TW201829549A - 聚醯亞胺、用於可撓性元件的聚醯亞胺膜、聚醯亞胺基板以及二胺 - Google Patents
聚醯亞胺、用於可撓性元件的聚醯亞胺膜、聚醯亞胺基板以及二胺 Download PDFInfo
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- TW201829549A TW201829549A TW106143998A TW106143998A TW201829549A TW 201829549 A TW201829549 A TW 201829549A TW 106143998 A TW106143998 A TW 106143998A TW 106143998 A TW106143998 A TW 106143998A TW 201829549 A TW201829549 A TW 201829549A
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Abstract
本發明是對由在分子結構中包括螺環基或酚酞基的二胺製備的聚醯亞胺進行說明,上述聚醯亞胺於較高的溫度下可提高尺寸穩定性,因此,可提供一種有效地用於可撓式基板的聚醯亞胺膜。
Description
本申請案主張以2017年1月31日申請的韓國專利申請案10-2017-0013726號、與2017年12月7日申請的10-2017-0167165號為基礎的優先權的利益,本說明書將上述申請案中所記載的所有內容包括作一部分。
本發明是有關於一種耐熱性及熱穩定性提高的聚醯亞胺及包括其的用於可撓式顯示器的聚醯亞胺膜。
聚醯亞胺(polyimide,PI)作為結晶度相對較低、或大部分具有非晶質結構的聚合物,其是一種不僅具有合成容易,可製作成薄膜且無需使用用於硬化的交聯基等優點,而且具有透明性、因堅固的鏈結構所實現的卓越耐熱性與耐化學性、優異的機械物性、電特性及尺寸穩定性的聚合物材料,目前廣泛地用作汽車、航空航天領域、軟性電路板、液晶顯示裝置(Liquid Crystal Display,LCD)用液晶配向膜、接著劑及塗覆劑等電性、電子材料。
然而,即便聚醯亞胺為具有較高的熱穩定性、機械物性、耐化學性及電特性的高性能聚合物材料,亦未能滿足顯示器領域所需的基本必要條件(即無色透明的性質),且存在需進一步降低熱膨脹係數的課題。例如,由杜邦公司售賣的Kapton的熱膨脹係數為約30 ppm/℃左右,其雖表現出較低的熱膨脹係數值,但仍無法滿足塑膠基板的要求條件。因此,目前較多的研究都朝向保持聚醯亞胺的基本特性且最小化其光學特性及熱特性的改變方面進行。
然而,為了使用於顯示器領域,需開發一種具有更低的熱膨脹係數,且具有較高的溶解度、透明度及熱安全性的用於可撓式顯示器的聚合物。
[發明欲解決的課題]
本發明欲解決的課題在於提供一種耐熱性及熱穩定性得到改善的聚醯亞胺。
本發明欲解決的另一課題在於提供一種包括上述聚醯亞胺的聚醯亞胺膜。
再者,本發明提供一種於分子結構中包括螺環基或酚酞基的新穎結構的二胺。
[解決課題的手段]
為了解決如上所述的技術課題,本發明提供一種由包括四羧酸二酐與選自下述化學式1a至化學式1e中的一種以上的二胺的聚合成分製備的聚醯亞胺。 [化學式1a][化學式1b][化學式1c][化學式1d][化學式1e]於上述化學式1b至化學式1e中, 上述R1
、R2
分別獨立地為選自氫原子、鹵素原子、羥基(-OH)、硫醇基(-SH)、硝基(-NO2
)、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基中的取代基。
根據一實施例,上述聚合成分可相對於上述二胺的總含量而包括30莫耳%至100莫耳%的以上述化學式1表示的二胺。
根據一實施例,上述聚醯亞胺的熱膨脹係數(CTE)可為50 ppm/℃以下。
根據一實施例,上述聚醯亞胺的玻璃轉移溫度(Tg)可為330℃以上。
為了解決本發明的另一課題,提供一種包括上述聚醯亞胺的用於可撓式顯示器的聚醯亞胺膜。
再者,本發明提供一種以下述化學式1a至化學式1e中的任一者表示的二胺。 [化學式1a][化學式1b][化學式1c][化學式1d][化學式1e]於上述化學式1a至化學式1e中, 上述R1
、R2
分別獨立地為選自氫原子、選自-F、-Cl、-Br及-I中的鹵素原子、羥基(-OH)、硫醇基(-SH)、硝基(-NO2
)、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基的取代基。
[發明的效果]
本發明的聚醯亞胺由包括兩個以上的苯基連接固定而成的螺環(Spiro)基或酚酞(cardo)基的二胺製備,藉此不僅具有較高的玻璃轉移溫度,而且對熱的尺寸穩定性可提高。由本發明的聚醯亞胺製備的聚醯亞胺膜具有優異的熱穩定性,因此適於伴隨高溫製程的可撓式器件、特別是使用氧化物(Oxide)薄膜電晶體(thin film transistor,TFT)與低溫多晶矽(low temperature polysilicon,LTPS)製程的有機發光二極體(organic light emitting diode,OLED)器件。
本發明可實施多種變換,可具有多種實施例,並於詳細說明中詳細地進行說明。然而,上述實施例並非意欲將本發明限定於特定的實施方式,應理解為包括包含於本發明的思想及技術範圍內的所有變換、等同物或替代物。於對本發明進行說明時,在判斷為對相關公知技術的具體說明會混淆本發明的主旨的情形時,省略其詳細說明。
於本說明書中,只要未特別提及,則所有化合物或有機基團可為經取代或未經取代者。此處,「經取代」是指化合物或有機基團中所包括的至少一個氫由選自由鹵素原子、碳數為1至10的烷基、鹵化烷基、碳數為3至30的環烷基、碳數為6至30的芳基、羥基、碳數為1至10的烷氧基、羧酸基、醛基、環氧基、氰基、硝基、胺基、磺酸基及其衍生物所組成的族群中的取代基替代。
再者,於本說明書中,只要未特別提及,則「其組合」是指兩個以上的官能基藉由如單鍵、雙鍵、三鍵、碳數為1至10的伸烷基(例如,伸甲基(-CH2
-)、伸乙基(-CH2
CH2
-)等)、碳數為1至10的氟伸烷基(例如,氟伸甲基(-CF2
-)、全氟伸乙基(-CF2
CF2
-)等)、如N、O、P、S、或Si的雜原子或包括其的官能基(例如,於分子內包括羰基(-C(=O)-)、醚基(-O-)、酯基(-COO-)、-S-、-NH-或-N=N-等的雜伸烷基)的連接基而鍵結、或兩個以上的官能基縮合或連接。
對伴隨高溫製程的可撓式器件要求高溫下的耐熱性,特別是於使用氧化物TFT(thin film transistor)與LTPS(low temperature polysilicon)製程的OLED(organic light emitting diode)器件的情形時,製程溫度為350℃以上,甚至接近500℃。
於此種溫度下,即便為具有優異的耐熱性的聚醯亞胺,亦容易熱分解,會發生因熱引起的收縮或膨脹。因此,為了製備可撓式器件,需開發一種如下的聚醯亞胺:可連同優異的機械特性一併於高溫下保持較高的透明性,並且表現出優異的熱穩定性。
本發明提供一種由具有新穎結構的二胺製備的超高耐熱性聚醯亞胺。
本發明的另一目的在於提供一種包括上述聚醯亞胺的聚醯亞胺膜。
本發明提供一種以選自下述化學式1a至化學式1e中的一者表示的二胺。 [化學式1a][化學式1b][化學式1c][化學式1d][化學式1e]於上述化學式1b至化學式1e中, 上述R1
、R2
分別獨立地為選自氫原子、鹵素原子、羥基(-OH)、硫醇基(-SH)、硝基(-NO2
)、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基中的取代基。
再者,本發明提供一種聚醯亞胺,其由包括四羧酸二酐與一種以上的二胺的聚合成分製備,上述二胺為以上述化學式1a至化學式1e中的任一者表示的二胺。
根據一實施例,於上述聚合成分中,相對於二胺的總含量,可包括30莫耳%至100莫耳%的以上述化學式1表示的二胺,較佳為可包括50莫耳%至100莫耳%的上述二胺。
本發明的二胺呈包括兩個以上的苯基連接固定而成的螺環基(spiro group)或酚酞基(cardo group)的結構,包括苯基未固定的基團的聚醯亞胺的玻璃轉移溫度雖上升,但CTE(熱膨脹係數)變高而熱穩定性會下降,但本發明可藉由固定苯基來提供一種玻璃轉移溫度較高且CTE的增加得到抑制而熱穩定性優異的聚醯亞胺。
根據一實施例,上述聚醯亞胺的玻璃轉移溫度可為330℃以上,較佳為可為350℃以上。
根據一實施例,上述聚醯亞胺的CTE可為50 ppm/℃以下,較佳為可為30 ppm/℃以下,例如可為10 ppm/℃至30 ppm/℃。
此時,上述CTE是於如下步驟中測定100℃至250℃區間的值:設定為於以測定長度成為16 mm的方式,將厚度為10 μm、寬度為5 mm、長度為5 cm的樣品(sample)夾持至夾具後,以0.02 N的力拉伸,將升溫速度設為5℃/分而上升至300℃(1次升溫),之後將其冷卻至50℃(1次冷卻),再次升溫至450℃(2次升溫)。
根據一實施例,較佳為上述四羧酸二酐與二胺能夠以1∶0.99至0.99∶1的莫耳比、較佳為1∶0.98至0.98∶1的莫耳比進行反應。
上述四羧酸二酐只要為通常用於製備聚醯亞胺者,則可使用任一種。例如,可用於製備聚醯亞胺的四羧酸二酐可為包括脂肪族、脂環族或芳香族的4價有機基團藉由交聯結構彼此連接而成的4價有機基團作為分子內的芳香族、脂環族或脂肪族的4價有機基團或其組合基團的四羧酸二酐。例如,可為包括選自由以下述化學式2a至化學式2e表示的4價有機基團及其組合所組成的族群中的4價有機基團結構的四羧酸二酐。 [化學式2a][化學式2b][化學式2c][化學式2d][化學式2e]於上述化學式2a至化學式2e中,上述R11
至R17
可分別獨立地為選自氫原子、鹵素原子(選自-F、-Cl、-Br及-I)、羥基(-OH)、硫醇基(-SH)、硝基(-NO2
)、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基中的取代基, 上述a1可為0至2的整數,a2為0至4的整數,a3為0至8的整數,a4及a5分別獨立地為0至3的整數,a6及a9分別獨立地為0至3的整數,a7及a8分別獨立地為0至9的整數, 另外,上述A11
及A12
可分別獨立地為選自由單鍵、-O-、-CR18
R19
-、-C(=O)-、-C(=O)NH-、-S-、-SO2
-、伸苯基及其組合所組成的族群中的一者,此時上述R18
及R19
可分別獨立地為選自由氫原子、碳數為1至10的烷基及碳數為1至10的氟烷基所組成的族群中的一者。
例如,使用於本發明的四羧酸二酐可使用於結構中包括選自由下述化學式(3a)至化學式(3r)所組成的族群中的4價有機基團的四羧酸二酐,但並不限定於此。
於上述化學式(3l)中,A2
可為選自由單鍵、-O-、-C(=O)-、-C(=O)NH-、-S-、-SO2
-、伸苯基及其組合所組成的族群中的一者,v為0或1的整數,於上述化學式(3r)中,x為1至10的整數。
再者,存在於以上述化學式(3a)至化學式(3r)表示的4價有機基團中的1個以上的氫原子可由選自包括-F、-Cl、-Br及-I的鹵素原子、羥基(-OH)、硫醇基(-SH)、硝基(-NO2
)、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基中的取代基取代。
本發明除了以上述化學式1表示的二胺以外,可更使用其他種類的二胺,上述二胺只要為通常用於製備聚醯亞胺者,則可使用任一種,具體而言,作為脂肪族、脂環族或芳香族的2價有機基團或其組合基團,可為脂肪族、脂環族或芳香族的2價有機基團直接連接或藉由交聯結構彼此連接而成的2價有機基團,例如可為包括選自由以下述化學式4a至化學式4g表示的2價有機基團及其組合所組成的族群中的2價有機基團結構的二胺。 [化學式4a][化學式4b][化學式4c][化學式4d][化學式4e]於上述化學式4a至化學式4e中, R21
至R28
可分別獨立地為選自由碳數為1至10的烷基(例如,甲基、乙基、丙基、異丙基、正丁基、第三丁基、戊基等)、鹵基、羥基、羧基、碳數為1至10的烷氧基(例如,甲氧基、乙氧基、丙氧基、第三丁氧基等)及碳數為1至10的氟烷基(例如,三氟甲基等)所組成的族群中的一者, 再者,A21
及A22
可分別獨立地為選自由單鍵、-O-、-CR'R"-(此時,R'及R"分別獨立地為選自由氫原子、碳數為1至10的烷基(例如,甲基、乙基、丙基、異丙基、正丁基、第三丁基、戊基等)及碳數為1至10的鹵代烷基(例如,三氟甲基等)所組成的族群中的一者)、-C(=O)-、-C(=O)O-、-C(=O)NH-、-S-、-SO-、-SO2
-、-O[CH2
CH2
O]y-(y為1至44的整數)、-NH(C=O)NH-、-NH(C=O)O-、碳數為6至18的單環式或多環式環伸烷基(例如,環伸己基等)、碳數為6至18的單環式或多環式伸芳基(例如,伸苯基、伸萘基、伸芴基等)及其組合所組成的族群中的一者, b1
、b4
及b5
分別獨立地為0至4的整數,b2
為0至6的整數,b3
為0至3的整數,b6
及b9
分別獨立地為0或1的整數,b7
及b8
分別獨立地為0至10的整數。
例如,使用於本發明的二胺可更使用於結構中包括選自由下述化學式(5a)至化學式(5t)所組成的族群中的2價有機基團的二胺,但並不限定於此。
存在於以上述化學式(5a)至化學式(5t)表示的2價有機基團中的1個以上的氫原子可由選自包括-F、-Cl、-Br及-I的鹵素原子、羥基(-OH)、硫醇基(-SH)、硝基(-NO2
)、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基中的取代基取代。
根據一實施例,上述聚合成分可更連同選自化學式1a至化學式1e中的二胺一併包括以下述化學式6表示的二胺。 [化學式6]於上述化學式6中, 上述R31
及R32
分別獨立地為選自包括-F、-Cl、-Br及-I的鹵素原子、羥基(-OH)、硫醇基(-SH)、硝基(-NO2
)、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基中的取代基, n及m分別獨立地為0至4的整數, Q1
為選自由單鍵、-O-、-CR18
R19
-、-C(=O)-、-C(=O)O-、-C(=O)NH-、-S-、-SO2
-、伸苯基及其組合所組成的族群中的一者,此時上述R18
及R19
分別獨立地為選自由氫原子、碳數為1至10的烷基及碳數為1至10的氟烷基所組成的族群中的一者。
可根據聚醯亞胺前驅物的典型聚合製備方法(如溶液聚合)來實施使上述四羧酸二酐與二胺反應的方法,具體而言,可藉由如下方法製備作為聚醯亞胺前驅物的聚醯胺酸:將二胺溶解於有機溶劑中後,於所獲得的混合溶液中添加四羧酸二酐以進行聚合反應。
上述反應可於惰性氣體或氮氣氣流中實施,且可於無水條件下執行。
再者,於進行上述聚合反應時,可於-20℃至60℃、較佳為0℃至45℃的溫度下實施。於反應溫度過高的情形時,反應性變高而分子量會變大,前驅物組成物的黏度上升,因此會於製程上不利。
具體而言,作為可使用於上述聚合反應的有機溶劑,可包括選自由γ-丁內酯、1,3-二甲基-咪唑啶酮、甲基乙基酮、環己酮、環戊酮、4-羥基-4-甲基-2-戊酮等酮類;甲苯、二甲苯、四甲基苯等芳香族烴類;乙二醇單乙醚、乙二醇單甲醚、乙二醇單丁醚、二乙二醇單乙醚、二乙二醇單甲醚、二乙二醇單丁醚、丙二醇單甲醚、丙二醇單乙醚、二丙二醇二乙醚、三乙二醇單乙醚等二醇醚類(賽路蘇);乙酸乙酯、乙酸丁酯、乙二醇單乙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇單乙醚乙酸酯、二丙二醇單甲醚乙酸酯、乙醇、丙醇、乙二醇、丙二醇、卡必醇、二甲基乙醯胺(DMAc)、N,N-二乙基乙醯胺、二甲基甲醯胺(DMF)、二乙基甲醯胺(DEF)、N-甲基吡咯啶酮(NMP)、N-乙基吡咯啶酮(NEP)、1,3-二甲基-2-咪唑啶酮、N,N-二甲基甲氧基乙醯胺、二甲基亞碸、吡啶、二甲基碸、六甲基磷醯胺、四甲基脲、N-甲基己內醯胺、四氫呋喃、間二噁烷、對二噁烷、1,2-二甲氧基乙烷、雙(2-甲氧基乙基)醚、1,2-雙(2-甲氧基乙氧基)乙烷、雙[2-(2-甲氧基乙氧基)]醚及其混合物所組成的族群中的一者。
較佳地,可列舉二甲基亞碸、二乙基亞碸等亞碸類溶劑、N,N-二甲基甲醯胺、N,N-二乙基甲醯胺等甲醯胺類溶劑、N,N-二甲基乙醯胺、N,N-二乙基乙醯胺等乙醯胺類溶劑、N-甲基-2-吡咯啶酮、N-乙烯基-2-吡咯啶酮等吡咯啶酮類溶劑、苯酚、鄰甲酚、間甲酚或對甲酚、二甲苯酚、鹵化苯酚、鄰苯二酚等酚類溶劑、六甲基磷醯胺或γ-丁內酯等,其等可單獨利用或作為混合物而利用,更佳地,可為選自N,N-二乙基乙醯胺(N,N-diethylacetamide,DEAc)、N,N-二乙基甲醯胺(N,N-diethylformamide,DEF)、N-乙基吡咯啶酮(N-ethylpyrrolidone,NEP)或其混合物中的一者。
根據一實施例,上述有機溶劑亦可更使用如二甲苯、甲苯的芳香族烴,再者,為了促進聚合物的溶解,亦可於上述溶劑中更添加相對於上述溶劑總量為約50重量%以下的鹼金屬鹽或鹼土類金屬鹽。
考量到膜形成製程時的塗佈性等加工性,根據上述製備方法製備的聚醯亞胺前驅物溶液較佳為包括能使上述組成物具有適當的黏度的量的固體成分。根據一實施例,能夠以聚醯亞胺前驅物的整體含量成為5重量%至20重量%、較佳為8重量%至18重量%、更佳為8重量%至12重量%的方式調節上述組成物的含量。
可選地,上述聚醯亞胺前驅物溶液可為以具有2,000 cP以上或3,000 cP以上的黏度的方式調節,上述聚醯亞胺前驅物溶液的黏度較佳為以具有10,000 cP以下、較佳為9,000 cP以下、更佳為8,000 cP以下的黏度的方式調節。於聚醯亞胺前驅物溶液的黏度超過10,000 cP的情形時,在對聚醯亞胺膜進行加工時,消泡的效率下降,因此不僅製程上的效率下降,而且所製備的膜因氣泡的產生而表面粗糙度欠佳,從而電特性、光學特性、機械特性會下降。
再者,本發明的聚醯亞胺的分子量可具有10,000 g/mol至200,000 g/mol、20,000 g/mol至100,000 g/mol或30,000 g/mol至100,000 g/mol的重量平均分子量。再者,本發明的聚醯亞胺的分子量分佈(Mw/Mn)較佳為1.1至2.5。於聚醯亞胺的重量平均分子量或分子量分佈脫離上述範圍的情形時,存在難以形成膜、或透射度、耐熱性及機械特性等聚醯亞胺類膜的特性下降的疑慮。
接著,將上述聚合反應後所獲得的聚醯亞胺前驅物醯亞胺化,藉此可製備透明的聚醯亞胺膜。此時,具體而言,上述醯亞胺化製程可包括化學醯亞胺化方法或熱醯亞胺化方法。
例如,可藉由如下方法獲得聚醯亞胺:於在所聚合的上述聚醯亞胺前驅物溶液中添加脫水劑及醯亞胺化觸媒後,以50℃至100℃的溫度加熱而藉由化學反應進行醯亞胺化、或同時使上述溶液回流與去除醇而進行醯亞胺化。
於上述化學醯亞胺化方法中,可使用吡啶、三乙胺、甲基吡啶或喹啉等作為上述醯亞胺化觸媒,除此之外,有經取代或未經取代的含氮雜環化合物、含氮雜環化合物的N-氧化物化合物、經取代或未經取代的胺基酸化合物、具有羥基的芳香族烴化合物或芳香族雜環狀化合物,特別是亦可使用1,2-二甲基咪唑、N-甲基咪唑、N-苄基-2-甲基咪唑、2-甲基咪唑、2-乙基-4-甲基咪唑、5-甲基苯并咪唑等低級烷基咪唑、異喹啉、3,5-二甲基吡啶、3,4-二甲基吡啶、2,5-二甲基吡啶、2,4-二甲基吡啶、4-正丙基吡啶等取代吡啶、對甲苯磺酸等。
可使用乙酸酐等酸酐作為上述脫水劑。
可選地,可藉由在將上述聚醯亞胺前驅物溶液塗佈至基板上後進行熱處理的方法而進行醯亞胺化。
上述聚醯亞胺前驅物溶液可呈溶解於有機溶劑中的溶液形態,於呈此種形態的情形時、或例如於在有機溶劑中合成聚醯亞胺前驅物的情形時,溶液可為所獲得的反應溶液其本身,亦可為以其他溶劑稀釋上述反應溶液所得者。再者,於以粉末形式獲得聚醯亞胺前驅物的情形時,亦可為將上述粉末溶解至有機溶劑而製成的溶液。
本發明提供一種聚醯亞胺膜的製備方法,其包括:將上述聚醯亞胺前驅物溶液塗佈至基板上的步驟;以及 對塗佈的上述聚醯亞胺前驅物溶液進行熱處理的步驟。
將上述聚醯亞胺前驅物溶液塗佈至基板,於紅外線(Infrared,IR)烘箱、熱風烘箱內或加熱板上進行熱處理,此時,上述熱處理溫度可為300℃至500℃、較佳為320℃至480℃的溫度範圍,亦可於上述溫度範圍內按照多步驟進行加熱處理。上述熱處理製程可進行20分鐘至70分鐘,較佳為可進行20分鐘至60分鐘左右。
含有於本發明的聚醯亞胺前驅物溶液中的上述有機溶劑可使用與上述合成反應時使用的有機溶劑相同者。
只要在不損害效果的範圍下,本發明亦可添加矽烷偶合劑、交聯性化合物及以有效率地進行醯亞胺化為目的的醯亞胺化促進劑等。
再者,上述聚醯亞胺類膜的霧度(Haze)具有1以下、較佳為0.9以下或0.7以下、更佳為0.5以下的霧度值,從而可提供一種透明性得到改善的聚醯亞胺膜。此時,上述聚醯亞胺膜的厚度可為8 μm至15 μm,較佳為可為10 μm至12 μm。
再者,可為如下的無色透明的聚醯亞胺膜:於5 μm至30 μm的膜厚範圍內,380 nm至760 nm波長的光的透射度為80%以上,黃色度(YI)為約25以下、較佳為約20以下、更佳為約16以下或15以下。由於具有如上所述般優異的透光度及黃色度,因此可表現出得到明顯改善的透明度及光學特性。
再者,上述聚醯亞胺類膜的面內相位差值(Rin
)可為約0 nm至100 nm,厚度方向的相位差值(Rth
)的絕對值為約1500 nm以下或0 nm至1000 nm以下、較佳為30 nm至800 nm以下、更佳為50 nm至700 nm以下。於上述厚度方向的相位差範圍內,可表現出適於顯示器的視感性,於厚度方向的相位差為1500 nm以上的情形時,在聚醯亞胺膜中產生相位差而光失真,因此視感性會明顯下降。
於本發明的又一實施例中,提供一種包括上述聚醯亞胺共聚物的成形品(article)。
上述成形品可為膜、纖維(fiber)、塗覆材料、接著材料等,但並不限定於此。上述成形品可使用上述共聚物與無機粒子的錯合物組成物而藉由乾濕法、乾式法、濕式法等形成,但並不限定於此。具體而言,上述成形品可如上所述般為光學膜,於此情形時,包括上述聚醯亞胺共聚物的組成物可藉由如下方式容易地製備:於利用旋轉塗覆等方法應用至基板上後,對其進行乾燥及硬化。
本發明的聚醯亞胺可對會於進行高熱製程時發生的熱變化表現出優異的耐熱性,因此可使用於如元件用基板、顯示器用覆蓋基板、光學膜(optical film)、積體電路(integrated circuit,IC)封裝體、黏合膜(adhesive film),多層可撓式印刷電路(flexible printed circuit,FPC)、膠帶、觸控面板、光碟用保護膜等的各種領域,
根據本發明的又一實施例,提供一種包括上述成形品的顯示裝置。具體而言,上述顯示裝置可列舉液晶顯示裝置(liquid crystal display device,LCD)、有機發光二極體(organic light emitting diode,OLED)等,特別是可適於使用需要高溫製程的LTPS(low temperature polysilicon)製程的OLED器件,但並不限定於此。
以下,詳細地對本發明的實施例進行說明,以便在本發明所屬的技術領域內具有常識者可容易地實施。然而,本發明能夠以多種不同的形態實現,並不限定於此處所說明的實施例。
<合成例1> 如下所述般製備以化學式10表示的二胺化合物(化合物10)。化合物A 化合物B 化合物10
將化合物A(20.0 g,42.4 mmol)與化合物B(15.7 g,84.8 mmol)分散至二甲基甲醛(200 ml),添加碘化銅(1.6 g,8.5 mmol),加熱攪拌12小時。於反應終止後,將溫度降至常溫,利用氯仿萃取過濾所得的固體,之後進行濃縮而製備中間物。於將上述中間物完全溶解至四氫呋喃(100 ml)中後,放入肼水溶液(10 ml),加熱攪拌1小時。於反應終止後,將溫度降至常溫,將過濾所得的濾液添加至水(250 mL)而生成沈澱。過濾上述沈澱而製備以上述化學式10表示的化合物(7.2 g,產率49%)。MS[M+H]+
=347 [化學式10]
<合成例2> 如下所述般製備以化學式11表示的二胺化合物(化合物11)。化合物A 化合物C 化合物11
於將上述化合物A(30.0 g,63.6 mmol)與化合物C(30.7 g,127.2 mmol)完全溶解至四氫呋喃(300 ml)後,添加1.5 M的碳酸鉀水溶液(150 ml),放入四-三苯基-膦鈀(1.24 g,1.08 mmol),之後加熱攪拌4小時。於反應終止後,將溫度降至常溫,利用水(300 mL)與乙醇(300 mL)清洗過濾所得的固體而製備以上述化學式11表示的化合物(20.0 g,產率91%)。MS[M+H]+
=347 [化學式11]
<合成例3> 如下所述般製備以化學式12表示的二胺化合物(化合物12)。化合物D 化合物E 化合物12
於將上述化合物D(30.0 g,47.2 mmol)與化合物E(16.3 g,94.4 mmol)完全溶解至四氫呋喃(250 ml)後,添加1.5 M的碳酸鉀水溶液(100 ml),放入四-三苯基-膦鈀(1.0 g,0.87 mmol),之後加熱攪拌4小時。於反應終止後,將溫度降至常溫,利用水(200 mL)與乙醇(200 mL)清洗過濾所得的固體而製備以上述化學式12表示的化合物(30.3 g,產率97%)。MS[M+H]+
=663 [化學式12]
<實施例1> 於乾燥包括聚合1 mol的BPDA(3,3',4,4'-聯苯四羧酸二酐)、0.5 mol的2,2'-雙(三氟甲基)-[1,1'-聯苯]-4,4'-二胺(2,2'-bis(trifluoromethyl)-[1,1'-biphenyl]-4,4'-diamine,TFDB)與0.5 mol的於上述合成例1中製備的以化學式10表示的二胺而製備的聚醯胺酸類樹脂20重量%與作為溶劑的DMAc(二甲基乙醯胺)80重量%的組成物後,以厚度成為10 μm的方式塗佈至作為載體基板的無鹼玻璃的一面,對所製備出的塗膜連續地實施100℃溫度下的乾燥製程及於300℃下進行60分鐘的硬化製程,而形成可撓式基板的聚合物層形成用聚醯亞胺膜。
<實施例2> 於乾燥包括聚合1 mol的BPDA與0.99 mol的於上述合成例2中製備的以化學式11表示的二胺而製備的聚醯胺酸類樹脂20重量%與作為溶劑的DMAc80重量%的組成物後,以厚度成為10 μm的方式塗佈至作為載體基板的無鹼玻璃的一面,對所製備出的塗膜連續地實施100℃溫度下的乾燥製程及於300℃下進行60分鐘的硬化製程,而形成可撓式基板的聚合物層形成用聚醯亞胺膜。
<實施例3> 於乾燥包括聚合1 mol的BPDA、0.5 mol的TFDB與0.5 mol的於上述合成例3中製備的以化學式12表示的二胺而製備的聚醯胺酸類樹脂20重量%與作為溶劑的DMAc80重量%的組成物後,以厚度成為10 μm的方式塗佈至作為載體基板的無鹼玻璃的一面,對所製備出的塗膜連續地實施100℃溫度下的乾燥製程及於300℃下進行60分鐘的硬化製程,而形成可撓式基板的聚合物層形成用聚醯亞胺膜。
<比較例1> 於乾燥包括聚合1 mol的BPDA與0.99 mol的TFDB而製備的聚醯胺酸類樹脂20重量%與作為溶劑的DMAc80重量%的組成物後,以厚度成為10 μm的方式塗佈至作為載體基板的無鹼玻璃的一面,對所製備出的塗膜連續地實施100℃溫度下的乾燥製程及於300℃下進行60分鐘的硬化製程,而形成包括聚醯亞胺類樹脂的可撓式基板的聚合物層形成用聚醯亞胺膜。
<比較例2> 使用以下述化學式表示的二胺(螺二芴(Spirobifluorene,SBF)),除此之外,藉由與實施例1相同的方法製備可撓式基板的聚合物層形成用聚醯亞胺膜。
藉由下述方法對在實施例1至實施例3、比較例1及比較例2中製備的膜的熱膨脹係數(CTE)、玻璃轉移溫度(Tg)及厚度方向的相位差(Rth)進行評估,將其結果示於表1。
1)熱膨脹係數(CTE)及玻璃轉移溫度(Tg) 於如下步驟中利用熱機械分析儀(Thermo Mechanical Analyzer,TMA)(TA公司的Q400)測定100℃至250℃區間的熱膨脹值:設定為於以測定長度成為16 mm的方式,將厚度為10 μm、寬度為5 mm、長度為5 cm的樣品夾持至夾具後,以0.02 N的力拉伸,將升溫速度設為5℃/分而上升至300℃(1次升溫),之後將其冷卻至50℃(1次冷卻),再次升溫至450℃(2次升溫)。此時,將於1次升溫製程中在升溫區間內表現出的反曲點設為Tg。
2)相位差(Rth) 利用Axoscan測定厚度為10 μm、寬度為5 cm、長度為5 cm的膜的厚度方向的相位差(Rth)。
[表1]
根據上述表1的結果可知,本案發明的聚醯亞胺膜的CTE值低於比較例1及比較例2的聚醯亞胺,且表現出較高的玻璃轉移溫度。特別是,實施例2的CTE值雖與比較例1相似,但具有更高的玻璃轉移溫度。根據本發明,於分子結構中包括兩個苯基連接固定而成的螺環基或酚酞基,藉此即便溫度上升,亦可限制苯基的移動,從而可進一步提高對熱的尺寸穩定性。再者,與比較例2對照可知,本發明的結構具呈線性(linear)結構,故而與現有的酚酞單體相比,可將CTE的增加最小化而謀求Tg的上升。
以上,詳細地對本發明的內容中的特定部分進行了記述,於業界具有常識者應瞭解,此種具體的記述僅為較佳的實施方式,本發明的範圍並不限制於此。因此,本發明的實質性的範圍由隨附的發明申請專利範圍與其等效物定義。
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Claims (8)
- 一種聚醯亞胺,其由包括四羧酸二酐及選自化學式1a至化學式1e中的一種以上的二胺的聚合成分製備: [化學式1a][化學式1b][化學式1c][化學式1d][化學式1e]在化學式1b至化學式1e中, R1 、R2 分別獨立地為氫原子或選自鹵素原子、羥基(-OH)、硫醇基(-SH)、硝基(-NO2 )、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基的取代基。
- 如申請專利範圍第1項所述的聚醯亞胺,其中相對於二胺的總含量,所述聚合成分包括30莫耳%至100莫耳%的選自化學式1a至化學式1e的二胺。
- 如申請專利範圍第1項所述的聚醯亞胺,其熱膨脹係數為50 ppm/℃以下。
- 如申請專利範圍第1項所述的聚醯亞胺,其玻璃轉移溫度為330℃以上。
- 如申請專利範圍第1項所述的聚醯亞胺,其中所述聚合成分更包括以化學式6表示的二胺: [化學式6]在化學式6中, R31 及R32 分別獨立地選自氫原子、鹵素原子、羥基(-OH)、硫醇基(-SH)、硝基(-NO2 )、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基, n及m分別獨立地為0至4的整數, Q1 為選自由單鍵、-O-、-CR18 R19 -、-C(=O)-、-C(=O)O-、-C(=O)NH-、-S-、-SO2 -、伸苯基及其組合所組成的族群中的一者,其中R18 及R19 分別獨立地為選自由氫原子、碳數為1至10的烷基及碳數為1至10的氟烷基所組成的族群中的一者。
- 一種用於可撓式元件的聚醯亞胺膜,其包括如申請專利範圍第1項至第5項中任一項所述的聚醯亞胺。
- 一種聚醯亞胺基板,用於氧化物薄膜電晶體(oxide TFT)或低溫多晶矽(LTPS),其包括如申請專利範圍第1項至第5項中任一項所述的聚醯亞胺。
- 一種二胺,其由選自化學式1a至化學式1e中的任一者表示: [化學式1a][化學式1b][化學式1c][化學式1d][化學式1e]在化學式1b至化學式1e中, R1 、R2 分別獨立地為選自氫原子、鹵素原子、羥基(-OH)、硫醇基(-SH)、硝基(-NO2 )、氰基、碳數為1至10的烷基、碳數為1至4的鹵代烷氧基、碳數為1至10的鹵代烷基及碳數為6至20的芳基中的取代基。
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