TWI612129B - Chemical compound for aligning liquid crystal molecule, liquid crystal panel, and method for fabricating liquid crystal panel - Google Patents

Abstract

A liquid crystal alignment compound includes a carbon chain structure, an adsorption functional group, and a first cross-linking functional group. The adsorption functional group is bonded to the carbon chain structure, wherein the adsorption functional group is polysiloxy. The first cross-linking functional group is bonded to the adsorption functional group, wherein the first cross-linking functional group includes a thermosetting functional group or a photo-curable functional group.

Description

Liquid crystal alignment compound, liquid crystal panel, and manufacturing liquid crystal Panel method

The invention relates to a liquid crystal alignment compound, a liquid crystal panel, and a method for manufacturing a liquid crystal panel.

Liquid crystal display devices have become the mainstream of the development of the display industry. As the main element of a liquid crystal display device, a liquid crystal panel restricts the liquid crystal molecules between two opposite substrates in an orderly manner, matches a polarizing plate, and controls the rotation of the liquid crystal molecules through an applied voltage to control the penetration of light.

The liquid crystal panel has an alignment film standing there, and the liquid crystal molecules are arranged in order. The alignment film can be completed by coating polyimide (PI) material and baking and rubbing, but the setting of the polyimide alignment film may cause an increase in material cost, bring additional sources of pollution and thickness The problem of unevenness.

Some embodiments of the present invention provide a liquid crystal alignment compound. The liquid crystal alignment compound has an alignment of liquid crystal molecules and an alignment with another liquid crystal. Ability of compounds to crosslink. Designing a liquid crystal alignment compound as the alignment layer can maintain the vertical alignment ability of the liquid crystal molecules, and the configuration of the polyimide (PI) alignment layer can be omitted, thereby preventing possible problems caused by the polyimide alignment layer. , Such as increased material costs, additional sources of pollution, and uneven thickness. In addition, the liquid crystal alignment compound can be designed to have a certain adsorption force on the substrate, or the liquid crystal alignment compound can absorb a certain amount of energy before cross-linking and tend to rely on the inner surface of the substrate, so as to avoid excessive liquid crystal alignment compound 110 remaining on the liquid crystal panel. In the liquid crystal layer.

According to some embodiments of the present invention, a liquid crystal alignment compound includes a carbon chain structure, an adsorption functional group, and a first cross-linking functional group. The adsorption functional group is only bonded to the carbon chain structure, wherein the adsorption functional group includes at least one silicon atom, at least one nitrogen atom, at least one oxygen atom, or at least one carbon atom. The first cross-linking functional group is bonded to the carbon chain structure, wherein the first cross-linking functional group includes a thermosetting functional group or a photo-curable functional group.

In some embodiments, the adsorption functional group is selected from the group consisting of a siloxy group, an alcohol group, an acid group, and an amino group.

、

以及

所組成的群組。 In some embodiments, the thermosetting functional group comprises an epoxy group, wherein the epoxy group is selected from the group consisting of

,

as well as

A group of people.

In some embodiments, the adsorption functional group is a polysiloxy group, wherein the polysiloxy group has a plurality of silicon atoms, and the polysiloxy group is Ring or column structure.

According to some embodiments of the present invention, the liquid crystal alignment compound includes a carbon chain structure, an adsorption functional group, and a first cross-linking functional group. The adsorption functional group is bonded to the carbon chain structure, wherein the adsorption functional group is polysiloxy. The first cross-linking functional group is bonded to the adsorption functional group, wherein the first cross-linking functional group includes a thermosetting functional group or a photo-curable functional group.

以及

所組成的群組。 In some embodiments, the adsorption functional group is selected from the group consisting of

as well as

A group of people.

In some embodiments, the first cross-linking functional group includes an epoxy group.

、

、

、

、

以及

所組成的群組。 In some embodiments, the first cross-linking functional group includes a polymerizable double bond, wherein the photo-curable functional group is selected from the group consisting of

,

,

,

,

as well as

A group of people.

According to some embodiments of the present invention, the compound further includes a second cross-linking functional group and is bonded to the first cross-linking functional group, wherein the second cross-linking functional group includes a thermosetting functional group or a photo-curable functional group.

In some embodiments, the carbon chain structure includes a benzene ring, a five-ring ring, a six-ring ring, or a heterocyclic ring.

以及

所組成的群組。 In some embodiments, the carbon chain structure is selected from the group consisting of

as well as

A group of people.

In some embodiments, the liquid crystal alignment compound is suitable for a display panel, and there is no alignment film on the inner surface of the two substrates of the display panel.

According to some embodiments of the present invention, the liquid crystal panel includes a first substrate, an opposite second substrate, a liquid crystal layer, and the aforementioned liquid crystal alignment compound. The liquid crystal layer is disposed between the first substrate and the second substrate, wherein the liquid crystal layer includes a plurality of liquid crystal molecules. The liquid crystal alignment compound is disposed between the first substrate and the second substrate. The first cross-linking functional groups corresponding to the liquid crystal alignment compound are all cross-linked to each other, and the liquid crystal alignment compound makes the liquid crystal molecules have a pretilt angle on the first substrate and the second substrate There is no alignment film on the inner surfaces of the first substrate and the second substrate.

In some embodiments, at least part of the adsorption functional group of the liquid crystal alignment compound is adsorbed on the first substrate.

According to some embodiments of the present invention, a method for manufacturing a liquid crystal panel includes mixing the aforementioned liquid crystal alignment compound and a plurality of liquid crystal molecules into a mixture; injecting the mixture between a first substrate and an opposite second substrate, and the first There is no alignment film on the inner surfaces of the substrate and the second substrate; and the liquid crystal molecules have a pretilt angle temporarily, and the first cross-linking functional group of the liquid crystal alignment compound is cross-linked on the inner surfaces of the first substrate and the second substrate. Therefore, at least a part of the liquid crystal molecules are restricted to the pretilt angle by the liquid crystal alignment compound.

In some embodiments, the step of causing the first cross-linking functional group of the liquid crystal alignment compound to cross-link on the inner surfaces of the first substrate and the second substrate is performed by a light method, a heating method, or a combination thereof.

In some embodiments, the step of making the liquid crystal molecules temporarily have a pretilt angle includes: applying an external voltage to the liquid crystal molecules.

In some embodiments, the method for manufacturing a liquid crystal panel further includes: adsorbing an adsorption functional group of a liquid crystal alignment compound on the inner surfaces of the first substrate and the second substrate.

In some embodiments, the step of causing the adsorption functional group of the liquid crystal alignment compound to be adsorbed on the inner surfaces of the first substrate and the second substrate is performed by a light method, a heating method, or a combination thereof.

100‧‧‧ mixture

110‧‧‧ Liquid crystal alignment compound

112‧‧‧ Cross-linking

120‧‧‧ liquid crystal molecules

200‧‧‧ the first substrate

202‧‧‧Inner surface

300‧‧‧second substrate

302‧‧‧Inner surface

400‧‧‧LCD panel

X‧‧‧ carbon chain structure

A‧‧‧functional group

LC‧‧‧LCD layer

T‧‧‧Pre-tilt

V‧‧‧Voltage

N ₀ ‧‧‧ Long axis direction

E1‧‧‧ plus energy

E2‧‧‧ plus energy

1A to 1E are schematic cross-sectional views of a liquid crystal panel according to an embodiment of the present invention at various stages of a manufacturing method.

Several embodiments of the present invention will be disclosed in the following drawings. For the sake of clear description, many practical details will be described in the following description. Of course However, it should be understood that these practical details should not be used to limit the invention. That is, in some embodiments of the present invention, these practical details are unnecessary. In addition, in order to simplify the drawings, some conventional structures and elements will be represented in the drawings in a simple and schematic manner.

1A to 1E are schematic cross-sectional views of a liquid crystal panel according to an embodiment of the present invention at various stages of a manufacturing method. Hereinafter, a plurality of stages of manufacturing a liquid crystal panel (or a display panel) will be described in detail. First, the mixture 100 is injected between the first substrate 200 and the opposite second substrate 300. Here, the mixture 100 can be formed by mixing the liquid crystal alignment compound 110 and the plurality of liquid crystal molecules 120. The mixture 100 may be referred to as a liquid crystal mixture or a liquid crystal layer.

、

或

，其中液晶分子120具有一長軸延伸方向N₀。 The liquid crystal molecules 120 may be various suitable liquid crystal molecules, for example:

,

or

The liquid crystal molecules 120 have a major axis extension direction N ₀ .

The liquid crystal alignment compound 110 may have a carbon chain structure X, a functional group A, and a first cross-linking functional group (not shown), wherein the carbon chain structure X may affect the orientation of the liquid crystal molecules 120, and the first cross-linking functional group may be under appropriate conditions. Cross-link with another first cross-linking functional group. The liquid crystal alignment compound 110 is a chemical molecule, and its molecular formula will be described in detail in the following embodiments.

Here, the functional group A of the liquid crystal alignment compound 110 in the mixture 100 can provide an adsorption force to the inner surface 202 of the first substrate 200 or the inner surface 302 of the second substrate 300, so that the liquid crystal alignment compound 110 can be adsorbed to the first group. If the inner surface 202 of the plate 200 and the inner surface 302 of the second substrate 300 are used, the functional group A may be referred to as an adsorption functional group A. However, in some cases, there are still some liquid crystal alignment compounds 110 that are not adsorbed on the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300, which may cause the alignment force received by the liquid crystal molecules 120 to be insufficient or Image sticking due to liquid crystal alignment compound 110 remaining.

In various embodiments of the present invention, referring to FIG. 1B, the liquid crystal alignment compound 110 can be selectively absorbed by the external energy E1, such as an illumination method, a heating method, or a combination thereof. In this way, most of the functional groups A of the liquid crystal alignment compound 110 can be adsorbed on the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300, thereby reducing the position of the liquid crystal alignment compound 110 in the first The liquid crystal alignment compound 110 in the center of the substrate 200 and the second substrate 300 is not limited in this embodiment.

In other embodiments, the adsorption force of the functional group A itself may be sufficiently high, so that almost all the liquid crystal alignment compounds 110 can be adsorbed on the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300. In this case, the step of increasing the adsorption force by applying external energy may be omitted.

Next, referring to FIG. 1C, an external voltage V is applied to the liquid crystal molecules 120, so that the liquid crystal molecules 120 adjacent to the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300 have a pre-tilt angle T (pre-tilt angle), or inclination. For example, in this embodiment, the external voltage V is applied to the first conductive layer (or pixel electrode, not labeled) on the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300. The second conductive layer (not labeled) is adjacent to the first conductive layer on the inner surface 202 and the second conductive layer on the inner surface 302 The liquid crystal molecules 120 of the conductive layer may have a pretilt angle.

Here, the term “the liquid crystal molecules have a pretilt angle” means that the long axis direction N _{0 of the} liquid crystal molecules is not completely perpendicular or parallel to the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300. The angle between the long axis extension direction N _{0 of the} molecule and the inner surface of the substrate is referred to as the pretilt angle T, where the range of the pretilt angle T is greater than 0 degrees and less than 90 degrees. In other words, when the liquid crystal molecules 120 are not applied with a voltage, the liquid crystal molecules 120 still have an included angle between the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300, which is referred to as a pretilt angle T. In contrast, “the liquid crystal molecules have no pretilt angle” means that the long axis extension direction of the liquid crystal molecules is completely perpendicular or parallel to the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300. In other words, when no voltage is applied to the liquid crystal molecules 120, the liquid crystal molecules 120 can still be perpendicular or parallel to the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300.

Here, the effects of the applied voltage on the liquid crystal molecules 120 located in the center of the mixture 100 and the liquid crystal molecules 120 adjacent to the inner surface 202 and the inner surface 302 are discussed separately. Since the liquid crystal molecules 120 located at the center of the mixture 100 are not restricted by the boundary conditions of the substrate, they are affected by the electric field and have a large rotation range. In contrast, the liquid crystal molecules 120 adjacent to the inner surface 202 and the inner surface 302 are limited by the substrate boundary conditions and the liquid crystal alignment compound 110, and although they are affected by the electric field, they have only a small rotation amplitude. In other words, the liquid crystal molecules 120 near the substrate surface are affected by the electric field less than the electric fields received by the liquid crystal molecules 120 in the center of the first substrate and the second substrate.

Although the liquid crystal alignment compound 110 is attached to the inner surface 202 and the inner surface 302 here, cross-link and curing have not yet occurred substantially. Or aggregate. Therefore, at this time, the liquid crystal alignment compound 110 can still be driven by the liquid crystal molecules 120.

Next, referring to FIG. 1D, the liquid crystal alignment compound 110 absorbs energy by applying an external energy E2, such as an illumination method, a heating method, or a combination of the foregoing, so that the first cross-linking functional group (not shown) of any two liquid crystal alignment compounds 110. At least one cross-linking bond 112 is formed on the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300. In this way, even if the applied voltage is removed, at least a part of the liquid crystal molecules 120 are restricted by the pretilt angle T due to the cross-linking bond 112. Here, the liquid crystal alignment compound 110 may have a single or a plurality of first cross-linking functional groups (not shown), and may generate a cross-linking bond 112 with a first cross-linking functional group (not shown) of another liquid crystal alignment compound 110. . Here, the cross-linking bonds 112 only schematically represent the state where a plurality of liquid crystal alignment compounds 110 are cross-linked and fixed with each other in a virtual frame. It should be understood that the cross-linking bonds 112 can be regarded as a single or A polymer network composed of a plurality of first cross-linking functional groups (not shown).

In various embodiments of the present invention, the liquid crystal alignment compound 110 is caused to form a pretilt angle on the inner surface 202 of the first substrate 200 and the inner surface 302 of the second substrate 300 under an applied voltage V, and cross-links substantially through the liquid crystal alignment compound. The rotation position of the liquid crystal molecules 120 is restricted from above, so that the pretilt angle of the liquid crystal molecules is fixed.

Thereby, referring to FIG. 1E, a liquid crystal panel 400 can be obtained. The liquid crystal panel 400 includes a first substrate 200, an opposite second substrate 300, a liquid crystal layer LC, and the aforementioned liquid crystal alignment compound 110. The liquid crystal layer LC is disposed between the first substrate 200 and the second substrate 300. The liquid crystal layer LC includes a plurality of liquid crystal molecules. 120. The liquid crystal alignment compound 110 is disposed between the liquid crystal layer LC and the first substrate 200 and between the liquid crystal layer LC and the second substrate 300. The first cross-linking functional groups corresponding to the liquid crystal alignment compound 110 are cross-linked to each other, and the liquid crystal alignment compound 110 causes the liquid crystal molecules 120 to have a pretilt angle T between the first substrate 200 and the second substrate 300.

Accordingly, in various embodiments of the present invention, the liquid crystal alignment compound 110 has the ability to align the liquid crystal molecules 120 and cross-link with another liquid crystal alignment compound 110. The liquid crystal alignment compound 110 is designed to have an effect similar to that of the alignment layer, which can maintain the pretilt angle of the liquid crystal molecules 120, and the configuration of the polyimide (PI) alignment layer can be omitted, thereby preventing the polyimide alignment layer. Multiple issues, such as increased material costs, additional sources of contamination, and uneven thickness. In addition, the functional group A of the liquid crystal alignment compound 110 can be designed to have an adsorption force on the substrate, or the liquid crystal alignment compound 110 can absorb a certain amount of energy before cross-linking and tend to rely on the inner surface of the substrate, avoiding too many liquid crystal alignment compounds. 110 remains.

The first embodiment of the liquid crystal alignment compound 110 is described below. The liquid crystal alignment compound 110 may include a carbon chain structure X, a functional group A, and a first cross-linking functional group Y. In this embodiment, the functional group A is only bonded to the carbon chain structure X, that is, the functional group A is not bonded to the first cross-linked functional group Y, and the first cross-linked functional group Y is bonded to the carbon chain structure X, that is, The first cross-linking functional group Y is not bonded to the functional group A. In other words, the carbon chain structure X is respectively bonded to the functional group A and the first cross-linking functional group Y, that is, the functional group A is bonded to the first cross-linking functional group Y via the carbon chain structure X. Specifically, the molecular structure of the liquid crystal alignment compound 110 may be configured as follows:

以及

所組成的群組。如前所述，官能基A可對於基板200/300的表面提供吸附力，使得液晶配向化合物110可以吸附於基板的表面，則官能基A可被稱為吸附官能基A。 The functional group A includes at least one silicon atom, at least one nitrogen atom, at least one oxygen atom, or at least one carbon atom. The functional group A may be selected from the group consisting of a siloxy group, an alcohol group, an acid group, and an amino group. For example, the functional group A is selected from the group consisting of Si (OH) ₃ , Si (Cl) ₃ , Si (OCH ₃ ) ₃ , Si (OC ₂ H ₅ ) ₃ , CO ₂ H, NH ₂ and NH. Group. In some embodiments, the functional group A is a polysiloxy group, wherein the polysiloxy group has a plurality of silicon atoms, and the polysiloxy group has a cyclic or columnar structure. For example, the polysiloxy group is selected from

as well as

A group of people. As described above, the functional group A can provide an adsorption force on the surface of the substrate 200/300, so that the liquid crystal alignment compound 110 can be adsorbed on the surface of the substrate, and the functional group A can be referred to as an adsorption functional group A.

、

、

、

、

、

、

、

以及

所組成的群組。於部分實施方式中，光固型官能基包含聚合性雙鍵，光固型官能基係選自由

、

、

、

、

以及

所組成的群組。 The first cross-linking functional group Y includes a thermosetting functional group or a photocurable functional group. In some embodiments, the thermosetting functional group comprises an epoxy group, wherein the epoxy group is selected from the group consisting of

,

,

,

,

,

,

,

as well as

A group of people. In some embodiments, the photocurable functional group includes a polymerizable double bond, and the photocurable functional group is selected from the group consisting of

,

,

,

,

as well as

A group of people.

、

以及

所組成的群組。 In some embodiments, the carbon chain structure X includes a benzene ring, a five-ring ring, a six-ring ring, or a heterocyclic ring. For example, the carbon chain structure X is selected from

,

as well as

A group of people.

In some embodiments of the present invention, when the functional group A is a siloxane group, the liquid crystal alignment compound 110 can be designed as follows:

Here, the functional group A and the first cross-linking functional group Y may be respectively bonded to the same carbon atom of the carbon chain structure X, for example, SO-I. Alternatively, the functional group A and the first cross-linking functional group Y may be respectively bonded to different carbon atoms of the carbon chain structure X, for example: SO-II, SO-III, SO-V, and SO-VI. In addition, since the first cross-linking functional group Y of SO-III is connected to the carbon chain structure X, the functional group A has more siloxane groups than SO-IV to adsorb to the substrate, and its adsorption capacity is better.

On the other hand, in some embodiments of the present invention, when the functional group A is an amine group, the liquid crystal alignment compound 110 can be designed as follows:

Here, the functional group A and the first cross-linking functional group Y may be respectively bonded to the same carbon atom of the carbon chain structure X, for example: NP-I. Alternatively, the functional group A and the first cross-linking functional group Y may be respectively bonded to different carbon atoms of the carbon chain structure X, for example: NP-II, NP-III, NP-IV, NP-V, and NP-VI.

In some embodiments, the liquid crystal alignment compound 110 may further include a second cross-linking functional group Z, and the second cross-linking functional group Z includes a thermosetting functional group or a photo-curable functional group, wherein the second cross-linking functional group Z and The types of the first cross-linking functional group Y can be the same or different. Compared to a single molecule having only one cross-linking functional group, having a plurality of cross-linking functional groups on a single molecule can make the pretilt angle of the liquid crystal alignment compound 110 more stable. In some embodiments, the second cross-linking functional group Z and the first cross-linking functional group Y are bonded, so that the second cross-linking functional group Z does not directly bond the carbon chain structure X, but it is not limited thereto. Specifically, its structure is as follows:

以及

。 In some embodiments, the first cross-linking functional group Y includes a photo-curable functional group, and the second cross-linking functional group Z includes a thermo-curable functional group. For example, the liquid crystal alignment compound 110 may be:

as well as

.

In other embodiments, the first cross-linking functional group Y includes a thermosetting functional group, and the second cross-linking functional group Z includes a photo-curable functional group.

It should be understood that the second cross-linking functional group Z can be designed to be bonded to the carbon chain structure X or the functional group A in practical applications. The second cross-linking functional group Z and the first cross-linking functional group should not be disclosed here. Y bonds limit the scope of the invention.

It has been disclosed above that the functional group A and the first cross-linking functional group Y are not bonded to each other, but a liquid crystal alignment compound 110 that maintains the structure by connecting the two through the carbon chain structure X. In practice, this should not limit the scope of the invention.

The second embodiment of the liquid crystal alignment compound 110 will be described below. In detail, the liquid crystal alignment compound 110 includes a carbon chain structure X, a functional group A, and a first cross-linking functional group Y. The functional group A is bonded to the carbon chain structure X, that is, the carbon chain structure X is not bonded to the first cross-linking functional group Y, and the first cross-linking functional group Y is bonded to the functional group A, that is, the first cross-linking functional group Y Not bonded to the carbon chain structure X. In other words, the functional group A is respectively bonded to the carbon chain structure X and the first cross-linking functional group Y, that is, the first cross-linking functional group Y is bonded to the carbon chain structure X via the functional group A. Specifically, the structure of the liquid crystal alignment compound 110 may be configured as follows:

以及

所組成的群組。如前所述，官能基A可對於基板200/300的表面提供吸附力，使得液晶配向化合物110可以吸附於基板的表面，則官能基A可被稱為吸附官能基A。 Here, the functional group A is polysiloxy, and the functional group A can be freely selected.

as well as

A group of people. As described above, the functional group A can provide an adsorption force on the surface of the substrate 200/300, so that the liquid crystal alignment compound 110 can be adsorbed on the surface of the substrate, and the functional group A can be referred to as an adsorption functional group A.

、

、

、

、

以及

所組成的群組。 As described above, the first cross-linking functional group Y includes a thermosetting functional group or a photocurable functional group. In some embodiments, the first cross-linking functional group Y includes an epoxy group. Alternatively, in some embodiments, the first cross-linking functional group Y includes a polymerizable double bond, wherein the photo-curable functional group is selected from the group consisting of

,

,

,

,

as well as

A group of people.

以及

所組成的群組。 In some embodiments, the carbon chain structure X includes a benzene ring, a five-ring ring, a six-ring ring, or a heterocyclic ring. In some embodiments, the carbon chain structure X is selected from the group consisting of

as well as

A group of people.

For example, the liquid crystal alignment compound 110 can be designed as follows:

The carbon chain structure X and the first cross-linking functional group Y may be respectively bonded to different atoms of the functional group A. For example, here, the carbon chain structure X tends to be bonded to a silicon atom, and the first cross-linking functional group Y tends to be bonded to an oxygen atom.

In some embodiments, the liquid crystal alignment compound 110 further includes a second cross-linking functional group Z, and the second cross-linking functional group Z includes a thermosetting functional group or a photo-curable functional group, preferably the second cross-linking functional group Z. Different from the first type of the cross-linking functional group Y, the liquid crystal alignment compound 110 can have both photo-sensitive and heat-sensitive functional groups at the same time, thereby making the pretilt angle more stable, but not limited thereto. In some embodiments, the second cross-linking functional group Z is bonded to the first cross-linking functional group Y instead of directly bonding to the functional group A. For example, the structure of the liquid crystal alignment compound 110 is as follows:

In one embodiment, the first cross-linking functional group includes a thermosetting functional group, and the second cross-linking functional group includes a photo-curable functional group. In another embodiment In the first cross-linking functional group, a photo-curing functional group is included, and the second cross-linking functional group includes a thermo-setting functional group.

In practical applications, the scope of the present invention should not be limited in this way. Both the second cross-linking functional group Z and the first cross-linking functional group Y can be bonded to the functional group A, and the second cross-linking functional group Z and the first cross-linking functional group The type of the bifunctional Y may be the same or different. Alternatively, the second cross-linking functional group Z, the first cross-linking functional group Y, the carbon chain structure X, and the functional group A may be combined in other ways.

According to this, the carbon chain structure X of the liquid crystal alignment compound 110 provides the ability to align. The liquid crystal molecules 120 can be pretilted by an applied voltage. The first cross-linking functional group of the liquid crystal alignment compound 110 provides the ability to cross-link the liquid crystal. The molecules 120 are constrained by the pretilt angle. The adsorption ability of the functional group A of the liquid crystal alignment compound 110 may affect the amount of the liquid crystal alignment compound 110 remaining in the liquid crystal layer of the liquid crystal panel.

In order to fully explain the feasible methods of various embodiments of the present invention, the following describes the synthesis methods of various liquid crystal alignment compounds 110. It should be understood that the methods or materials listed herein do not limit the scope of the present invention, and those skilled in the art can appropriately change the solvents, catalysts, or materials therein.

Take for example the first compound SO-I listed.

First, compound 1 and a mixed solvent of dichloromethane and methanol (MeOH-CH ₂ Cl ₂ ) were sequentially added to a drying container. After dissolving Compound 1 with stirring, an acid is added at room temperature to catalyze the reaction. The above acid may be, for example, p-toluenesulfonic acid (p-TSA). After the reaction at room temperature, a saturated aqueous solution of sodium bicarbonate was added to stop the reaction. After extraction, concentration, chromatography, and purification, compound 2 was obtained.

In another drying container, compound 2, a base, and a mixed solvent of toluene and methanol (MeOH-toluene) are sequentially added. The above-mentioned base may be, for example, potassium hydroxide, sodium hydroxide, calcium carbonate, sodium carbonate, potassium carbonate, etc. . After dissolving Compound 2 and the base with stirring, Compound 3 was added. Next, let the reactants mix The reaction is performed at a suitable temperature for a period of time, for example, after 8 hours of reaction at 70 degrees Celsius, the temperature is returned, and then a saturated aqueous solution of ammonium chloride is added to stop the reaction. Then through extraction, concentration, chromatography and purification steps, compound No. 4 can be obtained.

In another embodiment of the present invention, a method for synthesizing the liquid crystal alignment compound 110 is described by taking the compound NP-I as an example.

First, add compound 5 and dichloride in this order in a dry container. Methane and methanol mixed solvents. After dissolving Compound 5 with stirring, a base such as potassium hydroxide, sodium hydroxide, calcium carbonate, sodium carbonate, potassium carbonate, etc. is added. Next, after reacting the reactants at room temperature for a certain time (for example, 18 hours), a saturated aqueous solution of ammonium chloride is added to stop the reaction. After extraction, concentration, chromatographic filtration, purification and other steps, compound 6 can be obtained.

In another drying container, compound 6, a base, and a mixed solvent of toluene and methanol (MeOH-toluene) are sequentially added. The above-mentioned base may be, for example, potassium hydroxide, sodium hydroxide, calcium carbonate, sodium carbonate, potassium carbonate, etc. . After dissolving Compound 6 and the base with stirring, Compound 3 was added. Next, the reactants are mixed at a suitable temperature for a period of time, for example, after 15 hours at 70 degrees Celsius, the temperature is raised, and the reaction is stopped by adding a saturated aqueous solution of ammonium chloride. After extraction, concentration, chromatography, purification and other steps, Compound 7 can be obtained.

Then, in a double-necked flask containing a magnet and a reflux device, compound 7, stannous chloride, and ethanol were added under a stable environment (such as nitrogen). After reacting the reactants under reflux for a certain period of time (for example, 18 hours), the temperature is increased, and the reaction is stopped by adding an aqueous solution of calcium bicarbonate. After extraction, concentration, chromatography, and purification, the final compound 8 can be obtained, that is, The aforementioned compound NP-I.

In yet another embodiment of the present invention, a method for synthesizing the liquid crystal alignment compound 110 is described by taking the compound PS-I as an example.

Add compound 9 and dichloromethane in a dry container, stir and dissolve compound 9, and then add a base and a solvent dichloromethane (CH ₂ Cl ₂ ). The base can be, for example, potassium hydroxide, sodium hydroxide, or calcium carbonate. , Sodium carbonate and potassium carbonate. Next, after the above compounds are uniformly stirred at room temperature, trimethylsilyl chloride (TMSCL) is added at room temperature, the reactants are mixed and reacted at room temperature for a certain time (for example, 12 hours), and then hydrogen is added Aqueous chloric acid solution is used to stop the reaction. After extraction, concentration, chromatography, purification and other steps, compound 10 can be obtained.

Next, in a double-necked flask containing magnets and a reflux device, first vacuum dry, and then add compound 10, long carbon chain compound 11, palladium metal catalyst, hydrogen carbonate under a stable environment (such as nitrogen). Sodium and the solvent toluene are added, the mixture is first stirred uniformly, and then a catalyst such as a triisobutyl phosphorus compound (P (t-Bu) ₃ ) is added. After reacting the reactants under reflux for a certain period of time (for example, 8 hours), the temperature is increased, and the reaction is stopped by adding an aqueous solution of ammonium chloride. After extraction, concentration, chromatographic filtration, purification and other steps, compound 12 can be obtained.

Then, in another dry container, add compound 12, dichloride A mixed solvent of methane and methanol, and the compound 12 is dissolved by stirring, and then an acid is added at room temperature to catalyze the reaction. The above acid may be, for example, p-toluenesulfonic acid (p-TSA). After the reaction at room temperature, a saturated aqueous solution of sodium bicarbonate was added to stop the reaction. After extraction, concentration, chromatography, and purification, compound 13 was obtained.

In another drying container, compound 13, a base, and a mixed solvent of toluene and methanol are added. The above-mentioned base may be, for example, potassium hydroxide, sodium hydroxide, calcium carbonate, sodium carbonate, potassium carbonate, and the like. After dissolving Compound 2 and the base with stirring, Compound 3 was added. Next, the reactants are mixed at a suitable temperature for a period of time, for example, after reacting for 12 hours at 70 degrees Celsius, the temperature is increased, and the reaction is stopped by adding a saturated aqueous solution of ammonium chloride. After extraction, concentration, chromatography, and purification, the final product can be obtained. Compound 14, the aforementioned compound PS-I.

Accordingly, in various embodiments of the present invention, the liquid crystal alignment compound 110 is designed to have a carbon chain structure, an adsorption functional group, and a cross-linking functional group. The liquid crystal alignment compound 110 can serve as an alignment layer to maintain the liquid crystal molecules 120 with an appropriate pretilt angle, and It has the effect of omitting the cost and avoiding the liquid crystal alignment compound 110 remaining. In addition, the use of polyimide (PI) can be omitted to reduce costs. Because the liquid crystal alignment compound replaces polyimide (PI), a liquid crystal panel with a narrow frame or even a frame can be further achieved.

Although the present invention has been disclosed in various embodiments as above, it is not intended to limit the present invention. Any person skilled in the art can make various modifications and retouches without departing from the spirit and scope of the present invention. The scope of protection shall be determined by the scope of the attached patent application.

100‧‧‧ mixture

110‧‧‧ Liquid crystal alignment compound

112‧‧‧ Cross-linking

120‧‧‧ liquid crystal molecules

200‧‧‧ the first substrate

300‧‧‧second substrate

400‧‧‧LCD panel

X‧‧‧ carbon chain structure

A‧‧‧ Adsorption functional group

LC‧‧‧LCD layer

T‧‧‧Pre-tilt

N ₀ ‧‧‧ Long axis direction

Claims (15)

A liquid crystal alignment compound includes: a carbon chain structure; and a polysiloxy group, which is only bonded to the carbon chain structure, wherein the polysiloxy group has a plurality of silicon atoms, and the polysiloxy group is a ring Or a columnar structure; and a first cross-linking functional group bonded to the carbon chain structure, wherein the first cross-linking functional group includes a thermosetting functional group or a photo-curable functional group. The compound according to claim 1, wherein the thermosetting functional group comprises an epoxy group, wherein the epoxy group is selected from the group consisting of

,

as well as

A group of people. The compound according to claim 1, wherein the polysiloxy group is selected from the group consisting of

as well as

A group of people. The compound of claim 1, wherein the first cross-linking functional group comprises an epoxy group. The compound according to claim 1, wherein the first cross-linking functional group comprises a polymerizable double bond, and the photo-curable functional group is selected from the group consisting of

,

,

,

as well as

A group of people. The compound according to claim 1, further comprising a second cross-linking functional group, which is bonded to the first cross-linking functional group, wherein the second cross-linking functional group includes a thermosetting functional group or a photo-curing functional group Functional group. The compound according to claim 1, wherein the carbon chain structure includes a benzene ring, a five-ring ring, a six-ring ring, or a heterocyclic ring. The compound according to claim 1, wherein the carbon chain structure is selected from the group consisting of

,

,

,

,

,

as well as

A group of people. The compound according to claim 1, wherein the liquid crystal alignment compound is suitable for a display panel, and there is no alignment film on the inner surface of the two substrates of the display panel. A liquid crystal panel includes: a first substrate and an opposite second substrate; a liquid crystal layer disposed between the first substrate and the second substrate, wherein the liquid crystal layer includes a plurality of liquid crystal molecules; and a plurality of liquid crystal molecules such as The liquid crystal alignment compound according to claim 1 is disposed between the first substrate and the second substrate, wherein the first cross-linking functional groups corresponding to the liquid crystal alignment compounds are all cross-linked to each other, and the liquid crystals The alignment compound causes the liquid crystal molecules to have a pretilt angle between the first substrate and the second substrate, and there is no alignment film on the inner surfaces of the first substrate and the second substrate. The liquid crystal panel according to claim 10, wherein at least a part of the polysiloxy groups of the liquid crystal alignment compounds are adsorbed on the first substrate. A method for manufacturing a liquid crystal panel, comprising: mixing a plurality of liquid crystal alignment compounds as described in claim 1 and a plurality of liquid crystal molecules into a mixture; and injecting the mixture between a first substrate and an opposite second substrate, and There is no alignment film on the inner surfaces of the first substrate and the second substrate; and the liquid crystal molecules have a pretilt angle temporarily, and the first cross-linking functional groups of the liquid crystal alignment compounds are in the first A substrate is cross-linked with the inner surface of the second substrate, so that at least a part of the liquid crystal molecules are restricted to the pretilt angle by the liquid crystal alignment compounds. The method for manufacturing a liquid crystal panel according to claim 12, wherein the step of causing the first cross-linking functional groups of the liquid crystal alignment compounds to crosslink on the inner surfaces of the first substrate and the second substrate is through a It can be performed in a light mode, a heating mode, or a combination thereof. The method for manufacturing a liquid crystal panel according to claim 12, wherein the step of temporarily providing the liquid crystal molecules with the pretilt angle includes: applying an external voltage to the liquid crystal molecules. The method for manufacturing a liquid crystal panel according to claim 12, further comprising: adsorbing the liquid crystal alignment compounds on the inner surfaces of the first substrate and the second substrate.