Polymerizable liquid crystal compound, method for producing same, polymerizable composition, polymer, retardation film, method for producing same, transfer laminate, optical member, method for producing same, and display device

Abstract

Provided is a polymerizable liquid crystal compound represented by general formula (I). [In general formula (I), J1 represents a monovalent group represented by general formula (J-1), and the symbols in general formula (I) and general formula (J-1) are as defined in the description.]

Description

Polymerizable liquid crystal compounds and methods for producing the same, polymerizable compositions, polymers, phase difference films and methods for producing the same, transfer laminates, optical components and methods for producing the same, and display devices.

[0001] This disclosure relates to polymerizable liquid crystal compounds, intermediates thereof, methods for producing the same, polymerizable compositions, polymers, phase difference films and methods for producing the same, transfer laminates, optical components and methods for producing the same, and display devices.

[0002] Conventionally, configurations have been proposed for display devices such as liquid crystal displays and light-emitting displays in which optical components such as phase difference films and polarizing plates are arranged on the panel surface. For example, in light-emitting displays such as organic light-emitting displays, highly reflective metal electrodes are provided in order to efficiently utilize the light from the light-emitting layer. On the other hand, the use of such metal electrodes increases ambient light reflection. Therefore, in light-emitting displays, it is known that a circular polarizer consisting of a quarter-wave plate that converts linearly polarized light to circularly polarized light and a polarizer is used on the viewing side in order to suppress such ambient light reflection.

[0003] Phase difference films include not only the quarter-wave plates mentioned above, but also half-wave plates that change the polarization plane of linearly polarized light by 90 degrees. These phase difference films can accurately convert a certain type of monochromatic light into a phase difference of 1 / 4λ or 1 / 2λ of the light wavelength. However, conventional phase difference films have the problem that the polarization output after passing through the phase difference film is converted into colored polarization. This is because the material constituting the phase difference film has wavelength dispersion with respect to the phase difference, resulting in a distribution of polarization states for each wavelength in white light, which contains light rays in the visible light range. To prevent this problem, it is necessary to control the wavelength dispersion so that the designed phase difference is achieved at each wavelength, and there is a need for a broadband phase difference film that can provide a uniform phase difference over a wide wavelength range of light, so-called phase difference film with inverse wavelength dispersion.

[0004] Furthermore, with the increasing functionality and widespread use of portable information terminals, there is a growing demand for thinner display devices, and consequently, for thinner phase difference films, which are a component of these devices. Therefore, development has been underway to create a phase difference layer with inverse wavelength dispersion in a single layer, by reducing or reversing the wavelength dispersion of the birefringence (Δn) (for example, Patent Documents 1-3). Note that the wavelength λ of the incident light on the phase difference film is plotted on the horizontal axis, and its birefringence (Δn = refractive index n for extraordinary light) is also being considered. ｅ - Refractive index n relative to ordinary light ０ It is generally said that if the slope of the graph obtained by plotting the birefringence on the vertical axis is positive (sloping upwards), then the wavelength dispersion of that birefringence is inverse, or the liquid crystal compound of the material constituting the phase difference film has inverse wavelength dispersion.

[0005] Patent No. 5899607 Patent No. 6427340 Patent No. 5962760

[0006] However, polymerizable liquid crystal compounds exhibiting inverse wavelength dispersion or flat wavelength dispersion, as disclosed in Patent Documents 1 to 3, etc., have insufficient solvent solubility, making it difficult to create inks suitable for film manufacturing such as phase difference layers, or making it difficult to create films that satisfy the required physical properties due to crystal precipitation during film manufacturing such as phase difference layers. Insufficient solvent solubility of polymerizable liquid crystal compounds limits the solvents that can be used, making it impossible to use solvents suitable for the manufacturing process, resulting in solvent residue in films such as phase difference layers and increasing the environmental burden. In view of the above-mentioned circumstances, the embodiments of this disclosure aim to provide a polymerizable liquid crystal compound having good solvent solubility and capable of forming a phase difference layer exhibiting inverse wavelength dispersion or flat wavelength dispersion, an intermediate for the polymerizable liquid crystal compound, a method for producing the polymerizable liquid crystal compound, a polymerizable composition containing the polymerizable liquid crystal compound, a polymer obtained by polymerizing the polymerizable liquid crystal compound or the polymerizable composition, a phase difference film having a phase difference layer containing a cured product of the polymerizable composition and a method for producing the same, a transfer laminate capable of transferring the phase difference layer, an optical member having the phase difference film and a method for producing the same, and a display device.

[0007] Aspects of the present disclosure relate to the following <1> to <20>. <1> A polymerizable liquid crystal compound represented by the following general formula (I).

[0008] [In the general formula (I), Ar represents an aromatic hydrocarbon group having 3 to 10 carbon atoms which may be unsubstituted or substituted by one or more substituents E. Any carbon atom of the aromatic hydrocarbon group may be substituted by a heteroatom, and the number N(π) of π electrons contained in the aromatic ring in the Ar group is 10 or less. J １ represents a monovalent group represented by the following general formula (J-1), L １ , L ２ , L ３ and L ４ each independently represent -O-, -S-, -OCH ２ -, -CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -, -CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -, -CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -, -CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or a single bond, A １ , A２ A ３ and A ４ Each of these independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group having 3 to 20 carbon atoms, which may be unsubstituted or substituted with one or more substituents E. However, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a heteroatom. １ and R ２ Each of these independently represents a group selected from the following general formula (R-1): General formula (R-1): -L ５ -R ｓｐ１ -Z １ In general formula (R-1), L ５ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐ１ This is one -CH ２- or two or more non-adjacent -CH ２ - may each independently be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH- or -C≡C- to represent an alkylene group having 1 to 20 carbon atoms or a single bond, and Z １ represents a polymerizable functional group. L ３ , L ４ , A ３ , and A ４ If there are a plurality of each, they may be the same or different. m1 and m2 each independently represent an integer of 1 to 4, and k represents an integer of 1 to 4.

[0009] (In General Formula (J-1), * represents the bonding position, and R ｘ and R ｙ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR ｗ１ , -SR ｗ２ , -COOR ｗ３ , -OCOR ｗ４ , -COR ｗ５ , -CONR ｗ６ R ｗ７ , -NR ｗ８ R ｗ９ , or a group represented by -L Ｅ -R ｓｐＥ -Z Ｅ (R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R ｗ６ and R ｗ７ each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, and R ｗ８ and R ｗ９ each independently represent a hydrogen atom, -OR ｗ１ , or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and -CH contained in the aliphatic hydrocarbon group ２- may be replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, or, R ｘ and R ｙ may be bonded to each other to form an aliphatic ring having 4 to 7 members, and the aliphatic ring may contain a hetero atom. However, R ｘ and R ｙ at least one of which may be a substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, -COOR ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ represents, or, R ｘ and R ｙ are bonded to each other to form an aliphatic ring which may contain a hetero atom having 4 to 7 members. ) The substituents E are each independently a halogen atom, a cyano group, a nitro group, -OR ａ , -NR ｂ R ｃ , -SR ｄ , -COOR ｅ , -OCOR ｆ , -COR ｇ , -SiR ｈ R ｉ R ｊ (R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , R ｉ , and R ｊ each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or, -L Ｅ -R ｓｐＥ -Z Ｅ represents a group represented by, or, an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and -CH ２ - contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, L Ｅis -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐＥ This is one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. Ｅ represents a polymerizable functional group. Substituents E and J are present in the compound. １ If there are multiple instances of each, they may be identical or different.

[0010] <2> In the general formula (I), Ar-(J １ ) ｋThe polymerizable liquid crystal compound described in <1> above, wherein is a divalent group represented by any of the following general formulas (Ar-1) to (Ar-7).

[0011] (In the general formulas (Ar-1) to (Ar-7), * indicates the bond position, Q １ is -N= or -CR ｋ The equals sign represents Q ２ is -O-, -S-, or -NR ｌ - represents R ｋ Each of these independently represents a hydrogen atom or a substituent E, and R ｌ J represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms. １ represents a monovalent group represented by the general formula (J-1), E represents the substituent E, and when n1 = 2 in general formulas (Ar-1) to (Ar-4), adjacent E members may be linked to each other to form an aliphatic ring or an aliphatic heterocycle, E １ n represents a hydrogen atom or the substituent E. n1 represents an integer from 0 to 2, n2 represents an integer from 0 to 1, k represents an integer from 1 to 4, k1 represents an integer from 0 to 2, k2 represents an integer from 1 to 3, and k3 represents an integer from 1 to 2. However, in general formula (Ar-1), k1 + n1 is an integer from 0 to 2, in general formulas (Ar-2) and (Ar-3), k + n1 is an integer from 1 to 4, in general formula (Ar-4), k2 + n1 is an integer from 1 to 3, and in general formulas (Ar-5) to (Ar-7), k3 + n2 is an integer from 1 to 2. Ar-(J １ ) ｋ Substituents E and J are contained within. １ If there are multiple instances of each, they may be identical or different.

[0012] <3> In the above general formula (I), A １ and A ２ The polymerizable liquid crystal compound according to <1> or <2>, wherein each of the following groups may independently be unsubstituted or substituted with one or more substituents E: a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, a cycloheptane-1,4-diyl group, or a cyclododecane-1,5-diyl group. <4> In the general formula (I), A ３ and A４ A polymerizable liquid crystal compound according to any one of <1> to <3> above, wherein each of the following groups may independently be unsubstituted or substituted with one or more substituents E: benzene-1,4-diyl group, cyclohexane-1,4-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, or 1,3-dioxane-2,5-diyl group. <5> A compound represented by the following general formula (Ar-im).

[0013] [In the general formula (Ar-im), Ar-(J １ ) ｋ This represents a divalent group represented by one of the following general formulas (Ar-1) to (Ar-7), and T １ , and T ２ These are, independently, -OH, -CHO, -COOH, -SH, and -NH. ２ , halogen atom, -CH ２ OH, -CH ２ SH, -CF ２ OH, -CF ２ SH represents -CH=CHCOOH, or -CH=CHOCOOH.

[0014] (In the general formulas (Ar-1) to (Ar-7), * indicates the bond position, Q １ is -N= or -CR ｋ The equals sign represents Q ２ is -O-, -S-, or -NR ｌ - represents R ｋ Each of these independently represents a hydrogen atom or a substituent E, and R ｌ J represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms. １ represents a monovalent group represented by the following general formula (J-1), E represents a substituent E, and when n1 = 2 in general formulas (Ar-1) to (Ar-4), adjacent E groups may be linked to each other to form an aliphatic ring or an aliphatic heterocycle. １n represents a hydrogen atom or substituent E. n1 represents an integer from 0 to 2, n2 represents an integer from 0 to 1, k represents an integer from 1 to 4, k1 represents an integer from 0 to 2, k2 represents an integer from 1 to 3, and k3 represents an integer from 1 to 2. However, in general formula (Ar-1), k1 + n1 is an integer from 0 to 2, in general formulas (Ar-2) and (Ar-3), k + n1 is an integer from 1 to 4, in general formula (Ar-4), k2 + n1 is an integer from 1 to 3, and in general formulas (Ar-5) to (Ar-7), k3 + n2 is an integer from 1 to 2.

[0015] (In the general formula (J-1), * represents the bond position, R ｘ and R ｙ Each of these is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, and -OR ｗ１ , -SR ｗ２ , -COOR ｗ３ , -OCOR ｗ４ , -COR ｗ５ , -CONR ｗ６ R ｗ７ , -NR ｗ８ R ｗ９ , or -L Ｅ -R ｓｐＥ -Z Ｅ The group represented by (R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R ｗ６ and R ｗ７ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, R ｗ８ and R ｗ９ These are, independently, hydrogen atoms, -OR ｗ１ (or represents an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of the above, and the aliphatic hydrocarbon group contains -CH ２ - may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, or R ｘ and R ｙThese atoms may bond to each other to form a 4- to 7-membered aliphatic ring, and the aliphatic ring may contain heteroatoms, however, R ｘ and R ｙ an aliphatic hydrocarbon group having 1 to 20 carbon atoms, -COOR, in which at least one of the following may be substituted. ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ It represents, or R ｘ and R ｙ These atoms are bonded to each other to form an aliphatic ring which may contain a heteroatom of 4 to 7 members.) Each substituent E is independently a halogen atom, a cyano group, a nitro group, or -OR ａ , -NR ｂ R ｃ , -SR ｄ , -COOR ｅ , -OCOR ｆ , -COR ｇ , -SiR ｈ R ｉ R ｊ (R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , R ｉ , and R ｊ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the aliphatic hydrocarbon group contains -CH ２ The - can be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, L Ｅ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐＥ This is one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. Ｅ represents a polymerizable functional group. Substituents E and J are present in the compound. １ If there are multiple instances of each, they may be identical or different.

[0016] <6> A method for producing a polymerizable liquid crystal compound represented by the following general formula (I-1), comprising simultaneously or sequentially condensing a compound represented by the following general formula (Ar-im1) with a compound represented by the general formula (mc-1) and a compound represented by the general formula (mc-2).

[0017] [In general formulas (Ar-im1), (mc-1), (mc-2), and (I-1), Ar-(J １ ) ｋ This represents a divalent group represented by one of the following general formulas (Ar-1) to (Ar-7):

[0018] (In the general formulas (Ar-1) to (Ar-7), * indicates the bond position, Q １ is -N= or -CR ｋ The equals sign represents Q ２ is -O-, -S-, or -NR ｌ - represents R ｋ Each of these independently represents a hydrogen atom or a substituent E, and R ｌ J represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms. １ represents a monovalent group represented by the following general formula (J-1), E represents a substituent E, and when n1 = 2 in general formulas (Ar-1) to (Ar-4), adjacent E groups may be linked to each other to form an aliphatic ring or an aliphatic heterocycle. １ n represents a hydrogen atom or substituent E. n1 represents an integer from 0 to 2, n2 represents an integer from 0 to 1, k represents an integer from 1 to 4, k1 represents an integer from 0 to 2, k2 represents an integer from 1 to 3, and k3 represents an integer from 1 to 2. However, in general formula (Ar-1), k1 + n1 is an integer from 0 to 2, in general formulas (Ar-2) and (Ar-3), k + n1 is an integer from 1 to 4, in general formula (Ar-4), k2 + n1 is an integer from 1 to 3, and in general formulas (Ar-5) to (Ar-7), k3 + n2 is an integer from 1 to 2.

[0019] (In the general formula (J-1), * represents the bond position, R ｘ and R ｙ Each of these is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, and -OR ｗ１ , -SR ｗ２ , -COOR ｗ３ , -OCOR ｗ４ , -COR ｗ５ , -CONR ｗ６ R ｗ７ , -NR ｗ８ R ｗ９, or -L Ｅ -R ｓｐＥ -Z Ｅ The group represented by (R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R ｗ６ and R ｗ７ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, R ｗ８ and R ｗ９ These are, independently, hydrogen atoms, -OR ｗ１ (or represents an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of the above, and the aliphatic hydrocarbon group contains -CH ２ - may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, or R ｘ and R ｙ These atoms may bond to each other to form a 4- to 7-membered aliphatic ring, and the aliphatic ring may contain heteroatoms, however, R ｘ and R ｙ an aliphatic hydrocarbon group having 1 to 20 carbon atoms, -COOR, in which at least one of the following may be substituted. ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ It represents, or R ｘ and R ｙ These atoms are bonded to each other to form an aliphatic ring that may contain a heteroatom of 4 to 7 members. ３ and L ４ These are independently -O-, -S-, and -OCH. ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond are represented. １ A ２ A ３ and A ４ Each of these independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group having 3 to 20 carbon atoms, which may be unsubstituted or substituted with one or more substituents E. However, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a heteroatom. １ and R ２ Each of these independently represents a group selected from the following general formula (R-1): General formula (R-1): -L ５ -R ｓｐ１ -Z １ In general formula (R-1), L ５ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐ１ This is one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. １ L represents a polymerizable functional group. ３ , L ４ A ３ , and A ４ If there are multiple instances of each, they may be the same or different. m1 and m2 each independently represent integers from 1 to 4. Substituents E each independently represent halogen atoms, cyano groups, nitro groups, -OR ａ , -NR ｂ R ｃ , -SR ｄ , -COOR ｅ , -OCOR ｆ , -COR ｇ , -SiR ｈ R ｉ R ｊ (R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , Rｇ , R ｈ , R ｉ , and R ｊ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the aliphatic hydrocarbon group contains -CH ２ The - can be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, L Ｅ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐＥ This is one -CH ２- or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. Ｅ represents a polymerizable functional group. The compound contains substituents E and J. １ If there are multiple instances of each, they may be identical or different.

[0020] <7> A polymerizable composition containing the polymerizable liquid crystal compound described in any of <1> to <4> above. <8> The polymerizable composition according to <7>, further containing at least one initiator selected from the group consisting of acylphosphine oxide polymerization initiators, α-aminoalkylphenone polymerization initiators, α-hydroxyketone polymerization initiators, and oxime ester polymerization initiators. <9> The polymerizable composition according to <7> or <8>, further containing a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound described in any of <1> to <4> above. <10> The polymerizable composition according to any of <7> to <9>, further containing a polymerizable compound different from the polymerizable liquid crystal compound described in any of <1> to <4> above, having two or more polymerizable functional groups in one molecule. <11> A polymerizable composition according to any one of <7> to <10>, further containing a polymerizable compound that dissolves in 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. <12> A polymer obtained by polymerizing the polymerizable liquid crystal compound according to any one of <1> to <4>. <13> A polymer obtained by polymerizing the polymerizable composition according to any one of <7> to <11>. <14> A phase difference film having a phase difference layer, wherein the phase difference layer contains a cured product of the polymerizable composition according to any one of <7> to <11>. <15> A phase difference film according to <14>, wherein the phase difference value Re(450) at a wavelength of 450 nm and the phase difference value Re(550) at a wavelength of 550 nm satisfy Re(450) / Re(550) < 1.05. <16> A method for producing a phase difference film, comprising the steps of: forming a film of a polymerizable composition according to any one of <7> to <11> above; oriented at least the polymerizable compound in the formed polymerizable composition; and polymerizing at least the polymerizable compound after the orientation step, thereby forming a phase difference layer. <17> A transfer laminate for transferring a phase difference layer, comprising a phase difference layer and a support that removably supports the phase difference layer, wherein the phase difference layer contains a cured product of the polymerizable composition according to any one of <7> to <11> above.<18> An optical member comprising a polarizing plate on a phase difference film as described in <14> or <15>. <19> A method for manufacturing an optical member, comprising: a step of preparing a transfer laminate for transferring a phase difference layer, comprising a phase difference layer and a support that peelably supports the phase difference layer, wherein the phase difference layer contains a cured product of a polymerizable composition as described in any of <7> to <11>; a transfer step of placing a transfer subject, which includes at least a polarizing plate, and the phase difference layer of the transfer laminate facing each other, and transferring the transfer laminate onto the transfer subject; and a peeling step of peeling the support from the transfer laminate transferred onto the transfer subject. <20> A display device comprising a phase difference film as described in <14> or <15>, or an optical member comprising a polarizing plate on the phase difference film.

[0021] According to embodiments of the present disclosure, it is possible to provide a polymerizable liquid crystal compound having good solvent solubility and capable of forming a phase difference layer exhibiting inverse wavelength dispersion or flat wavelength dispersion, an intermediate for the polymerizable liquid crystal compound, a method for producing the polymerizable liquid crystal compound, a polymerizable composition containing the polymerizable liquid crystal compound, a polymer obtained by polymerizing the polymerizable liquid crystal compound or the polymerizable composition, a phase difference film having a phase difference layer containing a cured product of the polymerizable composition and a method for producing the same, a transfer laminate capable of transferring the phase difference layer, an optical member having the phase difference film and a method for producing the same, and a display device.

[0022] Figure 1 is a schematic cross-sectional view showing one embodiment of a phase difference film. Figure 2 is a schematic cross-sectional view showing one embodiment of a phase difference film. Figure 3 is a schematic cross-sectional view showing one embodiment of a phase difference film. Figure 4 is a schematic cross-sectional view showing one embodiment of a transfer laminate. Figure 5 is a schematic cross-sectional view showing one embodiment of a transfer laminate. Figure 6 is a schematic cross-sectional view showing one embodiment of a transfer laminate. Figure 7 is a schematic cross-sectional view showing one embodiment of an optical member. Figure 8 is a schematic cross-sectional view showing one embodiment of a display device.

[0023] The embodiments and examples of this disclosure will be described below with reference to the drawings, etc. However, this disclosure can be implemented in many different ways and should not be interpreted as being limited to the embodiments and examples described below. In addition, in order to make the explanation clearer, the drawings may schematically represent the width, thickness, shape, etc. of each part compared to the actual embodiment, but these are merely examples and should not limit the interpretation of this disclosure. In addition, in this specification and each drawing, the same reference numerals are used for elements that are the same as those described above with respect to previously shown drawings, and detailed explanations may be omitted as appropriate. Also, for the convenience of explanation, the terms "above" or "below" may be used in the explanation, but the up and down directions may be reversed. In this specification, when a certain component or region is said to be "above (or below)" another component or region, unless otherwise specified, this includes not only the case where it is directly above (or directly below) the other component, but also the case where it is above (or below) the other component, that is, it includes the case where another component is included between them above (or below) the other component.

[0024] In this disclosure, orientation regulating force refers to the effect of aligning the liquid crystal compounds in the phase difference layer in a specific direction. In this disclosure, (meth)acrylic refers to acrylic or methacrylic, respectively, and (meth)acrylate refers to acrylate or methacrylate, respectively. Furthermore, in this specification, the terms "plate," "sheet," and "film" are not distinguished from each other solely on the basis of their names, and "film surface (plate surface, sheet surface)" refers to the surface that coincides with the planar direction of the film-like member (plate member, sheet member) when the film-like member (plate member, sheet member) in question is viewed holistically and from a broad perspective.

[0025] A. Polymerizable Liquid Crystal Compounds The polymerizable liquid crystal compounds of this disclosure are compounds represented by the following general formula (I).

[0026] [In general formula (I), Ar represents an aromatic hydrocarbon group having 3 to 10 carbon atoms, which may be unsubstituted or substituted with one or more substituents E. Any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom, and the number of π electrons N(π) contained in the aromatic ring in the Ar group is 10 or less. J １ This represents a monovalent group represented by the following general formula (J-1), L １ , L ２ , L ３ and L ４ These are independently -O-, -S-, and -OCH. ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond are represented. １ A ２ A ３ and A ４Each of these independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group having 3 to 20 carbon atoms, which may be unsubstituted or substituted with one or more substituents E. However, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a heteroatom. １ and R ２ Each of these independently represents a group selected from the following general formula (R-1): General formula (R-1): -L ５ -R ｓｐ１ -Z １ In general formula (R-1), L ５ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐ１ This is one -CH ２ - or two or more non-adjacent -CH ２Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. １ L represents a polymerizable functional group. ３ , L ４ A ３ , and A ４ If there are multiple instances of each, they may be the same or different. m1 and m2 each independently represent integers from 1 to 4, and k also represents an integer from 1 to 4.

[0027] (In the general formula (J-1), * represents the bond position, R ｘ and R ｙ Each of these is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, and -OR ｗ１ , -SR ｗ２ , -COOR ｗ３ , -OCOR ｗ４ , -COR ｗ５ , -CONR ｗ６ R ｗ７ , -NR ｗ８ R ｗ９ , or -L Ｅ -R ｓｐＥ -Z Ｅ The group represented by (R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R ｗ６ and R ｗ７ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, R ｗ８ and R ｗ９ These are, independently, hydrogen atoms, -OR ｗ１ (or represents an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of the above, and the aliphatic hydrocarbon group contains -CH ２ - may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, or R ｘand R ｙ These atoms may bond to each other to form a 4- to 7-membered aliphatic ring, and the aliphatic ring may contain heteroatoms, however, R ｘ and R ｙ an aliphatic hydrocarbon group having 1 to 20 carbon atoms, -COOR, in which at least one of the following may be substituted. ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ It represents, or R ｘ and R ｙ These atoms are bonded to each other to form an aliphatic ring which may contain a heteroatom of 4 to 7 members.) Each substituent E is independently a halogen atom, a cyano group, a nitro group, or -OR ａ , -NR ｂ R ｃ , -SR ｄ , -COOR ｅ , -OCOR ｆ , -COR ｇ , -SiR ｈ R ｉ R ｊ (R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , R ｉ , and R ｊ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the aliphatic hydrocarbon group contains -CH ２ The - can be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, L Ｅ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐＥ This is one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. Ｅ represents a polymerizable functional group. Substituents E and J are present in the compound. １ If there are multiple instances of each, they may be identical or different.

[0028] The compound represented by the general formula (I) in this disclosure is the specific R １ From R ２Because the main chain structure leading to it has a specific structure, the orientation between molecules is improved, and it is a compound that exhibits liquid crystalline properties on its own. Furthermore, the compound represented by general formula (I) of this disclosure is a polymerizable liquid crystal compound because it has a polymerizable group at its terminus. The compound represented by general formula (I) of this disclosure has an Ar group (an aromatic hydrocarbon group in which the number of π electrons N(π) in the aromatic ring is 10 or less) in the main chain portion, and a specific monovalent group represented by general formula (J-1) (-N(H)-N=C(R Ｘ ) R Ｙ Because it has a structure in which the side chains of ) are bonded, the axis of -N(H)-N=C= in the specific monovalent group represented by the general formula (J-1) is R １ From R ２ Because it is maintained at an angle nearly perpendicular to the main chain leading to it, the compound represented by general formula (I) of this disclosure exhibits inverse wavelength dispersibility or flat dispersion. Furthermore, the compound represented by general formula (I) of this disclosure has a number of π electrons N(π) in the aromatic ring in the Ar group contained in the main chain portion that is 10 or less, does not contain an aromatic ring with a large number of π electrons N(π) that is rigid and reduces solvent solubility, and the side chain is a specific monovalent group represented by general formula (J-1), contains a -N(H)-N=C bond, and R Ｘ and R Ｙ It does not contain an aromatic ring group, R ｘ and R ｙ an aliphatic hydrocarbon group having 1 to 20 carbon atoms, -COOR, in which at least one of the following may be substituted. ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ (where R represents) ｗ３ , R ｗ５ , R ｗ６ and R ｗ７ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, or R ｘ and R ｙ Because these groups are bonded to each other to form an aliphatic ring which may contain a heteroatom of 4 to 7 members, solvent solubility is improved. The compound represented by general formula (I) of this disclosure has a structure in which a side chain of a specific monovalent group represented by general formula (J-1) is bonded to an Ar group contained in the main chain portion, R １ From R２ The orderliness of the main chain leading to the final product results in good orientation. Thus, the polymerizable liquid crystal compound represented by general formula (I) of this disclosure has good solvent solubility and can form a phase difference layer exhibiting inverse wavelength dispersibility and flat wavelength dispersibility.

[0029] L in general formula (I) １ , L ２ , L ３ and L ４ These are independently -O-, -S-, and -OCH. ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C-, or single bond. Represents a divalent linking group or single bond. Note L ３ and L ４ If multiple instances of these elements appear independently, they may be identical or different.

[0030] L １ and L ２More specifically, from the viewpoints of liquid crystalline properties, ease of raw material availability, and ease of synthesis, -COO-, -OCO-, and -OCH were selected independently. ２ -ien-CH ２ O-, -CF ２ O-, -OCF ２ -ien-CH ２ CH ２ -, -CF ２ CF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ It is preferable that the symbols represent -OCO-, -CH=CH-, -CF=CF-, -C≡C-, or a single bond, such as -COO-, -OCO-, or -OCH ２ -ien-CH ２ O-, -CF ２ O-, -OCF ２ -ien-CH ２ CH ２ -, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -CH=CH-, -C≡C-, or more preferably represent a single bond, such as -COO-, -OCO-, -OCH ２ -ien-CH ２ O-, -CF ２ O-, -OCF ２ It is even more preferable to represent a single bond, such as -COO-, -OCO-, or -OCH. ２ -ien-CH ２ It is even more preferable to represent O- or a single bond, such as -COO-, -OCO-, or -OCH. ２ -, or -CH ２ It is particularly preferable to represent it as O-.

[0031] L３ and L ４ More specifically, from the viewpoint of ease of obtaining raw materials and ease of synthesis, -O-, -S-, and -OCH were chosen independently. ２ -ien-CH ２ O-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ It is preferable that -OCO- or -OCH represents a single bond, and if there are multiple, they may be the same or different, and each can independently represent -O-, -OCH, etc. ２ -ien-CH ２ O-, -COO-, -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO- or single bond is more preferable, and if there are multiple, they may be the same or different, and each can be independently -O-, -COO-, -OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ - or single bond is particularly preferred.

[0032] A in general formula (I) １ A ２ A ３ and A ４Each of these independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group having 3 to 20 carbon atoms, which may be 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, and more specifically, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom. The aromatic hydrocarbon group may be an aromatic heterocyclic group, may have a fused ring structure, or may be a structure in which an alicyclic hydrocarbon group and an aromatic hydrocarbon group are fused. A ３ and A ４ If each of these appears independently multiple times, they may be the same or different. Note that A in general formula (I) １ A ２ A ３ and A ４ The substituent E, which may be substituted, will be described later.

[0033] Examples of divalent alicyclic hydrocarbon groups having 3 to 20 carbon atoms include cycloalkanediyl groups having 3 to 20 carbon atoms and alicyclic fused ring groups having 10 to 20 carbon atoms.

[0034] Divalent cycloalkanediyl groups with 3 to 20 carbon atoms include: cyclopropanediyl group; cyclobutanediyl groups such as cyclobutane-1,2-diyl group and cyclobutane-1,3-diyl group; cyclopentanediyl groups such as cyclopentane-1,2-diyl group and cyclopentane-1,3-diyl group; cyclohexane-1,2-diyl group, cyclohexane-1,3-diyl group, and cyclohexane-1,4- Cyclohexanediyl groups such as diyl groups; cycloheptanediyl groups such as cycloheptane-1,2-diyl, cycloheptane-1,3-diyl, and cycloheptane-1,4-diyl; cyclooctanediyl groups such as cyclooctane-1,2-diyl, cyclooctane-1,3-diyl, cyclooctane-1,4-diyl, and cyclooctane-1,5-diyl; cyclodecane-1,2-diyl groups Examples include cyclodecanediyl groups such as cyclodecane-1,3-diyl group, cyclodecane-1,4-diyl group, and cyclodecane-1,5-diyl group; cyclododecanediyl groups such as cyclododecane-1,2-diyl group, cyclododecane-1,3-diyl group, cyclododecane-1,4-diyl group, and cyclododecane-1,5-diyl group; cyclotetradecanediyl groups such as cyclotetradecane-1,2-diyl group, cyclotetradecane-1,3-diyl group, cyclotetradecane-1,4-diyl group, cyclotetradecane-1,5-diyl group, and cyclotetradecanediyl groups such as cycloeicosane-1,2-diyl group and cycloeicosane-1,10-diyl group; and the cycloalkanediyl group may be unsubstituted or substituted with one or more substituents E. The cycloalkanediyl group may have any carbon atom substituted with an oxygen atom, a sulfur atom, or a nitrogen atom. Examples include a tetrahydropyran-2,5-diyl group, a 1,3-dioxane-2,5-diyl group, and a tetrahydrothiopyran-2,5-diyl group.

[0035] Examples of divalent alicyclic condensed ring groups having 10 to 20 carbon atoms include decalindiyl groups such as decahydronaphthalene-2,5-diyl, decahydronaphthalene-2,6-diyl, and decahydronaphthalene-2,7-diyl; adamantanediyl groups such as adamantane-1,2-diyl and adamantane-1,3-diyl; and bicyclo[2.2.1]heptanediyl groups such as bicyclo[2.2.1]heptane-2,3-diyl, bicyclo[2.2.1]heptane-2,5-diyl, and bicyclo[2.2.1]heptane-2,6-diyl. The alicyclic condensed ring groups may be unsubstituted or substituted with one or more substituents E. Furthermore, any carbon atom in the alicyclic condensed ring group may be substituted with an oxygen atom, a sulfur atom, or a nitrogen atom.

[0036] The aforementioned divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms is L １ , L ３ (or L ２ , L ４ Based on the differences in the stereochemistry of the carbon atoms bonded to the alicyclic hydrocarbon group, cis and trans stereoisomers may exist. The divalent alicyclic hydrocarbon group having 3 to 20 carbon atoms may be cis, trans, or a mixture of cis and trans isomers, but it is preferable that it be trans or cis, and more preferably trans, because it has good orientation.

[0037] Examples of divalent aromatic hydrocarbon groups that may be substituted with heteroatoms include divalent aromatic hydrocarbon groups having 6 to 20 carbon atoms that may be substituted with heteroatoms. Examples of aromatic hydrocarbon rings constituting such heteroatom-substituted aromatic hydrocarbon groups include benzene rings, naphthalene rings, anthracene rings, and phenanthrene rings, while examples of aromatic heterocycles include furan rings, pyridine rings, pyrimidine rings, and pyrazine rings.

[0038] Examples of divalent aromatic hydrocarbon groups having 6 to 20 carbon atoms that may be substituted with the heteroatom, and groups formed by the condensation of an alicyclic hydrocarbon group and an aromatic hydrocarbon group, include benzene-1,4-diyl group (1,4-phenylene group), pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, pyrazine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, phenanthrene-2,7-diyl group, 9,10-dihydrophenanthrene-2,7-diyl group, 1,2,3,4,4a,9,10a-octahydrophenanthrene-2,7-diyl group, or fluorene-2,7-diyl group, and the alicyclic hydrocarbon group and aromatic hydrocarbon group may be unsubstituted or substituted with one or more substituents E.

[0039] Among these, A １ and A ２ Each of these groups is independently preferred, particularly as it facilitates the improvement of liquid crystalline properties and the orientation of the polymer, and is preferably an alicyclic hydrocarbon group having 3 to 12 carbon atoms, which may be unsubstituted or substituted with one or more substituents E; more preferably a cycloalkanediyl group having 3 to 12 carbon atoms; more preferably a cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cycloheptane-1,4-diyl group, or cyclododecane-1,5-diyl group, which may be unsubstituted or substituted with one or more substituents E; and especially preferably a cyclohexane-1,4-diyl group, which may be unsubstituted or substituted with one or more substituents E.

[0040] Also, A in general formula (I) ３ and A ４Each of these groups is preferable, in particular, because it facilitates the improvement of liquid crystalline properties and the orientation of the polymer, and these groups are benzene-1,4-diyl group, cyclohexane-1,4-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2,6-diyl group, naphthalene-1,4-diyl group, 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group, or 1,3-dioxane-2,5-diyl group.

[0041] A in general formula (I) ３ and A ４ Each of these groups is preferably an unsubstituted or substituted group E, such as a benzene-1,4-diyl group, a naphthalene-2,6-diyl group, or a cyclohexane-1,4-diyl group, more preferably a benzene-1,4-diyl group or a cyclohexane-1,4-diyl group, and particularly preferably a benzene-1,4-diyl group. These groups facilitate the improvement of the liquid crystalline properties of the polymerizable liquid crystal compound of this embodiment and the orientation of the polymer.

[0042] In general formula (I), m1 and m2 each independently represent integers from 1 to 4. When the liquid crystalline properties and orientation of the polymerizable compound of this embodiment are important, it is preferable that one or both of m1 and m2 are integers from 1 to 3, more preferably that both m1 and m2 are integers from 1 to 3, and even more preferably that both m1 and m2 are 1 or 2.

[0043] R １ and R ２ Each of these independently represents a group selected from the following general formula (R-1). General formula (R-1): -L ５ -R ｓｐ１ -Z １ In general formula (R-1), L ５ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C-, or single bond are represented.

[0044] In general formula (R-1), L ５ More specifically, from the viewpoint of ease of obtaining raw materials and ease of synthesis, they can be independently selected as -O-, -S-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH ２ CH ２ -COO-, -CH ２ CH ２ It is preferable that -OCO- or a single bond be represented, and it is more preferable that each independently represents -O-, -COO-, -OCO-, -O-CO-O-, or a single bond. If there are multiple, they may be the same or different.

[0045] In general formula (R-1), R ｓｐ１ This is one -CH ２ - or two or more non-adjacent -CH ２Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. ｓｐ１ The alkylene group in this may be a straight-chain alkylene group.

[0046] In general formula (R-1), R ｓｐ１ More specifically, from the viewpoint of ease of obtaining raw materials and ease of synthesis, each is independently one -CH ２ - or two or more non-adjacent -CH ２ It is more preferable that each of the - symbols independently represents an alkylene group or single bond having 1 to 12 carbon atoms, which may be replaced by -O-, -COO-, or -OCO-; it is even more preferable that each of the - symbols independently represents an alkylene group or single bond having 1 to 12 carbon atoms; and it is even more preferable that each of the - symbols independently represents an alkylene group having 2 to 10 carbon atoms; if there are multiple - symbols, they may be the same or different.

[0047] In general formula (R-1), Z １ * represents a polymerizable functional group. The polymerizable functional group can be any group used in conventional polymerizable liquid crystal compounds without limitation. Preferably, each polymerizable functional group independently represents a group selected from the following formulas (Z-1) to (Z-8). In the following formulas (Z-1) to (Z-8), * (asterisk) represents R ｓｐ１ This indicates the bonding position.

[0048] (In formulas (Z-1) to (Z-8), R ｚ Each of these is independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, or a trifluoromethyl group.

[0049] When ultraviolet polymerization is used as the polymerization method, Z １ Formulas (Z-1), (Z-2), (Z-3), (Z-5), and (Z-7) are preferred, formulas (Z-1), (Z-3), and (Z-7) are more preferred, formula (Z-1) is even more preferred, and in formula (Z-1), R ｚIt is particularly preferable that the group is a hydrogen atom, a methyl group, or a trifluoromethyl group.

[0050] Each substituent E is independently a halogen atom, a cyano group, a nitro group, or -OR ａ , -NR ｂ R ｃ , -SR ｄ , -COOR ｅ , -OCOR ｆ , -COR ｇ , -SiR ｈ R ｉ R ｊ (R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , R ｉ , and R ｊ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the aliphatic hydrocarbon group contains -CH ２ The dash may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-.

[0051] Examples of the halogen atoms include fluorine, chlorine, bromine, and iodine atoms. ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , R ｉ , and R ｊ The aliphatic hydrocarbon group having 1 to 6 carbon atoms in the compound may be saturated or unsaturated, linear, branched, or cyclic, and the aliphatic hydrocarbon group contains -CH ２The - can be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-. Specifically, examples include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, cyclohexyl group, vinyl group, ethynyl group, propane-2-in-1-yl group, acetylmethyl group, acetylthiomethyl group, methylcarbonatemethyl group, etc. The number of carbon atoms in the aliphatic hydrocarbon group may be 1 to 4, 1 or 2, or 1.

[0052] -OR ａ Examples include hydroxyl groups or alkoxy groups having 1 to 6 carbon atoms. Examples of alkoxy groups having 1 to 6 carbon atoms include methoxy groups, ethoxy groups, n-propoxy groups, isopropoxy groups, n-butoxy groups, and n-pentyloxy groups. -NR ｂ R ｃ For example, an amino group (-NH ２ Examples include methylamino groups, dimethylamino groups, and diisopropylamino groups. -SR ｄ Examples include mercapto groups or alkylthio groups having 1 to 6 carbon atoms. Examples of alkylthio groups having 1 to 6 carbon atoms include methylthio groups, ethylthio groups, n-propylthio groups, t-butylthio groups, etc. -COOR ｅ Examples include carboxyl groups or alkoxycarbonyl groups having 1 to 6 carbon atoms. Examples of alkoxycarbonyl groups having 1 to 6 carbon atoms include methoxycarbonyl groups, ethoxycarbonyl groups, n-propoxycarbonyl groups, isopropoxycarbonyl groups, n-pentyloxycarbonyl groups, etc. -OCOR ｆExamples include formyloxy groups or alkylcarbonyloxy groups having 1 to 6 carbon atoms. Examples of alkylcarbonyloxy groups having 1 to 6 carbon atoms include methylcarbonyloxy groups, ethylcarbonyloxy groups, n-propylcarbonyloxy groups or isopropylcarbonyloxy groups, n-butoxycarbonyloxy groups, t-butoxycarbonyloxy groups, etc. -COR ｇ Examples include a formyl group or an alkylcarbonyl group having 1 to 6 carbon atoms. Examples of alkylcarbonyl groups having 1 to 6 carbon atoms include a methylcarbonyl group (acetyl group), an ethylcarbonyl group, an n-propylcarbonyl group or an isopropylcarbonyl group, an n-butylcarbonyl group, a t-butylcarbonyl group, and the like. -SiR ｈ R ｉ R ｊ Examples include silyl groups or trialkylsilyl groups having 1 to 6 carbon atoms. Examples of trialkylsilyl groups having 1 to 6 carbon atoms include trimethylsilyl group, dimethylethylsilyl group, and t-butyldimethylsilyl group. Ｅ , R ｓｐＥ , and Z Ｅ These are, respectively, the L ５ , R ｓｐ１ , and Z １ It may be the same as L. Ｅ , R ｓｐＥ , and Z Ｅ Each of the L molecules is present in the molecule. ５ , R ｓｐ１ , and Z １ It may be the same as or different from it.

[0053] The aliphatic hydrocarbon group having 1 to 20 carbon atoms, which may be substituted by one or more of the substituents, may be saturated or unsaturated, linear, branched, or cyclic, and the aliphatic hydrocarbon group contains -CH ２The dash may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-. Specifically, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, 2-ethylhexyl group, n-octyl group, n-decyl group, n-dodecyl group, n-tridecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, methylcyclohexyl group, ethylcyclohexyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, tricyclo[5.2.1.0 ２，６ ] Decyl group, tricyclo[3.3.1.1 ３，７ ] Decyl group, tetracyclo[6.2.1.1 ３，６ . 0 ２，７ Examples include dodecyl group, adamantyl group, cyclopentylmethyl group, cyclohexylmethyl group, cyclohexylheptyl group, vinyl group, propenyl group, butenyl group, ethynyl group, propane-2-in-1-yl group, fluoromethyl group, cyanomethyl group, nitromethyl group, hydroxymethyl group, methoxymethyl group, aminomethyl group, and acetylmethyl group. The number of carbon atoms in the aliphatic hydrocarbon group may be 1 to 20, 1 to 12, or 1 to 6.

[0054] A １ A ２ A ３ and A ４ From the viewpoint of liquid crystalline properties and ease of synthesis, substituent E is a fluorine atom, a chlorine atom, a nitro group, an alkoxy group having 1 to 6 carbon atoms, or an alkyl group having 1 to 20 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom, and the alkyl group contains -CH ２- may be 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 group in which - is replaced by a fluorine atom, a chlorine atom, an alkoxy group having 1 to 6 carbon atoms, or an alkyl group having 1 to 12 carbon atoms in which any hydrogen atom may be substituted with a fluorine atom, and -CH ２ The group may be one in which - is replaced by a group selected from -O-, -COO-, or -OCO-, and may be a fluorine atom, a chlorine atom, an alkoxy group having 1 to 6 carbon atoms, or a linear or branched alkyl group having 1 to 8 carbon atoms in which any hydrogen atom may be replaced by a fluorine atom. Also, A ３ and A ４ substituents E may be substituted, among others, R １ and R ２ A, which is connected to each other ３ and A ４ A substituent E that may be substituted is -L Ｅ -R ｓｐＥ -Z Ｅ It may also be a base represented by .

[0055] In general formula (I), Lc1: -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, though not limited to these, include groups represented by Lc-1 to Lc-424 below. In polymerizable liquid crystal compounds represented by general formula (I), Lc1 and Lc2 may be the same or different.

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066] In the groups represented by Lc-1 to Lc-424, L ３ and L ４ In this case, m represents 1 or 2, with 2 being preferred. ｓｐ１ In this case, n represents 1 to 20, but among them R ｓｐ１ In this case, n is preferably 2 or more, more preferably 4 or more, on the other hand, it is preferably 12 or less, and more preferably 10 or less. Also, Z １ In equation (Z-1), R ｚ Each of these elements is independently preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.

[0067] On the other hand, in general formula (I), Ar represents an aromatic hydrocarbon group having 3 to 10 carbon atoms that is either unsubstituted or substituted with one or more substituents E. Any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom, and the number of π electrons N(π) contained in the aromatic ring in the Ar group is 10 or less. The heteroatom may be an oxygen atom, a sulfur atom, or a nitrogen atom. Examples of aromatic rings constituting an aromatic hydrocarbon group having 3 to 10 carbon atoms that may be substituted with a heteroatom include a benzene ring, a naphthalene ring, a furan ring, a thiophene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a benzofuran ring, a benzothiophene ring, a benzoxazole ring, a benzothiazole ring, an indole ring, a benzimidazole ring, and the like.

[0068] In the general formula (I), Ar-(J １ ) ｋ This may represent a divalent group represented by any of the following general formulas (Ar-1) to (Ar-7).

[0069] (In the general formulas (Ar-1) to (Ar-7), * indicates the bond position, Q １ is -N= or -CR ｋ The equals sign represents Q ２ is -O-, -S-, or -NR ｌ - represents R ｋ Each of these independently represents a hydrogen atom or a substituent E, and R ｌ J represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms. １ represents a monovalent group represented by the general formula (J-1), E represents the substituent E, and when n1 = 2 in general formulas (Ar-1) to (Ar-4), adjacent E members may be linked to each other to form an aliphatic ring or an aliphatic heterocycle, E １represents a hydrogen atom or the substituent E. n1 represents an integer of 0 to 2, n2 represents an integer of 0 to 1, k represents an integer of 1 to 4, k1 represents an integer of 0 to 2, k2 represents an integer of 1 to 3, and k3 represents an integer of 1 to 2. However, in the general formula (Ar-1), k1 + n1 is an integer of 0 to 2, in the general formulas (Ar-2) and (Ar-3), k + n1 is an integer of 1 to 4, in the general formula (Ar-4), k2 + n1 is an integer of 1 to 3, and in the general formulas (Ar-5) to (Ar-7), k3 + n2 is an integer of 1 to 2. Ar-(J １ ) ｋ contains the substituents E and J １ respectively, and when there are a plurality of each, they may be the same or different from each other.)

[0070] The substituent E in the general formulas (Ar-1) to (Ar-7) is the same as the substituent E described in A １ , A ２ , A ３ and A ４ . However, when n1 = 2 in the general formulas (Ar-1) to (Ar-4), adjacent Es may be linked to each other to form an aliphatic ring or an aliphatic heterocyclic ring. That is, adjacent Es may be linked to each other to form an alicyclic ring having 5 to 8 members, more preferably 5 to 6 members, or a heterocyclic ring containing at least one heteroatom selected from an oxygen atom, a nitrogen atom, or a sulfur atom.)

[0071] In the general formula (Ar-1), R ａ , R ｃ , and R ｄ each independently represent a hydrogen atom or a substituent E, and R ｂ , and R ｅ each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms. The substituent E in R ａ , R ｃ , and R ｄ is the same as the substituent E described in A １ , A ２ , A ３ and A ４ . The R ｂThe aliphatic hydrocarbon group having 1 to 6 carbon atoms in may be a linear, branched or cyclic alkyl group. Specifically, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, a cyclopentyl group, a cyclohexyl group and the like can be mentioned. The number of carbon atoms of the alkyl group may be 1 to 4, may be 1 or 2, and may be 1.

[0072] Q １ represents -N= or -CR ｋ =, but R ｋ is a hydrogen atom, -OR ａ , -SR ｄ , or may be an alkyl group having 1 to 4 carbon atoms. Q １ has good solvent solubility and, from the viewpoints of wavelength dispersion characteristics and stability, may be -N=, -CH=, -C(-OCH ３ )= or -C(-SCH ３ )=.

[0073] Q ２ represents -O-, -S- or -NR ｌ -, but R ｌ is a hydrogen atom or may be an alkyl group having 1 to 4 carbon atoms. Q ２ has good solvent solubility and, from the viewpoints of wavelength dispersion characteristics and ease of production and stability, may be -O-, -S-, -NH- or -N(CH ３ )-.

[0074] In the general formula (Ar-1), the combination of Q １ and Q ２ includes the following formulas (Ar-1-1) to (Ar-1-6), but from the viewpoints of having good solvent solubility, wavelength dispersion characteristics, and ease of production and stability, it may be at least one selected from the group consisting of the following formulas (Ar-1-2), (Ar-1-3), and (Ar-1-5).

[0075] (In the formula, J １ , R ｋ , R ｌE, n1, and k1 are as described above. (* indicates the bonding position.)

[0076] When n1 is 1 or 2, or when n2 is 1, the substituent E is, in terms of good solvent solubility, wavelength dispersion characteristics, ease of manufacture and stability, is particularly suitable for halogen atoms, -OR ａ , -COOR ｅ , -OCOR ｆ , or may be an aliphatic hydrocarbon group. The halogen atom may be a fluorine atom, a chlorine atom, or a bromine atom. -OR ａ This may be an alkoxy group having 1 to 4 carbon atoms, and may be a methoxy group or an ethoxy group. -COOR ｅ Among these, it may be a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, or an isopropoxycarbonyl group, and may be a methoxycarbonyl group. -OCOR ｆ The aliphatic hydrocarbon group may be a methyl carbonyloxy group, an ethyl carbonyloxy group, an n-propyl carbonyloxy group, or an isopropyl carbonyloxy group, and may be a methyl carbonyloxy group. The aliphatic hydrocarbon group may be a linear, branched, or cyclic alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 8 carbon atoms, an alkyl group having 1 to 6 carbon atoms (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, an n-pentyl group, a cyclopentyl group, a cyclohexyl group, etc.), an alkyl group having 1 to 4 carbon atoms, or a methyl group or an ethyl group. n1 may be 0 or 1, and n1 and n2 may each independently have good solvent solubility and may be 0 from the viewpoint of wavelength dispersion characteristics, manufacturing, and solubility.

[0077] In the general formula (I), Ar-(J １ ) ｋIt may be a divalent group represented by any of the general formulas (Ar-1), (Ar-2), (Ar-3), (Ar-5), (Ar-6), or (Ar-7) having good solvent solubility and wavelength dispersion characteristics, and may be a divalent group represented by any of the general formulas (Ar-1), (Ar-2), or (Ar-3). Also, in the general formula (I), Ar-(J １ ) ｋ It may be a divalent group represented by either the general formula (Ar-2) or the general formula (Ar-3), in terms of having good solvent solubility, wavelength dispersion characteristics, and ease of manufacture. It may be a divalent group represented by the general formula (Ar-3), in terms of having good solvent solubility and readily exhibiting inverse wavelength dispersion.

[0078] In general formula (I), Ar-(J １ ) ｋ It is preferable, but not limited to, that the group represented is selected from the group consisting of formulas (a-1) to (a-11) below, in terms of having good solvent solubility, wavelength dispersion characteristics, and ease of manufacture due to the availability of raw materials. In particular, it may be a group selected from the group consisting of formulas (a-1), (a-2), (a-6), and (a-7) below, in terms of having good solvent solubility, wavelength dispersion characteristics, and ease of manufacture, or a group selected from the group consisting of formulas (a-1) and (a-6) below.

[0079]

[0080] In the general formula (I), J １ represents a monovalent group represented by the following general formula (J-1), and * represents the bond position.

[0081] (In the general formula (J-1), * represents the bond position, R ｘ and R ｙ Each of these is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, and -OR ｗ１ , -SR ｗ２ , -COOR ｗ３ , -OCOR ｗ４ , -COR ｗ５, -CONR ｗ６ R ｗ７ , -NR ｗ８ R ｗ９ , or, -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by (R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R ｗ６ and R ｗ７ each independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, and R ｗ８ and R ｗ９ each independently represents a hydrogen atom, -OR ｗ１ , or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and -CH ２ - in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, or R ｘ and R ｙ may be bonded to each other to form an aliphatic ring having 4 to 7 members, and the aliphatic ring may contain a hetero atom. However, at least one of R ｘ and R ｙ is an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted, -COOR ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ represents, or R ｘ and R ｙ are bonded to each other to form an aliphatic ring which may contain a hetero atom having 4 to 7 members.).

[0082] R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R / / 原文此处多了个 ｗ６ 的换行,推测有误,已修正 ｗ６ , R ｗ７ , R ｗ８ and R ｗ９The aliphatic hydrocarbon group having 1 to 6 carbon atoms in the compound may be saturated or unsaturated, linear, branched, or cyclic, and the aliphatic hydrocarbon group contains -CH ２ The - can be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-. Specifically, examples include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, cyclohexyl group, vinyl group, propenyl group, butenyl group, ethynyl group, propane-2-in-1-yl group, acetylmethyl group, acetylthiomethyl group, methylcarbonatemethyl group, etc. The number of carbon atoms in the aliphatic hydrocarbon group may be 1 to 4, 1 or 2, or 1.

[0083] -OR ｗ１ Examples include hydroxyl groups or alkoxy groups having 1 to 6 carbon atoms. Examples of alkoxy groups having 1 to 6 carbon atoms include methoxy groups, ethoxy groups, n-propoxy groups, isopropoxy groups, n-butoxy groups, n-pentyloxy groups, and acetylmethoxy groups. -SR ｗ２ Examples include mercapto groups or alkylthio groups having 1 to 6 carbon atoms. Examples of alkylthio groups having 1 to 6 carbon atoms include methylthio groups, ethylthio groups, n-propylthio groups, t-butylthio groups, etc. -COOR ｗ３ Examples include carboxyl groups or alkoxycarbonyl groups having 1 to 6 carbon atoms. Examples of alkoxycarbonyl groups having 1 to 6 carbon atoms include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, n-pentyloxycarbonyl group, etc. -OCOR ｗ４Examples include formyloxy groups or alkylcarbonyloxy groups having 1 to 6 carbon atoms. Examples of alkylcarbonyloxy groups having 1 to 6 carbon atoms include methylcarbonyloxy groups, ethylcarbonyloxy groups, n-propylcarbonyloxy groups or isopropylcarbonyloxy groups, n-butoxycarbonyloxy groups, t-butoxycarbonyloxy groups, etc. -COR ｗ５ Examples include a formyl group or an alkylcarbonyl group having 1 to 6 carbon atoms. Examples of alkylcarbonyl groups having 1 to 6 carbon atoms include a methylcarbonyl group (acetyl group), an ethylcarbonyl group, an n-propylcarbonyl group or an isopropylcarbonyl group, an n-butylcarbonyl group, a t-butylcarbonyl group, and the like. -CONR ｗ６ R ｗ７ For example, an amide group (-CONH ２ Examples include methylamide groups and dimethylamide groups. -NR ｗ８ R ｗ９ For example, an amino group (-NH ２ Examples include hydroxyamino groups (-NHOH), methylamino groups, dimethylamino groups, and diisopropylamino groups. Ｅ , R ｓｐＥ , and Z Ｅ These are, respectively, the L ５ , R ｓｐ１ , and Z １ It may be the same as L. Ｅ , R ｓｐＥ , and Z Ｅ Each of the L molecules is ５ , R ｓｐ１ , and Z １ It may be the same as or different from it.

[0084] The aliphatic hydrocarbon group having 1 to 20 carbon atoms, which may be substituted by one or more of the substituents, may be saturated or unsaturated, linear, branched, or cyclic, and the aliphatic hydrocarbon group contains -CH ２The dash may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-. Specifically, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, 2-ethylhexyl group, n-octyl group, n-decyl group, n-dodecyl group, n-tridecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, methylcyclohexyl group, ethylcyclohexyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, tricyclo[5.2.1.0 ２，６ ] Decyl group, tricyclo[3.3.1.1 ３，７ ] Decyl group, tetracyclo[6.2.1.1 ３，６ . 0 ２，７ Examples include dodecyl group, adamantyl group, cyclopentylmethyl group, cyclohexylmethyl group, cyclohexylheptyl group, vinyl group, propenyl group, butenyl group, ethynyl group, propane-2-in-1-yl group, fluoromethyl group, cyanomethyl group, nitromethyl group, hydroxymethyl group, methoxymethyl group, aminomethyl group, and acetylmethyl group. The number of carbon atoms in the aliphatic hydrocarbon group may be 1 to 20, 1 to 12, or 1 to 6.

[0085] Or, R ｘ and R ｙ These may bond to each other to form a 4- to 7-membered aliphatic ring, which may contain heteroatoms and unsaturated bonds. The 4- to 7-membered aliphatic ring may contain -CH ２ - is -O-, -S-, -NR ｍ -, -CS-, or -CO- may be substituted (where R ｍ is the aforementioned R l (This may be the same as above), =CH- may be replaced with =N-, and may be substituted with one or more substituents. ｘ and R ｙAs substituents on the aliphatic ring, R ｘ and R ｙ Among the monovalent groups, it may be a group other than a hydrogen atom, and the halogen atom, cyano group, nitro group, -OR ｗ１ , -SR ｗ２ , -COOR ｗ３ , -OCOR ｗ４ , -COR ｗ５ , -CONR ｗ６ R ｗ７ , -NR ｗ８ R ｗ９ , or -L Ｅ -R ｓｐＥ -Z Ｅ The group represented by (R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R ｗ６ and R ｗ７ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, R ｗ８ and R ｗ９ These are, independently, hydrogen atoms, -OR ｗ１ (or represents an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of the above, and the aliphatic hydrocarbon group contains -CH ２ The group in which - may be replaced is -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-. ｘ and R ｙ Among the aliphatic ring substituents, halogen atoms and -OR atoms are particularly suitable due to their good solvent solubility, wavelength dispersion characteristics, and structural stability. ｗ１ , or represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms, and the aliphatic hydrocarbon group contains -CH ２ - may be replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, and the group may be a halogen atom, -OR ｗ１ , or may be an aliphatic hydrocarbon group having 1 to 6 carbon atoms, a halogen atom, -ORｗ１ Alternatively, it may be an alkyl group having 1 to 6 carbon atoms.

[0086] R ｘ and R ｙ At least one of them is an aliphatic hydrocarbon group having 1 to 20 carbon atoms, which may be substituted, -COOR ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ It represents, or R ｘ and R ｙ These atoms are bonded to each other to form an aliphatic ring which may contain a heteroatom of 4 to 7 members, but among them, R is selected from the viewpoint of wavelength dispersion characteristics and solubility. ｘ and R ｙ an aliphatic hydrocarbon group having 1 to 20 carbon atoms, -COOR, in which at least one of the following may be substituted. ｗ３ , or -COR ｗ５ It represents, or R ｘ and R ｙ These may be aliphatic rings bonded to each other, which may contain heteroatoms forming a 4-7 membered ring, and may be substituted with aliphatic hydrocarbon groups having 1 to 10 carbon atoms, -COOR ｗ３ , or -COR ｗ５ It represents, or R ｘ and R ｙ These may be aliphatic rings that are bonded to each other and may contain heteroatoms forming a 4- to 7-membered ring. In particular, from the viewpoint of wavelength dispersion characteristics and solubility, R ｘ and R ｙ an aliphatic hydrocarbon group having 1 to 6 carbon atoms, or -COOR, in which at least one of the following may be substituted. ｗ３ It represents, or R ｘ and R ｙ The aliphatic ring may contain heteroatoms forming a 4- to 7-membered ring by bonding with each other. The substituents of the aliphatic hydrocarbon group may be halogen atoms, cyano groups, -OR ｗ１ , or -NR ｗ８ R ｗ９ The substituents of the aliphatic ring may be halogen atoms, -OR ｗ１ Alternatively, it may be an alkyl group having 1 to 6 carbon atoms.

[0087] In particular, R is favored due to its wavelength dispersion characteristics, good solvent solubility, and the ease of obtaining and manufacturing raw materials. ｘ and R ｙ One of the terms represents an aliphatic hydrocarbon group having 1 to 6 carbon atoms, which may be substituted, and the other is -OR ｗ１ , -COOR ｗ３ , -OCOR ｗ４ , or -COR ｗ５ R ｘ and R ｙ It is preferable that the aliphatic rings may contain heteroatoms forming a 4- to 7-membered ring by bonding with each other. ｘ and R ｙ If the atoms are bonded to each other and form an aliphatic ring that may contain heteroatoms of a 4- to 7-membered ring, this is preferable because it tends to exhibit inverse wavelength dispersion.

[0088] As the monovalent group represented by general formula (J-1), it is preferable to represent a group selected from formulas (j-1) to (j-78) below, in terms of wavelength dispersion characteristics, good solvent solubility, and ease of obtaining raw materials and manufacturing, but it is not limited to these. In particular, a group selected from the group consisting of formulas (j-2), (j-5), (j-6), (j-7), (j-8), (j-9), (j-10), (j-11), (j-14), (j-23), formula (j-67), formula (j-69), formula (j-77), and formula (j-78) below is preferably used in terms of wavelength dispersion characteristics, good solvent solubility, and ease of obtaining raw materials and manufacturing, and a group selected from the group consisting of formulas (j-2), (j-5), (j-6), formula (j-67), formula (j-69), and formula (j-77), and formula (j-78) below is more preferably used.

[0089]

[0090] (In the formula, * indicates the bonding position.)

[0091] Furthermore, examples of compounds represented by general formula (I) include the following compounds (1) to (73). In the table, Ar-(J １ ) ｋ This is represented by a group selected from formulas (a-1) to (a-11), and Ar-(J １ )ｋ J inside １ Let be represented by a group selected from formulas (j-1) to (j-78), where Lc1 is -L １ -A １ - (L ３ -A ３ ) ｍ１ -L ５ -R ｓｐ１ -Z １ Lc2 is -L ２ -A ２ - (L ４ -A ４ ) ｍ２ -L ５ -R ｓｐ１ -Z １ It represents.

[0092]

[0093]

[0094] Compounds represented by general formula (I) can be produced, for example, by the following methods. These methods include appropriately combining known organic synthesis reactions (e.g., condensation reactions, esterification reactions, Williamson reactions, Ullmann reactions, Wittig reactions, Schiff base formation reactions, benzylation reactions, Sonogashira reactions, Suzuki-Miyaura reactions, Negishi reactions, Kumada reactions, Hiyama reactions, Buchwald-Hartwig reactions, Friedelcraft reactions, Heck reactions, aldol reactions, Daff reactions, etc.) described in books such as "Methoden der Organischen Chemie," "Organic Reactions," "Organic Syntheses," "Comprehensive Organic Synthesis," and "New Experimental Chemistry Course," depending on the structure. Examples of production methods are shown below, but this disclosure is not limited to these structures or production methods.

[0095] The compound represented by general formula (I) may use the compound represented by the following general formula (Ar-im) as an intermediate.

[0096] [In the general formula (Ar-im), Ar-(J １ ) ｋThis represents a divalent group represented by one of the following general formulas (Ar-1) to (Ar-7), and T １ , and T ２ These are, independently, -OH, -CHO, -COOH, -SH, and -NH. ２ , halogen atom, -CH ２ OH, -CH ２ SH, -CF ２ OH, -CF ２ SH represents -CH=CHCOOH, or -CH=CHOCOOH.

[0097] (In the general formulas (Ar-1) to (Ar-7), * indicates the bond position, Q １ Q ２ J １ , and E, as well as n1, n2, k, k1, k2, and k3, are each independently synonymous with the respective symbols in the general formulas (Ar-1) to (Ar-7).

[0098] T １ , and T ２ These are, independently, -OH, -CHO, -COOH, -SH, and -NH. ２ , halogen atom, -CH ２ OH, -CH ２ SH, -CF ２ OH, -CF ２ SH represents -CH=CHCOOH or -CH=CHCOOH, but L １ , and L ２ It should be selected appropriately according to the structure. For example, T １ or T ２ If -OH, L １ or L ２ ga-OCO-,-O-,-OCH ２ -, -O-CO-O-, -OCO-NH-, -O-NH-, -OCF ２ -, -OCO-CH=CH-, -OCO-CH ２ CH ２ -, -OCO-CH ２ It can be used as an intermediate if - １ or T ２ In the case of -CHO, L １ or L ２It can be used as an intermediate when -CH=N-, -CH=N-N=CH-, and -CH=CH-. １ or T ２ If -COOH, L １ or L ２ is -CO-, -COO-, -CO-S-, -CO-NH-, -COO-CH=CH-, -COO-CH ２ CH ２ -, -COO-CH ２ It can be used as an intermediate if - １ or T ２ In the case of -SH, L １ or L ２ -SCO-, -S-, -SCH ２ -, -SCF ２ It can be used as an intermediate if - １ or T ２ ga-NH ２ In the case of L １ or L ２ It can be used as an intermediate when the compound is -NH-CO-, -NH-COO-, -NH-CO-NH-, -NH-O-, -N=N-, or -N=CH-. １ or T ２ If it is a halogen atom, L １ or L ２ ga-CH ２ CH ２ -COO-, -CH ２ It can be used as an intermediate when the bond is -COO-, -CH=CH-, -C≡C-, -CF=CF-, or a single bond. １ or T ２ ga-CH ２ In the case of OH, L １ or L ２ ga-CH ２ O-, -CH ２ It can be used as an intermediate when it is -OCO-. １ or T ２ ga-CH ２ In the case of SH, L １ or L ２ ga-CH ２ It can be used as an intermediate when it is S-. １ or T ２ ga-CF２ In the case of OH, L １ or L ２ ga-CF ２ It can be used as an intermediate when it is O-. １ or T ２ ga-CF ２ In the case of SH, L １ or L ２ ga-CF ２ It can be used as an intermediate when it is S-. １ or T ２ If -CH=CHCOOH, then L １ or L ２ It can be used as an intermediate when -CH=CH-COO-. １ or T ２ If -CH=CHOCOOH, then L １ or L ２ It can be used as an intermediate when -CH=CH-OCO-.

[0099] Compounds represented by the general formula (Ar-im) can be produced, for example, from amine compounds via hydrazine compounds, as described in Chemical Communications (Cambridge, United Kingdom) (2016), 52(56), 8733-8736. Depending on the reaction conditions, T １ or T ２ The reaction may be carried out after protecting the compound with a protecting group.

[0100] (In the formula, Ar, T １ , and T ２ The signs are equivalent to each sign in the general formula (Ar-im), and R ｘ and R ｙ (These symbols are equivalent to the symbols in general formula (J-1).)

[0101] The starting material, an amine compound, can also be produced, for example, by reducing a nitro compound, and in this case T １ or T ２The amino group may be protected with a protecting group before the reaction. A general reducing agent can be used for reduction. The starting amine compound can be prepared by referring to, for example, Journal of the American Chemical Society (2009), 131(31), 11049-11061 or Bioorganic & Medicinal Chemistry Letters (2012), 22(24), 7451-7455 regarding the introduction of the amino group. Alternatively, commercially available compounds may be appropriately selected and used as the starting amine compound.

[0102] For example, L １ and L ２ A polymerizable liquid crystal compound represented by the following general formula (I-1), where each of the elements is *-OCO- (where * indicates the bonding position with Ar), can be produced by preparing a compound represented by the following general formula (Ar-im1), a compound represented by the general formula (mc-1), and a compound represented by the general formula (mc-2), and then simultaneously or sequentially carrying out a condensation reaction of the compound represented by the following general formula (Ar-im1), the compound represented by the general formula (mc-1), and the compound represented by the general formula (mc-2).

[0103] (In general formulas (Ar-im1), (mc-1), (mc-2), and (I-1), Ar-(J １ ) ｋ This represents a divalent group represented by any of the general formulas (Ar-1) to (Ar-7), and is synonymous with each sign of the divalent group represented by any of the general formulas (Ar-1) to (Ar-7), A １ A ２ A ３ A ４ , L ３ , L ４ , R １ and R ２ Furthermore, m1 and m2 are each independently synonymous with the respective symbols in the general formula (I).

[0104] The compound represented by the general formula (Ar-im1) is, in the compound represented by the general formula (Ar-im), T １ and T２ The same synthesis can be performed if the group is -OH.

[0105] Next, we have the compound represented by the general formula (Ar-im1) and the general formula (mc-1): HOOC-A １ - (L ３ -A ３ ) ｍ１ -R １ Compound represented by (A １ , L ３ A ３ , R １ , and m1 have the same meaning as above), and general formula (mc-2): HOOC-A ２ - (L ４ -A ４ ) ｍ２ -R ２ Compound represented by (A ２ , L ４ A ４ , R ２ By simultaneously or sequentially condensing the compounds represented by the following general formula (I-1), the compounds represented by the following general formula (mc-1) can be produced. The order in which the compounds represented by general formula (mc-1) and general formula (mc-2) are sequentially condensed is arbitrary. An intermediate may be obtained by condensing the compound represented by general formula (mc-1) with the compound represented by general formula (Ar-im1), and then the compound represented by general formula (mc-2) may be further condensed with the intermediate. Alternatively, an intermediate may be obtained by condensing the compound represented by general formula (mc-2) with the compound represented by general formula (Ar-im1), and then the compound represented by general formula (mc-1) may be further condensed with the intermediate. If the structures of the compound represented by general formula (mc-1) and the compound represented by general formula (mc-2) are the same, then the compounds represented by general formula (mc-1) and general formula (mc-2) can be condensed simultaneously. In essence, the compound represented by general formula (I-1) can be produced by condensing the compound represented by general formula (Ar-im1) with the compound represented by general formula (mc-1) at a 2:1 molar equivalent ratio.

[0106]

[0107] Furthermore, the polymerizable liquid crystal compound represented by general formula (I) of this disclosure may not use the compound represented by general formula (Ar-im) and the substituent E may be introduced later, depending on the type and substitution position of substituent E. Also, the polymerizable liquid crystal compound represented by general formula (I) of this disclosure may not use the compound represented by general formula (Ar-im) and the substituent E may be introduced later. １ This can also be obtained by introducing [a certain method].

[0108] Furthermore, each intermediate used in the manufacturing process may be a commercially available product as appropriate, or it may be synthesized as appropriate by conventionally known methods.

[0109] In this disclosure, the structure of polymerizable liquid crystal compounds can be analyzed by appropriately combining nuclear magnetic resonance spectroscopy (NMR), pyrolysis gas chromatography-mass spectrometry (Py-GC-MS), and matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOFMS).

[0110] Furthermore, the polymerizable liquid crystal compounds of this disclosure are polymerizable liquid crystal compounds capable of forming a phase difference layer exhibiting inverse wavelength dispersion or flat wavelength dispersion. When a polymerizable composition containing only the polymerizable liquid crystal compounds of this disclosure and a photopolymerization initiator is prepared, a cured film (phase difference layer) is formed, and the phase difference value is measured, it is preferable that Re(450) / Re(550) is in the range of 0.60 or more and less than 1.05, more preferably in the range of 0.60 or more and less than 1.00, even more preferably in the range of 0.60 or more and less than 0.95, and even more preferably in the range of 0.60 or more and less than 0.93. In addition, it is preferable that Re(650) / Re(550) is greater than 1.00, and even more preferably in the range of 1.02 or more and 1.10 or less. The following measurement methods can be used as test methods for the phase difference value. [Test Method] A polymerizable composition is prepared by dissolving 100 parts by mass of the polymerizable liquid crystal compound of this disclosure and 4 parts by mass of 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one in 900 parts by mass of cyclopentanone. This polymerizable composition is then rubbed onto glass with a polyimide alignment film [the alignment-treated glass substrate is coated with polyimide LX-1400 manufactured by Hitachi Chemical Co., Ltd. and then rubbed]. Polyimide LX-1400 is spin-coated onto the glass substrate, and the unspin-coated glass surface is placed on a hot plate at 80°C for 1 minute to dry and produce a polyimide coating on the glass substrate. The polyimide-coated glass substrate is baked in an oven at 230°C for 30 minutes. The polyimide coating on the polyimide-coated glass substrate is rubbed to obtain glass with a polyimide alignment film after rubbing. The rubbing conditions are as follows. The film was formed by coating an alignment film with a roll rotation speed of 600 rpm, a travel speed of 30 mm / sec, and 3 reciprocations, so that the cured film thickness would be 1 μm. After drying for 120 seconds at a temperature 10°C above the solid-liquid crystal phase transition temperature (°C) of the polymerizable liquid crystal compound contained, the film was irradiated with ultraviolet light at a dose of 400 mJ / cm². ２A phase difference layer is formed by irradiation, and the in-plane phase difference Re(450) for a wavelength of 450 nm and the in-plane phase difference Re(550) for a wavelength of 550 nm are measured using a phase difference measuring device (KOBRA series, manufactured by Oji Instruments Co., Ltd.). (A1) First, in order to stabilize the light source of the phase difference measuring device, leave it for more than 60 minutes after turning on the light source. Then, select waveplate measurement and obtain data from the reference analyzer. (A2) Use the wavelength dispersion characteristic mode and set the measurement conditions as follows and perform the measurement. (Measurement conditions) ・Measurement mode: Standard ・Tilt central angle: Leading axis ・Incident angle: 0° ・Average number of measurements: 3 times ・Average refractive index of the layer to be measured: The measured value (average refractive index) of the orientation measurement sample was entered using an Abbe refractometer (manufactured by Atago) with sodium D line (589 nm) as the light source, in accordance with JIS K7142:2014. ・Thickness: Enter the total thickness of the horizontal alignment layer and the phase difference layer. Furthermore, similar results can be obtained by forming a phase difference layer using the method shown in Example 1 described later and measuring the phase difference value.

[0111] Furthermore, the polymerizable liquid crystal compounds of this disclosure preferably have a solid-liquid crystal phase transition temperature of 25°C to 200°C, more preferably 30°C to 180°C, and even more preferably 30°C to 150°C, as this expands the range of usable substrates. A lower solid-liquid crystal phase transition temperature reduces the load in the liquid crystal orientation process and allows use on substrates that are sensitive to high temperatures. Here, the solid-liquid crystal phase transition temperature refers to the temperature at which the liquid crystal compound changes from a solid to a liquid crystal. In this disclosure, the solid-liquid crystal phase transition temperature is confirmed during heating by texture observation using a polarizing microscope equipped with a temperature control stage. That is, in polarizing microscope observation, the point at which the solid melts and becomes liquid during heating, and which becomes bright-field in crossed nicol observation (polarizing plates are orthogonal), can be identified as the solid-liquid crystal phase transition temperature.

[0112] Furthermore, the polymerizable liquid crystal compound of this disclosure is preferably solvable in 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, in order to broaden the range of usable substrates, more preferably solvable in 20% by mass or more, and even more preferably solvable in 30% by mass or more.

[0113] B. Polymerizable Compositions The polymerizable compositions of this disclosure are compositions comprising at least the polymerizable liquid crystal compound of this disclosure.

[0114] Since the polymerizable composition of this disclosure contains the polymerizable liquid crystal compound of this disclosure, as described above, it can be a polymerizable composition that has good solvent solubility and can form a phase difference layer exhibiting inverse wavelength dispersion and flat wavelength dispersion. Since the polymerizable composition of this disclosure contains the polymerizable liquid crystal compound of this disclosure, it is easy to prepare a composition (ink) containing a solvent suitable for film manufacturing such as a phase difference layer, crystal precipitation is less likely to occur during film manufacturing such as a phase difference layer, and it is possible to create a film that satisfies the required physical properties. Because the polymerizable liquid crystal compound has good solvent solubility, a solvent suitable for the manufacturing process can be used as the solvent that can be used in the polymerizable composition.

[0115] The polymerizable composition of this disclosure contains at least the polymerizable liquid crystal compound of this disclosure, but more preferably contains a photopolymerization initiator. Furthermore, the polymerizable composition of this disclosure may contain polymerizable liquid crystal compounds different from the polymerizable liquid crystal compound of this disclosure, in order to adjust the phase difference and wavelength dispersibility, as well as the orientation, solubility, and phase transition temperature, and may also contain other components to the extent that the effects are not impaired. The components constituting the polymerizable composition of this disclosure will be described in order below.

[0116] 1. Polymerizable Liquid Crystal Compounds in the Polymerizable Compositions of the Present Disclosure The polymerizable liquid crystal compounds in the polymerizable compositions of the Present Disclosure may be the same as those described in "A. Polymerizable Liquid Crystal Compounds" above, so the description here is omitted. In the polymerizable compositions of the Present Disclosure, one polymerizable liquid crystal compound may be used alone, or two or more may be used in combination. In this embodiment, in order to obtain a polymerizable composition that has good solvent solubility and can form a phase difference layer exhibiting inverse wavelength dispersion and flat wavelength dispersion, the content ratio of the polymerizable liquid crystal compound in the Present Disclosure 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, per 100 parts by mass of solid content of the polymerizable composition. In this Disclosure, solid content refers to all components excluding the solvent, and for example, polymerizable liquid crystal compounds different from the polymerizable liquid crystal compounds of the Present Disclosure, as described later, are included in the solid content even if they are in liquid form.

[0117] 2. Photopolymerization Initiator In this embodiment, the photopolymerization initiator can be appropriately selected from conventionally known substances. Specific examples of such photopolymerization initiators include, for example, aromatic ketones containing thioxanthones, α-aminoalkylphenones, α-hydroxyketones, acylphosphine oxides, oxime esters, aromatic onium salts, organic peroxides, thio compounds, hexaarylbiimidazole compounds, ketooxime ester compounds, borate compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having carbon-halogen bonds, and alkylamine compounds. Among these, at least one selected from the group consisting of acylphosphine oxide polymerization initiators, α-aminoalkylphenone polymerization initiators, α-hydroxyketone polymerization initiators, and oxime ester polymerization initiators is preferred because it hardens to the interior of the coating film and improves durability.

[0118] Examples of acylphosphine oxide polymerization initiators include bis(2,4,6-trimethylbenzoyl)-phenyl-phosphine oxide (manufactured by Sigma-Aldrich, etc.), bis(2,6-dimethoxybenzoyl)-2,4,4-trimethyl-pentylphenylphosphine oxide, and 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (manufactured by Tokyo Chemical Industry Co., Ltd., etc.).

[0119] Examples of α-aminoalkylphenone polymerization initiators include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one (manufactured by Sigma-Aldrich, etc.), 2-benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone (manufactured by Sigma-Aldrich, etc.), and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]-1-butanone (manufactured by Sigma-Aldrich, etc.).

[0120] Examples of α-hydroxyketone polymerization initiators include 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]-phenyl}-2-methyl-propan-1-one (manufactured by Sigma-Aldrich, etc.), 2-hydroxy-4'-hydroxyethoxy-2-methylpropiophenone (manufactured by Sigma-Aldrich, etc.), 1-hydroxycyclohexyl-phenyl-ketone (manufactured by Tokyo Chemical Industry Co., Ltd., etc.), and oligo{2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone} (for example, trade name: ESACURE ONE, manufactured by Lambertie, etc.).

[0121] 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), ethanoone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-,1-(o-acetyloxime) (trade name: Irgacure OXE-02, manufactured by BASF), methanone, ethanoone, 1-[9-ethyl-6-(1,3-dioxolane,4-(2-methoxyphenoxy)-9H-carbazole-3-yl]-,1-(o-acetyloxime) (trade name: Adeka Arcules N-1919T, manufactured by ADEKA Corporation), etc.

[0122] In this embodiment, the photopolymerization initiator can be used alone or in combination of two or more. In this embodiment, the content ratio of the photopolymerization initiator 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, per 100 parts by mass of solid content of the polymerizable composition, from the standpoint of promoting the curing of the polymerizable compound.

[0123] 3. Polymerizable Liquid Crystal Compounds Different from the Polymerizable Liquid Crystal Compounds of the Present Disclosure In the polymerizable compositions of the present disclosure, polymerizable liquid crystal compounds different from the polymerizable liquid crystal compounds of the present disclosure can be appropriately selected from among those conventionally known. These may be polymerizable liquid crystal compounds with general normal dispersion (positive dispersion) where the slope of the graph obtained by plotting the wavelength λ of incident light on the phase difference film on the horizontal axis and its birefringence on the vertical axis is negative (downward sloping to the right), or they may be polymerizable liquid crystal compounds with inverse wavelength dispersion, or they may be polymerizable liquid crystal compounds that substantially do not exhibit wavelength dispersion (flat dispersion or low wavelength dispersion). Examples of polymerizable liquid crystal compounds different from the polymerizable liquid crystal compounds of the present disclosure include, for example, the polymerizable liquid crystal compounds described in Japanese Patent No. 5463666, Japanese Patent No. 4186981, Japanese Patent No. 5962760, and Japanese Patent No. 5826759, which exhibit inverse wavelength dispersion. Examples of compounds exhibiting flat dispersion include those described in Recueil des Travaux Chimiques des Pays-Bas (1996), 115(6), 321-328.

[0124] In this embodiment, it is preferable that the polymerizable liquid crystal compound has a polymerizable functional group at at least one end of the rod-shaped mesogen, and more preferably that the polymerizable liquid crystal compound has polymerizable functional groups at both ends of the rod-shaped mesogen, as this facilitates orientation when combined with the polymerizable liquid crystal compound. A polymerizable liquid crystal compound having two or more polymerizable functional groups in one molecule can improve the hardness and durability of the coating film. Examples of polymerizable liquid crystal compounds used in this disclosure include a polymerizable liquid crystal compound represented by the following general formula (II-1) and a polymerizable liquid crystal compound represented by the following general formula (II-2), which have a structure similar to the main chain portion of the polymerizable compound.

[0125] (In the formula, Z １０ , and Z ２０ Each of these independently represents a polymerizable functional group, R ｓｐ１０ , and R ｓｐ２０ Each of these independently represents a single bond or an alkylene group with 1 to 20 carbon atoms, but one -CH ２ - or two or more non-adjacent -CH ２ - can be replaced with -O-, -COO-, -OCO-, -OCOO-, L １０ , L ２０ and L ３０ These are independently -O-, -S-, and -OCH. ２ -ien-CH ２ O-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -CF=CF-, -C≡C-, or single bond are represented by A １０ , and A ２０ Each of these independently represents a benzene-1,4-diyl group, a cyclohexane-1,4-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, but A １０ , and A ２０ Each of the groups may be independently unsubstituted or substituted with an alkyl group, a halogenated alkyl group, an alkoxy group, a halogenated alkoxy group, a halogen atom, a cyano group, or a nitro group, where R is a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a cyano group, a nitro group, an isocyano group, a thioisocyano group, or one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents a linear or branched alkyl group having 1 to 20 carbon atoms, which may be substituted 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 s1 and s2 represent 0, 1, 2, 3, or 4, but if s1 and s2 independently represent 2, 3, or 4, then there are 2, 3, or 4 A ２０ , L １０ They may be the same or different.

[0126] The polymerizable functional group of the polymerizable liquid crystal compound is Z of the polymerizable compound. １Examples of polymerizable liquid crystal compounds include polymerizable functional groups such as oxirane rings, oxetane rings, and other cyclic ether-containing groups, as well as ethylenically double-bond-containing groups. Among these, ethylenically double-bond-containing groups are preferred due to their photocurability and ease of handling. An example of a cyclic ether group is a glycidyl group. Examples of ethylenically double-bond-containing groups include vinyl groups, allyl groups, and (meth)acryloyl groups, among which (meth)acryloyl groups are preferred.

[0127] In this embodiment, from the viewpoint of orientation, the polymerizable liquid crystal compound is preferably one or more compounds selected from the compounds represented by the following general formula (III) and the compounds represented by the following general formula (IV).

[0128] (In general formula (III), R ２１ R is a hydrogen atom or a methyl group. ２２ is, -(CH ２ ) ｐ - or - (C ２ H ４ O) ｐ’ Represents a base represented by -. L ２３ Ar ３ Ar represents a benzene-1,4-diyl group, a cyclohexane-1,4-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group. ３ L may be unsubstituted or substituted with an alkyl group, halogenated alkyl group, alkoxy group, halogenated alkoxy group, halogen atom, cyano group or nitro group, and there may be multiple L ２３ and Ar ３ These may be the same or different. ２３ -F, -Cl, -CN, -OCF ３ , -OCF ２ H, -NCO, -NCS, -NO ２, -NHC(=O)-R ２４ , -C(=O)-OR ２４ , -OH, -SH, -CHO, -SO ３ H, -NR ２４ ２ , -R ２５ , or -OR ２５ R ２４ R represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ２５ represents an alkyl group having 1 to 6 carbon atoms. b is an integer between 2 and 5, and p and p' are independently integers between 2 and 10.

[0129] (In general formula (IV), R ３１ and R ３２ Each of them independently has a hydrogen atom or a methyl group, R ３３ is, -(CH ２ ) ｑ - or - (C ２ H ４ O) ｑ’ The group represented by - is R ３４ is, -(CH ２ ) ｒ - or - (OC ２ H ４ ) ｒ’ Represents a base represented by -. L ３４ Ar ４ Ar represents a benzene-1,4-diyl group, a cyclohexane-1,4-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group. ４ L may be unsubstituted or substituted with an alkyl group, halogenated alkyl group, alkoxy group, halogenated alkoxy group, halogen atom, cyano group or nitro group, and there may be multiple L ３４ and Ar ４ These can be the same or different. c is an integer between 2 and 5 (inclusive), and q, q', r, and r' are each independent integers between 2 and 10 (inclusive).

[0130] In general formula (III), p and p', and in general formula (IV), q, q', r and r' are preferably between 2 and 8, more preferably between 2 and 6, and even more preferably between 2 and 5, from the viewpoint of orientation. ３ and Ar ４ Each of these represents a benzene-1,4-diyl group, a cyclohexane-1,4-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a tetrahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group, but among these, the benzene-1,4-diyl group, the naphthalene-2,6-diyl group, or the cyclohexane-1,4-diyl group is more preferred. ３ and Ar ４ The substituents that may be present include alkyl groups, halogenated alkyl groups, alkoxy groups, halogenated alkoxy groups, halogen atoms, cyano groups, or nitro groups, but more preferably alkyl groups having 1 to 5 carbon atoms, halogen atoms, etc. Also, R in general formula (III) ２４ and R ２５ The alkyl group having 1 to 6 carbon atoms in R may be linear, branched, or cyclic. Examples include linear alkyl groups such as methyl, ethyl, n-propyl, n-butyl, n-pentyl, and n-hexyl groups; branched alkyl groups such as i-propyl, i-butyl, t-butyl, and 2-methylbutyl groups; and cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl groups. ２４ In particular, it is preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ２５ In particular, it is preferable that the alkyl group has 1 to 5 carbon atoms, and more preferably that it is an alkyl group having 1 to 3 carbon atoms. ２３ In particular, from the standpoint of orientation, -Cl, -CN, and -OCF ３ , -OCF ２ H, -NCO, -NCS, -NO２ , -NHC(=O)-R ２５ , -C(=O)-OR ２４ , -OH, -SH, -CHO, -SO ３ H, -NR ２４ ２ , -R ２５ , or -OR ２５ Preferably, -Cl, -CN, -OCF ３ OR -C (=O) -OR ２４ , -R ２５ , or -OR ２５ It is preferable that it be so.

[0131] As the mesogenic structure contained in the polymerizable liquid crystal compound, the substructures represented by the following chemical formulas (V-1) to (V-6) are preferably used, and among them, at least one substructure selected from the group consisting of the following chemical formulas (V-1), (V-2), (V-4), (V-5), and (V-6) containing three or more ring structures is preferably used. In the substructures represented by the following chemical formulas (V-1) to (V-6), the hydrogen atoms in the phenylene group and naphthylene group may be substituted with alkyl groups having 1 to 3 carbon atoms or halogen atoms.

[0132]

[0133] Suitable specific examples of compounds represented by general formula (III) and general formula (IV) include, but are not limited to, those shown in the following chemical formulas (1) to (22).

[0134] (g is an integer between 2 and 5.)

[0135]

[0136] As polymerizable liquid crystal compounds different from those of the present disclosure, they should be appropriately selected so that when the phase difference value is measured, Re(450) / Re(550) is within the range of 0.60 or more and less than 1.05. As polymerizable liquid crystal compounds different from those of the present disclosure, Re(450) / Re(550) can be selected from those of 0.60 or more and less than 1.20, but it is preferable to select from those of 0.80 or more and less than 1.20, and even more preferable to select from those of 0.90 or more and less than 1.20. The phase difference value here is measured in the same manner as the phase difference value test method described above.

[0137] Furthermore, in this embodiment, it is preferable that a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound of this disclosure be dissolved in at least 20% by mass or more of 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 polymerizable composition. Improved solvent solubility of the polymerizable composition is preferable because it facilitates the formation of a uniform coating film when forming a coating film using the polymerizable composition, reduces the load on the manufacturing process and equipment for drying the solvent, expands the range of usable substrates, and broadens the liquid crystal phase transition temperature of the composition, widening the process margin during orientation and resulting in more uniform and better orientation.

[0138] In this embodiment, polymerizable liquid crystal compounds different from the polymerizable liquid crystal compounds of this disclosure can be used individually or in combination of two or more. In this embodiment, the content ratio of polymerizable liquid crystal compounds different from the polymerizable liquid crystal compounds of this disclosure is not limited and can be adjusted as appropriate to adjust the desired phase difference, etc., but is preferably 7 parts by mass or more and 49.9 parts by mass or less, 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, per 100 parts by mass of solid content of the polymerizable composition. Furthermore, the content ratio of polymerizable liquid crystal compounds different from the polymerizable liquid crystal compounds of this disclosure can be adjusted as appropriate to adjust the desired phase difference, etc., but is preferably 50 parts by mass or less, more preferably 45 parts by mass or less, and may be 40 parts by mass or less, per 100 parts by mass of the total amount of polymerizable liquid crystal compounds of this disclosure and polymerizable liquid crystal compounds different from the polymerizable liquid crystal compounds of this disclosure.

[0139] 4. Other Components The polymerizable composition of this embodiment may contain other components as long as they do not impair the effect. Specifically, other components may include leveling agents, antioxidants, light stabilizers, and solvents from the viewpoint of coating properties. It may also contain polymerizable compounds that do not exhibit liquid crystalline properties on their own but can be used together with the polymerizable liquid crystal compound of this disclosure to adjust the phase difference, inverse wavelength dispersion, phase transition temperature, hardness, and durability. These can be appropriately selected from conventionally known materials.

[0140] To improve the hardness and durability of the coating film, it is preferable to further include a polymerizable compound having two or more polymerizable functional groups in one molecule. In addition to the polymerizable liquid crystal compounds mentioned above, polymerizable compounds that do not have liquid crystal properties can also be used as polymerizable compounds having two or more polymerizable functional groups in one molecule. Polymerizable compounds having two or more polymerizable functional groups in one molecule can also be so-called polyfunctional monomers, for example, 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, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentyl glycol di(meth)acrylate, dimethylolpropane tri(meth)acrylate, dipentylpropane tetra(meth)acrylate, dipentylpropane Examples include pentaerythritol penta(meth)acrylate, tripentaerythritol octa(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, isocyanuric acid tri(meth)acrylate, isocyanuric acid di(meth)acrylate, polyester tri(meth)acrylate, polyester di(meth)acrylate, bisphenol di(meth)acrylate, diglycerin tetra(meth)acrylate, adamantyl di(meth)acrylate, isoboronyl di(meth)acrylate, dicyclopentane di(meth)acrylate, tricyclodecane di(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, and modified versions of these with PO, EO, etc. Polymerizable compounds having three or more polymerizable functional groups in one molecule, such as pentaerythritol triacrylate (PETA), dipentaerythritol hexaacrylate (DPHA), pentaerythritol tetraacrylate (PETTA), dipentaerythritol pentaacrylate (DPPA), and trimethylolpropane triacrylate (TMPTA), are preferred because the crosslinking reaction proceeds and the durability of the coating film is improved.In this embodiment, when a polymerizable compound that does not have liquid crystalline properties is used, its content 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, per 100 parts by mass of solids of the polymerizable composition. In this embodiment, as a polymerizable compound different from the polymerizable liquid crystalline compound of this disclosure, it is preferable to dissolve it 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. This is because it improves the solvent solubility of the polymerizable composition, makes it easier to form a uniform coating film when forming a coating film using the polymerizable composition, reduces the load on the manufacturing process and manufacturing equipment for drying the solvent, and expands the range of usable substrates.

[0141] As a leveling agent, it is preferable to use a fluorine-based or silicone-based leveling agent. Specific examples of leveling agents include, for example, the Megafac series manufactured by DIC Corporation, described in Japanese Patent Application Publication No. 2010-122325, the TSF series manufactured by Momentive Performance Materials Japan, and the Futergent series manufactured by Neos Corporation. In this embodiment, when a leveling agent is used, its content is preferably 0.001 parts by mass or more and 5 parts by mass or less per 100 parts by mass of solid content of the polymerizable composition.

[0142] The polymerizable composition of this embodiment may contain a solvent as needed, from the viewpoint of coating properties. The solvent can be appropriately selected from conventionally known solvents that can dissolve or disperse each component 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); alkyl halogenated 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, the solvent can be used alone or in combination of two or more to form a mixed solvent.

[0143] The polymerizable composition of this embodiment is suitable for various applications due to its good orientation properties. As a liquid crystal composition, the polymerizable composition of this embodiment is suitable for applications such as phase difference films and various optical components, as described later.

[0144] C. Polymers The polymers of the present disclosure are obtained by polymerizing the polymerizable liquid crystal compound or polymerizable composition of the present disclosure. The polymerization method can be appropriately selected according to the polymerizable functional groups contained in the polymerizable liquid crystal compound of the present disclosure. Polymers obtained by polymerizing the polymerizable liquid crystal compound or polymerizable composition of the present disclosure without orientation can be used, for example, as light scattering plates, depolarizing plates, and moiré fringe prevention plates. Polymers obtained by polymerizing the polymerizable liquid crystal compound or polymerizable composition of the present disclosure after orientation have optical anisotropy and are suitably used in phase difference films and various optical component applications described later.

[0145] D. Phase Difference Film The phase difference film of this disclosure is a phase difference film having a phase difference layer, wherein the phase difference layer is made of a cured product of the polymerizable composition of this disclosure. In the above embodiment, since the phase difference layer of the phase difference film is made of a cured product of the polymerizable composition, it has a phase difference layer that exhibits inverse wavelength dispersion and flat wavelength dispersion. Because the polymerizable liquid crystal compound of this disclosure contained in the polymerizable composition has good solvent solubility, it is easy to prepare a polymerizable composition (ink) containing a solvent suitable for the production of the phase difference layer, so that crystal precipitation is less likely to occur during the production of the phase difference layer, and it is possible to form a phase difference layer that satisfies the required physical properties. Because the polymerizable liquid crystal compound has good solvent solubility, a solvent suitable for the manufacturing process can be used, so that solvent is less likely to remain in the phase difference layer, and the stability of the phase difference layer is also increased.

[0146] The layer structure of the phase difference film will be explained with reference to the figures. Figures 1 to 3 each show one embodiment of the phase difference film of the present disclosure. One embodiment of the phase difference film 10 shown in the example of Figure 1 is a phase difference film in which an alignment film 3 and a phase difference layer 1 are laminated in that order on a substrate 2. One embodiment of the phase difference film 10 shown in the example of Figure 2 is a phase difference film consisting only of a phase difference layer 1. Another embodiment of the phase difference film 10 shown in the example of Figure 3 has the phase difference layer 1 directly formed on the substrate 2'. The phase difference film shown in the example of Figure 3 may be provided with means for exerting an orientation restricting force on the surface of the substrate 2' on the side of the phase difference layer 1. Here, in the present disclosure, orientation restricting force refers to the effect of aligning the oriented components in the phase difference layer in a specific direction.

[0147] 1. Phase Difference Layer The phase difference layer 1 of the embodiment of this disclosure consists of a cured product of the polymerizable composition of this disclosure containing the polymerizable liquid crystal compound of this disclosure. Here, the polymerizable liquid crystal compound and the polymerizable composition of this disclosure may be the same as those described in the embodiment of this disclosure, so their description is omitted here.

[0148] Preferably, the phase difference layer is cured in a state in which the oriented main chain portion of the polymerizable liquid crystal compound of the present disclosure, and any further polymerizable liquid crystal compounds, are substantially horizontally oriented with respect to the film surface. The cured product of the polymerizable composition of the embodiment of the present disclosure includes a structure in which at least a portion of the polymerizable functional groups of the polymerizable compound are polymerized. Because such a structure in which at least a portion of the polymerizable functional groups of the polymerizable compound is included, the phase difference layer of this embodiment is a phase difference layer with improved durability.

[0149] Phase difference can be measured using a phase difference measuring device (KOBRA series, manufactured by Oji Instruments Co., Ltd.). By irradiating the phase difference layer surface perpendicularly or obliquely with the measurement light, the anisotropy that increases or decreases the phase difference of the phase difference layer, as well as the degree of orientation in the vertical (thickness) direction of the liquid crystal, can be confirmed from the chart of the optical phase difference and the angle of incidence of the measurement light.

[0150] Furthermore, it can be confirmed that the phase difference layer contains a structure in which at least a portion of the polymerizable functional groups of the polymerizable liquid crystal compound contained in the polymerizable composition of the present disclosure, or any other polymerizable liquid crystal compounds that may be included, are polymerized by sampling and analyzing the material from the phase difference layer. NMR, IR, GC-MS, XPS, TOF-SIMS, and combinations thereof can be applied as analytical methods.

[0151] The phase difference layer may contain other components such as photopolymerization initiators, leveling agents, antioxidants, and photostabilizers. Components that may decompose completely when irradiated with light to react the polymerizable functional groups of the polymerizable liquid crystal compound, such as photopolymerization initiators, may not be included in the phase difference layer.

[0152] The thickness of the phase difference layer can be set appropriately depending on the application. For example, when the phase difference film of this disclosure is used to make a broadband quarter-wave plate, the film thickness of the resulting phase difference film should be adjusted so that the Re(550) of the resulting phase difference film is 113 nm to 163 nm, preferably 135 nm to 140 nm, and particularly preferably about 137.5 nm. When it is used to make a half-wave plate, the film thickness should be adjusted so that the Re(550) of the resulting optical film is 250 nm to 300 nm, preferably 273 nm to 277 nm, and particularly preferably about 275 nm.

[0153] Furthermore, the film thickness can be adjusted to obtain the desired phase difference by appropriately adjusting the amount of polymerizable composition applied and the concentration of the polymerizable liquid crystal compound. The phase difference value (retardation value, Re(λ)) of the resulting phase difference layer is determined by the following formula, so in order to obtain the desired Re(λ), the film thickness d should be adjusted. Re(λ) = d × Δn(λ) (In the formula, Re(λ) represents the phase difference value at a wavelength of λnm, d represents the film thickness, and Δn(λ) represents the birefringence at a wavelength of λnm.) The thickness of the phase difference layer may be 0.1 μm or more and 5 μm or less, or 0.5 μm or more and 3 μm or less.

[0154] The wavelength dispersion characteristics of the phase difference film of this disclosure can be arbitrarily determined by the content of the polymerizable liquid crystal compound of this disclosure and other polymerizable liquid crystal compounds that may be contained in the phase difference layer. Furthermore, in order to approach ideal wavelength dispersion, when a polymerizable composition containing only the polymerizable liquid crystal compound of this disclosure and a photopolymerization initiator is prepared by the method shown in Example 1 below and a cured film (phase difference layer) is formed, it is preferable that Re(450) / Re(550) is in the range of 0.60 or more and less than 1.05, more preferably in the range of 0.60 or more and less than 1.00, even more preferably in the range of 0.78 or more and less than 0.95, and even more preferably in the range of 0.80 or more and less than 0.93. Furthermore, it is preferable that Re(650) / Re(550) is greater than 1.00, and even more preferably in the range of 1.02 or more and 1.10 or less.

[0155] 2. Alignment Film In this specification, an alignment film refers to a layer for aligning the liquid crystalline components contained in the phase difference layer in a certain direction. As the alignment film used in the embodiments of this disclosure, it is preferable to use a horizontal alignment film because the polymerizable composition of the embodiments of this disclosure is easily aligned horizontally. The horizontal alignment film is a film that, when provided as a coating film, aligns the long axis of the mesogen of the liquid crystalline components contained in the phase difference layer substantially horizontally with respect to the horizontal alignment film surface (film surface). As the horizontal alignment film, conventionally known films can be appropriately selected and used. For example, an alignment film to which alignment restricting force has been imparted by a rubbing method, a photo-alignment method, a shaping method, etc., can be cited. Among these, a horizontal alignment film to which alignment restricting force has been imparted by a rubbing method, a photo-alignment method, or a shaping method is preferred.

[0156] When orientation-regulating force is imparted by the rubbing method, the horizontal orientation film uses a polymer that exhibits orientation-regulating force through rubbing. Examples of such polymers include polyvinyl alcohol, polyimide, polyamide, and their derivatives, with polyvinyl alcohol being preferred.

[0157] The method for forming the horizontally aligned film by the rubbing method can be appropriately selected from conventionally known methods. For example, after forming a coating film containing the polymer on the transparent substrate, the horizontally aligned film can be obtained by rubbing it using a known rubbing roller or the like.

[0158] When forming a horizontally aligned film by photo-alignment, a photo-aligning composition containing a photo-aligning material that exhibits orientation-regulating force upon irradiation with polarized light is used as the alignment film composition. The photo-aligning material may be a photo-dimerizable material or a photo-isomerizable material. Specifically, examples include polymers having cinnamate, coumarin, benzylidenephthalimidine, benzylideneacetophenone, diphenylacetylene, stilbazole, uracil, quinolinone, maleimide, or cinnamyridene acetate derivatives. Among these, polymers having at least one of cinnamate and coumarin, and their derivatives, are preferred. Specific examples of such photodimerizing materials include, for example, the compounds described in Japanese Patent Publication No. 9-118717, Japanese Patent Publication No. 10-506420, Japanese Patent Publication No. 2003-505561, WO2010 / 150748, and Japanese Patent Publication No. 2015-151548.

[0159] The method for forming a photo-aligned film by the photo-alignment method can be appropriately selected from conventionally known methods. For example, a photo-aligned film can be obtained by uniformly coating the photo-alignable composition onto the transparent substrate, irradiating it with polarized light, and then irradiating the entire surface of the coating with light.

[0160] Furthermore, when forming a horizontally aligned film by a molding method, the composition for the alignment film can be appropriately selected from those capable of molding the desired fine uneven shape. For example, a molding composition containing an ultraviolet-curable resin, a thermosetting resin, an electron beam-curable resin, etc., can be used. Among these, an ultraviolet-curable resin is preferred because it facilitates the formation of the alignment film. Specific examples of ultraviolet-curable resins include, for example, the polymerizable monomers and oligomers mentioned above, as well as urethane acrylate, epoxy acrylate, polyester acrylate, polyether acrylate, melamine acrylate, etc., which can be used individually or in combination of two or more.

[0161] The method for forming the horizontally aligned film by the molding method can be appropriately selected from conventionally known methods. For example, by uniformly applying the molding composition onto the transparent substrate, bringing the coating into contact with a mold having a desired fine uneven shape, applying pressure, and irradiating with ultraviolet light, an oriented film with the desired fine uneven shape can be obtained.

[0162] Furthermore, the horizontal alignment film may be one which has been patterned and in which parts having alignment properties are arranged in a pattern. Known horizontal alignment films can be used, and are not particularly limited, but examples include rubbing alignment films that have been patterned by mask rubbing, photoalignment films that have been patterned by mask exposure, and alignment films that have been patterned by printing or the like.

[0163] The thickness of the horizontal alignment film can be set as appropriate, as long as it can orient the polymerizable rod-shaped liquid crystal compound horizontally, and is not particularly limited, but is usually 1 nm or more, preferably 60 nm or more, and from the viewpoint of thin film formation, it is 15 μm or less, preferably 10 μm or less, more preferably 1 μm or less, and even more preferably 0.3 μm or less.

[0164] 3. Substrate In this embodiment, the substrate can be a glass substrate, a metal foil, a resin substrate, etc. Among these, the substrate is preferably transparent and can be appropriately selected from conventionally known transparent substrates. Examples of transparent substrates include glass substrates, acetylcellulose resins such as triacetylcellulose, 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, and transparent resin substrates formed using resins such as polyethersulfone, polycarbonate, polysulfone, polyether, polyetherketone, acronitrile, methacrylonitrile, cycloolefin polymer, and cycloolefin copolymer.

[0165] The transparent substrate described above preferably has a transmittance of 80% or more in the visible light region, and more preferably 90% or more. Here, the transmittance of the transparent substrate can be measured according to JIS K7361-1:1997 (Plastics - Test method for total light transmittance of transparent materials).

[0166] Furthermore, when forming a phase difference layer using a roll-to-roll method, the transparent substrate is preferably a flexible material that can be wound into a roll. Examples of such flexible materials include cellulose derivatives, norbornene polymers, cycloolefin polymers, polymethyl methacrylate, polyvinyl alcohol, polyimide, polyarylate, polyethylene terephthalate, polysulfone, polyethersulfone, amorphous polyolefin, modified acrylic polymer, polystyrene, epoxy resin, polycarbonate, and polyesters. In this embodiment, it is preferable to use cellulose derivatives or polyethylene terephthalate. Cellulose derivatives are particularly excellent in optical isotropy, and therefore can be made to have excellent optical properties. Polyethylene terephthalate is also preferred because it has high transparency and excellent mechanical properties.

[0167] The thickness of the substrate used in this embodiment is not particularly limited as long as it can provide the necessary self-supporting properties depending on the application of the phase difference film, but is usually in the range of 10 μm to 1000 μm. In particular, the thickness of the substrate is preferably in the range of 25 μm to 125 μm, and more preferably in the range of 30 μm to 100 μm. If the thickness is greater than the above range, for example, when a long phase difference film is formed and then cut to form a single-sheet phase difference film, the amount of processing waste may increase or the cutting blade may wear out more quickly.

[0168] The substrate used in this embodiment is not limited to a single layer configuration, but may have a configuration in which multiple layers are laminated. In the case of a configuration with multiple laminated layers, layers of the same composition may be laminated, or multiple layers of different compositions may be laminated. For example, if the alignment film used in this embodiment contains an ultraviolet-curable resin, a primer layer may be formed on the substrate to improve the adhesion between the transparent substrate and the ultraviolet-curable resin. This primer layer may have adhesion to both the substrate and the ultraviolet-curable resin, be transparent in visible light, and allow ultraviolet light to pass through. For example, vinyl chloride / vinyl acetate copolymers, urethane-based primers, etc., can be appropriately selected and used.

[0169] Furthermore, an anchor coat layer may be laminated on the substrate. The strength of the substrate can be improved by this anchor coat layer. As the anchor coat material, metal alkoxides, particularly metal silicon alkoxide sols, can be used. Metal alkoxides are usually used as alcohol-based solutions. Since the anchor coat layer needs to be a uniform and flexible film, the thickness of the anchor coat layer is preferably 0.04 μm to 2 μm, and more preferably 0.05 μm to 0.2 μm. When the substrate has an anchor coat layer, the adhesion between the substrate and the anchor coat layer may be improved by further laminating a binder layer between the substrate and the anchor coat layer, or by incorporating a material that strengthens adhesion to the substrate into the anchor coat layer. The binder material used to form the binder layer can be any material that can improve the adhesion between the substrate and the anchor coat layer without particular limitations. Examples of binder materials include silane coupling agents, titanium coupling agents, zirconium coupling agents, and the like.

[0170] 4. Method for Manufacturing a Phase Difference Film The method for manufacturing a phase difference film according to the embodiment of the present disclosure comprises the steps of forming a phase difference layer by: forming a film of the polymerizable composition according to the embodiment of the present disclosure (film formation step); oriented at least the polymerizable compound in the formed polymerizable composition (orientation step); and polymerizing at least the polymerizable compound after the orientation step (polymerization step). The polymerizable composition can be the same as that described in "B. Polymerizable Composition" above, so its description is omitted here.

[0171] (1) Film formation process of polymerizable composition A polymerizable composition is uniformly applied to a support to form a film. As described above, the film thickness is adjusted to give a desired phase difference by appropriately adjusting the amount of polymerizable composition applied and the concentration of the polymerizable liquid crystal compound. The support here may be the substrate, or it may be the alignment film of the substrate equipped with the alignment film.

[0172] The coating method can be any method that can accurately form a film of the desired thickness, and can be selected as appropriate. Examples include gravure coating, reverse coating, knife coating, dip coating, spray coating, air knife coating, spin coating, roll coating, printing, immersion and pull-up, curtain coating, die coating, casting, bar coating, extrusion coating, and E-type coating methods.

[0173] (2) Orientation step Next, the polymerizable liquid crystal compound in the polymerizable composition that has been filmed is at least oriented. The polymerizable liquid crystal compound in the polymerizable composition that has been filmed is heated to a temperature at which orientation is possible. This heat treatment allows the main chain portion having orientation properties of the polymerizable liquid crystal compound of the present disclosure and, if necessary, polymerizable liquid crystal compounds other than the polymerizable compound of the present disclosure that are further contained to be oriented and dried, and the oriented state can be fixed. The temperature at which orientation is possible varies depending on each substance in the polymerizable composition, so it is necessary to adjust it as appropriate. For example, it is preferable to perform the heating in the range of 60°C to 200°C, and more preferably in the range of 60°C to 100°C. Known heating and drying means can be appropriately selected and used as the heating means. The heating time can be appropriately selected, but for example, it is selected in the range of 10 seconds to 2 hours, preferably 20 seconds to 30 minutes.

[0174] (3) Polymerization step After the orientation step, at least the polymerizable compound is polymerized. In the orientation step, the polymerizable compound can be polymerized by, for example, light irradiation of the coating film fixed in a state in which the orientation of the polymerizable compound and any further polymerizable liquid crystal compounds is maintained, thereby obtaining a phase difference layer made of a cured product of the polymerizable composition. Ultraviolet irradiation is preferably used as the light irradiation. Ultraviolet irradiation can be performed using ultraviolet light emitted from light rays such as ultra-high pressure mercury lamps, high pressure mercury lamps, low pressure mercury lamps, carbon arcs, xenon arcs, and metal halide lamps. The irradiation amount of the energy source can be appropriately selected, for example, 10 mJ / cm as the integrated exposure amount at an ultraviolet wavelength of 365 nm. ２ More than 10000mJ / cm ２ The following range is preferable.

[0175] 5. Applications The phase difference film of this disclosure is suitably used, for example, as an anti-reflective quarter-wave plate, and is suitably used as an optical component for various display devices as described later.

[0176] E. Transfer Laminate The transfer laminate of the present disclosure comprises a phase difference layer and a support that removably supports the phase difference layer, wherein the phase difference layer is made of a cured product of the polymerizable composition of the present disclosure, and is a transfer laminate for transferring a phase difference layer.

[0177] The transfer laminate of this embodiment has excellent optical properties because the phase difference layer is made of a cured product of the polymerizable composition, thereby suppressing the precipitation of polymerizable compounds. The transfer laminate of this embodiment allows for the transfer of the phase difference layer of this disclosure, for example, a thin film without a substrate, to any other optical component. The transfer laminate of this embodiment provides, for example, a phase difference film 10 consisting only of the phase difference layer 1 shown in the example of Figure 2, or a phase difference film consisting of a laminate 26 in which an alignment film 23 and a phase difference layer 21 are laminated without a substrate, as shown in the example of Figure 5. In other words, an alignment film or the like may be laminated on the phase difference layer used for transfer of the transfer laminate, as long as the phase difference layer is at least peelable. The configuration of such a transfer laminate will be described below, but the polymerizable composition of the embodiment of this disclosure has been described above, so its description will be omitted here.

[0178] The layer structure of the transfer laminate will be described with reference to the figures. Figures 4 and 5 show one embodiment of the transfer laminate of the present disclosure, respectively. One embodiment of the transfer laminate 20 shown in the example of Figure 4 is a transfer laminate in which an alignment film 13 and a phase difference layer 11 are laminated in this order on a second substrate 12, serving as a support 15 that peels off the phase difference layer and a phase difference layer 16 for transfer. In the transfer laminate shown in the example of Figure 4, the peel strength between the second substrate 12 and the alignment film 13 is greater than the peel strength between the alignment film 13 and the phase difference layer 11, so that the phase difference layer 11 (16) can be peeled off at the interface 17 between the alignment film and the phase difference layer and transferred. One embodiment of the transfer laminate 30 shown in the example of Figure 5 is a transfer laminate in which an alignment film 23 and a phase difference layer 21 are laminated in this order on a second substrate 22, serving as a support 25 that peels off the phase difference layer and a phase difference layer 26 for transfer. In the transfer laminate shown in the example of Figure 5, the peel strength between the second substrate 22 and the alignment film 23 is lower than the peel strength between the alignment film 23 and the phase difference layer 21. As a result, the phase difference layer 26, which is the phase difference layer 21 and the alignment film 23, is peeled off at the interface 27 between the second substrate 22 and the alignment film 23, and the phase difference layer 26 that can be transferred is an example of a transfer laminate.

[0179] For example, whether the delamination strength between the second substrate and the orientation film is greater or less than the delamination strength between the orientation film and the phase difference layer can be determined by delaminating the phase difference layer and observing which interface the delamination occurs at. The interface at which the delamination occurs can be analyzed, for example, by IR.

[0180] Furthermore, one embodiment of the transfer laminate 40 shown in the example of Figure 6 is a transfer laminate in which a phase difference layer 31 is laminated on a second substrate 32 as a support 35 that resiliently supports the phase difference layer, and a phase difference layer 36 for transfer, in that order.

[0181] The following describes this embodiment, but the phase difference layer can be the same as the phase layer described in "D. Phase Difference Film" above, so its description will be omitted here. Also, the alignment film and substrate can be the same as the alignment film and substrate described in "D. Phase Difference Film" above, but the following methods can be used to adjust the peel strength.

[0182] To obtain the transfer laminate 20 shown in the example in Figure 4, if the peel strength between the second substrate 12 and the alignment film 13 is greater than the peel strength between the alignment film 13 and the phase difference layer 11, for example, a method can be used in which the solvent contained in the alignment film forming composition is capable of dissolving the second substrate. Preferably, a resin substrate is used as the second substrate, and surface treatment to improve adhesion to the substrate surface may also be performed. In such a case, the adhesion between the resin substrate and the alignment film can be improved. Furthermore, in order to reduce the peel strength between the alignment film and the phase difference layer so that the peel strength between the substrate and the alignment film is greater than the peel strength between the alignment film and the phase difference layer, it is also preferable to make the solvent resistance of the alignment film relatively high. When the solvent resistance of the alignment film is relatively high, when the polymerizable composition is applied to the alignment film to form the phase difference layer, the alignment film becomes less likely to dissolve in the solvent in the polymerizable composition, thus reducing the adhesion between the alignment film and the phase difference layer.

[0183] On the other hand, in order to obtain the transfer laminate 30 shown in the example of Figure 5, the peel strength between the second substrate 22 and the alignment film 23 may be made smaller than the peel strength between the alignment film 23 and the phase difference layer 21. For example, the surface of the substrate may be treated with a release agent, or a release layer may be formed. This improves the peelability of the substrate, and the peel strength between the substrate and the alignment layer can be made smaller than the peel strength between the alignment layer and the phase difference layer. Examples of release agents include surface treatments such as fluorine treatment and silicone treatment. Examples of materials for the release layer include fluorine-based release agents, silicone-based release agents, and wax-based release agents. Examples of methods for forming the release layer include applying the release agent by coating methods such as dip coating, spray coating, and roll coating. Also, in order to obtain the transfer laminate 40 shown in the example of Figure 6, the surface of the substrate may be treated with a release agent, or a release layer may be formed, as necessary.

[0184] The substrate used in the transfer laminate may or may not be flexible, but it is preferable that it be flexible in order to make it easier to peel off. The thickness of the substrate used in the transfer laminate is usually in the range of 20 μm to 200 μm in the case of a sheet of the above material, taking into account a balance between sufficient self-supporting strength and flexibility that can be adapted to the manufacturing and transfer process of the transfer laminate of this embodiment.

[0185] The phase difference layer that can be provided from the transfer laminate of this disclosure is suitably used for the same purposes as the phase difference film, for example, suitably used as an anti-reflective quarter-wave plate, can be transferred to optical components for various display devices, and is suitably used to provide thin-film optical components.

[0186] F. Optical component The optical component of the present disclosure comprises a polarizing plate on the phase difference film of the present disclosure.

[0187] The optical member of this embodiment will be described with reference to the figures. Figure 7 is a schematic cross-sectional view showing one embodiment of the optical member. In the example of the optical member 60 in Figure 7, a polarizing plate 50 is arranged on the phase difference film 10 of the present disclosure. An adhesive layer may be provided between the phase difference film 10 and the polarizing plate 50 as needed (not shown).

[0188] In this embodiment, the polarizing plate is a plate-like material that allows only light vibrating in a specific direction to pass through, and can be appropriately selected from conventionally known polarizing plates. For example, polyvinyl alcohol film, polyvinyl formal film, polyvinyl acetal film, ethylene-vinyl acetate copolymer saponified film, etc., dyed with iodine or dye and stretched can be used. In addition, in this embodiment, the adhesive or bonding agent for the adhesive layer can be appropriately selected from conventionally known ones, and any bonding form such as pressure-sensitive adhesives, two-component curing adhesives, ultraviolet curing adhesives, thermosetting adhesives, and heat-melt adhesives can be suitably used.

[0189] The optical component of this embodiment may further include, in addition to the polarizing plate, other layers that are present in known optical components. Examples of such other layers include, but are not limited to, other phase difference layers different from the phase difference layer of this embodiment, as well as anti-reflective layers, diffusion layers, anti-glare layers, anti-static layers, protective films, etc.

[0190] The optical element of this embodiment can be suitably used, for example, as an optical element that suppresses external light reflection, or as a wide-viewing-angle polarizing plate for various display devices.

[0191] The method for manufacturing the optical component of this disclosure is not particularly limited, and any method of laminating a polarizing plate on the phase difference film of this disclosure can be appropriately selected and used. For example, a manufacturing method in which a polarizing plate is laminated on the phase difference film of this disclosure via an adhesive layer or bonding layer can be used.

[0192] Furthermore, a method for manufacturing an optical member according to one embodiment of the present disclosure includes a transfer laminate preparation step of preparing the transfer laminate of the present disclosure, a transfer step of placing a transfer target including at least a polarizing plate and the phase difference layer of the transfer laminate facing each other and transferring the transfer laminate onto the transfer target, and a peeling step of peeling the support from the transfer laminate transferred onto the transfer target.

[0193] According to the method for manufacturing an optical member of one embodiment of the present disclosure using the transfer laminate, an optical member can be obtained that comprises a polarizing plate and only the phase difference layer of the phase difference film of the present disclosure. The transfer laminate used in the method for manufacturing an optical member of one embodiment of the present disclosure can be the same as that described in "E. Transfer Laminate" above, so its description is omitted here. In addition, the object to be transferred used in the method for manufacturing an optical member of one embodiment of the present disclosure typically includes an adhesive layer and a polarizing plate, but is not limited to these, and may further include layers similar to the other layers that the optical member of one embodiment of the present disclosure may have.

[0194] G. Display Device The display device according to this disclosure is characterized by comprising the phase difference film of the above embodiment or the optical member of the above embodiment. Examples of display devices include, but are not limited to, light-emitting display devices and liquid crystal display devices.

[0195] In particular, because it includes the phase difference film or optical member of this embodiment, it has the effect of improving the viewing angle while suppressing external light reflection in light-emitting devices such as organic light-emitting devices that have a transparent electrode layer, a light-emitting layer, and an electrode layer in that order.

[0196] An example of a light-emitting display device, which is one embodiment, will be described with reference to the figures. Figure 8 is a schematic cross-sectional view showing one embodiment of an optical member. In the example of the organic light-emitting display device 100 in Figure 8, a polarizing plate 50 is arranged on the light-emitting surface side of the phase difference film 10, and on the opposite side, a transparent electrode layer 71, a light-emitting layer 72, and an electrode layer 73 are arranged in this order. As the light-emitting layer 72, for example, a configuration in which a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection layer are stacked in the order from the transparent electrode layer 71 side can be cited. 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 any known components as appropriate. The light-emitting display device manufactured in this way can be applied to both passively driven organic EL displays and actively driven organic EL displays, for example. Note that the display device of this embodiment is not limited to the above configuration, and can be any known configuration selected as appropriate.

[0197] Examples and comparative examples are shown below to further illustrate this disclosure. Each compound produced was prepared using JEOL JNM-LA400WB manufactured by JEOL Ltd. １ The chemical structure was confirmed by 1H NMR measurement. Furthermore, the phase transition temperature of each fabricated compound was confirmed during heating by texture observation using a polarizing microscope (Olympus BX51) equipped with a temperature control stage. C represents the crystalline phase, N represents the nematic phase, and I represents the isotropic liquid phase. For example, "C 130 N 180 I" indicates that the crystalline phase transitioned to the nematic phase at 130°C, and the nematic phase transitioned to the isotropic liquid phase at 180°C.

[0198] In this disclosure, unless otherwise specified, all parameters shall be values ​​measured at a temperature of 25°C ± 2°C and a relative humidity of 40% to 65%. Furthermore, before starting each measurement, the target sample shall be exposed to the above atmosphere for at least 30 minutes before measurement and evaluation.

[0199] Furthermore, in this disclosure, unless otherwise specified, the orientation and in-plane phase difference Re in the evaluation items below refer to the average value of nine measured values. The nine measurement points are determined by drawing lines that divide the area inside the margin (1 cm from the outer edge of the measurement sample) into four equal parts in the vertical and horizontal directions, and using these nine points as the measurement centers. If the measurement sample is a rectangle, the area inside the margin (1 cm from the outer edge of the rectangle) is used as the margin, and measurements are taken at the nine points at the intersections of the lines that divide the area inside the margin into four equal parts in the vertical and horizontal directions, and the average value is calculated. If the measurement sample is a shape other than a rectangle, such as a circle, ellipse, triangle, or pentagon, draw a rectangle with the largest area that can be inscribed in this shape, and perform nine measurements on this rectangle using the method described above. If at least one side of the rectangle of the measurement sample is 5 mm or less, any seven locations inside the rectangle will be used as the measurement centers, and the average value of the five measurements obtained by excluding the maximum and minimum values ​​from the seven measurements will be used.

[0200] [Production Example 1: Production of Polymerizable Liquid Crystal Compound 1 represented by Formula (1-1)] 2-aminobenzene-1,4-diol (10 g), acetic acid (100 mL), and concentrated hydrochloric acid (100 mL) were added to a 3 L flask equipped with a stirrer and stirred. After cooling to 5°C, 0.5 M aqueous sodium nitrite solution (800 mL) was added dropwise over 3 hours, and tin(II) chloride dihydrate (7.5 g) was added and stirring continued for 3 hours. Potassium carbonate was added to the reaction solution to adjust the pH to 7, then 200 mL of methylene chloride was added and stirred for 15 minutes. After standing, the aqueous layer was removed from the flask. Next, 5 g of sodium sulfate, ethyl pyruvate (9.3 g), and sodium acetate (9.8 g) were added to the flask and stirred at room temperature for 17 hours. The resulting reaction solution was concentrated and purified by silica gel columnography to obtain the intermediate represented by Formula (1-1-1) (3 g).

[0201] Cyclohexane-1,4-dicarboxylic acid=hydrogen=4-[6-(acryloyloxy)hexyloxy]phenyl (an intermediate represented by formula (1-1-2)) was synthesized by referring to the method described in Japanese Patent Application Publication No. 2021-1150.

[0202] In a 100 mL flask equipped with a stirrer, 3 g of the intermediate represented by formula (1-1-1), 13 g of cyclohexane-1,4-dicarboxylic acid=hydrogen=4-[6-(acryloyloxy)hexyloxy]phenyl (intermediate represented by formula (1-1-2)), 0.05 g of dimethylaminopyridine, and 15 mL of methylene chloride were added and stirred. After cooling to 5°C, 4 g of N,N'-diisopropylcarbodiimide (manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over 10 minutes, and stirring was continued for another hour. 50 mL of methanol was added to the reaction mixture, and the precipitated white solid was collected by filtration to obtain the target polymerizable liquid crystal compound 1 represented by formula (1-1) (4 g).

[0203] Phase transition temperature (when heating): C 97 N 219 I １ 1H NMR (CDCl ３ (δ ppm) :7.52 (d, 1H), 7.35 (d, 1H), 7.29 (d, 1H), 6.98-6.96 (m, 4H), 6.89-6.87 (m, 4H), 6.38-6.35 (m, 2H), 6.35 (s, 1H), 6.16-6.09 (m, 2H), 5.81 (d, 2H) , 4.23 (q, 2H), 4.17 (t, 4H), 3.94 (t, 4H), 2.90 (s, 3H), 2.72-2.58 (m, 4H) , 2.33-2.29 (m, 8H), 1.81-1.68 (m, 16H), 1.56-1.41 (m, 8H), 1.43 (t, 3H)

[0204]

[0205] [Production Example 2: Production of Polymerizable Liquid Crystal Compound 2 represented by Formula (1-2)] The process was carried out in the same manner as in Production Example 1, except that 2-methylpropyl 2-oxopropanoate (11.5 g, manufactured by Aurora) was used instead of ethyl pyruvate (9.3 g) to obtain 4 g of the compound represented by formula (1-2-1). The intermediate represented by formula (1-1-2) was reacted with the compound represented by formula (1-1-2) in the same manner as in Production Example 1, except that the intermediate represented by formula (1-1-1) (3 g) was used instead of the compound represented by formula (1-2-1) (4 g) to obtain polymerizable liquid crystal compound 2 represented by formula (1-2) (4.2 g).

[0206] Phase transition temperature (when heating): C 87 N 210 I １ 1H NMR (CDCl ３ ; δppm) :7.50 (d, 1H), 7.32 (d, 1H), 7.28 (d, 1H), 6.98-6.96 (m, 4H), 6.89-6.86 (m, 4 H), 6.38-6.35 (m, 2H), 6.35 (s, 1H), 6.16-6.10 (m, 2H), 5.81 (d, 2H), 4.17 (t, 4H), 4.03 (q, 2H), 3.94 (t, 4H), 2.90 (s, 3H), 2.72-2.58 (m, 4H), 2.33-2.29 (m , 8H), 2.01-1.88 (m, 1H), 1.81-1.68 (m, 16H), 1.56-1.41 (m, 8H), 0.89 (d, 6H)

[0207]

[0208] [Production Example 3: Production of Polymerizable Liquid Crystal Compound 3 represented by Formula (1-3)] In the same manner as in Production Example 1, except that butyl 2-oxopropanoate (11.5 g, manufactured by Aurora) was used instead of ethyl pyruvate (9.3 g), 4 g of the compound represented by formula (1-3-1) was obtained. In the same manner as in Production Example 1, except that the compound represented by formula (1-3-1) (4 g) was used instead of the intermediate represented by formula (1-1-1) (3 g), the intermediate represented by formula (1-1-2) was reacted with the compound represented by formula (1-1-2) to obtain polymerizable liquid crystal compound 3 (4 g) represented by formula (1-3).

[0209] Phase transition temperature (when heating): C 90 N 200 I １ 1H NMR (CDCl ３ (δ ppm) :7.52 (d, 1H), 7.35 (d, 1H), 7.28 (d, 1H), 6.98-6.96 (m, 4H), 6.89-6.86 ( m, 4H), 6.38-6.35 (m, 2H), 6.35 (s, 1H), 6.16-6.10 (m, 2H), 5.81 (d, 2H), 4.23 (q, 2H), 4.17 (t, 4H), 3.94 (t, 4H), 2.90 (s, 3H), 2.72-2.58 (m, 4H), 2.32-2.28 (m, 8H), 1.81-1.68 (m, 18H), 1.54-1.41 (m, 10H), 0.99 (t, 3H)

[0210]

[0211] [Production Example 4: Production of Polymerizable Liquid Crystal Compound 4 represented by Formula (1-4)] 3 g of the compound represented by Formula (1-4-1) was obtained in the same manner as in Production Example 1, except that cyclopent-3-ene-1,2-dione (7.7 g, manufactured by Aurora) was used instead of ethyl pyruvate (9.3 g) in Production Example 1. 4 g of polymerizable liquid crystal compound 4 represented by Formula (1-4) was obtained by reacting it with the intermediate represented by Formula (1-1-2) in the same manner as in Production Example 1, except that the compound represented by Formula (1-4-1) (3 g) was used instead of the intermediate represented by Formula (1-1-1) (3 g) in Production Example 1.

[0212] Phase transition temperature (when heating): C 101 N 211 I １ 1H NMR (CDCl ３ (δ ppm) :7.99 (d, 1H), 7.53 (d, 1H), 7.37 (d, 1H), 7.29 (d, 1H), 6.98-6.96 (m, 4H), 6.93-6.91 (m, 1H), 6.89-6.87 (m, 4H), 6.38-6.35 (m, 2H), 6.35 (s, 1H), 6. 16-6.10 (m, 2H), 5.81 (d, 2H), 4.16 (t, 4H), 3.93 (t, 4H), 3.43 (d, 2H), 2.7 2-2.58 (m, 4H), 2.32-2.28 (m, 8H), 1.81-1.68 (m, 16H), 1.56-1.41 (m, 8H)

[0213]

[0214] [Production Example 5: Production of Polymerizable Liquid Crystal Compound 5 represented by Formula (1-5)] 2.5 g of the compound represented by Formula (1-5-1) was obtained in the same manner as in Production Example 1, except that γ-crotonolactone (6.7 g, manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of ethyl pyruvate (9.3 g) in Production Example 1. 3.5 g of the polymerizable liquid crystal compound 5 represented by Formula (1-5) was obtained by reacting it with the intermediate represented by Formula (1-1-2) in the same manner as in Production Example 1, except that the intermediate represented by Formula (1-1-1) (3 g) was used instead of the compound represented by Formula (1-5-1) (2.5 g).

[0215] Phase transition temperature (when heating): C 104 N 220 I １ 1H NMR (CDCl ３ ; δppm) :7.58 (tt, 1H), 7.52 (d, 1H), 7.35 (d, 1H), 7.29 (d, 1H), 6.98-6.96 (m, 4H), 6.89-6.87 (m, 4H), 6.38-6.35 (m, 2H), 6.35 (s, 1H), 6.16-6.09 (m, 3H), 5.81 (d, 2H), 4.90 (q, 2H), 4.17 (t, 4H), 3.93 (t, 4H), 2.72-2 .58 (m, 4H), 2.32-2.28 (m, 8H), 1.81-1.68 (m, 16H), 1.56-1.41 (m, 8H)

[0216]

[0217] [Production Example 6: Production of Polymerizable Liquid Crystal Compound 6 represented by Formula (1-6)] The process was carried out in the same manner as in Production Example 1, except that 1-amino-2,6-naphthalenediol (14 g, manufactured by Aurora) was used instead of 2-aminobenzene-1,4-diol (10 g) to obtain 4.3 g of the compound represented by Formula (1-6-1). The intermediate represented by Formula (1-1-2) was reacted with the compound represented by Formula (1-1-2) in the same manner as in Production Example 1, except that the intermediate represented by Formula (1-1-1) (3 g) was used instead of the compound represented by Formula (1-6-1) (4.3 g) to obtain polymerizable liquid crystal compound 6 represented by Formula (1-6) (4.2 g).

[0218] Phase transition temperature (when heating): C 10⁹ N 22⁺ １ 1H NMR (CDCl ３; δppm): 8.20 (d, 1H), 8.00 (d, 1H), 7.81 (d, 1H), 7.67 (d, 1H), 7.60 (d, 1H), 6.98-6.96 (m, 4H), 6.89-6.87 (m, 4H), 6.38-6.36 (m, 2H), 6.35 (s, 1H), 6.16-6.09 (m, 2H), 5.81 (d, 2H), 4.23 (q, 2H), 4.17 (t, 4H), 3.94 (t, 4H), 2.90 (s, 3H), 2.72-2.58 (m, 4H), 2.32-2.28 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.41 (m, 8H), 1.43 (t, 3H)

[0219]

[0220] [Production Example 7: Production of Polymerizable Liquid Crystal Compound 7 represented by Formula (1-7)] In the same manner as in Production Example 1, 1-amino-2,6-naphthalenediol (14 g, manufactured by Aurora) was used instead of 2-aminobenzene-1,4-diol (10 g), and 2-methylpropyl 2-oxopropanoate (11.5 g, manufactured by Aurora) was used instead of ethyl pyruvate (9.3 g), to obtain 4.7 g of the compound represented by formula (1-7-1). In the same manner as in Production Example 1, the intermediate represented by formula (1-1-2) was reacted with the compound represented by formula (1-1-2), except that the intermediate represented by formula (1-1-1) (3 g) was used instead of the compound represented by formula (1-7) (4.7 g), to obtain polymerizable liquid crystal compound 7 represented by formula (1-7) (4.5 g).

[0221] Phase transition temperature (when heating): C 98 N 223 I １ 1H NMR (CDCl ３; δppm) :8.20 (d, 1H), 8.00 (d, 1H), 7.81 (d, 1H), 7.67 (d, 1H), 7.60 (d, 1H), 6.98-6.96 (m, 4 H), 6.89-6.87 (m, 4H), 6.38-6.35 (m, 2H), 6.35 (s, 1H), 6.16-6.09 (m, 2H), 5.81 (d, 2H) H), 4.23 (q, 2H), 4.17 (t, 4H), 3.94 (t, 4H), 2.90 (s, 3H), 2.72-2.58 (m, 4H), 2.32-2 .28 (m, 8H)), 2.01-1.88 (m, 1H), 1.81-1.68 (m, 16H), 1.53-1.41 (m, 8H), 0.89 (d, 6H)

[0222]

[0223] [Production Example 8: Production of Polymerizable Liquid Crystal Compound 8 represented by Formula (1-8)] The process was carried out in the same manner as in Production Example 1, except that 1-amino-2,6-naphthalenediol (14 g, manufactured by Aurora) was used instead of 2-aminobenzene-1,4-diol (10 g) and butyl 2-oxopropanoate (11.5 g, manufactured by Aurora) was used instead of ethyl pyruvate (9.3 g), to obtain 4.1 g of the compound represented by formula (1-8-1). The process was carried out in the same manner as in Production Example 1, except that the compound represented by formula (1-8-1) (4.1 g) was used instead of the intermediate represented by formula (1-1-1) (3 g), to obtain polymerizable liquid crystal compound 8 (4.5 g) represented by formula (1-8).

[0224] Phase transition temperature (when heating): C 102 N 206 I １ 1H NMR (CDCl ３; δppm) :8.21 (d, 1H), 8.02 (d, 1H), 7.83 (d, 1H), 7.68 (d, 1H), 7.60 (d, 1H), 6.98-6.96 (m, 4H), 6 .89-6.87 (m, 4H), 6.38-6.35 (m, 2H), 6.35 (s, 1H), 6.16-6.09 (m, 2H), 5.81 (d, 2H), 4.23 (q, 2H), 4.17 (t, 4H), 3.94 (t, 4H), 2.90 (s, 3H), 2.72-2.58 (m, 4H), 2.32-2.28 (m, 8H), 1 .81-1.68 (m, 16H), 1.53-1.41 (m, 8H) 1.79-1.71 (m, 2H), 1.50-1.42 (m, 2H), 0.99 (t, 3H)

[0225]

[0226] [Production Example 9: Production of Polymerizable Liquid Crystal Compound 9 represented by Formula (1-9)] The process was carried out in the same manner as in Production Example 1, except that 1-amino-2,6-naphthalenediol (14 g, manufactured by Aurora) was used instead of 2-aminobenzene-1,4-diol (10 g), and cyclopent-3-ene-1,2-dione (7.7 g, manufactured by Aurora) was used instead of ethyl pyruvate (9.3 g), to obtain 3.8 g of the compound represented by formula (1-9-1). The process was carried out in the same manner as in Production Example 1, except that the compound represented by formula (1-9-1) (3.8 g) was used instead of the intermediate represented by formula (1-1-1) (3 g), to obtain 4 g of polymerizable liquid crystal compound 9 represented by formula (1-9).

[0227] Phase transition temperature (when heating): C 117 N 220 I １ 1H NMR (CDCl ３; δppm) :8.23 (d, 1H), 8.04 (d, 1H), 7.99 (d, 1H), 7.81 (d, 1H), 7.67 (d, 1H), 7.60 (d , 1H), 6.98-6.96 (m, 5H), 6.89-6.87 (m, 4H), 6.38-6.35 (m, 2H), 6.35 (s, 1H) , 6.16-6.09 (m, 2H), 5.81 (d, 2H), 4.17 (t, 4H), 3.94 (t, 4H), 3.43 (d, 2H), 2 .72-2.58 (m, 4H), 2.32-2.28 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.41 (m, 8H)

[0228]

[0229] [Production Example 10: Production of polymerizable liquid crystal compound 10 represented by formula (1-10)] In the same manner as in Production Example 1, 1-amino-2,6-naphthalenediol (14 g, manufactured by Aurora) was used instead of 2-aminobenzene-1,4-diol (10 g), and γ-crotonolactone (6.7 g, manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of ethyl pyruvate (9.3 g), and 3.3 g of the compound represented by formula (1-10-1) was obtained. In the same manner as in Production Example 1, the intermediate represented by formula (1-1-2) was reacted with the compound represented by formula (1-1-2), except that the intermediate represented by formula (1-1-1) (3 g) was used instead of the intermediate represented by formula (1-1-1) (3.3 g), to obtain polymerizable liquid crystal compound 10 (4 g) represented by formula (1-10).

[0230] Phase transition temperature (when heating): C 120 N 226 I １ 1H NMR (CDCl ３; δppm) :8.21 (d, 1H), 8.02 (d, 1H), 7.82 (d, 1H), 7.69 (d, 1H), 7.61 (d, 1H), 7.58 (t t, 1H), 6.98-6.96 (m, 4H), 6.89-6.87 (m, 4H), 6.38-6.35 (m, 2H), 6.35 (s, 1H) ), 6.16-6.09 (m, 3H), 5.81 (d, 2H), 4.90 (q, 2H), 4.17 (t, 4H), 3.94 (t, 4H), 2 .72-2.58 (m, 4H), 2.32-2.28 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.41 (m, 8H)

[0231]

[0232] [Comparative Manufacturing Example 1: Manufacturing of Comparative Compound 1 represented by formula (C1-1)] Comparative compound 1 represented by the following formula (C1-1) was synthesized with reference to the synthesis of compound 4 in Example 4 of Japanese Patent No. 5962760.

[0233]

[0234] [Comparative Manufacturing Example 2: Manufacturing of Comparative Compound 2 represented by formula (C1-2)] Comparative compound 2 represented by the following formula (C1-2) was synthesized with reference to Japanese Patent No. 5899607.

[0235]

[0236] <Solvent Solubility of Polymerizable Liquid Crystal Compounds> Solubility tests were performed on the compounds obtained in the above production example and comparative production example. The total weight of the compound and each solvent was set to 100% by weight, and the solubility in methyl ethyl ketone (MEK), cyclohexanone, or dioxolane solvents at 20% by weight or 30% by weight of the compound was visually evaluated after 30 minutes at 25°C. The evaluation results are shown in Table 13. (Observation conditions for solvent solubility) 1 ml of the obtained solution was placed in a sample bottle (product name: AS ONE, Labran screw-cap bottle 6 ml 9-852-04) and observed under the following conditions. Observation was performed under indoor fluorescent lighting (color temperature 4000-6500K, color rendering index Ra≧80, illuminance approximately 500-1000 lx). The sample bottles were placed on a black matte background (HEIKO Cut Paper, 148 x 100 mm, black), at a distance of 20 cm from the observer, and visually observed under a light source. During observation, the container was tilted at approximately 45 degrees to utilize transmitted light and check for the presence of precipitates or suspended matter derived from the compound. If necessary, the container was gently mixed by hand (5 times or less) and observed again. (Evaluation criteria for solvent solubility) A: The compound is completely dissolved by visual inspection, and no precipitates or suspended matter derived from the compound are observed. C: Precipitates and / or suspended matter derived from the compound are visible.

[0237]

[0238] [Example 1] (1) Preparation of polymerizable composition Polymerizable composition 1 was prepared by dissolving 100 parts by mass of a polymerizable liquid crystal compound (polymerizable liquid crystal compound 1 represented by formula (1-1)) and 4 parts by mass of a photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one: manufactured by Sigma-Aldrich, Irgacure 907) in 900 parts by mass of cyclopentanone.

[0239] (2) Production of phase difference film or transfer laminate (2-1) Preparation of composition for photo-alignment film According to the description in Production Example 1 of Japanese Patent No. 5626493, 1.30 g of hydroxyethyl methacrylate, 3.95 g of a photo-aligning 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 mixture was purified by reprecipitation to obtain copolymer 1 obtained by copolymerizing the photo-aligning monomer represented by the following chemical formula with hydroxyethyl methacrylate. A composition for photo-alignment film with the following composition was prepared: Copolymer 1: 0.1 parts by mass, Hexamethoxymethylmelamine (HMM): 0.01 parts by mass, p-toluenesulfonic acid monohydrate (PTSA): 0.0015 parts by mass, Propylene glycol monomethyl ether (PGME): 2.1 parts by mass

[0240]

[0241] (2-2) Formation of horizontally aligned film The photo-alignment film composition was applied by bar coating to one side of a PET substrate (manufactured by Toyobo Co., Ltd., E5100, 38 μm thick) so that the film thickness after curing would be 0.2 μm. The substrate was then heated in a 120°C oven for 1 minute to dry and heat-cur it, forming a cured coating film. Subsequently, polarized ultraviolet light containing a 313 nm emission line was exposed to the surface of the cured coating film using an Hg-Xe lamp and a Gran-Taylor prism in a direction perpendicular to the substrate normal at an exposure dose of 100 mJ / cm². ２ By irradiating with this, a horizontally aligned film was formed.

[0242] (2-3) Preparation of phase difference film or transfer laminate The polymerizable composition 1 was applied to the formed orientation film so that the film thickness after curing would be 1 μm, thereby forming a polymerizable composition film. After that, it was dried in an oven at 120°C for 60 seconds, and then exposed to ultraviolet (UV) light at a dose of 150 mJ / cm using a Fusion H-bulb. ２ Irradiation was performed to form a phase difference layer and obtain a phase difference film or a transfer laminate.

[0243] [Examples 5-13] (1) Production of polymerizable composition Polymerizable compositions 5-13 were obtained in the same manner as in Example 1, except that in Example 1, the polymerizable liquid crystal compound (polymerizable liquid crystal compound 1 represented by formula (1-1)) was replaced with a polymerizable liquid crystal compound obtained in any one of Production Examples 2-10 as shown in Table 14. (2) Production of phase difference film or transfer laminate Phase difference film or transfer laminate 5-13 were obtained in the same manner as in Example 1, except that in Example 1, one of polymerizable compositions 5-13 was used instead of polymerizable composition 1.

[0244] [Comparative Example 1] (1) A comparative polymerizable composition 1 was obtained in the same manner as in Example 1, except that the polymerizable liquid crystal compound (polymerizable liquid crystal compound 1 represented by formula (1-1)) was changed to comparative compound 1 represented by formula (C1-1). (2) A comparative phase difference film or transfer laminate 1 was obtained in the same manner as in Example 1, except that comparative polymerizable composition 1 was used instead of polymerizable composition 1.

[0245] [Evaluation] <Sample Preparation> The PET substrates of the phase difference films obtained in each example and comparative example were peeled off, the phase difference layer and horizontal alignment film were cut into 5 cm x 5 cm pieces, and the phase difference layer and horizontal alignment film were transferred to adhesive glass. The orientation and wavelength dispersion were evaluated using these samples.

[0246] <Orientation> The sample was placed between the polarizer and analyzer of a polarizing microscope. The absorption axis of the polarizer of the polarizing microscope and the absorption axis of the analyzer were orthogonal, and the slow axis of the liquid crystal layer of the sample and the absorption axis of the polarizer of the polarizing microscope were aligned parallel. In this state, the number of bright spots was counted and evaluated according to the following criteria. The polarizing microscope used was an Olympus product name "BX51". The field of view for counting the number of bright spots was approximately 2.2 mm × 1.7 mm, the magnification of the eyepiece was 10x, and the magnification of the objective lens was 10x. (Evaluation criteria for orientation) A: Uniform orientation is obtained, and the number of bright spots is 10 or less B: Not as well-oriented as A is obtained, and the number of bright spots is more than 10 but 30 or less C: No orientation or the number of bright spots is more than 30

[0247] <Phase Difference (Wavelength Dispersion)> The in-plane phase difference Re for wavelengths of 450 nm, 550 nm, and 650 nm was measured using a phase difference measuring device (KOBRA-WR, manufactured by Oji Instruments Co., Ltd.). (A1) First, to stabilize the light source of the KOBRA-WR, it was left for more than 60 minutes after turning on the light source. Then, waveplate measurement was selected and data from the reference analyzer was obtained. (A2) The measurement was performed using the wavelength dispersion characteristic mode, with the measurement conditions set as follows: (Measurement conditions) ・Measurement mode: Standard ・Tilt central angle: Leading axis ・Incident angle: 0° ・Average number of measurements: 3 times ・Average refractive index of the layer to be measured: The measured value (average refractive index) of the orientation measurement sample was entered using an Abbe refractometer (manufactured by Atago) with sodium D line (589 nm) as the light source, in accordance with JIS K7142:2014. ・Thickness: The total thickness of the horizontal alignment layer and the phase difference layer was entered. The wavelength dispersion was evaluated from the x and y values ​​calculated using the measured phase difference as follows: x = (in-plane phase difference Re at 450 nm) / (in-plane phase difference Re at 550 nm) y = (in-plane phase difference Re at 650 nm) / (in-plane phase difference Re at 550 nm) (Evaluation criteria for wavelength dispersion) A: 0.60 ≤ x < 0.95, 1.00 < y ... inverse wavelength dispersion B: 0.95 ≤ x < 1.05, 1.00 < y ... flat dispersion C: 1.05 ≤ x, 1.00 ≥ y ... normal dispersion

[0248] <Storage Stability of Composition (Ink)> The stability of the polymerizable composition (ink) was evaluated after storage at 25°C for 24 hours following its manufacture. The stability of the composition (ink) was evaluated by visually inspecting the composition after storage and checking for the presence or absence of precipitate formation. (Observation Conditions for Storage Stability) 40 ml of the stored composition (ink) was placed in a sample bottle (AS ONE, Labran screw-cap bottle 50 ml No. 7 (9-852-09)) and observed under the following conditions. Observation was performed under indoor fluorescent lighting (color temperature 4000-6500K, color rendering index Ra≧80, illuminance approximately 500-1000 lx). The sample bottle was placed on a black matte background (HEIKO cut paper, colored high quality, 148 x 100 mm, black), and observed visually from a distance of 20 cm from the observer under the light source. During observation, the container was tilted at approximately 45 degrees to utilize transmitted light and check for the presence or absence of precipitate formation. If necessary, the container was gently mixed by hand (5 times or less) and observed again. (Storage stability evaluation criteria) A: No precipitate is visible to the naked eye C: Precipitation is visible to the naked eye

[0249]

[0250] [Examples 2-4] (1) Production of polymerizable composition In Example 1, polymerizable compositions 2-4 were obtained in the same manner as in Example 1, except that instead of using compound 1, which is a polymerizable liquid crystal compound of the present disclosure, in a content of 100% by mass in the polymerizable liquid crystal compound, the polymerizable liquid crystal compound of the present disclosure and a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound of the present disclosure were mixed according to Table 15 below. As a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound of the present disclosure, a compound represented by polymerizable liquid crystal compound B-1, which is represented by the following chemical formula, was prepared. (2) Production of phase difference film or transfer laminate In Example 1, phase difference film or transfer laminate 2-4 were obtained in the same manner as in Example 1, except that polymerizable compositions 2-4 were used instead of polymerizable composition 1.

[0251]

[0252] [Examples 14-40] (1) Production of polymerizable composition In Example 1, polymerizable compositions 14-40 were obtained in the same manner as in Example 1, except that instead of using compound 1, which is a polymerizable liquid crystal compound of the present disclosure, in a content of 100% by mass in the polymerizable liquid crystal compound, the polymerizable liquid crystal compound of the present disclosure and a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound of the present disclosure were mixed according to Table 15 below. (2) Production of phase difference film or transfer laminate In Example 1, phase difference film or transfer laminate 14-40 were obtained in the same manner as in Example 1, except that polymerizable compositions 14-40 were used instead of polymerizable composition 1.

[0253]

[0254] [Evaluation] The orientation, wavelength dispersibility, and storage stability of the compositions of each example were evaluated in the same manner as in Example 1. The evaluation results are shown in Table 16.

[0255]

[0256] [Examples 41-70] (1) Production of polymerizable compositions Polymerizable compositions 41-70 were obtained in the same manner as in Example 1, except that instead of using compound 1, which is a polymerizable liquid crystal compound of the present disclosure, in a content of 100% by mass in the polymerizable liquid crystal compound, the polymerizable liquid crystal compound of the present disclosure and other polymerizable compounds were mixed according to Table 17 below. The following polymerizable compounds were prepared as other polymerizable compounds.・DPHA (M-405): Dipentaerythritol penta and hexaacrylate, trade name Aronics M-405, manufactured by Toagosei Co., Ltd. ・PETTA (M-450): Pentaerythritol tri and tetraacrylate, trade name Aronics M-450, manufactured by Toagosei Co., Ltd. ・TMPTA (M-309): Trimethylolpropane triacrylate, trade name Aronics M-309, manufactured by Toagosei Co., Ltd. (2) Production of phase difference film or transfer laminate Phase difference film or transfer laminate 41 to 70 was obtained in the same manner as in Example 1, except that polymerizable compositions 41 to 70 were used instead of polymerizable composition 1 in Example 1.

[0257] The orientation, wavelength dispersibility, and storage stability of each example were evaluated in the same manner as in Example 1. The evaluation results are shown in Table 18.

[0258]

[0259]

[0260] 1 Phase difference layer 2, 2' Substrate 3 Alignment film 10 Phase difference film 11, 21, 31 Phase difference layer 12, 22, 32 Second substrate 13, 23 Alignment film 15, 25, 35 Peelable support 16, 26, 36 Phase layer for transfer 17 Interface between alignment film and phase difference layer 27 Interface between second substrate and alignment film 20, 30, 40 Laminate for transfer 50 Polarizing plate 60 Optical component 71 Transparent electrode layer 72 Light-emitting layer 73 Electrode layer 100 Light-emitting device

Claims

A polymerizable liquid crystal compound represented by the following general formula (I). [In general formula (I), Ar represents an aromatic hydrocarbon group having 3 to 10 carbon atoms, which may be unsubstituted or substituted with one or more substituents E. Any carbon atom of the aromatic hydrocarbon group may be substituted with a heteroatom, and the number of π electrons N(π) contained in the aromatic ring in the Ar group is 10 or less. J １ This represents a monovalent group represented by the following general formula (J-1), L １ 、 L ２ 、 L ３ and L ４ each independently represents -O-, -S-, -OCH ２ -, -CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -, -CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -, -CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -, -CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or a single bond, A １ A ２ A ３ and A ４ Each of these independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group having 3 to 20 carbon atoms, which may be unsubstituted or substituted with one or more substituents E. However, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a heteroatom. R １ and R ２ Each of these independently represents a group selected from the following general formula (R-1), General form (R-1): -L ５ -R ｓｐ１ -Z １ In general formula (R-1), L ５ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐ１ This is one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. １ This represents a polymerizable functional group. L ３ , L ４ A ３ , and A ４ If there are multiple instances of each, they may be identical or different. 　 m1 and m2 each independently represent integers from 1 to 4, and k also represents an integer from 1 to 4. (In general formula (J-1), * indicates the bonding position, R ｘ and R ｙ are each independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, -OR ｗ１ , -SR ｗ２ , -COOR ｗ３ , -OCOR ｗ４ , -COR ｗ５ , -CONR ｗ６ R ｗ７ , -NR ｗ８ R ｗ９ , or, -L Ｅ -R ｓｐＥ -Z Ｅ a group represented by (R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R ｗ６ and R ｗ７ each independently represent a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, and R ｗ８ and R ｗ９ each independently represent a hydrogen atom, -OR ｗ１ , or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and -CH ２ - contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, or R ｘ and R ｙ may be bonded to each other to form an aliphatic ring having 4 to 7 members, and the aliphatic ring may contain a hetero atom, However, R ｘ and R ｙ at least one of which is an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, -COOR ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ represents, or R ｘ and R ｙ are bonded to each other to form an aliphatic ring which may contain a heteroatom in a 4- to 7-membered ring.) 　 Each substituent E is independently a halogen atom, a cyano group, a nitro group, or -OR ａ , -NR ｂ R ｃ , -SR ｄ , -COOR ｅ , -OCOR ｆ , -COR ｇ , -SiR ｈ R ｉ R ｊ (R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , R ｉ , and R ｊ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the aliphatic hydrocarbon group contains -CH ２ The hyphen may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-. L Ｅ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐＥ This is one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. Ｅ This represents a polymerizable functional group. Compounds containing substituents E and J １ If there are multiple instances of each, they may be identical or different. In the general formula (I), Ar-(J １ ) ｋ The polymerizable liquid crystal compound according to claim 1, wherein is a divalent group represented by any of the following general formulas (Ar-1) to (Ar-7). (In the general formulas (Ar-1) to (Ar-7), * indicates the bond position.) Q １ is -N= or -CR ｋ Represents =, Q ２ is -O-, -S-, or -NR ｌ - represents, R ｋ Each of these independently represents a hydrogen atom or a substituent E, and R ｌ This represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms. J １ This represents a monovalent group represented by the general formula (J-1), E represents the substituent E, and when n1 = 2 in general formulas (Ar-1) to (Ar-4), adjacent E atoms may be linked to each other to form an aliphatic ring or an aliphatic heterocycle. １ This represents a hydrogen atom or the substituent E. n1 represents an integer between 0 and 2, and n2 represents an integer between 0 and 1. k represents an integer from 1 to 4, k1 represents an integer from 0 to 2, k2 represents an integer from 1 to 3, and k3 represents an integer from 1 to 2. However, in general formula (Ar-1), k1 + n1 is an integer from 0 to 2; in general formulas (Ar-2) and (Ar-3), k + n1 is an integer from 1 to 4; in general formula (Ar-4), k2 + n1 is an integer from 1 to 3; and in general formulas (Ar-5) to (Ar-7), k3 + n2 is an integer from 1 to 2. Ar-(J １ ) ｋ Substituents E and J are contained within. １ If there are multiple instances of each, they may be identical or different. 　 In the above general formula (I), A １ and A ２ The polymerizable liquid crystal compound according to claim 1 or 2, wherein each of the groups may independently be unsubstituted or substituted with one or more substituents E, being a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, a cycloheptane-1,4-diyl group, or a cyclododecane-1,5-diyl group. 　 In the above general formula (I), A ３ and A ４ The polymerizable liquid crystal compound according to claim 1 or 2, wherein each of the groups may independently be unsubstituted or substituted with one or more substituents E, being a benzene-1,4-diyl group, a cyclohexane-1,4-diyl group, a pyridine-2,5-diyl group, a pyrimidine-2,5-diyl group, a naphthalene-2,6-diyl group, a naphthalene-1,4-diyl group, a 1,2,3,4-tetrahydronaphthalene-2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group. 　 A compound represented by the following general formula (Ar-im). [In the general formula (Ar-im), Ar-(J １ ) ｋ This represents a divalent group represented by one of the following general formulas (Ar-1) to (Ar-7): T １ , and T ２ These are, independently, -OH, -CHO, -COOH, -SH, and -NH. ２ , halogen atom, -CH ２ OH, -CH ２ SH, -CF ２ OH, -CF ２ SH represents -CH=CHCOOH, or -CH=CHOCOOH. (In the general formulas (Ar-1) to (Ar-7), * indicates the bond position.) Q １ is -N= or -CR ｋ Represents =, Q ２ is -O-, -S-, or -NR ｌ - represents, R ｋ Each of these independently represents a hydrogen atom or a substituent E, and R ｌ This represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms. J １ This represents a monovalent group represented by the following general formula (J-1), E represents a substituent E, and when n1 = 2 in general formulas (Ar-1) to (Ar-4), adjacent E atoms may be linked to each other, forming an aliphatic ring or an aliphatic heterocycle. E １ represents a hydrogen atom or substituent E. n1 represents an integer between 0 and 2, and n2 represents an integer between 0 and 1. k represents an integer from 1 to 4, k1 represents an integer from 0 to 2, k2 represents an integer from 1 to 3, and k3 represents an integer from 1 to 2. However, in general formula (Ar-1), k1 + n1 is an integer from 0 to 2; in general formulas (Ar-2) and (Ar-3), k + n1 is an integer from 1 to 4; in general formula (Ar-4), k2 + n1 is an integer from 1 to 3; and in general formulas (Ar-5) to (Ar-7), k3 + n2 is an integer from 1 to 2. (In general formula (J-1), * indicates the bonding position, R ｘ and R ｙ Each of these is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, and -OR ｗ１ , -SR ｗ２ , -COOR ｗ３ , -OCOR ｗ４ , -COR ｗ５ , -CONR ｗ６ R ｗ７ , -NR ｗ８ R ｗ９ , or -L Ｅ -R ｓｐＥ -Z Ｅ The group represented by (R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R ｗ６ and R ｗ７ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, R ｗ８ and R ｗ９ These are, independently, hydrogen atoms, -OR ｗ１ (or represents an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of the above, and the aliphatic hydrocarbon group contains -CH ２ - may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, or R ｘ and R ｙ These may bond to each other to form a 4- to 7-membered aliphatic ring, and this aliphatic ring may contain heteroatoms. However, R ｘ and R ｙ an aliphatic hydrocarbon group having 1 to 20 carbon atoms, -COOR, in which at least one of the following may be substituted. ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ It represents, or R ｘ and R ｙ These atoms are bonded to each other to form an aliphatic ring that may contain heteroatoms of 4 to 7 members. 　 Each substituent E is independently a halogen atom, a cyano group, a nitro group, or -OR ａ , -NR ｂ R ｃ , -SR ｄ , -COOR ｅ , -OCOR ｆ , -COR ｇ , -SiR ｈ R ｉ R ｊ (R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , R ｉ , and R ｊ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the aliphatic hydrocarbon group contains -CH ２ The hyphen may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-. L Ｅ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐＥ This is one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. Ｅ This represents a polymerizable functional group. Compounds containing substituents E and J １ If there are multiple instances of each, they may be identical or different. 　 A method for producing a polymerizable liquid crystal compound represented by the following general formula (I-1), comprising simultaneously or sequentially condensing a compound represented by the following general formula (Ar-im1) with a compound represented by the general formula (mc-1) and a compound represented by the general formula (mc-2). [In general formulas (Ar-im1), (mc-1), (mc-2), and (I-1), Ar-(J １ ) ｋ This represents a divalent group represented by one of the following general formulas (Ar-1) to (Ar-7): (In the general formulas (Ar-1) to (Ar-7), * indicates the bond position.) Q １ is -N= or -CR ｋ Represents =, Q ２ is -O-, -S-, or -NR ｌ - represents, R ｋ Each of these independently represents a hydrogen atom or a substituent E, and R ｌ This represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms. J １ This represents a monovalent group represented by the following general formula (J-1), E represents a substituent E, and when n1 = 2 in general formulas (Ar-1) to (Ar-4), adjacent E atoms may be linked to each other, forming an aliphatic ring or an aliphatic heterocycle. E １ represents a hydrogen atom or substituent E. n1 represents an integer between 0 and 2, and n2 represents an integer between 0 and 1. k represents an integer from 1 to 4, k1 represents an integer from 0 to 2, k2 represents an integer from 1 to 3, and k3 represents an integer from 1 to 2. However, in general formula (Ar-1), k1 + n1 is an integer from 0 to 2; in general formulas (Ar-2) and (Ar-3), k + n1 is an integer from 1 to 4; in general formula (Ar-4), k2 + n1 is an integer from 1 to 3; and in general formulas (Ar-5) to (Ar-7), k3 + n2 is an integer from 1 to 2. (In general formula (J-1), * indicates the bonding position, R ｘ and R ｙ Each of these is independently a hydrogen atom, a halogen atom, a cyano group, a nitro group, and -OR ｗ１ , -SR ｗ２ , -COOR ｗ３ , -OCOR ｗ４ , -COR ｗ５ , -CONR ｗ６ R ｗ７ , -NR ｗ８ R ｗ９ , or -L Ｅ -R ｓｐＥ -Z Ｅ The group represented by (R ｗ１ , R ｗ２ , R ｗ３ , R ｗ４ , R ｗ５ , R ｗ６ and R ｗ７ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms, R ｗ８ and R ｗ９ These are, independently, hydrogen atoms, -OR ｗ１ (or represents an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of the above, and the aliphatic hydrocarbon group contains -CH ２ - may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-, or R ｘ and R ｙ These may bond to each other to form a 4- to 7-membered aliphatic ring, and this aliphatic ring may contain heteroatoms. However, R ｘ and R ｙ an aliphatic hydrocarbon group having 1 to 20 carbon atoms, -COOR, in which at least one of the following may be substituted. ｗ３ , -COR ｗ５ , or -CONR ｗ６ R ｗ７ It represents, or R ｘ and R ｙ These atoms are bonded to each other to form an aliphatic ring that may contain heteroatoms of 4 to 7 members. L ３ and L ４ each independently represents —O—, —S—, —OCH ２ —, —CH ２ O—, —CH ２ CH ２ —, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO—O—, —CO—NH—, —NH—CO—, —OCO—NH—, —NH—COO—, —NH—CO—NH—, —NH—O—, —O—NH—, —SCH ２ —, —CH ２ S—, —CF ２ O—, —OCF ２ —, —CF ２ S—, —SCF ２ —, —CH═CH—COO—, —CH═CH—OCO—, —COO—CH═CH—, —OCO—CH═CH—, —COO—CH ２ CH ２ —, —OCO—CH ２ CH ２ —, —CH ２ CH ２ [[ID=3 six]]—COO—, —CH ２ CH ２ —OCO—, —COO—CH ２ —, —OCO—CH ２ —, —CH ２ —COO—, —CH ２ —OCO—, —CH═CH—, —N═N—, —CH═N—, —N═CH—, —CH═N—N═CH—, —CF═CF—, —C≡C— or a single bond, A １ A ２ A ３ and A ４ Each of these independently represents a divalent alicyclic hydrocarbon group or aromatic hydrocarbon group having 3 to 20 carbon atoms, which may be unsubstituted or substituted with one or more substituents E. However, any carbon atom of the alicyclic hydrocarbon group or aromatic hydrocarbon group may be substituted with a heteroatom. R １ and R ２ Each of these independently represents a group selected from the following general formula (R-1), General form (R-1): -L ５ -R ｓｐ１ -Z １ In general formula (R-1), L ５ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐ１ This is one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. １ This represents a polymerizable functional group. L ３ , L ４ A ３ , and A ４ If there are multiple instances of each, they may be identical or different. 　 m1 and m2 each independently represent integers from 1 to 4. 　 Each substituent E is independently a halogen atom, a cyano group, a nitro group, or -OR ａ , -NR ｂ R ｃ , -SR ｄ , -COOR ｅ , -OCOR ｆ , -COR ｇ , -SiR ｈ R ｉ R ｊ (R ａ , R ｂ , R ｃ , R ｄ , R ｅ , R ｆ , R ｇ , R ｈ , R ｉ , and R ｊ Each of these independently represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms), or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the aliphatic hydrocarbon group contains -CH ２ The hyphen may be replaced with -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, or -NH-CO-. L Ｅ is -O-, -S-, -OCH ２ -ien-CH ２ O-, -CH ２ CH ２ -, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ２ -ien-CH ２ S-, -CF ２ O-, -OCF ２ -, -CF ２ S-, -SCF ２ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ２ CH ２ -, -OCO-CH ２ CH ２ -ien-CH ２ CH ２ -COO-, -CH ２ CH ２ -OCO-, -COO-CH ２ -, -OCO-CH ２ -ien-CH ２ -COO-, -CH ２ -OCO-, -CH=CH-, -N=N-, -CH=N-, -N=CH-, -CH=N-N=CH-, -CF=CF-, -C≡C- or single bond, R ｓｐＥ This is one -CH ２ - or two or more non-adjacent -CH ２ Each of the hyphens independently represents an alkylene group or single bond having 1 to 20 carbon atoms, which may be replaced by -O-, -COO-, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH-, or -C≡C-. Ｅ This represents a polymerizable functional group. Compound contains substituents E and J １ If there are multiple instances of each, they may be identical or different. 　 A polymerizable composition containing the polymerizable liquid crystal compound described in claim 1 or 2. The polymerizable composition according to claim 7, further comprising at least one initiator selected from the group consisting of acylphosphine oxide polymerization initiators, α-aminoalkylphenone polymerization initiators, α-hydroxyketone polymerization initiators, and oxime ester polymerization initiators. 　 The polymerizable composition according to claim 7, further comprising a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound described in claim 1 or 2. 　 The polymerizable composition according to claim 7, further comprising a polymerizable compound having two or more polymerizable functional groups in one molecule, which is different from the polymerizable liquid crystal compound described in claim 1 or 2. The polymerizable composition according to claim 7, further comprising a polymerizable compound that dissolves in 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. 　 A polymer obtained by polymerizing the polymerizable liquid crystal compound according to claim 1 or 2. 　 A polymer obtained by polymerizing the polymerizable composition according to claim 7 or 8. A phase difference film having a phase difference layer, wherein the phase difference layer contains a cured product of the polymerizable composition described in claim 7 or 8. 　 The phase difference film according to claim 14, wherein the phase difference value Re(450) at a wavelength of 450 nm and the phase difference value Re(550) at a wavelength of 550 nm satisfy Re(450) / Re(550) < 1.

05. A step of forming a film of the polymerizable composition according to claim 7 or 8, A step of at least oriented the polymerizable compound in the polymerizable composition that has been formed into a film, A method for producing a phase difference film, comprising the step of forming a phase difference layer by further comprising the step of polymerizing the polymerizable compound at least after the orientation step. 　 The device comprises a phase difference layer and a support that provides a peelable support for the phase difference layer. The phase difference layer contains a cured product of the polymerizable composition according to claim 7 or 8. A transfer laminate for transferring a phase difference layer. 　 An optical member comprising a polarizing plate on a phase difference film as described in claim 14. 　 A step of preparing a transfer laminate for transferring a phase difference layer, comprising a phase difference layer and a support that removably supports the phase difference layer, wherein the phase difference layer contains a cured product of the polymerizable composition described in claim 7 or 8; A transfer step of placing a transfer target, which includes at least a polarizing plate, and the phase difference layer of the transfer laminate facing each other, and transferring the transfer laminate onto the transfer target, A peeling step of peeling the support from the transfer laminate transferred onto the transfer target, A method for manufacturing an optical component. 　 A display device comprising a phase difference film according to claim 14, or an optical member having a polarizing plate on the phase difference film.

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