TWI613205B - 含硼化合物、有機發光二極體的發光層以及有機發光二極體裝置 - Google Patents
含硼化合物、有機發光二極體的發光層以及有機發光二極體裝置 Download PDFInfo
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- TWI613205B TWI613205B TW105121773A TW105121773A TWI613205B TW I613205 B TWI613205 B TW I613205B TW 105121773 A TW105121773 A TW 105121773A TW 105121773 A TW105121773 A TW 105121773A TW I613205 B TWI613205 B TW I613205B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 50
- 239000002019 doping agent Substances 0.000 claims abstract description 23
- 239000000463 material Substances 0.000 claims description 47
- 230000003111 delayed effect Effects 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000000243 solution Substances 0.000 description 69
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 24
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 21
- 238000004896 high resolution mass spectrometry Methods 0.000 description 17
- 238000002347 injection Methods 0.000 description 17
- 239000007924 injection Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
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- 239000000126 substance Substances 0.000 description 10
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- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
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- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
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- FJMNNXLGOUYVHO-UHFFFAOYSA-N aluminum zinc Chemical compound [Al].[Zn] FJMNNXLGOUYVHO-UHFFFAOYSA-N 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
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- 229910052762 osmium Inorganic materials 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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Abstract
一種含硼化合物,其具有如式(I)所示之一結構,藉此,有利於作為有機發光二極體的發光層的摻雜物,使有機發光二極體具有高效率、可降低成本並可提供寬廣的光調色能力等優點。
Description
本發明是有關於一種含硼化合物、有機發光二極體的發光層以及有機發光二極體裝置,且特別是有關於一種可作為有機發光二極體發光層之摻雜物(dopant)的含硼化合物、包含此含硼化合物的有機發光二極體的發光層以及有機發光二極體裝置。
有機發光二極體(Organic Light Emitting Diode,OLED)係指以有機分子作為發光層材料,並以電壓驅動其發光的元件。與液晶顯示器相較,OLED具有輕量、廣視角、高對比、低耗電、高應答速度、高發光效率、易於調整光色、可應用於可撓基板,而成為業者關注的對象。
最早期的OLED係使用螢光(fluorescence)材料,即利用激子由單重激發態(singlet excited state)回到單重基態(singlet ground state),並以螢光的形式釋放能量,然而,螢光材料的內部量子效率(internal quantum
efficiency,IQE)最高僅能到達25%,而其餘的75%則以熱之非輻射(non-radiative)方式釋出,故效率不佳。
另有業者發展出使用磷光材料的OLED,其係將貴金屬如銥(Ir)、鉑(Pt)、鋨(Os)、釕(Ru)導入發光層的有機分子中形成錯合物,以產生自旋-軌域耦合(spin-orbital coupling)效應,而可同時得到激子由單重激發態回到單重基態的螢光形式以及電子由三重激發態(triplet excited state)回到單重基態的磷光形式,而使內部量子效率達到100%。導入貴金屬雖可大幅提升OLED的效率,然而,貴金屬的價格高昂,導致磷光材料的成本高居不下,此外,目前尚無法利用磷光材料順利製造出藍光OLED。
熱激活延遲螢光(Thermal Activated Delayed Fluorescence;TADF)材料是繼螢光材料與磷光材料之後發展出的第三代有機發光材料,此類材料之單重激發態與三重激發態的能階差(△EST)很小,而使位於三重激發態的電子可以通過反系間穿越(Reverse Intersystem Crossing;RISC)轉換至單重激發態,故可充分利用單重激發態與三重激發態的激子以輻射方式放出能量(螢光及延遲螢光),使內部量子效率達到100%。TADF材料具有高效率、成本低(不需使用貴金屬)、可提供寬廣的光調色能力(可製造出藍光OLED)而成為關注的焦點。
然而,現今以TADF材料製成的OLED鮮少可提供足以與磷光材料匹配的外部量子效率(external
quantum efficiency;EQE)。研究指出TADF材料所使用的化合物,其分子結構攸關著OLED的性能,例如,目前已知將最高佔據分子軌域(Highest Occupied Molecular Orbital;HOMO)安排在供電子基團(donor)、將最低未佔分子軌域(Lowest Unoccupied Molecular Orbital;LUMO)安排在受電子基團(acceptor),並使HOMO與LUMO部分重疊有利於增強TADF性質,且藉由增加供電子基團平面與受電子基團平面的扭轉角(twist angle)可降低△EST,以提高RISC的機率。然而,過大的扭轉角又可能抑制激子由單重激發態回到單重基態的輻射衰減,而減損發光效益。
此外,在眾多化合物之中,含硼化合物因硼具有空P軌道,可與周圍的π電子雲產生交互作用而被認為具有應用有機發光材料的潛力,然而,目前已知的含硼化合物,其內部量子效率鮮少超過30%,且具有對空氣及水氣敏感的缺失,使其在有機發光材料上的應用難以突破。
因此,如何改良含硼化合物的結構,使其供電子基團與受電子基團的配置恰當而具有TADF材料特性(即內部量子效率為100%),而可突破含硼化合物以往在有機發光材料應用上的限制,並使其製成的OLED具有優良的效率,係相關業界與學界努力的目標。
依據本發明之一目的,是提供一種含硼化合
物,藉由其分子結構,使其具有TADF材料特性,而有利於作為OLED發光層的摻雜物(dopant),其可使OLED具有高效率、低成本並可提供寬廣的光調色能力等優點。
本發明之另一目的,是提供一種OLED的發光層,其使用上述之含硼化合物作為摻雜物,而使OLED具有高效率、低成本並可提供寬廣的光調色能力等優點。
本發明之又一目的,是在提供一種OLED裝置,其具有高效率、低成本並可提供寬廣的光調色能力等優點。
依據前述的含硼化合物,R1可各自獨立為式(i)或式(ii)所示之一結構:
其中m與q各自獨立為0至4的整數,R3與R5各自獨立為甲氧基(methoxy group)或叔丁基(tert-butyl group)。
依據前述的有機發光二極體的發光層,其中摻雜物於發光層中的摻雜濃度為5%至30%。
依據本發明一態樣之又一實施方式,提供一種有機發光二極體裝置,包含上述的有機發光二極體的發光層。
100‧‧‧有機發光二極體裝置
110‧‧‧陽極
120‧‧‧電洞注入層
141‧‧‧主體材料
142‧‧‧摻雜物
150‧‧‧電子傳輸層
130‧‧‧電洞傳輸層
140‧‧‧發光層
160‧‧‧電子注入層
170‧‧‧陰極
為讓本發明之上述和其他目的、特徵、優點與實施例能更明顯易懂,所附圖式之說明如下:第1圖是繪示依照本發明一實施方式的一種有機發光二極體的發光層的剖面示意圖;第2圖是繪示依照本發明另一實施方式的一種有機發光二極體裝置的剖面示意圖;第3A圖是實施例1的1H-NMR光譜圖;第3B圖是實施例1的13C-NMR光譜圖;第3C圖是實施例1的高解析質譜儀(High resolution mass spectrometry;HRMS)結果圖;第3D圖是實施例1的另一1H-NMR光譜圖;第4A圖是實施例2的1H-NMR光譜圖;第4B圖是實施例2的13C-NMR光譜圖;第4C圖是實施例2的HRMS結果圖;第4D圖是實施例2的另一1H-NMR光譜圖;第5A圖是實施例3的1H-NMR光譜圖;第5B圖是實施例3的13C-NMR光譜圖;第5C圖是實施例3的HRMS結果圖;第5D圖是實施例3的另一1H-NMR光譜圖;第6A圖是實施例4的1H-NMR光譜圖;第6B圖是實施例4的13C-NMR光譜圖;第6C圖是實施例4的HRMS結果圖;第6D圖是實施例4的另一1H-NMR光譜圖;
第7A圖是實施例1瞬態光致發光(transient photoluminescence)圖;第7B圖是實施例2的瞬態光致發光圖;第7C圖是實施例3的瞬態光致發光圖;第7D圖是實施例4的瞬態光致發光圖;第8圖是實施例1~4的吸收光譜圖(absorption spectra);第9圖是實施例1~4的光致發光光譜圖(photoluminescence spectra);第10圖是OLED裝置A、B、C、D的外部量子效率與電流效率(Current efficiency)和亮度(Luminance)的關係圖;第11圖是OLED裝置A、B、C、D的外部量子效率與電流密度(Current density)的關係圖;以及第12圖是OLED裝置A、B、C、D的電致發光光譜圖(electroluminescent spectra)。
藉由上述結構,含硼化合物以9,10-二硼蒽(9,10-diboraanthracence;DBA)作為受電子基團,R1作為供電子基團,使含硼化合物具有TADF特性,當其受電壓驅動,可以螢光和延遲螢光的形式釋放能量,而有利於作為OLED發光層的摻雜物,其可使OLED具有高效率、低成本並可提供寬廣的光調色能力等優點。
式(i)中,m各自獨立為0至4的整數,其中m為0是指式(i)上方兩個苯環的氫皆未被取代,而m為1~4的整數是指(i)上方兩個苯環的氫可被R3取代,R3可為但不限於甲氧基或叔丁基。當式(i)中R3的數目大於1時,多個R3可相同或相異。
式(ii)中,q各自獨立為0至4的整數,其中q為0是指式(ii)上方兩個苯環的氫皆未被取代,而q為1~4的整數是指(ii)上方兩個苯環的氫可被R5取代,R5可為但不限於甲氧基或叔丁基。當式(ii)中R5的數目大於1時,多個R5可相同或相異。
請參照第1圖,其係繪示依照本發明一實施方式的一種有機發光二極體的發光層140的剖面示意圖。第1圖中,發光層140包含主體材料141和摻雜物142,其中摻雜物142係前述具有如式(I)所示之結構的含硼化合物,藉此,可使包含此發光層140的OLED具有高效率、低成本並可提供寬廣的光調色能力等優點。關於具有如式(I)所示之結構的含硼化合物請參照前文,在此不予以贅述。
摻雜物142於該發光層140中的摻雜濃度可為5%至30%。前述摻雜濃度的定義係依據摻雜物142之蒸鍍
速率與主體材料141之蒸鍍速率的比值,例如,當摻雜物142之蒸鍍速率為主體材料141之蒸鍍速率的二十分之一,則摻雜濃度為5%;又例如,當摻雜物142之蒸鍍速率為主體材料141之蒸鍍速率的十分之三,則摻雜濃度為30%。
藉由於發光層140中摻雜有摻雜物142,可使主體材料141的能量轉移到摻雜物142,而可改變主體材料141的光色及發光效率,而可擴大OLED的應用層面。
主體材料141可為高三重態能量主體材料(high triplet energy host material),主體材料141可為電洞傳輸型(hole transport type)、電子傳輸型(electron transport type)或雙極型(bi-polar type),實際應用時,可依據OLED所需的光色進行選擇,例如,主體材料可具有如式(1)至式(9)其中任一者所式之一結構:
(5)、(6)、
式(1)的化學名稱縮寫為CzPS(9,9'-(sulfonylbis(4,1-phenylene))bis(9H-carba zole))、式(2)的化學名稱縮寫為CBP(4,4'-di(9H-carbazol-9-yl)-1,1'-biphenyl)、式(3)的化學名稱縮寫為mCBP(3,3'-di(9H-carbazol-9-yl)-1,1'-biphenyl)、式(4)的化學名稱縮寫為mCP(1,3-di(9H-carbazol-9-yl)benzene)、式(5)的化學名稱縮寫為BCPO(bis(4-(9H-carbazol-9-yl)phenyl)(phenyl)phosphine oxide)、式(6)的化學名稱縮寫為TCTA(tris(4-(9H-carbazol-9-yl)phenyl)amine)、式(7)的化學名稱縮寫為DPEPO(oxybis(2,1-phenylene))bis(diphenylphosphine oxide)、式(8)的化學名稱縮寫為PPT(dibenzo[b,d]thiophene-2,8-diylbis(diphenylphosphine oxide)、式(9)的化學名稱縮寫為
TCB(1,3,5-tri(9H-carbazol-9-yl)benzene)。上述式(1)、式(3)~式(9)可用於發藍光、綠光或紅光的OLED,式(2)可用於發綠光或紅光的OLED。
一種有機發光二極體裝置,包含前述有機發光二極體的發光層,藉此,可使包含此發光層的OLED裝置具有高效率、低成本並可提供寬廣的光調色能力等優點。
請參照第2圖,其係繪示依照本發明另一實施方式的一種有機發光二極體裝置100的剖面示意圖,第2圖中,有機發光二極體裝置100包含陽極110、電洞注入層120、電洞傳輸層130、發光層140、電子傳輸層150、電子注入層160與陰極170,其中關於發光層140請參照前文,在此不予以贅述。
具體來說,陽極110的材料可為透明導電金屬氧化物或金屬,其中透明導電金屬氧化物可為銦錫氧化物(ITO,SnO2:In2O3)、氧化鋅(ZnO)或鋁鋅氧化物(AZO,Al:ZnO),金屬可為鎳(Ni)、金(Au)、鉑(Pt),當使用金屬時,陽極110的厚度較佳為小於15nm。
電洞注入層120材料的選擇係考量其HOMO能階,以有助於增加陽極110與電洞傳輸層130間電洞的傳遞為佳,電洞注入層120的材料可為但不限於HATCN(2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene)、MoO3、
NPB(4,4'-bis(N-(1-naphthyl)-N-phenylamino)biphenyl)或NPNPB(N,N'-di-phenyl-N,N'-di-(4-(N,N-di-phenyl-amino)pheny)benzidine)。
電洞傳輸層130的材料可為但不限於NPB或TCTA。
電子傳輸層150的材料可為但不限於TPBI(1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene)、TmPyPb(3,3'-[5'-[3-(3-pyridinyl)phenyl][1,1':3',1''-terphenyl]-3,3''-diyl]bispyridine)、BCP(bathocuproine)、BAlq(bis(2-methyl-8-quinolinolato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum)、TAZ(3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole)。
電子注入層160的材料可為但不限於LiF。
陰極170的材料可為但不限於鎂銀混合物、氟化鋰/鋁混合物或鋁。
有機發光二極體裝置100可更包含基板(圖未示),製造有機發光二極體裝置100時,可將陽極110、電洞注入層120、電洞傳輸層130、發光層140、電子傳輸層150、電子注入層160與陰極170依序沉積於基板上,基板可為透明玻璃基板或塑膠基板。
實施例1的合成方法如下:首先配製正丁基鋰(nBuLi)溶液、9-(4-溴-3,5-二甲基苯基)-9H-咔唑(9-(4-bromo-3,5-dimethylphenyl)-9H-carbazole)溶液以及9,10-二溴-9,10-二硼蒽(9,10-dibromo-9,10-diboraanthracene)溶液,正丁基鋰溶液是將2.5mmol的正丁基鋰溶解於1.0mL的正己烷(hexane),以形成2.5M正丁基鋰溶液。9-(4-溴-3,5-二甲基苯基)-9H-咔唑溶液是將567mg(1.62mmol)的9-(4-溴-3,5-二甲基苯基)-9H-咔唑溶解於40mL的乙醚(Et2O)所形成。9,10-二溴-9,10-二硼蒽溶液是將270mg(0.809mmol)的9,10-二溴-9,10-二硼蒽溶解於25mL的甲苯(toluene)中所形成。
將正丁基鋰溶液於10分鐘內緩慢滴入-78℃、攪拌狀態下的9-(4-溴-3,5-二甲基苯基)-9H-咔唑溶液以形成反應溶液,使反應溶液回溫至0℃並維持30分鐘,之後將反應溶液再度降溫至-78℃,將9,10-二溴-9,10-二硼蒽
溶液緩慢滴入反應溶液中,同時攪拌,滴定完成後反應溶液緩慢回復至室溫並攪拌8小時。將反應溶液以減壓方式除去揮發物以獲得粗產物。將粗產物以30mL的氯化銨水溶液(NH4Cl(aq))和30mL的二氯甲烷(dichloromethane)進行萃取後濃縮,接著再以矽膠管柱分離(沖提液:正己烷/二氯甲烷=10:1)進行純化,最後得到黃色固體產物439mg,產率為76%。請參照第3A圖至第3C圖,第3A圖是實施例1的1H-NMR光譜圖,第3B圖是實施例1的13C-NMR光譜圖,第3C圖是實施例1的HRMS結果圖,由1H NMR、13C NMR及HRMS量測結果可知,實施例1的產物為式(I-1-1)所示的含硼化合物無誤(1H NMR(400MHz,CDCl3):δ 8.18(d,J=7.6Hz,4H),7.77(dd,J=3.6,5.2Hz,4H),7.63-7.59(m,8H),7.49-7.45(m,4H),7.33-7.29(m,8H),2.22(s,12H);13C NMR(100MHz,CDCl3):δ141.1,139.7,139.0,134.0,125.8,124.5,124.5,123.3,120.3,119.7.110.1,22.8;HRMS Calcd for C52H40B2N2:714.3378.Found:714.3386)。
實施例2的合成方法如下:首先配製正丁基鋰溶液、9-(4-溴-3,5-二甲基苯基)-3,6-二叔丁基-9H-咔唑(9-(4-bromo-3,5-dimethylphenyl)-3,6-di-tert-butyl-9H-carbazole)溶液以及9,10-二溴-9,10-二硼蒽溶液,正丁基鋰溶液是將3.30mmol的正丁基鋰溶解於1.32mL的正己烷,以形成2.5M正丁基鋰溶液。9-(4-溴-3,5-二甲基苯基)-3,6-二叔丁基-9H-咔唑溶液是將1.02g(2.20mmol)的9-(4-溴-3,5-二甲基苯基)-3,6-二叔丁基-9H-咔唑溶解於40mL的乙醚所形成。9,10-二溴-9,10-二硼蒽溶液是將367mg(1.10mmol)的9,10-二溴-9,10-二硼蒽溶解於25mL的甲苯所形成。
將正丁基鋰溶液於10分鐘內緩慢滴入-78℃、攪拌狀態下的9-(4-溴-3,5-二甲基苯基)-3,6-二叔丁基-9H-咔唑溶液以形成反應溶液,使反應溶液回溫至0℃並維持30分鐘,之後將反應溶液再度降溫至-78℃,將9,10-二溴-9,10-二硼蒽溶液緩慢滴入反應溶液中,同時攪拌,滴定完成後反應溶液緩慢回復至室溫並攪拌8小時。將反應溶液以減壓方式除去揮發物以獲得粗產物。將粗產物以30mL的氯化銨水溶液和30mL的二氯甲烷進行萃取後濃縮,接著再以矽膠管柱分離(沖提液:正己烷/二氯甲烷=10:1)進行純化,最後得到橘色固體產物723mg,產率為70%。請參照第4A圖至第4C圖,第4A圖是實施例2的1H-NMR光譜圖,第4B圖是實施例2的13C-NMR光譜圖,第4C圖是實施例2的HRMS結果圖,由1H NMR、13C NMR及HRMS量測
結果可知,實施例2的產物為式(I-1-2)所示的含硼化合物無誤(1H NMR(400MHz,CDCl3):δ 8.16(d,J=1.4Hz,4H),7.76(dd,J=3.2,5.2Hz,4H),7.60-7.50(m,12H),7.29(s,4H),2.20(s,12H),1.48(s,36H);13C NMR(100MHz,CDCl3):δ142.6,139.5,139.5,139.5,139.0,133.9,124.1,123.4,123.3,116.2,109.5,34.7,32.1,22.7;HRMS Calcd for C68H72B2N2:938.5882.Found:938.5884)。
實施例3的合成方法如下:首先配製正丁基鋰溶液、9-(4-溴-3,5-二甲基苯基)-3,6-二甲氧基-9H-咔唑(9-(4-bromo-3,5-dimethylphenyl)-3,6-dimethoxy-9H-carbazole)溶液以及9,10-二溴-9,10-二硼蒽溶液,正丁基鋰溶液是將4.56mmol的正丁基鋰溶解於1.82mL的正己烷,以形成2.5M正丁基鋰溶液。9-(4-溴-3,5-二甲基苯基)-3,6-二甲氧基-9H-咔唑溶液是將1.25g(3.04mmol)的9-(4-溴-3,5-二甲基苯基)-3,6-二甲氧基-9H-咔唑溶解於40mL的乙醚所形成。9,10-二溴-9,10-二硼蒽溶液是將507mg(1.52mmol)的9,10-二溴-9,10-二硼蒽溶解於25
mL的甲苯所形成。
將正丁基鋰溶液於10分鐘內緩慢滴入-78℃、攪拌狀態下的9-(4-溴-3,5-二甲基苯基)-3,6-二甲氧基-9H-咔唑溶液以形成反應溶液,使反應溶液回溫至0℃並維持30分鐘,之後將反應溶液再度降溫至-78℃,將9,10-二溴-9,10-二硼蒽溶液緩慢滴入反應溶液中,同時攪拌,滴定完成後反應溶液緩慢回復至室溫並靜置8小時。將反應溶液以減壓方式除去揮發物以獲得粗產物。將粗產物以30mL的氯化銨水溶液和30mL的二氯甲烷進行萃取後濃縮,接著再以矽膠管柱分離(沖提液:正己烷/二氯甲烷=10:1)進行純化,最後得到橘色固體產物837mg,產率為66%。請參照第5A圖至第5C圖,第5A圖是實施例3的1H-NMR光譜圖,第5B圖是實施例3的13C-NMR光譜圖,第5C圖是實施例3的HRMS結果圖,由1H NMR、13C NMR及HRMS量測結果可知,實施例3的產物為式(I-1-3)所示的含硼化合物無誤(1H NMR(400MHz,CDCl3):δ 7.75(dd,J=3.2,5.2Hz,4H),7.60-7.58(m,8H),7.52(d,J=8.8,4H),7.27(s,4H),7.10(dd,J=2.4,8.8Hz,4H),3.97(s,12H),2.20(s,12H);13C NMR(100MHz,CDCl3):δ153.9,139.6,139.0,137.4,136.5,133.9,124.1,123.5,115.2,111.1,102.8,56.2,22.8;HRMS Calcd for C56H48B2N2O4:834.3800.Found:834.3778)。
實施例4的合成方法如下:首先配製正丁基鋰溶液、4-溴-3,5-二甲基-N,N-二苯基苯胺(4-bromo-3,5-dimethyl-N,N-diphenylaniline)溶液以及9,10-二溴-9,10-二硼蒽溶液,正丁基鋰溶液是將3.78mmol的正丁基鋰溶解於1.51mL的正己烷,以形成2.5M正丁基鋰溶液。4-溴-3,5-二甲基-N,N-二苯基苯胺溶液是將888mg(2.52mmol)的4-溴-3,5-二甲基-N,N-二苯基苯胺溶解於40mL的乙醚所形成。9,10-二溴-9,10-二硼蒽溶液是將420mg(1.26mmol)的9,10-二溴-9,10-二硼蒽溶解於25mL的甲苯所形成。
將正丁基鋰溶液於10分鐘內緩慢滴入-78℃、攪拌狀態下的4-溴-3,5-二甲基-N,N-二苯基苯胺溶液以形成反應溶液,使反應溶液回溫至0℃並維持30分鐘,之後將反應溶液再度降溫至-78℃,將9,10-二溴-9,10-二硼蒽溶液緩慢滴入反應溶液中,同時攪拌,滴定完成後反應溶液緩慢回復至室溫並靜置8小時。將反應溶液以減壓方式除去揮發物以獲得粗產物。將粗產物以30mL的氯化銨水溶液和30mL的二氯甲烷進行萃取後濃縮,接著再以矽膠管柱分離(沖提液:正己烷/二氯甲烷=10:1)進行純化,最後得到紅色固體產物534mg,產率為59%。請參照第6A圖至第6C圖,
第6A圖是實施例4的1H-NMR光譜圖,第6B圖是實施例4的13C-NMR光譜圖,第6C圖是實施例4的HRMS結果圖,由1H NMR、13C NMR及HRMS量測結果可知,實施例4的產物為式(I-1-4)所示的含硼化合物無誤(1H NMR(400MHz,CDCl3):δ7.68(dd,J=3.2,5.6Hz,4H),7.51(dd,J=3.2,5.2Hz,4H),7.30-7.26(m,8H),7.19-7.16(m,8H),7.02-6.98(m,4H),6.81(s,4H),1.97(s,12H);13C NMR(100MHz,CDCl3):δ 148.2,139.0,138.8,133.5,129.1,124.1,124.1,122.3,122.1,22.7;HRMS Calcd for C52H44B2N2:718.3691.Found:718.3687)。
請參照第7A圖至第7D圖,第7A圖是實施例1瞬態光致發光圖,第7B圖是實施例2的瞬態光致發光圖,第7C圖是實施例3的瞬態光致發光圖,第7D圖是實施例4的瞬態光致發光圖。第7A圖至第7D圖是將實施例1~4的含硼化合物溶解於甲苯中,配製為10-5M的溶液,於300K、真空條件下進行量測的結果。由第7A圖可知,實施例1的螢光生命週期(τ1)為91.84ns、延遲螢光生命週期(τ2)為3.66μs。由第7B圖可知,實施例2的螢光生命週期為108.75ns、延遲螢光生命週期為2.68μs。由第7C圖可知,實施例3的螢光生命週期為103.37ns、延遲螢光生命週期為1.15μs。由第7D圖可知,實施例4的螢光生命週期為35.04ns、延遲
螢光生命週期為1.29μs。由第7A圖至第7D圖的量測結果可知,實施例1~4的含硼化合物具有TADF材料特性。
請參照第8圖和第9圖,第8圖是實施例1~4的吸收光譜圖,第9圖是實施例1~4的光致發光光譜圖。第8圖與第9圖是將實施例1~4的含硼化合物溶解於二氯甲烷中,配製為10-5M的溶液,於300K的溫度下進行量測的結果。由第8圖與第9圖可觀察出實施例1~4的最大吸收波長(λAbsmax)、最大放射波長(λPLmax),記錄於表一中。另外,表一中的EHOMO為HOMO能階,是藉由低能量表面功率函數量測儀(AC2)獲得,ELUMO為LUMO能階,是藉由EHOMO-Eband gap獲得,Eband gap是藉由吸收光譜進行能隙的估計而獲得,Eband gap=1241/λonset(nm)。
將實施例1~實施例4的含硼化合物,於合成後放置於大氣環境下,歷時近5個月或5個月以上,再分別量測其1H-NMR光譜圖,觀察實施例1~實施例4的含硼化合物
於大氣環境下結構是否改變。請同時參照第3A圖與第3D圖,其中第3A圖是實施例1的1H-NMR光譜圖,其係2016年1月3日之量測結果,第3D圖是實施例1的另一1H-NMR光譜圖,其係2016年6月20日之量測結果,由第3A圖與第3D圖可知,實施例1的含硼化合物於大氣環境下放置5個月以上,其結構並未改變,故具有空氣/水氣穩定度。請同時參照第4A圖與第4D圖,其中第4A圖是實施例2的1H-NMR光譜圖,其係2015年12月22日之量測結果,第4D圖是實施例2的另一1H-NMR光譜圖,其係2016年6月20日之量測結果,由第4A圖與第4D圖可知,實施例2的含硼化合物於大氣環境下放置5個月以上,其結構並未改變,故具有空氣/水氣穩定度。請同時參照第5A圖與第5D圖,其中第5A圖是實施例3的1H-NMR光譜圖,其係2016年1月31日之量測結果,第5D圖是實施例3的另一1H-NMR光譜圖,其係2016年6月20日之量測結果,由第5A圖與第5D圖可知,實施例3的含硼化合物於大氣環境下放置近5個月,其結構並未改變,故具有空氣/水氣穩定度。請同時參照第6A圖與第6D圖,其中第6A圖是實施例4的1H-NMR光譜圖,其係2015年12月19日之量測結果,第4D圖是實施例4的另一1H-NMR光譜圖,其係2016年6月20日之量測結果,由第6A圖與第6D圖可知,實施例4的含硼化合物於大氣環境下放置6個月以上,其結構並未改變,故具有空氣/水氣穩定度。
OLED裝置A:係以實施例1的含硼化合物(I-1-1)作為發光層的摻雜物,摻雜濃度為10%(重量百分比)。OLED裝置A依序包含陽極、電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層與陰極,關於OLED裝置A的結構可參照第2圖,OLED裝置A的材質組成與厚度如下:ITO(130nm)/NPB(40nm)/TCTA(10nm)/CBP:含硼化合物(I-1-1)(10%)(30nm)/TmPyPb(60nm)/LiF(1nm)/Al(100nm)。
OLED裝置B:係以實施例2的含硼化合物(I-1-2)作為發光層的摻雜物,摻雜濃度為10%(重量百分比)。OLED裝置B依序包含陽極、電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層與陰極,關於OLED裝置B的結構可參照第2圖,OLED裝置B的材質組成與厚度如下:ITO(130nm)/NPB(40nm)/TCTA(10nm)/CBP:含硼化合物(I-1-2)(10%)(30nm)/TmPyPb(60nm)/LiF(1nm)/Al(100nm)。
OLED裝置C:係以實施例3的含硼化合物(I-1-3)作為發光層的摻雜物,摻雜濃度為10%(重量百分比)。OLED裝置C依序包含陽極、電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層與陰極,關於OLED裝置C的結構可參照第2圖,OLED裝置C的材質組成與厚度如下:ITO(130nm)/NPB(40nm)/TCTA(10nm)/CBP:含硼化合物(I-1-3)(10%)(30nm)/TmPyPb(60nm)/LiF(1nm)/Al(100nm)。
OLED裝置D:係以實施例4的含硼化合物(I-1-4)作為發光層的摻雜物,摻雜濃度為10%(重量百分比)。OLED裝置D依序包含陽極、電洞注入層、電洞傳輸層、發光層、電子傳輸層、電子注入層與陰極,關於OLED裝置C的結構可參照第2圖,OLED裝置D的材質組成與厚度如下:ITO(130nm)/NPB(40nm)/TCTA(10nm)/CBP:含硼化合物(I-1-4)(10%)(30nm)/TmPyPb(60nm)/LiF(1nm)/Al(100nm)。OLED裝置A~D所使用的化學物質結構如下:
請參照第10圖至第12圖,第10圖是OLED裝置A、B、C、D的外部量子效率(EQE)與電流效率和亮度的關
係圖,第11圖是OLED裝置A、B、C、D的外部量子效率與電流密度的關係圖,第12圖是OLED裝置A、B、C、D的電致發光光譜圖。並將OLED裝置A、B、C、D的啟動電壓(Vd)、最大亮度(L)與其對應電壓、最大外部量子效率(ηext)與其對應電壓、最大電流效率(ηc)與其對應電壓、最大功率效率(ηp)及其對應電壓列於表二,並將OLED裝置A、B、C、D於8V的最大放射波長λ以及色度座標(CIE)列於表三。前述啟動電壓又稱為起始電壓,其為亮度為1Cd/m2時的電壓。此外表二、表三中各數值是藉由矽光電二極體(silicon photodiode)搭配電源量測單元儀器(Keithley 2400 SourceMeter)來量測,所得實驗數據再根據OLED元件效率公式計算而得,關於量測方式與計算公式係為習用,在此不再予以贅述。
由表二可知,OLED裝置A、B、C、D的外部量子效率皆大於或等於21.1%,其中OLED裝置A、B更分別高達41.5%以及35.1%,顯示依據本發明的含硼化合物,有利於作為OLED發光層的摻雜物,使用其所製成的OLED裝置具有高效率的優點,此外,依據本發明的含硼化合物,不需如磷光材料需要搭配貴金屬,故可降低成本。此外,由表三可知,OLED裝置A、B、C、D的最大放射波長λ以及色度座標皆不同,顯示OLED裝置A、B、C、D具有不同的光色,因此依據本發明的含硼化合物可提供寬廣的光調色能力。
雖然本發明已以實施方式揭露如上,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,當可作各種之更動與潤飾,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。
Claims (7)
- 如申請專利範圍第3項所述之有機發光二極體的發光層,其中該摻雜物於該發光層中的摻雜濃度為5%至30%。
- 一種有機發光二極體裝置,包含:如申請專利範圍第3項至第6項中任一項所述之有機發光二極體的發光層。
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