TWI716791B - 純化方法 - Google Patents
純化方法 Download PDFInfo
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- TWI716791B TWI716791B TW107146352A TW107146352A TWI716791B TW I716791 B TWI716791 B TW I716791B TW 107146352 A TW107146352 A TW 107146352A TW 107146352 A TW107146352 A TW 107146352A TW I716791 B TWI716791 B TW I716791B
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- formation inhibitor
- peroxide formation
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- 238000000034 method Methods 0.000 title claims abstract description 43
- 238000000746 purification Methods 0.000 title claims abstract description 33
- 239000003112 inhibitor Substances 0.000 claims abstract description 62
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 42
- 239000003960 organic solvent Substances 0.000 claims abstract description 32
- 150000002978 peroxides Chemical class 0.000 claims abstract description 28
- 239000002904 solvent Substances 0.000 claims abstract description 28
- -1 phenolic peroxide Chemical class 0.000 claims abstract description 26
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 238000009835 boiling Methods 0.000 claims abstract description 15
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 239000004065 semiconductor Substances 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 15
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 claims description 11
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 claims description 7
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 6
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- LGXAANYJEHLUEM-UHFFFAOYSA-N 1,2,3-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1C(C)C LGXAANYJEHLUEM-UHFFFAOYSA-N 0.000 claims description 3
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 claims description 3
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 claims description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 claims description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 3
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 claims description 3
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 claims description 3
- 229940116333 ethyl lactate Drugs 0.000 claims description 3
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 claims description 2
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 claims description 2
- UOHRPWGJMYLLPA-UHFFFAOYSA-N FC(C1=C(C(=CC(=C1)C(F)(F)F)C(C)(C)C)O)(F)F Chemical compound FC(C1=C(C(=CC(=C1)C(F)(F)F)C(C)(C)C)O)(F)F UOHRPWGJMYLLPA-UHFFFAOYSA-N 0.000 claims description 2
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000486 o-cresyl group Chemical group [H]C1=C([H])C(O*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- WDRJNKMAZMEYOF-UHFFFAOYSA-N 4-(trifluoromethoxy)phenol Chemical compound OC1=CC=C(OC(F)(F)F)C=C1 WDRJNKMAZMEYOF-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 description 6
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- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
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- 238000003756 stirring Methods 0.000 description 3
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
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- 150000002739 metals Chemical class 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
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- 229920006362 Teflon® Polymers 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- OIPDQRKFJGFVSP-UHFFFAOYSA-N benzene-1,4-diol 4-tert-butylphenol Chemical compound C1(O)=CC=C(O)C=C1.C(C)(C)(C)C1=CC=C(C=C1)O OIPDQRKFJGFVSP-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
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Abstract
提供了純化方法,其包括:(a)提供有機溶劑及酚類過氧化物形成抑制劑,其中所述有機溶劑具有標準大氣壓下的第一沸點(bp1
),且所述酚類過氧化物形成抑制劑具有標準大氣壓下的第二沸點(bp2
),滿足以下不等式(I): bp2
≤ (1.10)(bp1
) (I);及 (b)將所述有機溶劑及所述酚類過氧化物形成抑制劑加熱至使所述有機溶劑及酚類過氧化物形成抑制劑蒸發的溫度,及(ii)冷凝所述蒸發的有機溶劑及過氧化物形成抑制劑,以提供所述有機溶劑及過氧化物形成抑制劑的純化混合物。所述方法特別適用於溶劑的純化,所述溶劑可用於製造半導體裝置的製程化學品中。
Description
本發明大體上係關於化學純化。更特定言之,本發明係關於有機溶劑及過氧化物形成抑制劑的共純化,以形成純化的溶劑混合物。本發明特別適用於製備可用於電子工業的溶劑混合物。
在半導體製造工業中,裝置製造中使用之製程材料及其相關的原材料可能受到如有機過氧化物之過氧化物的污染。有機溶劑(如醚及酯)在大氣氧存在下特別容易形成有機過氧化物。在敏感的有機溶劑中包含乳酸乙酯、丙二醇單甲醚、二丙二醇單甲醚及丙二醇單甲醚乙酸酯,其通常用於光微影材料中。在溶劑或含有溶劑之組合物的儲存過程中可能發生此等溶劑中之過氧化物形成。光微影材料中過氧化物的存在會不利地影響所形成之圖案,例如其厚度或臨界尺寸。此可能導致形成之半導體裝置中之缺陷及產量損失。從安全角度來看,半導體製程化學品中存在過氧化物可另外為有問題的。特別地,過氧化物會造成嚴重的火災及爆炸危險,且亦可能具有毒性及腐蝕性。因此將希望最小化或消除有機溶劑中過氧化物的形成。
致力於最小化有機溶劑中過氧化物的形成,已提出向純化的有機溶劑中加入過氧化物形成抑制劑,例如在美國專利第3,221,030號中。然而,工業抑制劑含有污染純溶劑的金屬及/或高沸點雜質。此等雜質會對半導體製造製程及所得電子裝置產生不利影響,特別是在先進半導體裝置之情況下,其中雜質減少之重要性日益增加。因此,將需要穩定形成過氧化物之溶劑同時最小化或避免金屬及/或高沸點污染物的方法。
因此,本領域中需要改良之純化方法,其解決了與目前先進技術相關的一或多個問題。
根據本發明之一個態樣,提供純化方法。純化方法包括:(a)提供有機溶劑及酚類過氧化物形成抑制劑,其中有機溶劑具有標準大氣壓下的第一沸點(bp1
),且酚類過氧化物形成抑制劑具有標準大氣壓下的第二沸點(bp2
),滿足以下不等式(I): bp2
≤ (1.10)(bp1
) (I);及 (b)將有機溶劑及酚類過氧化物形成抑制劑加熱至使有機溶劑及酚類過氧化物形成抑制劑蒸發的溫度,及(ii)冷凝蒸發的有機溶劑及酚類過氧化物形成抑制劑,以提供有機溶劑及酚類過氧化物形成抑制劑之純化混合物。
為了解決與目前先進技術相關的一或多個問題,已開發了新的純化方法,藉由所述方法可同時加工有機溶劑及酚類過氧化物形成抑制劑以形成此等組分之純化混合物。本發明之方法特別適用於電子工業。
一或多種有機溶劑可在本發明之方法中一起處理。適合之有機溶劑包含例如:醚,如異戊基醚、甲基第三丁基醚、四氫呋喃、2-丁氧基乙醇、丙二醇單甲基醚(PGME)、二丙二醇單甲醚(DPM)、二丙二醇二甲醚及三丙二醇單甲醚(TPM);酯,如3-乙氧基丙酸乙酯、乳酸乙酯及丙二醇單甲基醚乙酸酯(PGMEA);醇,如異丙醇、甲基異丁基甲醇(MIBC)、丙二醇、二丙二醇及三丙二醇;芳族物,如二異丙基苯及三異丙基苯;及酮,如丙酮、環戊酮及環己酮;以及其組合。溶劑通常選自醚及酯。
適合之過氧化物形成抑制劑的選擇將取決於所要純化的特定溶劑。抑制劑應可溶於溶劑中。適合之酚類過氧化物形成抑制劑包含非氟化或氟化酚,例如苯酚、2-甲基苯酚、2-(三氟甲基)苯酚、4-甲氧基苯酚、2,4-二甲基-6-第三丁基苯酚、2,4-二(三氟甲基)-6-第三丁基苯酚、2,6-二-第三丁基苯酚、4-第三丁基鄰苯二酚以及其組合。其中,2-甲基苯酚、2,4-二甲基-6-第三丁基苯酚以及其組合為典型的。通常,過氧化物形成抑制劑的用量為按總抑制劑及溶劑計之1至1000 ppm、較佳10至100 ppm。較佳地,純化的溶劑抑制劑產物中過氧化物形成抑制劑的含量與預純化組分的比例大致相同,但此將取決於例如組分的相對沸點及純化方法條件。
適當的溶劑-抑制劑配對將取決於例如溶劑及抑制劑的相對沸點。溶劑具有標準大氣壓下的第一沸點(bp1
),且過氧化物形成抑制劑具有標準大氣壓下室溫第二沸點(bp2
),滿足以下不等式(I): bp2
≤ (1.10)(bp1
) (I) 或更佳地滿足以下不等式(II): (0.90)(bp1
) < bp2
< (1.10)(bp1
) (II) 或更佳地滿足以下不等式(III): (0.95)(bp1
) < bp2
< (1.05)(bp1
) (III)。
當滿足此等不等式時,當使用對於單獨的溶劑而言典型的純化條件時,基於預純化組分的使用量,可在純化的混合物中獲得足夠含量的過氧化物形成抑制劑。由此可同時純化溶劑及抑制劑。較佳地,過氧化物形成抑制劑的沸點bp2
低於溶劑的沸點bp1
。
特別適合之溶劑/抑制劑組合包含例如2-丁氧基乙醇/苯酚、異戊醚/苯酚、二丙二醇二甲醚/苯酚、丙二醇/2-甲基苯酚、二丙二醇單甲醚/2-甲基苯酚、二異丙基苯/2-甲基苯酚、三異丙基苯/4-甲氧基苯酚、三丙二醇單甲醚/2,4-二甲基-6-第三丁基苯酚(Topanol A)、環戊酮/2,6-二第三丁基苯酚及三丙二醇/4-第三丁基鄰苯二酚。
溶劑-抑制劑混合物藉由熱純化方法,如蒸餾及/或分餾方法純化。熱純化方法包含將溶劑-抑制劑混合物加熱至有效地使混合物沸騰的溫度。所述方法之適合溫度將取決於例如溶劑及過氧化物形成抑制劑的沸點,以及進行所述方法的壓力。可基於組分的壓力-溫度曲線容易地確定適合之溫度。
熱純化方法可在標準壓力(760托)下進行,或更佳在減壓下進行。較佳地,藉由對溶劑-抑制劑混合物施加真空及加熱來進行熱純化方法。施加真空允許比在標準壓力下進行的此類方法將另外所需之溫度更低的溫度。在真空下純化為進一步有利的,因為其降低了在回收過程中形成非所需副反應物雜質之可能性。所述方法之適合壓力取決於例如溶劑-抑制劑混合物的蒸氣壓及組分的分壓。典型的減壓純化方法可例如在0.01至50托之壓力下進行。
藉由將溶劑-抑制劑混合物暴露於高溫相對較短的時間進行蒸餾對於降低在回收過程中形成非所需副反應物雜質之可能性亦為有利的。例如,可能需要進行蒸餾步驟少於五分鐘的時間、少於三分鐘的時間或少於兩分鐘的時間。
熱純化步驟可藉由短滯留時間蒸餾技術進行。適合之此類技術包含例如刮膜蒸發、升膜蒸發、薄膜蒸發、(離心)分子蒸餾、降膜蒸餾或其組合。用於此類方法之適合之此類方法及工具為熟知的,且揭示於例如美國專利號7,560,579 B2中。
根據本發明之方法,溶劑及過氧化物形成抑制劑可在引入至熱純化工具中之前預先混合。可藉由將抑制劑添加至溶劑組分中來製備混合物。然後通常攪拌或另外攪動混合物以形成均質混合物。或者,可將溶劑及抑制劑分別引入至熱純化工具中。
以下非限制性實例說明本發明。
實例
實例1
將195 g Dowanol™ TPM二醇醚(陶氏化學公司(The Dow Chemical Company))及0.002 g Topanol™ A抑制劑(2,4-二甲基-6-第三丁基苯酚,TCI America)在塑膠燒杯中混合且攪拌以確保混合。將100 g所得混合物加入短程刮膜式蒸發器中且進行蒸餾。蒸發器包含UIC-GmbH短路蒸餾裝置、用於擦拭葉片的IKA RW 20數位電機及Vacuubrand GMBH RZ2.5旋轉葉片泵。將混合物以10-12公克/分鐘之速率自蒸發器頂部饋入。總表面積為0.02 m2
的蒸發器為使用熱油控制溫度的有夾套的硼矽酸鹽玻璃圓筒。在加熱表面內,使用鐵氟龍(Teflon)輥來分配饋入材料。饋入材料與加熱表面之滯留時間或接觸時間約為30-60秒。位於加熱表面中心的內部冷凝器用於冷凝餾出物相,所述餾出物相自蒸發器的上部區收集在接收器燒瓶中。將非揮發性底部物自蒸發器之底部區收集在單獨的接收器燒瓶中。饋入速率由蠕動泵控制。夾套溫度最初設定為40℃,直至收集到一些底部物,且接著將溫度變為60℃,隨後進行調整,通常在穩態下為50-56℃,以控制蒸餾分離。蒸發器在穩態下的壓力約為100毫托。設計穩態製程條件以實現95-98%塔頂物的目標分離。將塔頂樣品收集在接收器燒瓶中。分析蒸餾前樣品及蒸餾後樣品的Topanol A抑制劑的含量。在蒸餾前及蒸餾後樣品中均觀察到9.1 g Topanol A抑制劑。
實例2
將200 g Dowanol™ DPM二醇醚(陶氏化學公司)及0.002 g 2-甲基苯酚抑制劑在塑膠燒杯中混合且攪拌以確保混合。使用實例1之程序進行100 g所得混合物的蒸餾,具有以下差異: 饋入速率: 10-12公克/分鐘 蒸發器壓力: 穩態時3.5托 夾套溫度: 最初45℃,經由蒸餾逐步增加至50℃。
分析蒸餾前樣品及蒸餾後樣品之鄰甲酚抑制劑的含量。蒸餾前樣品的抑制劑含量為20.2 ppm,且蒸餾後樣品含量為10.7 ppm。
實例3
將20 L Dowanol™ TPM二醇醚(陶氏化學公司)及10 ppm Topanol A抑制劑(TCI America)在圓底燒瓶中混合且攪拌以確保混合。使用短程真空蒸餾進行所得混合物的蒸餾。使用Agilent 8800 ICP質譜系統分析個別預蒸餾TPM二醇醚及抑制劑以及所得餾出物之金屬雜質含量。資料概述於表1中,其中金屬含量以十億分率(ppb)提供。 表1
nd=低於偵測極限
實例4
將實例3中得到的餾出物樣品置於兩個容器中,且在4℃及35℃下儲存。將未抑制的TPM二醇醚樣品分別置於另外兩個容器中,且在4℃及35℃下儲存。藉由移液管定期自容器中取出容器中之樣品,且藉由氧化還原電位滴定分析總過氧化物含量。結果顯示於圖1-2中,顯示了對於過氧化物抑制的餾出物及未抑制的溶劑,在4℃及35℃下過氧化物含量隨時間的變化。
將參看以下附圖描述本發明,在所述附圖中: 圖1為顯示根據本發明純化的過氧化物抑制溶劑及比較未抑制溶劑在4℃下的過氧化物含量隨時間變化的圖;且 圖2為顯示根據本發明純化的過氧化物抑制溶劑及比較未抑制溶劑在35℃下的過氧化物含量隨時間變化的圖。
Claims (12)
- 一種純化方法,其包括:(a)提供有機溶劑及酚類過氧化物形成抑制劑,其中所述過氧化物形成抑制劑的用量為按總抑制劑及溶劑計之1至1000ppm,其中所述有機溶劑具有標準大氣壓下的第一沸點(bp1),且所述酚類過氧化物形成抑制劑具有標準大氣壓下的第二沸點(bp2),滿足以下不等式(III):(0.95)(bp1)<bp2<(1.05)(bp1) (III);及(b)將所述有機溶劑及所述酚類過氧化物形成抑制劑加熱至使所述有機溶劑及酚類過氧化物形成抑制劑蒸發的溫度,及(ii)冷凝所述蒸發的有機溶劑及酚類過氧化物形成抑制劑,以提供所述有機溶劑及酚類過氧化物形成抑制劑的純化混合物。
- 如申請專利範圍第1項之純化方法,其中所述純化方法為蒸餾法。
- 如申請專利範圍第1項或第2項之純化方法,其中所述純化方法在真空下進行。
- 如申請專利範圍第1項或第2項之純化方法,其中所述有機溶劑及所述酚類過氧化物形成抑制劑在所述加熱步驟之前混合。
- 如申請專利範圍第1項或第2項之純化方法,其中bp2小於bp1。
- 如申請專利範圍第1項或第2項之純化方法,其中所述酚類過氧化物形成抑制劑選自苯酚、2-甲基苯酚、2-(三氟甲基)苯酚、4-甲氧基苯酚、4-(三氟甲氧基)苯酚、2,4-二甲基-6-第三丁基苯酚、2,4-二(三氟甲基)-6-第三丁基苯酚、2,6-二-第三丁基苯酚、4-第三丁基鄰苯二酚以及其組合。
- 如申請專利範圍第7項之純化方法,其中所述酚類過氧化物形成抑制劑選自2-甲基苯酚、2,4-二甲基-6-第三丁基苯酚以及其組合。
- 如申請專利範圍第1項或第2項之純化方法,其中所述有機溶劑選自以下中之一或多者:異戊基醚、2-丁氧基乙醇、二丙二醇單甲醚、二丙二醇二甲醚、三丙二醇單甲醚、3-乙氧基丙酸乙酯、乳酸乙酯、丙二醇、三丙二醇、二異丙基苯、三異丙基苯、環戊酮、環己酮以及其組合。
- 如申請專利範圍第8項之純化方法,其中所述有機溶劑為三丙二醇單甲醚且所述酚類過氧化物形成抑制劑為2,4-二甲基-6-第三丁基苯酚,或其中所述溶劑為二丙二醇單甲醚且所述酚類過氧化物形成抑制劑為2-甲基苯酚。
- 如申請專利範圍第9項之純化方法,其中所述有機溶劑為三丙二醇單甲醚且所述酚類過氧化物形成抑制劑為2,4-二甲基-6-第三丁基苯酚。
- 一種如申請專利範圍第1至10項之純化方法製備的有機溶劑及酚類過氧化物形成抑制劑的純化混合物。
- 一種如申請專利範圍第11項之純化混合物用於製造半導體裝置的用途。
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