、nsal2And nsal3Each independently represents a natural number of 1 to 5.
6. The liquid crystal composition according to claim 1, wherein the total content of the following compounds contained in the liquid crystal composition is 50 to 95% by mass relative to the total content of the compounds of the general formulae (N-1), (N-2) and (N-3);
the compound is Z in the compound represented by the general formula (N-1)N11And ZN12At least one of which is a linking group other than a single bond, ZN21And ZN22At least one of which is a linking group other than a single bond, ZN31And ZN32At least one of the above-mentioned compounds is a linking group other than a single bond.
7. A liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 6.
8. A liquid crystal display device for driving an active matrix, which comprises the liquid crystal composition according to any one of claims 1 to 6.
9. A VA-type, IPS-type, FFS-type, PSA-type or PSVA-type liquid crystal display element using the liquid crystal composition according to any one of claims 1 to 6.
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| PCT/JP2018/044885 WO2019124094A1 (en) | 2017-12-21 | 2018-12-06 | Liquid crystal composition |
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| WO2019124094A1 (en) | 2019-06-27 |
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