CN1365347A - 蒽衍生物和使用此衍生物的电致发光器件 - Google Patents
蒽衍生物和使用此衍生物的电致发光器件 Download PDFInfo
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- CN1365347A CN1365347A CN01800733A CN01800733A CN1365347A CN 1365347 A CN1365347 A CN 1365347A CN 01800733 A CN01800733 A CN 01800733A CN 01800733 A CN01800733 A CN 01800733A CN 1365347 A CN1365347 A CN 1365347A
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/28—Anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/50—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed
- C07C15/52—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic non-condensed containing a group with formula
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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Abstract
通式(I)的蒽衍生物和有机电致发光器件,该器件有至少一个夹在一对电极间的且含该衍生物的有机发光层,式中X和Y各自独立代表一个得自芳环的三价基团;(1)A1到A4各自独立代表芳基或是一个单价杂环基,或者(2)A1和A3代表氢原子,A2和A4代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代;R1到R16各自独立代表氢原子、卤原子、氰基、硝基、烷基等;Q代表亚环烷基等;p代表选自0、1和2的数。当此新型蒽衍生物用作有机电致发光器件的构成材料时,此新型衍生物呈现出高发光效率及优异的耐热性能。
Description
技术领域
本发明涉及一种新的有机化合物和一种使用该有机化合物的有机电致发光(下文中电致发光将称作EL)器件。更具体地说,本发明涉及一种用作有机EL器件构成材料的蒽衍生物和使用该蒽衍生物且呈现高发光效率及优异耐热性能的有机EL器件。
技术背景
利用电场中发光现象的电致发光器件因自发光作用而表现出很高的自分辨率,因其完全为固体器件而具有优异的抗冲击性。因此,有机EL器件可应用于薄膜显示器和液晶显示器的背照明及面光源领域。
目前实际应用的EL器件是分散型的EL器件,由于分散型EL器件需要几十伏或更高及10千赫或更高的交流电压,使得EL器件的驱动电路很复杂。
因此,能够以10伏或更低电压驱动且达到更高发光度的有机EL器件的研究非常活跃。例如已提出透明电极/空穴注入层/发光层/背面电极构成的多层结构的有机EL器件(《应用物理通信》51卷913-915页和日特开昭63(1988)264629)。在这些有机EL器件中,空穴穿过置于有机EL器件内的空穴注入层被有效注入到发光层。有机EL器件所用的发光层可以是单层,但是单层结构不能使电子传输性能和空穴传输性能达到很好的平衡,已通过采用多层层状结构的方法对有机EL器件的性能进行改进。
将多层结构成型所带来的问题是有机EL器件的制造工艺复杂,制造所需时间增加,且诸如必须将每层成型为足够薄的膜之类的限制条件增多。并且,近年来由于信息设备需要减小尺寸和更为轻便,因而要求更低的驱动电压。因此,已着手开发研究能有助于减小重量和降低驱动电压的发光材料和空穴传输材料。已知蒽可用作发光材料,但是蒽不太容易成型为均匀薄膜。因此就尝试在蒽中引入各种取代基。例如,已提出一些稠合多环芳烃用于有机EL器件的发光材料(日特开平4(1992)-178488,平6(1994)-228544,平6(1994)-228545,平6(1994)-228546,平6(1994)-228547,平6(1994)-228548,平6(1994)-228549,平8(1996)-311442,平8(1996)-12600,平8(1996)-12969,平10(1998)-72579。)
但是,采用上述材料的有机EL器件所存在的问题是发光效率和耐热性不够。
发明内容
基于上述情况出台了本发明,目的在于提供一种新的化合物,当此化合物用作有机EL器件构成材料时呈现出高发光效率及优异耐热性能,和使用此化合物的有机EL器件。
为达到上述目的,本发明人进行了深入研究,由此发现通过使用具有特殊结构的蒽衍生物可达到此目的。以此为根据得以完成本发明。
本发明概述如下。
[1]一种通式(I)所代表的蒽衍生物:式中X和Y各自独立代表一个6到30个碳原子的取代或未取代的三官能度芳环基团或是一个4到30个碳原子的取代或未取代的三官能度杂环基团;(1)A1到A4各自独立代表一个6到30个碳原子的取代或未取代的芳基或是一个4到30个碳原子的取代或未取代的单价杂环基,或者(2)A1代表氢原子,A2代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代,A3代表氢原子且A4代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代;R1到R16各自独立代表氢原子、卤原子、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的烷硫基、取代或未取代的芳硫基、取代或未取代的氨基或是取代或未取代的芳基;R1到R16所代表的相邻基团可通过彼此之间成键而成环;Q代表5到30个碳原子的取代或未取代的亚环烷基、6到30个碳原子的取代或未取代的亚芳基或是4到30个碳原子的取代或未取代的二价杂环基;p代表选自0、1和2的数。
[2]一种通式(II)所代表的蒽衍生物:式中(1)A1到A4各自独立代表一个6到30个碳原子的取代或未取代的芳基或是一个4到30个碳原子的取代或未取代的单价杂环基,或者(2)A1代表氢原子,A2代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代,A3代表氢原子且A4代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代;R1到R16各自独立代表氢原子、卤原子、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的烷硫基、取代或未取代的芳硫基、取代或未取代的氨基或是取代或未取代的芳基;R1到R16所代表的相邻基团可通过彼此之间成键而成环;Q代表5到30个碳原子的取代或未取代的亚环烷基、6到30个碳原子的取代或未取代的亚芳基或是4到30个碳原子的取代或未取代的二价杂环基;p代表选自0、1和2的数。
[3]一种通式(II’)所代表的蒽衍生物:式中(1)A1到A4各自独立代表一个6到30个碳原子的取代或未取代的芳基或是一个4到30个碳原子的取代或未取代的单价杂环基,或者(2)A1代表氢原子,A2代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代,A3代表氢原子且A4代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代;R1到R16各自独立代表氢原子、卤原子、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的烷硫基、取代或未取代的芳硫基、取代或未取代的氨基或是取代或未取代的芳基;R1到R16所代表的相邻基团可通过彼此之间成键而成环;Q代表5到30个碳原子的取代或未取代的亚环烷基、6到30个碳原子的取代或未取代的亚芳基或是4到30个碳原子的取代或未取代的二价杂环基;p代表选自0、1和2的数。
[4]一种通式(III)所代表的蒽衍生物:式中X和Y各自独立代表一个6到30个碳原子的取代或未取代的三官能度芳环基团或是一个4到30个碳原子的取代或未取代的三官能度杂环基团;R1到R20各自独立代表氢原子、卤原子、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的烷硫基、取代或未取代的芳硫基、取代或未取代的氨基或是取代或未取代的芳基;R1到R20所代表的相邻基团可通过彼此之间成键而成环;Q代表5到30个碳原子的取代或未取代的亚环烷基、6到30个碳原子的取代或未取代的亚芳基或是4到30个碳原子的取代或未取代的二价杂环基;p代表选自0、1和2的数。
[5]一种有机电致发光器件,包括含[1]到[4]所述的任一项的蒽衍生物的发光区。
[6]一种有机电致发光器件,包括含[1]到[4]任一种项所述的衍生物的有机发光层。
[7]一种[5]和[6]任一项所述的有机电致发光器件,其中有机发光层进一步包括能形成复合场所的物质。
[8]一种[7]所述的有机电致发光器件,其中能形成复合场所的物质是一种荧光量子产率为0.3到1.0的荧光性物质。
[9]一种[7]和[8]任一项所述的有机电致发光器件,其中能形成复合场所的物质是至少一种选自苯乙烯基胺化合物、喹吖酮衍生物、红荧烯衍生物、香豆素衍生物、苝衍生物、吡喃衍生物和荧蒽衍生物的化合物。
[10]一种[5]到[9]任一项所述的有机电致发光器件,其中在有机发光层与阴极或阳极之间形成一硫族化合物层、金属卤化物层或金属氧化物层。
实施本发明的最优选方案
通式(I)中,X和Y各自独立代表一个6到30个碳原子的取代或未取代的三价芳环基团或是一个4到30个碳原子的取代或未取代的三价杂环基团。
6到30个碳原子的三价芳环基团的实例包括通过将诸如苯、萘、联苯、联三苯、三亚苯、、并四苯、苉、苝、并五苯、蔻、玉红省、蒽、苯并[a]蒽、苯并[a]芘、联四苯和联二蒽的芳族化合物消去三个氢原子得到的三价基团。4到30个碳原子的三价杂环基团的实例包括通过将诸如呋喃、噻吩、吡咯、2-羟基吡咯、苯并呋喃、异苯并呋喃、1-苯并噻吩、2-苯并噻吩、吲哚、异吲哚、二氢吲哚、咔唑、2-羟基吡喃、2-羟基苯并呋喃、1-羟基-2-苯并吡喃、氧杂蒽、4-羟基噻喃、吡啶、喹啉、异喹啉、4-羟基四氢喹啉、菲啶、吖啶、噁唑、异噁唑、噻唑、异噻唑、呋咱、咪唑、吡唑、苯并咪唑、1-羟基咪唑、1,8-二氮萘、吡啶、嘧啶、哒嗪、喹喔啉、喹唑啉、2,3-二氮杂萘(phthaladine)、嘌呤、萘嵌间二氮杂苯、1,10-菲咯啉、噻蒽、吩噻噁、,吩噁嗪、,吩噻嗪、吩嗪、硅杂环戊二烯、硅杂苯和二苯并(b,f)吖庚因的杂环化合物消去三个氢原子得到的三价基团。
上面的通式(I)中,(1)A1到A4各自独立代表一个6到30个碳原子的取代或未取代的芳基或是一个4到30个碳原子的取代或未取代的单价杂环基,6到30个碳原子的芳基的实例包括苯基、萘基、联苯基、蒽基、联三苯基和苯乙烯基。4到30个碳原子的单价杂环基的实例包括与X和Y所代表基团实例中所述的三价杂环基相对应的单价杂环基。
上面的通式(I)中,(2)A1和A3各自代表氢原子且A2和A4各自代表一个苯乙烯基,其中苯乙烯基的苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代。当有多个取代基时,取代基可通过彼此之间成键而形成一个环结构。苯乙烯基的实例可以是苯基亚乙烯基、三亚苯基亚乙烯基、萘基亚乙烯基、联苯基亚乙烯基、联三苯基亚乙烯基和蒽基亚乙烯基。
上面的通式(I)中,R1到R16各自独立代表氢原子、卤原子、氰基、硝基、1到6个碳原子的取代或未取代的烷基、1到6个碳原子的取代或未取代的烷氧基、5到18个碳原子的取代或未取代的芳氧基、7到18个碳原子的取代或未取代的芳烷氧基、1到20个碳原子的取代或未取代的烷硫基、6到18个碳原子的取代或未取代的芳硫基、取代或未取代的氨基、1到6个碳原子的取代或未取代的酯基或是5到16个碳原子的取代或未取代的芳基。
1到6个碳原子的烷基的实例包括甲基、乙基、丙基、异丙基、丁基、异丁基、仲丁基、叔丁基、各种构型的戊基和各种构型的己基。1到6个碳原子的烷氧基的实例包括甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、各种构型的戊氧基和各种构型的己氧基。5到18个碳原子的芳氧基的实例包括苯氧基、甲苯氧基和萘氧基。7到18个碳原子的芳烷氧基的实例包括苄氧基、苯乙氧基和萘甲氧基。1到20个碳原子的烷硫基和6到18个碳原子的芳硫基的实例包括甲硫基、乙硫基、苯硫基和甲苯硫基。5到16个碳原子的芳基取代的氨基的实例包括二苯氨基、二萘氨基和萘苯氨基。1到6个碳原子的酯基的实例包括甲氧羰基、乙氧羰基、丙氧羰基和异丙氧羰基。卤原子的实例包括氟原子、氯原子和溴原子。R1到R16所代表的相邻基团可通过彼此之间成键而成环。
上面的通式(I)中,Q代表5到30个碳原子的取代或未取代的亚环烷基、6到30个碳原子的取代或未取代的亚芳基或是4到30个碳原子的取代或未取代的二价杂环基。5到30个碳原子的亚环烷基的实例包括亚环戊基、亚环己基和亚环庚基。6到30个碳原子的亚芳基的实例包括亚苯基、亚萘基、亚联苯基、亚蒽基和亚联三苯基。4到30个碳原子的二价杂环基的实例包括与X和Y所代表基团实例中所述的三价杂环基相对应的二价杂环基。
上面的通式(I)中,p代表选自0、1和2的数,当p代表0时,两边的基团通过单键键连。
通式(I)到(III)所代表化合物中的每一基团有取代基时,取代基的实例包括R1到R16所代表基团的实例中述及的基团。与R1到R16所代表的基团类似,相邻取代基可通过彼此之间成键而成环。
通式(I)所代表的蒽衍生物是选自具有上述结构化合物的一种化合物。上述化合物中,优选玻璃化转变温度为100℃或更高温度的化合物,更优选玻璃化转变温度为120℃或更高温度的化合物。
通式(I)所代表的蒽衍生物的优选方案进一步包括下面通式(III)所代表的蒽衍生物:上面的通式(III)中,X、Y、Q和p的定义同通式(I),R1到R20所代表的原子或基团与R1到R16所代表的原子或基团相同。
R1到R20所代表的相邻基团可通过彼此之间成键而成环。R1到R16所代表的相邻基团通常是通过彼此之间成键而成环。
对通式(I)所代表的蒽衍生物的制备方法不做特殊限定,可采用各种方法。例如可按下述方法有效制备所预期的蒽衍生物。
下面说明通式(I)中A1=A3、A2=A4和X=Y时所代表的化合物的制备方法。将通式(1-a)所代表的卤素化合物:式中A1、A2和X的定义同上且Z代表卤原子,与烷基锂试剂反应而转化为锂化合物。得到的锂化合物与通式(1-b)所代表的联二蒽酮化合物反应:式中R1到R16的定义同上,得到通式(1-c)所代表的双酚衍生物:式中A1、A2和R1到R16的定义同上。按常规方法由双酚衍生物形成芳环可得到通式(I)所代表的蒽衍生物。
本发明的有机EL器件是一种在一对电极间至少放置一层有机发光层的器件。有机EL器件的构造例如包括下列构造:
(1)阳极/发光层/阴极;
(2)阳极/空穴注入层/发光层/阴极;
(3)阳极/发光层/电子注入层/阴极;
(4)阳极/空穴注入层/发光层/电子注入层/阴极;
(5)阳极/有机半导体层/发光层/阴极;
(6)阳极/有机半导体层/阻电子层/发光层/阴极
(7)阳极/有机半导体层/发光层/增粘层/阴极
(8)阳极/空穴注入层/空穴传输层/发光层/电子注入层/阴极
但是,有机EL器件的构造不限于上述实例。
上述构造中,优选采用构造(8)。优选通式(I)、(II)、(II’)和(III)所代表的蒽衍生物包含在上述构造的发光区如发光层、空穴传输层、电子注入层或空穴注入层(非电极层)内。更优选蒽衍生物包含在发光层内。
一般来说,是在能透光的基材上制造有机EL器件。透光基材是支承有机EL器件的基底。优选透光基材在400到700nm可见光范围内的透光率为50%或更高,还优选使用平滑的基材。
最好使用玻璃板或合成树脂板作为基材。玻璃板的实例包括由钠玻璃、含钡和锶的玻璃、铅玻璃、铝硅酸盐玻璃、硼硅酸盐玻璃、硼硅酸钡玻璃和水晶制成的板。合成树脂板的实例包括由聚碳酸酯树脂、丙烯酸树脂、聚对苯二甲酸乙二醇酯、聚醚硫醚树脂和聚砜树脂制成的板。
优选采用具有大功函(4eV或更高)的材料如金属、合金、导电化合物及这些材料混合物所制成电极作为阳极。阳极材料的实例包括金属如金和导电化合物如CuIn、ITO(铟锡氧化物)、SnO2、ZnO和In-Zn-O。可按照诸如蒸发沉积法和喷涂法的方法将上述阳极材料成型为薄膜来制成阳极。当从发光介质层所发射的光是穿过阳极获得时,优选阳极对所发射光的透光率大于10%。还优选阳极的薄片电阻率为几百Ω/□或更小。阳极的厚度一般选定在10nm到1μm范围,根据所用材料的不同,优选范围可能会有所不同,但优选在10到200nm范围。
优选采用具有小功函(4eV或更低)的材料如金属、合金、导电化合物及这些材料混合物所制成电极作为阴极。阴极材料的实例包括钠、钠-钾合金、镁、锂、镁-银混合物、铝/氧化铝、Al/LiO2、Al/LiF、铝-锂合金、铟和稀土金属。
可按照诸如蒸发沉积法和喷涂法的方法将上述材料成型为薄膜来制成阴极。
当从发光介质层所发射的光是穿过阴极获得时,优选阴极对所发射光的透光率大于10%。还优选阴极的薄片电阻率为几百Ω/□或更小。阴极的厚度一般选定在10nm到1μm范围,优选在50到200nm范围。
本发明的有机EL器件中,优选上述方法制成的一对电极中的至少一个电极的表面上有一层硫族化物、金属卤化物或金属氧化物。具体地说,优选在阳极位于发光介质层一侧的表面有一金属如硅或铝的硫族化物(包括氧化物)层,在阴极位于发光介质层一侧的表面有一金属卤化物或金属氧化物层。由于有一层上述材料,就能改进驱动稳定性。
硫族化物的优选实例包括SiOx(1≤x≤2)、AlOx(1≤x≤1.52)、SiON和SiAlON。金属卤化物的优选实例包括CsF、LiF、MgF2、CaF2和稀土金属的氟化物。金属氧化物的优选实例包括CsO2、Li2O、MgO、SrO、BaO和CaO。
优选采用具有如下综合功能的材料层作为本发明有机EL器件的发光层:
(1)注入功能:施加电场时,从阳极或空穴注入层注入空穴或者从阴极或电子注入层注入电子的功能。
(2)传输功能:电场力作用下传输所注入的电荷载流子(电子和空穴)的功能。
(3)发光功能:提供电子和空穴复合的场所并通过复合发光。
空穴注入与电子注入的难易程度可能不同。用空穴迁移率表示的空穴传输能力与用电子迁移率表示的电子传输能力可以不同。优选空穴或电子之一被传输。上述通式(I)、(II)、(II’)和(III)任一式所代表的蒽衍生物满足上面的三个条件,可用该蒽衍生物作为主要组分形成发光层。
可采用能形成复合场所的物质作为构成有机EL器件发光层的材料之一。能形成复合场所的物质是肯定能为从两边电极注入的电子和空穴进行复合提供场所的物质,或是能提供虽不发生电子与空穴复合但能传输复合能量并发光的场所的物质。因此,与单独使用蒽衍生物相比,当联用能形成复合场所的物质时,电子和空穴将在发光层中心周围以更浓的比例被复合,可提高发光的亮度。
从上述现象的立场看,优选具有高荧光量子产率的物质用作本发明有机EL器件发光层中能形成复合场所的物质。特别是更优选荧光量子产率为0.3到1.0的物质。用作能形成复合场所的物质选自苯乙烯胺化合物、喹吖二酮衍生物、红荧烯衍生物、香豆素衍生物、苝衍生物、吡喃衍生物和荧蒽衍生物的化合物及选自这些化合物的混合化合物。能形成复合场所的物质的更多实例包括共轭大分子化合物如聚(亚芳基亚乙烯基)衍生物和1到50个碳原子的烷基和烷氧基取代的聚亚芳基和亚乙烯基衍生物。
优选根据发光层所发射光的颜色来选择能形成复合场所的物质。例如,当希望发蓝光时,优选采用苝、苯乙烯胺衍生物或氨基取代的二苯乙烯基亚芳基衍生物。当希望发绿光时,优选采用喹吖二酮衍生物或香豆素衍生物。当希望发黄光时,优选采用红荧烯衍生物。当希望发橙色或橘红色光时,优选采用二氰基甲基吡喃衍生物。
本发明中,优选将本发明通式(I)、(II)、(II’)和(III)任一式所代表的蒽衍生物用作能形成复合场所的物质。
本发明的有机EL器件中,根据发光层的发光亮度和发光颜色来决定器件中能形成复合场所的物质的用量。优选用量范围为0.1到20份(质量)/100份(质量)上述有机化合物。能形成复合场所的物质的用量少于0.1份(质量)时,发光亮度就会降低。用量超过20份(质量)时,耐热性会下降。因此,为维持有机EL器件发光亮度和耐热性之间有很好平衡,优选用量在0.5到20份(质量)/100份上述有机化合物,更优选为1.0到10份(质量)/100份上述有机化合物。
除了用上述化合物外,根据所希望的色调,还可使用下示化合物作为构成有机EL器件有机发光层的材料。例如为获得紫外区到紫色区的发射光,优选使用下面通式(IV)所代表的化合物:式中X代表下面通式所表示的二价基团a代表2到5的整数,Y代表下式所示的芳基:或
通式(IV)所代表的化合物中,苯基、亚苯基、和萘基可以有一或多个选自1到4个碳原子的烷基、1到4个碳原子的烷氧基、羟基、磺酰基、羰基、氨基、二甲氨基和二苯氨基的取代基。当有多个这些基团时,基团间可以彼此键联,形成一个饱和的五元或六元环基团。在此化合物中,优选在苯基、亚苯基和萘基的对位成键,因为这样的键合为刚性且当通过蒸发沉积法形成光滑薄膜时不会发生化学分解反应。通式(IV)所代表的化合物的具体实例包括下式所示化合物。
上面示出的化合物中,优选对联四苯和对联五苯。
例如,为达到发射蓝到绿光的目的,可使用苯并噻唑、苯并咪唑或苯并噁唑荧光增白剂,喔星型(oxinoid)化合物的金属螯合物或苯乙烯基苯化合物。上述化合物的实例包括日特开昭59(1984)-194393中所公开的化合物。适合用作上述化合物的化合物的更多实例包括《Chemistry of Synthetic Dies》(1971)628到637页和640页中所列出的化合物。
可使用日特开昭63(1988)-295695中所公开的化合物作为喔星型化合物的金属螯合物。上述化合物的典型实例包括8-羟基喹啉的金属配合物如三(8-羟基喹啉)铝和epintridione二锂。
例如可使用欧洲专利0319881和0373582中所公开的化合物作为苯乙烯基苯化合物。也可使用日特开平2(1990)-252793中所公开的二苯乙烯基吡嗪衍生物作为发光层的材料。也可使用欧洲专利0387715中所公开的多苯基化合物作为发光层的材料。
可使用除荧光增白剂、喔星型化合物的金属螯合物或苯乙烯基苯化合物外的其它化合物作为发光层的材料。这类化合物的实例包括下列化合物:12-羟基酞吡呤(J.Appl.Phys.,27卷,L713(1988));1,4-二苯基-1,3-丁二烯和1,1,4,4-四苯基-1,3-丁二烯(Appl.Phys.Lett.,56卷,L799(1990));萘胺衍生物(日特开平2(1990)-305886);苝衍生物(日特开平2(1990)-189890);噁二唑衍生物((日特开平2(1990)-216791和HAMADA等人在第38届应用物理大会的论文);醛连氮衍生物(日特开平2(1990)-220393);吡嗪衍生物(日特开平2(1990)-220394);环戊二烯衍生物(日特开平2(1990)-289675);吡咯并吡咯衍生物(日特开平2(1990)-296891);苯乙烯胺衍生物(Appl.Phys.Lett.,56卷,L799(1990));香豆素化合物(日特开平2(1990)-191694);和国际专利申请WO90/13148和Appl.Phys.Lett.第158卷18期1982页(1991)中所述的大分子化合物。
本发明中,特别优选使用欧洲专利0388768和日特开平3(1991)-231970中所公开的芳族二次甲基化合物作为发光层的材料。上述化合物的实例包括4,4’-双(2,2-二叔丁基苯基乙烯基)联苯、4,4’-双(2,2-二苯基乙烯基)联苯及这些化合物的衍生物。
用作发光层材料的化合物的更多实例包括日特开平5(1993)-258862述及的通式(Rs-Q)2-Al-O-L所代表的化合物。通式中,L代表6到24个碳原子(包括苯基部分)的烃基,O-L代表酚根配体;Q代表8-羟基喹啉根配体且Rs代表连接在8-羟基喹啉环上的选用来防止有多于2个8-羟基喹啉根与铝原子配位的取代基。上述化合物具体实例包括二(2-甲基-8-羟基喹啉根)(对苯基苯酚根)合铝(III)和二(2-甲基-8-羟基喹啉根)(1-萘酚根)合铝(III)。
按照日特开平6(1994)-9953所公开的掺杂方法可达到高效率混合发射蓝光和绿光的目的。此方法中,上述发光材料可用作主体,深蓝到绿色的荧光染料如香豆素荧光染料可用作掺杂剂,且该荧光染料也可用作主体。具体地说,具有二苯乙烯基亚芳基骨架结构的发光材料且优选4,4’-双(2,2-二苯基乙烯基)联苯用作主体,苝衍生物且例如优选二苯乙烯基亚芳基衍生物用作掺杂剂。
对用于发射白光的发光层不做特殊限定。可使用下列发光层:
(1)指定有机EL器件中每层的能量水平且利用隧道穿透注入机制发
光的发光层(欧洲专利0390551)。
(2)在一种与器件(1)类似的利用隧道穿透注入机制的器件实施例中所述的发射白光的发光器件(日特开平3(1991)-230584)。
(3)两层结构的发光层(日特开平2(1990)-220390和平2(1990)-216790)。
(4)分成多层的发光层,每层由不同发光波长的材料组成(日特开平4(1992)-51491)
(5)发光层中,发射蓝光的发光材料(荧光峰值波长:380-480)和发射绿光的发光材料(荧光峰值波长:480-580)层叠放置且进一步包含发射红光的荧光材料(日特开平6(1994)-207170)
(6)发光层中,发射蓝光的发光层含发射蓝光的荧光染料,发射绿光的发光层有一个含发射红光的荧光染料的区域且进一步包含发射绿光的荧光材料(日特开平7(1995)-142169)。
这些发光层中,优选采用具有结构(5)的发光层。
优选采用下示化合物作为发射红光的荧光材料。
用上述材料来形成发光层的方法可采用常规方法如蒸发沉积法、旋涂法和Langmuir-Blodgrtt方法(LB法)。特别优选发光层是分子沉积膜。分子沉积膜是一种通过将原料化合物进行气相沉积的方法形成的膜或是一种通过将溶液中或液态的原料化合物固化形成的膜。分子沉积膜有别于LB法形成的膜(分子堆积膜),聚集结构有所不同,是更为有序的结构,由于结构的差异而功能有所不同。
按日特开昭57(1982)-51781中所公开内容,也可通过将粘结材料如树脂与原料化合物溶于溶剂制成溶液,然后按旋涂方法形成薄膜制成发光层。
对上述方法所制的发光层的厚度不做特殊限定,可根据具体情况合理选定。优选厚度在5nm到5μm范围。发光层可由包括选自上述材料的一或多种材料的单层构成,或者可以是上述发光层与所包括的化合物不同于上述发光层所含化合物的发光层构成的多层结构。
空穴注入和传输层是促进空穴注入到发光层和将空穴传输至发光区的材料层。此层具有较大的空穴迁移率,且电离能一般低至5.5eV或更低。优选能在较小的电场强度下传输空穴至发光层的材料。例如优选当施加104到106V/cm的电场强度时,空穴迁移率至少为10-6cm2/V.秒。对与本发明的二苯乙烯基亚芳基衍生物混合并形成空穴注入和传输层的材料不做特殊限定,只要材料具有上述所期望的性能即可。此材料适宜从光导材料中的空穴传输材料常用材料和EL器件空穴注入层常用材料中选用。
形成空穴注入和传输层的材料的实例如下:三唑衍生物(美国专利3112197);噁二唑衍生物(美国专利3189447);咪唑衍生物(日特开昭37(1962)-16096);多芳基烷烃衍生物(美国专利3615402、3820989和3542544,日特开昭45(1970)-555和昭51(1976)-10983,日特开昭51(1976)-93244、昭55(1980)-17105、昭56(1981)-4148、昭55(1980)-108667、昭55(1980-156953)和昭56(1981)-36656);吡唑啉衍生物和吡唑酮衍生物((美国专利3180729和4278746,日特开昭55(1980)-88064、昭55(1980)-88065、昭49(1974)-105573、昭55(1980)-51086、昭56(1981)-80051、昭56(1981)-88141、昭57(1982)-45545、昭54(1979)-112637和昭55(1980)-74546);苯二胺衍生物(美国专利3615404,日特开昭51(1976)-10105、昭46(1971)-3712、和昭47(1972)-25336,日特开昭54(1979)-53435、昭54(1979)-110536和昭54(1979)-119925);芳胺衍生物(美国专利3567450、3180703、3240597、3658520、4232103、4175961和4012376,日特开昭49(1974)-35702和昭(39(1964)-27577,日特开昭55(1980)-144250、昭56(1981)-119132和昭56(1981)-22437,西德专利1110518);胺取代的查耳酮衍生物(美国专利3526501);噁唑衍生物(美国专利3527203);苯乙烯基蒽衍生物(日特开昭56(1981)46234);芴酮衍生物(日特开昭54(1979)-110837);腙衍生物(美国专利3717462,日特开昭54(1979)59143、昭55(1980)-52063、昭55(1980)-52064、昭55(1980)-46760、昭55(1980)-85495、昭57(1982)-11350、昭57(1982)-148749和平2(1990)311591);芪衍生物(日特开昭61(1986)-210363、日特开昭61(1986)-228451、日特开昭61(1986)-14642、昭61(1986)-72255、昭62(1987)-47646、昭62(1987)-36674、昭62(1987)-10652、昭62(1987)-30255、昭60(1985)-93455、昭60(1985)-94462、昭60(1985)-174749和昭60(1985)-175052);硅氮烷衍生物(美国专利4950950);聚硅烷化合物(日特开昭平2(1990)-204996);苯胺共聚物(日特开平2(1990)282263);和导电大分子齐聚物,特别是噻吩齐聚物(日特开平(1989)211399)。
上述材料可用作空穴注入层材料。下列材料也可用作空穴注入层:卟啉化合物(日特开昭63(1988)-295695);芳族叔胺化合物和苯乙烯基胺化合物(美国专利4127412和日特开昭53(1978)-27033、昭54(1979)-58445、昭54(1979)-149634、昭54(1979)-64299、昭55(1980)-79450、昭55(1980)-144250、昭56(1981)-119132、昭61(1986)295558、昭61(1986)-98353和昭63(1988)-295695)。
更多的实例包括美国专利5061569中所公开的分子中有两个集合芳环的化合物,如4,4’-双(N-(1-萘基)-N-苯基氨基)联苯,和日特开平4(1992)-308688中所公开的带有以星状键连的三个三苯胺单元的化合物,如4,4’,4″-三(N-(3-甲基苯基)-N-苯基氨基)三苯胺。还可使用上述作为发光层材料的芳族二次甲基化合物和无机化合物如P型硅和P型SiC作为空穴注入层。
为形成空穴注入和传输层,可按照常规方法如真空蒸发沉积法、旋涂法、浇铸法和LB法将上述化合物制成薄膜。对空穴注入和传输层的厚度不做特殊限定,厚度一般为5nm到5μm。当本发明化合物包含在空穴传输区时,空穴注入和传输层可由包括选自上述材料的一或多种材料的单层构成,或者可以是上述空穴注入和传输层与所包括的化合物不同于上述空穴注入和传输层所含化合物的空穴注入和传输层构成的多层结构。
有机半导体层是一种促进空穴或电子注入到发光层的材料层。优选此层具有10-10S/cm或更高的电导率。可使用日特开平8(1996)-193191所公开的诸如含噻吩齐聚物、含芳胺齐聚物的导电型齐聚物和导电型接枝共聚物如含芳胺的接枝共聚物作为有机半导体层的材料。
电子注入层是促进电子注入到发光层且具有较大的电子迁移率的材料层。增粘层是由与阴极能很好粘结的材料制成的电子注入层。优选使用8-羟基喹啉及其衍生物的金属配合物作为电子注入层。可用作电子注入层的8-羟基喹啉及其衍生物的金属配合物的实例包括喔星型化合物的金属螯合物,包括喔星(一般是指8-喹啉醇或称8-羟基喹啉)的螯合物在内,如三(8-羟基喹啉)铝。
噁二唑衍生物的实例包括下面通式(V)到(VII)所代表的电子转移化合物:式中Ar1、Ar2、Ar3、Ar5、Ar6和Ar9各自代表一个可带有取代基的芳基,Ar1和Ar2、Ar3和Ar5及Ar6和Ar9可代表相同或相异的基团,Ar4、Ar7和Ar8各自代表一个可带有取代基的亚芳基,Ar7和Ar8可代表相同或相异的基团。
上面通式(V)到(VII)中的芳基的实例包括苯基、联苯基、蒽基、苝基和芘基。亚芳基的实例包括亚苯基、亚萘基、亚联苯基、亚蒽基、亚苝基和亚芘基。上述基团的取代基的实例包括1到10个碳原子的烷基、1到10个碳原子的烷氧基和氰基。具有优异薄层成型性的化合物可用作电子转移化合物。
电子转移化合物的实例包括下式所示的化合物,式中,Me代表甲基且t-Bu代表叔丁基。
作为本发明有机EL器件的制造方法,可以按上述方法,用上述材料先形成阳极、发光层和(必要的话)空穴注入层及电子注入层,然后再形成阴极的方法来制造有机EL器件。也可以相反的次序来制造有机EL器件,例如先制成阴极,最后制成阳极。
作为一个具体实施方案,下面将说明按此次序,在透光基材上形成阳极、空穴注入层、发光层、电子注入层和阴极构造的有机EL器件的制造方法。
首先形成阳极。按照诸如蒸发沉积法或喷涂法的方法在透光基材上形成阳极材料薄膜,所形成的薄膜厚度为1μm以下,优选10到200nm范围内。然后在阳极上形成空穴注入层。如上所述,可按照诸如真空蒸发沉积法、旋涂法、浇铸法和LB法的方法形成空穴注入层。优选采用真空蒸发沉积法,因该方法能得到均匀薄膜且可防止形成针孔。按照真空蒸发沉积法形成空穴注入层时,根据所用的化合物(空穴注入层材料)及要形成的空穴注入层的结晶结构和复合结构情况,真空蒸发沉积法所用的条件有所不同。一般来说,优选蒸发沉积源的温度选定在50到450℃范围,真空度选定在10-7到10-3托范围,蒸发沉积速度选定在0.01到50nm/秒范围,基板温度选定在-50到300℃范围,膜厚选定在5nm到5μm。
在空穴注入层上形成发光层。采用所期望的有机发光材料,按照诸如真空蒸发沉积法、喷涂法、旋涂法和浇铸法的方法形成有机发光材料薄膜。优选采用真空蒸发沉积法,因该方法能得到均匀薄膜且可防止形成针孔。按照真空蒸发沉积法形成发光层时,根据所用的化合物,真空蒸发沉积法所用的条件有所不同。一般来说,可以选用与上述形成空穴注入层时所用条件相同范围的条件。
在上文所形成的发光层上形成电子注入层。与形成空穴注入层和发光层的方法类似,优选采用真空蒸发沉积法,因为必须要形成均匀薄膜。真空蒸发沉积法所用条件选用与上述形成空穴注入层和发光层时所用条件相同范围的条件。
本发明蒽衍生物的添加方法将根据蒽衍生物所在的材料层而有所不同。当采用真空沉积法时,蒽衍生物可与其它材料同时进行真空蒸发沉积。当采用旋涂法时,蒽衍生物可以与其它材料的混合物形式使用。
最后一步是形成阴极薄层,得到有机EL器件。阴极由金属构成,可采用真空蒸发沉积法或喷涂法成型。优选真空蒸发沉积法,这样在阴极成型过程中就可避免对前几步形成的有机层造成损害。
优选将制造有机EL器件的设备减压同时维持减压条件下的压力之后再进行制造有机EL器件所经过的从阳极成型到阴极成型的步骤。
使用有机EL器件时,当阳极连接正电极(+)和阴极连接负电极(-),且施加3到40V电压时可观察到发光现象。当阳极连接负电极(-)和阴极连接正电极(+)时则完全观察不到发光现象。当施加交流电压时,仅当阳极连接正电极(+)和阴极连接负电极(-)可观察到均匀发光现象。不限制所施加的交流电的波形。
参照下面的实施例,将更具体地说明本发明。但是本发明不受这些实施例的限定。实施例1(合成化合物E1)
氩气氛下,将9.3g(30mmol)3,5-二苯基溴苯溶于由50ml无水甲苯和50ml无水四氢呋喃(THF)制成的混合溶剂中,得到的溶液在干冰冷却的-20℃甲醇浴中进行冷却。向冷溶液中加入正丁基锂(1.5M己烷溶液,21ml,32mmol),得到的混合物于-20℃下搅拌1小时。然后加入3.8g(10mmol)联二蒽酮,得到的混合物先在-20℃下搅拌1小时,再在室温下搅拌6小时,然后静置过夜。将反应混合物用50ml饱和氯化铵水溶液冷却。将形成的固体物质过滤分离,并用水、甲醇和丙酮洗涤,得到7.3g(收率:87%)白色固体状双酚化合物。
氩气氛下,将上面得到的7.3g(8.6mmol)双酚化合物悬浮于100ml乙酸中。向得到的悬浮液中加入57%氢碘酸(11ml,83mmol,10当量),得到的混合物于80℃下搅拌8小时。加入50ml的50%磷酸来冷却反应产物。将形成的固体物质过滤分离,并用水、甲醇和丙酮洗涤,得到5.9g(收率;84%)白色固体。按照元素分析法和电场退吸质谱测定法(FD-MS)对所得产物进行测定,结果如下:
元素分析(%):C:94.52;H:5.38(按C64H42计算的理论值:C:94.78;H:5.22)
FD-MS:m/z=810(M+,100)(按C64H42计算的分子量=810)实施例2(合成化合物E7)
氩气氛下,将20g(64mmol)1,3,5-三溴苯和3.6g(5.1mmol,4%Pd)二氯二(三苯基膦)合钯溶于500ml无水THF中。向得到的溶液中滴加由27g(0.13mol)3-溴喹啉与3.7g(0.16mol)镁制成的格氏试剂,得到的混合物回流条件下加热4小时。将反应产物加水冷却。分离出有机层,用饱和氯化钠水溶液洗涤,然后用无水硫酸镁干燥。蒸馏出溶剂后,用柱色谱法(硅胶/己烷+10%二氯甲烷)提纯产物,得到8.4g(收率:32%)白色固体。
氩气氛下,将上面得到的8.4g(20mmol)白色固体溶于由50ml无水甲苯和50ml无水THF制成的混合溶剂中,得到的溶液在干冰冷却的-20℃甲醇浴中进行冷却。向冷溶液中加入正丁基锂(1.5M己烷溶液,15ml,22mmol),得到的混合物于-20℃下搅拌1小时。然后加入2.6g(6.8mmol)联二蒽酮,得到的混合物先在-20℃下搅拌1小时,再在室温下搅拌6小时,然后静置过夜。将反应混合物用50ml饱和氯化铵水溶液冷却。将形成的固体物质过滤分离,并用水、甲醇和丙酮洗涤,得到4.8g(收率:67%)白色固体状双酚化合物。然后将上面得到的4.8g(4.6mmol)双酚化合物悬浮于50ml乙酸中。向得到的悬浮液中加入57%氢碘酸(6ml,46mmol,10当量),得到的混合物于80℃下搅拌8小时。加入30ml的50%次磷酸来冷却反应产物。将形成的固体物质过滤分离,并用水、甲醇和丙酮洗涤,得到3.8g(收率;81%)白色固体。按照元素分析法和电场退吸质谱测定法(FD-MS)对所得产物进行测定,结果如下:
元素分析(%):C:89.02;H:4.22;N:5.38(按C76H48N4计算的理论值:C:89.91;H:4.57;N:5.52)
FD-MS:m/z=1016(M+,100)(按C76H48N4计算的分子量=1016)实施例3(合成化合物E14)
氩气氛下,将15g(38mmol)N-(3,5-二溴苯基)咔唑和1.1g(1.5mmol,4%Pd)二氯二(三苯基膦)合钯溶于500ml无水THF中。向得到的溶液中滴加由6.0g(38mmol)溴苯与1.1g(46mmol)镁制成的格氏试剂,得到的混合物回流条件下加热4小时。将反应产物加100ml水冷却。分离出有机层,用饱和氯化钠水溶液洗涤,然后用无水硫酸镁干燥。蒸馏出溶剂后,用柱色谱法(硅胶/己烷+10%二氯甲烷)提纯产物,得到8.0g(收率:53%)白色固体。
氩气氛下,将上面得到的8.0g(20mmol)白色固体溶于由50ml无水甲苯和50ml无水THF制成的混合溶剂中,得到的溶液在干冰冷却的-20℃甲醇浴中进行冷却。向冷溶液中加入正丁基锂(1.5M己烷溶液,15ml,22mmol),得到的混合物于-20℃下搅拌1小时。然后加入2.6g(6.8mmol)联二蒽酮,得到的混合物先在-20℃下搅拌1小时,再在室温下搅拌6小时,然后静置过夜。将得到的产物用50ml饱和氯化铵水溶液冷却。将形成的固体物质过滤分离,并用水、甲醇和丙酮洗涤,得到4.9g(收率:71%)白色固体状双酚化合物。然后将上面得到的4.9g(4.8mmol)双酚化合物悬浮于50ml乙酸中。向得到的悬浮液中加入57%氢碘酸(6ml,48mmol,10当量),得到的混合物于80℃下搅拌8小时。加入30ml的50%次磷酸来冷却反应产物。将形成的固体物质过滤分离,并用水、甲醇和丙酮洗涤,得到4.4g(收率;92%)白色固体。按照元素分析法和电场退吸质谱测定法(FD-MS)对所得产物进行测定,结果如下:
元素分析(%):C:91.98;H:4.52;N:2.64(按C76H48N2计算的理论值:C:92.28;H:4.89;N:2.83)FD-MS:m/z=988(M+,100)(按C76H48N2计算的分子量=988)实施例4(合成化合物E31)
氩气氛下,将20g(64mmol)1,3,5-三溴苯和3.6g(5.1mmol,4%Pd)二氯二(三苯基膦)合钯溶于500ml无水THF中。向得到的溶液中滴加由23g(0.13mmol)2-溴-5-甲基噻吩与3.7g(0.16mol)镁制成的格氏试剂,得到的混合物回流条件下加热4小时。将反应产物加100ml水冷却。分离出有机层,用饱和氯化钠水溶液洗涤,然后用无水硫酸镁干燥。蒸馏出溶剂后,用柱色谱法(硅胶/己烷+10%二氯甲烷)提纯产物,得到7.8g(收率:35%)白色固体。
氩气氛下,将上面得到的7.8g(22mmol)白色固体溶于由50ml无水甲苯和50ml无水THF制成的混合溶剂中,得到的溶液在干冰冷却的-20℃甲醇浴中进行冷却。向冷溶液中加入正丁基锂(1.5M己烷溶液,16ml,24mmol),得到的混合物于-20℃下搅拌1小时。然后加入2.8g(7.3mmol)联二蒽酮,得到的混合物先在-20℃下搅拌1小时,再在室温下搅拌6小时,然后静置过夜。将得到的反应产物用50ml饱和氯化铵水溶液冷却。将形成的固体物质过滤分离,并用水、甲醇和丙酮洗涤,得到5.1g(收率:76%)白色固体状双酚化合物。然后将上面得到的5.1g(5.5mmol)双酚化合物悬浮于50ml乙酸中。向得到的悬浮液中加入57%氢碘酸(6ml,48mmol,10当量),得到的混合物于80℃下搅拌8小时。加入30ml的50%次磷酸来冷却反应产物。将形成的固体物质过滤分离,并用水、甲醇和丙酮洗涤,得到3.8g(收率;81%)白色固体。按照元素分析法和电场退吸质谱测定法(FD-MS)对所得产物进行测定,结果如下:
元素分析(%):C:80.53;H:4.49(按C60H42N2S4计算的理论值:C:80.86;H:4.75)
FD-MS:m/z=890(M+,100)(按C60H42N2S4计算的分子量=890)实施例5(制造有机EL器件)
将具有铟锡氧化物透明电极的玻璃基片(GEOMATEC公司生产)放在异丙醇中用超声波振荡器清洁5分钟,然后紫外线照射条件下用臭氧清洁30分钟,将其固定到真空蒸发沉积设备的夹具上。
在基片具有透明电极线的一侧表面上形成60nm厚的N,N’-双(N,N’-二苯基-4-氨基苯基)-N,N’-二苯基-4,4’-二氨基-1,1’-联苯的膜(下文称作TPD232膜)。所形成的TPD232膜用作空穴注入层。
在所形成的TPD232膜上,形成20nm厚的4,4’-双[N-(1-萘基)-N-苯基]联苯的膜(下文称作NPD膜)。所形成的NPD膜用作空穴传输膜。
在所形成的NPD膜上,形成40nm厚的化合物E1的膜。所形成的膜用作发光层。
在所形成的化合物E1的膜上,形成20nm厚的三(8-羟基喹啉)铝的膜(下文称作Alq膜)。Alq膜用作电子注入膜。
在所形成的Alq膜上,将Li(SAES GETTERS公司生产)和Alq进行二元真空蒸发沉积,所形成的Alq:Li膜用作电子注入层(阳极)。
在所形成的Alq:Li膜上,真空蒸发沉积上铝,形成金属阳极。这样就制成了有机EL器件。
当向得到的器件施加6V电压时,发射出蓝光,最大亮度为43000cd/cm2和3.0cd/A。器件所得光谱的峰值波长约450nm,且达到很好的色纯度,色度坐标为(0.150,0.131)。实施例6(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E4替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并进行耐热试验。结果示于表1。
耐热试验按下述步骤实施:
[耐热试验]
测定所制器件的亮度,所得值用作初始亮度(I0)。然后将器件在85℃的恒温器内放500小时。从恒温器中取出器件,静置到温度降至室温。测定上述条件下放置500小时后的亮度(I500)。按照下面的公式,用亮度降低率(%)来评价耐热性。
亮度降低率=(I0-I500)×100/I0实施例7(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E7替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并进行耐热试验。结果示于表1。实施例8(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E9替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并进行耐热试验。结果示于表1。实施例9(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E13替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并进行耐热试验。结果示于表1。实施例10(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E14替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并进行耐热试验。结果示于表1。实施例11(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E17替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并进行耐热试验。结果示于表1。实施例12(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E31替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并进行耐热试验。结果示于表1。比较实施例1(制造有机EL器件)
在一个100ml烧瓶中,放入25g(0.1mol)4-溴苄溴和19g(0.11mol)亚磷酸三乙酯,将得到的混合物加热条件下搅拌3小时。反应完成后,将反应溶液真空浓缩,得到亚磷酸酯。所得亚磷酸酯用于下面的反应,无须提纯。
在一个500ml烧瓶中,放入上面得到的亚磷酸酯、10ml(0.1mol)苯甲醛和200ml二甲亚砜,用0℃的冰水冷却。然后,缓慢加入13.4g(0.12mol)叔丁醇钾,得到的混合物室温下维持搅拌一夜。反应完成后,将反应溶液倒入500ml水中,有机层用乙酸乙酯萃取处理。用硫酸镁干燥后,用旋转蒸发器将有机层真空浓缩,得到黄色晶体。所得晶体用重结晶法(100ml异丙醇)提纯,得到15g(收率:59%)目标化合物4-溴芪。合成化合物E32
氩气流下,在配有冷凝器的500ml三颈瓶中放入1.6g(66mmol)镁、一小片碘和50mlTHF。得到的混合物室温下搅拌30分钟后,滴加由7.8g(30mmol)4-溴芪溶于100mlTHF制备的溶液。加完后,将得到的混合物于60℃下搅拌1小时,制成格氏试剂。
氩气流下,在配有冷凝器的500ml三颈瓶中放入5.1g(10mmol)10,10’-二溴-9,9’-联二蒽、0.4g(5%摩尔)二氯二(三苯基瞵)合钯、1ml(1M,1mmol)二异丁基氢化铝的甲苯溶液和100mlTHF。室温下,向得到的混合物中滴加上文所制的格氏试剂。然后将得到的混合物加热条件下加热并搅拌一夜。反应完成后,用冰水冷却反应溶液。滤出所形成的晶体,依次用50ml甲醇和50ml丙酮洗涤,得到3.5g黄色粉末。按NMR、IR和FD-MS方法测定结果,鉴定该黄色粉末为化合物E32(收率50%)。实施例14(合成化合物E33)
在一个100ml烧瓶中,放入25g(0.1mol)3-溴苄溴和19g(0.11mol)亚磷酸三乙酯,将得到的混合物加热条件下搅拌3小时。反应完成后,将反应溶液真空浓缩,得到亚磷酸酯。所得亚磷酸酯用于下面的反应,无须提纯。
在一个500ml烧瓶中,放入上面得到的亚磷酸酯、10ml(0.1mol)苯甲醛和200ml二甲亚砜,用0℃的冰水冷却。然后,缓慢加入13.4g(0.12mol)叔丁醇钾,得到的混合物室温下维持搅拌一夜。反应完成后,将反应溶液倒入500ml水中,有机层用乙酸乙酯萃取处理。用硫酸镁干燥后,用旋转蒸发器将有机层真空浓缩,得到黄色晶体。所得晶体用重结晶法(100ml异丙醇)提纯,得到20g(收率:77%)目标化合物3-溴芪。合成化合物E33
氩气流下,在配有冷凝器的500ml三颈瓶中放入1.6g(66mmol)镁、一小片碘和50mlTHF。得到的混合物室温下搅拌30分钟后,滴加由7.8g(30mmol)3-溴芪溶于100mlTHF制备的溶液。加完后,将得到的混合物于60℃下搅拌1小时,制成格氏试剂。
氩气流下,在配有冷凝器的500ml三颈瓶中放入5.1g(10mmol)10,10’-二溴-9,9’-联二蒽、0.4g(5%摩尔)二氯二(三苯基瞵)合钯、1ml(1M,1mmol)二异丁基氢化铝的甲苯溶液和100mlTHF。室温下,向得到的混合物中滴加上文所制的格氏试剂。然后将得到的混合物加热条件下加热并搅拌一夜。反应完成后,用冰水冷却反应溶液。滤出所形成的晶体,依次用50ml甲醇和50ml丙酮洗涤,得到1.4g黄色粉末。按NMR、IR和FD-MS方法测定结果,鉴定该黄色粉末为化合物E33(收率20%)。实施例15(合成化合物E35)
按下述方法合成化合物E35:合成2-溴芪
在一个100ml烧瓶中,放入25g(0.1mol)2-溴苄溴和19g(0.11mol)亚磷酸三乙酯,将得到的混合物加热条件下搅拌3小时。反应完成后,将反应溶液真空浓缩,得到亚磷酸酯。所得亚磷酸酯用于下面的反应,无须提纯。
在一个500ml烧瓶中,放入上面得到的亚磷酸酯、10ml(0.1mol)苯甲醛和200ml二甲亚砜,用0℃的冰水冷却。然后,缓慢加入13.4g(0.12mol)叔丁醇钾,得到的混合物室温下维持搅拌一夜。反应完成后,将反应溶液倒入500ml水中,有机层用乙酸乙酯萃取处理。用硫酸镁干燥后,用旋转蒸发器将有机层真空浓缩,得到黄色晶体。所得晶体用柱色谱法(硅胶,展开剂:己烷)提纯,得到24g(收率:92%)目标化合物2-溴芪。合成化合物E35
氩气流下,在配有冷凝器的500ml三颈瓶中放入1.6g(66mmol)镁、一小片碘和50mlTHF。得到的混合物室温下搅拌30分钟后,滴加由7.8g(30mmol)2-溴芪溶于100mlTHF制备的溶液。加完后,将得到的混合物于60℃下搅拌1小时,制成格氏试剂。
氩气流下,在配有冷凝器的500ml三颈瓶中放入5.1g(10mmol)10,10’-二溴-9,9’-联二蒽、0.4g(5%摩尔)二氯二(三苯基瞵)合钯、1ml(1M,1mmol)二异丁基氢化铝的甲苯溶液和100mlTHF。室温下,向得到的混合物中滴加上文所制的格氏试剂。然后将得到的混合物加热条件下加热并搅拌一夜。反应完成后,用冰水冷却反应溶液。滤出所形成的晶体,依次用50ml甲醇和50ml丙酮洗涤,得到5.7g黄色粉末。按NMR、IR和FD-MS方法测定结果,鉴定该黄色粉末为化合物E35(收率80%)。实施例16到18(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用表1所示的化合物替换化合物E1。使用实施例16到18中制成的器件,证实其发光性能并进行耐热试验。用实施例16和17中制造的器件测定色度坐标。结果示于表1。实施例19(合成化合物E42)
在一个100ml烧瓶中,放入25g(0.1mol)4-溴苄溴和19g(0.11mol)亚磷酸三乙酯,将得到的混合物加热条件下搅拌3小时。反应完成后,将反应溶液真空浓缩,得到亚磷酸酯。所得亚磷酸酯用于下面的反应,无须提纯。
在一个500ml烧瓶中,放入上面得到的亚磷酸酯、12g(0.1mol)苯乙酮和200ml二甲亚砜,用0℃的冰水冷却。然后,缓慢加入13.4g(0.12mol)叔丁醇钾,得到的混合物室温下维持搅拌一夜。反应完成后,将反应溶液倒入500ml水中,有机层用乙酸乙酯萃取处理。用硫酸镁干燥后,用旋转蒸发器将有机层真空浓缩,得到黄色晶体。所得晶体用重结晶法(100ml异丙醇)提纯,得到12g(收率:44%)目标化合物4-溴-β-甲基芪。合成化合物E42
氩气流下,在配有冷凝器的500ml三颈瓶中放入1.6g(66mmol)镁、一小片碘和50mlTHF。得到的混合物室温下搅拌30分钟后,滴加由8.2g(30mmol)4-溴-β-甲基芪溶于100mlTHF制备的溶液。加完后,将得到的混合物于60℃下搅拌1小时,制成格氏试剂。
氩气流下,在配有冷凝器的500ml三颈瓶中放入5.1g(10mmol)10,10’-二溴-9,9’-联二蒽、0.4g(5%摩尔)二氯二(三苯基瞵)合钯、1ml(1M,1mmol)二异丁基氢化铝的甲苯溶液和100mlTHF。室温下,向得到的混合物中滴加上文所制的格氏试剂。然后将得到的混合物加热条件下加热并搅拌一夜。反应完成后,用冰水冷却反应溶液。滤出所形成的晶体,依次用50ml甲醇和50ml丙酮洗涤,得到4.4g黄色粉末。按NMR、IR和FD-MS方法测定结果,鉴定该黄色粉末为化合物E42(收率60%)。实施例20(合成化合物E43)
在一个100ml烧瓶中,放入25g(0.1mol)3-溴苄溴和19g(0.11mol)亚磷酸三乙酯,将得到的混合物加热条件下搅拌3小时。反应完成后,将反应溶液真空浓缩,得到亚磷酸酯。所得亚磷酸酯用于下面的反应,无须提纯。
在一个500ml烧瓶中,放入上面得到的亚磷酸酯、12g(0.1mol)苯乙酮和200ml二甲亚砜,用0℃的冰水冷却。然后,缓慢加入13.4g(0.12mol)叔丁醇钾,得到的混合物室温下维持搅拌一夜。反应完成后,将反应溶液倒入500ml水中,有机层用乙酸乙酯萃取处理。用硫酸镁干燥后,用旋转蒸发器将有机层真空浓缩,得到黄色晶体。所得晶体用重结晶法(100ml异丙醇)提纯,得到17g(收率:63%)目标化合物3-溴-β-甲基芪。合成化合物E43
氩气流下,在配有冷凝器的500ml三颈瓶中放入1.6g(66mmol)镁、一小片碘和50mlTHF。得到的混合物室温下搅拌30分钟后,滴加由8.2g(30mmol)3-溴-β-甲基芪溶于100mlTHF制备的溶液。加完后,将得到的混合物于60℃下搅拌1小时,制成格氏试剂。
氩气流下,在配有冷凝器的500ml三颈瓶中放入5.1g(10mmol)10,10’-二溴-9,9’-联二蒽、0.4g(5%摩尔)二氯二(三苯基瞵)合钯、1ml(1M,1mmol)二异丁基氢化铝的甲苯溶液和100mlTHF。室温下,向得到的混合物中滴加上文所制的格氏试剂。然后将得到的混合物加热条件下加热并搅拌一夜。反应完成后,用冰水冷却反应溶液。滤出所形成的晶体,依次用50ml甲醇和50ml丙酮洗涤,得到5.3g黄色粉末。按NMR、IR和FD-MS方法测定结果,鉴定该黄色粉末为化合物E43(收率72%)。实施例21(合成化合物E44)
在一个500ml烧瓶中,放入23g(0.1mol)苄膦酸乙酯、20g(0.1mol)4-溴苯乙酮和200ml二甲亚砜,用0℃的冰水冷却。然后,缓慢加入13.4g(0.12mol)叔丁醇钾,得到的混合物室温下维持搅拌一夜。反应完成后,将反应溶液倒入500ml水中,有机层用乙酸乙酯萃取处理。用硫酸镁干燥后,用旋转蒸发器将有机层真空浓缩。所得产物用柱色谱法(硅胶,展开剂:己烷)提纯,得到26g(收率:88%)目标化合物3-溴-α-甲基芪。合成化合物E44
氩气流下,在配有冷凝器的500ml三颈瓶中放入1.6g(66mmol)镁、一小片碘和50mlTHF。得到的混合物室温下搅拌30分钟后,滴加由8.2g(30mmol)3-溴-α-甲基芪溶于100mlTHF制备的溶液。加完后,将得到的混合物于60℃下搅拌1小时,制成格氏试剂。
氩气流下,在配有冷凝器的500ml三颈瓶中放入5.1g(10mmol)10,10’-二溴-9,9’-联二蒽、0.4g(5%摩尔)二氯二(三苯基瞵)合钯、1ml(1M,1mmol)二异丁基氢化铝的甲苯溶液和100mlTHF。室温下,向得到的混合物中滴加上文所制的格氏试剂。然后将得到的混合物加热条件下加热并搅拌一夜。反应完成后,用冰水冷却反应溶液。滤出所形成的晶体,依次用50ml甲醇和50ml丙酮洗涤,得到5.8g黄色粉末。按NMR、IR和FD-MS方法测定结果,鉴定该黄色粉末为化合物E44(收率79%)。实施例22(测定玻璃化转变温度)
为评价耐热性,按差示扫描量热法(DSC)测定化合物E1、E32、E33和E42的玻璃化转变温度(Tg),结果分别为160℃、163℃、142℃和140℃。玻璃化转变温度全部都在140℃以上。比较实施例2(测定玻璃化转变温度)
为评价耐热性,按DSC方法测定比较实施例1所用化合物H1的Tg,结果低至96℃。实施例23(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E42替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并获得色度坐标。结果示于表1。最大发光亮度为30000cd/m2。实施例24(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E43替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并获得色度坐标。结果示于表1。实施例25(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用化合物E44替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并获得色度坐标。结果示于表1。比较实施例3(制造有机EL器件)
按实施例5所采用的相同步骤制造有机EL器件,不同之处是用下式所示的化合物H3替换化合物E1来制成发光层。使用制成的器件,证实其发光性能并获得色度坐标。结果示于表1。
表1
化合物 电压 亮度 发光颜 效率 耐热性 色度坐标
(V) (nit) 色 (cd/A) (亮度降低率)
(%)实施例5 E1 6 95 蓝 3.0 5 (0.150,0.131)实施例6 E4 6 130 蓝 3.5 7 -实施例7 E7 6 161 蓝 3.7 4 -实施例8 E9 6 95 蓝 2.7 3 -实施例9 E13 6 210 黄蓝 7.8 12 -实施例10 E14 6 120 蓝 3.7 6 -实施例11 E17 6 60 蓝绿 4.0 5 -实施例12 E31 6 313 蓝 4.8 8 -实施例16 E32 6 210 蓝 2.2 1 (0.150,0.135)实施例17 E33 6 120 蓝 4.3 2 (0.171,0.130)实施例18 E35 6 170 蓝 4.9 4 -实施例23 E42 6 157 蓝紫 3.0 - (0.170,0.130)实施例24 E43 6 130 蓝紫 2.4 - (0.155,0.103)实施例25 E44 6 161 蓝紫 2.6 - (0.155,0.112)比较实施例1 H1 6 120 蓝绿 1.7 45 (0.182,0.288)比较实施例2 H2 6 313 蓝 1.6 - (0.162,0.160)比较实施例3 H3 6 120 蓝绿 2.0 - (0.210,0.320)
如表1所示,包含用本发明蒽衍生物所形成发光层的有机EL器件呈现出高发光效率、低亮度降低率和高耐热性。之所以表现出这些性能,是因为这些蒽衍生物具有140℃以上的高玻璃化转变温度且具有发射蓝到绿区强荧光的性能。表1结果还显示,本发明有机EL器件所发射的蓝光比比较实施例器件所发光具有更好的色纯度。
相比之下,比较实施例1、3和4呈现较低的发光效率。并且比较实施例1和4的有机EL器件呈现很强的绿光,不能用作发射蓝光的器件。
工业应用
本发明的蒽衍生物适合用作有机EL器件的构成材料。特别是当蒽衍生物用作发光材料时,呈现出很好的发光效率和优异的耐热性(使用寿命),所得到的器件用作具有能发射蓝到绿区荧光性质的器件。
Claims (14)
1.一种通式(I)所代表的蒽衍生物:式中X和Y各自独立代表一个6到30个碳原子的取代或未取代的三官能度芳环基团或是一个4到30个碳原子的取代或未取代的三官能度杂环基团;(1)A1到A4各自独立代表一个6到30个碳原子的取代或未取代的芳基或是一个4到30个碳原子的取代或未取代的单价杂环基,或者(2)A1代表氢原子,A2代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代,A3代表氢原子且A4代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代;R1到R16各自独立代表氢原子、卤原子、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的烷硫基、取代或未取代的芳硫基、取代或未取代的氨基或是取代或未取代的芳基;R1到R16所代表的相邻基团可通过彼此之间成键而成环;Q代表5到30个碳原子的取代或未取代的亚环烷基、6到30个碳原子的取代或未取代的亚芳基或是4到30个碳原子的取代或未取代的二价杂环基;p代表选自0、1和2的数。
2.一种通式(II)所代表的蒽衍生物:式中(1)A1到A4各自独立代表一个6到30个碳原子的取代或未取代的芳基或是一个4到30个碳原子的取代或未取代的单价杂环基,或者(2)A1代表氢原子,A2代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代,A3代表氢原子且A4代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代;R1到R16各自独立代表氢原子、卤原子、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的烷硫基、取代或未取代的芳硫基、取代或未取代的氨基或是取代或未取代的芳基;R1到R16所代表的相邻基团可通过彼此之间成键而成环;Q代表5到30个碳原子的取代或未取代的亚环烷基、6到30个碳原子的取代或未取代的亚芳基或是4到30个碳原子的取代或未取代的二价杂环基;p代表选自0、1和2的数。
3.一种通式(II’)所代表的蒽衍生物:式中(1)A1到A4各自独立代表一个6到30个碳原子的取代或未取代的芳基或是一个4到30个碳原子的取代或未取代的单价杂环基,或者(2)A1代表氢原子,A2代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代,A3代表氢原子且A4代表一个苯乙烯基,其中苯基部分和乙烯基的α位或β位可以被1到30个碳原子的烷基取代;R1到R16各自独立代表氢原子、卤原子、氰基、硝基、取代或未取代的烷基、取代或未取代的烷氧基、取代或未取代的芳氧基、取代或未取代的烷硫基、取代或未取代的芳硫基、取代或未取代的氨基或是取代或未取代的芳基;R1到R16所代表的相邻基团可通过彼此之间成键而成环;Q代表5到30个碳原子的取代或未取代的亚环烷基、6到30个碳原子的取代或未取代的亚芳基或是4到30个碳原子的取代或未取代的二价杂环基;p代表选自0、1和2的数。
5.一种有机电致发光器件,包括含权利要求1所述的蒽衍生物的发光区。
6.一种有机电致发光器件,包括含权利要求1所述的蒽衍生物的有机发光层。
7.一种按权利要求5的有机电致发光器件,其中有机发光层进一步包括能形成复合场所的物质。
8.一种按权利要求6的有机电致发光器件,其中有机发光层进一步包括能形成复合场所的物质。
9.一种按权利要求7的有机电致发光器件,其中能形成复合场所的物质是一种荧光量子产率为0.3到1.0的荧光性物质。
10.一种按权利要求8的有机电致发光器件,其中能形成复合场所的物质是一种荧光量子产率为0.3到1.0的荧光性物质。
11.一种按权利要求7的有机电致发光器件,其中能形成复合场所的物质是至少一种选自苯乙烯基胺化合物、喹吖酮衍生物、红荧烯衍生物、香豆素衍生物、苝衍生物、吡喃衍生物和荧蒽衍生物的化合物。
12.一种按权利要求8的有机电致发光器件,其中能形成复合场所的物质是至少一种选自苯乙烯基胺化合物、喹吖酮衍生物、红荧烯衍生物、香豆素衍生物、苝衍生物、吡喃衍生物和荧蒽衍生物的化合物。
13.一种按权利要求5的有机电致发光器件,其中在有机发光层与阴极或阳极之间形成一硫族化合物层、金属卤化物层或金属氧化物层。
14.一种按权利要求6的有机电致发光器件,其中在有机发光层与阴极或阳极之间形成一硫族化合物层、金属卤化物层或金属氧化物层。
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EP (1) | EP1182183B1 (zh) |
KR (1) | KR100843819B1 (zh) |
CN (1) | CN1226250C (zh) |
AT (1) | ATE451344T1 (zh) |
DE (1) | DE60140720D1 (zh) |
TW (1) | TW574342B (zh) |
WO (1) | WO2001072673A1 (zh) |
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-
2001
- 2001-03-23 DE DE60140720T patent/DE60140720D1/de not_active Expired - Lifetime
- 2001-03-23 CN CNB018007333A patent/CN1226250C/zh not_active Expired - Fee Related
- 2001-03-23 EP EP01915727A patent/EP1182183B1/en not_active Expired - Lifetime
- 2001-03-23 WO PCT/JP2001/002330 patent/WO2001072673A1/ja active Application Filing
- 2001-03-23 AT AT01915727T patent/ATE451344T1/de not_active IP Right Cessation
- 2001-03-23 KR KR1020017014307A patent/KR100843819B1/ko not_active IP Right Cessation
- 2001-03-28 TW TW90107379A patent/TW574342B/zh not_active IP Right Cessation
- 2001-03-28 US US09/818,846 patent/US20020048687A1/en not_active Abandoned
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2003
- 2003-07-02 US US10/610,930 patent/US6797848B2/en not_active Expired - Lifetime
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CN102097596A (zh) * | 2006-03-21 | 2011-06-15 | 株式会社半导体能源研究所 | 发光元件、发光装置和电子装置 |
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CN104035292A (zh) * | 2013-03-07 | 2014-09-10 | 佳能株式会社 | 电子照相感光构件和各自包括其的电子照相设备与处理盒 |
CN104035292B (zh) * | 2013-03-07 | 2017-10-13 | 佳能株式会社 | 电子照相感光构件和各自包括其的电子照相设备与处理盒 |
CN109956897A (zh) * | 2019-04-24 | 2019-07-02 | 上海钥熠电子科技有限公司 | 一种9,9’-联蒽衍生物的化合物、包含其的oled显示面板和电子设备 |
Also Published As
Publication number | Publication date |
---|---|
US6797848B2 (en) | 2004-09-28 |
TW574342B (en) | 2004-02-01 |
KR100843819B1 (ko) | 2008-07-03 |
US20020048687A1 (en) | 2002-04-25 |
EP1182183A4 (en) | 2002-06-19 |
KR20020026864A (ko) | 2002-04-12 |
US20040100188A1 (en) | 2004-05-27 |
EP1182183A1 (en) | 2002-02-27 |
CN1226250C (zh) | 2005-11-09 |
WO2001072673A1 (fr) | 2001-10-04 |
DE60140720D1 (de) | 2010-01-21 |
EP1182183B1 (en) | 2009-12-09 |
ATE451344T1 (de) | 2009-12-15 |
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