WO2017098988A1 - 重合性化合物及び光学異方体 - Google Patents
重合性化合物及び光学異方体 Download PDFInfo
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- WO2017098988A1 WO2017098988A1 PCT/JP2016/085717 JP2016085717W WO2017098988A1 WO 2017098988 A1 WO2017098988 A1 WO 2017098988A1 JP 2016085717 W JP2016085717 W JP 2016085717W WO 2017098988 A1 WO2017098988 A1 WO 2017098988A1
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- 0 *[n]1cccc1 Chemical compound *[n]1cccc1 0.000 description 14
- SFLGSKRGOWRGBR-UHFFFAOYSA-N C1OCc2ccccc12 Chemical compound C1OCc2ccccc12 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N C1Oc2ccccc2O1 Chemical compound C1Oc2ccccc2O1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 description 1
- KVRZARWOKBNZMM-UHFFFAOYSA-N C1SCc2ccccc12 Chemical compound C1SCc2ccccc12 KVRZARWOKBNZMM-UHFFFAOYSA-N 0.000 description 1
- AIUOUEPKBRDPLG-UHFFFAOYSA-N C1Sc(cccc2)c2O1 Chemical compound C1Sc(cccc2)c2O1 AIUOUEPKBRDPLG-UHFFFAOYSA-N 0.000 description 1
- HCMLNPZTRYNCMA-UHFFFAOYSA-N C1Sc2ccccc2S1 Chemical compound C1Sc2ccccc2S1 HCMLNPZTRYNCMA-UHFFFAOYSA-N 0.000 description 1
- YJUFGFXVASPYFQ-UHFFFAOYSA-N C1c(cccc2)c2SC1 Chemical compound C1c(cccc2)c2SC1 YJUFGFXVASPYFQ-UHFFFAOYSA-N 0.000 description 1
- LPAGFVYQRIESJQ-UHFFFAOYSA-N C1c2ccccc2NC1 Chemical compound C1c2ccccc2NC1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
- HBEDSQVIWPRPAY-UHFFFAOYSA-N C1c2ccccc2OC1 Chemical compound C1c2ccccc2OC1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 1
- CPUOMPRQOCEZSL-UHFFFAOYSA-N C=C(c1ccccc1C=C1)C1=O Chemical compound C=C(c1ccccc1C=C1)C1=O CPUOMPRQOCEZSL-UHFFFAOYSA-N 0.000 description 1
- XEIIBIDCHSRPFE-UHFFFAOYSA-N C=C1c([nH]cc2)c2C=C1 Chemical compound C=C1c([nH]cc2)c2C=C1 XEIIBIDCHSRPFE-UHFFFAOYSA-N 0.000 description 1
- UIKUOLDBDOKVHN-UHFFFAOYSA-N O=C(c1ccccc11)N(CCCCCCI)C1=O Chemical compound O=C(c1ccccc11)N(CCCCCCI)C1=O UIKUOLDBDOKVHN-UHFFFAOYSA-N 0.000 description 1
- JPOIEKODRGNQRZ-UHFFFAOYSA-N S=C(c1ccccc11)N(CCCCCCI)C1=S Chemical compound S=C(c1ccccc11)N(CCCCCCI)C1=S JPOIEKODRGNQRZ-UHFFFAOYSA-N 0.000 description 1
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- G—PHYSICS
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
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- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
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- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
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Definitions
- the present invention relates to a compound having a polymerizable group, a polymerizable composition containing the compound, a polymerizable liquid crystal composition, and an optical anisotropic body using the polymerizable liquid crystal composition.
- a compound having a polymerizable group is used in various optical materials.
- a polymer having a uniform orientation by aligning a polymerizable composition containing a polymerizable compound in a liquid crystal state and then polymerizing it.
- Such a polymer can be used for polarizing plates, retardation plates and the like necessary for displays.
- two or more types of polymerization are used to satisfy the required optical properties, polymerization rate, solubility, melting point, glass transition temperature, polymer transparency, mechanical strength, surface hardness, heat resistance and light resistance.
- a polymerizable composition containing a functional compound is used. In that case, the polymerizable compound to be used is required to bring good physical properties to the polymerizable composition without adversely affecting other properties.
- the problem to be solved by the present invention is to provide a polymerizable liquid crystal compound having reverse wavelength dispersion or low wavelength dispersion having high solubility in various solvents. At the same time, it is added to the polymerizable composition, and the reverse wavelength dispersibility or low wavelength has high adhesion to the substrate (or alignment film) of the optically anisotropic substance obtained by polymerizing the polymerizable composition with ultraviolet light. It is to provide a polymerizable liquid crystal compound having dispersibility. Furthermore, a polymerizable composition containing a polymerizable liquid crystal compound having reverse wavelength dispersion or low wavelength dispersion, a polymer obtained by polymerizing the polymerizable composition, and an optical anisotropic using the polymer Is to provide a body.
- the present inventors have found that a low wavelength dispersive and / or reverse wavelength dispersible compound having a partial structure represented by the formula (AO-1) in the molecule. It led to development. That is, the present invention provides the following formula (AO-1) in the molecule:
- n 0 represents an integer of 2 or more
- R 0 represents a linear or branched alkylene group having 2 to 20 carbon atoms
- an arbitrary hydrogen atom in the alkylene group is a fluorine atom or a chlorine atom.
- a plurality of R 0 may be the same or different, and a polymerizable low wavelength dispersible or polymerizable reverse wavelength dispersible compound having a partial structure represented by:
- a polymerizable composition containing the compound, a resin using the compound, a resin additive, an oil, a filter, an adhesive, an adhesive, an oil, an ink, a pharmaceutical, a cosmetic, a detergent, a building material, and a packaging material , Liquid crystal materials, organic EL materials, organic semiconductor materials, electronic materials, display elements, electronic devices, communication equipment, automobile parts, aircraft parts, machine parts, agricultural chemicals and foods and products using them, polymerizable liquid crystal compositions, polymerization Providing an optically anisotropic body using a polymer and the polymer obtained by polymerizing a liquid crystal composition.
- the compound of the present invention has high solubility in various solvents, and hardly produces precipitates when an optical anisotropic body is produced.
- the optical anisotropic body is applied to various substrates (or alignment films) such as glass and plastic. Since the adhesiveness is high, it is useful for optical materials such as retardation films.
- the present invention provides an inversely dispersible compound having a specific structure in the molecule, and also a polymerizable composition containing the compound, a resin, a resin additive, an oil, a filter, an adhesive, and an adhesive using the compound.
- Agents, oils and fats, inks, pharmaceuticals, cosmetics, detergents, building materials, packaging materials, liquid crystal materials, organic EL materials, organic semiconductor materials, electronic materials, display elements, electronic devices, communication equipment, automobile parts, aircraft parts, machine parts, Agrochemicals and foods, products using them, polymerizable liquid crystal compositions, polymers obtained by polymerizing the polymerizable liquid crystal compositions, and optical anisotropic bodies using the polymers are provided.
- the film when the birefringence ⁇ n increases as the wavelength ⁇ decreases, the film is “positively dispersive”.
- the film When the birefringence ⁇ n decreases as the wavelength ⁇ decreases, the film is generally referred to by those skilled in the art as being “reverse wavelength dispersive” or “reverse dispersive”.
- the value Re (450) / Re (550) obtained by dividing the in-plane retardation (Re (450)) at a wavelength of 450 nm by the in-plane retardation Re (550) at a wavelength of 550 nm is 0.95 or less.
- a compound constituting the retardation film is referred to as a reverse dispersion compound.
- a compound constituting a retardation film having Re (450) / Re (550) of greater than 0.95 and 1.05 or less is referred to as a low wavelength dispersible compound.
- the method for measuring the phase difference is as follows.
- the polyimide film for alignment film is applied to a glass substrate having a thickness of 0.7 mm using a spin coating method, dried at 100 ° C. for 10 minutes, and then baked at 200 ° C. for 60 minutes to obtain a coating film.
- the obtained coating film is rubbed using a commercially available rubbing apparatus.
- a cyclopentanone solution containing 20% by mass of the compound to be evaluated is applied to the rubbed substrate by a spin coating method and dried at 100 ° C. for 2 minutes. After cooling the obtained coating film to room temperature, a film to be evaluated is obtained by irradiating with ultraviolet rays at an intensity of 30 mW / cm 2 for 30 seconds using a high-pressure mercury lamp. The retardation of the obtained film is measured using a retardation film / optical material inspection apparatus RETS-100 (manufactured by Otsuka Electronics Co., Ltd.).
- a film is prepared using a composition obtained by adding a compound to be evaluated (10% by mass, 20% by mass or 30% by mass) to the base liquid crystal composed of the above, and the phase difference is measured by extrapolation.
- R 0 represents a linear or branched alkylene group having 2 to 20 carbon atoms, and any hydrogen atom in the alkylene group may be substituted with a fluorine atom or a chlorine atom.
- a plurality of R 0 represent groups which may be the same or different. From the viewpoint of liquid crystallinity, ease of synthesis, solubility in various solvents, and adhesion to various base materials (or alignment films), R 0 may have any hydrogen atom substituted with a fluorine atom or a chlorine atom.
- n 0 represents an integer of 2 or more, and when there are a plurality of n 0, they may be the same or different, but the liquid crystallinity, ease of synthesis, various solvents From the viewpoint of the solubility of the resin and the adhesion to various substrates (or alignment films), n 0 preferably represents an integer of 2 or more, and more preferably 2 or 3.
- P 0 represents a polymerizable group
- k 0 represents an integer of 0 to 10
- Sp 0 represents a linear or branched alkylene group having 1 to 30 carbon atoms or a single bond
- one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO.
- (Sp 0 ) k0 may be a group having a partial structure represented by the general formula (AO-1), provided that P 0- (Sp 0 ) k0- is -O It preferably has a group represented by the formula:
- P 0 represents a polymerizable group
- P-20 the following formulas (P-1) to (P-20)
- these polymerizable groups are polymerized by radical polymerization, radical addition polymerization, cationic polymerization and anionic polymerization.
- the formula (P-1), formula (P-2), formula (P-3), formula (P-4), formula (P-5), formula (P ⁇ 7), formula (P-11), formula (P-13), formula (P-15) or formula (P-18) are preferred, and formula (P-1), formula (P-2), formula (P-18) P-7), formula (P-11) or formula (P-13) is more preferred, formula (P-1), formula (P-2) or formula (P-3) is more preferred, and formula (P- Particular preference is given to 1) or formula (P-2).
- Sp 0 represents a linear or branched alkylene group having 1 to 30 carbon atoms or a single bond, and the alkylene group is one —CH 2 — or adjacent. Two or more —CH 2 — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO.
- —O—, —CO—NH—, —NH—CO—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH —OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —CH ⁇ CH—, —N ⁇ N—, —CH ⁇ NN—CH—, —CF ⁇ CF— or —C may be replaced by ⁇ C, but Sp 0 may be those when the plurality of are the same or different and raw materials readily available Ease of synthesis and the liquid crystal from the viewpoint of one -CH 2 - or nonadjacent two or more -CH 2 - are each independently -O -, - S -, - COO -, - OCO —, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO
- It preferably represents a linear or branched alkylene group having 1 to 20 carbon atoms or a single bond, and one —CH 2 — or two or more non-adjacent —CH 2 — are each independently Number of carbon atoms that may be replaced by O—, —COO—, —OCO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH ⁇ CH— or —C ⁇ C more preferably represents a linear or branched alkylene group or a single bond 1 to 20, one -CH 2 - or adjacent Though not two or more -CH 2 - are each independently of -O -, - COO -, - it is particularly preferable that the good 1 -C be replaced represents an alkylene group or a single bond 12 to OCO- .
- k 0 represents an integer of 0 to 10, preferably an integer of 0 to 5, more preferably an integer of 0 to 3, It is particularly preferable to represent an integer of 3.
- the general formula (I-0-R) represents the above (Sp 0 ) k0 group moiety. It preferably includes a partial structure represented by the general formula (AO-1), and the general formula (I-0-R) is a group represented by P 0 — ((CH 2 ) m0 —O) k01 —.
- P 0 represents the polymerizable group
- a preferable polymerizable group is the same as that defined for P 0
- m0 represents an integer of 2 to 10
- k01 represents 2 to 3
- the plurality of m0s may be the same or different.
- the low wavelength dispersibility and / or reverse wavelength dispersibility compound of the present invention is represented by the general formula (I).
- R 1 and R 2 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 80 carbon atoms, the group may have a substituent, and any carbon atom is An atom may be substituted, but at least one of R 1 and R 2 represents a group represented by the general formula (I-0-R),
- a 1 and A 2 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl.
- the group may be unsubstituted or substituted by one or more substituents L, where L is a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano Group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, Oisoshiano group, or one -CH 2 - or nonadjacent two or more -CH 2 - are each independently -O -, - S
- Linear or branched having 1 to 20 carbon atoms which may be substituted by —CH ⁇ CH—, —OCO—CH ⁇ CH—, —CH ⁇ CH—, —CF ⁇ CF— or —C ⁇ C—
- P L represents a polymerizable group, preferably polymerizable group identical to that defined above P 0 what And, Sp L is one -CH 2 - or nonadjacent two or more -CH 2 - are each independently -O -, - COO -, - good number of carbon atoms be replaced by OCO- 1 to 10 linear alkylene groups or a single bond, and when a plurality of Sp L are present, they may be the same or different, and X L represents —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO —, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇
- KL represents an integer of 0 to 10, and when there are a plurality of L in the compound, they may be the same or different, and the substituent L is a fluorine atom, a chlorine atom, pentafluorosulfuranyl.
- Group, nitro group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, or any hydrogen atom may be replaced by a fluorine atom, one —CH 2 — or two not adjacent
- the above —CH 2 — is independently —O—, —S—, —CO—, —COO—, —OCO—, —O—CO—O—, —CH ⁇ CH—, —CF ⁇ CF—.
- a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by a group selected from —C ⁇ C—, and is preferably a fluorine atom, a chlorine atom, or any hydrogen atom Is replaced by a fluorine atom
- one —CH 2 — or two or more non-adjacent —CH 2 — may be each independently substituted with a group selected from —O—, —COO—, or —OCO—. More preferably, it represents a linear or branched alkyl group having 1 to 12 carbon atoms, and a fluorine atom, a chlorine atom, or an arbitrary hydrogen atom may be substituted with a fluorine atom.
- Z 1 and Z 2 are each independently —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—, —OCO—, —CO —S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH— COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 -COO
- Straight chain of 1 to 20 carbon atoms which may be substituted by —, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —CH ⁇ CH—, —CF ⁇ CF— or —C ⁇ C— represents a Jo or branched alkyl group, any hydrogen atom in the alkyl group may be substituted by a fluorine atom, or, L G is P LG - represented by - (Sp LG -X LG) kLG Wherein P LG represents a polymerizable group, a preferred polymerizable group represents the same as defined above for P 0 , and Sp LG represents one —CH 2 — or adjacent group.
- X LG is -O —, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, — CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO —, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2
- KLG represents an integer of 0 to 10
- m1 and m2 integer from 0 to 6 each independently is M1 + m2 represents an integer of 0 to 6. It is preferable that it is a compound represented by this.
- R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 80 carbon atoms, and the hydrocarbon group may have a substituent, and The carbon atom of may be substituted with a hetero atom, but at least one of R 1 and R 2 represents a group represented by the general formula (I-0-R).
- each of R 1 and R 2 is independently a hydrogen atom from the viewpoint of liquid crystallinity and ease of synthesis
- a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or any hydrogen atom in the group may be substituted with a fluorine atom
- One —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO.
- a hydrogen atom, a fluorine atom, a chlorine atom, or one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —COO—, —OCO—, — A straight chain having 1 to 12 carbon atoms that may be substituted by O—CO—O—.
- a branched alkyl group more preferably a hydrogen atom, a fluorine atom, a chlorine atom, or a straight-chain alkyl group having 1 to 12 carbon atoms or a straight-chain alkoxy group, more preferably 1 to 1 carbon atom. It is particularly preferred to represent 12 linear alkyl groups or linear alkoxy groups. From the viewpoint of mechanical strength and liquid crystallinity in the case of an optical film, it is more preferable that R 1 and R 2 each independently represent a group represented by the general formula (I-0-R).
- a 1 and A 2 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, Naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl Represents a group, these groups may be unsubstituted or substituted by one or more of the above-described substituents L.
- a 1 and A 2 are each independently 1,4-phenylene group, 1,4-cyclohexylene group, naphthalene which may be unsubstituted or substituted by one or more substituents L -2,6-diyl groups are preferred and each independently represents the following formula (A-1) to formula (A-11)
- each group independently represents a group selected from formula (A-1) to formula (A-8), and each independently represents a group selected from formula (A-1). It is particularly preferable to represent a group selected from the formula (A-4). From the viewpoint of reverse dispersion, it is represented by Z 2 adjacent to the group represented by group and G 1 is represented by A 1 that binds to a group represented by Z 1 adjacent to the group represented by G 1
- the group represented by A 2 which is bonded to the group represents a 1,4-cyclohexylene group which is each independently unsubstituted or optionally substituted by one or more of the above-described substituents L. And more preferably a group represented by the above formula (A-2).
- the group represented by A 1 and A 2 there are a plurality, refractive index anisotropy, ease of synthesis, from the viewpoint of solubility in a solvent, wherein A 1 and A 2 other than A 1 and A
- the group represented by 2 represents a 1,4-phenylene group or a naphthalene-2,6-diyl group that are each independently unsubstituted or optionally substituted by one or more substituents L.
- each independently represents a group selected from the above formula (A-1), formula (A-3) to formula (A-11), and each independently represents formula (A-1) And more preferably a group selected from formula (A-3) to formula (A-8), each independently from formula (A-1), formula (A-3), or formula (A-4). It is particularly preferred to represent a selected group.
- Z 1 and Z 2 are each independently —O—, —S—, —OCH 2 —, —CH 2 O—, —CH 2 CH 2 —, —CO—, —COO—. , —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, — NH—CO—NH—, —NH—O—, —O—NH—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —, —OCO—
- Z 1 and Z 2 are —OCH 2 —, —CH 2 O—, —COO—, —OCO—, —CF 2 O—, —OCF from the viewpoints of liquid crystallinity, availability of raw materials, and ease of synthesis.
- m1 and m2 each independently represent an integer from 0 to 6, but m1 + m2 represents an integer from 0 to 6.
- m1 and m2 preferably each independently represent an integer of 1 to 3, and each independently 1 or It is particularly preferred to represent 2. From the viewpoint of ease of synthesis, m1 and m2 are more preferably the same.
- G 1 represents a divalent group having at least one aromatic ring selected from the group consisting of an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and in the group represented by G 1 number of ⁇ electrons contained in the aromatic ring is 12 or more, group represented by G 1 may be substituted by unsubstituted or substituted with one or more of the aforementioned substituents L G.
- G 1 is preferably a group having an absorption maximum from 300 nm to 900 nm, and more preferably a group having an absorption maximum from 310 nm to 500 nm.
- G 1 is represented by the following general formula (M-1) to general formula (M-6).
- T 1 can be replaced by the following formula (T1-1) to formula (T1-6)
- a bond may be present at any position, and arbitrary —CH ⁇ may be independently replaced by —N ⁇ , and —CH 2 — may be independently —O—, — S—, —NR T — (wherein R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), —CS— or —CO— may be substituted.
- R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
- R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
- CS— or —CO— may be substituted.
- T1-1 is coupled to T 1 of the formula (M-6) from the formula (M-1) to the T 1 of the formula (M-6)
- These groups may be substituted or unsubstituted. Which may be substituted by one or more of the above-mentioned substituents LG).
- T 2 may be replaced by the following general formula (T2-1) or general formula (T2-2)
- W 1 represents an optionally substituted aromatic group having 1 to 40 carbon atoms and / or a non-aromatic group, and the aromatic group is a hydrocarbon ring or a heterocyclic ring.
- the non-aromatic group may be a hydrocarbon group or a group in which any carbon atom of the hydrocarbon group is substituted with a hetero atom (however, oxygen atoms are not directly bonded to each other).
- W 2 is a hydrogen atom, or one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO—, —COO—, — OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—.
- W W 2 is a group having 2 to 30 carbon atoms having at least one aromatic group
- the group may be unsubstituted or substituted by one or more substituents
- L W W 2 may represent a group represented by P W — (Sp W —X W ) kW —, where P W represents a polymerizable group, and Sp W represents a spacer group or a single bond.
- X W is —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO. —, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, — CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —, —OCO—CH
- KLW represents an integer of 0 to 10, if the substituents L W in the compound there are a plurality of them may be the same or different and Y is a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, A diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group or one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO
- atom Represents a linear or branched alkyl group of 1 to 20, wherein any hydrogen atom in the alkyl group may be substituted with a fluorine atom, or Y represents P Y — (Sp Y —X Y ) kY -Y may represent a group represented by-, P Y represents a polymerizable group, a preferred polymerizable group represents the same as defined for P 0 above, and Sp Y represents one of -CH
- a linear alkylene group having 1 to 10 carbon atoms in which 2 — or two or more non-adjacent —CH 2 — may be each independently substituted by —O—, —COO—, —OCO—, or Represents a single bond
- KY represents an integer of 0 to 10
- W 1 and W 2 may be combined to form a ring structure.
- T 1 represents the same meaning as described above, and R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
- R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
- M-1-4 represents a group selected from formula (M-1-4) or a group selected from formula (M-1-5) is more preferable, and a group represented by formula (M-1-5) is particularly preferable.
- T 1 represents the same meaning as described above, and R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), and preferably represents a group selected from formula (M-3- 4) or a group selected from formula (M-3-5) is more preferable, and a group represented by formula (M-3-5) is particularly preferable.
- T 1 represents the same meaning as described above, and R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), and preferably represents a group selected from formula (M-4- 4) or a group selected from formula (M-4-5) is more preferable, and a group represented by formula (M-4-5) is particularly preferable.
- T 1 is represented by the formula (T1-1), the formula (T1-2), the formula (T1- 3), preferably a group selected from the formula (T1-6), more preferably a group selected from the formula (T1-3) and the formula (T1-5), and the formula (T1-3) It is particularly preferred to represent. More specifically, examples of the group represented by the formula (T1-1) include the following formulas (T1-1-1) to (T1-1-7)
- R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. These groups may be unsubstituted or substituted with one or more of the above-mentioned substituents. preferably represents a group selected from the group L G may be substituted.), formula (T1-1-2), formula (T1-1-4), formula (T1-1-5), formula ( It is more preferable to represent a group selected from T1-1-6) and formula (T1-1-7). Examples of the group represented by the formula (T1-2) include the following formulas (T1-2-1) to (T1-2-8)
- R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. These groups may be unsubstituted or substituted with one or more of the above-mentioned substituents. preferably represents a group selected from the group L G may be substituted.
- Examples of the group represented by the formula (T1-4) include the following formulas (T1-4-1) to (T1-4-6)
- a bond may be present at any position, and R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. These groups may be unsubstituted or substituted with one or more of the above-mentioned substituents. preferably represents a group selected from the group L G may be substituted.).
- R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. These groups may be unsubstituted or substituted with one or more of the above-mentioned substituents. preferably represents a group selected from the group L G may be substituted.).
- Examples of the group represented by the formula (T1-5) include the following formulas (T1-5-1) to (T1-5-9)
- a bond may be present at any position, and R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. These groups may be unsubstituted or substituted with one or more of the above-mentioned substituents. preferably represents a group selected from the group L G may be substituted.).
- R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms. These groups may be unsubstituted or substituted with one or more of the above-mentioned substituents. preferably represents a group selected from the group L G may be substituted.).
- Examples of the group represented by the formula (T1-6) include the following formulas (T1-6-1) to (T1-6-7)
- the above substituent LG is a fluorine atom, a chlorine atom, a pentafluorosulfuranyl group, a nitro group, a methylamino group, a dimethylamino group, diethylamino group.
- a group, a diisopropylamino group, or any hydrogen atom may be replaced by a fluorine atom, and one —CH 2 — or two or more non-adjacent —CH 2 — may be independently —O— Substituted by a group selected from: —S—, —CO—, —COO—, —OCO—, —O—CO—O—, —CH ⁇ CH—, —CF ⁇ CF— or —C ⁇ C—. It is preferably a linear or branched alkyl group having 1 to 20 carbon atoms, and a fluorine atom, a chlorine atom, or an arbitrary hydrogen atom may be substituted with a fluorine atom.
- the two or more —CH 2 — each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted with a group selected from —O—, —COO— or —OCO—.
- the fluorine atom, the chlorine atom, or any hydrogen atom represents a linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms which may be substituted with a fluorine atom.
- it represents a fluorine atom, a chlorine atom, or a linear alkyl group or linear alkoxy group having 1 to 8 carbon atoms.
- T 2 represents the same meaning as described above, and preferably represents a group selected from Formula (M-7-1) to Formula (M-12-1). It is more preferable that the group represented by the formula (M-7-1) or the formula (M-8-1) is particularly preferable.
- Y is a hydrogen atom, a fluorine atom, a chlorine atom, a nitro group, a cyano group or any hydrogen in the group from the viewpoint of liquid crystallinity and ease of synthesis.
- the atom may be substituted with a fluorine atom, and one —CH 2 — or two or more non-adjacent —CH 2 — may each independently represent —O—, —S—, —CO—, —COO.
- Y may be any hydrogen atoms in the hydrogen atom or a group substituted by fluorine atoms, one -CH 2 - or nonadjacent two or more -CH 2 - are each independently - More preferably, it represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by O—, —COO— or —OCO—, and Y represents a hydrogen atom or any hydrogen atom in the group Is more preferably a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted with a fluorine atom, and Y represents a hydrogen atom or a linear alkyl group having 1 to 12 carbon atoms. It is particularly preferred.
- W 1 is optionally substituted aromatic and / or non-aromatic from 1 to 80 carbon atoms from the viewpoint of liquid crystallinity and ease of synthesis.
- the aromatic group contained in W 1 is unsubstituted or may be substituted by one or more substituents L W from the viewpoints of availability of raw materials and ease of synthesis.
- the ring structure may have a bond at an arbitrary position, and may form a group in which two or more aromatic groups selected from these groups are linked by a single bond.
- CH ⁇ may each independently be replaced by —N ⁇
- —CH 2 — each independently represents —O—, —S—, —NR T — (wherein R T represents a hydrogen atom or a carbon atom) Represents an alkyl group of the number 1 to 20, and may be replaced by —CS— or —CO—, but does not contain an —O—O— bond, and these groups are unsubstituted or include one or more preferably represents a group selected from the above may be substituted by a substituent L W.).
- the group represented by the above formula (W-1) is a group represented by the following formula (W-1-1), which may be unsubstituted or substituted by one or more of the above-described substituents L W. (W-1-7)
- the group represented by the above formula (W-2) is a group represented by the following formula (W-2-1) which may be unsubstituted or substituted by one or more of the above-described substituents L W (W-2-8)
- these groups may have a bond at an arbitrary position), preferably a group selected from the group represented by the above formula (W-3) is unsubstituted. Or may be substituted by one or more of the above-described substituents L W (Formula (W-3-1) to Formula (W-3-6))
- the group represented by the above formula (W-4) is a group represented by the following formula (W-4-1), which may be unsubstituted or substituted by one or more of the above-described substituents L W (W-4-9)
- the group represented by the above formula (W-5) is a group represented by the following formula (W-5-1), which may be unsubstituted or substituted by one or more of the above-described substituents L W. (W-5-13)
- these groups may have a bond at an arbitrary position, and RT represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms).
- RT represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
- Examples of the group represented by the above formula (W-6) include those represented by the following formula (W-6-1) which may be unsubstituted or substituted by one or more of the above-described substituents L W. (W-6-12)
- the group represented by the above formula (W-7) is a group represented by the following formula (W-7-1) which may be unsubstituted or substituted by one or more of the above-described substituents L W. (W-7-8)
- these groups may have a bond at an arbitrary position, and RT represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms).
- RT represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
- Examples of the group represented by the above formula (W-8) include those represented by the following formula (W-8-1), which may be unsubstituted or substituted by one or more of the above-described substituents L W. (W-8-19)
- the group represented by the above formula (W-9) is a group represented by the following formula (W-9-1), which may be unsubstituted or substituted by one or more of the above-described substituents L W (W-9-7)
- these groups may have a bond at an arbitrary position), preferably a group selected from the group represented by the above formula (W-10) is unsubstituted. Or may be substituted by one or more of the above-described substituents L W below (W-10-1) to (W-10-16)
- the group represented by the above formula (W-11) is a group represented by the following formula (W-11-1) which may be unsubstituted or substituted by one or more of the above-described substituents L W (W-11-10)
- the group represented by the above formula (W-12) is a group represented by the following formula (W-12-1), which may be unsubstituted or substituted by one or more of the above-described substituents L W (W-12-4)
- the group represented by the above formula (W-13) is a group represented by the following formula (W-13-1) which may be unsubstituted or substituted by one or more of the above-described substituents L W (W-13-10)
- the group represented by the above formula (W-17) is a group represented by the following formula (W-17-1) which may be unsubstituted or substituted by one or more of the above-described substituents L W (W-17-16)
- the group represented by the above formula (W-18) is a group represented by the following formula (W-18-1) which may be unsubstituted or substituted by one or more of the above-described substituents L W. (W-18-4)
- RT represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.
- the group containing a carbocycle or a heterocycle included in W 1 is unsubstituted or may be substituted by one or more of the above-described substituents L W (W-1-1), (W -1-2), formula (W-1-3), formula (W-1-4), formula (W-1-5), formula (W-1-6), formula (W-2-1) , Formula (W-6-9), Formula (W-6-11), Formula (W-6-12), Formula (W-7-2), Formula (W-7-3), Formula (W ⁇ 7-4), formula (W-7-6), formula (W-7-7), formula (W-7-8), formula (W-9-1), formula (W-12-1), Formula (W-12-2), Formula (W-12-3), Formula (W-12-4), Formula (W-13-7), Formula (W-13-9), Formula (W-13) ⁇ 10), more preferably a group selected from formula (W-14), formula (W-18-1), and formula (W-18-4).
- substituents L W may be substituted by the formula (W-2-1), the formula (W-7-3), the formula (W-7-7), the formula ( More preferably, it represents a group selected from W-14), which is unsubstituted or optionally substituted by one or more of the above-mentioned substituents L W (W-7-3), (W -7-7), a group selected from the formula (W-14) is more preferable, and the group (W—) which is unsubstituted or may be substituted by one or more of the above-described substituents L W It is even more preferred to represent a group represented by 7-7), which may be unsubstituted or substituted by one or more of the above-described substituents L W (W-7-7- 1)
- W 2 is a hydrogen atom, or an arbitrary hydrogen atom in the group is a fluorine atom, from the viewpoint of availability of raw materials and ease of synthesis.
- One —CH 2 — or two or more non-adjacent —CH 2 — may be each independently —O—, —CO—, —COO—, —OCO—, —O—.
- W 2 is a hydrogen atom, or, any hydrogen atom in the group may be substituted by a fluorine atom, 1 Of -CH 2 - or adjacent have not more than one -CH 2 - are each independently -O -, - CO -, - COO -, - OCO- 20 from a good 1 -C be replaced by It is more preferable to represent a linear or branched alkyl group or a group represented by P W — (Sp W —X W ) kW —, and W 2 represents a hydrogen atom or one —CH 2 - or adjacent have not more than one -CH 2 - straight-chain alkyl group are each independently 12 from a good 1 -C be replaced by -O-, or, P W - (Sp W - Even more preferably, it represents a group represented by X W ) kW —.
- P W represents a polymerizable group
- a preferable polymerizable group represents the same as defined for P 0 above
- Sp W represents a linear or branched alkylene group having 1 to 30 carbon atoms or In the alkylene group, a single bond —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO—, —COO—.
- X W is -O that -, - S -, - OCH 2 -, - CH 2 O -, - CO -, - COO -, - OCO -, - CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —SCH 2 —, —CH 2 S—, —CF 2 O—, —OCF 2 —, —CF 2 S—, —SCF 2 —, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —COO—, —CH 2 CH 2 —OCO—, —COO—CH 2 CH 2 —, —OCO—CH 2 CH 2 —, —CH 2 CH 2 —
- P W represents the formulas (P-1) and (P-2) defined by P 0 described above. ), Formula (P-7), formula (P-11) or formula (P-13) is preferred, and formula (P-1), formula (P-2) or formula (P-3) is More preferred is formula (P-1) or (P-2).
- Sp W is preferably an alkylene group or a single bond having 1 to 10 carbon atoms, more preferably an alkylene group or a single bond having 1 to 8 carbon atoms, and an alkylene group or a single bond having 1 to 6 carbon atoms.
- X W is preferably —O— or a single bond.
- kW is preferably an integer of 0 to 5, more preferably an integer of 0 to 3, and kW is particularly preferably an integer of 1 to 3.
- W 2 preferably includes a partial structure represented by the general formula (AO-1), specifically, the general formula (AO-1) Or a group represented by P W — (Sp W —X W ) kW — or a group represented by H — ((CH 2 ) m2 —O) k2 — (CH 2 ) m3 — Wherein k2 represents an integer of 2 to 10 and m2 represents an integer of 1 to 10, but a plurality of m2 may be the same integer or different, m3 Represents an integer of 0 to 10, but when m3 is 0, it represents a single bond. M2 is more preferably an integer from 1 to 6, k2 is more preferably an integer from 2 to 4, m3 is more preferably an integer from 0 to 8, and
- W 1 and W 2 may be combined to form a ring structure, in which case the cyclic group represented by —NW 1 W 2 is unsubstituted or substituted with one or more of the above-described substituents.
- any —CH ⁇ may be independently replaced by —N ⁇ , and —CH 2 — may be independently —O—, —S—, —NR T — (where R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.), May be replaced by —CS— or —CO—, but does not contain an —O—O— bond, and these groups are may be substituted by unsubstituted or one or more of the aforementioned substituents L W.) preferably represents a group selected from.
- the group represented by the above formula (W-19) is a group represented by the following formula (W-19-1) which may be unsubstituted or substituted by one or more of the above-described substituents L W. (W-19-3)
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-21 represents a group represented by the above formula (W-21).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- R T represents a group represented by the above formula (W-22).
- the group represented by the above formula (W-23) is unsubstituted or may be substituted by one or more of the above-described substituents L W as described below.
- Formula (W-23-1) to Formula (W-23-3) is unsubstituted or may be substituted by one or more of the above-described substituents L W as described below.
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- R T represents a group represented by the above formula (W-25).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-26 represents a group represented by the above formula (W-26).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-27 preferably represents a group represented by the above formula (W-27).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-28 represents a group represented by the above formula (W-28).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-29 preferably represents a group represented by the above formula (W-29).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-32 preferably represents a group represented by the above formula (W-32).
- W-32-1 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-32-5 which are substituted or optionally substituted by one or more of the above-mentioned substituents L W
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-33 represents a group represented by the above formula (W-33).
- the group represented by the above formula (W-34) is unsubstituted or substituted by one or more of the above-described substituents L W as described below.
- Formula (W-34-1) to Formula (W-34-5) is unsubstituted or substituted by one or more of the above-described substituents L W as described below.
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-35 represents a group represented by the above formula (W-35).
- W-35-1 which may be substituted or substituted by one or more of the above-described substituents L W
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-37 preferably represents a group represented by the above formula (W-37).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-39 represents a group represented by the above formula (W-39).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-40 represents a group represented by the above formula (W-40).
- W-40-1 which may be substituted or substituted by one or more of the above-mentioned substituents L W
- the cyclic group represented by —NW 1 W 2 may be unsubstituted or substituted with one or more of the above-described substituents L W ( W-19-1), Formula (W-21-2), Formula (W-21-3), Formula (W-21-4), Formula (W-23-2), Formula (W-23-3) ), Formula (W-25-1), Formula (W-25-2), Formula (W-25-3), Formula (W-30-2), Formula (W-30-3), Formula (W -35-1), a formula (W-36-2), a formula (W-36-3), a formula (W-36-4), a group selected from formula (W-40-1) preferable.
- W 1 and W 2 may be combined to form a ring structure, in which case the cyclic group represented by ⁇ CW 1 W 2 is unsubstituted or contains one or more of the above-mentioned substituents
- any —CH ⁇ may be independently replaced by —N ⁇ , and —CH 2 — may be independently —O—, —S—, —NR T — (where R T represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.), May be replaced by —CS— or —CO—, but does not contain an —O—O— bond, and these groups are may be substituted by unsubstituted or one or more of the aforementioned substituents L W.) preferably represents a group selected from.
- the group represented by the above formula (W-41) is a group represented by the following formula (W-41-1) which may be unsubstituted or substituted by one or more of the above-described substituents L W. (W-41-3)
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-43 represents a group represented by the above formula (W-43).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-44 represents a group represented by the above formula (W-44).
- the group represented by the above formula (W-45) is unsubstituted or substituted by one or more of the above-described substituents L W as described below.
- Formula (W-45-1) to Formula (W-45-4) is unsubstituted or substituted by one or more of the above-described substituents L W as described below.
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-46 represents a group represented by the above formula (W-46).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- R T represents a group represented by the above formula (W-47).
- W-47 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-47-3 which are substituted or optionally substituted by one or more of the above-mentioned substituents L W
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-48 represents a group represented by the above formula (W-48).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-49 preferably represents a group represented by the above formula (W-49).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- R T represents a group represented by the above formula (W-50).
- W-50 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-50-6 which are substituted or optionally substituted by one or more of the above-mentioned substituents L W
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-51 represents a group represented by the above formula (W-51).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-54 represents a group represented by the above formula (W-54).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-55 represents a group represented by the above formula (W-55).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-57 represents a group represented by the above formula (W-57).
- W-57-1 which may be substituted or substituted by one or more of the above-mentioned substituents L W
- the group represented by the above formula (W-58) is preferably unsubstituted or substituted by one or more of the above-described substituents L W as shown below (W— 58-1) to formula (W-58-6)
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- R T represents a group represented by the above formula (W-59).
- W-59 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-59-3 which are substituted or optionally substituted by one or more of the above-mentioned substituents L W
- the group represented by the above formula (W-60) is unsubstituted or substituted by one or more of the above-described substituents L W as described below.
- Formula (W-60-1) to Formula (W-60-4) is unsubstituted or substituted by one or more of the above-described substituents L W as described below.
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-61 represents a group represented by the above formula (W-61).
- R T represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
- W-62-1 represents a group represented by the above formula (W-62).
- W-62-1 which is substituted or optionally substituted by one or more of the above-mentioned substituents L W
- a group selected from formula (W-57-1) and formula (W-62-1) that is unsubstituted or optionally substituted by one or more of the above-described substituents L W more preferably represents an, represent a group represented by it may be substituted formula (W-57-1) by unsubstituted or substituted with one or more of the aforementioned substituents L W is further More preferable.
- the total number of ⁇ electrons contained in W 1 and W 2 is preferably 4 to 24 from the viewpoints of wavelength dispersion characteristics, storage stability, liquid crystallinity, and ease of synthesis.
- the above substituent L W is a fluorine atom, chlorine atom, pentafluorosulfuranyl group, nitro group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, or Any hydrogen atom may be substituted with a fluorine atom, and one —CH 2 — or two or more non-adjacent —CH 2 — are each independently —O—, —S—, —CO.
- 1 carbon atom which may be substituted by a group selected from —, —COO—, —OCO—, —O—CO—O—, —CH ⁇ CH—, —CF ⁇ CF— or —C ⁇ C—.
- a fluorine atom, a chlorine atom, or any hydrogen atom may be substituted with a fluorine atom, and one —CH 2 — or adjacent one is not two or more -CH 2 - is More preferably, it represents a linear or branched alkyl group having 1 to 12 carbon atoms which may be independently substituted with a group selected from —O—, —COO— or —OCO—, and is a fluorine atom.
- the chlorine atom or an arbitrary hydrogen atom represents a linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms which may be substituted with a fluorine atom, a fluorine atom, a chlorine atom, Or it is especially preferable to represent a C1-C8 linear alkyl group or a linear alkoxy group.
- G 1 represents the following formulas (G-1) to (G-22)
- Y is more preferably a hydrogen atom, s, t, u, and v are more preferably 0, and the following formula ( G-11-1) to formula (G-20-1)
- the compounds represented by the general formula (I) are preferably compounds represented by the following formulas (I-1) to (I-99).
- the compound represented by the general formula (I) is a known organic synthetic reaction (for example, condensation reaction, esterification reaction, Williamson reaction, Wittig reaction, ⁇ reaction) described in Organic reactions, Organic synthesis, New Experimental Chemistry Course, etc.
- the head reaction, Suzuki-Miyaura reaction, Friedel-Craft reaction, Heck reaction, aldol reaction, etc.) can be produced by appropriately combining them according to the structure.
- the compound represented by the formula (I-2) can be produced according to the following scheme.
- Protecting the hydroxyl group of benzyloxyphenol with a tetrahydropyranyl group provides a compound represented by the formula (1-2-2).
- the compound represented by the formula (1-2-3) is obtained by deprotecting the benzyl group of the compound represented by the formula (1-2-2).
- the compound represented by the formula (1-2-3) and 2- [2- (2-chloroethoxy) ethoxy] ethanol are etherified to obtain the compound represented by the formula (1-2-4).
- the compound represented by the formula (1-2-4) is acrylated and the tetrahydropyranyl group is deprotected to obtain the compound represented by the formula (1-2-5).
- a compound represented by the formula (1-2-6) is obtained by condensing the compound represented by the formula (1-2-5) and the compound represented by the formula (1-7-2). The tert-butyl group of the compound represented by the formula (1-2-6) is deprotected to obtain the compound represented by the formula (1-2-7).
- a compound represented by formula (1-2-8) is condensed with a compound represented by formula (1-2-1) to obtain a compound represented by formula (1-2-8).
- a compound represented by the formula (1-2) is obtained by condensing the compound represented by the formula (1-2-8) and 2-hydrazinobenzothiazole.
- the compound represented by the formula (I-6) can be produced according to the following scheme.
- the compound represented by the formula (I-5-3) is hydrolyzed to obtain the compound represented by the formula (I-5-4).
- a compound represented by formula (I-6-4) is obtained by condensing a compound represented by formula (I-5-4) and a compound represented by formula (I-6-3).
- a compound represented by formula (I-6-4) and a compound represented by formula (I-6-2) are condensed to obtain a compound represented by formula (I-6).
- the compound of the present invention is preferably used in a nematic liquid crystal composition, a smectic liquid crystal composition, a chiral smectic liquid crystal composition, and a cholesteric liquid crystal composition.
- a compound other than the present invention may be added.
- polymerizable compounds used by mixing with the polymerizable compound of the present invention include those represented by the general formula (X-11)
- P 11 , P 12 and P 13 each independently represent a polymerizable group
- Sp 11 , Sp 12 and Sp 13 each independently represent a single bond or an alkylene group having 1 to 20 carbon atoms.
- X 11, X 12 and X 13 are each independently —O—, —S—, —OCH 2 —, —CH 2 O—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO.
- W 11 and W 12 each independently represent a hydrogen atom or a methyl group
- Sp 14 and Sp 15 each independently represent an alkylene group having 2 to 18 carbon atoms
- X 14 and X 15 each independently -O-, -COO-, -OCO- or a single bond
- Z 13 and Z 14 each independently represent -COO- or -OCO-
- a 15 , A 16 and A 17 each independently And may be unsubstituted or substituted by a fluorine atom, a chlorine atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms.
- 4-phenylene group is preferred, and the following formulas (X-11a-1) to (X-11a-4)
- W 11 , W 12 , Sp 14 and Sp 15 have the same meaning as in formula (X-11a)
- W 11 , W 12 , Sp 14 and Sp 15 have the same meaning as in formula (X-11a)
- W 11 , W 12 , Sp 14 and Sp 15 have the same meaning as in formula (X-11a)
- W 11 , W 12 , Sp 14 and Sp 15 have the same meaning as in formula (X-11a)
- W 11 , W 12 , Sp 14 and Sp 15 have the same meaning as in formula (X-11a)
- preferable bifunctional polymerizable compounds include those represented by the following general formulas (X-11b-1) to (X-11b-3):
- W 13 and W 14 each independently represent a hydrogen atom or a methyl group
- Sp 16 and Sp 17 each independently represent an alkylene group having 2 to 18 carbon atoms. Is mentioned.
- compounds in which Sp 16 and Sp 17 are each independently an alkylene group having 2 to 8 carbon atoms are particularly preferred.
- P 14 represents a polymerizable group
- Sp 18 represents a single bond or an alkylene group having 1 to 20 carbon atoms, but one —CH 2 — or two or more non-adjacent — CH 2 — may be replaced by —O—, —COO—, —OCO—, —O—CO—O—
- X 16 represents a single bond, —O—, —COO—, or —OCO—.
- Z 15 represents a single bond, —COO— or —OCO—
- L 11 is independently a fluorine atom, a chlorine atom, one —CH 2 — or two or more non-adjacent —CH 2 —.
- —O—, —CO—NH—, —NH—CO—, —CH ⁇ CH—COO—, —CH ⁇ CH—OCO—, —COO—CH ⁇ CH—, —OCO—CH ⁇ CH—, —CH ⁇ CH—, —CF ⁇ CF— or —C ⁇ C— represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted.
- a polymerizable compound that does not exhibit liquid crystallinity can be added to the extent that the liquid crystallinity of the composition is not significantly impaired.
- any compound that is recognized as a polymer-forming monomer or polymer-forming oligomer in this technical field can be used without particular limitation. Specific examples include those described in “Photocuring Technology Data Book, Materials (Monomer, Oligomer, Photopolymerization Initiator)” (supervised by Kunihiro Ichimura, Kiyosuke Kato, Technonet).
- the compound of the present invention can be polymerized without using a photopolymerization initiator, but a photopolymerization initiator may be added depending on the purpose.
- concentration of the photopolymerization initiator is preferably 0.1% by mass to 15% by mass, more preferably 0.2% by mass to 10% by mass, and 0.4% by mass to 8% by mass with respect to the compound of the present invention. % Is more preferable.
- the photopolymerization initiator include benzoin ethers, benzophenones, acetophenones, benzyl ketals, and acylphosphine oxides.
- the photopolymerization initiator examples include 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one (IRGACURE 907), benzoic acid [1- [4- (phenylthio) benzoyl] heptylidene] Amino (IRGACURE OXE 01) etc. are mentioned.
- the thermal polymerization initiator examples include azo compounds and peroxides.
- Specific examples of the thermal polymerization initiator include 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis (isobutyronitrile) and the like.
- One type of polymerization initiator may be used, or two or more types of polymerization initiators may be used in combination.
- a stabilizer can be added to the liquid crystal composition of the present invention in order to improve its storage stability.
- the stabilizer examples include hydroquinones, hydroquinone monoalkyl ethers, tert-butylcatechols, pyrogallols, thiophenols, nitro compounds, ⁇ -naphthylamines, ⁇ -naphthols, nitroso compounds, and the like. It is done.
- the addition amount is preferably in the range of 0.005% by mass to 1% by mass, more preferably 0.02% by mass to 0.8% by mass, and 0.03% by mass with respect to the composition. To 0.5% by mass is more preferable.
- One kind of stabilizer may be used, or two or more kinds of stabilizers may be used in combination. Specific examples of the stabilizer include those represented by formulas (X-13-1) to (X-13-35).
- n represents an integer of 0 to 20
- the polymerizable liquid crystal composition containing the compound of the present invention is used for applications such as films, optical elements, functional pigments, pharmaceuticals, cosmetics, coating agents, synthetic resins, Depending on the purpose, metals, metal complexes, dyes, pigments, dyes, fluorescent materials, phosphorescent materials, surfactants, leveling agents, thixotropic agents, gelling agents, polysaccharides, ultraviolet absorbers, infrared absorbers, antioxidants Further, metal oxides such as ion exchange resin and titanium oxide can be added.
- the polymer obtained by polymerizing the polymerizable liquid crystal composition containing the compound of the present invention can be used for various applications.
- a polymer obtained by polymerizing a polymerizable liquid crystal composition containing the compound of the present invention without orientation can be used as a light scattering plate, a depolarizing plate, and a moire fringe prevention plate.
- polymerizing after orientating has optical anisotropy, and is useful.
- Such an optical anisotropic body includes, for example, a substrate obtained by rubbing a polymerizable liquid crystal composition containing the compound of the present invention with a cloth, a substrate on which an organic thin film is formed, or an alignment film on which SiO 2 is obliquely deposited. It can be produced by polymerizing the polymerizable liquid crystal composition after it is supported on a substrate having it or sandwiched between substrates.
- Examples of the method for supporting the polymerizable liquid crystal composition on the substrate include spin coating, die coating, extrusion coating, roll coating, wire bar coating, gravure coating, spray coating, dipping, and printing.
- an organic solvent may be added to the polymerizable liquid crystal composition during coating.
- the organic solvent hydrocarbon solvents, halogenated hydrocarbon solvents, ether solvents, alcohol solvents, ketone solvents, ester solvents, aprotic solvents and the like can be used.
- Toluene or hexane as the solvent methylene chloride as the halogenated hydrocarbon solvent, tetrahydrofuran, acetoxy-2-ethoxyethane or propylene glycol monomethyl ether acetate as the ether solvent, methanol, ethanol or alcohol as the alcohol solvent Isopropanol, acetone, methyl ethyl ketone, cyclohexanone, ⁇ -butyl lactone or N-methyl pyrrolidinone as the ketone solvent, ethyl acetate or cellosolve as the ester solvent, and dimethyl as the aprotic solvent It can be mentioned formamide or acetonitrile.
- the polymerizable liquid crystal composition may be used alone or in combination, and may be appropriately selected in consideration of the vapor pressure and the solubility of the polymerizable liquid crystal composition.
- a method for volatilizing the added organic solvent natural drying, heat drying, reduced pressure drying, or reduced pressure heat drying can be used.
- it is also effective to provide an intermediate layer such as a polyimide thin film on the substrate or to add a leveling agent to the polymerizable liquid crystal material.
- the method of providing an intermediate layer such as a polyimide thin film on a substrate is effective for improving the adhesion between a polymer obtained by polymerizing a polymerizable liquid crystal material and the substrate.
- Examples of the alignment treatment other than the above include use of flow alignment of liquid crystal material, use of electric field or magnetic field. These orientation means may be used alone or in combination. Furthermore, a photo-alignment method can be used as an alignment treatment method instead of rubbing. As a shape of the substrate, in addition to a flat plate, a curved surface may be included as a constituent part.
- substrate can be used regardless of an organic material and an inorganic material.
- organic material used as the substrate material examples include polyethylene terephthalate, polycarbonate, polyimide, polyamide, polymethyl methacrylate, polystyrene, polyvinyl chloride, polytetrafluoroethylene, polychlorotrifluoroethylene, polyarylate, polysulfone, and triacetyl.
- Cellulose, cellulose, polyetheretherketone and the like can be mentioned, and examples of the inorganic material include silicon, glass and calcite.
- the polymerizable liquid crystal composition containing the compound of the present invention When the polymerizable liquid crystal composition containing the compound of the present invention is polymerized, it is desirable that the polymerization proceeds rapidly. Therefore, a method of polymerizing by irradiating active energy rays such as ultraviolet rays or electron beams is preferable. When ultraviolet rays are used, a polarized light source or a non-polarized light source may be used. Further, when the polymerization is carried out with the liquid crystal composition sandwiched between two substrates, at least the substrate on the irradiation surface side must have appropriate transparency to the active energy rays.
- the orientation state of the unpolymerized part is changed by changing conditions such as an electric field, a magnetic field, or temperature, and further irradiation with active energy rays is performed. Then, it is possible to use a means for polymerization. Moreover, it is preferable that the temperature at the time of irradiation is in the temperature range in which the liquid crystal state of the polymerizable liquid crystal composition of the present invention is maintained.
- the polymerization is carried out at a temperature as close to room temperature as possible from the viewpoint of avoiding unintentional induction of thermal polymerization, that is, typically at a temperature of 25 ° C. It is preferable to make it.
- the intensity of the active energy ray is preferably 0.1 mW / cm 2 to 2 W / cm 2 . When the intensity is 0.1 mW / cm 2 or less, a great amount of time is required to complete the photopolymerization and the productivity is deteriorated. When the intensity is 2 W / cm 2 or more, the polymerizable liquid crystal compound or the polymerizable liquid crystal is used. There is a risk that the composition will deteriorate.
- the optical anisotropic body obtained by polymerization can be subjected to heat treatment for the purpose of reducing initial characteristic changes and achieving stable characteristic expression.
- the heat treatment temperature is preferably in the range of 50 to 250 ° C.
- the heat treatment time is preferably in the range of 30 seconds to 12 hours.
- optical anisotropic body manufactured by such a method may be peeled off from the substrate and used alone or without peeling. Further, the obtained optical anisotropic bodies may be laminated or bonded to another substrate for use.
- reaction vessel 166.5 g of the compound represented by the formula (I-2-4), 77.4 g of triethylamine, and 830 mL of dichloromethane were added. 55.4 g of acryloyl chloride was added dropwise while cooling with ice, followed by stirring at room temperature for 4 hours. The reaction solution was washed with brine and purified by column chromatography (alumina) to obtain an oily substance. To this was added 35 mL of 10% hydrochloric acid, 580 mL of methanol, and 580 mL of tetrahydrofuran, and the mixture was stirred at room temperature for 2 hours.
- reaction solution was washed with a saturated aqueous sodium hydrogen carbonate solution, water and brine in this order, and the solvent was distilled off. Purification was performed by column chromatography (silica gel) to obtain 116.8 g of a compound represented by the formula (I-2-5).
- reaction vessel 50 mL of hydrazine monohydrate and 50 mL of ethanol were added. An ethanol solution of 5.0 g of 1-bromohexane was added dropwise and stirred at 50 ° C. The reaction solution was diluted with dichloromethane and washed with water and brine in this order. After drying with sodium sulfate, the solvent was distilled off to obtain 2.8 g of a compound represented by the formula (I-3-1).
- reaction solution 5.0 g of a compound represented by formula (I-6-4), 1.5 g of a compound represented by formula (I-6-2), 60 mg of ( ⁇ ) -10-camphorsulfonic acid, 100 mL of tetrahydrofuran And stirred at room temperature for 8 hours.
- the reaction solution was purified by column chromatography (silica gel) and recrystallization (dichloromethane / hexane) to obtain 6.4 g of a compound represented by the formula (I-6).
- Transition temperature (temperature rise 5 ° C./min): C 106 N 125 I 1 H NMR (CDCl 3 ) ⁇ 0.92 (t, 3H), 1.11 (q, 2H), 1.25 (m, 2H), 1.36 (m, 2H), 1.48 (m, 4H), 1.68-1.81 (m, 12H), 1.93 (t, 4H), 2.32 (m, 3H), 2.58 (m, 2H), 2.71 (m, 1H) ), 3.30 (s, 3H), 3.48 (m, 2H), 3.62 (m, 2H), 3.85 (t, 2H), 3.94 (t, 2H), 4.17 (T, 2H), 4.47 (t, 2H), 5.82 (d, 2H), 6.12 (q, 2H), 6.40 (d, 2H), 6.87 (d, 2H) , 6.96 (m, 3H), 7.16 (t, 1H), 7.22 (m, 1H), 7.33 (t, 1H), 7.70 (q, 2H), 7.88 ( d
- Transition temperature (temperature increase 5 ° C./min, temperature decrease 5 ° C./min): C 101-105 (N 82) I 1 H NMR (CDCl 3 ) ⁇ 0.92 (t, 3H), 1.08-1.91 (m, 26H), 2.06 (d, 2H), 2.24 (d, 2H), 2.
- a compound represented by the formula (I-12-1) was produced by the method described in Patent Document 2.
- a reaction vessel 47.8 g of a compound represented by the formula (I-2-7), 15.3 g of a compound represented by the formula (I-12-1), 1.3 g of N, N-dimethylaminopyridine, 300 mL of dichloromethane was added.
- 14.7 g of diisopropylcarbodiimide was added dropwise with ice cooling, and the mixture was stirred at room temperature for 6 hours.
- the reaction solution was filtered, and the filtrate was washed with hydrochloric acid, water and brine in this order.
- Example 2 the compound represented by the formula (1-13-1) was produced using 2- (2-chloroethoxy) ethanol instead of 2- [2- (2-chloroethoxy) ethoxy] ethanol.
- a compound represented by the formula (I-13-2) was produced by the method described in JP2011-207765A.
- a compound represented by formula (1-15-3) is produced by the method described in 515-526, and a compound represented by formula (1-15-5) is produced by the method described in JP-A-2009-179563. did.
- the compounds (I-1) to (I-17) of the present invention have the same or higher solubility in various solvents than the comparative compounds (R-1) to (R-3).
- Examples 35 to 51, Comparative Examples 4 to 6 The polyimide solution for alignment film was applied to a cycloolefin polymer substrate using a spin coating method, dried at 60 ° C. for 10 minutes, and then baked at 100 ° C. for 60 minutes to obtain a coating film. The obtained coating film was rubbed. The rubbing treatment was performed using a commercially available rubbing apparatus.
- a coating solution having a composition of 18.9% for the evaluation target, 1% for the photopolymerization initiator Irgacure 907 (manufactured by BASF), 0.1% for 4-methoxyphenol and 80% for chloroform was prepared.
- This coating solution was applied to a rubbed cycloolefin polymer substrate by a spin coating method. After drying at 60 ° C. for 2 minutes, a coating film to be evaluated was prepared by irradiating ultraviolet rays with an intensity of 40 mW / cm 2 for 25 seconds using a high-pressure mercury lamp. The coating film was cut into a grid pattern with a cutter in accordance with JIS K5600-5-6, and a 2 mm square grid pattern was measured. Is shown in the table below.
- Classification 0 No peeling on any base.
- Classification 1 Small peeling of the coating film at the intersection of cuts is confirmed (less than 5%).
- Classification 2 The coating film is peeled off at the intersection along the cut line (5% or more and less than 15%).
- Classification 3 The coating film is partially or totally peeled along the cut line (15% or more and less than 35%).
- Classification 4 The coating film is largely and completely peeled along the cut line (35% or more and less than 65%).
- Classification 5 Classification 4 or more (65% or more).
- the compounds (I-1) to (I-17) of the present invention have the same degree of peeling or are less likely to occur than the comparative compounds (R-1) to (R-3). .
- the compound of the present invention is useful as a constituent member of the polymerizable composition.
- the optical anisotropic body using the polymeric liquid crystal composition containing the compound of this invention is useful for uses, such as an optical film.
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Abstract
Description
《位相差の測定》
配向膜用ポリイミド溶液を厚さ0.7mmのガラス基材にスピンコート法を用いて塗布し、100℃で10分乾燥した後、200℃で60分焼成することにより塗膜を得る。得られた塗膜を市販のラビング装置を用いてラビング処理する。
A1及びA2は各々独立して1,4-フェニレン基、1,4-シクロヘキシレン基、ピリジン-2,5-ジイル基、ピリミジン-2,5-ジイル基、ナフタレン-2,6-ジイル基、ナフタレン-1,4-ジイル基、テトラヒドロナフタレン-2,6-ジイル基、デカヒドロナフタレン-2,6-ジイル基又は1,3-ジオキサン-2,5-ジイル基を表すが、これらの基は無置換であるか又は1つ以上の置換基Lによって置換されても良く、Lはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LはPL-(SpL-XL)kL-で表される基を表しても良く、ここでPLは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLが複数存在する場合それらは同一であっても異なっていても良く、XLは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLが複数存在する場合それらは同一であっても異なっていても良く(ただし、PL-(SpL-XL)kL-には-O-O-結合を含まない。)、kLは0から10の整数を表すが、化合物内にLが複数存在する場合それらは同一であっても異なっていても良く、置換基Lはフッ素原子、塩素原子、ペンタフルオロスルフラニル基、ニトロ基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、又は、任意の水素原子はフッ素原子に置換されても良く、1個の-CH2-又は隣接していない2個以上の-CH2-は各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-O-CO-O-、-CH=CH-、-CF=CF-又は-C≡C-から選択される基によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すことが好ましく、フッ素原子、塩素原子、又は、任意の水素原子はフッ素原子に置換されても良く、1個の-CH2-又は隣接していない2個以上の-CH2-は各々独立して-O-、-COO-又は-OCO-から選択される基によって置換されても良い炭素原子数1から12の直鎖状又は分岐状アルキル基を表すことがより好ましく、フッ素原子、塩素原子、又は、任意の水素原子はフッ素原子に置換されても良い炭素原子数1から12の直鎖状又は分岐状アルキル基若しくはアルコキシ基を表すことがさらに好ましく、フッ素原子、塩素原子、又は、炭素原子数1から8の直鎖アルキル基若しくは直鎖アルコキシ基を表すことが特に好ましい。
Z1及びZ2は各々独立して-O-、-S-、-OCH2-、-CH2O-、-CH2CH2-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-、-N=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、Z1が複数存在する場合それらは同一であっても異なっていても良く、Z2が複数存在する場合それらは同一であっても異なっていても良く、
G1は芳香族炭化水素環又は芳香族複素環からなる群から選ばれる少なくとも1つの芳香族環を有する2価の基を表すが、G1で表される基中の芳香族環に含まれるπ電子の数は12以上であり、G1で表される基は無置換であるか又は1つ以上の置換基LGによって置換されても良く、置換基LGはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LGはPLG-(SpLG-XLG)kLG-で表される基を表しても良く、ここでPLGは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLGは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLGが複数存在する場合それらは同一であっても異なっていても良く、XLGは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLGが複数存在する場合それらは同一であっても異なっていても良く(ただし、PLG-(SpLG-XLG)kLG-には-O-O-結合を含まない。)、kLGは0から10の整数を表すが、化合物内にLGが複数存在する場合それらは同一であっても異なっていても良く、m1及びm2は各々独立して0から6の整数を表すが、m1+m2は0から6の整数を表す。)で表される化合物であることが好ましい。
W2は水素原子、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、W2は少なくとも1つの芳香族基を有する、炭素原子数2から30の基を表しても良いが、当該基は無置換であるか又は1つ以上の置換基LWによって置換されても良く、若しくは、W2はPW-(SpW-XW)kW-で表される基を表しても良く、ここでPWは重合性基を表し、SpWはスペーサー基又は単結合を表し、SpWが複数存在する場合それらは同一であっても異なっていても良く、XWは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XWが複数存在する場合それらは同一であっても異なっていても良く(ただし、PW-(SpW-XW)kW-には-O-O-結合を含まない。)、kWは0から10の整数を表し、
置換基LWはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LWはPLW-(SpLW-XLW)kLW-で表される基を表しても良く、ここでPLWは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpLWは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLWが複数存在する場合それらは同一であっても異なっていても良く、XLWは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLWが複数存在する場合それらは同一であっても異なっていても良く(ただし、PLW-(SpLW-XLW)kLW-には-O-O-結合を含まない。)、kLWは0から10の整数を表すが、化合物内に置換基LWが複数存在する場合それらは同一であっても異なっていても良く、
Yは水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基又は1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくはYはPY-(SpY-XY)kY-で表される基を表しても良く、PYは重合性基を表し、好ましい重合性基は上記P0で定義したものと同一のものを表し、SpYは上述の1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表し、SpYが複数存在する場合それらは同一であっても異なっていても良く、XYは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XYが複数存在する場合それらは同一であっても異なっていても良く(ただし、PY-(SpY-XY)kY-には-O-O-結合を含まない。)、kYは0から10の整数を表すが、W1及びW2は一緒になって環構造を形成しても良い。)から選ばれる基を表す。)から選ばれる基を表すことがより好ましい。溶媒への溶解性、合成の容易さの観点から、G1は上記の式(M-1)、式(M-3)、式(M-4)、式(M-7)、式(M-8)から選ばれる基を表すことがさらに好ましく、式(M-1)、式(M-7)、式(M-8)から選ばれる基を表すことがさらにより好ましく、式(M-7)、式(M-8)から選ばれる基を表すことが特に好ましい。
(実施例1)式(I-1)で表される化合物の製造
転移温度(昇温5℃/分):C 89-123 I
1H NMR(CDCl3)δ 1.05(t,3H),1.70(m,2H),2.70(t,2H),3.58-3.73(m,6H),3.75(t,2H),4.02(t,2H),4.27(t,2H),5.84(dd,1H),6.12(dd,1H),6.42(dd,1H),6.65(d,2H),7.00(d,2H),7.15-7.45(m,5H),7.51-7.70(m,5H),7.78(dd,1H),8.17(s,1H),11.7(s,1H)ppm.
LCMS:694[M+1]
(実施例2)式(I-2)で表される化合物の製造
転移温度(昇温5℃/分):C 75-108 N 180 I
1H NMR(CDCl3)δ 0.94(t,3H),1.10(m,2H),1.25(m,2H),1.29-1.57(m,11H),1.80-2.08(m,6H),2.30(m,2H),2.54(m,1H),3.67-3.78(m,6H),3.85(t,2H),4.11(t,2H),4.32(t,2H),5.84(dd,1H),6.15(dd,1H),6.40(dd,1H),6.82-7.00(m,4H),7.08-7.60(m,4H),7.65-8.10(m,3H)、8.40(s,1H)、11.6(s,1H)ppm.
LCMS:826[M+1]
(実施例3)式(I-3)で表される化合物の製造
転移温度(昇温5℃/分):C 131 I
1H NMR(CDCl3)δ 0.88-0.94(m,6H),1.10(m,2H),1.22-1.52(m,13H),1.72(m,6H),1.94(t,4H),2.32(m,4H),2.53-2.62(m,3H),3.69-3.77(m,6H),3.86(t,2H),4.12(t,2H),4.27-4.34(m,4H),5.83(dd,1H),6.16(dd,1H),6.43(dd,1H),6.91(d,2H),6.97-7.02(m,3H),7.16(t,1H),7.23(dd,1H),7.33(t,1H),6.66-7.72(m,3H),7.90(d,1H)ppm.
LCMS:910[M+1]
(実施例4)式(I-4)で表される化合物の製造
転移温度(昇温5℃/分):C 90 Sm 218 N 265 I
1H NMR(CDCl3)δ 0.88(m,6H),1.01-1.19(m,8H),1.32-1.45(m,6H),1.71-1.76(m,6H),1.88-1.99(m,3H),2.17(m,12H),2.31(m,4H),2.53(m,2H),2.67(m,1H),3.70-3.76(m,6H),3.85(t,2H),4.11(t,2H),4.31(m,4H),5.82(d,2H),6.15(q,2H),6.43(d,2H),6.92(m,5H),7.14-7.26(m,2H),7.33(t,1H),7.68(m,3H),7.88(s,1H)ppm.
(実施例5)式(I-5)で表される化合物の製造
転移温度(昇温5℃/分):C 77 S 90 N 109 I
1H NMR(CDCl3)δ 0.89(t,3H),1.20-1.35(m,10H),1.61-1.69(m,6H),1.78(m,2H),1.90(m,2H),2.07(t,4H),2.23(d,4H),2.50(m,2H),3.69-3.76(m,12H),3.83-3.87(m,8H),4.11(t,4H),4.32(t,6H),5.82(d,2H),6.15(q,2H),6.42(d,2H),6.83-6.98(m,10H),7.13(t,1H),7.32(t,1H),7.53(t,1H),7.66(t,2H),8.13(s,1H)ppm.
(実施例6)式(I-6)で表される化合物の製造
転移温度(昇温5℃/分):C 85 N 128 I
1H NMR(CDCl3)δ 1.22-1.28(m,4H),1.44-1.47(m,8H),1.60-1.82(m,12H),1.90(m,2H),2.07(t,4H),2.24(d,4H),2.53(m,2H),3.30(s,3H),3.50(t,2H),3.66(t,2H),3.85-3.89(m,6H),3.93(t,4H),4.17(t,4H),4.53(t,2H),5.82(d,2H),6.13(q,2H),6.40(d,2H),6.83-6.90(m,6H),6.95-6.98(m,4H),7.14(t,1H),7.32(t,1H),7.52(t,1H),7.67(t,2H),8.33(s,1H)ppm.
(実施例7)式(I-7)で表される化合物の製造
転移温度(昇温5℃/分):C 106 N 125 I
1H NMR(CDCl3)δ 0.92(t,3H),1.11(q,2H),1.25(m,2H),1.36(m,2H),1.48(m,4H),1.68-1.81(m,12H),1.93(t,4H),2.32(m,3H),2.58(m,2H),2.71(m,1H),3.30(s,3H),3.48(m,2H),3.62(m,2H),3.85(t,2H),3.94(t,2H),4.17(t,2H),4.47(t,2H),5.82(d,2H),6.12(q,2H),6.40(d,2H),6.87(d,2H),6.96(m,3H),7.16(t,1H),7.22(m,1H),7.33(t,1H),7.70(q,2H),7.88(d,1H),8.01(s,1H)ppm.
(実施例8)式(I-8)で表される化合物の製造
転移温度(昇温5℃/分):C 89-95 N 145 I
1H NMR(CDCl3)δ 1.24(m,4H),1.65(m,4H),1.91(m,2H),2.05-2.25(m,12H),2.55(m,2H),3.30(s,3H),3.51(m,2H),3.67(m,2H),3.84-3.89(m,6H),4.05(t,4H),4.36(t,4H),4.54(t,2H),5.84(dd,2H),6.13(dd,2H),6.41(dd,2H),6.84-6.89(m,6H),6.97-7.00(m,4H),7.14(t,1H),7.33(t,1H),7.52(d,1H),7.67(dd,2H),8.34(s,1H)ppm.
LCMS:1076[M+1]
(実施例9)式(I-9)で表される化合物の製造
転移温度(昇温5℃/分)C 71 N 115 I
1H NMR(CDCl3)δ 1.19-1.29(m,4H),1.41-1.82(m,22H),1.91(m,2H),2.08(m,4H),2.24(m,4H),2.53(m,2H),3.62(m,3H),3.67(m,2H),3.84-3.90(m,5H),3.94(t,4H),4.15-4.19(m,6H),4.53(t,2H),5.76(dd,1H),5.82(dd,2H),6.08(dd,1H),6.12(dd,2H),6.37(dd,1H),6.40(dd,2H),6.84-6.90(m,6H),6.95-6.98(m,4H),7.14(t,1H),7.32(t,1H),7.53(d,1H),7.65(d,1H),7.69(d,1H),8.34(s,1H)ppm.
LCMS:1244[M+1]
(実施例10)式(I-10)で表される化合物の製造
転移温度(昇温5℃/分、降温5℃/分):C 101-105(N 82)I
1H NMR(CDCl3)δ 0.92(t,3H),1.08-1.91(m,26H),2.06(d,2H),2.24(d,2H),2.51(m,2H),3.30(s,3H),3.51(dd,2H),3.67(dd,2H),3.87(quin,4H),3.94(t,2H),4.17(t,2H),4.54(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.86(m,3H),6.97(m,2H),7.16(m,2H),7.32(t,1H),7.65(d,1H),7.70(d,1H),7.82(d,1H),8.36(s,1H)ppm.
(実施例11)式(I-11)で表される化合物の製造
転移温度(昇温5℃/分):C 67-100 I
1H NMR(CDCl3)δ 1.00(t,3H),1.28(m,2H),1.45-1.81(m,12H),1.97(br,1H),2.13(m,2H),2.26(m,2H),2.57(tt,1H),2.65(t,2H),3.27(s,3H),3.37(m,2H),3.50(m,2H),3.70(t,2H),3.95(q,4H),4.17(t,2H),4.33(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.87(d,2H),6.98(m,3H),7.15(t,1H),7.25(m,5H),7.32(t,1H),7.64(m,2H),7.69(d,1H),7.91(s,1H)ppm.
(実施例12)式(I-12)で表される化合物の製造
LCMS:1153[M+1]
(実施例13)式(I-13)で表される化合物の製造
LCMS:1088[M+1]
(実施例14)式(I-14)で表される化合物の製造
LCMS:1259[M+1]
(実施例15)式(I-15)で表される化合物の製造
LCMS:1222[M+1]
(実施例16)式(I-16)で表される化合物の製造
LCMS:1188[M+1]
(実施例17)式(I-17)で表される化合物の製造
1H NMR(CDCl3)δ 0.92(t,3H),1.05-1.83(m,32H),1.93(t,5H),2.33(m,4H),2.55(m,2H),2.71(m、1H),3.30(s,3H),3.62(m,2H),3.85(t,2H),3.94(t,2H),4.17(t,2H),4.48(t,2H),5.82(dd,1H),6.12(dd,1H),6.40(dd,1H),6.88(d,2H),6.99(m,3H),7.17(t,1H),7.23(dd,1H),7.34(t,1H),7.66(d,1H),7.71(d,1H),7.89(d,1H),8.02(s,1H)ppm.
LCMS:978[M+1]
実施例1から実施例17と同様の方法及び公知の方法を用いて、上述の式(I-18)から式(I-99)で表される化合物を製造した。
(実施例18~34、比較例1~3)
実施例1から実施例17記載の式(I-1)から式(I-17)で表される化合物及び特許文献1記載の化合物(R-1)、特許文献2記載の化合物(R-2)、特許文献3記載の化合物(R-3)を評価対象の化合物とした。
(実施例35~51、比較例4~6)
配向膜用ポリイミド溶液をシクロオレフィンポリマー基材にスピンコート法を用いて塗布し、60℃で10分乾燥した後、100℃で60分焼成することにより塗膜を得た。得られた塗膜をラビング処理した。ラビング処理は、市販のラビング装置を用いて行った。
分類0:いずれの基盤目にもはがれがない。
分類1:カットの交差点における塗膜の小さなはがれが確認される(5%未満)。
分類2:塗膜がカットの線に沿って、交差点においてはがれている(5%以上15%未満)。
分類3:塗膜がカットの線に沿って部分的、全面的にはがれている(15%以上35%未満)。
分類4:塗膜がカットの線に沿って部分的、全面的に大きくはがれを生じている(35%以上65%未満)。
分類5:分類4以上(65%以上)。
Claims (13)
- 分子内に少なくとも1つの下記一般式(I-0-R)
- 一般式(I)
A1及びA2は各々独立して1,4-フェニレン基、1,4-シクロヘキシレン基、ピリジン-2,5-ジイル基、ピリミジン-2,5-ジイル基、ナフタレン-2,6-ジイル基、ナフタレン-1,4-ジイル基、テトラヒドロナフタレン-2,6-ジイル基、デカヒドロナフタレン-2,6-ジイル基又は1,3-ジオキサン-2,5-ジイル基を表すが、これらの基は無置換であるか又は1つ以上の置換基Lによって置換されても良く、Lはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LはPL-(SpL-XL)kL-で表される基を表しても良く、ここでPLは重合性基を表し、SpLは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLが複数存在する場合それらは同一であっても異なっていても良く、XLは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLが複数存在する場合それらは同一であっても異なっていても良く、kLは0から10の整数を表すが、化合物内にLが複数存在する場合それらは同一であっても異なっていても良く、Z1及びZ2は各々独立して-O-、-S-、-OCH2-、-CH2O-、-CH2CH2-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-OCO-NH-、-NH-COO-、-NH-CO-NH-、-NH-O-、-O-NH-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-、-N=CH-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、Z1が複数存在する場合それらは同一であっても異なっていても良く、Z2が複数存在する場合それらは同一であっても異なっていても良く、G1は芳香族炭化水素環又は芳香族複素環からなる群から選ばれる少なくとも1つの芳香族環を有する2価の基を表すが、G1で表される基中の芳香族環に含まれるπ電子の数は12以上であり、G1で表される基は無置換であるか又は1つ以上の置換基LGによって置換されても良く、LGはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LGはPLG-(SpLG-XLG)kLG-で表される基を表しても良く、ここでPLGは重合性基を表し、SpLGは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLGが複数存在する場合それらは同一であっても異なっていても良く、XLGは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLGが複数存在する場合それらは同一であっても異なっていても良く、kLGは0から10の整数を表すが、化合物内にLGが複数存在する場合それらは同一であっても異なっていても良く、
m1及びm2は各々独立して0から6の整数を表すが、m1+m2は0から6の整数を表すが、ただし、一般式(I)中には-O-O-結合を含まない。)で表される請求項2に記載の化合物。 - 一般式(I)において、G1が下記の一般式(M-1)から一般式(M-6)
W2は水素原子、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、W2は少なくとも1つの芳香族基を有する、炭素原子数2から30の基を表しても良いが、当該基は無置換であるか又は1つ以上の置換基LWによって置換されても良く、若しくは、W2はPW-(SpW-XW)kW-で表される基を表しても良く、ここでPWは重合性基を表し、SpWは炭素原子数1から30の直鎖状又は分岐状アルキレン基又は単結合を表すが、該アルキレン基は1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-又は-C≡Cで置き換えられていても良く、SpWが複数存在する場合それらは同一であっても異なっていても良く、XWは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XWが複数存在する場合それらは同一であっても異なっていても良く、kWは0から10の整数を表し、LWはフッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくは、LWはPLW-(SpLW-XLW)kLW-で表される基を表しても良く、ここでPLWは重合性基を表し、SpLWは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpLWが複数存在する場合それらは同一であっても異なっていても良く、XLWは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XLWが複数存在する場合それらは同一であっても異なっていても良く、kLWは0から10の整数を表すが、化合物内にLWが複数存在する場合それらは同一であっても異なっていても良く、
Yは水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基又は1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-S-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-CH=CH-、-CF=CF-又は-C≡C-によって置換されても良い炭素原子数1から20の直鎖状又は分岐状アルキル基を表すが、当該アルキル基中の任意の水素原子はフッ素原子に置換されても良く、若しくはYはPY-(SpY-XY)kY-で表される基を表しても良く、PYは重合性基を表し、SpYは1個の-CH2-又は隣接していない2個以上の-CH2-が各々独立して-O-、-COO-、-OCO-によって置換されても良い炭素原子数1から10の直鎖状アルキレン基又は単結合を表すが、SpYが複数存在する場合それらは同一であっても異なっていても良く、XYは-O-、-S-、-OCH2-、-CH2O-、-CO-、-COO-、-OCO-、-CO-S-、-S-CO-、-O-CO-O-、-CO-NH-、-NH-CO-、-SCH2-、-CH2S-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH=CH-COO-、-CH=CH-OCO-、-COO-CH=CH-、-OCO-CH=CH-、-COO-CH2CH2-、-OCO-CH2CH2-、-CH2CH2-COO-、-CH2CH2-OCO-、-COO-CH2-、-OCO-CH2-、-CH2-COO-、-CH2-OCO-、-CH=CH-、-N=N-、-CH=N-N=CH-、-CF=CF-、-C≡C-又は単結合を表すが、XYが複数存在する場合それらは同一であっても異なっていても良く、kYは0から10の整数を表すが、W1及びW2は一緒になって環構造を形成しても良い。)から選ばれる基を表す。)から選ばれる基を表す、請求項3又は請求項4に記載の化合物。 - 前記一般式(T2-1)又は一般式(T2-2)中のW2が前記一般式(AO-1)で表される部分構造を含む、請求項5に記載の化合物。
- 前記一般式(I)において、G1が式(M-7)又は式(M-8)で表される請求項5又は請求項6に記載の化合物。
- 前記一般式(I)において、R1とR2のうちいずれか一方のみが一般式(I-0-R)で表される基を表す、請求項3~請求項7のいずれか一項に記載の化合物。
- 請求項1~請求項8のいずれか一項に記載の化合物を含有する組成物。
- 請求項1~請求項8のいずれか一項に記載の化合物を含有する液晶組成物。
- 請求項9又は請求項10に記載の組成物を用いた重合体。
- 請求項11記載の重合体を用いた光学異方体。
- 請求項1~請求項8のいずれか一項に記載の化合物を用いた樹脂、樹脂添加剤、オイル、フィルター、接着剤、粘着剤、油脂、インキ、医薬品、化粧品、洗剤、建築材料、包装材、液晶材料、有機EL材料、有機半導体材料、電子材料、表示素子、電子デバイス、通信機器、自動車部品、航空機部品、機械部品、農薬及び食品並びにそれらを使用した製品。
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JP6624696B2 (ja) | 2019-12-25 |
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