KR101674608B1 - Composition for manufacturing optical elements with negative optical dispersion and optically anisotropic body manufactured therefrom - Google Patents

Abstract

The present invention relates to a composition for producing an optical element having negative optical dispersion and an optical anisotropic body made therefrom. According to the present invention, an optically anisotropic material having a thin thickness while exhibiting a stable inverse wavelength dispersion using the composition for an optical element can be manufactured by a more simplified method, and it can be produced by a liquid crystal display device such as a broadband? / 4 wavelength plate And can be applied as an optical film for use.

Description

TECHNICAL FIELD [0001] The present invention relates to a composition for producing an optical element having a negative optical dispersion and an optical anisotropic body produced therefrom. BACKGROUND ART < RTI ID = 0.0 >

The present invention relates to a composition for producing an optical element having negative optical dispersion and an optical anisotropic body made therefrom.

A phase retarder is an optical film used for realizing, for example, a wide viewing angle of a liquid crystal display device. The retardation value of the phase retarder depends on the wavelength. The wavelength dispersion of the retardation value is divided into three types as follows. That is, the wavelength dispersion of the retardation value is a function of the retardation value of the retardation value, which is the retardation value, that is, the retardation value has a larger wavelength dispersion as the shorter wavelength side, the flat dispersion that the retardation value hardly changes from the shorter wavelength side to the longer wavelength side, It can be divided into dispersion. In the case of a phase retarder, it is preferable to exhibit inverse dispersion, because it has a predetermined retardation (e.g.,? / 2 or? / 4) in a wide wavelength band.

However, since most phase retarders formed from a conventional resin film exhibit a positive dispersion, various types of liquid crystal compositions capable of providing reverse dispersion have been proposed. Typically, the liquid crystal composition comprises a rod-like liquid crystal material and a non-liquid crystalline material oriented perpendicularly to the long axis of the liquid crystal material. However, when the mixing ratio of the non-liquid crystalline substance is low, the reverse dispersion is not induced, and when the mixing ratio is high, the liquid crystal composition loses the liquid crystal property. In addition, the reverse dispersion and the birefringence are complementary, and the birefringence is relatively decreased when the content of the non-liquid crystalline substance is increased to improve the back scattering property.

Therefore, it is required to develop a substance capable of inducing strong reverse dispersion and to develop a composition capable of inducing reverse dispersion while having a low content of non-liquid crystalline substance.

Korean Patent Publication No. 10-2006-0130713 (December 19, 2006) Japanese Unexamined Patent Application Publication No. 2010-241919 (October 28, 2010) Korean Registered Patent No. 10-1012892 (Mar.

Accordingly, the present invention is intended to provide a composition for producing an optical element capable of providing a more stable and stable reverse dispersion.

The present invention also provides an optically anisotropic material produced from the composition.

According to the present invention, there is provided a composition for an optical element comprising a polymerizable liquid crystal compound represented by the following formula (1) and a reactive mesogenic compound having at least one polymerizable functional group:

[Chemical Formula 1]

In Formula 1,

A ¹ , A ² , A ³ , A ⁴ , E ¹ , E ² , E ³ , and E ⁴ are each independently a single bond or a divalent linking group;

D ¹ , D ² , D ³ and D ⁴ each independently represent a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a bivalent cyclic group having at least one aromatic ring or aliphatic ring or heterocyclic ring, A combination thereof;

G ¹ , G ² , G ³ , and G ⁴ are each independently an alkylene group having 1 to 10 carbon atoms;

J ¹ , J ² , J ³ , and J ⁴ are each independently a hydrogen group or a polymerizable group;

L ¹ , L ² , L ³ , and L ⁴ are each independently O, S, or Se;

M ¹ and M ² are each independently N, P, or As;

Q is an alkynylene group having 2 to 6 carbon atoms, -CR ¹ = CR ² -, or a substituted or unsubstituted aromatic or heteroaromatic linking group, and R ¹ and R ² are each independently H, F, Cl, CN, An alkyl group having 1 to 10 carbon atoms, or an acyl group having 1 to 10 carbon atoms;

p and q are each independently 1 to 5.

According to the present invention, the reactive mesogenic compound may be a compound represented by the following Formula 4:

[Chemical Formula 4]

In Formula 4,

P is a polymerizable group,

S is a spacer group having 1 to 20 carbon atoms,

X is -O-, -S-, -CO-, -COO-, -OCO-, -OCOO- or a single bond,

n is 0 or 1,

MG is a mesogenic group,

Wherein R has the meaning given for an alkyl radical of 1 to 25 carbon atoms, halogen, cyano, or P- (SX) _n -, wherein one or more non-adjacent CH ₂ groups in the alkyl radical, a non-direct connection -O-, -S-, -NH-, -N ( CH 3) -, -CO-, -COO-, -OCO-, -OCO-O-, -S-CO-, -CO-S- or -C? C-.

The composition may further include a polymerization initiator and a solvent.

In addition, the composition may further comprise a non-mesogenic compound having at least two polymerizable functional groups.

On the other hand, according to the present invention, there is provided an optically anisotropic material comprising a cured product or polymer of the composition.

According to the present invention, there is provided an optical element for a liquid crystal display device including the optically anisotropic element.

According to the present invention, an optically anisotropic material having a thin thickness while exhibiting a stable inverse wavelength dispersion using the composition for an optical element can be manufactured by a more simplified method, and it can be produced by a liquid crystal display device such as a broadband? / 4 wavelength plate And can be applied as an optical film for use.

Hereinafter, a composition for producing an optical element having a negative optical dispersion degree according to embodiments of the present invention and an optically anisotropic material produced therefrom will be described.

Prior to that, the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. And, the singular forms used herein include plural forms unless the phrases expressly have the opposite meaning. Also, as used herein, the meaning of "comprising" or "containing" embodies certain features, areas, integers, steps, acts, elements or components, But does not exclude the addition of components.

On the other hand, the inventors of the present invention have found that when a composition comprising a polymerizable liquid crystal compound having a structure represented by the following formula (1) and a reactive mesogenic compound having at least one polymerizable functional group is used in repeated studies on liquid crystal compounds, It has been confirmed that an optically anisotropic material having a thin thickness can be produced by a simpler method while exhibiting an inverse wavelength dispersion, and the present invention has been completed.

According to an embodiment of the present invention,

A polymerizable liquid crystal compound represented by the following formula (1); And

A reactive mesogenic compound having at least one polymerizable functional group

A composition for an optical element comprising:

[Chemical Formula 1]

In Formula 1,

A ¹ , A ² , A ³ , A ⁴ , E ¹ , E ² , E ³ , and E ⁴ are each independently a single bond or a divalent linking group;

D ¹ , D ² , D ³ and D ⁴ each independently represent a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, a bivalent cyclic group having at least one aromatic ring or aliphatic ring or heterocyclic ring, A combination thereof;

G ¹ , G ² , G ³ , and G ⁴ are each independently an alkylene group having 1 to 10 carbon atoms;

J ¹ , J ² , J ³ , and J ⁴ are each independently a hydrogen group or a polymerizable group;

L ¹ , L ² , L ³ , and L ⁴ are each independently O, S, or Se;

M ¹ and M ² are each independently N, P, or As;

Q is an alkynylene group having 2 to 6 carbon atoms, -CR ¹ = CR ² -, or a substituted or unsubstituted aromatic or heteroaromatic linking group, and R ¹ and R ² are each independently H, F, Cl, CN, An alkyl group having 1 to 10 carbon atoms, or an acyl group having 1 to 10 carbon atoms;

p and q are each independently 1 to 5.

First, the polymerizable liquid crystal compound represented by the above formula (1) comprises two main chains connecting an aryl group between two maleimide derivatives, and the two main chains are connected to each other by the Q.

According to the present invention, L ¹ , L ² , L ³ , and L ⁴ in formula (1) may each independently be a group 16 element (VIA) nonmetal; Preferably oxygen (O), sulfur (S) or selenium (Se); More preferably oxygen (O).

In Formula 1, M ¹ and M ² may each independently be a Group 15 element (VA) non-metallic element; Preferably nitrogen (N), phosphorus (P) or arsenic (As); And more preferably nitrogen (N).

In Formula 1, A ¹ , A ² , A ³ , A ⁴ , E ¹ , E ² , E ³ , and E ⁴ may each independently be a single bond or a divalent linking group. The 'bivalent linking group' may be replaced by -O-, -S-, -CO-, -COO-, -OCO-, -O-COO-, -CO-NR-, -NR-CO-, -NR-CO _{-NR-, -OCH 2 -, -CH 2} O-, -SCH--, -CH 2 S-, -CF 2 O-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CH _{2 CH 2 -, - (CH} 2) 3 -, - (CH 2) 4 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 -, -C = C- , or -C And R may be each independently hydrogen or an alkyl group having 1 to 10 carbon atoms.

In Formula 1, D ¹ , D ² , D ³ , and D ⁴ each independently represent a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms; A divalent cyclic group having at least one aromatic or aliphatic or heterocyclic ring; Or a combination thereof. According to the present invention, each of D ¹ to D ⁴ independently represents -Ph-, -Ph (OCH ₃ ) -, -CH ₂ Ph-, -PhCH ₂ -, -CH ₂ CH ₂ -Ph-, or -PhCH ₂ CH ₂ -; Ph is 1,4-phenylene.

In Formula 1, G ¹ , G ² , G ³ , and G ⁴ each independently represent an alkylene group having 1 to 10 carbon atoms, preferably an alkylene group having 2 to 9 carbon atoms.

In formula (1), J ¹ , J ² , J ³ , and J ⁴ may each independently be hydrogen or a polymerizable group, wherein the 'polymerizable group' is a group selected from the group consisting of an unsaturated bond or a (meth) Means any polymerizable functional group. Preferably, J ¹ , J ² , J ³ , and J ⁴ each independently represent a hydrogen group, a vinyl group, an acrylate group, a methacrylate group, a propenyl ether group, an epoxy group, or the like.

In Formula 1, Q is a bridge connecting two main chains, which is an alkynylene group having 2 to 6 carbon atoms, -CR ¹ ═CR ² -, or a substituted or unsubstituted aromatic or heteroaromatic linking group, R ¹ and R ² are each independently H, F, Cl, CN, an alkyl group having 1 to 10 carbon atoms, or an acyl group having 1 to 10 carbon atoms. Here, the 'substituted or unsubstituted aromatic or heteroaromatic linking group' means phenylene, biphenylene or any divalent linking group including them, preferably bis (phenylethynyl) benzene or bis Ethynyl) biphenyl, and the like. According to the present invention, Q is selected from the group consisting of -Ph-Ph-, -Ph-C≡C-Ph-, -Ph-C≡CC≡C-Ph-, -Ph-C≡C-Ph- -, -Ph-C? C-Ph-Ph-C? C-Ph-, etc., wherein Ph may be 1,4-phenylene.

Thus, the polymerizable liquid crystal compound of the present invention represented by the above formula (1) can be, for example, a polymerizable liquid crystal compound represented by the following formula (2)

(2)

In Formula 2, A ¹ to A ⁴ , D ¹ to D ⁴ , E ¹ to E ⁴ , G ¹ to G ⁴ , J ¹ to J ⁴ , Q, p and q are as defined in Formula 1, .

Specific examples of the polymerizable liquid crystal compound of the present invention represented by the above formula (1) include the following formulas (3a) to (3d). In the following formulas (3a) to (3d), n may be 1 to 10, preferably 2 to 9, However, the polymerizable liquid crystal compound of the present invention is not limited to the following exemplary compounds.

[Chemical Formula 3]

(3b)

[Chemical Formula 3c]

(3d)

The polymerizable liquid crystal compound represented by the above formula (1) can be prepared by applying a known reaction, and a more detailed production method will be described in detail in the Examples section of this specification.

On the other hand, the composition for an optical element according to the present invention includes a reactive mesogenic compound having at least one polymerizable functional group.

The reactive mesogenic compound may be a compound represented by the following general formula (4), although it may be conventional in the art to which the present invention belongs.

[Chemical Formula 4]

In Formula 4,

P is a polymerizable group,

S is a spacer group having 1 to 20 carbon atoms,

X is -O-, -S-, -CO-, -COO-, -OCO-, -OCOO- or a single bond,

n is 0 or 1,

MG is a mesogenic group,

Wherein R has the meaning given for an alkyl radical of 1 to 25 carbon atoms, halogen, cyano, or P- (SX) _n -, wherein one or more non-adjacent CH ₂ groups in the alkyl radical, a non-direct connection -O-, -S-, -NH-, -N ( CH 3) -, -CO-, -COO-, -OCO-, -OCO-O-, -S-CO-, -CO-S- or -C? C-.

In Formula 4, P is a polymerizable group, preferably a vinyl group, an acrylate group, a methacrylate group, a propenyl ether group, or an epoxy group.

In the formula (4), S may be a linear or branched alkylene group having 1 to 20 carbon atoms, preferably 1 to 20 carbon atoms, and at least one adjacent CH group in the alkylene group may be - -O-, -S-, -NH-, -N (CH) -, -CO-, -O-CO-, -S-CO-, -O-COO-, -CO-S-, -, -CHF-, -CHCl-, -CH (CN) -, -CH = CH-, or -C? C-.

In Formula 4, MG is a mesogenic group, preferably, a group represented by the following Formula 5:

[Chemical Formula 5]

In Formula 5,

Y ¹ , Y ² and Y ³ are each independently 1,4-phenylene in which one or more CH groups are substituted or unsubstituted by N; One or two non-adjacent CH ₂ groups are 1,4-cyclohexylene, 1,4-cyclohexenylene, or naphthalene-2,6-diyl substituted or unsubstituted by O, S or O and S ; All of which groups may be mono- or polysubstituted by halogen, cyano, nitro, or an alkyl, alkoxy or alkanoyl group of 1 to 7 carbon atoms in which at least one hydrogen atom may be replaced by F or Cl,

Z ¹ and Z ² are each independently -COO-, -OCO-, -CH ₂ CH ₂ -, -OCH ₂ -, -CH ₂ O-, -CH═CH-, -C≡C-, -CH = CH-COO-, -OCO-CH = CH- or a single bond,

m is 0, 1 or 2;

Y ¹ , Y ² and Y ³ in Formula 5 are each independently 1,4-phenylene (Phe), 1,4-phenylene (PheL) substituted by at least one group L, or 1,4 -cyclohexylene (Cyc), and wherein the groups L are _{F, Cl, CN, NO 2} , CH 3, C 2 H 5, OCH 3, OC 2 H 5, COCH 3, COC 2 H 5, CF 3, OCF ₃ , OCHF ₃ , OCH ₂ F ₅ to be. And Z ¹ and Z ² each independently may be -COO-, -OCO-, -CH ₂ CH ₂ - or -CH = CH-COO-.

Non-limiting examples, groups represented by the above formula 5 ^{-Phe-Z 2 -Phe-, -Phe-} Z 2 -Cyc-, -PheL-Z 2 -Phe-, -PheL-Z 2 -Cyc-, - ^{Phe-Z 2 -PheL-, -Phe-} Z 1 -Phe-Phe-, -Phe-Z 1 -Phe-Cyc-, -Phe-Z 1 -Phe-Z 2 -Phe-, -Phe-Z 1 - ^{Phe-Z 2 -Cyc-, -Phe-} Z 1 -Cyc-Z 2 -Phe-, -Phe-Z 1 -Cyc-Z 2 -Cyc-, -Phe-Z 1 -PheL-Z 2 -Phe-, ^{-Phe-Z 1 -Phe-Z 2} -PheL-, -PheL-Z 1 -Phe-Z 2 -PheL-, -PheL-Z 1 -PheL-Z 2 -Phe-, or -PheL-Z ¹ -PheL -Z ² -PheL- and the like.

The reactive mesogenic compounds may be represented by one or more compounds selected from the group of compounds represented by the following formulas (6a) to (6g)

[Chemical Formula 6a]

[Formula 6b]

[Chemical Formula 6c]

[Chemical formula 6d]

[Formula 6e]

(6f)

[Chemical Formula 6g]

In the above formulas (6a) to (6g)

x and y are each independently an integer of 1 to 12,

A is a 1,4-phenylene or 1,4-cyclohexylene group,

R ¹ is halogen, cyano, or an alkyl or alkoxy group having 1 to 12 carbon atoms,

Q ¹ and Q ² are each independently H, halogen, CN, alkyl having 1 to 7 carbon atoms, alkoxy or alkanoyl group.

Meanwhile, the composition for an optical element according to the present invention comprises 150 to 300 parts by weight, preferably 150 to 250 parts by weight, more preferably 170 to 230 parts by weight of the reactive mesogenic compound per 100 parts by weight of the polymerizable liquid crystal compound Section. That is, it is advantageous that the reactive mesogenic compound is contained in an amount of 150 parts by weight or more based on 100 parts by weight of the polymerizable liquid crystal compound so that the reverse dispersion required in the present invention can be sufficiently induced. However, when the reactive mesogenic compound is contained in excess, the liquid crystal properties of the composition may be deteriorated. Therefore, in order to prevent this, it is advantageous that the reactive mesogenic compound is contained in an amount of 300 parts by weight or less based on 100 parts by weight of the polymerizable liquid crystal compound.

On the other hand, the composition for an optical element according to the present invention may further contain a polymerization initiator and a solvent in addition to the polymerizable liquid crystal compound and the reactive mesogenic compound represented by the formula (1). Herein, the polymerization initiator and the solvent may be applied without particular limitations as long as they are conventional in the technical field to which the present invention belongs. The content of the polymerization initiator can be determined within a conventional range that can sufficiently induce the polymerization reaction and prevent deterioration of the physical properties of the composition due to excessive addition, and is preferably 0.01 to 10 parts by weight, relative to 100 parts by weight of the polymerizable liquid crystal compound. 5 parts by weight. The content of the solvent may be determined within a conventional range of giving a proper viscosity to the composition, and may be preferably 100 to 300 parts by weight based on 100 parts by weight of the polymerizable liquid crystal compound.

The composition for an optical element according to the present invention may further comprise, if necessary, a non-mesogenic compound having at least two polymerizable functional groups. The non-mesogenic compound may be included for the purpose of increasing the crosslinking of the polymer, and is preferably selected from the group consisting of alkyl acrylates having 1 to 20 carbon atoms and alkyl dimethacrylates having 1 to 20 carbon atoms May be at least one compound, more preferably trimethylpropane trimethacrylate, pentaerythritol tetraacrylate, and the like.

The composition for an optical element according to the present invention may further contain a surfactant and a stabilizer, if necessary. The surfactant may be a conventional compound such as a fluorine surfactant. The stabilizing agent may be added to prevent spontaneous polymerization reaction during storage of the composition, and a product such as butylated hydroxytoluene (BHT) or Irganox (Ciba AG, Basel, Switzerland) may be used .

According to another embodiment of the present invention, there is provided an optically anisotropic material comprising a cured product or a polymer of the composition for an optical element.

The optically anisotropic material may include a cured product or polymer in which at least a part of the terminal polymerizable group of the polymerizable liquid crystal compound of Formula 1 and the terminal polymerizable group of the mesogenic compound is addition polymerized or crosslinked.

Particularly, the optical anisotropic medium according to the present invention can exhibit an inverse wavelength dispersion satisfying the following formulas I and II by including a cured product or polymer of the above-mentioned polymerizable liquid crystal compound.

(Formula I)

DELTA n _{(450 nm )} / DELTA n _{(550 nm )} < 1.0

(Formula II)

? N _{(650 nm )} /? N _{(550 nm )} > 1.0

(In the above formulas I and II,? N (?) Means the specific refractive index at the wavelength? Within the liquid crystal phase)

Thus, by using the composition for an optical element according to the present invention, it is possible to form an optically anisotropic material having a thin thickness and exhibiting an inverse wavelength dispersion, in a simpler process, unlike the former laminated optically anisotropic material.

On the other hand, the optical anisotropy can be produced by coating and drying the composition for optical element on a support, aligning the liquid crystal compound, and then irradiating ultraviolet rays or the like to polymerize.

Here, the support is not particularly limited, but a glass plate, a polyethyleneterephthalate film, a cellulose-based film, or the like can be used. As a method of applying the polymerizable liquid crystal composition to a support, known methods can be applied without any particular limitation. For example, a roll coating method, a spin coating method, a bar coating method, a spray coating method, and the like can be applied.

As a method of orienting the composition for an optical element, known methods such as rubbing the formed composition layer or applying a magnetic field or electric field to the formed composition layer may be applied.

The thickness of the optically anisotropic material may be adjusted depending on the application, and may be adjusted preferably in the range of 0.01 to 100 탆.

The optical anisotropic material of the present invention can be used as an optical element such as a retardation film, an optical compensation plate, an orientation film, a polarizer, a viewing angle enlargement plate, a reflection film, a color filter, a holographic element, a photo- have.

Hereinafter, the functions and effects of the present invention will be described in more detail with reference to specific embodiments of the present invention. It is to be understood, however, that these embodiments are merely illustrative of the invention and are not intended to limit the scope of the invention.

[Scheme 1: Examples 1 to 9]

Example  1: Compound S1 -2-a Synthesis of

Approximately 110 g of methyl 4-hydroxybenzoate (S1-1), about 70 ml of 3-bromopropanol and about 140 g of potassium carbonate were dissolved in acetone, followed by stirring under reflux for about 24 hours. The reaction mixture was cooled to room temperature and filtered to remove the solid and distillation under reduced pressure. Column chromatography purification yielded about 150 g of compound S1-2-a (n = 3).

Example  2: Compound S1 Synthesis of -2-b

About 95 g of the compound S1-2-b (n = 6) was obtained under the same conditions and conditions as in Example 1, except that 6-bromohexanol was used instead of 3-bromopropanol.

Example  3: Compound S1 Synthesis of -2-c

About 160 g of compound S1-2-c (n = 9) was obtained under the same conditions and conditions as in Example 1, except that 9-bromomonanol was used instead of 3-bromopropanol.

Example  4: Compound S1 Synthesis of -3-a

About 120 g of the compound S1-2-a according to Example 1 and about 28 g of pyridinium paratoluene sulfonate were dissolved in dichloromethane and then cooled to about 0 占 폚. To this was added dropwise a solution of about 76 ml of 3,4-dihydro-2H-pyran in dichloromethane, followed by stirring for about 12 hours. The reaction solution was washed with brine, chemically dried, and then distilled under reduced pressure to obtain about 170 g of compound S1-3-a (n = 3).

Example  5: Compound S1 Synthesis of -3-b

About 123 g of the compound S1-3-b (n = 6) was obtained under the same conditions and conditions as in Example 4, except that about 90 g of the compound S1-2-b according to Example 2 was used instead of the compound S1-2-a .

Example  6: Compound S1 Synthesis of -3-c

About 191 g of the compound S1-3-c (n = 9) was obtained under the same conditions and conditions as in Example 4, except that about 150 g of the compound S1-2-c according to Example 3 was used instead of the compound S1-2-a .

Example  7: Compound S1 -4-a

About 160 g of the compound S1-3-a according to Example 4 was dissolved in methanol, and sodium hydroxide (2M, 300 ml) was added. This was refluxed and stirred for about 2 hours and then distilled under reduced pressure. The reaction was dissolved in water and dichloromethane, and then adjusted to pH 5 with 3M hydrochloric acid. The organic layer was separated, chemically dried, distilled under reduced pressure, and washed with hexane to obtain about 144 g of a white solid compound S1-4-a (n = 3).

Example  8: Compound S1 Synthesis of -4-b

(N = 6), which was a white solid, was obtained in the same manner as in Example 7, except that about 120 g of the compound S1-3-b according to Example 5 was used instead of the compound S1-3-a. About 110 g was obtained.

Example  9: Compound S1 Synthesis of -4-c

The compound S1-4-c (n = 9), which was a white solid, was obtained in the same manner and under the same conditions as in Example 7 except that about 190 g of the compound S1-3-c according to Example 6 was used instead of the compound S1-3- About 174 g was obtained.

[Scheme 2: Examples 10 to 18]

Example  10: Compound S2 -2-a Synthesis of

Approximately 110 g of methyl 4-hydroxy-3-methoxybenzoate (S2-1), about 70 ml of 3-bromopropanol and about 140 g of potassium carbonate were dissolved in acetone, and about 24 Lt; / RTI > The reaction mixture was cooled to room temperature and filtered to remove the solid and distillation under reduced pressure. Column chromatography purification afforded about 55 g of the compound S2-2-a (n = 3).

Example  11: Compound S2 Synthesis of -2-b

About 49 g of the compound S2-2-b (n = 6) was obtained under the same conditions and conditions as in Example 10 except that 6-bromohexanol was used instead of 3-bromopropanol.

Example  12: Compound S2 Synthesis of -2-c

Approximately 51 g of the compound S2-2-c (n = 9) was obtained under the same conditions and conditions as in Example 10, except that 9-bromomonanol was used in place of 3-bromopropanol.

Example  13: Compound S2 Synthesis of -3-a

About 50 g of the compound S2-2-a according to Example 10 and about 28 g of pyridinium paratoluene sulfonate were dissolved in dichloromethane and then cooled to about 0 占 폚. To this was added dropwise a solution of about 76 ml of 3,4-dihydro-2H-pyran in dichloromethane, followed by stirring for about 12 hours. The reaction solution was washed with brine, chemically dried, and then distilled under reduced pressure to obtain about 59 g of the compound S2-3-a (n = 3).

Example  14: Compound S2 Synthesis of -3-b

About 43 g of the compound S2-3-b (n = 6) was obtained under the same conditions and conditions as in Example 13, except that about 40 g of the compound S2-2-b according to Example 11 was used instead of the compound S2-2-a .

Example  15: Compound S2 Synthesis of -3-c

About 55 g of a compound S2-3-c (n = 9) was obtained under the same conditions and conditions as in Example 13, except that about 50 g of the compound S2-2-c according to Example 12 was used instead of the compound S2-2-a .

Example  16: Compound S2 -4-a

About 55 g of the compound S2-3-a according to Example 13 was dissolved in methanol, and sodium hydroxide (2M, 300 ml) was added. This was refluxed and stirred for about 2 hours and then distilled under reduced pressure. The reaction was dissolved in water and dichloromethane, and then adjusted to pH 5 with 3M hydrochloric acid. The organic layer was separated, chemically dried, distilled under reduced pressure, and then washed with hexane to obtain about 42 g of a white solid compound S2-4-a (n = 3).

Example  17: Compound S2 Synthesis of -4-b

(N = 6), which was a white solid, by the same method and under the same conditions as in Example 16 except that about 40 g of the compound S2-3-b according to Example 14 was used instead of the compound S2-3-a. Approximately 33 g was obtained.

Example  18: Compound S2 Synthesis of -4-c

(N = 9), which was a white solid, by the same method and under the same conditions as in Example 16, except that about 50 g of the compound S2-3-c according to Example 15 was used instead of the compound S2-3-a. About 43 g was obtained.

[Scheme 3: Examples 19 to 20]

Example  19: Compound S3 Synthesis of -2

About 300 g of 3,6-dihydroxyphthalonitrile (S3-1) and about 1.9 kg of potassium hydroxide were dissolved in water, and the mixture was stirred under reflux for about 3 hours. The reaction solution was cooled to about 0 < 0 > C, treated with 30% sulfuric acid and extracted with ethyl acetate. The organic layer extracted therefrom was chemically dried and distilled under reduced pressure to obtain about 359 g of compound S3-2.

Example  20: Compound S3 Synthesis of -3

About 359 g of the compound S3-2 according to Example 19 and about 600 g of 4-iodoaniline were dissolved in acetic acid and stirred at reflux for about 2 hours. The reaction solution was cooled to room temperature, diluted with water, and extracted with ethyl acetate. The organic layer extracted from this was chemically dried and distilled under reduced pressure to obtain about 312 g of compound S3-3.

[Scheme 4: Examples 21 to 23]

Example  21: Compound S1 -5-a

About 10 g of the compound S3-3 according to Example 20, about 17 g of the compound S1-4-a according to Example 7 and about 12 g of N- (3-dimethylaminopropyl) -N'-ethylcarbodiimide hydrochloride) were dissolved in dichloromethane Lt; 0 > C. To this, about 1.5 g of dimethylaminopyridine and about 15 g of diisopropylethylamine were added, and the mixture was stirred for about 3 hours.

The reaction solution was diluted with dichloromethane, washed with 1N hydrochloric acid and brine and dried chemically. Subsequently, the reaction product was obtained through filtration and vacuum distillation, and the product was purified by column chromatography to obtain about 24 g of a compound S1-5-a (n = 3).

Example  22: Compound S1 Synthesis of -5-b

About 25 g of the compound S1-5-b (n = 6) was obtained under the same conditions and conditions as in Example 21 except that about 20 g of the compound S1-4-b according to Example 8 was used instead of the compound S1-4-a .

Example  23: Compound S1 Synthesis of -5-c

About 21 g of the compound S1-5-c (n = 9) was obtained under the same conditions and conditions as in Example 21 except that about 20 g of the compound S1-4-c according to Example 9 was used instead of the compound S1-4-a .

[Scheme 5: Examples 24 to 26]

Example  24: Compound S2 -5-a

About 10 g of the compound S3-3 according to Example 20, about 20 g of the compound S2-4-a according to Example 10, and about 12 g of EDC were dissolved in dichloromethane and then cooled to about 0 占 폚. To this, about 1.5 g of dimethylaminopyridine and about 15 g of diisopropylethylamine were added, and the mixture was stirred for about 3 hours.

The reaction solution was diluted with dichloromethane, washed with 1N hydrochloric acid and brine and dried chemically. Subsequently, the reaction product was obtained by filtration and distillation under reduced pressure, and the product was purified by column chromatography to obtain about 19 g of the compound S2-5-a (n = 3).

Example  25: Compound S2 Synthesis of -5-b

About 22 g of the compound S2-5-b (n = 6) was obtained under the same conditions and conditions as in Example 24 except that about 20 g of the compound S2-4-b according to Example 11 was used instead of the compound S2-4-a .

Example  26: Compound S2 Synthesis of -5-c

About 25 g of the compound S2-5-c (n = 9) was obtained under the same conditions and conditions as in Example 24 except that about 20 g of the compound S2-4-c according to Example 12 was used instead of the compound S2-4-a .

[Scheme 6: Examples 27 to 29]

Example  27: Compound S1 -6-a

About 20 g of the compound S1-5-a according to Example 21, about 1.5 g of 1,4-diethynylbenzene, about 0.47 g of bis (triphenylphosphine) palladium (II) dichloride, and About 122 mg of copper iodide was dissolved in a mixed solution of about 100 ml of triethylamine and about 50 ml of dimethylformamide. It was stirred at about 70 < 0 > C for about 5 hours and cooled to precipitate crystals. Thereafter, the product was purified by column chromatography to obtain about 18 g of compound S1-6-a (n = 3).

Example  28: Compound S1 Synthesis of -6-b

About 15 g of the compound S1-6-b (n = 6) was obtained under the same conditions and conditions as in Example 27, except that about 20 g of the compound S1-5-b according to Example 22 was used instead of the compound S1-5-a .

Example  29: Compound S1 Synthesis of -6-c

About 14 g of the compound S1-6-c (n = 9) was obtained under the same conditions and conditions as in Example 27, except that about 20 g of the compound S1-5-c according to Example 23 was used instead of the compound S1-5-a .

[Scheme 7: Examples 30 to 32]

Example  30: Compound S1 Synthesis of -7-a

About 20 g of the compound S1-5-a according to Example 21, about 1.5 g of 4,4'-diethynylbiphenyl (Chem.Commun., 2010, 46, 4547) Phosphine) palladium (II) dichloride, and about 122 mg of copper iodide were dissolved in a mixed solution of about 100 ml of triethylamine and about 50 ml of dimethylformamide. It was stirred at about 70 < 0 > C for about 5 hours and cooled to precipitate crystals. Thereafter, the product was purified by column chromatography to obtain about 17 g of the compound S1-7-a (n = 3).

Example  31: Compound S1 Synthesis of -7-b

About 14 g of a compound S1-7-b (n = 6) was obtained under the same conditions and conditions as in Example 30 except that about 20 g of the compound S1-5-b according to Example 22 was used instead of the compound S1-5-a .

Example  32: Compound S1 Synthesis of -7-c

About 17 g of compound S1-7-c (n = 9) was obtained under the same conditions and conditions as in Example 30 except that about 20 g of the compound S1-5-c according to Example 23 was used instead of the compound S1-5-a .

[Scheme 8: Examples 33 to 35]

Example  33: Compound S2 -6-a

About 20 g of the compound S2-5-a according to Example 24, about 1.5 g of 1,4-diethynylbenzene, about 0.47 g of bis (triphenylphosphine) palladium (II) dichloride, and About 122 mg of copper iodide was dissolved in a mixed solution of about 100 ml of triethylamine and about 50 ml of dimethylformamide. It was stirred at about 70 < 0 > C for about 5 hours and cooled to precipitate crystals. Thereafter, the product was purified by column chromatography to obtain about 14 g of the compound S2-6-a (n = 3).

Example  34: Compound S2 Synthesis of -6-b

About 16 g of the compound S2-6-b (n = 6) was obtained under the same conditions and conditions as in Example 33 except that about 20 g of the compound S2-5-b according to Example 25 was used instead of the compound S2-5-a .

Example  35: Compound S2 Synthesis of -6-c

About 12 g of the compound S2-6-c (n = 9) was obtained under the same conditions and conditions as in Example 33, except that about 20 g of the compound S2-5-c according to Example 26 was used instead of the compound S2-5-a .

[Scheme 9: Examples 36 to 38]

Example  36: Compound S2 Synthesis of -7-a

About 20 g of the compound S2-5-a according to Example 24, about 1.5 g of 4,4'-diethynylbiphenyl (Chem.Commun., 2010, 46, 4547) Phosphine) palladium (II) dichloride, and about 122 mg of copper iodide were dissolved in a mixed solution of about 100 ml of triethylamine and about 50 ml of dimethylformamide. It was stirred at about 70 < 0 > C for about 5 hours and cooled to precipitate crystals. Thereafter, the product was purified by column chromatography to obtain about 16 g of the compound S2-7-a (n = 3).

Example  37: Compound S2 Synthesis of -7-b

About 18 g of the compound S2-7-b (n = 6) was obtained under the same conditions and conditions as in Example 36 except that about 20 g of the compound S2-5-b according to Example 25 was used instead of the compound S2-5-a .

Example  38: Compound S2 Synthesis of -7-c

About 13 g of a compound S2-7-c (n = 9) was obtained under the same conditions and conditions as in Example 36 except that about 20 g of the compound S2-5-c according to Example 26 was used instead of the compound S2-5-a .

[Scheme 10: Examples 39 to 41]

Example  39

(Synthesis of compound RD-01)

About 10 g of the compound S1-6-a according to Example 27 and about 0.4 g of pyridinium paratoluene sulfonate (PPTS) were dissolved in tetrahydrofuran and refluxed for about 2 hours. Subsequently, all of the solvent of the reaction solution was removed by distillation under reduced pressure, diluted with dichloromethane, and washed with brine. The organic layer was dried chemically and distilled under reduced pressure to obtain a white solid compound.

The white solid compound was dissolved in about 90 ml of dimethylacetamide and then cooled to about 0 캜. To this, about 6.7 g of acryloyl chloride was added dropwise over about 30 minutes, and the mixture was stirred at room temperature for about 2 hours. The reaction solution was diluted with diethyl ether and washed with an aqueous solution of sodium chloride. After the organic portion was collected and chemically dried, the solvent was distilled off under reduced pressure. The obtained product was purified by column chromatography to obtain about 9.3 g of compound RD-01 (n = 3).

The NMR spectrum of the obtained compound RD-01 is as follows.

¹ H NMR (CDCl _3, standard TMS) δ (ppm): 8.07 (8H, m), 7.68 (8H, m), 7.44 (8H, m), 6.92 (8H, m), 6.43 (4H, dd) , 6.06 (4H, dd), 5.80 (4H, dd), 4.15 (8H, m), 3.99 (8H, m), 2.01

Then, the structure of the compound RD-01 was observed with a polarizing microscope, and the phase transition temperature was measured. As a result, an isotropic liquid crystal phase appeared when the temperature exceeded about 230 ° C. In this way, it was confirmed that the compound RD-01 forms a nematic phase at a temperature range of about 180 ° C to 230 ° C.

Example  40

(Synthesis of compound RD-02)

About 9.1 g of the compound RD-02 (n = 6) was obtained under the same conditions and conditions as in Example 39, except that the compound S1-6-b according to Example 28 was used instead of the compound S1-6-a.

The NMR spectrum of the obtained compound RD-02 is as follows.

¹ H NMR (CDCl _3, standard TMS) δ (ppm): 8.11 (8H, m), 7.71 (8H, m), 7.45 (8H, m), 6.96 (8H, m), 6.44 (4H, dd) , 6.09 (4H, dd), 5.90 (4H, dd), 4.16 (8H, m), 3.91 (8H, m), 1.65

Then, the structure of the compound RD-02 was observed with a polarizing microscope, and the phase transition temperature was measured. As a result, the temperature was changed from about 185 ° C to a nematic phase of the crystal phase, and when the temperature exceeded about 245 ° C, an isotropic liquid crystal phase appeared. In this way, it was confirmed that compound RD-02 forms a nematic phase at a temperature range of about 185 캜 to 245 캜.

Example  41

(Synthesis of compound RD-03)

About 8 g of compound RD-03 (n = 9) was obtained under the same conditions and conditions as in Example 39, except that the compound S1-6-c according to Example 29 was used instead of the compound S1-6-a.

The NMR spectrum of the obtained compound RD-03 is as follows.

¹ H NMR (CDCl _3, standard TMS) δ (ppm): 8.03 (8H, m), 7.64 (8H, m), 7.40 (8H, m), 6.92 (8H, m), 6.43 (4H, dd) , 6.01 (4H, dd), 5.95 (4H, dd), 4.17 (8H, m), 3.92 (8H, m), 1.71

Then, the structure of the compound RD-03 was observed with a polarizing microscope, and the phase transition temperature was measured. As a result, the temperature was changed from about 210 ° C to a nematic phase of the crystal phase, and when the temperature exceeded about 250 ° C, an isotropic liquid crystal phase appeared. In this way, it was confirmed that compound RD-03 forms a nematic phase at a temperature range of about 210 ° C to 250 ° C.

[Scheme 11: Examples 42 to 43]

Example  42

(Synthesis of compound RD-04)

About 7.7 g of compound RD-04 (n = 6) was obtained under the same conditions and conditions as in Example 39, except that the compound S1-7-b according to Example 31 was used instead of the compound S1-6-a.

The NMR spectrum of the obtained compound RD-05 is as follows.

¹ H NMR (CDCl _3, standard TMS) δ (ppm): 8.02 (8H, m), 7.74-7.51 (20H, m), 7.45 (8H, m), 6.91 (8H, m), 6.43 (4H, (8H, m), 1.57 (8H, m), 1.24 (16H, m), 6.04 (4H, dd), 5.94 )

Then, the structure of the compound RD-04 was observed with a polarizing microscope, and the phase transition temperature was measured. As a result, an isotropic liquid crystal phase appeared when the temperature exceeded about 220 ° C. In this way, it was confirmed that the compound RD-04 forms a nematic phase at a temperature range of about 190 캜 to 220 캜.

Example  43

(Synthesis of compound RD-05)

About 8.3 g of the compound RD-05 (n = 9) was obtained under the same conditions and conditions as in Example 39, except that the compound S1-7-c according to Example 32 was used instead of the compound S1-6-a.

The NMR spectrum of the obtained compound RD-06 is as follows.

¹ H NMR (CDCl _3, standard TMS) δ (ppm): 8.04 (8H, m), 7.71-7.50 (20H, m), 7.49 (8H, m), 6.92 (8H, m), 6.41 (4H, m), 1.58 (8H, m), 1.31 (4H, dd), 5.90 (4H, dd), 4.20 (8H, m), 3.96 )

Then, the structure of the compound RD-05 was observed with a polarizing microscope and the phase transition temperature was measured. As a result, an isotropic liquid crystal phase appeared when the temperature exceeded about 235 ° C. In this way, it was confirmed that compound RD-05 forms a nematic phase at a temperature range of about 220 캜 to 235 캜.

[Scheme 12: Examples 44 to 46]

Example  44

(Synthesis of compound RD-06)

About 7.8 g of compound RD-06 (n = 3) was obtained under the same conditions and conditions as in Example 39 except that the compound S2-6-a according to Example 33 was used instead of the compound S1-6-a.

The NMR spectrum of the obtained compound RD-06 is as follows.

¹ H NMR (CDCl _3, standard TMS) δ (ppm): 7.66-7.41 (22H, m), 6.81 (4H, m), 4.14 (8H, m), 3.96 (8H, m), 3.73 (12H, s), 2.02 (8 H, m)

The structure of the compound RD-06 was observed with a polarizing microscope and the phase transition temperature was measured. As a result, as the temperature increased, the crystal phase changed to a nematic phase at about 200 ° C, and when the temperature exceeded 230 ° C, an isotropic liquid crystal phase appeared. In this way, it was confirmed that the compound RD-06 forms a nematic phase at a temperature range of about 200 캜 to 230 캜.

Example  45

(Synthesis of compound RD-07)

About 8.3 g of the compound RD-07 (n = 6) was obtained under the same conditions and conditions as in Example 39 except that the compound S2-6-b according to Example 34 was used instead of the compound S1-6-a.

The NMR spectrum of the obtained compound RD-07 is as follows.

¹ H NMR (CDCl _3, standard TMS) δ (ppm): 7.64-7.40 (22H, m), 6.79 (4H, m), 4.16 (8H, m), 3.94 (8H, m), 3.76 (12H, s), 1.64 (8H, m), 1.55 (8H, m), 1.29 (16H, m)

Then, the structure of the compound RD-07 was observed with a polarizing microscope, and the phase transition temperature was measured. As a result, an isotropic liquid crystal phase appeared when the temperature exceeded about 245 ° C. In this way, it was confirmed that compound RD-07 forms a nematic phase at a temperature range of about 220 캜 to 245 캜.

Example  46

(Synthesis of compound RD-08)

About 7 g of compound RD-08 (n = 9) was obtained under the same conditions and conditions as in Example 39, except that the compound S2-6-c according to Example 35 was used instead of the compound S1-6-a.

NMR spectrum of the obtained compound RD-08 is as follows.

¹ H NMR (CDCl _3, standard TMS) δ (ppm): 7.59-7.37 (22H, m), 6.7 (4H, m), 4.15 (8H, m), 3.94 (8H, m), 3.69 (12H, s), 1.72 (8H, m), 1.55 (8H, m), 1.25 (40H, m)

The structure of the compound RD-08 was observed with a polarizing microscope, and the phase transition temperature was measured. As a result, the temperature was changed from about 225 ° C to a nematic phase of the crystal phase, and when the temperature exceeded about 245 ° C, an isotropic liquid crystal phase appeared. In this way, it was confirmed that compound RD-08 forms a nematic phase at a temperature range of about 225 ° C to 245 ° C.

[Scheme 13: Example 47]

Example  47

(Synthesis of compound RD-09)

About 9.3 g of the compound RD-09 (n = 9) was obtained under the same conditions and conditions as in Example 39, except that the compound S2-7-c according to Example 38 was used instead of the compound S1-6-a.

NMR spectrum of the obtained compound RD-09 is as follows.

¹ H NMR (CDCl _3, standard TMS) δ (ppm): 7.54-7.44 (26H, m), 6.71 (4H, m), 4.04 (8H, m), 3.81 (8H, m), 3.76 (12H, s), 1.74 (8H, m), 1.50 (8H, m), 1.30 (40H, m)

Then, the structure of the compound RD-09 was observed with a polarizing microscope, and the phase transition temperature was measured. As a result, the temperature was changed from about 210 ° C to a nematic phase of the crystal phase, and when the temperature exceeded about 250 ° C, an isotropic liquid crystal phase appeared. In this way, it was confirmed that the compound RD-09 forms a nematic phase at a temperature range of about 210 ° C to 250 ° C.

Manufacturing example  One

(Preparation of Composition for Optical Element)

About 66.67 parts by weight of a mesogenic compound represented by the following formula (a), about 69.73 parts by weight of a mesogenic compound represented by the following formula (b), 100 parts by weight of an initiator (Irgacure 907, Ciba- About 3.33 parts by weight of an initiator (Irgacure 1076, manufactured by Ciba-Geigy), about 3.33 parts by weight of a fluorinated surfactant (FC-171, 3M), and about 166.67 parts by weight of toluene, The composition was prepared.

(A)

[Formula b]

(Preparation of retardation film)

The composition was coated on a TAC film coated with a norbornene-based photo-alignment material by a roll coating method, and then dried at about 80 ° C for 2 minutes to orient the liquid crystal molecules. Thereafter, the film was irradiated with unpolarized UV using a high-pressure mercury lamp of 200 mW / cm 2 as a light source to fix the orientation state of the liquid crystal to prepare a retardation film.

The quantitative retardation value of the produced retardation film was measured using Axoscan (manufactured by Axomatrix). At this time, the thickness was independently measured and the value of Δn was obtained from the obtained value. As a result, Δn (450 nm), Δn (550 nm), and Δn (650 nm) were measured to be 0.083, 0.09, and 0.092, respectively. Therefore, the value of DELTA n (450 nm) / DELTA n (550 nm) was 0.92 and the value of DELTA n (650 nm) / DELTA n (550 nm) was 1.02 and it was confirmed that the conditions according to the above formulas I and II were satisfied.

Manufacturing example  2

(Preparation of Composition for Optical Element)

About 100 parts by weight of the RD-02 compound according to Example 40, about 134.29 parts by weight of the mesogenic compound represented by Formula (a), about 45.49 parts by weight of the mesogenic compound represented by Formula (b), initiator (Irgacure 907, Ciba- About 2.86 parts by weight of an initiator (Irgacure 1076, manufactured by Ciba-Geigy), about 2.86 parts by weight of a fluorinated surfactant (FC-171, 3M), and about 214.29 parts by weight of toluene, The composition was prepared.

(Preparation of retardation film)

The composition was coated on a TAC film coated with a norbornene-based photo-alignment material by a roll coating method, and then dried at about 80 ° C for 2 minutes to orient the liquid crystal molecules. Thereafter, the film was irradiated with unpolarized UV using a high-pressure mercury lamp of 200 mW / cm 2 as a light source to fix the orientation state of the liquid crystal to prepare a retardation film.

The quantitative retardation value of the produced retardation film was measured using Axoscan (manufactured by Axomatrix). At this time, the thickness was independently measured and the value of Δn was obtained from the obtained value. As a result, Δn (450 nm), Δn (550 nm), and Δn (650 nm) were measured to be 0.07, 0.082, and 0.085, respectively. Therefore, the value of DELTA n (450 nm) / DELTA n (550 nm) was 0.87 and the value of DELTA n (650 nm) / DELTA n (550 nm) was 1.03 and it was confirmed that the conditions according to the above formulas I and II were satisfied.

Claims (20)

A polymerizable liquid crystal compound represented by the following formula (1); And
At least one reactive mesogenic compound selected from the group of compounds represented by the following general formulas (6a) to (6g)
A composition for an optical element comprising:
[Chemical Formula 1]

In Formula 1,
^{A 1, A 2, A 3} , A 4, E 1, E 2, E 3, and E ⁴ are each independently a single bond, -O-, -S-, -CO-, -COO- , -OCO- , -O-COO-, -CO-NR- , -NR-CO-, -NR-CO-NR-, -OCH 2 -, -CH 2 O-, -SCH 2 -, -CH 2 S-, - _{CF 2 O-, -OCF 2 -,} -CF 2 S-, -SCF 2 -, -CH 2 CH 2 -, - (CH 2) 3 -, - (CH 2) 4 -, -CF 2 CH 2 - _{, -CH 2 CF 2 -, -CF} 2 CF 2 -, -C = C-, or -C≡C-, and; Each R is independently hydrogen or an alkyl group having 1 to 10 carbon atoms;
D ¹ , D ² , D ³ and D ⁴ each independently represent -Ph-, -Ph (OCH ₃ ) -, -CH ₂ Ph-, -PhCH ₂ -, -CH ₂ CH ₂ -Ph-, PhCH ₂ CH ₂ -; Wherein Ph is 1,4-phenylene;
G ¹ , G ² , G ³ , and G ⁴ are each independently an alkylene group having 1 to 10 carbon atoms;
J ¹ , J ² , J ³ , and J ⁴ each independently represent an acrylate group, a methacrylate group, or an epoxy group;
L ¹ , L ² , L ³ , and L ⁴ are each independently 0;
M ¹ and M ² are each independently N;
Q is -Ph-Ph-, -Ph-C≡C-Ph-, -Ph-C≡CC≡C-Ph-, -Ph-C≡C-Ph-C≡C-Ph- or -Ph-C C-Ph-Ph-C? C-Ph-; Wherein Ph is 1,4-phenylene;
p and q are each independently 1 to 5;

[Chemical Formula 6a]

[Formula 6b]

[Chemical Formula 6c]

[Chemical formula 6d]

[Formula 6e]

(6f)

[Chemical Formula 6g]

In the above formulas (6a) to (6g)
x and y are each independently an integer of 1 to 12,
A is a 1,4-phenylene or 1,4-cyclohexylene group,
R ¹ is halogen, cyano, or an alkyl or alkoxy group having 1 to 12 carbon atoms,
Q ¹ and Q ² are each independently H, halogen, CN, alkyl having 1 to 7 carbon atoms, alkoxy or alkanoyl group.
delete delete The method according to claim 1,
G ¹ , G ² , G ³ , and G ⁴ in Formula 1 are each independently an alkylene group having 2 to 9 carbon atoms.
delete delete delete delete delete delete delete delete delete delete delete The method according to claim 1,
With respect to 100 parts by weight of the polymerizable liquid crystal compound,
150 to 300 parts by weight of the reactive mesogenic compound,
0.01 to 5 parts by weight of a polymerization initiator, and
100 to 300 parts by weight of a solvent
Wherein the composition for an optical element is a composition for an optical element.
The method according to claim 1,
Further comprising a non-mesogenic compound having at least two polymerizable functional groups,
Wherein the non-mesogenic compound is at least one compound selected from the group consisting of alkyl acrylates having 1 to 20 carbon atoms and alkyl dimethacrylates having 1 to 20 carbon atoms.
An optically anisotropic composition comprising a cured product or polymer of the composition according to claim 1.
19. The method of claim 18,
An optically anisotropic material satisfying the following formulas I and II:
(Formula I)
DELTA n _{(450 nm )} / DELTA n _{(550 nm )} < 1.0
(Formula II)
? N _{(650 nm )} /? N _{(550 nm )} > 1.0
In the above formula (I) and formula (II),? N (?) Means the specific refractive index at the wavelength? Within the liquid crystal phase.
An optical element for a liquid crystal display device comprising the optically anisotropic element according to claim 18.