Polymerizable liquid crystal compound, polymerizable composition, phase difference film, layered body for transfer, optical member

Abstract

The present application is a polymerizable liquid crystal compound represented by the following general formula (1). General formula (1) (Each symbol in general formula (1) is as described in the specification.)

Description

[0001] This application is a divisional application, whose parent application application number is 201880065915.7 (PCT / JP2018 / 037765), application date is October 10, 2018, and the invention title is: Polymerizable liquid crystal compound, polymerizable composition, polymer, retardation film and method for manufacturing the same, transfer laminate, optical component and method for manufacturing the same, and display device. Technical Field

[0002] This invention relates to a polymerizable liquid crystal compound, a polymerizable composition, a polymer, a phase retardation film and a method for manufacturing the same, a transfer laminate, an optical component and a method for manufacturing the same, and a display device. Background Technology

[0003] Previously, regarding display devices such as liquid crystal displays or light-emitting displays, the industry proposed a configuration in which optical components such as phase retardation films and polarizing plates are arranged on the panel surface.

[0004] For example, in light-emitting display devices such as organic light-emitting display devices, metal electrodes with excellent reflectivity are provided in order to utilize the light from the light-emitting layer more effectively. On the other hand, the use of these metal electrodes increases the reflection of external light. Therefore, it is known that in light-emitting display devices, in order to suppress this reflection of external light, a circularly polarizing plate comprising a quarter-wavelength plate that converts linearly polarized light into circularly polarized light and a polarizer is used on the visual recognition side.

[0005] In addition to the aforementioned quarter-wavelength plate, retardation films also include half-wavelength plates that shift the polarization plane of linearly polarized light by 90 degrees. These retardation films can accurately convert a specific monochromatic light into a phase difference of 1 / 4λ or 1 / 2λ of the light wavelength. However, existing retardation films have the problem that polarized light output from the film can be converted into colored polarized light. This is because the materials constituting the retardation film have wavelength dispersion based on the phase difference. Compared to white light, which exists as a mixture of light in the visible light region, the polarization state of the light at each wavelength is distributed. To prevent this problem, the wavelength dispersion must be controlled to achieve the designed phase difference at each wavelength. This requires a broadband retardation film that can provide a uniform phase difference for light over a wide wavelength range, i.e., a retardation film with inverse wavelength dispersion.

[0006] Methods for manufacturing phase retardation films include: stretching the film; or, for example, coating a polymeric composition containing a liquid crystal compound onto an oriented support, drying the solvent to orient the liquid crystal compound, and then polymerizing it by ultraviolet light or heat.

[0007] As a phase retardation film with inverse wavelength dispersion, a method has been proposed, for example, to stack two phase retardation layers by assigning angles to each other in the direction of the orientation axis (Patent Documents 1 and 2). However, such a stack has problems such as requiring two phase retardation layers, and the manufacturing process of stacking the two phase retardation layers is more complicated or the thickness of the phase retardation film increases.

[0008] With the increasing functionality and popularity of portable information terminals, there is a growing demand to reduce the thickness of display devices. As a result, there is also a pursuit of thinner phase retardation films, which are components of these devices.

[0009] Therefore, in order to construct a retardation layer with reverse wavelength dispersion in a single layer, the industry is promoting the development of liquid crystal compounds with reverse wavelength dispersion that reduce or reverse the wavelength dispersion of birefringence (Δn) (e.g., Patent Documents 3-4). Furthermore, it is generally considered that: taking the wavelength λ of the incident light relative to the retardation film as the horizontal axis, and taking its birefringence (Δn = refractive index n relative to the anomalous light) as... e When the slope of the curve obtained by plotting the refractive index n0 relative to ordinary light on the vertical axis is positive (rising to the right), the wavelength dispersion of its birefringence is inverse, or the liquid crystal compound constituting the phase difference film has inverse wavelength dispersion.

[0010] However, existing liquid crystal compounds with reverse wavelength dispersion, such as those in Patent Documents 3-4, have a small birefringence (Δn). Therefore, in order to obtain the required phase difference (Re(λ) = birefringence Δn(λ) × film thickness d), the film thickness must be increased.

[0011] Furthermore, for example, in a quarter-wavelength plate, if ideal reverse wavelength dispersion is obtained, all wavelengths in the visible light region can be converted into circularly polarized light, thus completely preventing the reflection of external light. However, the reverse wavelength dispersion of existing liquid crystal compounds is insufficient, and it is desirable to achieve near-ideal reverse wavelength dispersion.

[0012] In Patent Document 5, a polymeric compound exhibiting a practically low melting point, excellent solubility in common solvents, and the ability to achieve the same polarization conversion over a wide wavelength range is disclosed. This compound has a structure with two side chains on a single tetravalent benzene ring group in its main chain. The polymeric compound of Patent Document 5 itself does not possess liquid crystal properties (Table 1 of Patent Document 5). While mixing an existing reverse-wavelength dispersible liquid crystal compound with the polymeric compound of Patent Document 5 suggests the creation of a reverse-wavelength dispersible optical film, the difference between its reverse-wavelength dispersibility and the ideal reverse-wavelength dispersibility is significant.

[0013] Patent Document 6 discloses a polymeric compound that exhibits high storage stability by not crystallizing when added to a polymeric composition. The polymeric compound is characterized by having a side chain on a trivalent benzene ring M in the main chain of the compound, and of the two substituents in the main chain direction of the trivalent benzene ring M, one substituent has a ring structure and the other substituent has a two-ring structure.

[0014] Furthermore, in Patent Document 7, a polymeric compound that does not crystallize when added to a polymeric composition and has high storage stability is disclosed, which has a structure with two side chains on a tetravalent benzene ring group of the main chain of the same compound as in Patent Document 6 and the same compound as in Patent Document 5.

[0015] Patent documents 6 and 7 disclosed only the following: when the polymeric compound is added to the polymeric composition, it does not crystallize and has high storage stability; when the polymeric compound is added to the parent liquid crystal to make an optical film, it is not easy to cause discoloration or peeling off from the substrate.

[0016] Prior art literature

[0017] Patent documents

[0018] Patent Document 1: Japanese Patent Application Publication No. 10-68816

[0019] Patent Document 2: Japanese Patent Application Publication No. 2001-4837

[0020] Patent Document 3: Japanese Patent Publication No. 2010-522893

[0021] Patent Document 4: Japanese Patent No. 5962760

[0022] Patent Document 5: International Publication No. 2014 / 061709

[0023] Patent Document 6: International Publication No. 2016 / 136533

[0024] Patent Document 7: International Publication No. 2016 / 104317 Summary of the Invention

[0025] The problem the invention aims to solve

[0026] In view of the actual situation described above, the present invention aims to provide: a polymeric liquid crystal compound with a large birefringence (Δn) and inverse wavelength dispersion, a polymeric composition comprising the polymeric liquid crystal compound, a polymer obtained by polymerizing the polymeric liquid crystal compound or the polymeric composition, a phase retardation film having a phase retardation layer comprising the polymeric composition, a method for manufacturing the same, a transfer laminate capable of transferring the phase retardation layer, an optical component having the phase retardation film, a method for manufacturing the same, and a display device.

[0027] means for solving problems

[0028] One embodiment of the present invention provides a polymeric liquid crystal compound represented by the following general formula (1).

[0029] [Chemistry 1]

[0030] General formula (1)

[0031]

[0032] (In general formula (1), L) 1 L 2 L 3 and L 4 Represent independently the following: -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-CO O-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -C OO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or single bond,

[0033] A 1 and A 2 Each of these groups independently represents a divalent alicyclic hydrocarbon group with 3 to 20 carbon atoms, either unsubstituted or substituted with one or more substituents E. Any carbon atom of this alicyclic hydrocarbon group may be substituted with a heteroatom.

[0034] A 3and A 4 Each of these groups independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group with 3 to 20 carbon atoms, either unsubstituted or substituted with one or more substituents E. Any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a heteroatom.

[0035] R 1 and R 2 Each group is independently represented by a group selected from the following general formula (R-1).

[0036] General formula (R-1): -L 5 -R sp1 -Z 1

[0037] In general formula (R-1), L 5 Represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OC O-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=NN=CH-, -CF=CF-, -C≡C- or single bond, R sp1 This indicates that one -CH2- or two or more non-adjacent -CH2- atoms can be independently replaced by an alkylene group or single bond with 1 to 20 carbon atoms, belonging to the categories -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. Z 1 It represents a polymeric functional group.

[0038] D 1 and D 2 Each group is independently represented by a group selected from the following general formula (D-1).

[0039] Substituents E, E 1 and E 2Each of the following groups can be independently represented: fluorine, chlorine, bromine, iodine, pentafluorosulfuryl, nitro, cyano, isocyanate, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyanate, or one -CH2- or two or more non-adjacent -CH2- groups that can be independently replaced by -O-, -S-, -CO-, or -COO-. A straight-chain or branched alkyl group with 1 to 20 carbon atoms, consisting of -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-, or -C≡C-, wherein any hydrogen atom in the alkyl group may be replaced by a fluorine atom, or, with substituents E, E 1 and E 2 -LE-R can be represented independently. spE -Z E The groups represented here, LE and R spE and Z E Respectively represent the above L 5 R sp1 and Z 1 Those with the same defined groups can be respectively combined with the above-mentioned L 5 R sp1 and Z 1 Whether the compounds are the same or different, multiple substituents E, E, are present in the compound respectively. 1 and E 2 In any case, they may be the same or different.

[0040] In L 3 L 4 A 3 and A 4 When multiple instances exist, they can be the same or different.

[0041] m1 and m2 independently represent integers from 1 to 4, and n1 and n2 independently represent integers from 0 to 3.

[0042] [Chemistry 2]

[0043] General formula (D-1)

[0044]

[0045] (In general formula (D-1), G) 1 This refers to an alkyl group having 1 to 6 hydrogen atoms or carbon atoms, which may be unsubstituted or substituted with one or more of the aforementioned substituents E.

[0046] Q 1 This refers to an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group, wherein any carbon atom of the aromatic hydrocarbon group may be replaced by a heteroatom, and the aromatic hydrocarbon group may be unsubstituted or substituted by one or more of the aforementioned substituents E.

[0047] J 1 This represents -O-, -S-, -COO-, -OCO-, -OCO-O-, and -NQ. 2 -、-N=CQ 2 -、-CO-NQ 2 -、-OCO-NQ 2 -or-O-NQ 2 -, Q 2 The following groups represent hydrogen atoms, alkyl groups with 1 to 20 carbon atoms, cycloalkyl groups with 3 to 12 carbon atoms, cycloalkenyl groups with 3 to 12 carbon atoms, organic groups with 2 to 30 carbon atoms having an aromatic hydrocarbon group (any carbon atom of which may be replaced by a heteroatom), or -(L 6 -A 5 ) q -L 7 -R sp2 -Z 2 The alkyl, cycloalkyl, cycloalkenyl, and aromatic hydrocarbon groups may be unsubstituted or substituted by one or more of the aforementioned substituents E. The alkyl group may be substituted by the cycloalkyl or cycloalkenyl group. One -CH2- or two or more non-adjacent -CH2- groups in the alkyl group may be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO2-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF-, or -C≡C-. One -CH2- or two or more non-adjacent -CH2- groups in the cycloalkyl or cycloalkenyl group may be independently replaced by -O-, -CO-, -COO-, -OCO-, or -O-CO-O-. 6 A 5 L 7 R sp2 and Z 2 Respectively represent the above L 1 ~L 4 A 1 ~A 4 L 5 R sp1 and Z 1 Those with the same defined groups can be respectively combined with the above-mentioned L 1 ~L 4 A 1~A 4 L 5 R sp1 and Z 1 Same or different, q represents an integer from 0 to 4, in L 6 and A 5 When multiple instances exist, they can be the same or different. Additionally, Q... 1 With Q 2 They can also be bonded to form a ring.

[0048] One embodiment of the present invention provides a polymerizable composition comprising the polymerizable liquid crystal compound of one embodiment of the present invention described above.

[0049] One embodiment of the present invention provides a polymerizable composition, which further comprises the polymerizable liquid crystal compound of the above-described embodiment of the present invention, and a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound.

[0050] One embodiment of the present invention provides a polymer obtained by polymerizing the polymeric liquid crystal compound of one embodiment of the present invention or the polymeric composition of one embodiment of the present invention described above.

[0051] One embodiment of the present invention provides a phase retardation film, which is a phase retardation film having a phase retardation layer, wherein the phase retardation layer contains a cured product of the polymeric composition of one embodiment of the present invention.

[0052] One embodiment of the present invention provides a method for manufacturing a retardation film, which includes a step of forming a retardation layer by having the following steps:

[0053] The process of forming a film from the polymeric composition of one embodiment of the present invention described above;

[0054] At least the process of orienting the polymeric compound in the polymeric composition after film formation; and

[0055] A process that polymerizes the aforementioned polymeric compound at least after the orientation process described above.

[0056] One embodiment of the present invention provides a transfer laminate for transferring a phase retardation layer. The transfer laminate includes a phase retardation layer and a support that peelably supports the phase retardation layer.

[0057] The aforementioned phase difference layer contains a cured product of the polymeric composition of an embodiment of the present invention.

[0058] One embodiment of the present invention provides an optical component having a polarizing plate on the phase retardation film of the above-described embodiment of the present invention.

[0059] One embodiment of the present invention provides a method for manufacturing an optical component, which includes the following steps:

[0060] The transfer lamination preparation process prepares a transfer lamination for transfer of a phase difference layer, the transfer lamination having a phase difference layer and a support that peelably supports the phase difference layer, and the phase difference layer containing a cured product of the polymeric composition of an embodiment of the present invention.

[0061] A transfer process in which a transfer object, comprising at least a polarizing plate, is positioned opposite the phase difference layer of the transfer laminate, and the transfer laminate is transferred onto the transfer object; and

[0062] The peeling process peels the support from the transfer laminate that has been transferred onto the transfer body.

[0063] In addition, one embodiment of the present invention provides a display device having a phase retardation film of one embodiment of the present invention described above, or an optical component of one embodiment of the present invention described above.

[0064] The effects of the invention

[0065] According to embodiments of the present invention, the following can be provided: a polymeric liquid crystal compound with a large birefringence (Δn) and reverse wavelength dispersion; a polymeric composition comprising the polymeric liquid crystal compound; a polymer obtained by polymerizing the polymeric liquid crystal compound or the polymeric composition; a phase retardation film having a phase retardation layer comprising the polymeric composition and a method for manufacturing the same; a transfer laminate capable of transferring the phase retardation layer; an optical component having the phase retardation film and a method for manufacturing the same; and a display device.

[0066] Brief description of the attached diagram

[0067] Figure 1 This is a schematic cross-sectional view illustrating one embodiment of the phase retardation film.

[0068] Figure 2 This is a schematic cross-sectional view illustrating one embodiment of the phase retardation film.

[0069] Figure 3 This is a schematic cross-sectional view illustrating one embodiment of the phase retardation film.

[0070] Figure 4 This is a schematic cross-sectional view illustrating one embodiment of a transfer lamination.

[0071] Figure 5 This is a schematic cross-sectional view illustrating one embodiment of a transfer lamination.

[0072] Figure 6 This is a schematic cross-sectional view illustrating one embodiment of a transfer lamination.

[0073] Figure 7 This is a schematic cross-sectional view illustrating one embodiment of the optical component.

[0074] Figure 8 This is a schematic cross-sectional view illustrating one embodiment of the display device. Detailed Implementation

[0075] Hereinafter, embodiments and examples of the present invention will be described with reference to the accompanying drawings. However, the present invention can be implemented in many different ways and is not limited to the description of the embodiments or examples illustrated below. Furthermore, the drawings sometimes schematically show the width, thickness, shape, etc. of various parts compared to the actual embodiments to make the explanation clearer, but these are merely examples and do not limit the interpretation of the present invention. Additionally, in this specification and the drawings, sometimes the same reference numerals are given to components that are described above with reference to existing drawings, and detailed descriptions are appropriately omitted. Furthermore, for ease of explanation, terms such as "above" or "below" are sometimes used, but the up and down directions may be reversed.

[0076] In this specification, when a component or region is located "above (or below)" other components or regions, unless otherwise specified, it includes not only the case where it is located directly above (or directly below) other components, but also the case where it is located above (or below) other components, that is, the case where other components are contained between the above (or below) other components.

[0077] In this invention, the so-called orientation constraint force refers to the effect of aligning the liquid crystal compounds in the phase difference layer in a specific direction.

[0078] In this invention, (meth)acrylic acid refers to either acrylic acid or methacrylic acid, and (meth)acrylate refers to either acrylate or methacrylate.

[0079] Furthermore, in this specification, the terms "plate," "sheet," and "membrane" are not distinguished from each other solely based on different names. "Membrane surface (plate surface, sheet surface)" refers to the surface that is aligned with the plane of the membrane-like (plate-like, sheet-like) component when viewed as a whole and globally.

[0080] A. Polymerizable liquid crystal compounds

[0081] The polymerizable liquid crystal compound of the present invention is a compound represented by the following general formula (1).

[0082] [Chemistry 3]

[0083] General formula (1)

[0084]

[0085] (In general formula (1), L) 1 L 2 L 3 and L 4 Represent independently the following: -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-CO O-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -C OO-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or single bond,

[0086] A 1 and A 2 Each of these groups independently represents a divalent alicyclic hydrocarbon group with 3 to 20 carbon atoms, either unsubstituted or substituted with one or more substituents E. Any carbon atom of this alicyclic hydrocarbon group may be substituted with a heteroatom.

[0087] A 3 and A 4 Each of these groups independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group with 3 to 20 carbon atoms, either unsubstituted or substituted with one or more substituents E. Any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a heteroatom.

[0088] R 1 and R 2 Each group is independently represented by a group selected from the following general formula (R-1).

[0089] General formula (R-1): -L 5 -R sp1 -Z 1

[0090] In general formula (R-1), L 5Represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OC O-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=NN=CH-, -CF=CF-, -C≡C- or single bond, R sp1 This indicates that one -CH2- or two or more non-adjacent -CH2- atoms can be independently replaced by an alkylene group or single bond with 1 to 20 carbon atoms, belonging to the categories -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. Z 1 It represents a polymeric functional group.

[0091] D 1 and D 2 Each group is independently represented by a group selected from the following general formula (D-1).

[0092] Substituents E, E 1 and E 2 Each of the following groups independently represents a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuryl 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, thioisocyano group, or one -CH2- or two or more non-adjacent -CH2- groups that can be independently replaced by -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-, or -C≡C-, and is a straight-chain or branched alkyl group with 1 to 20 carbon atoms, wherein any hydrogen atom in the alkyl group can be replaced by a fluorine atom, or, the substituent E, E 1 and E 2 -L can be represented independently.E -R spE -Z E The group represented here, L E R spE and Z E Respectively represent the above L 5 R sp1 and Z 1 Those with the same defined groups can be respectively combined with the above-mentioned L 5 R sp1 and Z 1 Whether the compounds are the same or different, multiple substituents E, E, are present in the compound respectively. 1 and E 2 In any case, they may be the same or different.

[0093] In L 3 L 4 A 3 and A 4 When multiple instances exist, they can be the same or different.

[0094] m1 and m2 independently represent integers from 1 to 4, and n1 and n2 independently represent integers from 0 to 3.

[0095] [Chemistry 4]

[0096] General formula (D-1)

[0097]

[0098] (In general formula (D-1), G) 1 This refers to an alkyl group having 1 to 6 hydrogen atoms or carbon atoms, which may be unsubstituted or substituted with one or more of the aforementioned substituents E.

[0099] Q 1 This refers to an organic group having 2 to 30 carbon atoms and an aromatic hydrocarbon group, wherein any carbon atom of the aromatic hydrocarbon group may be replaced by a heteroatom, and the aromatic hydrocarbon group may be unsubstituted or substituted by one or more of the aforementioned substituents E.

[0100] J 1 This represents -O-, -S-, -COO-, -OCO-, -OCO-O-, and -NQ. 2 -、-N=CQ 2 -、-CO-NQ 2 -、-OCO-NQ 2 -or-O-NQ 2 -, Q 2The term represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or an organogroup having an aromatic hydrocarbon group having 2 to 30 carbon atoms, wherein any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom, or -(L 6 -A 5 ) q -L 7 -R sp2 -Z 2 The alkyl, cycloalkyl, cycloalkenyl, and aromatic hydrocarbon groups may be unsubstituted or substituted by one or more of the aforementioned substituents E. The alkyl group may be substituted by the cycloalkyl or cycloalkenyl group. One -CH2- or two or more non-adjacent -CH2- groups in the alkyl group may be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO2-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF-, or -C≡C-. One -CH2- or two or more non-adjacent -CH2- groups in the cycloalkyl or cycloalkenyl group may be independently replaced by -O-, -CO-, -COO-, -OCO-, or -O-CO-O-. 6 A 5 L 7 R sp2 and Z 2 Respectively represent the above L 1 ~L 4 A 1 ~A 4 L 5 R sp1 and Z 1 Those with the same defined groups can be respectively combined with the above-mentioned L 1 ~L 4 A 1 ~A 4 L 5 R sp1 and Z 1 Same or different, q represents an integer from 0 to 4, in L 6 and A 5 When multiple instances exist, they can be the same or different. Additionally, Q... 1 With Q 2 They can also be bonded to form a ring.

[0101] The compound represented by the general formula (1) of the present invention, due to the specific R mentioned above, 1 To R 2The main chain structure has a specific structure, thus increasing the orientation of molecules and making it a compound that independently exhibits liquid crystal properties. In addition, the compound represented by the general formula (1) of the present invention is a polymeric liquid crystal compound because it has polymeric groups at the ends.

[0102] The compound represented by the general formula (1) of the present invention has a high degree of molecular orientation due to the presence of biphenyl groups in the main chain portion. In addition, each of the two benzene rings of the biphenyl group has one side chain, for a total of two side chains, thus becoming a liquid crystal compound with reverse wavelength dispersion and a large birefringence (Δn).

[0103] Compounds exhibiting reverse wavelength dispersibility typically have poor solubility, but the compound represented by general formula (1) of this invention, through A adjacent to the biphenylene group, exhibits good solubility. 1 and A 2 The presence of alicyclic hydrocarbon groups can improve the reduced solubility.

[0104] The polymeric liquid crystal compound represented by the general formula (1) of the present invention has a large birefringence (Δn) and reverse wavelength dispersion, so a phase retardation layer with the required reverse wavelength dispersion can be obtained with a small amount of use, and a thinner phase retardation layer can be obtained.

[0105] Furthermore, since the polymerizable liquid crystal compound represented by the general formula (1) of the present invention has a large birefringence (Δn) and reverse wavelength dispersion, the phase difference of the material with the desired reverse wavelength dispersion can be adjusted by adding a small amount to other liquid crystal compounds.

[0106] L in general formula (1) 1 L 2 L 3 and L 4Represent independently the following: -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-CO O-, -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=NN=CH-, -CF=CF-, -C≡C- or a single bond. These represent divalent linker groups or single bonds. Furthermore, in L... 3 and L 4 When multiple instances exist independently, they can be the same or different.

[0107] As L 1 and L 2 More specifically, from the viewpoints of liquid crystal properties, availability of raw materials, and ease of synthesis, it is preferable to represent -COO-, -OCO-, -OCH2-, -CH2O-, -CF2O-, -OCF2-, -CH2CH2-, -CF2CF2-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -CH=CH-, -CF=CF-, -C≡C-, or single bonds, more preferably -COO-, - OCO-, -OCH2-, -CH2O-, -CF2O-, -OCF2-, -CH2CH2-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -CH=CH-, -C≡C- or a single bond, more preferably representing -COO-, -OCO-, -OCH2-, -CH2O-, -CF2O-, -OCF2- or a single bond, more preferably representing -COO-, -OCO-, -OCH2-, -CH2O- or a single bond, particularly preferably representing -COO-, -OCO-, -OCH2- or -CH2O-.

[0108] As L3 and L 4 More specifically, from the viewpoint of the availability and ease of synthesis of raw materials, it is preferable that each of the following is independently represented: -O-, -S-, -OCH2-, -CH2O-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, or a single bond. When multiple bonds exist, they may be the same or different; more preferably, they are individually... The terms -O-, -OCH2-, -CH2O-, -COO-, -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, or single bonds can be represented independently. When multiple terms exist, they can be the same or different. It is particularly preferred that they can be represented independently as -O-, -COO-, -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, or single bonds.

[0109] A in general formula (1) 1 and A 2 Each of the above refers independently to an alicyclic hydrocarbon group with 3 to 20 divalent carbon atoms that is either unsubstituted or substituted by one or more substituents E. Any carbon atom of the alicyclic hydrocarbon group may be substituted with a heteroatom. More specifically, any carbon atom of the alicyclic hydrocarbon group may be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom.

[0110] Examples of alicyclic hydrocarbon groups with 3 to 20 carbon atoms that are divalent include: cycloalkanedyl groups with 3 to 20 carbon atoms and alicyclic condensed cycloalkanes with 10 to 20 carbon atoms.

[0111] Examples of divalent cycloalkanediyl groups with 3 to 20 carbon atoms include: cyclopropyldiyl; cyclobutane-1,2-diyl, cyclobutane-1,3-diyl, etc. (cyclobutanediyl); cyclopentane-1,2-diyl, cyclopentane-1,3-diyl, etc. (cyclopentanediyl); cyclohexane-1,2-diyl, cyclohexane-1,3-diyl, cyclohexane-1,4-diyl, etc. (cyclohexanediyl); cycloheptane-1,2-diyl, cycloheptane-1,3-diyl, cycloheptane-1,4-diyl, etc. (cycloheptanediyl); cyclooctane-1,2-diyl, cyclooctane-1,3-diyl, cyclooctane-1,4-diyl, cyclooctane-1,5-diyl, etc. (cyclooctanediyl); cyclodecane-1,2-diyl Cyclodecane-1,3-diyl, cyclodecane-1,4-diyl, cyclodecane-1,5-diyl, etc.; cyclododecane-1,2-diyl, cyclododecane-1,3-diyl, cyclododecane-1,4-diyl, cyclododecane-1,5-diyl, etc.; cyclotetradecane-1,2-diyl, cyclotetradecane-1,3-diyl, cyclotetradecane-1,4-diyl, cyclotetradecane-1,5-diyl, cyclotetradecane-1,7-diyl, etc.; cycloeicosane-1,2-diyl, cycloeicosane-1,10-diyl, etc., etc., where the above cycloalkyldiyl groups may be unsubstituted or substituted with one or more substituents E.

[0112] Any carbon atom in the aforementioned cycloalkanediyl group can be replaced with an oxygen atom, a sulfur atom, or a nitrogen atom, for example: tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrothiaran-2,5-diyl, etc.

[0113] Examples of alicyclic condensation cycloalkanes with 10 to 20 divalent carbon atoms include: decahydronaphthalene-2,5-diyl, decahydronaphthalene-2,6-diyl, decahydronaphthalene-2,7-diyl, etc.; adamantane-1,2-diyl, adamantane-1,3-diyl, etc.; bicyclo[2.2.1]heptane-2,3-diyl, bicyclo[2.2.1]heptane-2,5-diyl, bicyclo[2.2.1]heptane-2,6-diyl, etc., etc. These alicyclic condensation cycloalkanes may be unsubstituted or substituted with one or more E substituents. Furthermore, any carbon atom in the above alicyclic condensation cycloalkanes may be replaced with an oxygen atom, a sulfur atom, or a nitrogen atom.

[0114] Among these, A is particularly effective in enhancing liquid crystal properties and the orientation of the polymer. 1 and A 2Each and every one of the following is preferably an alicyclic hydrocarbon group with 3 to 12 carbon atoms that is unsubstituted or can be substituted by one or more substituents E; more preferably a cycloalkyldiyl group with 3 to 12 carbon atoms; even more preferably cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, cycloheptane-1,4-diyl, or cyclododecane-1,5-diyl that is unsubstituted or can be substituted by one or more substituents E; and particularly preferably cyclohexane-1,4-diyl that is unsubstituted or can be substituted by one or more substituents E.

[0115] The aforementioned divalent alicyclic hydrocarbon groups with 3 to 20 carbon atoms may exist based on L 1 L 3 (or L) 2 L 4 The differences in the spatial configuration of the carbon atoms in the bond result in cis- and trans-stereoisomers. The alicyclic hydrocarbon group with 3 to 20 divalent carbon atoms can be cis-, trans-, or a mixture of cis- and trans-isomers. In terms of good orientation, trans- or cis- isomers are preferred, and trans- isomers are more preferred.

[0116] A in general formula (1) 3 and A 4 Each of these groups independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group with 3 to 20 carbon atoms, either unsubstituted or substituted with one or more substituents E. Any carbon atom in the alicyclic or aromatic hydrocarbon group may be replaced with a heteroatom; more specifically, any carbon atom in the alicyclic or aromatic hydrocarbon group may be replaced with an oxygen, sulfur, or nitrogen atom. The aforementioned aromatic hydrocarbon group can be an aromatic heterocyclic group, may have a condensed ring structure, or may be a structure formed by the condensation of an alicyclic hydrocarbon group and an aromatic hydrocarbon group. Furthermore, in A... 3 and A 4 When multiple instances exist independently, they can be the same or different.

[0117] A 3 and A 4 Examples of divalent aromatic hydrocarbon groups that can be substituted by heteroatoms include: divalent aromatic hydrocarbon groups with 6 to 20 carbon atoms that can be substituted by heteroatoms. Examples of aromatic hydrocarbon rings constituting these heteroatom-substituted aromatic hydrocarbon groups include: benzene rings, naphthalene rings, anthracene rings, phenanthrene rings, etc. Examples of aromatic heterocycles include: furan rings, pyridine rings, pyrimidine rings, pyrazine rings, etc.

[0118] In addition, A 3 and A 4 In this context, the alicyclic hydrocarbon group with 3 to 20 carbon atoms, which is divalent as described above, can be used with A 1 and A 2 The above-mentioned alicyclic hydrocarbon groups with 3 to 20 carbon atoms are identical.

[0119] A 3 and A 4 Among them, the alicyclic or aromatic hydrocarbon groups with 3 to 20 divalent carbon atoms that can be substituted by heteroatoms can be exemplified by, for example: benzene-1,4-diyl(1,4-phenylene), cyclohexane-1,4-diyl, cyclohexene-1,4-diyl, tetrahydropyran-2,5-diyl, 1,3-dioxane-2,5-diyl, tetrahydrothiaran-2,5-diyl, 1,4-bicyclo(2,2,2)octylene, decahydronaphthalene-2,6-diyl, pyridine-2 5-diyl, pyrimidin-2,5-diyl, pyrazine-2,5-diyl, 1,2,3,4-tetrahydronaphthyl-2,6-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, phenanthrene-2,7-diyl, 9,10-dihydrophenanthrene-2,7-diyl, 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl or fluorene-2,7-diyl, etc. The above alicyclic hydrocarbon groups and aromatic hydrocarbon groups may be unsubstituted or substituted with one or more substituents E.

[0120] As A in general formula (1) 3 and A 4 Among them, A is particularly effective in enhancing liquid crystal properties and the orientation of the polymer. 3 and A 4 The preferred materials are, independently and preferably, benzene-1,4-diyl, cyclohexane-1,4-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, or 1,3-dioxane-2,5-diyl.

[0121] A in general formula (1) 3 and A 4 The preferred groups are phenyl-1,4-diyl, naphthalene-2,6-diyl, or cyclohexane-1,4-diyl, either unsubstituted or substituted with one or more E substituents, more preferably phenyl-1,4-diyl or cyclohexane-1,4-diyl, and particularly preferably phenyl-1,4-diyl. These groups readily enhance the liquid crystallinity of the polymerizable liquid crystal compound of this embodiment and improve the orientation of the polymer.

[0122] The substituent E can independently represent a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuryl, nitro, cyano, isocyano, amino, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, trimethylsilyl, dimethylsilyl, thioisocyano, or one -CH2- or two or more non-adjacent -CH2- groups can each be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, or -CO-. A straight-chain or branched alkyl group with 1 to 20 carbon atoms, consisting of 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-, or -C≡C-, wherein any hydrogen atom in the alkyl group may be replaced by a fluorine atom, or the substituent E may be independently represented by -L. E -R spE -Z E The group represented here, L E R spE and Z E Respectively represent the following L 5 R sp1 and Z 1 Those with the same defined groups can be respectively combined with the above-mentioned L 5 R sp1 and Z 1 In the case of multiple substituents E in a compound, they may be the same or different.

[0123] From the viewpoint of liquid crystal properties and ease of synthesis, the substituent E is preferably a fluorine atom, chlorine atom, pentafluorosulfuryl group, nitro group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, or any hydrogen atom that can be replaced with a fluorine atom, and one -CH2- or two or more non-adjacent -CH2- groups can be independently replaced with a straight-chain or branched alkyl group with 1 to 20 carbon atoms selected from -O-, -S-, -CO-, -COO-, -OCO-, -O-CO-O-, -CH=CH-, -CF=CF- or -C≡C-. More preferably, it is a straight-chain or branched alkyl group with 1 to 12 carbon atoms, in which a fluorine atom, chlorine atom, or any hydrogen atom can be replaced with a fluorine atom and one -CH2- or two or more non-adjacent -CH2- can be independently replaced with a group selected from -O-, -COO- or -OCO-. More preferably, it is a straight-chain or branched alkyl group or alkoxy group with 1 to 12 carbon atoms, in which a fluorine atom, chlorine atom, or any hydrogen atom can be replaced with a fluorine atom. Particularly preferred is a straight-chain alkyl group or straight-chain alkoxy group with 1 to 8 carbon atoms, in which a fluorine atom, chlorine atom, or carbon atom can be replaced with a fluorine atom.

[0124] Additionally, as can be found in A 3 and A 4 The substituent E is used for substitution, especially when R is bonded to it. 1 and R 2 A 3 and A 4 The substituent E that is substituted is preferably -L. E -R spE -Z E The group to be represented.

[0125] In general formula (1), m1 and m2 independently represent integers from 1 to 4.

[0126] When emphasizing the liquid crystal properties and orientation properties of the polymeric compound in this embodiment, it is preferable that one or both of m1 and m2 are integers from 1 to 3, more preferably that both of m1 and m2 are integers from 1 to 3, and even more preferably that both of m1 and m2 are 1 or 2.

[0127] R 1 and R 2 Each group is independently selected from the following general formula (R-1).

[0128] General formula (R-1): -L 5 -R sp1 -Z 1

[0129] In general formula (R-1), L 5 Represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OC O-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-, -CO O-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=NN=CH-, -CF=CF-, -C≡C- or single bond.

[0130] In general formula (R-1), L is used as 5 More specifically, from the perspective of the availability and ease of synthesis of raw materials, L5 Preferably, each of the following can be independently represented as -O-, -S-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH2CH2-COO-, -CH2CH2-OCO-, or a single bond. More preferably, each of the following can be independently represented as -O-, -COO-, -OCO-, -O-CO-O-, or a single bond. When multiple bonds exist, they can be the same or different.

[0131] In general formula (R-1), R sp1 This indicates that one -CH2- or two or more non-adjacent -CH2- atoms can be independently replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C- with 1 to 20 carbon atoms, or by a single bond.

[0132] In general formula (R-1), R is... sp1 More specifically, from the perspective of the availability and ease of synthesis of raw materials, R sp1 More preferably, each -CH2- can be independently represented by one -CH2- or two or more non-adjacent -CH2-, each of which can be independently replaced by -O-, -COO-, or -OCO-, which are alkylene groups with 1 to 12 carbon atoms or single bonds. More preferably, each of which can be independently represented by alkylene groups with 1 to 12 carbon atoms or single bonds. More preferably, each of which can be independently represented by alkylene groups with 2 to 10 carbon atoms. In the case of multiple alkylene groups, each of which can be the same or different.

[0133] In general formula (R-1), Z 1 This indicates a polymerizable functional group. This polymerizable functional group can be used without restriction with groups already employed in existing polymerizable liquid crystal compounds.

[0134] The polymerizable functional group is preferably a group selected independently from formulas (Z-1) to (Z-8) below. Furthermore, in formulas (Z-1) to (Z-8) below, * (asterisk) indicates a group related to R. sp1 The bond position.

[0135] [Chemistry 5]

[0136]

[0137] (In equations (Z-1) to (Z-8), R) z Each of the following atoms can be represented independently: hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, or trifluoromethyl.

[0138] In the case of ultraviolet polymerization as a polymerization method, Z 1Preferably, formulas (Z-1), (Z-2), (Z-3), (Z-5), and (Z-7) are used; more preferably, formulas (Z-1), (Z-3), and (Z-7) are used; even more preferably, formula (Z-1) is used; and particularly preferably, in formula (Z-1), R... z In the case of hydrogen atoms, methyl groups, or trifluoromethyl groups.

[0139] In general formula (1), Lc1 is represented as -L 1 -A 1 -(L 3 -A 3 ) m1 -L 5 -R sp1 -Z 1 and Lc2: -L 2 -A 2 -(L 4 -A 4 ) m2 -L 5 -R sp1 -Z 1 Specific examples can be listed by the groups represented by Lc-1 to Lc-244 below, but are not limited to these. In the polymerizable liquid crystal compound represented by general formula (1), Lc1 and Lc2 may be the same or different.

[0140] [Table 1]

[0141]

[0142] [Table 2]

[0143]

[0144] [Table 3]

[0145]

[0146] [Table 4]

[0147]

[0148] [Table 5]

[0149]

[0150] [Table 6]

[0151]

[0152] In the groups represented by Lc-1 to Lc-244 above, L 3 and L 4 In this context, m1 and m2 represent 1 or 2, preferably 2. R sp1In this context, n represents 1 to 20, where R sp1 The n in the formula is preferably 2 or more, more preferably 4 or more, and on the other hand, preferably 12 or less, more preferably 10 or less.

[0153] In addition, Z 1 In equation (Z-1), R is... z Each of the following is preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0154] On the other hand, in general formula (D-1), G 1 The alkyl group represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms. This alkyl group may be unsubstituted or substituted with one or more of the aforementioned substituents E, wherein the substituent E is preferably F, Cl, CF3, OCF3, or a cyano group. G 1 Preferably, it is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms that is unsubstituted or substituted with one or more F atoms, G 1 More preferably, it is a hydrogen atom.

[0155] Q 1 An organic group having 2 to 30 carbon atoms and containing an aromatic hydrocarbon group is preferred. It is an organic group having 2 to 30 carbon atoms and containing an aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles, where any carbon atom of the aromatic hydrocarbon group can be replaced by a heteroatom. Preferably, the aromatic ring is a group selected from formulas (Q-1) to (Q-22).

[0156] In terms of good wavelength dispersibility, organic groups having an aromatic heterocycle in which one or more carbon atoms are replaced by heteroatoms are preferred. In terms of good wavelength dispersibility and high birefringence, organic groups having an aromatic heterocycle as a condensed ring of a 5-membered or 6-membered ring are even more preferred. Regarding the aromatic heterocycle as a condensed ring of a 5-membered or 6-membered ring, for example, it is preferred that one or more carbon atoms of the group selected from the following formulas (Q-10), (Q-11), (Q-21), and (Q-22) are replaced by heteroatoms.

[0157] [Chemistry 6]

[0158]

[0159] These groups have bonds at any position. Q a Indicates -O-, -S-, -NR Qa -(where R is in the formula) Qa These groups represent alkyl groups with 1 to 8 hydrogen atoms or carbon atoms, or -CO-. In these groups, -CH= can be independently replaced by -N=, and -CH2- can be independently replaced by -O-, -S-, or -NR. Qa-(where R is in the formula) Qa The alkyl group (representing an alkyl group with 1 to 8 hydrogen atoms or carbon atoms) is -SO-, or -SO2-, or -CO- (except where oxygen atoms are directly bonded to each other). One or more hydrogen atoms bonded to these rings may be replaced with the aforementioned substituent E. Examples of alkyl groups constituting the aforementioned alkyl groups include: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, etc. The number of carbon atoms in the aforementioned alkyl groups is preferably 1 to 4, more preferably 1 or 2, and even more preferably 1.

[0160] The group represented by formula (Q-1) is preferably a group selected from formulas (Q-1-1) to (Q-1-8) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E, and these groups have bonds at any position.

[0161] [Chemistry 7]

[0162]

[0163] The group represented by formula (Q-7) is preferably a group selected from formulas (Q-7-1) to (Q-7-7) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E, and these groups have bonds at any position.

[0164] [Chemistry 8]

[0165]

[0166] As the group represented by formula (Q-10), it is preferably a group selected from formulas (Q-10-1) to (Q-10-9) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0167] [Chemistry 9]

[0168]

[0169] (where R is in the formula) Q This refers to alkyl groups having 1 to 6 hydrogen atoms or carbon atoms. These groups have bonds in any position.

[0170] As the group represented by formula (Q-11), it is preferably a group selected from formulas (Q-11-1) to (Q-11-12) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0171] [Chemistry 10]

[0172]

[0173] (where R is in the formula) QThis refers to alkyl groups having 1 to 6 hydrogen or carbon atoms. These groups have bonds in any position.

[0174] As the group represented by formula (Q-13), it is preferably a group selected from formulas (Q-13-1) to (Q-13-19) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0175] [Chemistry 11]

[0176]

[0177] (where R is in the formula) Q This refers to alkyl groups having 1 to 6 hydrogen atoms or carbon atoms. These groups have bonds in any position.

[0178] As the group represented by formula (Q-14), it is preferably a group selected from formulas (Q-14-1) to (Q-14-10) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0179] [Chemistry 12]

[0180]

[0181] (where R is in the formula) Q This refers to alkyl groups having 1 to 6 hydrogen atoms or carbon atoms. These groups have bonds in any position.

[0182] As the group represented by formula (Q-15), it is preferably a group selected from formulas (Q-15-1) to (Q-15-4) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0183] [Chemistry 13]

[0184]

[0185] (where R is in the formula) Q This refers to alkyl groups having 1 to 6 hydrogen atoms or carbon atoms. These groups have bonds in any position.

[0186] As the group represented by formula (Q-16), it is preferably a group selected from formulas (Q-16-1) to (Q-16-16) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0187] [Chemistry 14]

[0188]

[0189] (where R is in the formula) QThis refers to alkyl groups having 1 to 6 hydrogen atoms or carbon atoms. These groups have bonds in any position.

[0190] As the group represented by formula (Q-17), it is preferably a group selected from formulas (Q-17-1) to (Q-17-4) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0191] [Chemistry 15]

[0192]

[0193] (where R is in the formula) Q This refers to alkyl groups having 1 to 6 hydrogen atoms or carbon atoms. These groups have bonds in any position.

[0194] As the group represented by formula (Q-18), it is preferably a group selected from formulas (Q-18-1) to (Q-18-6) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0195] [Chemistry 16]

[0196]

[0197] (where R is in the formula) Q This refers to alkyl groups having 1 to 6 hydrogen atoms or carbon atoms. These groups have bonds in any position.

[0198] As the group represented by formula (Q-19), it is preferably a group selected from formulas (Q-19-1) to (Q-19-6) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0199] [Chemistry 17]

[0200]

[0201] (where R is in the formula) Q This refers to alkyl groups having 1 to 6 hydrogen atoms or carbon atoms. These groups have bonds in any position.

[0202] As the group represented by formula (Q-20), it is preferably a group selected from formulas (Q-20-1) to (Q-20-9) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0203] [Chemistry 18]

[0204]

[0205] (where R is in the formula) QThis refers to alkyl groups having 1 to 6 hydrogen atoms or carbon atoms. These groups have bonds in any position.

[0206] As the group represented by formula (Q-21), it is preferably a group selected from formulas (Q-21-1) to (Q-21-3) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0207] As the group represented by formula (Q-22), it is preferably a group selected from formulas (Q-22-1) to (Q-22-3) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0208] [Chemistry 19]

[0209]

[0210] Q 1 The aromatic group contained therein is more preferably a group selected from the above formulas (Q-1-1), (Q-7-1), (Q-7-2), (Q-7-7), (Q-8), (Q-10-2), (Q-10-3), (Q-10-4), (Q-10-5), (Q-10-6), (Q-10-7), (Q-10-8), (Q-10-9), (Q-11-2), (Q-11-3), (Q-11-4), (Q-11-5), (Q-11-6), (Q-11-7), (Q-11-8), and (Q-11-9) that are unsubstituted or can be substituted by one or more of the above-mentioned substituents E. -9), formula (Q-11-10), formula (Q-11-11), formula (Q-11-12), formula (Q-21-1), formula (Q-21-2), formula (Q-22-1), and formula (Q-22-2), particularly preferably groups selected from formula (Q-10-2), formula (Q-10-3), formula (Q-10-4), formula (Q-10-5), formula (Q-10-6), formula (Q-10-7), formula (Q-10-8), formula (Q-10-9), formula (Q-21-1), formula (Q-21-2), formula (Q-22-1), and formula (Q-22-2) that are unsubstituted or can be substituted by one or more of the above-mentioned substituents E.

[0211] Additionally, as Q 1 Substituent E in cases where the aromatic group is substituted QPreferably, it is a straight chain with 1 to 20 carbon atoms, representing a fluorine atom, chlorine atom, bromine atom, iodine atom, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, thioisocyano group, or one -CH2- or two or more non-adjacent -CH2- groups that can be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-. Or a branched alkyl group, wherein any hydrogen atom in the alkyl group may be replaced with a fluorine atom, more preferably a straight-chain or branched alkyl group with 1 to 20 carbon atoms, representing a fluorine atom, a chlorine atom, a bromine atom, or one -CH2- or two or more non-adjacent -CH2- atoms, each of which may be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, wherein any hydrogen atom in the alkyl group may be replaced with a fluorine atom.

[0212] In addition, Q 1 Particularly preferred are groups selected from the following formulas (Q-10-2), (Q-10-2a), (Q-10-3), (Q-10-3a), (Q-10-3b), (Q-10-6), (Q-10-6a), (Q-10-6b), (Q-10-6c), (Q-10-6d), (Q-10-7), (Q-10-7a), (Q-10-7b), (Q-10-7c), (Q-10-7d), (Q-10-7e), (Q-10-7f), (Q-10-9), (Q-10-9a), (Q-10-9b), (Q-21-1), (Q-21-2), (Q-22-1), and (Q-22-2).

[0213] [Chemistry 20]

[0214]

[0215] J 1 This represents -O-, -S-, -COO-, -OCO-, -OCO-O-, and -NQ. 2 -、-N=CQ 2 -、-CO-NQ 2 -、-OCO-NQ 2 -or-O-NQ 2 -, Q 2The following groups represent hydrogen atoms, alkyl groups with 1 to 20 carbon atoms, cycloalkyl groups with 3 to 12 carbon atoms, cycloalkenyl groups with 3 to 12 carbon atoms, organic groups with 2 to 30 carbon atoms having an aromatic hydrocarbon group (any carbon atom of which may be replaced by a heteroatom), or -(L 6 -A 5 ) q -L 7 -R sp2 -Z 2 The alkyl, cycloalkyl, cycloalkenyl, and aromatic hydrocarbon groups may be unsubstituted or substituted by one or more of the aforementioned substituents E. The alkyl group may be substituted by the cycloalkyl or cycloalkenyl group. One -CH2- or two or more non-adjacent -CH2- groups in the alkyl group may be independently replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO2-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF-, or -C≡C-. One -CH2- or two or more non-adjacent -CH2- groups in the cycloalkyl or cycloalkenyl group may be independently replaced by -O-, -CO-, -COO-, -OCO-, or -O-CO-O-. 6 A 5 L 7 R sp2 and Z 2 Respectively represent the above L 1 ~L 4 A 1 ~A 4 L 5 R sp1 and Z 1 Those with the same defined groups can be respectively combined with the above-mentioned L 1 ~L 4 A 1 ~A 4 L 5 R sp1 and Z 1 Same or different, q represents an integer from 0 to 4, in L 6 and A 5 When multiple instances exist, they can be the same or different.

[0216] In terms of good birefringence and ease of synthesis, as J 1 Preferably, -O-, -S-, or -N=CQ 2 -or-NQ 2Furthermore, in terms of good wavelength dispersion and birefringence, -O-, -S-, or -NQ are preferred. 2 -

[0217] Here, Q 2 Preferably, it is an alkyl or alkenyl group with 1 to 20 carbon atoms, a cycloalkyl group with 3 to 12 carbon atoms, or a cycloalkenyl group with 3 to 12 carbon atoms, which can be substituted by one or more of the above-mentioned substituents E and one -CH2- or two or more non-adjacent -CH2- can be independently replaced by -O-, -CO-, -COO-, -OCO-, or -O-CO-O-, or an alkyl or alkenyl group that can be substituted by the cycloalkyl, cycloalkenyl, or aryl group, or represents -(L 6 -A 5 )qL 7 -R sp2 -Z 2 .

[0218] Q 2 The appropriate choice can be made depending on the purpose. For example, regarding birefringence, Q... 2 Preferably, it has a structure free of heteroatoms. Additionally, in Q... 2 For structures containing more heteroatoms, where one -CH2- or two or more non-adjacent -CH2- atoms can be independently replaced by -O-, -CO-, -COO-, -OCO-, or -O-CO-O-, it is preferable to improve the solvent solubility of the compound and increase the options for the substrate. Furthermore, regarding improved durability through increased film curing degree, Q is preferred. 2 -(L 6 -A 5 )qL 7 -R sp2 -Z 2 .

[0219] Examples of unsubstituted alkyl or alkenyl groups having 1 to 20 carbon atoms, cycloalkyl groups having 3 to 12 carbon atoms, cycloalkenyl groups having 3 to 12 carbon atoms, and alkyl or alkenyl groups that may be substituted by the cycloalkyl, cycloalkenyl, or aryl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, 1-methylpentyl, n-heptyl, 1-ethylpentyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, 3,7-dimethyloctyl, n-undecyl, n-dodecyl, vinyl, allyl, isopropenyl, butynyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclooctenyl, cyclopentylmethyl, cyclohexylmethyl, benzyl, etc.

[0220] As Q 2The substituents in the group are preferably fluorine, chlorine, bromine, cyano, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino, or one -CH2- or two or more non-adjacent -CH2- groups that can be independently replaced by -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- or -C≡C- are straight-chain or branched alkyl groups with 1 to 20 carbon atoms, and are further preferably fluorine atoms, chlorine atoms, cyano groups, hydroxyl groups, or one -CH2- or two or more non-adjacent -CH2- can be independently replaced by -O-, -CO-, -COO-, -OCO-, or -O-CO-O- are straight-chain or branched alkyl groups with 1 to 20 carbon atoms.

[0221] Regarding birefringence, solvent solubility, or durability, Q... 2 Preferably, it is an alkyl or alkenyl group with 1 to 20 carbon atoms, a cycloalkyl group with 3 to 12 carbon atoms, or a cycloalkenyl group with 3 to 12 carbon atoms, or an alkyl or alkenyl group with 3 to 12 carbon atoms, which can be substituted by one or more of the above-mentioned substituents E and one -CH2- or two or more non-adjacent -CH2- can be independently replaced by -O-, -CO-, -COO-, -OCO-, or -O-CO-O-, or an alkyl or alkenyl group that can be substituted by the cycloalkyl or cycloalkenyl group, or represents -(L 6 -A 5 )qL 7 -R sp2 -Z 2 More preferably, any hydrogen atom may be replaced by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- atoms may be independently replaced by a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a cycloalkyl group having 3 to 12 carbon atoms, or an alkyl group that may be substituted by such cycloalkyl group, or representing -(L 6 -A 5 )qL 7 -R sp2 -Z 2 Further preferably, it is a straight-chain or branched alkyl group with 1 to 12 carbon atoms or a cycloalkyl group with 3 to 12 carbon atoms, wherein one -CH2- or two or more non-adjacent -CH2- atoms can each be replaced with -O-, or an alkyl group that can be substituted by the cycloalkyl group, or represents -(L 6 -A 5 )qL 7 -R sp2 -Z2 .

[0222] Additionally, -(L 6 -A 5 )qL 7 -R sp2 -Z 2 The preferred structure is more ideally the same as the above-mentioned L. 1 ~L 4 A 1 ~A 4 L 5 R sp1 and Z 1 The defined preferred structures are the same. q represents an integer from 0 to 4, more preferably an integer from 0 to 2, even more preferably 0 or 1, and particularly preferably 0.

[0223] Regarding birefringence and solvent solubility, concerning Q 2 Preferably, the hydrogen atom can be replaced by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- can be independently replaced by a straight-chain or branched alkyl group with 2 to 20 carbon atoms, or a cycloalkyl group with 3 to 12 carbon atoms, or the above-mentioned alkyl group that can be replaced by the cycloalkyl group; more preferably, the hydrogen atom can be replaced by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- can be independently replaced by a straight-chain or branched alkyl group with 2 to 20 carbon atoms, or a -O-, -CO-, -COO-, -OCO-; even more preferably, the hydrogen atom can be replaced by a fluorine atom and one -CH2- or two or more non-adjacent -CH2- can be independently replaced by a straight-chain alkyl group with 2 to 20 carbon atoms, or a -O-, -CO-, -COO-, -OCO-.

[0224] Q 2 The number of carbon atoms in it is preferably 4 or more, and more preferably 12 or less.

[0225] Or Q 1 With Q 2 They can also be bonded to form a ring, in which case, for example, -NQ can be enumerated. 1 Q 2 The cyclic group represented, or -N=CQ 1 Q 2 The cyclic group represented. Q 1 With Q 2 The ring formed together with the bonded nitrogen or carbon atom can be exemplified by rings having an aromatic ring and a carbon number of 2 to 30, more preferably 2 to 18, and even more preferably 2 to 14. Among these, -NQ 1 Q 2The cyclic group represented is preferably a group selected from formulas (QQ-1) to (QQ-22) that is unsubstituted or can be substituted by one or more of the above-mentioned substituents E. -N=CQ 1 Q 2 The cyclic group represented is preferably represented by the following formula (QQ-23) or formula (QQ-24).

[0226] [Chemistry 21]

[0227]

[0228] In the groups selected from formulas (QQ-1) to (QQ-22), -CH= can be independently replaced with -N=, and -CH2- can be independently replaced with -O-, -S-, or -NR. Q2 -(where R is in the formula) Q2 The alkyl group (representing an alkyl group with 1 to 8 hydrogen atoms or carbon atoms) is -SO-, or -SO2-, or -CO- (except where oxygen atoms are directly bonded to each other). One or more hydrogen atoms bonded to these rings can be replaced by the substituent E described above. Examples of alkyl groups constituting the above-mentioned alkyl groups include: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, hexyl, etc. The number of carbon atoms in the above-mentioned alkyl groups is preferably 1 to 4, more preferably 1 or 2, and even more preferably 1.

[0229] J 1 and Q 1 From the viewpoints of wavelength dispersion characteristics, liquid crystal properties, and ease of synthesis, the total number of π electrons contained is preferably 4 to 24, and more preferably 4 to 20.

[0230] In terms of readily available raw materials, good solubility, and high birefringence, D 1 and D 2 Particularly preferred are groups selected from formulas (D-1) to (D-47) below.

[0231] [Chemistry 22]

[0232]

[0233] [Chemistry 23]

[0234]

[0235] E that can be substituted on the benzene ring of biphenylene 1 and E 2 Each can be independently identical to the aforementioned substituent E.

[0236] E, which can be substituted on the benzene ring of a biphenylene group. 1 and E 2In terms of good birefringence and ease of synthesis, E 1 and E 2 Preferably, the fluorine atom, chlorine atom, hydroxyl group, mercapto group, methyl amino group, dimethyl amino group, or one -CH2- or two or more non-adjacent -CH2- groups can be independently replaced by a straight-chain or branched alkyl group with 1 to 6 carbon atoms, such as -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-.

[0237] In addition, n1 and n2 each independently represent integers from 0 to 3, preferably from 0 to 2, and more preferably 0 or 1.

[0238] Additionally, in E 1 and E 2 When the substitutions are performed independently on the biphenylene rings, the preferred substitution positions are the 6- and 6'-positions of the biphenylene ring, which are advantageous for birefringence. In this case, the torsion angle of the two benzene rings in the biphenylene ring increases, making it easier to cleave the π-electron conjugated structure.

[0239] The structure of the biphenyl group in the main chain portion preferably represents a group selected from the following formulas (Co-1) to (Co-8).

[0240] [Chemistry 24]

[0241]

[0242] Furthermore, as compounds represented by general formula (1), examples include compounds (i) to (xci). In the table, Core represents the structure of a biphenylene, and Lc1 represents -L 1 -A 1 -(L 3 -A 3 ) m1 -L 5 -R sp1 -Z 1 Lc2 represents -L 2 -A 2 -(L 4 -A 4 ) m2 -L 5 -R sp1 -Z 1 .

[0243] [Table 7]

[0244]

[0245] [Table 8]

[0246]

[0247] Furthermore, representative structural formulas of compounds (i) to (xci) in Tables 7 and 8 are illustrated below, but are not limited to these.

[0248] [Chemistry 25]

[0249]

[0250] [Chemistry 26]

[0251]

[0252] [Chemistry 27]

[0253]

[0254] [Chemistry 28]

[0255]

[0256] [Chemistry 29]

[0257]

[0258] [Chemistry 30]

[0259]

[0260] [Chemistry 31]

[0261]

[0262] [Chemistry 32]

[0263]

[0264] The compound represented by general formula (1) can be manufactured, for example, by the following method. As a method, it can be manufactured by appropriately combining known organic synthesis reactions (e.g., condensation reactions, esterification reactions, Williamson reactions, Ulmann reactions, Wittsch reactions, Schiff base formation reactions, benzylation reactions, sago reactions, Suzuki-Miyaura reactions, Negishi reactions, Kumada reactions, Hiyama reactions, Buchwald-Hartwig reactions, Friedrich-Cleift reactions, Heck reactions, aldol condensation reactions, Duff reactions, etc.) as described in Methods of Organic Chemistry, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, and New Experimental Chemistry Lectures, depending on its structure. Examples of manufacturing methods are given below, but the present invention is not limited to these structures or manufacturing methods.

[0265] For example, in L 1 and L 2 They are respectively *-OCO- (* indicates the bonding position with the biphenylene) and G 1 In the case of compounds containing hydrogen atoms, they can be manufactured, for example, in the following manner.

[0266] First, prepare a 4,4′-dihydroxybiphenyl, or a compound represented by formula (ip-1) with a substituent E, and then prepare an intermediate A represented by formula (ip-2) with an aldehyde group introduced at the desired position by means of a Duff reaction or the like.

[0267] [Chemistry 33]

[0268]

[0269] Next, through condensation reactions, etc., intermediate A represented by formula (ip-2) reacts with HOOC-A. 1 -(L 3 -A 3 ) m1 -R 1 The intermediate B (A) is represented 1 L 3 A 3 R 1 (where m1 represents the same meaning as above) reacts to obtain intermediate C represented by formula (ip-3), and further, the obtained intermediate C represented by formula (ip-3) reacts with HOOC-A 2 -(L 4 -A 4 ) m2 -R 2 The intermediate D(A) represents 2 L 4 A 4 R 2 The reaction of intermediates A and B (where m2 represents the same meaning as above) yields intermediate E as represented by formula (ip-4). If intermediate B and intermediate D have the same structure, intermediate E can be obtained by reacting intermediate A with intermediate B.

[0270] [Chemistry 34]

[0271]

[0272] [Chemistry 35]

[0273]

[0274] Next, let the intermediate E represented by equation (ip-4) be, for example, with Q. 1 -J1 The intermediate F, represented by -NH2, reacts to obtain the compound represented by formula (1-ex1).

[0275] [Chemistry 36]

[0276]

[0277] Furthermore, the intermediate A represented by the above formula (ip-2) is based on E. 1 and E 2 Types or replacement positions, D 1 and D 2 The substitution position, for example, can also be introduced by subjecting 3,4-methylenedioxyphenol (manufactured by Tokyo Chemical Industry Co., Ltd.) or its derivatives to a Duff reaction to introduce an aldehyde group, and then by subjecting it to a Suzuki-Miyaura coupling reaction.

[0278] Additionally, for example, D, which becomes a side chain component, is pre-introduced into intermediate A as represented by equation (ip-2). 1 and D 2 After intermediate G, the intermediate G is then reacted with HOOC-A. 1 -(L 3 -A 3 ) m1 -R 1 The intermediate B (A) is represented 1 L 3 A 3 R 1 (and m1 indicates the same meaning as above) or HOOC-A 2 -(L 4 -A 4 ) m2 -R 2 The intermediate D(A) represents 2 L 4 A 4 R 2 (and m2 represents the same meaning as above) react to obtain the compound represented by formula (1-ex1).

[0279] In addition, commercially available products may be used for the intermediates used in the manufacturing process, or they may be synthesized using other known methods.

[0280] In this invention, the structure of polymerizable liquid crystal compounds can be analyzed by appropriately combining nuclear magnetic resonance spectroscopy (NMR), thermal decomposition gas chromatography-mass spectrometry (Py-GC-MS), and matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOFMS).

[0281] The polymerizable liquid crystal compound of the present invention is a polymerizable liquid crystal compound with good orientation, a large birefringence (Δn), and reverse wavelength dispersion. For example, by the method shown in Example 1 below, a polymerizable composition comprising only the polymerizable liquid crystal compound of the present invention and a photopolymerization initiator is prepared, a cured film (phase reversal layer) is formed, and the birefringence (Δn) of the cured film is measured. In this case, the birefringence is preferably 0.075 or higher, and more preferably 0.08 or higher.

[0282] Furthermore, regarding the polymerizable liquid crystal compound of the present invention, in order to achieve good reverse wavelength dispersion and make it close to ideal reverse wavelength dispersion, when preparing a polymerizable composition containing only the polymerizable liquid crystal compound of the present invention and a photopolymerization initiator, forming a cured film (phase difference layer), and measuring the phase difference value, Re(450) / Re(550) is preferably in the range of 0.50 or more and less than 0.95, more preferably in the range of 0.55 or more and less than 0.93, more preferably in the range of 0.60 or more and less than 0.90, particularly preferably in the range of 0.60 or more and less than 0.83, and may also be in the range of 0.60 or more and less than 0.80. Additionally, Re(650) / Re(550) is preferably greater than 1, more preferably in the range of 1.02 or more and less than 1.1.

[0283] The following are some experimental methods for measuring phase difference.

[0284] [Trial Method]

[0285] A polymeric composition was obtained by dissolving 100 parts by weight of the polymeric liquid crystal compound of the present invention and 4 parts by weight of 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropane-1-one in 900 parts by weight of cyclopentanone. The obtained polymeric composition was then coated onto a glass substrate with a polyimide alignment film after rubbing treatment [product name: alignment-treated glass substrate, manufactured by EHC Co., Ltd., which is coated with Polyimide LX-1400 manufactured by Hitachi Chemical Co., Ltd. and rub-treated. The rubbing treatment conditions are as follows: roller speed: 600 rpm, moving speed: 30 mm / sec, number of passes: 3 round trips] to a cured film thickness of 1 μm. The film was dried at a temperature equal to the solid-liquid crystal phase transition temperature (°C) of the contained polymeric liquid crystal compound plus 10°C for 120 seconds, and then subjected to an irradiation dose of 400 mJ / cm². 2 Irradiation with ultraviolet light creates a phase difference layer. The in-plane phase difference Re(450) at a wavelength of 450 nm and the in-plane phase difference Re(550) at a wavelength of 550 nm are measured using a phase difference measuring device (e.g., product name: KOBRA-WR, manufactured by Oji Measurement & Control Co., Ltd.).

[0286] Furthermore, the same result can be obtained by forming a phase difference layer and measuring the phase difference value using the method shown in Example 1 below.

[0287] Furthermore, regarding the expansion of the options for substrates that can be used with the polymerizable liquid crystal compound of the present invention, the solid-liquid crystal phase transition temperature is preferably 25°C or higher and 200°C or lower, more preferably 30°C or higher and 180°C or lower, and even more preferably 30°C or higher and 150°C or lower. If the solid-liquid crystal phase transition temperature is low, the load in the liquid crystal alignment process can be reduced, or it can be used on substrates that are not resistant to high temperatures.

[0288] Here, the solid-liquid crystal phase transition temperature refers to the temperature at which a liquid crystal compound changes from a solid to a liquid crystal. In this invention, the solid-liquid crystal phase transition temperature is confirmed by textural observation using a polarizing microscope equipped with a temperature-controlled stage, during heating. That is, in polarizing microscope observation, the point at which the solid melts into a liquid state upon heating and becomes a bright field of view when observed with orthogonal Nikkor polarizing microscopes (with polarizing plates in an orthogonal state) is defined as the solid-liquid crystal phase transition temperature.

[0289] In addition, regarding the expansion of the options for usable substrates, the polymeric liquid crystal compound of the present invention is preferably dissolved in at least 10% by mass or more in at least one solvent selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone, and more preferably dissolved in at least 20% by mass or more.

[0290] B. Polymerizing compositions

[0291] The polymerizable composition of the present invention is a composition comprising at least the polymerizable liquid crystal compound of the present invention described above.

[0292] Since the polymeric composition of the present invention contains the polymeric liquid crystal compound of the present invention described above, it can be made into a polymeric composition with a large birefringence (Δn) and reverse wavelength dispersion as described above.

[0293] The polymerizable composition of the present invention comprises at least the polymerizable liquid crystal compound of the present invention described above, and preferably also contains a photopolymerization initiator.

[0294] Furthermore, the polymerizable composition of the present invention may contain a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound of the present invention, in terms of adjusting phase difference or reverse wavelength dispersion, or adjusting orientation, solubility, or phase transition temperature. Additionally, other components may be included to the extent that they do not impair the effect. Hereinafter, each component constituting the polymerizable composition of the present invention will be described sequentially.

[0295] 1. The polymeric liquid crystal compound of the present invention described above.

[0296] In the polymeric composition of the present invention, the polymeric liquid crystal compound of the present invention may be the same as that described in "A. Polymeric Liquid Crystal Compound" above, so the description is omitted here.

[0297] In the polymeric composition of the present invention, the polymeric liquid crystal compound of the present invention may be used alone or in combination of two or more. In this embodiment, in order to obtain a polymeric composition with a large birefringence (Δn) and reverse wavelength dispersion, the content ratio of the polymeric liquid crystal compound of the present invention relative to 100 parts by mass of the solid content of the polymeric composition is preferably 50 parts by mass or more and 99.9 parts by mass or less, more preferably 54 parts by mass or more and 99 parts by mass or less, and even more preferably 57 parts by mass or more and 98 parts by mass or less.

[0298] Furthermore, in this invention, the solid component refers to all components other than the solvent. For example, the polymeric liquid crystal compound described below, which is different from the polymeric liquid crystal compound of this invention, is included in the solid component even if it is in liquid form.

[0299] 2. Photopolymerization initiator

[0300] In this embodiment, the photopolymerization initiator can be appropriately selected from existing known initiators. Specific examples of such photopolymerization initiators include, for example, aromatic ketones including thioxanthone, α-aminoalkylphenyl ketones, α-hydroxy ketones, acylphosphine oxides, oxime esters, aromatic onium salts, organic peroxides, sulfur-containing compounds, hexaaryl biimidazole compounds, ketoxime ester compounds, borate ester compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having carbon-halogen bonds, and alkylamine compounds, etc., wherein, in order to cure to the interior of the coating film to improve durability, at least one initiator selected from the group consisting of acylphosphine oxide-based polymerization initiators, α-aminoalkylphenyl ketone-based polymerization initiators, α-hydroxy ketone-based polymerization initiators, and oxime ester-based polymerization initiators is preferred.

[0301] Examples of acylphosphine oxide polymerization initiators include: bis(2,4,6-trimethylbenzoyl)phenylphosphine oxide (e.g., trade name: Irgacure 819, manufactured by BASF), bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphenylphosphine oxide, and 2,4,6-trimethylbenzoyl-diphenylphosphine oxide (trade name: Lucirin TPO, manufactured by BASF, etc.).

[0302] In addition, examples of α-aminoalkylphenyl ketone polymerization initiators include: 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropane-1-one (e.g., Irgacure 907, manufactured by BASF), 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone (e.g., Irgacure 369, manufactured by BASF), and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]-1-butanone (Irgacure 379EG, manufactured by BASF), etc.

[0303] In addition, examples of α-hydroxy ketone polymerization initiators include: 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propanoyl)benzyl]phenyl}-2-methyl-propane-1-one (e.g., trade name: Irgacure 127, manufactured by BASF), 2-hydroxy-4′-hydroxyethoxy-2-methylphenylacetone (e.g., trade name: Irgacure 2959, manufactured by BASF), 1-hydroxy-cyclohexyl-phenyl-one (e.g., trade name: Irgacure 184, manufactured by BASF), and oligomeric {2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]acetone} (e.g., trade name: ESACURE ONE, manufactured by Lamberti).

[0304] Examples of oxime ester polymerization initiators include: 1,2-octanedione, 1-[4-(phenylthio)-,2-(O-benzoyl oxime)] (trade name: Irgacure OXE-01, manufactured by BASF), ethyl ketone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-, 1-(o-acetyl oxime) (trade name: Irgacure OXE-02, manufactured by BASF), methyl ketone, ethyl ketone, 1-[9-ethyl-6-(1,3-dioxolane,4-(2-methoxyphenoxy)-9H-carbazole-3-yl]-, 1-(o-acetyl oxime) (trade name: ADEKA OPT-N-1919, manufactured by ADEKA), etc.

[0305] In this embodiment, the photopolymerization initiator can be used alone or in combination of two or more.

[0306] In this embodiment, the content ratio of the photopolymerization initiator, in terms of promoting the curing of the polymeric compound, is preferably 0.1 parts by mass or more and 10 parts by mass or less, and more preferably 1 part by mass or more and 8 parts by mass or less, relative to 100 parts by mass of the solid content of the polymeric composition.

[0307] 3. Polymerizable liquid crystal compounds different from the polymerizable liquid crystal compounds of the present invention.

[0308] In the polymeric composition of the present invention, the polymeric liquid crystal compound, different from the polymeric liquid crystal compound of the present invention described above, may be appropriately selected from conventionally known polymeric liquid crystal compounds. This may be a typical normally dispersed (positively dispersed) polymeric liquid crystal compound whose slope is negative (decreasing to the right) when plotted with the wavelength λ of the incident light relative to the retardation film as the horizontal axis and its birefringence as the vertical axis; it may be a polymeric liquid crystal compound exhibiting reverse wavelength dispersion; or it may be a polymeric liquid crystal compound that substantially does not exhibit wavelength dispersion (flat dispersion or low-wavelength dispersion). Examples of polymeric liquid crystal compounds different from the polymeric liquid crystal compound of the present invention, exhibiting reverse wavelength dispersion, include those described in Japanese Patent Nos. 5463666, 4186981, 5962760, and 5826759. Examples of compounds exhibiting flat dispersion include compounds described in Recueil des Travaux Chimiques des Pays-Bas (1996), 115(6), 321-328.

[0309] In this embodiment, in combination with the above-described polymeric liquid crystal compound, in terms of ease of orientation, a polymeric liquid crystal compound having polymeric functional groups at at least one end of the rod-shaped mesomorph is preferred, and a polymeric liquid crystal compound having polymeric functional groups at both ends of the rod-shaped mesomorph is more preferred. A polymeric liquid crystal compound having two or more polymeric functional groups per molecule can improve the hardness or durability of the coating film.

[0310] Examples of polymerizable liquid crystal compounds used in this invention include polymerizable liquid crystal compounds represented by the following general formula (II-1) having the same structure as the main chain portion of the polymerizable compounds described above, and polymerizable liquid crystal compounds represented by the following general formula (II-2).

[0311] [Chemistry 37]

[0312] General formula (II-1)

[0313]

[0314] General formula (II-2)

[0315]

[0316] (where Z) 10 and Z 20 Each of the above represents a polymeric functional group, R.sp10 and R sp20 Each of the following can independently represent a single bond or an alkylene group with 1 to 20 carbon atoms, and one -CH2- or two or more non-adjacent -CH2- can be replaced by -O-, -COO-, -OCO-, or -OCOO-. 10 L 20 and L 30 Each of these can be represented independently as -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-, -CF=CF-, -C≡C- or a single bond, A 10 and A 20 Each of the following can be represented independently as phenyl-1,4-diyl, cyclohexane-1,4-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, tetrahydronaphthalene-2,6-diyl, or 1,3-dioxane-2,5-diyl, A 10 and A 20 Each of the following groups is independent and unsubstituted, or may be substituted with alkyl, haloalkyl, alkoxy, haloalkoxy, halogen atom, cyano, or nitro groups. R represents a hydrogen atom, fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuryl, cyano, nitro, isocyano, thioisocyano, or one -CH2- or two or more non-adjacent -CH2- groups that may be independently substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, or -O. Alkyl groups with 1 to 20 carbon atoms, including -CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF-, or -C≡C-. s1 and s2 represent 0, 1, 2, 3, or 4. When s1 and s2 independently represent 2, 3, or 4, there are 2, 3, or 4 A atoms. 20 L 10 (They can be the same or different)

[0317] As polymerizable functional groups possessed by polymerizable liquid crystal compounds, examples of Z-related functional groups in the aforementioned polymerizable compounds can be listed. 1 The same applies. Examples of polymerizable functional groups in polymerizable liquid crystal compounds include groups containing cyclic ethers such as ethylene oxide rings and oxetane rings, and groups containing vinyl double bonds. Among these, groups containing vinyl double bonds are preferred for their photocurability and excellent workability. Examples of cyclic ether groups include glycidyl groups. Furthermore, examples of groups containing vinyl double bonds include vinyl, allyl, and (meth)acryloyl groups, with (meth)acryloyl groups being preferred.

[0318] In this embodiment, the polymerizable liquid crystal compound, in terms of orientation, is preferably one or more compounds selected from the compounds represented by general formula (III) and the compounds represented by general formula (IV) below.

[0319] [Chemistry 38]

[0320] General Formula (III)

[0321]

[0322] (In general formula (III), R) 21 R represents a hydrogen atom or a methyl group. 22 It represents -(CH2) p - or -(C2H4O) p′ - The group to be represented. L 23 Ar represents the linking group represented by direct bonding, or -O-, -OC(=O)-, or -C(=O)-O-. 3 This indicates benzene-1,4-diyl, cyclohexane-1,4-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, tetrahydronaphthalene-2,6-diyl, or 1,3-dioxane-2,5-diyl, Ar 3 Multiple L groups may be unsubstituted or substituted with alkyl, haloalkyl, alkoxy, haloalkoxy, halogen atom, cyano or nitro groups. 23 and Ar 3 They can be the same or different. R 23 This indicates -F, -Cl, -CN, -OCF3, -OCF2H, -NCO, -NCS, -NO2, -NHC(=O)-R 24 -C(=O)-OR 24 , -OH, -SH, -CHO, -SO3H, -NR 24 2. -R 25 、or -OR 25 R 24R indicates an alkyl group having 1 or more hydrogen atoms and 6 or fewer carbon atoms. 25 This indicates an alkyl group with 1 or more but less than 6 carbon atoms. (b is an integer of 2 or more but less than 5, and p and p′ are each an independent integer of 2 or more but less than 10.)

[0323] [Chemistry 39]

[0324] General Formula (IV)

[0325]

[0326] (In general formula (IV), R) 31 and R 32 Each can be represented independently by a hydrogen atom or a methyl group, R 33 It represents -(CH2) q - or -(C2H4O) q’ - The group represented, R 34 It represents -(CH2) r - or -(OC2H4) r′ - The group to be represented. L 34 Ar represents the linking group represented by direct bonding, or -O-, -OC(=O)-, or -C(=O)-O-. 4 This indicates benzene-1,4-diyl, cyclohexane-1,4-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, naphthalene-1,4-diyl, tetrahydronaphthalene-2,6-diyl, or 1,3-dioxane-2,5-diyl, Ar 4 Multiple L groups may be unsubstituted or substituted with alkyl, haloalkyl, alkoxy, haloalkoxy, halogen atom, cyano or nitro groups. 34 and Ar 4 They can be the same or different. c is an integer greater than 2 and less than 5, and q, q′, r, and r′ are each independently an integer greater than 2 and less than 10.

[0327] In terms of orientation, p, p′ in general formula (III), q, q′, r and r′ in general formula (IV) are preferably 2 or more and 8 or less, more preferably 2 or more and 6 or less, and even more preferably 2 or more and 5 or less.

[0328] Additionally, Ar 3 and Ar 4 These represent phenyl-1,4-diyl, cyclohexane-1,4-diyl, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthyl-2,6-diyl, naphthyl-1,4-diyl, tetrahydronaphthyl-2,6-diyl, or 1,3-dioxane-2,5-diyl, with phenyl-1,4-diyl, naphthyl-2,6-diyl, or cyclohexane-1,4-diyl being more preferred. As Ar 3 and Ar4 The substituents that may be present include alkyl, haloalkyl, alkoxy, haloalkoxy, halogen atom, cyano or nitro, and more preferably alkyl, halogen atom, etc., having 1 or more and 5 or fewer carbon atoms.

[0329] In addition, R in general formula (III) 24 and R 25 The alkyl group having 1 to 6 carbon atoms can be any of straight-chain, branched, or cyclic. Examples include: straight-chain alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl; branched alkyl groups such as isopropyl, isobutyl, tert-butyl, and 2-methylbutyl; and cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. As R 24 Preferably, it is an alkyl group having 1 or more hydrogen atoms and 5 or fewer carbon atoms, and more preferably an alkyl group having 1 or more hydrogen atoms and 3 or fewer carbon atoms. As R 25 Preferably, the alkyl group has 1 or more but less than 5 carbon atoms, and more preferably, it is an alkyl group with 1 or more but less than 3 carbon atoms.

[0330] As R 23 In terms of orientation, R 23 Preferred saturates are -Cl, -CN, -OCF3, -OCF2H, -NCO, -NCS, -NO2, and -NHC(=O)-R. 25 -C(=O)-OR 24 , -OH, -SH, -CHO, -SO3H, -NR 24 2. -R 25 、or -OR 25 More preferably -Cl, -CN, -OCF3 or -C(=O)-OR 24 -R 25 、or -OR 25 .

[0331] The mesocrystalline structure contained in the polymerizable liquid crystal compound is preferably a partial structure represented by the following chemical formulas (V-1) to (V-6), wherein at least one partial structure represented by the following chemical formulas (V-1), (V-2), (V-4), (V-5), and (V-6) containing three or more ring structures is preferably used. The hydrogen atoms in the phenylene or naphthyl group of the partial structure represented by the following chemical formulas (V-1) to (V-6) may also be replaced by alkyl or halogen atoms having one or more but less than three carbon atoms.

[0332] [Chemistry 40]

[0333]

[0334] Suitable specific examples of compounds represented by general formula (III) and general formula (IV) can be listed as those represented by the following chemical formulas (1) to (22), but are not limited to these.

[0335] [Chemistry 41]

[0336]

[0337] (g is an integer from 2 to 5.)

[0338] [Chemistry 42]

[0339]

[0340] As described above, the polymeric liquid crystal compound of the present invention exhibits excellent reverse wavelength dispersibility, so even when a compound showing a wide range of wavelength dispersibility is added, the phase difference value of the cured composition easily shows reverse wavelength dispersibility. When the phase difference value of the polymeric liquid crystal compound of the present invention is measured as described above, there is a tendency for the Re(450) / Re(550) ratio to be relatively smaller.

[0341] Therefore, as a polymeric liquid crystal compound different from the polymeric liquid crystal compound of the present invention, in terms of adjusting to ideal wavelength dispersion, it is preferable to further contain a polymeric liquid crystal compound in which, in the following test method, the ratio (Re(450) / Re(550)) of the in-plane phase difference (Re(450)) at a wavelength of 450 nm to the in-plane phase difference (Re(550)) at a wavelength of 550 nm is greater than the Re(450) / Re(550) of the polymeric liquid crystal compound of the present invention. As a polymeric liquid crystal compound different from the polymeric liquid crystal compound of the present invention, it can be selected from those with Re(450) / Re(550) of 0.6 or more and less than 1.2, preferably from those with 0.8 or more and less than 1.2, and even more preferably from those with 0.9 or more and less than 1.2.

[0342] [Trial Method]

[0343] A polymerizable composition was obtained by dissolving 100 parts by mass of a polymerizable liquid crystal compound and 4 parts by mass of 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropane-1-one in 900 parts by mass of cyclopentanone. The obtained polymerizable composition was then coated onto an alignment film of a glass substrate [product name: alignment-treated glass substrate, manufactured by EHC Co., Ltd.] with a polyimide alignment film after rubbing treatment, to a cured film thickness of 1 μm. The film was dried at the solid-liquid phase transition temperature (°C) of the polymerizable liquid crystal compound plus 10°C for 120 seconds, followed by irradiation with a dose of 400 mJ / cm². 2Ultraviolet light is irradiated to form a phase difference layer. The in-plane phase difference Re(450) at a wavelength of 450 nm and the in-plane phase difference Re(550) at a wavelength of 550 nm are measured by a phase difference measuring device (e.g., product name: KOBRA-WR, manufactured by Oji Measurement & Control Co., Ltd.).

[0344] Furthermore, in this embodiment, regarding the improvement of the solvent solubility of the polymeric composition, it is preferable that the polymeric liquid crystal compound, different from the polymeric liquid crystal compound of the present invention, dissolves in at least 20% by mass or more in at least one solvent selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone. If the solvent solubility of the polymeric composition is improved, a uniform coating film is easily formed when using the polymeric composition to form a coating film, the load on the manufacturing process or manufacturing apparatus used for solvent drying is reduced, the selection of usable substrates is expanded, and the liquid crystal phase transition temperature of the composition is extended, the process allowance during orientation is increased, and the orientation becomes more uniform. These aspects are preferred.

[0345] In this embodiment, polymeric liquid crystal compounds different from the polymeric liquid crystal compounds of the present invention may be used alone or in combination of two or more.

[0346] In this embodiment, the content ratio of the polymeric liquid crystal compound, which is different from the polymeric liquid crystal compound of the present invention, can be appropriately adjusted to adjust the required phase difference, etc., and is not limited. It is preferably 7 parts by mass or more and 49.9 parts by mass or less relative to 100 parts by mass of the solid content of the polymeric composition, more preferably 10 parts by mass or more and 45 parts by mass or less, and even more preferably 10 parts by mass or more and 42 parts by mass or less.

[0347] Furthermore, the content ratio of the polymeric liquid crystal compound different from that of the present invention can be appropriately adjusted to adjust the required phase difference, etc. The total mass of the polymeric liquid crystal compound of the present invention and the polymeric liquid crystal compound different from that of the present invention is 100 parts by mass, preferably 50 parts by mass or less, and more preferably 45 parts by mass or less.

[0348] 4. Other ingredients

[0349] The polymeric composition of this embodiment may also contain other components within the scope of non-destructive effects. Specifically, other components may include leveling agents, antioxidants, light stabilizers, or solvents from a coating point of view. Additionally, it may contain polymeric compounds that do not exhibit liquid crystal properties when used alone but can adjust phase difference or inverse wavelength dispersion, phase transition temperature, hardness, and durability when used with the polymeric liquid crystal compound of the present invention. These can be achieved by appropriately selecting and using materials already known in the art.

[0350] To improve the hardness or durability of the coating film, it is preferable to also contain a polymeric compound having two or more polymeric functional groups per molecule. In addition to polymeric liquid crystal compounds as described above, polymeric compounds that do not possess liquid crystal properties can also be used as polymeric compounds having two or more polymeric functional groups per molecule.

[0351] As polymeric compounds having two or more polymerizable functional groups in one molecule, so-called multifunctional monomers can also be used, such as: trimethylolpropane tri(meth)acrylate, tripropylene glycol di(meth)acrylate, diethylene glycol di(meth)acrylate, dipropylene glycol di(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, di-trimethylolpropane tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, 1,6-hexanediol di(meth)acrylate, neopentyl glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, di-trimethylolpropane tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dimethylolpropane tri(meth)acrylate, dimethylolpropane tetra ... Pentylenetetroxide pentamethacrylate, tripentaerythritol octamethacrylate, tetrapentaerythritol decamethacrylate, isocyanuric acid trimethacrylate, isocyanuric acid dimethacrylate, polyester trimethacrylate, polyester dimethacrylate, bisphenol dimethacrylate, diglycerol tetramethacrylate, adamantyl dimethacrylate, isobornyl dimethacrylate, dicyclopentane dimethacrylate, tricyclodecane dimethacrylate, di-trimethylolpropane tetramethacrylate, or those modified with PO, EO, etc. To improve the durability of the coating by performing a crosslinking reaction, polymeric compounds having three or more polymeric functional groups per molecule, such as pentaerythritol triacrylate (PETA), dipentaerythritol hexaacrylate (DPHA), pentaerythritol tetraacrylate (PETTA), dipentaerythritol pentaacrylate (DPPA), and trimethylolpropane triacrylate (TMPTA), are preferred.

[0352] In this embodiment, when using a polymeric compound that does not have liquid crystal properties, the content of the compound is preferably 40 parts by mass or less, more preferably 30 parts by mass or less, and even more preferably 20 parts by mass or less, relative to 100 parts by mass of the solid component of the polymeric composition.

[0353] In this embodiment, as a polymeric compound different from the polymeric liquid crystal compound of the present invention, it is preferable to dissolve 20% by mass or more in at least one solvent selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone, in order to improve the solvent solubility of the polymeric composition, facilitate the formation of a uniform coating film when using the polymeric composition to form a coating film, reduce the load on the manufacturing process or manufacturing apparatus used to dry the solvent, and expand the options of substrates that can be used.

[0354] As a leveling agent, a fluorinated or silicone-based leveling agent is preferred. Specific examples of leveling agents include the MEGAFAC series manufactured by DIC Co., Ltd., the TSF series manufactured by Momentive Performance Materials Japan Co., Ltd., and the FTERGENT series manufactured by NEOS Co., Ltd., as described in Japanese Patent Application Publication No. 2010-122325. In this embodiment, when a leveling agent is used, its content ratio is preferably set to 0.001 parts by mass or more and 5 parts by mass or less relative to 100 parts by mass of the solid content of the polymerizable composition.

[0355] Regarding coating properties, the polymerizable composition of this embodiment may also contain a solvent as needed. As the solvent, any suitable solvent can be selected from existing known solvents capable of dissolving or dispersing the components contained in the polymerizable composition. Specifically, examples include: hydrocarbon solvents such as hexane, cyclohexane, and toluene; ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone; ether solvents such as tetrahydrofuran, 1,3-dioxolane, and propylene glycol monoethyl ether (PGME); haloalkyl solvents such as chloroform and dichloromethane; ester solvents such as ethyl acetate and propylene glycol monomethyl ether acetate; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; and alcohol solvents such as methanol, ethanol, and propanol. In this embodiment, one solvent may be used alone or in combination of two or more solvents as a mixed solvent.

[0356] The polymeric composition of this embodiment is suitable for various applications due to its good orientation. The polymeric composition of this embodiment can be used as a liquid crystal composition, for example, in applications such as retardation films or various optical components.

[0357] C. Polymer

[0358] The polymer of the present invention is obtained by polymerizing the polymerizable liquid crystal compound of the present invention described above, or the polymerizable composition of the present invention described above. The polymerization method may be appropriately selected based on the polymerizable functional groups contained in the polymerizable liquid crystal compound of the present invention.

[0359] The polymer obtained by polymerizing the polymeric liquid crystal compound or the polymeric composition of the present invention without orienting it can be used, for example, as a light scattering plate, a polarizing plate, or an anti-mottle stripe plate.

[0360] Furthermore, the polymer obtained by polymerizing the polymeric liquid crystal compound or the polymeric composition of the present invention after orientation has optical anisotropy and can be suitably used for the following applications as phase retardation films or various optical components.

[0361] D. Phase difference film

[0362] The phase retardation film of the present invention is a phase retardation film having a phase retardation layer, and the phase retardation layer comprises a cured product of the polymeric composition of the present invention.

[0363] Regarding the phase retardation film of this embodiment, since the phase retardation layer contains a cured product of the polymeric composition described above, it has good orientation and a large birefringence (Δn), and exhibits reverse wavelength dispersion, as described above.

[0364] The layer composition of the retardation film is explained with reference to the figure. Figures 1-3 Each of these embodiments represents one implementation of the phase difference film of the present invention. Figure 1 One embodiment of the phase retardation film 10 shown in the example is a phase retardation film on which an alignment film 3 and a phase retardation layer 1 are sequentially stacked on a substrate 2. Figure 2 One embodiment of the retardation film 10 shown in the example is a retardation film that only includes the retardation layer 1. Additionally, Figure 3 One embodiment of the phase retardation film 10 shown in the example is in which the phase retardation layer 1 is formed directly on the substrate 2'. Alternatively, [the following can be done]... Figure 3 The example illustrates a phase retardation film attachment: a component exhibiting an orientation-restricting force on the surface of the phase retardation layer 1 side of the substrate 2′. Here, in this invention, the orientation-restricting force refers to the effect of aligning the oriented components in the phase retardation layer in a specific direction.

[0365] 1. Phase difference layer

[0366] The phase retardation layer 1 of the embodiments of the present invention comprises a cured product of the polymeric composition of the present invention containing the polymeric liquid crystal compound of the present invention.

[0367] Here, the polymerizable liquid crystal compound and the polymerizable composition of the present invention described above are the same as those described in the polymerizable liquid crystal compound and polymerizable composition of the embodiments of the present invention, and therefore are omitted here.

[0368] The retardation layer is preferably formed by curing the oriented main chain portion of the polymeric liquid crystal compound of the present invention, and possibly further containing the polymeric liquid crystal compound, in a substantially horizontally oriented state relative to the film surface. The cured product of the polymeric composition of the embodiments of the present invention comprises a structure in which at least a portion of the polymeric functional groups of the polymeric compound has been polymerized. Because it comprises such a structure in which at least a portion of the polymeric functional groups of the polymeric compound has been polymerized, the retardation layer of this embodiment is a retardation layer with improved durability.

[0369] Phase difference can be measured using an automated birefringence measuring device (e.g., manufactured by Oji Measurement & Control Co., Ltd., trade name: KOBRA-WR). By incident the measuring light perpendicularly or obliquely to the surface of the phase difference layer, and by analyzing a graph of the optical phase difference versus the incident angle of the measuring light, the degree of anisotropy that causes the phase difference of the phase difference layer to increase or decrease, or the degree of orientation of the liquid crystal in the vertical (thickness) direction, can be determined.

[0370] Furthermore, if the phase retardation layer contains at least a portion of the polymeric liquid crystal compound of the present invention contained in the polymeric composition of the present invention, or may also contain a polymerized structure of the polymeric functional groups of the polymeric liquid crystal compound, this can be confirmed by analyzing the material collected from the phase retardation layer. As analytical methods, NMR, IR, GC-MS, XPS, TOF-SIMS, and combinations thereof can be applied.

[0371] The retardation layer may also contain other components such as photopolymerization initiators, leveling agents, antioxidants, and light stabilizers. Regarding photopolymerization initiators and other components that may decompose entirely during light irradiation to react the polymerizable functional groups of the aforementioned polymerizable liquid crystal compound, there are cases where they are not included in the retardation layer.

[0372] The thickness of the phase retardation layer can be set appropriately according to the intended use.

[0373] When the phase retardation film of the present invention is, for example, a broadband 1 / 4 wavelength plate, the film thickness can be adjusted so that the Re(550) of the obtained phase retardation film is 113 mm or more and 163 nm or less, preferably 135 mm or more and 140 nm or less, and particularly preferably about 137.5 nm. When it is a 1 / 2 wavelength plate, the film thickness can be adjusted so that the Re(550) of the obtained optical film is 250 nm or more and 300 nm or less, preferably 273 nm or more and 277 nm or less, and particularly preferably about 275 nm.

[0374] Furthermore, by appropriately adjusting the coating amount of the polymeric composition and the concentration of the polymeric liquid crystal compound, the film thickness can be adjusted to impart the desired phase difference. The phase difference value (retardation value, Re(λ)) of the obtained phase difference layer is determined as follows, therefore, in order to obtain the desired Re(λ), only the film thickness d needs to be adjusted.

[0375] Re(λ)=d×Δn(λ)

[0376] (In the formula, Re(λ) represents the phase difference at wavelength λnm, d represents the film thickness, and Δn(λ) represents the birefringence at wavelength λnm)

[0377] The thickness of the phase difference layer is preferably 0.1 μm or more and 5 μm or less, and more preferably 0.5 μm or more and 3 μm or less.

[0378] Because the polymeric liquid crystal compound of the present invention has a large birefringence (Δn), it is possible to achieve phase difference with a thinner film than existing ones.

[0379] The wavelength dispersion characteristics of the retardation film of the present invention can be arbitrarily determined according to the content of the polymeric liquid crystal compound of the present invention and other polymeric liquid crystal compounds that may be contained in the retardation layer. If the content of the polymeric liquid crystal compound of the present invention is increased in the retardation layer, the reverse wavelength dispersion characteristics tend to increase.

[0380] Furthermore, in order to approach ideal reverse wavelength dispersion, a polymeric composition containing only the polymeric liquid crystal compound of the present invention and the photopolymerization initiator was prepared by the method shown in Example 1 below, and a cured film (phase retardation layer) was formed. In this case, Re(450) / Re(550) is preferably in the range of 0.75 or more and less than 0.95, more preferably in the range of 0.78 or more and less than 0.93, and even more preferably in the range of 0.80 or more and less than 0.90. In addition, Re(650) / Re(550) is preferably more than 1, and more preferably in the range of 1.02 or more and less than 1.1.

[0381] 2. Orientation film

[0382] In this specification, an alignment film refers to a layer used to align the liquid crystal components contained in the retardation layer in a certain direction.

[0383] As an orientation film used in embodiments of the present invention, a horizontally oriented film is preferred in terms of facilitating the horizontal orientation of the polymeric composition described in the embodiments of the present invention.

[0384] A horizontally aligned film is simply a film in which the long axis of the mesopacity of the liquid crystal component contained in the retardation layer is substantially horizontally aligned with respect to the horizontally aligned film surface (film surface) by means of a coating.

[0385] As a horizontally oriented film, existing well-known horizontally oriented films can be appropriately selected, such as oriented films that have been given orientation restraint by rubbing, photo-orientation, shaping, etc. Among them, horizontally oriented films that have been given orientation restraint by rubbing, photo-orientation, or shaping are preferred.

[0386] In cases where orientation-restricting forces are imparted through friction, a polymer that exhibits orientation-restricting forces through friction is used in horizontally oriented films. Examples of such polymers include polyvinyl alcohol, polyimide, polyamide, and derivatives thereof, with polyvinyl alcohol being preferred.

[0387] The method for forming a horizontally oriented film using the friction method can be any appropriate method selected from existing known methods. For example, after forming a coating containing the polymer on the above-mentioned transparent substrate, a horizontally oriented film can be obtained by rubbing it with a known friction roller or the like.

[0388] In the case of forming a horizontally aligned film by photo-alignment, a photo-alignment composition containing a photo-alignment material that exhibits orientation-restricting force when irradiated with polarized light is used as the composition for the alignment film. This photo-alignment material can be either a photodimerization type or a photoisomerization type. Specifically, examples include polymers containing cinnamate, coumarin, benzyl phthalimide, benzyl acetophenone, diphenylacetylene, styrylpyridine, uracil, quinolinone, maleimide, or 5-phenyl-2,4-pentadienoic acid derivatives, among which polymers containing at least one of cinnamate and coumarin, and their derivatives, are preferred. Specific examples of such photodimerizing materials include compounds described in Japanese Patent Application Publication Nos. 9-118717, 10-506420, 2003-505561, WO2010 / 150748, and 2015-151548.

[0389] The method for forming a photo-aligned film using the photo-alignment method can be any appropriate method selected from existing known methods. For example, the photo-alignment composition is uniformly coated onto the above-mentioned transparent substrate, polarized light is irradiated, and then the entire surface of the coating is irradiated with light, thereby obtaining a photo-aligned film.

[0390] Furthermore, when forming a horizontally oriented film by a shaping method, the composition for the orientation film can be appropriately selected from those capable of shaping the desired fine unevenness. For example, a shaping composition containing a UV-curable resin, a thermosetting resin, or an electron beam curable resin can be used. In terms of ease of forming the orientation film, a UV-curable resin is preferred. Specific examples of UV-curable resins include the aforementioned polymerizable monomers and polymerizable oligomers, as well as urethane acrylates, epoxy acrylates, polyester acrylates, polyether acrylates, melamine acrylates, etc., which can be used alone or in combination of two or more.

[0391] The method for forming a horizontally oriented film using the shaping method can be appropriately selected from existing known methods. For example, the shaping composition is uniformly coated onto the above-mentioned transparent substrate, the coating is brought into contact with a mold having the desired micro-uneven shape, pressure is applied, and ultraviolet light is irradiated, thereby obtaining an oriented film with the desired micro-uneven shape.

[0392] Furthermore, the aforementioned horizontal alignment film can also be patterned to form a patterned shape for the areas that have been patterned and possess alignment properties. Known horizontal alignment films can be used as patterned films, and there are no particular limitations. Examples include: rubbing alignment films obtained by patterning through masking rubbing; photoalignment films obtained by patterning through masking exposure; and alignment films obtained by patterning alignment films through printing or the like.

[0393] Regarding the thickness of the horizontally oriented film, it can be set appropriately as long as it allows the polymeric rod-shaped liquid crystal compound to be oriented in the horizontal direction, and there is no particular limitation. It is usually 1 nm or more, preferably 60 nm or more. From the viewpoint of thin film formation, it can be 15 μm or less, preferably 10 μm or less, more preferably 1 μm or less, and even more preferably 0.3 μm or less.

[0394] 3. Substrate

[0395] In this embodiment, the substrate may include glass substrates, metal foils, resin substrates, etc. Preferably, the substrate is transparent and can be appropriately selected from existing known transparent substrates. Besides glass substrates, transparent substrates may also include: transparent resin substrates formed using resins such as triacetyl cellulose, polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, and polylactic acid, olefin resins such as polypropylene, polyethylene, and polymethylpentene, acrylic resins, polyurethane resins, polyethersulfone or polycarbonate, polysulfone, polyether, polyetherketone, acrylonitrile, methacrylonitrile, cyclic olefin polymers, and cyclic olefin copolymers.

[0396] The transmittance of the aforementioned transparent substrate in the visible light region is preferably 80% or more, more preferably 90% or more. Here, the transmittance of the transparent substrate can be measured by JIS K7361-1 (Test method for total transmittance of plastic-transparent materials).

[0397] In addition, when the phase difference layer is formed by roller-to-roll, it is preferable that the transparent substrate is a flexible material that can be rolled into a roll.

[0398] Examples of such flexible materials include: cellulose derivatives, norbornene polymers, cyclic olefin polymers, polymethyl methacrylate, polyvinyl alcohol, polyimide, polyarylate, polyethylene terephthalate, polysulfone, polyethersulfone, amorphous polyolefins, modified acrylic polymers, polystyrene, epoxy resin, polycarbonate, and polyesters. In this embodiment, cellulose derivatives and polyethylene terephthalate are preferred. This is because cellulose derivatives, in particular, exhibit excellent optical isotropy, thus allowing for the production of materials with superior optical properties. Furthermore, polyethylene terephthalate is preferred due to its high transparency and excellent mechanical properties.

[0399] The thickness of the substrate used in this embodiment is not particularly limited as long as it is within the range that can impart the required self-supporting properties, depending on the application of the phase difference film, and is usually in the range of about 10 μm or more and about 1000 μm or less.

[0400] The thickness of the substrate is preferably in the range of 25 μm or more and 125 μm or less, and more preferably in the range of 30 μm or more and 100 μm or less. This is because if the thickness exceeds the above range, for example, when cutting a strip-shaped retardation film to form a single-piece retardation film, there is a risk of increased processing debris or accelerated wear of the cutting blade.

[0401] The composition of the substrate used in this embodiment is not limited to a single-layer composition; it may also have a composition consisting of multiple layers. In the case of a composition consisting of multiple layers, layers of the same composition may be stacked, or multiple layers with different compositions may be stacked.

[0402] For example, if the orientation film used in this embodiment contains a UV-curable resin, a base coating may be formed on the substrate to improve the adhesion between the transparent substrate and the UV-curable resin. This base coating only needs to be adhesive to both the substrate and the UV-curable resin, be optically transparent, and allow UV light to pass through; for example, a vinyl chloride / vinyl acetate copolymer or a urethane-based coating may be appropriately selected.

[0403] Alternatively, an adhesive coating can be laminated onto the substrate. This adhesive coating can improve the strength of the substrate. Metal alkoxides, especially metal silicon alkoxide sols, can be used as the adhesive coating material. Metal alkoxides can be used as common alcohol-based solutions. Since the adhesive coating must be a uniform and flexible film, its thickness is preferably about 0.04 μm or more and about 2 μm or less, more preferably about 0.05 μm or more and about 0.2 μm or less.

[0404] When the substrate has an adhesive coating, an adhesive layer may be further laminated between the substrate and the adhesive coating, or the adhesive coating may contain a material that strengthens the adhesion between the substrate and the substrate, thereby improving the adhesion between the substrate and the adhesive coating. As the adhesive material used to form the adhesive layer, materials that improve the adhesion between the substrate and the adhesive coating can be used without particular limitation. Examples of adhesive materials include silane coupling agents, titanium coupling agents, and zirconium coupling agents.

[0405] 4. Manufacturing method of phase retardation film

[0406] The method for manufacturing a retardation film according to an embodiment of the present invention includes a step of forming a retardation layer by having the following steps:

[0407] The process of forming a film from the polymeric composition of the embodiments of the present invention described above (film forming process);

[0408] At least the process of orienting the polymeric compound in the polymeric composition after film formation (orientation process); and

[0409] A process (polymerization process) in which the above-mentioned polymerizable compound is polymerized at least after the orientation process described above.

[0410] As the polymerizable composition, the same as that described in "B. Polymerizable Composition" above can be used, so the description is omitted here.

[0411] (1) Film-forming process of polymeric composition

[0412] A polymeric composition is uniformly coated onto a support to form a film.

[0413] As described above, the film thickness can be adjusted in a way that imparts the desired phase difference by appropriately adjusting the coating amount of the polymeric composition and the concentration of the polymeric liquid crystal compound.

[0414] The support here can be the aforementioned substrate or the alignment film of a substrate having the aforementioned alignment film.

[0415] The coating method can be any method that can form a film with good thickness accuracy as required, and an appropriate method can be selected. Examples include: gravure coating, reverse coating, blade coating, dip coating, spray coating, air knife coating, spin coating, roller coating, printing, dip-coating, curtain coating, die coating, casting, rod coating, extrusion coating, and E-die coating.

[0416] (2) Orientation process

[0417] Next, at least the polymeric liquid crystal compound in the polymeric composition after film formation is oriented. The polymeric liquid crystal compound in the polymeric composition after film formation is adjusted to a temperature at which it can be oriented, and then heated. Through this heat treatment, the oriented main chain portion of the polymeric liquid crystal compound of the present invention, and any polymeric liquid crystal compounds that are different from the polymeric compound of the present invention and may be further included as needed, can be oriented and dried, and can be immobilized while maintaining the above-mentioned orientation state.

[0418] The orientation temperature varies depending on the substances in the polymerizable composition, and therefore must be adjusted accordingly. For example, it is preferably carried out in a range of 60°C or higher and 200°C or lower, and more preferably in a range of 60°C or higher and 100°C or lower.

[0419] As a heating method, well-known heating and drying methods can be appropriately selected and used.

[0420] In addition, the heating time can be selected appropriately, for example, within the range of 10 seconds or more and 2 hours or less, preferably 20 seconds or more and 30 minutes or less.

[0421] (3) Polymerization process

[0422] After the above-described orientation process, the polymeric compound is polymerized at least once. In the above-described orientation process, the coating film, which is fixed in a state that maintains the orientation of the polymeric compound and the polymeric liquid crystal compound that may be further contained, is subjected to light irradiation, for example, thereby polymerizing the polymeric compound and obtaining a phase retardation layer containing the above-described polymeric composition.

[0423] Ultraviolet (UV) irradiation can be appropriately used for light irradiation. UV irradiation can utilize UV ​​light emitted from ultra-high pressure mercury lamps, high pressure mercury lamps, low pressure mercury lamps, carbon arc lamps, xenon arc lamps, metal halide lamps, etc. The irradiation dose from the energy source can be appropriately selected, preferably based on the cumulative exposure at a wavelength of 365 nm, for example, 10 mJ / cm². 2 Above and 10000 mJ / cm 2 Within the following range.

[0424] 5. Applications

[0425] The phase retardation film of the present invention can be suitably used, for example, as a quarter-wavelength anti-reflective plate, and can be suitably used in various optical components for display devices as described below.

[0426] E. Transfer laminate

[0427] The transfer laminate of the present invention includes a phase difference layer and a support that peelably supports the phase difference layer, and

[0428] The aforementioned phase retardation layer comprises a cured product of the polymeric composition of the present invention.

[0429] The transfer layer is used for the transfer of the phase difference layer.

[0430] The transfer laminate of this embodiment, since the phase retardation layer contains a cured product of the polymeric composition, suppresses the precipitation of polymeric compounds and exhibits excellent optical properties. Based on the transfer laminate of this embodiment, the phase retardation layer of the present invention, for example, a substrate-free thin film, can be transferred to any other optical component.

[0431] According to this embodiment, the transfer laminate can provide, for example... Figure 2 The example shown is a retardation film 10 containing only the retardation layer 1. Figure 5 The example shown is a phase retardation film comprising a laminate 26 with an alignment film 23 and a phase retardation layer 21 stacked together, without a substrate. That is, as long as the phase retardation layer can be at least peeled off, an alignment film or the like can also be stacked on the phase retardation layer for transfer of the laminate for transfer.

[0432] The structure of this transfer laminate will be described below, but the polymeric composition of the embodiments of the present invention described above is as described above, so the description is omitted here.

[0433] The layer structure of the transfer laminate is explained with reference to the figure. Figure 4 and Figure 5 Each of these represents an embodiment of the transfer laminate of the present invention.

[0434] Figure 4 One embodiment of the transfer laminate 20 shown in the example is a transfer laminate in which an alignment film 13 and a phase difference layer 11 are sequentially laminated on a second substrate 12 as a phase difference layer 16 for transfer and a support 15 that can be peeled off to support the phase difference layer. Figure 4 The transfer laminate illustrated is an example of a transfer laminate in which the phase difference layer 11 (16) can be transferred by making the peel strength between the second substrate 12 and the alignment film 13 greater than the peel strength between the alignment film 13 and the phase difference layer 11.

[0435] Figure 5 One embodiment of the transfer laminate 30 shown in the example is a transfer laminate in which an alignment film 23 and a phase difference layer 21 are sequentially laminated on a second substrate 22 as a phase difference layer 26 for transfer and a support 25 that can peel off the phase difference layer. Figure 5 The transfer laminate illustrated is an example of a transfer laminate in which the peel strength between the second substrate 22 and the alignment film 23 is less than the peel strength between the alignment film 23 and the phase difference layer 21, and peeling occurs at the interface 27 between the second substrate 22 and the alignment film 23, so that the phase difference layer 21 and the alignment film 23 can be transferred as a phase difference layer 26 for transfer.

[0436] For example, whether the peel strength between the second substrate and the alignment film is greater or less than the peel strength between the alignment film and the retardation layer can be determined by peeling the retardation layer and identifying at which interface peeling occurs. The interface at which peeling occurs can be analyzed, for example, using IR (Infrared Resonance) technology.

[0437] in addition, Figure 6 One embodiment of the transfer laminate 40 shown in the example is a transfer laminate in which a phase difference layer 31 is sequentially laminated on a second substrate 32 as a phase difference layer 36 for transfer and a support 35 that peelably supports the phase difference layer.

[0438] The following describes this embodiment, but the phase difference layer can be the same as the phase difference layer described in "D. Phase Difference Film" above, so the description is omitted here.

[0439] Alternatively, the alignment film and substrate may be the same as those described in “D. Phase Difference Film” above, but the following methods may be used as examples of methods to adjust the peel strength.

[0440] In order to obtain Figure 4 The transfer laminate 20 illustrated in the diagram has a peel strength between the second substrate 12 and the alignment film 13 that is greater than the peel strength between the alignment film 13 and the retardation layer 11. For this purpose, for example, a method can be used where the solvent included in the alignment film forming composition is a solvent capable of dissolving the second substrate. As the second substrate, a resin substrate is preferably used; alternatively, the surface of the substrate may be subjected to a surface treatment to improve adhesion. In this case, the adhesion between the resin substrate and the alignment film can be improved.

[0441] Furthermore, in order to reduce the peel strength between the alignment film and the retardation layer, and to make the peel strength between the substrate and the alignment film greater than that between the alignment film and the retardation layer, it is preferable to have a relatively high solvent resistance in the alignment film. When the solvent resistance of the alignment film is relatively high, when the polymeric composition is coated on the alignment film to form the retardation layer, the alignment film is less likely to dissolve in the solvent in the polymeric composition, thus reducing the adhesion between the alignment film and the retardation layer.

[0442] On the other hand, in order to obtain Figure 5 In the transfer laminate 30 illustrated, the peel strength between the second substrate 22 and the alignment film 23 is less than the peel strength between the alignment film 23 and the retardation layer 21. For this purpose, a release treatment may be performed on the surface of the substrate, or a release layer may be formed. This improves the peelability of the substrate, making the peel strength between the substrate and the alignment layer less than the peel strength between the alignment layer and the retardation layer.

[0443] As a demolding process, surface treatments such as fluorine treatment and silicone treatment can be listed.

[0444] Materials used as release agents include, for example, fluorine-based release agents, silicone-based release agents, and wax-based release agents. Methods for forming the release layer include, for example, applying the release agent by dipping, spraying, or roller coating.

[0445] In addition, in order to obtain Figure 6 The transfer laminate 40 shown in the example can also have a release treatment applied to the surface of the substrate as needed, or a release layer can be formed.

[0446] The substrate used for transfer lamination may or may not be flexible, but in terms of ease of peeling off the substrate, flexibility is preferred.

[0447] Regarding the thickness of the substrate used for the transfer laminate, in order to balance sufficient self-supporting strength and flexibility that is as suitable as possible for the manufacturing of the transfer laminate and the transfer process of this embodiment, it is generally preferred to be in the case of sheet material of the above-mentioned material in the range of 20 μm or more and 200 μm or less.

[0448] The phase retardation layer provided by the transfer laminate of the present invention can be suitably used for the same purposes as the phase retardation film described above, for example, it can be suitably used as a quarter-wavelength plate for anti-reflection, can be transferred to optical components for various display devices, and is suitable for providing optical components for thin films.

[0449] F. Optical components

[0450] The optical component of the present invention has a polarizing plate on the phase difference film of the present invention described above.

[0451] The optical components of this embodiment will be described with reference to the figures. Figure 7 This is a schematic cross-sectional view illustrating one embodiment of the optical component.

[0452] At Figure 7 In the example of the optical component 60, a polarizing plate 50 is disposed on the phase retardation film 10 of the present invention. An adhesive layer (not shown) may also be provided between the phase retardation film 10 and the polarizing plate 50 as needed.

[0453] In this embodiment, the polarizing plate is a plate-shaped material that allows light vibrating in a specific direction to pass through, and can be appropriately selected from existing known polarizing plates. For example, polyvinyl alcohol films, polyvinyl formal films, polyvinyl acetal films, ethylene-vinyl acetate copolymer saponified films, etc., which are formed by dyeing with iodine or dyes and then stretching can be used.

[0454] Furthermore, in this embodiment, the adhesive or bonding agent used as the adhesive layer (bonding layer) can be appropriately selected from the existing known types, and any bonding form such as pressure-sensitive adhesive, two-component curing adhesive, ultraviolet curing adhesive, thermosetting adhesive, and hot melt adhesive can be used.

[0455] In the optical component of this embodiment, in addition to the polarizing plate, other layers commonly found in known optical components may also be included. Examples of such other layers include phase retardation layers different from the phase retardation layer of this embodiment, as well as anti-reflection layers, diffusion layers, anti-glare layers, antistatic layers, protective films, etc., but these are not limited to these.

[0456] The optical components of this embodiment can be suitably used, for example, as optical components to suppress external light reflection or as wide-field-of-view polarizing plates for various display devices.

[0457] The manufacturing method of the optical component of the present invention is not particularly limited, and any method for stacking polarizers on the phase retardation film of the present invention can be appropriately selected. For example, a manufacturing method in which polarizers are stacked on the phase retardation film of the present invention using an adhesive layer or bonding layer can be cited.

[0458] Furthermore, as a method for manufacturing an optical component according to one embodiment of the present invention, a method for manufacturing an optical component having the following steps can be listed:

[0459] The transfer lamination preparation process prepares the transfer lamination of the present invention described above.

[0460] A transfer process in which a transfer object, comprising at least a polarizing plate, is positioned opposite the phase difference layer of the transfer laminate, and the transfer laminate is transferred onto the transfer object; and

[0461] The peeling process peels off the transfer laminate that was transferred from the support body to the transfer body.

[0462] According to a method for manufacturing an optical component using an embodiment of the present invention employing the above-described transfer laminate, an optical component comprising only a polarizing plate and the aforementioned retardation layer in the retardation film of the present invention can be obtained.

[0463] The transfer laminate used in the method for manufacturing an optical component according to one embodiment of the present invention may be the same as the transfer laminate described in "E. Transfer Laminate" above, so the description is omitted here.

[0464] Furthermore, the transfer body used in the manufacturing method of the optical component according to one embodiment of the present invention can typically include a transfer body having an adhesive layer and a polarizing plate, but is not limited to these, and may further have other layers that are the same as those that the optical component according to one embodiment of the present invention may have.

[0465] G. Display device

[0466] The display device of the present invention is characterized by having the phase difference film of the present embodiment or the optical component of the present embodiment described above.

[0467] Display devices include, but are not limited to, light-emitting display devices and liquid crystal display devices.

[0468] In particular, since it has the phase difference film of this embodiment or the optical component of this embodiment, it has the effect of suppressing external light reflection and improving the viewing angle, especially in light-emitting display devices such as organic light-emitting display devices that have a transparent electrode layer, a light-emitting layer and an electrode layer in sequence.

[0469] Referring to the figures, an example of a light-emitting display device as one embodiment will be described. Figure 8 This is a schematic cross-sectional view illustrating one embodiment of the optical component.

[0470] At Figure 8In the example of the organic light-emitting display device 100, a polarizing plate 50 is disposed on the light-emitting surface side of the phase difference film 10, and a transparent electrode layer 71, a light-emitting layer 72 and an electrode layer 73 are sequentially provided on the opposite side.

[0471] As the light-emitting layer 72, examples include a configuration in which a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection layer are sequentially stacked from the transparent electrode layer 71 side. In this embodiment, the transparent electrode layer, hole injection layer, hole transport layer, light-emitting layer, electron injection layer, electrode layer, and other components can be appropriately used from known sources. A light-emitting display device manufactured in this way can be applied, for example, to both passively driven and actively driven organic EL displays.

[0472] Furthermore, the display device of this embodiment is not limited to the above configuration, and may be configured with a known configuration of appropriate selection.

[0473] Example

[0474] Regarding the various compounds manufactured, JEOL JNM-LA400WB manufactured by Japan Electronics Corporation was used. 1 The chemical structure was confirmed by H NMR determination.

[0475] Furthermore, the phase transition temperatures of each manufactured compound were confirmed by observing its texture using a polarizing microscope (manufactured by Olympus, BX51) equipped with a temperature-controlled stage, while simultaneously heating. C indicates crystallization, N indicates nematic phase, and I indicates isotropic liquid. For example, "C 130 N180 I" indicates that the compound transitions from crystallization to a nematic phase at 130°C and from a nematic phase to an isotropic liquid at 180°C.

[0476] [Manufacturing Example 1: Manufacture of Compound 1 represented by Formula (1-1)]

[0477] First, 27 g (150 mmol) of 4,4′-dihydroxybiphenyl (represented by formula (1-1-1)) and 46 g (330 mmol) of hexamethylenetetramine (represented by formula (1-1-1)) were dissolved in 320 mL of trifluoroacetic acid in a 500 mL round-bottom flask, and the reaction was carried out at 110 °C for 3 hours. After the reaction was completed, 3 L of hydrochloric acid with a concentration of 4 equivalences was added under ice bath and the mixture was stirred overnight. After stirring, the precipitate was filtered. Water (1 L) was added to the crude product and the mixture was stirred for 1 hour for suspension purification. The precipitate was filtered, and the obtained crystals were dried to obtain 17.5 g (21 mmol, yield 21%) of the intermediate represented by formula (1-1-2).

[0478] A solution of 43 g (210 mmol) of N,N-dicyclohexylcarbodiimide (DCC) in 50 mL of dichloromethane was added dropwise to a suspension of 172 g (1.0 mol) of cyclohexanedicarboxylic acid, 53 g (200 mmol) of 6-(4-hydroxyphenyl)hexyl acrylate (DKSH), and 0.98 g (8.0 mmol) of N,N-dimethylaminopyridine (DMAP). After the addition was complete, the mixture was stirred for 12 hours, and the precipitate was filtered off. The precipitate was then washed with an aqueous solution of sodium bicarbonate and 1N hydrochloric acid, and the solvent was removed by distillation. The crude product was purified by open-column chromatography to synthesize carboxylic acid derivative 1 represented by formula (1-1-3).

[0479] Then, a solution of 17.0 g (29 mmol) of the intermediate represented by formula (1-1-2), 132 g (76 mmol) of the carboxylic acid derivative represented by formula (1-1-3), and 0.14 g (1.2 mmol) of N,N-dimethylaminopyridine (DMAP) in dichloromethane (70 mL) was added dropwise. After the addition was complete, the mixture was stirred for 12 hours, and the precipitate was filtered off by distillation. Chloroform (70 mL) was added to the crude product, and the mixture was stirred for 1 hour for suspension purification. The precipitate was filtered off, and the obtained crystals were dried to obtain 223 g (22 mmol, yield 75%) of the intermediate represented by formula (1-1-4).

[0480] 5.0 g (30 mmol) of 2-hydrazinobenzothiazole and 2.5 g (45 mmol) of potassium hydroxide were added to N,N-dimethylformamide (90 mL), and the mixture was heated at 80 °C. After reaching the specified temperature, 9.2 g (36 mmol) of hexyl p-toluenesulfonate was added dropwise. The mixture was stirred for 4 hours after the addition was complete. After the reaction was complete, 10 mL of water was added for extraction, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography, and the solvent was removed by distillation, thus obtaining 33.0 g (12 mmol, 40% yield) of the intermediate represented by formula (1-1-5).

[0481] 22.0 g (1.9 mmol) of the intermediate represented by formula (1-1-4) obtained above and 15 mg of 12 equivalent hydrochloric acid were dissolved in 10 mL of tetrahydrofuran. A solution of 31.2 g (5.0 mmol) of the intermediate represented by formula (1-1-5) in 3 mL of tetrahydrofuran was added dropwise. After the addition was complete, the mixture was stirred for 12 hours, and then added dropwise to 50 mL of methanol. The resulting precipitate was filtered, and the solvent was removed by distillation. Methanol (20 mL) was added to the obtained crude product, and the mixture was stirred for 1 hour for suspension purification. The precipitate was filtered, and the obtained crystals were dried to obtain compound 1 represented by formula (1-1) 1.4 g (0.94 mmol, yield 49%).

[0482] Phase transition temperature (at increasing temperature): C 130 N 180 I

[0483] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.8 3(dd, 2H), 4.34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 2.70-2.55(m, 4H), 2 .45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 20H), 0.88(t, 6H).

[0484] [Chemistry 43]

[0485]

[0486] [Manufacturing Example 2: Manufacture of Compound 2 represented by Formula (1-2)]

[0487] 4.0 g (24 mmol) of 2-amino-6-fluorobenzothiazole was added to 20 mL of ethylene glycol. Then, 3.6 g (71 mmol) of hydrazine monohydrate and 1.9 g (55 mmol) of 12 equivalent hydrochloric acid were added dropwise under ice bath conditions, and the mixture was stirred at 130 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and then 300 mL of water was added. The precipitate was filtered, and the resulting crystals were dried to obtain 43.5 g (19 mmol, 80% yield) of the intermediate.

[0488] In the manufacture of Manufacturing Example 1, in the step of obtaining intermediate 3, an equimolar amount of the above intermediate 4 was used instead of 2-hydrazinobenzothiazole to obtain intermediate 5 represented by formula (1-2-5). Otherwise, 1.2 g (0.78 mmol, yield 41%) of compound 2 represented by formula (1-2) was obtained in the same manner as in Manufacturing Example 1.

[0489] Phase transition temperature (at increasing temperature): C 141 N 208 I

[0490] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.52 (d, 2H), 7.21 (d, 2H), 7.05-6.75 (m, 12H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd, 2H), 4.34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 2.70-2.55(m, 4H), 2.45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 20H), 0.88(t, 6H).

[0491] [Chemistry 44]

[0492]

[0493] [Manufacturing Example 3: Manufacture of Compound 3 represented by Formula (1-3)]

[0494] In the manufacturing process of intermediate 4 in manufacturing example 2, equimolar amounts of 2-amino-6-ethoxybenzothiazole were used instead of 2-amino-6-fluorobenzothiazole. Otherwise, intermediate 63.1 g (16 mmol, yield 68%) was obtained in the same manner as in the manufacturing process of intermediate 4 in manufacturing example 2.

[0495] In the manufacture of Manufacturing Example 1, intermediate 6 was used instead of 2-hydrazinobenzothiazole in the step of obtaining intermediate 3 to obtain intermediate 7 represented by formula (1-3-5). Otherwise, 1.3 g (0.83 mmol, yield 43%) of compound 3 represented by formula (1-3) was obtained in the same manner as in Manufacturing Example 1.

[0496] Phase transition temperature (at increasing temperature): C 147 N 241 I

[0497] 1H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.52 (d, 2H), 7.21 (d, 2H), 7.05-6.75 (m, 12H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd, 2H), 4. 34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 3.65(t, 4H), 2.70-2.55(m, 4H), 2 .45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 26H), 0.88(t, 6H).

[0498] [Chemistry 45]

[0499]

[0500] [Manufacturing Example 4: Manufacture of Compound 4 represented by Formula (1-4)]

[0501] In the manufacture of Manufacturing Example 1, an equimolar amount of 1-bromo-2-(2-methoxyethoxy)ethane was used instead of hexyl p-toluenesulfonate in the step of obtaining intermediate 3 to obtain intermediate 8 represented by formula (1-4-5). Otherwise, 1.2 g (0.77 mmol, yield 40%) of compound 4 represented by formula (1-4) was obtained in the same manner as in Manufacturing Example 1.

[0502] Phase transition temperature (at increasing temperature): C 116 N 205 I

[0503] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 8.13 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7. 20(m, 6H), 7.05-6.85(m, 10H), 6.41(dd, 2H), 6.25-6.10(m, 2H), 5.83(dd, 2H), 4.53(t, 4H), 4.18(t, 4H), 4.02-3.85(m, 8H), 3.65(t, 4H), 3.51(t, 4H ), 3.32(s, 4H), 2.70-2.55(m, 4H), 2.45-2.35(m, 8H), 1.95-1.30(m, 20H).

[0504] [Chemistry 46]

[0505]

[0506] [Manufacturing Example 5: Manufacture of Compound 5 represented by Formula (1-5)]

[0507] In the manufacturing process of intermediate 4 in manufacturing example 2, an equimolar amount of 5-methoxy[1,3]thiazo[5,4-b]pyridine-2-amine was used instead of 2-amino-6-fluorobenzothiazole. Otherwise, 92.4 g (12 mmol, yield 52%) of intermediate was obtained in the same manner as in the manufacturing process of intermediate 4 in manufacturing example 2.

[0508] In the manufacture of Manufacturing Example 1, intermediate 9 was used instead of 2-hydrazinobenzothiazole in the step of obtaining intermediate 3 to obtain intermediate 10 represented by formula (1-5-5). Otherwise, compound 5 represented by formula (1-5) 1.1 g (0.69 mmol, yield 36%) was obtained in the same manner as in Manufacturing Example 1.

[0509] Phase transition temperature (at increasing temperature): C 134 N 176 I

[0510] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.52 (d, 2H), 7.21 (d, 2H), 7.05-6.75 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd, 2H), 4.34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 2.70-2.55(m, 4H), 2.45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 26H), 0.88(t, 6H).

[0511] [Chemistry 47]

[0512]

[0513] [Manufacturing Example 6: Manufacture of Compound 6 represented by Formula (1-6)]

[0514] 21 g (110 mmol) of 2-bromo-5-hydroxybenzaldehyde and 20 g (110 mmol) of 2-formyl-4-methoxyphenylboronic acid were dissolved in toluene:ethanol = 3:1 (400 mL). 100 mL of 2M sodium carbonate aqueous solution was added, and the mixture was heated at 60 °C. After reaching the specified temperature, 2.4 g (2.1 mmol) of tetrakis(triphenylphosphine)palladium(O) was added, and the mixture was heated at 80 °C. The mixture was stirred for 10 hours after reaching the specified temperature. After the reaction was complete, the mixture was cooled to room temperature, the insoluble residue was filtered off, and the organic layer was extracted and concentrated. The residue was purified by silica gel column chromatography, and the solvent was removed by distillation, thus obtaining intermediate 11 11 g (44 mmol, yield 42%). The structure of the target compound was identified by 1H-NMR.

[0515] In Manufacturing Example 1, intermediate 11 was used in place of intermediate 1 represented by formula (1-1-2) with the carboxylic acid derivative 1 represented by formula (1-1-3) to obtain intermediate 12. In Manufacturing Example 1, intermediate 12 was used in place of intermediate 2 represented by formula (1-1-4). Otherwise, compound 6 represented by formula (1-6) 1.1 g (0.74 mmol, yield 39%) was obtained in the same manner as in Manufacturing Example 1.

[0516] Phase transition temperature (at increasing temperature): C 165 N 180 I

[0517] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.92 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.8 3(dd, 2H), 4.34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 2.70-2.55(m, 4H), 2 .45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 20H), 0.88(t, 6H).

[0518] [Chemistry 48]

[0519]

[0520] [Manufacturing Example 7: Manufacture of Compound 7 represented by Formula (1-7)]

[0521] In the manufacture of intermediate 11 in Manufacturing Example 6, 5-bromo-2-hydroxy-4-methylbenzaldehyde was used in place of 2-bromo-5-hydroxybenzaldehyde in an equimolar amount, and 3-formyl-4-methoxyphenylboronic acid was used in place of 2-formyl-4-methoxyphenylboronic acid in an equimolar amount to obtain intermediate 13.

[0522] In Manufacturing Example 1, intermediate 14 was obtained by replacing intermediate 1 represented by formula (1-1-2) with the carboxylic acid derivative 1 represented by formula (1-1-3). In Manufacturing Example 1, intermediate 2 represented by formula (1-1-4) was replaced with intermediate 14. Otherwise, 0.81 g (0.53 mmol, yield 24%) of compound 7 represented by formula (1-7) was obtained in the same manner as in Manufacturing Example 1.

[0523] Phase transition temperature (at increasing temperature): C 152 N 171 I

[0524] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 9H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd, 2H), 4.34 (t, 4H), 4.17 (t, 4H), 3.97 (t, 4H), 2.70-2.55 (m, 7H), 2. 45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 20H), 0.88(t, 6H).

[0525] [Chemistry 49]

[0526]

[0527] [Manufacturing Example 8: Manufacture of Compound 8 represented by Formula (1-8)]

[0528] 6-Bromohexanol (7.3 g, 41 mmol) was added to a DMF (250 mL) suspension of ethyl 4-hydroxybenzoate (7.0 g, 44 mmol) and potassium carbonate (6.5 g, 47 mmol), and the mixture was stirred at 80 °C for 8 hours. After the reaction was complete, the reaction solution was diluted with water, extracted with ethyl acetate, and the solvent was removed by distillation. An aqueous solution of potassium hydroxide (2.8 g, 47 mmol) was added to the obtained crude product, and the mixture was reacted at 100 °C for 4 hours for hydrolysis. After the reaction was complete, an aqueous solution of hydrochloric acid was added, followed by extraction with ethyl acetate, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography, and the solvent was removed by distillation, thus obtaining p-(6-hydroxyhexyloxy)benzoic acid in 83% (8.7 g, 37 mmol).

[0529] Next, a suspension of (6-hydroxyethoxy)benzoic acid (7.1 g, 30 mmol), acryloyl chloride (2.5 g, 27 mmol), and dimethylaniline (DMA) (3.3 g, 27 mmol) in tetrahydrofuran (150 mL) was stirred for 12 hours. After the reaction was complete, water and ethyl acetate were added for separation. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography, followed by distillation to remove the solvent, thus obtaining 4-[6-(acryloyloxy)hexyloxy]benzoic acid in 85% (7.4 g, 26 mmol).

[0530] Trans-4-hydroxycyclohexanecarboxylic acid (5.0 g, 32 mmol) and triethylamine (5.3 g, 52 mmol) were dissolved in tetrahydrofuran (25 mL) under a nitrogen atmosphere while being stirred at a temperature below 10 °C. Chloromethyl ether (3.0 g, 37 mmol) was slowly added dropwise, and the mixture was stirred at room temperature for 8 hours. The organic layer was extracted with ethyl acetate and water, washed with saturated sodium bicarbonate solution and water, and dried with anhydrous magnesium sulfate to obtain 4.8 g (26 mmol, 80% yield) of trans-4-hydroxycyclohexanecarboxylic acid methoxymethyl ester.

[0531] A solution of N,N-dicyclohexylcarbodiimide (DCC) in dichloromethane (5 mL) was added dropwise to a suspension of 7.4 g (26 mmol) of 4-[6-(acryloyloxy)hexyloxy]benzoic acid, 4.7 g (25 mmol) of trans-4-hydroxycyclohexanecarboxylic acid methoxymethyl ester, and 0.12 g (1.0 mmol) of N,N-dimethylaminopyridine (DMAP) in dichloromethane (150 mL). After the addition was complete, the mixture was stirred for 12 hours. The precipitate was filtered, washed with sodium bicarbonate aqueous solution and 1N hydrochloric acid, and the solvent was removed by distillation. 0.40 g (2.1 mmol) of p-toluenesulfonic acid (pTSA) was added to a tetrahydrofuran (20 mL) solution of the obtained crude product, and the mixture was heated and stirred at 40 °C for 8 hours. The organic layer was extracted with ethyl acetate and water, washed with saturated sodium bicarbonate solution and water, dried with anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue was recrystallized with methanol to obtain 25.4 g (13 mmol, yield 52%) of the carboxylic acid derivative represented by formula (1-8-3).

[0532] [Transformation 50]

[0533]

[0534] In Manufacturing Example 1, carboxylic acid derivative 2 represented by formula (1-8-3) was used instead of carboxylic acid derivative 1 represented by formula (1-1-3). Otherwise, compound 8 represented by formula (1-8) was obtained in 0.98 g (0.66 mmol, yield 32%) in the same manner as in Manufacturing Example 1.

[0535] Phase transition temperature (at increasing temperature): C 134 N 167 I

[0536] 1H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.8 3(dd, 2H), 4.52(t, 4H), 4.20(t, 4H), 3.95(t, 4H), 2.70-2.55(m, 4H), 2 .45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 20H), 0.88(t, 6H).

[0537] [Chemistry 51]

[0538]

[0539] [Manufacturing Example 9: Manufacture of Compound 9 represented by Formulas (1-9)]

[0540] Intermediate 2, represented by formula (1-1-4), is obtained in the same manner as in manufacturing example 1.

[0541] 22.0 g (1.9 mmol) of intermediate and 0.82 g (3.8 mmol) of 3-methyl-2-benzothiazolinone hydrazone hydrochloride were dissolved in 30 mL of 1-propanol and stirred under reflux for 1 hour. After the reaction was complete, the mixture was cooled to room temperature, and then 30 mL of THF was added to dissolve it. A 10% sodium bicarbonate aqueous solution was added dropwise to the reaction solution to precipitate the solid. The precipitate was filtered, washed, and dried to obtain compound 9 (represented by formula (1-9)) 0.9 g (0.66 mmol, yield 33%). The structure of the target compound was identified by 1H-NMR.

[0542] Phase transition temperature (at increasing temperature): C 140 N 165 I

[0543] 1 H NMR (DMSO; δppm): 8.49 (s, 2H), 8.14 (s, 2H), 7.85 (d, 2H), 7.66 (d, 2H), 7.45 (d, 2H), 7.40-7.30 (m, 4H), 7.08 (t, 2H), 6.88 (s, 8H), 6.41 (dd , 2H), 6.25-6.10(m, 2H), 5.83(dd, 2H), 4.06(t, 4H), 3.97(t, 4H), 3.36(s, 6H), 2.30-2.20(m, 4H), 1.90-1.65(m, 12H), 1.60-1.35(m, 20H)

[0544] [Chemistry 52]

[0545]

[0546] [Manufacturing Example 10: Manufacture of Compound 10 represented by Formula (1-10)]

[0547] In the manufacture of Manufacturing Example 1, in the step of obtaining intermediate 3, equimolar amounts of 1-(2-bromoethoxy)butane were used instead of hexyl p-toluenesulfonate to obtain intermediate 16 represented by formula (1-10-5). Otherwise, 1.33 g (0.87 mmol, yield 43%) of compound 10 represented by formula (1-10) was obtained in the same manner as in Manufacturing Example 1.

[0548] Phase transition temperature (at increasing temperature): C 122 N 167 I

[0549] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd, 2H) , 4.34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 3.65-3.50(m, 8H), 2.70-2.55(m, 4 H), 2.45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 12H), 0.88(t, 6H)

[0550] [Chemistry 53]

[0551]

[0552] [Manufacturing Example 11: Manufacture of Compound 11 represented by Formula (1-11)]

[0553] 3.2 g (24 mmol) of 2-aminobenzoxazole was added to 20 mL of ethylene glycol. Then, 3.6 g (71 mmol) of hydrazine monohydrate and 1.9 g (55 mmol) of 12 equivalent hydrochloric acid were added dropwise under ice bath conditions, and the mixture was stirred at 130 °C for 5 hours. After the reaction was complete, the mixture was cooled to room temperature, and then 300 mL of water was added. The precipitate was filtered, and the resulting crystals were dried to obtain 173.5 g (19 mmol, yield 80%) of the intermediate.

[0554] In the manufacture of Manufacturing Example 1, in the step of obtaining intermediate 3, an equimolar amount of the above intermediate 17 was used instead of 2-hydrazinobenzothiazole, and an equimolar amount of 1-(2-bromoethoxy)butane was used instead of hexyl p-toluenesulfonate to obtain intermediate 18 represented by formula (1-11-5). Otherwise, 1.2 g (0.78 mmol, yield 41%) of compound 11 represented by formula (1-11) was obtained in the same manner as in Manufacturing Example 1.

[0555] Phase transition temperature (at increasing temperature): C 119 N 169 I

[0556] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.55 (m, 2H), 7.41-7.20 (m, 8H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.8 3(dd, 2H), 4.34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 2.70-2.55(m, 4H), 2 .45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 20H), 0.88(t, 6H)

[0557] [Chemistry 54]

[0558]

[0559] [Manufacturing Example 12: Manufacture of Compound 12 represented by Formula (1-12)]

[0560] In the manufacture of Manufacturing Example 1, in the step of obtaining intermediate 3, 1-bromo-2-ethylhexane was used instead of hexyl p-toluenesulfonate in an equimolar amount to obtain intermediate 19 represented by formula (1-12-5). Otherwise, compound 12 represented by formula (1-12) 1.3 g (0.84 mmol, yield 44%) was obtained in the same manner as in Manufacturing Example 1.

[0561] Phase transition temperature (at increasing temperature): C 125 N 168 I

[0562] 1H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7. 20(m, 6H), 7.05-6.85(m, 10H), 6.41(dd, 2H), 6.25-6.10(m, 2H), 5.83(dd, 2H), 4.34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 2.70-2.55(m, 4H), 2.45-2.35 (m, 8H), 1.97-1.67 (m, 24H), 1.51-1.32 (m, 18H), 0.99 (t, 6H), 0.88 (t, 6H)

[0563] [Chemistry 55]

[0564]

[0565] [Manufacturing Example 13: Manufacture of Compound 13 represented by Formula (1-13)]

[0566] In the manufacture of Manufacturing Example 1, in the step of obtaining intermediate 3, an equimolar amount of tetrahydrofuran methyl bromide was used instead of hexyl p-toluenesulfonate to obtain intermediate 20 represented by formula (1-13-5). Otherwise, compound 13 represented by formula (1-13) 1.9 g (0.79 mmol, yield 41%) was obtained in the same manner as in Manufacturing Example 1.

[0567] Phase transition temperature (at increasing temperature): C 119 N 171 I

[0568] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H) , 5.83(dd, 2H), 4.34(t, 4H), 4.17(t, 4H), 3.85-3.79(m, 6H), 2.70-2.55(m, 4H), 2.45-2.35(m, 8H), 1.91-1.60(m, 28H), 1.51-1.32(m, 4H)

[0569] [Chemistry 56]

[0570]

[0571] [Manufacturing Example 14: Manufacture of Compound 14 Represented by Formula (1-14)]

[0572] According to existing reports (Macromolecules (Washington, DC, United States), 40(15), 5337-5343; 2007), 6-chlorohexyl acrylate was synthesized.

[0573] A solution of 7.6 g (55 mmol) of 2-(4-hydroxyphenyl)ethanol in 30 mL of dimethylformamide was added dropwise to a suspension of 9.5 g (50 mmol) of 6-chlorohexyl acrylate and 14 g (100 mmol) of potassium carbonate in 100 mL of dimethylformamide. After the addition was complete, the reaction vessel was heated to 90 °C and reacted for 5 hours. After the reaction was complete, 200 mL of ethyl acetate was added, and the mixture was washed with pure water and saturated brine. The organic layer was dried with anhydrous sodium sulfate to synthesize 6-(4-(2-hydroxyethyl)phenyl)hexyl acrylate.

[0574] In the method for synthesizing carboxylic acid derivative 1 of manufacturing example 1, 6-(4-(2-hydroxyethyl)phenyl)hexyl acrylate was used instead of 6-(4-hydroxyphenyl)hexyl acrylate, thereby synthesizing 4.2 g (9.4 mmol) of carboxylic acid derivative 3 represented by formula (1-14-3).

[0575] [Chemistry 57]

[0576]

[0577] In Manufacturing Example 1, carboxylic acid derivative 3 represented by formula (1-14-3) was used instead of carboxylic acid derivative 1 represented by formula (1-1-3). Otherwise, compound 14 represented by formula (1-14) 1.2 g (0.75 mmol, yield 35%) was obtained in the same manner as in Manufacturing Example 1.

[0578] Phase transition temperature (at increasing temperature): C 118 N 169 I

[0579] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 ( m, 2H), 7.05-6.85 (m, 14H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd, 2H), 4. 51(t, 4H), 4.34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 3.02(t, 4H), 2.70-2.55(m , 4H), 2.45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 20H), 0.88(t, 6H)

[0580] [Chem.58]

[0581]

[0582] [Manufacturing Example 15: Manufacture of Compound 15 represented by Formula (1-15)]

[0583] In the method for synthesizing carboxylic acid derivative 2 of Example 8, methyl 3-(4-hydroxyphenyl)propionate was used instead of ethyl 4-hydroxybenzoate in an equimolar amount, thereby synthesizing 3.9 g (8.7 mmol) of carboxylic acid derivative 4 represented by formula (1-15-3).

[0584] [Chemistry 59]

[0585]

[0586] In Manufacturing Example 1, carboxylic acid derivative 4 represented by formula (1-15-3) was used instead of carboxylic acid derivative 1 represented by formula (1-1-3). Otherwise, compound 15 represented by formula (1-15) 1.3 g (0.81 mmol, yield 41%) was obtained in the same manner as in Manufacturing Example 1.

[0587] Phase transition temperature (at increasing temperature): C 105 N 172 I

[0588] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd, 2H) , 4.52(t, 4H), 4.19(t, 4H), 3.99(t, 4H), 3.65-3.50(m, 8H), 2.70-2.55(m, 1 2H), 2.45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 12H), 0.88(t, 6H)

[0589] [Transformation 60]

[0590]

[0591] [Manufacturing Example 16: Manufacture of Compound 16 represented by Formula (1-16)]

[0592] According to existing reports (Journal of Polymer Science, Part A: Polymer Chemistry, 49(3), 770-780; 2011), 3-[4-[[6-[(1-bridgedoxy-2-propen-1-yl)oxy]hexyl]oxy]phenyl]-2-acrylic acid was synthesized.

[0593] In the method for synthesizing carboxylic acid derivative 2 of Example 8, 3-[4-[[6-[(1-bridgedoxy-2-propen-1-yl)oxy]hexyl]oxy]phenyl]-2-acrylic acid was used instead of 4-[6-(acryloyloxy)hexyloxy]benzoic acid, thereby synthesizing 3.8 g (8.6 mmol) of carboxylic acid derivative 5 represented by formula (1-16-3).

[0594] [Chemistry 61]

[0595]

[0596] In Manufacturing Example 1, carboxylic acid derivative 5 represented by formula (1-16-3) was used instead of carboxylic acid derivative 1 represented by formula (1-1-3). Otherwise, compound 16 represented by formula (1-16) 1.0 g (0.67 mmol, yield 38%) was obtained in the same manner as in Manufacturing Example 1.

[0597] Phase transition temperature (at increasing temperature): C 141 N 165 I

[0598] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.55 (m, 6H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.35-6.10 (m, 4H), 5.8 3(dd, 2H), 4.34(t, 4H), 4.17(t, 4H), 3.97(t, 4H), 2.70-2.55(m, 4H), 2 .45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.30(m, 20H), 0.88(t, 6H)

[0599] [Chemistry 62]

[0600]

[0601] [Manufacturing Example 17: Manufacture of Compound 17 Represented by Formula (1-17)]

[0602] Intermediate 2, represented by formula (1-1-4), is obtained in the same manner as in manufacturing example 1.

[0603] 22.0 g (1.9 mmol) of the intermediate, 0.27 g (3.8 mmol) of hydroxylamine chloride, and 0.52 g (3.8 mmol) of sodium acetate trihydrate were dissolved in 11 mL of tetrahydrofuran and stirred at room temperature for 3 hours. After the reaction was complete, the solvent was removed by distillation, and the mixture was extracted with ethyl acetate and washed with water. The crude product was concentrated and then suspended in 10 mL of methanol and stirred for 1 hour for purification. The precipitate was filtered off, and the obtained solid was dried to obtain 241.9 g (1.8 mmol, yield 93%) of the intermediate represented by formula (1-17-6).

[0604] [Chemistry 63]

[0605]

[0606] Under a nitrogen atmosphere and at 60°C, 241.5 g (1.4 mmol) of the obtained intermediate and 0.9 g (2.8 mmol) of cesium carbonate were dissolved in 2.8 mL of toluene. Under a nitrogen atmosphere, 0.95 g (3.6 mmol) of 2-iodobenzothiazole, 50 mg (0.3 mmol) of 1,10-phenanthroline, 0.16 g (0.6 mmol) of sodium potassium tartrate tetrahydrate, and 27 mg (0.14 mmol) of copper(I) iodide were added, and the mixture was stirred at 60°C for 2 hours. After the reaction was complete, the insoluble matter was separated by filtration, followed by extraction with water and ethyl acetate, and the solvent was removed by distillation. The residue was purified by silica gel column chromatography, and the solvent was removed by distillation, thus obtaining compound 17, represented by formula (1-17), 0.84 g (0.63 mmol, yield 45%).

[0607] Phase transition temperature (at increasing temperature): C 135 N 167 I

[0608] 1 H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6. 10(m, 2H), 5.83(dd, 2H), 4.34(t, 4H), 4.17(t, 4H), 2.70-2.55(m, 4H), 2.45-2.35(m, 8H), 1.95-1.65(m, 20H), 1.55-1.41(m, 4H)

[0609] [Chemistry 64]

[0610]

[0611] [Comparative Manufacturing Example 1: Manufacturing of Comparative Compound 1 Represented by Formula (C1-1)]

[0612] Referring to the synthesis of compound 4 in Example 4 of Japanese Patent No. 5962760, comparative compound 1 represented by the following formula (C1-1) was synthesized.

[0613] [Chemistry 65]

[0614] Equation (C1-1)

[0615]

[0616] [Comparative Manufacturing Example 2: Manufacturing of Comparative Compound 2 Represented by Formula (C1-2)]

[0617] Referring to the synthesis of the compound represented by formula (1-3) in Example 3 of International Publication No. 2016 / 136533, comparative compound 2 represented by formula (C1-2) was synthesized.

[0618] [Chemistry 66]

[0619] Equation (C1-2)

[0620]

[0621] [Example 1]

[0622] (1) Manufacturing of polymeric compositions

[0623] Polymerizable composition 1 is prepared by dissolving 100 parts by mass of a polymerizable liquid crystal compound (compound 1 represented by formula (1-1)) and 4 parts by mass of a photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropane-1-one: manufactured by Ciba Specialty Chemicals, Irgacure 907) in 900 parts by mass of cyclopentanone.

[0624] (2) Manufacturing of phase difference film or transfer laminate

[0625] (2-1) Preparation of compositions for photo-alignment films

[0626] According to Manufacturing Example 1 of Japanese Patent 5626493, 1.30 g of hydroxyethyl methacrylate, 3.95 g of the photo-oriented monomer represented by the following chemical formula, and 50 mg of α,α′-azobisisobutyronitrile (AIBN) as a polymerization catalyst were dissolved in 25 ml of dioxane and reacted at 90°C for 6 hours. After the reaction was completed, the copolymer was purified by reprecipitation to obtain copolymer 1 obtained by copolymerizing the photo-oriented monomer represented by the following chemical formula with hydroxyethyl methacrylate.

[0627] A composition for preparing a photo-alignment film with the composition shown below.

[0628] Copolymer 1: 0.1 parts by weight

[0629] • Hexamethoxymethyl melamine (HMM): 0.01 parts by weight

[0630] p-Toluenesulfonic acid monohydrate (PTSA): 0.0015 parts by weight

[0631] • Propylene glycol monomethyl ether (PGME): 2.1 parts by weight

[0632] [Chemistry 67]

[0633] Photooriented monomers

[0634]

[0635] (2-2) Formation of horizontally oriented films

[0636] The aforementioned photoalignment film composition was applied to one side of a PET substrate (manufactured by Toyobo Co., Ltd., E5100, 38μm thickness) using a rod coating method to achieve a cured film thickness of 0.2μm. The coating was then dried and thermally cured in an oven at 120°C for 1 minute to form a cured coating film. Subsequently, using an Hg-Xe lamp and a Glan Taylor prism, the surface of the cured coating film was exposed to an exposure of 100mJ / cm² in the vertical direction from the substrate normal. 2 A horizontally oriented film is formed by irradiating the film with polarized ultraviolet light containing an emission spectral line of 313 nm.

[0637] (2-3) Fabrication of phase retardation film or transfer laminate

[0638] The polymeric composition 1 was coated onto the formed alignment film to achieve a cured film thickness of 1 μm, thereby forming a film. Subsequently, the film was dried in an oven at the drying temperatures shown in Table 9 for 120 seconds, and then irradiated with an H vacuum tube manufactured by Fusion Corporation at an irradiation dose of 400 mJ / cm². 2 Irradiation with ultraviolet light (UV) forms a phase retardation layer, resulting in a phase retardation film or a laminate for transfer.

[0639] [Examples 2-17, Comparative Examples 1-2]

[0640] (1) Manufacturing of polymeric compositions

[0641] In Example 1, the composition of each component was changed according to Table 9 below. Otherwise, polymeric compositions 2 to 17 and comparative polymeric compositions 1 to 2 were obtained in the same manner as in Example 1.

[0642] (2) Manufacturing of phase difference film or transfer laminate

[0643] In Example 1, polymeric compositions 2 to 17 and comparative polymeric compositions 1 to 2 were used instead of polymeric composition 1. Otherwise, phase difference films or transfer laminates 2 to 17 and comparative phase difference films or transfer laminates 1 to 2 were obtained in the same manner as in Example 1.

[0644] [evaluate]

[0645] <Sample Preparation>

[0646] The sample was obtained by peeling the retardation film obtained in each embodiment and each comparative example from the PET substrate and transferring the retardation layer and the horizontal alignment film onto the adhesive glass.

[0647] <Orientation>

[0648] The orientation of the phase difference layer was evaluated using polarization microscopy on a three-level scale.

[0649] (Evaluation criteria for orientation)

[0650] A: Uniform orientation is observed visually, and over 90% orientation is observed under a polarizing microscope.

[0651] B: Orientation of level A was not obtained under visual inspection; the orientation area observed under a polarizing microscope was more than 50% but less than 90%.

[0652] C: No orientation is visible to the naked eye, and the oriented area is less than 50% when observed under a polarizing microscope.

[0653] <Phase difference (wavelength dispersion)>

[0654] The in-plane phase difference Re at wavelengths of 450nm, 550nm, and 650nm was measured using a phase difference measuring device (manufactured by Oji Measurement & Control Co., Ltd., KOBRA-WR).

[0655] Wavelength dispersion is evaluated based on the measured phase difference and the x and y values ​​calculated as follows.

[0656] x = (In-plane phase difference Re at 450nm) / (In-plane phase difference Re at 550nm)

[0657] y = (In-plane phase difference Re at 650nm) / (In-plane phase difference Re at 550nm)

[0658] (Evaluation criteria for wavelength dispersion)

[0659] A: 0.6 ≤ x < 0.90, 1 < y ... inverse wavelength dispersion

[0660] B: 0.90≤x<0.95, 1<y··· Inverse wavelength dispersion

[0661] C: 0.95 ≤ x < 1, 1 < y

[0662] D: 1≤x, 1≥y, ... Normal dispersion

[0663] Birefringence

[0664] Since the phase difference Re(λ) = birefringence Δn(λ) × film thickness d exists, the birefringence Δn at 550nm can be evaluated based on the in-plane phase difference Re and film thickness d at 550nm.

[0665] A: 0.08 or more

[0666] B: 0.075 ≤ Δn < 0.08

[0667] C: Not reaching 0.075

[0668] Solvent solubility

[0669] Solubility tests were performed on the compounds obtained in the above manufacturing examples and comparative manufacturing examples. The solubility of the compound in cyclopentanone was evaluated visually at 25°C for 30 minutes when the total mass of the compound and cyclopentanone was set at 100% by mass and the compound was 10% by mass.

[0670] (Evaluation criteria for orientation)

[0671] A: Completely dissolved under visual inspection

[0672] C: Insoluble matter is visible to the naked eye.

[0673] [Table 9]

[0674]

[0675] Furthermore, on a glass substrate with a polyimide alignment film after rubbing treatment [product name: alignment-treated glass substrate, manufactured by EHC Co., Ltd., the alignment-treated glass substrate is coated with Polyimide LX-1400 manufactured by Hitachi Chemical Co., Ltd. and then rubbing-treated. The rubbing treatment conditions are as follows: roller speed: 600 rpm, moving speed: 30 mm / s, number of times: 3 round trips], the above-mentioned polymeric compositions 1 to 17 and comparative polymeric compositions 1 to 2 were respectively coated to a cured film thickness of 1 μm and formed into films. Subsequently, for each film, after drying in an oven at a temperature of 10°C above the solid-liquid phase transition temperature of the polymeric liquid crystal compound contained in each polymeric composition for 120 seconds, an H vacuum tube manufactured by Fusion Co., Ltd. was used to irradiate it with a dose of 400 mJ / cm. 2Irradiation with ultraviolet light (UV) forms a phase retardation layer, resulting in a phase retardation film or a laminate for transfer.

[0676] For the formed phase difference layer, the in-plane phase difference Re was measured in the same manner as above. The wavelength dispersion of the polymeric compositions 1 to 17 containing polymeric liquid crystal compounds 1 and the comparative polymeric liquid crystal compound 1, as well as the comparative polymeric composition 1, was "A" in the above evaluation criteria. The wavelength dispersion of the comparative polymeric composition 2 containing the comparative polymeric liquid crystal compound 2 was "C" in the above evaluation criteria.

[0677] [Examples 18-47]

[0678] (1) Manufacturing of polymeric compositions

[0679] In Example 1, the polymeric liquid crystal compound of the present invention and a polymeric liquid crystal compound different from the polymeric liquid crystal compound of the present invention were mixed and used according to Table 10 below, instead of using compound 1, which is the polymeric liquid crystal compound of the present invention, at a content of 100% by mass in the polymeric liquid crystal compound. Otherwise, polymeric compositions 18 to 47 were obtained in the same manner as in Example 1.

[0680] Furthermore, as a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound of the present invention, compounds represented by the following chemical formulas B-1 to B-6 are prepared.

[0681] (2) Manufacturing of phase difference film or transfer laminate

[0682] In Example 1, polymeric compositions 18-47 were used instead of polymeric composition 1. Otherwise, phase difference films or transfer laminates 18-47 were obtained in the same manner as in Example 1.

[0683] [Chemistry 68]

[0684] Polymerizable liquid crystal compound B-1

[0685]

[0686] Polymerizable liquid crystal compound B-2

[0687]

[0688] Polymerizable liquid crystal compound B-3

[0689]

[0690] Polymerizable liquid crystal compound B-4

[0691]

[0692] Polymerizable liquid crystal compound B-5

[0693]

[0694] Polymerizable liquid crystal compound B-6

[0695]

[0696] Furthermore, the wavelength dispersion of the polymerizable liquid crystal compounds B-1 to B-6 was evaluated in the following manner.

[0697] A polymerizable composition was obtained by dissolving 100 parts by mass of a polymerizable liquid crystal compound and 4 parts by mass of 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropane-1-one in 900 parts by mass of cyclopentanone. The obtained polymerizable composition was then coated onto an alignment film of a glass substrate [product name: alignment-treated glass substrate, manufactured by EHC Co., Ltd.] with a polyimide alignment film after rubbing treatment, to a cured film thickness of 1 μm. Subsequently, the film was dried in an oven at the solid-liquid phase transition temperature of the contained polymerizable liquid crystal compound plus 10°C for 120 seconds, and then irradiated with an H vacuum tube manufactured by Fusion Co., Ltd. at an irradiation dose of 400 mJ / cm². 2 A phase retardation layer is formed by irradiation with ultraviolet (UV) light.

[0698] For the formed phase difference layer, the in-plane phase difference Re was measured in the same manner as above. The wavelength dispersion of polymeric liquid crystal compounds B-1 to B-5 was "D" in the above evaluation criteria, and the wavelength dispersion of polymeric liquid crystal compound B-6 was "C" in the above evaluation criteria.

[0699] [evaluate]

[0700] <Sample Preparation>

[0701] The samples obtained by peeling the PET substrate of the retardation film obtained in each embodiment and transferring the retardation layer and the horizontal alignment film onto the adhesive glass were evaluated in the same manner as in Example 1.

[0702] The evaluation results are shown in Table 10.

[0703] [Examples 48-62]

[0704] (1) Manufacturing of polymeric compositions

[0705] In Example 1, according to Table 11 below, two or more polymerizable liquid crystal compounds of the present invention, or a mixture of the polymerizable liquid crystal compound of the present invention and at least one polymerizable liquid crystal compound selected from polymerizable liquid crystal compounds different from those of the present invention and other polymerizable compounds, were used instead of Compound 1, which is the polymerizable liquid crystal compound of the present invention, in a content of 100% by mass. Otherwise, polymerizable compositions 48 to 62 were obtained in the same manner as in Example 1.

[0706] Furthermore, as other polymerizable compounds, the following polymerizable compounds are prepared.

[0707] • DPHA (M-405): Dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate, trade name ARONIX M-405, manufactured by Dong-A Synthetic Co., Ltd.

[0708] • PETTA (M-450): Pentaerythritol triacrylate and pentaerythritol tetraacrylate, trade name ARONIX M-450, manufactured by Dong-A Synthetic Co., Ltd.

[0709] • TMPTA (M-309): Trimethylolpropane triacrylate, trade name ARONIX M-309, manufactured by Dong-A Synthetic Co., Ltd.

[0710] (2) Manufacturing of phase difference film or transfer laminate

[0711] In Example 1, polymeric compositions 48-62 were used instead of polymeric composition 1. Otherwise, phase difference films or transfer laminates 48-62 were obtained in the same manner as in Example 1.

[0712] Furthermore, in Examples 60 to 62, a TAC substrate (manufactured by Fujitac Co., Ltd.) was used instead of a PET substrate.

[0713] The samples obtained by peeling off the substrate of the phase retardation film obtained in each embodiment and transferring the phase retardation layer and the horizontal alignment film onto adhesive glass were evaluated in the same manner as in Example 1.

[0714] The evaluation results are shown in Table 11.

[0715]

[0716] Symbol Explanation

[0717] 1. Phase difference layer

[0718] 2, 2′ Substrate

[0719] 3. Orientation film

[0720] 10. Phase retardation film

[0721] Phase difference layers 11, 21, 31

[0722] 12, 22, 32 Second substrate

[0723] 13, 23, 33 Orientation films

[0724] 15, 25, 35 Peelable support bodies

[0725] 16, 26, and 36 are phase difference layers supplied for transfer.

[0726] 17. Interface between alignment film and phase difference layer

[0727] 27 Interface between the second substrate and the alignment film

[0728] 20, 30, 40 transfer laminates

[0729] 50 polarizing plate

[0730] 60 Optical components

[0731] 71 Transparent Electrode Layer

[0732] 72 Emissive Layer

[0733] 73 Electrode Layer

[0734] 100 Light-emitting display devices

Claims

1. A polymerizable liquid crystal compound, represented by the following general formula (1); General formula (1): In general formula (1), L 1 L 2 L 3 and L 4 Represent independently the following: -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-CO O-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -CO O-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, A 1 and A 2 Each of these groups independently represents a divalent alicyclic hydrocarbon group with 3 to 20 carbon atoms, either unsubstituted or optionally substituted with one or more substituents E, wherein any carbon atom of the alicyclic hydrocarbon group is optionally substituted with a heteroatom. A 3 and A 4 Each of these groups independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group with 3 to 20 carbon atoms, either unsubstituted or optionally substituted with one or more substituents E, wherein any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group is optionally substituted with a heteroatom. R 1 and R 2 Each group is independently selected from the following general formula (R-1). General formula (R-1): -L 5 -R sp1 -Z 1 In the general formula (R-1), L 5 Represents -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- or single bond, R sp1 Z represents one -CH2- or two or more non-adjacent -CH2- atoms, each independently replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-, with 1 to 20 carbon atoms, forming an alkylene group or a single bond. 1 Indicates a polymeric functional group; D 1 and D 2 Each group is independently selected from the following general formula (D-1). Substituents E, E 1 and E 2 Each of the following groups independently represents a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuryl 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, thioisocyano group, or one -CH2- or two or more non-adjacent -CH2- groups optionally independently replaced by -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-, or -C≡C-, and is a straight-chain or branched alkyl group with 1 to 20 carbon atoms, wherein any hydrogen atom in the alkyl group is optionally replaced by a fluorine atom, or, the substituent E, E 1 and E 2 Each can be represented independently – L E -R spE -Z E The base represented here, L E Represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OC O-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- or single bond, R spE This indicates one -CH2- or two or more non-adjacent -CH2- atoms, each independently replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-, representing an alkylene group or single bond with 1 to 20 carbon atoms. Z E Indicates a polymeric functional group. L E R spE and Z E Optionally with the L 5 R sp1 and Z 1 Same or different, Multiple substituents E, E, are present in the compound. 1 and E 2 In any case, each can choose either the same or different. In L 3 L 4 A 3 and A 4 If multiple instances exist, each can be chosen to be either the same or different. m1 and m2 independently represent integers from 1 to 4, and n1 and n2 independently represent integers from 0 to 3. General formula (D-1): In general formula (D-1), G 1 The alkyl group represents an alkyl group having 1 to 6 hydrogen atoms or carbon atoms, which may be optionally unsubstituted or substituted with one or more of the aforementioned substituents E. Q 1 The expression indicates that the selected material is either unsubstituted or substituted with one or more of the substituents E, and is selected from the following formulas (Q-1-1), (Q-7-1), (Q-7-2), (Q-7-7), (Q-8), (Q-10-2), (Q-10-3), (Q-10-4), (Q-10-5), (Q-10-6), (Q-10-7), (Q-10-8), (Q-10-9), and (Q-10-10-2). -11-2), formula (Q-11-3), formula (Q-11-4), formula (Q-11-5), formula (Q-11-6), formula (Q-11-7), formula (Q-11-8), formula (Q-11-9), formula (Q-11-10), formula (Q-11-11), formula (Q-11-12), formula (Q-21-1), formula (Q-21-2), formula (Q-22-1), and the groups in formula (Q-22-2), J 1 This represents -O-, -S-, -COO-, -OCO-, -OCO-O-, and -NQ. 2 -、-N=CQ 2 -、-CO-NQ 2 -、-OCO-NQ 2 - or - O-NQ 2 -, Q 2 The term represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, or an organogroup having an aromatic hydrocarbon group having 2 to 30 carbon atoms, wherein any carbon atom of the aromatic hydrocarbon group is optionally substituted with a heteroatom, or -(L 6 -A 5 ) q -L 7 -R sp2 -Z 2 The alkyl, cycloalkyl, cycloalkenyl, and aromatic hydrocarbon groups are optionally unsubstituted or substituted with one or more of the aforementioned substituents E. The alkyl group is optionally substituted with the cycloalkyl or cycloalkenyl group. One -CH2- or two or more non-adjacent -CH2- groups in the alkyl group are optionally independently substituted with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -SO2-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF-, or -C≡C-. One -CH2- or two or more non-adjacent -CH2- groups in the cycloalkyl or cycloalkenyl group are optionally independently substituted with -O-, -CO-, -COO-, -OCO-, or -O-CO-O-. L 6 represents -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- or a single bond, A 5 This indicates an alicyclic or aromatic hydrocarbon group with 3 to 20 divalent carbon atoms, either unsubstituted or optionally substituted with one or more substituents E, wherein any carbon atom of the alicyclic or aromatic hydrocarbon group may be optionally substituted with a heteroatom. L 7 represents -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- or a single bond, R sp2 This indicates one -CH2- or two or more non-adjacent -CH2- atoms, each independently replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-, representing an alkylene group or single bond with 1 to 20 carbon atoms. Z 2 Indicates a polymeric functional group. L 6 A 5 L 7 R sp2 and Z 2 Optionally with the L 1 ~L 4 A 3 ~A 4 L 5 R sp1 and Z 1 Same or different, q represents an integer from 0 to 4, in L 6 and A 5 If multiple instances exist, each can be chosen to be either the same or different. In the formula, R Q These groups represent alkyl groups with 1 to 6 hydrogen atoms or carbon atoms, and these groups have bonds in any position.

2. A polymerizable liquid crystal compound, represented by the following general formula (1'); General formula (1'): #imgpt6# In general formula (1'), L 1 L 2 L 3 and L 4 Represent independently the following: -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-CO O-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH2CH2-, -OCO-CH2CH2-, -CH2CH2-COO-, -CH2CH2-OCO-, -CO O-CH2-, -OCO-CH2-, -CH2-COO-, -CH2-OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, A 1 and A 2 Each of these groups independently represents a divalent alicyclic hydrocarbon group with 3 to 20 carbon atoms, either unsubstituted or optionally substituted with one or more substituents E, wherein any carbon atom of the alicyclic hydrocarbon group is optionally substituted with a heteroatom. A 3 and A 4 Each of these groups independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group with 3 to 20 carbon atoms, either unsubstituted or optionally substituted with one or more substituents E, wherein any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group is optionally substituted with a heteroatom. R 1 and R 2 Each group is independently selected from the following general formula (R-1). General formula (R-1): -L 5 -R sp1 -Z 1 In the general formula (R-1), L 5 Represents -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- or single bond, R sp1 Z represents one -CH2- or two or more non-adjacent -CH2- atoms, each independently replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-, with 1 to 20 carbon atoms, forming an alkylene group or a single bond. 1 Indicates a polymeric functional group; D 1 and D 2 Each of the groups is independently selected from formulas (D-1) to (D-31) and (D-34) to (D-47) below. Substituents E, E 1 and E 2 Each of the following groups independently represents a fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuryl 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, thioisocyano group, or one -CH2- or two or more non-adjacent -CH2- groups optionally independently replaced by -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-, or -C≡C-, and is a straight-chain or branched alkyl group with 1 to 20 carbon atoms, wherein any hydrogen atom in the alkyl group is optionally replaced by a fluorine atom, or, the substituent E, E 1 and E 2 Each can be represented independently – L E -R spE -Z E The base represented here, L E Represents -O-, -S-, -OCH2-, -CH2O-, -CH2CH2-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OC O-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- or single bond, R spE This indicates one -CH2- or two or more non-adjacent -CH2- atoms, each independently replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-, representing an alkylene group or single bond with 1 to 20 carbon atoms. Z E Indicates a polymeric functional group. L E R spE and Z E Optionally with the L 5 R sp1 and Z 1 Same or different, Multiple substituents E, E, are present in the compound. 1 and E 2 In any case, each can choose either the same or different. In L 3 L 4 A 3 and A 4 If multiple instances exist, each can be chosen to be either the same or different. m1 and m2 independently represent integers from 1 to 4, and n1 and n2 independently represent integers from 0 to 3.

3. The polymerizable liquid crystal compound as described in claim 1, wherein the compound is selected from the group consisting of compounds represented by the following chemical formulas.

4. A polymerizable composition comprising the polymerizable liquid crystal compound according to any one of claims 1 to 3.

5. The polymerizable composition of claim 4, further comprising a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound of any one of claims 1 to 3.

6. A polymer obtained by polymerizing the polymerizable liquid crystal compound according to any one of claims 1 to 3.

7. A polymer obtained by polymerizing the polymeric composition of claim 4 or 5.

8. A phase retardation film having a phase retardation layer, wherein the phase retardation layer contains a cured product of the polymeric composition of claim 4 or 5.

9. A method for manufacturing a retardation film, comprising a step of forming a retardation layer by means of the following steps: The process of forming a film from the polymeric composition of claim 4 or 5; At least the process of orienting the polymeric compound in the polymeric composition after film formation; and A process that polymerizes the polymeric compound at least after the orientation process.

10. A transfer laminate for transferring a phase retardation layer, the transfer laminate comprising a phase retardation layer and a support capable of peelably supporting the phase retardation layer. The phase difference layer contains a cured product of the polymeric composition of claim 4 or 5.

11. An optical component having a polarizing plate on the phase retardation film of claim 8.

12. A method for manufacturing an optical component, comprising the following steps: A transfer lamination preparation process prepares a transfer lamination for transfer of a phase difference layer, the transfer lamination having a phase difference layer and a support capable of peelably supporting the phase difference layer, wherein the phase difference layer contains a cured product of the polymeric composition of claim 4 or 5. The transfer process involves aligning a transfer object, which includes at least a polarizing plate, with the phase difference layer of the transfer laminate, and transferring the transfer laminate onto the transfer object. and The peeling process peels the support from the transfer laminate that has been transferred onto the transfer body.

13. A display device comprising a phase retardation film as claimed in claim 8, or an optical component comprising a polarizing plate on the phase retardation film.

Images