CN1088527C - Methd for pattern-processing of photosensitive resin composition - Google Patents
Methd for pattern-processing of photosensitive resin composition Download PDFInfo
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- CN1088527C CN1088527C CN 97102015 CN97102015A CN1088527C CN 1088527 C CN1088527 C CN 1088527C CN 97102015 CN97102015 CN 97102015 CN 97102015 A CN97102015 A CN 97102015A CN 1088527 C CN1088527 C CN 1088527C
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Abstract
The present invention discloses a method for an imaging process of photosensitive resin compositions, which comprises coating positive photosensitive resin compositions containing polyamide and diazoquinone compounds on a base plate. After previously being baked, the base plate is irradiated by light, and then an exposed part is dissolved in an alkaline water solution containing anionic surfactants to remove photosensitive resin in order to obtain images so as to obtain the images. When the alkaline water solution containing anionic surfactants in the present invention is used for development, the images having no scum and high resolution can be obtained.
Description
Background of the present invention
The field of the invention
The present invention relates to obtaining no scum silica frost, the method for the imaging process of the photosensitive resin composition of high-definition picture.
Prior art
In semi-conductor industry, ultraviolet curable resin such as photoresist, photo-sensistive polyimide or the like recently by in the process through being commonly used to prepare very fine circuit such as IC, LSI or the like or requiring to pack as dielectric film or diaphragm.The characteristics of ultraviolet curable resin are can obtain by simple relatively equipment the resin image of high precision.Especially since in developing process swelling not, comprise the phenol phenolic novolac and make the image that positive photoresist that base material makes photosensitizer with diazonium quinone etc. can form the excellent resolution rate.In addition, because developer is an alkaline aqueous solution, positive photoresist is good at secure context.As mentioned above, ultraviolet curable resin has many characteristics, therefore is often used in the top semi-conductive precision circuit of preparation etc.On the other hand; in being used as the photosensitivity heat stable resin of semi-conductive dielectric film or diaphragm as photo-sensistive polyimide; similar with photoresist; have positive light-sensitive heat stable resin developed (seeing for example JP-A-64-60630, JP-B-1-46862 etc.), and on resin, caused attention as the dielectric film of highly integrated semiconductor or diaphragm as high resolving power, characteristics such as developer free from environmental pollution.
Most of positive light-sensitive resin combinations comprise the combination of alkali-soluble polymer and above-mentioned diazonium quinone as photosensitizer.At unexposed portion, these diazonium quinone (quinonediazide) compounds are insoluble to the aqueous solution of alkali, and through overexposure, they have produced chemical change and have become in the aqueous solution of alkali solvable.Correspondingly, utilize the deliquescent difference of exposed portion and unexposed portion, remove exposed portion, can prepare the film image that is coated with that only comprises unexposed portion thus by aqueous alkali.
Aqueous alkali as developer is generally Tetramethylammonium hydroxide (representing with TMAH after this).When comprising photoresist that conventional phenol linear phenol-aldehyde resin makes base material and be developed, the development that can produce with the aqueous solution of TMAH.Yet, in as JP-B-1-46862, introduce with in the photosensitive resin composition that comprises the polybenzoxazole precursor, exist undeveloped portion (scum silica frost) to remain in the shortcoming of exposed portion, this should all be removed in order to avoid damage resolution.
General introduction of the present invention
A target of the present invention provides that the photosensitive resin composition imaging process obtains high resolving power and the method that do not cause the scum silica frost that causes in the conventional imaging process.
By following introduction, it is obvious that additional objects and advantages of the present invention will become.
According to the present invention, it provides the method for photosensitive resin composition imaging process, comprise to comprise and be coated on the substrate by the polyamide of following formula (1) expression and the positive light-sensitive resin combination of diazonium naphtoquinone compounds, to use rayed behind its preliminary drying, the dissolving exposed portion has obtained image like this to remove exposed portion in containing the aqueous alkali of anionic surfactant afterwards:
X is the tetravalence aromatic group in the formula; Y is the divalence aromatic group; Z is
R wherein
1And R
2Be divalent organic group, R
3And R
4Be any monovalent organic radical group; A and b are mole fraction; A+b=100mol%, a=60.0-100mol%; B=0-40.0mol%.And n=2-500.Detailed introduction of the present invention
Is made up of diaminophenol with X structure and dicarboxylic acid with Y structure and when heating this polyamide for about 300-400 ℃ the polyamide of formula (1) expression, the generation ring-closure reaction causes polyamide to be transformed into to be called the heat-resistant resin of polybenzoxazole.Usually, the positive light-sensitive resin combination develops with aqueous alkali.For example, because the base material phenol phenolic novolac of photoresist has the hydroxyl of phenol, photoresist can be developed.Similarly, because the diaminophenol with X structure has the hydroxyl of phenol, the positive light-sensitive resin by the polyamide of formula (1) expression that comprises as base material also can be developed.Yet the development of this ultraviolet curable resin is lower than to comprise as the photoresist of the phenol phenolic novolac of base material and at exposed portion and produces scum silica frost, thereby resolution is compromised.
Consider that this is to contain a hydroxyl owing on each phenyl ring of phenol phenolic novolac, and only on amine moiety, contain a hydroxyl by the polyamide of formula (1) expression.In order to improve cementability by replacing under diaminophenol that a part has an X structure the occasion for the synthetic polyamide of the silicon diamines of Z structure with formula (1), dissolving resin step-down, thereby produce more scum silica frost, it is very poor that resolution becomes.But, when resin combination is handled with the aqueous alkali that contains anionic surfactant of the present invention, can not cause scum silica frost fully.Though reason it be unclear that, this is considered to owing to anionic surfactant makes the reason that affinity improves between resin and the developer.
In polyamide of the present invention (1), X comprises, for example:
A represents-CH in the formula
2-,-O-,-S-,-SO
2-,-CO-,-NHCO-or-C (CF
3)
2-etc., but be not limited to these.
In formula (1), Y comprises, for example:
Wherein A represents-CH
2-,-O-,-S-,-SO
2-,-CO-,-NHCO-or-C (CF
3)
2-etc., but be not limited to these.
And in formula (1), Z comprises, for example:
Deng, but be not limited to these.
When need be to the cementability of substrate such as silicon chip, the Z in the formula (1) be used and the amount that can part mostly be 40.0mol% most is used.When b partly surpasses 40mol%, dissolving resin becomes very low and promptly uses the method for imaging process of the present invention also to cause scum silica frost to make imaging process impossible.
By way of parenthesis, when these X, Y and Z are used, they each can be separately or with on two or a plurality of mixing use.
The exemplary that is used for anionic surfactant of the present invention is the alkali metal salt of the alkali metal salt of alkyl benzene sulphonate, alkyl benzene sulphonate, naphthalene sulfonic acids, the ammonium salt of naphthalene sulfonic acids etc.Wherein concrete example comprises dodecylbenzene sulfonic acid, neopelex, sodium naphthalene sulfonate etc.But anionic surfactant is not limited to these.By way of parenthesis, here the anionic surfactant of expression be included in the aqueous alkali produce it alkali salt to form the compound of anionic surfactant.
Based on the total amount of the aqueous solution of alkali, be preferably 0.1 to 10% weight for contained anionic surfactant in the aqueous alkali of developer in the present invention.When consumption during less than 0.1% weight, scum silica frost is easy to produce and when consumption during greater than 10% weight, in the film thickness loss increasing of non-exposed portion and the resolution that can not get.
Alkaline aqueous solution of the present invention is for dissolving and removes alkali-soluble polymer and it and be necessary for alkali compounds and be dissolved in wherein aqueous solution.Alkali compounds comprises for example inorganic base, for example NaOH, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammoniacal liquor etc.; Primary amine such as ethamine, n-propylamine etc.; Secondary amine such as diethylamine, di-n-butylamine etc.; Tertiary amine such as triethylamine, methyl-diethyl-amine etc.; Hydramine such as dimethylethanolamine, triethanolamine etc.; With quaternary ammonium salt such as Tetramethylammonium hydroxide, tetraethyl ammonium hydroxide etc.They can be separately or use with two kinds or multiple mixing.Wherein, tetramethyl oxyammonia preferably.The concentration of alkali compounds is 0.1 to 10% weight, preferably from 1 to 3% weight.
Be used for photosensitive resin composition of the present invention and comprise polyamide, diazonium naphtoquinone compounds and solvent, also can contain polyamic acid if desired as Main Ingredients and Appearance.Polyamic acid has carboxyl, so the dissolubility raising, and development time can be shortened.
Be used for diazonium quinone of the present invention for having 1,2-benzoquinones two-fold nitride or 1, the compound of 2-naphthoquinones two-fold nitride structure and be, disclosed known compound in 772,972,2,797,213 and 3,669,658 as U.S.2.It comprises, for example the compound of being represented by following structural formula:
Wherein Q be hydrogen atom,
And at least one Q is in each compound
Deng.
In above-claimed cpd, preferably (d), (e), (f) and (g), and (f) be particularly preferred.
The method for preparing image comprises application composition on appropriate carriers, for example silicon chip, stupalith, aluminium etc.Coating can with for example with the spinner spin coating, with sprayer spraying, dip-coating, seal be coated with, roller coating etc. carries out.Then, coat film dry 1 to 10 fen clock time under about 60-180 ℃ of temperature.Drying means can wait and carry out with stove, infrared dryer, hot platform, and according to efficient and be easy to temperature control, hot platform is preferred.When hot platform was used, drying was preferably carried out under 80 to 130 ℃ of temperature.When temperature was lower than 80 ℃, not exclusively dry, this was undesirable.When temperature surpassed 130 ℃, excessively dry, this was undesirable.Drying is preferably carried out 2 to 4 fens clock times under 100 ℃ to 120 ℃.
Then, the coat film of Ganing shines with chemical ray by required pattern.Can use X ray, electron ray, ultraviolet ray, visible light etc. as chemical ray, and the ray with wavelength 200 to 500nm is particularly preferred.In order to obtain high-resolution image, be more preferably adopted with the i-line stepping of wavelength 365nm or with the g-line stepping of wavelength 436nm.
The introduction of embodiment preferred
Example as follows is used for introducing especially the present invention.Example 1 synthesizing polyamides
The hexafluoro-2 of 33.6 parts of weight of dissolving (0.100mol) in the pyridine of the N,N-dimethylacetamide of 150 parts of weight and 33.2 parts of weight (0.420mol), two (3-amino-4-hydroxy the phenyl)-propane of 2-.
Then, 21.3 parts of weight (0.105mol) are dissolved in 100 parts of terephthalyl chlorides in the weight ring hexanone and are added drop-wise in the above-mentioned solution in ° to-15 ℃ and 30 minutes in temperature-10, afterwards at room temperature agitating solution 4 hours to finish reaction.Filter reaction mixture is poured filtrate in the water then with the subject polymer (A) of precipitation by following formula (A) expression.By filtering collecting precipitation, wash and dry a whole day is whole night under 80 ℃ of vacuum.
The preparation photosensitive resin composition
The polyamide (A) that 100 parts of weight of (back is expressed as NMP) dissolving are synthesized in the N-of 200 parts of weight N-methyl-2-2-pyrrolidone N-and 25 parts of diazonium naphtoquinone compounds (D) that weight is represented by following structural formula (D), then, gained solution obtains photosensitive resin composition by the Teflon filtrator filtration of 0.2 μ m:
The evaluation of photosensitivity
This photosensitive resin composition is spun on the silicon chip and heats 3 minutes with solvent flashing on 120 ℃ hot platform, forms then to have filming of 5 μ m thickness.This is filmed by a TOPPAN PRINTING CO., and the face shield that LTD. produces (test pattern NO.1, image that stays and the image of removing are drawn with 50-0.88 μ m width) uses ultraviolet ray by high-pressure sodium lamp with 200mJ/cm
2Speed irradiation.Gained is filmed with the Tetramethylammonium hydroxide that comprises 1.20 parts of weight, stir the dissolving that the groove method developed 30 seconds and remove filming of exposed portion 98.3 the developer of the pure water of part weight and the dodecylbenzene sulfonic acid of 0.5 part of weight adopts, then 10 seconds of water flush away developer.As a result, obtained to have the image that line width 2.5 μ m do not have scum silica frost.
Film thickness loss in developing process ((because the thickness before the reduction/development of development film thickness) * 100 (%), this value is the smaller the better) is 10% and satisfactory.Example 2 synthesizing polyamides
The hexafluoro-2 of 33.0 parts of weight of dissolving (0.090mol) in the N,N-dimethylacetamide of 150 parts of weight, two (the 3-aminopropyls)-1,1,3 of 1.3-of two (the 3-amino-4-hydroxy phenyl) propane of 2-and 2.5 parts of weight (0.010mol), 3-tetramethyl disiloxane.
Next, the terephthalyl chloride that will be dissolved in the 21.3 parts of weight (0.105mol) in 100 parts of weight ring hexanones under-10 ℃ to-15 ℃ temperature in 30 minutes is added drop-wise in the solution, and the potpourri of gained at room temperature stirs 4 hours to finish reaction then.After reaction mixture filters solution is poured in the water to be settled out the subject polymer (B) by following formula (B) expression.By filtering collecting precipitation, dry a whole day is whole night under 80 ℃ of vacuum to wash the back.
The preparation photosensitive resin composition
The polyamide that is synthesized (B) of 100 parts of weight of dissolving and 25 parts of weight such as example 1 used same diazonium naphtoquinone compounds (D) in the NMP of 200 parts of weight, afterwards, the solution of gained filters to obtain photosensitive resin composition by the Teflon filtrator of 0.2 μ m.The evaluation of photosensitivity
Under the condition identical, carry out spin coating, preliminary drying and exposure as example 1.Afterwards, employing is stirred the groove method and was developed for 60 seconds with dissolving and remove filming of exposed portion with the developer of the Tetramethylammonium hydroxide that comprises 1.20 parts of weight, 93.80 parts pure water and 5.00 parts of weight dodecylbenzene sulfonic acids, then 10 seconds of water flush away developer.As a result, obtained the image that line width 5 μ m do not have scum silica frost.Current film thickness loss is 8% and satisfactory.Example 3 synthesizing polyamides
In the NMP of 400 parts of weight, dissolve 1 of 43.6 parts of weight (0.175mol), two (ν-aminopropyl)-1,1 of 3-, 3, the benzophenone tetracarboxylic dianhydride of 3-tetramethyl disiloxane and 57.5 parts of weight (0.178mol) at room temperature stirred the solution obtain 7 hours then.Reaction mixture is poured in the water, by filter collecting the precipitation that obtains, obtains polyamic acid (C) by following structural formula (C) expression 80 ℃ of following vacuum drying then:
The preparation photosensitive resin composition
Add 30 parts of weight such as example 1 used same diazonium naphtoquinone compounds (D) forms a solution in the polyamic acid (C) of the example 1 gained polyamide (A) of 80 parts of weight and 20 parts of weight, the Teflon filtrator of this solution by 0.2 μ m filters and obtains a photosensitive resin composition.The evaluation of photosensitivity
Under the condition identical, carry out spin coating, preliminary drying and exposure as example 1, afterwards, employing is stirred the groove method and was developed for 20 seconds with dissolving and remove filming of exposed portion with the developer of the dodecylbenzene sulfonic acid that comprises the pure water of the Tetramethylammonium hydroxide of 1.20 parts of weight, 98.50 parts of weight and 0.30 part of weight, afterwards 10 seconds of water flush away developer.The result has obtained the image that line width 2 μ m do not have scum silica frost.At this moment film thickness loss is 13% and satisfactory.Example 4
Except the diazonium naphtoquinone compounds (E) with following structural formula (E) expression replaces diazonium naphtoquinone compounds (D),, obtained having the image that line width 3 μ m do not have scum silica frost to estimate with example 1 identical method.Current thickness loss is 9% and satisfactory.
Example 5 and 6
Except the consumption of dodecylbenzene sulfonic acid changes 0.1% weight and 10% weight respectively into, to carry out the evaluation of photosensitivity as example 1 identical method.Example 7 synthesizing polyamides
Except replace the paraphthaloyl chloride of 21.3 parts of weight (0.105mol) with the oxidation dibenzoyl chlorine of 31.0 parts of weight (0.105mol), to have obtained polyamide (F) as example 1 same method by following formula (F) expression.
The preparation photo-sensitive composition
Except the diazonium naphtoquinone compounds (H) with following formula (H) expression replaces diazonium naphtoquinone compounds (D),, made the photo-sensitive composition of polyamide (F) with the same method of example 1.
The evaluation of photosensitivity
With method, carry out the evaluation of the photosensitivity of the composition for preparing above with example 1.As a result, obtained having the image that line width 2 μ m do not have scum silica frost.Current thickness loss is 10% and satisfactory.Example 8 synthesizing polyamides
Except replace the paraphthaloyl chloride of 21.3 parts of weight (0.105mol) with the oxidation dibenzoyl chlorine of 31.0 parts of weight (0.105mol), obtained the polyamide of representing by following formula (G) (G) with method with example 2.
Preparation photo-sensitive composition (G)
Except replacing diazonium naphtoquinone compounds (D), prepared the photo-sensitive composition of polyamide (G) with method with example 1 with example 7 used diazonium naphtoquinone compounds (H).The evaluation of photosensitivity
With the evaluation of preparation composition photosensitivity above carrying out with the method for example 1, the result has obtained having the image that line width 3 μ m do not have scum silica frost.Current film thickness loss is 11% and satisfactory.Comparative Examples 1
Except developer replaces with the developer that the pure water of the Tetramethylammonium hydroxide that comprises 1.20 parts of weight and 98.80 parts of weight does not contain dodecylbenzene sulfonic acid, to carry out same evaluation with example 1.Comparative Examples 2
Except developer replaces with the developer that the pure water of the Tetramethylammonium hydroxide that comprises 2.00 parts of weight and 98.00 parts of weight does not contain dodecylbenzene sulfonic acid, carry out the evaluation same as example 2.Comparative Examples 3
Except developer comprising the Tetramethylammonium hydroxide of 1.20 parts of weight, the developer of the dodecylbenzene sulfonic acid of the pure water of 86.80 parts of weight and 12.00 parts of weight replaces, and carries out the evaluation same as example 1.Comparative Examples 4
Except developer replaces with the developer of the dodecylbenzene sulfonic acid of the pure water of the Tetramethylammonium hydroxide that comprises 1.20 parts of weight, 98.75 parts of weight and 0.05 part of weight, carry out the evaluation same as example 1.
The result who obtains in example and Comparative Examples is as shown in table 1.
Table 1
| Alkali-soluble polymer | Photosensitizer | Anionic surfactant | The back scum silica frost develops | Resolution (μ m) | Film thickness loss (%) | ||
| Example | 1 | A | D | 0.5wt.％ | Do not have | 2.5 | 10 |
| 2 | B | D | 5.0wt.％ | Do not have | 5 | 8 | |
| 3 | A/C＝50/50 | D | 0.3wt.％ | Do not have | 2 | 13 | |
| 4 | A | E | 0.5wt.％ | Do not have | 3 | 9 | |
| 5 | A | D | 0.1wt.％ | Do not have | 2.5 | 9 | |
| 6 | A | D | 10wt.％ | Do not have | 5 | 11 | |
| 7 | F | H | 0.5wt.％ | Do not have | 2 | 10 | |
| 8 | G | H | 0.5wt％ | Do not have | 3 | 11 | |
| Comparative Examples | 1 | A | D | - | Have | 10 | 9 |
| 2 | B | E | - | Have | 15 | 7 | |
| 3 | A | D | 12wt.％ | Do not have | 5 | 47 | |
| 4 | A | D | 0.05wt.％ | Have | 12 | 10 | |
Annotate: anionic surfactant; Dodecylbenzene sulfonic acid
Claims (11)
1. the method for photosensitive resin composition imaging process, it comprises and applies the positive light-sensitive resin combination that comprises by the polyamide of following formula (1) expression and diazonium naphtoquinone compounds on a substrate:
Wherein X is the tetravalence aromatic radical; Y is the divalence aromatic radical; Z is
, R here
1And R
2Be divalent organic group, R
3And R
4Be any monovalent organic radical group; A and b represent mole fraction; A+b=100%; A=60.0-100mol%; B=0-40.0mol% and n=2-500 will use rayed behind its preliminary drying, and the dissolving exposed portion thereby obtains image removing ultraviolet curable resin in containing the alkaline aqueous solution of alkyl benzene sulphonate afterwards.
2. according to the method for the imaging process of claim 1, alkyl benzene sulphonate wherein is a dodecylbenzene sulfonic acid.
3. according to the method for the imaging process of claim 1, wherein based on the general assembly (TW) of alkaline aqueous solution, the amount of the anionic surfactant that contains in the alkaline aqueous solution is a 0.1-10% weight.
4. according to the method for the imaging process of claim 1, wherein alkaline aqueous solution is the aqueous solution of NaOH, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammoniacal liquor, ethamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyl-diethyl-amine, dimethylethanolamine, triethanolamine or tetraethyl ammonium hydroxide.
5. according to the method for the imaging process of claim 4, wherein alkaline aqueous solution is the aqueous solution of tetraethyl ammonium hydroxide.
6. according to the method for the imaging process of claim 1, the group of one of structural formula expression below wherein the X in the formula (1) of expression polyamide serves as reasons:
Wherein A represents-CH
2-,-O-,-S-,-SO
2-,-CO-,-NHCO-or-C (CF
3)
2
7. according to the method for the imaging process of claim 1, wherein represent the serve as reasons group of one of following structural formula expression of Y in the formula (1) of polyamide:
Wherein A represents-CH
2-,-O-,-S-,-SO
2-,-CO-,-NHCO-or-C (CF
3)
2-.
8. according to the method for the imaging process of claim 1, the group of one of structural formula expression below serving as reasons wherein by the Z in the formula (1) of expression polyamide:
9. according to the method for the imaging process of claim 1, the serve as reasons compound of one of following structural formula expression of diazonium naphtoquinone compounds wherein:
In the formula Q be hydrogen atom,
And at least one Q is in above-claimed cpd
10. according to the method for the imaging process of claim 1, wherein polyamide has following any structural formula:
11. according to the method for the imaging process of claim 1, wherein the diazonium naphtoquinone compounds has following arbitrary structural formula:
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| CN 97102015 CN1088527C (en) | 1997-01-06 | 1997-01-06 | Methd for pattern-processing of photosensitive resin composition |
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|---|---|---|---|
| CN 97102015 CN1088527C (en) | 1997-01-06 | 1997-01-06 | Methd for pattern-processing of photosensitive resin composition |
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