CN113620805A - Polymerizable compound, composition, and optically anisotropic body - Google Patents
Polymerizable compound, composition, and optically anisotropic body Download PDFInfo
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- CN113620805A CN113620805A CN202110836384.0A CN202110836384A CN113620805A CN 113620805 A CN113620805 A CN 113620805A CN 202110836384 A CN202110836384 A CN 202110836384A CN 113620805 A CN113620805 A CN 113620805A
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- 239000000203 mixture Substances 0.000 title claims abstract description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 203
- -1 2, 4-cyclopentadien-2, 5-diyl Chemical group 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 22
- 125000004423 acyloxy group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 125000001188 haloalkyl group Chemical group 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 11
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 11
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229920006254 polymer film Polymers 0.000 claims description 10
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
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- 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 4
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 101000986989 Naja kaouthia Acidic phospholipase A2 CM-II Proteins 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
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- 230000000996 additive effect Effects 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
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- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- HSFWJUIIFWCPBM-UHFFFAOYSA-N 4-carbonochloridoyloxybutyl prop-2-enoate Chemical compound ClC(=O)OCCCCOC(=O)C=C HSFWJUIIFWCPBM-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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- RNPZEWACDMXHOX-UHFFFAOYSA-N ClCCCCCCC(C(=C)C)=O Chemical compound ClCCCCCCC(C(=C)C)=O RNPZEWACDMXHOX-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
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- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 229940090181 propyl acetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
-
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
-
- 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/30—Polarising elements
- G02B5/3083—Birefringent or phase retarding elements
Abstract
Disclosed is a polymerizable compound selected from compounds of the general formula (1). Further, a polymerizable composition and an optically anisotropic body formed from the polymerizable compound are disclosed. The polymerizable compound can exhibit one or more of favorable substrate high adhesion in RM optical retardation films, is highly transparent to Vis-light, exhibits reduced random yellowing, and exhibits good high temperature stability.
Description
Technical Field
The present invention relates to a polymerizable compound and a method for producing the same, a polymerizable composition and a method for producing the same, and applications of the polymerizable compound and the polymerizable composition in various optically anisotropic bodies.
Background
Polymerizable (mesogenic) compounds (RM) are gaining increasing attention as starting materials for the preparation of various optically anisotropic bodies. The prior art generally applies a solution of a polymerizable compound onto a substrate, aligns it, and cures it by heating or irradiating an active energy ray, thereby forming an optically anisotropic polymer film, also called an optically anisotropic body, having uniform orientation. The film orientation may be planar (liquid crystal molecules oriented substantially parallel to the layer), homeotropic (rectangular or perpendicular to the layer) or tilted, as well as cholesteric.
The optically anisotropic body includes, but is not limited to, an optical retardation film (retardation film), an optical compensation film, a vision expanding film, a reflective film, a selective reflective film, an antireflection film, a brightness enhancement film, a liquid crystal alignment film, a polarizing element, a circular polarizing element, an elliptical polarizing element, and other various optical elements according to the application field.
Polymerizable compounds, while stable at room temperature, degrade at elevated temperatures. For example, when heated for a period of time, the optical properties of the dispersion or retardation degrade, resulting in a degradation of the properties of the optically anisotropic body over time. According to different studies, this can be attributed to a low degree of polymerization, a correspondingly high residual radical content of the polymer, shrinkage or thermo-oxidative degradation of the polymer, etc.
The optically anisotropic body is required to have various properties such as optical properties, polymerization rate, solubility, melting point or glass transition temperature, transparency, mechanical strength, surface hardness, heat resistance and light resistance, which are required. In most cases, it is desirable to use a polymerizable composition containing two or more polymerizable compounds. Thus, the characteristics of the optically anisotropic body depend not only on the kind of the polymerizable compound used but also on the ratio of the polymerizable compounds.
In one example, the desired characteristics of the optical retardation film (e.g., homogeneous alignment, film structure, film adhesion, temperature stability, and optical properties) are all dependent on the particular composition of the polymerizable composition. For this purpose, one possible way of adjusting the alignment distribution in the direction perpendicular to the film plane is to rationally select the ratio of mono-reactive mesogenic compound and di-reactive mesogenic compound. Furthermore, RM optical retardation films with low diacrylate content are well suited for applications where good adhesion of the RM optical retardation film to the substrate is important. However, in RM optical retardation films with low diacrylate content, the optical retardation usually drops significantly, especially due to polymer shrinkage.
Therefore, it is required to develop a polymerizable compound or a polymerizable composition, the use of which can solve the above-mentioned technical problems.
Disclosure of Invention
It is an object of the present invention to provide a polymerizable compound capable of exhibiting one or more of favorable high substrate adhesion in an RM optical retardation film, high transparency to Vis-light, exhibiting reduced random yellowing, and exhibiting good high temperature stability and the like. Further, the compound can exhibit not only favorable substrate high adhesion in RM optical retardation films, but also good high temperature stability.
It is a second object of the present invention to further provide a polymerizable composition and a polymerizable composition solution comprising the polymerizable compound described above and below.
It is a further object of the present invention to provide the use of the polymerizable compounds and polymerizable compositions described above and below.
To achieve the above object, in one aspect, the present invention provides a polymerizable compound selected from compounds of the general formula (1),
in the formula (I), the compound is shown in the specification,
P1and P2Each independently represents a polymerizable group;
L1-L4each independently represents a single bond, -O-, -S-, -NH-, -CO-, -OCO-, -COO-、-SCO-、 -COS-、-OCOO-、-NHCO-、-CONH-、-OCH2-、-CH2O-、-SCH2-、-CH2S-、 -OCF2-、-CF2O-、-SCF2-、-CF2S-、-CH＝CHOCO-、-CH＝CHCOO-、- OCOCH＝CH-、-COOCH＝CH-、-CH2CH2OCO-、-CH2CH2COO-、- OCOCH2CH2-、-COOCH2CH2-、-CH2OCO-、-CH2COO-、-OCOCH2-、 -COOCH2-, -CH ═ CH-, -N ═ CH-, -CH ═ N-, -N ═ N-, -CH ═ CF-, -CF ═ CH-, -N ═ CF-, -CF ═ N-, -C ≡ C-, or alkylene having a carbon number of 1 to 30; one or more-CH's in said alkylene group2-may be substituted by-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; l is1-L4When plural, they may be the same or different;
C1and C2Each independently represents-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、 -OCF2-、-CF2O-、-SCF2-、-CF2S-、-CH＝CHOCO-、-CH＝CHCOO-、- OCOCH＝CH-、-COOCH＝CH-、-CH2CH2OCO-、-CH2CH2COO-、- OCOCH2CH2-、-COOCH2CH2-、-CH2OCO-、-CH2COO-、-OCOCH2-、 -COOCH2-, -CH ═ CH-, -N ═ CH-, -CH ═ N-, -N ═ N-, -CH ═ CF-, -CF ═ CH-, -N ═ CF-, -CF ═ N-, -C ≡ C-, or a single bond;
ring a represents a group selected from:
(a)1, 4-cyclohexylene; in which 1-CH is present2-or non-adjacent more than 2-CH2-may be substituted by-O-, -S-, -NH-;
(b)1, 4-phenylene; wherein 1-CH-present or non-adjacent 2 or more-CH-may be substituted by-N ═ g;
(c)1, 4-cyclohexenylene, 2, 4-cyclopentadien-2, 5-diyl, thiophen-2, 5-diyl, furan-2, 5-diyl, piperidin-2, 5-diyl, naphthalen-2, 6-diyl, naphthalen-1, 4-diyl, naphthalen-1, 5-diyl, 1,2,3, 4-tetrahydronaphthalen-2, 6-diyl and decahydronaphthalen-2, 6-diyl;
the above groups (a), (b) or (c) may be each independently substituted with halogen, cyano, alkyl group having 1 to 30 carbon atoms, haloalkyl group having 1 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, haloalkoxy group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, haloalkenyl group having 2 to 30 carbon atoms, alkenyloxy group having 2 to 30 carbon atoms, haloalkenyloxy group having 2 to 30 carbon atoms, alkoxycarbonyl group having 1 to 30 carbon atoms, haloalkoxycarbonyl group having 1 to 30 carbon atoms, alkylcarbonyl group having 1 to 30 carbon atoms, haloalkylcarbonyl group having 1 to 30 carbon atoms, alkanoyloxy group having 1 to 30 carbon atoms or haloalkoyloxy group having 1 to 30 carbon atoms;
R1and R2Each independently represents an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, a haloalkylcarbonyl group having 1 to 30 carbon atoms, an alkanoyloxy group having 1 to 30 carbon atoms or a haloalkoyloxy group having 1 to 30 carbon atoms; m and n each independently represent an integer of 0 to 8.
As the compound of the general formula (1), wherein the polymerizable group is selected from the following groups:
in the formula, R3Each independently represents a hydrogen atom, a halogen, a cyano group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, a haloalkylcarbonyl group having 1 to 30 carbon atoms, an alkanoyloxy group having 1 to 30 carbon atoms or a haloalkoyloxy group having 1 to 30 carbon atoms.
As the compound of the general formula (1), wherein, P1And P2Each independently represents a group of (P-1) and (P-2).
A compound represented by the general formula (1), wherein ring a represents a 1, 4-phenylene group; wherein 1-CH-present or non-adjacent 2 or more-CH-may be substituted by-N ═ group; and/or ring A may be substituted with halogen, cyano, alkyl group having 1 to 30 carbon atoms, haloalkyl group having 1 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, haloalkoxy group having 1 to 30 carbon atoms, alkanoyloxy group having 1 to 30 carbon atoms and haloalkoyloxy group having 1 to 30 carbon atoms.
Preferably, ring A may be substituted with halogen, cyano, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkoxy group having 1 to 20 carbon atoms, alkyl acyloxy group having 1 to 20 carbon atoms and haloalkyloxy group having 1 to 20 carbon atoms.
Further preferably, ring A may be substituted with halogen, cyano, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkoxy group having 1 to 10 carbon atoms, alkanoyloxy group having 1 to 10 carbon atoms and haloalkoyloxy group having 1 to 10 carbon atoms.
More preferably, ring A may be substituted with halogen, cyano, alkyl group having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, haloalkoxy group having 1 to 6 carbon atoms, alkanoyloxy group having 1 to 6 carbon atoms and haloalkoyloxy group having 1 to 6 carbon atoms.
As the compound of the general formula (1), wherein L1-L2Each independently represents an alkylene group having 1 to 30 carbon atoms; one or more-CH's in said alkylene group2-may be substituted by-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; and/or, L3-L4Each independently represents a single bond, -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、 -CH2O-、-SCH2-、-CH2S-、-OCF2-、-CF2O-、-SCF2-、-CF2S-。
Preferably, L1-L2Each independently represents an alkylene group having 1 to 30 carbon atoms; and/or, L3-L4Each independently represents-OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-.
Further preferably, L1-L2Each independently represents an alkylene group having 2 to 20 carbon atoms; and/or, L3-L4Each independently represents-OCO-, -COO-, -SCO-, -COS-, -OCOO-.
More preferably, L1-L2Each independently represents an alkylene group having 2 to 15 carbon atoms; and/or, L3-L4Each independently represents-OCO-, -COO-.
As the compound of the general formula (1), wherein C1And C2Each independently represents-OCO-, -COO-, -SCO-, -COS-, -OCOO-.
Preferably, C1And C2Each independently represents-OCO-, -COO-, -OCOO-.
In another aspect, the present invention also provides a polymerizable composition comprising a mono-reactive mesogenic compound and a di-reactive mesogenic compound, characterized in that said di-reactive mesogenic compound comprises a compound of general formula (1) as described above and below.
The polymerizable composition as described above and below, wherein the bireactive mesogenic compound further comprises a compound of general formula (2),
in the formula (I), the compound is shown in the specification,
P1' and P2' each independently represents a polymerizable group;
L1’-L4' each independently represents a single bond, -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、 -OCF2-、-CF2O-、-SCF2-、-CF2S-、-CH＝CHOCO-、-CH＝CHCOO-、- OCOCH＝CH-、-COOCH＝CH-、-CH2CH2OCO-、-CH2CH2COO-、- OCOCH2CH2-、-COOCH2CH2-、-CH2OCO-、-CH2COO-、-OCOCH2-、 -COOCH2-, -CH ═ CH-, -N ═ CH-, -CH ═ N-, -N ═ N-, -CH ═ CF-, -CF ═ CH-, -N ═ CF-, -CF ═ N-, -C ≡ C-, or alkylene having a carbon number of 1 to 30; one or more-CH's in said alkylene group2-may be substituted by-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; l is1’-L4' when plural, they may be the same or different;
C1' and C2' each independently represents-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、 -OCF2-、-CF2O-、-SCF2-、-CF2S-、-CH＝CHOCO-、-CH＝CHCOO-、- OCOCH＝CH-、-COOCH＝CH-、-CH2CH2OCO-、-CH2CH2COO-、- OCOCH2CH2-、-COOCH2CH2-、-CH2OCO-、-CH2COO-、-OCOCH2-、 -COOCH2-, -CH ═ CH-, -N ═ CH-, -CH ═ N-, -N ═ N-, -CH ═ CF-, -CF ═ CH-, -N ═ CF-, -CF ═ N-, -C ≡ C-, or a single bond;
ring a' represents a group selected from:
(a)1, 4-cyclohexylene; in which 1-CH is present2-or non-adjacent more than 2-CH2-may be substituted by-O-, -S-, -NH-;
(b)1, 4-phenylene; wherein 1-CH-present or non-adjacent 2 or more-CH-may be substituted by-N ═ g;
(c)1, 4-cyclohexenylene, 2, 4-cyclopentadien-2, 5-diyl, thiophen-2, 5-diyl, furan-2, 5-diyl, piperidin-2, 5-diyl, naphthalen-2, 6-diyl, naphthalen-1, 4-diyl, naphthalen-1, 5-diyl, 1,2,3, 4-tetrahydronaphthalen-2, 6-diyl and decahydronaphthalen-2, 6-diyl;
the above groups (a), (b) or (c) may be each independently substituted with halogen, cyano, alkyl group having 1 to 30 carbon atoms, haloalkyl group having 1 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, haloalkoxy group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, haloalkenyl group having 2 to 30 carbon atoms, alkenyloxy group having 2 to 30 carbon atoms, haloalkenyloxy group having 2 to 30 carbon atoms, alkoxycarbonyl group having 1 to 30 carbon atoms, haloalkoxycarbonyl group having 1 to 30 carbon atoms, alkylcarbonyl group having 1 to 30 carbon atoms, haloalkylcarbonyl group having 1 to 30 carbon atoms, alkanoyloxy group having 1 to 30 carbon atoms or haloalkoyloxy group having 1 to 30 carbon atoms;
R1' and R2' each independently represents an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, a haloalkylcarbonyl group having 1 to 30 carbon atoms, an alkanoyloxy group having 1 to 30 carbon atoms or a haloalkoyloxy group having 1 to 30 carbon atoms; m and n each independently represent an integer of 0 to 4.
As the compound of the general formula (2), wherein the polymerizable group is selected from the following groups:
in the formula, R3Each independently represents a hydrogen atom, a halogen, a cyano group, an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, a haloalkylcarbonyl group having 1 to 30 carbon atoms, an alkanoyloxy group having 1 to 30 carbon atoms or a haloalkoyloxy group having 1 to 30 carbon atoms.
As a compound of the general formula (2), wherein P1' and P2' independently represent a group of (P-1) and (P-2).
As the compound of the general formula (2), wherein ring a' represents a 1, 4-phenylene group; wherein 1-CH-present or non-adjacent 2 or more-CH-may be substituted by-N ═ group; and/or ring A' may be substituted with halogen, cyano, alkyl group having 1 to 30 carbon atoms, haloalkyl group having 1 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, haloalkoxy group having 1 to 30 carbon atoms, alkanoyloxy group having 1 to 30 carbon atoms and haloalkoyloxy group having 1 to 30 carbon atoms.
Preferably, ring A' may be substituted with halogen, cyano, alkyl group having 1 to 20 carbon atoms, haloalkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, haloalkoxy group having 1 to 20 carbon atoms, alkyl acyloxy group having 1 to 20 carbon atoms and haloalkyloxy group having 1 to 20 carbon atoms.
Further preferably, the ring A' may be substituted with halogen, cyano, alkyl group having 1 to 10 carbon atoms, haloalkyl group having 1 to 10 carbon atoms, alkoxy group having 1 to 10 carbon atoms, haloalkoxy group having 1 to 10 carbon atoms, alkanoyloxy group having 1 to 10 carbon atoms and haloalkoyloxy group having 1 to 10 carbon atoms.
More preferably, ring A' may be substituted with halogen, cyano, alkyl group having 1 to 6 carbon atoms, haloalkyl group having 1 to 6 carbon atoms, alkoxy group having 1 to 6 carbon atoms, haloalkoxy group having 1 to 6 carbon atoms, alkanoyloxy group having 1 to 6 carbon atoms and haloalkoyloxy group having 1 to 6 carbon atoms.
As a compound of the general formula (2), wherein L1’-L2' each independently represents an alkylene group having 1 to 30 carbon atoms; one or more-CH's in said alkylene group2-may be substituted by-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; and/or, L3’-L4' each independently represents a single bond, -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、-OCF2-、-CF2O-、-SCF2-、-CF2S-。
Preferably, L1’-L2' each independently represents an alkylene group having 1 to 30 carbon atoms; and/or, L3-L4Each independently represents-OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-.
Further preferably, L1’-L2' each independently represents an alkylene group having 2 to 20 carbon atoms; and/or, L3’-L4' each independently represents-OCO-, -COO-, -SCO-, -COS-, -OCOO-.
More preferably, L1’-L2' each independently represents an alkylene group having 2 to 15 carbon atoms; and/or, L3’-L4' each independently represents-OCO-, -COO-.
As a compound of the general formula (2), wherein C1' and C2' each independently represents-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-.
Preferably, C1' and C2' each independently represents-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -OCOO-.
Polymerizable composition as described above and below wherein the bireactive mesogenic compound is present in an amount of 80 to 99 wt. -%, based on the total weight of the polymerizable composition.
Preferably, the content of the bireactive mesogenic compound is from 85 to 98 wt%, based on the total weight of the polymerizable composition; more preferably, the content of the bireactive mesogenic compound is 90 to 97 wt. -%, based on the total weight of the polymerizable composition; and, most preferably, the content of the bireactive mesogenic compound is 92 to 96.5 wt%, based on the total weight of the polymerizable composition.
The polymerizable composition as described above and below, wherein the compound of the general formula (1) as described above and below is contained in an amount of 6 to 18% by weight based on the total weight of the polymerizable composition.
Preferably, the compound of formula (1) is present in an amount of 8 to 15 wt%, based on the total weight of the polymerizable composition; more preferably, the compound of formula (1) is present in an amount of 9 to 14 weight percent based on the total weight of the polymerizable composition; and, most preferably, the compound of formula (1) is present in an amount of 10 to 12 wt%, based on the total weight of the polymerizable composition.
In one embodiment, the bireactive mesogenic compound consists of a compound of formula (1) and a compound of formula (2).
The polymerizable composition as described above and below wherein the content of the mono-reactive mesogenic compound is from 0.5 to 10 wt. -%, based on the total weight of the polymerizable composition.
Preferably, the content of the mono-reactive mesogenic compound is 1 to 8 wt. -%, based on the total weight of the polymerizable composition; more preferably, the content of the mono-reactive mesogenic compound is 1.5 to 6 wt. -%, based on the total weight of the polymerizable composition; and, most preferably, the content of the mono-reactive mesogenic compound is 2 to 5 wt%, based on the total weight of the polymerizable composition.
The polymerizable composition as described above and below further comprising an additive.
As the additives, there are included, but not limited to, polymerization initiators, sensitizers, stabilizers, leveling agents, surfactants, polymerization inhibitors, antioxidants, colorants, dispersants, lubricants, hydrophobizing agents, adhesives, flow improvers, antifoaming agents, deaerators, diluents, thixotropic agents, gelling agents, catalysts, metals, metal complexes, luminescent materials, and the like.
Advantageously, the additive is present in an amount of from 0.01 to 10 weight percent, preferably from 0.02 to 8 weight percent, more preferably from 0.05 to 5 weight percent, and most preferably from 0.1 to 2 weight percent, based on the total weight of the polymerizable composition.
In yet another aspect, the present invention also provides a polymerizable composition solution comprising the polymerizable composition described above and below and an organic solvent.
As the organic solvent, it is preferable that the polymerizable composition has good solubility and can be removed by drying at 100 ℃. Organic solvents, including, but not limited to,
although not particularly limited, the polymerizable liquid crystal compound is preferably an organic solvent exhibiting good solubility, and is preferably an aromatic solvent such as toluene, xylene, cumene, mesitylene, or the like; ester solvents such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, and the like; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and cyclopentanone; ether solvents such as tetrahydrofuran, 1, 2-dimethoxyethane and anisole, and amide solvents such as N, N-dimethylformamide and N-methyl-2-pyrrolidone; propylene glycol monomethyl ether acetate, diethylene glycol monomethyl ether acetate, gamma-butyrolactone, chlorobenzene, and the like.
The organic solvents mentioned above and below may be used alone or in combination of two or more.
From the viewpoint of solution stability, it is preferable to use one or more of a ketone-based solvent, an ether-based solvent, an ester-based solvent and an aromatic solvent.
As the polymerizable composition solution, the organic solvent is contained in an amount of 30 to 95% by weight, preferably 40 to 90% by weight, more preferably 50 to 85% by weight, and, most preferably, 60 to 80% by weight, based on the total weight of the polymerizable composition solution.
In preparing the polymerizable composition solution, heating and/or stirring is advantageously performed in order to promote dissolution of the polymerizable composition.
In a further aspect, the present invention also provides an optically anisotropic body comprising a substrate and a polymer film formed by solution curing the above and below polymerizable composition, and, if necessary, an orientation film.
In one embodiment, a substrate, an orientation film, if necessary, and a polymer film formed by curing a polymerizable composition solution are sequentially laminated to form an optically anisotropic body.
In another embodiment, a substrate, an orientation film if necessary, and a polymer film formed by curing a polymerizable composition solution are sequentially laminated, and then a second orientation film if necessary, and a second polymer film formed by curing a polymerizable composition solution described above and below or a polymerizable composition solution different therefrom are sequentially laminated thereon.
The substrate of the optically anisotropic body includes, but is not limited to, a glass substrate, a metal substrate, a ceramic substrate, and a polymer substrate. Further, as the polymer base material, for example, there may be: cellulose derivatives, polyolefins, polyesters, polyolefins, polycarbonates, polyacrylates, polyarylates, polyether sulfones, polyamides, polyimides, polyphenylene sulfides, polyphenylene oxides or polystyrenes, and the like.
The process suitability for optical anisotropy-based processes, particularly from the viewpoint of heat resistance and chemical stability, is preferably polyester, polystyrene, polyolefin, cellulose derivative, polyarylate, polycarbonate.
The alignment film material as the optically anisotropic body includes, but is not limited to, polyimide, polysiloxane, polyamide, polyvinyl alcohol, polycarbonate, polystyrene, polyphenylene ether, polyarylate, polyethylene terephthalate, polyethersulfone, epoxy resin, acrylic resin, epoxy acrylic resin, coumarin, chalcone, cinnamate, anthraquinone, azo compound, arylvinyl compound, and the like.
As the orientation treatment, stretching treatment, rubbing treatment, polarized ultraviolet and visible light irradiation, ion beam treatment, or the like may be mentioned. Preferably, the orientation treatment is rubbing treatment or polarized uv-vis irradiation.
As a coating method for obtaining the optically anisotropic body of the present invention, a method known in the art, such as a coater method, a bar coating method, a spin coating method, a gravure printing method, a flexographic printing method, an ink jet method, a die coating method, a CAP coating method, and dipping, can be used. After the polymerizable composition solution is applied, it is dried.
In the solution polymerization of the polymerizable composition of the present invention, it is desirable to carry out the polymerization rapidly, and therefore it is preferable to carry out the polymerization by irradiating an active energy ray such as ultraviolet visible light or an electron ray. In the case of using ultraviolet visible light, a polarized light source may be used, or an unpolarized light source may be used.
The optically anisotropic body of the present invention is advantageously a retardation film. The retardation film of the present invention is produced in the same manner as the optically anisotropic body of the present invention.
When the polymerizable compound in the polymerizable composition solution is polymerized in a planar alignment state, a retardation film having birefringence in the plane with respect to the substrate can be obtained.
When the polymerizable compound and the polymerizable chiral compound in the polymerizable composition solution are polymerized in a planar orientation state, a retardation film having birefringence out of plane with respect to the substrate can be obtained.
When the polymerizable compound and the polymerizable discotic compound in the polymerizable composition solution are polymerized in a planar orientation, a retardation film having birefringence in both in-plane and out-of-plane with respect to the base material can be obtained.
When the substrate has the same retardation, the retardation film of the present invention can be obtained as a birefringent retardation film by adding the birefringence of the retardation film to the birefringence of the substrate. The birefringence of both may be in the same direction or in different directions within the plane of the substrate.
Detailed Description
In the present invention, technical terms are further explained and defined in detail.
The term "liquid crystal" or "mesogenic compound" denotes a compound which forms a mesogenic or liquid crystalline phase under certain conditions.
The term "polymerizable mesogen" or "polymerizable compound" is abbreviated RM and denotes polymerizable liquid crystalline or mesogenic compounds, especially monomeric compounds.
The term "mono-reactive" or "di-reactive" means that the polymerizable mesogen or polymerizable compound has one or two polymerizable groups.
The term "polymerizable group" means a group which is polymerized by means of light, heat or a catalyst to form a polymer of higher molecular weight.
The term "film" denotes a rigid or flexible coating or layer having mechanical stability; optionally, the membrane may be present alone; located over the support substrate; or sandwiched between two substrates.
The term "R" or "Re" denotes an optical retardation amount, particularly a phase retardation amount between ordinary light and extraordinary light.
The term "Rλ"or" Reλ"represents the amount of phase retardation when light is incident perpendicularly to the film surface at a wavelength of λ nm.
The term "Rin"or" Rein"indicates the phase delay amount at the initial time.
The present invention will be further described with reference to the following synthetic examples and examples, but the present invention is not limited to the application thereof. Unless otherwise indicated, percentages in the examples are uniformly percentages by mass.
Synthesis example 1: synthesis of Compound A
Synthesis of intermediate A-1:
adding 10g of 6-hydroxy-2-anthracenecarboxylic acid into a 500ml reaction bottle, then adding 8.4g of diisopropylethylamine and 200ml of dichloromethane, then dropwise adding 4-acryloyloxybutyl chloroformate at the temperature of 0-5 ℃, preserving heat for 2 hours after dropwise adding, performing aftertreatment, washing an organic layer by using 6N hydrochloric acid, drying and concentrating to obtain a viscous solid, adding ethanol, pulping, performing suction filtration, and crystallizing the solid again by using a mixed solvent of dichloromethane and petroleum ether to obtain the solid, wherein the content of a liquid phase is 96.7%, and the yield is 74%.
Synthesis of Compound A:
putting 10g of the compound A-1 into a reaction bottle, adding 200ml of dichloromethane and 2 drops of DMF, then dropwise adding oxalyl chloride at the temperature of 20-25 ℃, preserving heat at the temperature of 25 ℃ for 4 hours after dropwise adding, removing the solvent and the redundant oxalyl chloride by rotary evaporation, adding 200ml of new dichloromethane and 2g of 1, 4-dihydroxy-2-methyl benzoate again, dropwise adding 4.8g of diisopropylethylamine at the temperature of 0-5 ℃, preserving heat for 2 hours after dropwise adding, washing by adding 6N hydrochloric acid for post-treatment, drying, concentrating, pulping with ethanol to obtain a solid, and crystallizing the solid with a mixture solvent of acetone/toluene/ethanol to obtain the compound A8.1 g with the yield of 69% and the liquid phase content of 94.2%.
The structure of compound a is characterized as:1H NMR(400MHz,DMSO-d6)：δ 8.79(s,2H), 8.72(s,2H),8.44(s,2H),8.05(d,J＝8Hz,2H),8.02(d,J＝9Hz,2H),7.88(dd,J＝8 Hz,2Hz,2H),7.41(d,J＝2Hz,2H),7.22(dd,J＝9Hz,2Hz,2H),7.10(m,1H), 6.95(d,J＝8.8Hz,2H),6.32(dd,J＝17.4,1.4Hz,2H),6.17(dd,J＝17.4,10.5Hz, 2H),5.84(dd,J＝10.3Hz,1.6Hz,2H),4.20(t,J＝5.9Hz,4H),4.10(t,J＝5.9Hz, 4H),3.94(s,3H),1.63-1.79(m,8H)。
synthesis example 2: synthesis of Compound B
Synthesis of intermediate B-1:
10g of 6-hydroxy-2-anthracenecarboxylic acid, 2.6g of o-methyl hydroquinone, 0.5g of potassium hydrogen sulfate and 100ml of trimethylbenzene, heating, refluxing and water dividing for 30h, cooling to room temperature, filtering, washing a filter cake twice by using methanol slurry, drying to obtain 19.7g of filter cake, and directly using the filter cake in the next reaction without purification.
Synthesis of Compound B:
adding 10g of intermediate B-1, 4.5g of triethylamine and 100ml of dichloromethane into a 250ml three-neck flask, dropwise adding 8.1g of chloroformic acid 4-acryloyloxy butyl ester at the controlled temperature of 0-5 ℃ under stirring, reacting for 1 hour after dropwise adding, then heating to 30 ℃ to react for 4 hours, adding 50ml of 10% hydrochloric acid for washing, washing with 2% sodium bicarbonate water solution to be neutral, concentrating to obtain 50ml of dichloromethane, adding 200ml of ethanol, separating out solids, performing suction filtration to obtain a crude product, drying, performing toluene column chromatography, washing with ethanol slurry, and drying to obtain 10.35g of a white product, wherein the content is 95.4%, and the yield is 64.5%.
The structure of compound B is characterized as:1H NMR(400MHz,DMSO-d6)：δ 8.72(s,2H), 8.70(s,2H),8.44(s,2H),8.05(d,J＝8Hz,2H),8.02(d,J＝9Hz,2H),7.88(dd,J＝8 Hz,2Hz,2H),7.41(d,J＝2Hz,2H),7.22(dd,J＝9Hz,2Hz,2H),7.13(m,1H), 6.95(d,J＝8.8Hz,2H),6.32(dd,J＝17.4,1.4Hz,2H),6.17(dd,J＝17.4,10.5Hz, 2H),5.94(dd,J＝10.3,1.6Hz,2H),4.25(t,J＝5.9Hz,4H),4.15(t,J＝5.9Hz, 4H),2.16(s,3H),1.68-1.79(m,8H)。
synthesis example 3: synthesis of Compound C
10g of intermediate B-1, 100g of DMF and 5.4g of potassium carbonate, heating to 80 ℃, adding 5.6g of 6-chloro-1-methacryloyl hexane, preserving the temperature for 12h after finishing the dropwise addition till the reaction end point, then cooling, adding water into the system, separating out a product, filtering, collecting a filter cake, and crystallizing the filter cake by using a dichloromethane/acetone/ethanol mixed solvent to obtain 9.4g of the product with the content of 92.7 percent and the yield of 60 percent.
The structure of compound C is characterized as:1H NMR(400MHz,DMSO-d6)：δ(8.01-8.84(t, 12H),7.31-7.54(m,3H),6.94-7.17(q,4H)6.42(d,2H),6.38(d,2H),4.17(t,4H), 4.04(t,4H),2.23(s,3H),2.01(s,3H)，1.84(m,4H),1.72(m,4H),1.66-1.36(m,8H)。
example 1:
durability test
The retardation (R) of each cured film was measured using an Axoscan ellipsometerin). Analysis of R Using a light Source with a wavelength of 550nmin. To determine the delay dispersion ratio Rin-450/Rin-550The retardation of the materials was measured at wavelengths of 450nm and 550nm, and if not otherwise stated, each film was then placed in an oven at 85 ℃ for a total time of 100 hours, and if not otherwise stated, after 100 hours the film was removed from the oven and cooled to room temperature, and the retardation curve was again recorded, the durability passing the R before and after the oven testinAnd Rin-450/Rin-550Is quantized.
Adhesion test
The adhesion of the film to the substrate was tested using the Nichiban 305 tape test. Thus 305 tape is adhered to the polymer film and then torn off sharply, and if the film is not removed, adhesion is considered to pass. The composition has the following components that X represents complete separation from the substrate, Delta represents certain adhesiveness, and o represents complete adhesiveness with the substrate.
The mixture used:
mixture CM-1
Mixture CM-2
Mixture CM-3
Experiment 1.1 the mixture CM-1 was dissolved at 33.3% solids in toluene/cyclopentanone (7: 3) and the solution was overcoated with alignment layer on a TAC substrate using Meyer rod # 05. The film was annealed at 65 ℃ for 120 seconds and cured under nitrogen using a fusion H bulb lamp (75% power, 10 m/min). The film was laminated to a pressure sensitive adhesive and covered with a green glass, so the total film stack was TAC/polymer film/pressure sensitive adhesive/glass, and the film was subjected to a durability test.
Experiment 1.2 the mixture CM-2 was dissolved at 33.3% solids in toluene/cyclopentanone (7: 3) and the solution was overcoated with alignment layer on a TAC substrate using Meyer rod # 05. The films were annealed at 65 ℃ for 120 seconds and cured using a fusion H bulb lamp (75% power, 10m/min) under nitrogen atmosphere, laminated to the pressure sensitive adhesive and covered with a green glass, so the total film stack was TAC/polymer film/pressure sensitive adhesive/glass and subjected to durability experiments.
Experiment 1.3 the mixture CM-3 was dissolved at 33.3% solids in toluene/cyclopentanone (7: 3) and the solution was overcoated with alignment layer on a TAC substrate using Meyer rod # 05. The film was annealed at 65 ℃ for 120 seconds and cured under nitrogen using a fusion H bulb lamp (75% power, 10 m/min). The film was laminated to a pressure sensitive adhesive and covered with a green glass, so the total film stack was TAC/polymer film/pressure sensitive adhesive/glass, and the film was subjected to a durability test.
See table 1 for results.
As can be seen from table 1, the polymerizable compound, the composition and the optically anisotropic body of the present invention can exhibit not only favorable substrate high adhesion in the RM optical retardation film but also good high temperature stability.
It should be understood that the detailed description of the invention is merely illustrative of the spirit and principles of the invention and is not intended to limit the scope of the invention. Furthermore, it should be understood that various changes, substitutions, deletions, modifications or adjustments may be made by those skilled in the art after reading the disclosure of the present invention, and such equivalents are also within the scope of the invention as defined in the appended claims.
Claims (10)
1. A polymerizable compound selected from compounds of the general formula (1),
in the formula (I), the compound is shown in the specification,
P1and P2Each independently represents a polymerizable group;
L1-L4each independently represents a single bond, -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、-OCF2-、-CF2O-、-SCF2-、-CF2S-、-CH＝CHOCO-、-CH＝CHCOO-、-OCOCH＝CH-、-COOCH＝CH-、-CH2CH2OCO-、-CH2CH2COO-、-OCOCH2CH2-、-COOCH2CH2-、-CH2OCO-、-CH2COO-、-OCOCH2-、-COOCH2-, -CH ═ CH-, -N ═ CH-, -CH ═ N-, -N ═ N-, -CH ═ CF-, -CF ═ CH-, -N ═ CF-, -CF ═ N-, -C ≡ C-, or alkylene having a carbon number of 1 to 30; one or more-CH's in said alkylene group2-may be substituted by-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; l is1-L4When plural, they may be the same or different;
C1and C2Each independently represents-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、-OCF2-、-CF2O-、-SCF2-、-CF2S-、-CH＝CHOCO-、-CH＝CHCOO-、-OCOCH＝CH-、-COOCH＝CH-、-CH2CH2OCO-、-CH2CH2COO-、-OCOCH2CH2-、-COOCH2CH2-、-CH2OCO-、-CH2COO-、-OCOCH2-、-COOCH2-, -CH ═ CH-, -N ═ CH-, -CH ═ N-, -N ═ N-, -CH ═ CF-, -CF ═ CH-, -N ═ CF-, -CF ═ N-, -C ≡ C-, or a single bond;
ring a represents a group selected from:
(a)1, 4-cyclohexylene; wherein 1 is present-CH2-or non-adjacent more than 2-CH2-may be substituted by-O-, -S-, -NH-;
(b)1, 4-phenylene; wherein 1-CH-present or non-adjacent 2 or more-CH-may be substituted by-N ═ group;
(c)1, 4-cyclohexenylene, 2, 4-cyclopentadien-2, 5-diyl, thiophen-2, 5-diyl, furan-2, 5-diyl, piperidin-2, 5-diyl, naphthalen-2, 6-diyl, naphthalen-1, 4-diyl, naphthalen-1, 5-diyl, 1,2,3, 4-tetrahydronaphthalen-2, 6-diyl and decahydronaphthalen-2, 6-diyl;
the above groups (a), (b) or (c) may be each independently substituted with halogen, cyano, alkyl group having 1 to 30 carbon atoms, haloalkyl group having 1 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, haloalkoxy group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, haloalkenyl group having 2 to 30 carbon atoms, alkenyloxy group having 2 to 30 carbon atoms, haloalkenyloxy group having 2 to 30 carbon atoms, alkoxycarbonyl group having 1 to 30 carbon atoms, haloalkoxycarbonyl group having 1 to 30 carbon atoms, alkylcarbonyl group having 1 to 30 carbon atoms, haloalkylcarbonyl group having 1 to 30 carbon atoms, alkanoyloxy group having 1 to 30 carbon atoms or haloalkoyloxy group having 1 to 30 carbon atoms;
R1and R2Each independently represents an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, a haloalkylcarbonyl group having 1 to 30 carbon atoms, an alkanoyloxy group having 1 to 30 carbon atoms or a haloalkoyloxy group having 1 to 30 carbon atoms; m and n each independently represent an integer of 0 to 8.
2. The polymerizable compound of claim 1 wherein the polymerizable group is selected from the group consisting of:
in the formula, R3Each independently represents a hydrogen atom, a halogen, a cyano group, a carbon number 1-30 alkyl, C1-30 haloalkyl, C1-30 alkoxy, C1-30 haloalkoxy, C2-30 alkenyl, C2-30 haloalkenyl, C2-30 alkenyloxy, C2-30 haloalkenyloxy, C1-30 alkoxycarbonyl, C1-30 haloalkoxycarbonyl, C1-30 alkylcarbonyl, C1-30 haloalkylcarbonyl, C1-30 alkanoyloxy or C1-30 haloalkoyloxy;
preferably, P1And P2Each independently represents a group of (P-1) and (P-2).
3. The polymerizable compound according to claim 1, wherein ring a represents a 1, 4-phenylene group; wherein 1-CH-present or non-adjacent 2 or more-CH-may be substituted by-N ═ group; and/or ring A may be substituted with halogen, cyano, alkyl group having 1 to 30 carbon atoms, haloalkyl group having 1 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, haloalkoxy group having 1 to 30 carbon atoms, alkanoyloxy group having 1 to 30 carbon atoms and haloalkoyloxy group having 1 to 30 carbon atoms.
4. The polymerizable compound of claim 1, wherein L1-L2Each independently represents an alkylene group having 1 to 30 carbon atoms; one or more-CH's in said alkylene group2-may be substituted by-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; and/or, L3-L4Each independently represents a single bond, -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、-OCF2-、-CF2O-、-SCF2-、-CF2S-。
5. The polymerizable compound according to claim 1, wherein C1And C2Each independently represents-OCO-, -COO-, -SCO-, -COS-, -OCOO-.
6. Polymerizable composition comprising a mono-reactive mesogenic compound and a di-reactive mesogenic compound, characterized in that said di-reactive mesogenic compound comprises a compound of general formula (1) according to claim 1.
7. The polymerizable composition of claim 6, wherein said bireactive mesogenic compound further comprises a compound of general formula (2),
in the formula (I), the compound is shown in the specification,
P1' and P2' each independently represents a polymerizable group;
L1’-L4' each independently represents a single bond, -O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、-OCF2-、-CF2O-、-SCF2-、-CF2S-、-CH＝CHOCO-、-CH＝CHCOO-、-OCOCH＝CH-、-COOCH＝CH-、-CH2CH2OCO-、-CH2CH2COO-、-OCOCH2CH2-、-COOCH2CH2-、-CH2OCO-、-CH2COO-、-OCOCH2-、-COOCH2-, -CH ═ CH-, -N ═ CH-, -CH ═ N-, -N ═ N-, -CH ═ CF-, -CF ═ CH-, -N ═ CF-, -CF ═ N-, -C ≡ C-, or alkylene having a carbon number of 1 to 30; one or more-CH's in said alkylene group2-may be substituted by-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-; l is1’-L4' when plural, they may be the same or different;
C1' and C2' each independently represents-O-, -S-, -NH-, -CO-, -OCO-, -COO-, -SCO-, -COS-, -OCOO-, -NHCO-, -CONH-, -OCH2-、-CH2O-、-SCH2-、-CH2S-、-OCF2-、-CF2O-、-SCF2-、-CF2S-、-CH＝CHOCO-、-CH＝CHCOO-、-OCOCH＝CH-、-COOCH＝CH-、-CH2CH2OCO-、-CH2CH2COO-、-OCOCH2CH2-、-COOCH2CH2-、-CH2OCO-、-CH2COO-、-OCOCH2-、-COOCH2-, -CH ═ CH-, -N ═ CH-, -CH ═ N-, -N ═ N-, -CH ═ CF-, -CF ═ CH-, -N ═ CF-, -CF ═ N-, -C ≡ C-, or a single bond;
ring a' represents a group selected from:
(a)1, 4-cyclohexylene; in which 1-CH is present2-or non-adjacent more than 2-CH2-may be substituted by-O-, -S-, -NH-;
(b)1, 4-phenylene; wherein 1-CH-present or non-adjacent 2 or more-CH-may be substituted by-N ═ group;
(c)1, 4-cyclohexenylene, 2, 4-cyclopentadien-2, 5-diyl, thiophen-2, 5-diyl, furan-2, 5-diyl, piperidin-2, 5-diyl, naphthalen-2, 6-diyl, naphthalen-1, 4-diyl, naphthalen-1, 5-diyl, 1,2,3, 4-tetrahydronaphthalen-2, 6-diyl and decahydronaphthalen-2, 6-diyl;
the above groups (a), (b) or (c) may be each independently substituted with halogen, cyano, alkyl group having 1 to 30 carbon atoms, haloalkyl group having 1 to 30 carbon atoms, alkoxy group having 1 to 30 carbon atoms, haloalkoxy group having 1 to 30 carbon atoms, alkenyl group having 2 to 30 carbon atoms, haloalkenyl group having 2 to 30 carbon atoms, alkenyloxy group having 2 to 30 carbon atoms, haloalkenyloxy group having 2 to 30 carbon atoms, alkoxycarbonyl group having 1 to 30 carbon atoms, haloalkoxycarbonyl group having 1 to 30 carbon atoms, alkylcarbonyl group having 1 to 30 carbon atoms, haloalkylcarbonyl group having 1 to 30 carbon atoms, alkanoyloxy group having 1 to 30 carbon atoms or haloalkoyloxy group having 1 to 30 carbon atoms;
R1' and R2' each independently represents an alkyl group having 1 to 30 carbon atoms, a haloalkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a haloalkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a haloalkenyl group having 2 to 30 carbon atoms, an alkenyloxy group having 2 to 30 carbon atoms, a haloalkenyloxy group having 2 to 30 carbon atoms, an alkoxycarbonyl group having 1 to 30 carbon atoms, a haloalkoxycarbonyl group having 1 to 30 carbon atoms, an alkylcarbonyl group having 1 to 30 carbon atoms, a haloalkylcarbonyl group having 1 to 30 carbon atoms, an alkanoyloxy group having 1 to 30 carbon atoms or a haloalkoyloxy group having 1 to 30 carbon atoms;
m and n each independently represent an integer of 0 to 4.
8. Polymerizable composition according to claim 6, wherein the content of said bireactive mesogenic compound is between 80 and 99% by weight; and/or the compound of formula (1) is present in an amount of 6 to 18 wt%, based on the total weight of the polymerizable composition.
9. A polymerizable composition solution comprising the polymerizable composition according to any one of claims 6 to 8 and an organic solvent.
10. An optically anisotropic body comprising a base material and a polymer film formed by solution-curing the polymerizable composition according to claim 9, and, if necessary, an alignment film; advantageously, the optically anisotropic body is selected from phase difference films.
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| CN115322795A (en) * | 2021-12-29 | 2022-11-11 | 上海先认新材料合伙企业(有限合伙) | Liquid crystal composition and application thereof |
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