TWI485145B - P型有機半導體材料與光電元件 - Google Patents

P型有機半導體材料與光電元件 Download PDF

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TWI485145B
TWI485145B TW101139632A TW101139632A TWI485145B TW I485145 B TWI485145 B TW I485145B TW 101139632 A TW101139632 A TW 101139632A TW 101139632 A TW101139632 A TW 101139632A TW I485145 B TWI485145 B TW I485145B
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Chih Ping Chen
Fang Yuan Tsai
Chien Tien Chen
Gue Wuu Hwang
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Ind Tech Res Inst
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    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Description

P型有機半導體材料與光電元件
本發明係有關於p型有機半導體材料,以及p型有機半導體材料於光電元件之應用。
有機半導體材料(organic semiconductor material)因具有半導體與光電特性,可應用於許多光電元件上,如有機薄膜電晶體(organic thin-film transistor,OTFT)、有機太陽能電池(organic solar cell)、有機發光二極體(organic light emitting diode,OLED)、與光感測器上。藉由溶液塗佈技術,可將有機半導體材料製成光電元件的主動層薄膜,形成質輕、價格便宜、製程方便以及大面積化的可撓式光電元件。目前有機半導體材料發展之主流以共軛高分子(conjugated polymer)為主,即主鏈以共軛型態相連。一般共軛高分子應用於光電元件上的主要缺點為載子遷移率(carrier mobility)較低,且吸光範圍較窄(400nm~650nm)所以侷限了元件的使用。因此有許多研究團隊相繼投入共軛高分子材料的合成,研發具有高載子遷移及更廣波域吸收的材料,進一步提升光電元件的效能。
在有機太陽能電池的應用上,其主動層材料也必需是高遷移率的電子與電洞傳輸材料,否則因為光激或電激生成之電荷會經由複合而消散,而降低有機太陽能電池的光電轉換效率(power conversion efficiency)。至於光吸收的部分,如能有效的增加材料的太陽光譜吸收能力,配合材料 高載子遷移速度的話,將有機會突破性發展有機太陽能電池之轉換效率。有機太陽能電池之發電原理,主要結合電子予體(donor)與電子受體(acceptor)材料,以異質接面的技術配合發展各種高分子當電子予體材料,結合碳60當電子受體材料,例如:聚(3-己烷基噻吩)(P3HT)摻混苯基-碳61-丁酸甲酯(PCBM),其光電轉換效率提升至3.5%。
目前仍需新穎的p型有機半導體材料取代P3HT,使有機太陽能電池具有更佳效能如更高的轉換效率。
本發明一實施例提供一種p型有機半導體材料,其結 構如下:,其中每一Con相同,係共軛寡聚物;以及每一EW相同,係拉電子基團。
本發明一實施例提供一種光電元件,包括主動層,且主動層包括上述之p型有機半導體材料。
本發明一實施例提供一種p型有機半導體材料,其結構如式1:
在式1中,每一Con相同,係共軛寡聚物,且每一EW相同,係拉電子基團。在本發明一實施例中,共軛寡聚物 Con可為下述單元所形成之共軛寡聚物:噻吩、苯、哌喃(Pyrane)、哌咯(Pyrroline)、呋喃(Furan)、苯并呋喃(Benzofuran)、苯并噻吩(Benzothiophene)、苯并噻二唑(Benzothiodiazole)、吡啶(Pyridine)、喹啉(Quinoline)、異喹啉(isoquinoline)、吡嗪(pyrazine)、嘧啶(Pyrimidine)、吡咯(Pyrrole)、吡唑(Pyrazole)、咪唑(Imidazole)、吲哚(Indole)、噻唑(Thiazole)、異噻唑(Isothiazole)、噁唑(Oxazole)、異噁唑(Isoxazole)、苯并噻唑(Benzothiazole)、苯并噁唑(Benzoxazole)、1,2,4-三噁唑(1,2,4-Triazole)、1,2,3-三噁唑(1,2,3-Triazole)、二氮菲(Phenanthroline)、噁二唑吡啶(Oxadiazolopyridine)、吡啶并吡嗪(Pyridopyrazine)、苯并噁二唑(Benzooxadiazole)、噻二唑吡啶(Thiadiazolopyridine)、哂吩(Selenophene)、噻二唑喹噁啉(Thiadiazoloquinoxaline)、噻嗯并吡嗪(Thienopyrazine)、喹噁啉(Quinoxaline)、或二酮吡咯并吡咯(Diketopyrrolopyrrole)。舉例來說,共軛的噻吩寡聚物之結構如式2所示:
在式2中,每一R1 各自獨立,擇自H或C3-10 烷基,且n係2至20之整數。
在本發明一實施例中,拉電子基團EW可為α-氰基丙烯酸烷基酯、乙烯丙二氰、鹵素、亞硝酸基(-NO2 )、或其他合適的拉電子基團。舉例來說,α-氰基丙烯酸烷基酯之 結構如式3所示,而乙烯丙二氰如式4所示。
在式3中,R2 係C3-10 烷基。
在本發明一實施例中,p型有機半導體材料的合成方式如下述。值得注意的是,用以合成本發明之p型有機半導體材料的合成方式並不限於下述步驟,本技術領域中具有通常知識者自可依其設備與起始材料的考量,自行更動合成步驟。
首先如式5所示,取順-二苯代乙烯(cis -stilbene)的硼化物與共軛寡聚物(如共軛的噻吩寡聚物)反應。值得注意的是,式5中共軛的噻吩寡聚物僅用以舉例,本發明之共軛寡聚物可為其他合適的共軛寡聚物。
在式5中,每一R11 相同,每一R12 相同、每一R13 相同、每一R14 相同、每一R15 相同、且每一R16 相同。上述R11 、R12 、R13 、R14 、R15 、R16 各自獨立,擇自H或C3-10 烷基。
接著如式6所示,取式5產物與拉電子基團(如α-氰基丙烯酸烷基酯)反應。值得注意的是,式6中α-氰基丙烯酸烷基酯僅用以舉例,本發明之拉電子基團可為其他合適的拉電子基團。
在式6中,每一R2 相同,係C3-10 烷基。由上述可知,本發明之p型有機半導體材料具有分子內鏡面的對稱結構,使結構具有規則性而分子間容易整齊排列,使材料更易成膜。若順-二苯代乙烯(cis -stilbene)兩側分別取代不同的共軛寡聚物及/或拉電子基團,則無法產生較佳的分子堆疊,使其光電特性受限,於光電應用上效果不佳。
本發明之p型有機半導體材料可應用於有機薄膜電晶體裝置之主動層材料、有機發光二極體裝置之主動層材料、或有機太陽能電池裝置之主動層材料。
例如,有機太陽能電池之主動層包含本發明之p型有 機半導體材料,與電子受體材料(acceptor)如苯基-碳61-丁酸甲酯(PC61 BM)或苯基-碳71-丁酸甲酯(PC71 BM)。在一實施例中,p型有機半導體材料與電子受體材料混合比例約為1:0.5至1:2時,其光電轉換效率最佳。
為了讓本發明之上述和其他目的、特徵、和優點能更明顯易懂,下文特舉數實施例配合所附圖式,作詳細說明如下:
【實施例】 實施例1 (P型有機半導體材料之合成)
取50毫升雙頸圓底瓶內置攪拌子與上接迴流管,真空乾燥後通入氮氣。接著將3,7-dibromo-5,5-spirofluorenyl[a,d]cycloheptene(Stif ,如J.Am.Chem.Soc.2007 , 129 ,7478.製備而得)(2501毫克,5毫莫耳)、Bis(pinacolato)diboron(2666毫克,10.5毫莫耳)、醋酸鉀(2356毫克,24毫莫耳)、與催化劑Pd(dppf)Cl2 (163毫克,0.2毫莫耳)依序加入圓底瓶中,再以針筒將100mL之去氧二氧陸環注入圓底瓶中。接著加熱反應瓶使其迴流反應18小時,再將反應瓶回溫至室溫並通入氧氣以淬息反應。以二氯甲烷(3×20毫升)萃取反應後之混合物,所得萃取液依序以硫酸鎂乾燥、以矽藻土過濾、再迴旋濃縮得粗產物。接著以甲醇(3×20毫升)清洗粗產物,得到2427毫克(4.08毫莫耳)的白色固體化合物1 如式7,產率82%。白色固體化合物1之 數據分析如下:1 H NMR(CDCl3 ,400 MHz,ppm):δ 7.97(d,J =7.8 Hz,2H),δ 7.73(d,J =7.6 Hz,2H),δ 7.70(dd,J =7.5,1.0 Hz,2H),δ 7.38(d,J =7.3,2H),δ 7.35(t,J =7.6 Hz,2H),δ 7.23(td,J =7.7,1.1 Hz,2H),δ 7.01(s,2H),δ 1.19(s,24H);13 C NMR(100 MHz,CDCl3 )δ 152.4,141.2,139.0,138.8,135.3,134.3,133.3,131.4,127.7,127.1,127.0,120.2,83.4,66.0,24.7。
取25毫升雙頸圓底瓶內置攪拌子並接上迴流管,依序加入化合物1 (406毫克,0.35毫莫耳)、碳酸鈉(223毫克,2.1毫莫耳)、5”-(4-溴)-3-3”-二己基-2,2’:5’,2”-三噻吩-5-醛(5" -(4-bromo)-3,3" -di-n-hexyl-2,2' :5' ,2" -terthiophene-5-carbaldehyde,209毫克,0.77毫莫耳)、與催化劑Pd(PPh3 )4 (35毫克,0.03毫莫耳)後,除去反應裝置內之氧氣並通入氮氣,接著以針筒將10mL已除氧之1,2-二甲氧基乙烷與1mL水注入圓底瓶中,開啟迴流裝置使其反應18小時。反應結束後將圓底瓶回溫至室溫,再將氧氣通入圓底瓶以淬息反應。以二氯甲烷(3×20毫升)萃取反應後之混合物,所得萃取液依序以硫酸鎂乾燥、過濾、及迴旋濃縮,再以管柱層析搭配衝提液(CH2 Cl2 /hexane,1/2)純化濃縮後之粗產物,得384毫克(0.31毫莫耳)的化合物2 如式7所示,產率為89%。化合物式2 之數據分析如下:1 H NMR(CDCl3 ,400 MHz,ppm):δ 9.82(s,2H),δ 8.03(d,J =7.7 Hz,2H),δ 7.80(d,J =7.5 Hz,2H),δ 7.58(s,2H),δ 7.44(t,J =7.3 Hz,2H),δ 7.41(dd,J =8.1,1.6 Hz,2H),δ 7.36(d,J =7.8 Hz,2H),δ 7.33(t,J =7.4 Hz,2H),δ 7.23(d,J =1.4 Hz,2H),δ 7.22(d,J =3.9 Hz,2H),δ 7.04(d,J =3.8 Hz,2H),δ 6.96(s, 2H),δ 6.79(s,2H),δ 2.81(t,J =7.7 Hz,4H),δ 2.68(t,J =7.6 Hz,4H),δ 1.72-1.55(m,8H),δ 1.43-1.31(m,24H),δ 0.92-0.88(m,12H);13 C NMR(CDCl3 ,100 MHz, ppm):δ182.48,152.18,142.16,141.96,141.16,141.06,140.25,140.18,139.04,139.01,138.32,135.90,134.37,133.60,132.92,132.70,129.49,128.23,127.75,127.53,126.95,126.30,126.05,123.98,120.53,66.01,31.66,31.61,30.28,29.51,29.46,29.16,29.12,22.57,22.57,14.10,14.05。
取50毫升圓底瓶內置攪拌子,將化合物2 (256毫克,0.20毫莫耳)、氰基乙酸辛酯(400毫克,2.1毫莫耳)、無水的20毫升的氯仿溶劑依序加入圓底瓶中,再加入兩滴三乙基胺。上述混合物於室溫下反應18小時,再加入水與二氯甲烷進行萃取,所得萃取液依序以硫酸鎂乾燥、過濾、及迴旋濃縮得粗產物。以管柱層析搭配沖提液(CH2 Cl2 /hexane,1/1)純化粗產物,得284毫克(0.18毫莫耳)的深紅色固體EtStif 如式7所示,產率為90%。EtStif 之數據分析如下:1 H NMR(CDCl3 ,400 MHz,ppm):δ8.20(s,1H),δ 8.03(d,J =7.8 Hz,2H),δ 7.80(d,J =7.4 Hz,2H),δ 7.58(s,2H),δ 7.45(t,J =7.4 Hz,2H),δ 7.41(dd,J =7.9,1.7 Hz,2H),δ 7.37-7.32(m,4H),δ 7.27(d,J =4.0 Hz,2H),δ 7.23(d,J =1.6 Hz,H),δ 7.05(d,J =3.9 Hz,2H),δ 6.97(s,2H),δ 6.79(s,2H),δ 4.29(t,J =6.8 Hz,4H),δ 2.82(t,J =7.8 Hz,4H),δ 2.69(t,J =7.5 Hz,4H),δ 1.78-1.57(m,12H),δ 1.41-1.25(m,44H),δ 0.92-0.87(m,18H);13 C NMR (CDCl3 ,100 MHz, ppm):δ163.09,152.36,145.85,142.18,141.9,141.72,141.2,140.69,140.37,139.02,138.77,135.89,133.91,133.53,32.92,132.82,132.68,129.49,128.23,128.08,127.53,126.94,126.22,126.05,123.96,120.52,115.98,97.59,77.20,66.50,65.99,31.75,31.66,31.58,30.19,30.14,29.55,29.33,29.17,29.15,29.12,28.54,25.78,22.61,22.58,22.55,14.09,14.06,14.04。
實施例2(有機太陽能電池元件)
本實施例製備如第1圖所示之有機太陽能電池裝置10,其包括氧化銦錫(ITO)陽極11;電洞傳輸層12,材料為聚3,4-乙基二氧噻吩:聚對苯乙烯磺酸Poly(3,4-ethylenedioxythiophene):poly(styrene-sulfonate)(PEDOT:PSS),形成於陽極11上;主動層13,包含本發明之p型有機半導體材料或市售之P3HT,形成於電洞傳輸層12上;以及陰極14為鈣(Ca)/鋁(Al)。
上述之主動層13由實施例1之EtStif (或市售之P3HT)與苯基-碳-丁酸甲酯([6,6]-phenyl-C-butyric acid methyl ester,PCBM)以1:0.8的重量比例摻混而組成,其中PCBM中的碳可以是碳61或是碳71的衍生物。效率的量測是在AM 1.5的太陽光照度下測量。
製備的步驟如下:
1.於實驗前一天配置主動層溶液(EtStif/PCBM或P3HT/PCBM,10mg/mL),攪拌一晚。
2.氧化銦錫(ITO)玻璃分別用丙酮及異丙醇以超音波震盪清洗15分鐘,以氮氣吹乾後,置於加熱板烘烤5分鐘。
3.將氧化銦錫(ITO)玻璃置於氧氣電漿下5分鐘。
4.以3000rpm/30sec旋轉塗佈聚3,4-乙基二氧塞吩:聚對苯乙烯磺酸(PEDOT:PSS,Baytron P-VP AI4083),之後放置手套箱以150℃加熱烤一小時。
5.在手套箱中以1200rpm/60sec旋轉塗佈主動層(EtStif /PCBM或P3HT/PCBM)。
6.將ITO玻璃置於140℃加熱板上退火20分鐘,靜置冷卻。
7.放至光罩上,蒸鍍鈣/鋁電極。
8.最後封裝整個元件並進行量測。
表1為本發明實施例1之EtStif 與市售之P3HT應用於有機太陽能電池中的光電轉換效率、短路電流、開路電壓、與填充因子。
與習知之P3HT/PCBM作為主動層的有機太陽能電池相較,含有本發明之p型有機半導體材料EtStif 之主動層的有機太陽能電池,其短路電流較低,開路電壓較高,填充因子較高,且轉換效率較高。
雖然本發明已以數個較佳實施例揭露如上,然其並非用以限定本發明,任何熟習此技藝者,在不脫離本發明之精神和範圍內,當可作任意之更動與潤飾,因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。
10‧‧‧有機太陽能電池
11‧‧‧陽極
12‧‧‧電洞傳輸層
13‧‧‧主動層
14‧‧‧陰極
第1圖係本發明一實施例中,有機太陽能電池的裝置圖。
10‧‧‧有機太陽能電池
11‧‧‧陽極
12‧‧‧電洞傳輸層
13‧‧‧主動層
14‧‧‧陰極

Claims (7)

  1. 一種p型有機半導體材料,其結構如下: 其中每一Con相同,其結構如下: 其中每一R1 各自獨立,擇自H或C3-10 烷基;以及n係2至20之整數;以及每一EW相同,係拉電子基團。
  2. 如申請專利範圍第1項所述之p型有機半導體材料,其中Con之結構如下:
  3. 如申請專利範圍第1項所述之p型有機半導體材料,其中EW係α-氰基丙烯酸烷基酯、乙烯丙二氰、鹵素、或亞硝酸基(-NO2 )。
  4. 如申請專利範圍第3項所述之p型有機半導體材料,其中α-氰基丙烯酸烷基酯之結構如下: 其中R2 係C3-10 烷基。
  5. 如申請專利範圍第1項所述之p型有機半導體材 料,其結構如下: 其中每一R2 相同,係C3-10 烷基;每一R11 相同、每一R12 相同、每一R13 相同、每一R14 相同、每一R15 相同、且每一R16 相同;以及R11 、R12 、R13 、R14 、R15 、及R16 各自獨立,擇自H或C3-10 烷基。
  6. 一種光電元件,包括一主動層,且該主動層包括申請專利範圍第1項所述之p型有機半導體材料。
  7. 如申請專利範圍第6項所述之光電元件,包括有機太陽能電池、有機發光二極體、或有機薄膜電晶體。
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10224489B2 (en) 2015-08-04 2019-03-05 Nichem Fine Technology Co., Ltd. Compound and organic electronic device using the same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI558688B (zh) * 2014-10-15 2016-11-21 彩豐精技股份有限公司 順式二苯乙烯/芴螺旋體衍生的光電材料
TWI534141B (zh) * 2014-10-15 2016-05-21 彩豐精技股份有限公司 以順式二苯乙烯/芴螺旋體衍生的雙極型化合物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010024149A (ja) * 2008-07-16 2010-02-04 Toyo Ink Mfg Co Ltd 7員環構造を有する化合物およびその用途

Family Cites Families (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4046577A (en) 1975-06-09 1977-09-06 The Richardson Company Photoreactive compositions comprising polymers containing alkoxyaromatic glyoxy groups
GB9226475D0 (en) 1992-12-18 1993-02-10 Cambridge Display Tech Ltd Chromophoric polymeric compositions
US6156494A (en) 1997-10-28 2000-12-05 Mosaic Technologies Serially directed combinatorial synthesis on fiber optic arrays
AUPP649498A0 (en) 1998-10-14 1998-11-05 Commonwealth Scientific And Industrial Research Organisation Organoboron derivatives and coupling thereof
US6706839B1 (en) 1999-02-10 2004-03-16 University Of Pittsburgh Chemical partitioning agents and methods of using same
TW503255B (en) 1999-09-27 2002-09-21 Ciba Sc Holding Ag Electroluminescent devices comprising diketopyrrolopyrroles
JP4259875B2 (ja) 2001-03-24 2009-04-30 メルク パテント ゲーエムベーハー スピロビフルオレン単位およびフルオレン単位を含む共役ポリマーおよびその使用
ES2323803T3 (es) 2002-01-22 2009-07-24 Telene Sas Complejos metalicos para uso en metatesis, reacciones radicalicas de transferencia de atomos, reacciones de polimerizacion por adicion y reacciones de vinilacion, metodos e intermedios para obtenerlos.
US20060030718A1 (en) 2002-03-28 2006-02-09 University Of Tennessee Research Foundation Cobalt-based catalysts for the cyclization of alkenes
WO2005002672A2 (en) 2003-07-01 2005-01-13 President And Fellows Of Harvard College Sirt1 modulators for manipulating cells/organism lifespan/stress response
KR20050031887A (ko) 2003-09-30 2005-04-06 교세라미타 가부시키가이샤 스틸벤 유도체, 그의 제조방법 및 전자사진 감광체
US8017634B2 (en) 2003-12-29 2011-09-13 President And Fellows Of Harvard College Compositions for treating obesity and insulin resistance disorders
CA2548671C (en) 2003-12-29 2015-02-24 President And Fellows Of Harvard College Compositions for treating or preventing obesity and insulin resistance disorders
US20070185343A1 (en) 2004-02-26 2007-08-09 Universiteit Gent Metal complexes for use in olefin metathesis and atom group transfer reactions
WO2006007411A2 (en) 2004-06-16 2006-01-19 President And Fellows Of Harvard College Methods and compositions for modulating bax-mediated apoptosis
KR20120082937A (ko) 2004-06-28 2012-07-24 스미또모 가가꾸 가부시키가이샤 바나듐 이핵 착체
CA2581174A1 (en) 2004-09-16 2006-03-30 Applera Corporation Fluorescent dye compounds, conjugates and uses thereof
WO2006036748A2 (en) 2004-09-22 2006-04-06 Symyx Technologies, Inc. Heterocycle-amine ligands, compositions, complexes, and catalysts, and methods of making and using the same
US20060276393A1 (en) 2005-01-13 2006-12-07 Sirtris Pharmaceuticals, Inc. Novel compositions for preventing and treating neurodegenerative and blood coagulation disorders
CA2595486A1 (en) 2005-01-20 2006-07-27 Sirtris Pharmaceuticals, Inc. Use of sirtuin-activating compounds for treating flushing and drug induced weight gain
US20070149466A1 (en) 2005-07-07 2007-06-28 Michael Milburn Methods and related compositions for treating or preventing obesity, insulin resistance disorders, and mitochondrial-associated disorders
WO2008005555A1 (en) 2006-07-07 2008-01-10 Gilead Sciences, Inc. Modulators of toll-like receptor 7
US20080214509A1 (en) 2007-03-02 2008-09-04 Robert Kerbel Methods for enhancing the efficacy of vascular disrupting agents
US20110110940A1 (en) 2008-04-15 2011-05-12 Oxigene, Inc. Methods for Enhancing the Efficacy of Vascular Disrupting Agents
CL2009000956A1 (es) 2008-04-21 2011-02-18 Univ California Composicion farmaceutica de liberacion sostenida que comprende un antagonista del receptor nmda particulado y un copolimero de tribloque, con una osmolaridad entre 100-500 mosm/l; y su uso para tratar un desorden otico, tal como enfermedad de meniere o perdida auditiva.
GB0812186D0 (en) 2008-07-03 2008-08-13 Dow Corning Modified polyolefins
GB0812185D0 (en) 2008-07-03 2008-08-13 Dow Corning Polymers modified by silanes
US10092580B2 (en) 2008-07-21 2018-10-09 Otonomy, Inc. Controlled-release otic structure modulating and innate immune system modulating compositions and methods for the treatment of otic disorders
TWI516264B (zh) 2010-05-06 2016-01-11 臺北醫學大學 芳香醯喹啉化合物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010024149A (ja) * 2008-07-16 2010-02-04 Toyo Ink Mfg Co Ltd 7員環構造を有する化合物およびその用途

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
『Emission Mechanism of Doubly ortho-Linked Quinoxaline/Diphenylfluorene or cis-Stilbene/Fluorene Hybrid Compounds Based on the Transient Absorption and Emission Measurements during Pulse Radiolysis』, Journal of the American Chemical Society (20090520), 131(19), pp. 6698-6707, Wei, Yi 等著 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10224489B2 (en) 2015-08-04 2019-03-05 Nichem Fine Technology Co., Ltd. Compound and organic electronic device using the same

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