JP7255111B2 - Polymerizable composition, polymer, retardation film and method for producing same, laminate for transfer, optical member and method for producing same, and display device - Google Patents

Description

TECHNICAL FIELD The present disclosure relates to a polymerizable composition, a polymer, a retardation film and its manufacturing method, a transfer laminate, an optical member and its manufacturing method, and a display device.

2. Description of the Related Art Conventionally, regarding display devices such as liquid crystal display devices and light-emitting display devices, there has been proposed a configuration in which an optical member such as a retardation film or a polarizing plate is arranged on a panel surface.
For example, in a light-emitting display device such as an organic light-emitting display device, a highly reflective metal electrode is provided in order to efficiently utilize light from a light-emitting layer. On the other hand, the use of the metal electrode increases external light reflection. Therefore, in a light-emitting display device, it is known that a circularly polarizing plate including a polarizer and a quarter-wave plate that converts linearly polarized light into circularly polarized light is used on the viewing side for the purpose of suppressing the reflection of external light. It is

In addition to the quarter-wave plate, the retardation film includes a half-wave plate that converts the plane of polarization vibration of linearly polarized light by 90 degrees. These retardation films are capable of converting a specific monochromatic light into a retardation of 1/4λ or 1/2λ of the light wavelength accurately. However, conventional retardation films have a problem that the polarized light output through the retardation film is converted into colored polarized light. This is because the material constituting the retardation film has a wavelength dispersion property with respect to the retardation, and the distribution of the polarization state for each wavelength occurs with respect to white light in which light rays in the visible light range are mixed. In order to prevent this problem, it is necessary to control the wavelength dispersion so that the retardation is designed at each wavelength. A retardation film having wavelength dispersion is desired.

The retardation film is produced by a method of stretching a film, for example, on an orientation-treated support, applying a polymerizable composition containing a liquid crystal compound, drying the solvent, orienting the liquid crystal compound, A method of producing by polymerizing with ultraviolet rays or heat is mentioned.
As a retardation film having reverse wavelength dispersion, for example, a method has been proposed in which two retardation layers are laminated with an angle in the orientation axis direction (Patent Documents 1 and 2). However, in such a laminate, two retardation layers are required, and there are problems such as the complexity of manufacturing when laminating the two retardation layers and the thickness of the retardation film becoming thicker. there were.

With the increasing sophistication and popularization of portable information terminals, it has been required to reduce the thickness of display devices.
Therefore, it is possible to form a retardation layer having reverse wavelength dispersion with one layer, so that the wavelength dispersion of the birefringence (Δn) is reduced or reversed, and the reverse wavelength dispersion is realized. Development of liquid crystal compounds shown in FIG. A graph obtained by plotting the wavelength λ of incident light to the retardation film on the horizontal axis and the birefringence (Δn = refractive index n _e for extraordinary light - refractive index n ₀ for ordinary light) on the vertical axis. When the slope of is positive (increasing to the right), it is generally said that the wavelength dispersion of the birefringence is opposite, or the liquid crystal compound of the material constituting the retardation film exhibits reverse wavelength dispersion. It is

However, conventional liquid crystal compounds exhibiting reverse wavelength dispersion, such as the compounds of Patent Documents 3 and 4, have a small birefringence (Δn). )×film thickness d), it was necessary to increase the film thickness. In addition, conventional liquid crystal compounds exhibiting reverse wavelength dispersion generally have low solubility in organic solvents, and it is difficult to form a uniform coating film when dissolved in an organic solvent and applied with ink to form a coating film. In addition, there is a problem that the load on the manufacturing process and manufacturing equipment for drying a large amount of solvent is increased.

Patent Document 5 discloses a polymerizable compound that has a practically low melting point, is highly soluble in general-purpose solvents, and can obtain an optical film capable of uniform polarization conversion in a wide wavelength range. Structures are disclosed having two side chains on a single tetravalent benzene ring group in the chain. It is shown that the polymerizable compound itself of Patent Document 5 does not have liquid crystallinity (Table 1 of Patent Document 5). An optical film having reverse wavelength dispersion is disclosed by mixing a conventional reverse wavelength dispersion liquid crystal compound with the polymerizable compound of Patent Document 5, but the reverse wavelength dispersion is an ideal reverse wavelength dispersion. There is a large gap between

Patent document 6 discloses that it has high transmittance in the visible region and has a long liquid crystal phase retention time at room temperature, so that it is easy to handle and can control wavelength dispersion characteristics without requiring complicated steps. , as a polymerizable liquid crystal composition capable of producing an optically anisotropic film exhibiting low wavelength dispersion characteristics and reverse wavelength dispersion, a direct or double bond at the 2- or 3-position of 1,4-phenylene as a core skeleton A polymerizable liquid crystal composition containing a compound represented by formula (1) having an aromatic ring via is disclosed. In Patent Document 6, by using the polymerizable liquid crystal composition, the birefringence Δn (450) for light with a wavelength of 450 nm and the birefringence Δn (550) for light with a wavelength of 550 nm are Δn (450)/ It is described that an optically anisotropic film satisfying the relationship Δn(550)≦1.05, that is, an optically anisotropic film exhibiting low wavelength dispersion characteristics or reverse wavelength dispersion characteristics can be produced. However, Δn(450)/Δn(550) realized by the compound represented by Formula (1) of Patent Document 6 is 0.996 at the minimum, and at most low wavelength dispersion (flat wavelength dispersion ) is obtained, and a reverse wavelength dispersion of less than 0.99 is not obtained. In addition, in the case of a structure in which an aromatic ring is bonded directly or via a double bond to the 2- or 3-position of 1,4-phenylene disclosed in Patent Document 6, the solubility in organic solvents is still insufficient. There is Although the examples of Patent Document 6 show that the compound represented by formula (1) of Patent Document 6 has high solvent solubility, it contains an alkylene group between the ring structures in the longitudinal direction, High solvent solubility is achieved by adopting a liquid crystal structure that enhances solubility. In addition, the polymerizable liquid crystal composition containing the compound represented by Formula (1) of Patent Document 6 has insufficient stability because the compound tends to precipitate during storage, as shown in Comparative Examples below. There was a problem that The stability of the composition (ink) is an important performance for producing an optically anisotropic film.

For example, if ideal inverse wavelength dispersion is obtained in a quarter-wave plate, all wavelengths in the visible light region can be converted into circularly polarized light, so that external light can be perfectly prevented from being reflected. However, conventional liquid crystal compounds exhibiting reverse wavelength dispersion are insufficient to exhibit ideal reverse wavelength dispersion by themselves, and it is desired to approach ideal reverse wavelength dispersion. Therefore, it has good solvent solubility, is difficult to precipitate, has good ink stability (solution stability), and is capable of adjusting the wavelength dispersion characteristics so as to approach the ideal reverse wavelength dispersion property. There has been a demand for a polymerizable liquid crystal composition that exhibits

JP-A-10-68816 JP-A-2001-4837 Japanese Patent Publication No. 2010-522893 Japanese Patent No. 5962760 International Publication No. 2014/061709 JP 2016-166344 A

In view of the circumstances as described above, the embodiments of the present disclosure provide a polymerizable composition having good solution stability and exhibiting reverse wavelength dispersion, a polymer obtained by polymerizing the polymerizable composition, and the polymerizable composition. A retardation film having a retardation layer containing a cured product of a composition and a method for producing the same, a transfer laminate capable of transferring the retardation layer, an optical member having the retardation film, and a transfer laminate using the transfer laminate It aims at providing the manufacturing method of an optical member, and a display apparatus.

One embodiment of the present disclosure includes a polymerizable liquid crystal compound (A) represented by the following general formula (1) and a polymerizable liquid crystal compound (B) represented by the following general formula (2), a polymerizable A composition is provided.

（一般式（１）中、Ｌ^１、Ｌ^２、Ｌ^３及びＬ^４はそれぞれ独立して、－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_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_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_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－又は単結合を表し、
Ａ^１及びＡ^２はそれぞれ独立して、無置換であるか又は１つ以上の置換基Ｅによって置換されていても良いシクロヘキサン－１，４－ジイル基、シクロペンタン－１，３－ジイル基、シクロヘプタン－１，３－ジイル基、シクロヘプタン－１，４－ジイル基、デカヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表し、
Ａ^３及びＡ^４はそれぞれ独立して、無置換であるか又は１つ以上の置換基Ｅによって置換されていても良いシクロヘキサン－１，４－ジイル基、シクロペンタン－１，３－ジイル基、シクロヘプタン－１，３－ジイル基、シクロヘプタン－１，４－ジイル基、ベンゼン－１，４－ジイル基、ピリジン－２，５－ジイル基、ピリミジン－２，５－ジイル基、ナフタレン－２，６－ジイル基、ナフタレン－２，７－ジイル基、ナフタレン－１，４－ジイル基、テトラヒドロナフタレン－２，６－ジイル基、デカヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表し、
Ｒ^１及びＲ^２はそれぞれ独立して、下記一般式（Ｒ－１）から選ばれる基を表し、
一般式（Ｒ－１）： －Ｌ^５－Ｒ^ｓｐ１－Ｚ^１
一般式（Ｒ－１）中、Ｌ^５は、－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_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_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_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－又は単結合を表し、Ｒ^ｓｐ１は、炭素原子数１～２０のアルキレン基又は単結合を表し、当該アルキレン基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－ＣＯＯ－、－ＯＣＯ－、－ＯＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－又は－Ｃ≡Ｃ－に置き換えられていても良く、Ｚ^１は重合性官能基を表す。
Ｄ^１及びＤ^２はそれぞれ独立して、下記一般式（Ｄ_ｇ－１）から選ばれる基を表し、
置換基Ｅ、Ｅ^１及びＥ^２はそれぞれ独立して、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、これらによって置換されていても良い炭素原子数１～２０のアルキル基を表し、当該アルキル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられていても良く、或いは、置換基Ｅ、Ｅ^１及びＥ^２はそれぞれ独立して、－Ｌ^Ｅ－Ｒ^ｓｐＥ－Ｚ^Ｅで表される基を表しても良く、ここでＬ^Ｅ、Ｒ^ｓｐＥ、及びＺ^Ｅは、それぞれ、前記Ｌ^５、Ｒ^ｓｐ１、及びＺ^１で定義されるものと同一のものを表すが、それぞれ前記Ｌ^５、Ｒ^ｓｐ１、及びＺ^１と同一であっても異なっていても良く、化合物内に置換基Ｅ、Ｅ^１及びＥ^２がそれぞれ複数存在する場合は、各々同一であっても異なっていても良く、
Ｌ^３、Ｌ^４、Ａ^３、及びＡ^４がそれぞれ複数存在する場合は、各々同一であっても異なっていても良い。
ｍ１及びｍ２はそれぞれ独立して１～４の整数を表し、ｎ１及びｎ２はそれぞれ独立して０～３の整数を表す。）

(In general formula (1), L ¹ , L ² , L ³ and L ⁴ are each independently -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ - , -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH- , -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, - CF ₂ S-, -SCF ₂ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ - , -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -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 represents a single bond,
A ¹ and A ² are each independently a cyclohexane-1,4-diyl group, a cyclopentane-1,3-diyl group, which may be unsubstituted or substituted with one or more substituents E, represents a cycloheptane-1,3-diyl group, a cycloheptane-1,4-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,3-dioxane-2,5-diyl group,
A ³ and A ⁴ are each independently a cyclohexane-1,4-diyl group, a cyclopentane-1,3-diyl group, which may be unsubstituted or substituted with one or more substituents E, cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, benzene-1,4-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2 ,6-diyl group, naphthalene-2,7-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane - represents a 2,5-diyl group,
R ¹ and R ² each independently represent a group selected from general formula (R-1) below,
General formula (R-1): -L ⁵ -R ^sp1 -Z ¹
In general formula (R-1), L ⁵ is -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 represents a single bond, R ^sp1 is carbon represents an alkylene group having 1 to 20 atoms or a single bond, in which one —CH ₂ — or two or more non-adjacent —CH ₂ — in the alkylene group are each independently —O—, —COO; -, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH- or -C≡C-, and Z ¹ is a polymerizable functional group represents
D ¹ and D ² each independently represent a group selected from the following general formula (D _g -1),
Substituents E, E ¹ and E ² are each independently fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or an alkyl group having 1 to 20 carbon atoms optionally substituted by these, one -CH ₂ - or two or more non-adjacent -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, - CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO- CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, or substituents E, E ¹ and E ² are Each independently may represent a group represented by -L ^E -R ^spE -Z ^E , wherein L ^E , R ^spE and Z ^E are respectively the L ⁵ , R ^sp1 and Z ¹ but may be the same as or different from L ⁵ , R ^sp1 and Z ¹ , and the substituents E, E ¹ and E ² in the compound are respectively When there are more than one, each may be the same or different,
When there are a plurality of L ³ , L ⁴ , A ³ and A ⁴ , they may be the same or different.
m1 and m2 each independently represent an integer of 1 to 4; n1 and n2 each independently represent an integer of 0 to 3; )

（一般式（Ｄ_ｇ－１）中、Ｇ^１は水素原子又は炭素原子数１～６のアルキル基を表すが、当該アルキル基は無置換であるか又は１つ以上の前記置換基Ｅによって置換されていても良く、
Ｑ^１は、芳香環を有する炭素原子数２～３０の有機基を表すが、当該芳香環は無置換であるか又は１つ以上の前記置換基Ｅによって置換されていても良く、
Ｊ^１は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ－、－ＯＣＯ－Ｏ－、－ＮＱ^２－、－Ｎ＝ＣＱ^２－、－ＣＯ－ＮＱ^２－、－ＯＣＯ－ＮＱ^２－又は－Ｏ－ＮＱ^２－を表し、Ｑ^２は水素原子、炭素原子数１～２０のアルキル基、炭素原子数３～１２のシクロアルキル基、炭素原子数３～１２のシクロアルケニル基、芳香環を有する炭素原子数２～３０の有機基、又は－（Ｌ^６－Ａ^５）_ｑ－Ｌ^７－Ｒ^ｓｐ２－Ｚ^２を表し、当該アルキル基、シクロアルキル基、シクロアルケニル基、及び芳香環はそれぞれ、無置換であるか又は１つ以上の前記置換基Ｅによって置換されていても良く、当該アルキル基は当該シクロアルキル基又はシクロアルケニル基によって置換されていても良く、当該アルキル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－は各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－ＳＯ_２－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられていても良く、当該シクロアルキル基又はシクロアルケニル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－は各々独立して－Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、又は－Ｏ－ＣＯ－Ｏ－に置き換えられていても良く、Ｌ^６、Ａ^５、Ｌ^７、Ｒ^ｓｐ２、及びＺ^２は、それぞれ、前記Ｌ^１～Ｌ^４、Ａ^３～Ａ^４、Ｌ^５、Ｒ^ｓｐ１、及びＺ^１で定義されるものと同一のものを表すが、それぞれ前記Ｌ^１～Ｌ^４、Ａ^３～Ａ^４、Ｌ^５、Ｒ^ｓｐ１、及びＺ^１と同一であっても異なっていても良く、ｑは０～４の整数を表し、Ｌ^６、及びＡ^５がそれぞれ複数存在する場合は、各々同一であっても異なっていても良い。或いは、Ｑ^１とＱ^２は結合して環を構成していても良い。）

(In the general formula (D _g -1), G ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group is unsubstituted or substituted with one or more substituents E It may be
Q ¹ represents an organic group having 2 to 30 carbon atoms and having an aromatic ring, and the aromatic ring may be unsubstituted or substituted with one or more substituents E;
J ¹ is -O-, -S-, -COO-, -OCO-, -OCO-O-, -NQ ² -, -N=CQ ² -, -CO-NQ ² -, -OCO-NQ ² - or -O-NQ ² -, where Q ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, an aromatic represents an organic group having 2 to 30 carbon atoms having a ring, or -(L ⁶ -A ⁵ ) _q -L ⁷ -R ^sp2 -Z ² , and the alkyl group, cycloalkyl group, cycloalkenyl group and aromatic ring; each may be unsubstituted or substituted by one or more of said substituents E, said alkyl group may be substituted by said cycloalkyl group or cycloalkenyl group, and in said alkyl group One -CH ₂ - or two or more non-adjacent -CH ₂ - are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S- , -S-CO-, -SO ₂ -, -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 1 in the cycloalkyl group or cycloalkenyl group each -CH ₂ - or two or more non-adjacent -CH ₂ - are each independently replaced with -O-, -CO-, -COO-, -OCO-, or -O-CO-O- L ⁶ , A ⁵ , L ⁷ , R ^sp2 , and Z ² are defined as L ¹ to L ⁴ , A ³ to A 4 , ^{L 5 ,} R ^sp1 , and Z ¹ above, respectively. but may be the same as or different from L ¹ to L ⁴ , A ³ to A ⁴ , L ⁵ , R ^sp1 , and Z ¹ , and q is 0 to 4 and when there are a plurality of L ⁶ and A ⁵ , they may be the same or different. Alternatively, Q ¹ and Q ² may combine to form a ring. )

（一般式（２）中、Ａ^coreは、無置換であるか又は１つ以上の置換基Ｅ^３によって置換されていても良い単環、縮合環又は環集合芳香族基である炭素原子数４～１６の三価又は四価の基を表し、
Ｍは、－ＣＨ＝ＣＨ－、－Ｎ＝ＣＨ－、－ＣＨ＝Ｎ－、又は－Ｎ＝Ｎ－を表し、
Ｄ^３は、インドレニン環構造を含む一価の基を表し、
Ｌ^１１、Ｌ^１２、Ｌ^１３及びＬ^１４はそれぞれ独立して、－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_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_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_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－又は単結合を表し、
Ａ^１１及びＡ^１２はそれぞれ独立して、無置換であるか又は１つ以上の置換基Ｅ^３によって置換されていても良いシクロヘキサン－１，４－ジイル基、シクロペンタン－１，３－ジイル基、シクロヘプタン－１，３－ジイル基、シクロヘプタン－１，４－ジイル基、デカヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表し、
Ａ^１３及びＡ^１４はそれぞれ独立して、無置換であるか又は１つ以上の置換基Ｅ^３によって置換されていても良いシクロヘキサン－１，４－ジイル基、シクロペンタン－１，３－ジイル基、シクロヘプタン－１，３－ジイル基、シクロヘプタン－１，４－ジイル基、ベンゼン－１，４－ジイル基、ピリジン－２，５－ジイル基、ピリミジン－２，５－ジイル基、ナフタレン－２，６－ジイル基、ナフタレン－２，７－ジイル基、ナフタレン－１，４－ジイル基、テトラヒドロナフタレン－２，６－ジイル基、デカヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表し、
Ｒ^１１及びＲ^１２はそれぞれ独立して、下記一般式（Ｒ－１１）から選ばれる基を表し、
一般式（Ｒ－１１）： －Ｌ^１５－Ｒ^ｓｐ１１－Ｚ^１１
一般式（Ｒ－１１）中、Ｌ^１５は、－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_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_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_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－又は単結合を表し、Ｒ^ｓｐ１１は、炭素原子数１～２０のアルキレン基又は単結合を表し、当該アルキレン基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－ＣＯＯ－、－ＯＣＯ－、－ＯＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－又は－Ｃ≡Ｃ－に置き換えられていても良く、Ｚ^１１は重合性官能基を表す。
置換基Ｅ^３は、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、これらによって置換されていても良い炭素原子数１～２０のアルキル基、当該アルキル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられていても良く、或いは、置換基Ｅ^３は、－Ｌ^Ｅ３－Ｒ^ｓｐＥ３－Ｚ^Ｅ３で表される基を表しても良く、ここでＬ^Ｅ３、Ｒ^ｓｐＥ３、及びＺ^Ｅ３は、それぞれ、前記Ｌ^１５、Ｒ^ｓｐ１１、及びＺ^１１で定義されるものと同一のものを表すが、それぞれ前記Ｌ^１５、Ｒ^ｓｐ１１、及びＺ^１１と同一であっても異なっていても良く、化合物内に置換基Ｅ^３が複数存在する場合それらは同一であっても異なっていても良く、
Ｍ、Ｄ^３、Ｌ^１３、Ｌ^１４、Ａ^１３、及びＡ^１４が複数現れる場合は、各々同一であっても異なっていても良い。
ｎ１１は１又は２の整数を表し、ｍ１１及びｍ１２はそれぞれ独立して１～４の整数を表す。）

(In the general formula (2), A ^core is a monocyclic, condensed ring, or ring assembly aromatic group that is unsubstituted or optionally substituted by one or more substituents E ³ , and has 4 carbon atoms. represents a trivalent or tetravalent group of ~16,
M represents -CH=CH-, -N=CH-, -CH=N-, or -N=N-,
^D3 represents a monovalent group containing an indolenine ring structure,
L ¹¹ , L ¹² , L ¹³ and L ¹⁴ are each independently -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -, -CO-, -COO- , -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, - NH—CO—NH—, —NH—O—, —O—NH—, —SCH ₂ —, —CH ₂ S—, —CF ₂ O—, —OCF ₂ —, —CF ₂ S—, —SCF ₂ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ -, -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -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 represents a single bond,
A ¹¹ and A ¹² are each independently a cyclohexane-1,4-diyl group or a cyclopentane-1,3-diyl group which may be unsubstituted or substituted with one or more substituents E ³ , cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl group,
A ¹³ and A ¹⁴ are each independently a cyclohexane-1,4-diyl group or a cyclopentane-1,3-diyl group which may be unsubstituted or substituted with one or more substituents E ³ , cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, benzene-1,4-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene- 2,6-diyl group, naphthalene-2,7-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3- represents a dioxane-2,5-diyl group,
R ¹¹ and R ¹² each independently represent a group selected from the following general formula (R-11),
General formula (R-11): -L ¹⁵ -R ^sp11 -Z ¹¹
In general formula (R-11), L ¹⁵ is -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 represents a single bond, R ^sp11 is carbon represents an alkylene group having 1 to 20 atoms or a single bond, in which one —CH ₂ — or two or more non-adjacent —CH ₂ — in the alkylene group are each independently —O—, —COO; -, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH- or -C≡C-, and Z ¹¹ is a polymerizable functional group represents
Substituent ^E3 is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group , a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms which may be substituted by these groups, and one —CH ₂ — in the alkyl group. or two or more -CH ₂ - which are not adjacent are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH -, -CH=CH-, -CF=CF- or -C≡C-, or the substituent E ³ is a group represented by -L ^E3 -R ^spE3 -Z ^E3 wherein L ^E3 , R ^spE3 , and Z ^E3 represent the same as defined in L ¹⁵ , R ^sp11 , and Z ¹¹ above, respectively, but L ¹⁵ , R ^sp11 above, respectively, , and Z ¹¹ may be the same or different, and if there are multiple substituents E ³ in the compound, they may be the same or different,
When multiple M, D ³ , L ¹³ , L ¹⁴ , A ¹³ and A ¹⁴ appear, they may be the same or different.
n11 represents an integer of 1 or 2, m11 and m12 each independently represents an integer of 1 to 4; )

One embodiment of the present disclosure provides a polymerizable composition, wherein in general formula (2), D ³ represents a group selected from general formula (D _g -2) below.

（一般式（Ｄ_ｇ－２）中、Ｒ^ｄ１及びＲ^ｄ２はそれぞれ独立して、炭素原子数１～２０のアルキル基を表し、当該アルキル基は無置換であるか又は１つ以上の前記置換基Ｅ^３によって置換されていても良く、当該アルキル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－は各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－ＳＯ_２－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－によって置換されていても良く、或いは、Ｒ^ｄ１及びＲ^ｄ２は互いに結合して３～７員環の非芳香族炭化水素環を形成していても良く、当該非芳香族炭化水素環は無置換であるか又は１つ以上の前記置換基Ｅ^３によって置換されていても良く、当該非芳香族炭化水素環の任意の炭素原子はヘテロ原子に置換されていても良く、
Ｒ^ｅ１、Ｒ^ｅ２、Ｒ^ｅ３及びＲ^ｅ４はそれぞれ独立して、水素原子、又は前記置換基Ｅ^３を表し、Ｒ^ｅ１、Ｒ^ｅ２、Ｒ^ｅ３及びＲ^ｅ４は互いに結合して３～７員環の非芳香族又は芳香族炭化水素環を形成していても良く、当該非芳香族又は芳香族炭化水素環は無置換であるか又は１つ以上の前記置換基Ｅ^３によって置換されていても良く、当該非芳香族又は芳香族炭化水素環の任意の炭素原子はヘテロ原子に置換されていても良い。＊（アスタリスク）はＭとの結合位置を示す。）

(In general formula (D _g -2), R ^d1 and R ^d2 each independently represent an alkyl group having 1 to 20 carbon atoms, and the alkyl group is unsubstituted or has one or more of the above-mentioned substituted optionally substituted by group E ³ , one —CH ₂ — or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —O—, —S—, — CO-, -COO-, -OCO-, -CO-S-, -S-CO-, _-SO2- , -O-CO-O-, -CO-NH-, -NH-CO-, -CH =CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C- Alternatively, R ^d1 and R ^d2 may combine with each other to form a 3- to 7-membered non-aromatic hydrocarbon ring, and is the non-aromatic hydrocarbon ring unsubstituted? or optionally substituted by one or more of said substituents E ³ , any carbon atom of said non-aromatic hydrocarbon ring optionally substituted by a heteroatom,
R ^e1 , R ^e2 , R ^e3 and R ^e4 each independently represent a hydrogen atom or the substituent ^E3 , and R ^e1 , R ^e2 , R ^e3 and R ^e4 are bonded to each other to form a 3- to 7-membered ring may form a non-aromatic or aromatic hydrocarbon ring of the non-aromatic or aromatic hydrocarbon ring may be unsubstituted or substituted by one or more of the substituents E ³ Optionally, any carbon atom of the non-aromatic or aromatic hydrocarbon ring may be replaced by a heteroatom. * (asterisk) indicates the binding position with M. )

In one embodiment of the present disclosure, in the general formula (D _g -1) of the general formula (1), J ¹ is -O-, -S-, -N=CQ ² - or -NQ ² - A polymerizable composition is provided.

One embodiment of the present disclosure is that in the general formula (D _g −1) of the general formula (1), J ¹ is —NQ ² —, and the Q ² has a hydrogen atom substituted with a fluorine atom. one -CH ₂ - or two or more non-adjacent -CH ₂ - may be independently replaced with -O-, -CO-, -COO-, or -OCO- A polymerizable composition, which is a linear or branched alkyl group having 2 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or the alkyl group optionally substituted by the cycloalkyl group. I will provide a.

One embodiment of the present disclosure provides a polymerizable composition further containing a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B).

One embodiment of the present disclosure provides a polymer obtained by polymerizing the polymerizable composition of one embodiment of the present disclosure.

One embodiment of the present disclosure is a retardation film having a retardation layer, the retardation layer contains a cured product of the polymerizable composition of the embodiment of the present disclosure, provides a retardation film do.

An embodiment of the present disclosure is a step of forming a film of the polymerizable composition of the embodiment of the present disclosure;
a step of orienting at least the polymerizable compound in the film-formed polymerizable composition;
Provided is a method for producing a retardation film, comprising a step of forming a retardation layer by including a step of polymerizing at least the polymerizable compound after the orientation step.

One embodiment of the present disclosure comprises a retardation layer and a support that releasably supports the retardation layer,
The retardation layer contains a cured product of the polymerizable composition of one embodiment of the present disclosure,
Provided is a transfer laminate for transferring a retardation layer.

An embodiment of the present disclosure provides an optical member including a polarizing plate on the retardation film of the embodiment of the present disclosure.

An embodiment of the present disclosure comprises a retardation layer and a support that releasably supports the retardation layer, wherein the retardation layer is a cured product of the polymerizable composition of the embodiment of the present disclosure. A step of preparing a transfer laminate to be subjected to transfer of the retardation layer containing
A transfer step of placing a transfer target including at least a polarizing plate and the retardation layer of the transfer laminate facing each other, and transferring the transfer laminate onto the transfer target;
A peeling step of peeling off the support from the transfer laminate transferred onto the transfer target;
A method for manufacturing an optical member is provided.

Further, one embodiment of the present disclosure provides a display device including the retardation film of the one embodiment of the present disclosure or the optical member of the one embodiment of the present disclosure.

According to embodiments of the present disclosure, a polymerizable composition having good solution stability and exhibiting reverse wavelength dispersion, a polymer obtained by polymerizing the polymerizable composition, and a cured product of the polymerizable composition a retardation film having a retardation layer and a method for producing the same, a transfer laminate capable of transferring the retardation layer, an optical member having the retardation film, a method for producing an optical member using the transfer laminate, Also, a display device can be provided.

FIG. 1 is a schematic cross-sectional view showing one embodiment of the retardation film. FIG. 2 is a schematic cross-sectional view showing one embodiment of the retardation film. FIG. 3 is a schematic cross-sectional view showing one embodiment of the retardation film. FIG. 4 is a schematic cross-sectional view showing an embodiment of the transfer laminate. FIG. 5 is a schematic cross-sectional view showing an embodiment of the transfer laminate. FIG. 6 is a schematic cross-sectional view showing one embodiment of the transfer laminate. FIG. 7 is a schematic cross-sectional view showing one embodiment of the optical member. FIG. 8 is a schematic cross-sectional view showing one embodiment of the display device.

Hereinafter, embodiments, examples, and the like of the present disclosure will be described with reference to the drawings and the like. However, the present disclosure can be implemented in many different aspects, and should not be construed as being limited to the descriptions of the embodiments, examples, and the like exemplified below. In addition, in order to make the description clearer, the drawings may schematically show the width, thickness, shape, etc. of each part compared to the actual embodiment, but this is only an example, and the interpretation of the present disclosure is not intended. It is not limited. In addition, in this specification and each figure, the same reference numerals may be given to the same elements as those described above with respect to the existing figures, and detailed description thereof may be omitted as appropriate. Also, for convenience of explanation, the terms "upper" and "lower" may be used, but the up-down direction may be reversed.
“In this specification, when a configuration, such as a member or a region, is “above (or below)” another configuration, such as another member or region, unless otherwise specified , this includes not only when directly above (or directly below) other structures, but also when above (or below) other structures, i.e. above (or below) other structures and in between another Including cases where components are included.

In the present disclosure, the alignment regulating force refers to the action of aligning the liquid crystal compound in the retardation 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.
In this specification, the terms "plate", "sheet", and "film" are not to be distinguished from each other based only on the difference in designation, and are referred to as "film surface (plate surface, sheet surface)". is the plane direction of the target film-like member (plate-like member, sheet-like member) when the target film-like member (plate-like member, sheet-like member) is viewed as a whole and in perspective point to

A. Polymerizable composition The polymerizable composition of the present disclosure includes a polymerizable liquid crystal compound (A) represented by the following general formula (1) and a polymerizable liquid crystal compound (B) represented by the following general formula (2). including.

（一般式（１）中、Ｌ^１、Ｌ^２、Ｌ^３及びＬ^４はそれぞれ独立して、－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_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_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_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－又は単結合を表し、
Ａ^１及びＡ^２はそれぞれ独立して、無置換であるか又は１つ以上の置換基Ｅによって置換されていても良いシクロヘキサン－１，４－ジイル基、シクロペンタン－１，３－ジイル基、シクロヘプタン－１，３－ジイル基、シクロヘプタン－１，４－ジイル基、デカヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表し、
Ａ^３及びＡ^４はそれぞれ独立して、無置換であるか又は１つ以上の置換基Ｅによって置換されていても良いシクロヘキサン－１，４－ジイル基、シクロペンタン－１，３－ジイル基、シクロヘプタン－１，３－ジイル基、シクロヘプタン－１，４－ジイル基、ベンゼン－１，４－ジイル基、ピリジン－２，５－ジイル基、ピリミジン－２，５－ジイル基、ナフタレン－２，６－ジイル基、ナフタレン－２，７－ジイル基、ナフタレン－１，４－ジイル基、テトラヒドロナフタレン－２，６－ジイル基、デカヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表し、
Ｒ^１及びＲ^２はそれぞれ独立して、下記一般式（Ｒ－１）から選ばれる基を表し、
一般式（Ｒ－１）： －Ｌ^５－Ｒ^ｓｐ１－Ｚ^１
一般式（Ｒ－１）中、Ｌ^５は、－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_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_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_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－又は単結合を表し、Ｒ^ｓｐ１は、炭素原子数１～２０のアルキレン基又は単結合を表し、当該アルキレン基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－ＣＯＯ－、－ＯＣＯ－、－ＯＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－又は－Ｃ≡Ｃ－に置き換えられていても良く、Ｚ^１は重合性官能基を表す。
Ｄ^１及びＤ^２はそれぞれ独立して、下記一般式（Ｄ_ｇ－１）から選ばれる基を表し、
置換基Ｅ、Ｅ^１及びＥ^２はそれぞれ独立して、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、これらによって置換されていても良い炭素原子数１～２０のアルキル基を表し、当該アルキル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられていても良く、或いは、置換基Ｅ、Ｅ^１及びＥ^２はそれぞれ独立して、－Ｌ^Ｅ－Ｒ^ｓｐＥ－Ｚ^Ｅで表される基を表しても良く、ここでＬ^Ｅ、Ｒ^ｓｐＥ、及びＺ^Ｅは、それぞれ、前記Ｌ^５、Ｒ^ｓｐ１、及びＺ^１で定義されるものと同一のものを表すが、それぞれ前記Ｌ^５、Ｒ^ｓｐ１、及びＺ^１と同一であっても異なっていても良く、化合物内に置換基Ｅ、Ｅ^１及びＥ^２がそれぞれ複数存在する場合は、各々同一であっても異なっていても良く、
Ｌ^３、Ｌ^４、Ａ^３、及びＡ^４がそれぞれ複数存在する場合は、各々同一であっても異なっていても良い。
ｍ１及びｍ２はそれぞれ独立して１～４の整数を表し、ｎ１及びｎ２はそれぞれ独立して０～３の整数を表す。）

(In general formula (1), L ¹ , L ² , L ³ and L ⁴ are each independently -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ - , -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH- , -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, - CF ₂ S-, -SCF ₂ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ - , -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -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 represents a single bond,
A ¹ and A ² are each independently a cyclohexane-1,4-diyl group, a cyclopentane-1,3-diyl group, which may be unsubstituted or substituted with one or more substituents E, represents a cycloheptane-1,3-diyl group, a cycloheptane-1,4-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,3-dioxane-2,5-diyl group,
A ³ and A ⁴ are each independently a cyclohexane-1,4-diyl group, a cyclopentane-1,3-diyl group, which may be unsubstituted or substituted with one or more substituents E, cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, benzene-1,4-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2 ,6-diyl group, naphthalene-2,7-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane - represents a 2,5-diyl group,
R ¹ and R ² each independently represent a group selected from general formula (R-1) below,
General formula (R-1): -L ⁵ -R ^sp1 -Z ¹
In general formula (R-1), L ⁵ is -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 represents a single bond, R ^sp1 is carbon represents an alkylene group having 1 to 20 atoms or a single bond, in which one —CH ₂ — or two or more non-adjacent —CH ₂ — in the alkylene group are each independently —O—, —COO; -, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH- or -C≡C-, and Z ¹ is a polymerizable functional group represents
D ¹ and D ² each independently represent a group selected from the following general formula (D _g -1),
Substituents E, E ¹ and E ² are each independently fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or an alkyl group having 1 to 20 carbon atoms optionally substituted by these, one -CH ₂ - or two or more non-adjacent -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, - CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO- CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, or substituents E, E ¹ and E ² are Each independently may represent a group represented by -L ^E -R ^spE -Z ^E , wherein L ^E , R ^spE and Z ^E are respectively the L ⁵ , R ^sp1 and Z ¹ but may be the same as or different from L ⁵ , R ^sp1 and Z ¹ , and the substituents E, E ¹ and E ² in the compound are respectively When there are more than one, each may be the same or different,
When there are a plurality of L ³ , L ⁴ , A ³ and A ⁴ , they may be the same or different.
m1 and m2 each independently represent an integer of 1 to 4; n1 and n2 each independently represent an integer of 0 to 3; )

（一般式（Ｄ_ｇ－１）中、Ｇ^１は水素原子又は炭素原子数１～６のアルキル基を表すが、当該アルキル基は無置換であるか又は１つ以上の前記置換基Ｅによって置換されていても良く、
Ｑ^１は、芳香環を有する炭素原子数２～３０の有機基を表すが、当該芳香環は無置換であるか又は１つ以上の前記置換基Ｅによって置換されていても良く、
Ｊ^１は、－Ｏ－、－Ｓ－、－ＣＯＯ－、－ＯＣＯ－、－ＯＣＯ－Ｏ－、－ＮＱ^２－、－Ｎ＝ＣＱ^２－、－ＣＯ－ＮＱ^２－、－ＯＣＯ－ＮＱ^２－又は－Ｏ－ＮＱ^２－を表し、Ｑ^２は水素原子、炭素原子数１～２０のアルキル基、炭素原子数３～１２のシクロアルキル基、炭素原子数３～１２のシクロアルケニル基、芳香環を有する炭素原子数２～３０の有機基、又は－（Ｌ^６－Ａ^５）_ｑ－Ｌ^７－Ｒ^ｓｐ２－Ｚ^２を表し、当該アルキル基、シクロアルキル基、シクロアルケニル基、及び芳香環はそれぞれ、無置換であるか又は１つ以上の前記置換基Ｅによって置換されていても良く、当該アルキル基は当該シクロアルキル基又はシクロアルケニル基によって置換されていても良く、当該アルキル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－は各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－ＳＯ_２－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられていても良く、当該シクロアルキル基又はシクロアルケニル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－は各々独立して－Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、又は－Ｏ－ＣＯ－Ｏ－に置き換えられていても良く、Ｌ^６、Ａ^５、Ｌ^７、Ｒ^ｓｐ２、及びＺ^２は、それぞれ、前記Ｌ^１～Ｌ^４、Ａ^３～Ａ^４、Ｌ^５、Ｒ^ｓｐ１、及びＺ^１で定義されるものと同一のものを表すが、それぞれ前記Ｌ^１～Ｌ^４、Ａ^３～Ａ^４、Ｌ^５、Ｒ^ｓｐ１、及びＺ^１と同一であっても異なっていても良く、ｑは０～４の整数を表し、Ｌ^６、及びＡ^５がそれぞれ複数存在する場合は、各々同一であっても異なっていても良い。或いは、Ｑ^１とＱ^２は結合して環を構成していても良い。）

(In the general formula (D _g -1), G ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group is unsubstituted or substituted with one or more substituents E It may be
Q ¹ represents an organic group having 2 to 30 carbon atoms and having an aromatic ring, and the aromatic ring may be unsubstituted or substituted with one or more substituents E;
J ¹ is -O-, -S-, -COO-, -OCO-, -OCO-O-, -NQ ² -, -N=CQ ² -, -CO-NQ ² -, -OCO-NQ ² - or -O-NQ ² -, where Q ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, an aromatic represents an organic group having 2 to 30 carbon atoms having a ring, or -(L ⁶ -A ⁵ ) _q -L ⁷ -R ^sp2 -Z ² , and the alkyl group, cycloalkyl group, cycloalkenyl group and aromatic ring; each may be unsubstituted or substituted by one or more of said substituents E, said alkyl group may be substituted by said cycloalkyl group or cycloalkenyl group, and in said alkyl group One -CH ₂ - or two or more non-adjacent -CH ₂ - are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S- , -S-CO-, -SO ₂ -, -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 1 in the cycloalkyl group or cycloalkenyl group each -CH ₂ - or two or more non-adjacent -CH ₂ - are each independently replaced with -O-, -CO-, -COO-, -OCO-, or -O-CO-O- L ⁶ , A ⁵ , L ⁷ , R ^sp2 , and Z ² are defined as L ¹ to L ⁴ , A ³ to A 4 , ^{L 5 ,} R ^sp1 , and Z ^{1 ,} respectively. but may be the same as or different from L ¹ to L ⁴ , A ³ to A ⁴ , L ⁵ , R ^sp1 , and Z ¹ , and q is 0 to 4 and when there are a plurality of L ⁶ and A ⁵ , they may be the same or different. Alternatively, Q ¹ and Q ² may combine to form a ring. )

（一般式（２）中、Ａ^coreは、無置換であるか又は１つ以上の置換基Ｅ^３によって置換されていても良い単環、縮合環又は環集合芳香族基である炭素原子数４～１６の三価又は四価の基を表し、
Ｍは、－ＣＨ＝ＣＨ－、－Ｎ＝ＣＨ－、－ＣＨ＝Ｎ－、又は－Ｎ＝Ｎ－を表し、
Ｄ^３は、インドレニン環構造を含む一価の基を表し、
Ｌ^１１、Ｌ^１２、Ｌ^１３及びＬ^１４はそれぞれ独立して、－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_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_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_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－又は単結合を表し、
Ａ^１１及びＡ^１２はそれぞれ独立して、無置換であるか又は１つ以上の置換基Ｅ^３によって置換されていても良いシクロヘキサン－１，４－ジイル基、シクロペンタン－１，３－ジイル基、シクロヘプタン－１，３－ジイル基、シクロヘプタン－１，４－ジイル基、デカヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表し、
Ａ^１３及びＡ^１４はそれぞれ独立して、無置換であるか又は１つ以上の置換基Ｅ^３によって置換されていても良いシクロヘキサン－１，４－ジイル基、シクロペンタン－１，３－ジイル基、シクロヘプタン－１，３－ジイル基、シクロヘプタン－１，４－ジイル基、ベンゼン－１，４－ジイル基、ピリジン－２，５－ジイル基、ピリミジン－２，５－ジイル基、ナフタレン－２，６－ジイル基、ナフタレン－２，７－ジイル基、ナフタレン－１，４－ジイル基、テトラヒドロナフタレン－２，６－ジイル基、デカヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表し、
Ｒ^１１及びＲ^１２はそれぞれ独立して、下記一般式（Ｒ－１１）から選ばれる基を表し、
一般式（Ｒ－１１）： －Ｌ^１５－Ｒ^ｓｐ１１－Ｚ^１１
一般式（Ｒ－１１）中、Ｌ^１５は、－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＨ_２ＣＨ_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_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_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－又は単結合を表し、Ｒ^ｓｐ１１は、炭素原子数１～２０のアルキレン基又は単結合を表し、当該アルキレン基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－ＣＯＯ－、－ＯＣＯ－、－ＯＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－又は－Ｃ≡Ｃ－に置き換えられていても良く、Ｚ^１１は重合性官能基を表す。
置換基Ｅ^３は、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、ニトロ基、シアノ基、イソシアノ基、アミノ基、ヒドロキシル基、メルカプト基、メチルアミノ基、ジメチルアミノ基、ジエチルアミノ基、ジイソプロピルアミノ基、トリメチルシリル基、ジメチルシリル基、チオイソシアノ基、又は、これらによって置換されていても良い炭素原子数１～２０のアルキル基、当該アルキル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－に置き換えられていても良く、或いは、置換基Ｅ^３は、－Ｌ^Ｅ３－Ｒ^ｓｐＥ３－Ｚ^Ｅ３で表される基を表しても良く、ここでＬ^Ｅ３、Ｒ^ｓｐＥ３、及びＺ^Ｅ３は、それぞれ、前記Ｌ^１５、Ｒ^ｓｐ１１、及びＺ^１１で定義されるものと同一のものを表すが、それぞれ前記Ｌ^１５、Ｒ^ｓｐ１１、及びＺ^１１と同一であっても異なっていても良く、化合物内に置換基Ｅ^３が複数存在する場合それらは同一であっても異なっていても良く、
Ｍ、Ｄ^３、Ｌ^１３、Ｌ^１４、Ａ^１３、及びＡ^１４が複数現れる場合は、各々同一であっても異なっていても良い。
ｎ１１は１又は２の整数を表し、ｍ１１及びｍ１２はそれぞれ独立して１～４の整数を表す。）

(In the general formula (2), A ^core is a monocyclic, condensed ring, or ring assembly aromatic group that is unsubstituted or optionally substituted by one or more substituents E ³ , and has 4 carbon atoms. represents a trivalent or tetravalent group of ~16,
M represents -CH=CH-, -N=CH-, -CH=N-, or -N=N-,
^D3 represents a monovalent group containing an indolenine ring structure,
L ¹¹ , L ¹² , L ¹³ and L ¹⁴ are each independently -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -, -CO-, -COO- , -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, - NH—CO—NH—, —NH—O—, —O—NH—, —SCH ₂ —, —CH ₂ S—, —CF ₂ O—, —OCF ₂ —, —CF ₂ S—, —SCF ₂ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ -, -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -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 represents a single bond,
A ¹¹ and A ¹² are each independently a cyclohexane-1,4-diyl group or a cyclopentane-1,3-diyl group which may be unsubstituted or substituted with one or more substituents E ³ , cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl group,
A ¹³ and A ¹⁴ are each independently a cyclohexane-1,4-diyl group or a cyclopentane-1,3-diyl group which may be unsubstituted or substituted with one or more substituents E ³ , cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, benzene-1,4-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene- 2,6-diyl group, naphthalene-2,7-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3- represents a dioxane-2,5-diyl group,
R ¹¹ and R ¹² each independently represent a group selected from the following general formula (R-11),
General formula (R-11): -L ¹⁵ -R ^sp11 -Z ¹¹
In general formula (R-11), L ¹⁵ is -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 represents a single bond, R ^sp11 is carbon represents an alkylene group having 1 to 20 atoms or a single bond, in which one —CH ₂ — or two or more non-adjacent —CH ₂ — in the alkylene group are each independently —O—, —COO; -, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH- or -C≡C-, and Z ¹¹ is a polymerizable functional group represents
Substituent ^E3 is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group , a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms which may be substituted by these groups, and one —CH ₂ — in the alkyl group. or two or more -CH ₂ - which are not adjacent are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH -, -CH=CH-, -CF=CF- or -C≡C-, or the substituent E ³ is a group represented by -L ^E3 -R ^spE3 -Z ^E3 wherein L ^E3 , R ^spE3 , and Z ^E3 represent the same as defined in L ¹⁵ , R ^sp11 , and Z ¹¹ above, respectively, but L ¹⁵ , R ^sp11 above, respectively, , and Z ¹¹ may be the same or different, and if there are multiple substituents E ³ in the compound, they may be the same or different,
When multiple M, D ³ , L ¹³ , L ¹⁴ , A ¹³ and A ¹⁴ appear, they may be the same or different.
n11 represents an integer of 1 or 2, m11 and m12 each independently represents an integer of 1 to 4; )

Since the compound represented by the general formula (1) of the present disclosure has a specific structure in the main chain structure from the specific R ¹ to R ² , the orientation between the molecules is improved, and the liquid crystallinity is improved by itself. It is a compound showing In addition, the compound represented by the general formula (1) of the present disclosure is a polymerizable liquid crystal compound because it has a polymerizable group at its terminal.
The compound represented by the general formula (1) of the present disclosure has a high orientation between molecules due to the biphenylene group contained in the main chain portion, and furthermore, one for each of the two benzene rings of the biphenylene group, a total of two Since it has a side chain, it becomes a liquid crystal compound having reverse wavelength dispersion and a large birefringence (Δn).
The polymerizable liquid crystal compound (A) represented by the general formula (1) of the present disclosure has a large birefringence (Δn) and reverse wavelength dispersion. It is possible to obtain a retardation layer having a thin film, and a thinner retardation layer can be obtained.
Compounds having reverse wavelength dispersion generally have poor solubility, but in the polymerizable liquid crystal compound (A) represented by general formula (1) of the present disclosure, A ¹ and A ² adjacent to the biphenylene group are The reduced solubility can be improved by introducing a cyclic hydrocarbon group. However, the polymerizable liquid crystal compound (A) represented by the general formula (1) of the present disclosure requires further improvement in solubility.

On the other hand, the compound represented by the general formula (2) of the present disclosure has a specific structure in the main chain structure from the specific R ¹¹ to R ¹² , so that the orientation between the molecules is good. It is a compound that exhibits liquid crystallinity at In addition, the compound represented by the general formula (2) of the present disclosure is a polymerizable liquid crystal compound because it has a polymerizable group at its terminal.
The compound represented by the general formula (2) of the present disclosure has an indolenine ring structure in the side chain portion via a double bond, so that it has a reverse wavelength compared to the case of having an aromatic ring in the prior art. It becomes easier to exhibit dispersibility, improves solvent solubility, and is less likely to precipitate, thereby improving the stability of the ink.
The indolenine ring structure has sp3 carbon atoms to which R ^d1 and R ^d2 are bonded, as in the following general formula (d _g ). When the side chain portion has an indolenine ring structure via a double bond due to the effect of the sp3 carbon atom to which the R ^d1 and R ^d2 are bonded, the directionality of the π-conjugated system of the side chain portion is changed in the liquid crystal compound. It is presumed that it is easy to adjust in the short axis direction, the absorption in the short axis direction of the liquid crystal compound is easily extended to the long wavelength region, and that reverse wavelength dispersion and flat wavelength dispersion are exhibited.
In addition, conventional compounds having reverse wavelength dispersion or flat wavelength dispersion generally have poor solubility, but the compound represented by the general formula (2) of the present disclosure has A ¹¹ and A By introducing an alicyclic hydrocarbon group to ¹² and further having an sp3 carbon atom to which the R ^d1 and R ^d2 are bonded, the solvent solubility is improved, and the sp3 carbon to which the R ^d1 and R ^d2 are bonded The three-dimensional structure of the atoms makes it difficult for precipitation to occur, and the stability of the ink is improved.
Since the polymerizable liquid crystal compound (B) represented by the general formula (2) of the present disclosure has good solvent solubility, it is dissolved in an organic solvent to prepare an ink, and the ink is used to form a coating film. In this case, it is easy to form a uniform coating film, and the load on the production process and production equipment for drying the solvent is reduced.

（一般式（ｄ_ｇ）において、Ｒ^ｄ１及びＲ^ｄ２はそれぞれ独立して、炭素原子数１～２０のアルキル基を表し、当該アルキル基は無置換であるか又は１つ以上の前記置換基Ｅ^３によって置換されていても良く、当該アルキル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－は各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－ＳＯ_２－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－によって置換されても良く、或いは、Ｒ^ｄ１及びＲ^ｄ２は互いに結合して３～７員環の非芳香族炭化水素環を形成していても良く、当該非芳香族炭化水素環は無置換であるか又は１つ以上の前記置換基Ｅ^３によって置換されていても良く、当該非芳香族炭化水素環の任意の炭素原子はヘテロ原子に置換されていても良いものである。）

(In general formula (d _g ), R ^d1 and R ^d2 each independently represent an alkyl group having 1 to 20 carbon atoms, and the alkyl group is unsubstituted or has one or more substituents E ³ , and one —CH ₂ — or two or more non-adjacent —CH ₂ — in the alkyl group are each independently —O—, —S—, —CO— , -COO-, -OCO-, -CO-S-, -S-CO-, _-SO2- , -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH -COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C- Alternatively, R ^d1 and R ^d2 may combine with each other to form a 3- to 7-membered non-aromatic hydrocarbon ring, and the non-aromatic hydrocarbon ring is unsubstituted or has one It may be substituted with the above substituent ^E3 , and any carbon atom of the non-aromatic hydrocarbon ring may be substituted with a hetero atom.)

As described above, although further improvement in solvent solubility is required, the polymerizable liquid crystal compound (A) represented by the general formula (1) having a large birefringence (Δn) and exhibiting reverse wavelength dispersion, By including a polymerizable liquid crystal compound (B) represented by the general formula (2), which has good solvent solubility, is difficult to precipitate and has improved solution stability, and exhibits flat wavelength dispersion and reverse wavelength dispersion, The polymerizable compositions of the present disclosure complement each other in their advantages, and can be a polymerizable composition that exhibits good solution stability and reverse wavelength dispersion.
The polymerizable composition of the present disclosure has a large birefringence (Δn), and the polymerizable liquid crystal compound (A) represented by the general formula (1) exhibiting reverse wavelength dispersion allows the birefringence (Δn) can also be made larger.
The polymerizable composition of the present disclosure has a large birefringence (Δn) and contains the polymerizable liquid crystal compound (A) having reverse wavelength dispersion, so that the polymerizable liquid crystal compound (B) and, if necessary, It is possible to adjust the retardation so as to exhibit a desired reverse wavelength dispersion by mixing other liquid crystal compounds.

In addition, the orientation of the polymerizable composition of the present disclosure is improved by using the composition of the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B). This is probably because the polymerizable composition of the present disclosure has a wide liquid crystal phase transition temperature as a composition, widens the process margin at the time of alignment, and easily assumes a liquid crystal state. Furthermore, the polymerizable composition of the present disclosure is a composition of the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B), so that the advantages of each complement each other, and the solubility of the composition A retardation layer having excellent in-plane uniformity in retardation value can be obtained by improving compatibility and orientation.

1. Polymerizable liquid crystal compound (A) represented by general formula (1)
L ¹ , L ² , L ³ and L ⁴ in general formula (1) are each independently -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ - , -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH- , -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, - CF ₂ S-, -SCF ₂ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ - , -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -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 represents a single bond. represents a divalent linking group or a single bond. In addition, when each of L ³ and L ⁴ independently appears in a plurality, they may be the same or different.

More specifically, L ¹ and L ² are each independently -COO-, -OCO-, -OCH ₂ -, and -CH ₂ O from the viewpoint of liquid crystallinity, availability of raw materials and ease of synthesis. -, -CF ₂ O-, -OCF ₂ -, -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 -, -CH ₂ CH ₂ -COO-, -CH ₂ CH ₂ -OCO-, -CH=CH- , -CF=CF-, -C≡C- or preferably represents a single bond, -COO-, -OCO-, -OCH ₂ -, -CH ₂ O-, -CF ₂ O-, -OCF ₂ - , -CH ₂ CH ₂ -, -COO-CH ₂ CH ₂ -, -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -CH ₂ CH ₂ -OCO-, -CH=CH-, -C≡C- or a single bond is more preferred, and -COO-, -OCO-, -OCH ₂ -, -CH ₂ O-, -CF ₂ O-, -OCF ₂ - or a single bond is more preferred, and -COO-, -OCO-, -OCH ₂ -, -CH ₂ O-, or even more preferably represents a single bond, -COO-, -OCO-, -OCH ₂ -, or -CH It is particularly preferred to represent ₂ O-.

More specifically, L ³ and L ⁴ are each independently -O-, -S-, -OCH ₂ -, -CH ₂ O-, - from the viewpoint of availability of raw materials and ease of synthesis. 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-, -COO-CH ₂ CH ₂ -, -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -CH ₂ CH ₂ -OCO- or preferably represents a single bond, and when there are a plurality of them, they may be the same or different, and each independently -O-, -OCH ₂ -, and -CH ₂ O- , -COO-, -OCO-, -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—, or a single bond is more preferable, and when there are a plurality of these, they may be the same or different. Also good.

A ¹ and A ² in general formula (1) are each independently an unsubstituted or optionally substituted cyclohexane-1,4-diyl group, cyclopentane- 1,3-diyl group, cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl group represents

Among these, A ¹ and A ² are each independently unsubstituted or substituted with one or more from the viewpoint of facilitating the improvement of the liquid crystallinity and the orientation of the polymer. a cyclohexane-1,4-diyl group, a cyclopentane-1,3-diyl group, a cycloheptane-1,3-diyl group, or a cycloheptane-1,4-diyl group optionally substituted by a group E; is more preferred, and a cyclohexane-1,4-diyl group, which may be unsubstituted or substituted by one or more substituents E, is particularly preferred.

The divalent alicyclic hydrocarbon group has cis-type and trans-type stereoisomers based on the difference in the configuration of the carbon atoms bonded to L ¹ and L ³ (or L ² and L ⁴ ). obtain. The divalent alicyclic hydrocarbon group may be cis-type, trans-type, or a mixture of cis-type and trans-type isomers. , trans or cis, and more preferably trans.

A ³ and A ⁴ in general formula (1) are each independently an unsubstituted or optionally substituted cyclohexane-1,4-diyl group, cyclopentane- 1,3-diyl group, cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, benzene-1,4-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5 -diyl group, naphthalene-2,6-diyl group, naphthalene-2,7-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl group. In addition, when A ³ and A ⁴ each appear independently in plural numbers, they may be the same or different.

A ³ and A ⁴ in the general formula (1) are each independently benzene-1,4-diyl because it facilitates improvement of liquid crystallinity and orientation of the polymer. 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, tetrahydronaphthalene- A 2,6-diyl group, a decahydronaphthalene-2,6-diyl group, or a 1,3-dioxane-2,5-diyl group is preferred.

A ³ and A ⁴ in general formula (1) are each independently a benzene-1,4-diyl group which may be unsubstituted or substituted with one or more substituents E, naphthalene-2 ,6-diyl group or cyclohexane-1,4-diyl group, more preferably benzene-1,4-diyl group or cyclohexane-1,4-diyl group, and benzene-1,4- A diyl group is particularly preferred. These groups make it easier to improve the liquid crystallinity of the polymerizable liquid crystal compound of the present embodiment and improve the orientation of the polymer.

Each of the substituents E is independently a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a pentafluorosulfuranyl group, a nitro group, a cyano group, an isocyano group, an amino group, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms which may be substituted by these, and one of the alkyl groups of -CH ₂ - or two or more non-adjacent -CH ₂ - are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, - S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, - OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, or each substituent E is independently -L ^E -R ^spE - may represent a group represented by ^ZE , where ^LE , ^RspE , and ^ZE are the same as defined for ^L5 , ^Rsp1 , and ^Z1, respectively, which will be described later; may be the same as or different from L ⁵ , R ^sp1 , and Z ¹ , and when a plurality of substituents E are present in the compound, they may be the same or different. . The alkyl group having 1 to 20 carbon atoms may be linear or branched.

From the viewpoint of liquid crystallinity and ease of synthesis, the substituent E is a fluorine atom, a chlorine atom, a pentafluorosulfuranyl group, a nitro group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, or any may be substituted with a fluorine atom, and one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, —CO—, -COO-, -OCO-, -O-CO-O-, -CH=CH-, -CF=CF- or -C≡C- having 1 to 20 carbon atoms which may be substituted by a group selected from wherein a fluorine atom, a chlorine atom or any hydrogen atom may be replaced by a fluorine atom, and one —CH ₂ — or two non-adjacent -CH ₂ - is each independently a linear or branched alkyl group having 1 to 12 carbon atoms which may be substituted by a group selected from -O-, -COO- or -OCO-; It is more preferable to represent a fluorine atom, a chlorine atom, or any hydrogen atom to represent a linear or branched alkyl group or alkoxy group having 1 to 12 carbon atoms which may be substituted with a fluorine atom. It is particularly preferred to represent a fluorine atom, a chlorine atom, or a straight-chain alkyl or straight-chain alkoxy group having 1 to 8 carbon atoms.
Further, the substituent E that may be substituted on A ³ and A ⁴ , and among them, the substituent E that may be substituted on A ³ and A ⁴ to which R ¹ and R ² are respectively bonded include - A group represented by L ^E -R ^spE -Z ^E is also preferred.

m1 and m2 in general formula (1) each independently represents an integer of 1 to 4;
When emphasizing the liquid crystallinity and orientation of the polymerizable compound of the present embodiment, it is preferable that one or both of m1 and m2 is an integer of 1 to 3, and both m1 and m2 are integers of 1 to 3. and more preferably both m1 and m2 are 1 or 2.

R ¹ and R ² each independently represent a group selected from general formula (R-1) below.
General formula (R-1): -L ⁵ -R ^sp1 -Z ¹
In general formula (R-1), L ⁵ is -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.

In the general formula (R-1), more ^specifically , from the viewpoint of availability of raw materials and ease of synthesis, each independently -O-, -S-, -COO-, -OCO -, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH ₂ CH ₂ -COO-, -CH ₂ CH ₂ -OCO - or preferably represents a single bond, each independently -O-, -COO-, -OCO-, -O-CO-O-, or more preferably represents a single bond, and when there are multiple They may be the same or different.

In general formula (R-1), R ^sp1 is one —CH ₂ — or two or more non-adjacent —CH ₂ — each independently —O—, —COO—, —OCO—, represents an alkylene group having 1 to 20 carbon atoms or a single bond which may be replaced by -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH- or -C≡C-;

In the general formula (R-1), more specifically, as R ^sp1 , from the viewpoint of availability of raw materials and ease of synthesis, each independently one —CH ₂ — or two non-adjacent More preferably, at least one —CH ₂ — each independently represents an alkylene group having 1 to 12 carbon atoms which may be substituted with —O—, —COO—, or —OCO—, or a single bond, each independently more preferably represents an alkylene group having 1 to 12 carbon atoms or a single bond, and each independently represents an alkylene group having 2 to 10 carbon atoms, and more preferably 4 to 8 carbon atoms. is more preferably an alkylene group, and when there are a plurality of groups, they may be the same or different.

In general formula (R-1), Z ¹ represents a polymerizable functional group. As the polymerizable functional group, groups used in conventional polymerizable liquid crystal compounds can be applied without limitation.
Preferably, the polymerizable functional groups each independently represent a group selected from the following formulas (Z-1) to (Z-8). In the following formulas (Z-1) to (Z-8), * (asterisk) indicates the binding position with R ^sp1 .

（式（Ｚ－１）～（Ｚ－８）中、Ｒ^ｚはそれぞれ独立して、水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、メチル基、エチル基、又はトリフルオロメチル基である。）

(in formulas (Z-1) to (Z-8), each R ^z 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; be.)

When ultraviolet polymerization is performed as the polymerization method, Z ¹ is represented by formula (Z-1), formula (Z-2), formula (Z-3), formula (Z-5), and formula (Z-7). Formula (Z-1), Formula (Z-3), and Formula (Z-7) are preferred, Formula (Z-1) is even more preferred, and in Formula (Z-1), R ^z is a hydrogen atom, A methyl group or a trifluoromethyl group is particularly preferred.

In general formula (1), 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 ) Specific examples of _m2 - ^L5 - ^Rsp1 - ^Z1 include, but are not limited to, groups represented by Lc-1 to Lc-244 below. In the polymerizable liquid crystal compound represented by general formula (1), Lc1 and Lc2 may be the same or different.

In the groups represented by Lc-1 to Lc-244, m1 or m2 in ^L3 or ^L4 each represents 1 or 2, with 2 being preferred. n in R ^sp1 represents 1 to 20, among which n in R ^sp1 is preferably 2 or more, more preferably 4 or more, on the other hand, preferably 12 or less, further 10 or less is preferably
In addition, in Z ¹ , R ^z in formula (Z-1) is each independently preferably a hydrogen atom or a methyl group, more preferably a hydrogen atom.

On the other hand, in the general formula (D _g -1), G ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group is unsubstituted or substituted with one or more substituents E It may be substituted, and the substituent E is preferably F, Cl, CF ₃ , OCF ₃ or a cyano group. G ¹ is more preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms which is unsubstituted or in which one or more hydrogen atoms are substituted with fluorine atoms, particularly preferably a hydrogen atom.

When Q ¹ represents an organic group having 2 to 30 carbon atoms and having an aromatic ring, the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocyclic ring. In this case, Q ¹ represents an organic group having 2 to 30 carbon atoms and having at least one aromatic ring selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocyclic rings. The aromatic ring is preferably a group selected from the following formulas (Q-1) to (Q-22).
From the viewpoint of good wavelength dispersion, it is preferably an organic group having an aromatic heterocyclic ring in which one or more of the carbon atoms is substituted with a hetero atom, and has good wavelength dispersion and high birefringence. In view of the above, it is more preferable to be an organic group having an aromatic heterocyclic ring which is a condensed 5- and 6-membered ring. The aromatic heterocyclic ring which is a condensed ring of a 5-membered ring and a 6-membered ring includes, for example, the following formulas (Q-10), (Q-11), (Q-21) and (Q-22) Heteroaromatic rings in which one or more of the carbon atoms of the selected group are replaced by heteroatoms are preferred.

These groups have a bond at any position. Q ^a represents —O—, —S—, —NR ^Qa — (wherein R ^Qa represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms) or —CO—, and in these groups -CH= may be independently replaced with -N=, and -CH ₂ - is each independently -O-, -S-, -NR ^Qa - (wherein R ^Qa is a hydrogen atom or represents an alkyl group having 1 to 8 carbon atoms.) may be replaced with -SO-, -SO ₂ - or -CO- (except when oxygen atoms are directly bonded to each other). One or more hydrogen atoms bonded to these rings may be substituted with the substituent E described above. Examples of the alkyl group constituting the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group and hexyl group. . The number of carbon atoms in the alkyl group is preferably 1 to 4, more preferably 1 or 2, and still more preferably 1.

The group represented by the formula (Q-1) includes the following formulas (Q-1-1) to (Q-1-8) which may be unsubstituted or substituted by one or more substituents E It is preferable to represent a group selected from and these groups have a bond at an arbitrary position.

The group represented by formula (Q-7) includes the following formulas (Q-7-1) to (Q-7-7) which may be unsubstituted or substituted by one or more substituents E It is preferable to represent a group selected from and these groups have a bond at an arbitrary position.

The group represented by formula (Q-10) includes the following formulas (Q-10-1) to (Q-10-9) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by formula (Q-11) includes the following formulas (Q-11-1) to (Q-11-12) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by formula (Q-13) includes the following formulas (Q-13-1) to (Q-13-19) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by formula (Q-14) includes the following formulas (Q-14-1) to (Q-14-10) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by formula (Q-15) includes the following formulas (Q-15-1) to (Q-15-4) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by formula (Q-16) includes the following formulas (Q-16-1) to (Q-16-16) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by formula (Q-17) includes the following formulas (Q-17-1) to (Q-17-4) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by formula (Q-18) includes the following formulas (Q-18-1) to (Q-18-6) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by formula (Q-19) includes the following formulas (Q-19-1) to (Q-19-6) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by the formula (Q-20) includes the following formulas (Q-20-1) to (Q-20-9) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

（式中、Ｒ^Ｑは水素原子又は炭素原子数１～６のアルキル基を表す。これらの基は任意の位置に結合手を有している。）

(In the formula, R ^Q represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. These groups have bonds at arbitrary positions.)

The group represented by formula (Q-21) includes the following formulas (Q-21-1) to (Q-21-3) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from
The group represented by formula (Q-22) includes the following formulas (Q-22-1) to (Q-22-3) which may be unsubstituted or substituted by one or more substituents E It is preferred to represent a group selected from

The aromatic group contained in Q ¹ is the above formula (Q-1-1), formula (Q-7-1), formula (Q- 7-2), formula (Q-7-7), formula (Q-8), formula (Q-10-2), formula (Q-10-3), formula (Q-10-4), formula ( Q-10-5), formula (Q-10-6), formula (Q-10-7), formula (Q-10-8), formula (Q-10-9), formula (Q-11-2 ), formula (Q-11-3), formula (Q-11-4), formula (Q-11-5), formula (Q-11-6), formula (Q-11-7), formula (Q -11-8), formula (Q-11-9), formula (Q-11-10), formula (Q-11-11), formula (Q-11-12), formula (Q-21-1) , Formula (Q-21-2), Formula (Q-22-1), and more preferably represents a group selected from Formula (Q-22-2), unsubstituted or one or more of the substituents E Formula (Q-10-2), Formula (Q-10-3), Formula (Q-10-4), Formula (Q-10-5), Formula (Q-10-6) which may be substituted by , Formula (Q-10-7), Formula (Q-10-8), and Formula (Q-10-9), Formula (Q-21-1), Formula (Q-21-2), Formula (Q -22-1) and a group selected from formula (Q-22-2).

Further, the substituent E when the aromatic group contained in Q ¹ is substituted includes, among others, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a nitro group, a cyano group, an isocyano group, an amino group, and a hydroxyl group. , a mercapto group, a methylamino group, a dimethylamino group, a diethylamino group, a diisopropylamino group, a thioisocyano group, or one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently — O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO- is preferably a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted with, wherein any hydrogen atom in the alkyl group may be substituted with a fluorine atom, and further, fluorine atom, chlorine atom, bromine atom, or one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —S—, —CO—, —COO; -, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, 1 to 20 carbon atoms which may be substituted by is a linear or branched alkyl group in which any hydrogen atom in the alkyl group may be substituted with a fluorine atom.

Furthermore, Q ¹ is the following formula (Q-10-2), formula (Q-10-2a), formula (Q-10-3), formula (Q-10-3a), formula (Q-10-3b ), formula (Q-10-6), formula (Q-10-6a), formula (Q-10-6b), formula (Q-10-6c), formula (Q-10-6d), formula (Q -10-7), formula (Q-10-7a), formula (Q-10-7b), formula (Q-10-7c), formula (Q-10-7d), formula (Q-10-7e) , Formula (Q-10-7f), Formula (Q-10-9), Formula (Q-10-9a), Formula (Q-10-9b), Formula (Q-21-1), Formula (Q- 21-2), formulas (Q-22-1) and formulas (Q-22-2).

J ¹ is -O-, -S-, -COO-, -OCO-, -OCO-O-, -NQ ² -, -N=CQ ² -, -CO-NQ ² -, -OCO-NQ ² - or -O-NQ ² -, where Q ² is a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a cycloalkenyl group having 3 to 12 carbon atoms, an aromatic represents an organic group having 2 to 30 carbon atoms having a ring, or -(L ⁶ -A ⁵ ) _q -L ⁷ -R ^sp2 -Z ² , and the alkyl group, cycloalkyl group, cycloalkenyl group and aromatic ring; each may be unsubstituted or substituted by one or more of said substituents E, said alkyl group may be substituted by said cycloalkyl group or cycloalkenyl group, and in said alkyl group One -CH ₂ - or two or more non-adjacent -CH ₂ - are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S- , -S-CO-, -SO ₂ -, -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 1 in the cycloalkyl group or cycloalkenyl group each -CH ₂ - or two or more non-adjacent -CH ₂ - are each independently replaced with -O-, -CO-, -COO-, -OCO-, or -O-CO-O- L ⁶ , A ⁵ , L ⁷ , R ^sp2 , and Z ² are defined as L ¹ to L ⁴ , A ¹ to A 4 , ^{L 5 ,} R ^sp1 , and Z ^{1 ,} respectively. but may be the same as or different from L ¹ to L ⁴ , A ¹ to A ⁴ , L ⁵ , R ^sp1 , and Z ¹ , and q is 0 to 4 and when there are a plurality of L ⁶ and A ⁵ , they may be the same or different.

J ¹ is preferably -O-, -S-, -N=CQ ² - or -NQ ² - because it has good birefringence and is easy to synthesize. -O-, -S-, or -NQ ² - is preferred in terms of good refraction.
Here, Q ² may be substituted with one or more of the substituents E, and one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O— , -CO-, -COO-, -OCO-, or -O-CO-O-, an alkyl or alkenyl group having 1 to 20 carbon atoms, or a cycloalkyl having 3 to 12 carbon atoms, which may be substituted with or a cycloalkenyl group having 3 to 12 carbon atoms, or the alkyl or alkenyl group optionally substituted by the cycloalkyl group, cycloalkenyl group, or aryl group, or -(L ⁶ -A ⁵ ) qL ⁷ -R ^sp2 -Z ² is preferred.
^Q2 can be appropriately selected depending on the purpose. For example, Q ² preferably has a structure containing no heteroatom in terms of birefringence. In addition, Q ² is a structure containing more heteroatoms, among which one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —CO Having a structure substituted with -, -COO-, -OCO- or -O-CO-O- is preferable from the viewpoint of improving the solvent solubility of the compound and increasing the choice of base materials for combination. Further, it is preferable that Q ² is -(L ⁶ -A ⁵ )qL ⁷ -R ^sp2 -Z ² from the viewpoint that durability is improved by improving the curing degree of the film.
unsubstituted alkyl or alkenyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 12 carbon atoms, cycloalkenyl group having 3 to 12 carbon atoms, the cycloalkyl group, cycloalkenyl group, or aryl group Examples of the alkyl or alkenyl group optionally substituted by a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, t-butyl group, n-pentyl group, n-hexyl group, 1-methylpentyl group, n-heptyl group, 1-ethylpentyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, 3,7-dimethyl octyl group, n-undecyl group, n-dodecyl group, vinyl group, allyl group, isopropenyl group, butynyl group, cyclopentyl group, cyclohexyl group, cyclopentenyl group, cyclohexenyl group, cyclooctenyl group, cyclopentylmethyl group, cyclohexylmethyl group , benzyl group and the like.

Substituents on Q ² include, among others, fluorine, chlorine, bromine, cyano, hydroxyl, mercapto, methylamino, dimethylamino, diethylamino, diisopropylamino or one —CH ₂ - or two or more non-adjacent -CH ₂ - are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO- , -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH= It is preferably a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted with CH-, -CH=CH-, -CF=CF- or -C≡C-, and fluorine an atom, a chlorine atom, a cyano group, a hydroxyl group, or one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —CO—, —COO—, -OCO- or a linear or branched alkyl group having 1 to 20 carbon atoms which may be replaced by -O-CO-O-.

Among them, Q ² may be substituted with one or more substituents E from the viewpoint of birefringence, solvent solubility, or durability, and one —CH ₂ — or two or more non-adjacent an alkyl group having 1 to 20 carbon atoms in which each of -CH ₂ - may be independently replaced with -O-, -CO-, -COO-, -OCO-, or -O-CO-O- or an alkenyl group, a cycloalkyl group having 3 to 12 carbon atoms, or a cycloalkenyl group having 3 to 12 carbon atoms, or the alkyl or alkenyl group optionally substituted by the cycloalkyl group or cycloalkenyl group or -(L ⁶ -A ⁵ )qL ⁷ -R ^sp2 -Z ² , any hydrogen atom may be substituted with a fluorine atom, and one —CH ₂ — or 2 or more non-adjacent —CH ₂ — may be independently replaced with —O—, —CO—, —COO—, —OCO—, linear or branched chain having 1 to 20 carbon atoms an alkyl group having 3 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, or the above alkyl group optionally substituted by the cycloalkyl group, or -(L ⁶ -A ⁵ )qL ⁷ -R ^sp2 -Z ² is preferred, and one -CH ₂ - or two or more non-adjacent -CH ₂ - may each be replaced with -O-, a straight group having 1 to 12 carbon atoms, which may be replaced with -O-. a chain or branched alkyl group, a cycloalkyl group having 3 to 12 carbon atoms, or the alkyl group optionally substituted by the cycloalkyl group, or -(L ⁶ -A ⁵ )qL It preferably represents ⁷ -R ^sp2 -Z ² .
Further, preferred structures of -(L ⁶ -A ⁵ )qL ⁷ -R ^sp2 -Z ² are each of the above L ¹ to L ⁴ , A ¹ to A ⁴ , L ⁵ , R ^sp1 and Z ¹ Desirably similar to the defined preferred structure. q represents an integer of 0 to 4, more preferably an integer of 0 to 2, more preferably 0 or 1, and particularly preferably 0.

Among them, in terms of birefringence and solvent solubility, Q ² may have one —CH ₂ — or two or more non-adjacent —CH ₂ — substituted with fluorine atoms for hydrogen atoms. A linear or branched alkyl group having 2 to 20 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms which may be independently replaced with -O-, -CO-, -COO-, or -OCO- Alternatively, it is preferably the alkyl group optionally substituted by the cycloalkyl group, hydrogen atoms may be substituted by fluorine atoms, and one —CH ₂ — or two or more non-adjacent each of -CH ₂ - is independently a linear or branched alkyl group having 2 to 20 carbon atoms which may be replaced by -O-, -CO-, -COO- or -OCO- More preferably, a hydrogen atom may be substituted with a fluorine atom, and one —CH ₂ — or two or more non-adjacent —CH ₂ — are each independently —O—, —CO—, —COO It is more preferably a straight-chain alkyl group having 2 to 20 carbon atoms which may be replaced by -, -OCO-.
The number of carbon atoms in ^Q2 is preferably 4 or more, more preferably 12 or less.

Alternatively, Q ¹ and Q ² may combine to form a ring, in which case, for example, a cyclic group represented by -NQ ¹ Q ² or represented by -N=CQ ¹ Q ² A cyclic group is mentioned. The ring formed together with the nitrogen atom or carbon atom to which Q ¹ and Q ² are bonded includes a ring having an aromatic ring and having 2 to 30 carbon atoms, and the number of carbon atoms is 2 ~18 is more preferred, and 2-14 is even more preferred. Among them, the cyclic group represented by -NQ ¹ Q ² is the following formulas (QQ-1) to (QQ-22) which may be unsubstituted or substituted with one or more substituents E It is preferred to represent a group selected from The cyclic group represented by -N=CQ ¹ Q ² preferably represents the following formula (QQ-23) or (QQ-24).

-CH= in the groups selected from formulas (QQ-1) to (QQ-24) may be independently replaced with -N=, and -CH ₂ - is each independently -O-, -S-, -NR ^Qa - (Wherein, R ^Qa represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.) May be replaced with -SO-, or -SO ₂ - or -CO- (However, the case where oxygen atoms are directly bonded to each other is excluded.). One or more hydrogen atoms bonded to these rings may be substituted with the substituent E described above. Examples of the alkyl group constituting the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group and hexyl group. . The number of carbon atoms in the alkyl group is preferably 1 to 4, more preferably 1 or 2, and still more preferably 1.

The total number of π electrons contained in J ¹ and Q ¹ is preferably 4 to 24, more preferably 4 to 20, from the viewpoint of wavelength dispersion characteristics, liquid crystallinity, and ease of synthesis.

D ¹ and D ² each represent a group selected from the following formulas (D-1) to (D-47), because the raw materials are easily available, the solubility is good, and the birefringence is high. is particularly preferred.

Each of E ¹ and E ² optionally substituted on the benzene ring of the biphenylene group may independently be the same as the substituent E described above.
E ¹ and E ² which may be substituted on the benzene ring of the biphenylene group include, among others, fluorine atom, chlorine atom, hydroxyl group, mercapto group, methylamino group, a dimethylamino group, or one -CH ₂ - or two or more non-adjacent -CH ₂ - are each independently -O-, -S-, -CO-, -COO-, -OCO- , -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, linear or branched chain having 1 to 6 carbon atoms which may be substituted by A linear alkyl group is preferred.

Also, each of n1 and n2 independently represents an integer of 0 to 3, preferably 0 to 2, more preferably 0 or 1.
Further, when E ¹ and E ² are each independently substituted by a biphenylene group, the substitution positions are preferably the 6- and 6′-positions of the biphenylene group from the viewpoint of good birefringence. . In such a case, the twist angle between the two benzene rings in the biphenylene group increases, making it easier to break the π-electron conjugated structure.

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

Further, the compounds represented by general formula (1) include, for example, compounds (i) to (xci) below. Core in the table represents the structure of a biphenylene group, Lc1 represents -L ¹ -A ¹ -(L ³ -A ³ ) _m1 -L ⁵ -R ^sp1 -Z ¹ , Lc2 represents -L ² -A ² -(L ⁴ -A ⁴ ) _m2 -L ⁵ -R ^sp1 -Z ¹ ;

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

The compound represented by general formula (1) can be produced, for example, by the following production method. Examples of the production method include known organic synthesis reactions described in Methoden der Organischen Chemie, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, Shin Jikken Kagaku Koza, etc. reaction, Wittig reaction, Schiff base formation reaction, benzylation reaction, Sonogashira reaction, Suzuki-Miyaura reaction, Negishi reaction, Kumada reaction, Hiyama reaction, Buchwald-Hartwig reaction, Friedel-Crafts reaction, Heck reaction, Aldol reaction, Duff reaction, etc.) can be appropriately combined depending on the structure. Examples of manufacturing methods are shown below, but the present disclosure is not limited to these structures and manufacturing methods.

For example, a compound in which L ¹ and L ² are each *-OCO- (* indicates the bonding position with a biphenylene group) and G ¹ is a hydrogen atom can be produced, for example, as follows. .
First, 4,4'-dihydroxybiphenyl or a compound represented by the formula (ip-1) further introduced with a substituent E is prepared, and an aldehyde group is introduced at a desired position by a Duff reaction or the like to prepare a compound represented by the formula (ip- 2) to produce intermediate A represented by

Next, intermediate A represented by formula (ip-2) and intermediate B represented by HOOC-A ¹ -(L ³ -A ³ ) _m1 -R ¹ (A ¹ , L ³ , A ³ , R ¹ and m1 have the same meanings as above) by condensation reaction or the like to obtain an intermediate C represented by the formula (ip-3), and further the obtained formula Intermediate C represented by (ip-3) and Intermediate D represented by HOOC-A ² -(L ⁴ -A ⁴ ) _m2 -R ² (A ² , L ⁴ , A ⁴ , R ² , and m2 have the same meaning as above) to obtain intermediate E represented by formula (ip-4). When intermediate B and intermediate D have the same structure, intermediate E can be obtained by reacting intermediate B with intermediate A.

Next, intermediate E represented by formula (ip-4) is reacted with intermediate F represented by, for example, Q ¹ -J ¹ -NH ₂ to obtain a compound represented by formula (1-ex1). can be obtained.

Intermediate A represented by ^the above formula (ip- ² ) can be, for ^example , 3,4-methylenedioxyphenol ⁽ (manufactured by Tokyo Kasei Kogyo Co., Ltd.) or a derivative thereof, is subjected to a Duff reaction to introduce an aldehyde group, and then subjected to a Suzuki-Miyaura coupling reaction.

Alternatively, for example, intermediate G represented by formula (ip-2) is prepared by previously introducing D ¹ and D ² as side chain moieties into intermediate G, and then HOOC-A is added to intermediate G. Intermediate B represented by ^1- (L ³ -A ³ ) _m1 -R ¹ (A ¹ , L ³ , A ³ , R ¹ and m1 have the same meanings as above) and HOOC-A ² -(L ⁴ -A ⁴ ) _m2 -R ² (A ² , L ⁴ , A ⁴ , R ² and m2 have the same meaning as above) by reacting the intermediate D with the formula A compound represented by (1-ex1) may be obtained.

Moreover, each intermediate used for manufacture may use a commercial item suitably, and can synthesize|combine suitably by a conventionally well-known method.

In this disclosure, the structures of the polymerizable liquid crystal compounds are determined by 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) and the like can be combined appropriately for analysis.

The polymerizable liquid crystal compound (A) represented by the general formula (1) of the present disclosure is a polymerizable liquid crystal compound that has good orientation, a large birefringence (Δn), and reverse wavelength dispersion. . For example, by the method shown in Example 1 below, a polymerizable liquid crystal compound (A) represented by the general formula (1) as a polymerizable liquid crystal compound and a polymerizable composition containing only a photopolymerization initiator are prepared and cured. When a film (retardation layer) is formed and the birefringence (Δn) of the cured film is measured, it is preferably 0.075 or more, more preferably 0.08 or more.
Further, in order to approach the ideal reverse wavelength dispersion, the polymerizable liquid crystal compound (A) represented by the general formula (1) of the present disclosure is prepared, for example, by the method described in Example 1 below. And the polymerizable liquid crystal compound represented by the general formula (1) (A), to prepare only a photopolymerization initiator, to form a cured film (retardation layer), when measuring the retardation value as described later In addition, Re (450) / Re (550) is preferably in the range of 0.50 or more and less than 0.95, more preferably in the range of 0.55 or more and less than 0.93. It is 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 or less, even if it is in the range of 0.60 or more and less than 0.80 good. Also, Re(650)/Re(550) is preferably more than 1, and more preferably in the range of 1.02 or more and 1.1 or less.

In addition, the polymerizable liquid crystal compound (A) represented by the general formula (1) of the present disclosure has a solid-liquid crystal phase transition temperature of 25° C. or higher and 200° C. or lower in terms of expanding the choices of usable base materials. is preferably 30° C. or higher and 180° C. or lower, and even more preferably 30° C. or higher and 150° C. or lower. If the solid-liquid crystal phase transition temperature is low, the load in the process of aligning the liquid crystal can be reduced, and it can be used for substrates that are vulnerable to high temperatures.
Here, the solid-liquid crystal phase transition temperature means the temperature at which the liquid crystal compound changes from solid to liquid crystal. In the present disclosure, the solid-liquid crystal phase transition temperature is confirmed at elevated temperature by texture observation using a polarizing microscope equipped with a temperature control stage. That is, the solid-liquid crystal phase transition temperature is defined as the point at which the solid melts and becomes liquid when the temperature is raised in the polarizing microscope observation, and the bright field is observed in the crossed Nicols observation of the polarizing microscope (the polarizing plates are perpendicular to each other). can do.

In addition, the polymerizable liquid crystal compound (A) represented by the general formula (1) of the present disclosure is added to at least one solvent selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone. % or more is preferable from the point of view of broadening the choices of usable base materials, and more preferably 20% by mass or more.

In the polymerizable composition of the present disclosure, the polymerizable liquid crystal compound (A) represented by the general formula (1) may be used singly or in combination of two or more.
In the present embodiment, since a polymerizable composition having a large birefringence (Δn) and reverse wavelength dispersion can be obtained, the polymerizable liquid crystal compound (A) represented by the general formula (1) is included. The proportion is preferably 10 parts by mass or more, more preferably 30 parts by mass or more, and even more preferably 50 parts by mass or more with respect to a total of 100 parts by mass of the polymerizable liquid crystal compound. On the other hand, from the viewpoint of obtaining a polymerizable composition with high solution stability, the content of the polymerizable liquid crystal compound (A) represented by the general formula (1) is 100 parts by mass in total of the polymerizable liquid crystal compounds. On the other hand, it is preferably 99 parts by mass or less, more preferably 95 parts by mass or less, and even more preferably 90 parts by mass or less.

Further, in the polymerizable composition of the present disclosure, the total content of the polymerizable liquid crystal compounds including the polymerizable liquid crystal compound (A) represented by the general formula (1) is the solid content of the polymerizable composition 100 mass It is preferably 70 parts by mass or more and 99.9 parts by mass or less, more preferably 80 parts by mass or more and 99.9 parts by mass or less, and 90 parts by mass or more and 99.9 parts by mass or less. is even more preferred.
In the present disclosure, the solid content refers to all components except the solvent, and for example, even if the polymerizable liquid crystal compound is liquid, it is included in the solid content.

2. Polymerizable liquid crystal compound (B) represented by general formula (2)
In general formula (2), ^D3 represents a monovalent group containing an indolenine ring structure. The monovalent group containing an indolenine ring structure may include the structure of the general formula (d _g ), may further have a substituent, and includes the benzene ring of the general formula (d _g ). A condensed ring may be formed, and a structure in which any hydrogen atom of the general formula (d _g ) is substituted with M is exemplified.

In the general formula (2), D ³ is, for example, a group selected from the following general formula (D _g -2), a group selected from the following general formula (D _g -3), or a group selected from the following general formula (D _g -4 ) and groups selected from

（一般式（Ｄ_ｇ－２）～（Ｄ_ｇ－４）中、Ｒ^ｄ１及びＲ^ｄ２は、それぞれ独立して、炭素原子数１～２０のアルキル基を表し、当該アルキル基は無置換であるか又は１つ以上の前記置換基Ｅ^３によって置換されていても良く、当該アルキル基中の１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－は各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－ＳＯ_２－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－によって置換されても良く、或いは、Ｒ^ｄ１及びＲ^ｄ２は互いに結合して３～７員環の非芳香族炭化水素環を形成していても良く、当該非芳香族炭化水素環は無置換であるか又は１つ以上の前記置換基Ｅ^３によって置換されていても良く、当該非芳香族炭化水素環の任意の炭素原子はヘテロ原子に置換されていても良く、
Ｒ^ｅ１、Ｒ^ｅ２、Ｒ^ｅ３及びＲ^ｅ４、並びに、Ｒ^ｄ３は、それぞれ独立して、水素原子、又は前記置換基Ｅ^３を表し、Ｒ^ｅ１、Ｒ^ｅ２、Ｒ^ｅ３及びＲ^ｅ４は互いに結合して３～７員環の非芳香族又は芳香族炭化水素環を形成していても良く、当該非芳香族又は芳香族炭化水素環は無置換であるか又は１つ以上の前記置換基Ｅ^３によって置換されていても良く、当該非芳香族又は芳香族炭化水素環の任意の炭素原子はヘテロ原子に置換されていても良い。＊（アスタリスク）はＭとの結合位置を示す。）

(In general formulas (D _g -2) to (D _g -4), R ^d1 and R ^d2 each independently represent an alkyl group having 1 to 20 carbon atoms, and the alkyl group is unsubstituted or may be substituted by one or more of the substituents E ³ , and one —CH ₂ — or two or more non-adjacent —CH ₂ — in the alkyl group are each independently — O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, _-SO2- , -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or may be substituted by —C≡C—, or R ^d1 and R ^d2 may be combined with each other to form a 3- to 7-membered non-aromatic hydrocarbon ring, and the non-aromatic hydrocarbon the ring may be unsubstituted or substituted by one or more of said substituents E ³ and any carbon atom of said non-aromatic hydrocarbon ring may be substituted by a heteroatom;
R ^e1 , R ^e2 , R ^e3 and R ^e4 , and R ^d3 each independently represent a hydrogen atom or the substituent E ³ , and R ^e1 , R ^e2 , R ^e3 and R ^e4 are bonded to each other; may form a 3- to 7-membered non-aromatic or aromatic hydrocarbon ring, and the non-aromatic or aromatic hydrocarbon ring is unsubstituted or one or more of the substituents E ³ and any carbon atom of the non-aromatic or aromatic hydrocarbon ring may be substituted with a heteroatom. * (asterisk) indicates the binding position with M. )

In general formula (d _g ), general formula (D _g -2), general formula (D _g -3), and general formula (D _g -4), R ^d1 and R ^d2 improve solvent solubility, stabilize from the viewpoint of improving the properties and adjusting the reverse wavelength dispersion property, each independently an unsubstituted alkyl group having 1 to 10 carbon atoms, or R ^d1 and R ^d2 are bonded to each other to form a 5- to 7-membered ring. It preferably forms a non-aromatic hydrocarbon ring. From the viewpoints of improving solvent solubility, improving stability, adjusting reverse wavelength dispersion, and manufacturing, R ^d1 and R ^d2 are each independently an unsubstituted alkyl group having 1 to 4 carbon atoms. , R ^d1 and R ^d2 are more preferably bonded to each other to form a 5- to 7-membered non-aromatic hydrocarbon ring, which is an unsubstituted alkyl group having 1 to 2 carbon atoms, or R It is even more preferred that ^d1 and ^Rd2 are bonded together to form a 6-membered non-aromatic hydrocarbon ring.

In general formula (D _g -2), general formula (D _g -3), and general formula (D _g -4), R ^e1 , R ^e2 , R ^e3 and R ^e4 , and R ^d3 are each independently may be a hydrogen atom, but from the viewpoint of adjustment of reverse wavelength dispersion and solvent solubility, at least one of R ^e1 , R ^e2 , R ^e3 and R ^e4 , and R ^d3 is substituted A group ^E3 may be introduced. Introduction of the substituent ^E3 to at least one of R ^e1 , R ^e2 , R ^e3 and R ^e4 , and R ^d3 facilitates exhibiting reverse wavelength dispersion.
Incidentally, the substituent ^E3 in the general formula (2) may be the same as the substituent E in the general formula (1), so the explanation is omitted here.
From the viewpoint of adjusting the reverse wavelength dispersion, when the substituent E 3 is introduced into at least one of R ^e1 , R ^e2 , R ^e3 and R ^e4 , and R ^d3 , among the substituents ^{E 3 ,} indolenine It is preferable to introduce a substituent capable of extending the π-conjugated system of the ring (a group that extends the π-conjugated system of the indolenine ring). Substituents capable of extending the π-conjugated system of the indolenine ring include, for example, a group having a vacant orbital capable of accepting a π-bonded electron pair, a lone electron pair, or a lone electron pair, or a group exhibiting an inductive effect. Specifically, a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom, a nitro group, a cyano group, or a hydroxyl group, one —CH ₂ —, or two or more -CH ₂ - that are not adjacent are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, - O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH- , -CH=CH-, -CF=CF- or -C≡C-, a linear or branched alkyl group having 1 to 20 carbon atoms, a halogen atom, a nitro group, a cyano group, an amino or a hydroxyl group, among which a linear or branched alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkyloxycarbonyl group having 1 to 10 carbon atoms, and a carbon atom A hydroxyalkyl group of number 1 to 10, a trifluoromethyl group, a halogen atom, a nitro group, an amino group, or a hydroxyl group are more preferable, and a linear or branched alkyl group having 1 to 10 carbon atoms, a halogen atom , a nitro group, an alkoxy group having 1 to 10 carbon atoms, and the like are more preferable.
benzene in which R ^e1 , R ^e2 , R ^e3 and R ^e4 are bonded to each other to form a 5- to 7-membered aromatic hydrocarbon ring, and R ^e1 , R ^e2 , R ^e3 and R ^e4 are bonded to each other; Formation of a condensed ring containing a ring is also preferable from the viewpoint of expanding the conjugated system of the indolenine ring structure.

In the general formula (2), D ³ preferably represents a group selected from the general formula (D _g -2) from the viewpoint of adjustment of reverse wavelength dispersion.

Specifically, D ³ represents a group selected from the following formulas (d-1) to (d-17), so that raw materials are easily available, solubility is good, and reverse wavelength dispersion is particularly preferable because it is easy to adjust the

In the general formula (2), M represents -CH=CH-, -N=CH-, -CH=N-, or -N=N-. From, -CH=CH-, -N=CH-, or -CH=N- is preferred, CH=CH- or -CH=N- is more preferred, and -CH=CH- is even more preferred . From the viewpoint of reverse wavelength dispersion, it is preferable that M is a transformer type and that D and A ^core are coupled.

In the general formula (2), —MD ³ is preferably a group selected from the following general formula (MD-1).

（一般式（ＭＤ－１）中、Ｒ^ｄ１及びＲ^ｄ２、Ｒ^ｅ１、Ｒ^ｅ２、Ｒ^ｅ３及びＲ^ｅ４は、それぞれ前記一般式（Ｄ_ｇ－２）と同様であり、Ｘ^１及びＸ^２はそれぞれ独立して、ＣＨ又はＮである。＊（アスタリスク）はＡ^coreとの結合位置を示す。）

(In the general formula (MD-1), R ^d1 and R ^d2 , R ^e1 , R ^e2 , R ^e3 and R ^e4 are respectively the same as in the general formula (D _g -2), and X ¹ and X ² are Each is independently CH or N. * (asterisk) indicates the bonding position with A ^core .)

In general formula (MD-1), at least one of X ¹ and X ² is preferably CH, and at least X ¹ is more preferably CH, from the viewpoint of ease of synthesis and stability. Even more preferably, ¹ and ^X2 are both CH.

In the general formula (2), n11 represents an integer of 1 or 2, and one or two ^-MD3 bonds to A ^core described later. -MD ³ is a trivalent group when one is bonded to A ^core described ^later , and A ^core is a tetravalent group when two are bonded to A ^core described later.
In the general formula (2), n11 may be appropriately selected to be 1 or 2 in order to adjust the chromatic dispersion characteristics.
Above all, when n11 is 1, reverse wavelength dispersion tends to be exhibited.
Among them, when n11 is selected to be 2, at least one of R ^e1 , R ^e2 , R ^e3 and R ^e4 , and R ^d3 is added to the Indian It is preferable to introduce a substituent capable of extending the conjugation of the renin ring structure.

In general formula (2), A ^core is a monocyclic, condensed ring or ring assembly aromatic group which is unsubstituted or optionally substituted by one or more substituents E ³ and has 4 to 4 carbon atoms. Represents 16 trivalent or tetravalent groups.
The monocyclic aromatic hydrocarbon ring that constitutes the monocyclic aromatic group includes a benzene ring, and the monocyclic aromatic heterocycle that constitutes the monocyclic aromatic group includes a furan ring, a pyridine ring, and a pyrimidine ring. ring, pyrazine ring, and the like. Examples of the condensed aromatic hydrocarbon ring constituting the condensed ring aromatic group include naphthalene ring, anthracene ring, phenanthrene ring, etc. The condensed aromatic heterocycle constituting the condensed ring aromatic group includes A quinoline ring, an acridine ring, a phenanthridine ring and the like can be mentioned. Ring assembly refers to a structure in which two rings have no shared atoms and are linked via a bond. and a structure in which at least two rings selected from the group consisting of the above monocyclic and condensed aromatic heterocycles are directly linked. Structures constituting the ring-assembled aromatic group having 4 to 16 carbon atoms include, for example, biphenyl, 2-phenylnaphthalene, 1-phenylnaphthalene and the like.

A trivalent or tetravalent group having 4 to 16 carbon atoms that is a monocyclic, condensed ring or ring assembly aromatic group may be unsubstituted, but is substituted with one or more substituents E ³ described later. It's okay to be.
From the viewpoint of ease of synthesis, the substituents in A ^core include, among others, a fluorine atom, a chlorine atom, a hydroxyl group, a mercapto group, a methylamino group, a dimethylamino group, or one —CH ₂ — or adjacent two or more —CH ₂ — are each independently —O—, —S—, —CO—, —COO—, —OCO—, —CO—S—, —S—CO—, —O—CO It is preferably a linear or branched alkyl group having 1 to 6 carbon atoms which may be substituted with -O-, -CO-NH-, or -NH-CO-.

Examples of the trivalent or tetravalent group having 4 to 16 carbon atoms which is an unsubstituted monocyclic, condensed ring or ring assembly aromatic group in A ^core include the following formulas (Co-11) to (Co -28), but is not limited to the following.
In formulas (Co-11) to (Co-28) below, one or more hydrogen atoms in the aromatic group may be substituted with one or more substituents E ³ .

（式（Ｃｏ－１１）から式（Ｃｏ－２８）において、－Ｍ－Ｄ^３は、前記一般式（２）と同様であり、Ｍ、Ｄ^３が複数現れる場合は、各々同一であっても異なっていても良い。＊（アスタリスク）はＬ^１１又はＬ^１２との結合位置を示す。）

(In formulas (Co-11) to (Co-28), —MD ³ is the same as in general formula (2) above, and when multiple M and D ³ appear, they may be the same. It may be different.* (asterisk) indicates the binding position with ^L11 or ^L12 .)

The ring structure of the monocyclic, condensed ring, or ring-aggregated aromatic group in A ^core is preferably benzene, naphthalene, or biphenyl from the viewpoint of ease of raw material procurement, and benzene from the viewpoint of wavelength dispersion. is preferable, and biphenyl is preferable from the viewpoint of improving the orientation between molecules and the birefringence. When the polymerizable liquid crystal compound of the present disclosure has a large birefringence (Δn), it is possible to realize a retardation with a thin film compared to conventional ones.
The trivalent or tetravalent group having 4 to 16 carbon atoms which is an unsubstituted monocyclic, condensed ring or ring assembly aromatic group in A ^core is represented by the above formulas (Co-11) to (Co-18) It is preferable to represent at least one of a group selected from and a group selected from the above formulas (Co-26) to (Co-28).

L ¹¹ , L ¹² , L ¹³ and L ¹⁴ in general formula (2) may each independently be the same as L ¹ , L ² , L ³ and L ⁴ in general formula (1), so here is omitted.
A ¹¹ and A ¹² in the general formula (2) may each independently be the same as A ¹ and A ² in the general formula (1), so the description thereof is omitted here.
A ¹³ and A ¹⁴ in the general formula (2) may each independently be the same as A ³ and A ⁴ in the general formula (1), so the description thereof is omitted here.

m11 and m12 in general formula (2) each independently represents an integer of 1 to 4;
When emphasizing the liquid crystallinity and orientation of the polymerizable compound of the present embodiment, it is preferable that one or both of m11 and m12 is an integer of 1 to 3, and both m11 and m12 are integers of 1 to 3. and more preferably both m11 and m12 are 1 or 2.

In general formula (2), R ¹¹ and R ¹² each independently represent a group selected from general formula (R-11), and general formula (R-11): -L ¹⁵ -R ^sp11 L ^{15 ,} R ^sp11 , and Z ¹¹ in −Z 11 may be the same as L ⁵ , R ^sp1 , and Z ¹ in general formula (1), respectively, and descriptions thereof are omitted here.

In general formula (2), Lc11: -L ¹¹ -A ¹¹ -(L ¹³ -A ¹³ ) _m11 -L ¹⁵ -R ^sp11 -Z ¹¹ and Lc12: -L ¹² -A ¹² -(L ¹⁴ -A ¹⁴ ) Specific examples of _m12 -L ¹⁵ -R ^sp11 -Z ¹¹ include groups represented by Lc-1 to Lc-244 listed in Tables 1 to 6 described in general formula (1). . In the polymerizable liquid crystal compound represented by formula (2), Lc11 and Lc12 may be the same or different.

Furthermore, the compound represented by the general formula (2) includes, for example, compounds (b1) to (b85) below. Lc11 in the table is -L ¹¹ -A ¹¹ -(L ¹³ -A ¹³ ) _m11 -L ¹⁵ -R ^sp11 -Z ¹¹ , and Lc12 is -L ¹² -A ¹² -(L ¹⁴ -A ¹⁴ ) _m12 -L ¹⁵ -R ^sp11 -Z ¹¹ ;

Furthermore, representative structural formulas of compounds (b1) to (b85) in Tables 9 to 10 are shown below, but are not limited to these. In the following, R ¹¹ and R ¹² each independently represent a group selected from the general formula (R-11), and among them, L ¹⁵ is -O-, -COO-, -OCO-, or -O —CO—O— is more preferred, and R ¹¹ and R ¹² may be the same or different. Further, each R ^sp11 more preferably independently represents an alkylene group having 1 to 20 carbon atoms, and R ¹¹ and R ¹² may be the same or different. Further, Z ¹¹ is more preferably represented by the above formula (Z-1), and in formula (Z-1), it is particularly preferable that R ^z is a hydrogen atom, a methyl group or a trifluoromethyl group.

The polymerizable liquid crystal compound (B) represented by general formula (2) can be produced, for example, by the following production method. Examples of the production method include known organic synthesis reactions described in Methoden der Organischen Chemie, Organic Reactions, Organic Syntheses, Comprehensive Organic Synthesis, Shin Jikken Kagaku Koza, etc. reaction, Wittig reaction, Schiff base formation reaction, benzylation reaction, Sonogashira reaction, Suzuki-Miyaura reaction, Negishi reaction, Kumada reaction, Hiyama reaction, Buchwald-Hartwig reaction, Friedel-Crafts reaction, Heck reaction, Aldol reaction, Duff reaction, etc.) can be appropriately combined depending on the structure. Examples of manufacturing methods are shown below, but the present disclosure is not limited to these structures and manufacturing methods.

For example, L ¹¹ and L ¹² are each *-OCO- (* indicates the bonding position with A ^core ), D ³ represents a group selected from general formula (D _g -2), and M is - Compounds in which CH=CH- can be produced, for example, as follows.
First, an indolenine compound represented by formula (ip-11) is prepared and subjected to bromination to obtain intermediate H represented by formula (ip-12).

On the other hand, an intermediate I in which an aldehyde group is introduced at the position where M is introduced in A ^core is prepared. When A ^core is a benzene ring, for example, 2,5-dihydroxybenzaldehyde is prepared. Further, for example, when A ^core is biphenyl, 4,4′-dihydroxybiphenyl or further substituent E ³ (in formulas (ip-13) and (ip-14), E ¹¹ and E ¹² are substituents E ³ and n12 or n13 is 0 or 1) is prepared, and an aldehyde group is introduced at a desired position by Duff reaction or the like to obtain a compound represented by formula (ip -14) to prepare intermediate I'.

Next, intermediate H represented by formula (ip-12) and 2,5-dihydroxybenzaldehyde represented by formula (ip-15), etc., introduce an aldehyde group at the position where M is introduced in A ^core . Intermediate J of formula (ip-16) is obtained by reaction with intermediate I obtained.

_Next , intermediate J of formula (ip-16) and intermediate K1 ⁽ A ^{11 ,} L ¹³ , A ^{13 , R 11} , and m11 have the same meaning as above) are reacted by a condensation reaction or the like to obtain an intermediate L represented by the formula (ip-17), and further the obtained formula (ip- 17) and intermediate K2 represented by HOOC-A ¹² -(L ¹⁴ -A ¹⁴ ) _m12 -R ¹² (A ¹² , L ¹⁴ , A ¹⁴ , R ¹² and m12 are (having the same meaning as above) to give a compound represented by the formula (2-ex1). When intermediate K1 and intermediate K2 have the same structure, a compound represented by formula (2-ex1) can be obtained by reacting intermediate K1 with intermediate J of formula (ip-16). can.

In addition, when a ring-assembled aromatic group such as biphenyl is used in the A ^core , depending on the type and substitution position of the substituent ^E3 and the substitution position of M, for example, 3,4-methylenedioxyphenol (Tokyo Chemical Industry Co., Ltd.) ) or its derivative by subjecting it to a Duff reaction to introduce an aldehyde group, followed by a Suzuki-Miyaura coupling reaction.

Further, for example, intermediate I, such as 2,5-dihydroxybenzaldehyde represented by formula (ip-15), in which an aldehyde group is introduced at the position where M is introduced in A ^core , is added to HOOC-A, which is the main chain portion. Intermediate K1 represented by ^11- (L ¹³ -A ¹³ ) _m1 -R ¹¹ (A ¹¹ , L ¹³ , A ¹³ , R ¹¹ and m11 have the same meanings as above) and HOOC-A ¹² -(L ¹⁴ -A ¹⁴ ) _m12 -R ¹² (A ¹² , L ¹⁴ , A ¹⁴ , R ¹² , and m12 have the same meaning as above), followed by reaction of the aldehyde A compound represented by formula (2-ex1) may be obtained by reacting intermediate H represented by formula (ip-12) with the group.

Further, in the case of a compound in which M is -CH=N-, it can be produced, for example, as follows.
A corresponding indolenine amine body is prepared as an intermediate H′ represented by the formula (ip-12′), and the intermediate H′ represented by the formula (ip-12′) and the formula (ip-15 ), such as 2,5-dihydroxybenzaldehyde represented by ), is reacted with an intermediate I having an aldehyde group introduced at the position where M is introduced in A ^core under acidic conditions to obtain an intermediate of formula (ip-16′) Except for obtaining J', it can be produced in the same manner as described above.

Moreover, each intermediate used for manufacture may use a commercial item suitably, and can synthesize|combine suitably by a conventionally well-known method.

The polymerizable liquid crystal compound (B) represented by the general formula (2) of the present disclosure is obtained, for example, by the method described in Example 1 below, as a polymerizable liquid crystal compound represented by the general formula (2). A polymerizable composition containing only the compound (B) and a photopolymerization initiator was prepared to form a cured film (retardation layer), and when the retardation value was measured as described later, Re (450)/Re (550) can exhibit a flat wavelength dispersion of 0.99 or more and less than 1.01 and a reverse wavelength dispersion of Re (450) / Re (550) of less than 0.99, Re (450) / Re(550) preferably exhibits a reverse wavelength dispersion of less than 0.99, more preferably less than 0.95. Further, in the polymerizable liquid crystal compound (B) represented by the general formula (2) of the present disclosure, Re (650) / Re (550) is preferably 1 or more, more preferably greater than 1, It is even more preferable to be in the range of 1.02 or more and 1.1 or less.

In the polymerizable composition of the present disclosure, the polymerizable liquid crystal compound (B) represented by the general formula (2) may be used singly or in combination of two or more.
In the present embodiment, since a polymerizable composition having high solution stability and excellent in-plane uniformity can be obtained, the content of the polymerizable liquid crystal compound (B) represented by the general formula (2) is It is preferably 1 part by mass or more, more preferably 5 parts by mass or more, and even more preferably 10 parts by mass or more, based on 100 parts by mass of the total amount of the liquid crystal compound. On the other hand, since a polymerizable composition having a large birefringence (Δn) and reverse wavelength dispersion can be obtained, the content of the polymerizable liquid crystal compound (B) represented by the general formula (2) is , the amount is preferably 90 parts by mass or less, more preferably 70 parts by mass or less, and even more preferably 50 parts by mass or less with respect to the total 100 parts by mass of the polymerizable liquid crystal compound.

3. Other Components The polymerizable composition of the present disclosure includes at least a polymerizable liquid crystal compound (A) represented by the general formula (1) and a polymerizable liquid crystal compound (B) represented by the general formula (2). Although it contains, it is preferable to further contain a photopolymerization initiator.
Further, the polymerizable composition of the present disclosure is further represented by the general formula (1) from the point of adjusting the retardation and reverse wavelength dispersion, and from the point of adjusting the orientation, solubility, and phase transition temperature. It may contain a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B) represented by the general formula (2), and further to the extent that the effect is not impaired. It may contain other components. Hereinafter, each component constituting the polymerizable composition of the present disclosure will be described in order.

3-1. Photopolymerization Initiator In the present embodiment, the photopolymerization initiator can be appropriately selected from conventionally known substances and used. Specific examples of such photopolymerization initiators include aromatic ketones including thioxanthone, α-aminoalkylphenones, α-hydroxyketones, acylphosphine oxides, oxime esters, and aromatic oniums. Preferred examples include salts, organic peroxides, thio compounds, hexaarylbiimidazole compounds, ketoxime ester compounds, borate compounds, azinium compounds, metallocene compounds, active ester compounds, compounds having a carbon-halogen bond, and alkylamine compounds. Among them, acylphosphine oxide-based polymerization initiators, α-aminoalkylphenone-based polymerization initiators, α-hydroxyketone-based polymerization initiators, and oxime ester-based polymerization initiators are used to improve durability by curing to the inside of the coating film. At least one selected from the group consisting of polymerization initiators is preferred.

Acylphosphine oxide-based polymerization initiators include, for example, bis(2,4,6-trimethylbenzoyl)-phenyl-phosphine oxide (eg, trade name: Irgacure 819, manufactured by BASF), bis(2,6-dimethoxy benzoyl)-2,4,4-trimethyl-pentylphenylphosphine oxide, 2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide (trade name: Lucirin TPO: manufactured by BASF, etc.), and the like.

Examples of α-aminoalkylphenone-based polymerization initiators include 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one (eg Irgacure 907, manufactured by BASF), 2- benzyl-2-(dimethylamino)-1-(4-morpholinophenyl)-1-butanone (eg Irgacure 369, manufactured by BASF), 2-(dimethylamino)-2-[(4-methylphenyl)methyl] -1-[4-(4-morpholinyl)phenyl]-1-butanone (Irgacure 379EG, manufactured by BASF) and the like.

Examples of α-hydroxyketone-based polymerization initiators include 2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]-phenyl}-2-methyl-propane -1-one (e.g., trade name: Irgacure 127, manufactured by BASF, etc.), 2-hydroxy-4'-hydroxyethoxy-2-methylpropiophenone (e.g., trade name: Irgacure 2959, manufactured by BASF, etc.), 1-hydroxy-cyclohexyl-phenyl-ketone (e.g., trade name: Irgacure 184, manufactured by BASF, etc.), oligo {2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propanone} ( For example, trade name: ESACURE ONE, manufactured by Lamberti, etc.).

Examples of oxime ester polymerization initiators include 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyloxime)] (trade name: Irgacure OXE-01, manufactured by BASF), ethanone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-,1-(o-acetyloxime) (trade name: Irgacure OXE-02, manufactured by BASF), methanone, ethanone , 1-[9-ethyl-6-(1,3-dioxolane, 4-(2-methoxyphenoxy)-9H-carbazol-3-yl]-, 1-(o-acetyloxime) (trade name ADEKA OPT- N-1919, manufactured by ADEKA) and the like.

In this embodiment, the photopolymerization initiator can be used singly or in combination of two or more.
In the present embodiment, the content of the photopolymerization initiator is 0.1 parts by mass or more and 10 parts by mass or less with respect to 100 parts by mass of the solid content of the polymerizable composition from the viewpoint of promoting the curing of the polymerizable compound. It is preferably 1 part by mass or more and 8 parts by mass or less.

3-2. A polymerizable liquid crystal compound different from the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B) In the polymerizable composition of the present disclosure, the polymerizable liquid crystal compound (A) represented by the general formula (1) And the polymerizable liquid crystal compound different from the polymerizable liquid crystal compound (B) represented by the general formula (2) can be appropriately selected from conventionally known compounds and used. The normal dispersion (positive dispersion) in which the slope of the graph obtained by plotting the wavelength λ of the incident light on the retardation film on the horizontal axis and the birefringence on the vertical axis is negative (downward to the right). It may be a polymerizable liquid crystal compound, a reverse wavelength dispersion polymerizable liquid crystal compound, or a polymerizable liquid crystal compound that does not substantially exhibit wavelength dispersion (flat dispersion or low wavelength dispersion). can be As a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B), for example, compounds exhibiting reverse wavelength dispersion are disclosed in Japanese Patent No. 5463666, Japanese Patent No. 4186981, Examples include polymerizable liquid crystal compounds described in No. 5,962,760 and Japanese Patent No. 5,826,759. Examples of compounds exhibiting flat dispersibility include compounds described in Recueil des Travaux Chimiques des Pays-Bas (1996), 115(6), 321-328.

In the present embodiment, it is preferable to use a polymerizable liquid crystal compound having a polymerizable functional group at at least one end of the rod-shaped mesogen because it is easily aligned in combination with the polymerizable liquid crystal compound, and both ends of the rod-shaped mesogen A polymerizable liquid crystal compound having a polymerizable functional group is more preferable. A polymerizable liquid crystal compound having two or more polymerizable functional groups in one molecule can improve the hardness and durability of a coating film.
As the polymerizable liquid crystal compound used in the present disclosure, for example, a polymerizable liquid crystal compound represented by the following general formula (I) having a structure similar to that of the main chain portion of the polymerizable compound, and a polymerizable liquid crystal compound represented by the following general formula (II ) and a polymerizable liquid crystal compound represented by.

（式中、Ｚ^１０、及びＺ^２０は各々独立して重合性官能基を表し、Ｒ^ｓｐ１０、及びＲ^ｓｐ２０は各々独立して単結合又は炭素原子数１～２０個のアルキレン基を表すが、１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－は－Ｏ－、－ＣＯＯ－、－ＯＣＯ－、－ＯＣＯＯ－に置き換えられても良く、Ｌ^１０、Ｌ^２０及びＬ^３０は各々独立して－Ｏ－、－Ｓ－、－ＯＣＨ_２－、－ＣＨ_２Ｏ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＳＣＨ_２－、－ＣＨ_２Ｓ－、－ＣＦ_２Ｏ－、－ＯＣＦ_２－、－ＣＦ_２Ｓ－、－ＳＣＦ_２－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＯＯ－ＣＨ_２ＣＨ_２－、－ＯＣＯ－ＣＨ_２ＣＨ_２－、－ＣＨ_２ＣＨ_２－ＣＯＯ－、－ＣＨ_２ＣＨ_２－ＯＣＯ－、－ＣＯＯ－ＣＨ_２－、－ＯＣＯ－ＣＨ_２－、－ＣＨ_２－ＣＯＯ－、－ＣＨ_２－ＯＣＯ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－、－Ｃ≡Ｃ－又は単結合を表し、Ａ^１０、及びＡ^２０は各々独立して、ベンゼン－１，４－ジイル基、シクロヘキサン－１，４－ジイル基、ピリジン－２，５－ジイル基、ピリミジン－２，５－ジイル基、ナフタレン－２，６－ジイル基、ナフタレン－１，４－ジイル基、テトラヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表すが、Ａ^１０、及びＡ^２０は各々独立して無置換であるか又はアルキル基、ハロゲン化アルキル基、アルコキシ基、ハロゲン化アルコキシ基、ハロゲン原子、シアノ基又はニトロ基に置換されていても良く、Ｒは水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、ペンタフルオロスルフラニル基、シアノ基、ニトロ基、イソシアノ基、チオイソシアノ基、若しくは、１個の－ＣＨ_２－又は隣接していない２個以上の－ＣＨ_２－が各々独立して－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯ－Ｓ－、－Ｓ－ＣＯ－、－Ｏ－ＣＯ－Ｏ－、－ＣＯ－ＮＨ－、－ＮＨ－ＣＯ－、－ＣＨ＝ＣＨ－ＣＯＯ－、－ＣＨ＝ＣＨ－ＯＣＯ－、－ＣＯＯ－ＣＨ＝ＣＨ－、－ＯＣＯ－ＣＨ＝ＣＨ－、－ＣＨ＝ＣＨ－、－ＣＦ＝ＣＦ－又は－Ｃ≡Ｃ－によって置換されても良い炭素原子数１～２０の直鎖又は分岐アルキル基を表し、ｓ１及びｓ２は０、１、２、３又は４を表すが、ｓ１及びｓ２がそれぞれ独立に２、３又は４を表す場合、２個、３個あるいは４個存在するＡ^２０、Ｌ^１０はそれぞれ同一であっても異なっていても良い。）

(wherein Z ¹⁰ and Z ²⁰ each independently represent a polymerizable functional group, R ^sp10 and R ^sp20 each independently represent a single bond or an alkylene group having 1 to 20 carbon atoms, One -CH ₂ - or two or more non-adjacent -CH ₂ - may be replaced with -O-, -COO-, -OCO-, -OCOO-, L ¹⁰ , L ²⁰ and L ³⁰ each independently represents -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, - O—CO—O—, —CO—NH—, —NH—CO—, —SCH ₂ —, —CH ₂ S—, —CF ₂ O—, —OCF ₂ —, —CF ₂ S—, —SCF ₂ -, -CH=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-, -CF=CF-, -C≡C- or a single bond, and A ¹⁰ and A ²⁰ are each independently a benzene-1,4-diyl group and a 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, tetrahydronaphthalene-2,6-diyl group or 1,3 -dioxane-2,5-diyl group, and A ¹⁰ and A ²⁰ are each independently unsubstituted or alkyl group, halogenated alkyl group, alkoxy group, halogenated alkoxy group, halogen atom, cyano or a nitro group, and 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 - are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S- , -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH- , -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C- represents a linear or branched alkyl group having 1 to 20 carbon atoms which may be substituted by s1 and s2 represents 0, 1, 2, 3 or 4, but when s1 and s2 each independently represent 2, 3 or 4, two, three or four A ²⁰ and L ¹⁰ are the same It can be different. )

Examples of the polymerizable functional group possessed by the polymerizable liquid crystal compound include those similar to ^Z1 and the like of the polymerizable compound. Examples of the polymerizable functional group possessed by the polymerizable liquid crystal compound include a cyclic ether-containing group such as an oxirane ring and an oxetane ring, and an ethylenic double bond-containing group. An ethylenic double bond-containing group is preferred from the standpoint of superiority. Cyclic ether groups include, for example, glycidyl groups. Examples of the ethylenic double bond-containing group include a vinyl group, an allyl group, a (meth)acryloyl group, etc. Among them, a (meth)acryloyl group is preferable.

In the present embodiment, the polymerizable liquid crystal compound is one or more selected from compounds represented by the following general formula (III) and compounds represented by the following general formula (IV), among others, from the viewpoint of orientation. are preferred.

（一般式（ＩＩＩ）中、Ｒ^２１は、水素原子又はメチル基を、Ｒ^２２は、－（ＣＨ_２）_ｐ－、又は－（Ｃ_２Ｈ_４Ｏ）_ｐ’－で表される基を表す。Ｌ^２３は、直接結合、又は、－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、若しくは－Ｃ（＝Ｏ）－Ｏ－で表される連結基を、Ａｒ^３は、ベンゼン－１，４－ジイル基、シクロヘキサン－１，４－ジイル基、ピリジン－２，５－ジイル基、ピリミジン－２，５－ジイル基、ナフタレン－２，６－ジイル基、ナフタレン－１，４－ジイル基、テトラヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表すが、Ａｒ^３は無置換であるか又はアルキル基、ハロゲン化アルキル基、アルコキシ基、ハロゲン化アルコキシ基、ハロゲン原子、シアノ基又はニトロ基に置換されていても良く、複数あるＬ^２３及びＡｒ^３はそれぞれ同一であっても異なっていても良い。Ｒ^２３は、－Ｆ、－Ｃｌ、－ＣＮ、－ＯＣＦ_３、－ＯＣＦ_２Ｈ、－ＮＣＯ、－ＮＣＳ、－ＮＯ_２、－ＮＨＣ（＝Ｏ）－Ｒ^２４、－Ｃ（＝Ｏ）－ＯＲ^２４、－ＯＨ、－ＳＨ、－ＣＨＯ、－ＳＯ_３Ｈ、－ＮＲ^２４ _２、－Ｒ^２５、又は－ＯＲ^２５を、Ｒ^２４は、水素原子又は炭素原子数１以上６以下のアルキル基を表し、Ｒ^２５は、炭素原子数１以上６以下のアルキル基を表す。ｂは２以上５以下の整数、ｐ及びｐ’はそれぞれ独立に２以上１０以下の整数である。

(In general formula (III), R ²¹ represents a hydrogen atom or a methyl group, and R ²² represents a group represented by —(CH ₂ ) _p — or —(C ₂ H ₄ O) _p′ — L ²³ is a direct bond or a linking group represented by -O-, -OC(=O)- or -C(=O)-O-, Ar ³ is 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, represents a tetrahydronaphthalene-2,6-diyl group or a 1,3-dioxane-2,5-diyl group, where Ar ³ is unsubstituted or an alkyl group, halogenated alkyl group, alkoxy group, or halogenated alkoxy group , a halogen atom, a cyano group or a nitro group, and a plurality of L ²³ and Ar ³ may be the same or different, and R ²³ is —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 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ²⁵ represents represents an alkyl group, b is an integer of 2 or more and 5 or less, p and p' are each independently an integer of 2 or more and 10 or less;

（一般式（ＩＶ）中、Ｒ^３１及びＲ^３２は各々独立に、水素原子又はメチル基を、Ｒ^３３は、－（ＣＨ_２）_ｑ－、又は－（Ｃ_２Ｈ_４Ｏ）_ｑ’－で表される基を、Ｒ^３４は、－（ＣＨ_２）_ｒ－、又は－（ＯＣ_２Ｈ_４）_ｒ’－で表される基を表す。Ｌ^３４は、直接結合、又は、－Ｏ－、－Ｏ－Ｃ（＝Ｏ）－、若しくは－Ｃ（＝Ｏ）－Ｏ－で表される連結基を、Ａｒ^４は、ベンゼン－１，４－ジイル基、シクロヘキサン－１，４－ジイル基、ピリジン－２，５－ジイル基、ピリミジン－２，５－ジイル基、ナフタレン－２，６－ジイル基、ナフタレン－１，４－ジイル基、テトラヒドロナフタレン－２，６－ジイル基又は１，３－ジオキサン－２，５－ジイル基を表すが、Ａｒ^４は無置換であるか又はアルキル基、ハロゲン化アルキル基、アルコキシ基、ハロゲン化アルコキシ基、ハロゲン原子、シアノ基又はニトロ基に置換されていても良く、複数あるＬ^３４及びＡｒ^４はそれぞれ同一であっても異なっていても良い。ｃは２以上５以下の整数、ｑ、ｑ’、ｒ及びｒ’はそれぞれ独立に２以上１０以下の整数である。）

(In general formula (IV), R ³¹ and R ³² are each independently a hydrogen atom or a methyl group, R ³³ is —(CH ₂ ) _q — or —(C ₂ H ₄ O) _q′ — R ³⁴ represents a group represented by —(CH ₂ ) _r — or —(OC ₂ H ₄ ) _r′ —, L ³⁴ is a direct bond, or —O—, Ar ⁴ is a benzene-1,4-diyl group, a 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, tetrahydronaphthalene-2,6-diyl group or 1,3- represents a dioxane-2,5-diyl group, wherein Ar ⁴ is unsubstituted or substituted with an alkyl group, halogenated alkyl group, alkoxy group, halogenated alkoxy group, halogen atom, cyano group or nitro group; a plurality of L ³⁴ and Ar ⁴ may be the same or different, c is an integer of 2 or more and 5 or less, q, q', r and r' are each independently 2 or more and 10 or less; is an integer.)

p, p' in general formula (III), q, q', r and r' in general formula (IV) are preferably 2 or more and 8 or less, and 2 or more and 6 or less from the viewpoint of orientation. is more preferable, and 2 or more and 5 or less is even more preferable.
Ar ³ and Ar ⁴ are respectively 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, tetrahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl group, especially benzene-1,4-diyl group, A naphthalene-2,6-diyl group or a cyclohexane-1,4-diyl group is more preferred. Substituents that Ar ³ and Ar ⁴ may have include an alkyl group, a halogenated alkyl group, an alkoxy group, a halogenated alkoxy group, a halogen atom, a cyano group or a nitro group, more preferably a carbon atom. Examples include an alkyl group having a number of 1 or more and 5 or less, a halogen atom, or the like.
In addition, the alkyl group having 1 to 6 carbon atoms in R ²⁴ and R ²⁵ in general formula (III) may be linear, branched, or cyclic. -linear alkyl groups such as propyl, n-butyl, n-pentyl and n-hexyl groups; branched alkyl groups such as i-propyl, i-butyl, t-butyl and 2-methylbutyl; Cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl groups are included. Among them, R ²⁴ is preferably a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. Among them, R ²⁵ is preferably an alkyl group having 1 to 5 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms.
Among them, R ²³ is —Cl, —CN, —OCF ₃ , —OCF ₂ H, —NCO, —NCS, —NO ₂ , —NHC(=O)—R ²⁵ , —C(= O) —OR ²⁴ , —OH, —SH, —CHO, —SO ₃ H, —NR ²⁴ ₂ , —R ²⁵ , or —OR ²⁵ , —Cl, —CN, —OCF ₃ or — It is more preferably C(=O)--OR ²⁴ , --R ²⁵ or --OR ²⁵ .

As the mesogenic structure contained in the polymerizable liquid crystal compound, partial structures represented by the following chemical formulas (V-1) to (V-6) are preferably used, and among them, the following chemical formula (V A partial structure represented by at least one selected from the group consisting of -1), (V-2), (V-4), (V-5), and (V-6) is preferably used. A hydrogen atom in a phenylene group or a naphthylene group in the partial structures represented by the following chemical formulas (V-1) to (V-6) may be substituted with an alkyl group having 1 to 3 carbon atoms or a halogen atom. .

Preferred specific examples of the compound represented by the general formula (III) and the compound represented by the general formula (IV) include those represented by the following chemical formulas (1) to (22). It is not limited.

（ｇは２～５の整数である。）

(g is an integer from 2 to 5.)

In this embodiment, the polymerizable liquid crystal compounds different from the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B) can be used singly or in combination of two or more.
In addition, the content of the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound different from the polymerizable liquid crystal compound (B) may be adjusted as appropriate to adjust the desired retardation or the like. The amount is preferably 30 parts by mass or less, more preferably 10 parts by mass or less with respect to 100 parts by mass of the total amount of the liquid crystal compound.

3-3. Other Components The polymerizable composition of the present embodiment may further contain other components as long as the effects are not impaired. Specifically, as other components, a leveling agent, an antioxidant, a light stabilizer, and from the viewpoint of coatability, a solvent and the like may be contained. In addition, even if it contains a polymerizable compound that does not exhibit liquid crystallinity by itself but can adjust retardation, reverse wavelength dispersion, phase transition temperature, hardness, durability, etc. by using it together with the polymerizable liquid crystal compound of the present disclosure good. For these materials, conventionally known materials may be appropriately selected and used.

In order to improve the hardness and durability of the coating film, it is preferable to further contain a polymerizable compound having two or more polymerizable functional groups in one molecule. As the polymerizable compound having two or more polymerizable functional groups in one molecule, in addition to the polymerizable liquid crystal compound as described above, a polymerizable compound having no liquid crystallinity can be used.
As the polymerizable compound having two or more polymerizable functional groups in one molecule, so-called polyfunctional monomers can also be used, 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) Acrylates, neopentyl glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, dipentaerythritol 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, isobornyl di(meth)acrylate, dicyclopentane di(meth)acrylate, tricyclodecane di(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, and modified with PO, EO, etc. The following are listed. Pentaerythritol triacrylate (PETA), dipentaerythritol hexaacrylate (DPHA), pentaerythritol tetraacrylate (PETTA), dipentaerythritol pentaacrylate (DPPA), A polymerizable compound having three or more polymerizable functional groups in one molecule, such as trimethylolpropane triacrylate (TMPTA), is preferred.
When a polymerizable compound having no liquid crystallinity is used in the present embodiment, the content is preferably 40 parts by mass or less, preferably 30 parts by mass or less, relative to 100 parts by mass of the solid content of the polymerizable composition. is more preferable, and 20 parts by mass or less is even more preferable.
In the present embodiment, the polymerizable compound different from the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B) of the present disclosure is selected from the group consisting of methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone. Dissolving 20% by mass or more in at least one selected solvent improves the solvent solubility of the polymerizable composition, and when forming a coating film using the polymerizable composition, a uniform coating film is easy to form, the load on the production process and production equipment for drying the solvent is reduced, and the choice of usable base material is expanded.

As the leveling agent, it is preferable to use a fluorine-based or silicone-based leveling agent. Specific examples of the leveling agent include, for example, the Megafac series manufactured by DIC Corporation described in JP-A-2010-122325, the TSF series manufactured by Momentive Performance Materials Japan, and the series manufactured by Neos. Futergent series etc. are mentioned. When a leveling agent is used in the present embodiment, the content is preferably 0.001 parts by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the solid content of the polymerizable composition.

From the viewpoint of coatability, the polymerizable composition of the present embodiment may contain a solvent, if necessary. The solvent may be appropriately selected from conventionally known solvents capable of dissolving or dispersing each component contained in the polymerizable composition. Specifically, for example, hydrocarbon solvents such as hexane, cyclohexane, and toluene, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, and cyclohexanone, tetrahydrofuran, 1,3-dioxolane, propylene glycol monoethyl ether ( PGME), alkyl halide 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, and sulfoxide solvents such as dimethylsulfoxide, 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 as a mixed solvent.

The polymerizable composition of the present embodiment is suitable for various uses because of its good orientation. The polymerizable composition of the present embodiment has good solution stability and is suitably used as a liquid crystal composition exhibiting reverse wavelength dispersion, for example, for retardation films and various optical members, which will be described later.

B. Polymer The polymer of the present disclosure is obtained by polymerizing the polymerizable composition of the present disclosure. The polymerization method is appropriately selected according to the polymerizable functional groups contained in the polymerizable liquid crystal compound (A) represented by the general formula (1) and the polymerizable liquid crystal compound (B) represented by the general formula (2). can be selected.
A polymer obtained by polymerizing the polymerizable composition of the present disclosure without orientation can be used, for example, as a light scattering plate, a depolarizing plate, and a moire fringe prevention plate.
In addition, the polymer obtained by polymerizing after orienting the polymerizable composition of the present disclosure has optical anisotropy, and is suitably used for retardation films and various optical members, which will be described later.

C. Retardation Film The retardation film of the present disclosure is a retardation film having a retardation layer, and the retardation layer contains a cured product of the polymerizable composition of the present disclosure.
In the retardation film of the present embodiment, since the retardation layer contains the cured product of the polymerizable composition, as described above, the retardation film exhibits reverse wavelength dispersion, good orientation, The in-plane uniformity of the retardation value is excellent.

The layer structure of the retardation film will be described with reference to the drawings. 1-3 each illustrate one embodiment of the retardation film of the present disclosure. One embodiment of the retardation film 10 shown in the example of FIG. 1 is a retardation film in which an alignment film 3 and a retardation layer 1 are laminated in this order on a substrate 2 . One embodiment of the retardation film 10 shown in the example of FIG. 2 is a retardation film consisting of the retardation layer 1 only. In one embodiment of the retardation film 10 shown in the example of FIG. 3, the retardation layer 1 is formed directly on the substrate 2'. The retardation film shown in the example of FIG. 3 may be provided with a means for exerting an orientation regulating force on the surface of the substrate 2' on the retardation layer 1 side. Here, in the present disclosure, the term "orientation regulating force" refers to the action of aligning the orientation component in the retardation layer in a specific direction.

1. Retardation Layer The retardation layer 1 of the embodiment of the present disclosure contains a cured product of the polymerizable composition of the present disclosure.
Here, the polymerizable composition of the present disclosure may be the same as that described in the polymerizable composition of the embodiment of the present disclosure, and thus description thereof is omitted here.

The retardation layer may include a main chain portion having orientation of the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B) contained in the polymerizable composition of the present disclosure, and further It is preferable that the polymerizable liquid crystal compound is cured in a substantially horizontal orientation with respect to the film surface. A 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 is polymerized. Since such a structure in which at least a part of the polymerizable functional group of the polymerizable compound is polymerized is included, the retardation layer of the present embodiment is a retardation layer with improved durability.

The phase difference can be measured by an automatic birefringence measuring device (for example, manufactured by Oji Scientific Instruments Co., Ltd., trade name: KOBRA-WR). The measurement light is incident perpendicularly or obliquely on the retardation layer surface, and from the chart of the optical retardation and the incident angle of the measurement light, the anisotropy that increases or decreases the retardation of the retardation layer, or the liquid crystal vertical (thickness It is possible to confirm the degree of orientation of the direction.

Further, the retardation layer includes the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B) contained in the polymerizable composition of the present disclosure, and the polymerizable liquid crystal compound that may be further included. The presence of a structure in which at least a part of the functional group is polymerized can be confirmed by collecting and analyzing the material from the retardation layer. As analytical methods, NMR, IR, GC-MS, XPS, TOF-SIMS and combinations thereof can be applied.

The retardation layer may contain other components such as a photopolymerization initiator, a leveling agent, an antioxidant, and a light stabilizer. If the retardation layer does not contain a component such as a photopolymerization initiator, which may be completely decomposed when light is irradiated to react the polymerizable functional group of the polymerizable liquid crystal compound. There is also

The thickness of the retardation layer may be appropriately set depending on the application.
The retardation film of the present disclosure, for example, when used as a broadband quarter-wave plate, Re (550) of the obtained retardation film is 113 nm or more and 163 nm or less, preferably 135 nm or more and 140 nm or less, particularly preferably about 137 The film thickness may be adjusted to about 5 nm, and in the case of a half-wave plate, the Re(550) of the obtained optical film is 250 nm or more and 300 nm or less, preferably 273 nm or more and 277 nm or less, particularly preferably about 275 nm. The film thickness may be adjusted so as to be about the same.

By appropriately adjusting the coating amount of the polymerizable composition and the concentration of the polymerizable liquid crystal compound, the film thickness can be adjusted so as to provide a desired retardation. The retardation value (retardation value, Re(λ)) of the obtained retardation layer is determined by the following formula. good.
Re(λ)=d×Δn(λ)
(Wherein, Re (λ) represents the retardation value at the wavelength λ nm, d represents the film thickness, and Δn (λ) represents the birefringence at the wavelength λ nm.)
The thickness of the retardation layer is preferably 0.1 μm or more and 5 μm or less, more preferably 0.5 μm or more and 3 μm or less.
Since the polymerizable liquid crystal compound (A) represented by the general formula (1) has a large birefringence (Δn), it is possible to achieve a retardation with a thinner film than before.

The wavelength dispersion characteristics of the retardation film of the present disclosure, depending on the content of the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B) in the retardation layer and the polymerizable liquid crystal compound that may be otherwise contained, It can be determined arbitrarily. When the content of the polymerizable liquid crystal compound (A) is increased in the retardation layer, the reverse wavelength dispersion characteristic tends to increase.
In the retardation layer of the present disclosure, Re (450) / Re (550) is preferably in the range of 0.75 or more and less than 0.95 in order to approximate ideal reverse wavelength dispersion, and further 0 It is preferably in the range of 0.78 or more and less than 0.93, and more preferably in the range of 0.80 or more and less than 0.90. Also, Re(650)/Re(550) is preferably greater than 1, and more preferably in the range of 1.02 or more and 1.1 or less.

2. Alignment Film In the present specification, the alignment film refers to a layer for aligning the liquid crystalline component contained in the retardation layer in a certain direction.
As the alignment film used in the embodiment of the present disclosure, it is preferable to use a horizontal alignment film because the polymerizable composition of the embodiment of the present disclosure is easily horizontally aligned.
If the horizontal alignment film is provided as a coating film, the long axis of the mesogen of the liquid crystalline component contained in the retardation layer is aligned substantially horizontally with respect to the horizontal alignment film surface (film surface). good.
As the horizontal alignment film, conventionally known ones can be appropriately selected and used. A horizontal alignment film to which an alignment regulating force is imparted by a rubbing method, a photo-alignment method or a shaping method is preferred.

When the alignment control force is applied by the rubbing method, a polymer that develops the alignment control force by rubbing is used for the horizontal alignment film. Examples of the polymer include polyvinyl alcohol, polyimide, polyamide and derivatives thereof, with polyvinyl alcohol being preferred.

A method for forming a horizontal alignment film by a rubbing method may be appropriately selected from conventionally known methods. For example, a horizontal alignment film can be obtained by forming a coating film containing the polymer on the transparent substrate and then rubbing the coating film with a known rubbing roller or the like.

When a horizontal alignment film is formed by a photo-alignment method, a photo-alignment composition containing a photo-alignment material that exhibits an alignment control force upon irradiation with polarized light is used as the alignment film composition. The photo-alignable material may be a photo-dimerization type material or a photo-isomerization type material. Specific examples include cinnamate, coumarin, benzylidenephthalimidine, benzylideneacetophenone, diphenylacetylene, stilbazole, uracil, quinolinone, maleimide, or a polymer having a cinnamylidene acetic acid derivative. Polymers having at least one of them and derivatives thereof are preferably used. Specific examples of such photodimerization type materials include, for example, JP-A-9-118717, JP-A-10-506420, JP-A-2003-505561, WO2010/150748, and JP-A-2015- The compounds described in JP-A-151548 can be mentioned.

A method for forming a photo-alignment film by a photo-alignment method may be appropriately selected from conventionally known methods. For example, a photo-alignment film can be obtained by uniformly coating the photo-alignment composition on the transparent substrate, irradiating polarized light, and then irradiating the entire coating film with light.

In addition, when the horizontal alignment film is formed by a molding method, the composition for the alignment film may be appropriately selected from those capable of molding the desired fine uneven shape. A molding composition containing a curable resin, an electron beam curable resin, or the like can be used. Among them, it is preferable to use an ultraviolet curable resin from the viewpoint of easy formation of an alignment film. Specific examples of the UV-curable resin include, in addition to the above polymerizable monomers and polymerizable oligomers, urethane acrylate, epoxy acrylate, polyester acrylate, polyether acrylate, melamine acrylate, and the like. More than one species can be used in combination.

A method for forming a horizontal alignment film by a molding method may be appropriately selected from conventionally known methods. For example, the molding composition is uniformly applied onto the transparent substrate, and the coating film is brought into contact with a mold on which a desired fine uneven shape is formed, then pressed and irradiated with ultraviolet rays. Thus, it is possible to obtain an alignment film having a desired fine concavo-convex shape.

Further, the horizontal alignment film may be one in which a patterning process is performed and portions having alignment performance are arranged in a pattern. As the patterned horizontal alignment film, a known one can be used, and there is no particular limitation. Examples include a rubbing alignment film patterned by mask rubbing, and a photo-alignment film patterned by mask exposure. Examples include a film, an alignment film obtained by patterning an alignment film by printing or the like, and the like.

The thickness of the horizontal alignment film is not particularly limited as long as the polymerizable rod-like liquid crystal compound can be horizontally aligned, and the thickness is not particularly limited, but is usually 1 nm or more, preferably 60 nm or more. From the viewpoint of thinning, the thickness is preferably 15 μm or less, preferably 10 μm or less, more preferably 1 μm or less, and even more preferably 0.3 μm or less.

3. Substrate In the present embodiment, substrates include glass substrates, metal foils, resin substrates, and the like. Among them, the substrate preferably has transparency, and can be appropriately selected from conventionally known transparent substrates. Examples of transparent substrates include glass substrates, acetylcellulose resins such as triacetyl cellulose, polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, and polylactic acid, polypropylene, polyethylene, polymethylpentene, and the like. It is formed using resins such as olefin resin, acrylic resin, polyurethane resin, polyether sulfone, polycarbonate, polysulfone, polyether, polyether ketone, acrylonitrile, methacrylonitrile, cycloolefin polymer, and cycloolefin copolymer. and a transparent resin substrate.

The transparent substrate preferably has a transmittance of 80% or more, more preferably 90% or more, in the visible light region. Here, the transmittance of the transparent base material can be measured according to JIS K7361-1 (Plastics—Testing method for total light transmittance of transparent materials).

Further, when the retardation layer is formed by the roll-to-roll method, the transparent substrate is preferably a flexible material that can be wound into a roll.
Such flexible materials include cellulose derivatives, norbornene-based polymers, cycloolefin-based polymers, polymethyl methacrylate, polyvinyl alcohol, polyimides, polyarylates, polyethylene terephthalate, polysulfones, polyethersulfones, amorphous polyolefins, modified acrylic polymers, polystyrene. , epoxy resins, polycarbonates, and polyesters. Among them, it is preferable to use a cellulose derivative or polyethylene terephthalate in the present embodiment. This is because the cellulose derivative is particularly excellent in optical isotropy, and can be made excellent in optical properties. Moreover, polyethylene terephthalate is preferable because of its high transparency and excellent mechanical properties.

The thickness of the substrate used in the present embodiment is not particularly limited as long as it is within a range in which the necessary self-supporting property can be imparted depending on the application of the retardation film, but is usually in the range of about 10 μm or more and 1000 μm or less. is.
Above all, 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 retardation film is formed and then cut to form a single-sheet retardation film, processing waste increases or the cutting blade wears. This is because the

The structure of the base material used in the present embodiment is not limited to a structure consisting of a single layer, and may have a structure in which a plurality of layers are laminated. When it has a configuration in which a plurality of layers are laminated, layers having the same composition may be laminated, or a plurality of layers having different compositions may be laminated.
For example, when the alignment film used in the present embodiment contains an ultraviolet curable resin, a primer layer is formed on the substrate to improve the adhesion between the transparent substrate and the ultraviolet curable resin. may This primer layer has adhesiveness to both the base material and the UV-curable resin, is optically transparent, and allows UV rays to pass through. , urethane, etc. can be appropriately selected and used.

Also, an anchor coat layer may be laminated on the substrate. The strength of the substrate can be improved by the anchor coat layer. A metal alkoxide, especially a metal silicon alkoxide sol can be used as the anchor coat material. Metal alkoxides are usually used as alcoholic solutions. Since the anchor coat layer needs to be a uniform and flexible film, the thickness of the anchor coat layer is preferably about 0.04 μm or more and 2 μm or less, more preferably about 0.05 μm or more and 0.2 μm or less.
When the substrate has an anchor coat layer, a binder layer may be further laminated between the substrate and the anchor coat layer, or the anchor coat layer may contain a material that enhances adhesion to the substrate. The adhesion between the material and the anchor coat layer may be improved. As the binder material used for forming the binder layer, any material capable of improving the adhesion between the substrate and the anchor coat layer can be used without particular limitation. Examples of binder materials include silane coupling agents, titanium coupling agents, and zirconium coupling agents.

4. Method for producing retardation film The method for producing a retardation film according to an embodiment of the present disclosure comprises:
A step of forming a film (film forming step) of the polymerizable composition of the embodiment of the present disclosure;
a step of orienting at least the polymerizable compound in the film-formed polymerizable composition (orientation step);
After the alignment step, a step of polymerizing at least the polymerizable compound (polymerization step) is provided to form a retardation layer.
As the polymerizable composition, the same one as in the above "A. Polymerizable composition" can be used, and thus description thereof is omitted here.

(1) Film forming step of polymerizable composition A film is formed by uniformly applying the polymerizable composition onto a support.
As described above, the coating amount of the polymerizable composition and the concentration of the polymerizable liquid crystal compound are appropriately adjusted to adjust the film thickness so as to give a desired retardation. It may be on the material, or on the alignment film of the base material provided with the alignment film.

The coating method may be selected as appropriate as long as it is a method capable of accurately forming a film with a desired thickness. For example, gravure coating method, reverse coating method, knife coating method, dip coating method, spray coating method, air knife coating method, spin coating method, roll coating method, printing method, immersion pick-up method, curtain coating method, die coating method, casting method, bar coating method, extrusion coating method, E-type coating method, and the like.

(2) Orientation Step Next, at least the polymerizable liquid crystal compound in the film-formed polymerizable composition is oriented. The polymerizable liquid crystal compound in the film-formed polymerizable composition is adjusted to a temperature at which it can be oriented and heated. By the heat treatment, a main chain portion having orientation of the polymerizable liquid crystal compound (A) represented by the general formula (1) and the polymerizable liquid crystal compound (B) represented by the general formula (2); If necessary, the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound different from the polymerizable liquid crystal compound (B) can be aligned and dried, and fixed while maintaining the alignment state. can be
The temperature at which orientation is possible varies depending on each substance in the polymerizable composition, and therefore needs to be adjusted as appropriate. For example, it is preferably performed within the range of 60° C. or higher and 200° C. or lower, and more preferably within the range of 60° C. or higher and 100° C. or lower.
As the heating means, known heating and drying means can be appropriately selected and used.
Moreover, the heating time may be selected as appropriate, and is selected, for example, within the range of 10 seconds to 2 hours, preferably 20 seconds to 30 minutes.

(3) Polymerization step After the orientation step, at least the polymerizable compound is polymerized. In the alignment step, the polymerizable compound is polymerized by, for example, irradiating the coating film, which is fixed while maintaining the alignment state of the polymerizable compound and the polymerizable liquid crystal compound that may be further contained, to polymerize the polymerizable compound. It is possible to obtain a retardation layer composed of a cured product of the polymerizable composition.
Ultraviolet irradiation is preferably used as the light irradiation. Ultra-high pressure mercury lamps, high-pressure mercury lamps, low-pressure mercury lamps, carbon arcs, xenon arcs, metal halide lamps, and other light sources can be used for ultraviolet irradiation. The irradiation amount of the energy beam source may be appropriately selected, and is preferably in the range of, for example, 10 mJ/cm ² or more and 10000 mJ/cm ^{2 or} less as an integrated exposure amount at an ultraviolet wavelength of 365 nm.

5. Applications The retardation film of the present disclosure is suitably used as, for example, an antireflection quarter-wave plate, and is suitably used as an optical member for various display devices as described later.

D. Transfer laminate The transfer laminate of the present disclosure includes a retardation layer and a support that releasably supports the retardation layer,
wherein the retardation layer comprises a cured product of the polymerizable composition of the present disclosure;
It is a laminate for transfer used for transferring a retardation layer.

Since the retardation layer of the transfer layered product of the present embodiment is made of a cured product of the polymerizable composition, precipitation of the polymerizable compound is suppressed and optical properties are excellent. According to the transfer laminate of the present embodiment, for example, the retardation layer of the present disclosure, which is a thin film containing no substrate, can be transferred to any other optical member or the like.
According to the transfer laminate of the present embodiment, for example, the retardation film 10 composed only of the retardation layer 1 shown in the example of FIG. A retardation film composed of a laminate 26 in which the film 23 and the retardation layer 21 are laminated can be provided. That is, an orientation film or the like may be laminated on the retardation layer used for transferring the transfer laminate, as long as the retardation layer can be at least peeled off.
Hereinafter, the configuration of such a transfer laminate will be described, but the polymerizable composition of the embodiment of the present disclosure is as described above, so the description is omitted here.

The layer structure of the transfer laminate will be described with reference to the drawings. 4 and 5 each illustrate one embodiment of the transfer laminate of the present disclosure.
One embodiment of the transfer laminate 20 shown in the example of FIG. It comprises a laminated laminate. In the transfer laminate 20 shown in the example of FIG. 4, the peel strength at the interface between the second base material 12 and the alignment film 13 is greater than the peel strength at the interface between the alignment film 13 and the retardation layer 11. As a result, separation is likely to occur at the interface 17 between the alignment film 13 and the retardation layer 11 . Therefore, the layered body in which the alignment film 13 is layered on the second base material 12 can be peeled off as the peelable support 15 from the transfer layered body 20 transferred onto the transferred body. Only the retardation layer 11 can be transferred as the transfer layer 16 including the retardation layer.
One embodiment of the transfer laminate 30 shown in the example of FIG. An alignment film 23 is further provided between 21 and the second base material 22 . In the transfer laminate 30 shown in the example of FIG. 5, the peel strength at the interface between the second base material 22 and the alignment film 23 is smaller than the peel strength at the interface between the alignment film 23 and the retardation layer 21. As a result, the interface 27 between the second base material 22 and the alignment film 23 is easily peeled off. Therefore, the second base material 22 can be peeled off as the peelable support 25 from the transfer layered product 30 transferred onto the transferred object, and the layered product of the retardation layer 21 and the alignment film 23 can be transferred as a transfer layer 26 containing a retardation layer.

For example, whether the peel strength between the second substrate and the alignment film is greater or smaller than the peel strength between the alignment film and the retardation layer depends on which interface the retardation layer is peeled off. You can check with At which interface the peeling occurs can be analyzed, for example, by IR or the like.

In addition, one embodiment of the transfer laminate 40 shown in the example of FIG. 6 includes a retardation layer 31 and a second base material 32 as a support 35 that releasably supports the retardation layer. . From the transfer layered product 40 transferred onto the transferred object, the second base material 32 can be peeled off as a peelable support 35, and only the retardation layer 31 is transferred to the transfer layer including the retardation layer. It can be transferred as layer 36 .

The present embodiment will be described below, but since the retardation layer can be the same as the retardation layer described in the above "C. Retardation film", description thereof will be omitted here.
In addition, the alignment film and the substrate can be the same as the alignment film and substrate described in "C. Retardation film" above, but examples of methods for adjusting the peel strength include the following methods. be able to.

In order to obtain the transfer laminate 20 shown in the example of FIG. For this purpose, for example, a method can be used in which the solvent contained in the alignment film-forming composition is capable of dissolving the second base material. A resin base material is preferably used as the second base material, and the surface of the base material may be subjected to a surface treatment to improve adhesion. In such a case, the adhesion between the resin substrate and the alignment film can be improved.
Further, in order to reduce the peel strength between the alignment film and the retardation 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 retardation layer, the solvent resistance of the alignment film is also preferred to be relatively high. When the alignment film has relatively high solvent resistance, the alignment film is less likely to dissolve in the solvent in the polymerizable composition when the retardation layer is formed by coating the polymerizable composition on the alignment film. Therefore, the adhesion between the alignment film and the retardation layer can be lowered.

On the other hand, in order to obtain the transfer laminate 30 shown in the example of FIG. In order to achieve this, for example, the surface of the substrate may be subjected to a release treatment, or a release layer may be formed. Thereby, the peelability of the base material can be enhanced, and the peel strength between the base material and the alignment layer can be made smaller than the peel strength between the alignment layer and the retardation layer.
Examples of the release treatment include surface treatments such as fluorine treatment and silicone treatment.
Materials for the release layer include, for example, fluorine-based release agents, silicone-based release agents, wax-based release agents, and the like. Examples of the method of forming the release layer include a method of applying a release agent by a coating method such as dip coating, spray coating, or roll coating.
Also, in order to obtain the transfer laminate 40 shown in the example of FIG. good too.

The base material used for the transfer laminate may or may not have flexibility, but it is preferable to have flexibility because the base material can be easily peeled off.
The thickness of the base material used for the transfer layered product is usually the above-described value, considering the balance between sufficient self-supporting strength and flexibility that can be applied to the production of the transfer layered product of the present embodiment and the transfer process. In the case of a sheet of material, it is preferably in the range of 20 μm to 200 μm.

The retardation layer that can be provided from the transfer laminate of the present disclosure is preferably used for the same applications as the retardation film, for example, is preferably used as an antireflection quarter-wave plate, optical for various display devices It can be transferred to a member and is suitably used to provide a thin film optical member.

E. Optical Member The optical member of the present disclosure includes a polarizing plate on the retardation film of the present disclosure.

The optical member of this embodiment will be described with reference to the drawings. FIG. 7 is a schematic cross-sectional view showing one embodiment of the optical member.
In the example of the optical member 60 of FIG. 7, the polarizing plate 50 is arranged on the retardation film 10 of the present disclosure. An adhesive layer (adhesive layer) may be provided between the retardation film 10 and the polarizing plate 50 (not shown), if necessary.

In the present embodiment, the polarizing plate is a plate-like plate that allows passage of only light oscillating in a specific direction, and can be appropriately selected from conventionally known polarizing plates. For example, a polyvinyl alcohol film, a polyvinyl formal film, a polyvinyl acetal film, a saponified ethylene-vinyl acetate copolymer film, and the like which are dyed with iodine or a dye and stretched can be used.
Further, in the present embodiment, the pressure-sensitive adhesive or adhesive for the pressure-sensitive adhesive layer (adhesive layer) may be appropriately selected from conventionally known ones, such as pressure-sensitive adhesives (adhesives), two-component curing adhesives, Any form of adhesion such as an ultraviolet curable adhesive, a heat curable adhesive, and a hot melt adhesive can be suitably used.

In addition to the polarizing plate, the optical member of this embodiment may further have other layers that are provided in known optical members. Examples of the other layers include other retardation layers different from the retardation layer of the present embodiment, antireflection layers, diffusion layers, antiglare layers, antistatic layers, protective films, and the like. , but not limited to these.

The optical member of the present embodiment can be suitably used, for example, as an optical member that suppresses reflection of external light or as a wide viewing angle polarizing plate for various display devices.

F. Method for Manufacturing Optical Member The method for manufacturing the optical member of the present disclosure is not particularly limited, and a method of laminating a polarizing plate on the retardation film of the present disclosure can be appropriately selected and used. For example, there is a production method of laminating a polarizing plate on the retardation film of the present disclosure via an adhesive layer or an adhesive layer.

Further, as a method for manufacturing an optical member according to an embodiment of the present disclosure,
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 retardation layer of the transfer laminate to face 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.

According to the method for manufacturing an optical member of one embodiment of the present disclosure using the transfer laminate, an optical member including only the retardation layer of the retardation film of the present disclosure and a polarizing plate is obtained. can be done.
The transfer laminate used in the method for manufacturing an optical member according to an embodiment of the present disclosure can be the same as that described in the above "E. Transfer laminate", so the description is omitted here. do.
In addition, a transfer target used in the method for manufacturing an optical member according to an embodiment of the present disclosure typically includes a transfer target having an adhesive layer and a polarizing plate, but is not limited to these. , it may further have the same layers as the other layers that the optical member in one embodiment of the present disclosure described above may have.

G. Display Device A display device according to the present disclosure includes the retardation film of the present embodiment or the optical member of the present embodiment.
Examples of display devices include light-emitting display devices and liquid crystal display devices, but are not limited to these.

Among them, in a light-emitting display device such as an organic light-emitting display device having a transparent electrode layer, a light-emitting layer, and an electrode layer in this order, because the retardation film of the present embodiment or the optical member of the present embodiment is provided. This has the effect of improving the viewing angle while suppressing reflection of external light.

An example of a light-emitting display device according to one embodiment will be described with reference to the drawings. FIG. 8 is a schematic cross-sectional view showing one embodiment of the optical member.
In the example of the organic light-emitting display device 100 of FIG. 8, the polarizing plate 50 is arranged on the light-emitting surface side of the retardation film 10, and the transparent electrode layer 71, the light-emitting layer 72, and the electrode layer are arranged on the opposite surface. 73 in this order.
As the light-emitting layer 72, for example, there is a structure in which a hole injection layer, a hole transport layer, a light-emitting layer, and an electron injection layer are stacked in this order from the transparent electrode layer 71 side. In this embodiment, the transparent electrode layer, the hole injection layer, the hole transport layer, the light emitting layer, the electron injection layer, the electrode layer, and other structures can be appropriately used known ones. The light-emitting display device manufactured in this manner can be applied to, for example, a passive drive type organic EL display and an active drive type organic EL display.
It should be noted that the display device of the present embodiment is not limited to the configuration described above, and may have an appropriately selected known configuration.

The chemical structure of each compound produced was confirmed by ¹ H NMR measurement using JEOL JNM-LA400WB manufactured by JEOL Ltd.
In addition, the phase transition temperature of each of the compounds produced was confirmed by texture observation with a polarizing microscope (manufactured by Olympus, BX51) equipped with a temperature control stage during heating. C stands for crystal, N for nematic phase, and I for isotropic liquid. For example, "C 130 N 180 I" indicates that the crystal transitioned to the nematic phase at 130°C, and the nematic phase transitioned to the isotropic liquid at 180°C.

[Production Example 1: Production of compound A-1 represented by formula (1-1)]
First, 27 g (150 mmol) of 4,4′-dihydroxybiphenyl represented by the formula (1-1-1) and 46 g (330 mmol) of hexamethylenetetramine were dissolved in 320 ml of trifluoroacetic acid in a 500 mL eggplant flask, and The reaction was carried out for 3 hours. After completion of the reaction, 3 L of 4N hydrochloric acid was added in an ice bath, and the mixture was stirred overnight. After the stirring was completed, the precipitate was filtered. Water (1 L) was added to the resulting crude product, and the mixture was stirred for 1 hour for suspension purification. By filtering the precipitate and drying the obtained crystals, 7.5 g (21 mmol, yield 21%) of intermediate 1 represented by formula (1-1-2) was obtained.

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

Next, 7.0 g (29 mmol) of the intermediate 1 represented by the formula (1-1-2) obtained above and 32 g (76 mmol) of the carboxylic acid derivative 1 represented by the formula (1-1-3) , N,N-Dimethylaminopyridine (DMAP) 0.14g (1.2mmol) suspension in dichloromethane (70mL), N,N-dicyclohexylcarbodiimide (DCC) 19g (90mmol) dichloromethane (14mL) solution was added dropwise. bottom. After completion of dropping, the mixture was stirred for 12 hours, the precipitate was filtered, and the solvent was distilled off. Chloroform (70 mL) was added to the resulting crude product, and the mixture was stirred for 1 hour for suspension purification. By filtering the precipitate and drying the obtained crystals, 23 g (22 mmol, yield 75%) of intermediate 2 represented by formula (1-1-4) was obtained.

5.0 g (30 mmol) of 2-hydrazinobenzothiazole and 2.5 g (45 mmol) of potassium hydroxide were added to N,N-dimethylformamide (90 mL) and heated at 80°C. After reaching a predetermined temperature, 9.2 g (36 mmol) of hexyl p-toluenesulfonate was added dropwise. After completion of dropping, the mixture was stirred for 4 hours. After completion of the reaction, 10 ml of water was added for extraction, and the solvent was distilled off. The residue was purified by silica gel chromatography, and the solvent was distilled off to obtain 3.0 g (12 mmol, yield 40%) of intermediate 3 represented by formula (1-1-5).

Intermediate 2 2.0 g (1.9 mmol) represented by the formula (1-1-4) obtained above, 15 mg of 12N hydrochloric acid was dissolved in 10 mL of tetrahydrofuran, and represented by the formula (1-1-5). A solution of 1.2 g (5.0 mmol) of intermediate 3 in tetrahydrofuran (3 mL) was added dropwise. After completion of dropping, the mixture was stirred for 12 hours and then dropped into 50 ml of methanol. After filtering the formed precipitate, the solvent was distilled off. Methanol (20 mL) was added to the resulting crude product, and the mixture was stirred for 1 hour for suspension purification. By filtering the precipitate and drying the obtained crystals, 1.4 g (0.94 mmol, yield 49%) of compound A-1 represented by formula (1-1) was obtained.

Phase transition temperature (at the time of temperature rise): C130N180I
¹ H NMR (CDCl ₃ ; δ ppm): 8.39 (s, 2H), 7.80 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m , 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd, 2H), 4. 34 (t, 4H), 4.17 (t, 4H), 3.97 (t, 4H), 2.70-2.55 (m, 4H), 2.45-2.35 (m, 8H) , 1.95-1.65 (m, 20H), 1.55-1.30 (m, 20H), 0.88 (t, 6H).

[Production Example 2: Production of compound A-2 represented by formula (1-2)]
4.7 g (24 mmol) of 2-amino-6-ethoxybenzothiazole was added to 20 ml of ethylene glycol. In an ice bath, 3.6 g (71 mmol) of hydrazine monohydrate and 1.9 g (55 mmol) of 12N hydrochloric acid were added dropwise, and the mixture was stirred at 130°C for 5 hours. After completion of the reaction, the mixture was cooled to room temperature, 300 ml of water was added, the precipitate was filtered, and the obtained crystals were dried to obtain 3.1 g (16 mmol, yield 68%) of intermediate 4.

In the production of Production Example 1, Intermediate 5 represented by Formula (1-2-1) was obtained by using Intermediate 4 instead of 2-hydrazinobenzothiazole in the step of obtaining Intermediate 3. 1.3 g (0.83 mmol, yield 43%) of compound A-2 represented by formula (1-2) was obtained in the same manner as in Production Example 1 except that

Phase transition temperature (at elevated temperature): C147N241I
1H NMR (CDCl3; δppm): 8.39 (s, 2H), 7.80 (s
, 2H), 7.52 (d, 2H), 7.21 (d, 2H), 7.05-6.75 (m, 1
2H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd,
2H), 4.34 (t, 4H), 4.17 (t, 4H), 3.97 (t, 4H), 3.6
5 (t, 4H), 2.70-2.55 (m, 4H), 2.45-2.35 (m, 8H),
1.95-1.65 (m, 20H), 1.55-1.30 (m, 26H), 0.88 (t
, 6H).

[Production Example 3: Production of compound A-3 represented by formula (1-3)]
In the production of Production Example 1, in the step of obtaining intermediate 3, an equimolar amount of 1-bromo-2-butoxyethane was used instead of iodohexane to obtain an intermediate represented by formula (1-3-1) 1.2 g (0.77 mmol, yield 40%) of compound A-3 represented by formula (1-3) was obtained in the same manner as in Production Example 1 except that 6 was obtained.

Phase transition temperature (at the time of temperature rise): C 120 N 184 I
1H NMR (CDCl ₃ ; δ ppm): 8.39 (s, 2H), 8.13 (s, 2H), 7.70-7.60 (m, 4H), 7.35-7.20 (m, 6H), 7.05-6.85 (m, 10H), 6.41 (dd, 2H), 6.25-6.10 (m, 2H), 5.83 (dd, 2H), 4.53 (t, 4H), 4.18 (t, 4H), 3.95 (t, 4H), 3.61 (t, 4H), 3.50 (t, 4H), 2.70-2.55 ( m, 4H), 2.45-2.35 (m, 8H), 1.95-1.30 (m, 28H).

[Production Example 4: Production of compound B-1 represented by formula (2-1)]
5 ml of hydrogen bromide (30% acetic acid solution) was dissolved in 100 ml of ethanol, 3.2 g (20 mmol) of 2,3,3-trimethylindolenine and 3.4 g (24 mmol) of 2,5-dihydroxybenzaldehyde were added, and the temperature was maintained at 70°C. and stirred for 3 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, the solvent was removed, the obtained crude product was dissolved in 300 mL of dichloromethane, and the organic layer was washed and concentrated. The residue was purified by silica gel chromatography, and the solvent was distilled off to obtain 1.4 g (3.8 mmol, yield 19%) of intermediate 7 represented by formula (2-1-2). The target structure was identified by ¹ H NMR.

Next, 1.0 g (2.8 mmol) of the intermediate 7 represented by the formula (2-1-2) obtained above and the carboxylic acid derivative 1 of the formula (1-1-3) 3. A suspension of 5 g (8.3 mmol) of N,N-dimethylaminopyridine (DMAP) and 10 mg (83 μmol) of N,N-dimethylaminopyridine (DMAP) in dichloromethane (10 mL) was added with 2.0 g (9.7 mmol) of N,N-dicyclohexylcarbodiimide (DCC) in dichloromethane. (1 mL) solution was added dropwise. After completion of dropping, the mixture was stirred for 12 hours, the precipitate was filtered, and the solvent was distilled off. Chloroform (10 mL) was added to the resulting crude product, and the mixture was stirred for 1 hour for suspension purification. The precipitate was filtered, chloroform (10 mL) was added to the resulting crude product, 280 mg (2.8 mmol) of triethylamine was added, and the mixture was stirred for 1 hour for suspension purification. By filtering the precipitate and drying the obtained crystals, 1.4 g (1.2 mmol, yield 45%) of compound B-1 represented by formula (2-1) was obtained. The target structure was identified by ¹ H NMR.

Phase transition temperature (at the time of temperature rise): C 87 N 160 I
¹ H NMR (CDCl ₃ ; δppm): 7.87 (s, 1H), 7.65 (d, 1H), 7.54 (d, 1H), 7.49 (d, 1H), 7.39- 7.22 (m, 5H), 7.04-7.01 (m, 4H), 6.96-6.93 (m, 4H), 6.32 (d, 2H), 6.17 (d, 2H), 5.93 (d, 2H), 4.12 (t, 4H), 3.96 (t, 4H), 2.86-2.81 (m, 1H), 2.67-2.64 (m, 3H), 2.33-2.17 (m, 8H), 1.75-1.59 (m, 16H), 1.49-1.35 (m, 14H)

[Production Example 5: Production of compound B-2 represented by formula (2-2)]
In the preparation of Preparation Example 4, an equimolar amount of 5-chloro-2,3,3-trimethylindolenine was used in place of 2,3,3-trimethylindolenine in the step of obtaining intermediate 7 to obtain intermediate got 8. Further, in the same manner as in Production Example 1, a carboxylic acid derivative 1 represented by Formula (1-1-3) was obtained.
Next, 1.0 g (2.5 mmol) of intermediate 8 obtained above, 3.2 g (7.6 mmol) of carboxylic acid derivative 1 represented by formula (1-1-3), N,N-dimethyl A solution of 1.8 g (8.8 mmol) of N,N-dicyclohexylcarbodiimide (DCC) in dichloromethane (1 mL) was added dropwise to a suspension of 9.2 mg (76 μmol) of aminopyridine (DMAP) in 10 mL of dichloromethane. After completion of dropping, the mixture was stirred for 12 hours, the precipitate was filtered, and the solvent was distilled off. Chloroform (10 mL) was added to the resulting crude product, and the mixture was stirred for 1 hour for suspension purification. The precipitate was filtered, chloroform (10 mL) was added to the resulting crude product, 260 mg (2.5 mmol) of triethylamine was added, and the mixture was stirred for 1 hour for suspension purification. By filtering the precipitate and drying the obtained crystals, 1.5 g (1.30 mmol, yield 52%) of compound B-2 represented by formula (2-2) was obtained. The target structure was identified by ¹ H NMR.

Phase transition temperature (at elevated temperature): C78N105I
¹ H NMR (CDCl ₃ ; δppm): 8.46 (s, 1H), 8.27 (d, 1H), 7.93 (s, 1H), 7.85 (d, 1H), 7.74 ( d, 1H), 7.47 (d, 1H), 7.31-7.25 (m, 2H), 7.04-7.01 (m, 4H), 6.96-6.93 (m, 4H), 6.87 (d, 1H), 6.32 (d, 2H), 6.17 (d, 2H), 5.93 (d, 2H), 4.12 (t, 4H), 3. 96 (t, 4H), 3.79 (s, 3H), 2.86-2.81 (m, 1H), 2.67-2.64 (m, 3H), 2.33-2.17 ( m, 8H), 1.75-1.59 (m, 16H), 1.49-1.35 (m, 14H)

[Comparative Production Example 1: Production of Comparative Compound C-1 Represented by Formula (C1-1)]
Comparative compound C-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.

[Comparative Production Example 2: Production of Comparative Compound C-2 Represented by Formula (C1-2)]
Comparative compound C-2 represented by the following formula (C1-2) was synthesized with reference to the synthesis of the compound represented by formula (1-3) in Example 3 of WO 2016/136533.

[Comparative Production Example 3: Production of Comparative Compound C-3 Represented by Formula (C1-3)]
Comparative intermediate 1 represented by formula (C1-3-2) was synthesized with reference to the synthesis of compound (ex-2) in Example 1 of JP-A-2016-166344. Further, in the same manner as in Production Example 1, a carboxylic acid derivative 1 represented by Formula (1-1-3) was obtained.

Next, 1.0 g (3.7 mmol) of the comparative intermediate 1 obtained above, 4.63 g (11 mmol) of the carboxylic acid derivative represented by the formula (1-1-3), N,N-dimethylamino A solution of 2.7 g (13 mmol) of N,N-dicyclohexylcarbodiimide (DCC) in dichloromethane (1 mL) was added dropwise to a suspension of 14 mg (110 μmol) of pyridine (DMAP) in 10 mL of dichloromethane. After completion of dropping, the mixture was stirred for 12 hours, the precipitate was filtered, and the solvent was distilled off. Chloroform (10 mL) was added to the resulting crude product, and the mixture was stirred for 1 hour for suspension purification. By filtering the precipitate and drying the obtained crystals, 2.3 g (2.4 mmol, yield 65%) of a comparative compound C-3 represented by the following formula (C1-3) was obtained. The target structure was identified by ¹ H NMR.

Phase transition temperature (at elevated temperature): C 98 N 117 I
¹ H NMR (CDCl ₃ ; δppm): 8.14 (d, 1H), 8.01 (s, 1H), 7.86 (d, 1H), 7.73 (d, 1H), 7.55- 7.47 (m, 3H), 7.30-7.25 (m, 2H), 7.04-7.01 (m, 4H), 6.96-6.93 (m, 4H), 6. 32 (d, 2H), 6.17 (d, 2H), 5.93 (d, 2H), 4.12 (t, 4H), 3.96 (t, 4H), 2.86-2.81 (m, 1H), 2.71-2.61 (m, 3H), 2.33-2.17 (m, 8H), 1.75-1.59 (m, 16H), 1.49-1 .35 (m, 8H)

[Comparative Production Example 4: Production of Comparative Compound C-4 Represented by Formula (C1-4)]
6-bromohexanol (8.5 g, 47 mmol) was added to a DMF (250 ml) suspension of methyl 3-(4-hydroxyphenyl)propionate (7.9 g, 44 mmol) and potassium carbonate (6.5 g, 47 mmol). , and stirred at 80° C. for 8 hours. After completion of the reaction, the reaction solution was diluted with water, extracted with ethyl acetate, and the solvent was distilled off. An aqueous solution of potassium hydroxide (2.6 g, 47 mmol) was added to the resulting crude product, and the mixture was reacted at 100° C. for 4 hours for hydrolysis. After completion of the reaction, an aqueous hydrochloric acid solution was added, and then ethyl acetate was added for extraction, and the solvent was distilled off. The residue was purified by silica gel chromatography, and the solvent was distilled off to obtain 4-(6-hydroxyhexyloxy)phenylpropionic acid with a yield of 68% (7.9 g, 30 mmol).
Then, 4-(6-hydroxyhexyloxy)phenylpropionic acid (7.9 g, 30 mmol), acryloyl chloride (3.0 g, 33 mmol), dimethylaniline (DMA) (3.6 g, 33 mmol) in tetrahydrofuran (150 mL) ) The suspension was stirred for 12 hours. After completion of the reaction, water and ethyl acetate were added for liquid separation. The solvent was distilled off, the residue was purified by silica gel chromatography, and the solvent was distilled off to obtain 4-[6-(acryloyloxy)hexyloxy]phenylpropionic acid with a yield of 70% (6.7 g, 21 mmol). ).
Trans-4-hydroxycyclohexanecarboxylic acid (5.0 g, 35 mmol) and triethylamine (5.3 g, 52 mmol) were dissolved in tetrahydrofuran (25 ml) and stirred under a nitrogen atmosphere while cooling at 10° C. or below. Chloromethyl methyl ether (3.0 g, 37 mmol) was slowly added dropwise thereto, and the mixture was stirred at room temperature for 8 hours. Ethyl acetate and water were added to extract the organic layer, the organic layer was washed with saturated aqueous sodium bicarbonate and water, and dried over anhydrous magnesium sulfate to give 4.8 g (28 mmol, Yield 80%).
4-[6-(acryloyloxy)hexyloxy]phenylpropionic acid 6.7 g (21 mmol), methoxymethyl trans-4-hydroxycyclohexanecarboxylate 4.8 g (28 mmol), N,N-dimethylaminopyridine (DMAP) 0 To a suspension of .12 g (1.0 mmol) in dichloromethane (150 ml) was added dropwise a solution of 5.6 g (27 mmol) of N,N-dicyclohexylcarbodiimide (DCC) in dichloromethane (5 mL). After the dropwise addition was completed, the mixture was stirred for 12 hours, the precipitate was filtered, washed with an aqueous sodium hydrogencarbonate solution and 1N hydrochloric acid, and the solvent was distilled off. 0.36 g (2.1 mmol) of p-toluenesulfonic acid (pTSA) was added to a tetrahydrofuran (20 ml) solution of the obtained crude product, and the mixture was heated and stirred at 40° C. for 8 hours. Ethyl acetate and water are added to extract the organic layer, the organic layer is washed with saturated aqueous sodium bicarbonate and water, dried over anhydrous magnesium sulfate, the solvent is distilled off under reduced pressure, and the residue is recrystallized with methanol. Thus, 3.8 g (8.6 mmol, yield 41%) of carboxylic acid derivative 2 represented by formula (1-4-3) was obtained.

In Comparative Production Example 3, instead of the carboxylic acid derivative 1 represented by the formula (1-1-3), an equimolar amount of the carboxylic acid derivative 2 represented by the formula (1-4-3) was used. 2.3 g (2.2 mmol, yield 61%) of a comparative compound C-4 represented by the following formula (C1-4) was obtained in the same manner as in Comparative Production Example 3. The target structure was identified by ¹ H NMR.

Phase transition temperature (at the time of temperature rise): C 67 N 82 I
¹ H NMR (CDCl ₃ ; δppm): 8.00 (d, 1H), 7.89 (d, 1H), 7.54-7.34 (m, 5H), 7.15-7.06 (m , 6H), 6.91-6.82 (m, 4H), 6.32 (d, 2H), 6.17 (d, 2H), 5.93 (d, 2H), 4.85-4. 74 (m, 2H), 4.19 (t, 4H), 3.94 (t, 4H), 2.94-2.88 (m, 4H), 2.73-2.53 (m, 6H) , 2.32-2.04 (m, 8H), 1.86-1.67 (m, 12H), 1.56-1.41 (m, 12H)

[Example 1]
(1) Production of polymerizable composition Polymerizable liquid crystal compound (90 parts by mass of compound A-1 represented by formula (1-1) and 10 parts of compound B-1 represented by formula (2-1) 100 parts by mass) and 4 parts by mass of a photopolymerization initiator (Irgacure 907 manufactured by Ciba Specialty Chemicals) were dissolved in 900 parts by mass of cyclopentanone to prepare a polymerizable composition 1.

(2) Production of retardation film or laminate for transfer (2-1) Preparation of composition for photo-alignment film A copolymer obtained by copolymerizing a photo-alignment monomer and hydroxyethyl methacrylate according to the description of Production Example 1 of Japanese Patent No. 5,626,493. Coalesced 1 was obtained.
A composition for photo-alignment film having the composition shown below 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

(2-2) Formation of Horizontal Alignment Film On one side of a PET substrate (manufactured by Toyobo Co., Ltd., E5100, thickness 38 μm), the composition for photo-alignment film is applied to a thickness of 0.2 μm after curing. and dried and heat-cured by heating in an oven at 120° C. for 1 minute to form a cured coating film. After that, the surface of the cured coating film was irradiated with polarized ultraviolet rays containing an emission line of 313 nm using a Hg-Xe lamp and a Glan-Taylor prism in the vertical direction from the substrate normal line at an exposure amount of 100 mJ/cm ² , thereby forming a horizontal alignment film. formed.

(2-3) Preparation of Retardation Film or Transfer Laminate On the formed alignment film, the polymerizable composition 1 is applied so that the film thickness after curing is 1 μm to form a polymerizable composition. filmed. Then, after drying in an oven for 120 seconds at the drying temperature shown in Table 11, a retardation layer was formed by irradiating ultraviolet rays (UV) at an irradiation amount of 400 mJ / cm ² using an H bulb manufactured by Fusion. A retardation film or a transfer laminate was obtained.

[Examples 2 to 10, Comparative Examples 1 to 6]
(1) Production of polymerizable composition In Example 1, polymerizable compositions 2 to 10 and comparative polymerizable compositions were prepared in the same manner as in Example 1, except that the composition of the polymerizable liquid crystal compound was changed according to Table 11 below. Compositions 1-6 were obtained.
(2) Production of Retardation Film or Laminate for Transfer In the same manner as in Example 1, retardation films or transfer laminates 2 to 10 and comparative retardation films or transfer laminates 1 to 6 were obtained.

[evaluation]
<Sample creation>
A sample was used in which the PET substrate of the retardation film obtained in each example and each comparative example was peeled off and the retardation layer and horizontal alignment film were transferred to glass with an adhesive.

<Solution stability>
The stability of the polymerizable composition obtained in each example and each comparative example was evaluated. The composition was stored at 25° C. for a specified period of time, and the composition (ink) stability after storage was visually observed to evaluate the composition (ink) stability based on the presence or absence of precipitates.
(Solution stability evaluation criteria)
A: No precipitation after storage for 30 days B: Precipitation for 7 days or more and less than 30 days C: Precipitation for 1 day or more and less than 7 days D: Precipitation for less than 1 day

<Orientation> The orientation of the retardation layer was evaluated in four stages by observing with a polarizing microscope.
(Evaluation Criteria for Orientation)
A: Visually uniform orientation is obtained, and 95% or more is oriented by polarizing microscope observation B: Visually uniform orientation is obtained, and the orientation area is 90% or more and less than 95% by polarizing microscope observation C : Not as oriented as A and B by visual observation, and the oriented area by polarizing microscope observation is 50% or more and less than 90% D: No orientation by visual observation, and the oriented area by polarizing microscope observation is less than 50%

<Phase difference (wavelength dispersion)>
In-plane retardation Re was measured at wavelengths of 450 nm, 550 nm, and 650 nm using a retardation measuring device (manufactured by Oji Scientific Instruments Co., Ltd., KOBRA-WR) x, which is calculated as follows using the measured retardation: Wavelength dispersion was evaluated from the y value.
x = (in-plane retardation Re at 450 nm)/(in-plane retardation Re at 550 nm)
y = (in-plane retardation Re at 650 nm)/(in-plane retardation Re at 550 nm)
(Wavelength dispersion evaluation criteria)
A: 0.60≦x<0.95, 1≦y Reverse wavelength dispersion B: 0.95≦x<0.99, 1≦y Reverse wavelength dispersion C: 0.99≦ x<1, 1≤y: flat wavelength dispersion D: 1≤x, 1>y: normal dispersion

<In-plane uniformity evaluation>
The retardation value Re of light with a wavelength of 550 nm of the obtained optical film was measured. A range of 10 cm square was set on the surface of the optical film, 10 points were measured in each range, and the difference (ΔRe) between the maximum value and the minimum value of the obtained retardation value was used to evaluate the in-plane uniformity. .
(Evaluation criteria for in-plane uniformity)
A: ΔRe was 2 nm or less.
B: ΔRe was more than 2 nm and 3 nm or less.
C: ΔRe was over 3 nm.
If the in-plane uniformity evaluation is A or B, the in-plane uniformity of the retardation value is excellent.

<Birefringence>
Since there is a relationship of retardation Re(λ)=birefringence Δn(λ)×film thickness d, the birefringence Δn at 550 nm was evaluated from the in-plane retardation Re at 550 nm and the film thickness d.
(Evaluation criteria for birefringence)
A: 0.08 or more B: 0.075 ≤ x < 0.08
C: less than 0.075

1 retardation layers 2, 2' substrate 3 alignment film 10 retardation films 11, 21, 31 retardation layers 12, 22, 32 second substrates 13, 23, 33 alignment films 15, 25, 35 peelable Supports 16, 26, 36 Retardation layer 17 for transfer Interface 27 between alignment film and retardation layer Interfaces 20, 30, 40 between second substrate and alignment film Transfer laminate 50 Polarizing plate 60 Optical member 71 Transparent electrode layer 72 Light-emitting layer 73 Electrode layer 100 Light-emitting display device

Claims (11)

A polymerizable composition comprising a polymerizable liquid crystal compound (A) represented by the following general formula (1) and a polymerizable liquid crystal compound (B) represented by the following general formula (2).

(In general formula (1), L ¹ , L ² , L ³ and L ⁴ are each independently -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ - , -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH- , -NH-COO-, -NH-CO-NH-, -NH-O-, -O-NH-, -SCH ₂ -, -CH ₂ S-, -CF ₂ O-, -OCF ₂ -, - CF ₂ S-, -SCF ₂ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ - , -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -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 represents a single bond,
A ¹ and A ² are each independently a cyclohexane-1,4-diyl group, a cyclopentane-1,3-diyl group, which may be unsubstituted or substituted with one or more substituents E, represents a cycloheptane-1,3-diyl group, a cycloheptane-1,4-diyl group, a decahydronaphthalene-2,6-diyl group or a 1,3-dioxane-2,5-diyl group,
A ³ and A ⁴ are each independently a cyclohexane-1,4-diyl group, a cyclopentane-1,3-diyl group, which may be unsubstituted or substituted with one or more substituents E, cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, benzene-1,4-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene-2 ,6-diyl group, naphthalene-2,7-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane - represents a 2,5-diyl group,
R ¹ and R ² each independently represent a group selected from general formula (R-1) below,
General formula (R-1): -L ⁵ -R ^sp1 -Z ¹
In general formula (R-1), L ⁵ is -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 represents a single bond, R ^sp1 is carbon represents an alkylene group having 1 to 20 atoms or a single bond, in which one —CH ₂ — or two or more non-adjacent —CH ₂ — in the alkylene group are each independently —O—, —COO; -, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH- or -C≡C-, and Z ¹ is a polymerizable functional group represents
D ¹ and D ² each independently represent a group selected from the following general formula (D _g -1),
Substituents E, E ¹ and E ² are each independently fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group, diethylamino group, diisopropylamino group, trimethylsilyl group, dimethylsilyl group, thioisocyano group, or an alkyl group having 1 to 20 carbon atoms optionally substituted by these, one -CH ₂ - or two or more non-adjacent -CH ₂ - in the alkyl group are each independently -O-, -S-, -CO-, -COO-, -OCO-, - CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO- CH=CH-, -OCO-CH=CH-, -CH=CH-, -CF=CF- or -C≡C-, or substituents E, E ¹ and E ² are Each independently may represent a group represented by -L ^E -R ^spE -Z ^E , wherein L ^E , R ^spE and Z ^E are respectively the L ⁵ , R ^sp1 and Z ¹ but may be the same as or different from L ⁵ , R ^sp1 and Z ¹ , and the substituents E, E ¹ and E ² in the compound are respectively When there are more than one, each may be the same or different,
When there are a plurality of L ³ , L ⁴ , A ³ and A ⁴ , they may be the same or different.
m1 and m2 each independently represent an integer of 1 to 4; n1 and n2 each independently represent an integer of 0 to 3; )

(In the general formula (D _g -1), G ¹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and the alkyl group is unsubstituted or substituted with one or more substituents E It may be
Q ¹ represents an organic group having 3 to 30 carbon atoms and having an aromatic heterocycle, and the aromatic heterocycle may be unsubstituted or substituted with one or more substituents E. ,
J ¹ represents -NQ ² -, in Q ² , hydrogen atoms may be substituted with fluorine atoms, and one -CH ₂ - or two or more non-adjacent -CH ₂ - are each independently a linear or branched alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 12 carbon atoms which may be substituted with -O-, -CO-, -COO-, -OCO- as Alternatively, L 6 , A 5 , L 7 , L ⁶ , A ⁵ , L ⁷ , or -(L ⁶ -A ⁵ )qL ⁷ -R ^sp2 -Z ² are the alkyl group optionally substituted by the cycloalkyl group. R ^sp2 and Z ² each represent the same as defined for L ¹ to L ⁴ , A ³ to A ⁴ , L ⁵ , R ^sp1 and Z ¹ above, but L ¹ to L ⁴ , A ³ to A ⁴ , L ⁵ , R ^sp1 and Z ¹ may be the same or different, and q represents an integer of 0 or 1; )

(In the general formula (2), A ^core is a monocyclic, condensed ring, or ring assembly aromatic group that is unsubstituted or optionally substituted by one or more substituents E ³ , and has 4 carbon atoms. represents a trivalent or tetravalent group of ~16,
M represents -CH=CH-,
D ³ represents a group selected from the following general formula (D _g -2),
L ¹¹ , L ¹² , L ¹³ and L ¹⁴ are each independently -O-, -S-, -OCH ₂ -, -CH ₂ O-, -CH ₂ CH ₂ -, -CO-, -COO- , -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -OCO-NH-, -NH-COO-, - NH—CO—NH—, —NH—O—, —O—NH—, —SCH ₂ —, —CH ₂ S—, —CF ₂ O—, —OCF ₂ —, —CF ₂ S—, —SCF ₂ -, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH-, -COO-CH ₂ CH ₂ -, -OCO-CH ₂ CH ₂ -, -CH ₂ CH ₂ -COO-, -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 represents a single bond,
A ¹¹ and A ¹² are each independently a cyclohexane-1,4-diyl group or a cyclopentane-1,3-diyl group which may be unsubstituted or substituted with one or more substituents E ³ , cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, decahydronaphthalene-2,6-diyl group or 1,3-dioxane-2,5-diyl group,
A ¹³ and A ¹⁴ are each independently a cyclohexane-1,4-diyl group or a cyclopentane-1,3-diyl group which may be unsubstituted or substituted with one or more substituents E ³ , cycloheptane-1,3-diyl group, cycloheptane-1,4-diyl group, benzene-1,4-diyl group, pyridine-2,5-diyl group, pyrimidine-2,5-diyl group, naphthalene- 2,6-diyl group, naphthalene-2,7-diyl group, naphthalene-1,4-diyl group, tetrahydronaphthalene-2,6-diyl group, decahydronaphthalene-2,6-diyl group or 1,3- represents a dioxane-2,5-diyl group,
R ¹¹ and R ¹² each independently represent a group selected from the following general formula (R-11),
General formula (R-11): -L ¹⁵ -R ^sp11 -Z ¹¹
In general formula (R-11), L ¹⁵ is -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 represents a single bond, R ^sp11 is carbon represents an alkylene group having 1 to 20 atoms or a single bond, in which one —CH ₂ — or two or more non-adjacent —CH ₂ — in the alkylene group are each independently —O—, —COO; -, -OCO-, -OCO-O-, -CO-NH-, -NH-CO-, -CH=CH- or -C≡C-, and Z ¹¹ is a polymerizable functional group represents
Substituent ^E3 is fluorine atom, chlorine atom, bromine atom, iodine atom, pentafluorosulfuranyl group, nitro group, cyano group, isocyano group, amino group, hydroxyl group, mercapto group, methylamino group, dimethylamino group , a diethylamino group, a diisopropylamino group, a trimethylsilyl group, a dimethylsilyl group, a thioisocyano group, or an alkyl group having 1 to 20 carbon atoms which may be substituted by these groups, and one —CH ₂ — in the alkyl group. or two or more -CH ₂ - which are not adjacent are each independently -O-, -S-, -CO-, -COO-, -OCO-, -CO-S-, -S-CO-, -O-CO-O-, -CO-NH-, -NH-CO-, -CH=CH-COO-, -CH=CH-OCO-, -COO-CH=CH-, -OCO-CH=CH -, -CH=CH-, -CF=CF- or -C≡C-, or the substituent E ³ is a group represented by -L ^E3 -R ^spE3 -Z ^E3 wherein L ^E3 , R ^spE3 , and Z ^E3 represent the same as defined in L ¹⁵ , R ^sp11 , and Z ¹¹ above, respectively, but L ¹⁵ , R ^sp11 above, respectively, , and Z ¹¹ may be the same or different, and if there are multiple substituents E ³ in the compound, they may be the same or different,
When multiple M, D ³ , L ¹³ , L ¹⁴ , A ¹³ and A ¹⁴ appear, they may be the same or different.
n11 represents an integer of 1 or 2, m11 and m12 each independently represents an integer of 1 to 4;

(In general formula (D _g -2), R ^d1 and R ^d2 are each independently an unsubstituted alkyl group having 1 to 10 carbon atoms, or R ^d1 and R ^d2 are bonded to each other to form 5 to forming a seven-membered non-aromatic hydrocarbon ring,
R ^e1 , R ^e2 , R ^e3 and R ^e4 each independently represent a hydrogen atom or the substituent E ³ , and R ^e1 , R ^e2 , R ^e3 and R ^e4 are bonded to each other to form a 3- to 7-membered ring may form a non-aromatic or aromatic hydrocarbon ring of the non-aromatic or aromatic hydrocarbon ring may be unsubstituted or substituted by one or more of the substituents E ³ Optionally, any carbon atom of the non-aromatic or aromatic hydrocarbon ring may be replaced by a heteroatom. * (asterisk) indicates the binding position with M. ) In the general formula (D _g -1) of the general formula (1), Q ¹ is an organic compound having 5 or more and 30 or less carbon atoms having an aromatic heterocyclic ring which is a condensed ring of a 5-membered ring and a 6-membered ring. group, wherein said heteroaromatic ring is unsubstituted or optionally substituted by one or more of said substituents E. In the general formula (D _g -1) of the general formula (1), one or more of the carbon atoms of the group selected from the following formula (Q-10) for Q ¹ is substituted with a hetero atom. represents an organic group having 5 to 30 carbon atoms and having an aromatic heterocycle, and the aromatic heterocycle may be unsubstituted or substituted with one or more substituents E , The polymerizable composition according to claim 1 or 2.

4. The polymerizable composition according to any one of claims 1 to 3, further comprising a polymerizable liquid crystal compound different from the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B). A polymer obtained by polymerizing the polymerizable composition according to any one of claims 1 to 4. A retardation film having a retardation layer, wherein the retardation layer contains a cured product of the polymerizable composition according to any one of claims 1 to 4. A step of forming a film of the polymerizable composition according to any one of claims 1 to 4;
A step of orienting at least the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B) in the film-formed polymerizable composition;
Production of a retardation film, comprising a step of forming a retardation layer by having a step of polymerizing at least the polymerizable liquid crystal compound (A) and the polymerizable liquid crystal compound (B) after the orienting step. Method. A retardation layer and a support that releasably supports the retardation layer,
The retardation layer contains a cured product of the polymerizable composition according to any one of claims 1 to 4,
A transfer layered product for transferring a retardation layer. An optical member comprising a polarizing plate on the retardation film according to claim 6 . A retardation layer and a support that releasably supports the retardation layer, wherein the retardation layer contains a cured product of the polymerizable composition according to any one of claims 1 to 4. , a step of preparing a transfer laminate to be subjected to transfer of the retardation layer;
A transfer step of placing a transfer target including at least a polarizing plate and the retardation layer of the transfer laminate to face each other, and transferring the transfer laminate onto the transfer target;
A peeling step of peeling off the support from the transfer laminate transferred onto the transfer target;
A method for manufacturing an optical member. A display device comprising the retardation film according to claim 6 or the optical member according to claim 9.

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