TWI461387B - 聯三伸苯基衍生物在有機電致發光元件上之應用 - Google Patents
聯三伸苯基衍生物在有機電致發光元件上之應用 Download PDFInfo
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Description
本發明是關於一種化合物及其有機發光二極體,尤其是一種聯三伸苯基衍生物及其有機發光二極體。
由於有機發光二極體(Organic light emitting diode,OLED)運用於平面顯示器相當具有優勢,因此許多研究學者都對OLED相當有興趣。其中發展穩定及高效率的三原色(紅、綠、藍)發光材料與發光元件對於OLED發展為商業產品是非常重要的。發展有機發光二極體元件的一項重要要求為發展RGB(紅綠藍)發光元件以符合彩色平面顯示器的需求。
特別是尋找有效率及壽命的藍光電致發光材料,因為其為將OLED實現為顯示及照明用途的重要元件。目前已有許多研究團隊成功地製備有效率的藍光螢光團(fluorophore)及其OLED。然而,到目前為止,色度y座標(Commission Internationale d’nclairage y coordinate value,CIEy
))0.15且具壽命的有效率材料非常稀少。目前仍缺乏良好的有機發光二極體化合物以符合上述需求。
綜合上述,目前亟需發展新穎的發光有機化合物,特別為深藍光發光材料,可有效地用於低耗能之有機發光二極體元件。
本發明之目的為提供一種新穎化合物及其在有機發光二極體之應用。
依據本發明之一實施例,一種聯三伸苯基衍生物,具有化學式(4)或(5),其中Ar1
及Ar2
為芳香族化合物,R1
、R2
及R23
係選自由氫、鹵素、氰基、三氟甲烷基、胺基、C1
-C10
烷基、C2
-C10
烯基、C2
-C10
炔基、C3
。
-C20
環烷基、C3
-C20
環烯基、C1
-C20
雜環烷基、C1
-C20
雜環烯基、芳基及雜芳基所組成的群組。
依據本發明之另一實施例,一種有機發光二極體,包括一陰極、一陽極、設置於陰極及陽極之間的一發光層,以及設置於發光層及陰極之間的發光層,其中發光層包含上述的聯三伸苯基衍生物。
本發明上述及其他態樣、特性及優勢可由附圖及實施例之說明而可更加了解。
一種聯三伸苯基衍生物,具有下列化學式(1):
,其中Ar為芳香族化合物,n為1至3,R1
-R17
係選自由氫、鹵素、氰基、三氟甲烷基、胺基、C1
-C10
烷基、C2
-C10
烯基、C2
-C10
炔基、C3
-C20
環烷基、C3
-C20
環烯基、C1
-C20
雜環烷基、C1
-C20
雜環烯基、芳基及雜芳基所組成的群組。
在一較佳實施例中,本發明之聯三伸苯基衍生物具有下列化學式(2)、(2-1)、(2-2)。
本案之Ar取代基較佳為苯基,其具有下列化學式(3):
,其中R18
-R22
係選自由氫、鹵素、氰基、三氟甲烷基、胺基、C1
-C10
烷基、C2
-C10
烯基、C2
-C10
炔基、C3
-C20
環烷基、C3
-C20
環烯基、C1
-C20
雜環烷基、C1
-C20
雜環烯基、芳基及雜芳基所組成的群組。
此外在一實施例中,化學式(2)之Ar為具有含氮取代基之苯環,例如化學式(4)或(5),其中化學式(4)之Ar1
及Ar2
為芳香族化合物,而化學式(5)之R23
係選自由氫、鹵素、氰基、三氟甲烷基、胺基、C1
-C10
烷基、C2
-C10
烯基、C2
-C10
炔基、C3
-C20
環烷基、C3
-C20
環烯基、C1
-C20
雜環烷基、C1
-C20
雜環烯基、芳基及雜芳基所組成的群組。
在此「芳基」指的是具有一或多個芳香環之碳氫基團。芳基基團範例包括苯基(phenyl,Ph)、亞苯基(phenylene)、萘基(naphthyl)、亞萘基(naphthylene)、芘基(pyrenyl)、蒽基(anthryl)、菲基(phenanthryl)及聯三伸苯基(triphenylenyl)。
「雜芳基」指的是具有一或多個芳香環之碳氫基團,且該芳香環包含至少一雜原子(例如,氮、氧或硫)。雜芳基基團範例可包括呋喃基(furyl)、亞呋喃基(furylene)、茀基(fluorenyl)、吡咯基(pyrrolyl)、噻吩基(thienyl)、噁唑基(oxazolyl)、咪唑基(imidazolyl)、噻唑基(thiazolyl)、吡啶基(pyridyl)、嘧啶基(pyrimidinyl)、喹唑啉基(quinazolinyl)、喹啉基(quinolyl)、異喹啉基(isoquinolyl)及吲哚基(indolyl)。
在此應註明的是烷基、烯基、炔基、環烷基、環烯基、雜環烷基、雜環烯基、芳基、以及雜芳基可包括經取代及未經取代之基團。
可能取代於環烷基、環烯基、雜環烷基、雜環烯基、芳基、以及雜芳基之取代基包含但不受限於C1
-C10
烷基、C2
-C10
烯基、C2
-C10
炔基、C3
-C20
環烷基、C3
-C20
環烯基、C1
-C20
雜環烷基、C1
-C20
雜環烯基、C1
-C10
烷氧基、芳基、芳氧基、雜芳基、雜芳氧基、胺基、C1
-C10
烷胺基、C1
-C20
二烷胺基、芳胺基、二芳胺基、C1
-C10
烷基磺胺(C1
-C10
alkylsulfonamino)、芳基磺胺(arylsulfonamino)、C1
-C10
烷基亞胺(C1
-C10
alkylimino)、芳基亞胺(arylimino)、C1
-C10
烷基磺亞胺(C1
-C10
alkylsulfonimino)、芳基磺亞胺(arylsulfonimino)、氫氧基、鹵素、硫代基(thio)、C1
-C10
烷硫基、芳硫基、C1
-C10
烷磺醯基(alkylsulfonyl)、芳磺醯基(arylsulfonyl)、醯基胺(acylamino)、胺基醯(aminoacyl)、胺基
硫醯(aminothioacyl)、醯胺基(amido)、脒基(amidino)、胍基(guanidine)、脲基(ureido)、硫脲基(thioureido)、腈基、硝基、亞硝基、疊氮基(azido)、醯基、硫醯基、醯氧基(acyloxy)、羧基、及羧酸酯等。另一方面,可能取代於烷基、烯基、或炔基之取代基包含除C1
-C10
烷基外之上述所有取代基。環烷基、環烯基、雜環烷基、雜環烯基、芳基、及雜芳基亦可互相稠合(fused)。
以下更加詳細敘述本發明化合物之製備流程及光譜資料。
1,4-二氫-1,4-環氧苯並(1,4-Dihydro-1,4-epoxytriphenylene)(A)
將9-溴菲(9-bromophenanthrene)(18.6g,72.3mmol)與氨基鈉(8.47g,217.0mmol)置於雙頸瓶中,抽真空通入氮氣後,加入無水THF(120mL)與呋喃(78.1mL,1.07mol),升溫至70℃迴流24小時,反應結束後,過濾去除鹽類,濃縮,以管柱層析法(SiO2
,正己烷)純化,得白色固體14.7g,產率83%。
2-(4-溴苯基)苯並(2-(4-Bromophenyl)triphenylene)(B)
將A
(4.00g,16.4mmol)、1-溴-4-碘苯(1-bromo-4-iodobenzene)(4.64
g,16.4mmol)、鋅(10.72g,163.9mmol)與PdCl2
(PPh3
)2
(1.16g,1.7mmol)置於雙頸瓶中,抽真空通入氮氣後,加入無水甲苯(100mL)與三乙基胺(23.00mL,165.9mmol),升溫至100℃反應24小時,反應結束後,過濾去除金屬、濃縮,以管柱層析法(SiO2
,正己烷)純化,得白色固體3.90g,產率62%。
2-(2,2-二苯基乙烯基)-4,4,5,5-四甲基-1,3,2-二氧硼戊環(2-(2,2-Diphenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)(C)
將2,2-二苯基乙烯基溴(2,2-diphenylvinyl bromide)(6.50g,25.1mmol)置於反應瓶中,加熱抽真空通氮氣後,加入無水THF(40mL)攪拌溶解,降溫至-78℃緩緩滴入n
-BuLi(20.0mL,50.2mmol,2.50M溶於正己烷),維持-78℃攪拌1小時,加入硼酸三丁酯(tri-n
-Butyl borate,請確認)(15.0mL,55.5mmol)反應8小時。終止反應後,混合物與2.0M HCl(100mL)進行酸化3小時,以乙酸乙酯萃取,收集有機層,再以硫酸鎂除水,濃縮靜置待固體析出,過濾得白色固體2,2-二苯基乙烯基硼酸(2,2-diphenylvinyl boronic acid),再將其與2,3-二甲-2,3-丁二醇(pinacol)(4.25g,36.0mmol)溶於甲苯中,升溫至迴流反應2小時,反應結束後,減壓濃縮去除溶劑,以管柱層析法(SiO2
,正己烷/二氯甲烷=1/1)純化,得無色液體4.10g,產率53%。
4,4,5,5-四甲基-2-(1,2,2-三苯基乙烯基)-1,3,2-二氧硼戊環(4,4,5,5-Tetramethyl-2-(1,2,2-triphenylvinyl)-1,3,2-dioxaborolane)(D)
將(2-乙烯基溴-1,1,2-三基)三苯((2-bromoethene-1,1,2-triyl)tribenzene)(5.00g,14.9mmol)置於反應瓶中,加熱抽真空通氮氣後,加入無水THF(50mL)攪拌溶解,降溫至-78℃緩緩滴入n
-BuLi(15.00mL,30.0mmol,2.50M溶於正己烷),維持-78℃攪拌1小時,加入B(OBu)3
(11.0mL,40.8mmol)反應8小時。終止反應後,混合物與2.0M HCl(100mL)進行酸化2小時,以乙酸乙酯萃取,收集有機層,再以硫酸鎂除水,濃縮靜置待固體析出,過濾得白色固體1,2,2-三苯基乙烯基硼酸(1,2,2-triphenylvinylboronic acid),再將其與2,3-二甲-2,3-丁二醇(1.73g,14.6mmol)溶於甲苯中,升溫至迴流反應2小時,反應結束後,減壓濃縮去除溶劑,以管柱層析法(SiO2
,正己烷/乙酸乙酯=20/1)純化,得白色固體2.41g,產率65%。
(E
)-2-(4-苯乙烯基苯基)苯並((E
)-2-(4-Styrylphenyl)triphenylene)(TSP)
將B
(400mg,1.04mmol)、(E
)-苯乙烯基硼酸((E
)-styrylboronic acid)(185mg,1.25mmol)、K2
CO3(aq)
(2.0M,4.00mL)與無水甲苯(12.0mL)置於雙頸瓶中,進行除氧充氮氣,於60℃下攪拌至完全溶解,開大氮氣快速加入Pd(PPh3
)4
(120mg,0.1mmol),將反應升溫至110℃攪拌48小時。反應結束後,減壓濃縮去除溶劑,以水與甲醇沖洗固體,最後進行昇華,溫度為230℃,得白色固體317mg,產率75%。
1
H NMR(400MHz,CDCl3
):δ
8.87(d,J
=1.6Hz,1H),8.77-8.65(m,5H),7.92(dd,J
=8.6,J
=1.6Hz,1H),7.80(d,J
=8.4Hz,2H),7.69-7.66(m,6H),7.56(d,J
=8.0Hz,2H),7.38(t,J
=7.6Hz,2H),7.28(d,J
=7.2
Hz,1H),7.20(s,2H).
13
C NMR(100MHz,CDCl3
):δ
140.3,139.3,137.3,136.7,130.2,130.1,129.8,129.6,129.0,129.0,128.7,128.2,127.7,127.6,127.4,127.3,127.3,127.1,126.6,126.1,124.0,123.4.123.4,121.5.
HRMS(m/z):[M+
]calcd.for C32
H22
,406.1722;found,406.1723
Anal.calcd for C32
H22
:C,94.55;H,5.45;found:C,94.42;H,5.50
2-(4-(2,2-二苯基乙烯基)苯基)苯並(2-(4-(2,2-Diphenylvinyl)phenyl)triphenylene)(TSDP)
將B
(451mg,1.18mmol)、C
(435mg,1.42mmol)、K2
CO3(aq)
(2.0M,8.00mL)與無水甲苯(24.0mL)置於雙頸瓶中,進行除氧充氮氣,於60℃下攪拌至完全溶解,開大氮氣快速加入Pd(PPh3
)4
(139mg,0.12mmol),將反應升溫至110℃攪拌48小時。反應結束後,減壓濃縮去除溶劑,以水與甲醇沖洗固體,最後進行昇華,溫度為250℃,得白色固體388mg,產率68%。
1
H NMR(400MHz,CDCl3
):δ
8.80(d,J
=1.6Hz,1H),8.71-8.63(m,5H),7.85(dd,J
=8.4,J
=1.6Hz,1H),7.67-7.64(m,4H),7.60(d,J
=8.4Hz,2H),7.39-7.27(m,10H),7.17(d,J
=8.4Hz,2H),7.04(s,1H).
13
C NMR(100MHz,CDCl3
):δ
143.4,142.9,140.5,139.2,139.2,136.8,130.4,130.2,130.1,130.1,129.8,129.8,129.6,128.9,128.8,128.3,127.7,127.6,127.6,127.6,127.3,127.3,127.2.126.8,126.0,123.9,123.4,123.3,121.4.
HRMS(m/z):[M+
]calcd.for C38
H26
,482.2035;found,482.2036
Anal.calcd for C38
H26
:C,94.57;H,5.43;found:C,94.35;H,5.33
2-(4-(1,2,2-三苯基乙烯基)苯基)苯並(2-(4-(1,2,2-Triphenylvinyl)phenyl)triphenylene,TSTP)
將B
(1.25g,3.26mmol)、D
(1.37g,3.58mmol)、K2
CO3(aq)
(2.0M,8.00mL)與無水甲苯(24.0mL)置於雙頸瓶中,進行除氧充氮氣,於60℃下攪拌至完全溶解,開大氮氣快速加入Pd(PPh3
)4
(381mg,0.33mmol),將反應升溫至110℃攪拌48小時。反應結束後,減壓濃縮去除溶劑,以水與甲醇沖洗固體,最後進行昇華,溫度為260℃,得白色固體1.50g,產率82%。
1
H NMR(400MHz,CDCl3
):δ
8.80(s,1H),8.72-8.63(m,5H),7.84(d,J
=8.4Hz,1H),7.66-7.64(m,4H),7.56(d,J
=8.0Hz,2H),7.18-7.04(m,17H).
13
C NMR(100MHz,CDCl3
):δ
143.7,143.1,141.2,140.5,139.3,138.7,132.0,131.4,131.4,130.0,129.8,129.8,129.6,128.8,127.8,127.7,127.7,127.3,127.2,126.5,126.5,126.1,123.8.123.3,121.4.
HRMS(m/z):[M+
]calcd.for C44
H30
,558.2348;found,558.2344
Anal.calcd for C44
H30
:C,94.59;H,5.41;found:C,94.45;H,5.39
二乙基4-(苯並基-2-yl)苯甲基磷酸根(Diethyl4-(triphenylen-2-yl)benzylphosphonate)(E)
將A
(760mg,3.11mmol)、鋅(1.85g,28.2mmol)與PdCl2
(PPh3
)2
(198mg,0.28mmol)置於雙頸瓶中,抽真空通入氮氣後,加入無水甲苯(30mL)、1-溴-4-碘苯甲基磷酸根(diethyl 4-iodobenzylphosphonate)(0.65ml,2.82mmol)與三乙基胺(3.91mL,28.2mmol),升溫至110℃反應48小時,反應結束後,過濾去除金屬、濃縮,以管柱層析法(SiO2
,二氯甲烷)純化,得白色固體0.90g,產率70%。
4-(萘基-1-yl(苯基)胺基)苯醛(4-(Naphthalen-1-yl(phenyl)amino)benzaldehyde)(F)
將4-溴苯醛(4-Bromobenzaldehyde)(1.00g,5.40mmol)、1-苯胺基萘(1-anilinonaphthalene)(1.42g,6.48mmol)、Pd(OAc)2
(25mg,0.11mmol)與置於高壓管中,抽真空通入氮氣後,加入無水鄰二甲苯(30mL)、三叔丁基膦(tri-tert-butylphosphine)(0.23ml,0.11mmol)與叔丁醇鈉(623mg,6.48mmol),升溫至120℃反應48小時,反應結束後,過濾去除金屬、濃縮,正己烷/二氯甲烷=1/1)純化,得黃色固體1.10g,產率63%。
4-甲基-N
-苯基-N
-p-甲苯基苯胺(4-Methyl-N
-phenyl-N
-p-tolylaniline)(G)
將4,4'-二甲基二苯基胺(4,4'-dimethyldiphenylamine)(0.99g,5.0mmol)、KOH(2.52g,45.0mmol)、CuCl(99mg,1.0mmol)與1,10-菲咯啉(1,10-phenanthroline)(180mg,1.0mmol)置於雙頸瓶中,抽真空通入氮氣後,加入甲苯(12mL)與碘苯(0.67mL,6.0mmol),升溫至120℃反應12小時,反應結束後,過濾去除金屬、濃縮,以管柱層析法(SiO2
,正己烷/二氯甲烷=1/1)純化,得白色固體916mg,產率67%。
1
H NMR(400MHz,CDCl3
):δ
7.22-7.18(m,2H),7.07-6.91(m,11H),2.31(s,6H).
13
C NMR(100MHz,CDCl3
):δ
148.3,145.4,132.3,129.8,129.0,124.4,122.9,121.7,20.8.
HRMS(m/z):[M+
]calcd.for C20
H19
N,273.1517;found,273.1516
4-(二p
-甲苯胺基)苯醛(4-(Dip
-tolylamino)benzaldehyde)(H)
將DFM(6.0ml)置於雙頸瓶中,抽真空通入氮氣後,在冰浴下緩緩加入POCl3
(0.86ml,5.27mmole),於0℃下攪拌30分鐘後,再將溶
於DFM(6.0ml)的G
(1.2g,4.39mmole)緩緩加入混合,升溫至70℃反應6小時,反應結束後,減壓蒸餾去除溶劑,以管柱層析法(SiO2
,正己烷/二氯甲烷=6/1)純化,得黃色固體1.26g,產率95%。
1
H NMR(400MHz,CDCl3
):δ
9.75(s,1H),7.62(d,J
=8.8Hz,2H),7.13(d,J
=8.0Hz,4H),7.05(d,J
=8.0Hz,4H),6.92(d,J
=8.8Hz,2H),2.33(s,6H).
13
C NMR(100MHz,CDCl3
):δ
190.4,153.7,143.5,135.0,131.3,130.3,128.3,126.4,118.2,21.0.
HRMS(m/z):[M+
]calcd.for C21
H19
NO,301.1467;found,301.1471
(E
)-9-乙基-3-(4-(苯並基-2-yl)苯乙烯基)-9H-咔唑((E
)-9-Ethyl-3-(4-(triphenylen-2-yl)styryl)-9H-carbazole)(TSCz)
將E
(100mg,0.22mmol)與N
-乙基咔唑-3-甲醛(N
-ethylcarbazole-3-carboxaldehyde)(59mg,0.26mmol)置於雙頸瓶中,抽真空通入氮氣後,加入無水THF(10mL);在冰浴下,將溶於THF(10ml)的叔丁醇鉀(potassium tert-butoxide)(49mg,0.44mmole)緩緩加入混合,於0℃反應15分鐘,反應結束後,減壓濃縮去除溶劑,最後進行昇華,溫度為260℃,得黃色固體90mg,產率78%。
1
H NMR(400MHz,CDCl3
):δ
8.89(d,J
=1.6Hz,1H),8.78-8.65(m,5H),8.28(d,J
=1.2Hz,1H),8.14(d,J
=7.6Hz,1H),7.94(dd,J
=8.4,J
=2.0Hz,1H),7.83(d,J
=8.0Hz,2H),7.73-7.65(m,7H),7.50-7.39(m,4H),7.27-7.23(m,2H),4.38(q,J
=7.2Hz,2H),1.45(t,J
=7.2Hz,3H).
13
C NMR(100MHz,CDCl3
):δ
140.2,139.6,139.4,137.2,130.0,
130.0,129.8,129.7,129.7,129.6,128.7,128.5,127.5,127.2,127.1,127.0,126.7,126.0,125.8,125.4,124.5,123.8,123.3.122.9,121.3,120.5,119.1,118.8,108.5,37.6,13.9.
HRMS(m/z):[M+
]calcd.for C40
H29
N,523.2300;found,523.2299
Anal.calcd for C40
H29
N:C,91.74;H,5.58;N,2.67;found:C,91.37;H,5.80;N,2.43
(E
)-N,N
-二苯基-4-(4-(苯並基-2-yl)苯乙烯基)苯胺((E
)-N
,N
-diphenyl-4-(4-(triphenylen-2-yl)styryl)aniline)(TSTA)
將E
(1.0g,2.20mmol)與4-二苯胺基苯甲醛(4-(N
,N
-diphenylamino)benzaldehyde)(0.72g,2.64mmol)置於雙頸瓶中,抽真空通入氮氣後,加入無水THF(20mL);在冰浴下,將溶於THF(20ml)的叔丁醇基(0.49g,4.40mmole)緩緩加入混合,於0℃反應15分鐘,反應結束後,減壓濃縮去除溶劑,最後進行昇華,溫度為260℃,得黃色固體1.04g,產率82%。
1
H NMR(400MHz,CD2
Cl2
):δ
8.93(d,J
=1.6Hz,1H),8.81-8.69(m,5H),7.98(dd,J
=8.4,J
=1.6Hz,1H),7.86(d,J
=8.0Hz,2H),7.73-7.68(m,6H),7.46(d,J
=8.4Hz,2H),7.31-7.27(m,4H),7.22-7.04(m,10H).
13
C NMR(100MHz,CD2
Cl2
):δ
147.9,140.0,139.7,137.5,131.8,130.5,130.4,130.1,130.0,129.7,129.3,128.8,127.9,127.8,127.3,126.7,126.5,125.0,124.4,123.8,123.5,121.7.
HRMS(m/z):[M+
]calcd.for C44
H31
N,573.2457;found,573.2460
Anal.calcd for C44
H31
N:C,92.11;H,5.45;N,2.44;found:C,91.94;H,5.46;N,2.45
(E
)-N
-苯基-N
-(4-(4-(苯並基-2-yl)苯乙烯基)苯基)萘基-1-胺((E
)-N
-phenyl-N
-(4-(4-(triphenylen-2-yl)styryl)phenyl)naphthalen-1-amine)(TSNA)
將E
(1.06g,2.33mmol)與F
(0.91g,2.80mmol)置於雙頸瓶中,抽真空通入氮氣後,加入無水THF(20mL);在冰浴下,將溶於THF(20ml)的叔丁基鉀(523mg,4.66mmole)緩緩加入混合,於0℃反應15分鐘,反應結束後,減壓濃縮去除溶劑,最後進行昇華,溫度為320℃,得黃色固體1.15g,產率79%。
1
H NMR(400MHz,CDCl3
):δ
8.90(s,1H),8.79-8.66(m,5H),7.98-7.91(m,3H),7.85-7.80(m,3H),7.71-7.63(m,6H),7.55-7.48(m,2H),7.42-7.37(m,4H),7.27-6.99(m,9H).
13
C NMR(100MHz,CDCl3
):δ
148.5,148.4,143.6,139.8,139.6,137.5,135.8,131.6,130.8,130.4,130.4,130.1,129.9,129.5,129.2,128.8,128.7,127.8,127.7,127.2,127.1,126.8,126.6,126.4,126.2,124.4,124.3,123.7,122.8,122.6,121.6,121.5.
HRMS(m/z):[M+
]calcd.for C48
H33
N,623.2613;found,623.2616
Anal.calcd for C48
H33
N:C,92.42;H,5.33;N,2.25;found:C,92.38;H,5.08;N,2.33
(E
)-4-甲基-N
-p
-甲苯基-N
-(4-(4-(苯並基-2-yl)苯乙烯基)苯基)苯胺((E
)-4-Methyl-N
-p
-tolyl-N
-(4-(4-(triphenylen-2-yl)styryl)phenyl)aniline)(TSMA)
將E
(1.20g,2.64mmol)與H
(0.96g,3.17mmol)置於雙頸瓶中,抽真空通入氮氣後,加入無水THF(20mL);在冰浴下,將溶於THF(20ml)的叔丁基鉀(593mg,5.28mmole)緩緩加入混合,於0℃反應15分鐘,反應結束後,減壓濃縮去除溶劑,最後進行昇華,溫度為290℃,得黃色固體1.15g,產率82%。
1
H NMR(400MHz,CD2
Cl2
):δ
8.92(d,J
=1.2Hz,1H),8.81-8.69(m,5H),7.97(d,J
=8.4,J
=1.6Hz,1H),7.85(d,J
=8.4Hz,2H),7.73-7.66(m,6H),7.41(d,J
=8.8Hz,2H),7.20-6.97(m,12H),2.33(s,6H).
13
C NMR(100MHz,CD2
Cl2
):δ
148.4,145.4,139.8,139.7,137.5,133.4,130.7,130.4,130.4,130.3,130.1,129.9,129.2,128.9,127.8,127.8,127.7,127.6,127.2,126.4,126.1,125.2,124.3,123.7,122.4,121.7,20.9.
HRMS(m/z):[M+
]calcd.for C46
H35
N,601.2770;found,601.2767
Anal.calcd for C46
H35
N:C,91.81;H,5.86;N,2.33;found:C,91.67;H,5.92;N,2.32
請參照表一,本發明之聯三伸苯基衍生物之放射波長為384至462nm,因此聯三伸苯基化合物可發射藍光,其波長半高寬(FWHM)為50-67nm。
此外,請參照圖1,為示意圖顯示具有聯三伸苯基衍生物的有機發光二極體結構之一實施例。有機發光二極體結構具有設置於陽極1及陰極2之間包含化合物的發光層3。發光層3係將發光材料摻雜至主體發光材料中所構成。有機發光二極體結構還包括從陽極1上方依序形成之電洞注入層7、電洞傳輸層4、電子阻擋層9、發光層3、電洞阻擋層6、電子傳輸層5及電子注入層8。其中,各層之實際厚度與圖中所顯示之尺寸並無
關係。其中,有機發光二極體之電子阻擋層9、電洞阻擋層6及電子注入層8為選擇性包含。
在一實施例中,本發明之聯三伸苯基衍生物可為發光層之一主體發光材料或其摻雜物。
在一摻雜物之有機發光二極體結構,其中以ITO做為基板,測試的陰極材料包括LiF/Al;DMPPP則用以作為發光層之主體材料並摻雜5%之本發明之化合物;測試的電洞傳輸層TCTA(4,4’,4”-tri(N-carbazolyl)triphenylamine);測試的電子傳輸層BCP(2,9-dimethyl-4,7-diphenyl-[1,10]phenanthroline);摻雜發光材料之對照組為BCzVBi(4,4'-(Bis(9-ethyl-3-carbazovinylene)-1,1'-biphenyl)。
例示測試裝置的個別詳細架構及其厚度(單位為nm)如下列,所得結果如表二:
裝置A:TCTA(50)/DMPPP:TSCz
(5%)(40)/BCP(30)/LiF(1)/Al(100)
裝置B:TCTA(50)/DMPPP:TSTA
(5%)(40)/BCP(30)/LiF(1)/Al(100)
裝置C:TCTA(50)/DMPPP:TSNA
(5%)(40)/BCP(30)/LiF(1)/Al(100)
裝置D:TCTA(50)/DMPPP:TSMA
(5%)(40)/BCP(30)/LiF(1)/Al(100)
裝置E:TCTA(50)/DMPPP:BCzVBi
(5%)(40)/BCP(30)/LiF(1)/Al(100)
其中分別包含摻雜發光物TSTA、TSNA
及TSMA
的裝置B、C及D在發光效率、電流效率、最大亮度、半高全寬、光色及元件壽命等性質方面都具有良好性能。
綜合上述,本發明之聯三伸苯基衍生物可放出藍光,其可作為主體發光材料及摻雜物,並可運用於有機發光二極體裝置之中以達成高效率、低操作電壓、高亮度之優勢。
以上所述之實施例僅是為說明本發明之技術思想及特點,其目的在使熟習此項技藝之人士能夠瞭解本發明之內容並據以實施,當不能以之限定本發明之專利範圍,即大凡依本發明所揭示之精神所作之均等變化或修飾,仍應涵蓋在本發明之專利範圍內。
1‧‧‧陽極
2‧‧‧陰極
3‧‧‧發光層
4‧‧‧電洞傳輸層
5‧‧‧電子傳輸層
6‧‧‧電洞阻擋層
7‧‧‧電洞注入層
8‧‧‧電子注入層
9‧‧‧電子阻擋層
圖1為示意圖顯示具有聯三伸苯基衍生物的有機發光二極體結構。
1...陽極
2...陰極
3...發光層
4...電洞傳輸層
5...電子傳輸層
6...電洞阻擋層
7...電洞注入層
8...電子注入層
9...電子阻擋層
Claims (11)
- 一種聯三伸苯基衍生物,具有下列化學式(4)或(5):
- 如請求項1所述之聯三伸苯基衍生物,其具有下列化學式(4):
- 如請求項1所述之聯三伸苯基衍生物,其具有下列化學式:
- 如請求項1所述之聯三伸苯基衍生物,係選自由(E )-9-乙基-3-(4-(苯並基-2-yl)苯乙烯基)-9H-咔唑((E )-9-Ethyl-3-(4-(triphenylen-2-yl)styryl)-9H-carbazole,TSCz)、(E )-N,N -二苯基-4-(4-(苯並基-2-yl)苯乙烯基)苯胺((E )-N ,N -diphenyl-4-(4-(triphenylen-2-yl)styryl)aniline,TSTA)、(E )-N -苯基-N -(4-(4-(苯並基-2-yl)苯乙烯基)苯基)萘基-1-胺((E )-N -phenyl-N -(4-(4-(triphenylen-2-yl)styryl)phenyl)naphthalen-1-amine,TSNA)及(E )-4-甲基-N -p -甲苯基-N -(4-(4-(苯並基-2-yl)苯乙烯基)苯基)苯胺((E )-4-Methyl-N -p -tolyl-N -(4-(4-(triphenylen-2-yl)styryl)phenyl)aniline,TSMA)所組成的群組。
- 一種有機發光二極體,包括:一陰極;一陽極;以及一發光層,設置於該陰極及該陽極之間,其中該發光層包含一聯三伸苯基衍生物,其中該聯三伸苯基衍生物具有下列化學式(4)或(5):
- 如請求項8所述之有機發光二極體,其具有下列化學式(4):
- 如請求項8所述之有機發光二極體,其中該聯三伸苯基衍生物其具有下列化學式(5):
- 如請求項8所述之有機發光二極體,其中該聯三伸苯基衍生物係選自由 (E )-9-乙基-3-(4-(苯並基-2-yl)苯乙烯基)-9H-咔唑((E )-9-Ethyl-3-(4-(triphenylen-2-yl)styryl)-9H-carbazole,TSCz)、(E )-N,N -二苯基-4-(4-(苯並基-2-yl)苯乙烯基)苯胺((E )-N,N -diphenyl-4-(4-(triphenylen-2-yl)styryl)aniline,TSTA)、(E )-N -苯基-N -(4-(4-(苯並基-2-yl)苯乙烯基)苯基)萘基-1-胺((E )-N -phenyl-N -(4-(4-(triphenylen-2-yl)styryl)phenyl)naphthalen-1-amine,TSNA)及(E )-4-甲基-N -p -甲苯基-N -(4-(4-(苯並基-2-yl)苯乙烯基)苯基)苯胺((E )-4-Methyl-N -p -tolyl-N -(4-(4-(triphenylen-2-yl)styryl)phenyl)aniline,TSMA)所組成的群組。
- 如請求項8所述之有機發光二極體,其中該聯三伸苯基衍生物為一主體發光材料。
- 如請求項8所述之有機發光二極體,其中該聯三伸苯基衍生物為一摻雜物。
- 如請求項8所述之有機發光二極體,其中該有機發光二極體為一藍色發光二極體。
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CN201110254005.3A CN102850177B (zh) | 2011-06-28 | 2011-08-24 | 联三伸苯基衍生物在有机电致发光组件上的应用 |
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