Colored photosensitive resin composition, color filter and image display device

A technology of photosensitive resin and composition, which is applied in the direction of instruments, optics, and optomechanical equipment, etc. It can solve problems such as difficulty in forming target height difference, poor surface, and insufficient surface, and achieve minimum surface roughness, physical properties and performance. The effect of high productivity

Pending Publication Date: 2019-08-06
DONGWOO FINE CHEM CO LTD
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AI-Extracted Technical Summary

Problems solved by technology

[0007] However, in the case of forming a black matrix, columnar spacer, or black columnar spacer using a conventional photosensitive resin composition, leveling (flatnes...
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Method used

Above-mentioned black matrix, columnar spacer, black matrix integral type columnar spacer are owing to utilize and comprise viscosity to be below 2.0mPa s when 20 ℃, vapor pressure is below 3.0mmHg when 20 ℃, and satisfy above-mentioned formula 1 It is manufactured from a colored photosensitive resin composition using a solvent, so it has excellent optical effects for basic light-shielding properties, and has excellent elastic modulus and reliability, excellent leveling, and excellent formation of height differences, making surface defects and surface roughness degree to minimize such advantages.
Based on the overall weight of the above-mentioned colored photosensitive resin composition, the content of the above-mentioned photopolym...
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Abstract

The present invention relates to a colored photosensitive resin composition, a color filter including a black matrix and/or a column spacer manufactured thereby, and an image display device includingthe color filter. According to the present invention, the viscosity of each solvent is equal to or less than 2.0 mPa*s at 20 DEG C and the vapor pressure of each solvent is equal to or less than 3.0 mmHg at 20 DEG C, and an entire solvent satisfies formula 1 (shown in the description), wherein Ai is the viscosity (mPa*s) of each solvent at 20 DEG C, Bi is the vapor pressure (mmHg) of each solventat 20 DEG C, and Mi is a weight ratio of each solvent in the entire solvent. According to the present invention, the colored photosensitive resin composition has excellent levelling properties, thereby being able to form a desired step and effectively suppressing surface defect or surface roughness of a formed black matrix, column spacer, or black matrix-integrated column spacer.

Application Domain

Technology Topic

Image

  • Colored photosensitive resin composition, color filter and image display device
  • Colored photosensitive resin composition, color filter and image display device
  • Colored photosensitive resin composition, color filter and image display device

Examples

  • Experimental program(3)

Example Embodiment

[0142] Synthesis example: Synthesis of alkali-soluble resin (B)
[0143] Put 277 g of methoxybutyl acetate into a 1L separable flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen introduction tube. After the temperature is raised to 80°C, it is added dropwise over 5 hours The 3,4-epoxy tricyclic [5.2.1.0 2,6 ]Decane-9-yl acrylate and 3,4-epoxy tricyclic [5.2.1.0 2,6 ] Decane-8-yl acrylate mixture [50:50 (molar ratio)] [The compound represented by the above chemical formula 1, R a =H] A mixed solution of 301 g, 49 g of methacrylic acid, and 23 g of azobisdimethylvaleronitrile dissolved in 350 g of methoxybutyl acetate, and matured for 3 hours to obtain a copolymer solution [solid content ( NV) 35.0% by weight]. The acid value (dry) of the obtained copolymer was 69.8 mgKOH/g, the weight average molecular weight (Mw) was 9,500, and the degree of dispersion Mw/Mn was 1.9.
[0144] [Chemical formula 1]
[0145]

Example

[0146] Examples and Comparative Examples: Manufacture of colored photosensitive resin composition
[0147] The colored photosensitive resin composition was produced according to the composition of Table 1 below. At this time, the physical and chemical properties of the solvent are shown in Table 2 below.
[0148] [Table 1]
[0149]
[0150] [Table 2]
[0151] No. species Viscosity (mPa·s) Vapor pressure (mmHg) |Δ(Viscosity-Vapor Pressure)| 1 Propylene glycol methyl ether acetate (PGMEA) 1.3 2.8 1.5 2 Ethylene glycol monoethyl ether acetate (EGA) 1.3 1.2 0.1 3 3-Methoxybutyl Acetate (3-MBA) 0.7 1.1 0.4 4 Diethylene glycol ethyl methyl ether (MEDG) 1.2 0.7 0.5 5 1,2-Propanediol diacetate (PGDA) 2.9 0.2 2.6 6 Propylene glycol monomethyl ether (PGME) 1.9 8.7 6.8

Example Embodiment

[0152] Experimental example
[0153] (1) Production of colored substrate
[0154] After washing a 5 cm×5 cm glass substrate (manufactured by Corning Incorporated) with a neutral lotion and water, it was dried. The colored photosensitive resin compositions produced in the examples and comparative examples were spin-coated on the glass substrates so that the final film thickness became 3.0 μm, and pre-baked at 100° C., dried for 90 seconds, and removed the solvent. Then, with 35mJ/cm 2 Exposure is exposed to form a pattern, and the non-exposed part is removed using an aqueous alkali solution. Next, post-baking was performed at 230°C for 30 minutes to produce a colored substrate.
[0155] (2) Measurement of viscosity
[0156] Using Brookfield Viscometer DV-I+, manufactured by Brookfield Viscometer at 20°C, the viscosity of the solvent and the colored photosensitive resin composition of Examples and Comparative Examples was measured.
[0157] (3) Measurement of optical characteristics (optical density, UV-vis)
[0158] For the cured film of the colored substrate manufactured by the above experimental example, the transmittance at 550 nm was measured with an optical densitometer (361T, manufactured by X-rite), and the optical density for a thickness of 1 μm was obtained, and it is shown in Table 3 below in.
[0159] In addition, with respect to the cured film formed as described above, the light characteristics were evaluated by UV-vis (UV-2550; manufactured by Shimadzu Corporation). At this time, the evaluation criteria are as follows, and the results are shown in Table 3 below.
[0160]
[0161] ○: Excellent, less than 10% light transmittance
[0162] △: Insufficient, light transmittance is greater than 10% and 12% or less
[0163] ×: Deterioration, light transmittance is greater than 12%
[0164]
[0165] ○: Excellent, light transmittance 15% or more
[0166] △: Insufficient, light transmittance is 13% or more and less than 15%
[0167] ×: deteriorated, light transmittance is less than 13%
[0168] (4) Measurement of flatness (DOP: Degree of Planarization)
[0169] The patterned substrate (5cm×5cm glass substrate) was spin-coated with the colored photosensitive resin composition produced in the above-mentioned Examples and Comparative Examples so that the final film thickness became 3.0 (±0.2) μm, respectively, at 100°C Before firing and drying for 90 seconds, the solvent is removed to form a pre-cured film. After that, with 35mJ/cm 2 The exposure amount exposes the entire surface to form an entire surface pattern, and develops using an alkali aqueous solution. Next, post-firing was performed at 230°C for 130 minutes to produce a whole-surface colored substrate. For the manufactured whole-surface colored substrate, use a film thickness meter (DEKTAK6M, manufactured by Veeco) to measure the thickness of the patterned part and the patternless part at the bottom, and then measure the flatness by using the pattern thickness of the lower substrate measured in advance. (DOP), and are described in Table 3 below.
[0170]
[0171] On a substrate prepared in advance so that the thickness of the lower pattern becomes 1.17 μm, coating is performed so that the thickness of the flattened portion without the lower pattern becomes 3.20 μm, and the flatness is measured by the following formula 3.
[0172] [Equation 3]
[0173]
[0174] In the above formula 3,
[0175] Refers to the thickness of the lower pattern, Refers to Value, It refers to the thickness of the part without a pattern in the lower part of the flat film formed from the colored photosensitive resin composition, It refers to the thickness of the part excluding the highest point of the lower pattern from the highest point of the flat film formed from the colored photosensitive resin composition.
[0176] ◎: Very excellent, 30% or more and less than 60%
[0177] ○: Excellent, 15% or more and less than 30%, 60% or more and less than 75%
[0178] △: less than 10% or more and less than 15%, 75% or more and less than 85%
[0179] ×: worse than 10%, 85% or more
[0180] (5) Evaluation of VCD surface unevenness
[0181] The colored photosensitive resin compositions produced in the above examples and comparative examples were spin-coated so that the final film thickness became 3.0 (±0.2) μm, and dried under reduced pressure (Vacuum Dry: VCD) until 65 Pa was measured. After that, the coated surface was confirmed with an optical microscope, and the surface defects caused by the decompression of the VCD and the tact time (Tacttime) were measured, and they were recorded in Table 3. figure 1 This is an example of an evaluation image that classifies VCD surface unevenness based on the following evaluation criteria.
[0182]
[0183] ◎: Very good, less than 5 surface irregularities
[0184] ○: Excellent, with 5 or more and less than 10 surface irregularities
[0185] △: Insufficient, surface irregularities are more than 10 and less than 20
[0186] ×: Deterioration, surface unevenness is more than 20
[0187] (6) Determination of reliability
[0188] The glass substrate manufactured in (2) above was cut into 3×3 cm, and the glass substrate was immersed in an NMP solution, and then heated at 100°C for 60 minutes. After that, only the NMP solution was extracted, and the degree of elution in the NMP solvent was measured for absorbance using a UV-vis spectrometer, and the results are shown in Table 3 below. At this time, the evaluation criteria are as follows.
[0189]
[0190] ○: Excellent, absorbance is 0.5 or less
[0191] △: Insufficient, absorbance is greater than 0.5 and 0.8 or less
[0192] ×: Deterioration, absorbance is greater than 0.8
[0193] (7) Evaluation of elastic recovery rate
[0194] Regarding the substrate manufactured by the above-mentioned (1) manufacturing of the colored substrate, the thickness and width of the pattern were measured using SNU (SIS-2000, SNU Corporation) in a reference state. After that, using a flat indenter of a hardness tester (Nano-indenter HM500, manufactured by Fisher), press at a speed of 2mN/sec until the pattern is deformed by 1μm, and hold at the position where the deformation is 1μm for 5 seconds (Holding Time). After that, the thickness and width of the pattern were measured by SNU, and the elastic recovery rate was measured from the thickness change of the front and back patterns. The specific evaluation criteria are as follows, and the evaluation results are described in Table 3 below.
[0195]
[0196] ◎: Very good, 98% or more
[0197] ○: Excellent, 96% or more and less than 98%
[0198] △: insufficient, 94% or more and less than 96%
[0199] ×: worse than 94%
[0200] [table 3]
[0201]
[0202] Referring to Table 3 above, it can be seen that when the value of formula 1 is satisfied, the flatness of the coating film is excellent, which is conducive to the formation of the designed height difference, and does not increase the surface unevenness caused by the VCD process and the process time. Features suitable for mass production.
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PUM

PropertyMeasurementUnit
Viscosity<= 2.0mPa·s
Acid value69.8mgKOH/g
Thickness3.2µm
tensileMPa
Particle sizePa
strength10

Description & Claims & Application Information

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