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

Abstract

A polymerizable liquid crystal compound according to the present invention is represented by general formula (I). (In general formula (I), Ar represents a divalent group that is represented by general formula (Ar-1), and the symbols in general formula (I) and general formula (Ar-1) are explained 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 Document 1). 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 a factor. 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

[0006] However, the inverse wavelength dispersive liquid crystal compounds disclosed in Patent Document 1, etc., have insufficient light resistance when forming optical films, and are prone to changes in phase difference and wavelength dispersiveness due to light. In view of the above circumstances, the embodiments of this disclosure aim to provide a polymerizable liquid crystal compound capable of forming a phase difference layer exhibiting good light resistance and inverse wavelength dispersiveness, 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 component having the phase difference film and a method for producing the same, and a display device.

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

[0008] [In general formula (I), Ar represents a divalent group represented by the following general formula (Ar-1), L １ , L ２ , L ３ and L ４Each 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[[ID=三十九]] 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, and A １ , A ２ , A ３ and A ４ each independently represents an alicyclic hydrocarbon group or an aromatic hydrocarbon group having 3 to 20 carbon atoms and being unsubstituted or substituted by one or more substituents E, and any carbon atom of the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be substituted by a hetero atom. R １ and R ２ each independently represents a group selected from the following general formula (R-1): General formula (R-1): -L ５ -R ｓｐ１ -Z １ In the general formula (R-1), L ５ represents -O-, -S-, -OCH It should be noted that in the above translation, there may be some inaccuracies in chemical formula representation. For more accurate translation of chemical-related content, it is recommended to refer to professional chemical dictionaries or consult relevant experts.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 L represents a polymerizable functional group. 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.

[0009] (In the general formula (Ar-1), * represents the bond position, Q１ represents -N= or -CR ａ =, and Q ２ represents -O-, -S-, -NR ｂ -, or -CR ｃ R ｄ -, and G １ is an alicyclic hydrocarbon group having 3 to 20 carbon atoms containing at least one double bond in the ring, and -CH ２ - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -NR ｅ -, -CS-, or -CO-, and represents a monovalent group which may be substituted by one or more substituents E, and R ａ , R ｃ , and R ｄ each independently represents a hydrogen atom or a substituent E, and R ｂ , and R ｅ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. E １ and E ２ each independently represents a hydrogen atom or a substituent E, or E １ and E ２ may be linked to each other to form an aliphatic ring or an aliphatic heterocyclic ring. ) Each of the substituents E independently represents a halogen atom, a cyano group, a nitro group, -OR ｆ , -NR ｇ R ｈ , -SR ｉ , -COOR ｊ , -OCOR ｋ , -COR ｌ , -SiR ｍ R ｎ R ｏ , an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or a group represented by -L Ｅ -R ｓｐＥ -Z Ｅ , or an alkyl group having 1 to 20 carbon atoms which may be substituted by one or more of these, and -CH ２- may be replaced with -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-, R ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, 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-, -CF=CF-, -C≡C-, or single bond are represented by 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. If there are multiple substituents E in the compound, they may be the same or different. ] <2> In the above general formula (I), A １ and A ２ The polymerizable liquid crystal compound according to <1>, 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. <3> In the general formula (I), A ３ and A ４ 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: 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. <4> In the general formula (I), G １ The polymerizable liquid crystal compound according to any one of <1> to <3> above, wherein the alicyclic hydrocarbon group has a total number of atoms constituting the ring of 5 to 8, and the number of π electrons contained in the alicyclic hydrocarbon group is 4 or more. <5> A compound represented by the following general formula (Ar-im).

[0010] (In the general formula (Ar-im), Q １ is -N= or -CR ａ The equals sign represents Q ２ -O-, -S-, -NR ｂ - or -CR ｃ R ｄ - represents G １This is an alicyclic hydrocarbon group having 3 to 20 carbon atoms and containing at least one intraring double bond, wherein the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -NR ｅ R represents a monovalent group which may be replaced by -, -CS-, or -CO-, and which may be substituted by one or more substituents E. ａ , R ｃ , and R ｄ Each of these independently represents a hydrogen atom or a substituent E, and R ｂ , and R ｅ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. １ and E ２ Each of these independently represents a hydrogen atom or a substituent E, or E １ and E ２ These elements may be linked to each other, forming an aliphatic ring or an aliphatic heterocycle. 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. The substituent E is independently a halogen atom, a cyano group, a nitro group, or -OR. ｆ , -NR ｇ R ｈ ,-SR ｉ , -COOR ｊ , -OCOR ｋ , -COR ｌ , -SiR ｍ R ｎ R ｏ , alicyclic hydrocarbon groups having 3 to 20 carbon atoms, or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an alkyl group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the alkyl group contains -CH ２- may be replaced with -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-, R ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, 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-, -CF=CF-, -C≡C-, or single bond are represented by 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. If there are multiple substituents E in the compound, they may be the same or different.) <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).

[0011] (In general formulas (Ar-im1), (mc-1), (mc-2), and (I-1), Q １ is -N= or -CR ａ The equals sign represents Q ２ -O-, -S-, -NR ｂ - or -CR ｃ R ｄ - represents G １ This is an alicyclic hydrocarbon group having 3 to 20 carbon atoms and containing at least one intraring double bond, wherein the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -NR ｅ R represents a monovalent group which may be replaced by -, -CS-, or -CO-, and which may be substituted by one or more substituents E. ａ , R ｃ , and R ｄ Each of these independently represents a hydrogen atom or a substituent E, and R ｂ , and R ｅ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. １ and E ２ Each of these independently represents a hydrogen atom or a substituent E, or E １ and E ２ These elements may be linked to each other, forming an aliphatic ring or an aliphatic heterocycle. 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 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 ２O-, -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 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 an integer from 1 to 4. Each substituent E independently represents a halogen atom, a cyano group, a nitro group, or -OR ｆ , -NR ｇ R ｈ ,-SRｉ , -COOR ｊ , -OCOR ｋ , -COR ｌ , -SiR ｍ R ｎ R ｏ , alicyclic hydrocarbon groups having 3 to 20 carbon atoms, or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an alkyl group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the alkyl group contains -CH ２ - may be replaced with -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-, R ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, 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-CH２ 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-, -CF=CF-, -C≡C-, or single bond are represented by 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-. Ｅrepresents a polymerizable functional group. If there are multiple substituents E in the compound, they may be the same or different. ] <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> above, 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> above, 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> above, 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) < 0.95. <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 described in any of <7> to <11>. <18> An optical member comprising a polarizing plate on a phase difference film 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 removably supports the phase difference layer, wherein the phase difference layer contains a cured product of the polymerizable composition described in any of <7> to <11>; 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; and a peeling step of peeling the support from the transfer laminate transferred onto the transfer target. <20> A display device comprising a phase difference film as described in <14> or <15> above, or an optical member having a polarizing plate on the phase difference film.

[0012] According to embodiments of the present disclosure, it is possible to provide a polymerizable liquid crystal compound capable of forming a phase difference layer exhibiting inverse wavelength dispersion with good light resistance, 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.

[0013] 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.

[0014] 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.

[0015] 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.

[0016] A. Polymerizable Liquid Crystal Compounds The polymerizable liquid crystal compounds of this disclosure are compounds represented by the following general formula (I).

[0017] [In general formula (I), Ar represents a divalent group represented by the following general formula (Ar-1), L １ , L ２ , L ３ and L ４These 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 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-, -OCH２ -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 L represents a polymerizable functional group. 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.

[0018] (In the general formula (Ar-1), * represents the bond position, Q１ is -N= or -CR ａ The equals sign represents Q ２ -O-, -S-, -NR ｂ - or -CR ｃ R ｄ - represents G １ This is an alicyclic hydrocarbon group having 3 to 20 carbon atoms and containing at least one intraring double bond, wherein the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -NR ｅ R represents a monovalent group which may be replaced by -, -CS-, or -CO-, and which may be substituted by one or more substituents E. ａ , R ｃ , and R ｄ Each of these independently represents a hydrogen atom or a substituent E, and R ｂ , and R ｅ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. １ and E ２ Each of these independently represents a hydrogen atom or a substituent E, or E １ and E ２ They may be linked to each other to form an aliphatic ring or an aliphatic heterocycle.) Each substituent E can independently be a halogen atom, a cyano group, a nitro group, or -OR ｆ , -NR ｇ R ｈ ,-SR ｉ , -COOR ｊ , -OCOR ｋ , -COR ｌ , -SiR ｍ R ｎ R ｏ , alicyclic hydrocarbon groups having 3 to 20 carbon atoms, or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an alkyl group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the alkyl group contains -CH ２- may be replaced with -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-, R ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, 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-, -CF=CF-, -C≡C-, or single bond are represented by 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. If multiple substituents E are present in the compound, they may be the same or different.

[0019] The compound represented by the general formula (I) in this disclosure is the specific R １ From R ２ Because the main chain structure has a specific structure, the orientation between molecules is improved, and the compound 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 terminal. The compound represented by general formula (I) of this disclosure has a structure in which a side chain of an alicyclic hydrocarbon group containing at least one intraring double bond is bonded to a fused ring group of a 6-membered ring and a 5-membered ring contained in the main chain portion. As a result, while maintaining a structure in which the axes of the main chain portion of the molecule and the alicyclic hydrocarbon group of the side chain are orthogonal, the plane of the aliphatic ring of the alicyclic hydrocarbon containing at least one intraring double bond is less likely to twist significantly with respect to the plane of the fused ring. Because the plane of the fused ring contained in the liquid crystalline main chain portion and the plane of the aliphatic ring of the side chain are less likely to twist, the plane of the fused ring and the plane of the aliphatic ring of the side chain tend to exist on roughly the same plane, and the compound represented by general formula (I) of this disclosure exhibits inverse wavelength dispersion (see reference example below). Furthermore, the compound represented by general formula (I) of this disclosure has a side chain that is an alicyclic hydrocarbon group containing at least one intraring double bond, and therefore exhibits lower photoreactivity and good lightfastness compared to the case of an aromatic ring group, and is less susceptible to changes in phase difference and wavelength dispersibility due to light. The compound represented by general formula (I) of this disclosure has a structure in which a side chain of an alicyclic hydrocarbon group containing at least one intraring double bond is bonded to a fused ring group in the main chain portion, and therefore exhibits good orientation due to its order. Thus, the polymerizable liquid crystal compound represented by general formula (I) of this disclosure can form a phase difference layer exhibiting reverse wavelength dispersibility with good lightfastness.

[0020] L in general formula (I) １ , L２ , 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.

[0021] L １ and L ２ More 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-.

[0022] L ３ 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 ２O-, -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.

[0023] 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.

[0024] 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.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] 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.

[0029] 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.

[0030] 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.

[0031] 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.

[0032] 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.

[0033] 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.

[0034] 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.

[0035] 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.

[0036] 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.

[0037] 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.

[0038] 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.

[0039] (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.

[0040] 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.

[0041] Each of the substituents E is independently a halogen atom, a cyano group, a nitro group, or -OR ｆ , -NR ｇ R ｈ ,-SR ｉ , -COOR ｊ , -OCOR ｋ , -COR ｌ , -SiR ｍ R ｎ R ｏ , alicyclic hydrocarbon groups having 3 to 20 carbon atoms, or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an alkyl group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the alkyl group contains -CH ２ - may be replaced with -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-, R ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0042] Examples of the halogen atoms include fluorine, chlorine, bromine, and iodine atoms. ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏThe alkyl group having 1 to 6 carbon atoms in the alkyl group may be a linear, branched, or cyclic alkyl group. Specifically, examples include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group. The number of carbon atoms in the alkyl group may be 1 to 4, 1 or 2, or 1.

[0043] -OR ｆ 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 ｇ R ｈ For example, an amino group (-NH ２ Examples include methylamino groups, dimethylamino groups, and diisopropylamino groups. -SR ｉ 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 ｊ 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-pentyloxycarbonyl group, etc. -OCOR ｋ Examples 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, isopropylcarbonyloxy groups, n-butoxycarbonyloxy groups, t-butoxycarbonyloxy groups, etc. -COR ｌExamples 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 ｍ R ｎ R ｏ 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.

[0044] Examples of alicyclic hydrocarbon groups having 3 to 20 carbon atoms include 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, and 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 groups and adamantyl groups. The alicyclic hydrocarbon group having 3 to 20 carbon atoms may be an alicyclic hydrocarbon group having 3 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 8 carbon atoms, or an alicyclic hydrocarbon group having 3 to 6 carbon atoms. 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.

[0045] A１ 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 - may be 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 substituted with a fluorine atom, or may be a fluorine atom, a chlorine atom, an alkoxy group having 1 to 2 carbon atoms, or an alkyl group having 1 to 2 carbon atoms in which any hydrogen atom may be substituted with 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 .

[0046] 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.

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] 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.

[0058] On the other hand, in general formula (I), Ar represents a divalent group represented by the following general formula (Ar-1).

[0059] (In the general formula (Ar-1), * represents the bond position, Q １ is -N= or -CR ａ The equals sign represents Q ２ -O-, -S-, -NR ｂ - or -CR ｃ R ｄ - represents G １ This is an alicyclic hydrocarbon group having 3 to 20 carbon atoms and containing at least one intraring double bond, wherein the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -NR ｅ R represents a monovalent group which may be replaced by -, -CS-, or -CO-, and which may be substituted by one or more substituents E. ａ , R ｃ , and R ｄ Each of these independently represents a hydrogen atom or a substituent E, and R ｂ , and R ｅ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. １ and E ２ Each of these independently represents a hydrogen atom or a substituent E, or E １ and E ２ These may be linked to each other to form an aliphatic ring or an aliphatic heterocycle. Each substituent E can independently be a halogen atom, a cyano group, a nitro group, or -OR ｆ , -NR ｇ R ｈ ,-SR ｉ , -COOR ｊ , -OCOR ｋ , -COR ｌ , -SiR ｍ R ｎ R ｏ , alicyclic hydrocarbon groups having 3 to 20 carbon atoms, or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an alkyl group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the alkyl group contains -CH ２- may be replaced with -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-, R ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, 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-, -CF=CF-, -C≡C-, or single bond are represented by 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. If multiple substituents E exist within the compound, they may be the same or different.)

[0060] The substituent E in the general formula (Ar-1) is A １ A ２ A ３ and A ４ Examples include substituents similar to those described in [previous section]. However, E in the general formula (Ar-1) is different. １ and E ２ They may be linked to each other to form an aliphatic ring or an aliphatic heterocycle. That is, E １ and E ２ These may be linked together to form an aliphatic heterocycle containing at least one heteroatom selected from oxygen, nitrogen, or sulfur atoms, with 5 to 8 members, and further 5 to 6 members.

[0061] R ａ , R ｃ , and R ｄ Each of these independently represents a hydrogen atom or a substituent E, and R ｂ , and R ｅ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ａ , R ｃ , and R ｄ The substituent E in A １ A ２ A ３ and A ４ Examples of substituents similar to those described in the previous section are R. ｂ and R ｅThe alkyl group having 1 to 6 carbon atoms in the alkyl group may be a linear, branched, or cyclic alkyl group. Specifically, examples include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, n-pentyl group, n-hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group. The number of carbon atoms in the alkyl group may be 1 to 4, 1 or 2, or 1.

[0062] Q １ is -N= or -CR ａ It represents =, R ａ is a hydrogen atom, -OR ｆ ,-SR ｉ Alternatively, it may be an alkyl group having 1 to 4 carbon atoms. Q １ From the standpoint of having good lightfastness, improved reverse wavelength dispersion, and ease of manufacture, -N=, -CH=, -C(-OCH) ３ ) =, or -C(-SCH ３ ) = is acceptable.

[0063] Q ２ -O-, -S-, -NR ｂ - or -CR ｃ R ｄ - represents R ｂ R may be a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. ｃ and R ｄ Each is independently a hydrogen atom, -OR ｆ ,-SR ｉ , or -NR ｇ R ｈ That's fine. Q ２ From the standpoint of having good lightfastness, improved reverse wavelength dispersion, and ease of manufacture, -O-, -S-, -NH-, or -N(CH) ３ ) - That's fine.

[0064] Q １ and Q ２The following combinations include (ar-1-1) to (ar-1-8), but from the standpoint of ease of manufacture, the following formulas (ar-1-2), (ar-1-3), (ar-1-6), (ar-1-7), or (ar-1-8) may be used. From the standpoint of good lightfastness and improved reverse wavelength dispersion, as well as stability and ease of manufacture, the following formulas (ar-1-2) or (ar-1-6) may be used.

[0065] (In the formula, G １ , R ａ , R ｂ , R ｃ , R ｄ , E １ , and E ２ These are as described above.

[0066] E １ and E ２ Because it tends to have good lightfastness and improved inverse wavelength dispersion, and also because it is easy to manufacture and source raw materials, at least one of them may be a hydrogen atom, and both may be hydrogen atoms. １ and E ２ If at least one of them is substituent E, then substituent E １ In terms of ease of manufacturing, halogen atoms, -OR ｆ , -COOR ｊ , -OCOR ｋ , may be an alicyclic hydrocarbon group or an alkyl group. The halogen atom may be a fluorine atom, a chlorine atom, or a bromine atom. -OR ｆ This may be an alkoxy group having 1 to 4 carbon atoms, and may be a methoxy group or an ethoxy group. -COOR ｊ 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 ｋThe substituent E 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 alkyl group may be a linear or branched alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 8 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. The alicyclic hydrocarbon group in substituent E may be a cyclopentyl group or a cyclohexyl group. E １ and E ２ These elements may be linked together to form a 5-6 membered aliphatic ring or an aliphatic heterocycle containing at least one heteroatom selected from oxygen, nitrogen, or sulfur atoms, in order to improve lightfastness, reverse wavelength dispersion, and structural stability.

[0067] G １ This is an alicyclic hydrocarbon group having 3 to 20 carbon atoms and containing at least one intraring double bond, wherein the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -NR ｅ This represents a monovalent group that may be replaced with -, -CS-, or -CO-, and may be substituted with one or more substituents E. Note that "-CS-" represents "-C(=S)-", and "-CO-" represents "-C(=O)-". Examples of alicyclic hydrocarbon groups having 3 to 20 carbon atoms and containing at least one intraring double bond include cyclopropene group, cyclobutene group, cyclopentene group, cyclohexene group, cyclohexadiene group, cycloheptadiene group, cyclooctadiene group, octahydronaphthalene group, hexahydronaphthalene group, bicyclo[2.2.1]heptene group, and 1,2,2a,3,4,5,5a,6,7,8-decahydroacenaphthalene group, and the -CH contained in the alicyclic hydrocarbon group ２ - is -O-, -S-, -NR ｅIt may be replaced with -, -CS-, or -CO-. Also, in the alicyclic hydrocarbon group, -CH ２ - is -C (=CH ２ ) - may be replaced with this. Note that the number of carbon atoms in an alicyclic hydrocarbon group having 3 to 20 carbon atoms includes the number of carbon atoms of substituents. An alicyclic hydrocarbon group having 3 to 20 carbon atoms that contains at least one intraring double bond may be an alicyclic hydrocarbon group having 3 to 12 carbon atoms that contains at least one intraring double bond.

[0068] G １ The total number of atoms constituting the ring in the alicyclic hydrocarbon group (carbon atoms, nitrogen atoms, oxygen atoms, sulfur atoms) is particularly good in terms of good light resistance, improved reverse wavelength dispersion, and structural stability, and may be 5 to 12, 5 to 8, 5 or 6. For example, G １ If the alicyclic hydrocarbon group is a cyclohexadiene group, the total number of atoms constituting the ring is 6; if it is a 2,5-dihydrofuran group, the total number of atoms constituting the ring is 5; if it is a hexahydronaphthalene group, the total number of atoms constituting the ring is 10; and if it is a bicyclo[2.2.1]heptene group, the total number of atoms constituting the ring is 7. G bonded to the fused ring of the main chain １ If an alicyclic hydrocarbon group is further bonded by a single bond to the alicyclic hydrocarbon group, the further bonded alicyclic hydrocarbon group is denoted as substituent E, and G １ It is not included in the total number of atoms constituting the ring in the alicyclic hydrocarbon group.

[0069] G １ The total number of carbon atoms constituting the ring in the alicyclic hydrocarbon group may be 3 to 6, or 4 to 6, from the standpoint of good light resistance, improved reverse wavelength dispersion, ease of manufacture, and structural stability.

[0070] G １ The number of π electrons N(π) contained in the alicyclic hydrocarbon group is determined by the plane of the fused ring of the main chain and G １The surface with becomes difficult to twist, and the reverse wavelength dispersion property is likely to be improved. Therefore, it is 2 or more, preferably 4 or more. The upper limit value of the number of π electrons may be 12 or less, may be 10 or less, may be 8 or less, or may be 6 or less. Incidentally, G １ The number of π electrons N(π) contained in the alicyclic hydrocarbon group of G ２ refers to the number of π electrons involved in the π bond formed by the atoms (carbon atom, nitrogen atom, oxygen atom, sulfur atom) constituting the ring. Among the number of π electrons involved in the π bond formed by the atoms constituting the ring, -CH ２ - is replaced by -C(=S)-, -C(=O)-, or -C(=CH

[0071] Examples of the alicyclic hydrocarbon group having 3 to 20 carbon atoms and containing at least one double bond in the ring, which may be substituted by the substituent E, include, but are not limited to, the following structures.

[0072] (In the formula, * represents the bonding position.)

[0073] Among them, from the viewpoint that the surface of the condensed ring of the main chain and the surface of G １ become difficult to twist and the reverse wavelength dispersion property is likely to be improved, the aliphatic ring G<000​​​​​​​​​​​​​​Further, since it becomes difficult for the plane of the condensed ring of the main chain and the plane of G １ to be twisted and it is easy to improve the reverse wavelength dispersibility, G １ has 3 to 6 carbon atoms, and when the total number of atoms constituting the ring of G １ is N(r) and the number of π electrons contained in the alicyclic hydrocarbon group of G １ is N(π), it is preferable to satisfy N(r) / N(π)≤2. N(r) / N(π) may be 1.5 or less. The lower limit value of N(r) / N(π) may usually be 1 or more.

[0076] Further, since it is easy to have good light resistance, the total number of heteroatoms contained in the alicyclic hydrocarbon group of G １ may be 4 or less, 3 or less, or 2 or less. Note that the total number of heteroatoms contained in the alicyclic hydrocarbon group of G １ includes the heteroatoms contained in the substituent.

[0077] Since it is easy to have good light resistance and easy to improve the reverse wavelength dispersibility, the alicyclic hydrocarbon group of G １ may have 5 to 8 atoms in total constituting the ring, 4 or more π electrons contained in the alicyclic hydrocarbon group, and 4 or less heteroatoms in total contained in the alicyclic hydrocarbon group. Further, the total number of atoms constituting the ring may be 5 or 6, the number of π electrons may be 4, and the total number of heteroatoms contained in the alicyclic hydrocarbon group may be 3 or less.

[0078] G １ may be unsubstituted, but as the substituent E that G １ may have, among others, from the viewpoints of being easy to have good light resistance and easy to improve the reverse wavelength dispersibility, and ease of production and stability, a halogen atom, -OR ｆ , -COOR ｊ , -OCOR ｋ , or an alkyl group may be suitable. The halogen atom may be a fluorine atom or a chlorine atom. -OR ｆ may be an alkoxy group having 1 to 4 carbon atoms, and may be a methoxy group or an ethoxy group. -COOR ｊAmong 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 ｋ The alkyl 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 alkyl group may be a linear or branched alkyl group having 1 to 15 carbon atoms, an alkyl group having 1 to 8 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, etc.), an alkyl group having 1 to 4 carbon atoms, or a methyl group or an ethyl group.

[0079] G １ As such, representing a group selected from formulas (g-1) to (g-41) is preferable in terms of good lightfastness, improved reverse wavelength dispersion, stability, and ease of obtaining raw materials and manufacturing, but is not limited to these.

[0080] G １In particular, considering its tendency to exhibit good lightfastness and improved reverse wavelength dispersion, as well as its ease of manufacture and stability, formulas (g-3), (g-4), (g-5), (g-6), (g-7), (g-8), (g-9), (g-10), (g-11), (g-16), (g-17), (g-18), (g-19), (g-20), (g-21), (g-22), (g-23), (g-24), (g-25), (g-26), (g-27), (g-28), (g-29), (g-30), (g-34), (g-38), (g-39), (g-40), It may be at least one selected from the group consisting of (g-41) and (g-3), (g-4), (g-6), (g-8), (g-9), (g-24), (g-26), (g-28), (g-29), (g-34), (g-38), (g-39), (g-40), and (g-41), and it may be at least one selected from the group consisting of (g-3), (g-6), (g-8), (g-9), (g-26), (g-28), (g-29), (g-38), and (g-41).

[0081] Furthermore, examples of compounds represented by general formula (I) include the following compounds (1) to (250). G in the table １ G in the general formula (Ar-1) １ Let Q be expressed in terms of a group selected from formulas (g-1) to (g-41), １ and Q ２ Q is in the general formula (Ar-1). １ and Q ２ This represents Lc1, which 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 This represents [the compound]. However, it is not limited to the compounds shown in the table.

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090] 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.

[0091] The compound represented by general formula (I) may use the compound represented by the following general formula (Ar-im) as an intermediate.

[0092] (In the general formula (Ar-im), Q １ Q ２ G １ , E １ and E ２ Each of these is independent and has the same meaning as the respective symbols in the general formula (Ar-1), and T １ , and T２ is, independently of each other, -OH, -CHO, -COOH, -SH, -NH ２ , a halogen atom, -CH ２ OH, -CH ２ SH, -CF ２ OH, -CF ２ SH, -CH=CHCOOH, or -CH=CH OCOOH. )

[0093] T １ , and T ２ is, independently of each other, -OH, -CHO, -COOH, -SH, -NH ２ , a halogen atom, -CH ２ OH, -CH ２ SH, -CF ２ OH, -CF ２ SH, -CH=CHCOOH, or -CH=CH OCOOH, but L １ , and L ２ may be appropriately selected according to the structure. For example, when T １ or T ２ is -OH, L １ or L ２ is -OCO-, -O-, -OCH ２ -, -O-CO-O-, -OCO-NH-, -O-NH-, -OCF ２ -, -OCO-CH=CH-, -OCO-CH ２ CH ２ -, -OCO-CH ２ - can be used as an intermediate. When T １ or T ２ is -CHO, L １ or L ２ is -CH=N-, -CH=N-N=CH-, -CH=CH- can be used as an intermediate. When T １ or T ２ is -COOH, L １ or L ２ is -CO-, -COO-, -CO-S-, -CO-NH-, -COO-CH=CH-, -COO-CH ２ CH ２ -, -COO-CH ２ - can be used as an intermediate. When T １ or T２ 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 bonds are -COO-, -CH=CH-, -C≡C-, -CF=CF-, or single bonds. 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-CF ２ 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 L１ 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-.

[0094] Compounds represented by the general formula (Ar-im) are, for example, described in Journal of Combinatorial Chemistry (2009), 11(2), 198-201, Synlett (2009), (1), 63-66, New Journal of Chemistry (2019), 43(9), 3725-3732, Organic Letters (2011), 13(19), 5100-5103, Advanced Synthesis & Catalysis (2013), 355(5), 981-987, and Organic & Biomolecular Chemistry. It can be manufactured by referring to (2011), 9(13), 4983-4986, Journal of Organic Chemistry (2015), 80(15), 7803-7809, etc.

[0095] Compounds represented by the general formula (Ar-im) are Q １ ga -N=, Q ２ -O-, -S-, or -NR ｂ -In this case, for example, it can be manufactured according to the following formula. See Journal of Combinatorial Chemistry (2009), 11(2), 198-201, R ４ to G １ By changing this, R in Synlett (2009), (1), 63-66 becomes G １ Changed and -NHMe's Me to NR ｂ It can be manufactured by changing it to [this].

[0096] (In the formula, Q ２ is -O-, -S-, or -NR ｂ - represents R ｂ G１ , E １ and E ２ Each of these is independent and has the same meaning as the respective symbols in the general formula (Ar-1), and T １ and T ２ Each of these is independently synonymous with the respective symbols of (Ar-im).

[0097] Furthermore, compounds represented by the general formula (Ar-im) are Q １ ga -N=, Q ２ ga-CR ｃ R ｄ -In this case, for example, it can be manufactured according to the following formula. Refer to New Journal of Chemistry (2019), 43(9), 3725-3732, and the methyl of methylbutanone is G １ It can be manufactured by changing it to this.

[0098] (In the formula, R ｃ , R ｄ G １ , E １ and E ２ Each of these is independent and has the same meaning as the respective symbols in the general formula (Ar-1), and T １ and T ２ Each of these is independently synonymous with the respective symbols of (Ar-im).

[0099] Furthermore, compounds represented by the general formula (Ar-im) are Q １ -CH=, Q ２ -O-, -S-, or -NR ｂ -In this case, for example, it can be manufactured according to the following formula. See Organic Letters (2011), 13(19), 5100-5103, R １ to G １ It can be manufactured by changing to the following. The starting material in the following formula can be produced by synthesizing an acetylene compound by the method described in J. Org. Chem. (2019), 84, 17, 10832-10842, and reacting it with 2-bromo-3-iodo1,4-dimethoxybenzene.

[0100] (In the formula, Q １-CH = Q ２ is -O-, -S-, or -NR ｂ - represents R ｂ G １ , E １ and E ２ Each of these is independent and has the same meaning as the respective symbols in the general formula (Ar-1), and T １ and T ２ Each of these is independently synonymous with the respective symbols of (Ar-im).

[0101] Furthermore, compounds represented by the general formula (Ar-im) are Q １ ga-CR ａ =, Q ２ ga-CR ｃ R ｄ - In this case, it can be prepared using a Grignard reagent according to the following formula. Refer to Journal of Organic Chemistry (2015), 80(15), 7803-7809 and set the pH of compound 14 to G １ It can be manufactured by changing it to this.

[0102] (In the formula, R ａ , R ｃ , R ｄ G １ , E １ and E ２ Each of these is independent and has the same meaning as the respective symbols in the general formula (Ar-1), and T １ and T ２ Each of these is independently synonymous with the respective symbols of (Ar-im).

[0103] Alternatively, compounds represented by the general formula (Ar-im) may be prepared using a coupling reaction as shown below. For details on the coupling reaction shown below, please refer to International Publication No. 2020 / 121823.

[0104] (In the formula, Q １ Q ２ G １ , E １ and E ２ Each of these is independent and has the same meaning as the respective symbols in the general formula (Ar-1), and T １ and T ２Each of these is independently synonymous with the respective signs of (Ar-im). X represents a halogen atom.

[0105] All of the above reactions depend on the reaction conditions, T １ or T ２ This process may be carried out under protective conditions. Furthermore, commercially available compounds may be appropriately selected or synthesized as starting materials and raw materials during production.

[0106] 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 the condensed ring group), 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).

[0107] (In general formulas (Ar-im1), (mc-1), (mc-2), and (I-1), Q １ Q ２ G １ , E １ , E ２ 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).

[0108] Compounds represented by the general formula (Ar-im1) are produced according to the method for producing the general formula (Ar-im) described above, T １ and T ２ However, it can be manufactured by procuring the -OH raw materials. As starting materials, commercially available products can be appropriately selected or obtained by synthesis. Depending on the reaction conditions, it may also be manufactured using raw materials in which a protecting group has been introduced to the -OH group, and then deprotected to obtain the general formula (Ar-im1).

[0109] 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.

[0110]

[0111] Furthermore, the polymerizable liquid crystal compound represented by the general formula (I) of this disclosure is E１ and E ２ Furthermore, depending on the type and substitution position of substituent E, a compound represented by the general formula (Ar-im) may not be used, and E may be added later. １ and E ２ Furthermore, substituent E may be introduced. Also, the polymerizable liquid crystal compound represented by general formula (I) of this disclosure does not use a compound represented by general formula (Ar-im), for example, but substituent G may be introduced later. １ This can also be obtained by introducing [a certain method].

[0112] 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.

[0113] 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).

[0114] Furthermore, the polymerizable liquid crystal compound of this disclosure is a polymerizable liquid crystal compound capable of forming a phase difference layer exhibiting inverse wavelength dispersion. When a polymerizable composition containing only the polymerizable liquid crystal compound 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 0.95, more preferably in the range of 0.60 or more and less than 0.93, even more preferably in the range of 0.60 or more and less than 0.90, particularly preferably in the range of 0.60 or more and 0.83, and may also be in the range of 0.60 or more and less than 0.80. In addition, it is preferable that Re(650) / Re(550) is greater than 1.00, and more preferably in the range of 1.02 or more and 1.10. 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.

[0115] The polymerizable liquid crystal compound of this disclosure is a polymerizable liquid crystal compound capable of forming a phase difference layer exhibiting inverse wavelength dispersion with good lightfastness, and was tested using an accelerated lightfastness tester (UV autofade meter U48AU manufactured by Suga Test Instruments Co., Ltd.) at a temperature of 63°C, humidity of 40%, and illuminance of 500 ± 100 W / m². ２ It is preferable that the variation value z (%) of the in-plane phase difference Re at a wavelength of 550 nm before and after a lightfastness test, in which the sample is irradiated for 48 hours, is less than 10%. z (%) = {1 - (in-plane phase difference Re after the lightfastness test at 550 nm) / (in-plane phase difference Re before the lightfastness test at 550 nm)} × 100

[0116] 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.

[0117] 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, and is more preferably solvable in 20% by mass or more.

[0118] B. Polymerizable Compositions The polymerizable compositions of this disclosure are compositions comprising at least the polymerizable liquid crystal compound of this disclosure.

[0119] Since the polymerizable composition of this disclosure contains the polymerizable liquid crystal compound of this disclosure, it is possible to obtain a polymerizable composition capable of forming a phase difference layer exhibiting reverse wavelength dispersion with good light resistance, as described above.

[0120] 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 inverse wavelength dispersion, 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.

[0121] 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 will be 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 can form a phase difference layer exhibiting reverse wavelength dispersion with good light resistance, 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.

[0122] 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.

[0123] 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.).

[0124] 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.).

[0125] 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.).

[0126] 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.

[0127] 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.

[0128] 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 Recuel des Travaux Chimiques des Pays-Bas (1996), 115(6), 321-328.

[0129] 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.

[0130] (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.

[0131] 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.

[0132] 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).

[0133] (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 independent integers between 2 and 10.

[0134] (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).

[0135] 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 preferable that it be 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, -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.

[0136] 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.

[0137]

[0138] 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).

[0139] (g is an integer between 2 and 5.)

[0140]

[0141] As described above, the polymerizable liquid crystal compounds of this disclosure exhibit inverse wavelength dispersibility, so even if compounds exhibiting broad wavelength dispersibility are added, the phase difference value of the cured product of the composition tends to exhibit inverse wavelength dispersibility. As described above, when the phase difference value of the polymerizable liquid crystal compounds of this disclosure is measured, the Re(450) / Re(550) tends to be relatively small. Therefore, in order to adjust to ideal wavelength dispersibility, the polymerizable liquid crystal compounds may further contain polymerizable liquid crystal compounds different from the polymerizable liquid crystal compounds of this disclosure in which the ratio of the in-plane phase difference (Re(450)) for a wavelength of 450 nm to the in-plane phase difference (Re(550)) for a wavelength of 550 nm (Re(550)) in the test method described below (Re(450) / Re(550)) is larger than the Re(450) / Re(550) of the polymerizable liquid crystal compounds of this disclosure that are included. As polymerizable liquid crystal compounds other than those disclosed herein, those with a Re(450) / Re(550) ratio of 0.60 or more and less than 1.20 may be selected, but those with a ratio of 0.80 or more and less than 1.20 may be selected, or those with a ratio of 0.90 or more and less than 1.20 may be selected. The phase difference value here is measured in the same manner as the phase difference value test method described above.

[0142] 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.

[0143] 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.

[0144] 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.

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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. The phase difference film of this embodiment has a phase difference layer that exhibits good light resistance and reverse wavelength dispersion because the phase difference layer is made of a cured product of the polymerizable composition.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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. Increasing the content of the polymerizable liquid crystal compound of this disclosure in the phase difference layer tends to increase the inverse wavelength dispersion characteristics. Furthermore, in order to approach ideal inverse 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 0.95, more preferably in the range of 0.78 or more and less than 0.93, and even more preferably in the range of 0.80 or more and less than 0.90. Furthermore, it is preferable that Re(650) / Re(550) is greater than 1, and more preferably in the range of 1.02 or more and 1.10 or less.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] 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).

[0171] 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.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] 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.

[0176] (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.

[0177] 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.

[0178] (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.

[0179] (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.

[0180] 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.

[0181] 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.

[0182] The transfer laminate of this embodiment has good light resistance and excellent optical properties because the phase difference layer is made of a cured product of the polymerizable composition. 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.

[0183] 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.

[0184] 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.

[0185] 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.

[0186] 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.

[0187] 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.

[0188] 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.

[0189] 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.

[0190] The phase difference layer that can be provided from the transfer laminate of this disclosure is suitably used for applications similar to 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.

[0191] F. Optical component The optical component of the present disclosure comprises a polarizing plate on the phase difference film of the present disclosure.

[0192] 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).

[0193] 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.

[0194] 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.

[0195] 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.

[0196] 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.

[0197] 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.

[0198] 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.

[0199] 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.

[0200] 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.

[0201] 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.

[0202] 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.

[0203] 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.

[0204] Furthermore, in this disclosure, unless otherwise specified, the orientation, in-plane phase difference Re, and in-plane phase difference Re after the lightfastness test in the evaluation items below refer to the average value of nine measured values. The nine measurement locations 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 intersection 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 intersection points of 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 inscribed in that shape, and perform nine measurements on that 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.

[0205] <Example> For the following model compounds Ex1 to Ex5, structural optimization was performed using density functional theory (DFT) calculations, and the G in the general formula (Ar-1) was found. １ The dihedral angle between the aliphatic ring of the alicyclic hydrocarbon group substituted at the position and the fused ring to which the alicyclic hydrocarbon group is bonded was calculated. Density functional theory (DFT) calculations were performed using Gaussian09 from Gaussian, with the functional B3LYP basis set 6-31g(d,p) and other parameters set to the default values ​​of Gaussian09 to optimize and obtain the most stable molecular structure. Note that the dihedral angle between the aliphatic ring of the alicyclic hydrocarbon group and the fused ring to which the alicyclic hydrocarbon group is bonded is the Q of the fused ring. １ =C- and the aliphatic ring G bonded to the fused ring. １ Atom G ｘ And, G ｘ Of the two atoms bonded, Q １ Atom G located on the side ｙ Using Q １ = C - G ｘ With respect to the plane formed by G, ｘ -G ｙ It can be determined by the angle formed by the two sides.

[0206]

[0207]

[0208] (Evaluation of inverse wavelength dispersion) Based on the most stable molecular structures of model compounds Ex1 to Ex5, it is known that the refractive index can be determined using the Lorenz-Lorenz equation from the molecular polarizability (α) obtained using the CAM-B3LYP functional and B3LYP basis set 6-31+G(2d,p). The birefringence between wavelengths of 400 nm and 780 nm can be determined from the difference between the refractive index in the direction of the major axis and the refractive index perpendicular to the major axis. (Reference: Science and Industry, 86 (2), pp. 43-48 (2012)) The obtained birefringences for each wavelength were fitted using Cauchy's formula, and if the resulting curve showed an increasing birefringence in the wavelength range of 400 nm to 550 nm ((birefringence at 450 nm) < (birefringence at 550 nm)), it was determined that the compound possessed inverse wavelength dispersion (○).

[0209]

[0210] G in the general formula (Ar-1) １ It has been shown that when a double bond is included in the alicyclic hydrocarbon group substituted at this position, the dihedral angle between the aliphatic ring of the alicyclic hydrocarbon group and the fused ring to which the alicyclic hydrocarbon group is bonded becomes smaller, and the twisting of the aliphatic ring of the side chain relative to the fused ring of the liquid crystal main chain is suppressed. It is thought that suppressing the twisting of the aliphatic ring of the side chain relative to the fused ring of the liquid crystal main chain maintains the planarity of the aliphatic ring of the side chain relative to the fused ring of the liquid crystal main chain, thus leading to the exhibiting of inverse wavelength dispersion.

[0211] [Production Example 1: Preparation of Polymerizable Liquid Crystal Compound 1 represented by Formula (1-1)] First, 3-ethynyl-2-cyclopentan-1-one was synthesized by the method described in J. Org. Chem. 2019, 84, 17, 10832-10842. In a 300 mL flask equipped with a stirrer, 2 g of 3-ethynyl-2-cyclopentan-1-one, 6 g of 2-bromo-3-iodo-1,4-dimethoxybenzene, and 20 mL of dimethylformamide (DMF) were added and stirred. In the same flask, under a nitrogen atmosphere, 10 mg of copper iodide, 130 mg of bis(triphenylphosphine)palladium(II) dichloride (manufactured by Tokyo Chemical Industry Co., Ltd.), and 5 mL of triethylamine were added, and the mixture was stirred at 50°C for 20 hours. The reaction mixture was transferred to a separatory funnel, 50 mL of toluene and 200 mL of water were added, and the mixture was shaken. After settling, the aqueous layer was removed. The toluene layer was transferred to a 200 mL flask, 10 g of sodium sulfate was added, and the mixture was stirred for 1 hour. The solids were then removed by filtration. Next, the toluene solution was transferred to a 300 mL flask, and under a nitrogen atmosphere, tris(dibenzylideneacetone)dipalladium(0) (1.5 g, manufactured by Tokyo Chemical Industry Co., Ltd.) and dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added and the mixture was stirred at 0°C. A solution of approximately 26% lithium bis(trimethylsilyl)amide (manufactured by Sigma-Aldrich) in tetrahydrofuran (THF) (15 mL) was added dropwise over 30 minutes, and the mixture was stirred for 1 hour. Triisopropylsilanthol (5 g, Sigma-Aldrich) was added and the mixture was stirred for a further 1 hour. Then, a 1 mol / L tetrahydrofuran solution of tetrabutylammonium fluoride (170 mL) was added, and the mixture was heated to 25°C and stirred for 1 hour. After concentrating the reaction mixture, it was purified by silica gel columnography to obtain intermediate 1 (2 g) represented by formula (1-1-1).

[0212] Intermediate 1 (2 g) represented by formula (1-1-1) was dissolved in methylene chloride, cooled to -60°C, and 21 mL of a 17% dichloromethane solution of boron tribromide was added dropwise to the methylene chloride solution over 15 minutes. The mixture was then heated to 25°C and stirred for another hour. 20 mL of water was added to the flask, the aqueous layer was removed using a separatory funnel, and the methylene chloride layer was concentrated and purified by silica gel columnography to obtain intermediate 2 (0.5 g) represented by formula (1-1-2).

[0213] With reference to the method described in the examples of Japanese Patent Publication No. 2021-1150, an intermediate 3 (cyclohexane-1,4-dicarboxylic acid = hydrogen = 4-[6-(acryloyloxy)hexyloxy]phenyl) represented by formula (1-1-3) (5 g) was obtained.

[0214] In a 50 mL flask equipped with a stirrer, intermediate 2 (0.5 g) represented by formula (1-1-2), intermediate 3 (2 g) represented by formula (1-1-3), dimethylaminopyridine (0.01 g), and 10 mL of methylene chloride were added and stirred. After the mixture was cooled to 5°C, N,N'-diisopropylcarbodiimide (1 g, Fujifilm Wako Pure Chemical Industries, Ltd.) was added and stirring was continued for a further 1 hour. Methanol (15 mL) was added to the resulting reaction solution, and the precipitated white solid was collected by filtration to obtain polymerizable liquid crystal compound 1 (0.8 g) represented by formula (1-1).

[0215] Phase transition temperature (when heating): C 119 N 195 I １ 1H NMR (CDCl ３ ; δppm) :7.47 (s, 1H), 7.25 (d, 1H), 7.16 (d, 1H), 6.99-6.97 (m, 4H), 6.89-6.87 (m, 4H) , 6.47 (t, 1H), 6.42 (d, 1H), 6.38 (d, 1H), 6.14 (d, 1H), 6.10 (d, 1H), 5.83 (d, 1H) ), 5.81 (d, 1H), 4.17 (t, 4H), 3.95 (t, 4H), 3.13-3.11 (m, 2H), 2.74-2.64 (m, 2H ), 2.63-2.62 (m, 4H), 2.38-2.32 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0216]

[0217] [Production Example 2: Production of Polymerizable Liquid Crystal Compound 2 represented by Formula (1-2)] Under nitrogen, (4,7-dimethoxy-1-benzothiophen-2-yl)boronic acid (1 g, manufactured by Aurora), 4-bromo-2,3-dihydrofuran (0.65 g, manufactured by Aldrich), and tetrakis(triphenylphosphine)palladium (0) (manufactured by Tokyo Chemical Industry Co., Ltd.) were dissolved in 15 mL of THF. 5 mL of 1 mol / L aqueous potassium carbonate solution was added, and the temperature was raised to 60 degrees Celsius and stirred for 2 hours. The temperature was lowered to room temperature, and toluene and water were added for liquid-liquid separation. The organic layer was washed with dilute hydrochloric acid, then with saturated aqueous sodium bicarbonate solution, and then with saturated brine. Anhydrous sodium sulfate was added and dried, and the solvent was removed by vacuum distillation to obtain a solid. This was dissolved in toluene, and the eluate was obtained by passing it through a silica gel column. Recrystallization was performed using a mixed solvent of ethanol and toluene to obtain 0.87 g of the compound represented by formula (1-2-1).

[0218] 0.87 g of the compound represented by formula (1-2-1) was dissolved in 10 mL of dichloromethane, and 0.83 g of boron tribromide was slowly added at room temperature. After stirring for 2 hours at room temperature, 5 mL of water was added and the mixture was stirred for a while. The organic layer was removed by liquid-liquid extraction, washed with saturated brine, and then dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain 0.70 g of the compound represented by formula (1-2-2).

[0219] In the same manner as in Production Example 1, intermediate 3 represented by formula (1-1-3) was reacted with intermediate 3 represented by formula (1-1-3) in the same manner as in Production Example 1, except that intermediate 2 represented by formula (1-1-2) (0.5 g) was replaced with compound (1-2-2) (0.7 g), to obtain polymerizable liquid crystal compound 2 represented by formula (1-2) (1.3 g).

[0220] Phase transition temperature (when heating): C 120 N 195 I １ 1H NMR (CDCl ３; δppm) :7.45 (s, 1H), 7.25 (d, 1H), 7.15 (d, 1H), 6.99-6.95 (m, 4H), 6.90-6.86 (m, 4H) ), 6.47 (t, 1H), 6.40 (d, 1H), 6.38 (d, 1H), 6.14 (d, 1H), 6.10 (d, 1H), 5.84 (d, 1H), 5.80 (d, 1H), 4.46-4.41 (t, 2H), 4.16 (t, 4H), 3.95 (t, 4H), 2.70 (t, 2H), 2.63-2.62 (m, 4H), 2.38-2.32 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0221]

[0222] [Production Example 3: Production of Polymerizable Liquid Crystal Compound 3 represented by Formula (1-3)] Under nitrogen, 2-chloro-4,7-dimethoxy-1,3-benzothiazole (1 g, Aldrich), (3-oxocyclopent-1-en-1-yl)boronic acid (0.55 g, Aldrich), and tetrakis(triphenylphosphine)palladium (0) (0.14 g, Tokyo Chemical Industry Co., Ltd.) were dissolved in 15 mL of THF. 5 mL of 1 mol / L potassium carbonate aqueous solution was added, and the temperature was raised to 60°C and stirred for 2 hours. The temperature was lowered to room temperature, toluene and water were added and liquid-liquid separated. The organic layer was washed with dilute hydrochloric acid, then with saturated sodium bicarbonate aqueous solution, and then with saturated brine. Anhydrous sodium sulfate was added and dried, and the solvent was removed under reduced pressure to obtain a solid. This was dissolved in toluene, and the eluate was obtained by passing it through a silica gel column. Recrystallization was performed using a mixed solvent of ethanol and toluene to obtain 0.87 g of the compound represented by formula (1-3-1).

[0223] 0.87 g of the compound represented by formula (1-3-1) was dissolved in 10 mL of dichloromethane, and 0.75 g of boron tribromide was slowly added at room temperature. After stirring for 2 hours at room temperature, 5 mL of water was added and the mixture was stirred for a while. The organic layer was removed by liquid-liquid extraction, washed with saturated brine, and then dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain 0.7 g of the compound represented by formula (1-3-2).

[0224] In the same manner as in Production Example 1, intermediate 3 represented by formula (1-1-3) was reacted with intermediate 3 represented by formula (1-1-3) in the same manner as in Production Example 1, except that intermediate 2 represented by formula (1-1-2) (0.5 g) was replaced with compound (1-3-2) (0.7 g), thereby obtaining polymerizable liquid crystal compound 3 represented by formula (1-3) (1.3 g).

[0225] Phase transition temperature (when heating): C 107 N 180 I １ 1H NMR (CDCl ３ ; δppm) :7.29 (d, 1H), 7.17 (d, 1H), 7.03-6.99 (m, 4H), 6.95-6.92 (m, 4H), 6.47 (t, 1H), 6.42 (d, 1H), 6.38 (d, 1H), 6.16 (d, 1H), 6.12 (d, 1H), 5.85 (d, 1H), 5.81 (d, 1H), 4.16 (t, 4H), 3.95 (t, 4H), 3.13-3.11 (m, 2H), 2.74-2.64 (m, 2H), 2 .63-2.60 (m, 4H), 2.38-2.32 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0226]

[0227] [Production Example 4: Production of Polymerizable Liquid Crystal Compound 4 represented by Formula (1-4)] 0.9 g of the compound represented by formula (1-4-1) was obtained in the same manner as in Production Example 2, except that 5-bromo-2,3-dihydrofuran (0.65 g, manufactured by Aldrich) was used instead of 0.65 g of 4-bromo-2,3-dihydrofuran. 0.72 g of the compound represented by formula (1-4-2) was obtained in the same manner as in Production Example 2, except that 0.9 g of the compound represented by formula (1-4-1) was used instead of 0.87 g of the compound represented by formula (1-2-1). 1.4 g of polymerizable liquid crystal compound 4 represented by formula (1-4) was obtained by reacting it with intermediate 3 represented by formula (1-1-3) in the same manner as in Production Example 1, except that intermediate 2 (0.5 g) represented by formula (1-1-2) was used instead of compound (1-4-2) (0.72 g).

[0228] Phase transition temperature (when heating): C 120 N 190 I １1H NMR (CDCl ３ ; δppm) :7.45 (s, 1H), 7.25 (d, 1H), 7.16 (d, 1H), 6.99-6.97 (m, 4H), 6.90-6.86 (m, 4 H), 6.40 (d, 1H), 6.38 (d, 1H), 6.14 (d, 1H), 6.10 (d, 1H), 5.84 (d, 1H), 5.80 (d , 1H), 4.16 (t, 4H), 3.95 (t, 4H), 3.75 (t, 2H), 3.13 (t, 2H), 2.63-2.62 (m, 4H) , 2.38-2.32 (m, 8H), 2.10-2.00 (m, 1H) 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0229]

[0230] [Production Example 5: Production of polymerizable liquid crystal compound 5 represented by formula (1-5)] 0.75 g of the compound represented by formula (1-5-1) was obtained in the same manner as in Production Example 3, except that 4,5-dihydro-2-furanylboronic acid (0.5 g, manufactured by Aldrich) was used instead of 0.55 g of (3-oxocyclopent-1-en-1-yl)boronic acid. 0.63 g of the compound represented by formula (1-5-2) was obtained in the same manner as in Production Example 3, except that 0.75 g of the compound represented by formula (1-5-1) was used instead of 0.87 g of the compound represented by formula (1-3-1). In the same manner as in Production Example 1, intermediate 3 represented by formula (1-1-3) was reacted with compound (0.63 g) represented by formula (1-5) to obtain polymerizable liquid crystal compound 5 (1.3 g) represented by formula (1-5).

[0231] Phase transition temperature (when heating): C 110 N 185 I １ 1H NMR (CDCl ３(δ ppm) :7.29 (d, 1H), 7.17 (d, 1H), 7.03-6.99 (m, 4H), 6.95-6.92 (m, 4H), 6.45 (d , 1H), 6.40 (d, 1H), 6.16 (d, 1H), 6.12 (d, 1H), 5.85 (d, 1H), 5.81 (d, 1H), 4 .17 (t, 4H), 3.95 (t, 4H), 3.76 (t, 2H), 3.13 (t, 2H), 2.63-2.60 (m, 4H), 2. 38-2.32 (m, 8H), 2.10-2.00 (m, 1H), 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0232]

[0233] [Production Example 6: Production of Polymerizable Liquid Crystal Compound 6 Represented by Formula (1-6)] 0.95 g of the compound represented by formula (1-6-1) was obtained in the same manner as in Production Example 2, except that 3-bromo-2-cyclopenten-1-one (0.70 g, manufactured by Aldrich) was used instead of 0.65 g of 4-bromo-2,3-dihydrofuran. 0.75 g of the compound represented by formula (1-6-2) was obtained in the same manner as in Production Example 2, except that 0.95 g of the compound represented by formula (1-6-1) was used instead of 0.87 g of the compound represented by formula (1-2-1). 1.5 g of polymerizable liquid crystal compound 6 (1.5 g) represented by formula (1-6) was obtained by reacting it with intermediate 3 represented by formula (1-1-3) in the same manner as in Production Example 1, except that intermediate 2 (0.5 g) represented by formula (1-1-2) was used instead of compound (1-6-2) (0.75 g).

[0234] Phase transition temperature (when heating): C 119 N 190 I １ 1H NMR (CDCl ３; δppm) :7.48 (s, 1H), 7.25 (d, 1H), 7.16 (d, 1H), 6.99-6.97 (m, 4H), 6.89-6.87 (m, 4H), 6.42 (d, 1H), 6.38 (d, 1H), 6.32 (t, 1H), 6.14 (d, 1H), 6.10 (d, 1H), 5.83 (d, 1H), 5.81 (d, 1H), 4.17 (t, 4H), 3.95 (t, 4H), 3.22 (d, 2H), 2.70 (s, 2H), 2 .63-2.62 (m, 4H), 2.38-2.32 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0235]

[0236] [Production Example 7: Production of polymerizable liquid crystal compound 7 represented by formula (1-7)] 1.0 g of the compound represented by formula (1-7-1) was obtained in the same manner as in Production Example 2, except that 3-bromo-2-cyclohexen-1-one (0.78 g, manufactured by Aldrich) was used instead of 0.65 g of 4-bromo-2,3-dihydrofuran. 0.74 g of the compound represented by formula (1-7-2) was obtained in the same manner as in Production Example 2, except that 1.0 g of the compound represented by formula (1-7-1) was used instead of 0.87 g of the compound represented by formula (1-2-1). 1.1 g of polymerizable liquid crystal compound 7 represented by formula (1-7) was obtained by reacting it with intermediate 3 represented by formula (1-1-3) in the same manner as in Production Example 1, except that intermediate 2 (0.5 g) represented by formula (1-1-2) was used instead of the compound represented by formula (1-7-2) (0.74 g).

[0237] Phase transition temperature (when heating): C 120 N 190 I １ 1H NMR (CDCl ３; δppm) :7.48 (s, 1H), 7.25 (d, 1H), 7.16 (d, 1H), 6.99-6.97 (m, 4H), 6.89-6.87 (m, 4H) , 6.42 (d, 1H), 6.38 (d, 1H), 6.36-6.30 (m, 1H), 6.14 (d, 1H), 6.10 (d, 1H), 5.83 (d, 1H), 5.81 (d, 1H), 4.17 (t, 4H), 3.95 (t, 4H), 3.28 (d, 2H), 2.74-2.64 (m, 6H ), 2.58-2.52 (m, 2H), 2.38-2.32 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0238]

[0239] [Production Example 8: Production of Polymerizable Liquid Crystal Compound 8 represented by Formula (1-8)] 0.95 g of the compound represented by Formula (1-8-1) was obtained in the same manner as in Production Example 2, except that 4-bromo-3,6-dihydro-2H-pyran (0.7 g, manufactured by Aldrich) was used instead of 0.65 g of 4-bromo-2,3-dihydrofuran. 0.73 g of the compound represented by Formula (1-8-2) was obtained in the same manner as in Production Example 2, except that 0.95 g of the compound represented by Formula (1-8-1) was used instead of 0.87 g of the compound represented by Formula (1-2-1). In the same manner as in Production Example 1, intermediate 3 represented by formula (1-1-3) was reacted with compound (0.73 g) represented by formula (1-8) to obtain polymerizable liquid crystal compound 8 (1.2 g) represented by formula (1-8).

[0240] Phase transition temperature (when heating): C 120 N 195 I １ 1H NMR (CDCl ３; δppm) :7.45 (s, 1H), 7.20 (d, 1H), 7.13 (d, 1H), 6.94-6.92 (m, 4H), 6.85-6.81 (m, 4H) ), 6.42 (d, 1H), 6.38 (d, 1H), 6.20-6.16 (m, 1H), 6.14 (d, 1H), 6.10 (d, 1H), 5. 83 (d, 1H), 5.81 (d, 1H), 4.35 (dd, 2H), 4.17 (t, 4H), 3.96 (t, 2H), 3.95 (t, 4H) , 2.63-2.52 (m, 6H), 2.38-2.32 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0241]

[0242] [Production Example 9: Production of polymerizable liquid crystal compound 9 represented by formula (1-9)] 0.82 g of the compound represented by formula (1-9-1) was obtained in the same manner as in Production Example 2, except that 5-bromo-3,4-dihydro-2H-pyran (0.70 g, manufactured by Aldrich) was used instead of 0.65 g of 4-bromo-2,3-dihydrofuran. 0.62 g of the compound represented by formula (1-9-2) was obtained in the same manner as in Production Example 2, except that 0.82 g of the compound represented by formula (1-9-1) was used instead of 0.87 g of the compound represented by formula (1-9-1) in Production Example 2. In the same manner as in Production Example 1, intermediate 3 represented by formula (1-1-3) was reacted with intermediate 3 represented by formula (1-1-3) in the same manner as in Production Example 1, except that intermediate 2 represented by formula (1-1-2) (0.5 g) was replaced with compound (1-9-2) (0.62 g), to obtain polymerizable liquid crystal compound 9 represented by formula (1-9) (1.3 g).

[0243] Phase transition temperature (when heating): C 120 N 195 I １ 1H NMR (CDCl ３; δppm) :7.47 (s, 1H), 7.20 (d, 1H), 7.13 (d, 1H), 6.94-6.92 (m, 4H), 6.85-6.81 (m, 4H) , 6.42 (d, 1H), 6.38 (d, 1H), 6.18-6.15 (m, 2H), 6.10 (d, 1H), 5.83 (d, 1H), 5.81 (d, 1H), 4.33 (q, 2H), 4.17 (t, 4H), 3.95 (t, 4H), 3.94 (t, 2H), 2.63-2.60 (m, 4H) ), 2.55-2.50 (m, 2H), 2.38-2.32 (m, 8H), 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0244]

[0245] [Production Example 10: Production of polymerizable liquid crystal compound 10 represented by formula (1-10)] 0.85 g of the compound represented by formula (1-10-1) was obtained in the same manner as in Production Example 2, except that 3-bromo-2-methylcyclopent-2-en-1-one (0.77 g, manufactured by Aurora Chemieliva) was used instead of 0.65 g of 4-bromo-2,3-dihydrofuran. 0.7 g of the compound represented by formula (1-10-2) was obtained in the same manner as in Production Example 2, except that 0.85 g of the compound represented by formula (1-10-1) was used instead of 0.87 g of the compound represented by formula (1-2-1) in Production Example 2. In the same manner as in Production Example 1, intermediate 3 represented by formula (1-1-3) was reacted with intermediate 3 represented by formula (1-1-3) in the same manner as in Production Example 1, except that intermediate 2 represented by formula (1-1-2) (0.5 g) was replaced with compound (1-10-2) (0.7 g), to obtain polymerizable liquid crystal compound 10 represented by formula (1-10) (1.3 g).

[0246] Phase transition temperature (when heating): C 119 N 190 I １ 1H NMR (CDCl ３; δppm) :7.48 (s, 1H), 7.25 (d, 1H), 7.16 (d, 1H), 6.99-6.97 (m, 4H), 6.89-6.87 (m, 4H) , 6.42 (d, 1H), 6.38 (d, 1H), 6.14 (d, 1H), 6.10 (d, 1H), 5.83 (d, 1H), 5.81 (d, 1H) ), 4.17 (t, 4H), 3.96 (t, 4H), 2.96-2.89 (m, 2H), 2.63-2.62 (m, 4H), 2.56-2.51 (m, 2H), 2.38-2.32 (m, 8H), 1.96 (s, 3H) 1.81-1.68 (m, 16H), 1.53-1.44 (m, 8H)

[0247]

[0248] [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.

[0249]

[0250] [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.

[0251]

[0252] [Comparative Production Example 3: Production of Comparative Compound 3 represented by formula (C1-3)] 0.75 g of the compound represented by formula (C1-3-1) was obtained in the same manner as in Production Example 2, except that bromocyclopentane (0.65 g, manufactured by Tokyo Chemical Industry Co., Ltd.) was used instead of 0.65 g of 4-bromo-2,3-dihydrofuran. 0.5 g of the compound represented by formula (C1-3-2) was obtained in the same manner as in Production Example 2, except that 0.75 g of the compound represented by formula (C1-3-1) was used instead of 0.87 g of the compound represented by formula (1-2-1). 0.8 g of the compound represented by formula (C1-3) was obtained by reacting it with intermediate 3 represented by formula (1-1-3) in the same manner as in Production Example 1, except that intermediate 2 (0.5 g) represented by formula (1-1-2) was used instead of compound (0.5 g) represented by formula (C1-3).

[0253] Phase transition temperature (when heating): C 10⁵ N 17⁰ I １ 1H NMR (CDCl ３ ; δppm) :7.45 (s, 1H), 7.20 (d, 1H), 7.12 (d, 1H), 6.95-6.95 (m, 4H), 6.85-6.80 (m, 4H), 6.42 (d, 1H), 6.38 (d, 1H), 6.14 (d, 1H), 6.10 (d, 1H), 5.83 (d, 1H), 5.81 (d, 1H), 4.17 (t, 4H), 3.95 (t, 4H), 3.03-2.96 (m, 1H), 2.63-2.62 (m, 4H), 2 .38-2.32 (m, 8H), 2.08-2.06 (m, 2H), 1.83-1.60 (m, 22H), 1.53-1.44 (m, 8H)

[0254]

[0255] [Example 1] (1) Preparation of polymerizable composition Polymerizable composition 1 was prepared by dissolving 100 parts by mass of a polymerizable liquid crystal compound (compound 1 represented by formula (1-1)) and 4 parts by mass of a photopolymerization initiator (2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, manufactured by Sigma-Aldrich, Irgacure 907) in 900 parts by mass of cyclopentanone.

[0256] (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

[0257]

[0258] (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.

[0259] (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.

[0260] [Examples 5-13] (1) Production of polymerizable composition Polymerizable compositions 5-13 were obtained in the same manner as in Example 1, except that the polymerizable liquid crystal compound (compound 1 represented by formula (1-1)) was changed according to Table 20 below. (2) Production of phase difference film or transfer laminate Polymerizable compositions 5-13 were obtained in the same manner as in Example 1, except that polymerizable compositions 5-13 were used instead of polymerizable composition 1 in Example 1.

[0261] [Comparative Examples 1-3] (1) Comparative polymerizable compositions 1-3 were obtained in the same manner as in Example 1, except that the polymerizable liquid crystal compound (compound 1 represented by formula (1-1)) was changed according to Table 20 below. (2) Comparative phase difference films or transfer laminates 1-3 were obtained in the same manner as in Example 1, except that comparative polymerizable compositions 1-3 were used instead of polymerizable composition 1.

[0262] [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, wavelength dispersion, and lightfastness of these samples were evaluated.

[0263] <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

[0264] <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: 0.6 ≤ x < 0.95, 1.00 < y ... inverse wavelength dispersion B: 0.95 ≤ x < 1.00, 1.00 < y C: 1.00 ≤ x, 1.00 ≥ y ... normal dispersion

[0265] <Lightfastness> Samples in which phase difference film and horizontal alignment film were transferred to adhesive glass were tested using an accelerated lightfastness tester (UV autofade meter U48AU manufactured by Suga Test Instruments Co., Ltd.) at a temperature of 63°C, humidity of 40%, and illuminance of 500±100 W / m². ２ A lightfastness test was conducted by irradiating the sample for 48 hours. (Phase difference variation measurement) The in-plane phase difference Re at a wavelength of 550 nm was measured before and after the lightfastness test, and the variation value before and after the lightfastness test was evaluated. z (%) = {1 - (In-plane phase difference Re after the lightfastness test at 550 nm) / (In-plane phase difference Re before the lightfastness test at 550 nm)} × 100 (Evaluation criteria for lightfastness and phase difference variation value) A: z < 10% B: 10% ≤ z

[0266]

[0267] [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 21 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.

[0268]

[0269] [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 19 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.

[0270]

[0271] [Evaluation] <Sample Preparation> The orientation, wavelength dispersion, and lightfastness of each example were evaluated in the same manner as in Example 1. The evaluation results are shown in Table 22.

[0272]

[0273] [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 23 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.

[0274] The orientation, wavelength dispersion, and lightfastness of each example were evaluated in the same manner as in Example 1. The evaluation results are shown in Table 24.

[0275]

[0276]

[0277] 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 a divalent group represented by the following general formula (Ar-1), L ２ , ２ , ２ , ２ , ２ , ２ , ２ , ２ and L ２ and 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. (In the general formula (Ar-1), * represents the bond position, Q １ is -N= or -CR ａ Represents =, Q ２ -O-, -S-, -NR ｂ - or -CR ｃ R ｄ - represents, G １ This is an alicyclic hydrocarbon group having 3 to 20 carbon atoms and containing at least one intraring double bond, wherein the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -NR ｅ R represents a monovalent group which may be replaced by -, -CS-, or -CO-, and which may be substituted by one or more substituents E. ａ , R ｃ , and R ｄ Each of these independently represents a hydrogen atom or a substituent E, and R ｂ , and R ｅ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. E １ and E ２ Each of these independently represents a hydrogen atom or a substituent E, or E １ and E ２ These elements may be linked to each other, forming an aliphatic ring or an aliphatic heterocycle. The substituent E is each independently a halogen atom, a cyano group, a nitro group, -OR ｆ , -NR ｇ R ｈ , -SR ｉ , -COOR ｊ , -OCOR ｋ , -COR ｌ , -SiR ｍ R ｎ R ｏ , an alicyclic hydrocarbon group having 3 to 20 carbon atoms, or -L Ｅ -R ｓｐＥ -Z Ｅ represents a group represented by, or an alkyl group having 1 to 20 carbon atoms which may be substituted by one or more of these, and -CH ２ - in the alkyl group 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 R ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, 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-, -CF=CF-, -C≡C-, or single bond are represented by 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. If multiple substituents E exist within a compound, they may be the same or different. In the above general formula (I), A １ and A ２ The polymerizable liquid crystal compound according to claim 1, 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. 　 In the above general formula (I), G １ The polymerizable liquid crystal compound according to claim 1 or 2, wherein the alicyclic hydrocarbon group has a total number of atoms constituting the ring of 5 to 8, and the number of π electrons contained in the alicyclic hydrocarbon group is 4 or more. 　 A compound represented by the following general formula (Ar-im). (In the general formula (Ar-im), Q １ is -N= or -CR ａ Represents =, Q ２ -O-, -S-, -NR ｂ - or -CR ｃ R ｄ - represents, G １ This is an alicyclic hydrocarbon group having 3 to 20 carbon atoms and containing at least one intraring double bond, wherein the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -NR ｅ R represents a monovalent group which may be replaced by -, -CS-, or -CO-, and which may be substituted by one or more substituents E. ａ , R ｃ , and R ｄ Each of these independently represents a hydrogen atom or a substituent E, and R ｂ , and R ｅ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. E １ and E ２ Each of these independently represents a hydrogen atom or a substituent E, or E １ and E ２ These elements may be linked to each other to form an aliphatic ring or an aliphatic heterocycle. 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. Each of the substituents E is independently a halogen atom, a cyano group, a nitro group, or -OR ｆ , -NR ｇ R ｈ ,-SR ｉ , -COOR ｊ , -OCOR ｋ , -COR ｌ , -SiR ｍ R ｎ R ｏ , alicyclic hydrocarbon groups having 3 to 20 carbon atoms, or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an alkyl group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the alkyl group contains -CH ２ - may be replaced with -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-, R ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 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-, -CF=CF-, -C≡C-, or single bond are represented by 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. If multiple substituents E exist within a compound, they may be the same 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), Q １ is -N= or -CR ａ Represents =, Q ２ -O-, -S-, -NR ｂ - or -CR ｃ R ｄ - represents, G １ This is an alicyclic hydrocarbon group having 3 to 20 carbon atoms and containing at least one intraring double bond, wherein the alicyclic hydrocarbon group contains -CH ２ - is -O-, -S-, -NR ｅ R represents a monovalent group which may be replaced by -, -CS-, or -CO-, and which may be substituted by one or more substituents E. ａ , R ｃ , and R ｄ Each of these independently represents a hydrogen atom or a substituent E, and R ｂ , and R ｅ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. E １ and E ２ Each of these independently represents a hydrogen atom or a substituent E, or E １ and E ２ These elements may be linked to each other to form an aliphatic ring or an aliphatic heterocycle. 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. Each of the substituents E is independently a halogen atom, a cyano group, a nitro group, or -OR ｆ , -NR ｇ R ｈ ,-SR ｉ , -COOR ｊ , -OCOR ｋ , -COR ｌ , -SiR ｍ R ｎ R ｏ , alicyclic hydrocarbon groups having 3 to 20 carbon atoms, or -L Ｅ -R ｓｐＥ -Z Ｅ A group represented by , or an alkyl group having 1 to 20 carbon atoms which may be substituted by one or more of these, and the alkyl group contains -CH ２ - may be replaced with -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-, R ｆ , R ｇ , R ｈ , R ｉ , R ｊ , R ｋ , R ｌ , R ｍ , R ｎ , and R ｏ Each of these independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. 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-, -CF=CF-, -C≡C-, or single bond are represented by 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. If multiple substituents E exist within a compound, they may be the same 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) < 0.

95. 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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