CN101944571B - 单层有机电致发光元件 - Google Patents
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- CN101944571B CN101944571B CN2010102497400A CN201010249740A CN101944571B CN 101944571 B CN101944571 B CN 101944571B CN 2010102497400 A CN2010102497400 A CN 2010102497400A CN 201010249740 A CN201010249740 A CN 201010249740A CN 101944571 B CN101944571 B CN 101944571B
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
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Abstract
本发明涉及单层有机电致发光元件,可以提供单层结构且在低电压可以发光的有机EL元件的有机EL染料以及使用了它的有机EL元件。使用的有机EL染料是由通式(1):(Y-L)nXm表示的。这里,X是价数为n的电荷输运基团,Y是发色基团,L是把电荷输运基团和发色基团结合的连结基团,而且m和n为1或更大的整数。
Description
本申请是申请日为2004年12月22日、申请号为200480038650.X、发明名称为“单层有机电致发光元件”的申请的分案申请。
技术领域
[1]本发明涉及单层有机电致发光(EL)元件。
背景技术
[2]现在,在电子器件领域,正在积极进行作为取代液晶的下一代发光材料的有机EL染料的开发。有机EL染料是一种在电流流过其分子的聚集薄膜时染料分子自身发光的物质,从理论上讲,以小的电力就可能发光。为此,以替代电力消耗大的液晶屏为目的的电子器件用监视器的应用和实用化的研究已经迅速展开。
[3]有机EL元件具有把有机空穴输运层和有机电子输运层置于阳极与阴极之间的结构,在有机空穴输运层和/或有机电子输运层中含有有机发光染料,因此,由电极注入的空穴与电子再结合而在从激发态驰豫到基态时发光。为此,把载流子输运与发光功能分离的多层结构,例如,含有空穴输运材料的空穴输运层与发光层的2层结构(如,非专利文献1)、或在其中增加含电子输运材料的电子输运层的3层结构所制作的面板,从而使空穴与电子的再结合效率高,在10V左右的低电压下就发光。不过,在所述的有机EL元件的情况下,如图6所示,就其功能而言,主要是在作为空穴输运层与电子输运层的发光层的界面上发光,因此就存在有难以得到足够的发光效率的缺点。
还有,以多层结构作为元件结构,在其多次的制膜工序中,必须要在对制膜进行精密的膜厚控制并形成没有针孔的膜,因此就有增加元件制造的时间与成本的问题。
与此相对,如果将元件结构制成单层结构,就有可能以较低的成本来制造。这里,作为单层结构的元件,已经提出了例如采用有空穴输运和电子输运两种能力的有机化合物的有机EL元件的方案(专利文献1),但驱动电压高达20V,而且发光辉度也不够。
专利文献1:特开平2-210790号公报
非专利文献1:C.W.Tang,S.A.Van SLYke,Appl.Phys.Lett.,51(12),21,1987年9月913-915)
发明内容
[4]本发明的目的在于提供解决了上述问题的、即使单层结构也可以在低电压发光的有机EL元件。
本发明人等对以往的单层有机EL元件的薄膜结构进行精心研究,结果发现:仅仅把具有空穴输运和电子输运两种能力的有机化合物结合是不够的,而如图5所示,把能输运电荷的有机化合物作为核用具有发光功能的有机化合物夹持,可以使空穴与电子分散在整体中,这样,即使在低驱动电压下也能得到足够的发光辉度。
[5]本发明的有机EL染料是以通式(1):(Y-L)nXm表示的化合物,其中,X表示价数为n的电荷输运基团,Y表示发色基团,L为把电荷输运基团和发色基团结合的连结基团,而m和n为1或更高的整数。
作为上述的组合,(Y-L)nXm可以是m与n为1的Y1-L-X;可以是m为1、n为2的Y1-L-X-L-Y1,还可能是Y1-L-X-L-Y2,Y1-L1-X-L2-Y1,Y1-L1-X-L2-Y2;
也可以是m为1、n为3的(Y1-L)3-X;还有,在n=m时可以是用上述通式(Y-L-X)n表示的Y1-L-X-L-Y1-L-X-L-Y1,Y1-L-X1-L-Y1-L-X2-L-Y1等。
还有,虽然上述制造例是把作为核的电荷输运基团用发色基团夹住所形成的,也可以把作为核的发色基团用电荷输运基团、空穴输运基团或电子输运基团夹住,或用空穴输运基团与电子输运基团夹住。
[6]虽然对于本发明的有机EL染料在低电压发光的原因还不清楚,但认为是由于电荷输运基团的存在提高了发光层的导电性,并且在电荷输运基团附近聚集了空穴或电子,结果是提高了空穴与电子的再结合效率。
由此,就有可能不用多层结构,而是如图1所示,在基板1上,隔着阳极2,层积发光层4,在其上设置阴极3,所形成的含有机EL染料的单层结构即使在低电压下也可以发光。不过,根据需要,也可以设置空穴注入层5(图2)、电子注入层6(图3)或两注入层5和6(图4)。
[7]还有,在所述X是空穴输运基团的情况下,其空穴输运基团中可以使用单环或多环芳香基团。该空穴输运基团可以使用选自蒽基、菲基、芘基、芴基以及联苯基中的任何1种。进而,也可以使用有叔胺基的空穴输运基团。
[8]还有,在上述Y为电子输运基团的情况下,其电子输运基团中可以使用含杂原子的单环或多环芳香基团。进而,在此电子输运基团中,可以用萘二酰亚胺基或苯二酰亚胺基。
萘二酰亚胺等受体为核的物质是有杂环骨架的物质,其电子集结,效率有下降的趋势。这时,在染料结构中连结有二苯胺等空穴输运部位的物质以更好的效率使电子与空穴集结。
[9][化学式1]
[10][化学式2]
[11]通过采用有这样的结构的染料,以萘二酰亚胺为核的化合物可以使空穴与电子有效集结在分子的周围,也就可以提高发光效率。
[12][化学式3]
[13]还有,上述式中的L可以使用通式(2)A1-R1-A2的物质。这里,A1表示与上述电荷输运基团结合的第1结合基,A2表示与上述发色基团结合的第2结合基,R1表示连结第1结合基与第2结合基的间隔基。
[14]上述R1可以采用亚烷基或主链中含杂原子的亚烷基。
[15]还有,上述A1可以用杂原子。进而,上述A2可以使用选自取代或未取代的烷基、醚基、硫醚基、取代或未取代的亚胺基、酰胺基以及酯基中的任何1种。
[16]还有,本发明的有机EL元件的特征在于,具有夹在一对电极之间的单层有机层,且所述有机层含有以上述通式(1)表示的有机EL染料。
[17]由于在发光层中使用了本发明的有机EL染料,可以提供即使是单层结构、也与多层结构元件有同等或更好的在低电压发光的有机EL元件。
由此,使得制造工艺简化、成本更低的有机EL染料的制造成为可能。
[18]
附图说明
[图1]本发明的单层有机EL元件的示意图
[图2]在本发明的单层有机EL元件的发光层的正极侧设置了空穴注入层的示意图
[图3]在本发明的单层有机EL元件的发光层的负极侧设置了电子注入层的示意图
[图4]在本发明的单层有机EL元件的发光层的正极侧设置了空穴注入层、负极侧设置里了电子注入层的示意图
[图5]本发明的单层有机EL元件的功能说明图
[图6]以往的有机EL元件的功能说明图
[图7]发光试验结果的照片,(a)、(b)、(c)和(d)分别表示外加电压3.6V、4.5V、7.7V和9.0V的例子。
[19]符号说明
1基板
2阳极
3阴极
4发光层
5空穴注入层
6电子注入层
具体实施方式
[20]下面来详细说明本发明的实施方式。
本发明的特别优选的有机EL染料是以通式(1):(Y-L)nX表示的化合物,其中,X表示价数为n的电荷输运基团,Y表示发色基团,L为把电荷输运基团和发色基团结合的连结基团,而n为1或更大的整数。
[21]为了提高从电极注入电荷的效率、使所注入的电荷有效迁移,在电荷输运基团中必需要高的电荷迁移率。
在电荷输运基团中使用空穴输运基团的情况下,空穴输运基团可以为单环或多环芳香基团,以多环芳香基团为优选,使用具有平面性的、电子给予性更大的稠环芳香基团为进一步优选。具体的例子可以列举有选自蒽基、菲基、芘基、芴基以及联苯基中的任何1种基团,以使用蒽基、菲基或芘基为进一步优选。
空穴输运基团的价数n以1~4为优选,2为更优选。
[22]还有,空穴输运基团中,也可以使用有叔胺基(-N(Ar1)(Ar2))的基团。
由于叔胺基具有电子给予性,可以提高空穴输运性能(空穴迁移率)。这里,Ar1、Ar2各自分别为取代或未取代的单环或多环芳香基。
有叔胺基的空穴输运基团的具体构成是,例如,空穴输运基团的价数至少是2价、取代部位之一是叔胺基、其余取代部位通过连结基与发色基结合;或是,取代部位之一是通过连结基为中介结合的叔胺基、其余取代部位则通过连结基与发色基结合。
[23]用电子输运基团作为电荷输运基团的情况下,电子输运基团可以使用含杂原子的单环或多环芳香基,以含杂原子的多环芳香基为优选,有杂原子的、平面性的、且电子接受能力大的稠环芳香基为进一步优选。具体列举的例子可以使用萘二酰亚胺基或苯二酰亚胺基,以萘二酰亚胺基为进一步优选。萘二酰亚胺基包括1,8,4,5-萘二酰亚胺基与2,3,6,7-萘二酰亚胺基。
电子输运基团的价数n以1~4为优选,2为更优选。
[24]连结基可以使用以通式(2):A1-R1-A2表示的化合物。这里,A1表示与上述电荷输运基团结合的第1结合基,A2表示与上述发色基团结合的第2结合基,R1表示连结第1结合基与第2结合基的间隔基。
作为间隔基的具体例子,以使用亚烷基或主链中含杂原子的亚烷基为优选。在亚烷基中,以使用亚甲基、亚乙基、三亚甲基为优选。还有,作为在主链上含有杂原子的亚烷基使用的是环氧乙基,以单元重复数为1至2为优选。此外,间隔基中,可以有烯、炔等不饱和键,此时,防止末端的染料与电荷输运基团堆积的效果好。进而,把电荷输运基与烯、炔等不饱和基团直接结合,也可以把电荷输运基和末端的染料固定在平面中。
[25]还有,可以使用杂原子来作为第1结合基,以使用氧原子、氮原子为优选。还有,第2结合基以使用选自取代或未取代的烷基、醚基、硫醚基、取代或未取代的亚氨基、酰胺基以及酯基中的任何一种为优选。
[26]这里来说明连结基的作用。
连结基通过连结了第1结合基与第2结合基,从而确保了发色基团与电荷输运基团的连结。进而,间隔基的存在确保了发色基团与电荷输运基团之间的物理距离,确保了发色基团与电荷输运基团的分子骨架选择的自由度,另一方面,抑制了发色基团与电荷输运基团的堆积,防止了发色基团的发光波长变化或发光强度的降低。进而,在第1结合基中使用杂原子,阻碍了电荷输运基团与发色基团之间的共轭及电子共振,从而有效防止了发色基团的发光波长的变化或发光强度的降低。
还有,第1结合基中使用杂原子,可以使分子整体为更刚直的结构,因而可以进一步抑制其堆积。进而,抑制了通电时的发热造成的结构变化,也可以进一步提高耐热性。
[27]发色基团可以列举有,例如,四苯基丁二烯和苝等多环芳香化合物、环戊二烯衍生物、二唑衍生物、香豆素衍生物、二苯乙烯基吡嗪衍生物、吖啶酮衍生物、喹吖啶酮衍生物、茋衍生物、二唑并吡啶衍生物、咪唑衍生物、(噻)二唑并吡啶衍生物、噻二唑衍生物以及四苯基噻吩衍生物等。
环戊二烯衍生物可以列举有1,2,3,4-四苯基-1,3-环戊二烯、1,2,3,4,5-五苯基-1,3-环戊二烯。
香豆素衍生物可以列举有香豆素1、香豆素6、香豆素7、香豆素30。
二苯乙烯基吡嗪衍生物可以列举有2,5-二-(2-(4-联苯基)乙烯基)吡嗪、2,5-二(4-乙基苯乙烯基)吡嗪、2,9-二(4-甲氧基苯乙烯基)吡嗪。
吖啶酮衍生物可以列举的是吖啶酮及其衍生物。
喹吖啶酮衍生物可以列举的是喹吖啶酮及其衍生物。
茋衍生物可以列举的是1,1,4,4-四苯基-1,3-丁二烯、4,4’-二(2,2-二苯基乙烯基)联苯。
[29]优选的发色基团与电荷输运基团的组合是,在电荷输运基团是空穴输运基团(电子给予性基团)时,发色基团是有电子接受性基团的染料。还有,在电荷输运基团是电子输运基团(电子接受性基团)时,发色基团优选具有电子给予性基团的染料。还有,与电荷输运基团连结的发色基团的数目随电荷输运基团的电荷输运能力的高低而定,通常,为了与电荷输运基团的电子给予性和电子接受性平衡,相当于每1分子电荷输运基团而言,发色基团的数目为2分子或更多,以2分子为更优选。
[30]由于在以蒽等具有给予体特性的化合物为核的情况下,几乎所有的染料都是受体,可以形成多种组合。另一方面,在萘二酰亚胺等受体的情况也一样,在分子周围集结了电子,因而有多种组合可以使用。特别是,在以蒽等具有给予体特性的化合物为核的情况,只要是其染料的骨架是具有杂环骨架的就可以。有卤原子的染料等也同样可以使用。
[31]本发明中优选使用的发色基团可以列举如下。
[32][化学式4]
(式中,R1和R2各自独立地表示可以有取代基的芳香烃基。)
[33]2.由以下通式表示的咪唑衍生物
[34][化学式5]
(式中,C、D表示含羧基的、可以有其它取代基的芳香烃基或杂环基团或环内含杂原子的芳香基团,C与D相同或不同均可。Y表示可以有羧基的碳原子。)
[36][化6]
(式中,R1、R2、R3和R4各自独立地表示可以有取代基的芳香烃基,X表示可以有取代基的氮原子、可以有取代基的硫原子、可以有取代基的氧原子或可以有取代基的硒原子;R3表示氢原子、氰基、羧基、可以有取代基的酰胺基、可以有取代基的酯基、可以有取代基的烷基、可以有取代基的芳香烃基或可以有取代基的杂环基。)
[37]4.由以下通式表示的噻二唑衍生物
[38][化7]
(式中,R1和R2表示氢原子、卤原子、氰基、硝基、羧基、可以有取代基的烷基、可以有取代基的芳烷基,可以有取代基的链烯基、可以有取代基的氨基、可以有取代基的酰胺基、可以有取代基的烷氧基、可以有取代基的烷氧羰基、可以有取代基的烷氧基磺酰基、可以有取代基的芳香烃基或可以有取代基的杂环基,X表示氢原子、卤原子、烷氧基或羟基。)
[39]5.由以下通式表示的2,3,4,5-四苯基噻吩衍生物1
[40][化学式8]
(式中,R12~R14各自独立地表示氢原子、直链、支链或环状烷基、取代或未取代的芳基,或取代或未取代的芳烷基,Ar1和Ar2表示取代或未取代的芳基,进而,Ar1和Ar2也可以与所结合的氮原子一起形成含氮杂环,Y1和Y2表示氢原子、卤原子、直链、支链或环状烷基、直链、支链或环状烷氧基、取代或未取代的芳基、取代或未取代的芳烷基或取代或未取代的氨基。)
[41]6.由以下通式表示的2,3,4,5-四苯基噻吩衍生物2
[42][化学式9]
(式中,Ar1~Ar6各自独立地表示取代或未取代的芳基,进而,Ar1与Ar2、Ar3与Ar4以及Ar5与Ar6也可以与所结合的氮原子一起形成含氮杂环。)
[43]下面来说明本发明的有机EL元件的构成。
如图1所示,本发明的有机EL元件具有基体1/阳极2/发光层4/阴极3的构成、有机层是只为发光层4的单层结构。
[44]基体起到支撑元件的作用,可以使用透明基板。透明基板可以使用例如玻璃和透明塑料片等。
[45]阳极可以采用含有功函数大(约4eV或更高)的金属、合金或导电性氧化物的电极材料。具体的例子,可以使用金、铂、钯、氧化铟、氧化锡铟(ITO)、氧化锡等。用蒸镀法或溅射法可以在基体上形成这些电极材料。这些电极材料可以是单独使用或使用多个而制成多层结构。
阳极的厚度为5~1000nm,以10~500nm为优选。
[46]阴极可以使用功函数小的金属,例如,锡、镁、铟、钙、铝、银或它们的合金。用蒸镀法或溅射法可以形成这些电极材料。这些电极材料可以是单独使用或使用多种制成多层结构。
阴极的厚度为5~1000nm,以10~500nm为优选。
[47]发光层可以是把本发明的有机EL染料用真空蒸镀法等物理制膜方法所制的膜,或者,也可以采用含有机EL染料与粘合剂树脂的溶液涂布的化学制膜法来制作。发光层的厚度为5~300nm,以10~150nm为更优选。
实施例
[48]虽然下面说明的是本发明的实施例,但是,本发明并不限于这些实施例。本领域技术人员可以根据本发明所述,采用公知的方法来合成各种有机EL染料。
本实施例中使用的有机EL染料是由下述方法合成的。
合成例1
(用蒽基为空穴输运基团的有机EL染料的合成)
(1)蒽的季盐2的合成
按照下面的流程图1,合成蒽的季盐2。
[49][化学式10]
流程图1
[50]在200mL的三口烧瓶中,用90mL无水二甲基甲酰胺(DMF)把2.06g(27.0mmol)的N-甲基乙醇胺溶解。然后冷却至-15℃,用0.5小时的时间加入1.08g(27mmol)的60%NaH。加毕后,在-15℃搅拌1h。然后,以结晶原样慢慢加入3.00g(13.5mmol)的9,10-二(氯甲基)蒽(1)。在加完之后的1小时后,温度上升至-10℃,整夜搅拌。反应结束之后,减压蒸去DMF,残渣用200mL二氯甲烷溶解,滤去不溶解的成分。向其中加入50mL的水,一边搅拌一边加入三氟乙酸(TFA)直至pH显示酸性。静置15分钟之后分成2层。把此操作进行2次,浓缩水相,冷冻干燥,得到2.43g的2,收率为33%。
[51](2)发色基团7的合成
按照下面的流程图2合成发色基团7。
[52][化学式11]
流程图2
[53]在50mL的三口烧瓶中,用20mL DMF使1.0g(0.0026mol)的二唑并吡啶羧酸与0.30g(0.0026mol)的N-羟基丁二酰亚胺溶解。用30分钟的时间向其中滴入0.54g(0.0026mol)的N,N’-二环己基碳二酰亚胺。滴毕,在室温下搅拌30小时。减压下馏去DMF。残渣在硅凝胶柱色谱中(氯仿)分离纯化,得到0.76g二唑并吡啶的活性酯7,收率为62%。
[54](3)有机EL染料8的合成
按照下面的流程图3合成有机EL染料8。
[55][化学式12]
流程图3
[56]在30mL的三口烧瓶中,用15mL DMF使0.35g(0.26mmol)的5与0.22g(0.57mmol)的染料7溶解。向其中加入79μL(2.2当量)的三乙胺。在室温下搅拌3小时。然后,减压下馏去DMF。残渣在硅凝胶柱色谱(展开剂:氯仿∶甲醇=10∶2)中分离,得到228mg的8,收率为82%。
[57]合成例2
(用萘二酰亚胺基为电子输运基团的有机EL染料的合成)
(1)萘二酰亚胺的季盐5的合成
按照下面的流程图4合成萘二酰亚胺的季盐5。
[58][化学式13]
流程图4
[59]在300mL的三口烧瓶中,用150mL无水THF使4.6g(17.3mmol)的萘-1,4,5,8-四羧酸二酐与12.0g(39.9mmol)的4溶解。然后,加热回流搅拌23小时。冷却后,加入30mL氯仿,过滤。由于向滤液中加入200mL甲醇就会析出沉淀物,因而将其过滤。把滤液浓缩后,残渣溶解在甲醇中,用水沉淀。干燥沉淀物,得到4.82g的5,收率为34%。
[60](2)发色基团7的合成
发色基团7使用由合成1的方法合成的物质。
[61](3)有机EL染料9的合成
按照下面的流程图5合成有机EL染料9。
[62][化学式14]
流程图5
[63]在30mL的三口烧瓶中,用15mL DMF使0.16g(0.26mmol)的2与0.22g(0.57mmol)的染料7溶解。向其中加入79μL(2.2当量)的三乙胺,室温搅拌3小时。然后,减压馏去DMF。残渣在硅凝胶柱色谱(展开剂:氯仿∶甲醇=10∶2)中分离,得到180mg的9,收率为51%。
[64]实施例1
(有空穴输运基团的有机EL元件的制作)
按照下述步骤制作采用ITO为阳极、铝为阴极的单层结构元件。
实验No.1
把20~50mg的有机EL染料8放在升华面板上计量之后,固定于电极上。把形成了ITO电极的玻璃板(15mm×15mm)装在蒸镀装置ULVACVPC-260中,用扩散泵对系统内进行减压(5×10-5托)。到达规定的真空度大约需要3小时。在系统内压力变为5×10-5托时,由通250V/40~65A的电流加热,蒸镀到染料层的膜厚变为30nm为止(蒸镀速度为)。在达到规定的蒸镀膜之后,切断电源,然后减压30分钟。其后,解除减压,装铝电极,开始用扩散泵减压。在系统内的压力变为5×10-5托时,由通250V/55~75A的电流加热,蒸镀到膜厚变为200nm为止(蒸镀速度为)。在膜厚变为120nm时切断电源,冷却蒸镀装置。冷却后,慢慢解除减压。开启蒸镀装置,取出元件。用环氧粘接剂把元件的蒸镀面粘接在装有干燥剂的样品瓶的口上。
[65]实验No.2和3
用有机EL染料8按照与实验No.1同样的方法制作染料层膜厚45nm、75nm的元件(分别为实施No.2和3)。
[66](发光试验)
采用AND制造的AD-8713 Dual DC Power Supply作为电流发生装置。
在元件的铝电极侧接负,ITO电极侧接正。设定上限电流为1.5A,用可变电压旋纽慢慢加上电压,进行发光实验。表1示出了结果。实验No.1~3各制作6个样品,共计制作18个样品。照度是指6个样品在外加电压9V时的值的平均值。
[67]
[表1]
[68]对在发光试验时发光层膜厚为30nm的元件的发光进行拍照(图7)。图1中的(a)、(b)、(c)和(d)分别示出了外加电压为3.6V、4.5V、7.7V和9.0V的结果。所制作的面板从3.6V的低电压开始发光。多层结构的有机EL元件中有良好能量效率的元件在约3~5V发光。与此相对,本发明的有机EL元件,作为单层结构,首次可以在与多层结构同样或更低的电压下发光。而且,随外加电压的上升,照度也提高了。
[69]实施例2
(有电子输运基团的有机EL染料的合成)
用50mg有机EL染料9,按与实施例1同样的方法,制作发光层膜厚为50nm的单层结构元件,进而进行发光试验,表2示出了结果。尽管驱动电压比实施例1的情况高,但是在10V以下发出了黄绿色的光。再有,照度是指6个样品在外加电压9V时的值的平均值。
[70]
[表2]
Claims (2)
2.一种包括含有通式:(Y-L)nXm表示的发色基团Y与电荷输运基团X连结而成的有机电致发光染料的发光层的有机电致发光元件,
式中,X表示电荷输运基团,其是由萘二酰亚胺基组成的电子输运基团,
式中,R1和R2相互独立并且表示可以有取代基的芳香烃基,和
L表示连结电荷输运基团和发色基团的连结基团,是以通式(2):
A1-R1-A2表示的,其中,A1表示与所述电荷输运基团结合的第1结合基、含有N-丙基哌嗪基;A2表示与所述发色基团结合的第2结合基,含有酰胺基;而且R1是连结第1结合基与第2结合基的间隔基,其含有亚烷基,
并且m和n分别为1或更大的整数。
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CN1965052A (zh) | 2007-05-16 |
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