TWI699357B - 用於有機電子裝置的組合物及使用其的有機電子裝置 - Google Patents
用於有機電子裝置的組合物及使用其的有機電子裝置 Download PDFInfo
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- TWI699357B TWI699357B TW108119389A TW108119389A TWI699357B TW I699357 B TWI699357 B TW I699357B TW 108119389 A TW108119389 A TW 108119389A TW 108119389 A TW108119389 A TW 108119389A TW I699357 B TWI699357 B TW I699357B
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- WCXKTQVEKDHQIY-UHFFFAOYSA-N 3-[3-[3-(3,5-dipyridin-3-ylphenyl)phenyl]-5-pyridin-3-ylphenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=NC=CC=2)=C1 WCXKTQVEKDHQIY-UHFFFAOYSA-N 0.000 description 2
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- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 238000005424 photoluminescence Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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Abstract
Description
本發明是關於一種用於有機電子裝置的組合物以及一種使用其之有機電子裝置,尤指一種作為發光層之材料的包含兩種主體化合物的組合物以及使用其之有機電子裝置。
隨著科技的進步,各種使用有機材料製成的有機電子裝置蓬勃發展,常見的有機電子裝置如有機發光二極體 (organic light emitting device,OLED)、有機光電晶體 (organic phototransistor)、有機光伏打電池 (organic photovoltaic cell)和有機光偵測器 (organic photodetector)。
OLED最初是由伊士曼柯達公司(Eastman Kodak)所發明並提出,伊士曼柯達公司的鄧青雲博士和Steven Van Slyke以真空蒸鍍法 (vacuum evaporation method)於形成有有機芳香二元胺電洞傳輸層的透明氧化銦錫 (indium tin oxide,ITO)玻璃上沉積一電子傳輸材料{例如三(8-羥基喹啉)鋁 [tris(8-hydroxyquinoline)aluminum(III),簡稱為Alq3
]};再於電子傳輸層上沉積一金屬電極,即可完成OLED的製作。OLED因兼具反應速率快、質輕、薄形化、廣視角、亮度高、對比高、無需設置背光源以及低耗能的優點,因此備受關注,但OLED仍具有低效率的問題。
為了克服低效率的問題,其中一種改善方式為於陰極和陽極間設置中間層,請參閱圖1所示,改良的OLED依序設置有一基板11、一陽極12、一電洞注入層13 (hole injection layer,HIL)、一電洞傳輸層14 (hole transport layer,HTL)、一發光層15 (an emitting layer,EL)、一電子傳輸層16 (electron transport layer,ETL)、一電子注入層17 (electron injection layer,EIL)和一陰極18。當於陽極12和陰極18施加一電壓時,由陽極12射出的電洞會穿過HIL和HTL並移動至EL,而由陰極18射出的電子會穿過EIL和ETL移動至EL,使電洞和電子在EL層重組成激子 (exciton),當激子由激發態衰退返回基態時即可產生光線。
另一改善方式為採用1,3,5-三(1-苯基-1H
-苯並咪唑-2-基)苯 (1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene,TPBi)作為OLED中發光層的主體材料。然而,即使使用了前述發光層材料,OLED的驅動電壓和電流效率仍有待改善,因此,本發明提供了一種新穎的組合物以克服現有技術存在的問題。
本發明的目的為提供一種用於有機電子裝置的組合物。
本發明另提供一種使用該組合物的有機電子裝置,藉此降低有機電子裝置的驅動電壓和提升有機電子裝置的電流效率。
為達上述目的,本發明提供一種用於有機電子裝置的組合物,其包含第一主體化合物和第二主體化合物。
於式(I)中,Y是單鍵、氧原子或硫原子。
於式(I)中,Z1
至Z3
各自獨立為CH,或式(I)中的Z1
至Z3
中相鄰的兩者相互連接形成一芳環(aryl ring),且Z1
至Z3
中剩餘的一者為CH;或式(I)中的Z1
至Z3
中相鄰的兩者相互連接形成具有至少一呋喃基(furan group)或至少一噻吩基(thiophene group)的一雜芳環(heteroaryl ring),且Z1
至Z3
中剩餘的一者為CH。
於式(I)中,X1
至X3
中的兩者各自為氮原子,且X1
至X3
中剩餘的一者為CH或氮原子。
於式(I)中,L’、L1
、和L2
各自獨立為環上碳數為6至18的芳撐基 (arylene group)。L’、L1
、和L2
彼此相同或不同。
於式(I)中,n’、n1和n2各自獨立為0至2的整數。n’、n1和n2彼此相同或不同。
於式(I)中,G1
和G2
係選自於下列所構成的群組:環上碳數為6至18的芳基、環上碳數為6至18的芳氧基(aryloxy group)、環上碳數為6至18的芳硫氧基(arylthioxy group)和包含N、O、或S原子且環上碳數為3至30的雜芳基(heteroaryl group)。G1
和G2
彼此相同或不同。
於式(II)中,L3
為環上碳數為6至18的芳撐基;n3為0至2的整數。
式(II)中,Q1
和Q2
各自獨立為CH,或式(II)中的Q1
和Q2
相互連接形成一芳環。
式(II)中,G4
和G5
係選自於下列所構成的群組:環上碳數為6至18的芳基、環上碳數為6至18的芳氧基、環上碳數為6至18的芳硫氧基和包含N原子、O原子、或S原子且環上碳數為3至30的雜芳基。
藉由包含三嗪部分(triazine moiety)或嘧啶部分(pyrimidine moiety)的第一主體化合物、以及包含至少二個咔唑部分(carbazole moiety)作為核心骨架的第二主體化合物,所述組合物中的該第一主體化合物和第二主體化合物可形成一激發錯體(exciplex)。意即,該第一主體化合物可作為激發錯體中的「受電子化合物」(acceptor compound),而該第二主體化合物可作為激發錯體中的「給電子化合物」(donor compound)。因此,所述用於有機電子裝置的組合物可降低包含其的有機電子裝置的驅動電壓並且提升其電流效率。
就式(I-II)和式(I-III)而言,Z1
為CH,而Z2
和Z3
則相互連接形成一呋喃基。就式(I-VI)和式(I-VII)而言,Z1
和Z2
相互連接形成一呋喃基,而Z3
則為CH。
就式(I-IV)和式(I-V)而言,Z1
為CH,而Z2
和Z3
則相互連接形成一噻吩基。就式(I-VIII)和式(I-IX)而言,Z1
和Z2
相互連接形成一噻吩基,而Z3
則為CH。
就式(I-X)而言,Z1
至Z3
皆為CH。就式(I-XI)而言,Z1
為CH,而Z2
和Z3
則相互連接形成一萘基。就式(I-XII)而言,Z1
和Z2
相互連接形成一萘基,而Z3
則為CH。
就式(I-XIII)而言,Z1
至Z3
皆為CH。就式(I-XIV)而言,Z1
為CH,而Z2
和Z3
則相互連接形成一萘基。就式(I-XV)而言,Z1
和Z2
相互連接形成一萘基,而Z3
則為CH。
較佳的,L’、L1
和L2
各自獨立為苯撐基(phenylene group)。
較佳的,n’是整數0或1。
較佳的,n1和n2各自獨立為整數0或1。在一些實施例中,n1和n2皆為整數0。在另一些實施例中,n1和n2皆為整數1。在另一些實施例中,n1為整數1而n2為整數0。在另一些實施例中,n1為整數0而n2為整數1。
具體而言,G1
和G2
可以是一特定的芳香族取代基(aromatic substitution)。所述特定的芳香族取代基可選自於由下列所構成的群組:、、、、、、和;其中,X為O、S或;
其中,*是鍵結位置;
p為1至5的整數、m為1至4的整數、n為1至3的整數;以及
A1
至A3
係各自獨立選自於由下列所構成的群組:氫原子、氘原子、鹵基(halo group)、氰基(cyano group)、硝基(nitro group)、碳數為1至6的烷基、碳數為2至6的烯基和碳數為2至6的炔基。
更佳的,G1
和G2
表示的環上碳數為6至18的芳基係選自於由下列所構成的群組:苯基(phenyl group)、萘基(naphthyl group)和3,5-二苯基苯基(3,5-diphenylphenyl group)。
該第一主體化合物也可以是美國發明專利公開案第2017/0213978號、第2017/0213970號、第2018/0159044號、和第2018/0155312號中所揭示的任一化合物。
就式(II-I)而言,Q1
和Q2
各自獨立為CH。就式(II-II)和式(II-III)而言,Q1
和Q2
相互連接形成一芳環。
較佳的,L3
為苯撐基。較佳的,n3是整數0或1。
具體而言,G4
和G5
可以是一特定的芳香族取代基。所述特定的芳香族取代基可選自於由下列所構成的群組:、、和;
其中,X’為O、S、或;*是鍵結位置;
p’為1至5的整數、m’為1至4的整數、n’為1至3的整數;以及
A4
至A6
係各自獨立選自於由下列所構成的群組:氫原子、氘原子、鹵基、氰基、硝基、碳數為1至6的烷基、碳數為2至6的烯基和碳數為2至6的炔基。
較佳的,G4
和G5
表示的環上碳數為6至18的芳基係選自於由下列所構成的群組:苯基、聯苯基(biphenylyl group)和萘基。
依據本發明,該第一主體化合物和該第二主體化合物的重量比為3:7至7:3。較佳的,該第一主體化合物和該第二主體化合物的重量比為4:6至6:4。在一些實施例中,該第一主體化合物和該第二主體化合物的重量比為4.5:5.5至5.5:4.5。
在說明書中,L’、L1
、L2
或L3
所指稱「環上碳數為6至18的芳撐基」,可以是環上碳數為6至18且未經取代的芳撐基,或是環上碳數為6至18且經至少一除了氫原子之外的取代基取代的芳撐基;所述在該芳撐基上的至少一取代基可選自於由下列所構成的群組:氘原子、鹵基、氰基、硝基、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基和碳數為1至12的烷氧基。
在說明書中,所述「芳基」可以是未經取代的芳基或是經至少一除了氫原子之外的取代基取代的芳基,該芳基的環上原子皆為碳原子;所述「雜芳基」可以是未經取代的雜芳基或是經至少一除了氫原子之外的取代基取代的雜芳基,該雜芳基的環上原子包含碳及其他如氧、硫或氮的雜原子。類似的,所述「芳氧基」可以是未經取代的芳氧基或是經至少一除了氫原子之外的取代基取代的芳氧基;所述「芳硫氧基」可以是未經取代的芳硫氧基或是經至少一除了氫原子之外的取代基取代的芳硫氧基。
所述在該芳基上的至少一取代基可選自於由下列所構成的群組:氘原子、鹵基、氰基、硝基、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基和碳數為1至12的烷氧基。所述在該雜芳基、該芳氧基或該芳硫氧基上的至少一取代基,可與前述在該芳基上的至少一取代基中任一者相似。
在說明書中,所述「烷基」可以是未經取代的烷基或是經至少一除了氫原子之外的取代基取代的烷基;所述「烯基」可以是未經取代的烯基或是經至少一除了氫原子之外的取代基取代的烯基;所述「炔基」可以是未經取代的炔基或是經至少一除了氫原子之外的取代基取代的炔基;前述烷基、烯基或炔基上的取代基可以是但不限於氘原子。
本發明另提供一種有機電子裝置,其包括一第一電極、一第二電極和設置於該第一電極和該第二電極間的一有機層,該有機層包括前述的組合物。
較佳的,該有機電子裝置為有機發光二極體。更佳的,該有機電子裝置是綠光OLED或紅光OLED。較佳的,本發明的組合物可作為發光層的主體材料,特別是作為綠光或紅光OLED的主體材料,但並非僅限於此。
具體而言,該OLED包括一形成於該第一電極上的電洞注入層、一形成於該電洞注入層上的電洞傳輸層、一形成於該電洞傳輸層上的發光層、一形成於該發光層上的電子傳輸層和一位於該電子傳輸層和該第二電極之間的電子注入層。
在一實施例中,所述有機層可為該發光層,也就是說,該發光層包含一第一主體材料,該第一主體材料即為前述包含該第一主體化合物和該第二主體化合物的組合物。
舉例而言,該發光層可以是一單層結構或是多層結構,當該發光層為多層結構時 (例如該發光層包括一第一發光層和一第二發光層),該第一發光層中的第一主體材料可以包括一前述組合物,該第二發光層中的第二主體材料可以包括另一前述組合物或傳統的主體材料化合物。
較佳的,該發光層是由包含所述第一主體化合物(例如化合物I-1至I-75)和第二主體化合物(例如化合物II-1至II-48)的所述組合物所製成。使用所述組合物作為發光層的主體材料的OLED可具有較佳的電流效率和較低的驅動電壓。
在另一些實施例中,所述有機層可另包含一摻雜物(dopant)。針對綠光OLED,發光層中的摻雜物可以為二氨基芴 (diaminoflourenes)、蒽二胺 (diaminoanthracenes)或具有苯基吡啶 (phenylpyridine)配位基的二價銥有機金屬化合物,但並不僅限於此。針對紅光OLED,發光層中的摻雜物可以為具有喹啉 (quinoline)配位基、異喹啉 (isoquinoline)配位基、熒蒽 (fluoranthene)配位基或二茚並 (periflanthene)配位基的二價銥有機金屬化合物,但並不僅限於此。藉由搭配前述各種發光層的主體材料,所述OLED可發出綠光或紅光。
較佳的,該電洞注入層可以為一雙層結構,即該OLED具有一第一電洞注入層和一第二電洞注入層,第一電洞注入層和第二電洞注入層設置於所述第一電極和所述電洞傳輸層之間。
所述第一和第二電洞注入層可由聚苯胺(polyaniline)或聚乙烯基二氧噻吩 (polyethylenedioxythiophene)所製成,但並不僅限於此。
較佳的,所述電洞傳輸層亦可以為一雙層結構,即該OLED具有一第一電洞傳輸層和一第二電洞傳輸層,第一電洞傳輸層和第二電洞傳輸層設置於所述雙層電洞注入層與所述發光層之間。
所述第一和第二電洞傳輸層可由N,N'-(4,4'-二聯苯基)二(N1
-(1-萘基))-N,N'-聯苯基苯-1,4-二胺 [N1
,N1'
-(biphenyl-4,4'-diyl)bis(N1
-(naphthalen-1-yl)-N4
,N4'
-diphenylbenzene-1,4-diamine)]或N,N'-二聯苯基-N,N'-二(1-萘基)-1,1'-聯苯-4,4'-二胺 [N4
,N4'
-di(naphthalen-1-yl)-N4
,N4'
-diphenylbiphenyl-4,4'-diamine,NPB]所製成,但並不僅限於此。
較佳的,該OLED包括一電洞阻擋層,該電洞阻擋層形成於所述電子傳輸層和所述發光層之間,可防止電洞由所述發光層移動至所述電子傳輸層,所述電洞阻擋層可由2,9-二甲基-4,7-二苯基-1,10-鄰二氮雜菲(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline,BCP)或2,3,5,6-四甲基苯基-1,4-鄰苯二甲醯亞胺(2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide),TMPP)所形成,但並不僅限於此。
較佳的,該OLED包括一電子阻擋層,該電子阻擋層形成於所述電洞傳輸層和所述發光層之間,可防止電子由所述發光層移動至所述電洞傳輸層,所述電子阻擋層可由9,9'-(1,1'-聯苯基)-4,4'-二基二-9H
-咔唑(9,9'-(1,1'-biphenyl)-4,4'-diylbis-9H
-carbazole,CBP)或4,4',4''-三(N
-咔唑基)三苯胺 (4,4',4''-tri(N
-carbazolyl)-triphenylamine,TCTA)所形成,但並不僅限於此。
當OLED設置有電洞阻擋層和/或電子阻擋層時,前述OLED相較於傳統的OLED具有較高的發光效率。
較佳的,該電子傳輸層是由例如3,3′-[5′-[3-(3-吡啶基)苯基][1,1′:3′,1″-三聯苯]-3,3″-二基]聯吡啶 ((3,3′-(5′-(3-(3-Pyridinyl)phenyl)(1,1′:3′,1″-terphenyl)-3,3″-diyl)bispyridine,TmPyPb)、3-(4-聯苯基)-5-(4-叔丁基苯基)-4-苯基-4H
-1,2,4-三嗪 (3-(Biphenyl-4-yl)-5-(4-tert
-butylphenyl)-4-phenyl-4H
-1,2,4-triazole,TAZ)、三(2,4,6-三甲基-3-(3-吡啶基)苯基)硼烷 (tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane,3TPYMB)、1,3-聯(3,5-二吡啶-3-基-苯基)苯 (1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene,BmPyPb)和9,10-二(3-(3-吡啶基)苯基)蒽 (9,10-bis(3-(pyridin-3-yl)phenyl)anthracene,DPyPA),但並非僅限於此。
所述電子注入層可由一電子注入材料製成,例如8-氧代萘-1-基鋰((8-oxidonaphthalen-1-yl)lithium(II)),但並非僅限於此。
所述第一電極可以為氧化銦錫電極(indium-doped tin oxide electrode),但並不僅限於此。
所述第二電極的功函數 (work function)低於第一電極的功函數。因此,第二電極可以是但不侷限於鋁電極、銦電極或鎂電極。
本發明的其他目的、功效和技術特徵,會以圖式、實施例和比較例進行更詳細的說明。
以下列舉數種實施例作為例示說明本發明的用於有機電子裝置的組合物及使用其的有機電子裝置的實施方式,以突顯本發明相較於現有技術的差異;熟習此技藝者可經由本說明書的內容輕易了解本發明所能達成的優點與功效,並且於不悖離本發明之精神下進行各種修飾與變更,以施行或應用本發明的內容。
合成化合物
I-1
至化合物
I-15
及化合物
I-28
做為第一主體化合物的化合物I-1和化合物I-2可藉由下述步驟合成,其合成路徑統整於合成機制R1中。
合成機制R1;
其中,中間物C1(Intermediate C1)是,而中間物C2(Intermediate C2)是。
化合物I-1和化合物I-2可分別採用中間物C2和中間物C1並依照美國發明專利公開案第2017/0213978號所記載的化合物VII和化合物VI的合成方法所獲得。
此外,化合物I-7同樣可依照美國發明專利公開案第2017/0213978號所記載的化合物III的合成方法所獲得。所述合成方法與使用中間物C1之合成機制R1的合成方法類似,但差異在於採用4-氯-2,6-二苯基嘧啶(4-chloro-2, 6-diphenylpyrimidine,CAS No. 29509-91-9)取代2-氯-4,6-二苯基-1,3,5-三嗪(2-chloro-4,6-diphenyl-1,3,5-triazine,CAS No. 3842-55-5)。
就化合物I-3至化合物I-6、化合物I-8至化合物I-15以及化合物I-28而言,可藉由類似於合成機制R1的合成方法,各別採用中間物C1或中間物C2、以及其他用於取代2-氯-4,6-二苯基-1,3,5-三嗪的包含三嗪環或嘧啶環之反應物,即可獲得前述化合物。所述用於合成化合物I-3至化合物I-6、化合物I-8至化合物I-15以及化合物I-28的特定之包含三嗪環或嘧啶環之反應物及中間物C1或中間物C2分別列於表2-1;此外,化合物I-3至化合物I-6、化合物I-8至化合物I-15以及化合物I-28以FD-MS作鑑定,且其化學結構式、產率、分子式和FD-MS分析而得的質量列於表2-1中;另外,化合物I-3至化合物I-6、化合物I-8至化合物I-15以及化合物I-28以氫核磁共振(1
H nuclear magnetic resonance,1
H-NMR)做鑑定,並將1
H-NMR圖譜結果列於表2-2中。
用於合成化合物
I-10
的反應物的製備
將1.0當量的二苯并呋喃-1-硼酸(dibenzo[b,d]furan-1-ylboronic acid)、1.1當量的2,4-二氯-6-(D5
)苯基-1,3,5-三嗪(2,4-dichloro-6-(D5
)phenyl-1,3,5-triazine)、0.015當量的三(二亞苄基丙酮)二鈀 [tris(dibenzylideneacetone)dipalladium(0),Pd2
(dba)3
]、和三苯基膦(triphenylphosphine,PPh3
)置於0.5 M的二甲醚(methoxymethane,DME)與2.0 M的碳酸鈉水溶液(Na2
CO3(aq)
)之混合溶液中並攪拌之;前述反應溶液加熱至約65°C至70°C,並於氮氣環境下攪拌24小時。待反應完成後,將水和甲苯加入前述反應溶液中使反應溶液分層;接著,萃取出的有機層以硫酸鈉乾燥,並以減壓蒸餾去除有機層中的溶劑,再將殘留物以甲醇清洗,最後可得白色固體產物,即為。其產率為80%。FD-MS分析結果:C21
H7
D5
ClN3
O,檢測值362.82。
表2-1:合成各化合物I-3至化合物I-6、化合物I-8至化合物I-15以及化合物I-28使用的中間物、反應物及其CAS編號、化學結構式、產率、分子式與以FD-MS分析所得質量
表2-2:化合物I-3至化合物I-6、化合物I-8至化合物I-15及化合物I-28的H1
-NMR結果
合成化合物
I-16
至化合物
I-19
及化合物
I-27
做為第一主體化合物的化合物I-16至I-19和I-27可藉由下述步驟合成,其合成路徑統整於合成機制R2中。
合成機制R2;
其中,中間物C1’(Intermediate C1’)是,而中間物C2’(Intermediate C2’)是。
中間物C1’和中間物C2’可將美國發明專利公開案第2017/0213970號的中間物D1和中間物D2再進行鈴木反應(Suzuki-Miyaura reaction)後所獲得。
將1.0當量的中間物C1’/中間物C2’、1.2當量的反應物Bn、0.01當量的乙酸鈀(Palladium(II) acetate,Pd(OAc)2
)和0.04當量的2-(二環己基膦基)聯苯(dicyclohexylphosphine(2-biphenyl),P(Cy)2
(2-biPh))置於0.5 M的甲苯/乙醇(體積比為10:1)與3.0 M的碳酸鉀水溶液之混合溶液中並攪拌之;前述反應溶液加熱至約100°C並於氮氣環境下攪拌12小時。待反應完成後,將水和甲苯加入前述反應溶液中使反應溶液分層;接著,萃取出的有機層以硫酸鈉乾燥,並以減壓蒸餾去除有機層中的溶劑後利用矽膠管柱層析純化殘留物,再以甲苯再結晶得到白色固體產物即為化合物I-16至化合物I-19或化合物I-27。
就化合物I-16至化合物I-19以及化合物I-27而言,可藉由合成機制R2的合成方法,各別採用中間物C1’或中間物C2’、以及包含三嗪環或嘧啶環之反應物Bn,即可獲得前述化合物。所述用於合成化合物I-16至化合物I-19以及化合物I-27的中間物C1’或中間物C2’和特定之包含三嗪環或嘧啶環之反應物及Bn分別列於表3-1;此外,化合物I-16至化合物I-19以及化合物I-27以FD-MS作鑑定,且其化學結構式、產率、分子式和FD-MS分析而得的質量同樣列於表3-1中;另外,化合物I-16至化合物I-19以及化合物I-27以1
H-NMR(500 MHz, CDCl3
)做鑑定,並將1
H-NMR圖譜結果列於表3-2中。
表3-1:化合物I-16至化合物I-19以及化合物I-27使用的中間物、反應物及其CAS No.、化學結構式、產率、分子式與以FD-MS分析所得質量
表3-2:化合物I-16至化合物I-19以及化合物I-27的H1
-NMR結果
合成化合物
I-20
至化合物
I-23
做為第一主體化合物的化合物I-20至化合物I-23可藉由下述步驟合成,其合成路徑統整於合成機制R3中。
合成機制R3;
其中,中間物Cn-B (Intermediate Cn-B)是(中間物C1-B)、(中間物C2-B)、(中間物C7-B)、或(中間物C3-B)。
化合物I-20至化合物I-23可分別依照美國發明專利公開案第2018/0159044號所記載的化合物V、化合物IX、化合物XIX和化合物VII的合成方法所獲得,其各自採用前述之中間物C1-B、中間物C2-B、中間物C7-B和中間物C3-B。
合成化合物
I-24
至化合物
I-26
做為第一主體化合物的化合物I-24和化合物I-25可藉由下述步驟合成,其合成路徑統整於合成機制R4中。
合成機制R4;
其中,中間物Dn-B (Intermediate Dn-B)是(中間物D1-B)、或(中間物D4-B)。
化合物I-24和化合物I-25可分別依照美國發明專利公開案第2018/0155312號所記載的化合物VI和化合物VII的合成方法所獲得,其各自採用前述之中間物D1-B和中間物D4-B。
此外,化合物I-26同樣可依照美國發明專利公開案第2018/0155312號所記載的化合物III的合成方法所獲得。所述合成方法與使用中間物D1-B之合成機制R4的合成方法類似,但差異在於採用4-氯-2,6-二苯基嘧啶取代2-氯-4,6-二苯基-1,3,5-三嗪。
用於有機電子裝置的組合物的
製備
藉由採用適當含量的表1中所列之第一主體化合物和表4中所列之第二主體化合物配製而得組合物1至組合物51,而組合物1至組合物51中各自採用的第一主體化合物和第二主體化合物之種類列於表5中。
在組合物1至組合物47中,其第一主體化合物和第二主體化合物的重量比皆為1:1;在組合物48至組合物50中,其第一主體化合物和第二主體化合物的重量比皆為6:4;而在組合物51,其第一主體化合物和第二主體化合物的重量比為4:6。
光致發光圖譜
(photoluminescence spectra
,
PL
圖譜
)
之分析
將厚度為500 Å的玻璃基板以丙酮和異丙醇進行清洗。於真空度維持在1x10-6
托耳(torr)的環境下,分別將表1中的化合物I-1至化合物I-28、表4中的化合物II-1至化合物II-4、以及表5中的組合物1至組合物53各自沉積於一玻璃基板,以製得化合物I-1至化合物I-28、化合物II-1至化合物II-4、以及組合物1至組合物53的PL試片。
其中,組合物2、8、9、13、14、16、17、19、28至39、42、43、45至47和52、以及前述組合物各自使用的第一主體化合物和第二主體化合物之PL試片以螢光分光光譜儀(型號:Hitachi Fl-7000)進行量測並獲得各組PL圖譜。各組PL圖譜中,前述各組合物及其第一主體化合物和第二主體化合物的最大放光波長(the wavelength at emission maximum,λmax)整理於表6中。
如表6和圖2所示,於各組PL圖譜中,組合物2、8、9、13、14、16、17、19、28至39、42、43、45至47的λmax相較於其各自包含的第一主體化合物和第二主體化合物的λmax,皆明顯出現紅移(red shift)至較長波長範圍的現象。然而,組合物52的λmax的紅移程度明顯小於組合物2、8、9、13、14、16、17、19、28至39、42、43、45至47的λmax的紅移程度。據此可證,各組合物2、8、9、13、14、16、17、19、28至39、42、43、45至47中的第一主體化合物和第二主體化合物皆形成激發錯體。
OLED
裝置的製備
將塗佈有1500 Å厚ITO層的玻璃基板 (以下簡稱為ITO基板)置於含有洗潔劑 (廠牌:Fischer Co.)的蒸餾水 (以Millipore Co.公司的濾器過濾二次而得的蒸餾水)中,並以超音波震盪30分鐘;更換蒸餾水後再以超音波震盪10分鐘以洗淨ITO基板,並重複上述洗淨步驟一次;洗淨後,將前述玻璃基板以異丙醇、丙酮和甲醇以超音波震盪洗淨,並使之乾燥;接著,將玻璃基板置於電漿表面清潔機內,並以氧電漿清潔玻璃基板5分鐘,再將清潔後的玻璃基板置於真空蒸鍍機內。
之後,將真空蒸鍍機的真空度維持在1x10-6
torr至3x10-7
torr,並於ITO基板上依序沉積各種有機材料和金屬材料,並獲得實施例1至43以及比較例1和2的OLED裝置。於此,該ITO基板上係依序沉積有第一電洞注入層 (HIL-1)、第二電洞注入層 (HIL-2)、電洞傳輸層 (HTL)、綠光/紅光發光層 (GEL/REL)、電子傳輸層 (ETL)、電子注入層 (EIL)和陰極 (Cthd)。
其中,HI是用於形成HIL-1和HIL-2的材料;HI-D是用於形成HIL-1的材料;HT是用於形成HT的材料;ET是用於形成ETL的材料;Liq是用於形成ETL和EIL的材料;所述組合物1至53各自是用於形成GEL/REL的主體材料(GH/RH),GD和RD各自是用於形成GEL/REL的摻雜物。
實施例的OLED裝置和比較例的OLED裝置最大的差異為比較例OLED裝置中GEL/REL的主體材料是以包含TPBi的組合物52和53所製成,而實施例的OLED裝置中GEL/REL的主體材料是以表5中的本發明之組合物1至51製成,上述商用材料的具體化學結構列於表7。
表7:商用OLED材料的化學結構
綠光
OLED
裝置的製備
紅光
OLED
裝置的製備
OLED
裝置的效能
1.
色度座標、驅動電壓和電流效率
為了評估OLED裝置的效能,分別將綠光和紅光OLED裝置連接於電源供應器(廠牌:Keithley;型號:2400),並以PR650的光度計檢測,所測得之色度以為國際照明委員會(Commission Internationale de L'Eclairage 1931,CIE)制定的色度座標(color coordinate (x,y))示之,檢測結果列於表10和表11中。其中,綠光OLED裝置是在9000尼特(1 nit=1 cd/m2
)的亮度下檢測,紅光OLED裝置是在3000尼特的亮度下檢測。
通過以下方法測量實施例1至43和比較例1和2的OLED裝置的特性。
(1)根據電壓的變化測量電流密度的變化
使用所述電源將電壓從0伏特(V)增加到6.2 V,並測量所述OLED裝置於各電壓下對應獲得的電流值。
(2) 根據電壓的變化測量亮度的變化
使用所述電源將電壓從0 V增加到6.2 V,並使用所述光度計測量所述OLED裝置於各電壓下對應獲得的亮度。
(3)電流效率的量測
電流效率(單位:cd/A)是由前述項目(1)和(2)獲得的亮度和電流密度計算而得。
(4) 色度座標(x,y)的量測
色度座標係以CIE色度決定;所述OLED裝置將電壓從0 V增加到6.2 V,並使用所述光度計紀錄其CIE (x,y)。
組合物1至4、6、8、9、11、15、18、20至29、31、33、35至38、40至43、45至51分別做為實施例1至37之綠光OLED裝置的發光層中的主體材料(GH)。組合物53則做為比較例1之綠光OLED裝置的發光層中的主體材料。實施例1至37和比較例1之OLED裝置的GH和特性列於表10中。
表10:實施例1至37和比較例1之OLED裝置的GH材料、CIE、驅動電壓和電流效率
組合物5、7、10、12、19和44分別做為實施例38至43之紅光OLED裝置的發光層中的主體材料(RH)。組合物53則做為比較例2之紅光OLED裝置的發光層中的主體材料。實施例38至43和比較例2之OLED裝置的RH和特性列於表11中。
表11:實施例38至43和比較例2之OLED裝置的RH材料、CIE、驅動電壓和電流效率
2.
壽命測試
(T95)
依據OLED壽命測試系統(Chroma model 58131)進行壽命測試(T95)。壽命T95係以當所述OLED裝置的亮度相對於初始亮度下降至95%時所需的時間做為定義,其中,綠光OLED裝置是在7000尼特的亮度下進行測試,紅光OLED裝置是在6000尼特的亮度下進行測試。
將實施例1至7、12、13、18、29至34、36和37之綠光OLED裝置中做為GH的組合物以及其壽命測試(T95)結果列於表12。
表12:綠光OLED裝置之實施例編號、其GH之組合物編號及其壽命測試結果
根據上述實驗結果,相較於包含商用的主體材料的組合物53做為綠光發光層中的主體材料,採用本發明之組合物1至4、6、8、9、11、15、18、20至29、31、33、35至38、40至43、45至51做為綠光發光層中的主體材料時,可降低所述綠光OLED裝置的驅動電壓並改善其電流效率。相似地,相較於包含商用的主體材料的組合物53做為紅光發光層中的主體材料,採用本發明之組合物5、7、10、12、19和44做為紅光發光層中的主體材料時,可降低所述紅光OLED裝置的驅動電壓並改善其電流效率。
更甚者,採用本發明之組合物1至4、6、8、9、21、22、27、42、43、45至48、50和51做為綠光發光層中的主體材料時,還可延長所述綠光OLED裝置的使用壽命。相似地,採用本發明之組合物5、7、12和44做為紅光發光層中的主體材料時,同樣可延長所述紅光OLED裝置的使用壽命。
原因應在於,與比較例的TPBi相比,特定的第一主體化合物具有合適的最低未占分子軌域(LUMO)能階,因此能更好地向發光層注入電子,而使致使用其的所述OLED裝置所需的驅動電壓較低。此外,特定的第一主體化合物和第二主體化合物的搭配各自形成如表6所示的激發錯體,而這樣的發光機制可有效地使用激子而獲得高效率之OLED裝置。
由此可證,本發明的組合物適合做為主體材料添加於綠光OLED裝置和紅光OLED裝置中,並可讓使用其的OLED裝置達到降低驅動電壓和改善電流效率、甚至延長使用壽命的功效。
上述實施例僅係為說明本發明之例示,並非於任何方面限制本發明所主張之權利範圍,所屬技術領域中具有通常知識者能根據本發明之精神針對例如取代基的數量、位置或排列加以調整。本發明所主張之權利範圍自應以申請專利範圍所述為準,而非僅限於上述具體實施例。
11‧‧‧基板
12‧‧‧陽極
13‧‧‧電洞注入層
14‧‧‧電洞傳輸層
15‧‧‧發光層
16‧‧‧電子傳輸層
17‧‧‧電子注入層
18‧‧‧陰極
圖1為OLED的側視剖面圖。
圖2為化合物I-4、II-2和組合物16的光致發光圖譜。
無
Claims (15)
- 一種用於有機電子裝置的組合物,其包括:一第一主體化合物,其係如下式(I)所示:
- 如請求項2所述之組合物,其中,該第一主體化合物和該第二主體化合物的重量比為3:7至7:3。
- 如請求項2所述之組合物,其中,L1和L2各自獨立為苯撐基。
- 如請求項2所述之組合物,其中,L3為苯撐基。
- 一種有機電子裝置,其包括一第一電極、一第二電極和設置於該第一電極和該第二電極間的一有機層,其中該有機層包括如請求項1至12中任一項所述的組合物。
- 如請求項13所述之有機電子裝置,其中,該有機電子裝置為一有機發光二極體。
- 如請求項14所述之有機電子裝置,其中,其中該有機發光二極體包括:一電洞注入層,其形成於該第一電極上;一電洞傳輸層,其形成於該電洞注入層上; 一發光層,其形成於該電洞傳輸層上,該發光層包含如請求項1至12中任一項所述的組合物;一電子傳輸層,其形成於該發光層上;和一電子注入層,其形成於該電子傳輸層和該第二電極之間。
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EP3291319B1 (en) * | 2016-08-30 | 2019-01-23 | Novaled GmbH | Method for preparing an organic semiconductor layer |
TWI658038B (zh) * | 2016-12-07 | 2019-05-01 | 彩豐精技股份有限公司 | 化合物及其有機電子裝置 |
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TW201726603A (zh) * | 2016-01-27 | 2017-08-01 | 彩豐精技股份有限公司 | 新穎化合物及包含其之有機電子裝置 |
TW201726601A (zh) * | 2016-01-27 | 2017-08-01 | 彩豐精技股份有限公司 | 新穎化合物及包含其之有機電子裝置 |
TW201726609A (zh) * | 2016-01-27 | 2017-08-01 | 彩豐精技股份有限公司 | 化合物及其有機電子裝置 |
TW201733973A (zh) * | 2016-03-24 | 2017-10-01 | 彩豐精技股份有限公司 | 化合物及其有機電子裝置 |
TW201811719A (zh) * | 2016-08-09 | 2018-04-01 | 彩豐精技股份有限公司 | 化合物及其有機電子裝置 |
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CN110563638A (zh) | 2019-12-13 |
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US11183641B2 (en) | 2021-11-23 |
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CN110571338B (zh) | 2022-03-04 |
JP6771785B2 (ja) | 2020-10-21 |
CN110563662A (zh) | 2019-12-13 |
TW202003478A (zh) | 2020-01-16 |
US20190372014A1 (en) | 2019-12-05 |
CN110563707A (zh) | 2019-12-13 |
KR20190138612A (ko) | 2019-12-13 |
KR102170538B1 (ko) | 2020-10-28 |
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