CN1583691A - 蒽化合物以及包括此蒽化合物的有机电致发光装置 - Google Patents
蒽化合物以及包括此蒽化合物的有机电致发光装置 Download PDFInfo
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- -1 Anthracene compound Chemical class 0.000 title claims abstract description 35
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 239000000126 substance Substances 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 230000005540 biological transmission Effects 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 230000005525 hole transport Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 description 30
- 239000010410 layer Substances 0.000 description 20
- 125000003368 amide group Chemical group 0.000 description 17
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000003282 alkyl amino group Chemical group 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 238000005424 photoluminescence Methods 0.000 description 6
- 125000005577 anthracene group Chemical group 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000003810 ethyl acetate extraction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 150000001454 anthracenes Chemical class 0.000 description 4
- 125000004986 diarylamino group Chemical group 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- KOUDKOMXLMXFKX-UHFFFAOYSA-N sodium oxido(oxo)phosphanium hydrate Chemical compound O.[Na+].[O-][PH+]=O KOUDKOMXLMXFKX-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 125000005240 diheteroarylamino group Chemical group 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ZSAUZZXFIZPTAU-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound BrC1=CC2=CC=CC=C2C=C1.BrC1=CC2=CC=CC=C2C=C1 ZSAUZZXFIZPTAU-UHFFFAOYSA-N 0.000 description 2
- ZZLCFHIKESPLTH-UHFFFAOYSA-N 4-Methylbiphenyl Chemical group C1=CC(C)=CC=C1C1=CC=CC=C1 ZZLCFHIKESPLTH-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- VJGHWMBHJMWHMF-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1.BrC1=CC=CC=C1 VJGHWMBHJMWHMF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane Chemical compound CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000005493 quinolyl group Chemical group 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BSHSCWRTJSBWLY-UHFFFAOYSA-N 1-cyclohexyl-4-phenylbenzene Chemical group C1CCCCC1C1=CC=C(C=2C=CC=CC=2)C=C1 BSHSCWRTJSBWLY-UHFFFAOYSA-N 0.000 description 1
- SRQOBNUBCLPPPH-UHFFFAOYSA-N 1-ethyl-4-phenylbenzene Chemical group C1=CC(CC)=CC=C1C1=CC=CC=C1 SRQOBNUBCLPPPH-UHFFFAOYSA-N 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 1
- XAIKOVRFTSBNNU-UHFFFAOYSA-N anthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1.C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 XAIKOVRFTSBNNU-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 229930006728 pinane Natural products 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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Abstract
本发明提供一种蒽化合物，具有化学式(I)或(II)，其中每个R1，R2，R3，R4，R5和R6独立地为碳数6至20的无取代或有取代的芳香基，碳数2至20的无取代或有取代的杂芳香基，或碳数1至12的无取代或有取代的烷基，其中取代基为C1－10烷基，C1－10烷氧基，或卤素。
Description
技术领域
本发明涉及一种用于有机电致发光装置的蒽(anthracene)化合物，特别有关于一种蒽化合物，其可作为有机电致发光装置的发光层或空穴传输层。
背景技术
有机电致发光装置(organic electroluminescent device)，亦称作有机发光二极管(organic light-emitting diode；OLED)，是以有机层作为主动层的一种发光二极管(LED)。由于有机电致发光装置具有低电压操作、高亮度、重量轻、广视角、以及高对比值等优点，近年来已渐渐使用于平面面板显示器(flatpanel display)上。
一般而言，OLED包括对电极，以及在电极之间的发光层。发光是导因于以下的现象，当电场施加于两电极时，阴极射出电子到发光层，阳极射出空穴到发光层。当电子与空穴在发光层中结合时，能阶转移到价键能带(valence bond band)，使它们释发出能量，而发出荧光(fluorescent light)。
蒽化合物(anthracene)已被用作空穴传输层和发光层的材料。例如，美国专利第6,465,115号中揭露一种作为空穴传输层的有机蒽物质，具有以下化学式：
其中Ar独立地为碳数5至20的有取代或无取代的芳香基。
在美国专利第5,759,444中揭露一种发光的蒽化合物，具有以下化学式：
其中A1至A4为碳数6至16的有取代或无取代的芳香基。在此蒽化合物中，在蒽环上的9和10位置上引进了双芳香氨基(diarylamino group)。可发现到双芳香氨基的加入，可以使此蒽发光材料具有空穴传输的特性。而且，加入双芳香氨基的取代基，一般认为可增加发光层与空穴传输层接口的稳定性，可以增加组件寿命。
发明内容
有鉴于此，本发明的目的即为提供一种新颖的蒽化合物(anthracene)，其含有双芳香氨基(diarylamino group)，双杂芳香氨基(diheteroarylaminogroup)，或双烷氨基(dialkylamino group)。
本发明的另一目的为提供一种有机电致发光装置，其包括本发明的蒽化合物。本发明的蒽化合物可作为有机电致发光装置中的发光层或空穴传输层。
为达成本发明的目的，本发明的蒽化合物具有化学式(I)或(II)
其中每个R1，R2，R3，R4，R5和R6独立地为碳数6至20的无取代或有取代的芳香基，碳数2至20的无取代或有取代的杂芳香基，或碳数1至12的无取代或有取代的烷基，其中取代基为C1-10烷基，C1-10烷氧基，或卤素。
本发明的有机电致发光装置包括一对电极，以及在此对电极之间的有机发光介质层。此有机发光介质层包括上述具有化学式(I)或(II)的蒽化合物。
图式的简单说明
图1显示化合物(2)和(3)在不同波长下的光致发光(PL)强度的图形。
具体实施方式
本发明的特征为，在本发明的蒽化合物中，在蒽环的1至4位置中的一个位置上，或者5至8位置中的一个位置上引进至少一个双芳香氨基(diarylamino group)，双杂芳香氨基(diheteroarylamino group)，或双烷氨基(dialkylamino group)作为取代基。
详而言之，在蒽环的1至4位置中的一个位置上引进一个双芳香氨基(diarylamino group)，双杂芳香氨基(diheteroarylamino group)，或双烷氨基(dialkylamino group)作为取代基。于是，本发明的蒽化合物具有化学式(I)
其中每个R1，R2，R5和R6独立地为碳数6至20的无取代或有取代的芳香基，碳数2至20的无取代或有取代的杂芳香基，或碳数1至12的无取代或有取代的烷基，其中取代基为C1-10烷基，C1-10烷氧基，或卤素。
可将双芳香氨基，双杂芳香氨基，和双烷氨基的任意两者，引进于蒽环上。例如，1至4位置中的一个位置上引进一个上述氨基，5至8位置中的一个位置上引进一个上述氨基。于是，本发明的蒽环具有化学式(II)
其中每个R1，R2，R3，R4，R5和R6独立地为碳数6至20的无取代或有取代的芳香基，碳数2至20的无取代或有取代的杂芳香基，或碳数1至12的无取代或有取代的烷基，其中取代基为C1-10烷基，C1-10烷氧基，或卤素。
对于化学式(I)和(II)化合物中的每个R1至R6，无取代或有取代的芳香基的具体例子包括苯基，2-甲基苯基，3-甲基苯基，4-甲基苯基，4-乙基苯基，联苯基(biphenyl)，4-甲基联苯基，4-乙基联苯基，4-环己基联苯基，联三苯基(terphenyl)，3，5-二氯苯基，萘基(naphthyl)，5-甲基萘基，蒽基(anthryl)，和蒎基(pyrenyl)。
无取代或有取代的杂芳香基的具体例子包括呋喃基(furanyl)，噻吩基(thiophenyl)，吡咯基(pyrrolyl)，吡喃基(pyranyl)，噻喃基(thiopyranyl)，吡啶基(pyridinyl)，噻唑基(thiazolyl)，咪唑基(imidazolyl)，嘧啶基(pyrimidinyl)，三嗪基(triazinyl)，吲哚基(indolyl)，喹啉基(quinolyl)，嘌呤基(purinyl)，和咔唑基(carbazolyl)。
无取代或有取代的烷基的具体例子包括甲基，乙基，丙基，丁基，sec-丁基，tert-丁基，戊基，己基，庚基，辛基，硬脂酰(stearyl)，2-苯基异丙基(2-phenylisopropyl)，三氯甲基，和三氟甲基。
当只有一个双芳香氨基(或双杂芳香氨基或双烷氨基)引进于蒽环的2位置上时，本发明的蒽化合物具有化学式(III)
其中R1，R2，R5，R6的定义同上。
当R1和R2为无取代或有取代的芳香基时，化学式(III)的具体例子包括
当一个双芳香氨基(或双杂芳香氨基或双烷氨基)引进于蒽环的2位置上，而另一个双芳香氨基(或双杂芳香氨基或双烷氨基)引进于蒽环的6位置上，则本发明的蒽化合物具有化学式(IV)
其中R1，R2，R3，R4，R5，R6的定义同上。
当R1至R4为无取代或有取代的芳香基时，化学式(IV)的具体例子包括
以下通过数个实施例以更进一步说明本发明的方法、特征及优点，但并非用来限制本发明的范围，本发明的范围应以所附的权利要求为准。
【实施例1】：
合成途径如下：
Compound(1)
Compound(2)
合成化合物(1)的方法
将蒽醌(anthraquinone)(1g，4.8mmol)，溴苯(bromobenzene)(1.66g，10.6mmol)，NaOtBu(1.1g，11.52mmol)和Pd(OAc)2(71mg，0.32mmol)的悬浮液，溶于50mL的无水甲苯中，经由注射器加入三-tert-丁基膦(tri-tert-butylphosphine)(257mg，1.28mmol)。加热反应混合物，回流(reflux)36小时。冷却后，加入50mL水，然后以乙酸乙酯萃取。以MgSO-4干燥后，以管柱层析法(column chromatography)纯化，得到化合物(1)(1.04g)。
合成化合物(2)的方法
将2-溴萘(2-bromonaphthalene)(2.3g，11mmol)溶于100mL THF中，将4.8mL的n-BuLi(11mmol，2.5M)于-78℃下慢慢加入溶液中。30分钟后，将溶于30mL THF内的化合物(1)(1.7g，4.7mmol)逐滴加入上述混合物中。使混合物回到室温。加入冷水(100mL)，分离有机相。将水相以乙酸乙酯萃取。有机相以MgSO4干燥，然后以旋转式汽化器(rotary evaporator)除去溶剂。将KI(2.8g，17mmol)，次磷酸钠单水合物(sodium hypophosphitemonohydrate)(3.8g，32mmol)，和30mL乙酸加入粗产物中。加热混合物以回流2小时。冷却后，收集白色沈淀，然后以管柱层析法纯化，得到化合物(2)(2.5g)。
图1显示在不同波长下，化合物(2)和(3)的光致发光(photoluminescent)(PL)强度的图形。其显示化合物(2)的最大强度的波长为504nm，表示化合物(2)发绿光。
此外，测得化合物(2)的HOMO能阶为5.40eV，与NPB(一种作为空穴传输层的常用材料)的HOMO能阶(5.5eV)非常接近。因此，本发明的化合物(2)适合于作为空穴传输层。
【实施例2】：合成化合物(3)的方法
合成途径如下：
Compound(3)
将2，4-二氟溴苯(2.5g，13mmol)溶于100mL的THF中，然后将5.2mL的nBuLi(13mmol，2.5M)于-78℃下慢慢加入混合物中。30分钟后，将上述混合物于-78℃下逐滴加入溶于30mL THF内的化合物(1)(2.1g，5.8mmol)中。使混合物达到室温。加入冷水(100mL)，分离有机相。将水相以乙酸乙酯萃取。有机相以MgSO4干燥，然后以旋转式汽化器除去溶剂。将KI(3.4g，20.5mmol)，次磷酸钠单水合物(4.9g，41.2mmol)，和30mL乙酸加入粗产物中。加热混合物以回流2小时。冷却后，收集白色沈淀，然后以管柱层析法纯化，得到化合物(3)(1.6g)。
图1显示在不同波长下，化合物(2)和(3)的光致发光(photoluminescent)(PL)强度的图形。其显示化合物(3)的最大强度的波长为513nm，表示化合物(3)发绿光。
此外，测得化合物(3)的HOMO能阶为5.85eV，与NPB(一种作为空穴传输层的常用材料)的HOMO能阶(5.5eV)非常接近。因此，本发明的化合物(3)适合于作为空穴传输层。
【实施例3】
合成途径如下：
Compound(4)
Compound(5)
合成化合物(4)的方法
将2，6-二胺基蒽醌(2，6-diaminoanthraquinone)(1.2g，5mmol)，溴苯(bromobenzene)(3.5g，22mmol)，NaOtBu(1.2g，12mmol)和Pd(OAc)2(149mg，0.66mmol)的悬浮液，溶于50mL的无水甲苯中，经由注射器加入三-tert-丁基膦(533mg，2.64mmol)。加热反应混合物，回流36小时。冷却后，加入50mL水，然后以乙酸乙酯萃取。以MgSO-4干燥后，以管柱层析法纯化，得到化合物(4)(1.1g)。
合成化合物(5)的方法
将2-溴萘(2-bromonaphthalene)(2.3g，11mmol)溶于100mL的THF中，然后将4.8mL的nBuLi(11mmol，2.5M)于-78℃下慢慢加入混合物中。30分钟后，将溶于30mL THF内的化合物(4)(2.7g，5mmol)逐滴加入上述混合物中。使混合物回到室温。加入冷水(100mL)，分离有机相。将水相以乙酸乙酯萃取。有机相以MgSO4干燥，然后以旋转式汽化器除去溶剂。将KI(3.0g，18mmol)，次磷酸钠单水合物(4.1g，34mmol)，和30mL乙酸加入粗产物中。加热混合物以回流2小时。冷却后，收集白色沈淀，然后以管柱层析法纯化，得到化合物(5)(3.1g)。
虽然本发明已以优选实施例揭露如上，然其并非用以限制本发明，对于本领域普通技术人员来说，在不脱离本发明的构思和范围内，当可做更动与润饰，因此本发明的保护范围当以所附的权利要求书所界定者为准。
Claims (10)
1.一种蒽化合物，具有化学式(I)或(II)
其中，每个R1，R2，R3，R4，R5和R6独立地为碳数6至20的无取代或有取代的芳香基，碳数2至20的无取代或有取代的杂芳香基，或碳数1至12的无取代或有取代的烷基，其中，该取代基为C1-10烷基，C1-10烷氧基，或卤素。
2.如权利要求1所述的蒽化合物，其为择自以下化学式之一
3.如权利要求1所述的蒽化合物，其为择自以下化学式之一
4.如权利要求1所述的蒽化合物，其可发光。
5.如权利要求1所述的蒽化合物，其具有空穴传输性质。
6.一种有机电致发光装置，其包括对电极，以及在该对电极之间的有机发光介质层，
其中，该有机发光介质层包括蒽化合物，具有化学式(I)或(II)
其中，每个R1，R2，R3，R4，R5和R6独立地为碳数6至20的无取代或有取代的芳香基，碳数2至20的无取代或有取代的杂芳香基，或碳数1至12的无取代或有取代的烷基，其中，该取代基为C1-10烷基，C1-10烷氧基，或卤素。
7.如权利要求6所述的有机电致发光装置，其中，该蒽化合物为择自以下化学式之一
8.如权利要求6所述的有机电致发光装置，其中，该蒽化合物为择自以下化学式之一
9.如权利要求6所述的有机电致发光装置，其中，该有机发光介质层包括发光层，且该发光层包括蒽化合物，其具有化学式(I)或(II)。
10.如权利要求6所述的有机电致发光装置，其中，该有机发光介质层包括发光层和空穴传输层，该空穴传输层包括蒽化合物，其具有化学式(I)或(II)。
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