CN1126006C - Composition of developing liquid - Google Patents
Composition of developing liquid Download PDFInfo
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- CN1126006C CN1126006C CN 99127536 CN99127536A CN1126006C CN 1126006 C CN1126006 C CN 1126006C CN 99127536 CN99127536 CN 99127536 CN 99127536 A CN99127536 A CN 99127536A CN 1126006 C CN1126006 C CN 1126006C
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Abstract
The present invention provides alkaline developing liquid for forming images after being used for the exposure of photosensitive resin. The composition comprises (A), water, (B), at least one alkali compound with the content of 0.01 to 5 wt%, and (C), at least one nonionic interfacial active agent with the content of 0.01 to 3.5 wt%, wherein (C), the nonionic interfacial active agent has the following structural formula (I): n is an integer from 6 to 23; at least two kinds of R<1>, R<2>, R<3>, R<4> and R<5> are aralkyl radicals or aromatic hydroxyl radicals.
Description
The present invention is the constituent of relevant a kind of developer solution, especially refer on a kind of field that is used in integrated circuit, printed circuit board (PCB), color liquid crystal device or colored filter, make photosensitive resin composition after filming, exposing, the constituent of the developer solution that forms image (pattern) is developed at unexposed position.
General colored filter is when making, photosensitive resin coating constituent on substrate normally, the mode of its coating has decoration method, print process, electricity work method and pigment dispersing method etc., with the pigment dispersing method is example, it is when making colored filter, at first with dispersible pigment dispersion, solvent, photoresist and relevant adjuvant hybrid modulation become the chromatic photosensitivity resin combination, coat this photoresist on the substrate then and carry out in advance roasting, afterwards with after the light shield exposure, again with the unexposed soluble resin of developer solution flush away, can make needed coloured image, and common visualization way there is immersion development, shake development, spray developing (spray), leave standstill development (puddle) etc.
Yet technology according to known developer solution, photosensitive resin composition is after filming and baking in advance, expose, remove unexposed and filming partly of not wanting though can alkaline-based developer dissolve, but be easy to generate do not develop position particle or dissolved matter remaining not when developing, the back of therefore developing is difficult to form accurate photoresist image.In order to improve the disappearance of video picture difference, Japanese kokai publication hei 10-10749 application for a patent for invention case discloses, make developer solution with water, alkali compounds, teepol, though this kind allotment has the developer solution of teepol to have effects such as no residue, video picture be good in use, but the dispersion stabilization of the defoaming of developer solution, operating temperature and chromatic photoresist is poor, and is therefore also undesirable in the use.
The modern inventor is because become known for the developer solution of photosensitive resin composition, when using, it can't take into account character such as the dispersion stabilization of development, defoamer, chromatic photoresist and serviceability temperature simultaneously, be in line with excelsior spirit, improved at above-mentioned disappearance.
The objective of the invention is providing that a kind of development property is good, defoaming is strong, the operating temperature height of allowing, and can take into account the dispersion stabilization of chromatic photoresist and avoid the constituent of the developer solution that can be used for photosensitive resin composition that residue generates.
The present invention is providing a kind of after photoresist exposure, and in order to the constituent of the developer solution that forms image, above-mentioned constituent comprises: (A) water; (B) alkali compounds of at least a content 0.01～5 weight %; (C) at least a content 0.01～3.5 weight % non-ionic surfactant;
Wherein, non-ionic surfactant (C) has following structural formula (I):
----structural formula (I)
Wherein, R
1, R
2, R
3, R
4, R
5Be to be selected from: hydrogen, alkyl (alkyl), aryl (aryl), aralkyl (aralkyl), halogen (halogen).R
6Be selected from: ethylidene (ethylene ,-C
2H
4-), propylidene (propylene ,-C
3H
6-), butylidene (butylene ,-C
4H
8-).R
7Be selected from: hydrogen, acetyl group (acetyl), alkyl (alkyl), aryl (aryl); N is 6～23 integer; And, R
1, R
2, R
3, R
4, R
5In at least wherein 2 be aralkyl or aryl.
Below at used herein each form part (A)～(C) specify.(A) water:
Generally speaking, developer solution is to be used as dispersion medium with solvent, and common solvent has: two kinds in organic solvent and water, wherein in the developer solution the organic solvent of normal use for example be: the halogen solvent of trichloroethanes; Only can destroy ozonosphere in the environment, and its inflammability is strong and foul smelling, therefore, at aspects such as environmental protection, health, safety disappearance is arranged all, and is not used gradually in view of the halogen solvent; Another kind of is the developer solution of dispersion medium with water because have hypotoxicity, do not have inflammability and management easily, liquid waste processing is easy and advantage such as with low cost, therefore, water has become the main dispersion medium of developer solution at present.(B) alkali compounds:
The effect of alkali compounds of the present invention is: dissolve the resin of non-image part, being suitable for alkali compounds of the present invention can be divided into: two kinds of organic basic compound and inorganic alkaline compounds, wherein:
(1) the machine alkali compounds is to be selected from: hydrogen-oxygen level Four ammonium salt compounds and organic amine, the object lesson of above-mentioned hydrogen-oxygen level Four ammonium salt compounds has: hydrogen-oxygen tetramethylammonium (tetramethylammonium hydroxide), 2-hydroxyl-hydrogen-oxygen trimethylammonium (2-hydroxyltrimethyl ammoniumhydroxide), and the object lesson of organic amine has: single methylamine (monomethylamine), dimethylamine (dimethyl-amine), trimethylamine (trimethylamine), single isopropylamine (monoiso-pyruamine), two-isopropylamine (di-isopyruamine), second-ethylaminoethanol (ethanolamine).
(2) inorganic alkaline compound used in the present invention can be alkaline metal or alkaline earth compound, and it can be selected from: at least a or two above potpourris of compounds such as lithium hydroxide, NaOH, potassium hydroxide, dibastic sodium phosphate, ammonium dihydrogen phosphate (ADP), sodium dihydrogen phosphate, potassium dihydrogen phosphate, lithium phosphate, lithium metasilicate, potassium silicate, sodium silicate, lithium carbonate, sal tartari, sodium carbonate, lithium borate, sodium borate, ammonium hydroxide; For to use acrylate (acrylate) be resin as for the cementing agent (binder) of photoresist, alkali compounds used in the present invention is to be preferable with the made alkaline aqueous solution of joining of alkali metal hydrogen oxygen compound.
The present invention is used in the constituent of developer solution of photoresist, and the use amount of above-mentioned alkali compounds is 0.01～5 weight %, is preferably 0.02～3.5 weight %, is more preferred from 0.03～1.5 weight %; When the weight percent of alkali compounds is lower than 0.01%, develop and render a service inadequately, the development variation, and when its weight percent was higher than 5%, the effectiveness of developing was too strong, wayward processing procedure is so development is also not good.(C) non-ionic surfactant
Non-ionic surfactant used in the present invention (C) is to have following structural (I):
--------structural formula (I)
The present invention has in the non-ionic surfactant (C) of structural formula (I), R
1, R
2, R
3, R
4, R
5Be hydrogen, alkyl (alkyl), aryl (aryl), aralkyl (aralkyl), halogen (halogen), and wherein contain two above aryl or aralkyls at least; Be R
1～R
5In at least two be aralkyl, or at least two be aryl, perhaps at least one is that aralkyl, one are aryl; R in non-ionic surfactant (C)
1～R
5Do not contain any or when only containing an aryl (or aralkyl), constituent is for the dispersion stabilization variation of chromatic photoresist, that is residue increases; In addition, non-ionic surfactant used in the present invention (C) also can produce above-mentioned disappearance if do not have said structure formula (I).
R in the structural formula of the present invention (I)
6Be ethylidene (ethylene ,-C
2H
4-), propylidene (propylene ,-C
3H
6-), butylidene (butylene ,-C
4H
8-).R
7Be hydrogen, acetyl group (acetyl), alkyl (alkyl), aryl (aryl); N is 6～23 integer, is preferably 6～1 8, is more preferred from 6～14, and when the value of n was lower than 6, this non-ionic surfactant (C) was poorly soluble with water (A), and development effect is poor, and when the value of n is higher than 23, the stability of factorization variation of chromatic photoresist.
Non-ionic surfactant of the present invention (C) can be following cited person, but not as limit, for example:
1) polyethylene oxide-3,5-hexichol ethylphenyl ether (9 moles of addition products of oxirane), English
Literary fame is called: Polyoxyethylene-3, and 5-bis (1-phenyl ethyl) phenyl ether, the n value of structural formula (I) is 9, the concrete structure formula is:
2) polyethylene oxide-3,5-hexichol ethylphenyl ether (12 moles of addition products of oxirane),
English name is: Polyoxyethylene-3, and 5-bis (1-phenyl ethyl) phenyl ether,
The n value of structural formula (I) is 12, and the concrete structure formula is:
3) polyethylene oxide-2,4,6-triphen ethylphenyl ether (9 moles of addition products of oxirane),
English name is: Polyoxyethylene-2, and 4,6-tris (1-phenyl ethyl) phenyl ether,
The n value of structural formula (I) is 9, and the concrete structure formula is:
4) polyethylene oxide-2,4,6-triphen ethylphenyl ether (12 moles of addition products of oxirane), English name is: Polyoxyethylene-2,4,6-tris (1-phenyl ethyl) phenyl ether, the n value of structural formula (I) is 12, the concrete structure formula is:
The present invention is except can using the non-ionic surfactant with structural formula (I), necessary fashion can further add other interfacial agent, for example: polyethylene oxide fatty acid ester (polyoxyethylene fatty acid ester), polyethylene oxide sorbitol anhydride fatty acid ether (polyoxyethylene sorbitan fatty acid ether), polyethylene oxide base ether (polyoxyethylenealkyl ether), polyethylene oxide aryl ether (polyoxyethylene alkyl aryl ether), polyethylene oxide phenyl ether compound or its potpourris such as (polyoxylene styrene phenol ether).
In the developer solution component of the present invention, the weight percent of above-mentioned non-ionic surfactant (C) is 0.01～3.5 weight %, is preferably 0.03～2.5 weight %, is more preferred from 0.04～1.5 weight %; When the weight percent of non-ionic surfactant (C) is lower than 0.01%, the dispersion stabilization variation of chromatic photoresist easily forms residue, and when the weight percent of aforementioned non-ionic surfactant (C) is higher than 3.5%, defoaming is poor, can influence the smooth operation of development.
Developer solution of the present invention is fit to use and is containing the photoresist that stains of colorant, above-mentioned photoresist is also without particular limitation, it can be the photosensitive resin composition of eurymeric or minus, only aspect the chromatic photosensitivity resin combination, it includes usually: compositions such as the binding resin of the pigment of organic or inorganic (colorant), alkali-soluble (binder resin), photosensitive compounds and solvent; The binding resin of above-mentioned alkali-soluble can be: the polymkeric substance of novolac resin (Novolac resin), acrylic resin (acrylate resin), maleic anhydride (Maleic anhydride) or its half ester (half ester), poly-hydroxy benzenes (polyhydroxy styrene) etc. are good with acrylic resin wherein; And aforementioned acrylic resin is meant that with (methyl) acrylate [(meth) acrylate] and/or (methyl) acrylic acid [(meth) acrylic acid] be Main Ingredients and Appearance, and its object lesson has: (1) methyl methacrylate (methyl methacrylate)/hydroxy benzenes (hydroxy styrene)/styrene (styrene)/methacrylic acid (methacrylic acid) multipolymer.(2) benzyl methacrylate (benzyl methacrylate)/methacrylic acid (methacrylic acid)/styrene (styrene) multipolymer.(3) methyl methacrylate (methyl methacrylate)/methacrylic acid (methacrylic acid)/styrene (styrene) multipolymer.(4) benzyl methacrylate (benzyl methacrylate)/methacrylic acid (methacrylic acid)/huge monomer of styrene (polystyrene macro monomer) multipolymer.(5) methyl methacrylate (methyl methacrylate)/methacrylic acid (methacrylic acid)/huge monomer of styrene (polystyrene macro monomer) multipolymer.(6) methyl methacrylate (methyl methacrylate)/benzyl methacrylate (benzyl methacrylate)/methacrylic acid (methacrylic acid) multipolymer.(7) methyl methacrylate (methyl methacrylate)/benzyl methacrylate (benzyl methacrylate)/2-hydroxyethyl methyl acrylate (2-hydroxy ethyl methacrylate) multipolymer.
Below to of the present invention each form and to do a detailed explanation:
[evaluation method of developer solution] one,
Development: observe the integrality that forms in the glass substrate epigraph.
Zero: good
*: bad two,
Residue: with the non-image position on 250 times the microscopic examination glass substrate whether residue is arranged.
Zero: no residue
△: level of residue is few
*: level of residue is many three,
Defoaming: with the prepared developer solution 20ml of 100ml graduated cylinder splendid attire, and sway with rectilinear
Machine swayed under appropriate frequency 30 minutes, left standstill afterwards to measure its foam height after one hour, again
According to foam height with following benchmark evaluation:
Zero: below the 1.5cm
*: 1.5cm is above four,
Operating temperature is measured: with the prepared developer solution of 100ml graduated cylinder splendid attire 20ml, and insert mercury
Thermometer places graduated cylinder the glass beaker that is filled with water afterwards, and surface level need be higher than developer solution liquid
Face, slowly heating of heating plate thereafter treats to get when developer solution is muddiness this muddy temperature, put again to
Cool off in the room temperature, treat to get this clarifying temp when developer solution is clarification again, reach with aforementioned muddy temperature
Clarifying temp is average, and makes following benchmark evaluation according to its temperature:
More than zero: 45 ℃
△：38～45℃
*: below 38 ℃ five,
Dispersion stabilization: get the chromatic photosensitivity resin composition that the developer solution 250g that is estimated adds 1g
Thing is after suitable mixed shaking, with 5 μ m filter paper filterings, again in 105 ℃ of bakings one hour, scale
Its filter net weight, according to this weight with following benchmark evaluation:
Zero: net weight is less than 0.04g
*: net weight is greater than 0.04g
[reference example]
Developer solution component of the present invention is to be used in photoresist exposure back to form the material of image, and the composition and the use amount of the constituent of above-mentioned photoresist are as shown in the table:
| Form part | The object lesson of composition | Use amount |
| Cementing agent | Methacrylic acid-benzyl methacrylate multipolymer | 8.40 kilogram |
| Photoresist | Two (methyl) acrylic acid neopentyl glycol glycol hydroxyl trimethylace tonitric ester | 0.24 kilogram |
| The light initiator | 2-benzyl-2-nitrogen, nitrogen-dimethylamine-1 (4-morpholino phenyl) 1-butanone [2-benzyl-2-N, N-dimethylamino-1-(4-morpholino-phenyl)-1-butanonel] | 0.14 kilogram |
| 4,4 '-two (diethylamine) benzophenone [4,4 '-bis (diethylamine) benzophenone] | 0.04 kilogram | |
| Organic solvent | Propylene glycol monomethyl ether acetate (Propyleneglycol methyl ether acetate) | 9.54 kilogram |
| Pigment | PR177 (Ciba-Geigy, trade name Red A2B) | 4.00 kilogram |
Above-mentioned each composition is mixed with swing-out stirrer, and the mode with rotary coating is applied in photosensitive resin composition on the glass substrate then, and after 110 ℃ of pre-down baking, again with 200mJ/cm
2Ultraviolet exposure, can form the base material that preparation forms image, to prepare to do the processing of developing.
[embodiment]
[embodiment 1]
The base material that reference example is made impregnated in the developer solution shown in table one embodiment 1 about 2 minutes, and then in 200 ℃ pre-roasting 60 minutes, can on aforementioned glass baseplate, form plated film; And the developer solution of present embodiment comprises: the potassium hydroxide of the water of 99.2 weight %, 0.07 weight %, and the polyethylene oxide of 0.1 weight %-3,5-hexichol ethylphenyl ether (9 moles of addition products of oxirane); Rerum natura after the development as shown in Table 2, promptly with the image on the microscopic examination substrate, good, the residue material of its development does not have as can be known, and the defoaming of developer solution, operating temperature and dispersion stabilization are all good.
[embodiment 2～5]
Mode of operation with embodiment 1, difference is the composition of developer solution as shown in Table 1, as shown in Table 2, forms and use amount via changing each, can obtain effects such as development property is good, the image of no residue, and defoaming, operating temperature and the dispersion stabilization of while developer solution is all good equally.
[comparative example]
[comparative example 1]
Mode of operation with embodiment 1, difference is that the composition with developer solution changes over shown in the table one, promptly the composition of this comparative example 1 comprises: the potassium hydroxide of the water of 89 weight %, 7 weight %, and the non-ionic surfactant of 4 weight %, the result after the development is stated from table two.
[comparative example 2～9]
Mode of operation is all with embodiment 1, and difference is the constituent composition and the use amount of developer solution, and the rerum natura of developer solution and development effect are stated from table two.
By above comparative descriptions as can be known, the present invention is via specific composition and use quantitative limitation, can improve the development effect of image really, also noresidue on the image, and the rerum naturas such as defoaming, operating temperature and dispersion stabilization of developer solution are all good simultaneously; And by comparative example 1 experiment showed, that when the use amount of potassium hydroxide and non-ionic surfactant is higher than 5 weight % and 3.5 weight % respectively its development effect is poor, the defoaming of developer solution and dispersion stabilization are also poor; Shown in comparative example 2, when the use amount of the alkali compounds (B) that uses as the present invention is lower than 0.01 weight %, the development of constituent is poor, and when the use amount of this alkali compounds (B) is higher than 5 weight %, the development effect of substrate epigraph is also poor, and this is by the physical property test susceptible of proof of comparative example 3; Consult comparative example 4, when interfacial agent of the present invention did not meet the qualification of structural formula (I), the level of residue of substrate epigraph was many, and the defoaming of developer solution and dispersion stabilization are also relatively poor; And experimental results show that by comparative example 5, when not using interfacial agent in the developer solution, the defoaming of this developer solution, operating temperature and dispersion stabilization are all relatively poor, and when interfacial agent changes over polyethylene oxide nonyl phenylate (8 moles of addition product polyoxyethylene of oxirane nonyl phenyl ether), with the image on the microscopic examination substrate, its level of residue is many, and the defoaming of developer solution and dispersion stabilization be variation also, and this is by comparative example 6 susceptible of proofs; Shown in comparative example 7,9, when making interfacial agent, defoaming in the developer solution and dispersion stabilization are also poor when only using polyethylene oxide sorbitol anhydride fatty acid ether or polyethylene oxide 16 oleoyl ethers (polyoxyethylene oleyl cetyl ether) in the developer solution; And when adopting the octadecyl benzene sulfonic acid sodium salt of anionic property interfacial agent in the developer solution (Japanese kokai publication hei 10-10749 patent application case), the defoaming of its developer solution, operating temperature and dispersion stabilization are all not good.
The above only is several preferable possible embodiments of the present invention, has the knack of this technology personage such as, and it all ought to be contained in the technical solution of the present invention scope according to modification or change that the present invention's spirit category is done.Table one: the proportion of composing of developer solution
The ※ total data is represented weight % table two: evaluation result
| Experiment numbers | Development | Residue | Defoaming | Operating temperature | Dispersion stabilization | |
| Embodiment | 1 | ○ | ○ | ○ | ○ | ○ |
| 2 | ○ | ○ | ○ | ○ | ○ | |
| 3 | ○ | △ | ○ | ○ | ○ | |
| 4 | ○ | ○ | ○ | ○ | ○ | |
| 5 | ○ | △ | ○ | ○ | ○ | |
| Comparative example | 1 | × | ○ | × | △ | × |
| 2 | × | ○ | ○ | ○ | ○ | |
| 3 | × | ○ | ○ | △ | ○ | |
| 4 | ○ | × | × | ○ | × | |
| 5 | ○ | ○ | × | × | × | |
| 6 | ○ | × | × | △ | × | |
| 7 | ○ | ○ | × | ○ | × | |
| 8 | ○ | ○ | × | × | × | |
| 9 | ○ | ○ | × | × | × | |
Claims (8)
1, a kind of constituent of developer solution, it is to use alkaline water system developer solution used when photoresist exposure back image forms, and it is characterized in that this constituent comprises:
(A) water;
(B) alkali compounds of at least a content 0.01～5 weight %;
(C) at least a content 0.01～3.5 weight % non-ionic surfactant; Wherein, non-ionic surfactant (C) has following structural formula (I):
----structural formula (I)
Wherein, R
1, R
2, R
3, R
4, R
5Be to be selected from: hydrogen, alkyl, aryl, aralkyl, halogen;
R
6Be selected from: ethylidene, propylidene, butylidene;
R
7Be selected from: hydrogen, acetyl group, alkyl, aryl;
N is 6～23 integer;
And, R
1, R
2, R
3, R
4, R
5In at least wherein 2 be aralkyl or aryl.
2, the constituent of developer solution according to claim 1 is characterized in that the R in the structural formula (I)
2, R
4Be aralkyl or aryl.
3, the constituent of developer solution according to claim 1 is characterized in that the R in the structural formula (I)
2, R
4Be phenethyl.
4, the constituent of developer solution according to claim 1 is characterized in that the R in the structural formula (I)
1, R
3, R
5Be aralkyl or aryl.
5, the constituent of developer solution according to claim 1 is characterized in that the R in the structural formula (I)
1, R
3, R
5Be phenethyl.
6, the constituent of developer solution according to claim 1 is characterized in that this alkaline aqueous solution is the aqueous solution of alkali metal compound.
7, the constituent of developer solution according to claim 1 is characterized in that this developer solution is to be applicable to the photoresist that stains that contains colorant.
8, the constituent of developer solution according to claim 1 is characterized in that this developer solution is to be applicable to the acrylic resin to be the photoresist that stains of cementing agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 99127536 CN1126006C (en) | 1999-12-30 | 1999-12-30 | Composition of developing liquid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 99127536 CN1126006C (en) | 1999-12-30 | 1999-12-30 | Composition of developing liquid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1301995A CN1301995A (en) | 2001-07-04 |
| CN1126006C true CN1126006C (en) | 2003-10-29 |
Family
ID=5284901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 99127536 Expired - Lifetime CN1126006C (en) | 1999-12-30 | 1999-12-30 | Composition of developing liquid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1126006C (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100580561C (en) * | 2003-07-16 | 2010-01-13 | 三菱瓦斯化学株式会社 | Anticorrosive developing composition |
| WO2007028294A1 (en) * | 2005-09-05 | 2007-03-15 | Byd Company Limited | A developer solution for photoresist |
| CN1928724B (en) * | 2005-09-05 | 2010-09-29 | 比亚迪股份有限公司 | Photoresistance developer |
| JP2007254510A (en) * | 2006-03-20 | 2007-10-04 | Fujifilm Corp | Liquid detergent |
| CN105589304B (en) * | 2016-03-04 | 2020-08-14 | 苏州晶瑞化学股份有限公司 | Developing solution for photoresist and preparation method and application thereof |
| CN106154771A (en) * | 2016-08-31 | 2016-11-23 | 珠海顺泽电子实业有限公司 | Activated water application in developer solution |
-
1999
- 1999-12-30 CN CN 99127536 patent/CN1126006C/en not_active Expired - Lifetime
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| Publication number | Publication date |
|---|---|
| CN1301995A (en) | 2001-07-04 |
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