CN112987510A - Interlayer immersion type photoetching method using negative black photoresist - Google Patents
Interlayer immersion type photoetching method using negative black photoresist Download PDFInfo
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- CN112987510A CN112987510A CN202110252945.2A CN202110252945A CN112987510A CN 112987510 A CN112987510 A CN 112987510A CN 202110252945 A CN202110252945 A CN 202110252945A CN 112987510 A CN112987510 A CN 112987510A
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- 229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 72
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000011229 interlayer Substances 0.000 title claims abstract description 13
- 238000001259 photo etching Methods 0.000 title description 8
- 238000007654 immersion Methods 0.000 title description 3
- 239000007788 liquid Substances 0.000 claims abstract description 39
- 238000000671 immersion lithography Methods 0.000 claims abstract description 13
- 239000010410 layer Substances 0.000 claims abstract description 12
- 239000000758 substrate Substances 0.000 claims abstract description 12
- 229920002545 silicone oil Polymers 0.000 claims abstract description 10
- 239000003960 organic solvent Substances 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 12
- 238000001723 curing Methods 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- 238000003825 pressing Methods 0.000 claims description 8
- 238000003848 UV Light-Curing Methods 0.000 claims description 7
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 claims description 5
- 229920006037 cross link polymer Polymers 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000003504 photosensitizing agent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 4
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 238000004528 spin coating Methods 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 239000000243 solution Substances 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002508 contact lithography Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000001579 optical reflectometry Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000002522 swelling effect Effects 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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Classifications
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/70—Microphotolithographic exposure; Apparatus therefor
- G03F7/70216—Mask projection systems
- G03F7/70341—Details of immersion lithography aspects, e.g. exposure media or control of immersion liquid supply
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- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
Abstract
The invention relates to an interlayer immersion lithography method using a negative black photoresist. The negative black photoresist is coated on the surface of a substrate and is softly baked, a layer of high-refractive-index liquid is flattened above the substrate, the mask is pressed by 1-3 kg of force, UV exposure is carried out, the residual high-refractive-index liquid is washed away by using an organic solvent, and subsequent development and complete curing are carried out. Compared with the prior art, the resolution can be greatly improved only by clamping a thin high-refractive-index liquid layer between the photoresist and the mask without the contact of a lens and the liquid, so that the cleaning process is greatly simplified. Most of the high-refractive-index liquid is silicone oil, and the properties of the photoresist and the mask cannot be influenced after cleaning. The techniques can be used to fabricate high resolution electronic devices, such as OLED black pixel definition layers.
Description
Technical Field
The invention belongs to the technical field of display, and particularly relates to a photoetching method using negative black photoresist.
Background
The OLED display device has the advantages of self-luminescence, no need of a backlight source, high contrast, thin thickness, wide viewing angle, high reaction speed, capability of being used for a flexible panel and the like, and is considered as a new application technology of a next-generation flat panel display. At present, for the preparation of the OLED display device, vacuum evaporation and printing technologies are generally adopted, which is currently the mainstream development technology in the world. The printing technology is considered to be an effective way for solving the high cost of the OLED and realizing a large area, has a wide development prospect, can be combined with a liquid functional material and advanced printing equipment to manufacture the OLED display screen, and can improve the utilization rate and the production efficiency of the material, reduce the manufacturing cost and improve the productivity.
Currently, the industry mainly uses a polyimide-based positive photoresist to manufacture a pixel defining layer of an Organic Light Emitting Diode (OLED), however, since the positive photoresist does not contain a black pigment, the pixel defining layer of the OLED is a yellow or brown translucent polymer film, so that the OLED device exhibits high external light reflectivity, thereby reducing visibility. Therefore, in order to improve the above problems, the OLED pixel defining layer can be fabricated using a high heat resistant negative black photoresist, and the black defining layer of high optical density (greater than 1/μm) perfectly solves the problem of external light reflection. However, the negative photoresist based on the polymer curing mechanism cannot obtain a high resolution pattern, mainly due to the swelling effect of the developer on the cured part.
Disclosure of Invention
The invention aims to solve the problem that the resolution ratio of a pattern obtained by the existing photoetching method using a negative black photoresist is insufficient, and provides a photoetching method using the negative black photoresist, which can obtain a high-resolution pattern, and specifically comprises the following steps:
1. spin coating a photoresist: spraying negative black photoresist on the surface of a substrate, accelerating to rotate a tray to reach the required rotation speed of 5000rpm, and keeping rotating for 1 minute at the speed;
2. soft baking: baking the substrate coated with the photoresist at a constant temperature of 110 ℃ for 100 seconds until the substrate is not sticky;
3. dropping high refractive index liquid: dripping liquid with refractive index larger than 1.3 on the surface of the photoresist after soft baking, wherein the dripping amount is not less than 50 mu L/cm2Forming a high refractive index liquid interlayer between the photoresist and the mask;
4. and (3) pressing a mask upwards: pressing the mask on the high-refractive-index liquid interlayer with a force of 1-3 kg;
5. UV exposure: the photoresist pressed on the upper mask was irradiated with UV light at an amount of 80mJ/cm2(e.g., incident power of 8mW/cm2Exposure time 10 seconds); after exposure, washing off residual high-refractive-index liquid on the surface of the photoresist by using an organic solvent, and drying by using nitrogen; after all samples are prepared, washing off residual high-refractive-index liquid on the surface of the mask by using an organic solvent and drying by using nitrogen;
6. hard baking: after removing the high-refractive-index liquid, continuously baking for 120 seconds at the constant temperature of 100 ℃;
7. and (3) developing: developing for 60 seconds by adopting TMAH aqueous solution with the weight percentage of 2.3%;
8. and (3) curing: dried at a constant temperature of 230 c and heat treated for 30 minutes to complete curing.
Preferably, the high refractive index liquid is silicone oil having a refractive index of 1.4.
Preferably, the negative black photoresist comprises a UV photoinitiator, a photosensitizer, a cross-linked polymer containing alternating carboxyl and carbon-carbon double bonds, a UV curing monomer, a black dye dispersion liquid and a solvent;
preferably, the mass percentage of the UV photoinitiator in the negative black photoresist is 1-8 wt%;
preferably, the mass percentage of the photosensitizer in the negative black photoresist is 1-5 wt%;
preferably, the mass percentage of the cross-linked polymer solution containing alternate carboxyl and carbon-carbon double bonds in the negative black photoresist is 10-30 wt%;
preferably, the mass percentage of the UV curing monomer in the negative black photoresist is 5-10 wt%;
preferably, the mass percentage of the black dye dispersion liquid in the negative black photoresist is 40-60 wt%;
preferably, the total mass percentage of the solvent in the negative black photoresist is 40 wt% to 80 wt%.
As a further preference, the UV curing monomer is one or more of dipentaerythritol hexaacrylate DPHA, pentaerythritol triacrylate PETA, trimethylolpropane triacrylate TMPTA; further preferred is pentaerythritol triacrylate PETA.
As a further preference, the solvent is one or more of propylene glycol monomethyl ether acetate PGMEA, N-methylpyrrolidone NMP, N-dimethylacetamide DMAc; further preferred is PGMEA.
Preferably, the residual high refractive index liquid is washed away using n-hexane after completion of the exposure.
The negative black photoresist used in the method has excellent photosensitivity and good adhesiveness; in the exposure process of the negative black photoresist, a UV photoinitiator and a photosensitizer form free radicals to attack a cross-linked polymer containing alternating carboxyl and carbon-carbon double bonds and a UV curing monomer, so that chain growth is carried out to form a highly cross-linked high molecular weight polymer. The high-molecular-weight polymer which is highly crosslinked is formed in the area exposed to the UV light, and is not dissolved by alkaline aqueous solution TMAH in the developing process, and the unexposed area is a monomer and an oligomer which contain a large amount of carboxyl and can be dissolved by the TMAH, so that the black pixel defining layer pattern of the OLED device can be realized.
Compared with the prior art, the method can realize the great improvement of the resolution ratio only by clamping a thin high-refractive-index liquid layer between the photoresist and the mask. Most of the liquid is silicone oil, and the properties of the photoresist and the mask cannot be influenced after cleaning. The technique can be used to fabricate high resolution electronic devices, such as OLED black pixel definition layers, which can form high resolution black pixel definition layer patterns with excellent visibility.
Compared with the traditional negative photoresist photoetching technology, the photoetching technology for the negative photoresist changes the air medium above the photoresist into the high-refractive-index liquid with a certain thickness, and improves the resolution ratio by utilizing the shortening of the wavelength of the UV light after passing through the high-refractive-index medium. Whether contact or non-contact photoetching is adopted, as long as the light receiving surface of the photoresist is in contact with a medium with high refractive index, the effect of shortening the wavelength of the incident photoresist can be achieved.
Compared with the traditional immersion lithography technology, the interlayer immersion lithography technology only sandwiches a small amount of high-refractive-index liquid between the mask and the photoresist by using a certain pressure, thereby achieving three advantages. First, the amount of high refractive index liquid used is greatly reduced. Secondly, the distance consistency between the mask and the photoresist is greatly improved due to the adhesion effect of the high-refractive-index liquid between the mask and the photoresist. Thirdly, the liquid does not need to be in contact with the lens, thereby greatly simplifying the cleaning process.
Drawings
FIG. 1 is a schematic illustration of the principles of photolithography in accordance with the present invention.
FIG. 2 is a comparison of a pattern formed by conventional contact lithography of a comparative example and interlayer immersion contact lithography of example 2 of the present invention; wherein (a)8 μm, air; (b)8 μm, silicone oil; (c)12 μm, air; (d)12 μm, silicone oil.
Detailed Description
To further illustrate the technical means and effects of the present invention adopted to achieve the predetermined objects, the following detailed description of the embodiments, structures, features and effects according to the present invention will be made with reference to the accompanying drawings and preferred embodiments.
Example 1-example 3:
1. preparing negative black photoresist according to different formulas: the specific formula is shown in table 1, and after the components of the photoresist are physically mixed, the components are fully stirred and subjected to ultrasonic treatment to form good dispersion, namely, the negative black photoresist is formed;
2. spin coating a photoresist: spraying negative black photoresist on the surface of a substrate, accelerating to rotate a tray to reach the required rotation speed of 5000rpm, and keeping rotating for 1 minute at the speed;
3. soft baking: baking the substrate coated with the photoresist at a constant temperature of 110 ℃ for 100 seconds until the substrate is not sticky;
4. dropping high refractive index liquid: dropping silicone oil (Shin-Estu, Japan) with refractive index of 1.4 on the surface of the photoresist after soft baking, with dropping amount of not less than 50 μ L/cm2Forming a silicone oil interlayer between the photoresist and the mask;
5. and (3) pressing a mask upwards: pressing a mask on the high-refractive-index liquid interlayer with a force of 1-3 kg, wherein the sizes of the mask patterns are 8 micrometers and 12 micrometers respectively;
6. UV exposure: the photoresist pressed on the upper mask was irradiated with UV light at an amount of 80mJ/cm2(e.g., incident power of 8mW/cm2Exposure time 10 seconds); after exposure, washing off residual high-refractive-index liquid on the surface of the photoresist by using an organic solvent, and drying by using nitrogen; after all samples are prepared, the residual high-refractive-index liquid on the surface of the mask is washed away by using an organic solvent and dried by using nitrogen.
7. Hard baking: after removing the high-refractive-index liquid, continuously baking for 120 seconds at the constant temperature of 100 ℃;
8. and (3) developing: developing for 60 seconds by adopting TMAH aqueous solution with the weight percentage of 2.3%;
9. and (3) curing: dried at a constant temperature of 230 c and heat treated for 30 minutes to complete curing.
Comparative example
1. Negative black photoresist was formulated as in example 2: the specific formula is shown in table 1, and after the components of the photoresist are physically mixed, the components are fully stirred and subjected to ultrasonic treatment to form good dispersion, namely, the negative black photoresist is formed;
2. spin coating a photoresist: spraying negative black photoresist on the surface of a substrate, accelerating to rotate a tray to reach the required rotation speed of 5000rpm, and keeping rotating for 1 minute at the speed;
3. soft baking: baking the substrate coated with the photoresist at a constant temperature of 110 ℃ for 100 seconds until the substrate is not sticky;
4. and (3) pressing a mask upwards: pressing the mask with a force of 1-3 kg, wherein the sizes of the mask patterns are respectively 8 μm and 12 μm;
5. UV exposure: the photoresist pressed on the upper mask was irradiated with UV light at an amount of 80mJ/cm2(e.g., incident power of 8mW/cm2Exposure time 10 seconds);
6. hard baking: continuously baking for 120 seconds at the constant temperature of 100 ℃;
7. and (3) developing: developing for 60 seconds by adopting TMAH aqueous solution with the weight percentage of 2.3%;
8. and (3) curing: dried at a constant temperature of 230 c and heat treated for 30 minutes to complete curing.
Table 1: photoresist composition
As shown in fig. 2: when the mask size was 8 μm, the pattern (a) formed by ordinary contact lithography did not see any pattern, while the pattern (b) with the silicone oil interlayer exhibited a clearer square pattern. When the mask size was 12 μm, (d) with the silicone oil had been very close to the mask pattern, and (c) there was still an excessive crosslinking phenomenon caused by the diffracted UV light. It is evident that the latter resolution is much higher than the former.
Although the present invention has been described with reference to the preferred embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but is intended to cover various modifications, equivalents and alternatives falling within the spirit and scope of the invention.
Claims (10)
1. An interlayer immersion lithography method using a negative black photoresist, characterized in that: the method specifically comprises the following steps:
(1) spin coating a photoresist: spraying negative black photoresist on the surface of a substrate, accelerating to rotate a tray to reach the required rotation speed of 5000rpm, and keeping rotating for 1 minute at the speed;
(2) soft baking: baking the base material coated with the photoresist at a constant temperature of 110 ℃ until the base material is not sticky;
(3) dropping high refractive index liquid: dripping liquid with refractive index larger than 1.3 on the surface of the photoresist after soft baking, wherein the dripping amount is not less than 50 mu L/cm2Between the photoresist and the maskA high refractive index liquid interlayer is formed between the two layers;
(4) and (3) pressing a mask upwards: pressing the mask on the high-refractive-index liquid interlayer with a force of 1-3 kg;
(5) UV exposure: the photoresist pressed on the upper mask was irradiated with UV light at an amount of 80mJ/cm2(e.g., incident power of 8mW/cm2Exposure time 10 seconds); after exposure, washing off residual high-refractive-index liquid on the surface of the photoresist by using an organic solvent, and drying by using nitrogen; after all samples are prepared, washing off residual high-refractive-index liquid on the surface of the mask by using an organic solvent and drying by using nitrogen;
(6) hard baking: after removing the high-refractive-index liquid, continuously baking for 120 seconds at the constant temperature of 100 ℃;
(7) and (3) developing: developing for 60 seconds by adopting TMAH aqueous solution with the weight percentage of 2.3%;
(8) and (3) curing: dried at a constant temperature of 230 c and heat treated for 30 minutes to complete curing.
2. The sandwich immersion lithography method as claimed in claim 1, characterized in that: the high-refractive-index liquid adopts silicone oil with the refractive index of 1.4.
3. The sandwich immersion lithography method as claimed in claim 1, characterized in that: the negative black photoresist comprises a UV photoinitiator, a photosensitizer, a cross-linked polymer containing alternating carboxyl and carbon-carbon double bonds, a UV curing monomer, black dye dispersion liquid and a solvent.
4. The sandwich immersion lithography method according to claim 3, characterized in that: the mass percentage of the UV photoinitiator in the negative black photoresist is 1 wt% -8 wt%.
5. The sandwich immersion lithography method according to claim 3, characterized in that: the mass percentage of the photosensitizer in the negative black photoresist is 1 wt% -5 wt%.
6. The sandwich immersion lithography method according to claim 3, characterized in that: the mass percentage of the cross-linked polymer solution containing alternate carboxyl and carbon-carbon double bonds in the negative black photoresist is 10-30 wt%.
7. The sandwich immersion lithography method according to claim 3, characterized in that: the mass percentage of the UV curing monomer in the negative black photoresist is 5 wt% -10 wt%.
8. The sandwich immersion lithography method according to claim 3, characterized in that: the mass percentage of the black dye dispersion liquid in the negative black photoresist is 40 wt% -60 wt%.
9. The sandwich immersion lithography method according to claim 3, characterized in that: the total mass percentage of the solvent in the negative black photoresist is 40 wt% -80 wt%.
10. The sandwich immersion lithography method according to claim 3, characterized in that: the UV curing monomer is one or more of dipentaerythritol hexaacrylate DPHA, pentaerythritol triacrylate PETA and trimethylolpropane triacrylate TMPTA.
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| CN202110252945.2A CN112987510A (en) | 2021-03-09 | 2021-03-09 | Interlayer immersion type photoetching method using negative black photoresist |
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| KR20190102878A (en) * | 2018-02-27 | 2019-09-04 | 울산과학기술원 | Photoresist composition, photolithography process using the same, and pixel define layer prepared by using the same |
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2021
- 2021-03-09 CN CN202110252945.2A patent/CN112987510A/en active Pending
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| US20060110676A1 (en) * | 2003-03-04 | 2006-05-25 | Jyun Iwashita | Resist material for liquid immersion lithography process and method for forming resist pattern using the resist material |
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Application publication date: 20210618 |