TW200804271A - Monomer and manufacturing method of liquid crystal display panel using the same - Google Patents

Abstract

A monomer disclosed, is represented by formula (1). B-A-R (1). "A" is represented by formula (2), (3), (4) or combinations thereof. At least one of "B" and "R" is represented by alkyl, alkoxy, ester, formula (5), (6), (7), (8), or combinations thereof; "T" is selected from oxygen, nitrogen, or combinations thereof, "X" is selected from hydrogen, alkyl, halogen, cyan, or combinations thereof. n is a positive integer.

Description

200804271

Sanda number: TW3053PA • Nine, invention description: [Technical field of invention] The present invention relates to a monomer and a method for manufacturing the same, and in particular to a liquid crystal molecule which is more easily miscible with A monomer and a method of manufacturing the same for a liquid crystal display panel. [Prior Art] In the current era of rapid technological development, liquid crystal display panels have been widely used in electronic display products, such as televisions, computer screens, pens, mobile phones, personal digital assistants, and the like. In particular, a multi-display field alignment (multi_d〇main aHgnment) type liquid crystal display panel prepared by using a polymer % 疋 alignment (PSA) technology has a fast reaction time, a wide viewing angle, a high aperture ratio, The advantages of high contrast and simple process have always been highly valued by the industry. In the PSA technology, in the process of preparing the display panel, a trace amount of a reactive monomer is added to the liquid crystal layer sandwiching the first and second substrates to mix the liquid crystal molecules with the reactive monomer. . Then, when a voltage and ultraviolet (UV) light are applied to the first and second substrates, the reactive monomer is phase-separated from the liquid crystal molecules, and is polymerized into a polymerization on the surfaces of the first and second substrates. Things. When the polymer is deposited on the interface of the first and second substrates in the liquid crystal layer, the polymer molecules are arranged in the direction of the liquid crystal molecules due to the interaction force between the polymer and the liquid crystal molecules. Therefore, liquid crystal molecules have a pre-tile angle in a certain direction 〇 7 200804271

Sanda number: TW3053PA However, since the mutual solubility of the conventional reactive monomer and liquid crystal molecules is not very good, the liquid crystal molecules and the reactive monomer are dropped through the liquid crystal dropping method (one dropfiU, ODF) in the first and second On one of the substrates, the reactive monomers are only distributed on the periphery or surface of the liquid crystal beads. That is, the reactive monomer is not uniformly mixed with the liquid crystal molecules or distributed in the liquid crystal layer. Therefore, when the first and second substrates are pressed together, the diffusion distance of the reaction type monomer and the liquid crystal molecules is different. Further, the reactive monomer is easily pushed by the liquid crystal molecules to the boundary of the liquid crystal beads, resulting in a higher concentration of reactive monomer between the two liquid crystal beads. Therefore, the pretilt angle at the boundary of the liquid crystal droplets is increased due to the concentration of the polymer polymerized by the reactive monomer, which causes the liquid crystal display panel to produce a lattice lattice defect (lattice mura), which seriously affects the liquid crystal display panel. Display quality. SUMMARY OF THE INVENTION In view of the above, an object of the present invention is to provide a single body and a method of manufacturing the same for a liquid crystal display panel. The design of the monomer structure can increase the degree of disturbance of the side chains of the monomers and avoid stacking of the monomers. As a result, the monomer will be more uniformly dissolved with the liquid crystal molecules to prevent the liquid crystal layer from easily changing from the liquid crystal state to the solid state. In addition, it is possible to avoid the problem of lattice defects caused by poor mutual solubility of the monomer and the liquid crystal molecules on the liquid crystal display panel and greatly improve the quality of the liquid crystal display panel. According to the object of the present invention, a monomer is proposed, which is represented by the chemical formula [1];

200804271 Sanda number: TVV3053PA B—A—* R [1] where ΠΑ ” is selected from the chemical formula [2], [3], [4] or a combination thereof;

Wherein at least one of "Β" and ''R" is selected from the group consisting of an alkyl group, an alkoxy group, an ester group, a chemical formula [5], [6], [7], [8] or a combination thereof;

Wherein "Τ" is selected from the group consisting of oxygen, nitrogen or a combination thereof, and "X" is selected from the group consisting of hydrogen, an alkyl group, a halogen element, a cyano group or a combination thereof, and the η system is a positive integer. According to an object of the present invention, a method of manufacturing a liquid crystal display panel is proposed. First, a first substrate having a first electrode and a second substrate having a second electrode are provided. Next, a liquid crystal layer is interposed between the first substrate and the second substrate, the liquid crystal layer is located between the first electrode and the second electrode, and the liquid crystal layer has a plurality of liquid crystal molecules and a plurality of monomers, and each single system is Chemical formula [1] is indicated. The above described objects, features, and advantages of the present invention will become more apparent and understood from the following description.

2nd ID: HV3053PA * [Embodiment] Please refer to FIG. 1 and FIG. 2A to FIG. 2D simultaneously. FIG. 1 is a flow chart showing a method of manufacturing a liquid crystal display panel according to an embodiment of the present invention, 2A~ 2D is a cross-sectional view showing a process of a method of manufacturing a liquid crystal display panel according to a first embodiment of the present invention. First, in step 11, as shown in FIG. 2A, a first substrate 21 and a second substrate 22 are provided. The first substrate 21 and the second substrate 22 respectively have a first electrode 21a and a second electrode 22a. . Next, in step 12, as shown in Fig. 2A, a liquid crystal layer 23 is interposed between the first substrate 21 and the second substrate 22, and the liquid crystal layer 23 is located between the first electrode 21a and the second electrode 22a. Among them, the liquid crystal layer 23 has a plurality of liquid crystal molecules 23a and a plurality of monomers 24 . Each monomer 24 can be a photosensitive monomer, and its chemical structure is represented by the chemical formula [1]: B-R [1] wherein the lanthanide is a hard core and contains a chemical formula [2] , [3], [4] or a combination of the above;

Wherein at least one of "R" and "B" may be selected from an alkyl group, an alkoxy group, an ester group, a chemical formula [5], [6], [7], [8] or a combination thereof. That is to say, at least one of nRn and ''B' may be a chemical formula [5], [6], 200804271

Erda number: TW3053PA ^ [7] or [8]. Alternatively, at least one of "R" and "B" may be a combination of chemical formulas [5] and [6], a combination of chemical formulas [5] and [7], or a combination of chemical formulas [5] and [8] . In the present embodiment, at least one of nR" &nB" is a combination of chemical formula [6], chemical formulas [5] and [6], a combination of chemical formulas [5] and [7], or a chemical formula [5]. The combination of ] and [8] is taken as an example, but the technique of the embodiment is not limited thereto.

Wherein ΠΤ" is selected from the group consisting of oxygen, nitrogen or a combination thereof, and "X" is selected from the group consisting of argon, an alkyl group, a halogen element, a cyano group or a combination thereof, and the η system is a positive integer. In the present embodiment, "11" may be selected from an alkyl group, an alkoxy group, an ester group or a combination thereof, and the oxime" may be selected from the chemical formulas [5], [6], [7], [8]. Or a combination of the above. Alternatively, "Β" and "quot" may be selected from the chemical formula [5], [6], [7], [8] or a combination thereof, and ''Β' and The substituents selected for R" may be the same or different. The η system may be a positive integer of 2 to 5, and the ΠΧ" may be selected from methyl, fluorine or chlorine. Further, if "R" is an alkoxy group, it may be represented by OCmH2m+1, and the m system may be A positive integer of 1 to 10. In addition, "R" and "Β" can be regarded as side chains of the monomer 24 which are connected to the left and right ends of the intermediate core "A". Then, in step 13, as shown in Fig. 2B, a voltage V is applied between the first electrode 21a and the second electrode 22a to rotate the liquid crystal molecules 23a. Moreover, the disturbance of the liquid crystal molecules 23a and the cells 24 can also be increased by one of heat source heating and one light source illumination, but not 11 200804271

• TW3053PA • Causes monomer 24 to produce complete polymerization, allowing monomer 24 to form a common layer. In other words, the heat source applied and the history of the light source will cause the monomer to prepolymerize or not cause the monomer 24 to produce a complete polymerization. Of course, it should be noted at this time that if the magnitude of the voltage V is not sufficient to allow the liquid crystal molecules 23a to rotate smoothly, the voltage may be applied in stages. For example, the first voltage is applied first, and then the second voltage is applied, and the first voltage and the second voltage are the same or different, but the first voltage and the second voltage are at the same level. The sum is the level of the voltage V that was originally applied to the second time. Alternatively, the first voltage is applied first, and then the second voltage is applied, and the first voltage and the second voltage are the same or different, but the first voltage and the second voltage are used. The sum of the sums is greater than the level of the voltage v when the original application is once. Furthermore, it must be noted that the steps of applying voltage or heating and illuminating can be applied simultaneously or sequentially. For example, in the embodiment, one of heating and illumination is performed first, and then a voltage is applied. Alternatively, apply a voltage first and then perform one of the heating and illuminating actions. Alternatively, one of the heating and illuminating actions is performed simultaneously with the application of the voltage. In addition, the second electrode 22a can be further divided into a plurality of regions, and the voltage applied to each region can be the same or different, and the applied voltage includes direct current, parent current, or a combination thereof. The first electrode 21a and the second electrode are, for example, a common electrode and a halogen electrode, respectively. Next, proceeding to step 14, as shown in Fig. 2C, the monomers 24 are polymerized upon application of this voltage V. That is, during the application of the voltage, the polymerization operation of the monomer 24 is performed. For example, based on monomer 24 is a photosensitive single 12 200804271

Sanda number: TW3053PA • The body can be illuminated on the upper surface of the second substrate 21 by an ultraviolet light 25 or other light source that causes the polymerization of the monomer 24 to illuminate the liquid crystal layer 23 so that the monomers 24 are at the first electrode. The surface of the 21a and the second electrode 22a is polymerized into a polymer layer 24a for use as an alignment film on the first substrate 21 and the second substrate 22. It is to be noted that when the liquid crystal layer 23 is irradiated with ultraviolet light 25 or other light source which causes the polymerization of the monomer 24, the liquid crystal layer 23 may be entirely irradiated or partitioned. When the liquid crystal layer 23 is irradiated in a partition, the irradiation energy of each region may be the same or different, and the energy sum of the partitioning of the liquid crystal layer 23 may be the same or different from the energy when the liquid crystal layer 23 is entirely irradiated. It should be noted that the voltages V applied in steps 13 and 14 may be the same or different, depending on the arrangement of the liquid crystal molecules 23a or other requirements. Then, proceeding to step 15, as shown in Fig. 2D, the voltage V is removed, and then the ultraviolet light 25 is removed or removed at the same time, and the liquid crystal display panel 26a is finally completed. At this time, the polymer 24a serves to provide a liquid crystal molecule 23a having a pre-tilt angle which is inclined with respect to the surfaces of the first electrode 21a and the second electrode 22a, and is advantageous for the liquid crystal molecules 23a to be slightly tilted in at least one specific direction. In general, the pretilt angle is less than 90 degrees, and preferably less than 60 degrees. Therefore, based on the above, the monomer 24 disclosed in the present embodiment can be applied in the process of preparing a liquid crystal display panel by a polymer-stabilized alignment (PSA) technique. Referring to Figures 3A to 3D, there are shown process cross-sectional views of a method of fabricating a liquid crystal display panel according to a second embodiment of the present invention. Please refer to FIG. 1 again. First, in step 11, as shown in FIG. 3A, a 13th 200804271 is provided.

Erda: TW3053PA • A substrate 21 and a second substrate 22, the first substrate 21 and the second substrate 22 respectively have a first electrode 21a and a second electrode 22a. The first electrode 21a and the second electrode 22a have a first alignment film 21b and a second alignment film 22b on the surface. Next, proceeding to step 12, as shown in Fig. 3A, a liquid crystal layer 23 is interposed between the first substrate 21 and the second substrate 22, and the liquid crystal layer 23 is located between the first electrode 21a and the second electrode 22a. That is, the liquid crystal layer 23 is located between the first alignment film 21b and the second alignment film 22b. The liquid crystal layer 23 has a plurality of liquid crystal molecules 23a and a plurality of cells 24, and the first alignment film 21b and the second alignment film 22b are used to tilt or align the liquid crystal molecules 23a in a specific direction. Each of the monomers 24 may be a photosensitive monomer, and its chemical structure is represented by the chemical formula [1].

Then, in step 13, as shown in Fig. 3B, a voltage V is applied between the first electrode 21a and the second electrode 22a to rotate the liquid crystal molecules 23a, and the liquid crystal molecules 23a and the monomer 24 are more uniformly mixed. Moreover, the disturbance of the liquid crystal molecules 23a and the monomer 24 can be increased by one of heat source heating and one light source illumination, but the monomer 24 is not completely polymerized, and the monomer 24 forms a polymer layer. . In other words, one of the applied heat source and a source of light will cause the monomer to prepolymerize or not cause any polymerization of the monomer 24. Of course, it should be noted at this time that if the magnitude of the applied voltage V does not allow the liquid crystal molecules 23a to rotate smoothly, the voltage may be applied in stages. For example, the first voltage is applied first, and then the second voltage is applied, and the first voltage and the second voltage are the same or different, but the first voltage and the second voltage are at the same level. The sum is the voltage when the original application is once V 14 200804271

II number: TW3053PA • The level. Alternatively, the first voltage is applied first, and then the second voltage is applied, and the first voltage and the second voltage are the same or different, but the first voltage and the second voltage are used. The sum of the sums is greater than the level of the voltage V when the original application is once. Furthermore, it must be noted that the steps of applying voltage or heating and illuminating can be applied simultaneously or sequentially at different times. For example, in the embodiment, one of heating and illumination is performed first, and then a voltage is applied. Alternatively, a voltage is applied first, and then one of heating and illumination is performed. Alternatively, one of the heating and illuminating actions is performed simultaneously with the application of the voltage. Further, the second electrode 22a can be further divided into a plurality of regions. The voltage applied to each region can be the same or different. The first electrode 21a and the second electrode 22a are, for example, a common electrode and a halogen electrode. It should be noted that the voltages V applied in steps 13 and 14 may be the same or different, depending on the arrangement of the liquid crystal molecules 23a or other requirements. Next, proceeding to step 14, as shown in Fig. 3C, the monomers 24 are polymerized upon application of this voltage V. That is, during the application of the voltage, the polymerization operation of the monomer 24 is performed. For example, based on the monomer 24 being a photosensitive monomer, the liquid crystal layer 23 may be irradiated on the surface of the upper surface of the second substrate 21 by an ultraviolet light 25 other light source capable of causing the polymerization of the monomer 24, so that the monomers 24 are The surfaces of the first alignment film 21b and the second alignment film 22b are polymerized into a polymer layer 24a. It is to be noted that, when the liquid crystal layer 23 is irradiated with ultraviolet light 25 other light source which causes polymerization of the monomer 24, the liquid crystal layer 23 may be entirely irradiated or partitioned. When the liquid crystal layer 23 is irradiated by the partition, the irradiation energy of each of the regions may be the same or different, and the energy of the partitioning of the liquid crystal layer 23 may be 15

200804271 Sanda number: TW3053PA The total amount of energy can be the same or different from the energy when all the liquid crystal layer 23 is irradiated. Then, in step 15, as shown in Fig. 3D, the voltage V' is removed and then the ultraviolet light 25 is removed or removed at the same time, and the liquid crystal display panel 26b is finally completed. At this time, the polymer layer 24a serves to provide the liquid crystal molecules 23a - a pretilt angle which is inclined with respect to the surfaces of the first electrode 21a and the second electrode 22a, and facilitates the liquid crystal molecules 23a to fall in at least one specific direction. Since the specific direction of the first alignment film 21b and the second alignment film 22b is existing before the formation of the polymer layer 24a, the pretilt direction of the liquid crystal molecules can be made more remarkable when the polymer layer 24a is formed. As to how the liquid crystal layer 23 in the above embodiment is sandwiched between the first substrate and the substrate 22, it will be described briefly below. Before the liquid helium layer 23 is interposed between the first substrate 21 and the second substrate 22, the non-display area (not, no) of the substrate of the first substrate 21 and the second substrate 22 is applied. Pivot glue. Then, the liquid crystal layer 23 is interposed between the first substrate 21 and the second 〇-〇 攸 U. At this time, the method of sandwiching the liquid crystal layer 23 is as follows. In the first mode, first, the group first substrate 21 and the second substrate 22 are paired. The sealant between the substrate φ ^ /, τ ′ and the substrate 21 has a /曰曰/inlet opening (not shown). Then, the liquid crystal layer 23 is injected between the first substrate 21 and the second substrate 22 through the liquid crystal of the sealant. ^ The method of first, and then the two substrates and then injecting the liquid crystal layer between the two substrates is a liquid crystal injection method. In the second mode, first, a sealant is applied to the non-display area (not shown) of the substrate of the first substrate 21 and the second substrate. Then, 16

200804271 · The iW3053PA is dropped into the liquid crystal layer 23 on the surface of one of the first substrate 21 and the second substrate 22 having the sealant, that is, the liquid crystal layer 23 is dropped into the region surrounded by the sealant on the substrate. Then, the liquid crystal layer 23 is interposed between the first substrate 21 and the second substrate 22 on the first substrate 21 and the second substrate 22, and the liquid crystal layer is first dropped onto a substrate and then the two substrates are assembled. It is called a one drop fill method (ODF). As for the chemical structure of the monomer 24, the following is exemplified here, but the technique of the present embodiment is not limited thereto. When "A" contains the chemical formula [2], [3], [4] or a combination thereof, and "R" is selected from an alkyl group, an alkoxy group, an ester group or a combination thereof, and When represented by the chemical formula [6], the monomer 24 is represented by the chemical formula [Η], [12], [13], [14], [15] or [16]:

17 [15] 200804271

Sanda number: TW3053PA

[16] wherein the left chain end functional groups of the chemical formulas [11], [13] and [15] may be selected from the group consisting of acrylates, methyl acrylates, and acrylate derivatives. A methacrylate group or a combination thereof. Further, the left chain end functional groups of the chemical formulas [12], [14], and [16] are selected from the group consisting of: a peptide, a compound, or a combination thereof. When "A" contains a chemical formula [2], [3], [4] or a combination of the above, r" is selected from a hospital base, an alkoxy group, an ester group or a combination thereof, and the lanthanide series When expressed by a combination of chemical formulas [5] and [6], a combination of chemical formulas [5] and [7], or a combination of chemical formulas [5] and [8], monomer 24 is represented by chemical formulas [17], [18], [19], [20], 1; 21] or R2] means:

X

18

200804271 Erda compiled. LW3053PA

19 [26] 200804271

Erda number: TW3053PA

[27]

[28] wherein the left chain end functional group of the chemical formula [23] to [25] may be selected from a vinyloxy group, a vinyloxy derivative or a combination thereof, and the chemical formula [26] to [28] The left chain end functional group may be selected from styrene, styryl derivatives or combinations thereof. When 1|' is represented by the chemical formula [2], [3] or [4], and 11, 11, and 圯, the combination of the chemical formulas [5] and [7] or the chemical formula [5] and [ The combination of 8] indicates that, when nRn and "B" are the same, the monomer 24 is represented by the chemical formula [29], [30] or [31]: 20 200804271

Sanda number: TW3053PA

twenty one

X

X 200804271 Number: TW3053PA

Wherein the left and right side chain end functional groups of the chemical formulas [29] to [31] may be selected from the group consisting of a vinyloxy group, a vinyloxy derivative or a combination thereof, and the left side of the chemical formula [32] to [34], The right side chain end functional group may be selected from a styryl group, a styryl derivative or a combination thereof. As to how the monomer 24 of the present embodiment is manufactured, six synthetic examples will be described, but the technique of the present embodiment is not limited thereto. The first synthesis example is an example of the chemical formula [11] (1-1) synthesis of 4-hydroxy-4'-ethyloxybiphenyl, as shown in the chemical formula [51] :

First, the reaction flask was filled with argon, and 8 mmol (mmol), 6 wt% sodium hydride and 200 ml of dry dimethoxyethane (DME) were placed in the reaction flask. . Next, when the reaction solution was cooled by ice, 2 mmol of 4,4'-dihydroxybiphenyl was added to the reaction solution. Then, warm 22 200804271

Second transport number: 1W3053PA • The reaction solution was allowed to reach room temperature, and the reaction solution was continuously stirred for 2 hours. Next, the reaction solution was cooled to minus 60 °C. Then, 1 mmol of bromoethane was gradually added dropwise to the reaction solution. Next, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred until the next day. Then, the reaction solution was poured into dilute hydrochloric acid, and the organic layer was extracted from the reaction solution through benzene. Next, the extracted organic layer was washed with distilled water and dried over anhydrous sodium sulfate. Then, the solvent was separated by distillation. Subsequently, the residue was purified by gel column chromatography, and crystallized from toluene to obtain 4-hydroxy-4 and ethyloxybiphenyl, as shown in the chemical formula [51]. (1-2) Synthetic monomers, as shown in chemical formula [52]:

First, fill the reaction flask with argon and add 1 millimole of 4-hydroxy-4'-ethyl〇xybiphenyl, 3 millimolar Triethylamine and 20 ml of methylene chloride were placed in the reaction flask. Next, when the reaction solution was cooled by ice, the methyl acryloyl chloride was gradually added dropwise to the reaction solution. Then, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred for 3 hours. Next, the reaction solution was poured into distilled water, and the organic layer was extracted from the reaction solution through benzene. Then, the extracted organic layer was washed with distilled water and dried over anhydrous sodium sulfate. Next, the solvent was separated by distillation. Then, the residue is purified by gel column chromatography and crystallized by acetone to obtain a monomer, as shown in Chemical Formula [52].

· TW3053PA " Show. Second synthetic example: an embodiment of the chemical formula [17] (2-1) synthesis of 4_(2-hydroxyethyloxy)_4,_ethyloxybiphenyl (4-(2_hydroxyethyl〇xy)_4,_ethyl 〇xybiphenyl), as shown in chemical formula [53]:

First, the reaction flask was filled with argon gas, and 4 mM, 60% by weight of sodium hydride and 200 liters of dried decyl oxyethylene were placed in the reaction flask. Next, when the reaction solution was cooled by ice, 丨 mmol of 4-light-based 4-ethyloxybiphenyl (4 y y 〇 〇 x 4 _ ethyi 〇 xybiphenyi) was further added to the reaction solution. Then, the reaction solution was warmed to room temperature, and the reaction > Next, the reaction solution was cooled to minus 6 Torr. [. Then, 1.5 Torr of bromoethanol was gradually added dropwise to the reaction solution. Next, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred until the next day. Then, the reaction solution was poured into dilute hydrochloric acid, and the organic layer was extracted from the reaction solution through benzene. Next, the extracted organic layer was washed with distilled water and dried over anhydrous sodium sulfate. Then, the solvent was separated by distillation. Next, the residue was purified by gel column chromatography, and crystallized from toluene to give 4-(2-hydroxyethyloxyethyloxybiphenyl) as shown in the chemical formula [53]. 2) Synthetic monomer, as shown in chemical formula [54]: 24 0 ~' 200804271

Sanda number: TW3053PA 〇C2H5 [54] First, the reaction flask is filled with argon and 1 millimolar of hydroxyethyloxy)-4'-ethyloxybiphenyl 4-(2_hydroxyethyloxy)-4, -ethyloxybiphenyl), 3 mmol of diethylamine and .20 ml of dichloromethane were placed in the reaction flask. Next, when the reaction solution was cooled by ice, 3 mmol of methylchloropropene was gradually added dropwise to the reaction solution. Then, the reaction solution was warmed to room temperature, and the reaction solution was stirred and stirred for 3 hours. Next, the reaction solution was poured into a steaming water and the organic layer was extracted from the reaction solution through benzene. Then, the organic layer extracted by main washing was washed with steaming water and dried over anhydrous sodium sulfate. Next, = by distillation to separate the solvent. Then, it was purified by gel column chromatography: residue, and crystallized by acetone to obtain a monomer, as shown in the chemical formula. Example of the third synthesis: a method of the chemical formula [23], although the same procedure (#3-1) and (1)) has the same procedure to obtain (2_glycosyloxy)-4'-ethyl Oxybiphenyl, omitted here no longer escape. (3-2) Synthetic monomer, as shown in chemical formula [55]:

J^°C2H5 [55] First, the reaction flask is filled with oxygen, and sodium nitride and milliliters are used. =曱=4 millimoles, 6_〇/. Inside. Next, when the reaction solution a is placed in the reaction bottle and the cold part of the ice is added, 1 millimole is added. 25 200804271

Erda number: TW3053PA 4-(2-hydroxyethyloxy)-4'-ethyloxybiphenyl in the reaction solution. Then, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred; 2 hours. Next, the reaction solution was cooled to minus 60 °C. Then, 3-mole 3-> 3-bromo-m-fluoropropane (3-bromo-m-ene) was gradually added dropwise to the reaction solution. Next, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred until the next day. Then, the reaction solution was poured into dilute hydrochloric acid, and the organic layer was extracted from the reaction solution through benzene. Next, the extracted organic layer was washed with distilled water and dried with anhydrous sodium sulfate. Then, the solvent was separated by distillation. Subsequently, the residue was purified by gel column chromatography and crystallized from toluene to obtain a monomer, as shown in the chemical formula [55]. The fourth synthesis example is the synthesis of 4-(2-bromoethyloxy)-4'-ethyloxybiphenyl (4-(2-bromoethyloxy)- in one embodiment of the chemical formula [26]. 4. ethyloxybiphenyl), as shown in chemical formula [56]:

First, the reaction flask was filled with nitrogen, and 8 mM, 60% by weight of sodium hydride and 200 ml of dry decyl oxyethylene were placed in the reaction flask. Next, when the reaction solution was cooled by ice, 2 mmol of 4-hydroxy-4'-ethyloxybiphenyl was further added to the reaction solution. Then, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred for 2 hours. Next, the reaction solution was cooled to minus 60 °C. Then, 2 mmol of 1,2-dibromoethane was gradually added dropwise to the reaction solution. Then, warm and reverse 26 200804271

Erzhi 3/t * iW3053PA * The solution should be allowed to reach room temperature and the reaction solution should be stirred until the next day. Then, the reaction solution was poured into dilute hydrochloric acid, and the organic layer was extracted from the reaction solution through benzene. Next, the extracted organic layer was washed with steam and dried with anhydrous sodium sulfate. Then, the solvent was separated by distillation. Next, the residue was purified by gel column chromatography to obtain 4-(2-bromoethyloxy)-4'-ethyloxybiphenyl as shown in the chemical formula [56]. (4-2) Synthetic monomer, as shown in chemical formula [57]:

First, the reaction flask was filled with argon gas, and 4 mmol, 60 wt% of sodium hydride, and 200 ml of dry didecyloxyethane were placed in the reaction flask. Next, when the reaction solution was cooled by ice, 1 mmol of 4-vinylphenol was further added to the reaction solution. Then, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred for 2 hours. Next, the reaction solution was cooled to minus 60 °C. Then, 1.5 mmol of 4-(2-bromoethyloxy)-4'-ethyloxybiphenyl was gradually added dropwise to the reaction solution. Next, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred until the next day. Then, the reaction solution was poured into dilute hydrochloric acid, and an organic layer was extracted from the reaction solution through benzene. Next, the extracted organic layer was washed with distilled water and dried with anhydrous sodium sulfate. Then, the solvent was separated by steaming. Next, the residue was purified by gel column chromatography to obtain a monomer as shown in the chemical formula [57]. Fifth synthetic example: an embodiment of the chemical formula P9] 27 200804271

Dimension: '1W3053PA (5-1) Synthesis of 4-(2-hydroxyethyloxy, 2, hydroxyethyloxy)biphenyl 1, 4-(2-hydroxyethyloxy)-4 ~(2-hydroxyethyloxy)biphenyl ), as shown in chemical formula [58]: H0~8~0H [58] First, the reaction flask is filled with argon and 4 mmol, 6 wt% sodium hydride and 200 ml dry 2 Mercaptoyloxyethane was placed in the reaction flask. Next, when the reaction solution was cooled by ice, 4,4'-dihydroxybiphenyl was added to the reaction solution. Then, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred for 2 hours. Next, the reaction solution was cooled to minus 60 °C. Then, 3 mmol of ethyl bromide was gradually added dropwise to the reaction solution. Next, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred until the day. Then, the reaction solution was poured into dilute hydrochloric acid, and the organic layer was extracted from the reaction solution through benzene. Next, the extracted organic layer was washed with distilled water and dried over anhydrous sodium sulfate. Then, the solvent was separated by distillation. Next, the residue is purified by gel column chromatography to obtain 4-(2-predylethyloxy)-4'-(2-pyridylethyloxy)biphenyl, as shown in the chemical formula [58]. Shown. (5-2) Synthetic monomer, as shown in the chemical formula [59]: 乂~. Set [59] First, the reaction flask was filled with argon, and 4 mmol, 60 wt% of sodium hydride and 200 ml of dry dimethyloxyethane were placed in the reaction flask. Then, when the reaction solution is cooled by ice, add 丨 莫 耳 28 200804271

Two-face tear: .i, W3053PA • 4_vinylbenzene in the reaction solution. Then, warm the reaction solution to the chamber /J2L and continue to disturb the reaction solution for 2 hours. Next, the reaction solution was cooled to minus 60 Torr. Then, 2 mmol of 4-(2-hydroxyethyloxy)4-(2-lightethylethyloxy)biphenyl was gradually added dropwise to the reaction solution. Next, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred until the next day. Then, the reaction solution was poured into dilute hydrochloric acid, and the organic layer was extracted from the reaction solution through benzene. Then, the extracted organic layer was washed with steam and washed with anhydrous sodium sulfate. Then, the solvent was separated by distillation. Next, the residue was purified by gel column chromatography to obtain a monomer as shown in the chemical formula [59]. Sixth Synthesis Example: Synthesis of 4-(2-bromoethyloxy)-4,-(2-bromoethyloxy)biphenyl (4-(2) in an embodiment (6-1) of Chemical Formula [32] -bromoethyloxy)-4'-(2_bromoethyloxy)biphenyl), as shown in chemical formula [60]: First, 'fill the reaction flask with argon and dry 4 mM, 60% by weight of sodium hydride and 200 ml. Dimercapto-oxyethane was placed in the reaction flask. Next, when the reaction solution was cooled by ice, 1 mmol of 4,4'-dihydroxybiphenyl was further added to the reaction solution. Then, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred for 2 hours. Next, the reaction solution was cooled to minus 60 °C. Then, 3 mmol of 1,2-dibromoethane was gradually added dropwise to the reaction solution. Next, warm the reaction solution to room temperature and continue to stir. 29

200804271 Sanda number: TW3053PA reaction solution until the next day. Then, the reaction solution was kneaded into dilute hydrochloric acid, and the organic layer was extracted from the reaction solution. After the pupa, ^ ^ ^ Μ瘵 水 法 法 extraction of the organic layer, and dried with anhydrous sodium sulfate. It is then distilled to separate the solvent. Next, the residue was purified through a gelatinization process to obtain 4-(2-bromoethyloxy)-4,-(2-bromoethyloxy)biphenyl, j. The formula [60] is shown. (6-2) Synthetic early body' as shown in chemical formula [61]:

First, the reaction flask was filled with argon gas, and 4 mmol, 6 wt% sodium hydride, and 200 ml of dry dimethoxy ethane were placed in the reaction flask. Next, when the reaction solution was cooled by ice, 1 mmol of 4-(2-ethylideneoxy)-4'-(2-pyridylethyloxy)biphenyl was further added to the reaction solution. Then, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred for 2 hours. Next, the reaction solution was cooled to minus 60 °C. Then, 3-bromo-2-propan-1- which is gradually added dropwise to the house is diluted into the reaction solution. Next, the reaction solution was warmed to room temperature, and the reaction solution was continuously stirred until the next day. Then, the reaction solution was poured into dilute hydrochloric acid, and the organic layer was extracted from the reaction solution through benzene. Next, the extracted organic layer was washed with distilled water and dried with anhydrous sodium sulfate. Then, the solvent was separated by distillation. Next, the residue was purified by gel column chromatography to obtain a monomer as shown in the chemical formula [61]. The dipole moment of the monomer 24 is on the short axis of the molecule, and the magnitude of the dipole moment of the monomer 24 needs to be controlled between 〇~5 Debye (D), 30 200804271 Sanda number: TW3053PA The good place is between 0 and 3. Among them, 1 Debye is equal to 3·33564 χ 1〇 _3〇库舍*米(C*m). The reason why the dipole moment of the monomer 24 is between 〇 and 3 is controlled, and since the dipole moment of the liquid crystal molecule 23a is also about 3, the mutual solubility of the liquid crystal molecules 23a and the monomer 24 can be increased. Further, the dipole moment of the unit 24 should not be too large or too small to affect the alignment of the electric molecules 23a generated when the voltage v is applied between the first electrode 仏 and the second electrode 22a. When 0 τ is an alkoxy group, it can be expressed as 0CmIl2m+], and the m value can be controlled between 1 and 10. The adjustment of the length of the carbon chain of T can adjust the mutual solubility of the body 24 and the liquid crystal molecule 23a, but the carbon bond of "R," does not affect the alignment force of the polymer 24a with respect to the liquid crystal molecule. a functional group such as a methacrylic acid group, a propyl group, a propyl group, a propylene group derivative, a methyl propyl group derivative, a woven organism, a acetyl group derivative, and a benzene combination. Absorbing light energy or 埶" into the above compound, the degree of knowledge of the polymer base" in this example, the B scale a ^ from the derivative, the stupid ethylene derivative or the above group 4 = B, in order to maintain Monomer 24 polymerizes into polymer 24a ¥=Early force®24's knot monomer Second:= ί: Sometimes it is polymerized into a polymer layer... It is called a stabilizer or accelerator, it is called The precursor (pre_(4) = u some of the above-described embodiments of the monomer or the two polymerized polymer layers 24a (four) are preferably provided so that 31 200804271

达305号: TW3053PA " In addition, it should be noted that one of the second electrode 22a and the first electrode 21a disclosed in the above embodiment of the present invention is intended to assist the pretilt direction or arrangement of the liquid crystal molecules 2 3 a . The direction can be more k-shaped to form a multi-domain alignment, so that one of the second electrode 22a and the first electrode 21a can have a plurality of openings (not shown) to make the second electrode One of 22a and the first electrode 21a forms a polygonal shape. The shapes formed by the openings are, for example, a comb shape, a branch shape, an X shape, a W shape, a V shape, or the like, or a combination thereof. Furthermore, if the material used for the second electrode 22a is a transparent material, the liquid crystal display panel is not a transparent liquid crystal display panel. When the material used in the square electrode 2 2 a is a reflective material, the liquid crystal display panel is called a reflective liquid crystal display panel. If the material used for the second electrode 22a is a transparent material and a reflective material used in combination or partition, the liquid crystal display panel is referred to as a transflective liquid crystal display panel. The transparent material comprises indium oxide, tin oxide, indium tin oxide, or the like, or a combination thereof. The reflective material comprises gold, silver, copper, aluminum, titanium, button, steel, condensed, crane, nitride of the above metal, alloy of the above metal, or a group of the above-mentioned embodiments of the present invention and the application thereof The method of manufacturing a liquid crystal display panel, the design of which has a single structure, can increase the degree of disturbance of the monomer: and avoid the stacking phenomenon of the monomers. In this way, if it is hard, it will be more uniformly dissolved with the liquid crystal molecules to prevent the liquid crystal state of the liquid crystal 2 from becoming solid. In addition, liquid crystal display can be avoided: the lattice defect caused by the poor mutual solubility of the liquid crystal molecules and the liquid crystal molecules can directly improve the display quality of the liquid crystal display panel. Yaheda 32 200804271

。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 。 It will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention. Therefore, the scope of the invention is defined by the scope of the appended claims. 33 200804271

1 = -3⁄43⁄43⁄43⁄4 : FW3053PA _ [Simple Description of the Drawings] Fig. 1 is a flow chart showing a method of manufacturing a liquid crystal display panel in accordance with a preferred embodiment of the present invention. 2A to 2D are cross-sectional views showing a process of a method of manufacturing a liquid crystal display panel according to a first embodiment of the present invention. 3A to 3D are cross-sectional views showing a process of a method of manufacturing a liquid crystal display panel according to a second embodiment of the present invention. [Main element symbol description] 21: First substrate 21a; First electrode 21b: First alignment film 22: Second substrate 22a: Second electrode 22b: Second alignment film 23: Liquid crystal layer 23a: Liquid crystal molecule 24: Monomer 24a: polymer 25: ultraviolet light 26a, 26b · liquid crystal display panel V · voltage 34

Claims (1)

200804271 Sanda number: TW3053PA * X. Patent application scope: 1. A monomer, represented by chemical formula [1]; B-A-R [1] where "A" is selected from the chemical formula [2], [3] ], [4] or a combination of the above; Wherein at least one of ''B' and "R' is selected from the group consisting of an alkyl group, an alkoxy group, an ester group, a chemical formula [5], [6], [7], [8] or a combination thereof; Wherein "T" is selected from the group consisting of oxygen, nitrogen or a combination thereof, and "X" is selected from the group consisting of hydrogen, an alkyl group, an elemental element, a cyano group or a combination thereof, and the η system is a positive integer. 2. The monomer of claim 1, wherein "R" is selected from the group consisting of an alkyl group, an alkoxy group, an ester group, or a combination thereof, and the ''Β' is selected from the formula [5], [6], [7], [8] or a combination thereof. 3. The monomer according to claim 1, wherein ''Β' and ''Rn are selected from the chemical formula [5], [ 6], [7], [8] or a combination of the above, and the substituents selected for ''B'' and '11'' are the same. 4. The monomer according to claim 1, wherein η is 2 35 200804271 Sanda number: TW3053PA 〜5 is a positive integer. 5. The monomer as claimed in claim 1, wherein "X" is selected from thiol, fluorine, chlorine or a combination thereof 6. The monomer according to claim 1, wherein "R" is OCmH2m+i, and m is a positive integer of 1 to 10. 7. The monomer as recited in claim 1 has a dipole moment, which is substantially 0 to 3 Debye (D) 〇8. The monomer described in Item 1 is represented by the chemical formula [11], [12], [13], [14], [15] or [16]: X 36 200804271 Sanda number: TW3053PA 9 · The monomer described in item 1 of the patent application is expressed by the chemical formula [17], [18], [19], R0], [21] or [22]: 37 200804271 Sanda number: TW3053PA 10. The monomer as described in item 1 of the patent application is in the chemical formula. [25] 11· The monomer described in item 1 of the patent application is expressed by the chemical formula [26], [27] or 08]: 38 200804271 II number: TW3053PA 12. The monomer as described in item 1 of the patent application is expressed by the chemical formula [29], [30] or [31]: 39 X X200804271 Sanda number: TW3053PA 13 · The monomer described in item 1 of the patent application is expressed by the chemical formula [32], [33] or [34]: 14) A method of manufacturing a liquid crystal display panel, comprising: 40 X 200804271. The second mobile number: i'W3053PA provides a first substrate having a first electrode and a second substrate having a second electrode; and a liquid crystal is interposed Between the first substrate and the second substrate, the liquid crystal layer is located between the first electrode and the second electrode, the liquid crystal layer has a plurality of liquid crystal molecules and a plurality of monomers, each of the single systems The chemical formula [1] represents B-A-R [1] wherein the lanthanide is selected from the chemical formula [2], [3], [4] or a combination thereof; Wherein at least one of "Β" and "R" is selected from the group consisting of an alkyl group, an alkoxy group, an ester group, a chemical formula [5], [6], [7], [8] or a combination thereof; Wherein "Τ" is selected from the group consisting of oxygen, nitrogen or a combination thereof, and "X" is selected from the group consisting of ruthenium, an alkyl group, a halogen element, a cyano group or a combination thereof, and the η system is a positive integer. 15. The method of claim 14, further comprising: applying a voltage between the first electrode and the second electrode. 16. The method of claim 15, further comprising: 41 200804271 Erda number: TW3053PA ^ Polymerizing the monomers upon application of the voltage. 17. The method of claim 16, further comprising: removing the voltage. 18. The method of claim 14, wherein "R" is selected from the group consisting of an alkyl group, an alkoxy group, an ester group, or a combination thereof, and the 'Έ" is selected from the group consisting of the chemical formulas [5], [6] ], [7], [8] or a combination of the above. 19. The method of claim 14, wherein "B" and nR" are selected from the chemical formula [5], [6], [ 7], [8] or a combination of the above, and the substituents selected by "Βπ and '义义" are the same. The method of claim 14, wherein the single system has a dipole The dipole moment, the dipole moment is substantially 0 to 3 Debye (D). 21. The method of claim 14, wherein n is a positive integer of 2 to 5. The method of claim 14, wherein "X" is selected from the group consisting of methyl, fluoro, chloro or a combination thereof. 23. The method of claim 14, wherein "R" is OCmH2m+i, and m is a positive integer from 1 to 10.