TWI252223B - Resist removing agent, resist removing composition and method for preparing the same and method for preparing N alkanol alkoxy alkanamide - Google Patents

Abstract

An amide compound, a resist removing agent, a resist removing composition and a method for preparing the same. The compound is N alkanol alkoxy alkanamide and is prepared by reacting alkanolamine with alkyl alkoxy alkanoate. The resist removing agent includes the N alkanol alkoxy alkanamide. The resist removing composition includes a mixture of alkanolamine with alkyl alkoxy, or a mixture of an attack inhibitor with N alkanol alkoxy alkanamide. The composition may either include a polar material. The resist removing agent and composition have excellent capability for removing resist and polymer from a substrate without attacking the layers underlying the resist.

Description

1252223, invention description (2) ~ 娀 娀 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明 发明method. In particular, the present invention relates to a photoresist removing agent and a composition comprising the alcohol-burning amine compound and the method for preparing the same. 1 off technology; fe π photoresist transfer program is a major program in the manufacture of semiconductor components. For example, the photoresist pattern used as a reticle on a semiconductor substrate must be removed after a different semiconductor component fabrication process, such as a process (dry or wet) or an ion implantation process. Moreover, if the photoresist pattern is biased, it must be removed to form a new photoresist pattern. Different material layers such as oxide layers,! The Lu layer, the polycrystalline layer, the metallic layer or the polyimide layer may be present under the photoresist layer. Therefore, an important consideration in the photoresist removal process is the complete removal of the photoresist layer as quickly as possible without eroding the underlying layers. Ministry of Economic Affairs, China Standards and Excise Department, Co., Ltd. A7 B7. The widely used photoresist removal agent contains an amine, such as a base amine, diethanolamine, monoethanolamine or methylethanolamine, and a polar solvent such as water or Ethanol, as its essential component. Since this conventional photoresist remover does not completely remove the polymer, another pre-removal step is required to remove the polymer. When performing a plasma etching or reactive ion etching (RIE) using a photoresist pattern as a mask, the polymer is formed by a component constituting a photoresist such as carbon (c), hydrogen (H) or oxygen (〇). ) a substance produced by the reaction with a plasma. In particular, when a metal layer is formed under the photoresist pattern, an organometallic polymer is produced. If the polymer or paper size is suitable for China's national standard rate (()NS) Λ4 specification (210 X 297 public Chu 1252223 A7 B7 V. Invention description (machine = polymer is not removed, for example, still exists in one connection In the case of a hole, it is expected that the contact resistance will increase and the semiconductor component will be produced. Therefore, in the use of the photoresist removal agent, it must be used on the substrate during the pre-removal step - polymer removal. Agents, such as nitric acid solutions. Conventional photoresist removers may invade the underlying layer. A typical underlying layer that is easily eroded is a metal layer. This is because the photoresist remover is mainly made up of metal layers that are easy to invade. The solvent or water composition n must be performed before the removal of the rinsing step to prevent the removal step. In the subsequent removal step, for example, isopropyl alcohol can be used. Therefore, since the acid-removing step (pre-removal step) and the lpA treatment step (post-removal step) are usually performed as well, the photoresist removal process is made more complicated and the processing time is extended, thereby reducing productivity. Due to the need for pre-removal Such as nitric acid, and subsequent removal of materials, such as IpA, and photoresist removal materials, thereby increasing manufacturing costs. In addition, due to the need for different tanks to accommodate nitric acid and IPA, the photoresist removal device becomes hopelessly The invention is outlined. (Please read the note on the back and then fill out this page.) Step by step. It is an object of the present invention to provide a novel guanamine compound which substantially overcomes the limitations of the prior art. Or one or more problems arising from the disadvantages. A second object of the present invention is to provide a photoresist removal agent formed by the novel guanamine compound, which has a photoresist and a polymer for removing Excellent ability without eroding the layer under the photoresist. A third object of the present invention is to provide a photoresist removal composition, which is m I- I - - I - ϋϋ • - I - I · The paper size is 13⁄4 in Chinese national standard rate (C'NS) Λ4 size (210X297 mm) 1252223

It has the ability to remove - photoresist and polymer without eroding the layer under the photoresist. 4 The object of the invention is to provide a method for preparing the guanamine compound. A fifth object of the present invention is to provide a method for preparing the photoresist removal composition. Accordingly, in order to attain the above object or other objects and advantages of the present invention, the present invention provides a compound having the formula R4-〇-R3-C〇-N-RiR2〇HiN alkanol alkoxyalkylguanamine. Wherein R1 is hydrogen, a hydrocarbon group of 1 to 3, or an aromatic hydrocarbon group having 1 to 3 rings. R2 is a hydrocarbon group of 1 to 3 or an aromatic hydrocarbon group having 1 to 3 rings. && The hydrocarbon-removing composition is independently composed of an N-alkanol alkoxyalkylamine and an erosion inhibitor. Further, in view of the present invention, the photoresist removal composition comprises Further, it may further comprise a polar substance having a dipole moment of not less than 3. In another aspect of the invention, the photoresist removing composition comprises an alkanohydrin and an alkyl alkoxy alkanoate. The photoresist removal composition comprises an intrusion inhibitor and a polar material. For another aspect of the invention, the method for preparing an N-alkanol alkoxy alkanoylamine comprises reacting an amine with an alkane The alkoxy alkanoate is mixed and reacted. As another aspect of the invention of the present invention, a method for preparing a photoresist removal composition comprises an alcohol decylamine and an alkyl alkoxy alkanoate. Mixing and reacting with an erosion inhibitor. The photoresist removal agent and photoresist removal composition of the present invention have a function for shifting Zhang scale applicable Chinese national standard and death (CNS) Λ4 Specification (210X 297 male toss) (Please read the notes on the back of this page and then fill in) order

C The Ministry of Economic Affairs, the Ministry of Economic Affairs, the Ministry of Economic Affairs, the Ministry of Economic Affairs, the Ministry of Economic Affairs, the Central Standard Rate, and the Industrial Standards: ^Printed by A7 B7. V. Inventions (4) Excellent ability in addition to photoresist. 'And the polymer and organometallic polymer can be effectively removed without eroding the underlying layer of the photoresist. BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a flow chart in which a solid line indicates a photoresist removal method using a photoresist removal agent or a photoresist removal composition of the present invention, and a broken line indicates a conventional step of removing the use of the present invention. Figure 2 is a block diagram of a photoresist removal device using a photoresist removal agent or photoresist removal composition of the present invention; Figure 3 is a diagram illustrating light removal using the photoresist of the present invention. A scanning electron micrograph of the pattern removal result. Fig. 4 is a view showing a scanning electron micrograph showing the result of removal of a photoresist pattern using a conventional photoresist removal group salt. Fig. 5 is a diagram showing the change in the content of the components in the photoresist composition, which was measured by a gas spectrometer at intervals of 8 hours for 48 hours. DESCRIPTION OF THE EXAMPLES Hereinafter, a method of ugly amine compound, a photoresist removing agent, a photoresist removing composition, and a method for preparing the same will be described in detail. One novel indoleamine compound of the present invention is an N-alkanol alkoxyalkylamine. In particular, the N-alkanol alkoxyalkylamine is represented by the formula (1): R4-〇-R3-CO-N-R1R2OH (1) wherein R! is a hydrogen atom, and one (^ to 匕a hydrocarbon group (lang, a non-cyclic hydrocarbon group having 1 to 5 carbon atoms), or an aromatic hydrocarbon group having a ring to a ring of 3; a core of a hydrocarbon group or a hydrocarbon having 1 to 3 rings The heart and the heart are each independently one (^ to (: 5 hydrocarbon group. In the preferred embodiment, the heart is a hydrogen original paper size of the State of China National Standard (CNS) Λ 4 specification (210Χ 297 mm) ) --:-------.--------Book ------Line: 'ί • . 丨C (Please read the notes on the back and fill out this page) 1252223 A7 B7 Ministry of Economic Affairs, the Ministry of Economics, the Bureau of Standards, Co., Ltd., Co., Ltd., Printing, Co., Ltd., 5, invention, (5), R2 is -CH^Hr, & is _CH2CH2·, and ^ is even. The indoleamine compound of the present invention includes a radical (-oh) which produces a nucleophilic reaction with the photoresist, and an alkoxy group (_〇1) which generates a hydrophilic reaction with the hydroxyl group (_0H). Subsequently, a photoresist having the indoleamine compound of the present invention is removed. The agent system is very effective in removing the photoresist. Therefore, according to the present invention In one embodiment, the N-alkanol alkoxyalkylguanamine compound itself constitutes a photoresist remover. In another embodiment of the invention, a photoresist remover composition comprises an N-alkanol alkoxy group. An alkalamine and an erosion inhibitor. Moreover, the photoresist remover composition optionally further comprises a polar substance having a dipole moment equal to or greater than 3. For example, in the photoresist removal composition, The content of the alkanol alkoxyalkylguanamine may be from 5 to 99.9 weight percent (% by weight) based on the total weight of the composition, and the content of the erosion inhibitor may be from 1 to 3% by weight. In the embodiment, the content of the N-alcoholic aromatization amine is from 9 to 9% by weight, and the content of the inhibitor is from 7 to 15% by weight. In other words, it has a polarity of a dipole moment equal to or greater than 3. The content of the substance may be from 1 to 3 Torr, and preferably from 0 to 20% by weight. The N-alcohol alkoxyalkylamine is a compound represented by the above formula (丨). It is represented by the following formula (2): R6-(〇H)n (2) wherein 'R6 is a (^ to (: 5 hydrocarbon group, one has a _C00H group) a aryl group having 1 to 3 rings, or an aromatic hydrocarbon group having 1 to 3 rings and having one -COOH group in at least one ring. The integer η may have a value ranging from 1 to 4 In the preferred embodiment, r6 is a benzene ring and invades (please read the back of the note first and then fill out this page)

C it, the paper scale applies to China's family standard ((:NS) Λ4 specifications (2丨0X297 public j 1252223 five, the central standard of the Ministry of Economic Affairs φ^ρ工消贽合竹社A7 B7 invention description (6) The etch inhibitor is catechol, wherein 11 is 2. Further, trihydroxybenzoic acid is a widely known erosion inhibitor represented by the formula (2), which can be used in the present invention. A polar substance equal to or greater than 3 may be water, methanol or dimethyl fluorene. A polar substance having a dipole moment equal to or greater than 3 exhibits a high solubility to the crosslinked polymer and the photoresist system. The polymer strongly bonded to the inside of the photoresist pattern and the exposed underlying surface can be effectively removed by the polar substance. Further, the photoresist removal itself is facilitated by the polar substance. Another embodiment of a photoresist removal composition of the present invention includes an alkanolamine which is an amine compound, and an alkyl alkoxy alkanoate which is a monoester compound. Further, alternatively, it may be further Containing an erosion inhibitor or an polar substance having a dipole moment equal to or greater than For example, in this embodiment, the content of the alkanolamine is 10 to 70% by weight of the photoresist removal composition, and the content of the alkyl alkoxy alkanoate is 10 Up to 70% by weight. In a preferred embodiment, the alkanolamine is present in an amount of from 5% to 4% by weight of the alkyl alkoxy alkanoate. In this example, the erosion inhibitor is The content is from 0.01 to 30% by weight of the photoresist removal composition. In a preferred embodiment, the content of the erosion inhibitor is from 7 to 15% by weight. Further, the content of the polar substance is the photoresist removal composition. 0. 01 to 30% by weight. In a preferred embodiment, the substance is 3 to 2% by weight. The N-alkanolamine suitable for use in the present invention is represented by the following formula (3):

Ri-NH-R2〇H (3) (Please read the notes on the back and fill out this page)

1252223 A7 B7 V. Inventive Note (7) wherein R! is a hydrogen atom, a hydrocarbyl group of Cl to ^, or an aromatic hydrocarbon group having a fluorene to a 3-ring, and R2 is a hydrocarbon group of 1 to 匸5 or An aromatic hydrocarbon group having a ring. In a preferred embodiment, Ri is hydrogen and & is a monohydric ethanolamine, i.e., a CH2CH2- oxime is suitably used in the present invention. The alkyl alkoxyalkanoate is represented by the following formula (4). ) R4-0-R3-C00-R5 (4) wherein 'R3, R4 and each independently are a hydrocarbon group of C! to C5. A preferred alkyl siloxane is a methyl group. A methoxypropionate wherein the rule 3 is -CH2CH2-, R4 is -(^113 and &5 is _CH3. Now the reaction mechanism of the composition according to the most recent embodiment will be described. First, as follows As shown in the reaction formula (5), the separation of the photoresist is caused by the nucleophilic reaction mechanism of the alkanolamine. Further, the nucleophilic reaction mechanism of the mercapto group in the alkaloid and the alkoxylate in the alkyl group The hydrophilic reaction mechanism of the alkoxy group is dissolved, and the residual inhibitor effectively prevents the underlying layer, especially a metal layer, from being invaded. Further, a polar substance such as Water, the polymer removal reaction is maximized. (Please read the note on the back and fill out this page)

After the drop of the central standard, the date bureau is responsible for the elimination of the

q m 0 m

NHzRfH

C= N—〇H (5) For convenience of explanation, the mechanism described in the reaction formula (5) is an example in which the intention is hydrogen. In order to completely form the composition, the composition can be heated to a room temperature >, the paper scale is applicable to the Chinese National Standard Rate (CNS) Λ 4 specification (210X297 public f) -10- τ消介合竹社印1252223 A7 _______B7 V. Invention description (8) '-~ Temperature of about 120 c. In a preferred embodiment, the composition is heated to a temperature of from about 80 C to about 90 °C. The reason for the heating is to accelerate the reaction of the alkanol alkoxyalkylamine by the composition in the reaction (5). Alternatively, a reaction catalyst such as platinum may be added to the reaction formula (5) to promote a faster reaction. The photoresist removal composition of the present invention is shown in Table 1 below. In Table 1, the contents of the preferred compositions are shown in parentheses. Table 1: Photoresist removal composition for removing photoresist composition stanol alkoxy alkanoylamine (% by weight) alkanolamine (% by weight) alkyl alkoxy alkanoate (% by weight) Residual inhibitor (% by weight) Polar substance (% by weight) 1 50 to 99.9 0.01 to 30 2 50 to 99.9 (70 to 90) 0.01 to 30 (7 to 15) 0.01 to 30 (3 to 20) 3 10 to 70 10 to 70 4 10 to 70 (30 to 40) 10 to 70 (30 to 40) 0·01 to 30 5 10 to 70 (30 to 40) 10 to 70 (30 to 40) 0.01 to 30 (7 to 15) Ϊ́.01 to 30 (3 to 20) The photoresist removing agent and the photoresist removing composition of the present invention have excellent ability to remove the photoresist and the polymer. Moreover, they do not invade the underlying layer of the photoresist, such as a metal layer. Moreover, the above materials are also less expensive than the components of conventional photoresist compositions. The N-alkanol alkoxyalkylguanamine, the decylamine-expound of the present invention, is prepared according to the following method of the present invention. First, an alkoxylamine ' as a monoamine compound represented by the formula (3) is mixed with a decyl alkoxylate ester represented by the formula (4) as a monoester compound. Mixture of this alkanolamine with a burnt alkoxylate. This paper scale is applicable to the Chinese National Standard (CNS) λ4 specification (2丨〇χ 297 mm). (Please read the back note and fill out this page)

-11- 1252223 A7 B7 V. INSTRUCTIONS (9) (Please read the precautions on the back and fill out this page) The ratio is 1:1 (weight ratio). Next, a reaction of an amine with vinegar is carried out to prepare an N-alkanol alkoxyalkylguanamine represented by the formula (1). In order to supply sufficient energy for this reaction, the temperature of the mixture is maintained at a temperature ranging from room temperature to about 12 art. In a preferred embodiment of this method, the mixture is heated to a temperature in the range of from about 80 °C to about 90 °C. The photoresist removal composition 1 or 2 exemplified in Table 1 is obtained by the above method, and the N-alkoxy alkoxyalkylamine is prepared in an appropriate ratio with an erosion inhibitor or a polar substance or both. Prepared by mixing.

Further, the composition 1 or 2 can be produced according to the following method of the present invention. First, 10 to 70% by weight of the alkanolamine and 1 to 70% by weight of the alkyl alkoxylate and 0 to 30% by weight of the erosion inhibitor or hydrazine to 3 Å by weight. The polar substance or a mixture of the two. Next, the temperature of the mixture is maintained at a temperature ranging from room temperature to about 120 °C. In a preferred embodiment of this method, the mixture is heated to a temperature in the range of from about 80 °C to about 90 °C. The reaction time, i.e., the reaction time, is from about 1 to about 24 hours, preferably from about 1 to about 12 hours. After the heating is completed, the reactants are separately placed for 1 to 7 hours to stabilize the chemical reactants. The Ministry of Economic Affairs, the central government of the Ministry of Economic Affairs, has only obtained a composition consisting essentially of an N-alkanol alkoxyalkylamine and an oxidative inhibitor or a polar substance or both. A small amount of unreacted alkanolamine and alkylalkoxy alkanoate may be present. The completion of the reaction can be recognized by visual or gas chromatography. In the visual confirmation, the layer separation between the observed components disappeared as a reaction. When it was observed that the separated component layer completely disappeared, the reaction was assumed to be completed. When the composition is analyzed by the gas chromatography method, the area percentage of the N-alkanol alkoxy alkaneamine is applicable to the Chinese standard ((NS, NS) Λ4 (210X 297 mm) -12· 1252223 Α7 Β7 5. Inventive Note (IQ) If the number of digits exceeds 80%, the reaction is completed. The regional percentile is defined as the area under the peak of the gas chromatographic spectrum of the ^ component. Read the notes on the back and fill out this page. } All the peaks of the components are divided by the sum of the regions, and the quotient is multiplied by 100 〇 in the preparation of compositions 3 to 5, the components are exemplified in The ratios of Table i are mixed and then reacted for 1 to 24 hours at a temperature ranging from room temperature to about 12 Torr. Typically, these compositions 3 to 5 are first formed before being used to remove the photoresist. However, if the temperature of the composition 3 to 5 is in contact with the photoresist, the temperature can be set within the above temperature range, and the above separation reaction step can be omitted. The sub-marker of the drop is in the sub-standard Feng Qibing-T-Consumer Hezhu Society. Steps for water to remove photoresist using the photoresist removal agent and photoresist removal composition of the present invention Referring to the solid line step in Figure i. Note that the conventional method is represented by both the solid and dashed steps in Figure 1. Various methods for completing semiconductor components, such as etching (dry or wet) Or ion implantation, using a photoresist pattern as a mask. Subsequently, the photoresist pattern formation on the substrate is allowed to contact a photoresist removal agent or composition listed in Table 1 to The photoresist or polymer or both are removed (step 11). This is accomplished by placing the photoresist remover or photoresist removal composition in a bath and then immersing the substrate in the bath. Optionally, the photoresist remover or photoresist removal composition can be sprayed onto the substrate as the substrate moves through the spray. The photoresist removal agent is formed while the photoresist removal composition 1 It is mixed with the 2 series σ' and the receiver can be immediately brought into contact with the substrate to remove the photoresist in the 丨 private removal step. The compositions 3 to 5 shown in Table 1 are first mixed, and then It may be allowed to immediately contact the substrate; however, before performing the removal step, the compositions 3 to 5 are preferably given time to react This reaction system at room temperature to scale in this paper rate applicable Chinese National Standard (CNS) Λ4 Specification (210Χ 297 mm) • 13 · 1252223 A7 B7

_ 贽 中 中 而 而 # # # # 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五 五Contact with the photoresist on the substrate until the reaction is completed - an equal additional time, such as an additional 1 to 7 hours after completion of the reaction. The photoresist removal step of the present invention using these compositions can be carried out at 7 Torr. Or lower, in particular, performed at a low temperature of 45 to 7 (TC. The contact time is preferably in the range of about 1 Torr to about 30 minutes. Optionally, when the structure formed on the substrate has a high heat When blocked, the unheated compositions 3 to 5 can be placed in a photoresist removal unit in contact with the substrate. Subsequently, the temperature of the photoresist removal unit can be adjusted to an amine at room temperature to the above temperature range. The temperature at which the ester can react to form the guanamine. Then, the reaction of removing the photoresist from the substrate can occur simultaneously by the reaction of the composition to form the guanamine. That is, in this method, the removal is performed. The separation reaction of the compositions 3 to 5 can be omitted before the step. The light of the present invention The remover or photoresist removal composition can be applied to photoresists suitable for short wavelength exposure, such as photoresists for ArF excimer lasers and photoresists for conventional 365 nm sources or For the KrF excimer laser (248nm) photoresist. After the photoresist is completely removed, the photoresist removal agent, photoresist removal composition and dissolved photoresist that are still present on the substrate are rinsed. (Step 13〇) ^This rinsing step is carried out using a rinsing solution such as deionized water. The rinsing step can be carried out in two steps if necessary. Finally, the substrate is dried using air. Rotary drying method or a drying method, for example, using isopropyl alcohol as a desiccant to remove deionized water remaining on the substrate (suitable for step paper)? Specifications (-2丨 mm)---- - -14- (Please read the notes on the back and fill out this page) Order - m 1252223 A7 B7 V. Inventive Note (12 Step 140), and dry. After drying step 140, the substrate is transported to the following Procedure. (Please read the note on the back and then fill out this page) A light 卩 i mask is formed in the following steps At the time of the completion of the subsequent steps, the photoresist is removed via the steps shown in Figure 1. The semiconductor component is completed via the repeated cell fabrication methods and photoresist removal steps. As shown, since the photoresist remover or photoresist removal composition of the present invention has excellent ability to remove photoresist or polymer, unlike the prior art, the pre-removal step 1〇〇 (dashed line) is not required. Moreover, since the layer under the photoresist is prevented from being eroded, it is also different from the prior art, and the post-removal step 120 (dashed line) can be omitted. Therefore, with conventional photoresist In contrast to the removal method, according to the present invention, the photoresist system can be completely removed by a simpler method, and the productivity of the semiconductor device can be significantly improved. Further, as described above, since the photoresist removal method is simplified, the photoresist removal device using the photoresist removal (tetra) green removal composition of the present invention can be made smaller or more compact. Referring to Fig. 2, the photoresist removing apparatus according to the present invention simply includes a photoresist removing unit 21G' - a flushing unit 220 and a drying unit. That is, the conventional pre-removal unit and the post-removal unit are not required. Therefore, compared with the prior art, the space of the photoresist removal device sand in the placket 200 can be significantly

Reduced. The details of the present invention are described with reference to the following embodiments, however, it must be understood that the present invention is not limited to the specific embodiments.

-15- 1252223 A7 B7 V. Description of invention (13)

Example 1 Preparation of Ethanol Methoxypropionamine (Please read the back note for the first page) #In this example, 200 ml of monoethanolamine as a monoalkanolamine and 200 ml of methyl as a monoester The methoxypropionate is mixed. This mixture was then tied at 9 Torr. (: heating for 5 hours. After heating, the reactant was allowed to stand at room temperature for 5 hours. The finally obtained material was analyzed by gas chromatography to confirm whether N-ethanol methoxypropionate was obtained. The amine product. Further, the product was analyzed by proton nuclear magnetic resonance CH-NMR spectroscopy to obtain the relative amount (in ppm) of the components. The NMR results of the product were as follows: 6.8 ppm (1H), 3.7 ppm (3H), 3.5 ppm (3H) and about 2.8 ppm (1H).

EXAMPLE II Preparation of N,N-Terbutylethanolmethoxypropionamide In this example, 200 ml of n,N-tert-butylethanolamine as a monoalkanolamine and 200 ml of a monoester were used. Methyl methoxypropionate is mixed. Subsequently, the mixture was heated at 9 ° C for 5 hours. After heating, the reaction was allowed to stand at room temperature for 5 hours.

The finished product of the Ministry of Standards and the Ministry of Standards only consumes the photo of the company. The final material is analyzed by gas chromatography to confirm whether the N, N-t-butylethanol methoxypropionamide product is obtained. .

EXAMPLE III Evaluation of a suitable temperature in the preparation & of N-ethanol methoxy-propionamide 200 ml of monoethanolamine as monoalkanolamine and 200 ml of methyl methoxy group as monoester in this example The propionate is mixed. With the paper scale, the Chinese national standard jujube (CNS) Λ4 specification (21〇'〆297 public Chu) -16-1252223 A7 B7 is applied. 5. After the invention description (14), in order to confirm the suitable reaction between this amine and Kuaixing The temperature, N-ethanol methoxypropanol was synthesized in the same manner as in Table 2, black broken i U / radiance, and the time required for complete synthesis was measured. The time of the synthesis of the day of the Fengmeng technique is determined by the passage of time until the gas chromatographic analysis shows that the area of the indoleamine exceeds 80%. • 1 1 — I - - · Reaction temperature (C) Reaction time (hours) 25 55 35 ------ ^ Λ —45 55 65 80 90 24 30 7~ 6 4 3 The -x price reduction cooperative prints from above and the reaction occurs at a higher temperature to produce H faster. Considering other processing conditions, the reaction temperature is preferably not more than 12 Gt. Therefore, the temperature at which the guanamine compound according to the present invention is prepared is desirably from room temperature to about 12 Torr. (In the preferred embodiment of the method, the reaction temperature is in the range of about 8 Torr to about 9 Å. Example IV Preparation of the photoresist removal composition and removal of the photoresist thereof As evaluated in Table 3, seven photoresist removal compositions were prepared with different contents of one-element ethanolamine (MEA), mercaptomethoxypropionate (MMp), catechol, and water. The system was heated at 8 ° C for 5 hours. Thereafter, the resulting material was allowed to stand at room temperature for 6 hours to complete the composition.

Item MEA (ml) MMP (ml) catechol (g) water (ml) Observations 1 50 350 60 100 〇 2 100 300 60 100 〇 3 150 250 60 100 Θ 4 1 200 200 60 100 Θ 5 250 150 60 100 ◎ _ 300 100 60 100 〇本纸标准 China's national standard rate (7:NS) A4^ (21〇X 297^tT (note the first note on the back and fill out this page)

, 1T R. -17- A7 1252223 _____B7 V. Description of invention (15) 7 350 50 60 100 〇 (〇: good, ◎: better, 〇: best) To be removed by using the above photoresist to remove the composition The photoresist was prepared by the following method on each of the seven substrate sheets. First, the borophosphoric acid phosphate glass (BPSG) layer forms a thickness of 5000 Å. Next, a titanium layer and a titanium nitride layer are each formed to a thickness of 200 Å and heated. Thereafter, a layer of 6,000 A was deposited and then flowed. A titanium nitride layer as a capping layer is formed on the aluminum layer, and then a laminated dielectric layer is formed to a thickness of 10,000 Å. Next, a photoresist is applied to the laminated dielectric layer and lithography is performed to form a photoresist pattern that defines a via. The photoresist pattern is cured and then the photoresist pattern is used as a mask, and the laminated dielectric layer is etched by a buffered oxidant etchant to form a via hole exposing the aluminum layer. After the formation of the via holes, the 7-layer substrate was impregnated into 7 wells each containing the 7 compositions listed in Table 3. The temperature in these tanks is maintained at 60 °C. After immersion for 20 minutes, the substrates were rinsed with water for 5 minutes and then dried, and then a scanning electron microscopy (SEM) was used to detect the substrates. These substrates were classified into good, preferred, and optimal three grades based on SEM observations, and these grades are shown in Table 3 using different symbols. The state of the substrate is indicated by the relative amounts of residual polymer and residual washout. This good state is similar to the state in which the composition is removed using a conventional photoresist. This preferred state is compared to the conventional state, and the improved state is obtained. This optimum state is compared with the conventional state, and a significant improvement is obtained. 1. Paper size is suitable for China's national standard jujube (CNS) Λ 4 specifications (210X29? public f") ~ - (Please read the note on the back and fill out this page)合竹社印来-18- 1252223 A7 B7 V. Description of Invention (16) Example v (Evaluation of Appropriate Execution Time In order to confirm the appropriate execution time, the composition of item 4 in Table 3 is used, and the photoresist is The removal time is shown in Table 4 for different execution times. The other execution conditions are the same as in Example Iv. The photoresist removal state and erosion state of an aluminum layer and a germanium layer are observed using SEM. The symbol of the rendered removal state is the same as Table 3. In Table 4, a symbol of "^ _ indicates that the underlying layer is not invaded. From the results of Table 4, a suitable one for removing the photoresist can be found. The reaction time is 10 to 30 minutes. (Please read the notes on the back and fill out this page.) Table 4: Different time ^^Removal performance item MEA (ml)

(◎: preferred, Θ: best) Example VI, 1Τ The central standard rate of the drip section is the result of the evaluation of the appropriate execution temperature. In order to confirm the proper execution temperature, the items in Table 3 are used. * The composition, and the photoresist is removed at different execution temperatures listed in Table 5. His execution conditions are the same as in the embodiment IV. An aluminum layer is a aw w long one stone layer. The removal state and the erosion state are observed using SEM. Cypress π from "

Don't be embarrassed, a symbol of X means that the bottom layer does not show the effect of erosion. And a circle means -19- by the Ministry of Economics, the label is marked ^^:^二消牝合社社

1252223 A7 _______ B7, invention description (17) The bottom layer shows the effect of the invaded surname. From the results of Table 5, it was found that a suitable reaction temperature for removing the photoresist is about 45. . In the lower temperature range of about 7 (^), this is because the bottom layer is not subject to discernible damage in this range. Table 5: Photoresist removal performance at different temperatures

^ S 1 MEA (ml) MMP (ml) catechol (g) water (ml) temperature (°C) The observation of the photoresist removal ability (A Si Si) is 1 ο 200 200 60 100 45 mouth '月丨氏戈 X 1 200 200 60 100 50 @~' — X 3 A 200 200 Ό〇100 |5? 4 200 200 200 200 60 60 100 Too 60 65 ◎ - 0 200 200 60 100 70 X

Example VII Comparison of Photoresist Removal Ability In this example, the via hole was formed using the photoresist pattern formed by the method of Example 4, and the photoresist was listed in item 4 of Table 3. The composition was removed, the execution time was 20 minutes, and the reaction temperature was 6 〇〇c. The final material was observed using SEM, and the results are shown in Figure 3. In a comparative example, the photoresist was removed using a conventional photoresist removal composition' in the same manner as in the above examples, and then the final material was observed using SEM. The observations are shown in Figure 4. ^ When comparing the SEM images shown in Figures 3 and 4, it can be found that when the photoresist removal composition according to the present invention is used, the photoresist system can be completely removed, and when a conventional photoresist composition is used, The photoresist is still partially residual. And, though (please read the note on the back and then fill out this page). Order the jade paper scale to cover the towel ^:; (brand (~CNS) A4^m (21〇X 297^t) -20- 1252223 A7 B7 V. INSTRUCTION DESCRIPTION OF THE INVENTION (18) However, in the embodiment of the present invention, the underlayer is not invaded, but in the embodiment using the conventional photoresist to remove the composition, the layer is partially invaded.

EXAMPLE VIII Consumption of the components of the photoresist removal composition during the photoresist removal period, the amount of the component of the photoresist removal composition shown in Table 3, item 4, was 8 hours by gas chromatography. Interval for analysis. The results of the analysis are shown in Fig. 5, where is the % of the area of the indoleamine, Δ is the % of the area of the monoethanolamine, and □ is the area % of the methyl methoxypropionate. From the results of Table 5, it can be seen that the % of the area of the indoleamine is a constant of about 8 %, even after 48 hours. Further, the % of the monoethanolamine is a constant of 3.4%. The area 甲基/0 of methyl methoxypropionate was reduced from 〇.9 to 〇·5 within 24 hours, and became almost 〇 after 40 hours. It is considered that the main active component of the composition of the present invention is decylamine, and the content of guanamine is little changed even after 48 hours, indicating that the composition of the present invention can be used for a long period of time without being rapidly consumed in the reaction. This display differs from the conventional photoresist removal composition which must be replaced every 24 hours, and the composition of the present invention significantly improves productivity and reduces manufacturing costs. The guanamine compound of the present invention has an excellent ability to remove a photoresist. Therefore, the photoresist removing agent or photoresist removing composition of the present invention having such a guanamine compound has an excellent ability to remove a photoresist and can effectively remove the compound and the organometallic polymer. Moreover, the layer under the photoresist is not eroded. Therefore, when the photoresist removal agent or photoresist removal composition of the present invention is used, it is not necessary to perform a pre-removal step for removing the polymer and a post-removal step for preventing the underlying layer from being eroded. . Therefore, the photoresist removal step paper size Tongzhou China National Standard (CNS) Λ 4 specifications (2 丨 0X297 mm) (please read the back note before filling this page), -0 Ding Economics Department Sub-standards bureau KT. Jie Jie He Zhushe printed -21 · 1252223 A7 Γ ______ Β 7 V, invention description (19) 'The simplification can be simplified and the program time can be shortened. Also, the temperature required to remove the photoresist can be set to a lower temperature. Furthermore, the photoresist removal device can be simplified and made more compact. It will be appreciated by those skilled in the art that various modifications and changes can be made without departing from the spirit or scope of the invention. Therefore, the invention and its modifications and variations are intended to be included within the scope of the appended claims. Component label control: 200 photoresist removal device 210 photoresist removal unit 220 rinsing unit 23 〇 drying unit (please read the note on the back and then fill out this page) Ministry of Economic Affairs, the squatter, 1: consumer cooperative The paper size is suitable for the state of China, China's national 榡 ( ([奶) eight 4 specifications (21 (^ 297 mm) -22-

Claims (1)

1252223 A8 B8 C8 D8, patent application scope Patent Application No. 871, 174, 154 It is of the formula: R4-〇-R3-CO-N-R1R2〇HG) wherein: the core is hydrogen, a hydrocarbon group of 匕5 to 匚5, or an aromatic hydrocarbon group having 1 to 3 rings; R2 is a Ci A nicotyl group to C5 or an aromatic hydrocarbon group having 1 to 3 rings; and R3 and R4 are each independently a hydrocarbon group of q to c5. 2. The photoresist removal agent of claim 1 wherein: Ri is hydrogen, r2 is _(: 112 (: 112-, r3 is -CH2CH2-, and R4 is -CH3. 3. - light) The composition is removed, comprising an N-alkanol alkoxyalkylamine and an erosion inhibitor, wherein the N-alkanol alkoxyalkylamine has the following general formula (1): R4-0-R3-CO-N -R1R20H (1) wherein: Ri is hydrogen, a hydrocarbon group of (^ to ^, or an aromatic hydrocarbon group having an is 3 ring; R2 is a (^ to (: 5 hydrocarbon group or an is 3 ring aromatic hydrocarbon group; 23- 1252223 Please fill out this page again) nu , ^-------- J^T- 丨iiii______ -24- A8 B8 C8 D8 1252223 VI. The patent application area accounts for 0.01 to 30% by weight of the photoresist removal composition. a corrosion inhibitor in the range; and a polar substance having a dipole moment of not less than 3 and ranging from 0·〇1 to 30% by weight of the composition, wherein the naphthyl alkoxy alkanoamine For those having the general formula (1): R4-〇-r3.c〇.n.r1r2oh (1) wherein: Ri is a gas, a Ci to C5, or an aromatic hydrocarbon having 1 to 3 rings , the ruler 2 is a hydrocarbyl group of Ci to C5 or an aromatic hydrocarbon group having 1 to 3 rings, and the R3 and R4 are each independently a hydrocarbon group of Q to C5; and the residuating inhibitor has the formula (2) Compound: Κ〇Η)η (2) wherein: R6 is a hydrocarbon group of 丨 to C5, a hydrocarbyl group of CiSC5 having a -COOH group, an aromatic hydrocarbon group having 1 to 3 rings, or 1 to 3 a ring and a -CO〇H-based aromatic hydrocarbon group, and η is an integer from 1 to 4. 11. A method for preparing a stanol alkoxy alkanoylamine, comprising: an alkoxylated amine and an alkylalkane Oxyalkane Mixing the ester; and reacting the alkanolamine with the alkyl alkoxy alkanoate to form a stanol alkoxyalkylguanamine, wherein the alkanolamine comprises the composition (;;)装--------订-------(Μ (Please read the note on the back and fill out this page) -25- ABCD 1252223 10 to 70 weight percent of Shenjing patent range a range; the alkyl alkoxyalkanoate is in the range of 10 to 70% by weight of the composition; and the N-alkanol alkoxyalkylamine is a compound having the formula (1): R4-〇 -R3-CO-N-RiR2〇H (!) wherein: Ri is hydrogen, a hydrocarbyl group of Ci to C5, or an aromatic hydrocarbon group having 1 to 3 rings; R2 is a hydrocarbyl group of Ci to Cs or one has 1 to a 3-ring aromatic hydrocarbon group; and R3 and R4 each independently a hydrocarbyl group of Ci to C5. The method of claim 11, wherein during the mixing: the alkanolamine has a general formula (3) : Ri-NH-R2OH (3) wherein: Ri is hydrogen, a Cl to C5 hydrocarbon group, or an aromatic hydrocarbon group having 1 to 3 rings, and R 2 is a Ci to C5 hydrocarbon group or a 1 to 3 ring Aromatic hydrocarbon group; and the alkyl alkoxyalkyl group The ester has the formula (4): R4·O-R3 - C 00 - R5 (4) wherein each of R3, R4 and R5 is a cigarette of C1 to C5. 13. The method of claim 12 , wherein: Ri is hydrogen, and -26- 1252223 A8 B8 C8 D8, and the patent application range R2 is _CH2CH2-. 14. The method of claim 12, wherein: the ruler 3 is _CH2CH2-, the R4 is ·CH3, and the I is -ch3. 15. The method of claim 301. 16. The method of claim 15, wherein the compound of the formula (2): R6-(〇H)n wherein: further comprises an erosion wherein the erosion inhibitor system (2) R6 is a Ci to C5 a hydrocarbon group, a hydrocarbon group having a _c 〇〇H of Cl to C5, an aromatic hydrocarbon group having 1 to 3 rings, an aromatic hydrocarbon group having 1 to 3 rings and a -COOH group, and η being 1 to An integer of 4. 17. The method of claim 16, wherein the inhibitor of the exclusion is one of the phthalic acid and the tribasic benzoic acid. 18. The method of claim 11, further comprising a polar material having a dipole moment of not less than 3. 19. The method of claim 18, wherein the polar substance is one of water, sterol and dimethyl hydrazine. 20. The method of claim 18, wherein the polar material comprises from 0.01 to 30 weight percent of the composition. 21. For the method of applying the patent scope item n, wherein during the mixing period, --- (13⁄4 first smell 1^ the back i sound? Please fill in this page again) *J»T· 'Green---- ----- -27- 1252223 Patent application scope A8 B8 C8 D8 The ratio of the alkanolamine to the succinyl oxy sulphuric acid vinegar is ι:] (based on the weight). 22) As claimed in the scope of claim u, wherein the reaction is carried out at a temperature ranging from room temperature to 120 °C. 23. For the method of claim n, the reaction is carried out in a period of time ranging from 1 to 24 hours. 24. A method for preparing a photoresist removal composition, comprising: mixing an alkanolamine, an alkyl alkoxy alkanoate with an erosion inhibitor to form a mixture; and causing the mixture to Reacting to form the photoresist removal composition, wherein during the mixing: the alkoxylated amine is in the range of from 1 〇 to 7 〇 by weight of the mixture, and the alkyl oxy sulphuric acid vinegar accounts for The range of 1 〇 to 7 〇 by weight of the mixture, and the erosive inhibitor is in the range of 0.01 to 30% by weight of the mixture; the alkanolamine has the formula (3) ·· Ri-NH-R2〇H (3) wherein: Ri is argon, a Ci to C5 candle group, or an aromatic hydrocarbon group having 1 to 3 rings, and R 2 is a Ci to C5 hydrocarbon group or a 1 to 3 ring aromatic hydrocarbon group; 28- 1252223 A8 B8 C8 D8 The alkyl alkoxy alkanoate has the general formula (4 R R 4 - R 3 - COO - R 5 , (4) wherein each of R 3 , R 4 and R 5 is a hydro group of Ci The corrosion inhibitor is a compound having the formula (2): Μ〇Η) η (2) R6 is a hydrocarbon group of 丨 to c5, · € () 〇Η; ϊ Cl to C: 5 hydrocarbon group, an anthracene group having a fluorene to 3 ring, or an aromatic hydrocarbon group having 1 to 3 rings and a -CO〇H group, and η is 1 to 25. The method of claim 24, wherein the method is carried out at a temperature ranging from room temperature to 120. (: in the range of the temperature. 26. The method of claim 24, the mixing Further, the method further comprises the method of claim 1, wherein the reaction is carried out in a range of from 1 to 24 hours on a shoulder. -29- ( 2.Η or; 7