KR102546067B1 - Reactive mesogen and liquid crystal composition including the same - Google Patents

Abstract

A reactive mesogen capable of improving display quality of a liquid crystal display device and a liquid crystal composition including the same are provided. The reactive mesogen is represented by Formula 1 below.
[Formula 1]

Description

Reactive mesogen and a liquid crystal composition containing the same {REACTIVE MESOGEN AND LIQUID CRYSTAL COMPOSITION INCLUDING THE SAME}

The present invention relates to a reactive mesogen and a liquid crystal composition containing the reactive mesogen. More specifically, the present invention relates to a reactive mesogen forming a liquid crystal alignment layer in a liquid crystal display device and a liquid crystal composition including the reactive mesogen.

In general, liquid crystal displays are classified into twisted nematic liquid crystal displays, horizontal electric field liquid crystal displays, vertical alignment liquid crystal displays, and the like, depending on characteristics of liquid crystal layers. The dual vertically aligned liquid crystal display is characterized in that it is aligned in a predetermined direction in a state where no electric field is applied and long axes of liquid crystal molecules are aligned perpendicular to the substrate surface. Accordingly, the vertically aligned liquid crystal display has a wide viewing angle and a high contrast ratio.

On the other hand, as a method for orienting the liquid crystal molecules in a predetermined direction, a rubbing method or an optical alignment method is used, and in a vertical alignment type liquid crystal display device, technologies for orienting the liquid crystal molecules in a predetermined direction using reactive mesogens are proposed. It is becoming.

An object of the present invention is to provide a novel reactive mesogen used in a liquid crystal display device.

An object of the present invention is to provide a novel reactive mesogen that stably forms an alignment layer in a liquid crystal display device and a liquid crystal composition including the same.

The reactive mesogen of one embodiment may be represented by Chemical Formula 1 below.

[Formula 1]

In Formula 1, A ₁ , A ₂ , and A ₃ are each independently a substituted or unsubstituted divalent hydrocarbon ring group or a substituted or unsubstituted divalent heterocyclic group. a1, b1 and b2 are each independently an integer of 0 or more and 6 or less, and a2 and a3 are each independently 0 or 1. L ₁ and L ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _k1 -, -S(CH ₂ ) _k1 -, -O(CF ₂ ) _k1 -, -S(CF ₂ ) _k1 -, -(CH ₂ ) _k1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _k1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, or -(CH ₂ ) _k1 -COO-(CH ₂ ) _k2 -O-, and k1 and k2 are each independently an integer from 0 to 4. . Z ₁ and Z ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _m1 -, -S(CH ₂ ) _m1 -, -O(CF ₂ ) _m1 -, -S(CF ₂ ) _m1 -, -(CH ₂ ) _m1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _m1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, -(CH ₂ ) _m1 -COO-, -(CH ₂ ) _m1 -COO-(CH ₂ ) _m2 -O-, -CH-(S _p -Pa)-, -CH ₂ CH-(S _p -Pa)- or -(CH-(S _p -Pa)-CH-(S _p -Pa))-, and m1 and m2 are each independently 0 It is an integer greater than or equal to 4. _Sp is a single bond or a spacer group, and Pa is a polymerization group.

이고, n1 및 n2는 각각 독립적으로 1 이상 12 이하의 정수이고, T₁ 및 T₂는 각각 독립적으로 -OH, -CH_3, -CF₃, -CHF₂, -CH₂F, -CH₂Br, -CHBr₂, -CHCl₂, 또는 -CH₂Cl 이며, 상기 T₁ 및 T₂ 중 적어도 하나는 -OH이다.B is an unsubstituted heterocyclic group, a substituted or unsubstituted Crown Ether group, or

And, n1 and n2 are each independently an integer of 1 or more and less than or equal to 12, and T ₁ and T ₂ are each independently -OH, -CH _3, -CF ₃ , -CHF ₂ , -CH ₂ F, -CH ₂ Br , -CHBr ₂ , -CHCl ₂ , or -CH ₂ Cl, and at least one of T ₁ and T ₂ is -OH.

Wherein A ₁ , A ₂ , and A ₃ are each independently a substituted or unsubstituted aromatic ring group having 6 or more and 30 or less ring carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 2 or more and 30 or less ring carbon atoms, and a substituted Alternatively, it may be an unsubstituted aliphatic ring group having 5 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaliphatic ring group having 2 or more and 30 or less ring carbon atoms.

A ₁ , A ₂ , and A ₃ may each independently be selected from the following substituted or unsubstituted ring compounds A-1 to A-22.

A ₁ , A ₂ , and A ₃ are each independently a deuterium atom, a halogen atom, -CN, -NO, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R ⁰ ) ₂ , -C(=O)R ⁰ , a substituted or unsubstituted silyl group, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group, an alkoxycarbonyl group, or an alkylcarbonyloxy group. Here, R ⁰ may be an alkyl group having 1 to 12 carbon atoms.

A ₁ , A ₂ , and A ₃ may be selected from A-22 to A-26.

또는

일 수 있다.The B is

or

can be

The B may be any one of the following B-1 to B-18.

The B may be any one of E-1 to E-13.

The Pa may be any one of the following P-1 to P-9.

Formula 1 may be selected from compounds shown in Compound Group 1 below.

[Compound group 1]

Formula 1 may be selected from compounds shown in Compound Group 2 below.

[Compound group 2]

Formula 1 may be selected from compounds shown in Compound Group 3 below.

[Compound group 3]

One embodiment provides a reactive mesogen represented by Formula 2 below.

[Formula 2]

In Formula 2, X is any one of the following X-1 to X-17.

Z ₁ and Z ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _m1 -, -S(CH ₂ ) _m1 -, -O(CF ₂ ) _m1 -, -S(CF ₂ ) _m1 -, -(CH ₂ ) _m1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _m1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, -(CH ₂ ) _m1 -COO-, -(CH ₂ ) _m1 -COO-(CH ₂ ) _m2 -O-, -CH-(S _p -Pa)-, -CH ₂ CH-(S _p -Pa)- or -(CH-(S _p -Pa)-CH-(S _p -Pa))-, and m1 and m2 are each independently 0 It is an integer greater than or equal to 4. _Sp is a single bond or a spacer group, and Pa is a polymerization group.

이고, n1 및 n2는 각각 독립적으로 1 이상 12 이하의 정수이고, T₁ 및 T₂는 각각 독립적으로 -OH, -CH_{3, -}CF₃, -CHF₂, -CH₂F, -CH₂Br, -CHBr₂, -CHCl₂, 또는 -CH₂Cl 이며, 상기 T₁ 및 T₂ 중 적어도 하나는 -OH이다.B is an unsubstituted heterocyclic group, a substituted or unsubstituted crown ether group, or

And, n1 and n2 are each independently an integer of 1 or more and less than or equal to 12, and T ₁ and T ₂ are each independently -OH, -CH _3, -CF ₃ , -CHF ₂ , -CH ₂ F, -CH ₂ Br , -CHBr ₂ , -CHCl ₂ , or -CH ₂ Cl, and at least one of T ₁ and T ₂ is -OH.

The B may be any one of the following B-1 to B-20 and E-1 to E-13.

The Pa may be any one of the following P-1 to P-9.

An embodiment may provide a liquid crystal composition including a liquid crystal compound and a first reactive mesogen represented by Chemical Formula 3 below.

[Formula 3]

In Formula 3, A ₁ , A ₂ , A ₃ , L ₁ , L ₂ , Z ₁ , Z ₂ , Pa, B, a1, a2, a3, b1 and b2 are the same as defined in Formula 1 above.

The liquid crystal composition may further include a second reactive mesogen represented by Chemical Formula 4 below.

[Formula 4]

In Formula 4, Pa and Pb each independently represent any one of the following P-1 to P-10 polymerization groups, except for the case where Pa and Pb are P-10 at the same time. p is an integer of 1 or more and 20 or less.

In Formula 4, A ₁ , A ₂ , A ₃ , L ₁ , L ₂ , Z ₁ , Z ₂ , a1, a2, a3, b1 and b2 are each the same as defined in Formula 1 above.

The liquid crystal composition may further include a third reactive mesogen represented by Chemical Formula 5 below.

[Formula 5]

In Formula 5, X may be any one of the following X-1 to X-17, and Z ₁ , Z ₂ , B and Pa are the same as defined in Formula 1 above.

The first reactive mesogen may be included in an amount of 0.1 parts by weight or more and 2 parts by weight or less based on 100 parts by weight of the liquid crystal compound.

The third reactive mesogen may be included in an amount of 1 part by weight or more and 10 parts by weight or less based on 100 parts by weight of the sum of the first reactive mesogen and the second reactive mesogen.

The liquid crystal compound may include a nematic liquid crystal compound.

The liquid crystal compound may include at least one of the following L-1 to L-10.

The reactive mesogen of an embodiment may stably form an alignment layer in a liquid crystal display device by having two reactive groups at the end of an anchoring group or a crown ether group at the end of the reactive mesogen.

The liquid crystal composition of one embodiment may improve alignment characteristics of the liquid crystal by providing a novel reactive mesogen together with the liquid crystal compound.

1 is a cross-sectional view illustrating a liquid crystal display including an alignment layer formed of a reactive mesogen according to an embodiment.
2 is a plan view schematically illustrating one pixel among pixels included in a liquid crystal display including an alignment layer formed of reactive mesogen according to an exemplary embodiment.
FIG. 3 is a cross-sectional view corresponding to line II' of FIG. 2 .
4 is a SEM image showing the surface of an alignment layer formed by providing a liquid crystal composition according to an embodiment.
5 is a cross-sectional view illustrating a liquid crystal display including an alignment layer formed of a reactive mesogen according to an exemplary embodiment.
6 to 14 show NMR spectra for confirming the synthesis of compounds 1 to 2, compounds 6 to 9, and compounds 12 to 14, which are examples of reactive mesogens.
15A to 15C are diagrams schematically illustrating a bonding relationship between a reactive mesogen and an electrode according to an embodiment.
16 is a diagram showing images of display quality of a liquid crystal display according to a content of reactive mesogens according to an exemplary embodiment.
17A and 17B are graphs showing voltage retention over time of the liquid crystal display.

Since the present invention may have various changes and various forms, specific embodiments are illustrated in the drawings and described in detail in the text. However, it should be understood that this is not intended to limit the present invention to the specific disclosed form, and includes all modifications, equivalents, and substitutes included in the spirit and scope of the present invention.

Like reference numerals have been used for like elements throughout the description of each figure. In the accompanying drawings, the dimensions of the structures are shown enlarged than actual for clarity of the present invention. Terms such as first and second may be used to describe various components, but the components should not be limited by the terms. These terms are only used for the purpose of distinguishing one component from another. For example, a first element may be termed a second element, and similarly, a second element may be termed a first element, without departing from the scope of the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise.

In this application, the terms "include" or "have" are intended to designate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, but one or more other features It should be understood that it does not preclude the possibility of the presence or addition of numbers, steps, operations, components, parts, or combinations thereof. In addition, when a part such as a layer, film, region, plate, etc. is said to be "on" another part, this includes not only the case where it is "directly on" the other part, but also the case where another part is present in the middle. Conversely, when a part such as a layer, film, region, plate, etc. is said to be "under" another part, this includes not only the case where it is "directly under" the other part, but also the case where there is another part in between. In addition, in the present application, being disposed "on" may include the case of being disposed not only on the top but also on the bottom.

As used herein, “substituted or unsubstituted” means a deuterium atom, a halogen atom, a cyano group, a nitrile group, a nitro group, an amino group, a silyl group, a boron group, a phosphine oxide group, an alkyl group, an alkenyl group, a fluorenyl group, an aryl It may mean substituted or unsubstituted with one or more substituents selected from the group consisting of groups and heterocyclic groups. In addition, each of the substituents exemplified above may be substituted or unsubstituted. For example, a biphenyl group may be interpreted as an aryl group or a phenyl group substituted with a phenyl group.

In the present specification, “forming a ring by combining with adjacent groups” may mean forming a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle by combining with adjacent groups. Hydrocarbon rings include aliphatic hydrocarbon rings and aromatic hydrocarbon rings. Heterocycles include aliphatic heterocycles and aromatic heterocycles. Hydrocarbon rings and heterocycles may be monocyclic or polycyclic. In addition, a ring formed by bonding with adjacent groups may be connected to another ring to form a spiro structure.

In this specification, "adjacent group" may refer to a substituent substituted on an atom directly connected to the atom on which the corresponding substituent is substituted, another substituent substituted on the atom on which the corresponding substituent is substituted, or a substituent sterically closest to the corresponding substituent. there is. For example, two methyl groups in 1,2-dimethylbenzene can be interpreted as "adjacent groups" to each other, and 2 methyl groups in 1,1-diethylcyclopentene The two ethyl groups can be interpreted as "adjacent groups" to each other.

In this specification, examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

In this specification, the alkyl group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkyl group is 1 or more and 30 or less, 1 or more and 20 or less, 1 or more and 10 or less, or 1 or more and 6 or less. Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, t-butyl group, i-butyl group, 2-ethylbutyl group, 3,3-dimethylbutyl group. , n-pentyl group, i-pentyl group, neopentyl group, t-pentyl group, cyclopentyl group, 1-methylpentyl group, 3-methylpentyl group, 2-ethylpentyl group, 4-methyl-2-pentyl group , n-hexyl group, 1-methylhexyl group, 2-ethylhexyl group, 2-butylhexyl group, cyclohexyl group, 4-methylcyclohexyl group, 4-t-butylcyclohexyl group, n-heptyl group, 1 -Methylheptyl group, 2, 2-dimethylheptyl group, 2-ethylheptyl group, 2-butylheptyl group, n-octyl group, t-octyl group, 2-ethyloctyl group, 2-butyloctyl group, 2-hexyl Siloctyl group, 3, 7-dimethyloctyl group, cyclooctyl group, n-nonyl group, n-decyl group, adamantyl group, 2-ethyldecyl group, 2-butyldecyl group, 2-hexyldecyl group, 2-octyl group Tyldecyl group, n-undecyl group, n-dodecyl group, 2-ethyldodecyl group, 2-butyldodecyl group, 2-hexyldodecyl group, 2-octyldodecyl group, n-tridecyl group, n-tetradecyl group, n -Pentadecyl group, n-hexadecyl group, 2-ethylhexadecyl group, 2-butylhexadecyl group, 2-hexylhexadecyl group, 2-octylhexadecyl group, n-heptadecyl group, n-octadecyl group , n- nonadecyl group, n- icosyl group, 2-ethyl icosyl group, 2-butyl icosyl group, 2-hexyl icosyl group, 2-octyl icosyl group, n-henicosyl group, n- docosyl group, n-tricot practical group, n-tetracosyl group, n-pentacosyl group, n-hexacosyl group, n-heptacosyl group, n-octacosyl group, n-nonacosyl group, and n-triacontyl group; not limited to these

,

,

, 및

등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group. The arylene group may be the same as the description for the aryl group except that it is divalent. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. The number of ring carbon atoms in the arylene group may be 6 or more and 30 or less, 6 or more and 20 or less, or 6 or more and 15 or less. Examples of the aryl group include a phenyl group, a naphthyl group, anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a quincphenyl group, a sexyphenyl group, a triphenylene group, a pyrenyl group, a fluorenyl group, a benzo fluoranthenyl group, A chrysenyl group etc. can be illustrated. However, the aryl group is not limited to those exemplarily described. In addition, the exemplified aryl group may be substituted or unsubstituted, and in the case of a substituted aryl group, two substituents may be bonded to each other to form a spiro structure. For example, when the fluorenyl group is substituted,

,

,

, and

etc. However, it is not limited thereto.

In the present specification, the heteroaryl group may be a heteroaryl group including one or more of O, N, and S as heterogeneous elements. The number of ring carbon atoms in the heteroaryl group is 2 or more and 30 or less, or 2 or more and 20 or less. Examples of the heteroaryl group include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, a triazole group, Acridyl group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phenoxazyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group , isoquinoline group, indole group, carbazole group, N-arylcarbazole group, N-heteroarylcarbazole group, N-alkylcarbazole group, benzooxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, thienothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl group, phenothia A jinyl group and a dibenzofuranyl group, but are not limited thereto.

In this specification, the description of the aryl group described above may be applied except that the arylene group is a divalent group. In addition, the divalent group of the biphenyl group, which is an aryl group, can be represented by a divalent biphenyl group.

In the present specification, the description of the heteroaryl group described above may be applied except that the heteroarylene group is a divalent group.

"는 화합물에서 연결되는 부분을 나타내는 것일 수 있다.In this specification "

" may indicate a part to be connected in a compound.

Hereinafter, a reactive mesogen according to an exemplary embodiment will be described. A reactive mesogen of one embodiment is represented by Formula 1 below.

[Formula 1]

In Formula 1, A ₁ , A ₂ , and A ₃ may each independently be a substituted or unsubstituted divalent hydrocarbon ring group or a substituted or unsubstituted divalent heterocyclic group. a1, b1 and b2 are each independently an integer of 0 or more and 6 or less, and a2 and a3 may each independently be 0 or 1.

Meanwhile, when a1, b1, and b2 are integers greater than or equal to 2, A ₁ -L ₁ , Z ₁ and Z ₂ may be the same or different from each other. For example, when b1 is 2 or more, Z ₁ may be any one of examples of Z ₁ described later repeated, or different exemplary compounds may be connected to each other. In addition, the same can be applied to the case where a2 is greater than (A ₁ -L ₁ ) and the case where b2 is greater than or equal to 2 (Z ₂ ).

A ₁ , A ₂ , and A ₃ are each independently a substituted or unsubstituted aromatic ring group having 6 or more and 30 or less ring carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 2 or more and 30 or less ring carbon atoms, a substituted or It may be an unsubstituted aliphatic ring group having 5 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaliphatic ring group having 2 or more and 30 or less ring carbon atoms. Meanwhile, a hetero atom in a heterocyclic group may be O, N, or S. In addition, A ₁ , A ₂ , and A ₃ may be polycyclic ring groups, and the polycyclic ring group may be adjacent ring groups or condensed ring groups formed by combining adjacent substituents and ring groups.

A ₁ , A ₂ , and A ₃ are divalent ring compounds, for example, a substituted or unsubstituted arylene group having 6 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted hetero group having 2 or more and 30 or less ring carbon atoms. It may be an arylene group. In addition, A ₁ , A ₂ , and A ₃ are divalent substituted or unsubstituted cycloalkanes or cycloalkenes having 5 or more and 30 or less ring carbon atoms, or divalent substituted or unsubstituted ring carbon atoms having 2 or more and 30 or less. It may be a heterocycloalkane or a heterocycloalkene.

Meanwhile, when a1 is an integer greater than or equal to 2, the same A ₁ -L ₁ may be repeated. Also, A ₁ -L ₁ may be different from each other connected to each other.

A ₁ , A ₂ , and A ₃ may each independently be selected from substituted or unsubstituted ring compounds of A-1 to A-22.

A ₁ , A ₂ , and A ₃ are each independently a deuterium atom, a halogen atom, -CN, -NO, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R ⁰ ) ₂ , -C(=O)R ⁰ , a substituted or unsubstituted silyl group, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group, an alkoxycarbonyl group, or an alkylcarbonyloxy group. Here, R ⁰ may be an alkyl group having 1 to 12 carbon atoms. A halogen atom can be F, Cl, Br, or I. Further, in the substituted silyl group, the substituent may be an aryl group, a cycloalkyl group, a straight-chain alkyl group, a branched-chain alkyl group, an alkoxy group, an alkylcarbonyl group, or an alkoxycarbonyl group. In this case, the number of carbon atoms in the alkyl group may be 1 or more and 25 or less.

For example, A ₁ , A ₂ , and A ₃ may each independently be selected from A-22 to A-26.

In Formula 1, B may correspond to an anchoring group. That is, B may be a bonding group that allows the reactive mesogen to be adsorbed to the provided substrate. For example, the anchoring group B may form a hydrogen bond with a transparent electrode formed on a base substrate provided in a liquid crystal display device to be described later.

로 표시되는 3차 아민(tertiary amine)일 수 있다. n1 및 n2는 각각 독립적으로 1 이상 12 이하의 정수이고, T₁ 및 T₂는 각각 독립적으로 -OH, -CH_{3, -}CF₃, -CHF₂, -CH₂F, -CH₂Br, -CHBr₂, -CHCl₂, 또는 -CH₂Cl 일 수 있다. 다만, T₁ 및 T₂ 중 적어도 하나는 -OH이다.In Formula 1, B is an unsubstituted heterocyclic group, a substituted or unsubstituted crown ether group, or

It may be a tertiary amine represented by n1 and n2 are each independently an integer of 1 or more and 12 or less, and T ₁ and T ₂ are each independently -OH, -CH _{3 , -CF 3} , -CHF ₂ , -CH ₂ F, -CH ₂ Br, - CHBr ₂ , -CHCl ₂ , or -CH ₂ Cl. However, at least one of T ₁ and T ₂ is -OH.

또는

일 수 있다. 이때, n1 및 n2는 각각 독립적으로 1 이상 12 이하의 정수일 수 있으며, n1 및 n2는 서로 동일할 수 있다. 또한, n1 및 n2는 서로 상이한 정수일 수 있다. 예를 들어, n1 및 n2는 2 일 수 있다.B is

or

can be In this case, n1 and n2 may each independently be an integer greater than or equal to 1 and less than or equal to 12, and n1 and n2 may be the same as each other. Also, n1 and n2 may be integers different from each other. For example, n1 and n2 may be 2.

The reactive mesogen of one embodiment includes a tertiary amine having at least one OH group as an anchoring group, so that the reactive mesogen can be stably bonded to the base substrate or electrode.

B may be an unsubstituted heterocyclic group. For example, B may be a heteroaromatic ring group having 3 or more and 20 or less ring carbon atoms or a heteroaliphatic ring group having 3 or more and 20 or less ring carbon atoms.

B may be one selected from the following B-1 to B-18.

B may be a substituted or unsubstituted crown ether group. For example, B may be a crown ether group having 4 to 20 ring carbon atoms. In one embodiment, the crown ether group may form a ring with carbon and oxygen atoms. Alternatively, in one embodiment, the crown ether group may include a hetero atom other than carbon and oxygen atoms to form a ring. For example, in one embodiment, the crown ether group may further include a nitrogen atom in addition to carbon and oxygen atoms to form a ring. The crown ether group may include a plurality of nitrogen atoms to form a ring. Specifically, the crown ether group is aza-12-crown-4 (aza-12-crown-4), aza-18-crown-6 (aza-18-crown-6), diaza-18-crown-6 (diaza- 18-crown-6) and the like. However, the embodiment is not limited thereto.

Also, in the substituted crown ether group, the substituent may be bonded to an adjacent group to form a ring. For example, substituents of the crown ether group may condense to form an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. Specifically, the crown ether group may be dicyclohexano-18-crown-6, dibenzo-19-crown-6, or the like. However, the embodiment is not limited thereto.

B may be selected from the following E-1 to E-13.

Pa may be a polymerization group. Pa may be a reactive group for polymerization, for example, Pa may be a reactive group for chain polymerization. Specifically, it may be a reactive group containing a -C=C- double bond or a -C≡C- triple bond.

Pa may be any one of the following P-1 to P-9.

L ₁ and L ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _k1 -, -S(CH ₂ ) _k1 -, -O(CF ₂ ) _k1 -, -S(CF ₂ ) _k1 -, -(CH ₂ ) _k1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _k1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, or -(CH ₂ ) _k1 -COO-(CH ₂ ) _k2 -O-. Here, k1 and k2 may each independently be an integer of 0 or more and 4 or less.

L ₁ and L ₂ may be connectors connecting core groups A ₁ , A ₂ , and A ₃ to each other. Alternatively, L ₁ and L ₂ may be a linking group connecting A ₁ , A ₂ , and A ₃ as core groups to a polymerizer Pa as a terminal reactive group or B as an anchoring group.

On the other hand, L ₁ and L ₂ are not limited to the linking group of the presented example, and the bonding order may be changed. For example, -O(CH ₂ ) _k1 - may include -(CH ₂ ) _k1 O-. This can also be applied to the other connectors presented.

Z ₁ and Z ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _m1 -, -S(CH ₂ ) _m1 -, -O(CF ₂ ) _m1 -, -S(CF ₂ ) _m1 -, -(CH ₂ ) _m1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _m1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, -(CH ₂ ) _m1 -COO-, -(CH ₂ ) _m1 -COO-(CH ₂ ) _m2 -O-, -CH-(S _p -Pa)-, -CH ₂ CH-(S _p -Pa)- or -(CH-(S _p -Pa)-CH-(S _p -Pa))-. In this case, m1 and m2 may each independently be an integer of 0 or more and 4 or less. Also, _Sp may be a single bond or a spacer group, and Pa may be a polymerization group.

The spacer group may connect a core group (eg, A ₁ or A ₃ ) and a polymerization group or a core group and an anchoring group. For example, the spacer group may be an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. However, the embodiment is not limited thereto, and, for example, the spacer group is -(CH ₂ ) _i1 -, -(CH ₂ CH ₂ O) _i1 -CH ₂ CH ₂ -, -CH ₂ CH ₂ -S-CH ₂ CH ₂ -, -CH ₂ CH ₂ -NH-CH ₂ CH ₂ -, or -(SiR ¹ R ² -O) _i1 -. At this time, R ¹ and R ² may each independently be a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. i1 may be an integer greater than or equal to 1 and less than or equal to 12.

부분은 액정 분자들을 소정 방향으로 배향시키기 위한 부분일 수 있다. 예를 들어,

부분은 수직 배향기에 해당하는 부분일 수 있다. 따라서, 화학식 1로 표시되는 일 실시예의 반응성 메소겐을 이용하여 액정 표시 장치의 배향층을 형성하는 경우 제공되는 액정 화합물은 수직 배향될 수 있다.On the other hand, in the reactive mesogen of one embodiment represented by Formula 1, the core part A ₁ , A ₂ , or A ₃ and the linking group L ₁ to L ₂ , and Z ₁ and Z ₂ including

The portion may be a portion for orienting liquid crystal molecules in a predetermined direction. for example,

The portion may be a portion corresponding to the vertical alignment group. Accordingly, when an alignment layer of a liquid crystal display is formed using the reactive mesogen represented by Chemical Formula 1 according to an exemplary embodiment, the provided liquid crystal compound may be vertically aligned.

The reactive mesogen represented by Chemical Formula 1 may be selected from compounds shown in Compound Group 1 below.

[Compound group 1]

The reactive mesogens exemplified in compound group 1 may include a tertiary amine having at least one -OH group as an anchoring group. Compounds 1 to 3 have two -OH groups in their anchoring groups, and compounds 4 to 5 have one -OH group in their anchoring groups. The reactive mesogens represented by Compounds 1 to 5 may have at least one -OH group to increase bonding strength to a substrate to which the reactive mesogens are applied.

In addition, in the case of compounds 4 to 5, one -OH group and one alkyl group are connected to the nitrogen atom of the amine group to increase the binding force of the reactive mesogen to the substrate, and at the same time, the solubility of the reactive mesogen to the liquid crystal compound can be improved

On the other hand, in the case of Compound 3 and Compound 5, the phenylene group, which is a core group, is substituted with F, which is a halogen atom. The reactive mesogen of compound 3 or compound 5 in which the core group is substituted with a halogen atom may have an effect of improving solubility in the liquid crystal compound compared to the unsubstituted compound.

In addition, Compound 1 and Compound 2 contain benzophenone in the core portion, which functions as an initiator to generate radicals, thereby inducing a polymerization reaction of reactive mesogens. Accordingly, the reactive mesogens represented by Compounds 1 and 2 may have an effect of generating free radicals compared to Compounds 3 to 5, thereby increasing the polymerization rate of the reactive mesogens.

The reactive mesogen represented by Chemical Formula 1 may be selected from compounds shown in Compound Group 2 below. In the embodiments disclosed in compound group 2, the reactive mesogen may include an unsubstituted heterocyclic group in an anchoring group.

[Compound group 2]

In addition, the reactive mesogen represented by Chemical Formula 1 may be selected from compounds represented in Compound Group 3 below. In the embodiments disclosed in compound group 3, the reactive mesogen may include a substituted or unsubstituted crown ether group in an anchoring group.

[Compound group 3]

In the case of compounds 12 to 14 of compound group 3, the binding energy of the reactive mesogen of one embodiment to the substrate to be applied may be increased by including a crown ether group at the terminal group.

However, the specific examples disclosed in Compound Group 1, Compound Group 2, and Compound Group 3 are examples of reactive mesogens, and the reactive mesogen represented by Chemical Formula 1 is disclosed in Compound Group 1, Compound Group 2, and Compound Group 3. It is not limited to compounds.

The reactive mesogen of one embodiment may be represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2, the core part X may be a part that functions as an initiator. Also, B is an anchoring group, and Pa may be a polymerizable group. b1 and b2 may each independently be an integer of 0 or more and 6 or less.

In Formula 2, X may be any one of the following X-1 to X-17.

X has a carbonyl group, and thus can act as an initiator that causes a polymerization reaction of reactive mesogens by generating radicals. When the reactive mesogen represented by Chemical Formula 2 is used, the polymerization reaction rate of the reactive mesogen may be increased, and finally, the degree of polymerization of the reactive mesogen may be improved.

Meanwhile, in Formula 2, B, Pa, Z ₁ and Z ₂ are the same as defined in Formula 1 above. In Formula 2, B, Pa, Z ₁ and Z ₂ may be applied in the same manner as described for B, Pa, Z ₁ and Z ₂ described above.

For example, in Chemical Formula 2, B is an anchoring group and may be selected from the following B-1 to B-20 and E-1 to E-13.

In addition, Pa in Formula 2 may be a polymerization group selected from P-1 to P-9.

The reactive mesogen represented by Formula 1 or Formula 2 described above may be used to form an alignment layer in a liquid crystal display device to be described later. For example, the reactive mesogen of one embodiment may be applied to a liquid crystal layer of a liquid crystal display device like a liquid crystal compound to form an alignment layer. Alternatively, the reactive mesogen of one embodiment may be provided together with an alignment agent constituting an alignment layer to form an alignment layer. In this case, the alignment agent may be composed of a polymer monomer, dimer, oligomer, or a mixture thereof such as polyimide, polyamic acid, polyamide, polyamicimide, polyester, polyethylene, polyurethane, or polystyrene. The reactive mesogen of an embodiment may directly form an alignment layer on an electrode on which an alignment layer is not formed.

In this case, the alignment layer formed by the reactive mesogen of an embodiment may be formed on at least one of an upper substrate and a lower substrate of the liquid crystal display.

An embodiment may provide a liquid crystal composition including a liquid crystal compound and a first reactive mesogen represented by Chemical Formula 3 below.

[Formula 3]

In Formula 3, A ₁ , A ₂ , and A ₃ may each independently be a substituted or unsubstituted divalent hydrocarbon ring group or a substituted or unsubstituted divalent heterocyclic group. a1, b1 and b2 are each independently an integer of 0 or more and 6 or less, and a2 and a3 may each independently be 0 or 1.

는 수직 배향기일 수 있다.In Formula 3, B is an anchoring group, Pa is a polymerization group,

may be a vertical aligner.

Meanwhile, in Formula 3, B, Pa, L ₁ to L ₂ , and Z ₁ to Z ₂ are the same as defined in Formula 1 above. In Formula 3, B, Pa, L ₁ to L ₂ , and Z ₁ to Z ₂ are B, Pa, L ₁ to L ₂ , and Z ₁ to Z ₂ in Formula 1 above. can

The first reactive mesogen represented by Chemical Formula 3 may form an alignment layer for aligning liquid crystal molecules, which are liquid crystal compounds, in a vertical direction on the substrate. For example, the alignment layer formed by the first reactive mesogen may be a vertical alignment inducing layer for aligning liquid crystal molecules in a direction perpendicular to the substrate.

The liquid crystal compound may include a nematic liquid crystal compound. The liquid crystal compound may represent one liquid crystal molecule or may include a plurality of different liquid crystal molecules.

For example, the liquid crystal compound may include at least one of the following L-1 to L-10.

In the liquid crystal composition of one embodiment, the first reactive mesogen may be included in an amount of 0.1 parts by weight or more and 2 parts by weight or less based on 100 parts by weight of the liquid crystal compound. When the content of the first reactive mesogen is less than 0.1 part by weight, it may not be easy to form an alignment layer capable of aligning liquid crystal compounds. Also, when the content of the first reactive mesogen exceeds 2 parts by weight, the solubility of the first reactive mesogen in the liquid crystal compound may decrease.

The reactive mesogen of an embodiment may further include a second reactive mesogen represented by the following Chemical Formula 4 in addition to the liquid crystal compound and the first reactive mesogen represented by Chemical Formula 3.

[Formula 4]

In Formula 4, Pa and Pb may be polymerizers. In addition, A ₁ , A ₂ , and A ₃ may each independently be a substituted or unsubstituted divalent hydrocarbon ring group or a substituted or unsubstituted divalent heterocyclic group. a1, b1 and b2 are each independently an integer of 0 or more and 6 or less, and a2 and a3 may each independently be 0 or 1.

는 액정 화합물을 배향시키는 수직 배향기일 수 있다.In Formula 4, L ₁ to L ₂ and Z ₁ to Z ₂ may be a linking group. Also, Z ₁ to Z ₂ may be a spacer group connected to a polymerization group, Pa to Pb. On the other hand, in Formula 4

may be a vertical alignment group that aligns the liquid crystal compound.

In Formula 4, L ₁ to L ₂ and Z ₁ to Z ₂ are the same as defined in Formula 1 above. L ₁ to L ₂ and Z ₁ to Z ₂ in Formula 4 may be applied in the same manner as described for L ₁ to L ₂ and Z ₁ to Z ₂ in Formula 1 above.

In the second reactive mesogen represented by Chemical Formula 4, Pa and Pb may each independently represent any one of the following polymer groups P-1 to P-10. In P-10, p may be an integer from 1 to 20. However, the case where both Pa and Pb are P-10 is excluded. That is, when Pa is P-10, Pb may be any one selected from P-1 to P-9, and when Pb is P-10, Pa may be any one selected from P-1 to P-9. there is.

인 경우는 일측의 말단에만 중합기를 갖는 것일 수 있다.That is, both ends of the second reactive mesogen included in the liquid crystal composition of one embodiment may have polymerizer groups. In addition, any one of Pa to Pb is

In the case of , it may have a polymerization group only at one end.

The liquid crystal composition of one embodiment may further include a third reactive mesogen represented by Chemical Formula 5 below.

[Formula 5]

In Formula 5, X may be any one represented by X-1 to X-17 below.

Meanwhile, in the reactive mesogen represented by Formula 5, Z ₁ , Z ₂ , B, Pa, b1 and b2 are the same as defined in Formula 1 above. Z ₁ to Z ₂ , B, Pa, b1 and b2 in Formula 5 may be applied in the same manner as described for Z ₁ to Z ₂ , B, Pa, b1 and b2 in Formula 1 above.

The liquid crystal composition of one embodiment may further include a third reactive mesogen represented by Chemical Formula 5 to increase the degree of polymerization of the reactive mesogen. In addition, the alignment layer of the liquid crystal display device formed by providing the liquid crystal composition of an embodiment including the third reactive mesogen may tilt the liquid crystal compound provided on the alignment layer at a predetermined angle. That is, the alignment layer formed by providing the liquid crystal composition containing the third reactive mesogen induces the pretilt angle of the liquid crystal compound to increase compared to the alignment layer formed by providing the liquid crystal composition not containing the third reactive mesogen. can

The third reactive mesogen may be included in an amount of 1 part by weight or more and 10 parts by weight or less based on 100 parts by weight of the sum of the first reactive mesogen and the second reactive mesogen included in the liquid crystal composition. When the content of the third reactive mesogen is less than 1 part by weight, the polymerization rate of the reactive mesogen may not be improved because a radical generating portion capable of functioning as an initiator is not sufficient. Also, when the content of the third reactive mesogen exceeds 10 parts by weight, excessive polymerization of the reactive mesogen may occur. Therefore, an alignment layer formed by providing the liquid crystal composition of one embodiment by excessive polymerization may not satisfy physical properties required for aligning the liquid crystal compound. For example, when the liquid crystal composition contains more than 10 parts by weight of the third reactive mesogen, the pretilt angle of the liquid crystal compounds arranged on the formed alignment layer may deviate from the required condition.

Referring to the accompanying drawings, a liquid crystal display device fabricated by providing a reactive mesogen or a liquid crystal composition according to an embodiment will be described.

1 is a diagram schematically illustrating a cross section of a liquid crystal display according to an exemplary embodiment. The liquid crystal display shown in FIG. 1 may include an alignment layer formed of reactive mesogen.

Referring to FIG. 1 , the liquid crystal display device DD has first and second substrates SUB1 and SUB2 facing each other, and a liquid crystal layer provided between the first and second substrates SUB1 and SUB2. (LCL). A first alignment layer ALN1 may be disposed on the first substrate SUB1, and a second alignment layer ALN2 may be disposed on the second substrate SUB2. The second alignment layer ALN2 may be disposed on one surface of the second substrate SUB2 facing the first substrate SUB1. A liquid crystal layer LCL may be disposed between the first alignment layer ALN1 and the second alignment layer ALN2.

The liquid crystal compound LC arranged between the first alignment layer ALN1 and the second alignment layer ALN2 may be vertically aligned with respect to the first and second substrates SUB1 and SUB2. Also, the liquid crystal compound LC may be arranged to be pretilted at a predetermined angle with respect to the first and second substrates SUB1 and SUB2.

At least one of the first alignment layer ALN1 and the second alignment layer ALN2 may be an alignment layer formed using the reactive mesogen of the above-described embodiment. That is, in the liquid crystal display device DD of an exemplary embodiment shown in FIG. 1 , the alignment layers ALN1 and ALN2 may be formed by reactive mesogens of an exemplary embodiment without providing a polyimide alignment layer or the like. For example, one of the first alignment layer ALN1 and the second alignment layer ALN2 may be an alignment layer formed using the reactive mesogen of the above-described embodiment, and the other may be an alignment layer formed of a polyimide alignment layer. there is. Specifically, the first alignment layer ALN1 may be formed of the reactive mesogen of the above-described embodiment, and the second alignment layer ALN2 may be an alignment layer formed of a polyimide alignment layer. Alternatively, the first alignment layer ALN1 may be an alignment layer formed of a polyimide alignment layer, and the second alignment layer ALN2 may be formed of the reactive mesogen of the above-described embodiment. In addition, both the first alignment layer ALN1 and the second alignment layer ALN2 may be formed by the reactive mesogen of one embodiment.

A sealing layer SL may be provided between the first and second substrates SUB1 and SUB2 of the liquid crystal display DD. The sealing layer SL may be disposed on the edges of the first substrate SUB1 and the second substrate SUB2 to protect the liquid crystal layer LCL by bonding the two facing substrates SUB1 and SUB2 to each other.

FIG. 2 is a plan view illustrating a portion of a pixel in the liquid crystal display device, and FIG. 3 may be a cross-sectional view of the liquid crystal display device taken along the line II′ shown in FIG. 2 . 2 and 3 may be exaggerated, enlarged or reduced from the actual picture for convenience of description.

The liquid crystal display of one embodiment shown in FIG. 3 may be a curved liquid crystal display. That is, the liquid crystal display shown in FIG. 3 may be curved with a predetermined curvature. The curved liquid crystal display may be flexible or rigid. The liquid crystal display shown in FIG. 3 may be concavely curved when viewed from the side of the second substrate SUB2, which is an upper substrate. However, the embodiment is not limited thereto, and may be convexly curved when viewed from the side of the second substrate SUB2.

2 and 3 show one pixel PX connected to one of the gate lines GL and one of the data lines DL for convenience of explanation, but the embodiment It is not limiting. For example, one gate line and one data line may be connected to a plurality of pixels, or a plurality of gate lines and a plurality of data lines may be connected to one pixel.

The first substrate SUB1 may include a first base substrate BS1 and a circuit layer formed on the first base substrate BS1. The first base substrate BS1 may be a polymer substrate, a plastic substrate, a glass substrate, or a quartz substrate. The first base substrate BS1 may be a transparent insulating substrate. The first base substrate BS1 may be flexible or rigid.

Referring to FIGS. 2 and 3 , the gate lines GL extend in the first direction D1. The gate lines GL may be formed on the first base substrate BS1. The data lines DL may be provided to extend in the second direction D2 crossing the gate lines GL and the first direction D1.

Each of the pixels PX includes a thin film transistor TFT, a pixel electrode PE connected to the thin film transistor TFT, and a storage electrode part. The thin film transistor TFT includes a gate electrode GE, a gate insulating layer GI, a semiconductor pattern SM, a source electrode SE, and a drain electrode DE. The storage electrode includes a storage line SLn extending in the first direction D1, a first branch electrode LSLn branched from the storage line SLn and extending in a second direction D2, and a second branch electrode RSLn. ) is further included.

The gate electrode GE protrudes from the gate lines GL or is provided on a portion of the gate lines GL. The gate electrode GE may be made of metal. The gate electrode GE may be formed of nickel, chromium, molybdenum, aluminum, titanium, copper, tungsten, or an alloy including these. The gate electrode GE may be formed of a single layer or a multilayer using metal. For example, the gate electrode GE may be a triple layer in which molybdenum, aluminum, and molybdenum are sequentially stacked, or a double layer in which titanium and copper are sequentially stacked. Alternatively, it may be a single film made of an alloy of titanium and copper.

The semiconductor pattern SM is provided on the gate insulating layer GI. The semiconductor pattern SM is provided on the gate electrode GE with the gate insulating layer GI interposed therebetween. A portion of the semiconductor pattern SM overlaps the gate electrode GE. The semiconductor pattern SM includes an active pattern (not shown) provided on the gate insulating layer GI and an ohmic contact layer (not shown) formed on the active pattern. The active pattern may be formed of an amorphous silicon thin film, and the ohmic contact layer may be formed of an n+ amorphous silicon thin film. The ohmic contact layer makes ohmic contact between the active pattern and the source electrode SE and the drain electrode DE, respectively.

The source electrode SE is provided branched from the data lines DL. The source electrode SE is formed on the ohmic contact layer and partially overlaps the gate electrode GE.

The drain electrode DE is spaced apart from the source electrode SE with the semiconductor pattern SM interposed therebetween. The drain electrode DE is formed on the ohmic contact layer and partially overlaps the gate electrode GE.

The source electrode SE and the drain electrode DE may be made of nickel, chromium, molybdenum, aluminum, titanium, copper, tungsten, or an alloy including these. The source electrode SE and the drain electrode DE may be formed of a single layer or a multilayer using metal. For example, the source electrode SE and the drain electrode DE may be a double layer in which titanium and copper are sequentially stacked. Alternatively, it may be a single layer made of an alloy of titanium and copper.

Accordingly, the upper surface of the active pattern between the source electrode SE and the drain electrode DE is exposed, and a conduction channel ( It becomes a channel part constituting a conductive channel. The source electrode SE and the drain electrode DE overlap a portion of the semiconductor pattern SM in an area excluding the channel portion formed to be spaced apart between the source electrode SE and the drain electrode DE.

The pixel electrode PE is connected to the drain electrode DE with the passivation layer PSV interposed therebetween. The pixel electrode PE partially overlaps the storage line SLn, the first branch electrode LSLn, and the second branch electrode RSLn to form a storage capacitor.

The passivation layer PSV covers the source electrode SE, the drain electrode DE, the channel portion, and the gate insulating layer GI, and has a contact hole CH exposing a part of the drain electrode DE. The passivation layer PSV may include, for example, silicon nitride or silicon oxide.

The pixel electrode PE is connected to the drain electrode DE through a contact hole CH formed in the passivation layer PSV. The pixel electrode PE is formed of a transparent conductive material. In particular, the pixel electrode PE is formed of transparent conductive oxide. The transparent conductive oxide may be indium tin oxide (ITO), indium zinc oxide (IZO), indium tin zinc oxide (ITZO), or the like.

Also, the first alignment layer ALN1 may be provided on the pixel electrode PE and the passivation layer PSV.

Meanwhile, in FIG. 3 , the liquid crystal display includes a first substrate SUB1, a second substrate SUB2 facing the first substrate SUB1, and between the first substrate SUB1 and the second substrate SUB2. A liquid crystal layer (LCL) is provided. The gate insulating layer GI is provided on the entire surface of the first base substrate BS1 and covers the gate lines GL. The alignment layers ALN1 and ALN2 may be formed on the first substrate SUB1 and the second substrate SUB2. The alignment layers ALN1 and ALN2 may arrange the liquid crystal compound LC provided between the first substrate SUB1 and the second substrate SUB2 to have a pretilt angle.

The second substrate SUB2 includes a second base substrate BS2, a color filter CF, a black matrix BM, and a common electrode CE. The second base substrate BS2 may be a polymer substrate, a plastic substrate, a glass substrate, or a quartz substrate. The second base substrate BS2 may be a transparent insulating substrate. The second base substrate BS2 may be flexible or rigid.

The color filter CF is provided on the second base substrate BS2 and provides color. In one embodiment of the present invention, it has been disclosed that the color filter CF is included in the second substrate SUB2, but it is not limited thereto, and the color filter CF may be included in the first substrate SUB1.

The black matrix BM is provided to correspond to the light blocking area of the first substrate SUB1. The light-blocking area may be defined as a region in which the data lines DL, the thin film transistor TFT, and the gate lines GL are formed. The black matrix BM is formed in the light blocking area to block light leakage. In one embodiment of the present invention, it has been disclosed that the black matrix BM is included in the second substrate SUB2, but it is not limited thereto, and the black matrix BM may also be included in the first substrate SUB1. Although not shown, an insulating layer (not shown) may be formed on the color filter CF and the black matrix BM.

The common electrode CE is provided on the second base substrate BS2 and forms an electric field together with the pixel electrode PE to drive the liquid crystal layer LCL. In one embodiment of the present invention, it has been disclosed that the common electrode CE is included in the second substrate SUB2, but it is not limited thereto, and the common electrode CE may be included in the first substrate SUB1. The common electrode CE may be formed of a transparent conductive material. The common electrode CE may be formed of, for example, a conductive metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), or indium tin zinc oxide (ITZO). A second alignment layer ALN2 may be disposed on the common electrode CE of the second base substrate BS2.

A liquid crystal layer LCL including a liquid crystal compound LC is provided between the first substrate SUB1 and the second substrate SUB2. The liquid crystal layer LCL may be provided by arranging liquid crystal compounds LC having dielectric anisotropy. The liquid crystal compound (LC) may be used without particular limitation as long as it is a commonly used liquid crystal molecule, and for example, an alkenyl-based liquid crystal compound or an alkoxy-based liquid crystal compound may be used. The liquid crystal compound (LC) used in the examples may have negative dielectric constant anisotropy, but is not limited thereto, and may have positive dielectric constant anisotropy.

The alignment layers ALN1 and ALN2 may be formed of spherical or elliptical particles having random sizes. Spherical or elliptical particles having random sizes may be formed by polymerization of reactive mesogens. For example, the alignment layers ALN1 and ALN2 may be layers formed by stacking random-sized particles formed by reactive mesogens.

4 shows a SEM (Scanning Electron Microscope) image of the surface of the alignment layer (ALN1 or ALN2) formed by the reactive mesogen. The surface images observed in FIG. 4 show an alignment layer formed by including the reactive mesogen of one embodiment and the reactive mesogen represented by Chemical Formula 6 below.

[Formula 6]

Table 1 shows reactive mesogens of an example used for Compound-I, Compound-II, and Compound-III, respectively, in SEM images. Compound-I is an alignment layer formed by including Compound 1 disclosed in Compound Group 1, Compound-II is an alignment layer formed by including Compound 4 disclosed in Compound Group 1, and Compound-III is an alignment layer formed by including Compound 6 disclosed in Compound Group 2. Corresponds to the alignment layer formed including.

Compound-I compound 1

Compound-II compound 4

Compound III compound 6

As shown schematically in FIG. 3, since the alignment layer formed by the reactive mesogen is formed by stacking random particles, as shown in the SEM image shown in FIG. 4, it can be observed that random protrusions are formed on the surface of the alignment layer. .

An average particle diameter of random particles formed by the reactive mesogen of one embodiment may be greater than or equal to 1 nm and less than 30 nm. In this case, the thickness of the alignment layers ALN1 and ALN2 may be greater than or equal to 30 nm and less than or equal to 40 nm, but the embodiment is not limited thereto.

In addition, in the example of the liquid crystal display shown in FIG. 3 , the pretilt angle of the liquid crystal compound LC disposed on the first alignment layer ALN1 and the liquid crystal compound LC disposed on the second alignment layer ALN2 The pretilt angles of may be different from each other. For example, the liquid crystal compound LC disposed adjacent to the second alignment layer ALN2 may be vertically aligned with the second substrate SUB2. In comparison, the liquid crystal compound LC disposed adjacent to the first alignment layer ALN1 may be tilted at a predetermined angle with respect to the first substrate SUB1.

That is, in the case of the curved liquid crystal display shown in FIG. 3 , the pretilt angle of the liquid crystal compound LC disposed on the first alignment layer ALN1 and the liquid crystal compound LC disposed on the second alignment layer ALN2 By differently adjusting the pretilt angles of , it is possible to improve alignment stability of the liquid crystal compound LC in the liquid crystal layer LCL, thereby improving texture defects of the liquid crystal display device. That is, the display quality of the liquid crystal display device may be improved by providing the liquid crystal composition including the reactive mesogen according to an embodiment to form an alignment layer.

Meanwhile, the liquid crystal display shown in FIGS. 1 to 3 may be a super vertical alignment (SVA) mode liquid crystal display. However, the embodiment is not limited thereto, and may be a liquid crystal display of another type of vertical alignment mode or horizontal alignment mode.

The reactive mesogen of one embodiment may be used in various types of liquid crystal display devices requiring a liquid crystal alignment layer in addition to being used in the liquid crystal display devices of FIGS. 1 to 3 described above. For example, the reactive mesogen and the liquid crystal composition including the reactive mesogen of one embodiment may be used in a photoluminescent liquid crystal display (PL-LCD). The photoluminescent liquid crystal display may include a color conversion member formed of phosphors or quantum dots.

5 is a cross-sectional view showing an embodiment of a photoluminescent liquid crystal display. The photoluminescent liquid crystal display includes a first substrate SUB1 and a second substrate SUB2 facing the first substrate SUB1, and the liquid crystal is interposed between the first substrate SUB1 and the second substrate SUB2. A layer LCL and a color conversion member CCL may be included.

The liquid crystal layer LCL may include the alignment layers ALN1 and ALN2 formed by the reactive mesogen of the above-described embodiment and the liquid crystal compound LC arranged between the alignment layers ALN1 and ALN2. The liquid crystal compound LC between the alignment layers ALN1 and ANL2 may be aligned perpendicularly to the substrates SUB1 and SUB2 or may be aligned by being pre-tilted to have a predetermined angle.

Meanwhile, with respect to the alignment layers ALN1 and ALN2 and the liquid crystal compound LC shown in FIG. 5 , the first alignment layer ALN1 and the second alignment layer ALN2 and the liquid crystal compound of FIGS. 1 to 3 are described above. The same content as the description for (LC) can be applied. For example, in one embodiment shown in FIG. 5 , at least one of the alignment layers ALN1 and ALN2 may be an alignment layer formed by the above-described reactive mesogen. Both the first alignment layer ALN1 and the second alignment layer ALN2 may be alignment layers formed by the above-described reactive mesogen. Alternatively, at least one of the first alignment layer ALN1 and the second alignment layer ALN2 may be an alignment layer formed by the aforementioned reactive mesogen, and the other may be an alignment layer including a polyimide alignment layer.

Although not shown in FIG. 5 , the first substrate SUB1 may include a base substrate and a first electrode layer formed on the base substrate. For example, the first electrode layer formed on the base substrate may be a pixel electrode layer. The second substrate SUB2 may include a base substrate and a second electrode layer formed on the base substrate. For example, the second electrode layer formed on the base substrate of the second substrate SUB2 may be a common electrode layer.

The base substrate may be a polymer substrate, a plastic substrate, a glass substrate, or a quartz substrate. Base substrates of the first and second substrates SUB1 and SUB2 may be transparent insulating substrates. The base substrate may be flexible or rigid.

A first polarizing member PO- 1 may be disposed on a lower surface of the first substrate SUB1. The first polarizing member PO-1 may have various embodiments. For example, the first polarizing member PO-1 may be provided in the form of a film and disposed on the rear surface of the first substrate SUB1, or may be attached by a separately provided adhesive member. Alternatively, the first polarizing member PO-1 may be provided in a liquid form and directly coated or deposited on the first substrate SUB1. Also, unlike what is shown in the figure, the first polarizing member PO- 1 may be disposed between the first substrate SUB1 and the first alignment layer ALN1.

The second polarizing member PO- 2 may be disposed between the liquid crystal layer LCL and the color conversion member CCL. The second polarizing member PO-2 may be made of a material having light transmittance. Accordingly, light transmitted through the liquid crystal layer LCL and provided may be provided to the color conversion member CCL through the second polarizing member PO- 2 .

The second polarizing member PO- 2 polarizes incident light and selectively reflects or transmits it. For example, the second polarization member PO-2 may be a polarization layer formed adjacent to the liquid crystal layer LCL, and may function as a polarization layer opposite to the first polarization member PO-1. Accordingly, the second polarizing member PO-2 may polarize the light incident on the second polarizing member PO-2 in a direction orthogonal to the polarizing direction of the first polarizing member PO-1.

The second polarization member PO-2 may be a coated polarization layer or a polarization layer formed by deposition. For example, the second polarizer PO- 2 may be an in-cell polarizer, and in an embodiment, the second polarizer PO- 2 may be a wire grid polarizer. . However, the embodiment is not limited thereto. Meanwhile, the arrangement of the second polarizing member PO- 2 is not limited to that shown in FIG. 5 and may be disposed on the second substrate SUB.

Light transmitted through the second polarization member PO- 2 may be provided to the color conversion member CCL. The color conversion member CCL may include a color conversion unit CCF and a black matrix BM. The color conversion unit CCF may convert color according to the energy of light incident through the second polarization member PO- 2 or may transmit the color as it is. Each of the filters CF1 , CF2 , and CF3 of the color conversion unit CCF may include at least one light conversion particle.

The light conversion particles absorb at least a portion of the incident light and emit light having a specific color or transmit it as it is. For example, the light conversion particles may be quantum dots (QDs).

Specifically, in the embodiment shown in FIG. 5 , the first filter CF1 , the second filter CF2 , and CF3 may generate red, green, and blue light, respectively. However, the embodiment is not limited thereto. For example, when a backlight unit (not shown) disposed under the first polarizing member PO- 1 and providing light to the liquid crystal layer LCL provides blue light. The first filter CF1 and the second filter CF2 may generate red light and green light, respectively, and the third filter CF3 may transmit and emit blue light provided from the backlight unit without including light conversion particles. there is.

Also, unlike the exemplary embodiment shown in the drawings, the color change member CCL may be disposed on the second substrate SUB2.

Hereinafter, with reference to Examples and Comparative Examples, a reactive mesogen according to an embodiment of the present invention and a liquid crystal composition of an embodiment including the reactive mesogen will be described in detail. In addition, the examples shown below are examples for helping understanding of the present invention, and the scope of the present invention is not limited thereto.

[Example]

1. Synthesis of reactive mesogens

Regarding the method for synthesizing a reactive mesogen according to an embodiment of the present invention, a method for synthesizing compounds 1 and 4 of compound group 1, compounds 6 to 9 of compound group 2, and compounds 12 to 14 of compound group 3 It is explained in detail by exemplifying. In addition, the method for synthesizing a reactive mesogen described below is only an example, and the method for synthesizing a reactive mesogen according to an embodiment of the present invention is not limited to the following example. For example, the synthesis process of a reactive mesogen according to an embodiment is not limited to the reaction conditions presented below, and any reaction conditions known in the art may be applied.

[Synthesis of Compound 1]

(Scheme 1)

Compound 1 (Compound 1) of compound group 1 can be prepared based on the preparation example of the reaction process of Scheme 1.

The synthesized compound 1 was confirmed using a ¹ H NMR (CDCl 3 , δ in ppm, 300 MHz) spectrum. The NMR spectrum and chemical shift values of Compound 1 synthesized according to Scheme 1 are shown in FIG. 6 . Referring to FIG. 6 , it can be confirmed from the measured NMR spectrum that Compound 1 was synthesized.

[Synthesis of Compound 4]

(Scheme 2)

Compound 4 of compound group 1 can be prepared based on the preparation example of the reaction process of Reaction Scheme 2.

The synthesized compound 4 was confirmed using a ¹ H NMR (CDCl 3 , δ in ppm, 300 MHz) spectrum. The NMR spectrum and chemical shift values of Compound 4 synthesized according to Scheme 2 are shown in FIG. 7 . Referring to FIG. 7 , it can be confirmed from the measured NMR spectrum that compound 4 was synthesized.

[Synthesis of Compound 6]

(Scheme 3)

화합물군 2의 화합물 6(Compound 6)은 반응식 3의 반응 과정의 제조예를 기초로 제조될 수 있다.

Compound 6 (Compound 6) of compound group 2 can be prepared based on the preparation example of the reaction process of Reaction Scheme 3.

The synthesized compound 6 was confirmed using a ¹ H NMR (CDCl 3 , δ in ppm, 300 MHz) spectrum. The NMR spectrum and chemical shift values of Compound 6 synthesized according to Reaction Scheme 3 are shown in FIG. 8 . Referring to FIG. 8 , it can be confirmed from the measured NMR spectrum that compound 6 was synthesized.

[Synthesis of Compound 7]

(Scheme 4)

화합물군 2의 화합물 7(Compound 7)은 반응식 4의 반응 과정의 제조예를 기초로 제조될 수 있다.

Compound 7 (Compound 7) of compound group 2 can be prepared based on the preparation example of the reaction process of Scheme 4.

The synthesized compound 7 was confirmed using a ¹ H NMR (CDCl 3 , δ in ppm, 300 MHz) spectrum. The NMR spectrum and chemical shift values of Compound 7 synthesized according to Reaction Scheme 4 are shown in FIG. 9 . Referring to FIG. 9 , it can be confirmed from the measured NMR spectrum that compound 7 was synthesized.

[Synthesis of Compound 8]

(Scheme 5)

Compound 8 (Compound 8) of compound group 2 can be prepared based on the preparation example of the reaction process of Reaction Scheme 5.

The synthesized compound 8 was confirmed using a ¹ H NMR (CDCl 3 , δ in ppm, 300 MHz) spectrum. The NMR spectrum and chemical shift values of Compound 8 synthesized according to Scheme 5 are shown in FIG. 10 . Referring to FIG. 10 , it can be confirmed from the measured NMR spectrum that compound 8 was synthesized.

[Synthesis of Compound 9]

(Scheme 6)

화합물군 2의 화합물 9(Compound 9)는 반응식 6의 반응 과정의 제조예를 기초로 제조될 수 있다.

Compound 9 (Compound 9) of compound group 2 can be prepared based on the preparation example of the reaction process of Scheme 6.

The synthesized compound 9 was confirmed using a ¹ H NMR (CDCl 3 , δ in ppm, 300 MHz) spectrum. The NMR spectrum and chemical shift values of Compound 9 synthesized according to Scheme 6 are shown in FIG. 11 . Referring to FIG. 11 , it can be confirmed from the measured NMR spectrum that compound 9 was synthesized.

[Synthesis of Compound 12]

(Scheme 7)

Compound 12 (Compound 12) of compound group 3 can be prepared based on the preparation example of the reaction process of Scheme 7.

The synthesized compound 12 was confirmed using a ¹ H NMR (CDCl 3 , δ in ppm, 300 MHz) spectrum. The NMR spectrum and chemical shift values of Compound 12 synthesized according to Scheme 7 are shown in FIG. 12 . Referring to FIG. 12, it can be confirmed from the measured NMR spectrum that compound 12 was synthesized.

[Synthesis of Compound 13]

(Scheme 8)

Compound 13 (Compound 13) of compound group 3 can be prepared based on the preparation example of the reaction process of Scheme 8.

The synthesized compound 13 was confirmed using a ¹ H NMR (CDCl 3 , δ in ppm, 300 MHz) spectrum. The NMR spectrum and chemical shift values of Compound 13 synthesized according to Scheme 8 are shown in FIG. 13 . Referring to FIG. 13, it can be confirmed from the measured NMR spectrum that compound 13 was synthesized.

[Synthesis of Compound 14]

(Scheme 9)

Compound 14 of compound group 3 (Compound 14) can be prepared based on the preparation example of the reaction process of Scheme 9.

The synthesized compound 14 was confirmed using a ¹ H NMR (CDCl 3 , δ in ppm, 300 MHz) spectrum. The NMR spectrum and chemical shift values of Compound 14 synthesized according to Scheme 9 are shown in FIG. 14 . Referring to FIG. 14, it can be confirmed from the measured NMR spectrum that compound 14 was synthesized.

2. Evaluation of physical properties of reactive mesogens

The solubility of the reactive mesogen with the liquid crystal compound and adsorption energy with the electrode were evaluated. Evaluation of solubility and adsorption energy was performed using a simulation program (Materials Studio), and the comparative and example compounds used are shown in Table 2. The simulation result value is a value derived using quantum calculation and molecular dynamics method.

division reactive mesogens chemical formula comparative example comparison compound

Example 1 compound 1

Example 2 compound 2

Example 3 compound 4

Example 4 compound 6

Example 5 compound 7

Example 6 compound 8

Example 7 compound 9

Example 8 compound 12

Example 9 compound 13

Example 10 compound 14

Simulation results for the comparative compounds disclosed in Table 2 and Compounds 1, 2, 4, Compounds 6 to 9, and Compounds 12 to 14 are shown in Table 3. In Table 3, the solubility ( Δδ ) shows the solubility of the liquid crystal compound in the case of mixing the comparative compound, which is a reactive mesogen, or the example compounds shown in Table 2. It can be seen that the smaller the "solubility ( Δδ )" value, the greater the solubility of the reactive mesogen in the liquid crystal compound. The liquid crystal compound used in the simulation corresponds to a nematic liquid crystal mixture. The adsorption energy represents the adsorption energy of the compounds of Comparative Examples to Examples with respect to an indium tin oxide (ITO) electrode. It can be seen that as the absolute value of the adsorption energy value increases, the adsorption energy of the reactive mesogen to the ITO electrode increases. Also, “self initiation efficiency” may be a value representing a rate at which free radicals are generated. As the value of "Self initiation efficiency" increases, free radicals are generated faster, so that the polymerization rate of reactive mesogens may increase.

division reactive mesogens Solubility ( Δδ) Adsorption energy (eV) Self initiation efficiency comparative example comparison compound 1.5 -0.49 0.167 Example 1 compound 1 5.1 -1.27 0.764 Example 2 compound 2 3.1 -1.34 0.247 Example 3 compound 4 1.3 -0.99 0.127 Example 4 compound 6 1.8 -0.40 0.138 Example 5 compound 7 1.6 -0.45 0.179 Example 6 compound 8 1.5 -0.51 0.236 Example 7 compound 9 1.5 -0.53 0.128 Example 8 compound 12 1.2 -0.73 0.235 Example 9 compound 13 1.1 -0.82 0.235 Example 10 compound 14 1.2 -0.97 0.367

Referring to the results of Table 3, in the case of Example 1, Example 2 and Example 3 using Compound 1, Compound 2 and Compound 4 of Compound Group 1, which are reactive mesogens of an example, the absolute value of adsorption energy is the comparative compound. It can be seen that it appears larger than the comparative example using. That is, it can be seen that the adsorption energy of the reactive mesogen of Example 1 to the ITO electrode is greater than that of the reactive mesogen of the Comparative Example compound. In particular, in the case of Examples 1 and 2 including the reactive mesogen having two -OH groups at the ends of the reactive mesogen, it can be seen that the adsorption energy is higher than that of Example 3. Accordingly, the reactive mesogens of Example represented by Compound 1, Compound 2, and Compound 4 have higher adsorption energy to the electrode than the reactive mesogens of Comparative Example, so that a stable alignment layer can be formed.

In addition, Example 3 has a smaller Δδ value representing the solubility of the reactive mesogen in the liquid crystal compound compared to Examples 1 to 2, so Example 3 is a liquid crystal compound compared to Examples 1 to 2. It can be seen that the solubility of That is, by introducing an alkyl group by replacing the -OH group in the terminal group corresponding to the anchoring group of the reactive mesogen, the effect of improving the solubility of the liquid crystal compound compared to Examples 1 and 2 can be exhibited.

Examples 4 to 7 corresponding to the novel reactive mesogens of one embodiment represented by Compounds 6 to 9 having an unsubstituted heterocyclic group at the terminal group have solubility and adsorption energy properties equivalent to those of the reactive mesogens of Comparative Examples showed

를 코어 부분에 포함하여 중합도가 높아질 수 있으며, 이에 따라 "Self initiation 효율" 이 크게 나타났다.The value of "Self initiation efficiency" was high in Example 1 and Example 2. The reactive mesogens of compound 1 and compound 2 can generate free radicals.

The degree of polymerization can be increased by including in the core part, and thus the "Self initiation efficiency" was greatly shown.

In Example 8, Example 9, and Example 10 using Compound 12, Compound 13, and Compound 14 of Compound Group 3, the absolute value of adsorption energy was higher than that of Comparative Example. That is, it can be seen that the reactive mesogen of Example having a crown ether group at the terminal group has higher adsorption energy to the ITO electrode than the reactive mesogen of the Comparative Example compound. Therefore, the reactive mesogens of Examples 8 to 10 having a crown ether group at the terminal group, which is an anchoring group, have high adsorption energy to the electrode, and thus can form a stable alignment layer.

In addition, since the Δδ value of the reactive mesogens of Examples 8 to 10 is smaller than that of Comparative Examples, Examples 8 to 10 have higher solubility in the liquid crystal compound than the reactive mesogens of Comparative Examples. can confirm that It can be seen that the "Self initiation" efficiency value also appears larger than that of the comparative example.

15A to 15C are diagrams schematically illustrating a bonding relationship between a reactive mesogen and an electrode layer provided with the reactive mesogen according to an exemplary embodiment. 15A to 15C may show a bonding relationship between the reactive mesogens of Compound 1, Compound 2, and Compound 4 disclosed in Table 2 and the electrode layer, respectively.

Referring to FIGS. 15A to 15C , an alignment layer ALN may be formed on the electrode layer EL. 15A to 15C , the electrode layer EL may be an ITO electrode. In FIGS. 15A to 15C , the alignment layer ALN may schematically represent a part of a stereochemical structure of a reactive mesogen compound. Particularly, the “BA” portion may be a portion corresponding to an anchoring group in a reactive mesogen according to an embodiment.

In the case of FIGS. 15A and 15B , since Compound 1 and Compound 2 have two -OH groups in their anchoring groups, it can be seen that the two -OH groups bond with the electrode layer EL, respectively. In comparison, in the case of FIG. 15C , it can be seen that only one -OH in the anchoring group of Compound 4 binds to the electrode layer EL, as for the reactive mesogen of Compound 4.

3. Manufacture of liquid crystal display and evaluation of display quality of liquid crystal display

(1) Manufacture of liquid crystal display devices

A first substrate on which pixel electrodes and the like are formed and a second substrate on which a common electrode and the like are formed are prepared. A liquid crystal composition is provided on a first substrate by a liquid crystal dropping method. The liquid crystal composition provided at this time includes a liquid crystal compound and Compound 2 of Compound Group 1. Compound 2 was provided in an adjusted amount of 0.1 part by weight, 0.15 part by weight, 0.25 part by weight, and 0.3 part by weight, respectively, based on 100 parts by weight of the liquid crystal compound.

Next, the first substrate and the second substrate on which the liquid crystal composition is dropped are bonded together. At this time, a sealing layer may be provided at an edge between the first substrate and the second substrate to couple the first substrate and the second substrate. After bonding the first substrate and the second substrate, UV light is irradiated to cure the sealing layer. At this time, a shadow mask is used to harden the sealing layer. Next, an electric field is applied between the first substrate and the second substrate to polymerize reactive mesogens in the liquid crystal composition, and thereby align the liquid crystal compound to be pretilted. Next, the electric field between the first substrate and the second substrate is removed, and UV light is additionally applied to the liquid crystal layer to polymerize unreacted reactive mesogens.

(2) Evaluation of display quality of liquid crystal display devices

16 shows a comparison of display quality according to a content of a reactive mesogen in a liquid crystal composition provided to a liquid crystal display device according to an embodiment.

Referring to FIG. 16 , it can be seen that as the content of compound 2, which is a reactive mesogen, increases, alignment of the liquid crystal compound in the outer region of the display device is improved, and thus display quality of the liquid crystal display device is improved.

4. Manufacturing of liquid crystal display and evaluation of electrical characteristics of liquid crystal display

(1) Manufacture of liquid crystal display devices

A first substrate on which pixel electrodes and the like are formed and a second substrate on which a common electrode and the like are formed are prepared. A liquid crystal composition is provided on a first substrate by a liquid crystal dropping method. The liquid crystal composition provided at this time includes a liquid crystal compound and compound 12 of compound group 3.

Next, the first substrate and the second substrate on which the liquid crystal composition is dropped are bonded together. At this time, a sealing layer may be provided at an edge between the first substrate and the second substrate to couple the first substrate and the second substrate. After bonding the first substrate and the second substrate, UV light is irradiated to cure the sealing layer. At this time, a shadow mask is used to harden the sealing layer. Next, an electric field is applied between the first substrate and the second substrate to polymerize reactive mesogens in the liquid crystal composition, and thereby align the liquid crystal compound to be pretilted. Next, the electric field between the first substrate and the second substrate is removed, and UV light is additionally applied to the liquid crystal layer to polymerize unreacted reactive mesogens.

(2) Evaluation of electrical characteristics of liquid crystal display devices

17A and 17B are graphs showing changes in a voltage holding ratio (VHR) in a liquid crystal display including reactive mesogens. 17A and 17B show changes in voltage retention over time at room temperature.

Figure 17a shows the change in voltage retention over time in the liquid crystal display including the comparative compounds of Table 2, and Figure 17b shows the change in voltage retention over time in the liquid crystal display including compound 12 of compound group 3. it is shown

Referring to the graph of FIG. 17A , in the case of the liquid crystal display using the comparative compound as the reactive mesogen, it can be seen that the voltage retention decreases over time. In comparison, referring to the graph of FIG. 17B , it can be seen that the voltage retention rate of the liquid crystal display including Compound 12, which is a reactive mesogen of one embodiment, is maintained at 99% or more even over time. On the other hand, in FIG. 17B, "non-exposure" is indicated in the X-axis column before polymerization of the reactive mesogen provided with the liquid crystal compound.

Referring to the results of FIGS. 17A and 17B, the reactive mesogen of one embodiment includes a crown ether group at the end group, thereby forming an alignment layer having a high binding energy to the electrode, and thus the alignment layer forms a liquid crystal compound. It turns out that it can orientate stably. In addition, from the fact that the voltage retention is maintained high, it can be seen that the alignment layer formed by the reactive mesogen stably aligns the liquid crystal compound, and thus the electrical characteristics of the liquid crystal display device are improved.

In one embodiment, the reactive mesogen includes at least one -OH group in an anchoring group, includes an unsubstituted heterocyclic group, or includes a substituted or unsubstituted crown ether group, so that the substrate of a liquid crystal display device provided with the reactive mesogen, or The bonding energy with the electrode layer can be increased. Accordingly, a liquid crystal display manufactured by providing the reactive mesogen of an embodiment or the liquid crystal composition including the reactive mesogen of an embodiment may have improved display quality. That is, due to the high binding energy of the reactive mesogen to the substrate, the alignment layer of the liquid crystal display can be stably formed, and thus the alignment properties of the liquid crystal compounds in the liquid crystal display can be improved. In addition, the reactive mesogen of an embodiment can improve the electrical characteristics of the liquid crystal display by increasing the bonding energy with the substrate or electrode layer of the liquid crystal display and stably orienting the liquid crystal compound to increase the voltage retention during driving the liquid crystal display. .

The reactive mesogen of an embodiment may improve the degree of polymerization of the reactive mesogen by introducing a core portion functioning as an initiator to induce a spontaneous polymerization reaction. In addition, an alignment layer capable of tilting the liquid crystal compound in a predetermined direction can be stably provided.

Although the above has been described with reference to preferred embodiments of the present invention, those skilled in the art or those having ordinary knowledge in the art do not deviate from the spirit and technical scope of the present invention described in the claims to be described later. It will be understood that the present invention can be variously modified and changed within the scope not specified.

Therefore, the technical scope of the present invention is not limited to the contents described in the detailed description of the specification, but should be defined by the claims.

SUB1: 1st board SUB2: 2nd board
ALN1: first alignment layer ALN2: second alignment layer
LC: liquid crystal compound

Claims (23)

A reactive mesogen represented by Formula 1 below:
[Formula 1]

In Formula 1,
A ₁ , A ₂ , and A ₃ are each independently a substituted or unsubstituted divalent hydrocarbon ring group or a substituted or unsubstituted divalent heterocyclic group;
a1, b1 and b2 are each independently an integer of 0 or more and 6 or less,
a2 and a3 are each independently 0 or 1;
L ₁ and L ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _k1 -, -S(CH ₂ ) _k1 -, -O(CF ₂ ) _k1 -, -S(CF ₂ ) _k1 -, -(CH ₂ ) _k1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _k1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, or -(CH ₂ ) _k1 -COO-(CH ₂ ) _k2 -O-;
k1 and k2 are each independently an integer of 1 or more and 4 or less,
Z ₁ and Z ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _m1 -, -S(CH ₂ ) _m1 -, -O(CF ₂ ) _m1 -, -S(CF ₂ ) _m1 -, -(CH ₂ ) _m1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _m1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, -(CH ₂ ) _m1 -COO-, -(CH ₂ ) _m1 -COO-(CH ₂ ) _m2 -O-, -CH-(S _p -Pa)-, -CH ₂ CH-(S _p -Pa)-, or -(CH-(S _p -Pa)-CH-(S _p -Pa))-;
m1 and m2 are each independently an integer of 1 or more and 4 or less,
_Sp is a single bond or a spacer group;
Pa is a polymerization group;
B is an unsubstituted heterocyclic group, a substituted or unsubstituted crown ether group, or

ego,
n1 and n2 are each independently an integer of 1 to 12 or less, and T ₁ and T ₂ are each independently -OH, -CH _{3 , -CF 3} , -CHF ₂ , -CH ₂ F, -CH ₂ Br, - CHBr ₂ , -CHCl ₂ , or -CH ₂ Cl;
At least one of T ₁ and T ₂ is -OH,
When B is an unsubstituted heterocyclic group, the B is represented by any of the following B-1 and B-3 to B-18:

. According to claim 1,
Wherein A ₁ , A ₂ , and A ₃ are each independently a substituted or unsubstituted aromatic ring group having 6 or more and 30 or less ring carbon atoms, a substituted or unsubstituted heteroaromatic ring group having 2 or more and 30 or less ring carbon atoms, and a substituted or a reactive mesogen which is an unsubstituted aliphatic ring group having 5 or more and 30 or less ring carbon atoms, or a substituted or unsubstituted heteroaliphatic ring group having 2 or more and 30 or less ring carbon atoms. According to claim 1,
Wherein A ₁ , A ₂ , and A ₃ are each independently selected from the following substituted or unsubstituted ring compounds of A-1 to A-22, the reactive mesogen.

According to claim 1,
A ₁ , A ₂ , and A ₃ are each independently a deuterium atom, a halogen atom, -CN, -NO, -NCO, -NCS, -OCN, -SCN, -C(=O)N(R ⁰ ) ₂ , -C(=O)R ⁰ , a substituted or unsubstituted silyl group, a cycloalkyl group having 3 to 20 ring carbon atoms, an alkoxy group, an alkoxycarbonyl group, or a reactive mesogen substituted with an alkylcarbonyloxy group:
Here, R ⁰ is an alkyl group having 1 or more and 12 or less carbon atoms. The reactive mesogen according to claim 1, wherein A ₁ , A ₂ , and A ₃ are each independently selected from the following A-22 to A-26.

According to claim 1,
The B is

or

phosphorus reactive mesogens. delete According to claim 1,
B is any one of the following E-1 to E-13 reactive mesogen.

According to claim 1,
Pa is any one of the following P-1 to P-9 reactive mesogen.

According to claim 1,
Chemical Formula 1 is a reactive mesogen selected from compounds shown in Compound Group 1 below.
[Compound group 1]

According to claim 1,
Chemical Formula 1 is a reactive mesogen selected from compounds shown in Compound Group 2 below.
[Compound group 2]

According to claim 1,
Chemical Formula 1 is a reactive mesogen selected from compounds shown in Compound Group 3 below.
[Compound group 3]

A reactive mesogen represented by Formula 2 below:
[Formula 2]

In Formula 2,
X is any one of the following X-1 to X-17,

Z ₁ and Z ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _m1 -, -S(CH ₂ ) _m1 -, -O(CF ₂ ) _m1 -, -S(CF ₂ ) _m1 -, -(CH ₂ ) _m1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _m1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, -(CH ₂ ) _m1 -COO-, -(CH ₂ ) _m1 -COO-(CH ₂ ) _m2 -O-, -CH-(S _p -Pa)-, -CH ₂ CH-(S _p -Pa)-, or -(CH-(S _p -Pa)-CH-(S _p -Pa))-;
m1 and m2 are each independently an integer of 1 or more and 4 or less,
_Sp is a single bond or a spacer group;
b1 and b2 are each independently an integer of 0 or more and 6 or less,
Pa is a polymerization group;
B is an unsubstituted heterocyclic group, a substituted or unsubstituted crown ether group, or

ego,
n1 and n2 are each independently an integer of 1 or more and 12 or less, and T ₁ and T ₂ are each independently -OH, -CH _{3, -CF 3} , -CHF ₂ , -CH ₂ F, -CH ₂ Br, - CHBr ₂ , -CHCl ₂ , or -CH ₂ Cl;
At least one of T ₁ and T ₂ is -OH. The reactive mesogen according to claim 13, wherein B is any one of the following B-1 to B-20 and the following E-1 to E-13.

The reactive mesogen according to claim 13, wherein Pa is any one of the following P-1 to P-9.

liquid crystal compounds; and
a first reactive mesogen represented by Chemical Formula 3; A liquid crystal composition comprising:
[Formula 3]

In Formula 3,
A ₁ , A ₂ , and A ₃ are each independently a substituted or unsubstituted divalent hydrocarbon ring group or a substituted or unsubstituted divalent heterocyclic group;
a1, b1 and b2 are each independently an integer of 0 or more and 6 or less,
a2 and a3 are each independently 0 or 1;
L ₁ and L ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _k1 -, -S(CH ₂ ) _k1 -, -O(CF ₂ ) _k1 -, -S(CF ₂ ) _k1 -, -(CH ₂ ) _k1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _k1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, or -(CH ₂ ) _k1 -COO-(CH ₂ ) _k2 -O-;
k1 and k2 are each independently an integer of 1 or more and 4 or less,
Z ₁ and Z ₂ are each independently a single bond, -O-, -S-, -CO-, -COO-, -OCOO-, -O(CH ₂ ) _m1 -, -S(CH ₂ ) _m1 -, -O(CF ₂ ) _m1 -, -S(CF ₂ ) _m1 -, -(CH ₂ ) _m1 -, -CF ₂ CH ₂ -, -(CF ₂ ) _m1 -, -CH=CH-, -CF= CF-, -C≡C-, -CH=CH-COO-, -(CH ₂ ) _m1 -COO-, -(CH ₂ ) _m1 -COO-(CH ₂ ) _m2 -O-, -CH-(S _p -Pa)-, -CH ₂ CH-(S _p -Pa)-, or -(CH-(S _p -Pa)-CH-(S _p -Pa))-;
m1 and m2 are each independently an integer of 1 or more and 4 or less,
_Sp is a single bond or a spacer group;
Pa is a polymerization group;
B is an unsubstituted heterocyclic group, a substituted or unsubstituted crown ether group, or

ego,
n1 and n2 are each independently an integer of 1 or more and 12 or less, and T ₁ and T ₂ are each independently -OH, -CH _{3, -CF 3} , -CHF ₂ , -CH ₂ F, -CH ₂ Br, - CHBr ₂ , -CHCl ₂ , or -CH ₂ Cl;
At least one of T ₁ and T ₂ is -OH,
When B is an unsubstituted heterocyclic group, the B is represented by any of the following B-1 and B-3 to B-18:

.
17. The liquid crystal composition of claim 16, wherein B is any one of B-19, B-20, and E-1 to E-13:

According to claim 16,
a second reactive mesogen represented by Chemical Formula 4; A liquid crystal composition further comprising:
[Formula 4]

In Formula 4,
Pa and Pb each independently represent any one of the following P-1 to P-10 polymerizers, except when Pa and Pb are P-10 at the same time, p is an integer of 1 or more and 20 or less;
A ₁ , A ₂ , A ₃ , L ₁ , L ₂ , Z ₁ , Z ₂ , a1, a2, a3, b1 and b2 are each the same as defined in claim 16 above.

According to claim 18,
A liquid crystal composition further comprising a third reactive mesogen represented by Chemical Formula 5:
[Formula 5]

In Formula 5,
X is any one of the following X-1 to X-17,

Z ₁ , Z ₂ , B and Pa are the same as defined in claim 16 above. The liquid crystal composition of claim 16, wherein the first reactive mesogen is included in an amount of 0.1 parts by weight or more and 2 parts by weight or less based on 100 parts by weight of the liquid crystal compound. According to claim 19,
The third reactive mesogen is
A liquid crystal composition comprising 1 part by weight or more and 10 parts by weight or less based on 100 parts by weight of the sum of the first reactive mesogen and the second reactive mesogen. 17. The liquid crystal composition of claim 16, wherein the liquid crystal compound includes a nematic liquid crystal compound. 17. The liquid crystal composition of claim 16, wherein the liquid crystal compound includes at least one of the following L-1 to L-10.

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