TW201712922A - 摻雜有機半導體之方法及摻雜組合物 - Google Patents
摻雜有機半導體之方法及摻雜組合物 Download PDFInfo
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- TW201712922A TW201712922A TW105122947A TW105122947A TW201712922A TW 201712922 A TW201712922 A TW 201712922A TW 105122947 A TW105122947 A TW 105122947A TW 105122947 A TW105122947 A TW 105122947A TW 201712922 A TW201712922 A TW 201712922A
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Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/20—Changing the shape of the active layer in the devices, e.g. patterning
- H10K71/231—Changing the shape of the active layer in the devices, e.g. patterning by etching of existing layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/26—Bombardment with radiation
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
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Abstract
一種形成n型摻雜半導體層之方法,其中藉由具有有機半導體之吸收範圍內的波長之光線照射包含該有機半導體及n型摻雜劑試劑之薄膜,且其中該n型摻雜劑前驅體之吸收最大波長短於該光線之任何波峰波長。該n型摻雜半導體層可為有機發光器件之電子注入層。
Description
因其用於諸如有機發光二極體(OLED)、有機光響應器件(詳言之有機光伏打器件及有機光感測器)、有機電晶體及記憶體陣列器件之器件中,含有活性有機材料之電子器件正吸引增強之注意。含有活性有機材料之器件提供諸如低重量、低功率消耗及可撓性之益處。此外,使用可溶性有機材料允許在器件製造中使用溶液處理,例如噴墨印刷或旋塗。
有機發光器件具有基板,其攜載陽極、陰極及含有介於陽極與陰極之間的發光材料之有機發光層。
在操作中,通過陽極將電洞注入至器件中且通過陰極注入電子。發光材料之最高佔用分子軌域(HOMO)中之電洞及最低未佔用分子軌域(LUMO)中之電子組合以形成以光線形式釋放其能量之激子。
如WO 98/10621中所揭示,陰極包括諸如鋁之金屬單層、鈣及鋁之雙層;且如L.S.Hung,C.W.Tang及M.G.Mason,Appl.Phys.Lett.70,152(1997)中所揭示,一層鹼或鹼土化合物及一層鋁之雙層。
電子傳輸或電子注入層可提供於陰極與發光層之間。
Bao等人「Use of a 1H-Benzoimidazole Derivative as an n-Type Dopant and To Enable Air-Stable Solution-Processed n-Channel Organic Thin-Film Transistors」J.Am.Chem.Soc.2010,132,8852-8853揭示藉
由將(4-(1,3-二甲基-2,3-二氫-1H-苯并咪唑-2-基)苯基)二甲胺(N-DMBI)與PCBM混合且藉由加熱激活N-DMBI來摻雜[6,6]-苯基C61丁酸甲酯(PCBM)。
US 2014/070178揭示一種有機發光二極體(OLED),其具有安置於基板上之陰極及藉由對電子傳輸材料及N-DMBI進行熱處理所形成之電子傳輸層。揭示形成於N-DMBI熱處理上之基團可為n型摻雜劑。
US8920944揭示用於摻雜有機半導電材料之n型摻雜劑前驅體。
在第一態樣中,本發明提供一種形成n型摻雜半導體層之方法,其中藉由具有有機半導體之吸收範圍內的波長之光線照射包含有機半導體及n型摻雜劑試劑之薄膜,且其中n型摻雜劑試劑之吸收最大波長短於光線之任何波峰波長。
在第二態樣中,本發明提供一種形成有機電子器件之n型摻雜層的方法,其中根據第一態樣形成n型摻雜層。
在第三態樣中,本發明提供一種組合物,其包含:(a)有機半導體,其包含含有C=N基、腈基、C=O基及C=S基中之一或多者之單元;及(b)n型摻雜劑試劑,其包含2,3-二氫-苯并咪唑基。
包含含有C=N基、腈基、C=O基及C=S基之單元及含有2,3-二氫-苯并咪唑基之n型摻雜劑試劑的本第三態樣之有機半導體可如本文任何位置所描述。
在第四態樣中,本發明提供一種自如第三態樣之組合物形成n型摻雜半導體層之方法,該方法包含激發有機半導體之步驟。可藉由電磁照射,視情況使用如參考第一態樣所描述之光線,或藉由熱處理來激發如第三態樣之組合物。
如本文所用之「n型摻雜劑試劑」意謂相比於不在25℃下激發有機半導體之摻雜程度,當激發有機半導體時(視情況藉由如本文所描
述之照射)更大程度地摻雜有機半導體之材料。
較佳地,如藉由唯電子器件量測所測定,當激發有機半導體時,摻雜程度至少大10倍,視情況至少100倍。較佳地,不在25℃下激發有機半導體,則幾乎不或不存在摻雜。
100‧‧‧有機發光二極體(OLED)
101‧‧‧基板
103‧‧‧陽極
105‧‧‧發光層
107‧‧‧電子注入層
109‧‧‧陰極
現將參考圖式更詳細地描述本發明,其中:圖1示意性地說明如本發明之一實施例之有機發光二極體(OLED);圖2顯示n型摻雜劑試劑及兩種半導電聚合物之吸收光譜;圖3顯示照射前後之n型摻雜劑試劑及第一種半導電聚合物之混合物的吸收光譜;圖4顯示照射前後之n型摻雜劑試劑及第二種半導電聚合物之混合物的吸收光譜;圖5為唯電子器件之電流密度對電壓圖,該器件包含根據本發明之一實施例藉由不同時長之照射進行n摻雜之有機半導體層;且圖6為唯電子器件之電流密度對電壓圖,該器件包含根據本發明之一實施例在照射之前及之後經n摻雜之有機半導體層。
未按任何比例繪製之圖1說明如本發明之一實施例之有機發光二極體(OLED)100,其經例如玻璃或塑料基板之基板101支撐。OLED 100包含陽極103、發光層105、電子注入層107及陰極109。
陽極103可為導電材料之單層或可形成自兩種或多於兩種導電層。陽極103可為例如氧化銦錫層之透明陽極。可使用透明陽極103及透明基板101以使光線射過基板。陽極可為不透明的,在此情況下基板101可為不透明的或透明的,且光線可射過透明陰極109。
發光層105含有至少一種發光材料。發光材料105可由單個發光
化合物組成或可為多於一種化合物之混合物,視情況摻雜有一或多種發光摻雜劑之主體。發光層105可含有至少一種當器件處於操作狀態時發出磷光光線之發光材料,或至少一種當器件處於操作狀態時發出螢光光線之發光材料。發光層105可含有至少一種磷光發光材料及至少一種螢光發光材料。
電子注入層107包含或由n型摻雜半導體組成。
陰極109形成自至少一層,視情況兩或多於兩層,用於將電子注入至器件中。
OLED 100可在陽極103與陰極109之間含有一或多個其他層,例如一或多個電荷傳輸、電荷阻斷或電荷注入層。較佳地,器件包含在陽極與發光層105之間包含導電材料之電洞注入層。較佳地,器件包含在陽極103與發光層105之間包含半導電電洞傳輸材料之電洞傳輸層。
如本文所用之「導電材料」意謂具有功函數之材料,例如金屬或退化半導體。
如本文所用之「半導體」意謂具有HOMO及LUMO能階之材料,且半導體層為包含半導電材料或由一或多種半導電材料組成之層。
藉由形成有機半導體(受體材料)及n型摻雜劑試劑之薄膜,且用來自具有長於n型摻雜劑試劑之吸收最大波長之波峰波長的光源之光線照射薄膜,以形成電子注入層。
較佳地,如本文所描述之有機半導體的波峰波長為在400-700nm範圍內之吸收光譜中顯示最強吸收之波峰。較佳地,n型摻雜劑試劑之最強吸收在低於400nm之波長處。
n型摻雜劑試劑具有深於(離真空較遠)有機半導體之LUMO能階的HOMO能階。視情況,n型摻雜劑試劑具有比有機半導體之LUMO能階深(離真空較遠)至少1eV之HOMO能階。因此,當在室溫下混合
有機半導體及n型摻雜劑試劑時,幾乎不或不出現自發性摻雜。
然而,本發明人已出人意料地發現,如本文所描述之將薄膜曝露於電磁輻射會引起n型摻雜,且電磁輻射不必處於可由n型摻雜劑試劑吸收之波長處。自光源發射之光線與有機半導體的吸收光譜之吸收特徵(例如吸收峰或吸收肩)適當重疊。視情況,自光源發射之光線具有有機半導體之吸收最大波長之25nm、10nm或5nm內之波峰波長,然而應瞭解,光線之波峰波長不必與有機半導體之吸收最大波長一致。
可藉由以下中之一或多者控制摻雜程度:有機半導體/n型摻雜劑試劑比率;光線之波峰波長;薄膜之照射持續時間;及光線之強度。應瞭解,當光線之波峰波長與有機半導體之吸收最大值一致時,激發將為最有效的。
視情況,照射時間在1秒與1小時之間,視情況在1至30分鐘之間。
較佳地,發射自光源之光線在400至700nm之範圍內。較佳地,電磁輻射具有大於400nm之波峰波長,視情況大於420nm,視情況大於450nm。視情況,n型摻雜劑試劑之吸收光譜中之吸收峰及發射自光源之光線的波長之間不存在重疊。應瞭解,在摻雜有機半導體之過程中,n型摻雜劑試劑形成陽離子。可藉由此陽離子之電化還原所形成之基團半佔用分子軌域(SOMO)可視為n型摻雜劑試劑之摻雜強度的指示物。較佳地,此基團之SOMO深於有機半導體之LUMO不多於0.5eV。視情況,n型摻雜劑試劑可具有與有機半導體之LUMO能階相同或更淺之SOMO能階。視情況,n型摻雜劑試劑可具有比有機半導體之LUMO能階深至少0.05eV之半佔用分子軌域(SOMO)能階。視情況,基團具有低於(淺於)真空能階約3.0eV之SOMO能階。
視情況,有機半導體具有離真空能階不多於3.2eV之LUMO能
階,視情況離真空能階不多於3.1或3.0eV。
任何合適的電磁輻射源可用於照射薄膜,其包含但不限於螢光管、白熾燈泡及有機或無機LED。視情況,電磁輻射源為無機LED陣列。電磁輻射源可產生具有一個或多於一個波峰波長之輻射。
較佳地,電磁輻射源具有至少2000mW之光輸出,視情況至少3000mW,視情況至少4000mW。
較佳地,不多於10%或不多於5%的電磁輻射源之光輸出來自具有低於或等於400nm之波長的輻射,視情況低於或等於420nm。較佳地,光輸出中無一者具有低於或等於400nm之波長,視情況低於或等於420nm。
不曝露於諸如UV光線之短波長光線來誘發n型摻雜可避免對OLED之材料造成損害。
n型摻雜有機半導體可為異質或退化半導體。
在製造有機電子器件(諸如如圖1中所描述之OLED)時,照射步驟可在器件形成期間或器件已形成後進行。較佳地,照射在器件已形成及囊封後進行。可在將薄膜曝露於極少或無誘發n型摻雜之光線的波長之環境中製造器件直到器件囊封後,例如由具有波長長於電磁輻射源之波長的光線照明之環境,諸如用黃光照明之無塵室。
在如圖1中所描述之OLED之情況下,n型摻雜劑試劑之薄膜及有機半導體107可形成於有機發光層105上方,且陰極109可形成於薄膜上方。
在形成於透明基板101上且具有透明陽極103之器件(諸如ITO)之情況下,隨後可透過陽極101照射薄膜,或在具有透明陰極之器件之情況下,可透過陰極109照射薄膜。可選擇用來誘發n型摻雜之波長以避免由位於電磁輻射源與薄膜之間的器件層所吸收之波長。
較佳地,電子注入層107與有機發光層105接觸。較佳地,有機
半導體之薄膜及n型摻雜劑試劑直接形成於有機發光層105上。
較佳地,摻雜有機半導體具有深於發光層材料之LUMO(若發光層包含主體材料及發光材料之混合物,則其可為發光材料之LUMO或主體材料之LUMO)不多於約1eV,視情況0.5eV或0.2eV之功函數。較佳地,摻雜有機半導體具有與發光層材料之LUMO相同或更淺之功函數。視情況,摻雜有機半導體具有低於3.0eV之功函數,視情況約2.1至2.8eV。
較佳地,陰極109與電子注入層107接觸。較佳地,陰極直接形成於有機半導體之薄膜及n型摻雜劑試劑上。
有機半導體之薄膜及n型摻雜劑試劑可沈積在空氣中。視情況底層,較佳有機發光層105,為交聯的。
OLED 100可為顯示器,視情況為全色顯示器,其中發光層105包含含有紅、綠及藍子像素之像素。
OLED 100可為發射白光之OLED。如本文所描述之發射白光的OLED可具有等效於在2500至9000K範圍內之溫度下由黑體發射之彼者的CIE x座標,及由黑體發射之該光線的CIE y座標之0.05或0.025內之CIE y座標,視情況等效於在2700至6000K範圍內之溫度下由黑體發射之彼者的CIE x座標。發射白光之OLED可含有複數種發光材料,較佳發射紅、綠及藍光之材料,更佳發射紅、綠及藍磷光之材料,其組合以產生白光。可在發光層105中提供所有發光材料,或可提供一個或多個額外發光層。
發射紅光之材料可具有光致發光光譜,其具有在約大於550達約700nm之範圍內的波峰,視情況在約大於560nm或大於580nm達約630nm或650nm之範圍內。
發射綠光之材料可具有光致發光光譜,其具有在約大於490nm達約560nm之範圍內的波峰,視情況自約500nm、510nm或520nm達
約560nm。
發射藍光之材料可具有光致發光光譜,其具有在達約490nm之範圍內的波峰,視情況約450至490nm。
可藉由將PMMA薄膜中之5wt%材料投射至石英基板上以達成0.3至0.4之透射率值,且使用由濱松(Hamamatsu)供應之設備C9920-02在氮氣環境中進行量測來量測材料之光致發光光譜。
有機半導體可為聚合或非聚合材料。較佳地,有機半導體為聚合物,更佳為共軛聚合物。
較佳地,有機半導體包含極性雙或參鍵,視情況選自C=N基、腈基或C=O基之鍵。較佳地,此等極性雙或參鍵基共軛至共軛聚合物主鏈上。有機半導體可包含苯并噻二唑單元。苯并噻二唑單元可為聚合物之單元。聚合重複單元可包含或由下式之重複單元組成:
其中R1在每次出現時為取代基,視情況選自烷基之取代基,視情況C1-20烷基,其中一或多個不相鄰C原子可經視情況經取代之芳香基或雜芳基、O、S、C=O或-COO-置換,且一或多個H原子可經F置換。
包含苯并噻二唑之重複單元可具有下式:
其中R1如上文所描述。
聚合物可包含含有苯并噻二唑重複單元及伸芳基重複單元之重複單元。
伸芳基重複單元包括但不限於茀、伸苯基、萘、蒽、茚并茀、菲及二氫菲重複單元,其中之每一者可經或未經一或多個取代基取代。
伸芳基重複單元之取代基(若存在)可選自C1-40烴基,較佳為C1-20烷基;可未經或經一或多個C1-10烷基取代之苯基。
伸芳基重複單元之一較佳類別為伸苯基重複單元,諸如式(VI)伸苯基重複單元:
其中w在每次出現時獨立地為0、1、2、3或4,視情況為1或2;n為1、2或3;且R7獨立地在每次出現時為取代基。
在存在之情況下,每一R7可獨立地為選自由以下各者組成之群:- 烷基,視情況C1-20烷基,其中一或多個不相鄰C原子可經視情況經取代之芳香基或雜芳基、O、S、C=O或-COO-置換,且一或多個H原子可經F置換;及- 式-(Ar7)r之群,其中每一Ar7獨立地為可未經或經一或多個取代基取代之芳香基或雜芳基,且r為至少1,視情況1、2或3,較佳為苯基之分支鏈或直鏈,其中之每一者可具有一或多個C1-20烷基。
在R7包含芳基或雜芳基,或芳基或雜芳基之直鏈或分支鏈之情況下,該或每一芳基或雜芳基可經一或多個選自由以下各者組成之群的取代基R8取代:烷基,例如C1-20烷基,其中一或多個不相鄰C原子可
經O、S、C=O及-COO-置換,且烷基之一或多個H原子可經F置換;氟;硝基;及氰基。
較佳地,每一R7在存在之情況下,獨立地選自C1-40烴基,且更佳選自C1-20烷基;未經取代之苯基;經一或多個C1-20烷基取代之苯基;苯基之直鏈或分支鏈,其中每一苯基可未經或經一或多個取代基取代;及可交聯基。
若n為1,則隨後式(VI)例示性重複單元包括下式:
式(VI)尤佳重複單元具有式(VIa):
式(VIa)之取代基R7與重複單元之鍵聯位置相鄰,其可在式(VIa)之重複單元與相鄰重複單元之間產生位阻,導致式(VIa)之重複單元相對於一個或兩個相鄰重複單元而在平面外扭轉。
n為2或3之例示性重複單元包括下式:
較佳重複單元具有式(VIb):
式(VIb)之兩個R7基可在其鍵結至之苯基環之間產生位阻,導致兩種苯基環相對於彼此而扭轉。
伸芳基重複單元之另一類別為視情況經取代之茀重複單元,諸如式(VII)之重複單元:
其中R7在每次出現時為相同的或不同的,且為如參考式(VI)所描述之取代基,且其中兩個R7基可經連結以形成環;R8為取代基;且d為0、1、2或3。
茀重複單元之芳族碳原子可未經取代,或可經一或多個取代基R8取代。例示性取代基R8為烷基,例如C1-20烷基,其中一或多個不相鄰C原子可經O、S、C=O及-COO-置換,視情況經取代之芳香基、視情況經取代之雜芳基、烷氧基、烷硫基、氟、氰基及芳基烷基。尤佳取代基包括C1-20烷基及經取代或未經取代之芳香基,例如苯基。芳香基之可選取代基包括一或多個C1-20烷基。
式(VII)之重複單元共軛至聚合物主鏈中之相鄰重複單元的芳香基或雜芳基之程度可藉由以下所控制:(a)穿過3-及/或6-位置鍵聯重複單元以在重複單元中限制共軛程度,及/或(b)在一或多個與鍵聯位置相鄰之位置中,用一或多個取代基R8取代重複單元以引起相鄰重複單元或單元之扭曲,例如在3-及6-位置中之一或兩者中攜載C1-20烷基取代基之2,7-鍵聯茀。
式(VII)之重複單元可為視情況經取代之式(VIIa)2,7-鍵聯重複單元:
視情況,式(VIIa)之重複單元在與2-或7-位置相鄰之位置中未經取代。穿過2-及7-位置之鍵及與此等鍵聯位置相鄰之取代基的缺失提供能夠在重複單元中提供相對高程度之共軛的重複單元。
式(VII)之重複單元可為視情況經取代之式(VIIb)之3,6-鍵聯重複單元
式(VIIb)之重複單元中之共軛程度相比於式(VIIa)之重複單元可相對較低。
另一例示性伸芳基重複單元具有式(VIII):
其中R7、R8及d如參考上文式(VI)及(VII)所描述。R7基之任一者可鍵聯至R7基之任一其他者以形成環。因此形成之環可未經取代或可經一或多個取代基取代,視情況一或多個C1-20烷基。
如本文任何位置所描述之聚合物適當具有藉由凝膠滲透層析法在約1x103至1x108,且較佳1x103至5x106之範圍內量測之聚苯乙烯-等效數量平均分子量(Mn)。本文任何位置所描述之聚合物的聚苯乙烯-等效重量平均分子量(Mw)可為1x103至1x108,且較佳為1x104至1x107。
如本文任何位置所描述之聚合物適當為非晶形聚合物。
例示性n型摻雜劑試劑包含2,3-二氫-苯并咪唑基,視情況2,3-二氫-1H-苯并咪唑基。n型摻雜劑試劑可具有式(I):
其中:每一R2獨立地為C1-20烴基,視情況C1-10烷基;R3為H或C1-20烴基,視情況H、C1-10烷基或C1-10烷基苯基;且每一R4獨立地為C1-20烴基,視情況C1-10烷基、苯基或經一或多個C1-10烷基取代之苯基。
例示性n型摻雜劑試劑包括下式:
N-DMBI揭示於Adv.Mater.2014,26,4268-4272中,其內容以引用之方式併入本文中。
OLED 100之發光材料可為螢光材料、磷光材料或螢光及磷光材料之混合物。發光材料可選自聚合及非聚合發光材料。例示性發光聚合物為共軛聚合物,例如聚苯及聚茀,其實例描述於Bernius,M.T.,Inbasekaran,M.,O'Brien,J.及Wu,W.,Progress with Light-Emitting Polymers.Adv.Mater.,12 1737-1750,2000中,其內容以引用之方式併入本文中。發光層107可包含主體材料及螢光或磷光發光摻雜劑。例示性磷光摻雜劑為列2或列3過渡金屬錯合物,例如釕、銠、鈀、錸、鋨、銥、鉑或金之錯合物。
OLED之發光層可未經圖案化,或可經圖案化以形成離散像素。每一像素可進一步分成子像素。發光層可含有單個發光材料,例如用於單色顯示器或其他單色器件,或可含有發射不同色彩之材料,詳言之用於全色顯示器之發射紅、綠及藍光之材料。
發光層可含有多於一種發光材料之混合物,例如一起提供白光發射之發光材料的混合物。複數個發光層可一起產生白光。
螢光發光層可由發光材料單獨組成或可進一步包含一或多個其他與發光材料混合之材料。其他例示性材料可選自電洞傳輸材料;電子傳輸材料及三元組-接收材料,例如如WO 2013/114118中所描述之三元組-接收聚合物,其內容以引用之方式併入本文中。
陰極可包含一或多個層。較佳地,陰極包含或由與包含或由一或多個導電材料組成之電子注入層接觸之層組成。例示性導電材料為金屬,較佳為具有至少4eV之功函數的金屬,視情況為鋁、銅、銀或金或鐵。例示性非金屬導電材料包括導電金屬氧化物,例如氧化銦錫及氧化銦鋅、石墨及石墨烯。金屬之功函數如在CRC Handbook of
Chemistry and Physics,12-114,第87版,CRC Press出版,David R.Lide編輯中所給出。若給出金屬之多於一種數值,則隨後首次所列之數值適用。
陰極可為不透明的或透明的。透明陰極尤其有利於主動型矩陣器件,因為穿過此類器件中之透明陽極之發射至少部分地經位於發射像素下方之驅動電路阻斷。
應瞭解,透明陰極器件不必具有透明陽極(除非需要完全透明器件),且因此用於底部發射之器件的透明陽極可經置換或補充有反射材料層,諸如鋁層。透明陰極器件之實例揭示於例如GB 2348316中。
可在陽極103及發光層105之間提供電洞傳輸層。
電洞傳輸層可為交聯的,尤其當上覆層自溶液沈積時。用於此交聯之可交聯基可為包含反應性雙鍵(諸如乙烯基或丙烯酸酯基,或苯并環丁烷基)之可交聯基。可藉由熱處理進行交聯,較佳在低於約250℃之溫度下,視情況在約100至250℃之範圍內。
電洞傳輸層可包含或可由電洞傳輸聚合物組成,其可為包含兩種或多於兩種不同重複單元之均聚物或共聚物。電洞傳輸聚合物可為共軛的或非共軛的。例示性共軛電洞傳輸聚合物為包含芳胺重複單元之聚合物,例如如WO 99/54385或WO 2005/049546中所描述,其內容以引用之方式併入本文中。包含芳胺重複單元之共軛電洞傳輸共聚物可具有一或多個選自伸芳基重複單元之共同重複單元,例如一或多個選自茀、伸苯基、菲、萘及蒽重複單元之重複單元,其中之每一者可獨立地未經或經一或多個取代基(視情況一或多個C1-40烴基取代基)取代。
如藉由循環伏安法所量測,位於陽極與發光層105之間的電洞傳
輸層(若存在)較佳具有低於或等於5.5eV之HOMO能階,更佳約4.8至5.5eV或5.1至5.3eV。可選擇電洞傳輸層之HOMO能階以使其在相鄰層之0.2eV以內,視情況在0.1eV以內,以在此等層之間對電洞傳輸提供小型障壁。
較佳電洞傳輸層,更佳交聯電洞傳輸層與發光層105相鄰。
電洞傳輸層可基本上由電洞傳輸材料組成或可包含一或多種其他材料。可在電洞傳輸層中提供發光材料,視情況磷光材料。
磷光材料可共價鍵結至電洞傳輸聚合物作為聚合物主鏈中之重複單元,作為聚合物之端基,或作為聚合物之側鏈。若在側鏈中提供磷光材料,則隨後其可直接鍵結至聚合物主鏈中之重複單元或其可自聚合物主鏈上經間隔基團間隔開。例示性間隔基團包括C1-20烷基及芳基-C1-20烷基,例如苯基-C1-20烷基。間隔基團之烷基的一或多個碳原子可經O、S、C=O或COO置換。
來自發光電洞傳輸層之發射及來自發光層105之發射可組合以產生白光。
如圖1中所說明,可在OLED之陽極103與發光層105之間提供導電電洞注入層(其可形成自導電有機或無機材料)來輔助自陽極至半導電聚合物層之電洞注入。摻雜有機電洞注入材料之實例包括視情況經取代之摻雜聚(伸乙基二氧噻吩)(PEDT),詳言之如EP 0901176及EP 0947123中所揭示之摻雜有電荷平衡多元酸(諸如聚苯乙烯磺酸酯(PSS))之PEDT、聚丙烯酸或氟化磺酸,例如納菲®(Nafion ®);如US 5723873及US 5798170中所揭示之聚苯胺;及視情況經取代之聚噻吩或聚(噻吩并噻吩)。導電無機材料之實例包括過渡金屬氧化物,諸如如Journal of Physics D:Applied Physics(1996),29(11),2750-2753中所揭示之VOx MoOx及RuOx。
n型摻雜劑試劑之薄膜及有機半導體較佳在囊封含有薄膜之器件後曝露於輻射來引起如本文所描述之n型摻雜,以防止濕氣及氧氣之進入。
合適的囊封劑包括玻璃片材、具有合適障壁特性之薄膜(諸如二氧化矽、一氧化矽、氮化矽或交替的聚合物之堆疊)及介電質或密閉容器。至於透明陰極器件,諸如一氧化矽或二氧化矽之透明囊封層可沈積至微米級之厚度,但在一個較佳實施例中,此層之厚度在20至300nm之範圍內。用於吸收任何可滲透過基板或囊封劑之大氣壓濕氣及/或氧氣的集氣劑材料可安置於基板與囊封體之間。
形成器件之基板較佳具有良好障壁特性以使基板連同囊封劑形成抗濕氣或氧氣進入之障壁。基板通常為玻璃,然而,特定言之當器件之可撓性合乎需要時可使用替代性基板。舉例而言,基板可包含一或多個塑膠層,例如交替塑膠及介電質障壁層之基板或薄玻璃及塑膠之層合物。
可藉由任何包括蒸發及溶液沈積法之方法形成發光層105及電子注入層107。較佳為溶液沈積法。
適於形成發光層105及電子注入層107之調配物可各自由形成彼等層之組分及一或多個合適溶劑形成。
較佳地,藉由沈積溶液來形成發光層105,其中溶劑為一或多種非極性溶劑材料,視情況為經一或多個選自C1-10烷基及C1-10烷氧基之取代基取代之苯,例如甲苯、二甲苯及甲基苯甲醚及其混合物。
視情況,藉由沈積溶液來形成經照射以形成電子注入層107之包含有機半導體及n型摻雜劑試劑之薄膜。
尤佳溶液沈積技術包括印刷及塗覆技術,諸如旋塗、噴墨印刷
及石印印刷。
塗覆方法尤其適於發光層之圖案化為不必要之器件,例如適於照明應用或簡單單色分段式顯示器。
印刷方法尤其適於高資訊內容顯示器,詳言之全色顯示器。可藉由在陽極上方提供圖案化層及界定用於印刷一種色彩(在單色器件之情況下)或多種色彩(在多色,詳言之全色器件之情況下)之槽孔來對器件進行噴墨印刷。圖案化層通常為經圖案化以界定如(例如)EP 0880303中所描述之槽孔的光阻層。
作為槽孔之替代方案,可將墨印刷至在圖案化層內經界定之槽。詳言之,可圖案化光阻以形成槽,其不同於槽孔,在複數個像素上方延伸且其可在槽端處關閉或打開。
其他溶液沈積技術包括浸塗、槽模塗佈、輥筒印刷及絲網印刷。
已參考有機發光器件之電子注入層描述摻雜有機半導體層,然而應瞭解,如本文所描述之所形成的層可用於其他有機電子器件中,例如作為有機光伏打器件或有機光探測器之電子萃取層;作為n型有機薄膜電晶體之輔助電極層或作為熱電產生器中之n型半導體。
藉由將伴有摻雜劑,或伴有摻雜劑之覆蓋層之共混物旋塗至玻璃基板上,以量測如本文所描述之原始及n型摻雜受體材料之UV可見吸收光譜。薄膜厚度在20至100nm之範圍內。
旋塗及乾燥後,將聚合物薄膜囊封於手套工作箱中,以切斷n型摻雜薄膜與空氣之任何接觸。
囊封後,用Carey-5000光譜儀進行UV-vis吸收量測,隨後連續曝露於可見光且重複UV-vis量測。
藉由方波伏安法量測如本文任何位置所描述之HOMO、SOMO及LUMO能階。
具有軟體之CHI660D電化學工作站(IJ Cambria Scientific Ltd)CHI 104 3mm玻璃狀碳盤工作電極(IJ Cambria Scientific Ltd)
參考電極(Ag/AgCl)(Havard Apparatus Ltd)
乙腈(高乾式無水級-ROMIL) (電池溶液溶劑)
甲苯(高乾式無水級) (樣品製備溶劑)
二茂鐵-FLUKA (參考標準)
六氟磷酸氫氧化四丁銨-FLUKA (電池溶液鹽)
於工作電極上旋轉受體聚合物成為薄膜(~20nm);在甲苯中量測呈稀溶液(0.3w%)狀之摻雜材料。
量測電池含有電解質、玻璃狀碳工作電極(於其上塗覆樣本成為薄膜)、鉑對立電極及Ag/AgCl參考玻璃電極。在實驗的末尾將二茂鐵添加至電池中作為參考材料(LUMO(二茂鐵)=-4.8eV)。
n型摻雜劑之電離引起咪唑鎓陽離子之形成。為了測定相對應的咪唑鎓基團之SOMO能階,陽離子首先在氧化掃描期間產生自中性摻雜劑分子,其亦允許測定中和摻雜劑分子之HOMO能階。
研究藉由摻雜劑1摻雜聚合物1及聚合物2。
藉由如WO 00/53656中所描述之鈴木聚合(Suzuki polymerisation)製備9,9-二辛基茀及二溴苯并噻二唑之2,7-二硼酸酯聚合物1。聚合物1具有2.9eV之LUMO能階。
如WO 01/49768中所描述,製備聚合物2。聚合物2具有3.1eV之LUMO能階。
自Sigma Aldrich獲得摻雜劑1(1,3-二甲基-2-苯基-2,3-二氫-1H-苯并咪唑)。摻雜劑1具有2.7eV之SOMO能階及4.7eV之HOMO能階。
圖2顯示聚合物1、聚合物2及摻雜劑1之UV-vis吸收光譜。
聚合物1在約330nm及470nm處具有吸收峰。
聚合物2在約375nm及535nm處具有吸收峰。
藉由旋塗使聚合物1及摻雜劑1之調配物沈積於玻璃層上以形成薄膜,使用購自Enfis Ltd,UK之ENFIS UNO Air Cooled Light Engine
用具有465nm之波峰波長的光線照射薄膜2小時。
在照射之前及之後量測薄膜之UV-vis光譜。光譜顯示於圖3中,其中實線為照射前之光譜且虛線為照射後之光譜。
在550nm至800nm之波長範圍中出現寬的、新的波峰,以及吸收中之微弱增加達約1000nm。
此等處於較高波長處之新的吸收特徵歸因於n型摻雜所致之電子間隙狀態(極化子及/或雙極化子狀態)之形成。
藉由旋塗使聚合物2及摻雜劑1之調配物沈積於玻璃層上以形成薄膜,使用購自Enfis Ltd,UK之ENFIS UNO Air Cooled Light Engine用具有465nm之波峰波長的光線照射薄膜2小時。
如摻雜實例2中所描,述沈積調配物且照射,除了使用購自Enfis Ltd,UK之ENFIS UNO Air Cooled Light Engine用具有520nm之波峰波長的光線照射薄膜2小時。
在照射之前及之後量測摻雜實例2且3之薄膜的UV-vis光譜。光譜顯示於圖4中,其中實線為照射前之光譜;虛線為在處465nm照射後之光譜(摻雜實例2)且點虛線為在520nm處照射後之光譜(摻雜實例3)。
如同摻雜實例1,在約600nm處出現之新的波峰歸因於n型摻雜。
製備具有以下結構之唯電子器件:玻璃基板/ITO/供體-受體層/Ag
藉由在鄰二甲苯中旋塗1wt%聚合物1:摻雜劑1之調配物(99:1wt%)至約100nm之厚度來形成供體-受體層。藉由蒸發銀至約100nm
之厚度來形成陰極。
使用購自Enfis Ltd,UK之ENFIS UNO Air Cooled Light Engine用具有465nm之波峰波長的光線穿過基板照射器件。
照射前及照射後量測器件之電流-電壓特徵達1秒、10秒、1分鐘、5分鐘及10分鐘且其顯示於圖5中。
如本文所描述之唯電子器件的電流密度可用於測定有機半導體之摻雜程度,電流密度與摻雜程度成比例。
如對於器件實例1所描述製備唯電子器件,除了聚合物1:摻雜劑1比率為95:5wt%且照射時間為30分鐘。
此器件之電流密度對電壓顯示於圖6中。對於此器件,二極體特徵缺失表明供體-受體層為退化半導體層。
儘管已根據特定例示性實施例描述本發明,但應瞭解,本文所揭示之特徵的各種修改、變更及/或組合將在不脫離如以下申請專利範圍中所闡述之本發明範疇的情況下對於熟習此項技術者顯而易見。
100‧‧‧有機發光二極體(OLED)
101‧‧‧基板
103‧‧‧陽極
105‧‧‧發光層
107‧‧‧電子注入層
109‧‧‧陰極
Claims (28)
- 一種形成n型摻雜半導體層之方法,其中藉由具有有機半導體之吸收範圍內的波長之光線照射包含該有機半導體及n型摻雜劑試劑之薄膜,且其中該n型摻雜劑試劑之吸收最大波長短於該光線之任何波峰波長。
- 如請求項1之方法,其中該有機半導體之吸收最大波長大於400nm。
- 如請求項1或2之方法,其中該n型摻雜劑試劑之吸收最大波長不多於350nm。
- 如請求項1或2之方法,其中該光線具有在400至700nm之範圍內的波峰波長。
- 如請求項1或2之方法,其中該n型摻雜劑試劑為(4-(1,3-二甲基-2,3-二氫-1H-苯并咪唑-2-基)苯基)二甲胺。
- 如請求項1或2之方法,其中該有機半導體包含選自C=N基、腈基、C=O基及C=S基之鍵。
- 如請求項1或2之方法,其中該有機半導體為聚合物。
- 如請求項7之方法,其中該聚合物為共軛聚合物。
- 如請求項1或2之方法,其中該有機半導體具有離真空能階不多於3.2eV之最低未佔用分子軌域能階。
- 如請求項1或2之方法,其中衍生自該n型摻雜劑試劑之基團的半佔用分子軌域能階比該有機半導體之該最低未佔用分子軌域能階離真空能階遠不多於0.5eV。
- 如請求項1或2之方法,其中藉由溶液沈積方法形成該薄膜。
- 如請求項1或2之方法,其中該薄膜形成於空氣中。
- 如請求項1或2之方法,其中該有機半導體:n型摻雜劑試劑比率 在99:1至50:50之範圍內。
- 一種形成有機電子器件之n型摻雜層的方法,其中根據請求項1至13中任一項形成該n型摻雜層。
- 如請求項14之方法,其中該有機電子器件為包含陽極、陰極及介於該陽極與該陰極之間的發光層之有機發光器件,且其中該n型摻雜層為介於該發光層與該陰極之間的電子注入層。
- 如請求項15之方法,其中藉由溶液沈積方法形成該發光層。
- 如請求項15或16之方法,其中該電子注入層與該發光層接觸。
- 如請求項15或16之方法,其中穿過該器件之陽極或陰極照射該薄膜。
- 如請求項15或16之方法,其中在該器件之囊封後照射該薄膜。
- 一種組合物,其包含:(a)有機半導體,其包含含有C=N基、腈基、C=O基及C=S基中之一或多者之單元;及(b)n型摻雜劑試劑,其包含2,3-二氫-苯并咪唑基。
- 如請求項20之組合物,其中該n型摻雜劑試劑包含2,3-二氫-1H-苯并咪唑基。
- 如請求項20或21之組合物,其中該n型摻雜劑試劑為式(I)之化合物:
- 如請求項20或21之組合物,其中該有機半導體為聚合物。
- 如請求項20或21之組合物,其中該有機半導體包含苯并噻二唑基。
- 如請求項20或21之組合物,其中該n型摻雜劑試劑為(4-(1,3-二甲基-2,3-二氫-1H-苯并咪唑-2-基)苯基)二甲胺。
- 一種自如請求項20至25中任一項之組合物形成n型摻雜半導體層之方法,該方法包含激發該有機半導體之步驟。
- 如請求項26之方法,其中藉由熱處理或電磁照射激發該有機半導體。
- 如請求項26或27之方法,其中該n型摻雜劑試劑為(4-(1,3-二甲基-2,3-二氫-1H-苯并咪唑-2-基)苯基)二甲胺。
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TWI667328B (zh) * | 2017-08-10 | 2019-08-01 | 大陸商昆山國顯光電有限公司 | 有機電致發光器件 |
TWI673894B (zh) * | 2017-11-18 | 2019-10-01 | 大陸商昆山國顯光電有限公司 | 有機電致發光器件 |
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JP6224758B2 (ja) * | 2016-03-29 | 2017-11-01 | 住友化学株式会社 | 発光素子及びその製造方法 |
KR20180025060A (ko) * | 2016-08-31 | 2018-03-08 | 엘지디스플레이 주식회사 | 유기발광소자 및 이를 구비한 유기발광 표시장치 |
KR20230133985A (ko) | 2017-04-07 | 2023-09-19 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 표시 장치, 전자 기기, 및 조명 장치 |
JP7108493B2 (ja) * | 2018-08-06 | 2022-07-28 | 日本放送協会 | 有機薄膜および有機薄膜の製造方法、有機エレクトロルミネッセンス素子およびその製造方法、表示装置、照明装置、有機薄膜太陽電池、薄膜トランジスタ |
JP2020088028A (ja) * | 2018-11-19 | 2020-06-04 | トヨタ自動車株式会社 | 熱電変換素子、熱電変換システム、及びそれらを用いる発電方法 |
CN110845420A (zh) * | 2019-11-05 | 2020-02-28 | 五邑大学 | 一种化合物及其制备方法和作为n-型掺杂剂的应用 |
CN113201244B (zh) * | 2021-04-30 | 2022-07-01 | 桂林理工大学 | 一种掺杂剂及其制备方法、应用、功能化乳胶漆 |
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US20080015269A1 (en) * | 2006-04-17 | 2008-01-17 | Bazan Guillermo C | Hybrid polymer light-emitting devices |
EP1912268B1 (de) * | 2006-10-09 | 2020-01-01 | Novaled GmbH | Verfahren zur räumlichen Strukturierung der Leuchtdichte von lichtermittierenden organischen Halbleiterbauelementen, danach hergestelltes Halbleiterbauelement und Verwendung desselben |
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WO2011127075A1 (en) * | 2010-04-05 | 2011-10-13 | The Board Of Trustees Of The Leland Stanford Junior University. | N-type doped organic materials and methods therefor |
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WO2013098648A1 (en) * | 2011-12-30 | 2013-07-04 | Imperial Innovations Ltd. | Unconventional chemical doping of organic semiconducting materials |
JP5993667B2 (ja) * | 2012-09-03 | 2016-09-14 | 日本放送協会 | 有機電界発光素子 |
CN104247073B (zh) * | 2012-04-16 | 2017-07-18 | 日本放送协会 | 有机电致发光元件及其制造方法 |
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US11289655B2 (en) | 2017-08-10 | 2022-03-29 | Kunshan Go-Visionox Opto-Electronics Co., Ltd. | Organic electroluminescent device |
TWI673894B (zh) * | 2017-11-18 | 2019-10-01 | 大陸商昆山國顯光電有限公司 | 有機電致發光器件 |
US11362295B2 (en) | 2017-11-18 | 2022-06-14 | Kunshan Go-Visionox Opto-Electronics Co., Ltd. | Organic electroluminescent device |
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US20170033286A1 (en) | 2017-02-02 |
JP2017033929A (ja) | 2017-02-09 |
CN106409665B (zh) | 2022-02-18 |
GB2540969B (en) | 2017-12-27 |
KR20170015182A (ko) | 2017-02-08 |
US9960352B2 (en) | 2018-05-01 |
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