TWI719456B - 雜芳族化合物及使用該雜芳族化合物的有機電激發光組件 - Google Patents
雜芳族化合物及使用該雜芳族化合物的有機電激發光組件 Download PDFInfo
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- TWI719456B TWI719456B TW108114203A TW108114203A TWI719456B TW I719456 B TWI719456 B TW I719456B TW 108114203 A TW108114203 A TW 108114203A TW 108114203 A TW108114203 A TW 108114203A TW I719456 B TWI719456 B TW I719456B
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Classifications
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Abstract
本發明提供一種雜芳族化合物及使用該雜芳族化合物作為有機電激發光元件發光層的螢光客體材料。該有機電激發光元件可以降低驅動電壓,或運作出較高的電流效率,或較長的半衰期。
Description
本發明是關於一種銥複合物,特別是關於使用該銥複合物的有機電激發光(下文稱為有機EL)元件。
有機電激發光(有機EL)元件是一種有機發光二極體(OLED),其中發光層是由有機化合物製成的膜,有機化合物可回應電流而發光。包含有機化合物的發光層被夾置於兩個電極之間。有機EL組件由於其高照度、重量輕、超薄外形、自照明而無需背光、低功耗、廣視角、高對比、製造方法簡單以及反應時間快速而被應用於平板顯示器。
典型上,有機EL是由位於兩個電極之間的有機材料層構成。有機材料層包括電洞傳輸層(hole transporting layer,HTL)、發光層(emitting layer,EML)、及電子傳輸層(electron transporting layer,ETL)。有機電激發光的基本原理涉及載子(carrier)的注入、傳輸、及複合以及激子(exciton)的形成,以進行發光。當向有機EL元件施加外部電壓時,電子和電洞分別從陰極和陽極注入。電子從陰極注入最低未佔用分子軌域(lowest unoccupied molecular orbital,LUMO) 中,而電洞從陽極注入最高佔用分子軌域(highest occupied molecular orbital,HOMO)中。隨後,電子在發光層中與電洞重組而形成激子,然後激子失活而發光。當發光分子吸收能量而達到激發態時,依據電子和電洞的自旋組合,激子可呈單重態或三重態。眾所周知,在電激發下形成的激子通常包括25%的單重態激子和75%的三重態激子。然而,在螢光材料中,75%的三重態激子中的電生成能量將作為熱量消散,因為從三重態衰減是自旋禁阻(spin forbidden)的。因此,螢光電激發光元件僅具有25%的內部量子效率(internal quantum efficiency),導致理論上最高的外部量子效率(EQE)僅有5%,因為元件的光輸出耦合效率只有約20%。相較於螢光電激發光元件,磷光有機EL元件利用自旋─軌域相互作用(spin-orbit interacttion)來促進單重態與三重態之間的系統間穿越(intersystem crossing),因此來自單重態和三重態的發光皆可取得,而且電激發光元件的內部量子效率可自25%升至100%。
對於使用有機EL元件的平板顯示器來說,有機EL元件中使用的有機材料仍無法令人滿意。如果可以在降低驅動電壓、或提高電流效率、或延長半衰期等等任何一方面,能有改善,都足以使有機EL元件或平板顯示器等相關產業有明顯的發展與提升。因此,本發明的目的之一,是提供一種有機化合物,可以降低有機EL元件的驅動電壓、或提高其電流效率、或延長其半衰期。
因此,本發明的目的是提供一種新的雜芳族化合物,可以作為有機EL元件發光層的螢光客體材料,能夠降低有機EL元件的驅動電壓、或提高其電流效率、或延長其半衰期,或改善功耗。
本發明的另一目的是提供一種雜芳族化合物,或使用該雜芳族化合物的有機電激發光元件,其可以較低的驅動電壓運作,或者操作出較高的電流效率,或較長的半衰期。
依據本發明,提供了一種可用於有機EL元件的雜芳族化合物。其中,發光顏色為藍色的有機電激發光元件,可以是優選。該雜芳族化合物可由下式(1)表示:式(1), X1
可以是二價橋並選自於由O、S、Se、CR4
R5
、NR6
和 SiR7
R8
組成的群組。X2
可以是不存在,也可以是二價橋並選自於由O、S、Se、CR9
R10
、NR11
和 SiR12
R13
組成的群組;其中X2
不存在可以是優選。A可以表示具有2、3、4、5、6、7、8或9個環(2至9個環)的經取代或未經取代的稠合環烴單元。m可為0、1、2、3或4(0至4)的整數。B可表示以下式(2):式(2), 其中環C可以表示苯環,也可以表示具有2、3、4或5個環的的經取代或未經取代的稠合環烴單元。Y可以表示二價橋並選自於由O、S、Se、CR14
R15
、NR16
和SiR17
R18
所組成的群組,其中S或CR14
R15
可以是優選,且其中R14
和R15
可以是各自獨立的以甲基為優選。 R3
至R18
可獨立為氫原子、鹵素、具有1至60個碳原子的經取代或未經取代烷基、具有6至60個碳原子的經取代或未經取代芳基、具有6至60個碳原子的經取代或未經取代芳烷基、具有3至60個碳原子的經取代或未經取代雜芳基、及具有6至60個碳原子的經取代或未經取代芳胺基。 其中可以理解的是,本發明所述的“X2
不存在”,是指式(1)結構的下面為開環,如下式(1’)所示:式(1’) 當X2
不存在的時候, R1
和R2
獨立為氫原子、鹵素、具有1至60個碳原子的經取代或未經取代烷基、具有6至60個碳原子的經取代或未經取代芳基、具有6至60個碳原子的經取代或未經取代芳烷基、具有3至60個碳原子的經取代或未經取代雜芳基、或具有6至60個碳原子的經取代或未經取代芳胺基;或者兩個或兩個以上的R1
可以選擇彼此連接,並可以與共同連接的苯環共同定義出至少一環烴;或者兩個或兩個以上的R2
可以選擇彼此連接,並可以與共同連接的苯環共同定義出至少一環烴。 式(1)右下方的苯環與(R2
)m
,以及式(1)左下方的苯環與(R1
)m
,最好都不要共同構成下列結構:式(1)右下方的苯環與(R2
)m
,以及式(1)左下方的苯環與(R1
)m
,都不共同構成上述結構的時候,將該雜芳族化合物,用於作為有機EL元件的發光層或有機薄膜層,可顯示出良好的特性。例如,但不限於,將該雜芳族化合物,用於作為發光層的客體材料,可以使元件發光顏色為藍色的元件驅動電壓,大幅降低,低至約3.0~3.5 V。與構成上述結構的雜芳族化合物相比,本發明元件驅動電壓降幅可以達到約14%,最多可以達到約23%。當X2不存在的時候,該雜芳族化合物可使電流效率約為6.0~6.9 cd/A,也就是至少有約6.0 cd/A,最高可以達到約6.9 cd/A。另外,當X2不存在的時候,該雜芳族化合物可使組件半衰期長達約235~450小時,也就是至少有約235小時,最長可以到達約450小時。
本發明進一步提供了一種有機電激發光元件。該有機電激發光元件包含由陰極和陽極組成的一電極對、及在該電極對之間的一發光層及一個或更多個有機薄膜層。該發光層和該有機薄膜層中之至少一者包含式(1)的雜芳族化合物。
本發明欲探究前述有機材料以及使用此類有機材料的有機EL裝置。在下文中將提供生產、結構以及要素的詳細描述以使本發明可充分地被理解。顯然本發明的應用並不限於本領域所屬技術領域技術人員所熟悉的特定細節。另一方面,普遍周知的常見元素和過程並未詳細描述于本發明中,且不應對本發明產生不必要的限制。現將在下文中更詳細地描述本發明的一些較佳實施方式。然而,應當理解的是,除了本文明確描述的實施例之外,本發明還可實施於各種其他實施例中,也就是說,本發明還可廣泛應用於其他實施例,且本發明的範圍不會因此受到明確的限制,只受隨附申請專利範圍的內容限制。
在本發明的一個實施例中,涉及一種雜芳族化合物,其可作為有機電激發光元件的螢光發光客體材料。其中,發光顏色為藍色的有機電激發光元件,可以是優選。該雜芳族化合物可由下式(1)表示:
式(1)。 X1
可以是二價橋並選自於由O、S、Se、CR4
R5
、NR6
和 SiR7
R8
組成的群組。X2
可以是不存在,也可以是二價橋並選自於由O、S、Se、CR9
R10
、NR11
和 SiR12
R13
組成的群組;其中X2
不存在可以是優選。A可以表示具有2、3、4、5、6、7、8或9個環(2至9個環)的經取代或未經取代的稠合環烴單元。m可為0、1、2、3或4(0至4)的整數。B可表示以下式(2):式(2), 其中環C可以表示苯環,也可以表示具有2、3、4或5個(2至5個)環的經取代或未經取代的稠合環烴單元。Y可以表示二價橋並選自於由O、S、Se、CR14
R15
、NR16
和SiR17
R18
所組成的群組,其中S為CR14
R15
可以是優選,且其中R14
和R15
可以是各自獨立的以甲基為優選。 R3
至R18
可各自獨立為氫原子、鹵素、具有1至60個碳原子的經取代或未經取代烷基(優選具有1至20個碳原子的經取代或未經取代烷基;更優選具有1至10個碳原子的經取代或未經取代烷基;最優選具有1至5個碳原子的經取代或未經取代烷基)、具有6至60個碳原子的經取代或未經取代芳基、具有6至60個碳原子的經取代或未經取代芳烷基、具有3至60個碳原子的經取代或未經取代雜芳基、及具有6至60個碳原子的經取代或未經取代芳胺基。 其中可以理解的是,本發明所述的“X2
不存在”,是指式(1)結構的下面為開環,如下式(1’)所示:式(1’) 當X2
不存在的時候, R1
和R2
獨立為氫原子、鹵素、具有1至60個碳原子的經取代或未經取代烷基(優選具有1至20個碳原子的經取代或未經取代烷基;更優選具有1至10個碳原子的經取代或未經取代烷基;最優選具有1至5個碳原子的經取代或未經取代烷基)、具有6至60個碳原子的經取代或未經取代芳基、具有6至60個碳原子的經取代或未經取代芳烷基、具有3至60個碳原子的經取代或未經取代雜芳基、或具有6至60個碳原子的經取代或未經取代芳胺基;或者兩個或兩個以上的R1
可以選擇彼此連接,並可以與共同連接的苯環共同定義出至少一環烴;或者兩個或兩個以上的R2
可以選擇彼此連接,並可以與共同連接的苯環共同定義出至少一環烴。 式(1)右下方的苯環與(R2
)m
,以及式(1)左下方的苯環與(R1
)m
,最好都不要共同構成下列結構:式(1)右下方的苯環與(R2
)m
,以及式(1)左下方的苯環與(R1
)m
,都不共同構成上述結構的時候,將該雜芳族化合物,用於作為有機EL元件的發光層或有機薄膜層,可顯示出良好的特性。例如,但不限於,將該雜芳族化合物,用於作為發光層的客體材料,可以使元件發光顏色為藍色的元件驅動電壓,大幅降低,低至約3.0~3.5 V。與構成上述結構的雜芳族化合物相比,本發明元件驅動電壓降幅可以達到約14%,最多可以達到約23%。 當X2
不存在的時候,該雜芳族化合物可使電流效率約為6.0~6.9 cd/A,也就是至少有約6.0 cd/A,最高可以達到約6.9 cd/A。另外,當X2
不存在的時候,該雜芳族化合物可使組件半衰期長達約235~450小時,也就是至少有約235小時,最長可以到達約450小時。 R1
最好是異於B。R2
也最好是異於B。 兩個或兩個以上的R2
可以選擇彼此連接,並可以與共同連接的苯環共同定義出至少一環烴。該至少一環烴與該苯環可以稠合 (fused with)或共同構成例如,但不限於萘基、二苯並呋喃基、或二苯並噻吩基(優選可以是萘基)。 兩個或兩個以上的R1
可以彼此連接,並可以與共同連接的苯環共同定義出至少一環烴。該至少一環烴與該苯環可以稠合(fused with)或共同構成例如,但不限於萘基、二苯並呋喃基、或二苯並噻吩基(優選可以是萘基)。 當X2
不存在的時候, R1
和R2
可以是獨立為氫原子、鹵素、具有1至60個碳原子(優選1至20個碳原子;更優選1至10個碳原子;最優選1至5個碳原子,例如是甲基)的經取代或未經取代烷基、具有6至60個碳原子的經取代或未經取代芳基(優選可以是苯基)、具有6至60個碳原子的經取代或未經取代芳烷基、具有3至60個碳原子的經取代或未經取代雜芳基、及具有6至60個碳原子的經取代或未經取代芳胺基。 當X2
是二價橋並選自於由O、S、Se、CR9
R10
、NR11
和 SiR12
R13
組成的群組的時候,其中可以O或SiR12
R13
可以是優選的,R1
和R2
可以獨立為氫原子、鹵素、具有1至60個碳原子(優選1至20個碳原子;更優選1至10個碳原子;最優選1至5個碳原子)的經取代或未經取代烷基、具有6至60個碳原子的經取代或未經取代芳基、具有6至60個碳原子的經取代或未經取代芳烷基、具有3至60個碳原子的經取代或未經取代雜芳基、及具有6至60個碳原子的經取代或未經取代芳胺基。
在一些實施方式,A可表示經取代或未經取代的萘基(naphthyl group)、經取代或未經取代的菲基(phenanthrenyl group)、經取代或未經取代的蒽基(anthracenyl group)、經取代或未經取代的芘基(pyrenyl group)、經取代或未經取代的䓛基(chrysenyl group)、經取代或未經取代的三亞苯基(triphenylenyl group)、經取代或未經取代的苝基(perylenyl group)、經取代或未經取代的聯四苯基(tetraphenylenyl group)、經取代或未經取代的7,14-二苯基苊[1,2-k]熒蒽基(7,14-diphenylacenaphtho[1,2-k]fluoranthene group)。
在一些實施方式中,A可以是以下化學式中的一種結構: , 其中,R19
至R24
可獨立為氫原子、具有1至30個碳原子(優選1至20個碳原子;更優選1至10個碳原子;最優選1至5個碳原子)的經取代或未經取代烷基、具有6至30個碳原子的經取代或未經取代芳基、具有6至30個碳原子的經取代或未經取代芳烷基、具有3至30個碳原子的經取代或未經取代雜芳基、及具有6至30個碳原子的經取代或未經取代芳胺基。所述的經取代的萘基,其取代基可以是兩個甲基、兩個2-甲基噻吩基、或兩個異丙基。再者,R19
至R24
可以分別獨立為甲基、苯基、甲苯基、二甲苯基、吡啶基、噻吩基、異丙基、2-甲基噻吩基、異丁基或下列化學式中的一種結構:,,,,。
在一些實施方式,該雜芳族化合物可以由以下式(3)至式(15)中的一個表示: 式(3), 式(4),式(5),式(6), 式(7), 式(8), 式(9), 式(10), 式(11), 式(12),式(13),其中,X1
可以是二價橋並選自於由O、S、Se、CR4
R5
、NR6
和 SiR7
R8
組成的群組。X2
可以是不存在,也可以是二價橋並選自於由O、S、Se、CR9
R10
、NR11
和 SiR12
R13
組成的群組;其中X2
不存在可以是優選。 R4
、R5
、R6
、R7
、R8
、R9
、R10
、R12
、及R13
可以獨立為氫原子、鹵素、具有1至60個碳原子(優選1至20個碳原子;更優選1至10個碳原子;最優選1至5個碳原子)的經取代或未經取代烷基、具有6至60個碳原子的經取代或未經取代芳基、具有6至60個碳原子的經取代或未經取代芳烷基、具有3至60個碳原子的經取代或未經取代雜芳基、及具有6至60個碳原子的經取代或未經取代芳胺基。其中,R4
至R8
、R9
至R13
可以獨立為甲基、正丁基、苯基、甲苯基、吡啶基、或下列化學式中的一種結構:,,,。 R6
和R11
可以獨立為甲基、異丙基、正丁基、苯基、甲苯基、二甲苯基、吡啶基、或下列化學式中的一種結構:,,,,,,。 對於式(1),B可表示以下式(2):式(2), 其中環C可以表示苯環,也可以表示具有2、3、4或5個環的的經取代或未經取代的稠合環烴單元(例如稠合芳環單元)。該稠合芳環單元(環C),可以是萘基、菲基、蒽基、芘基、䓛基、三亞苯基、聯四苯基、或苝基。 A可以表示具有2、3、4、5、6、7、8或9個環的經取代或未經取代的稠合環烴單元。m可為0、1、2、3或4的整數。 Y可以表示二價橋並選自於由O、S、Se、CR14
R15
、NR16
和SiR17
R18
所組成的群組。R14
至R18
可獨立為氫原子、鹵素、具有1至60個碳原子(優選1至20個碳原子;更優選1至10個碳原子;最優選1至5個碳原子)的經取代或未經取代烷基、具有6至60個碳原子的經取代或未經取代芳基、具有6至60個碳原子的經取代或未經取代芳烷基、具有3至60個碳原子的經取代或未經取代雜芳基、及具有6至60個碳原子的經取代或未經取代芳胺基。其中,R8
、R9
、R11
、R12
可以獨立為甲基、乙基、正丙基、苯基、甲苯基、吡啶基、或正丁基。R10
可以是苯基、異丙基、二甲苯基、吡啶基、甲基、正丁基、甲苯基、或下列化學式中的一種結構:,。 對於式(1),R3
可以是氫原子、鹵素、具有1至60個碳原子的經取代或未經取代烷基、具有6至60個碳原子的經取代或未經取代芳基、具有6至60個碳原子的經取代或未經取代芳烷基、具有3至60個碳原子的經取代或未經取代雜芳基、及具有6至60個碳原子的經取代或未經取代芳胺基。R3
也可以是苯基、甲基、異丙苯基、吡啶基、異丁苯基、2-甲基噻吩基、或下列化學式中的一種結構:,。
較佳地,但不受限的,是該雜芳族化合物可以為以下化合物中之一:化合物1 化合物2 化合物3 化合物4化合物5 化合物6 化合物7 化合物8化合物9 化合物10 化合物11 化合物12化合物13 化合物14 化合物15 化合物16化合物17 化合物18 化合物19 化合物20化合物21 化合物22 化合物23 化合物24化合物25 化合物26 化合物27 化合物28化合物29 化合物30 化合物31 化合物32化合物33 化合物34 化合物35 化合物36化合物37 化合物38 化合物39 化合物40化合物41 化合物42 化合物43 化合物44化合物45 化合物46 化合物47 化合物48化合物49 化合物50 化合物51 化合物52化合物53 化合物54 化合物55 化合物56化合物57 化合物58 化合物59 化合物60化合物61 化合物62 化合物63 化合物64化合物65 化合物66 化合物67 化合物68化合物69 化合物70 化合物71 化合物72化合物73 化合物74 化合物75 化合物76化合物77 化合物78 化合物79 化合物80化合物81 化合物82 化合物83 化合物84化合物85 化合物86 化合物87 化合物88化合物89 化合物90 化合物91 化合物92化合物93 化合物94 化合物95 化合物96化合物97 化合物98 化合物99 化合物100化合物101 化合物102 化合物103 化合物104化合物105 化合物106 化合物107 化合物108化合物109 化合物110 化合物111 化合物112化合物113 化合物114 化合物115 化合物116化合物117 化合物118 化合物119 化合物120化合物121 化合物122 化合物123 化合物124化合物125 化合物126 化合物127 化合物128化合物129 化合物130 化合物131 化合物132化合物133 化合物134 化合物135 化合物136化合物137 化合物138 化合物139 化合物140化合物141 化合物142 化合物143 化合物144化合物145 化合物146 化合物147 化合物148化合物149 化合物150 化合物151 化合物152化合物153 化合物154 化合物155 化合物156化合物157 化合物158 化合物159 化合物160化合物161 化合物162 化合物163 化合物164化合物165 化合物166 化合物167 化合物168化合物169 化合物170 化合物171 化合物172化合物173 化合物174 化合物175 化合物176化合物177 化合物178 化合物179 化合物180化合物181 化合物182 化合物1783 化合物184化合物185 化合物186 化合物187 化合物188化合物189 化合物190 化合物191 化合物192化合物193 化合物194 化合物195 化合物196化合物197 化合物198 化合物199 化合物200化合物201 化合物202 化合物203 化合物204化合物205 化合物206 化合物207 化合物208化合物209 化合物210 化合物211 化合物212化合物213 化合物214 化合物215 化合物216化合物217 化合物218 化合物219 化合物220化合物221 化合物222 化合物223 化合物224化合物225 化合物226 化合物227 化合物228化合物229 化合物230 化合物231 化合物232化合物233 化合物234 化合物235 化合物236化合物237 化合物238 化合物239 化合物240化合物241 化合物242 化合物243 化合物244化合物245 化合物246 化合物247 化合物248化合物249 化合物250 化合物251 化合物252化合物253 化合物254 化合物255 化合物256化合物257 化合物258 化合物259 化合物260化合物261 化合物262 化合物263 化合物264化合物265 化合物266 化合物267 化合物268化合物269 化合物270 化合物271 化合物272化合物273 化合物274 化合物275 化合物276化合物277 化合物278 化合物279 化合物280化合物281 化合物282 化合物283 化合物284化合物285 化合物286 化合物287 化合物288化合物289 化合物290 化合物291 化合物292化合物293 化合物294 化合物295 化合物296化合物297 化合物298 化合物299 化合物300化合物301 化合物302 化合物303 化合物304化合物305 化合物306 化合物307 化合物308化合物309 化合物310 化合物311 化合物312化合物313 化合物314 化合物315化合物316 化合物317 化合物318化合物319 化合物320 化合物321化合物322 化合物323 化合物324化合物325 化合物326 化合物327化合物328 化合物329 化合物330化合物331 化合物332 化合物333化合物334 化合物335 化合物336化合物337 化合物338 化合物339化合物340 化合物341 化合物342 化合物343化合物344 化合物345 化合物346 化合物347化合物348 化合物349 化合物350 化合物351化合物352 化合物353 化合物354 化合物355化合物356 化合物357,及 化合物358。
在本發明的另一個實施方式中,提供了一種有機電激發光元件,其發光顏色優選可以是藍色。該有機電激發光元件包含由陰極和陽極組成的電極對、及在該電極對之間的發光層及一個或多個有機薄膜層。該發光層和有機薄膜層中的至少一個包含式(1)的雜芳族化合物。
在一些實施方式中,發光層所包含的雜芳族化合物可以是螢光客體材料。特別的,這樣的發光層可以發出藍色的螢光,且其元件驅動電壓可以被降低。
在本發明的另一實施方式中,該有機電激發光組件為一發光面板。在本發明的其他實施方式中,該有機電激發光組件為背光面板。
以下將通過實施例來清楚闡明本發明的雜芳族化合物的細節製備。然而,本發明並不限於這些實施例。實施例1至實施例18只是舉例說明本發明的雜芳族化合物的製備,而實施例19也僅只是舉例說明若干有機EL元件的製造及測試報告而已,並非用以限制本發明。 實施例1
將10 g (36.6 mmol)的2-溴-9,9-二甲基-9H-芴、6.64 g (43.9 mmol)的甲基2-鄰氨基苯甲酸、0.3 g (1.46 mmol)的乙酸鈀(Pd(OAc)2
)、17.9 g (54.9 mmol)的碳酸銫(CS2
CO3
)、及120 ml 的鄰二甲苯(o-xylene),五者脫氣並置於氮氣下,然後加熱回流12小時。在反應完成後,可以讓混合物冷卻至室溫。隨後,減壓以將溶劑從有機層移除,用柱層析純化粗產物,得到10 g的黃色油狀甲基2-((9,9-二甲基-9H-芴-2-基)胺基)苯甲酸(79.6 %)。1
H NMR (CDCl3
,400 MHz):化學位移(ppm) 8.97(s, 1H), 8.11(d, 1H), 7.87(d, 1H), 7.75-7.64(m, 3H), 7.41-7.29(m, 3H), 7.08(m, 1H), 6.92(d, 1H), 6.77(d, 1H), 3.79(s, 3H), 1.57(s, 3H) , 1.54(s, 3H)。
2-(2-((9,9-二甲基-9H-芴-2-基)胺基)苯基)-丙烷-2-醇(2-(2-((9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)- propan-2-ol)的合成
將甲基2-((9,9-二甲基-9H-芴-2-基)胺基)苯甲酸(10 g,29.1 mmol)的化合物,與100 ml的四氫呋喃(THF)混合。對此,在室溫下,慢慢加入59 ml,3M的甲基溴化鎂(CH3
MgBr),得到混合物。接著在室溫下攪拌混合物3小時。在反應完成後,加入氯化銨溶液,得到反應混合物。然後,用乙酸乙酯/水進行萃取,分離出有機層。減壓以將溶劑從有機層移除,用柱層析純化粗產物,得到9 g的黃色油狀2-(2-((9,9-二甲基-9H-芴-2-基)胺基)苯基)-丙烷-2-醇(90 %)。1
H NMR (CDCl3
,400 MHz):化學位移(ppm) 8.91(s, 1H),7.81(d, 1H), 7.59(d, 1H), 7.54(d, 1H), 7.35-7.39(m, 3H), 7.29(m, 1H), 6.92(m, 1H), 6.76-6.74(d, 2H), 6.58(d, 1H), 3.88(s, 1H), 1.53(s, 3H) , 1.51(s, 3H) , 1.35(s, 6H)。
7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b]-吖啶(7,7,13,13-tetramethyl-7,13-dihydro-5H-indeno-[1,2-b]-acridine)的合成
將化合物2-(2-((9,9-二甲基-9H-芴-2-基)胺基)苯基)-丙-2-醇(2-(2-((9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)-propan-2-ol) 27 g (78.6 mmol)與400 ml的二氯甲烷(CH2
Cl2
)混合。對此,在室溫下,慢慢加入51 ml的甲基磺酸(CH3
SO3
H)和37 ml的磷酸(H3
PO4
),得到混合物。接著在室溫下攪拌混合物12小時。反應完成後,加入冰水(ice-cold water),得到反應混合物。隨後,將20 %氫氧化鈉溶液加入混合物,然後用乙酸乙酯/水進行萃取,分離出有機層。減壓將溶劑從有機層移除。用柱層析純化粗產物,得到15 g的黃色固體狀7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b] 吖啶(58.8%)。1
H NMR (CDCl3
,400 MHz):化學位移(ppm) 8.95(s, 1H),7.79(s, 1H), 7.72(d, 1H), 7.43(d, 1H), 7.36(d, 1H), 7.25(m, 1H), 7.16(dd, 1H), 7.04(m, 1H), 6.87(s, 1H),6.81-6.78(m, 2H) 1.55(s, 6H), 1.38(s, 6H)。
將2.9g(8.9mmol)的7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b]吖啶(7,7,13,13-tetramethyl-7,13- dihydro-5H-indeno-[1,2-b]acridine)、3g(8.9mmol)的9,10-二溴蒽、0.08g (0.36mmol)的乙酸鈀(Pd(OAc)2
)、2.56g (26.7mmol)的叔丁醇鈉(NaOtBu;sodium tert-butoxide)、及50ml的鄰二甲苯(o-Xylene),五者的混合物脫氣並置於氮氣下,然後在140℃加熱12小時。反應完成後,使混合物冷卻至室溫。隨後,將150 ml的甲醇加到混合物中,得到的沉澱物經過濾並用甲醇洗滌,得到黃色固體。產率:21.23g,23%。1
H NMR (CDCl3
, 400 MHz):化學位移(ppm) 8.11 (d, 2H), 7.91(d, 2H),7.83(d, H), 7.54 (d, 2H), 7.45-7.41(m, 5H), 7.35(m, H), 7.25 (m, H), 7.05-7.02(m, 2H), 6.79(m, H),6.69(d, H) ,6.58(d, H), 1.56(s, 6H), 1.39(s, 6H)。
將1.2 g (2.07 mmol) 5-(10-溴蒽-9-基)- 7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b]吖啶、0.45g (2.27 mmol)雙-對-甲苯基胺、0.004 g (0.02 mmol)的乙酸鈀(Pd(OAc)2
)、0.3 g (3.1 mmol)的叔丁醇鈉(NaOtBu)、及20 ml的鄰二甲苯(o-Xylene)的混合物脫氣並置於氮氣下,然後在140℃加熱12小時。反應完成後,使混合物冷卻至室溫。隨後,將60 ml的甲醇加到混合物中,得到的沉澱物經過濾並用甲醇洗滌,得到黃色固體。產率:0.68 g,47 %。1
H NMR (CDCl3
, 400 MHz):化學位移(ppm) 8.13(d, 2H),7.92(d, 2H), 7.85(d, H), 7.52(d, H), 7.47-7.42(m, 5H), 7.36(m, H) , 7.27(m, H), 7.07-7.03(m, 4H), 6.79(m, H),6.71(m, 3H) ,6.59-6.54(m, 5H), 2.35(s, 6H), 1.57(s, 6H), 1.38(s, 6H)。MS(m/z ,EI+
): 696.7。 實施例2
3.41 g (10.5 mmol) 7,7,13,13-四甲基-7,13-二氫-5H-茚並[1,2-b]吖啶(7,7,13,13-tetramethyl-7,13- dihydro-5H-indeno-[1,2-b]acridine), 3 g (10.5 mmol) 1,5-二溴萘(1,5-dibromonaphthalene), 0.02 g (0.1 mmol) Pd(OAc)2
, 1.51 g (15.8 mmol)叔丁醇鈉(sodium tert-butoxide), 和50 ml鄰二甲苯的混合物脫氣並置於氮氣下,然後在140℃加熱12小時。反應完成後,使混合物冷卻至室溫。隨後,將150 ml的甲醇加到混合物中,得到的沉澱物經過濾並用甲醇洗滌。用柱層析純化粗產物,得到黃色固體。產率:1.5 g, 27 %。1
H NMR (CDCl3
, 400 MHz):化學位移(ppm) 8.09(d, 2H),7.93(d, H), 7.84(d, H), 7.55(d, 2H), 7.45-7.41(m, 2H), 7.37(m, H) , 7.26(m, H), 7.07-7.03(m, 3H), 6.76(m, H),6.69(s, H) ,6.56(d, H), 1.56(s, 6H), 1.39(s, 6H)。
1.5 g (2.83 mmol)的5-(5-溴萘-1-基)-7,7,13,13-四甲基-7,13-二氫-5H-茚並-[1,2-b]吖啶、0.61 g (3.11 mmol)的雙-對-甲苯基胺、0.006 g (0.02 mmol)的乙酸鈀(Pd(OAc)2
)、0.41 g (4.2 mmol) 的叔丁醇鈉(NaOtBu)、及30 ml的鄰二甲苯(o-Xylene),五者的混合物脫氣並置於氮氣下,然後在140℃加熱12小時。反應完成後,使混合物冷卻至室溫。隨後,將60 ml的甲醇加到混合物中,得到的沉澱物經過濾並用甲醇洗滌,得到黃色固體。產率:0.95 g, 52 %.1
H NMR (CDCl3
, 400 MHz):化學位移(ppm)8.01(d, H),7.75-7.71(m, 3H), 7.64(s, H), 7.45(m, 2H), 7.37(m, H), 7.17-7.11(m, 2H) , 7.04-6.97(m, 6H), 6.83(m, 2H), 6.75(s, H),6.68(d, H) ,6.59-6.54(m, 4H), 2.37(s, 6H), 1.55(s, 6H), 1.37(s, 6H). MS(m/z, EI+
): 646.6。 實施例3-9
將5 g (19 mmol)的3-溴二苯並[b,d]噻吩、3.45 g (22.8 mmol) 的甲基2-鄰氨基苯甲酸、0.17 g (0.76 mmol) 的乙酸鈀(Pd(OAc)2
)、9.28 g (28.5 mmol) 的碳酸銫(CS2
CO3
)、及60 ml 的鄰二甲苯(o-xylene),五者的混合物脫氣並置於氮氣下,然後加熱回流12小時。在反應完成後,可以讓混合物冷卻至室溫。隨後,減壓以將溶劑從有機層移除,用柱層析純化粗產物,得到4.8g黃色油狀的甲基2-(二苯並[b,d]噻吩-3-基胺)苯甲酸 (75.8%)。1
H NMR (CDCl3
, 400 MHz):化學位移(ppm)8.99(s, 1H),8.14(d, 1H), 7.89(d, 1H), 7.79-7.68(m, 3H), 7.45-7.33(m, 3H), 7.12(m, 1H), 6.97(d, 1H), 6.81(d, 1H), 3.79(s, 3H)。
將甲基2-(二苯並[b,d]噻吩-3-基胺)苯甲酸 (4.8 g, 14.4 mmol)的化合物,與50 ml的四氫呋喃(THF)混合。對該混合物,在室溫下,慢慢加入28ml,3M的甲基溴化鎂(CH3
MgBr),得到混合物。接著在室溫下攪拌混合物3小時。在反應完成後,加入氯化銨溶液,得到反應混合物。然後,用乙酸乙酯/水進行萃取,分離出有機層。減壓以將溶劑從有機層移除,用柱層析純化粗產物,得到4.5 g黃色油狀的2-(2-(二苯並[b,d]噻吩-3-基胺)苯基) 2-丙醇(93.7%)。1
H NMR (CDCl3
, 400 MHz):化學位移(ppm) 8.94(s, 1H),7.83(d, 1H), 7.62(d, 1H), 7.55(d, 1H), 7.41-7.36(m, 3H), 7.29(m, 1H), 6.94(m, 1H), 6.78-6.75(d, 2H), 6.59(d, 1H), 3.91(s, 1H), 1.35(s, 6H)。
將化合物2-(2-(二苯並[b,d]噻吩-3-基胺)苯基) 2-丙醇(10 g, 30 mmol) ,與150 ml的二氯甲烷(CH2
Cl2
)混合。對此混合物,在室溫下,慢慢加入19 ml的甲基磺酸(CH3
SO3
H)和37 ml的磷酸(H3
PO4
),得到混合物。接著在室溫下攪拌混合物12小時。反應完成後,加入冰水(ice-cold water),得到反應混合物。隨後,將20 %氫氧化鈉溶液加入混合物,然後用乙酸乙酯/水進行萃取,分離出有機層。減壓將溶劑從有機層移除。用柱層析純化粗產物,得到5.3 g黃色固體狀的12,12-二甲基-7,12-二氫苯並[4,5]噻吩[3,2-b]-吖啶 (56%)。1
H NMR (CDCl3
,400 MHz):化學位移(ppm) 8.97(s, 1H),7.81(s, 1H), 7.73(d, 1H), 7.45(d, 1H), 7.38(d, 1H), 7.28(m, 1H), 7.18(dd, 1H), 7.07(m, 1H), 6.89(s, 1H),6.83-6.79(m, 2H), 1.38(s, 6H)。
將2.63g(8.33mmol)的12,12-二甲基-7,12-二氫苯-[4,5]-噻吩[3,2-b]-吖啶、3g(8.33mmol)的1,6-二溴芘、0.02g (0.08mmol)的乙酸鈀(Pd(OAc)2
)、1.2g (12.5mmol)的叔丁醇鈉(NaOtBu;sodium tert-butoxide)、及50ml的鄰二甲苯(o-Xylene),五者混合物脫氣並置於氮氣下,然後在140℃加熱12小時。反應完成後,使混合物冷卻至室溫。隨後,將150 ml的甲醇加到混合物中,得到的沉澱物經過濾並用甲醇洗滌,並以管柱層析法純化粗產物,得到黃色固體。產率:1.54 g, 32 %.1
H NMR (CDCl3
, 400 MHz): chemical shift (ppm) 8.33(d, H), 7.89-7.81(m, 3H), 7.54(d, 4H), 7.42(d, H), 7.36-7.32(m, 2H), 7.27(s, H), 7.08-7.03(m, 3H), 6.94(s, H), 6.74(m, H), 6.57(d, H), 1.41(s, 6H)。
將1.5 g (2.52 mmol) 7-(6-溴芘-1-基)-12,12- 二甲基-7,12-二氫苯並[4,5]噻吩[3,2-b]吖啶、0.55g (2.77 mmol)的雙-對-甲苯胺、0.006g (0.02mmol)的乙酸鈀(Pd(OAc)2
)、0.36g (3.78mmol)的叔丁醇鈉(NaOtBu;sodium tert-butoxide)、及30ml的鄰二甲苯(o-Xylene),五者混合物脫氣並置於氮氣下,然後在140℃加熱12小時。反應完成後,使混合物冷卻至室溫。隨後,將60 ml的甲醇加到混合物中,得到的沉澱物經過濾並用甲醇洗滌,得到黃色固體。產率:0.86 g, 48 %.1
H NMR (CDCl3
, 400 MHz) :化學位移(ppm) 8.35(d, H), 8.03 (d, H), 7.92(d, H), 7.75(d, 4H), 7.55-7.59(m, 3H), 7.33(s, H), 7.15-7.01(m, 9H), 6.84(m, H), 6.55-6.59(m, 5H), 2.36(s, 6H), 1.42(s, 6H). MS(m/z, EI+
): 710.6。 實施例11-18
我們已使用相同的合成方法得到一系列中間體。所以,以下的化合物(產物),都可以類似地合成而得。
生產有機電激發光元件的方法舉例(GENERAL METHOD OF PRODUCING ORGANIC EL DEVICE)
提供阻值為9~12歐姆/平方(ohm/square)及厚度為120~160 nm的銦錫氧化物塗層玻璃(以下稱為ITO基板),並在超聲波浴(例如洗滌劑、去離子水)中進行多步驟清洗。在氣相沉積有機層之前,通過紫外光(UV)和臭氧進一步處理清洗過的ITO基板。ITO基板的所有預處理過程都在潔淨室(100級)內進行。
在高真空設備下(10-7
Torr)利用電阻加熱的石英舟以氣相沉積將這些有機層依序塗布到ITO基板上。通過石英晶體監視器來精確監控或設定各層的厚度和氣相沉積速率(0.1~0.3 nm/sec)。如上所述,還可以使個別層包含不只一種化合物,即通常摻雜有摻雜材料的主體材料。此可通過來自兩個或多個來源的共氣相沉積成功地實現,表示本發明的雜芳族化合物是熱穩定的。
使用二吡嗪並[2,3-f:2',3'-h]喹喔啉-2,3,6,7,10,11-六腈(dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile)(HAT-CN)形成有機EL組件的電洞注入層。N,N-雙(萘-1-基)-N,N-雙(苯基)-聯苯胺(NPB)最常用來作為電洞傳輸層。10,10-二甲基-13-(3-(芘-1-基)苯基)-10H-茚並[2,1-b]三亞苯 (10,10-dimeth-yl-13-(3-(pyren-1-yl)phenyl)-10H-indeno [2,1-b]triphenylene) (H1) 及10,10-二甲基-12-(4-(芘-1-基)苯基)-10H-茚並[2,1-b]三亞苯 (10,10-dimethyl-12-(4- (pyren-1-yl)phenyl)-10H-indeno[2,1-b]triphenylene) (H2) 可用來作為有機 EL 元件中的發光主體 (emitting host),且N1,N1,N6,N6-四-甲苯芘- 1,6-二胺(D1)可作為藍光客體 (blue guest),以進行對照比較。下列通式所示的化合物HB3用來作為電洞阻擋材料 (hole blocking material;HBM),且 2- (萘-1-基)-9-(4-(1-(4-(10-(萘-2-基)蒽-9-基)苯基)-1H-苯並[d]咪唑-2-基)苯基) -1,10-啡啉 (2-(naphthalen-1-yl)-9-(4-(1-(4-(10-(naphthalene-2-yl)anthracen-9-yl)phenyl)-1H-benzo[d]imidazol-2-yl)phenyl)-1,10-phenanthroline) (ET2) 用來作為電子傳輸材料 (electron transporting material;ETM) 以與 8-羥基喹啉酯基-鋰 (8-hydroxyquinolato -lithium, LiQ) 進行共沉積 (co-deposition)。本發明中用於製作對照和示例性有機EL組件的OLED材料和本發明示例性雜芳族化合物的化學結構,例如,但不限於以下所示:
典型的有機 EL 組件由諸如 Al、Mg、Ca、Li、K 或其合金的低功函數金屬材料所構成,並通過熱蒸鍍方式成為陰極,低功函數金屬可輔助電子從陰極注入至電子傳輸層。此外,為了減少電子注入的屏障,並且改進有機 EL 元件性能,在陰極與電子傳輸層之間引入薄膜電子注入層。電子注入層的常規材料是具有低功函數的金屬鹵化物或金屬氧化物,例如:LiF、LiQ、MgO 或 Li2
O。另一方面,在有機 EL 元件製造之後,通過使用 PR650 光譜掃描光譜儀 (PR650 spectra scan spectrometer) 測量 EL 光譜 (EL spectra) 和 CIE 座標 (CIE coordination)。此外,利用吉時利 2400 可程式化設計電壓-電流源 (Keithley 2400 programmable voltage-current source) 取得電流/電壓 (current/voltage)、發光/電壓 (luminescence/voltage) 及良率/電壓 (yield/ voltage) 的特性。上述設備是於室溫 (約 25℃) 及大氣壓力環境中操作。 實施例19
使用與上述方法類似的過程製作具有下列元件結構(如圖1所示)的發螢光有機EL組件:ITO/HAT-CN(20 nm)/NPB(110 nm)/摻雜5%發光客體材料的發光主體 (30 nm)/HB3/摻雜50% LiQ的ET2(35 nm)/LiQ(1 nm)/Al(160 nm)。在圖1所示的組件中,將電洞注入層(HIL)20(HAT-CN)沉積到透明電極10(ITO)上,將電洞傳輸層30(NPB)沉積到電洞注入層20上,將螢光發光層40(發光主體)沉積到電洞傳輸層(HTL)30上,將電洞阻擋層50(HB3)沉積到螢光發光層40上,將電子傳輸層60(ET2)沉積到電洞阻擋層(HBL)50上,將電子注入層70(LiQ)沉積到電子傳輸層(ETL)60上,並將金屬電極80(Al)沉積到電子注入層70上。將該實施例的有機EL組件的I-V-B(1000 尼特亮度時)等測試報告舉例總結於下表1。。 表1
根據上述示例的有機EL元件的測試報告總結,可知用作發光顏色為藍色之有機EL元件的發光客體材料,表現出比現有技術的材料更多或更佳的性能。舉例來說,本發明使用式(1)的雜芳族化合物作為發光客體材料,來與主體材料例如H1或H2搭配的有機EL元件,可具有較低的驅動電壓、或更高的發光電流效率、或更長的半衰期,或更低的功耗。
總而言之,本發明提供了一種可用於有機EL元件的雜芳族化合物。其中,發光顏色為藍色的有機電激發光元件,可以是優選。該雜芳族化合物可由下式(1)表示:
式(1), X1
可以是二價橋並選自於由O、S、Se、CR4
R5
、NR6
和 SiR7
R8
組成的群組。X2
可以是不存在,也可以是二價橋並選自於由O、S、Se、CR9
R10
、NR11
和 SiR12
R13
組成的群組;其中X2
不存在可以是優選。A可以表示具有2、3、4、5、6、7、8或9個環的經取代或未經取代的稠合環烴單元。m可為0、1、2、3或4的整數。B可表示以下式(2):式(2), 其中環C可以表示苯環,也可以表示具有2、3、4或5個環的的經取代或未經取代的稠合環烴單元。Y可以表示二價橋並選自於由O、S、Se、CR14
R15
、NR16
和SiR17
R18
所組成的群組,其中為S或CR14
R15
可以是優選,且其中R14
和R15
可以是獨立以的為甲基為優選。 式(1)右下方的苯環與(R2
)m
,以及式(1)左下方的苯環與(R1
)m
,最好都不要共同構成下列結構:
根據上述教導顯然可以作出許多的修改及變化。因此,應當瞭解的是,在隨附申請專利範圍的範圍內,可以以本文具體描述的方式以外的其他方式來實施本發明。雖然,本文中已說明並描述了具體實施例,但對於所屬技術領域技術人員來說,顯而易見的是可以在不偏離欲單獨由隨附申請專利範圍限制的情況下對本發明作出許多修改。
10‧‧‧透明電極
20‧‧‧電洞注入層
30‧‧‧電洞傳輸層
40‧‧‧發光層
50‧‧‧電洞阻擋層
60‧‧‧電子傳輸層
70‧‧‧電子注入層
80‧‧‧金屬電極
圖1為本發明的有機EL元件的一個實施方式。
10‧‧‧透明電極
20‧‧‧電洞注入層
30‧‧‧電洞傳輸層
40‧‧‧發光層
50‧‧‧電洞阻擋層
60‧‧‧電子傳輸層
70‧‧‧電子注入層
80‧‧‧金屬電極
Claims (8)
- 一種以下式(1)的雜芳族化合物:
- 一種有機電激發光元件,包含由陰極和陽極組成的電極對、及在該電極對之間的發光層及一個或多個有機薄膜層,其中該發光層和該有機薄膜層中的至少一個包含如請求項1所述的雜芳族化合物。
- 如請求項4所述的有機電激發光元件,其中包含式(1)的雜芳族化合物的發光層為螢光客體材料。
- 如請求項4所述的有機電激發光元件,其中包含式(1)的雜芳族化合物的發光層發射藍色的螢光。
- 如請求項4所述的有機電激發光元件,其中該有機電激發光組件為發光面板或背光面板。
- 如請求項1所述的雜芳族化合物,其中該至少一環烴與該共同連接的苯環共同構成萘基、二苯並呋喃基、或二苯並噻吩基。
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