CN104262193A - Dinitrodiphenylamine diazoresin, photoresist composition containing same and preparation method of photoresist composition - Google Patents
Dinitrodiphenylamine diazoresin, photoresist composition containing same and preparation method of photoresist composition Download PDFInfo
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- CN104262193A CN104262193A CN201410476040.3A CN201410476040A CN104262193A CN 104262193 A CN104262193 A CN 104262193A CN 201410476040 A CN201410476040 A CN 201410476040A CN 104262193 A CN104262193 A CN 104262193A
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- resin
- diazo resin
- methyl
- diazo
- photoetching compositions
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- CEVQHGGRQWLHSM-NSHDSACASA-N C[C@@H](c(cc(cc1[N+](OC)=O)[O]#N)c1N(C)c1ccccc1)[N+](O)=O Chemical compound C[C@@H](c(cc(cc1[N+](OC)=O)[O]#N)c1N(C)c1ccccc1)[N+](O)=O CEVQHGGRQWLHSM-NSHDSACASA-N 0.000 description 1
Abstract
The invention relates to dinitrodiphenylamine diazoresin, a photoresist composition containing the same and a preparation method of the photoresist composition. The composition is formed by dissolving raw materials containing the following components in parts by weight: 4-6 parts of film-forming resin, 10-15 parts of diazoresin and 0.1-1 part of background dyes into 200-300 parts of organic solvent. When being used as a photosensitizer to be applied to a negative photoresist of an LCD, the dinitrodiphenylamine diazoresin is strong in dry etching resistance and high in resolution ratio, in addition, the adhesive force between the photoresist and a film layer can be improved, the photoresist cannot not fall off in a developing process, and the technological process of using a thickening agent HMDS can be omitted.
Description
Technical field
The present invention relates to display manufacture field, be specifically related to a kind of dinitro diphenylamine diazo resin, photoetching compositions containing above-mentioned diazo resin and preparation method thereof.
Background technology
Photoresist material is the key function material carrying out photoetching process in large-scale integrated circuit industry.Photoresist material is after UV-irradiation, there is series of chemical, the dissolution rate of photoresist material in developing solution before and after exposure is changed, more just can by specific high precision Graphic transitions to substrate surface to be processed through processes such as development, post bake, etching and stripings.
According to the difference of photoetching process, photoresist material can be divided into positive photoresist and the large class of negative photoresist two.Along with the develop rapidly of large-scale integrated circuit industry, integrated circuit (IC) products and the variation of kind and updating of photoetching process, to the critical material used in photo-etching technological process, particularly the requirement of photoresist material is higher, and kind and the performance of photoresist material are more diversified, specialized.
Diazo naphthoquinone resin is applied in LCD photoresist material at present, but because diazo naphthoquinone resin exists poor heat stability, not easily preserves, is easy to the shortcomings such as deliquescence, therefore, need badly a kind of thermally-stabilised height, anti-dry etching ability is strong, resolving power is high photoresist material are provided.
Summary of the invention
The object of this invention is to provide that a kind of thermostability is high, the diazo resin that can improve the anti-dry etching ability of photoresist material and resolving power and the photoetching compositions containing this diazo resin.
To achieve these goals, one aspect of the present invention provides a kind of diazo resin, and described diazo resin structure is shown below:
Wherein, n is the integer of more than 2; The integer of preferred 2-10; Be more preferably 6.
R
-for hexafluoro-phosphate radical, Witco 1298 Soft Acid root, dodecyl sodium sulfonate root, tosic acid root, sym-toluenesulfonic acid root or naphthalenesulfonate anion; Preferred sym-toluenesulfonic acid root negatively charged ion.
W is CH
2or
x is hydrogen, methoxyl group, methyl, is preferably hydrogen; Y is nitro; Z is methyl, ethyl, is preferably methyl.
Described diazo resin can be the diphenylamine diazonium vitriol and the paraformaldehyde or 4 that contain organic sulfonic acid anion, the polycondensate of 4 '-bi-methoxy methyldiphenyl base ether.Described diazo resin preferred formaldehyde contracting N-methyl-2,6-dinitro diphenylamine 4-diazonium sym-toluenesulfonic acid resin.R in this resin
-for sym-toluenesulfonic acid root negatively charged ion, W are CH
2, X is hydrogen, Y is nitro, Z is methyl.
Another aspect of the present invention, a kind of photoetching compositions containing above-mentioned diazo resin is provided, described composition by comprise the film-forming resin of 4-6 weight part, the diazo resin of 10-15 weight part, the background dye of 0.1-1 weight part raw material dissolve in the organic solvent of 200-300 weight part and formed.
Described film-forming resin is water-fast polymkeric substance, comprises one or more in epoxy resin, polyvinyl acetal resin and urethane resin.
Described background dye is one or more in alkaline bright blue, Viola crystallina, Victoria pure blue, indigo, methyl violet, malachite green or solvent blue.
Described organic solvent is one or more in ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, dihydroxypropane single-ether, methylethylketone, N-BUTYL ACETATE, dioxane, N-Methyl pyrrolidone, methyl alcohol or tetrahydrofuran (THF).
The process for preparation of described photoetching compositions is: background dye be dissolved in organic solvent, after thoroughly dissolving, then adds film-forming resin, diazo resin, then filters, to obtain final product.
Described filtration in described process for preparation adopts filter paper to filter.
The present invention also provides a kind of using method of described photoetching compositions, be specially expose time, the anhydrous offset plate of exposure area when being subject to UV-irradiation, the diazo resin generation photoresponse in sensitive layer, generate radical cation, and combine with its film-forming resin is crosslinked; During development, exposed portion retains because of crosslinked, and unexposed portion is developed liquid removing because not reacting, obtain negative image (see Fig. 1).
Expose time, because nitro electron attraction causes benzene diazonium mainly heterolytic fission to occur, produce a large amount of pentanoic positively charged ions, except reacting with-OH the nucleophilic reagent on film-forming resin, also can with SiO
2film surface and H
2the hydrogen bond crosslinks that O molecule is formed, result is photoresist material and the SiO of exposed portion
2surface is bonded together by hydrogen bond, can not depart from, and the photoresist material of unexposed portion does not have this adhesive effect in developing process, removes after development.This strengthens the dissolubility difference of exposed portion and unexposed portion greatly, improves sensitivity and resolving power simultaneously.
Above-mentioned developing solution is preferably with the Na of 1-5 mass parts
2siO
3, the phenylcarbinol of 8-10 mass parts, the sodium lauryl sulphate of 4-8 mass parts is dissolved in the water of 80-120 mass parts and is formed.
Beneficial effect of the present invention:
1, synthesize the high dinitro diphenylamine diazo resin of thermostability as sensitizer, apply in LCD negative photoresist, anti-dry etching ability is strong, and resolving power is also high.
2, in exposure process, part diazo resin can improve the sticking power of photoetching (PR) glue and rete with the hydrogen bond crosslinks of SiO and the SiON film surface in blocking layer ESL or passivation layer PVX, there will not be PR glue to come off in developing process, thus tackifier HMDS before saving mask, also will be used to strengthen the technological process of the sticking power of PR glue and SiO and SiON.
Accompanying drawing explanation
Fig. 1 is the use mechanism figure of photoetching compositions of the present invention.
Fig. 2 a and Fig. 2 b is the gel permeation chromatography GPC result of MDNDDS diazo resin.
Embodiment
Below in conjunction with embodiment, the invention will be further described, instead of limit the scope of the invention.
Embodiment 1
The preparation of following example formaldehyde contracting N-methyl-2,6-dinitro diphenylamine 4-diazonium sym-toluenesulfonic acid resin.
1) 3,5-dinitrobenzene-4-chlorobenzenesulfonic acid (DNCBA, I)
60g (0.38mol) 4-chloro-benzoic acid joins in the vitriol oil of 240g98% in batches, then dropwise adds 60g (0.95mol) 98% concentrated nitric acid, system heat release, keeps temperature not higher than 110 DEG C.At 125 DEG C, stir 4h after dripping off, cooling, pours on trash ice, and a large amount of white solid is separated out, and suction filtration drying obtains product I (83g, productive rate 90%).
2) 3,5-dinitrobenzene-4-chloroaniline (DNCPA, II)
In 20% oleum that I (61g, 0.25mol) joins 150mL and 200mL1,2-ethylene dichloride mixed solution, in 15min, add NaN in batches
3(18.5g, 0.28mol), weak exotherm, maintenance system temperature is lower than 25 DEG C.After slow heating for some time, system starts very exothermic, reflux 2h, is then cooled to room temperature, occur layering, remove 1,2-ethylene dichloride layer, residual solution is fallen on ice, separate out milk yellow microlite, suction filtration washing and drying, obtains II (43g, productive rate 80%).
3) N-methyl-2,6-dinitrobenzenes-4-ADPA (MDNAD, III)
II (70g, 0.32mol) joins in 84mL (0.89mol) acetic anhydride, and reflux 1h, is cooled to room temperature.Be poured into water by mixed solution, a large amount of white solid is separated out, and suction filtration is also washed, and obtains the acetylate of 83gII (productive rate 99%).By the acetylate (83g, 0.32mol) of II and the anhydrous Na of porphyrize
2cO
3(19.6g, 0.18mol) under agitation joins in methylphenylamine (244mL, 2.18mol), is heated to 150 DEG C of reaction 5h.Cool overnight, has a large amount of red brown solid to separate out, solid collected by filtration, and washing, then joins in the mixed solution of 200mL concentrated hydrochloric acid and 300mL ethanol, reflux 3h.There is a large amount of reddish-brown microlite to separate out after cooling, collected by suction, with washing on a small quantity, obtaining the hydrochloride (74.3g, productive rate 72%) of product III.
4) N-methyl-2,6-dinitro diphenylamine-4-diazonium salt (MDNDDS, IV)
The hydrochloride (32.5g, 0.1mol) of III joins in 240g trash ice and 588mL10% sulfuric acid mixture liquid, with ice-water bath maintenance system temperature 0-5 DEG C.Under agitation dropwise add the solution that (13.8g, 0.2mol) Sodium Nitrite is dissolved in 65.7mL water, drip off the crude solid continuing to stir 2h, IV and separate out, collecting by filtration, is dissolved in 2L water, and the insoluble impurity of filtering.108g ZnCl is added in filtrate
2saturated solution, a large amount of red precipitate is separated out, and collecting by filtration, obtains the 1/2ZnCl of product IV
2double salt red solid (32.2g, productive rate 65%).
5) preparation of formaldehyde contracting N-methyl-2,6-dinitro diphenylamine 4-diazo resin (V)
By above-mentioned diazonium salt IV and paraformaldehyde condensation, make diazo resin, polymerization process: diazonium salt IV (0.039mol) under agitation joins in 52mL98% sulfuric acid in batches, after dissolving completely, at 0-5 DEG C, add the paraformaldehyde (1.4g, 0.047mol) of porphyrize in batches, add and keep this temperature 5h.Reaction mixture is slowly poured in the frappe ethanol of 230mL, and stir, after enough water dissolution, then use enough ZnCl
2saturated solution, have a large amount of solid to separate out, suction filtration, washing with alcohol 2 times, air-dry in ventilating kitchen, obtain corresponding water-soluble formaldehyde contracting MDNDDS diazo resin V.MDNDDS diazo resin characterization data:
Infrared IR (KBr): ν=2225cm
-1(s, C-N
2 +), 1592cm
-1, 1540cm
-1(vs, Ar);
Nuclear-magnetism
1h NMR (400MHz, DMSO-d
6, δ): 9.58-9.34 (m, 2H, Ar H), 7.64-6.96 (m, ≈ 3.5H, Ar H), 3.96-3.91 (m, ≈ 1.3H, CH
2) 3.48-3.31 (m, 3H, CH
3).
Gel permeation chromatography (Gel Permeation Chromatography, GPC) analytical results is shown in Fig. 2 a and Fig. 2 b.
6) preparation of formaldehyde contracting N-methyl-2,6-dinitro diphenylamine 4-diazonium sym-toluenesulfonic acid resin VI
Above-mentioned water-soluble formaldehyde contracting MDNDDS diazo resin (0.04mol) is dissolved in 200mL, filters out impurities.Under agitation, drip the saturated aqueous solution of (9.99g, 0.045mol) sym-toluenesulfonic acid sodium in filtrate, start anionresin occurs, pH is now 2.5, adds the NaCO of 10%
3solution regulates pH to 7, and the precipitation that suction filtration obtains, washes 3 times with water, 27 DEG C of dried in vacuo overnight, obtains formaldehyde contracting N-methyl-2,6-dinitro diphenylamine 4-diazonium sym-toluenesulfonic acid resin VI (13.41g, productive rate 77%).
Similarly, can by the method for the 6th step, the saturated solution containing the negatively charged ion such as hexafluoro-phosphate radical, Witco 1298 Soft Acid root is used to replace the saturated aqueous solution of sym-toluenesulfonic acid sodium, formaldehyde contracting N-methyl-2 can be prepared, the dinitro diphenylamine diazo resins such as 6-dinitro diphenylamine-4-diazonium phosphofluoric acid resin, formaldehyde contracting N-methyl-2,6-dinitro diphenylamine-4-diazonium Witco 1298 Soft Acid resin.
Embodiment 2
The present embodiment provides photoetching compositions containing diazo resin and process for preparation thereof.The preparation of diazonium photoresist material: 0.1g Victoria pure blue is dissolved in 250g ethylene glycol monoethyl ether, add formaldehyde contracting N-methyl-2 again, 6-dinitro diphenylamine-4-diazonium phosphofluoric acid resin (embodiment 1 prepares) 10g, polyvinyl formal maleic acid ester 5g, filter with filter paper after thoroughly dissolving, obtained photoresist material.
Embodiment 3
The present embodiment provides photoetching compositions containing diazo resin and process for preparation thereof.The preparation of diazonium photoresist material: 0.5g Viola crystallina is dissolved in 200g dihydroxypropane single-ether, add formaldehyde contracting N-methyl-2 again, 6-dinitro diphenylamine-4-diazonium Witco 1298 Soft Acid resin 12g, polyvinyl formal phthalic ester 6g, filter with filter paper after thoroughly dissolving, obtained photoresist material.
Embodiment 4
The present embodiment provides photoetching compositions containing diazo resin and process for preparation thereof.The preparation of diazonium photoresist material: 1g alkaline bright blue is dissolved in 300g ethylene glycol monomethyl ether, add formaldehyde contracting N-methyl-2 again, 6-dinitro diphenylamine-4-diazonium sym-toluenesulfonic acid resin 14g, polyvinyl butyral acetal phthalic ester 4g, filter with filter paper after thoroughly dissolving, obtained photoresist material.
Embodiment 5
Thermal decomposition performance during the pressed powder state of diazo resin is related to the storage period of diazo resin solid itself, and thermal decomposition performance during solid film state is then related to the storage period of the press plate be made up of this diazo resin.
Traditional diazo resin is that pentanoic 4-diazo resin (DDS) structure is as follows:
The diazo resin of the present embodiment is with N-methyl-2,6-dinitro diphenylamine-4-diazonium salt (MDNDDS) for example, and its structure is as follows:
Mole thermolytic rate (D
t%) obtain by calculating the method heating the reduction that front and back UV spectrum absorbs.The D of MDNDDS resin at 80 DEG C
t% lists in table 1.As can be seen from the table, the thermostability of MDNDDS resin is better than DDS resin all greatly.As the D of MDNDDS resin after heating 34h
t% is that 50%, DDS resin heating 9h is over regard to having decomposed.As can be seen here, when using MDNDDS resin as diazo sensitizer, the shelf-life of diazo sensitizer will be extended.
The thermolysis situation of DDS and MDNDDS diazo resin at 80 DEG C, table 1
The research of contriver shows, MDNDDS and diazo resin thereof all demonstrate the thermostability more superior than traditional DDS diazo resin, so when using MDNDDS diazo resin as sensitizer, the short storage period problem of photoresist material can obtain efficient solution certainly.
Contrast experiment
Experimental subjects:
Comparative example 1: by 1.5g sensitizer (2,3,4-trihydroxybenzophenone esterification 2-diazonium-1-naphthoquinones-5-SULPHURYL CHLORIDE, it is 1mol2,3, the esterification reaction product of 4-trihydroxybenzophenone and 2.35mol2-diazonium-1-naphthoquinones-5-SULPHURYL CHLORIDE) and 8.5g linear phenolic resin be dissolved in 25g glycol methyl ether acetate, filter with filter paper, obtained photoresist material.
Meanwhile, using the preparation-obtained photoresist material of embodiment of the present invention 2-4 as experimental group, under identical application conditions, test as follows:
By the photoresist material of comparative example 1 and experimental group with 2000-6000 turn/rotating speed of min is applied to plasma enhanced chemical vapor deposition (PECVD Deposition) SiO
2(thickness is
) glass substrate on, 100 DEG C are formed containing the films of photoresist material for front baking 2-10 minute, and then expose with exposure machine, exposure intensity is 30-180mJ/cm
2, with developing liquid developing 20 seconds, after oven dry, namely obtain image.
Intermediate-resolution of the present invention refers to the minimum width that the amplitude between the lines that more than obtain after photoetching compositions according to the method described above exposure imaging 2 arrange at equal intervals can be reproduced on photosensitive surface.
Minimum exposure amount required when sensitivity refers to and obtains 3.5 μm of images according to above-mentioned exposure imaging method.
Table 2 contrast and experiment
| Embodiment | Resolving power (μm) | PR dropping situations |
| Embodiment 2 | 3.0 | Nothing |
| Embodiment 3 | 3.1 | Nothing |
| Embodiment 4 | 2.9 | Nothing |
| Comparative example 1 | 3.1 | Big area comes off |
Dinitro diphenylamine diazo resin of the present invention not only good heat stability can be found out by the result of table 2, be easy to preserve; And when being applied in LCD negative photoresist, anti-dry etching ability is strong, and resolving power is also high; In addition, in exposure process, part diazo resin can improve the sticking power of PR glue and rete with the hydrogen bond crosslinks of SiO and the SiON film surface in ESL or PVX, there will not be PR glue to come off in developing process, thus HMDS before saving mask, also will be used to strengthen the technological process of the sticking power of PR glue and SiO and SiON.
Although above with general explanation, embodiment and test, the present invention is described in detail, and on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (16)
1. a diazo resin, is characterized in that, its structural formula is shown below:
Wherein, n is the integer of more than 2;
R
-for hexafluoro-phosphate radical, Witco 1298 Soft Acid root, dodecyl sodium sulfonate root, tosic acid root, sym-toluenesulfonic acid root or naphthalenesulfonate anion;
W is CH
2or
X is hydrogen, methoxyl group or methyl;
Y is nitro;
Z is methyl or ethyl.
2. diazo resin according to claim 1, is characterized in that, n is the integer of 2-10.
3. diazo resin according to claim 1 and 2, is characterized in that, R
-for sym-toluenesulfonic acid root negatively charged ion.
4. diazo resin according to claim 1 and 2, is characterized in that, W is CH
2or
5. diazo resin according to claim 1 and 2, is characterized in that, X is hydrogen.
6. diazo resin according to claim 1 and 2, is characterized in that, Z is methyl.
7. diazo resin according to claim 1 and 2, is characterized in that, R
-for sym-toluenesulfonic acid root negatively charged ion, W is CH
2or
x is hydrogen, and Z is methyl.
8. a photoetching compositions, it is characterized in that, described composition is dissolved by the raw material of the background dye of the diazo resin described in any one of claim 1-7 comprising the film-forming resin of 4-6 weight part, 10-15 weight part, 0.1-1 weight part and is formed in the organic solvent of 200-300 weight part.
9. photoetching compositions according to claim 8, is characterized in that, described film-forming resin comprises one or more in epoxy resin, polyvinyl acetal resin and urethane resin.
10. photoetching compositions according to claim 8, is characterized in that: described background dye is one or more in alkaline bright blue, Viola crystallina, Victoria pure blue, indigo, methyl violet, malachite green or solvent blue.
11. photoetching compositions according to claim 8, is characterized in that: described organic solvent is one or more in ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, dihydroxypropane single-ether, methylethylketone, N-BUTYL ACETATE, dioxane, N-Methyl pyrrolidone, methyl alcohol or tetrahydrofuran (THF).
The preparation method of the photoetching compositions described in 12. 1 kinds of claim 8-11, is characterized in that:
Background dye is dissolved in organic solvent, after thoroughly dissolving, then adds film-forming resin, diazo resin, then filter.
13. preparation methods according to claim 12, is characterized in that:
Filter paper is adopted to carry out described filtration.
The using method of the photoetching compositions described in 14. 1 kinds of claim 8-11, is characterized in that:
When exposing, the anhydrous offset plate of exposure area is subject to UV-irradiation, the diazo resin generation photoresponse in sensitive layer, generates radical cation, and combines with film-forming resin is crosslinked;
During development, exposed portion retains because of crosslinked, and unexposed portion is developed liquid removing because not reacting, obtain negative image.
15. using method according to claim 14, wherein:
The photoresist material of exposed portion and SiO
2surface is bonded together by hydrogen bond, and the photoresist material of unexposed portion is removed after development.
16. using method according to claims 14 or 15, wherein:
Described developing solution is with the Na of 1-5 mass parts
2siO
3, the phenylcarbinol of 8-10 mass parts, the sodium lauryl sulphate of 4-8 mass parts is dissolved in the water of 80-120 mass parts and is formed.
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|---|---|---|---|
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|---|---|---|---|
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| CN104530342A (en) * | 2015-01-09 | 2015-04-22 | 京东方科技集团股份有限公司 | Diazoresin, photoresist composition and preparation method of photoresist composition |
| CN105807563A (en) * | 2016-05-16 | 2016-07-27 | 京东方科技集团股份有限公司 | Photoresist composition and preparation method and composition method thereof |
| CN107145037A (en) * | 2017-07-07 | 2017-09-08 | 京东方科技集团股份有限公司 | A kind of photoetching compositions and preparation method |
| CN109671856A (en) * | 2017-10-13 | 2019-04-23 | 中华映管股份有限公司 | Organic LED structure and its manufacturing method |
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104530342A (en) * | 2015-01-09 | 2015-04-22 | 京东方科技集团股份有限公司 | Diazoresin, photoresist composition and preparation method of photoresist composition |
| WO2016110051A1 (en) * | 2015-01-09 | 2016-07-14 | 京东方科技集团股份有限公司 | Diazoresin, photoresist composition and preparation method of photoresist composition |
| CN104530342B (en) * | 2015-01-09 | 2017-08-08 | 京东方科技集团股份有限公司 | Diazo resin, photoetching compositions and its compound method |
| US10303053B2 (en) | 2015-01-09 | 2019-05-28 | Boe Technology Group Co., Ltd. | Diazo-resin, photoresist composition and method of preparing same |
| CN105807563A (en) * | 2016-05-16 | 2016-07-27 | 京东方科技集团股份有限公司 | Photoresist composition and preparation method and composition method thereof |
| CN105807563B (en) * | 2016-05-16 | 2020-01-14 | 京东方科技集团股份有限公司 | Photoresist composition, preparation method and patterning method thereof |
| CN107145037A (en) * | 2017-07-07 | 2017-09-08 | 京东方科技集团股份有限公司 | A kind of photoetching compositions and preparation method |
| CN107145037B (en) * | 2017-07-07 | 2020-05-12 | 京东方科技集团股份有限公司 | Photoresist composition and preparation method thereof |
| CN109671856A (en) * | 2017-10-13 | 2019-04-23 | 中华映管股份有限公司 | Organic LED structure and its manufacturing method |
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