TW200917543A - Organic thin film transistor and organic thin film light-emitting transistor - Google Patents
Organic thin film transistor and organic thin film light-emitting transistor Download PDFInfo
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- TW200917543A TW200917543A TW097123235A TW97123235A TW200917543A TW 200917543 A TW200917543 A TW 200917543A TW 097123235 A TW097123235 A TW 097123235A TW 97123235 A TW97123235 A TW 97123235A TW 200917543 A TW200917543 A TW 200917543A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/47—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing ten carbon atoms
- C07C13/48—Completely or partially hydrogenated naphthalenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
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Description
200917543 九、發明說明: 【發明所屬之技術領域】 本發明係關於—種具有有機半導體層之有機薄膜電晶體 及有機薄膜發光電晶體,特別是關於包含具有較高之電子 場效遷移率之化合物且可高迷動作之有機薄媒電晶體,使 用其作為發光元件之有機薄膜發光電晶體及適合其之化合 物。 【先前技術】 薄膜電晶體(TFT)廣泛使用為液晶顯示裝置等之顯示用 開關元件。代表性TFT之截面結構如圖3所示。如該圖所 不,TFT於基板上順次具有閘極電極及絕緣體層,於絕緣 體層上具有空出特;^間隔而形成之源極電極及沒極電極。 於包含兩電極之一部分表面’於電極間露出之絕緣體層上 形成有半導體層。於如此構成之TFT中,+導體層形成通 道區域,可利用於閘極電極上施加之電壓而控制於源極電 極與沒極電極之間流動的電流,藉此進行開/關動作。 先則’ TFT係使用非晶態或多晶石夕而製作,但存在使用 如此之石夕的TFT之製作中使用的CVD裝置非常昂貴,使用 TFT,顯示裝置等之大型化隨之產生製造成本大幅度增加 之門題點又’成臈非晶態或多晶矽之製程於非常高之溫 度下進行’因此存在可使用4基板之材料的種類會受到限 制,從而不能使用輕量之樹脂基板等問題。
,為解決該問題,提出有使用有機物代替非晶態或多晶矽 的丁FT(以下有時略記為有機TFT)。作為以有機物形成TFT 132167.doc 200917543 時使用之成獏方法,已知有真空蒸鑛法或塗佈法等,藉由 其等成膜方法,可抑制製造成本上升且實現元件之^型 化’可使成臈時必需之製程溫度為較低之溫度。因此,以 有機TFT’存在選擇基板中使用之材料時限制較少的優 點.期待其實用化,正不斷廣泛地提出研究報止。 作為有機TFT中使用之有機物半導體,於p型中,共軛 系聚合物或噻吩等之多聚體、金屬酞菁化合物、稠五=等& 縮合芳香族烴^單質或者與其他化合物之混合物的狀態 使用。又,作為n型FET(場效應電晶體)之材料例如已知 有1,4,5,8-萘四曱酸二酐(NTCDA)、^^,仏四氰基 萘_2,6-喹啉二曱烷⑴ quinodimethane、TCNNqD)、M,5,8_ 萘四曱酸二醯亞胺 (NTCDI)或氟化狄菁。
一另一方面,作為同樣地使用電導的元件存在有機電激發 光(EL)元件,但有機EL元件通常於100 nma下之超薄膜的 膜厚方向上施加1G5 v/em以上的強電場強制性使電荷流 動,相對於此,於有機TFT之情形時,必需以i〇5 v/cm以 下之電%使電荷高速流過數μιη以上之距離,有機物自身 而要進而向之導電性。然而,先前之有機TFT中之上述化 合物的電子場效遷移率小,回應速度慢,於作為電晶體之 冋速回應性方面存在問題。又,開/關比亦較小。 其中所明之開7關比,係施加閘極電壓時(開路)於源極_ 汲極間流動之電流,除以不施加閘極電壓時(斷路)於源極_ 汲極間流動之電流的值;所謂接通電流,通常係使閘極電 132167.doc 200917543 壓增加’於源極-没極間流動 動之電流飽和時之電流值(飽和 電流)。 又,於專利文獻i或非專利文獻卜2中,揭示有藉由稀 煙結構與芳香族烴基或者料族雜環基之組合顯示出較高 遷移率(high mobility)之有機化合物,但其等存在回應速 度慢之缺點。 又,於非專利文獻3中,㈣有组合乙炔結構與苯環之4 聚體結構顯示出有機電晶體特性,但存在遷移率低之缺 點。 專利文獻1 : PCT國際申請公表w〇2〇〇6/1132〇5號公報 非專利文獻 1 : Hong Meng 等,Journal 〇f Amedcan
Chemical Society,第 128卷,第 9304 頁,2006 年 非專利文獻2 : Lay-Lay Chua等,Nature,第 434卷,第 194 頁,2005年 非專利文獻 3 : T.Oyamada等,japanese Journai 〇f Applied
Physics,第 45卷,第 L1331 頁,2006年 【發明内容】 發明所欲解決之問題 本發明係為解決上述課題而成者’其目的在於提供一種 回應速度(驅動速度)高速,且開/關比大之有機薄膜電晶 體,利用其之有機薄膜發光電晶體及適合其之有機化合 物。 解決問題之技術手段 本^明者專人’為達成上述目的而反覆銳意研究,纟士果 132167.doc 200917543 發現藉由於有機薄膜雷曰 寻膜電曰曰體之有機半導體層使用具有下述 通式(1)所表示之結構的有 有機化5物,可使回應速度(驅動 速度)阿速化,從而完成本發明。 二P晋:發明提供一種有機薄膜電晶體,其係於基板上至 5極電極、源極電極及汲極電極3個端子、絕緣 體層以及有機半導體層,藉由於閉極電極上施加電麼而控 層極間電流的有機薄膜電⑽,上述有機半導體 具有下述通式⑴之結構的有機化合物: [化1]
、 B1及B2分別獨立係碳數為6〜60之2價芳香族烴基 二為1〜60之2價芳香族雜環基,分別獨立係氣 、/素原子、氰基、碳數為1〜30之烷基、碳數為丨〜^ ^基、碳數為1〜30之烧氧基、碳數為^之函烧氧 數為1〜胺基、碳數為2〜60之二烧基胺基(烧 二、it互鍵結而形成含氮原子之環結構)、碳數為1〜3〇 只酿基、碳數為卜⑽之齒炫基確酿基、碳數為^ :'基、碳數為1〜30之*烷硫基、碳數為3〜30之烷基矽 :t *數為6〜6G之芳香族煙基或者碳數為卜60之芳香族 雜力衣基·,,tl-隹u 匕等各基亦可具有取代基,又,R广I、R广 中相鄰接者$ / 間亦可形成飽和或不飽和之環狀結構]。 132167.doc 200917543 :’本發明係提供一種有機薄膜發光電晶體,其係於有 機薄膜電晶體中,利用於源極_汲極間流動之電流獲得發 光’且藉由於閘極電極上施加電壓而控制發光。 又, 合物: [化2] 本發明係提供一種如 下述通式(2)所表示之有機化
(2) [式中 又, 合物: [化3] u及R!2刀別獨立係碳數為1〜3 〇之烷基]。 本發明係提供一種如·+、 禋女下述通式(3)所表示之有機化
㈣立係2價之/獨立係叙數為1〜30之炫基,;83及34分 或2價之碳數:數為1〇〜6〇的2環以上之縮合芳香族經基 發明之效果6〇的2環以上之縮合芳香族雜環基卜 本發明之古 、薄膜電晶體’回應速度(驅動速度)高迷 132167.doc -10· 200917543 化,且開/關比大,作為電晶 可發光之有機薄臈發光電晶體 體之性能較高 且可利用為 【實施方式】 本發明係-種有機薄臈電晶體,立係、 有間極電極、源極電極及 …板上至〉、設置 及有機半導體層,藉由於 千、邑緣體層以 ㈤位電極上施加電壓而 極-汲極間電流的有機薄 二制源 含具有下述通式⑴之結構的有機化合物。導體層包 [化4]
於上 返通式⑴中’ &及32分別獨 芳香族煙基或碳數為價芳香族二數為6 6°之2價 亦可具有取代基。 之2仏方香族雜環基,此等各基 之=述通式⑴中’較好的是Ml分別獨立係包含苯環 於上述通式(1)中,較好 f的疋及B2分別獨立俜句冬 環之芳香族雜環之基。 包3 5員 作為上述& 2之方日私烴基的具 有取代基之苯、萘、貧、雜β 了列舉亦可具 三苯、corannulene、蔻、丄μ、, 陡葬伸 tdphenykne)、六苯并 尹一本(hexabenzo 本开寇(heXabenzoc〇r〇nene)、sum_ne 232167.doc 200917543 等之2價殘基。 又’作為上述Bl及B2之芳香族雜環基之具體例,可列舉 亦可具有取代基之。比咬、吼嗓、嗜琳、茶咬、唾料、吩 Ο y 嗪、一鼠雜蒽、°比°定幷㈣ ' 喷咬幷啥嗤琳…比嗪幷啥号 啉、啡琳、味嗤 '二苯并嗟吩、嘆嗯幷喧吩、二嗟嗯幷嚷 二苯并Μ、苯并二°夫喃 '二硫雜苯并二茚、二硫雜 ^節、二苯并石西吩、二石西雜苯并二節、二砸雜茚幷節雜 一苯并石夕羅等之2價殘基。 於上述通式⑴中,較好的是Ml相對於Ml 稱結構,更好的是—…輛結構 作為上述Β丨及心亦可且右 ,、有之取代基,可列舉與後述之 〜Rio相同者。 ;述通式(1)中,Rl〜RiQ分別獨立係氫原子、函素原 L氛基、碳數為1〜30之燒基、碳數為卜30之齒院基、碳 =1〜30之繼、碳數為㈣之㈣基、碳數為㈣ 、:胺基&數為2〜60之二烷基胺基(烷基亦可相互鍵结 碳=含氮原子之環結構)' 瑞數為之烧基績醯基: =為1〜%之^基伽基、碳數為1〜3〇之㈣基、碳數 = 硫基、碳數為㈣之㈣錢基、碳數為 方㈣《或者碳數為⑽之芳㈣雜環基, 2 有取代基,X’RlW中相鄰接者之 '、可形成飽和或不飽和之環狀結構。 又,較好的是於通式⑴中,R1〜R10分別獨立係氯原子、 132167.doc 200917543 函素原子、碳數為卜30之烧基或碳數為卜3〇之函燒基。 二=的是於通式⑴中’Rl、R2、R^〜R7、 〇、虱原子,且R3及Rs之至少一者係碳數為1〜30之 烷基、碳數 為… …基、函素原子或氰基,化合物成 為更緻牷之配向結構。 . 有機 X月之有機溥膜電晶體中使用之具有特定結構的 有機化合物,其士 L β β 導)之雔炻妯土一頌不卩型(電洞傳導)及η型(電子傳 (' 可藉由與後述之源極、汲極電極的組合而 為Ρ型元件驅動亦可作為η型元件驅動,於上述通式⑴ 用電子接叉性基作為於Β!〜I上取代之基或者 由此可降低最低非佔據分子軌道(LUMO)位準, 作為η型半導體發揮機能。作為電子接受性基,較好的是 虱原子、函素原子、氰基、碳數為卜30之函院基' 碳數為 1〜30之齒燒氧基、碳數為之㈣梅。又,使用 推電子性基作為Rl〜Rl〇及於1鳴取代之基,由此可提古 D ^佔據分子軌道⑽MQ)位準,作為p ^ 能。作為推電子性基,較好的是A原子、碟數為㈣2 基、碳數為1〜3〇之燒氧基、碳數為卜3〇之炫胺基、碳數為凡 160之"'院基胺基(燒基亦可相互鍵結而形成含氮原子之 壤結構)。 明下對通式⑴iRl〜Rl0所表示之各基的具體例加以說 作為上述函素原子,可列舉氟、氯、漠及峨原子。 作為上述貌基,可列舉?基、乙基、丙基、異丙基、正 132167.doc • 13. 200917543 丁基、第二丁基、異丁基、第三丁基、正戊基、正己基、 正庚基、正辛基、正壬基、正癸基、正十一院基、正十二 烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷 基、正十七烧、正十八烷基、正十九烧基、正二十烷基、 正二十一烷基、正二十二烷基、正二十三烷基、正二十四 烷基、正二十五烷基、正二十六烷基、正二十七烷基、正 二十八烷基、正二十九烷基、正三十烷基等。 作為上述鹵烷基,例如可列舉氯曱基、丨_氣乙基、2-氯 乙基、2-氣異丁基、U·二氯乙基、丨,3_二氯異丙基、2,3_ 二氯-第三丁基、1,2,3-三氣異丙基、溴甲基、卜溴乙基、 2-溴乙基、2-溴異丁基、ι,2_二溴乙基、丨,3_二溴異丙基、 2,3- —溴-第二丁基、ι,2,3-三溴丙基、埃甲基、卜礙乙 基、2-碘乙基、2-碘異丁基、i,2-二碘乙基、L3-二碘異丙 基、2,3-二碘-第三丁基、^^三碘丙基、氟曱基、丨_氟 甲基、2-氟甲基、2-氟異丁基、二氟乙基、二氟甲 基、二氟甲基、五氟乙基、全氟丙基、全氟丁基、全氟環 己基等。 上述烷氧基係以-OX1所表示之基,作為X1之例,可列舉 與上述烷基中所說明者相同之例;上述鹵烷氧基係以_〇χ2 所表示之基,作為-X2之例,可列舉與上述鹵烷基中所說 明者相同之例。 上述烷硫基係以-SX1所表示之基,作為χ1之例,可列舉 與上述烷基中所說明者相同之例;上述鹵烷硫基係以_sx2 所表不之基’作為-X2之例’可列舉與上述鹵烷基中所說 132167.doc -14- 200917543 明者相同之例。 上述烧胺基係以-NHX1所表示之基,二烷基胺基係 以-ΝΧ1Χ3所表示之基,χΐ及X3分別可列舉與上述烷基中所 說明者相同之例。再者,二烷基胺基之烷基亦可相互鍵結 形成包含氮原子之環狀結構,作為環狀結構,例如可列舉 吡咯烧、痕啶等。 上述烷基磺醯基係以-SOaX1所表示之基,作為χ1之例,
可列舉與上述烷基中所說明者相同之例;上述函烷基磺醯 基係以-S〇2X2所表示之基,作為X2之例,可列舉與上述齒 烧基中所說明者相同之例。 恩暴 作為上述^香族經基,例如可列舉苯基、萘基 菲基、第基、茈基、稠四苯基、稠五苯基等。 作為上述芳香族雜環基,例如可列舉二噻嗯幷苯基、苯 并咬'基、苯并嗟吩基、啥琳基…基、二苯并咳喃 基、二苯并噻吩基、苯并噻二唑基等。 2作為3上述烷基矽烷基,係_8ίχ1χ2χ3所表示之基,χΐ、 及X刀別可列舉與上述院基中所說明者相同之例。 作為上述飽和環狀結構,可列舉環丁基、環戊基、環己 基、1,4-二呤烷基等。 作為上述不鮮環狀結構,可列舉與上述芳香族煙基、 上边芳香族雜環基中所說明者相同之例。 :::亦可進而取代上述通式⑴所示之各基的取代基, 基 方管族雜玉衣基、烷基、烷氧基、芳氧 爪土、院氧基幾基、胺基、_素原子、氰基、硝 132167.doc 200917543 基、羥基、羰基等。 又’本發明提供下述通式(2)所表示之有機化人物 [化5] R”
(2)
於上述通式(2)中,Rll及Rl2分別獨立係碳數為㈣之烧 基,作為其具體例,可列舉與上述通式( 一 々# 4 丨〜Ri。所表示 之石厌數為1〜30之烷基的具體例相同之基。 又,本發明提供以下通式(3)所表示之有 [化 6] m
JL '()中,Rl3〜心分別獨立係碳數為"〇之广 基,作#1 ^彻 厌数马1〜30之烷 U例,可列舉與上述 之碳數為1〜30之;P莫M a R10所表不 之烷基的具體例相同之基。 於上述通式(3)中,b, ; R x 1 〇〜6 0的2環以上之縮合芳香族=立^2 =碳數為 環以上之縮合芳香族雜浐其 土以貝之奴數為4〜60的2 通式⑴及β2所身- 乍為其具體例,可列舉上述 2所表不之芳香族基令之2環以上之基,且 132167.doc -】6 · 200917543 碳數對應者。 以下,列舉本發明之有機薄膜電晶體的有機半導體層中 使用之通式(1)、(2)或(3)所表示之有機化合物的具體例, 但本發明並不限定於其等。 [化7]
132167.doc 17- 200917543 [化8]
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1 ; 132167.doc • 24- 200917543 200917543 [化16】
又’错由广如電晶體之電子元件中使用材料之純度較高 ,可獲得電子場效遷移率或開/關比較高之元件。因 此八有上述通式⑴之結構的有機化合物,較理想的是視 需要利用管柱層析法、再結晶、蒸餘、昇華等方法加以純 化。較好的是可藉由反覆利用其等純化方法或者組合複數 種方法而使純度提高。$而較理想的是至少重❸次以上 昇華純化作為純化之最終步驟。藉由使用其等方法,較好 的使用以HPLC測定之純度為90%以上之材料,進而較好的 是95%以上、特別好的是99%以上的材料藉此可提高有 132167.doc • 26 · 200917543 機薄膜電晶體之電子場效遷移率或開/關比,弓丨出材料本 身持有之性能。 以下,對本發明之有機薄膜電晶體的元件構成加以說 明。 作為本發明之有機薄膜電晶體的元件構成,若為於基板 上至夕叹置有閘極電極、源極電極及汲極電極3個端子、 絕緣體層以及有機半導體層,藉由於閘極電極上施加電壓 而控制源極-沒極間電流的有#薄膜電晶冑,則並無限 疋,亦可為除有機半導體層之成分以外具有公知之元件構 成者。 其等中,作為代表性之有機薄膜電晶體的元件構成,將 兀件A〜D不於圖中。如此,根據電極之位置、層之積 層順序等已知數種構成’本發明之有機薄膜電晶體具有場 效應電晶體(FET : Field Effect Transistor)結構。有機薄膜 ” /、有.有機半導體層(有機化合物層)、相互空出特 定間距對向而形成之源極電極及汲極電極、自源極電極與 汲極電極刀別空出特定之距離而形成之閘極電極,並且藉 由於閘極電極上施加電壓而控制於源極_汲極電極間流動 之電流。其中,源極電極與汲極電極之間隔係由使用本發 明之有機薄膜電晶體的用途所決定的,通常為〇1 咖’較好的是1叫〜1·,更好的是1 μηι〜100 μηι,進-步更好的是5 μηι〜1〇〇 。 一件A D中,以圖2之元件β為例加以更詳細之說明,元 件B之有機溥膜電晶體,於基板上順次具有閘極電極及絕 132167.doc -27- 200917543 緣體層,於絕緣體層上具有空出特定之間隔而形成之—斜 源極電極及汲極電極,於其上形成有機半導體層。有機半 導體層形成通道區域’藉由用施加於閘極電極上之電壓杵 制於源極電極與汲極電極之間流動的電流進行開/關= 本發明之有機薄膜電晶體,除上述元件A〜D以外之元件 構成之外,亦提出有各種構成作為有機薄膜電晶體,若為
藉由用施加於閘極電極上之電壓控制於源極電極與汲極電 極之間流動的電流進行開/關動作或者表現出增帽等效果 的組合,則並不限定於其等元件構成,例如亦可為具^如 由產業技術综合研究所之吉田等人於第49次應用物理學關° 係聯合講演會講演論文集27a_M_3(2〇〇2年3月)中提出之丁 部與底部接觸型有機薄膜電晶體(參照圖5),或者 1 學之工藤等人於電氣學會論文諸^84(1998)第144〇頁中提 出之縱形有機薄臈電晶體(參照圖6)之元件構成者。 (基板) 本發明之有機薄膜電晶體中之基板擔負著支財機薄膜 電晶體之結構的作用’作為材料,除了玻璃之外,亦可使 用金屬氧化物或氮化物等無機化合物,塑膠膜㈣τ, PES ’ PC)或金屬基板或者其等之複合體或積層體等。又, 於可藉由基板料之構成要素充分支財機薄膜電晶體之 尨構之情形時’亦可不使用基板。又,作為基板之材料多 =石夕⑻晶圓。於此情形時’可將以自身用作間極電極 兼基板。又,亦可將Si之表面氧化形成叫活用為絕緣 132167.doc -28- 200917543 層。於此情形時,亦可於基板兼閑極電極
Au等之金屬層作為導線連接用電極。 土板上成膜 (電極) 作為本發明之有機薄膜 s ^ ^ r旳閘極電極、源極電極 及^及極電極之材料,若為導電性材料則光& 玎蚀田办△ 以往材科則並無特別之限定, 了使用叙、金、銀、鎳 ,π ^ Α 扪鐵、錫、銻鉛、鈕、 姻、纪、碎、鍊、銀、紹 膝^ 鳍鉬、鎢、氧化錫. ^乳化鋼.錫_)、摻氣氧化辞、鋅、碳、石墨、玻 璃石墨、«料及碳㈣u、n鉀
航、鈦、錳、錯、鉉、炉 ,. A 、 鎵銳、納、11、 鋁、鎂/銅混合物、鎂/銀混合物、 X 4, , , ^ 鎮/銘此合物、鎂/銦混 '、:化鋁混合物、鋰/鋁混合物等,其等可藉由濺 鍍法或真空蒸鍍法進行成膜。 =發明之有機薄膜電晶體中’作為源極電極、汲極電 ^利用使用含有上述導電性材料之溶液、浆料、油 性電極材料而形成者。又,作為溶劑或 =之V 是含有6〇質量%以上、較好的是9。質量 之水用以抑制有機丰莫押J。k 機丰導體知壞的溶劑或分散介質。 3有金屬微粒子之分散物,在丨上+ 朦等,較好的是含有=:亦可使用公知之導電 nm 1π Φ 1 丁 ^ 马 0.5 ηηι〜50 nm、1 :之金屬微粒子的分散物。作為該金屬 :v:可使懸、金、銀、錦、絡、銅、鐵、錫、錄 :、鋼mm、錯、,、鶴、辞 132167.doc -29- 200917543 人車父好的是使用分散物形成電極,該分散物係使用主要包 有機材料之/刀散穩定劑,將其等金屬微粒子分散於水或 任意有機溶劑的分散介質中的分散物。作為如此之金屬微 拉子之分散物的製造方法,可列舉氣相蒸發法、錢法、 纟屬4氣合成㈣物理性生成法或者膠體法、共沈殿法等 以液相還原金屬離子而生成金屬微粒子之化學性生成法, .1 交好的是藉由日本專利特開平u-moo號公報、日本專利 C 肖開平U_80647號公報、曰本專利特開平u-319538號公 報、日本專利特開2000_239853公報等中揭示之谬體法, 日本專利特開2__254185公報、日本專利特開2__5則 號公報、日本專利特開·_352555號公報、日本專利特 開2_·124157號公報、日纟專利特開2_-123634號公報 等中揭示之氣相蒸發法製造之金屬微粒子的分散物。 使用其等金屬微粒子分散物成形上述電極,使溶劑乾燥 之後’視需要於峨〜3,C、較好的是⑽〜贿之範 〇 111内加熱成形狀模樣,藉此使金屬微粒子熱融著,形成具 有目標形狀之電極圖案。 進而,作為閉極電極、源極電極及沒極電極之材料,較 好的是使用以摻雜等使導電率提高之公知的導電性聚合 物,例如可適宜使用導電性聚苯胺、導電性聚吡咯、導; 性聚嗔吩(聚乙稀二氧。塞吩與聚苯乙婦續酸之錯合物等)、 聚乙稀二氧嗟吩(PED0T)與聚苯乙烤績酸之錯合物等。藉 由其等材料可降低源極電極與沒極電極之有機半導體層的 132167.doc -30- 200917543 形成源極電極及汲極電極之 例中,於與有機半導體層之接觸面雷較好=即使於上述 電阻,即製作電流控制震置 。此時之 獲得較大之遷移率而必 阻:子…移率對應,為 極材料之功函數鱼有機半導:儘可能小。其通常係由電 U機體層之能級的大小關係所決 於本發明之有機薄 θ δ , t曰曰體中’較好的是源極電極及汲 f
=極的:少-者係包含功函數為4切以上之物質,且/ / 一者係包含功函數為“eV以下之物質。 將電極材料之功函數A a ^ - ()°又為a,將有機半導體層之游離 電位⑽設為b,將有機半導體層之電子親和力⑽設為 :’較好的是滿足以下關係式。其中,a、…均係將真空 位準作為基準之正值。 於p型有機薄膜電晶體之情形時,較好的是b_a<i5 (式())更好的疋b-a< 1.0 eV。於與有機半導體層之關 係中,若T維持上述關係則可獲得高性能之Μ,特別是 選擇電極材料之功函數儘可能大者較好,較好的是功函數 為4.0 eV以上,更好的是功函數為4 2 eV以上。 金屬之功函數值,若自例如化學便覽基礎編^第々%頁 丁第3版日本化學會編丸善股份有限公司發行1983 年)中揭不之具有4.0 eV或其以上之功函數的有效金屬之上 述列表中選擇即可,高功函數金屬主要有Ag(4.26,4.52, 4.64 ’ 4.74 eV),Al(4.06,4.24,4.41 eV),八邮」, 5.37,5,47 eV),Be(4.98 eV),Bi(4.34 eV),Cd(4.08 132167.doc -31 - 200917543 eV} > Co(5.0 eV),Cu(4.65 eV) . Fe(4.5 > 4.67 > 4.81 eV),Ga(4.3 eV) ’ Hg(4.4 eV),ΐΓ(5·42,5 76 eV),Mn(4」 eV) ’ Mo(4.53,4·55 ’ 4.95 eV),Nb(4.02,4.36,4.87 eV) ’ Ni(5.04 ’ 5.22,5.35 eV) ’ 〇s(5.93 eV),pb(4 25 eV) - Pt(5.64 eV) > Pd(5.55 eV) . Re(4.72 eV) , Ru(4.71 • eV) ^ Sb(4.55 ^ 4.7 eV) - Sn(4.42 eV),Ta(4.0 , 4.15 - 4.8 eV) ’ Ti(4.33 eV) ’ V(4.3 eV) ’ W(4.47,4.63,5.25 eV), ^, Zr(4.05 eV)。其等中,較好的是貴金屬(Ag,Au,cu ,
Pt) ’ Νι ’ Co ’ 〇s ’ Fe ’ Ga,lr,Μη,Mo,Pd,Re,RU, V,W。除金屬以外,較好的是如IT〇、聚苯胺或pED〇T : PSS之導電性聚合物及碳。作為電極材料,可含有一種或 者複數種其等高功函數之物質,若功函數滿足上述式⑴則 並不受到特別之限制。 於η型有機薄膜電晶體之情形時,較好的是< 1 $ eV(式(Π)) ’更好的是&<<1() eV。於與有機半導體層之 〇 關係中,若可維持上述關係則可獲得高性能之裝置,特別 是選擇電極材料之功函數儘可能小者較好,較好的是功函 數為4·3 eV以下,更好的是功函數為3.7 eV以下。 作為低功函數金屬之具體例,若自例如化學便覽基礎 編II-弟493頁(修訂第3版日本化學會編丸善股份有限公 司發行1983年)中揭示之具有4.3 ev或其以下之功函數的 有效金屬之上述列表中選擇即可,可列舉Ag(4.26 eV),
Al(4.〇6 ’ 4.28 eV) ’ Ba(2.52 eV),Ca(2.9 eV),Ce(2.9 eV) ’ Cs(1.95 eV) ’ Er(2.97 eV),Eu(2_5 eV) ’ Gd(3.1 132167.doc •32- 200917543 eV),Hf(3.9 eV),Ιη(4.09 eV),Κ(2·28),La(3.5 eV),
Li(2.93 eV),Mg(3.66 eV),Na(2.36 eV),Nd(3.2 ev),
Rb(4.25 eV),Sc(3.5 eV),Sm(2.7 eV),Ta(4.〇,4 15 eV),Υ(3·1 eV),Yb(2.6 eV),Zn(3.63 eV)等。其等中, 較好的是 Ba,Ca,Cs,Er,Eu,Gd,Hf,κ,La , Li
Mg,Na,Nd,Rb,Y,Yb,Zn。作為電極材,可含有一 種或者複數種其等低功函數之物質,若功函數滿足上述式
(Π)則並不受到特別之限制。但是,低功函數金屬若與大 氣中之水分或氧接觸則容易產生劣化,較理想的是視需要 塗覆如Ag或Au之於空氣中穩定之金屬。塗覆必需之膜厚 須為〗0 nm以上,膜厚變得越厚則越可以自氧或水保護, 但自實用上、提高生產性等理由考慮較理想的是【_以 下。 邗马上迷電極之形成 — -—批秋、-电卞射末 洛鑛、誠、大氣壓電衆法、離子電鑛、化學氣相基鑛、 電鑛、無電電鍍、旋轉式塗佈、印刷或噴墨等方法形成。 :法需要進行圖案化之方法,# :使用公知之光微 衫法或者舉離法,將佶用 ^ # , 34方法而形成之導電性薄膜形 成電極之方法;藉由熱轉印、 2 '贺墨專,於鋁或銅等之金屬 V白上形成抗蝕劑層進行 、本验道兩 J之方法。X,可藉由直接喷墨 法將導電性聚合物之溶液或 分散液箄ϋΐϋμ 一刀散液、含有金屬微粒子之 塗佈膜。谁而介 心法或者雷射剝離法等形成 寬佈臈。進而亦可使用藉由凸版 等印刷法將含有導電性聚 +版、絲網印刷 x s物或金屬微粒子之導電性油 132I67.doc -33 - 200917543 墨導電性襞料等圖案化之方法。 由此而形成之電極的膜厚若可導通電流則並無特別之限 制,較好的是〇 2 n 圄—认_ 更好的疋4如1〜30〇 nm之範 成電^ 之範圍内,則不會產生由於膜厚較薄而造 成電壓降低之現象。又,因並不過厚 並不耗費時間,於積層保護層或有機半導體層等其他層; 潰形時T並不產生階差地使積層膜圓滑。 f / 本實鈿之有機薄膜電晶體中,例如為提高佈植效 率/亦可於有機半導體層與源極電極及汲極電極之間設置 緩衝層4乍為緩衝層,對於n型有機薄膜電晶體,於有機 ^之陰極中使用之W、U2〇、CsF、NaC〇3、κα、
MgF2 CaC03等具有鹼金屬、驗土金屬離子鍵之化合物較 理想。又,亦可插入Alq等在有機中用作電子佈植層、 電子傳輸層之化合物。 對於P型有機薄膜電晶體,FeCl3、TCNQ、F4_tcnq、 HAT 等之氰基化合物 ’ CFx 或 Ge02、Si02、Mo03、V205、 V02、V203、MnO、Mn304、Zr02、W03、Ti02、ln203、
ZnO、NiO、Hf〇2、Ta205、Re〇3、PbOJ 鹼金屬、鹼土金 屬以外之金屬氧化物,ZnS、ZnSe等無機化合物較理想。 其等氧化物於較多之情形時造成氧缺陷,其適於電洞佈 植。進而’ TPD或NPD等胺系化合物或者CuPc等有機EL元 件中用作電洞佈植層、電洞傳輸層之化合物亦可。又,較 理想的是包含兩種以上上述化合物者。 已知緩衝層具有藉由降低載子之佈植能障而降低臨界電 132167.doc •34· 200917543 Μ,以低電壓驅動電晶體之效I,但A我們發現對於本發 明之化合物而言,不僅有低電壓效果而且有使遷移率提高 之效果。其原因在於:於有機半導體與絕緣體層之界面: 在載子陷阱,若施加閘極電壓而引起載子佈植,則最初佈 植之載子被埋入陷阱中而被使用,藉由插入緩衝層,可以 低電壓埋入陷阱而提高遷移率。緩衝層若於電極與有機半 導體層之間較薄地存在即可,其厚度為〇1 nm〜3〇 _ ,較 好的是0.3 nm〜20 nm。 (絕緣體層) 作為本發明之有機薄膜電晶體中之絕緣體層的材料,若 為具有絕緣性且可形成為薄膜者,則並無特別之限定,可 ,用金屬氧化物(包括矽之氧化物)、金屬氮化物(包括矽之 氮化物)、高分子、有機低分子等於室溫下之電阻率㈣ ◦cm以上之材料,特別是相對介電常數較高之無機氧化物 被膜較好。 作為無機氧化物,可列舉氧切、氧化、氧化组、氧 化鈦、氧化錫、氧化鈒、鈇酸鋇銷、錯鈦酸鋇、錯欽酸 釔-鈦S夂鉛鑭、鈦酸鎇、鈦酸鋇、氟化鋇鎂、鑭氧化物、 敗氧化物、鎂氧化物、叙氧化物、鈦酸叙、銳氧化物、鈦 酸锶鉍、鈕酸鰓鉍、五氧化二鈕、鉅酸鈮酸鉍、三氧化二 釔以及將其等組合者,較好的是氧化矽、氧化鋁 '氧化 组、氧化鈦。 又,亦可適宜使用氮化矽(Si3N4、SixNy(x 化銘等無機氮化物。 132167.doc •35- 200917543 進而,絕緣體層亦可由包含金屬醇鹽之前驅物形成,將 該前㈣之溶液’塗t於例如基板上’對其進行包含熱處 理之化學溶液處理,藉此形成絕緣體層。 作為上述金屬醇鹽中之金屬,例如可自過渡金屬、鋼系 元素或主族元素中選擇,具體而言可列舉鋇㈣、錄 (Sr)、鈦(Ti)、錢(Bi)、组(Ta)、錯(Zr)、鐵㈣、錄⑽、
錳(Μη)、鉛(Pb)、鑭(La)、鋰(u)、納(Na)、鉀(κ)、麵 (Rb)、鉋(CS)、鲂㈣、鈹㈣、鎮(Mg)、約(Ca)、鈮 (Nb) h(Tl)、水(Hg)、銅(cu)、銘(c。)、姥⑽)、銳㈣ 及釔(Y)等。又,作為上述金屬醇鹽中之醇鹽,例如可列 舉自包含曱醇、乙醇、丙醇、異丙醇、丁醇、異丁醇等之 醇類,包含曱氧基乙醇、乙氧基乙醇、丙氧基乙醇、丁氧 基乙醇、戊氧基乙醇、庚氧基乙醇、曱氧基丙醇、乙氧基 丙醇、丙氧基丙醇、丁氧基丙醇、戊氧基丙醇、庚氧基丙 醇之烷氧基醇類等衍生者。 於本發明中,若以如上述之材料構成絕緣體層,則變得 谷易於絕緣體層中產生空乏層,可減低電晶體動作之臨界 電壓。又,於上述材料中,特別是若以Si3N4、、 SiONx(x、y>〇)等氮化矽形成絕緣體層,則變得更容易產 生空乏層’可進一步減低電晶體動作之臨界電壓。 作為使用有機化合物之絕緣體層,亦可使用聚醯亞胺、 聚醯胺、聚酯、聚丙烯酸酯、光自由基聚合系、光陽離子 聚合系光硬化性樹脂、含有丙烯腈成分之共聚物、聚乙烯 紛、聚乙烯醇、酚醛清漆樹脂及氰乙基普魯蘭等。 132167.doc •36· 200917543 其他,除蠟、聚乙烯、聚氯芘、聚對苯二甲酸乙二酯、 聚甲醛、聚氣乙烯、聚偏二氟乙烯、聚甲基丙烯酸曱酯、 聚颯、聚碳酸酯 '聚醯亞胺氰乙基普魯蘭、聚(乙烯 酚)(PVP)、聚(曱基丙烯酸曱酯)(PMMA)、聚碳酸酯(PC)、 聚苯乙烯(PS)、聚烯烴、聚丙烯醯胺、聚(丙烯酸)、酚醛 清漆樹脂、可溶酚醛樹脂、聚醯亞胺'聚二曱苯、環氧樹 月曰之外,亦可使用普魯蘭等具有較高介電常數之高分子材 料。
、’邑緣體層中使用之有機化合物材料,作為高分子材料, 特別好的是具有斥水性之材料。藉由具有斥水性,可抑制 、邑緣體層與有機半導體層之相互作用,利帛有機半導體本 5有之凝聚性提高有機半導體層之結晶性而使裝置性能 提高。作為如此之例,可列舉Yasuda等JPn LAppl . phys. .42 (2003) ρρ· 66U-6618中揭示之聚對二曱苯衍生物 或者 Janos Veres 等 Chem Μ_,ν〇ι Μ (2〇〇句 pp 45仏 4555中揭示者。 又’如圖1及圖4所示般使用頂問極結構時,若將如此之 有機化合物用作絕緣體層之材料,則可減少給有機半導體 層帶來之損壞而成膜,故而係有效之方法。 ^絕緣體層可為使用複數種如上述之無機或 混合層,亦可為其等之積層結構物。於此情形 料混合,之材料與具有斥水性之材 仃積層,藉此而控制裝置之性能。 又,上述絕緣體層亦可包含陽極氧化膜,或包含該陽極 132167.doc •37- 200917543 氧化膜料構成。較好極氧化料行 理、。陽極氧化膜,可藉由對可陽極氧化之金屬以公知之方 法進行陽極氧化而形成。作為可陽極氧化處理之 可 列舉铭或纽,對陽極氧化處理之方法並無特別之限制,可 使用公知之方法。藉由進行陽搞氧几由 進仃陽極聽處理,形成氧化被 膜。作為陽極氧化處理中使用之電解液,若為可形成多孔 狀氧化被膜者則可使用任意者,通常使用疏酸、碟酸、草 酸、鉻酸、賴、胺基續酸、苯續酸等或者組合有其等之 2種以上之混酸或其等之鹽。陽極氧化之處理條件由於使 用之電解液而產生各種變化,因此並非一概特定,通常較 合適的是電解液之濃度為U0質量%、電解液之溫度為 5〜70C、電流密度〇.5〜60 A/cm2、電壓為丨〜丨⑼伏特、電解 時間為!〇秒〜5分鐘之範圍。較好之陽極氧化處理係使用硫 酸、破酸或删酸之水溶液作為電解液,以直流電流進行處 理之方法,亦可使用交流電流。其等酸之濃度較好的是 5〜45質量%,較好的是於電解液之溫度為2〇〜5〇。〇、電流 密度為0.5〜20 A/cm2進行20〜250秒之電解處理。 、,作為絕緣體層之厚度’若層之厚度較薄,則施加於有機 半導體上之有效電壓變大,因此可降低裝置自身之驅動電 壓、臨界電壓,但是相反源極_閘極間之$漏電流變大, 因此必需選擇適宜之膜厚’ 4常為1〇随〜5 _、較好的是 50 nm〜2 μπι、更好的是1〇〇μπι 〇 又,於上述絕緣體層與有機半導體層之間,亦可實施任 思之配向處理。作為其較好之例,係於絕緣體層表面實施 132167.doc -38· 200917543 斥水化處理等,使絕緣體層與有機半導體層之相互作用減 低,從而使有機半導體層之結晶性提高的方法,具體而 言’將石夕炫偶合劑,例如十八炫基三氯石夕烧、三氯f基石夕 亂烧或者烧經鱗酸、烧煙磺酸、烷烴羧酸等自動組合配向 膜材料,於液相或氣相之狀態下,與絕緣膜表面接觸而形 成自動組合膜後,適度地實施乾燥處理之方法。又,為用 於液晶配向,較好的是於《g絲^时屯 平乂 丁町疋於絕緣臈表面設置由聚醯亞胺等構 成之膜,對其表面進行摩擦處理之方法。 作為上述絕緣體層之形成方法,可列舉真空蒸鑛法、分 子束蟲晶法、離子團束法、低能量離子束法、離子電鑛 法、CVD法、減鍍法、日本專利特開平u_6屬號公報、 日本專利特開平u.1332G5m公報、日本專利特開觸_ 121804號公報、日本專利特開2〇〇〇_1472〇9號公報、日本 專利特開200(M85362號公報中揭示之大氣壓電衆法等乾 式製程,$塗法、旋塗法、刮塗、浸潰塗層法、洗鑄法、 a °、 棒式塗佈法、模塗法等塗佈之方法、印刷或喷墨 等之圖案化的方法等濕式製程’可根據材料使用。濕式製 程可使用如下夕士 4 . w 添 法·將視需要使用界面活性劑等分散助 劑’於任意有機溶劑或水中分散有無機氧化物之微粒子而 =的,體,進行塗佈、乾燥的方法;或者將氧化物先驅 ,鹽體之溶液塗佈、乾燥,即所謂之溶膠凝膠法。 务月之有機薄膜電晶體中之有機半導體層之膜厚,並 '、·、特別之限制,通常為0.5— _,較好的是2nm〜25〇 nm 〇 132167.doc -39- 200917543 又’有機半導體層之形成方法,可並無特別限定地適用 A知之方法,例如可藉由分子束蒸鍍法法)、真处蒸 鍵法、化學蒸鍵、利用於溶劑中溶解有材料之溶液的:錄 法、旋轉式塗佈法、德谢、土 ^ 押次‘塑法、棒式塗佈法、輥塗法等印 刷、塗佈法以及烘乾、電聚合、分子束蒸鑛、於溶液中之 自我組裝、及其等之組合的方法,以如上述之有機半導體 層之材料形成。 一若使有機半導體層之結晶性提高,則電子場效遷移率提 高,因此於使用於氣相中成膜(蒸錢、濺鍍等)之情形時, 較理想的是以高溫保持成膜中之基板溫度。該溫度較好的 是50〜25(TC,更好的是7〇〜15〇t。又無論成膜方法若 於成膜後實施退火,則可獲得高性能裝置,故較好。退火 之,度較好的是50, ’更好的是70,,時間較好 的是10分鐘〜12小時,更好的是1小時〜1〇小時。 於本發明中,有機半導體層可使用—種選自通式⑴之 材料’亦可組合複數種,或者使用稍五苯或b塞吩寡醋等公 知之半導體’複數種混合薄膜或積層而使用。 作為本發明之有機薄膜電晶體的形成方法,並益特別之 :定’亦可使用公知之方法’若依照所期望之元件構成, 凡全不與大氣接觸地按照基板投入、閘極電極形成、絕緣 體層形成、有機半導體層形成、源極電極形成、淡極電極 形成之-系列元件製作步驟形成’則可防止與大氣接觸而 由於大氣中之水分或氧等產生之元件性能阻害,故較好。 不得已,-旦必需與大氣接觸時,較好的是將有機半導體 132167.doc • 40- 200917543 半導體;大氣接觸之步驟,於有機 二之二Γ前’對積層有機半導體層之面(例如於元 件B之十月形時,係於絕緣層部分積層有源極電極 極之表面UX紫外線照射、紫外線/臭氧照射、 電聚等進行清淨化•活化之後,積層有機半導體層:、風 進而,例如亦可考膚大痛φ人女 产 J哼應大虱中合有之氧、水等對 影響,於有機電晶體元件之外周面的整個面或者一 Μ形成阻氣層。作為形餘氣層之材料 域常用者,例如可列舉聚乙❹ 文用於该領 j Μ料乙料、乙稀·乙料共聚物、 :亂乙稀、聚偏二氯乙稀、聚氣三氟乙烯等。進而,亦可 使用於上述絕緣體層中例示之具有絕緣性之無機物。 亡發明又提供一種有機薄膜發光電晶體,其係於 機薄膜電晶體中’利用流過源極_沒極間之電流獲奸
先,且藉由於間極電極上施加電塵而控制發光。 X 本發明中之有機薄膜電晶體亦可使用自源極、沒極電極 佈植之電荷用作發光元件。藉由以閉極電極控制於源極· 沒極電極間流動之電流,可控制發光強度。即,將有機薄 膜電晶體用作發光元件(有機叫。可統合用以控制發光之 光元件,因此可提高顯示器之開孔率或使製作 “墙早化而降低成本,賦予於實用上之較大優點。於用 作有機發光電晶體時,以於上述詳細說明中敍述之内容已 =夠’但為使本發明之有機薄膜電晶體作為有機發光電晶 動作,必需自源極、沒極之—者佈植電洞,自另一者佈 植電子為使發光性能提高,較好的是滿足以下之條件。 I32I67.doc •41 · 200917543 (源極、沒極) 為提高電洞之佈植性,較好的是至少一 ^ 電極。所謂電洞佈植電極,係包含上二=洞佈植性 上之物質的電極。 數為4.2 eV以 又,為提高電子之佈植性,較好的是至少 植性電極。所謂電子佈植性電極,係 、固為電子佈 4.3 eV以下之物質的電極。更好的是具有二:函數為 性,且另-個為電子佈植性之電為::佈植 體》 力钱涛胰發光電晶 (元件構成) 為提南電洞之佈植性,較好的是於至少一個 :導體層之間插入電洞佈植層。電洞佈植層可 :件:”電洞佈植材料、電洞傳輸材料之胺系材料。 有機半導=電子之佈植性’較好的是於至少—個電極與 曰之間插入電子佈植性層。與電洞相同,電子 佈植層可使用於有機EL元件中使用之電子佈植材料。 更好的是於一個電極下具備電洞佈植層,且於另__ 極下具備電子佈植層的有機薄膜發光電晶體。 又,,於本實施之有機薄膜發光電晶體中,例如亦可 機半導體層與源極電極及汲極電極之間設置緩 佈植效率。 屬乂徒阿 實施例 繼而’使用實施例對本發明加以更詳細之說明。 合成例1(化合物(2)之合成) 132167.doc •42- 200917543 以如下方式合成上述化合物(2)。合成路徑如下所示。 [化 17]
於3 00毫升之三口燒瓶中放入4,4'-二溴芪3.00 g(8.87 mmol)、四(三苯基膦)ΙεΟ.513 g(0.443 mmol)、埃化銅(I) 0.169 g(0.886 mmol),進行氬氣取代。於其中添加三乙胺 22毫升、4-乙炔基甲苯3.09 g(26.6 mmol),於氬氣環境下 加熱回流9小時。過濾反應液,以二氣甲烷、甲醇清洗所 得之固體,獲得化合物(2)2.36 g(5.77 mmol,產率為 65%)。藉由90 MHz W-NMR及FD-MS(場解吸質譜)之測定 確認其係目標物。FD-MS之測定結果如下所示。 FD-MS,calcd for C48H3〇S2=408,found,m/z=408(M+, 100) 又,將本化合物於280°C下昇華純化。藉由昇華純化獲 得之化合物(2)的純度為99.5%。 再者,於合成例1中,FD-MS(場解吸質譜)之測定中使用 的裝置及測定條件如下所示。 <FD-MS 測定 > 裝置:HX110(日本電子公司製造) 條件:加速電壓8 kV 掃描範圍111/^=5 0〜15 00 132167.doc -43 - 200917543 合成例2(化合物(29)之合成) 以如下方式合成上述化合物(29)。合成路徑如下所示。 [化 18] ΕίΟ ^Ph^Cul·
(化合物(B)之合成) 於300毫升之三口燒瓶中添加化合物(A)10.9 g(36.2 mmol)、亞填酸三乙S旨12.0 g(72.3 mmol)。將反應器於150 °C下加熱回流3小時,其後於減壓下進行蒸餾,自反應物 中除去雜質。將於燒瓶中殘留之殘渣進而以管柱層析法加 以純化,獲得化合物(B)9.71 g(27.2 mmol,產率為75%)。 (化合物(C)之A成) 於300毫升之三口燒瓶中添加化合物(B)4.0 g(11.2 mmol)、四(三苯基膦)Ιε0.647 g(0.560 mmol)、块化銅(I) 0.213 g(l. 12 mmol),進行氬氣取代。於其中添加三乙胺 16毫升、四氫呋喃56毫升、4-乙炔基甲苯2.60 g(22.4 132167.doc -44- 200917543 mmol),於氬氣環境下加熱回流8小時。過遽反應液,以二 氣甲烷、甲醇清洗所得之固體,獲得化合物(C)3.41 g(8.69 mmol,產率為 78%)。 (化合物(E)之合成) 於300毫升之三口燒瓶中添加化合物(D)2.00 g(8.51 mmol)、四(三苯基膦)le 0.492 g(0.426 mmol)、蛾化銅(I) 0.162 g(0.852 mmol),進行氬氣取代。於其中添加三乙胺 20毫升、四氫呋喃20毫升、4-乙炔基曱苯1.48 g( 12.8 mmol),於氬氣環境下加熱回流9小時。過濾反應液,以二 氯曱烷、甲醇清洗所得之固體,獲得化合物(E)l.73 g(6.40 mmol,產率為 75%)。 (化合物(29)之合成) 於300毫升之三口燒瓶中添加化合物(C)1.35 g(3.44 mmol),進而添加10毫升之THF。於其中每次少量添加第 三丁醇鉀0.463 g(4· 13 mmol)。將反應器於室溫下攪拌30分 鐘之後,進而添加化合物(E) 1.40 g(3.78 mmol)之THF溶液 10毫升,於室溫下攪拌2小時。過濾反應液,以二氯甲 烷、甲醇清洗所得之固體,獲得化合物(29)0.874 g( 1.72 mmol,產率為 50%)。藉由 90 MHz h-NMR及 FD-MS(場解 吸質譜)之測定確認其係目標物。FD-MS之測定結果如下 所示。再者,FD-MS之測定中使用的裝置以及測定條件與 合成例1相同。 FD-MS,calcd for C48H3〇S2=508,found,m/z=508(M+, 100) 132167.doc -45- 200917543 實施例1 (有機薄膜電晶體之製造) 以如下步驟製作有機薄膜電晶體。首先,將Si基板(兼 用作p型電阻係數1 Ω cm閘極電極)以熱氧化法使表面氧 化,於基板上製作300 nm之熱氧化膜作為絕緣體層。進 而,藉由乾式蝕刻將於基板之一面成膜之Si02膜完全除去 之後,藉由濺鍍法以20 nm之膜厚成膜鉻,進而於其上藉 錢鑛成膜100 mm之金(Au),取出作為電極。將該基板以 巾性洗劑、純水、丙酮及乙醇各進行30分鐘超音波清洗, 進而進行臭氧清洗。 繼而,將上述基板設置於真空蒸鍍裝置(ULVAC公司製 造,EX-400)中,於絕緣體層上以〇 〇5 nm/s之蒸鍍速度成 膜上述化合物(2)作為膜厚5〇 nm之有機半導體層。繼而, 通過金屬遮罩以50 nm之膜厚成膜金,藉此形成互相並不 連接之源極電極及汲極電極以使間隔(通道長L)成為75 μηι。此時以使源極電極與汲極電極之寬度(通道寬w)成為 I 5 mm之方式成膜而製作有機薄膜電晶體(參照圖乃。 對所得之有機薄膜電晶體之閘極電極施加_4〇 V之閘極 電壓,於源極-汲極間施加電壓使電流流動。於此情形 時於有機半導體層之通道區域(源極_汲極間)引起電洞, 作為P型電晶體動作。其結果,於電流飽和區域之源極_汲 極電極間之電流的開/關比為3χ1〇5。又,藉由下述式(A)算 出電洞之電子場效遷移率μ,係6xl〇-2 cm2/Vs。
Id=(W/2L) * 〇μ - (Vg-Vt)2(A) 式中,Id係源極-汲極間電流、W係通道寬、^係通道長' 132167.doc •46· 200917543 ==之每單位♦電容、一極臨界電 實施例2(有機薄膜電晶體之製造) 使用化合物(75)代替化合物 # , ρΛ. ^ )作為有機半導體層之材 枓除此之外,以與實施例丨相同之 薄膜雷曰鲈啦 式進仃’製作有機 溥膜電S曰體。對所得之有機薄膜 闾夕古4、 日體以與實施例1相 门之方式,以_40 V之閘極電壓ν推 ^ 進Ρ型驅動。測定源
極-及極電極間之電流的 故φ 斤出電洞之電子場效遷 移率μ,將結果表示於表1。 實施例3(有機薄膜電晶體之製造) 、使用化σ物(21)代替化合物⑺作為有機半導體層之材 料’除此之外,以與實施例⑶同之方式成膜至有機半導 體層 '繼而’通過金屬遮罩以⑽_之蒸鑛速度真空装 链C峨替心作為源極汲極電極,其後以0.05 nm/s之蒸鑛 速^鑛50 nn^Ag,被覆Ca,製作有機薄膜電晶體。對 所知之有機薄臈電晶體,以與實施例1相同之方式,以 〇 V之閘極電壓VG進行n型驅動。測定源極-汲極電極間 之電流的開/關比算出電洞之電子場效遷移率μ,將結果表 示於表1。 實施例4(有機薄膜電晶體之製造) 作為源極-汲極電極,以〇 〇5 nm/s之蒸鍍速度真空蒸鍍 10 nm之緩衝層河〇〇3,插入至Au與化合物(2)之薄膜間代 替單獨使用Au,除此之外,以與實施例丨相同之方式進 行’製作有機薄膜電晶體。對所得之有機薄膜電晶體,以 132167.doc -47· 200917543 與Λ %例1相同之方式’以-40 V之閘極電壓Vg進行p型驅 動。測定源極-汲搞雷 ^ 電極間之電^的開/關比,算出電洞之 電子場效遷移率P,將結果表示於表1。 比較例1(有機薄膜電晶體之製造) 以與實施例1相同之方式實施基板之清洗、閘極電極成 膜、絕緣體I。繼而使聚對苯乙块(PPV)[分子量(Mn)為 86_,分子量分布(Mw/Mn=5⑶以3質量%溶解於甲笨
中^上述成膜至絕緣體層之基板上藉由旋塗法成膜,於 氮風%i兄下、12CTC下使其乾燥成膜為有機半導體層。繼 而’於真空蒸鑛裝置中通過金屬遮罩以5G nm之膜厚成膜 金(Au) ’藉此形成互相不接觸之源極及汲極電極,製作有 機薄膜電晶體。 對所得之有機薄膜電晶體,以與實施例丨相同之方式, 以40 V之閘極電壓%進行?型驅動。測定源極·沒極電極 間之電流的開/關比’算出電洞之電子場效遷移率p,將結 果表示於表1。 比較例2 使用聚對苯乙块(PPV)作為有機半導體層之材料,以與 比較例1完全相同地成膜至有機半導體層。其後,以與實 施例3相同地進行,通過金屬遮罩成膜以作為源極_沒極^ 極,於其上被覆Ag而製作有機薄膜電晶體。 對所得之有機薄膜電晶體,以與實施例3相同之方式, 以+40 V之閘極電壓%進行n型驅動。測定源極-沒極電極 間之電流㈣/關比’ 電洞之電子場效遷移率^,將結 132167.doc -48· 200917543 果表示於表1。 [表1] 有機半導體層之 化合物種類 電晶體 之種類 電子場效遷移率 (cm2/Vs) 開/關比 實施例1 (2) P型 6xl〇·2 3xl05 實施例2 (75) P型 2x1 Ο·2 2x106 實施例3 (21) η型 2x10'3 2x104 實施例4 (2) Ρ型 4χ10-2 8x105 比較例1 PPV Ρ型 lxlO'5 lxlO3 比較例2 PPV η型 lxlO'4 lxlO3 實施例5(有機薄膜發光電晶體之製造) 以如下步驟製作有機薄膜發光電晶體。首先,將Si基板 (兼用作P型電阻係數1 Ω cm閘極電極)以熱氧化法使表面氧 化,於基板上製作300 nm之熱氧化膜作為絕緣體層。進 而,藉由乾式蝕刻將於基板之一面成膜之Si02膜完全除去 I: 之後,藉由滅鐘法以20 nm之膜厚成膜鉻,進而於其上藉 由滅鐘成膜100 mm之金(Au),取出作為電極。將該基板以 中性洗劑、純水、丙酮及乙醇各進行30分鐘超音波清洗。 繼而,將其設置於真空蒸鍍裝置(ULVAC公司製造,EX-900)中,於絕緣體層(Si02)上以0.05 nm/s之蒸鍍速度成膜 上述化合物(2)作為膜厚100 nm膜厚之有機半導體發光 層。繼而,以與上述相同之方式,設置通道長75 μηι、通 道寬5 mm之金屬遮罩,於將基板相對於蒸發源傾斜45度之 132167.doc -49- 200917543 狀態下,通過遮罩以50 nm之臈厚成臈金。繼而,於將基 板於逆方向上傾斜45度之狀態下,蒸鍍100 nmiMg,藉 此裝作互相不接觸之源極電極及汲極電極實質上具備電洞 佈植性電極(Au)與電子傳輸性電極(Mg)之有機薄膜發光電 晶體。(參照圖8) 右於源極-汲極間施加_1〇〇 v且於閘極電極上施加-⑽ V ’則獲得4〇 cd/m2之藍色發氺。於固。士士 邑發先於圖9中表示發射光譜。 產業上之可利用性 且=詳細說明,本發明之有機薄膜電晶體,由於使用 體層之材料„ . 特疋、、“冓之化合物作為有機半導 回應速度(驅動速度)高速,且開/關比大, 作為電晶體之性能較其 光電晶體。 °亦可用作可發光之有機薄膜發 【圖式簡單說明】 圖1係表示本發明之有 之圖 機薄膜電晶體的元件構成之一 例 圖2係表示本發明之 之圖。 有機涛膜電晶體的元件構成之一例 圖3係表示本發明之有 之圖。 有機薄膜電晶體的元件構成之一例 圖4係表示本發明之 例 之圖。 圖5係表示本發 之圖。 - 有機缚臈電晶體的元件構成之一 例 有機薄膜電晶體的元件構成之一 132167.doc * 5〇 - 200917543 圖6係表示本發明之有機薄膜電晶體的元件構成之一例 之圖。 圖7係表示本發明之實施例中之有機薄膜電晶體的元件 構成之一例之圖。 _圖8係表示本發明之實施例中之有機薄膜發光電晶體的 元件構成之一例之圖。
圖9係表示實施例5中所得之本發明之有 體的發射光譜之圖。 機薄膜發光電晶 132167.doc -51 -
Claims (1)
- 200917543 十、申請專利範圍: L種有機薄膜電晶體,其係於基板上至少設置有問極電 極 '源極電極及沒極電極3個端子、絕緣體層以及有機 半導體層’藉由於閘極電極上施加電壓而控制源極-汲極 間電他者,上述有機半導體層包含具有下述通式⑴之結 構的有機化合物: ~ [化1][於式中βαβ2分別獨立係碳數為6〜6〇之2價芳香族炉 基或碳數為1〜60之2價芳香族雜環基,Rl〜R1〇分別獨立^ 虱原子素原子、氰基、碳數為卜川之烧基 1〜3〇之㈣基、碳數為㈣之燒氧基、碳數為㈣^ ==1〜30之燒胺基、碳數為2〜6。之二炫基胺 ί(烧基亦可相互鍵結而形成含氮原子之環結構)、碳數 為1〜30之烷基磺醯基、碳 數為1〜30之鹵烷基磺醯基、碳 為〜30之烷硫基、碳數為1〜之 * 3〜30之烷基矽烷基、碳 & “、石厌數為 .,— 數為6〜60之芳香族烴基或者碳數 為1〜60之芳香族雜環基, 此·#各基亦可具有取代基, 又,Ri〜R5、R6〜Rw中相鄰 和之環狀結構]。 #者之間亦可形成飽和或不飽 132167.doc 200917543 1 , B 2刀別獨立係包含苯環之2價芳香族烴 本%之2價芳香族雜環基。 土或者包含 月求項1之有機薄膜電晶體,其中 Βι及心分別獨立係 、34通式⑴中, 環基。 之Μ族雜環的芳香族雜 4·如°月求項1之有機薄臈電晶體,其中於上辻 6,及32係相對 、上述通式(1)中, 5·如請求項!之有機Γ2所夹之雙鍵為對稱結構。 基或碳數為心原子、碳數為〜 6 ·如請求項]夕 ^ H、、 ㈣電晶體,其中於上述通式⑴中, 之至少一以5山、HR9及^係氫原子,且WR8 “妷數為1〜30之烷基、碳數為1〜30之_烷 基、南素原子或氰基。 齒坑 7. -種有機薄膜發光電晶體’其係於 膜電晶體φ,月N噴1之有機溥 1用於源極-汲極間流動之電流獲得發光, 8. 曰由於閘極電極上施加電壓而控制發光。 極電極二7之有機缚膜發光電晶體’其中源極電極及汲 至少—者係包含功函數為4.2 eV以上之物質, 且/或至少-古> A A人 9·如請求…之有功函數為4.3^以下之物質。 、冑機薄膜電晶體’其中於源極電極及沒極 -、有機半導體層之間具有緩衝層。 1 0 ·如請求項7 $女j4lt ^ 、、 有機溥膜發光電晶體,其中於源極電極及 /及極電極與有機半導體層之間具有緩衝層。 132I67.doc 200917543 u· —種有機化合物,[化2] 其係以下 述通式(2)所表示:t2g词且係碳數為1〜30之烷基,b3&b 別獨立係2價之碳數為1〇〜6〇的2環以上之縮合J 起基或2價之碳數A 4 Α Λ 矢 基]。 60的2環以上之縮合芳香族雜環 132167.doc
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TWI421645B (zh) * | 2009-06-01 | 2014-01-01 | Taiwan Tft Lcd Ass | 圖案化的方法以及用於圖案化的堆疊結構 |
US8946688B2 (en) | 2009-12-14 | 2015-02-03 | Idemitsu Kosan Co., Ltd. | Polycyclic ring-fused compound and organic thin film transistor utilizing the same |
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JPWO2011087130A1 (ja) * | 2010-01-18 | 2013-05-20 | 株式会社クラレ | アセチレン化合物およびそれを含有している有機半導体材料 |
TW201327817A (zh) * | 2011-12-16 | 2013-07-01 | Ind Tech Res Inst | 雙載子電晶體元件結構及其製造方法 |
US10141528B1 (en) * | 2017-05-23 | 2018-11-27 | International Business Machines Corporation | Enhancing drive current and increasing device yield in n-type carbon nanotube field effect transistors |
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TWI421645B (zh) * | 2009-06-01 | 2014-01-01 | Taiwan Tft Lcd Ass | 圖案化的方法以及用於圖案化的堆疊結構 |
US8946688B2 (en) | 2009-12-14 | 2015-02-03 | Idemitsu Kosan Co., Ltd. | Polycyclic ring-fused compound and organic thin film transistor utilizing the same |
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