CN102141743A - Photoresist peeling solution composition with metal protection - Google Patents
Photoresist peeling solution composition with metal protection Download PDFInfo
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- CN102141743A CN102141743A CN 201010262392 CN201010262392A CN102141743A CN 102141743 A CN102141743 A CN 102141743A CN 201010262392 CN201010262392 CN 201010262392 CN 201010262392 A CN201010262392 A CN 201010262392A CN 102141743 A CN102141743 A CN 102141743A
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Abstract
The invention discloses a photoresist peeling solution composition with metal protection. The photoresist peeling solution composition consists of the following substances in percentage by weight: 0.1 to 10 percent of quaternary ammonium hydroxide, 5 to 30 percent of water-soluble alkanol amine, 55 to 94.4 percent of water-soluble organic polar solvent and 0.5 to 5 percent of sugar alcohol additive, wherein the water-soluble organic polar solvent is sulfone, sulfoxide, amide or lactam solvent. Compared with the conventional peeling solution composition, the photoresist peeling solution composition has excellent corrosion resistance to a metal-based coating covered by photoresist, particularly copper and aluminum at the same time of ensuring excellent photoresist peeling performance, and has excellent side corrosion protection effect on the copper. Meanwhile, the peeling solution composition has low volatility and low toxicity, is easily cleaned by using deionized water, and has good maneuverability. The composition is used for peeling and dissolving a photoresist mask in a semiconductor element manufacturing process.
Description
Technical field
The present invention relates to a kind of novel photoresist lift off fluid composition, be used for semiconductor element manufacture process peeling off and dissolve for the photoresist mask.
Background technology
Semiconductor element has large amount of complex and extremely trickle structure, needs to make through the technology in many stages, and wherein photoetching process need be used tens to tens times repeatedly.Photoetching process is generally as follows: substrate is enclosed conductive metal film through plating, evenly coat photoresist again, after given pattern exposure, use developer to make photoresist form given line pattern, then use etching solution that conductive metal film is carried out etching and form circuit, at last above-mentioned photoresist pattern is peeled off.
Photoresist lift off mainly contains two kinds of dry method and wet methods, and wherein dry method adopts plasma ashing to handle to change photoresist into the ashing material, remove, but this method stays photoresist residue or sidewall protection deposited film etc. easily, need further handle; Wet method then is to use remover composition that photoresist is dissolved or is partly dissolved, and peels off from substrate thus.The photoresist of this method is residual few, convenient post-treatment.For photoresist lift off liquid, it is effective that requirement is peeled off, conductive metal layer under preferably can covering photoresist does not have erosion, in addition in semiconductor is made, the user is for the economy of stripper, environmental pollution, safety of operators, toxicity, also have in various degree concern to the problems such as dissolubility that peel photoresist.
It is many that alkanolamine or azanol etc. mixed the example that uses during at present common stripper was formed with the different solvents auxiliary agent.The patent aspect, following example is arranged: organic amine such as alkyl group hydramine MEA and diethylene glycol list methane ether (EDG), r-butyrolactone (GBL), 1, the polar solvent more than a kind in 3-dimethyl-2-imidazolone (DMI), N-Methyl pyrrolidone (NMP), the dimethyl sulfoxide (DMSO) (DMSO) mixes (Jap.P. JP63231343A); Organic amine compound and diethylene glycol monoalky lether, dimethyl acetamide (DMAc), NMP, DMSO isopolarity solvent (Jap.P. JP4124668A); Alkanolamine and amide solvent such as N-methylacetamide (MAc), DMAc, dimethyl formamide (DMF), N, N-diethyl acetamides (DEAc) etc. mix (U.S. Pat 4770713A); Organic amine compound such as MEA and 2-(2-amino ethoxy) ethanol (AEE) and polar solvent such as DMAc, DMF, NMP, DMSO, carbitol acetate ester and methoxyl acetoxy-propane mix (U.S. Pat 4617251A); Alkanolamine, dihydroxy benzenes and DMSO (Jap.P. JP5281753A); Azanol and alkanolamine are the remover composition (U.S. Pat 5334332A) of major component.
In the above example, amine is as alkaline matter, peel off for the dissolving of photoresist to play a major role, so content is all more than 10%, most between 30%-60% than higher.When amine substance content is lower than 15%, the peeling off effect and will have a greatly reduced quality of this kind stripper, even photoresist occurs and do not peel off undissolved phenomenon.And, if do not add any antiseptic, then the metal level under the photoresist is had corrosive attack, so the stripper of this kind often can not well solve the erosion problem to metal because the amine of too high amount makes that whole system basicity is higher.And these strippers form the weak point that also has other, have big toxicity such as some composition such as azanol etc., to operating personnel's security presence hidden danger; Some solvent or auxiliary agent are more difficult to get, and need oneself synthetic or on the high side, make product economy not good;
Stripper is also by the forming of inorganic alkali solution, but because inorganic base solubleness in most of organic solvents is extremely low, limited the application of this composition: the aqueous solution of inorganic base is serious unusually for the erosion of metal level; If adopt specific solvent to cooperate the dissolving inorganic base, the effect of then peeling off is good inadequately.Under this background, organic base is generally quaternary ammonium hydroxide and cooperates the stripper that forms to obtain using comparatively widely with polar organic solvent.(Jap.P. JP7201704A; Chinese patent CN1224864C; U.S. Pat 4518765A; U.S. Pat 5091103A) this kind stripper for photoresist to peel off effect fine, forming great majority is the material of low-volatile low-toxic.
Yet under the situation of not adding auxiliary agent, this stripper is more serious for oxidation, the erosion of metal level such as aluminium, particularly copper, shows as the copper surface discolouration, the blackout of growing dim.The way that addresses this problem is normally added corrosion inhibiter, as: add (Chinese patent CN1312535C such as aromatic hydroxy compound or sugar alcohol; Chinese patent CN1224864C); Add triazole class compounds (Jap.P. JP2000162788A; Chinese patent CN1682155A; Chinese patent CN1130454C); Add thio-based compound (Jap.P. JP2000273663A; Chinese patent CN1264066C).Protection does not have effect substantially but aromatic hydroxy compound or sugar alcohol compound are for copper; And triazole compounds biodegradabilities such as benzotriazole dissolubility not good enough, in water is lower, and water flushing back antiseptic may remain in wafer surface, can produce harmful effect to the back operation.Or the like problem limited Application of Additives.Some stripper solves erosion problem to metal by the basic composition that changes solution, but tends to cause the decline of photoresist lift off effect like this.In addition, in the former research, the little lateral erosion problem of copper post in stripping process at wafer surface carried out deep discussion, seldom sees the stripper constituent with good copper lateral erosion protection.
Summary of the invention
For solving existing stripper for the metal erosion problem of copper particularly, and lateral erosion protection problem at copper, technical matters to be solved by this invention is a kind of photoresist lift off fluid composition with metal coating of exploitation, said composition is being possessed excellent photoresist lift off performance simultaneously, for the copper base under the photoresist with aluminium basely do not have erosion substantially, and has good copper lateral erosion protective value; This remover composition has low volatility and hypotoxicity simultaneously, cleans easily, has avoided possible residue to cause harmful effect for successive process.
Inventor's development of new stripper, expectation can reach following requirement:
1. splitting time is short, peel off effective, residual impurity particulate not after peeling off;
2. metallic copper and aluminium aggressivity under photoresist being covered are low;
In stripping process for the copper post of wafer surface, the lateral erosion protection is respond well;
4. have low volatility and hypotoxicity, can not bring harm operating personnel's health;
5. vaporization loss is little under serviceability temperature, convenient utilization again;
6. water-soluble good, be easy to clean, clean the back noresidue.
For reaching above-mentioned requirements, the inventor has carried out a large amount of experiments to the fiting effect that the various one-tenth of stripper are grouped into, and finally finds an effectively combination, and this combination is splendid for the protectiveness of metallic copper and aluminium, and is respond well to the lateral erosion protection of copper; Its composition is the low-volatile water-soluble substances of low toxicity simultaneously; And all compositions all to the positive effect of having peeled off of photoresist, are peeled off respond well.Particularly, the photoresist lift off fluid composition with metal coating of the present invention's exploitation is made up of following four kinds of materials: (A) quaternary amines oxyhydroxide; (B) water-soluble alkanolamine; (C) water soluble organic polar solvent; (D) adjuvant, wherein:
(A) compound of the preferred following general formula of the quaternary amines oxyhydroxide of composition (I) expression.
In the following formula, R1, R2, R3, R4 represent alkyl or the hydroxyalkyl of carbon number 1-4 respectively independently.
Above-mentioned quaternary amines oxyhydroxide can be enumerated tetramethyl ammonium hydroxide (TMAH), tetraethyl ammonium hydroxide (TEAH), tetrapropylammonium hydroxide, tetrabutylammonium, hydroxide four pentyl ammonium, hydroxide monomethyl tripropyl ammonium, hydroxide dimethyl diethyl ammonium, hydroxide (2-hydroxyethyl) trimethyl ammonium (choline), hydroxide (2-hydroxyethyl) triethyl ammonium, hydroxide (2-hydroxyethyl) tripropyl ammonium, hydroxide (1-hydroxyethyl) trimethyl ammonium or the like.This compounds is organic base, can react with the photoresist composition, makes stripper dissolve photoresist rapidly; And they are water-soluble substances, can be clean by washing easily.Should (A) composition be the important component of stripping photoresist, but can and aluminium base corrosive attack be arranged to the copper base when using separately.This wherein, from can conveniently obtaining and the actual effect aspect of peeling off is considered, more preferably TMAH, TEAH and choline etc.This (A) composition generally adopts a kind of, also can use two or more mixing.
(A) content of composition is 0.1-10% by weight percentage, is preferably 0.5-3%.If (A) component content is very few, then the performance of stripping photoresist is low, the incomplete phenomenon of photoresist lift off may occur; When (A) component content is too high, also not obvious to the raising of whole stripping performance, and itself can strengthen the difficulty of metal coating for corrosion of metal.
(B) alkanolamine of composition has monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, triisopropanolamine, N-methylethanolamine, N-ehtylethanolamine, N-butylethanolamine, N, N-dimethylethanolamine etc. for example.In this patent, it is copper protection in stripping process that this compounds mainly acts on, and avoids copper to be stripped from corrosion; Because this compounds itself is an alkaline matter, has certain promotion for peeling off of photoresist, and can not play inhibition to stripping photoresist simultaneously as some protective agent.In the time of (B) composition high-load itself, do not use the main composition that also can be used as stripper, and this kind stripper also has partial corrosion for metal with (A) components matching.But we find in experiment, in certain content range, (B) composition with (A) be present in system jointly in the middle of on the contrary the copper base is not had erosion substantially: copper-plated wafer is soaked in after this stripper forms certain hour, and copper face can not produce the vestige that is etched; The copper post does not have tangible lateral erosion yet.(B) composition can be regarded as copper protective agent in body series, has certain stripping photoresist effect simultaneously.And (B) content of composition can increase and decrease with the size of (A) component content.This wherein considers from the practical effect aspect, preferably uses monoethanolamine or triethanolamine.
(B) content of composition is preferably 5-30%, more preferably 10-25% by weight percentage.If it is (B) component content is low excessively, then not obvious for the protection of copper.
(C) the water soluble organic polar solvent of composition, can use sulfone class sulfoxide classes such as dimethyl sulfoxide, dimethyl sulfone, diethyl sulfone, tetramethylene sulfone for example, N, dinethylformamide, N, N-dimethyl acetamide, N-NMF, N, amide-types such as N-diethyl acetamide, lactams such as N-N-methyl-2-2-pyrrolidone N-, N-ethyl-2-pyrrolidone, N-propyl group-2-Pyrrolidone.Organic solvent is used for dissolving (A) composition and (B) composition, and has the effect of swelling dissolving for the photoresist of being crossed by alkali reaction, impels peeling off of photoresist.If (C) become the component selections mistake, then photoresist lift off liquid peels off effect and will obviously descend and even not peel off.During the stripper of this patent is formed, (C) the preferred dimethyl sulfoxide (DMSO) of composition.
(C) content of composition is generally the surplus except that (A), (B), (D) composition, is 55-94.4% by weight percentage, is preferably 69-88.5%.Under the constant situation of (A) component content, along with the decline of (C) component content, stripper also descends to the effect of peeling off of photoresist thereupon; As (C) when component content is too small, photoresist will be difficult to be stripped from.
(D) the glycitols adjuvant of composition has fructose, glucose, galactose, sorbose, sweet mellow wine, sorbierite and xylitol etc. for example.In this stripper combination, the effect of adjuvant is to strengthen the protective effect of composition for metallic aluminium, avoid stripper be combined in the stripping process to aluminium base erosion.Because the erosion action to metallic aluminium mainly is that composition (A) causes, therefore in the ordinary course of things, (D) content of composition should increase and decrease along with the variation of (A) component content.
(D) content of composition is 0.5-5% by weight percentage, is preferably 1-3%.Under the constant situation of (A) component content, along with the decline of (D) component content, stripper also descends to the protection effect of metallic aluminium thereupon; As (D) when component content is too small, the erosion of metallic aluminium is serious.On the other hand, under the constant situation of (A) component content, along with the rising of (D) component content, stripper is peeled off effect and will be descended thereupon photoresist; If (D) component content is too high, then photoresist will be difficult to be stripped from.
The preparation method that the present invention has the remover composition of metal coating there is no special feature, take by weighing by weight percentage (A), (B), (C) and (D) after, adopt ordinary skill in the art means mixed dissolution to get final product.
The remover composition that the present invention has metal coating can be used to peel off and can list: 1. the eurymeric photoresist that contains diazo naphthoquinone compound and novolac resin with the photoresist of alkaline aqueous solution development; 2. contain and be exposed and acidic compound, decomposed by acid and the compound that the dissolubility of alkaline aqueous solution is increased and the eurymeric photoresist of alkali soluble resin; 3. contain and be exposed and acidic compound, decomposed by acid and the eurymeric photoresist of the alkali soluble resin of group that the dissolubility of alkaline aqueous solution is increased; 4. contain negative photoresist of the acidic compound of photic energy, crosslinking chemical and alkali soluble resin or the like, but be not limited to above a few class.
What further specify is, use remover composition of the present invention to carry out lift-off processing after, generally carry out general ultrapure water rinsing processing and dried and can remove stripper fully.
With respect to existing remover composition, the present invention is possessing excellent photoresist lift off performance simultaneously, and it is low to cover Metal Substrate coatings corrosivity down for photoresist, for the copper base with aluminium basely do not have erosion substantially, particularly protects effect obvious for the lateral erosion of copper.Remover composition of the present invention has low volatility and hypotoxicity, thereby reduces environmental problem greatly and for operating personnel's toxicity problem; Be water-soluble substances owing to form, easily clean by washed with de-ionized water, the harmful effect of having avoided residue may cause for the semiconductor element successive process.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.These embodiment are interpreted as only being used to the present invention is described and are not used in restriction protection scope of the present invention.After the content of having read the present invention's record, those skilled in the art can make various changes or modifications the present invention, and these equivalences change and modify and fall into claim of the present invention institute restricted portion equally.
The preparation process of photoresist lift off liquid does not all have special feature among following examples 1-13 and the comparative example 1-8, take by weighing by weight percentage (A), (B), (C) and (D) after, adopt ordinary skill in the art means mixed dissolution to get final product.
1, the fissility of photoresist
In 90 ℃, the wafer that will be covered with photoresist (available alkaline aqueous solution development) pattern floods wherein, measures the time that photoresist layer is peeled off fully, estimates according to following metewand with the photoresist lift off liquid constant temperature shown in the following table 1.The result is as shown in table 1.
(evaluation criterion)
Zero: peeling rate and existing stripper are than identical or very fast;
△: peeling rate is slightly slower than existing stripper;
*: peeling rate is much slower than existing stripper.
2, to the anticorrosive property of copper or aluminium
With the photoresist lift off liquid constant temperature shown in the following table 1 in 90 ℃, the wafer dipping that will form copper layer overlay film (or aluminium lamination overlay film) but not be covered with photoresist wherein, take out after 60 minutes, use microscope to carry out surface observation (enlargement factor: 40,100 and 400), estimate according to following metewand.The result is as shown in table 1.
(evaluation criterion)
Zero: copper layer or aluminium lamination are not seen erosion fully;
△: the surface has fragmentary erosion to exist;
*: visible serious erosion the in copper or aluminium surface.
3, to the lateral erosion protective value of copper
Photoresist lift off liquid constant temperature shown in the following table 1 in 90 ℃, copper post (copper column diameter 82-84 micron, D have been formed with the surface
0) but the wafer dipping that is not covered with photoresist is wherein, takes out after 60 minutes, measures copper column diameter D
1, the reduction ((D of calculating copper column diameter
0-D
1)/D
0), estimate according to following metewand.The result is as shown in table 1.
(evaluation criterion)
Zero: the vary in diameter of copper post is less than or equal to 3%;
△: the vary in diameter of copper post comprises 10% between 3% to 10%;
*: the vary in diameter of copper post is greater than 10%.
Table 1:
In the last table 1:
TMAH: Tetramethylammonium hydroxide
TEAH: tetraethyl ammonium hydroxide
MEA: monoethanolamine
TEA: triethanolamine
DMSO: dimethyl sulfoxide (DMSO)
D1: sorbierite
D2: xylitol
Result by table 1 can confirm, in the stripper system, contain (A) composition quaternary amines oxyhydroxide simultaneously and (B) the embodiment 1-13 of the water-soluble alkanolamine of composition and comparative example 3 are not all observed to covering the corrosion of copper layer the lateral erosion protective value excellence of stripper simultaneously; And contain (A) composition or (B) comparative example 1 of composition separately; 2,5,6 and (B) 3 pairs less relatively of comparative examples of composition cover the copper layer and then have in various degree corrosion; the lateral erosion of copper protection effect is also bad, as can be known the effect of copper protection by (A) composition and (B) acting in conjunction of composition obtain.In addition, by comparative example 7 and 8 as can be seen, (D) composition in the system provides good aluminium protective value, but this composition does not have any protective effect for metallic copper.Embodiment 1-8 comprises that simultaneously (A) composition, (B) composition, (C) composition reach (D) remover composition of composition; they are good for the protectiveness of copper base and aluminium base coatings; lateral erosion protection to copper is respond well, also good to the stripping performance of photoresist simultaneously.
In sum, the invention provides a kind of like this photoresist lift off fluid composition, possessing excellent stripping performance simultaneously, good for metallic copper under the photoresist and aluminium protective value.Because this remover composition composition all has low volatility and hypotoxicity, and be water-soluble substances, so environmental properties and operability are also splendid.Stripper of the present invention is used to peel off the class photoresist that available alkaline aqueous solution develops, and protects copper base or aluminium base coatings under the photoresist covering not to suffer erosion in stripping process simultaneously; Peel off the copper post that finishes the back wafer surface and also can not produce side etching phenomenon substantially.
Claims (13)
1. photoresist lift off fluid composition with metal coating, form by the material of following percentage by weight:
Quaternary amines oxyhydroxide 0.1-10%;
Water-soluble alkanolamine 5-30%;
Water soluble organic polar solvent 55-94.4%;
Glycitols adjuvant 0.5-5%;
Above-mentioned water soluble organic polar solvent is sulfone class, sulfoxide class, amide-type or lactams solvent.
2. the described photoresist lift off fluid composition with metal coating of claim 1 is characterized in that, quaternary amines oxyhydroxide is the compound with following general formula (I) expression,
In the formula (I), R1, R2, R3, R4 represent alkyl or the hydroxyalkyl of carbon number 1-4 respectively independently.
3. the described photoresist lift off fluid composition of claim 2 with metal coating; it is characterized in that quaternary amines oxyhydroxide is tetramethyl ammonium hydroxide, tetraethyl ammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium, hydroxide four pentyl ammonium, hydroxide monomethyl tripropyl ammonium, hydroxide dimethyl diethyl ammonium, hydroxide (2-hydroxyethyl) trimethyl ammonium (choline), hydroxide (2-hydroxyethyl) triethyl ammonium, hydroxide (2-hydroxyethyl) tripropyl ammonium or hydroxide (1-hydroxyethyl) trimethyl ammonium.
4. the described photoresist lift off fluid composition with metal coating of claim 2 is characterized in that quaternary amines oxyhydroxide is selected from tetramethyl ammonium hydroxide, tetraethyl ammonium hydroxide and choline, or its potpourri.
5. claim 2 or 3 or 4 described photoresist lift off fluid compositions with metal coating is characterized in that the content of quaternary amines oxyhydroxide is 0.5-3% by weight percentage.
6. the described photoresist lift off fluid composition of claim 1 with metal coating; it is characterized in that; water-soluble alkanolamine is monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diisopropanolamine, triisopropanolamine, N-methylethanolamine, N-ehtylethanolamine, N-butylethanolamine or N, the N-dimethylethanolamine.
7. the described photoresist lift off fluid composition with metal coating of claim 6 is characterized in that water-soluble alkanolamine is monoethanolamine, triethanolamine, or its potpourri.
8. claim 6 or 7 described photoresist lift off fluid compositions with metal coating is characterized in that the content of water-soluble alkanolamine is 10-25% by weight percentage.
9. the described photoresist lift off fluid composition of claim 1 with metal coating; it is characterized in that; the water soluble organic polar solvent is dimethyl sulfoxide (DMSO), dimethyl sulfone, diethyl sulfone, tetramethylene sulfone, N; dinethylformamide, N; N-dimethyl acetamide, N-NMF, N, N-diethyl acetamide, N-N-methyl-2-2-pyrrolidone N-, N-ethyl-2-pyrrolidone or N-propyl group-2-Pyrrolidone.
10. the described photoresist lift off fluid composition with metal coating of claim 9 is characterized in that, the content of water soluble organic polar solvent is 69-88.5% by weight percentage.
11. the described photoresist lift off fluid composition with metal coating of claim 1 is characterized in that the glycitols adjuvant is fructose, glucose, galactose, sorbose, sweet mellow wine, sorbierite or xylitol.
12. the described photoresist lift off fluid composition with metal coating of claim 11 is characterized in that the glycitols adjuvant is sorbierite or xylitol.
13. claim 11 or 12 described photoresist lift off fluid compositions with metal coating is characterized in that the glycitols content of additive is 1-3% by weight percentage.
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