TWI508342B - 氧碳-、擬氧碳-、軸烯化合物及其用法 - Google Patents
氧碳-、擬氧碳-、軸烯化合物及其用法 Download PDFInfo
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Description
本發明係關於氧碳-、擬氧碳-、軸烯化合物及其做為摻雜有機半導體基質材料的有機摻雜劑以改變其電性質、做為阻擋層材料及電荷注入層及做為電極材料之用法,本發明亦相關於一種有機半導體材料及相關於一種電子組件,其中使用氧碳-、擬氧碳-及軸烯化合物。
在本申請案中所有環原子為sp2-脂環基化及某程度地可能攜帶外環C-C雙鍵的脂環基係指定為軸烯,亦參考H.Hopf及G.Maas,Angew.Chem.(1992),8,955。氧碳-及擬氧碳化合物係已知為非苯型芳香族化合物,參考,例如,G.Seitz,Nachr.Chem.Tech.Lab.28(1980),804-807頁。第一個氧碳化合物,克酮酸鉀,係由L.Gmelin於1825自鉀及炭製造,這些化合物,其中至少一個氧原子由另一個雜原子取代,係指定為擬氧碳化合物,如為該技藝專家所熟知。
多年來已知有機半導體關於其電傳導性可由摻雜大大地影響之,此種有機半導體基質材料可由具有良好電子給予體性質的化合物或是由具有良好電子接受體性質的化合物所製造,已知強的電子接受體例如四氰基醌二甲烷(TCNQ)或2,3,5,6-四氟-四氰基-1,4-苯醌二甲烷(F4TCNQ)可用於摻雜電子給予體材料(HT),M.Pfeiffer、A.Beyer、T.Fritz、K.Leo,應用物理信件,73(22),3202-3204(1998),及J.Blochwitz、M.Pfeiffer、T.Fritz、K.Leo,應用物理信件,73(6),729-731(1998),它們藉由電子轉移方法在似電子給予體基質材料(電洞傳送材料)產生一般稱的電洞,此電
洞的數目及移動率或多或少顯著影響基質材料的電導性,例如,N,N’-全芳基化聯苯胺TPD
或N,N’,N”-全芳基化星狀化合物例如物質TDATA
,或是,然而,某些金屬酞菁化合物,例如特別是酞菁鋅ZnPc
亦已知為具有電洞傳送性質的基質材料。
然而,先前所提及化合物在經摻雜半導有機層或是具有此種經摻雜層的相對應電子組件之製造的技術使用之缺點因為在大型製造工廠的製造方法或是技術規模的製造方法無法總是足夠精確的,此造成在方法內的高控制-及調節花費以達到所欲產品品質或是不欲的產品裕度,而且,在先前已知有機給予體相關於電子組件例如發光二極體(OLEDs)、場效電晶體(FET)或太陽電池本身的使用存在一些缺點因為在處理摻雜劑時所指出製造困難會造成電子組件的不欲不規則性或是造成電子組件的不欲老化作用,然而,同時應考慮所要使用的摻雜劑具有適合於該應用情況的極高電子親和力(還原電位)及其他性質,因為例如,摻雜劑亦共同決定在所提供條件下的有機半導體層的電導率及其他電性質。基質材料的HOMO及摻雜劑的LUMO之能量位置對摻雜效果為決定性的。
本發明具克服該技藝缺點的工作,特別是使一種新的有機內消旋化合物為可提供的,它們可特別用做摻雜有機半導體的摻雜劑,而且其可在製造方法容易地處理及其產生一種電子組件,其有機半導材料可再製地製造。
此工作係藉由本申請案的獨立項申請專利範圍所解
決,較佳具體實施例係得自子申請專利範圍。
在根據本發明的化合物中LUMO的位置為如此低的使得進一步技術上感興趣電洞傳送材料可第一次有效地被摻雜,因為LUMO的該極低位置及因為該化合物的相關高還原電位甚至太陽電池的性能效率可顯著改善。此外,這些化合物因為其高極性故在有機層為非常擴散穩定的,製造方法可被較佳地控制及於是以較少花費及在相同條件下可以更可再製方式由較高蒸發溫度及較低揮發性進行,然而,藉由使得氧碳、擬氧碳及軸烯化合物提供做為摻雜劑,這些化合物使得於在低擴散係數的特別組件中已給予摻雜劑的有利電子親和性情況下有機半導體基質的足夠電傳導為可能,其確保組件結構在時間上為均一的。而且,接點進入經摻雜層的電荷載體注入可由摻雜劑改善。而且,經摻雜有機半導體材料及所得電子組件可因為根據本發明使用的化合物而具有改善的長時間穩定性,此對例如隨時間的摻雜濃度之降低有關係,此進一步對相鄰於電子組件的未經摻雜層排列的經摻雜層之穩定性有關使得光電組件具有增加的光電性質長時間穩定性例如於已知長度的的光產額,太陽電池的效率或類似結果。
具根據本發明使用的化合物的基板之蒸發速率可使用例如石英厚度監測器決定,如習慣用於,例如OLEDs的製造。特別是,基質材料及摻雜劑的蒸發速率之比值可由使用兩個個別石英厚度監測器個別測量它們而量度之以調整摻雜比。
要了解根據本發明所使用的化合物較佳為使得它們或多或少蒸發或是實際上未分解,然而,若必要,甚至可使用有目的的前軀體做為摻雜源,其會釋出根據本發明所使用的化合物,這些前軀體可為例如,揮發性或非揮發性無機或有機酸的酸添加鹽類,或是它們的電荷傳送複合物,此酸及/或電子給予體較佳為不揮發或是僅些微揮發或是使用該電荷傳送複合物本身做為摻雜劑。
摻雜劑係以一種方式較佳地選擇使得其在已知相同條件下,例如,特別是,在已知基質材料(例如酞菁鋅或是下文進一步所引用的另一種基質材料)摻雜濃度(莫耳比、摻雜劑:基質、層厚度、電流強度)產生與F4TCNQ一樣高的導電度或是較佳為較F4TCNQ為高,例如,導電率(姆歐/公分)大於/等於1.1倍、1.2倍或大於/等於1.5倍或兩倍的F4TCNQ做為摻雜劑的導電率。
根據本發明所使用摻雜劑係以一種方式較佳地選擇使得在溫度自100℃改變至RT(20℃)之後以此種摻雜劑摻雜的半導有機材料仍具有20%,較佳為30%,特佳為50%或60%的於100℃的導電率(姆歐/公分)值。
數種較佳氧碳-、擬氧碳-及軸烯化合物會示於下文,其可有利地用於本發明目的。
[3]軸烯衍生物
R1=甲基、異丙基、第三-丁基
[4]軸烯衍生物
[5]軸烯衍生物
氧碳-、擬氧碳-及[6]軸烯結構的進一步衍生物
氧碳-、擬氧碳-及軸烯結構的製備
第一個氧碳化合物,克酮酸鉀,係由L.Gmelin於1825自鉀及炭製造,氧碳化合物及它們的酯類與鹵化物類較佳為與富含電子化合物例如脂族及芳香族胺、芳香族及雜環芳香族化合物反應,A.H.Schmidt,合成(1980)961,在路易士酸或CH-酸性化合物存在下藉由強鹼例如芳基乙腈、1,3-二酮、環戊二烯、丙二腈、接受體-取代二芳基甲烷、缺電子二雜環芳基甲烷由四氯環丙烯及酚得到的反應產物特別適合用於根據本發明應用。[3]軸烯係在氧化反應發生後得
到,R.West等,有機化學期刊(1975)40 2295;T.Kazuka、T.Shinji化學協會期刊(1994)519;T.Fukunaga等,JACS(1976)98 610。
二氯方酸及酚,其接著氧化為4[軸烯]亦進一步為非常適合的,R.West,S.K.Koster,有機化學期刊(1975)40 2300;CH-酸性丙二酸二腈的親核性陰離子亦可較佳為在將醇分離為二負方酸化合物下而以酯取代,T.Fukanaga美國化學協會期刊(1976)98 610;W.Ziegenbein,H.-E.Sprenger Angew.化學(1967)79 581;G.Seitz等Chem.Ber.(1987)120 1691。這些經CN-取代的化合物的氧化反應在過去僅電化學地成功,T.A.Blinka,R.West,Tetrahedron Lett.(1983)24 1567。[4]軸烯亦可由二醌乙烯的熱二聚過程製備,R.West,S.K.Koster,JOC(1975)40 2300。
以丙二腈取代的第一種克酮酸衍生物能夠由Fatiadi,有機化學期刊(1980)45 1338,美國化學協會期刊(1978)100 2586產生,這些化合物的氧化反應亦由他A.J.Fatiadi,L.M.Doane電化學地檢查,J.Electroanal.Chem.(1982)135 193-209。
然而,甚至[6]軸烯為已知,H.Hopf,A.K.Wick Helv.Chim.Acta(1961)46 380-6。
少數之後的代表性化合物已及/或用於電子照相做為於電視螢幕的電激發光材料,做為染料,做為光導電體,做為有機氧化劑,美國專利第4003943(1977)號,日本專利07-168377,日本專利2004010703 A(2004),美國專利第
4133821(1979)號。
新環狀氧碳-及擬氧碳衍生物的製備
實例
a)1,3-雙(二氰基亞甲基)茚滿-2-烯亞基-雙(4-氧代-[3,5-二-第三丁基]-2,5-環己二烯亞基)-環丙烷
將4,75公克雙(4-氧代-[3,5-二-第三丁基]-2,5-環己二烯亞基)-環丙烷、3,5公克1,3-雙(二氰基亞甲基)-茚滿及60毫克-丙氨酸溶解於12毫升醋酸酐及於攪拌下回流加熱,將混合物與60毫升甲苯配料,使之冷卻及藉由吸引移出紅-褐色結晶固體,接著將混合物以苯/甲苯洗及再結晶。
產率:4.6公克
將2.5公克的該紅-褐色結晶在氬氣下溶解於100毫升氯仿及使用4.7公克紅色亞鐵氰化鉀及8.8公克KOH於150毫升水中的溶液混合,在1小時密集攪拌之後,有機相係使用Na2SO4乾燥及蒸發至低堆塊及將產品再結晶。
產率:2.3公克黑-綠色結晶於分解下fp.>250℃
b)(2E,2'
E,2”E)-2,2'
,2”-(環丙烷-1,2,3-三烯亞基)叁(2-五氟苯乙腈)
將4公克(20毫莫耳)五氟苯乙腈於10毫升乙二醇二甲醚的溶液逐滴加至1.6公克NaH於40毫升乙二醇二甲醚及使用冰水冷卻,接著逐滴加入0.9公克四氯環丙烯於10毫升乙二醇二甲醚的溶液。在於室溫攪拌24小時之後將深色混合物倒至冰水及使用CHCl3
萃取,提出物為黑色固體。
將4公克粗中間產物溶解於50毫升CHCl3
,及將50毫升水(包含2公克K2
CO3
)加至此溶液,於攪拌下將0.5毫升溴加至此深綠色2-相混合物,之後,分離兩相,及有機相在於Na2
SO4
乾燥後使用旋轉蒸發器蒸發,剩餘有機固體使用合適溶劑再結晶。產率:約70%。
FP:182℃。
c)(2E,2'
E,2”E)-2,2'
,2”-(環丙烷-1,2,3-三烯亞基)叁(2-[2'
,3'
,5'
,6'
-四氟吡啶-4'
-基]乙腈)。
將4.75公克2,3,5,6-四氟吡啶乙腈於10毫升乙二醇二甲醚的溶液逐滴加至0.4公克LiH於60毫升乙二醇二甲醚。之後將1.1公克四氯環丙烯逐滴加至該溶液及攪拌過夜。將混合物倒至冰水及使用EtOAc萃取,在乾燥提出物及蒸發之後留下4.6公克固體。
將2.25公克固體溶解於50毫升AcOH,及加入5毫升HNO3
(65%),將水加至該橙-褐色溶液,及分離所得沉澱物,以水洗及乾燥。產率:1公克。Fp:170℃。
d)(2E,2'
E,2”E)-2,2'
,2”-(環丙烷-1,2,3-三烯亞基)叁(2-(2,6-二氯-3,5-二氟-4-(三氟甲基)苯基)乙腈)。
將0.29公克LiH懸浮於68毫升乙二醇二甲醚,及冷卻,及於氬氣環境下緩慢加入5公克2,6-二氯-3,5-二氟-4-(三氟甲基)苯基)乙腈)於6毫升乙二醇二甲醚,將混合物加熱至室溫,及將0.8公克四氯環丙烯逐滴加入,及將混合物攪拌過夜。將溶液倒至冰水,分離所得沉澱物及乾燥之。產率:4.75公克。
將3.5公克產物溶解於冰醋酸,及在冷卻下逐滴加入7毫升HNO3
,接著加入水,及分離所得沉澱物。使用合適溶劑再結晶產物。產率:72%。Fp.:185℃。
e)(2E,2'
E,2”E)-2,2'
,2”-(環丙烷-1,2,3-三烯亞基)叁(2-(2,3,5,6-四氟-4-氰基-苯乙腈)(2-2,3,5,6-四氟-4-三氟甲基-苯乙腈)。
內鹽:2,3-雙(氰基(4-氰基-2,3,5,6-四氟苯基)甲基)-1-三乙胺)環丙-2-烯-1-叉。
將5.34公克四氯環丙烯及13.8公克2,3,5,6-四氟-4-氰基芐甲腈於300毫升CH2
Cl2
冷卻,及加入17.1公克三乙胺,攪拌所得產物及將之加熱至室溫。接著加入水,及移出所得黃色固體,清洗及於空氣乾燥。產率:93%。
將1.15公克2,3,5,6-四氟-4-(三氟甲基)-芐甲腈於15毫升THF逐滴加至0.46公克LDA於55毫升THF,冷卻溶液,及逐滴加入2公克內鹽於DMPU的懸浮液。將溶液倒至冰水,移出沉澱物及以水洗及接著於真空中乾燥。產率:100%。
將2.7公克的要氧化物質溶解於70毫升AcOH,及將5.5毫升HNO3
(65%)逐滴加入,接著使用水沉澱要氧化物質。在分離後,以水洗及於真空中乾燥,產物以產率90%得到。Fp:>250℃。
f)(2E,2'
E,2”E,2'''
E)-2,2'
,2”,2'''
-(環丙烷-1,2,3,4-四烯亞基)四個(2-2'
,3'
,5'
,6'
-四氟-4'
-氰苯基)乙腈。
將1.2公克1,2-雙-甲苯磺醯-3,4-雙-二甲胺-quadratat與
2.14公克2,3,5,6-四氟-4-氰基-芐甲腈於20毫升吡啶加熱16小時並攪拌。濃縮溶液及倒入冰水。之後使用EtOAc萃取,濃縮該經乾燥萃取物產生可使用合適溶劑再結晶的產物。Fp.:>250℃。
基質材料
本發明敘述一種合適摻雜劑以用於有機半導材料例如習慣用於OLEDs或有機太陽電池的電洞傳送材料HT,該半導材料較佳為本質電洞傳導的。下列可應用於根據本發明的氧碳-及擬氧碳形式的摻雜劑。
該基質材料係部份(>10或>25重量%)或實質上(>50重量%或>75重量%)或是完全由金屬酞菁複合物、卟啉複合物、特別是金屬卟啉複合物、寡聚賽吩-、寡聚苯基-、寡聚苯苯撐乙烯-或是齊聚芴化合物所組成,其中寡聚物較佳為包含2-500或更多,較佳為2-100或2-50或2-10或更多基體,寡聚物亦可包含>4、>6或>10或更多基體,特別是亦對上文所指示範圍,於是,例如,4或6-10基體,6或10-100基體或10-500基體。單體及寡聚物可為經取代的或未經取代的及甚至所引用寡聚物的嵌段-或混合聚合物可存在及具有三芳香基胺單元的化合物或是旋環-雙芴化合物存在。所引用基質材料亦可與彼此以組合存在,選擇性地亦與其他基質材料以組合存在。該基質材料可具有電子提供取代基例如烷基-或烷氧基,其具有降低的游離能或是降低該基質材料的游離能。
用做基質材料的該金屬酞菁複合物或是卟啉複合物可
具有主族金屬原子或是子族金屬原子,金屬原子Me可為4-、5-或6-配位的,例如以氧代-(Me=O)、二氧代-(O=Me=O)亞胺-、二亞胺-、羥基-、二羥基-、胺基-或二胺基複合物的形式,且不限於這些。酞菁複合物或是卟啉複合物可每一個為部分氫化的,然而,內消旋環系統較佳為未受干擾。酞菁可包含,例如,鎂、鋅、鐵、鎳、鈷、鎂、銅或釩(=VO)做為中心原子。於卟啉複合物的情況相同或其他金屬原子或氧金屬原子可存在。
特別是,此種可摻雜電洞傳送材料HT
可為芳基化聯苯胺,例如,N,N’-全芳基化聯苯胺或是其他二元胺例如形式TPD
(其中一個、多個或是所有芳基可具有芳香族雜原子),合適芳基化星狀化合物例如N,N’,N”-全芳基化星狀化合物例如化合物TDATA
(其中一個、多個或是所有芳基可具有芳香族雜原子)。芳基可包含苯基、萘基、吡啶、喹啉、異喹啉、噠嗪、嘧啶、吡嗪、吡唑、咪唑、噁唑、呋喃、吡咯、吲哚或類似物,特別是上文所引用化合物的每一個。特定化合物的苯基可由賽吩基部份或完全取代。
所使用材料較佳為完全由金屬酞菁複合物、樸啉複合物、具有三芳香基胺的化合物或旋環雙芴化合物所組成。
要了解甚至其他合適有機基質材料,特別是可使用具有半傳導性質的電洞傳導材料。
摻雜
摻雜可特別是以一種方式發生使得基質分子與摻雜劑的莫耳比值,或是在寡聚基質材料的情況基質單體數目與摻雜劑的比值為1:100000,較佳為1:10000,特佳為1:5至1:1000,例如1:10至1:100,例如1:50至1:100或是1:25至1:50。
摻雜劑的蒸發
使用根據本發明所使用的摻雜劑進行特定基質材料(此處較佳地顯示為電洞傳導材料HT)的摻雜可由下列方法的其中一個或是其組合產生:
a)使用一種HT來源及一種摻雜劑來源於真空下混合蒸發。
b)HT及摻雜劑的循序沉積及後續藉由熱處理的摻雜劑向內擴散。
c)藉由摻雜劑溶液摻雜HT層及後續藉由熱處理的溶劑蒸發。
d)藉由摻雜劑層施用於表面進行HT層的表面摻雜。
摻雜可以以一種方式進行使得摻雜劑自在加熱及/或照射下會釋出摻雜劑的前軀體化合物蒸發,照射可由電磁輻
射,特別是可見光、UV光或IR光,例如藉由雷射光或是亦可藉由其他輻射形式,進行。蒸發所需熱量可基本上可由照射提供及亦可以一種有目的的方式照射進入要蒸發的化合物或前軀體或化合物複合物例如電荷傳送複合物的某個帶以藉由轉化為激發態離解複合物而促進化合物的蒸發。要了解在下文所敘述的蒸發條件係關於沒有照射的蒸發條件及均勻蒸發條件係用於比較目的。
例如,下列可用做前軀體化合物:
a)摻雜劑及惰性、非揮發性物質的混合物或化學計量或混合結晶型化合物,例如聚合物、分子篩、氧化鋁、矽膠、及寡聚物或是具有高蒸發溫度的另一種有機或無機物質,其中摻雜劑係主要由凡德瓦爾力及/或鍵結至該物質的氫橋所鍵結。
b)摻雜劑及一種或多或少電子供體形式的非揮發性化合物V的混合物或化學計量或混合結晶型化合物,其中一種或多或少完全電荷轉移發生於該摻雜劑及該化合物V之間如同在電荷轉移複合物與或多或少富含電子聚芳香族或是雜環芳香族或是具有高蒸發溫度的另一種有機或無機物質。
c)摻雜劑及與該摻雜劑一起蒸發及具有與要摻雜物質HT相同或更高游離能的物質的混合物或化學計量或混合結晶型化合物,使得該物質不會形成電洞的陷阱於該有機基質材料。根據本發明該物質亦可與此處的基質材料相同,例如為金屬酞菁化合物或是聯苯胺。進一步合適揮發
性共物質例如對苯二酚、1,4-對苯二胺或是1-胺基-4-羥基苯或是其他化合物形式醌氫醌或是其他電荷轉移複合物。
電子組件
包含這些化合物的複數個電子組件或設備可使用根據本發明的有機化合物製造以產生可特別是以層或電力線路徑的形式排列的經摻雜有機半導材料。特別是,可使用根據本發明該摻雜劑係用以製造有機、發光二極體(OLED)、有機太陽電池、有機二極體,特別是那些具有高整流比例如103
-107
,較佳為104
-107
或105
-107
或有機場效電晶體。該經摻雜層的傳導率及/或接點進入該經摻雜層的電荷載體注入之改善可使用根據本發明該摻雜劑改善。特別是在OLEDs的情況組件可具有pin結構或是反結構且不限於此。然而,根據本發明該摻雜劑的用途不限於上文所引用的有利具體實施例。
示例具體實施例
本發明將以一些示例具體實施例詳細敘述。
要根據本發明使用的化合物,特別是,得自先前所敘述氧碳-及擬氧碳-化合物物質類的先前所指出示例化合物現在以下列方式用做不同電洞導體的摻雜劑,此部分係用於建構某些微電子或光電組件,例如,OLED。摻雜劑可在高溫下於高真空(約2 x 10-4
巴斯卡)與基質的電洞傳送材料同時蒸發,基質材料的典型基材蒸發速率為0.2奈米/秒(密度約1.5公克/公分3
),在相同假設密度根據所欲摻雜比值摻雜劑的蒸發速率可在0.001及0.5奈米/秒之間變化。
在下列實例電流測量係在1伏特於經摻雜HT材料1毫米長及約0.5毫米寬的電流路徑執行,在這些條件下ZnPc實際上沒有傳導任何電流。
實例:
實例1
使用二氰基亞甲基雙(4-氧代-[3,5-二-第三丁基]-2,5-環己二烯亞基)環丙烷摻雜ZnPc
導電率:1,5 x 10-5
姆歐/公分
實例2
使用二氰基亞甲基雙(4-氧代-[3,5-二-第三丁基]-2,5-環己二烯亞基)環丙烷摻雜旋環-TTP
導電率:3,6 x 10-7
姆歐/公分
實例3
使用1,3-雙(二氰基亞甲基)茚滿-2-亞甲基-雙(4-氧代-[3,5-二-第三丁基]-2,5-環己二烯亞基)環丙烷摻雜ZnPc。導電率:5,8 x 10-6
姆歐/公分
實例4
使用1,3-雙(二氰基亞甲基)茚滿-2-亞甲基-雙(4-氧代-[3,5-二-第三丁基]-2,5-環己二烯亞基)環丙烷摻雜旋環-TTP。導電率:5 x 10-7
姆歐/公分
實例5
使用(2E,2'
E,2”E)-2,2'
,2”-(環丙烷-1,2,3-三亞甲基)参(2-五氟苯基乙腈)10%摻雜N4
,N4'
-(二苯基-4,4'
-二基)雙(N4
,N4'
,N4'
-三苯基聯苯-4,4'
-二元胺)。導電率:3.21 x 10-6
姆歐/公分
實例6
使用(2E,2'
E,2”E)-2,2'
,2”-(環丙烷-1,2,3-三亞甲基)参(2-五氟苯基乙腈)10%摻雜旋環-TTP。導電率:1.89 x 10-6
姆歐/公分。
實例7
使用(2E,2'
E,2”E)-2,2'
,2”-(環丙烷-1,2,3-三亞甲基)参(2-五氟苯基乙腈)10%摻雜4,4'
-雙(10,11-二氫-5H-二苯駢[b,f]吖庚因-5-基)聯苯。導電率:1.55 x 10-7
姆歐/公分。
實例8
使用(2E,2'
E,2”E)-2,2'
,2”-(環丙烷-1,2,3-三亞甲基)参(2-[2'
,3'
,5'
,6'
-四氟吡啶-4'
-基]乙腈)5%摻雜旋環-TTP。導電率:4.35 x 10-5
姆歐/公分。
實例9
使用(2E,2'
E,2”E)-2,2'
,2”-(環丙烷-1,2,3-三亞甲基)参(2-[2'
,3'
,5'
,6'
-四氟吡啶-4'
-基]乙請)5%摻雜a-NPD。導電率:1.28 x 10-5
姆歐/公分。
實例10
使用(N,N'
,N”,N'''
-環丁烷-1,2,3,4-四亞甲基)四苯胺5%摻雜ZnPc。導電率:1.3 x 10-6
姆歐/公分。
實例11
使用(2E,2'
E,2”E,2'''
E)-2,2'
,2”,2'''
-(環丁烷-1,2,3,4-四亞甲基)N,N'
,N”,N'''
-環丁烷-1,2,3,4-四亞甲基)四個(2-全氟苯基)乙腈)5%摻雜旋環-TTP。導電率:3.3 x 10-5
姆歐/公
分。
在先前敘述及在申請專利範圍所揭示的本發明特徵可本質上個別地及以任何組合以在各種具體實施例實現本發明。
Claims (16)
- 一種有機內消旋化合物做為有機摻雜劑以摻雜有機半導基質材料、做為阻擋層、做為電荷注入層或做為有機半導體本身之用途,其特徵在於該內消旋化合物係為一具有下列分子式的氧碳-、擬氧碳-及軸烯化合物:
- 如申請專利範圍第1項所述的用途,其中,Y係為全氟烷基。
- 如申請專利範圍第1項或第2項所述的用途,其中,芳基係部份或完全氟化。
- 如申請專利範圍第1項所述的用途,其中,雜芳基係由吡啶基、嘧啶基、三氮雜苯及噁二唑選出。
- 如申請專利範圍第1項所述的用途,其中,R1 -R8 係獨立地由全氫化及/或部分氫化的烷基中選出。
- 一種具有下列分子式的軸烯化合物
- 如申請專利範圍第6項所述的軸烯化合物,其中,雜芳基係選自吡啶基、嘧啶基、三氮雜苯及噁二唑。
- 一種如申請專利範圍第6項或第7項所述的軸烯化合物或是其自由基陰離子鹽類或二陰離子鹽類做為一有機鐵磁體之用途。
- 一種如申請專利範圍第6項或第7項所述的軸烯化合物或是具有一給予者的電荷轉移複合物做為一有機鐵磁體之用途。
- 一種如申請專利範圍第6項或第7項所述的化合物或是其自由基陰離子鹽類或二陰離子鹽類做為一有機導體之用途。
- 一種如申請專利範圍第6項或第7項所述的化合物或是具有一給予者的電荷轉移複合物做為一有機導體之用途。
- 一種包含至少一種有機半導體基質化合物及一摻雜劑的有機半導材料,其特徵在於該摻雜劑係為如申請專利範圍第6項所述的一或更多軸烯化合物。
- 如申請專利範圍第12項所述的有機半導材料,其中該摻雜劑與一基質分子的莫耳摻雜比及/或是該摻雜劑與一聚合基質分子的單體單元的摻雜比係介於1:1與1:100,000之間。
- 一種具有電功能活性區域的電子組件,其特徵在於該電功能活性區域係使用至少一或更多如申請專利範圍第6項所述的軸烯化合物來製造。
- 如申請專利範圍第14項的電子組件,其中該電功能活性區域係包含以至少一摻雜劑摻雜的一有機半導基質材料,以使用至少一種或更多如申請專利範圍第6項中任一項的該軸烯化合物改變該有機半導基質材料的電性質。
- 如申請專利範圍第14項或第15項所述的電子組件,其為一有機發光二極體、一光電池、一有機太陽電池、一有機二極體或一有機場效電晶體的形式。
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Families Citing this family (116)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100026176A1 (en) * | 2002-03-28 | 2010-02-04 | Jan Blochwitz-Nomith | Transparent, Thermally Stable Light-Emitting Component Having Organic Layers |
DE502005009802D1 (de) * | 2005-11-10 | 2010-08-05 | Novaled Ag | Dotiertes organisches Halbleitermaterial |
US7919010B2 (en) * | 2005-12-22 | 2011-04-05 | Novaled Ag | Doped organic semiconductor material |
ATE394800T1 (de) | 2006-03-21 | 2008-05-15 | Novaled Ag | Heterocyclisches radikal oder diradikal, deren dimere, oligomere, polymere, dispiroverbindungen und polycyclen, deren verwendung, organisches halbleitendes material sowie elektronisches bauelement |
EP1837927A1 (de) * | 2006-03-22 | 2007-09-26 | Novaled AG | Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern |
DE102007012794B3 (de) * | 2007-03-16 | 2008-06-19 | Novaled Ag | Pyrido[3,2-h]chinazoline und/oder deren 5,6-Dihydroderivate, deren Herstellungsverfahren und diese enthaltendes dotiertes organisches Halbleitermaterial |
DE102007018456B4 (de) * | 2007-04-19 | 2022-02-24 | Novaled Gmbh | Verwendung von Hauptgruppenelementhalogeniden und/oder -pseudohalogeniden, organisches halbleitendes Matrixmaterial, elektronische und optoelektronische Bauelemente |
EP1988587B1 (de) | 2007-04-30 | 2016-12-07 | Novaled GmbH | Oxokohlenstoff-, Pseudooxokohlenstoff- und Radialenverbindungen sowie deren Verwendung |
EP1990847B1 (de) * | 2007-05-10 | 2018-06-20 | Novaled GmbH | Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials |
DE102007031220B4 (de) | 2007-07-04 | 2022-04-28 | Novaled Gmbh | Chinoide Verbindungen und deren Verwendung in halbleitenden Matrixmaterialien, elektronischen und optoelektronischen Bauelementen |
JP5279254B2 (ja) * | 2007-12-18 | 2013-09-04 | キヤノン株式会社 | 有機発光素子及び表示装置 |
US8057712B2 (en) * | 2008-04-29 | 2011-11-15 | Novaled Ag | Radialene compounds and their use |
DE102008061843B4 (de) | 2008-12-15 | 2018-01-18 | Novaled Gmbh | Heterocyclische Verbindungen und deren Verwendung in elektronischen und optoelektronischen Bauelementen |
DE102009013685B4 (de) | 2009-03-20 | 2013-01-31 | Novaled Ag | Verwendung einer organischen Diode als organische Zenerdiode und Verfahren zum Betreiben |
CN102482574B (zh) | 2009-06-18 | 2014-09-24 | 巴斯夫欧洲公司 | 用作场致发光器件的空穴传输材料的菲并唑化合物 |
DE102010023619B4 (de) | 2009-08-05 | 2016-09-15 | Novaled Ag | Organisches bottom-emittierendes Bauelement |
WO2011051404A1 (de) | 2009-10-28 | 2011-05-05 | Basf Se | Heteroleptische carben-komplexe und deren verwendung in der organischen elektronik |
EP2513125B1 (de) | 2009-12-14 | 2014-10-29 | Basf Se | Metallkomplexe, enthaltend diazabenzimidazolcarben-liganden und deren verwendung in oleds |
DE102010004453A1 (de) | 2010-01-12 | 2011-07-14 | Novaled AG, 01307 | Organisches lichtemittierendes Bauelement |
EP2367215A1 (en) * | 2010-03-15 | 2011-09-21 | Novaled AG | An organic photoactive device |
WO2011131185A1 (de) | 2010-04-21 | 2011-10-27 | Novaled Ag | Mischung zur herstellung einer dotierten halbleiterschicht |
JP5810152B2 (ja) * | 2010-04-27 | 2015-11-11 | ノヴァレッド・アクチエンゲゼルシャフト | 有機半導体材料および電子部品 |
US9178173B2 (en) | 2010-06-14 | 2015-11-03 | Novaled Ag | Organic light emitting device |
DE102010023620B4 (de) | 2010-06-14 | 2016-09-15 | Novaled Ag | Organisches, bottom-emittierendes Bauelement |
EP2586074B1 (en) | 2010-06-24 | 2016-12-28 | Basf Se | An organic field effect transistor with improved current on/off ratio and controllable threshold shift |
DE102010031979B4 (de) | 2010-07-22 | 2014-10-30 | Novaled Ag | Halbleiterbauelement, Verfahren zu dessen Herstellung, Verwendung des Halbleiterbauelementes und Inverter mit zwei Halbleiterbauelementen |
TWI526418B (zh) * | 2011-03-01 | 2016-03-21 | 諾瓦發光二極體股份公司 | 有機半導體材料及有機組成物 |
US9154477B2 (en) | 2011-05-26 | 2015-10-06 | First Data Corporation | Systems and methods for encrypting mobile device communications |
US9315724B2 (en) | 2011-06-14 | 2016-04-19 | Basf Se | Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs |
CN103732603B (zh) | 2011-06-14 | 2017-05-31 | Udc 爱尔兰有限责任公司 | 包含氮杂苯并咪唑碳烯配体的金属配合物及其在oled中的用途 |
DE102011055233A1 (de) | 2011-11-10 | 2013-05-16 | Novaled Ag | Lichtemittierende Vorrichtung und flächige Anordnung mit mehreren lichtemittierenden Vorrichtungen |
EP2780409A4 (en) | 2011-11-15 | 2015-09-16 | Basf Se | ORGANIC SEMICONDUCTOR COMPONENT AND MANUFACTURING METHOD THEREFOR |
EP2789028B1 (en) | 2011-12-06 | 2019-02-06 | Novaled GmbH | Organic light emitting device and method of producing |
DE102012100642B4 (de) | 2012-01-26 | 2015-09-10 | Novaled Ag | Anordnung mit mehreren organischen Halbleiterbauelementen und Verfahren zum Herstellen sowie Verwendung der Anordnung |
WO2013118812A1 (ja) * | 2012-02-10 | 2013-08-15 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子 |
TW201341347A (zh) | 2012-03-15 | 2013-10-16 | Novaled Ag | 芳香胺三聯苯化合物及其在有機半導體元件中的應用 |
EP2875039B1 (en) | 2012-07-19 | 2016-09-14 | UDC Ireland Limited | Dinuclear metal complexes comprising carbene ligands and the use thereof in oleds |
US9966539B2 (en) | 2012-08-31 | 2018-05-08 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
EP2706584A1 (en) | 2012-09-07 | 2014-03-12 | Novaled AG | Charge transporting semi-conducting material and semi-conducting device |
JP6333262B2 (ja) | 2012-09-20 | 2018-05-30 | ユー・ディー・シー アイルランド リミテッド | 電子用途のためのアザジベンゾフラン |
CN105051927B (zh) | 2013-03-20 | 2020-10-16 | Udc 爱尔兰有限责任公司 | 在oled中用作效率促进剂的氮杂苯并咪唑卡宾配体 |
WO2014177518A1 (en) | 2013-04-29 | 2014-11-06 | Basf Se | Transition metal complexes with carbene ligands and the use thereof in oleds |
EP2816644B1 (en) * | 2013-06-21 | 2017-08-16 | Novaled GmbH | Battery comprising a radialene compound as electroactive material |
WO2014202399A1 (en) * | 2013-06-21 | 2014-12-24 | Novaled Gmbh | Battery |
EP3266789B1 (en) | 2013-07-02 | 2019-09-25 | UDC Ireland Limited | Monosubstituted diazabenzimidazole carbene metal complexes for use in organic light emitting diodes |
CN109021022B (zh) | 2013-07-31 | 2021-04-16 | Udc 爱尔兰有限责任公司 | 发光的二氮杂苯并咪唑碳烯金属配合物 |
EP3063153B1 (en) | 2013-10-31 | 2018-03-07 | Idemitsu Kosan Co., Ltd. | Azadibenzothiophenes for electronic applications |
KR102175791B1 (ko) * | 2013-12-03 | 2020-11-09 | 엘지디스플레이 주식회사 | 유기 화합물 및 이를 포함하는 유기전계발광소자 |
KR20240005971A (ko) | 2013-12-06 | 2024-01-12 | 메르크 파텐트 게엠베하 | 화합물 및 유기 전자 소자 |
WO2015082046A2 (de) | 2013-12-06 | 2015-06-11 | Merck Patent Gmbh | Substituierte oxepine |
US10347851B2 (en) | 2013-12-20 | 2019-07-09 | Udc Ireland Limited | Highly efficient OLED devices with very short decay times |
DE102014102934B4 (de) | 2014-03-05 | 2016-01-07 | Novaled Gmbh | Behälter für die Verarbeitung organischer optoelektronischer Materialien |
WO2016016791A1 (en) | 2014-07-28 | 2016-02-04 | Idemitsu Kosan Co., Ltd (Ikc) | 2,9-functionalized benzimidazolo[1,2-a]benzimidazoles as hosts for organic light emitting diodes (oleds) |
EP2982676B1 (en) | 2014-08-07 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | Benzimidazo[2,1-B]benzoxazoles for electronic applications |
US10784448B2 (en) | 2014-08-08 | 2020-09-22 | Udc Ireland Limited | Electroluminescent imidazo-quinoxaline carbene metal complexes |
EP2993215B1 (en) | 2014-09-04 | 2019-06-19 | Idemitsu Kosan Co., Ltd. | Azabenzimidazo[2,1-a]benzimidazoles for electronic applications |
EP3015469B1 (en) | 2014-10-30 | 2018-12-19 | Idemitsu Kosan Co., Ltd. | 5-(benzimidazol-2-yl)benzimidazo[1,2-a]benzimidazoles for electronic applications |
WO2016079667A1 (en) | 2014-11-17 | 2016-05-26 | Idemitsu Kosan Co., Ltd. | Indole derivatives for electronic applications |
CN107074895B (zh) | 2014-11-18 | 2020-03-17 | Udc 爱尔兰有限责任公司 | 用于有机发光二极管中的Pt-或Pd-碳烯络合物 |
JPWO2016092883A1 (ja) * | 2014-12-08 | 2017-04-27 | 株式会社Joled | 表示素子および表示装置ならびに電子機器 |
EP3034507A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 1-functionalized dibenzofurans and dibenzothiophenes for organic light emitting diodes (OLEDs) |
EP3034506A1 (en) | 2014-12-15 | 2016-06-22 | Idemitsu Kosan Co., Ltd | 4-functionalized carbazole derivatives for electronic applications |
EP3054498B1 (en) | 2015-02-06 | 2017-09-20 | Idemitsu Kosan Co., Ltd. | Bisimidazodiazocines |
EP3053918B1 (en) | 2015-02-06 | 2018-04-11 | Idemitsu Kosan Co., Ltd. | 2-carbazole substituted benzimidazoles for electronic applications |
EP3061759B1 (en) | 2015-02-24 | 2019-12-25 | Idemitsu Kosan Co., Ltd | Nitrile substituted dibenzofurans |
KR102261644B1 (ko) | 2015-03-11 | 2021-06-08 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
EP3070144B1 (en) | 2015-03-17 | 2018-02-28 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
EP3072943B1 (en) | 2015-03-26 | 2018-05-02 | Idemitsu Kosan Co., Ltd. | Dibenzofuran/carbazole-substituted benzonitriles |
EP3075737B1 (en) | 2015-03-31 | 2019-12-04 | Idemitsu Kosan Co., Ltd | Benzimidazolo[1,2-a]benzimidazole carrying aryl- or heteroarylnitril groups for organic light emitting diodes |
KR102661925B1 (ko) | 2015-06-03 | 2024-05-02 | 유디씨 아일랜드 리미티드 | 매우 짧은 붕괴 시간을 갖는 고효율 oled 소자 |
CN105176519B (zh) * | 2015-09-01 | 2017-06-27 | 中节能万润股份有限公司 | 一种oled光电材料及其应用 |
EP3150604B1 (en) | 2015-10-01 | 2021-07-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolylyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
EP3150606B1 (en) | 2015-10-01 | 2019-08-14 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazoles carrying benzofurane or benzothiophene groups for organic light emitting diodes |
US20180291028A1 (en) | 2015-10-01 | 2018-10-11 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying benzimidazolo[1,2-a]benzimidazolyl groups, carbazolyl groups, benzofurane groups or benzothiophene groups for organic light emitting diodes |
US20180269407A1 (en) | 2015-10-01 | 2018-09-20 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole carrying triazine groups for organic light emitting diodes |
CN108349987A (zh) | 2015-11-04 | 2018-07-31 | 出光兴产株式会社 | 苯并咪唑稠合杂芳族类 |
WO2017093958A1 (en) | 2015-12-04 | 2017-06-08 | Idemitsu Kosan Co., Ltd. | Benzimidazolo[1,2-a]benzimidazole derivatives for organic light emitting diodes |
US9634009B1 (en) | 2015-12-18 | 2017-04-25 | International Business Machines Corporation | System and method for source-drain extension in FinFETs |
EP3182478B1 (en) | 2015-12-18 | 2018-11-28 | Novaled GmbH | Electron injection layer for an organic light-emitting diode (oled) |
US20190006601A1 (en) | 2015-12-21 | 2019-01-03 | Idemitsu Kosan Co., Ltd. | Nitrogen-containing heterocyclic compounds and organic electroluminescence devices containing them |
KR20170074170A (ko) | 2015-12-21 | 2017-06-29 | 유디씨 아일랜드 리미티드 | 삼각형 리간드를 갖는 전이 금속 착체 및 oled에서의 이의 용도 |
EP3208861A1 (en) | 2016-02-19 | 2017-08-23 | Novaled GmbH | Electron transport layer comprising a matrix compound mixture for an organic light-emitting diode (oled) |
EP3208862A1 (en) | 2016-02-22 | 2017-08-23 | Novaled GmbH | Charge transporting semi-conducting material and electronic device comprising it |
EP3208863B1 (en) | 2016-02-22 | 2019-10-23 | Novaled GmbH | Charge transporting semi-conducting material and electronic device comprising it |
WO2017178864A1 (en) | 2016-04-12 | 2017-10-19 | Idemitsu Kosan Co., Ltd. | Seven-membered ring compounds |
KR101872962B1 (ko) | 2016-08-31 | 2018-06-29 | 엘지디스플레이 주식회사 | 유기 화합물과 이를 포함하는 유기발광다이오드 및 유기발광표시장치 |
JP7149263B2 (ja) * | 2017-03-28 | 2022-10-06 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
CN106848084B (zh) * | 2017-03-31 | 2019-12-17 | 上海天马有机发光显示技术有限公司 | 一种oled显示面板、制作方法及含有其的电子设备 |
JP2020522876A (ja) | 2017-04-13 | 2020-07-30 | メルク パテント ゲーエムベーハー | 有機電子デバイス用組成物 |
DE102017111137A1 (de) | 2017-05-22 | 2018-11-22 | Novaled Gmbh | Organische elektrolumineszente Vorrichtung |
EP3418285B1 (en) | 2017-06-20 | 2020-05-06 | Idemitsu Kosan Co., Ltd. | Composition comprising a substituted ir complex and a phenylquinazoline bridged with a heteroatom |
WO2019002198A1 (en) | 2017-06-26 | 2019-01-03 | Merck Patent Gmbh | HOMOGENEOUS MIXTURES |
JP7247121B2 (ja) | 2017-07-05 | 2023-03-28 | メルク パテント ゲーエムベーハー | 有機電子デバイスのための組成物 |
US11591320B2 (en) | 2017-07-05 | 2023-02-28 | Merck Patent Gmbh | Composition for organic electronic devices |
CN107528007B (zh) | 2017-07-28 | 2020-03-10 | 上海天马有机发光显示技术有限公司 | 一种有机发光二极管、显示面板及显示装置 |
EP3466954A1 (en) | 2017-10-04 | 2019-04-10 | Idemitsu Kosan Co., Ltd. | Fused phenylquinazolines bridged with a heteroatom |
TWI785142B (zh) | 2017-11-14 | 2022-12-01 | 德商麥克專利有限公司 | 用於有機電子裝置之組成物 |
EP3502116B1 (en) | 2017-12-20 | 2020-11-25 | Novaled GmbH | Compound and an organic semiconducting layer comprising the same |
WO2019229011A1 (de) | 2018-05-30 | 2019-12-05 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
CN110746427A (zh) * | 2018-07-23 | 2020-02-04 | 上海和辉光电有限公司 | 一种p型半导体掺杂化合物及其用途 |
CN109928894B (zh) * | 2018-10-09 | 2022-05-03 | 宁波卢米蓝新材料有限公司 | 一种含有多元环的化合物、应用及有机电致发光器件 |
EP3653619A1 (en) | 2018-11-16 | 2020-05-20 | Novaled GmbH | Compound, organic electronic device comprising the same, and display device and lighting device comprising the same |
US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
CN112534602B (zh) | 2019-07-25 | 2024-05-10 | 出光兴产株式会社 | 混合物、有机电致发光元件和电子设备 |
CN110483495B (zh) * | 2019-09-16 | 2020-04-28 | 长春海谱润斯科技有限公司 | 一种杂环化合物及其有机电致发光器件 |
CN112624990A (zh) * | 2019-10-08 | 2021-04-09 | 广州华睿光电材料有限公司 | 含氮杂环取代的环丙烷类化合物及其应用 |
CN112876476A (zh) * | 2019-11-29 | 2021-06-01 | 上海和辉光电有限公司 | 作为p型掺杂的化合物、oled器件和有机太阳能电池 |
CN115443265A (zh) * | 2020-04-03 | 2022-12-06 | 住友化学株式会社 | 化合物 |
US20230225201A1 (en) | 2020-06-12 | 2023-07-13 | Novaled Gmbh | Organic Light Emitting Diode and Device Comprising the Same |
EP3989303A1 (en) * | 2020-10-22 | 2022-04-27 | Novaled GmbH | Organic compound of formula (i) for use in organic electronic devices, an organic electronic device comprising a compound of formula (i) and a display device comprising the organic electronic device |
EP3989302A1 (en) * | 2020-10-22 | 2022-04-27 | Novaled GmbH | Organic compound of formula (i) for use in organic electronic devices, an organic electronic device comprising a compound of formula (i) and a display device comprising the organic electronic device |
EP3989301A1 (en) * | 2020-10-22 | 2022-04-27 | Novaled GmbH | Organic electronic device comprising a compound of formula (1), display device comprising the organic electronic device as well as compounds of formula (1) for use in organic electronic devices |
EP3989305A1 (en) * | 2020-10-22 | 2022-04-27 | Novaled GmbH | Organic electronic device comprising a compound of formula (1), display device comprising the organic electronic device as well as compounds of formula (1) for use in organic electronic devices |
CN115867531A (zh) | 2020-06-22 | 2023-03-28 | 诺瓦尔德股份有限公司 | 用于有机电子器件的式(i)有机化合物、包含式(i)化合物的有机电子器件和包含所述有机电子器件的显示器件 |
JP2023553379A (ja) | 2020-12-07 | 2023-12-21 | オーティーアイ ルミオニクス インコーポレーテッド | 核形成抑制被膜及び下地金属被膜を用いた導電性堆積層のパターニング |
CN114843410A (zh) * | 2021-01-30 | 2022-08-02 | 北京夏禾科技有限公司 | 一种叠层有机电致发光器件 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004002741A (ja) * | 2002-03-22 | 2004-01-08 | Mitsubishi Chemicals Corp | 高分子化合物、1,4−フェニレンジアミン誘導体、電荷輸送材料、有機電界発光素子材料および有機電界発光素子 |
Family Cites Families (91)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2566208A (en) * | 1948-10-13 | 1951-08-28 | Monsanto Chemicals | Dielectric composition of halogenated aromatic hydrocarbon and organic antimony compound as a corrosion inhibitor |
CH354066A (de) | 1955-07-05 | 1961-05-15 | Metal & Thermit Corp | Verfahren zur Herstellung von Alkoholen |
CH354065A (de) | 1955-07-05 | 1961-05-15 | Metal & Thermit Corp | Verfahren zur Herstellung von Alkoholen |
US3083242A (en) * | 1956-09-19 | 1963-03-26 | M & T Chemicals Inc | Preparation of certain organomagnesium chlorides in ethylene polyethers |
DE1140576B (de) * | 1961-09-21 | 1962-12-06 | Bayer Ag | Verfahren zur Herstellung von Arylmagnesiumhalogeniden |
US3563751A (en) * | 1967-07-20 | 1971-02-16 | Du Pont | Hexaarylbiimidazole-acridine dye compositions |
US3558671A (en) * | 1967-08-30 | 1971-01-26 | Du Pont | Fluoro- and cyano-substituted 7,7,8,8-tetracyanoquinodimethans and intermediates thereto |
US4003943A (en) | 1974-12-20 | 1977-01-18 | E. I. Du Pont De Nemours And Company | Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same |
US4005091A (en) * | 1974-12-20 | 1977-01-25 | E. I. Du Pont De Nemours And Company | Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same |
US3963769A (en) * | 1974-12-20 | 1976-06-15 | E. I. Du Pont De Nemours And Company | Substituted trimethylene cyclopropanes, salts thereof, intermediates and methods of making the same |
US4066569A (en) * | 1975-12-30 | 1978-01-03 | Hughes Aircraft Company | Dopants for dynamic scattering liquid crystals |
US4133821A (en) | 1977-03-15 | 1979-01-09 | Wisconsin Alumni Research Foundation | Alkylidenediquinocyclopropanes and Diarylcyclopropenes and method for preparation |
DE3574028D1 (en) * | 1984-11-13 | 1989-12-07 | Secr Defence Brit | Alpha-hydroxy carboxylic acid derivatives suitable for use in liquid crystal materials and devices |
US4585895A (en) * | 1985-02-20 | 1986-04-29 | Xerox Corporation | Processes for the preparation of mixed squaraine compositions |
JPS61254582A (ja) * | 1985-05-04 | 1986-11-12 | Mitsubishi Chem Ind Ltd | テトラキス(1,3−ジチオ−ル−2−イリデン)〔4〕ラジアレン類 |
US4618453A (en) * | 1985-05-30 | 1986-10-21 | The United States Of America As Represented By The Secretary Of The Navy | Conductive heterocyclic ladder polymers |
JPS63172274A (ja) | 1987-01-12 | 1988-07-15 | Alps Electric Co Ltd | 光導電性被膜およびそれを用いた電子写真感光体 |
JPS63172275A (ja) | 1987-01-12 | 1988-07-15 | Alps Electric Co Ltd | 光導電性被膜およびそれを用いた電子写真感光体 |
US4769292A (en) * | 1987-03-02 | 1988-09-06 | Eastman Kodak Company | Electroluminescent device with modified thin film luminescent zone |
US4960916A (en) * | 1989-09-29 | 1990-10-02 | United States Of America As Represented By The Secretary Of The Navy | Organometallic antimony compounds useful in chemical vapor deposition processes |
DE4024871A1 (de) * | 1990-08-06 | 1992-02-13 | Basf Ag | Perlfoermige antistatische expandierbare styrolpolymerisate |
US5093698A (en) * | 1991-02-12 | 1992-03-03 | Kabushiki Kaisha Toshiba | Organic electroluminescent device |
DE4106122A1 (de) * | 1991-02-27 | 1992-09-03 | Bayer Ag | Neue naphthalimide, diese enthaltende toner und die verwendung der neuen naphthalimide als additive fuer toner |
JP2998268B2 (ja) * | 1991-04-19 | 2000-01-11 | 三菱化学株式会社 | 有機電界発光素子 |
JPH04338760A (ja) | 1991-05-15 | 1992-11-26 | Konica Corp | 電子写真感光体 |
US5393614A (en) * | 1992-04-03 | 1995-02-28 | Pioneer Electronic Corporation | Organic electroluminescence device |
DE59301378D1 (de) * | 1992-04-22 | 1996-02-22 | Ciba Geigy Ag | Substituierte Tetracyanochinodimethane, Verfahren zu deren Herstellung und deren Verwendung als pi-akzeptoren und elektrische Halbleiter |
JPH07168377A (ja) | 1993-12-16 | 1995-07-04 | Konica Corp | 電子写真感光体 |
FI95574C (fi) * | 1994-02-16 | 1996-02-26 | Valtion Teknillinen | Elektroneja johtavia molekyylivalmisteita |
EP0676461B1 (de) * | 1994-04-07 | 2002-08-14 | Covion Organic Semiconductors GmbH | Spiroverbindungen und ihre Verwendung als Elektrolumineszenzmaterialien |
US6013982A (en) * | 1996-12-23 | 2000-01-11 | The Trustees Of Princeton University | Multicolor display devices |
US5811833A (en) * | 1996-12-23 | 1998-09-22 | University Of So. Ca | Electron transporting and light emitting layers based on organic free radicals |
JPH10270171A (ja) * | 1997-01-27 | 1998-10-09 | Junji Kido | 有機エレクトロルミネッセント素子 |
DE19756361A1 (de) * | 1997-12-18 | 1999-06-24 | Philips Patentverwaltung | Organische lichtemittierende Diode mit Terbiumkomplex |
JPH11251067A (ja) * | 1998-03-02 | 1999-09-17 | Junji Kido | 有機エレクトロルミネッセント素子 |
DE19836408A1 (de) | 1998-08-12 | 2000-02-24 | Basf Ag | Verfahren zur Herstellung von Grignardverbindungen |
JP3389888B2 (ja) | 1998-11-09 | 2003-03-24 | 東レ株式会社 | 発光素子 |
DE19858856A1 (de) * | 1998-12-19 | 2000-06-21 | Merck Patent Gmbh | Verfahren zur Herstellung von Arylmetallverbindungen und deren Umsetzung mit Elektrophilen |
US6103459A (en) * | 1999-03-09 | 2000-08-15 | Midwest Research Institute | Compounds for use as chemical vapor deposition precursors, thermochromic materials light-emitting diodes, and molecular charge-transfer salts and methods of making these compounds |
JP2001131174A (ja) * | 1999-11-02 | 2001-05-15 | Sony Corp | バソフェナントロリン化合物及びその製造方法 |
JP3924648B2 (ja) * | 1999-11-02 | 2007-06-06 | ソニー株式会社 | 有機電界発光素子 |
US6824890B2 (en) * | 2000-05-03 | 2004-11-30 | The Regents Of The University Of California | Soluble tetrahedral compounds for use in electroluminescent devices |
EP1160888A1 (en) * | 2000-05-29 | 2001-12-05 | Sony International (Europe) GmbH | Hole transporting agents and photoelectric conversion device comprising the same |
JP3998903B2 (ja) * | 2000-09-05 | 2007-10-31 | 出光興産株式会社 | 新規アリールアミン化合物及び有機エレクトロルミネッセンス素子 |
US6699597B2 (en) * | 2001-08-16 | 2004-03-02 | 3M Innovative Properties Company | Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein |
JP3823312B2 (ja) * | 2001-10-18 | 2006-09-20 | 日本電気株式会社 | 有機薄膜トランジスタ |
KR100691543B1 (ko) * | 2002-01-18 | 2007-03-09 | 주식회사 엘지화학 | 새로운 전자 수송용 물질 및 이를 이용한 유기 발광 소자 |
DE10207859A1 (de) * | 2002-02-20 | 2003-09-04 | Univ Dresden Tech | Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung |
DE10212926A1 (de) * | 2002-03-22 | 2003-10-16 | Infineon Technologies Ag | Halbleiterspeicherzelle und Halbleiterspeichereinrichtung |
JP2004002740A (ja) * | 2002-03-22 | 2004-01-08 | Mitsubishi Chemicals Corp | 高分子化合物、1,4−フェニレンジアミン誘導体、電荷輸送材料、有機電界発光素子材料および有機電界発光素子 |
US20100026176A1 (en) * | 2002-03-28 | 2010-02-04 | Jan Blochwitz-Nomith | Transparent, Thermally Stable Light-Emitting Component Having Organic Layers |
AU2002323418A1 (en) | 2002-04-08 | 2003-10-27 | The University Of Southern California | Doped organic carrier transport materials |
TWI314947B (en) * | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
DE10224021B4 (de) * | 2002-05-24 | 2006-06-01 | Novaled Gmbh | Phosphoreszentes lichtemittierendes Bauelement mit organischen Schichten |
US6706828B2 (en) * | 2002-06-04 | 2004-03-16 | Crompton Corporation | Process for the oligomerization of α-olefins having low unsaturation |
JP3960131B2 (ja) | 2002-06-05 | 2007-08-15 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、及びそれを用いた有機エレクトロルミネッセンス素子および表示装置 |
ES2197818B1 (es) | 2002-06-11 | 2005-02-01 | Institut Quimic De Sarria Cets | 2,7,12,17 alquenil, aril y heteroaril derivados del 3,6,13,16-tetraazaporficeno, y procedimiento, compuesto intermedio y utilizaciones correspondientes. |
US7074534B2 (en) * | 2002-07-10 | 2006-07-11 | E. I. Du Pont De Nemours And Company | Polymeric charge transport compositions and electronic devices made with such compositions |
JP4047110B2 (ja) | 2002-09-11 | 2008-02-13 | 株式会社小松製作所 | 建設機械 |
DE10261662A1 (de) | 2002-12-20 | 2004-07-01 | Friedrich-Schiller-Universität Jena | Neue mit Pyrazinen verknüpfte 1,4,5,8-Tetraazafulvalene und Verfahren zu ihrer Herstellung |
EP1611484B1 (de) * | 2003-03-19 | 2021-11-10 | Heliatek GmbH | Photoaktives bauelement mit organischen schichten |
JP2004335557A (ja) | 2003-04-30 | 2004-11-25 | Ricoh Co Ltd | 縦型有機トランジスタ |
EP1477892B1 (en) * | 2003-05-16 | 2015-12-23 | Sap Se | System, method, computer program product and article of manufacture for inputting data in a computer system |
DE10338406A1 (de) * | 2003-08-18 | 2005-03-24 | Novaled Gmbh | Dotierte organische Halbleitermaterialien sowie Verfahren zu deren Herstellung |
DE10339772B4 (de) * | 2003-08-27 | 2006-07-13 | Novaled Gmbh | Licht emittierendes Bauelement und Verfahren zu seiner Herstellung |
US7655961B2 (en) * | 2003-10-02 | 2010-02-02 | Maxdem Incorporated | Organic diodes and materials |
DE10357044A1 (de) | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten |
DE102004010954A1 (de) | 2004-03-03 | 2005-10-06 | Novaled Gmbh | Verwendung eines Metallkomplexes als n-Dotand für ein organisches halbleitendes Matrixmaterial, organisches Halbleitermaterial und elektronisches Bauteil |
CN100506892C (zh) * | 2004-04-30 | 2009-07-01 | 住友化学株式会社 | 具有氧碳基的聚合物及其用途 |
US7540978B2 (en) * | 2004-08-05 | 2009-06-02 | Novaled Ag | Use of an organic matrix material for producing an organic semiconductor material, organic semiconductor material and electronic component |
CN101894917B (zh) * | 2004-12-06 | 2012-08-29 | 株式会社半导体能源研究所 | 发光元件和使用该元件的发光装置 |
WO2006067800A1 (en) | 2004-12-24 | 2006-06-29 | Council Of Scientific And Industrial Research | Triorganoantimony compounds for pesticidal use |
EP1869141B1 (de) * | 2005-04-14 | 2020-03-11 | Merck Patent GmbH | Verbindungen für organische elektronische vorrichtungen |
US7563518B2 (en) * | 2005-07-28 | 2009-07-21 | Eastman Kodak Company | Low voltage organic electroluminescent element |
US7582893B2 (en) * | 2005-09-15 | 2009-09-01 | Spansion Llc | Semiconductor memory device comprising one or more injecting bilayer electrodes |
US20070116984A1 (en) * | 2005-09-21 | 2007-05-24 | Doosan Corporation | Spiro-compound for electroluminescent display device and electroluminescent display device comprising the same |
DE502005009802D1 (de) * | 2005-11-10 | 2010-08-05 | Novaled Ag | Dotiertes organisches Halbleitermaterial |
US7919010B2 (en) * | 2005-12-22 | 2011-04-05 | Novaled Ag | Doped organic semiconductor material |
ATE394800T1 (de) * | 2006-03-21 | 2008-05-15 | Novaled Ag | Heterocyclisches radikal oder diradikal, deren dimere, oligomere, polymere, dispiroverbindungen und polycyclen, deren verwendung, organisches halbleitendes material sowie elektronisches bauelement |
DE102006039423A1 (de) | 2006-08-23 | 2008-02-28 | Werner, Johannes | Halbleitende Polyaddukte mit kolumnarer Struktur |
EP1918350B1 (en) * | 2006-10-24 | 2010-08-11 | Semiconductor Energy Laboratory Co., Ltd. | Anthracene derivative, and light emitting element, light emitting device, electronic device using anthracene derivative |
DE102007012794B3 (de) * | 2007-03-16 | 2008-06-19 | Novaled Ag | Pyrido[3,2-h]chinazoline und/oder deren 5,6-Dihydroderivate, deren Herstellungsverfahren und diese enthaltendes dotiertes organisches Halbleitermaterial |
EP1988587B1 (de) * | 2007-04-30 | 2016-12-07 | Novaled GmbH | Oxokohlenstoff-, Pseudooxokohlenstoff- und Radialenverbindungen sowie deren Verwendung |
EP1990847B1 (de) * | 2007-05-10 | 2018-06-20 | Novaled GmbH | Verwendung von chinoiden Bisimidazolen und deren Derivaten als Dotand zur Dotierung eines organischen halbleitenden Matrixmaterials |
US8057712B2 (en) * | 2008-04-29 | 2011-11-15 | Novaled Ag | Radialene compounds and their use |
EP2180029B1 (en) * | 2008-10-23 | 2011-07-27 | Novaled AG | Radialene compounds and their use |
CN102482574B (zh) * | 2009-06-18 | 2014-09-24 | 巴斯夫欧洲公司 | 用作场致发光器件的空穴传输材料的菲并唑化合物 |
WO2011131185A1 (de) * | 2010-04-21 | 2011-10-27 | Novaled Ag | Mischung zur herstellung einer dotierten halbleiterschicht |
TWI526418B (zh) * | 2011-03-01 | 2016-03-21 | 諾瓦發光二極體股份公司 | 有機半導體材料及有機組成物 |
JP2015010052A (ja) * | 2013-06-28 | 2015-01-19 | 三星ディスプレイ株式會社Samsung Display Co.,Ltd. | シクロブタン誘導体及びそれを用いた有機電界発光素子 |
US10326079B2 (en) * | 2015-04-27 | 2019-06-18 | Hodogaya Chemical Co., Ltd. | Organic electroluminescent device |
-
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2004002741A (ja) * | 2002-03-22 | 2004-01-08 | Mitsubishi Chemicals Corp | 高分子化合物、1,4−フェニレンジアミン誘導体、電荷輸送材料、有機電界発光素子材料および有機電界発光素子 |
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