TW201600499A - 用於製備石墨烯奈米帶的鄰三聯苯 - Google Patents
用於製備石墨烯奈米帶的鄰三聯苯 Download PDFInfo
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- TW201600499A TW201600499A TW104114381A TW104114381A TW201600499A TW 201600499 A TW201600499 A TW 201600499A TW 104114381 A TW104114381 A TW 104114381A TW 104114381 A TW104114381 A TW 104114381A TW 201600499 A TW201600499 A TW 201600499A
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Abstract
本發明係關於通式(I)之鄰三聯苯;
□其中R1、R2、R3及R4獨立地選自由以下組成之群:H;CN;NO2;及飽和、不飽和或芳族C1-C40烴殘基,其可經F、Cl、OH、NH2、CN及/或NO2 1倍至5倍取代,且其中一或多個-CH2-基團可經-O-、-NH-、-S-、-C(=O)O-、-OC(=O)-及/或-C(=O)-置換;及X與Y相同或不同,且選自由以下組成之群:F、Cl、Br、I及三氟甲烷磺酸酯(trifluoromethanesulfonate;OTf);
及其用於製備石墨烯奈米帶之用途以及一種自該等鄰三聯苯製備石墨烯奈米帶之方法。
Description
本發明係關於鄰三聯苯及其用於製備石墨烯奈米帶之用途以及一種自該等鄰三聯苯製備石墨烯奈米帶之方法。
石墨烯由二維碳層組成且擁有多個突出的特性。其不僅比鑽石更硬,極其耐撕裂且不透氣,但其亦為極佳的電及熱導體。由於此等突出的特性,石墨烯在物理學、材料科學及化學中已接收到相當大的關注。基於石墨烯之電晶體被視為目前使用的矽組分之潛在後繼者。然而,因為石墨烯為半金屬,其與矽相比缺乏電子帶隙且因此不具有對電子應用為至關重要之開關能力。
石墨烯奈米帶(通常縮寫為GNR)為來源於石墨烯晶格之具有超薄寬度之石墨烯帶。其為基於新穎石墨烯之電子裝置之有前景的構建塊。除導電鋸齒形邊緣(ZGNR)與主要半導體扶手椅邊緣石墨烯奈米帶(AGNR)之間的最重要區別以外,GNR幾何形狀之更一般的變化允許經由一維(ID)量子限制進行間隙調諧。一般而言,帶寬度增加導致帶隙整體減小,其中AGNR之疊加振盪特徵最大化。
製備GNR之標準『自上而下』方法,諸如石墨烯晶格之光
刻圖案化及碳奈米管之解鏈(例如描述於US 2010/0047154及US 2011/0097258中),僅產生不同GNR之混合物。另外,寬度低於10nm之奈米帶之比例相當低或甚至為零。然而,對於高效率電子裝置,石墨烯奈米帶之寬度需要受到精確控制且較佳低於10nm,且其邊緣需要為光滑的,因為即使微小偏離於理想邊緣形狀嚴重降低電子特性。
由於此類『自上而下』方法之固有限制,實現結構上定義明
確的GNR仍為難以捉摸的。經由溶液介導之脫氫環化反應(例如J.Wu,L.Gherghel,D.Watson,J.Li,Z.Wang,C.D.Simpson,U.Kolb,K.Mullen,Macromolecules 2003,36,7082-7089;L.Dossel,L.Gherghel,X.Feng,K.Mullen,Angew.Chem.Int.Ed.2011,50,2540-2543;Y.Fogel,L.Zhi,A.Rouhanipour,D.Andrienko,H.J.Rader,K.Mullen,Macromolecules 2009,42,6878-6884;及A.Narita等人,Nature Chemistry 2014,6,126-132)及表面輔助脫氫環化反應(例如J.Cai等人,Nature 2010,470-473;S.Blankenburg等人,ACS Nano 2012,6,2020;S.Linden等人,Phys.Rev.Lett.2012,108,216801)之『自下而上』化學合成方法最近已顯現為用於合成GNR之有前景的途徑。
與『自上而下』方法相比,基於溶液介導或表面輔助之脫氫
環化反應之『自下而上』化學合成方法提供機會藉由使特製三維聚伸苯基前驅體反應來製成定義明確且均勻的GNR。此等基於聚伸苯基之聚合前驅體由可在現代合成化學能力內定製結構之小分子構成。
然而,所有此等『自下而上』方法迄今為止僅允許製備微量
的石墨烯奈米帶。此外,所得石墨烯奈米帶經常由於其主鏈中之統計學上配置之「扭結」而定義不清楚,或僅具有低分子量。
因此,本發明之一目標為提供製備石墨烯奈米帶之新穎方
法。本發明之又一目標為提供用於製備石墨烯奈米帶之適合的寡聚伸苯基單體及適合的聚合前驅體。
藉由通式(I)之鄰三聯苯解決該問題;
其中R1、R2、R3及R4獨立地選自由以下組成之群:H;CN;NO2;及飽和、不飽和或芳族C1-C40烴殘基,其可經F、Cl、OH、NH2、CN及/或NO2 1倍至5倍取代,且其中一或多個-CH2-基團可經-O-、-NH-、-S-、-C(=O)O-、-OC(=O)-及/或-C(=O)-置換;及X與Y相同或不同,且選自由以下組成之群:F、Cl、Br、I、三氟甲烷磺酸酯(trifluoromethanesulfonate;OTf)。
較佳地,R1、R2、R3及R4獨立地選自由以下組成之群:H、未經取代之C1-C40烷基殘基及未經取代之C1-C40烷氧基殘基。
更佳地,R1及R2獨立地選自由以下組成之群:H、未經取代之C1-C20烷基殘基及未經取代之C1-C20烷氧基殘基;且R3及R4為H。
在本申請案之一個具體實例中,R1及R2為H。
在本發明之上下文中,表述「C1-C40烴殘基」包括所有種類
之由碳原子及氫原子組成之殘基。實例為直鏈或分支鏈C1-C40烷基、直鏈或分支鏈C2-C40烯基、直鏈或分支鏈C2-C40炔基及C6-C40芳基。
當可能時,C1-C40烷基殘基可為直鏈或分支鏈的。實例為甲
基、乙基、正丙基、異丙基、正丁基、第二丁基、異丁基、第三丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、1,1,3,3-四甲基戊基、正己基、1-甲基己基、1,1,3,3,5,5-六甲基己基、正庚基、異庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、1,1,3,3-四甲基丁基及2-乙基己基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、十九烷基、二十烷基、二十一烷基、二十二烷基、二十三烷基、二十四烷基、二十五烷基、二十六烷基、二十七烷基、二十八烷基、二十九烷基、三十烷基、三十一烷基、三十二烷基、三十三烷基、三十四烷基、三十五烷基、三十六烷基、三十七烷基、三十八烷基、三十九烷基及四十烷基。
C2-C40烯基殘基為直鏈或分支鏈烯基殘基,例如乙烯基、烯
丙基、甲代烯丙基、異丙烯基、2-丁烯基、3-丁烯基、異丁烯基、正戊-2,4-二烯基、3-甲基-丁-2-烯基、正辛-2-烯基、正十二-2-烯基、異十二烯基、正十二-2-烯基及正十八-4-烯基。
C2-40炔基殘基為直鏈或分支鏈的。實例為乙炔基、1-丙炔-3-
基、1-丁炔-4-基、1-戊炔-5-基、2-甲基-3-丁炔-2-基、1,4-戊二炔-3-基、1,3-戊二炔-5-基、1-己炔-6-基、順-3-甲基-2-戊烯-4-炔-1-基、反-3-甲基-2-戊烯-4-
炔-1-基、1,3-己二炔-5-基、1-辛炔-8-基、1-壬炔-9-基、1-癸炔-10-基及1-二十四炔-24-基。
C6-C40芳基殘基之實例為苯基、萘基、聯苯基、三聯苯基、芘基、茀基、菲基、蒽基、并四苯基、并五苯基或并六苯基。
C1-C40烷氧基為直鏈或分支鏈烷氧基,例如甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、第二丁氧基、第三丁氧基、戊氧基、異戊氧基、第三戊氧基、庚氧基、辛氧基、異辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基、十八烷氧基、十九烷氧基、二十烷氧基、二十一烷氧基、二十二烷氧基、二十三烷氧基、二十四烷氧基、二十五烷氧基、二十六烷氧基、二十七烷氧基、二十八烷氧基、二十九烷氧基、三十烷氧基、三十一烷氧基、三十二烷氧基、三十三烷氧基、三十四烷氧基、三十五烷氧基、三十六烷氧基、三十七烷氧基、三十八烷氧基、三十九烷氧基及四十烷氧基。
本發明之問題進一步藉由使用通式(I)之鄰三聯苯用於製備石墨烯奈米帶來解決。
因此,本發明之另一態樣為一種製備石墨烯奈米帶之方法,其包含以下步驟
(a)使通式(I)之鄰三聯苯聚合以形成具有通式(II)重複單元之聚合前驅體,
其中R1、R2、R3及R4如上文所定義;及(b)使該聚合前驅體脫氫環化以形成具有通式(III)重複單元之石墨烯奈米帶,
其中R1、R2、R3及R4如上文所定義。
在本發明之一較佳具體實例中,在溶液中執行(a)聚合。
舉例而言,具有通式(II)重複單元之聚合前驅體可藉由在二甲基甲醯胺(dimethylformamide;DMF)中或在甲苯與DMF之混合物中之山本聚縮合(Yamamoto-polycondensation)獲得(T.Yamamoto,Progr.Polym.Sci.1992,17,1153-1205;T.Yamamoto,Bull.Chem.Soc.Jpn.1999,72,621-638;T.Yamamoto,T.Kohara,A.Yamamoto,Bull.Chem.Soc.Jpn.1981,54,1720-1726。)。用於山本聚縮合之適合催化劑可自雙(環辛二烯)鎳(0)、1,5-環辛二烯及2,2'-聯吡啶之化學計算量混合物例如在甲苯與DMF之混合物中製備。取決於特定取代基R1及R2,聚縮合反應在50℃至110℃溫度下、較佳在70℃至90℃溫度下進行。藉由小心地將反應混合物滴入稀甲醇鹽酸中實現山本聚縮合反應之中止及鎳殘基之分解。通常,形成白色沈澱,其可藉由過濾來收集。其他適合的聚縮合反應依賴於例如厄爾曼型(Ullmann-type)偶合及格拉澤型(Glaser-type)偶合。藉由適合的共單體,鄰三聯苯亦可應用於例如鈴木-宮浦型(Suzuki-Miyaura-type)偶合、根岸型(Negishi-type)偶合、施蒂勒型(Stille-type)偶合及熊田型(Kumada-type)偶合。
在本發明之一個具體實例中,在溶液中執行(b)脫氫環化。
舉例而言,具有通式(III)重複單元之石墨烯奈米帶之製備可使用路易斯酸(Lewis acid),如氯化鐵(FeCl3)、氯化鉬(MoCl5)或三氟甲磺酸銅(Cu(OTf)2)在二氯甲烷與硝基甲烷之混合物中執行。替代地,石墨烯奈米帶之製備可使用苯基碘(III)雙(三氟乙酸鹽)(PIFA)及BF3醚合物在無水二氯甲烷中進行。已知當PIFA經路易斯酸活化時,其容易與寬範圍之基質反應,以極佳產率得到聯芳基產物(Takada,T.;Arisawa,M.;Gyoten,M.;Hamada,R.;Tohma,H.;Kita,Y.J.Org.Chem.1998,63,7698-7706)。此外,其可應用於三伸苯基
(King,B.T.;Kroulik,J.;Robertson,C.R.;Rempala,P.;Hilton,C.L.;Korinek,J.D.;Gortari,L.M.J.Org.Chem.2007,72,2279-2288.)及六迫六苯并蒄(HBC)衍生物(Rempala,P.;Kroulik,J.;King,B.T.J.Org.Chem.2006,71,5067-5081.)之合成。重要的是,藉由此程序排除了在施加氯化鐵時經常觀測到的不希望的氯化。此類類型之脫氫環化反應之適合變化可在文章「石墨烯型分子之合成中之脫氫環化」(M.Kivala,D.Wu,X.Feng,C.Li,K.Mullen,Materials Science and Technology 2013,373-420)及其中所引用之文獻中找到。
一般而言,藉由在溶液中執行脫氫環化獲得之石墨烯奈米帶
之分子量在1,000g/mol至1,000,000g/mol、較佳20,000g/mol至200,000g/mol範圍內變化。
在本發明之另一較佳具體實例中,在惰性表面上執行(a)
聚合及(b)脫氫環化。因此,藉由在高真空條件下在此表面上直接生長來製備具有通式(III)重複單元之石墨烯奈米帶。藉此,首先使通式(I)之鄰三聯苯在高溫下聚合以形成具有通式(II)重複單元之聚合前驅體,其接著在進一步高溫下反應形成具有通式(III)重複單元之石墨烯奈米帶。
使用超高真空(UHV)條件之表面輔助自下而上方法已描述
於J.Cai等人,Nature 466,第470-473頁(2010)中及此後的少數公開案(S.Blankenburg等人,ACS Nano 2012,6,2020;S.Linden等人,Phys.Rev.Lett.2012,108,216801)中。替代地,可使用WO 2014/045148 A1中所揭示之表面輔助自下而上方法。此方法具有不需要施加超高真空之優點。
在本發明之上下文中,表述「惰性表面」包括使通式(I)
之鄰三聯苯及/或具有通式(II)重複單元之聚合前驅體吸附/沈積,且隨後
聚合及/或脫氫環化而不與該等化合物自身不可逆地反應之所有種類的固體基質之表面。「惰性表面」可較佳地充當聚合及/或脫氫環化反應之催化劑。
惰性表面可為金屬表面,諸如Au、Ag、Cu、Al、W、Ni、Pt或Pd表面,較佳為Au及/或Ag表面。該表面亦可為金屬氧化物表面,諸如氧化矽、氮氧化矽、矽酸鉿、氮化矽酸鉿、矽酸鋯、二氧化鉿及二氧化鋯或氧化鋁、氧化銅、氧化鐵。該表面亦可由半導體材料,諸如矽、鍺、砷化鎵、碳化矽及二硫化鉬製成。該表面亦可為諸如氮化硼、氯化鈉或方解石之材料。
該表面可為導電、半導電或絕緣的。
在表面上之沈積可藉由真空沈積(昇華)方法、基於溶液之
方法(諸如旋塗、噴塗、浸塗、印刷、電噴霧沈積)或雷射誘導之解吸附或轉移方法進行。沈積方法亦可為直接表面至表面轉移。較佳地,藉由真空沈積方法進行沈積。較佳地,其為真空昇華方法。
取決於上文所描述之表面輔助方法,反應步驟(a)及(b)
中所施加之壓力通常低於10-5毫巴,經常低於10-5毫巴。
較佳地,藉由熱活化誘導步驟(a)中之聚合。然而,亦可
使用誘導聚合之任何其他能量輸入,諸如輻射。活化溫度取決於所用表面及通式(I)之鄰三聯苯之取代模式。通常,溫度在100℃至300℃範圍內。
視情況,步驟(a)可重複一次或數次然後在步驟(b)中進
行部分或完全脫氫環化。
如上文所指示,本發明之方法之步驟(b)包括至少部分、
較佳完全地脫氫環化具有通式(II)重複單元之聚合前驅體以形成具有通式(III)重複單元之石墨烯奈米帶。脫氫環化反應通常在200℃至500℃範圍
內之溫度下執行。
較佳地,表面輔助方法在方法步驟(a)與(b)之間不包含
任何中間步驟。步驟(a)及(b)可直接彼此跟隨及/或重疊。
一般而言,藉由在表面上直接生長獲得之具有通式(III)重
複單元之石墨烯奈米帶之分子量在2,000g/mol至1,000,000g/mol、較佳4,000g/mol至100,000g/mol範圍內變化。
可藉由掃描穿隧顯微鏡(STM)技術有效研究共價黏結之二
維分子陣列。表面受限共價鍵形成之實例涉及厄爾曼偶合、亞胺化、卟啉之交聯及雜環碳烯與多元胺之寡聚。用於在表面上直接生長石墨烯奈米帶及石墨烯網狀物之化學驅動協定就在最近已由Müllen(MPI-P Mainz,Germany)及Fasel(EMPA Dübendorf,Switzerland)之組建立(Bieri,M.;Treier,M.;Cai,J.;Aït-Mansour,K.;Ruffieux,P.;Gröning,O.,Gröning,P.;Kastler,M.;Rieger,R.;Feng,X.;Müllen,K.;Fasel,R.;Chem.Commun.2009,45,6919;Bieri,M.;Nguyen,M.T.;Gröning,O.;Cai,J.;Treier,M.;Aït-Mansour,K.;Ruffieux,P.;Pignedoli,C.A.;Passerone,D.;Kastler,M.;Müllen,K.;Fasel,R.;J.Am.Chem.Soc.2010,132,16669;Treier,M.;Pignedoli,C.A.;Laino,T.;Rieger,R.;Müllen,K.;Passerone,D.;Fasel,R.Nature Chemistry 2011,3,61;Cai,J.;Ruffieux,P.;Jaafar,R.;Bieri,M.;Braun,T.;Blankenburg,S.;Muoth,M.;Seitsonen,A.P.;Saleh,M.;Feng,X.;Müllen,K.;Fasel,R.Nature 2010,466,470-473。)。在不受理論束縛的情況下,可自此等研究推斷金屬表面上之奈米帶形成經由自由基路徑進行。在經由超高真空(UHV)昇華(10-11毫巴至10-5毫巴,較佳10-10毫巴至10-7毫巴)將官能化單體沈積在表面上之後,脫鹵被認為發生在藉由退火至
100℃至200℃之熱活化之後。此產生擴散在表面上且彼此偶合之雙自由基物質,導致碳-碳鍵形成。此等自由基加成反應在中間熱水準(100℃至300℃,較佳150℃至220℃)下進行且為隨後在更高溫度(200℃至500℃,較佳380℃至420℃)下之脫氫環化之前提條件。僅當在第一階段期間形成足夠分子量之聚合物質時,隨後才將進行分子之完全石墨化,其中避免了材料自表面之熱解吸附。
對於UHV表面輔助聚合及脫氫環化,需要剛性及平面度足
夠高之官能單體,該等官能單體輔助金屬基質上之平面定向。此外,該方法允許石墨烯奈米帶之拓撲定製,因為其形狀藉由前驅體單體之官能性圖案及幾何形狀確定。單體設計中不需要溶解烷基鏈,因為此表面受限協定中不涉及基於溶劑之方法。
本申請案之又一態樣為一種用於製備石墨烯奈米帶之聚合
前驅體,其具有通式(II)重複單元,
其中R1、R2、R3及R4如上文所定義。
本申請案之另一態樣為具有通式(III)重複單元之石墨烯奈
米帶,
其中R1、R2、R3及R4如上文所定義。
通式(I)之鄰三聯苯可根據以下所示之流程1至3合成。
所用之反應條件及溶劑純粹為說明性的;當然其他條件及溶劑亦可使用且可易於由熟習此項技術者確定。作為合成通式(I)之鄰三聯苯之起始材料,使用市售2,5-二鹵苯胺1(流程1)。在反應順序之第一步驟中,使2,5-二鹵苯胺1與水合氯醛2及鹽酸羥胺在鹼性條件下反應以形成(2,5-二鹵苯基)-2-(羥亞胺基)乙醯胺3。
接著,使(2,5-二鹵苯基)-2-(羥亞胺基)乙醯胺3在高溫下經受
硫酸以產生4,7-二鹵吲哚啉-2,3-二酮4。
流程1
向4,7-二鹵吲哚啉-2,3-二酮4及氫氧化鈉於水中之溶液中添
加過氧化氫水溶液,且將反應混合物加熱至50℃(流程2)。在冷卻及酸處理之後,獲得2-胺基-3,6-二鹵苯甲酸5,隨後使其與碘及亞硝酸異戊酯反應以產生1,4-二溴-2,3-二碘苯6。
接著,使1,4-二溴-2,3-二碘苯6經受兩次連續鈴木偶合反應
(流程3)。1,4-二溴-2,3-二碘苯6與硼酸9之第一鈴木偶合反應可例如在催化量之肆(三苯基膦)鈀(0)(Pd(PPh3)4)及鹼(如碳酸鈉)存在下在二噁烷中在高溫下執行。由此獲得之單偶合聯苯(IV)可經受第二鈴木反應。通式(I)之鄰三聯苯可例如藉由將單偶合聯苯(IV)、芳基硼酸10、鈀(0)催化劑及鹼之反應混合物在二噁烷中加熱至100℃後維持幾天來合成。在純化之後,可使通式(I)之鄰三聯苯經受聚合。
流程3
利用本文所揭示之石墨烯奈米帶之各種製品,包括電子裝
置、光學裝置及光電裝置,諸如場效電晶體(例如薄膜電晶體)、光伏打裝置、有機發光二極體(OLED)、互補金屬氧化物半導體(CMOS)、互補反相器、D正反器、整流器及環形振盪器,亦在本發明之範圍內,同樣為製造該等製品的方法。
因此,本發明之另一態樣為具有如上文所定義之通式(III)
重複單元之石墨烯奈米帶在電子、光學或光電裝置中之用途。較佳地,裝置為有機場效電晶體裝置、有機光伏打裝置或有機發光二極體。
因此,本發明進一步提供製備展現定義明確的電子帶隙之半
導體材料之方法,該電子帶隙可藉由選擇分子前驅體而為特定應用進行定製。該等方法可包括:製備包括本文所揭示之溶解或分散於液體介質(諸如溶劑或溶劑混合物)中的本發明化合物中之一或多者的組成物;將該組成物沈積在基板上以提供半導體材料前驅體;及處理(例如加熱)該半導體前驅體以提供包括本文所揭示之化合物中之一或多者的半導體材料(例如薄膜半導體)。在各種具體實例中,液體介質可為有機溶劑、無機溶劑(諸如水)或其組合。在一些具體實例中,組成物可進一步包括一或多種獨立地選自以下之添加劑:清潔劑、分散劑、黏合劑、相容劑、固化劑、引發劑、保濕劑、消泡劑、潤濕劑、pH調節劑、殺生物劑及抑菌劑。舉例而言,
可包括界面活性劑及/或聚合物(例如聚苯乙烯、聚乙烯、聚-α-甲基苯乙烯、聚異丁烯、聚丙烯、聚甲基丙烯酸甲酯及其類似物)作為分散劑、黏合劑、相容劑及/或消泡劑。在一些具體實例中,可藉由印刷,包括噴墨印刷及各種接觸印刷技術(例如網版印刷、凹版印刷、平版印刷、移印、石印印刷、彈性凸版印刷及微接觸印刷)進行沈積步驟。在其他具體實例中,可藉由旋塗、滴落澆鑄、區域澆鑄、浸塗、刮塗、噴塗或真空過濾進行沈積步驟。
本發明進一步提供諸如本文所描述之各種裝置之製品,其包
括具有本發明之半導體材料之複合材料及基板組件及/或介電組件。基板組件可選自摻雜矽、氧化銦錫(ITO)、ITO塗佈之玻璃、ITO塗佈之聚醯亞胺或其他塑膠、鋁或單獨或塗佈在聚合物或其他基板上之其他金屬、摻雜聚噻吩及其類似物。介電組件可由以下製備:無機介電材料,諸如各種氧化物(例如SiO2、Al2O3、HfO2);有機介電材料,諸如各種聚合材料(例如聚碳酸酯、聚酯、聚苯乙烯、聚鹵乙烯、聚丙烯酸酯);及自組裝超晶格/自組裝奈米介電(SAS/SAND)材料(例如描述於Yoon,M-H.等人,PNAS,102(13):4678-4682(2005)中);以及混合有機/無機介電材料(例如描述於US 2007/0181961 A1中)。複合材料亦可包括一或多個電觸點。用於源電極、汲電極及閘電極之適合材料包括金屬(例如Au、Al、Ni、Cu)、透明導電氧化物(例如ITO、IZO、ZITO、GZO、GIO、GITO)及導電聚合物(例如聚(3,4-伸乙二氧基噻吩)聚(苯乙烯磺酸鹽)(PEDOT:PSS)、聚苯胺(PANI)、聚吡咯(PPy))。本文所描述之複合材料中之一或多者可體現在各種有機電子、光學及光電裝置內,諸如有機薄膜電晶體(OTFT),具體言之,有機場效電晶體(OFET),以及感測器、電容器、單極電路、互補電路(例如反相器電
路)及其類似裝置。
因此,本發明之又一態樣為一種包含薄膜半導體之電子、光
學或光電裝置,薄膜半導體包含具有如上文所定義之通式(III)重複單元之石墨烯奈米帶。較佳地,裝置為有機場效電晶體裝置、有機光伏打裝置或有機發光二極體。
其中本發明之石墨烯奈米帶為有用之其他製品為光伏打裝
置或太陽能電池。本發明化合物可展現寬的光吸收及/或極正向偏移之還原電位,使其為此類應用所需。因此,本文所描述之化合物可在光伏打設計中用作n型半導體,該光伏打設計包括形成p-n接面之相鄰p型半導體材料。化合物可呈薄膜半導體形式,其可沈積在基板上以形成複合材料。在此類裝置中採用本發明化合物在熟習此項技術者之知識範圍內。
因此,本發明之另一態樣係關於製造併入有本發明之半導體
材料之有機場效電晶體之方法。本發明之半導體材料可用於製造包括以下之各種類型之有機場效電晶體:頂閘頂部接觸電容器結構、頂閘底部接觸電容器結構、底閘頂部接觸電容器結構及底閘底部接觸電容器結構。
在某些具體實例中,可使用SiO2作為介電質,以頂部接觸
幾何形狀用本發明石墨烯奈米帶在摻雜矽基板上製造OTFT裝置。在特定具體實例中,可在室溫下或在高溫下沈積併入有至少一種本發明化合物之主動半導體層。在其他具體實例中,可藉由如本文所描述之旋塗或印刷來施加併入有至少一種本發明化合物之主動半導體層。對於頂部接觸裝置,可使用遮蔽罩、電子束光刻及剝離技術或在熟習此項技術者之知識範圍內之其他適合的建構方法將金屬觸點在膜頂部上圖案化。
圖1至圖7展示:圖1:3',6'-二溴-1,1':2',1"-三聯苯8(鄰三聯苯(I),其中R1=R2=R3=R4=H,且X=Y=Br)之合成途徑。
圖2:1,4-二溴-2,3-二碘苯6之1H NMR(300MHz,CD2Cl2)。
圖3:1,4-二溴-2,3-二碘苯6之13C NMR(75MHz,CD2Cl2)。
圖4:3',6'-二溴-1,1':2',1"-三聯苯8之1H NMR(300MHz,CD2Cl2)。
圖5:3',6'-二溴-1,1':2',1"-三聯苯8之13C NMR(75MHz,CD2Cl2)。
圖6:在Au表面上聚合及脫氫環化之後自3',6'-二溴-1,1':2',1"-三聯苯8獲得之9-AGNR之STM影像。
圖7:展示STM影像與AGNR結構之化學模型疊加之放大。
藉由以下實施例更詳細地說明本發明。
實施例
實施例1 (2,5-二鹵苯基)-2-(羥亞胺基)乙醯胺3之製備
如S.-J.Garden,J.-C.Torres,A.-A.Ferreira,R.-B.Silva,A.-C.Pinto,Tetrahedron Lett.1997,38,1501中所描述合成(2,5-二鹵苯基)-2-(羥亞胺基)乙醯胺3。因此,在1L圓底燒瓶中置放10g(39.85mmol)2,5-二鹵苯胺1、7.91g(47.82mmol)水合氯醛、4.15g(59.78mmol)鹽酸羥胺及48g硫
酸鈉。添加300mL乙醇及300mL水且將反應混合物在80℃下攪拌12h。在冷卻至室溫之後,將沈澱物過濾,用乙酸乙酯與己烷(1:10)之混合物洗滌且在真空下乾燥,獲得72%產率之呈白色固體狀之(2,5-二鹵苯基)-2-(羥亞胺基)乙醯胺3。
1H-NMR:(300MHz,DMSO):δ=12.54(s,1H),9.51(s,1H),8.15(d,1H),7.6(m,2H),7.34(dd,1H)ppm。
13C-NMR:(300MHz,DMSO):δ=160.45,143.10,136.73,134.18,129.15,126.50,120.58,114.96ppm。
實施例2 4,7-二鹵吲哚啉-2,3-二酮4之製備
如S.-J.Garden等人,Tetrahedron Lett.1997,38,1501中所描述,將濃硫酸(45mL)在250mL圓底燒瓶中加熱至50℃。添加經乾燥之(2,5-二鹵苯基)-2-(羥亞胺基)乙醯胺3(5g,15.6mmol)且將反應混合物加熱至100℃後維持30min。將所得紫色混合物冷卻至室溫且傾入冰水(300mL)中以沈澱呈淺橙色固體狀之4,7-二鹵吲哚啉-2,3-二酮4。將沈澱物過濾且在真空中乾燥,獲得呈56%產率之4。
1H-NMR:(300MHz,DMSO):δ=11.43(s,1H),7.66(d,1H),7.17(d,1H)ppm。
13C-NMR:(300MHz,DMSO):δ=181.08,158.94,151.06,
140.64,127.86,118.36,103.68ppm。
實施例3 2-胺基-3,6-二鹵苯甲酸5之製備
根據出版物:V.Lisowski,M.Robba,S.Rault,J.Org.Chem.2000,65,4193中所描述之合成程序合成2-胺基-3,6-二鹵苯甲酸5。因此,將4,7-二鹵吲哚啉-2,3-二酮4(3g,10mmol)溶解於50mL 5%氫氧化鈉中且加熱至50℃。逐滴添加30%過氧化氫(50mL)且將所得混合物在50℃下攪拌額外30min。在冷卻至室溫之後,將溶液過濾且用1M鹽酸酸化至pH 4。將米色沈澱物過濾且在真空中乾燥,獲得呈65%產率之2-胺基-3,6-二鹵苯甲酸5。
1H-NMR:(300MHz,DMSO):δ=13.73(b s,1H),7.38(d,1H),6.79(d,1H),5.58(b s,1H)ppm。
13C-NMR:(300MHz,DMSO):δ=167.32,144.12,134.32,121.09,118.96,107.86ppm。
實施例4 1,4-二溴-2,3-二碘苯6之製備
根據文章:O.S.Miljanic,K.P.C.Vollhardt,G.D.Whitener Synlett
2003,29-34中公佈之程序合成1,4-二溴-2,3-二碘苯6。向碘(2.58g,10.17mmol)及亞硝酸異戊酯(1.64mL,12.21 mmol)於200mL 1,2-二氯乙烷中之攪拌及回流溶液中逐滴添加2-胺基-3,6-二鹵苯甲酸5於15mL二噁烷中之溶液。將所得混合物回流1h,冷卻至室溫,過濾且用5%硫代硫酸鈉水溶液洗滌濾液。有機相經硫酸鎂脫水且蒸發溶劑。藉由用己烷進行急驟管柱層析純化所得殘餘物,獲得60%產率之呈無色針狀物狀之1,4-二溴-2,3-二碘苯6。光譜資料與文獻值一致。
1H-NMR:(300MHz,CD2Cl2):δ=7.45(s,2H)ppm。
13C-NMR:(300MHz,CD2Cl2):δ=133.25,128.09,117.52ppm。
實施例5 3',6'-二溴-1,1':2',1"-三聯苯8之製備
將1,4-二溴-2,3-二碘苯6(250mg,0.5mmol)及苯硼酸(65.63mg,0.5mmol)溶解於10mL二噁烷中且添加1mL 2M碳酸鈉水溶液。使氬氣鼓泡通過溶液歷時45min,且接著添加肆(三苯基膦)鈀(0)(60mg,0.1mol%)。使氬氣鼓泡通過溶液歷時額外15min且將反應混合物在80℃下攪拌2天。在冷卻至室溫之後,用水/二氯甲烷萃取溶液,有機相經硫酸鎂脫水且蒸發溶劑。藉由管柱層析(PE:DCM 9:1)純化粗混合物,獲得呈60%產率之單偶合產物7。
將第二碘在類似鈴木偶合反應中與額外當量之苯硼酸偶
合。將溶液在100℃下在氬氣下攪拌3天。藉由管柱層析(PE:DCM 9:1)純化粗反應混合物,獲得呈10%產率之3',6'-二溴-1,1':2',1"-三聯苯8。可自乙醇再結晶無色固體。
1H-NMR:(300MHz,CD2Cl2):δ=7.49(s,2H),7.12-7.05(m,6H),6.93-6.90(m,4H)ppm。
13C-NMR:(300MHz,CD2Cl2):δ=144.24,140.56,133.14,130.23,127.85,127.45,123.63ppm。
FD-MS:m/z=388.0。
實施例6 石墨烯奈米帶之表面輔助製備
將Au(111)單晶(Surface Preparation Laboratory,Netherlands)用作用於生長N=9扶手椅石墨烯奈米帶(9-AGNR)之基板。首先藉由重複氬離子轟擊及退火至480℃之循環來清潔基板,且接著冷卻至室溫以便沈積。藉由以約1Å/min速率進行昇華將3',6'-1,1':2',1"-三聯苯8沈積至清潔表面上。接著將Au(111)基板在175℃下後退火10min以誘導聚合且在400℃下後退火10min以形成GNR。將來自Omicron Nanotechnology公司,Germany之低溫STM(LT-STM)用於特性化9-AGNR樣品之形態。模型與STM影像之間一致,證明可在Au(111)表面上自3',6'-二溴-1,1':2',1"-三聯苯8合成9-AGNR(圖6)。
Claims (15)
- 一種通式(I)之鄰三聯苯;
- 如申請專利範圍第1項之鄰三聯苯,其中R1、R2、R3及R4獨立地選自由以下組成之群:H;未經取代之C1-C40烷基殘基;及未經取代之C1-C40烷氧基殘基。
- 如申請專利範圍第1項之鄰三聯苯,其中R1及R2獨立地選自由以下組成之群:H、未經取代之C1-C20烷基殘基及未經取代之C1-C20烷氧基殘基;且R3及R4為H。
- 如申請專利範圍第1項之鄰三聯苯,其中R1、R2、R3及R4為H。
- 如申請專利範圍第1項之鄰三聯苯,其中X與Y相同。
- 如申請專利範圍第1項之鄰三聯苯,其中X及Y為Br。
- 一種如申請專利範圍第1項之鄰三聯苯之用途,其用於製備石墨烯奈米帶。
- 一種製備石墨烯奈米帶之方法,其包含以下步驟(a)使如申請專利範圍第1項之鄰三聯苯聚合以形成具有通式(II)重複單元之聚合前驅體,
- 如申請專利範圍第8項之方法,其中在溶液中執行該(a)聚合。
- 如申請專利範圍第8項之方法,其中在溶液中執行該(b)脫氫環化。
- 如申請專利範圍第8項之方法,其中在惰性表面上執行該(a)聚合及該(b)脫氫環化。
- 一種用於製備石墨烯奈米帶之聚合前驅體,其具有通式(II)重複單元,
- 一種石墨烯奈米帶,其具有通式(III)重複單元,
- 一種電子、光學或光電裝置,其包含含如申請專利範圍第13項之石墨烯奈米帶之薄膜半導體。
- 如申請專利範圍第14項之裝置,其中該裝置為有機場效電晶體裝置、有機光伏打裝置或有機發光二極體。
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