TWI473781B - 醌型化合物及其應用於半導體基體材料、電子及光電結構元件 - Google Patents

醌型化合物及其應用於半導體基體材料、電子及光電結構元件 Download PDF

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TWI473781B
TWI473781B TW97124804A TW97124804A TWI473781B TW I473781 B TWI473781 B TW I473781B TW 97124804 A TW97124804 A TW 97124804A TW 97124804 A TW97124804 A TW 97124804A TW I473781 B TWI473781 B TW I473781B
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Zeika Olaf
Faltin Ina
Lux Andrea
Willmann Steffen
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Novaled Ag
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Description

醌型化合物及其應用於半導體基體材料、電子及光電結構元 件
本發明係關於一種醌型化合物及其用做摻雜劑以摻雜電子及/或光電結構元件中有機半導體基體材料、做為電荷注入層、做為電洞阻擋層、做為電極材料、做為傳送材料本身、做為儲存材料，及係關於有機半導體材料及電子或光電結構元件。
藉由摻雜以改變有機半導體的電性質，特別是導電率為已知，如在無機半導體例如矽半導體的情況亦同。此處，起初為非常低的導電率之增加，及依據所使用摻雜劑的形式而定，在該半導體費米能位之變化可經由產生電荷載體於基體材料而達到。此處摻雜造成電荷傳送層導電率的增加，結果使得歐姆損失減少，及在接點與該有機層之間的改良電荷載體傳送。無機摻雜劑例如鹼土金屬(例如銫)或路易士酸(例如FeCl3 、SbCl5 )在有機基體材料的情況一般為不利的因為它們的高擴散係數，因為它們損傷電子結構元件的功能及穩定性，參考D. Oeter, Ch. Ziegler, W.Gopel合成金屬(1993)61 147-50;Y.Yamamoto等(1965)2015;J. Kido等Jpn J. Appl. Phys. 41 (2002)L358-60。此外，後者摻雜劑具如此高的蒸氣壓使得技術用途為非常存疑的，而且，這些化合物的還原電位對技術上摻雜真正有興趣的電洞導體材料常為太低的。此外，這些摻雜劑的非常積極反應行為使得技術用途為困難的。
本發明的基本目的為提供一種可用做摻雜劑、做為電荷注入層、做為電洞阻擋層、做為電極材料、做為傳送材 料本身或是做為儲存材料及可克服該技藝缺點。這些化合物較佳為具足夠高的還原電位，於基體材料不具任何干擾影響及提供基體材料中電荷載體數目的有效提高及相當易於處理。
本發明進一步目的在於顯示使用這些化合物的可能性及提供有機半導體材料及使用所揭示化合物的電子或光電結構元件。
例如，應了解材料上與醌型化合物為相同的化合物但僅以另一種氧化狀態存在的雙陰離子及自由基陰離子係為醌型化合物的衍生物。
第一目的係由如申請專利範圍第1項的醌型化合物所解決，進一步目的係由進一步獨立申請專利範圍的主題所解決及較佳具體實施例係提供於子申請專利範圍。
令人驚訝地發現根據本發明的醌型化合物較先前已知受體化合物產生顯著較強及/或更穩定摻雜劑，在此期間該新穎醌型結構係以中性形式用做p-摻雜劑，與有機半導體基體材料相反。
特別是，在做為電結構元件的應用中當根據本發明使用化合物時電荷傳送層的導電率顯著提高及/或接點及該有機層之間的電荷載體傳送顯著改善。不受限於此觀念，假設在根據本發明使用醌型結構的應用CT複合物特別是藉由自特定周圍材料的至少一個電子之轉移而於經摻雜層中形成，基體材料的陽離子亦形成，其可在基體材料移動。以此方式，基體材料獲得相較於未經摻雜基體材料的導電 率為高的導電率，未經摻雜基體材料的導電率一般為<10-8 姆歐/公分，特別是常為<10-10 姆歐/公分。應小心基體材料具足夠高的純度，此種純度可使用傳統方法，例如，梯度昇華，得到，此種基體材料的導電率可藉由摻雜而提高至大於10-8 姆歐/公分，常為>10-5 姆歐/公分。此對具氧化電位大於-0.5伏特比Fc/Fc+ ，較佳為大於0伏特比Fc/Fc+ ，較佳為大於+0.2伏特比Fc/Fc+ 的基體材料為真。指標Fc/Fc+ 係表示用做電位的電化學決定，例如，循環伏安法的參考之氧化還原對二茂鐵/二茂鐵離子。
醌型化合物亦可用做電洞注入層，於是，例如，陽極/接受體/電洞傳送體的層結構可產生，電洞傳送體可為純的層或是混合層，特別是，電洞傳送體亦可使用接受體摻雜。陽極可為，例如，ITO。接受體層可為，例如，0.5-100奈米厚。
根據本發明進一步建立所敘述醌型化合物亦可用做電子結構組件中的注入層，較佳為介於電極與半導體層(其亦可為摻雜的)之間，或是亦可用做電子結構元件中的阻擋層，較佳為介於發射極及傳送層之間。根據本發明所使用的化合物相對於與空氣的反應性具令人驚訝為較高的穩定性。
摻雜
酞花菁複合物，例如，Zn(ZnPc)、Cu(CuPc)、Ni(NiPc)或其他金屬可用做可p-摻雜基體材料，及酞花菁配位基亦可為經取代的。亦可選擇性地使用萘並菁及樸啉的其他金 屬複合物。而且，芳香酯或雜芳香酯胺或聯苯胺衍生物亦可用做基體材料，其可為經取代的或未經取代的，例如TPD、a-TPD、TDATA，特別是亦可為旋環-鏈結衍生物例如旋環TTB。特別是，a-NPD及旋環TTB可用做基體材料。
除了多環芳烴雜芳香族例如特別是咪唑、噻吩、噻唑衍生物，雜三亞苯之外，其他亦可用做基體材料，選擇性地亦可使用二聚的、寡聚的或聚合的雜芳香族。雜芳香族較佳為經取代的，特別是芳基-取代的，例如苯基-或萘基- 取代的，它們亦可以旋環化合物存在。
要了解在本發明所提供基體材料可彼此或是與其他物質混合而使用，要了解亦可使用具半導體性質的合適其他有機基體材料。
摻雜濃度
摻雜劑較佳為以相對於基體分子或是相對於聚合基體分子的單體為1:1的摻雜濃度存在，較佳為以1:2或更少的摻雜濃度，特佳為1:5或更少或1:10或更少。摻雜濃度可在1:1至1:100,000的範圍，特別是在1:5至1:10,000的範圍，或是1:10至1:1,000的範圍，例如在1:10至1:100或1:25至1:50的範圍且不限於上述範圍。
進行摻雜
使用根據本發明所使用的化合物摻雜特別基體材料可由下列方法的其中一個或組合進行：a)在真空與一個基體材料來源及一個摻雜劑的混合蒸發。
b)基體材料及p-摻雜劑於基板上的依序沉積及接著特別是藉由熱處理擴散摻雜劑。
c)由p-摻雜劑溶液摻雜基體層及接著特別是藉由熱處理蒸發溶劑。
d)藉由施用於表面的摻雜劑層表面摻雜基體材料層。
e)基體分子及摻雜劑溶液的製造及由習知方法例如溶劑蒸發或離心後續製造此溶液層。
摻雜亦可選擇性地以此種方式發生使得摻雜劑自前驅體化合物(其在加熱及/照射期間釋出摻雜劑)蒸發出，例 如，羰基化合物、二氮化合物或類似化合物可用做在摻雜劑釋出期間放出CO、氮或類似物質的前驅體化合物及亦可使用其他合適前驅體例如，鹽類，如鹵化物或類似鹽類。蒸發所需熱量基本上可由照射提供及亦可以標的方式輻射為某些帶的化合物或前驅體或要被蒸發的化合物複合物例如電荷轉移複合物的某些帶以藉由複合物的離解，例如藉由轉移為激發態，而促進化合物蒸發。然而，複合物亦特別是足夠穩定的以在所提供條件下以不離解方式蒸發或是施用於基板，要了解亦可使用其他合適方法以進行摻雜。
於是，有機半導體的p-摻雜層可以此方式產生，其可以多重方式使用。
半導體層
半導體層可由根據本發明所使用的醌型結構製造，這些半導體層可選擇性地非線性地設計，例如傳導路徑、接點或類似方式。此處醌型結構可與用做基體材料的另一種化合物一起做為p-摻雜劑及摻雜比可為1:1或更少。所使用摻雜劑亦可以相對於特定其他化合物或成分的較高量存在使得摻雜劑：化合物的比值可為>1:1的比值，例如在2:1、5:1、10:1或20:1或更高的比值。在製造經摻雜層的情況，且不限於此，特定其他成分可為一種例如可用做基體材料的成分。所使用摻雜劑亦可選擇性地以純的形式存在，例如純的層。
包含摻雜劑或基本上由摻雜劑組成或完全由摻雜劑組成的區域可以電流傳導方式與排列於此種基板上的有機半 導體材料及/或無機半導體材料接觸。
特別是醌型結構可根據本發明較佳地用做p-摻雜劑，例如以1:1或1:2的比值。例如，當使用ZnPc、旋環TTB或a-NPD做為基體時，可藉由根據本發明所使用的拉電子化合物做為p-摻雜劑達到具於室溫在10-5 姆歐/公分或更高範圍，例如10-3 姆歐/公分或更高，例如，10-2 姆歐/公分的導電率之半導體層。當使用酞花菁鋅做為基體時，可達到大於10-8 姆歐/公分的導電率，例如10-6 姆歐/公分。另一方面，未經摻雜酞花菁鋅的導電率最大為10-10 姆歐/公分。
要了解具摻雜劑的層或結構可包含一或更多不同醌型結構。
電子結構元件
當使用所敘述化合物以產生可特別是以層或電傳導路徑的形式排列之p-摻雜有機半導體材料時，複數個包含電傳導路徑的電結構元件或設備可使用p-摻雜有機半導體層產生。在本發明觀點，觀念”電結構元件”亦包含光電結構元件。結構元件的電功能活性區域的電性質例如導電率、發光性質或類似性質可由使用所敘述化合物而有利地改變，於是，可改善所摻雜層導電率及/或可達到自接點進入經摻雜層的電荷載體注入之改善。
本發明包含特別是有機發光二極體(OLED)、有機太陽電池、場效電晶體、有機二極體，特別是那些具高整流比例如103 -107 ，較佳為104 -107 或105 -107 ，及由拉電子醌型結構所製造的有機場效電晶體。應了解以根據本發明方式拉 電子機或接受體基或拉電子結構具較氫為更強的拉電子作用，觀念”拉電子芳基-及雜芳基”係表示芳香族及/或雜芳香族，它們根據本發明為缺電子的及具較苯為低的電子密度。
在電結構元件元件中基於有機基體材料的p-摻雜層可存在於，例如，下列層結構中，其中個別層的基底材料或基體材料較佳為有機的：p-i-n:p-摻雜半導體-本質半導體-n-摻雜半導體，n-i-p:n-摻雜半導體-本質半導體-p-摻雜半導體，"i"再次為一種未經摻雜層，"p"為一種p-摻雜層，此處接點物質為電洞-注入的及例如ITO或金的層或接點可提供於p-側，或是為電子注入的，及ITO、鋁或銀的層或接點可提供於n-側。
在上述結構中若必要i層亦可省略，在此情況可得到具p-n或n-p過渡的層序列。然而，所敘述化合物的使用並不限於上文所引用示例具體實施例，特別是，層結構可由額外合適層的引入而補充或改良。特別地是，具此種層序列的OLEDs，特別是，具pin結構或與之相反的結構，可使用所敘述化合物產生。
特別是，金屬-絕緣體-p-摻雜半導體形式(min)或是亦可選擇性地pin形式的有機二極體可在所敘述p-摻雜劑的協助下，例如以酞花菁鋅為基礎製造。這些二極體顯示105 及更高的整流比(整流比，相關於在通道方向的電流對比在結構部份反方向的電流)，而且，具p-n過渡的電結構元件可使用所引用化合物製造，於此相同半導體材料用於p-或 n-摻雜側(均相p-n過渡)。
然而，根據本發明化合物亦可以層、傳導路徑、點接點或類似形式使用於電結構元件，若它們相對於另一組件為佔多數的，例如，以純或基本上純的形式做為注入層。
現在使用下列實例以說明性方式敘述本發明進一步目的及優點，這些實例係僅考慮為說明性及不做為限制本發明範圍。
醌型化合物的製備
根據本發明醌型化合物可根據已知方法藉由氧化反應由適當二氫化合物合成，此二氫化合物可由CH-酸性化合物的親核取代反應由缺電子芳香族或雜芳香族製備，參考L. Brucsis, K. Friedrich Chem. Ber. 109 (1976)2469-74;S. Yamaguchi等Bull. Chem. Soc. Jpn. 62 (1989)3036-7; E.L.Martin美國專利第3558671號，此處所示係使用實例六氟苯a 及氰四氟苯乙腈化合物b 於下列式子。
在CH-酸性反應物上的保護基例如，烷基、苄基、三烷基甲矽基或硫代烷基對第二取代反應為有利的。
合成實例
二氫化合物
4,4'-十氟二苯並氫基-2,3,5,6,2',3',5',6'-八氟-駢苯烯的合成
於些微乙二醇二甲醚的2當量二五氟苯基-第三丁基甲烷於冰冷卻及保護氣體下緩慢配料為2當量氫化鈉於乙二醇二甲醚的懸浮液，在進行添加之後混合物於室溫更攪拌30分鐘，迅速加入1當量十氟二苯基及於60℃加熱混合物3小時。在冷卻結束後，使用水沉澱混合物及以些微甲醇及醚洗，所得到產物在保護氣體環境下於沸騰二苯基醚數分鐘分裂出丁烷而轉化為黃橙色產物，其可在冷離後由吸引移除。Fp.:>250℃。
雙[1-氰基-1-(4-氰基-四氟苯基)-亞甲基]-2,5-二氟-苯基-1,4-二甲腈的合成
將2.5毫莫耳四氟對苯二甲腈與5.1毫莫耳NaH於氬氣下懸浮於50毫升二甲氧基乙烯，將6.0毫莫耳(1.28公克)2-第三丁基-4'-氰基四氟苯基乙腈於5毫升二甲氧基乙烯於5℃滴入混合物。在於室溫攪拌30小時後，將混合物倒入200毫升冰水及使用氫氯酸酸化，濾出所得到紫色固體及於真空乾燥。產物藉由自合適溶劑再結晶而純化及接著在250℃於二苯基醚分裂出丁烷。在冷離後，加入乙醚及將混合物調整為冷的，藉由吸引移除所沉澱產物及於真空乾燥。(產率1.55公克)。ESE-MS分析(陰性偵測，自於 MeOH/0.5毫莫耳濃度NH4OAc溶液直接進入)：m/z=587 [M-H]- ，293 [M-2H]2- 。
醌型化合物的製備(氧化反應)
3,6-雙[1-氰基-1-(4-氰基-苯基)-亞甲基]-2,5-二氟-環己-1,4-二烯-1,4-二甲腈的合成
使用冰醋酸將相對應二氫化合物配料且不需進一步純化為完全溶液及加入冷卻至0℃的硝酸與氫溴酸的混合物。在添加完成之後仍將混合物於室溫攪拌，使用水配料直到固體開始沉澱及於室溫進一步攪拌。藉由吸引移除橙色固體，以水洗及於真空乾燥(在所有階段產率為76%)。
DI-MS(EI):m/z=586 [M]+ ，19 F-NMR (CD3 CN): δ=-100.5 (m, 2F)，-127.7 (m, 4F)，-131.6 (m, 4F)ppm。
摻雜應用實例
一種非常缺電子及拉電子醌型化合物非常清潔地提供。
放置於容器的缺電子醌型化合物與基體材料同時蒸發，根據示例具體實施例基體材料係為酞花菁鋅、旋環TTB或a-NPD。p-摻雜劑與基體材料可以一種方式蒸發使得在真空蒸發系統中沉澱於基板上的層具p-摻雜劑與基體材料為1:10的摻雜比。
將使用p-摻雜劑摻雜的特別有機半導體材料層施用於 排列於玻璃基板上的ITO層(氧化銦錫)。在施用p-摻雜有機半導體層之後，藉由氣相沉積合適金屬而施用金屬陰極以產生有機發光二極體。要了解有機發光二極體亦可具一般稱的倒反層結構，於此層序列為：玻璃基板-金屬陰極-p-摻雜有機層-透明傳導保護層(例如ITO)，要了解可依據應用提供其他層於個別所引用層之間。
使用3,6-雙[1-氰基-1-(4-氰基-苯基)-亞甲基]-2,5-二氟-環己-1,4-二烯-1,4-二甲腈的摻雜
摻雜性能係由3,6-雙[1-氰基-1-(4-氰基-苯基)-亞甲基]-2,5-二氟-環己-1,4-二烯-1,4-二甲腈(5莫耳%)與旋環TTB的共蒸發檢查及測量所得到混合層的導電率。發現摻雜層的導電率為1.8x10-4 姆歐公分-1 。
在上文敘述及在申請專利範圍的本發明特徵可以個別地及以任何組合在其不同具體實施例對實現本發明為必要的。

Claims (9)

  1. 一種具結構1的醌型化合物： 其中：每一個R1 -R4 係獨立地選自鹵素、CN、全氟化C1 -C10 烷基、拉電子芳基及雜芳基；每一個X及Y係獨立地選自 且Z=CN；Ar係獨立地選自受體-取代的及/或全鹵化的芳香族烴；及雜芳基係選自取代或未經取代的拉電子芳香族雜環化合物。
  2. 如申請專利範圍第1項的醌型化合物，其特徵在於R1 -R4 係選自氟及全氟化C1 -C10 烷基。
  3. 如申請專利範圍第1或2項的醌型化合物，其特徵在於Ar係選自全氟化芳香族烴。
  4. 一種如申請專利範圍第1項的醌型化合物的用途，該醌型化合物在電子及光電結構元件中係用做p-摻雜有機半導體基體材料的摻雜劑或做為電荷注入層。
  5. 一種包含有機基體化合物及p-摻雜劑的有機半導體材料，其特徵在於該p-摻雜劑係為如申請專利範圍第1 項的化合物。
  6. 如申請專利範圍第5項的有機半導體材料，其特徵在於摻雜劑與基體分子的莫耳摻雜比或是摻雜劑與聚合基體分子的單體的摻雜比係為介於1：1及1：100之間。
  7. 一種具電功能活性區域的電子或光電結構元件，其特徵在於該電活性區域係包含至少一種如申請專利範圍第1項的化合物。
  8. 如申請專利範圍第7項的電子或光電結構元件，其特徵在於該電活性區域係包含使用至少一種摻雜劑摻雜的有機半導體基體材料以使用至少一種如申請專利範圍第1項的化合物改變該半導體材料的電性質。
  9. 如申請專利範圍第7項的電子及光電結構元件係為有機發光二極體、光電池、有機太陽電池、有機二極體或有機場效電晶體的形式。
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US20170012203A1 (en) 2017-01-12
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