PHOTORESIST STRIPPING COMPOSITION

Abstract

A photoresist stripping composition comprising an organic amine and a method is provided. The photoresist stripping composition comprising an organic amine having the following formula (1).

##STR00001##

Claims

1. A photoresist stripping composition comprising an organic amine having the following formula (1): ##STR00009## wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of hydrogen and C.sub.1-C.sub.5 alkyl.

2. The photoresist stripping composition of claim 1, wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of hydrogen and C.sub.1-C.sub.4 alkyl.

3. The photoresist stripping composition of claim 1, wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of hydrogen and C.sub.1-C.sub.2 alkyl.

4. The photoresist stripping composition of claim 1, wherein the organic amine having the above formula (1) comprises the following compounds: ##STR00010##

5. The photoresist stripping composition of claim 1, wherein the composition comprises water.

6. The photoresist stripping composition of claim 1, wherein the composition comprises one or more glycol ethers.

7. A method of stripping a photoresist, comprising: (1) providing a substrate having a photoresist; (2) spraying a photoresist stripping composition to the substrate or dipping the substrate into a photoresist stripping composition, wherein the photoresist stripping composition comprises an organic amine having the following formula (1): ##STR00011## wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of hydrogen and C.sub.1-C.sub.5 alkyl.

8. The method of claim 7, wherein the substrate is selected from the group consisting of a semiconductor wafer, a printed wire board, an OLED display and a liquid crystal display.

9. Use of an organic amine in a photoresist stripping composition, wherein said organic amine has the following formula (1): ##STR00012## wherein R.sub.1 and R.sub.2 are each independently selected from the group consisting of hydrogen and C.sub.1-C.sub.5.

10. The use of claim 9, wherein said use comprise inhibiting the corrosion of interconnect metal.

Description

EXAMPLES

Materials

[0045] Photoresist: SFP-1400 solution (from MERCK).

[0046] Solvents: diethylene glycol butyl ether (from Dow Chemical Company, 99%).

[0047] Amines: 3-(dimethylamino)-1,2-propanediol (available from DU-HOPE INTERNATIONAL GROUP COMPANY; monoethanolamine, N-methylethanolamine, monoisopropanolamine and aminoethylethanolamine (all available from Dow Chemical Company, 99%)

[0048] Copper foil with thickness of 1 mm (from Alfa Aesar, 99.999%)

Terminologies of Different Chemicals are Shown Below

[0049] BuCb: diethylene glycol butyl ether

[0050] DMAPD: 3-(dimethylamino)-1,2-propanediol

[0051] MEA: monoethanolamine

[0052] NMEA: N-methylethanolamine

[0053] MIPA: monoisopropanolamine

[0054] AEEA: aminoethylethanolamine

[0055] MAPD: 1-(Methylamino)-2,3-Propanediol (Adamas Reagent Co., Ltd Purity 98%)

Examples 1-6 and Comparative Examples 1-24

[0056] The photoresist stripping compositions were prepared by mixing the components listed in Table 1 below:

TABLE-US-00001 TABLE 1 Component A Weight % Component B Weight % Component C Weight % Example 1 DMAPD 20 BuCb 30 water 50 2 DMAPD 12 BuCb 18 water 70 3 DMAPD 50 BuCb 50 4 DMAPD 30 BuCb 70 5 DMAPD 50 water 50 6 DMAPD 30 water 70 Comparative Example 1 MEA 20 BuCb 30 water 50 2 MEA 12 BuCb 18 water 70 3 MEA 50 BuCb 50 4 MEA 30 BuCb 70 5 MEA 50 water 50 6 MEA 30 water 70 7 NMEA 20 BuCb 30 water 50 8 NMEA 12 BuCb 18 water 70 9 NMEA 50 BuCb 50 10 NMEA 30 BuCb 70 11 NMEA 50 water 50 12 NMEA 30 water 70 13 MIPA 20 BuCb 30 water 50 14 MIPA 12 BuCb 18 water 70 15 MIPA 50 BuCb 50 16 MIPA 30 BuCb 70 17 MIPA 50 water 50 18 MIPA 30 water 70 19 AEEA 20 BuCb 30 water 50 20 AEEA 12 BuCb 18 water 70 21 AEEA 50 BuCb 50 22 AEEA 30 BuCb 70 23 AEEA 50 water 50 24 AEEA 30 water 70

Example 7

[0057] 2 mL of SFP-1400 photoresist solution was coated onto the surface of glass substrate with the size of 100 mm×100 mm×1 mm. The substrate was spun at the rotation speed of 500 rpm for 10 seconds, and then the rotation speed was accelerated to 1000 rpm and maintained for 30 seconds. The spin-coated substrate was baked at 130° C. for 10 min to evaporate the solvent completely and cure the photoresist film. In the following stripping step, 30 g of each above example or comparative example was prepared in a container. The baked substrate was put into the container at 22° C., with shaking Finally, the time was recorded for completely removing the photoresist from the substrate. The results were listed in Tables 2 and 3 below.

[0058] The photoresist stripping results of the examples or comparative examples were listed in the tables below. The performance was evaluated by stripping time. The shorter time it takes to remove photoresist film from the substrate, the better performance the stripping solutions have. Higher water content can shorten the stripping time. MEA, NMEA, MIPA and AEEA are typical organic amines used in the photoresist stripping composition. As shown in Tables 2 and 3, the stripping time was categorized into 4 groups for comparison. 3-(dimethylamino)-1,2-propanediol could provide similar performance

TABLE-US-00002 TABLE 2 # Component A Weight % Component B Weight % Component C Weight % Performance Example 1 DMAPD 20 BuCb 30 water 50 O Comparative Example 1 MEA 20 BuCb 30 water 50 ⊙ 7 NMEA 20 BuCb 30 water 50 ◯ 13 MIPA 20 BuCb 30 water 50 Δ 19 AEEA 20 BuCb 30 water 50 Δ ⊙ <60 seconds; ◯ 60~65 seconds; Δ 65~70 seconds; X >70 seconds

TABLE-US-00003 TABLE 3 # Component A Weight % Component B Weight % Component C Weight % Performance Example 2 DMAPD 12 BuCb 18 water 70 Δ Comparative Example 2 MEA 12 BuCb 18 water 70 ◯ 8 NMEA 12 BuCb 18 water 70 Δ 14 MIPA 12 BuCb 18 water 70 Δ 20 AEEA 12 BuCb 18 water 70 X ⊙ <30 seconds; ◯ 30~40 seconds; Δ 40~50 seconds; X >50 seconds

Example 8

[0059] The highly pure copper foil with calendering thickness of 1 mm (from Alfa Aesar, 99.999%) was cut into squares with weight of 0.90±0.01 g. A copper oxide (CuO or Cu.sub.2O) passivation layer was formed on the surface of the copper foil. The copper pieces were then immersed in a 5% HCl aqueous solution for 5 minutes in order to completely remove the passivation layer and ensure the 99.999% purity. The acid-treated copper pieces were rinsed with 20 mL DI water and dried by nitrogen gas flow. Each copper piece was put in a 10 mL glass bottle with 5 g formulation of the examples or comparative examples at 54° C. for 30 min. Then, the copper pieces were taken out. ICP-OES (PerkinElmer 5300DV) was used to determine the content of copper ions remaining in the solvent. The results were listed in Tables 4 and 5 below.

[0060] The amounts of copper ions in the formulations were detected to evaluate the copper corrosion performance The copper ions in ppm levels are also categorized into 4 groups. As shown in Tables 4 and 5, MEA, NMEA and MIPA caused serious copper corrosion because a large amount of copper ions in the liquid formulations were detected. The formulations comprising 3 -(dimethylamino)-1,2-propanediol and AEEA showed the retardant corrosion effect.

TABLE-US-00004 TABLE 4 # Component A Weight % Component B Weight % Performance Example 3 DMAPD 50 BuCb 50 ◯ 4 DMAPD 30 BuCb 70 ⊙ Comparative Example 3 MEA 50 BuCb 50 ◯ 4 MEA 30 BuCb 70 × 9 NMEA 50 BuCb 50 ◯ 10 NMEA 30 BuCb 70 × 15 MIPA 50 BuCb 50 Δ 16 MIPA 30 BuCb 70 × 21 AEEA 50 BuCb 50 ◯ 22 AEEA 30 BuCb 70 Δ ⊙: <1 ppm; ◯: 1~2 ppm; Δ: 2~4 ppm; ×: >4 ppm

TABLE-US-00005 TABLE 5 # Component A Weight % Component C Weight % Performance Example 5 DMAPD 50 water 50 ◯ 6 DMAPD 30 water 70 ⊙ Comparative Example 5 MEA 50 water 50 ◯ 6 MEA 30 water 70 × 11 NMEA 50 water 50 ◯ 12 NMEA 30 water 70 × 17 MIPA 50 water 50 ◯ 18 MIPA 30 water 70 × 23 AEEA 50 water 50 ⊙ 24 AEEA 30 water 70 ⊙ ⊙: <1 ppm; ◯: 1~2 ppm; Δ: 2~4 ppm; ×: >4 ppm

Examples 9-13 and Comparative Examples 25-46

[0061] The highly pure copper foil with calendering thickness of 1 mm (from Alfa Aesar, 99.999%) was cut into 1 cm*1 cm pieces. The copper pieces were then immersed in a 2% HCl aqueous solution for 5 minutes in order to completely remove CuO or Cu.sub.2O. Each copper piece was put in a 10 mL glass bottle with 5 g formulation of the examples or comparative examples in Tables 6 and 7 below. The bottles were quickly shaked for two or three minutes and then were kept in an oven at 60° C. for 4 hours. Then, the copper pieces were taken out. ICP-OES (PerkinElmer 5300DV) was used to determine the content of copper ions remaining in the solution. The results were listed in Tables 6 and 7 below.

TABLE-US-00006 TABLE 6 Examples MAPD, % MEA, % MIPA, % NMEA, % BuCb, % Water, % Cu Ion, ppm Example 9 99.7 / / / / 0 0.3 Example 10 95.0 / / / / 5.0 0.2 Example 11 80.0 / / / / 20.0 0.5 Example 12 50.0 / / / / 50.0 1.4 Example 13 30 / / / 70 0 2.1 Comparative / 99.7 / / / 0 21.8 Example 25 Comparative / 95.0 / / / 5.0 13.0 Example 26 Comparative / 80.0 / / / 20.0 13.6 Example 27 Comparative / 50.0 / / / 50.0 13.0 Example 28 Comparative / 30 / / 70 0 50.0 Example 29 Comparative / / 99.7 / / 0 37.5 Example 30 Comparative / / 95.0 / / 5.0 36.6 Example 31 Comparative / / 80.0 / / 20.0 26.4 Example 32 Comparative / / 50.0 / / 50 19.2 Example 33 Comparative / / 30 / 70 0 126.0 Example 34 Comparative / / / 99.7 / 0 38.7 Example 35 Comparative / / / 95.0 / 5.0 26.0 Example 36 Comparative / / / 80.0 / 20.0 7.8 Example 37 Comparative / / / 50.0 / 50.0 4.3 Example 38 Comparative / / / 30 70 0 131.0 Example 39 Comparative / / / / / / 11.0 Example 40

TABLE-US-00007 TABLE 7 Examples MAPD, % MIPA, % bis-imidazoline, % bentzotriazole, % Cu Ion, ppm Example 9 99.7 / / / 0.3 Comparative Example 41 / 99.9 0.1 / 41 Comparative Example 42 / 99.5 0..5 / 35 Comparative Example 43 / 99.0 1.0 / 33 Comparative Example 44 / 99.9 / 0.1 29 Comparative Example 45 / 99.5 / 0..5 18 Comparative Example 46 / 99.0 / 1.0 16