CN101861291A - 苯并*衍生物及使用该衍生物的有机电致发光元件 - Google Patents
苯并*衍生物及使用该衍生物的有机电致发光元件 Download PDFInfo
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- CN101861291A CN101861291A CN200880116295A CN200880116295A CN101861291A CN 101861291 A CN101861291 A CN 101861291A CN 200880116295 A CN200880116295 A CN 200880116295A CN 200880116295 A CN200880116295 A CN 200880116295A CN 101861291 A CN101861291 A CN 101861291A
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- 238000005554 pickling Methods 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000213 sulfino group Chemical group [H]OS(*)=O 0.000 description 1
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
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- JFLKFZNIIQFQBS-FNCQTZNRSA-N trans,trans-1,4-Diphenyl-1,3-butadiene Chemical group C=1C=CC=CC=1\C=C\C=C\C1=CC=CC=C1 JFLKFZNIIQFQBS-FNCQTZNRSA-N 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Images
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- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
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- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
- C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
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- C07C255/52—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of six-membered aromatic rings being part of condensed ring systems
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- C07C43/235—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring and to a carbon atom of a ring other than a six-membered aromatic ring
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C07D209/56—Ring systems containing three or more rings
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- 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
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
- C07D333/10—Thiophene
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
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Abstract
由下述式(1)表示的稠环芳烃衍生物，式(1)中，Ra及Rb分别表示氢原子或者取代基，m、n分别独立地表示1～13的整数，m、n为2以上时，Ra、Rb可分别相同或不同，L1表示单键、或者取代或未取代的2价连接基团，其中，式(1)的稠环芳烃衍生物不具有蒽环。
Description
技术领域
本发明涉及作为有机电致发光元件用材料有用的新型稠环芳烃衍生物(苯并
衍生物)及使用该衍生物的有机电致发光元件。
背景技术
有机电致发光元件(以下有时将电致发光简略记为EL)是利用以下原理的自发光元件，所述原理为：通过施加电场，利用由阳极注入的空穴与由阴极注入的电子的复合能，荧光材料进行发光。
有机EL元件的进展显著，另外，由于有机EL元件具有低施加电压驱动、高亮度、发光波长多样性、高速应答性、薄型且轻量的发光器件可制作等特征，因此期待应用于广泛的用途中。
有机EL元件中使用的发光材料，对元件发出的光的颜色和发光寿命影响很大，因此一直以来积极地对其进行研究。
作为发光材料，例如已知有：三(8-羟基喹啉)铝络合物等螯合络合物、香豆素衍生物、四苯基丁二烯衍生物、二苯乙烯基亚芳基衍生物、噁二唑衍生物等发光材料。利用这些发光材料，得到从蓝色到红色的可见区域的发光。
另外，正在研究使用磷光性化合物作为发光材料，并将三线态的能量用于发光。例如，已知使用铱络合物作为发光材料的有机EL元件显示高发光效率。
另外，已知有使用聚苯乙烯(PPV)作为共轭类高分子的有机EL元件。在该元件中涂布PPV形成单层膜并确认发光。
另外，在专利文献1中使用含有9，10-二-(2-萘基)蒽衍生物的层作为有机层。
专利文献1：美国专利第5935721号
本发明的目的在于提供作为有机EL元件用材料适宜的有机材料。
发明内容
本发明人着眼于苯并
衍生物作为有机EL元件用材料，进行了深入的研究。结果发现，具有规定结构的苯并
衍生物对于有机EL元件的长寿命化、高效率化以及低电压化有效，从而完成了本发明。
根据本发明，提供以下的稠环芳烃衍生物等。
1.一种稠环芳烃衍生物，其由下述式(1)表示，
式(1)中，Ra及Rb分别表示氢原子或者取代基，m、n分别独立地表示1～13的整数，m、n为2以上时，Ra、Rb可分别相同或不同，L1表示单键或者取代或未取代的2价连接基团，其中，式(1)的稠环芳烃衍生物不具有蒽环。
2.根据1所述的稠环芳烃衍生物，其由下述式(2)表示，
式(2)中，Ra及Rb分别表示氢原子或者取代基，m、n分别独立地表示1～13的整数，m、n为2以上时，Ra、Rb可分别相同或不同，L2表示单键或者取代或未取代的2价连接基团，其中，式(2)的稠环芳烃衍生物不具有蒽环。
3.根据1或2所述的稠环芳烃衍生物，其中，L1或L2为取代或未取代的环碳原子数6～50的亚芳基。
4.一种有机电致发光元件用材料，其中，含有上述1～3中任一项所述的稠环芳烃衍生物。
5.根据4所述的有机电致发光元件用发光材料，其为发光材料。
6.一种有机电致发光元件，其中，具有阳极和阴极以及在所述阳极及阴极之间夹持的包含发光层的1层以上的有机薄膜层，所述有机薄膜层的至少一层含有权利要求1～3中任一项所述的化合物。
7.根据6所述的有机电致发光元件，其中，所述发光层含有所述稠环芳烃衍生物。
8.根据7所述的有机电致发光元件，其中，所述发光层含有所述稠环芳烃衍生物作为主体材料。
9.根据6～8中任一项所述的有机电致发光元件，其中，所述发光层还含有荧光性掺杂物和磷光性掺杂物中的至少一种。
10.根据9所述的有机电致发光元件，其中，所述荧光性掺杂物为芳基胺化合物。
11.根据9所述的有机电致发光元件，其中，所述荧光性掺杂物为苯乙烯基胺化合物。
12.根据9所述的有机电致发光元件，其中，所述磷光性掺杂物为金属络合化合物。
根据本发明，得到作为有机EL元件用材料适宜的稠环芳烃衍生物。
使用本发明的稠环芳烃衍生物的有机EL元件寿命长以及高效率，且可以进行低电压驱动。
附图说明
图1是作为本发明的一个实施方式的有机EL元件的概略截面图。
具体实施方式
以下，对本发明的稠环芳烃衍生物进行具体说明。
本发明的稠环芳烃衍生物是由下述式(1)表示的化合物。
(式(1)中，Ra及Rb分别表示氢原子或者取代基，m、n分别独立地表示1～13的整数，m、n为2以上时，Ra、Rb可分别相同或不同，L1表示单键、或者取代或未取代的2价连接基团，其中，式(1)的稠环芳烃衍生物不具有蒽环)。
另外，式(1)中，L1的结合位置可以是苯并
环具有的14个结合位置中的任意一个。
同样，Ra及Rb的结合位置可以是除L1的结合位置之外的13个结合位置中的任意一个。
作为Ra及Rb表示的取代基的例子，可以列举：烷基(优选碳原子数1～20、更优选碳原子数1～12、特别优选碳原子数1～8，可以列举例如甲基、乙基、异丙基、叔丁基、正辛基、正癸基、正十六烷基、环丙基、环戊基、环己基等)、烯基(优选碳原子数2～20、更优选碳原子数2～12、特别优选碳原子数2～8，可以列举例如：乙烯基、烯丙基、2-丁烯基、3-戊烯基等)、炔基(优选碳原子数2～20、更优选碳原子数2～12、特别优选碳原子数2～8，可以列举例如：丙炔基、3-戊炔基等)、取代或未取代的芳基(优选碳原子数6～20、特别优选6～14，可以列举例如：苯基、萘基、联苯基、萘基苯基、苯基萘基、萘基萘基、菲基、芴基。其中不包括蒽环。作为芳基的取代基，可以列举芳基(优选碳原子数6～20、特别优选6～14，可列举例如苯基、萘基、菲基。其中不包括蒽环)、杂环基(优选碳原子数1～30、更优选碳原子数1～12，可以列举咪唑基、吡啶基、喹啉基、呋喃基、噻吩基、哌啶基、吗啉基、苯并噁唑基、苯并咪唑基、苯并噻唑基、咔唑基、苯并呋喃基、二苯并呋喃基、苯并苯硫基、二苯并苯硫基等))、取代或未取代的氨基(优选碳原子数0～20、更优选碳原子数0～12、特别优选碳原子数0～6，可以列举例如氨基、甲基氨基、二甲基氨基、二乙基氨基、二苯基氨基、二苄基氨基等)、烷氧基(优选碳原子数1～20、更优选碳原子数1～12、特别优选碳原子数1～8，可以列举例如甲氧基、乙氧基、丁氧基等)、芳氧基(优选碳原子数6～20、更优选碳原子数6～16、特别优选碳原子数6～12，可以列举例如苯氧基、2-萘氧基等)、酰基(优选碳原子数1～20、更优选碳原子数1～16、特别优选碳原子数1～12，可以列举例如乙酰基、苯甲酰基、甲酰基、新戊酰基等)、烷氧羰基(优选碳原子数2～20、更优选碳原子数2～16、特别优选碳原子数2～12，可以列举例如甲氧羰基、乙氧羰基等)、芳氧羰基(优选碳原子数7～20、更优选碳原子数7～16、特别优选碳原子数7～10，可以列举例如：苯氧羰基等)、酰氧基(优选碳原子数2～20、更优选碳原子数2～16、特别优选碳原子数2～10，可以列举例如乙酰氧基、苯甲酰氧基等)、酰氨基(优选碳原子数2～20、更优选碳原子数2～16、特别优选碳原子数2～10，可以列举例如乙酰氨基、苯甲酰氨基等)、烷氧羰基氨基(优选碳原子数2～20、更优选碳原子数2～16、特别优选碳原子数2～12，可以列举例如甲氧羰基氨基等)、芳氧羰基氨基(优选碳原子数7～20、更优选碳原子数7～16、特别优选碳原子数7～12，可以列举例如苯氧羰基氨基等)、取代或未取代的磺酰氨基(优选碳原子数1～20、更优选碳原子数1～16、特别优选碳原子数1～12，可以列举例如甲烷磺酰氨基、苯磺酰氨基等)、取代或未取代的氨磺酰基(优选碳原子数0～20、更优选碳原子数0～16、特别优选碳原子数0～12，可以列举例如氨磺酰基、甲基氨磺酰基、二甲基氨磺酰基、苯基氨磺酰基等)、取代或未取代的氨基甲酰基(优选碳原子数1～20、更优选碳原子数1～16、特别优选碳原子数1～12，可以列举例如氨基甲酰基、甲基氨基甲酰基、二乙基氨基甲酰基、苯基氨基甲酰基等)、烷硫基(优选碳原子数1～20、更优选碳原子数1～16、特别优选碳原子数1～12，可以列举例如甲基硫基、乙基硫基等)、芳硫基(优选碳原子数6～20、更优选碳原子数6～16、特别优选碳原子数6～12，可以列举例如苯硫基等)、取代或未取代的磺酰基(优选碳原子数1～20、更优选碳原子数1～16、特别优选碳原子数1～12，可以列举例如甲磺酰基、甲苯磺酰基等)、取代或未取代的亚磺酰基(优选碳原子数1～20、更优选碳原子数1～16、特别优选碳原子数1～12，可以列举例如甲烷亚磺酰基、苯亚磺酰基等)、取代或未取代的脲基(优选碳原子数1～20、更优选碳原子数1～16、特别优选碳原子数1～12，可以列举例如脲基、甲基脲基、苯基脲基等)、取代或未取代的磷酸酰胺基(优选碳原子数1～20、更优选碳原子数1～16、特别优选碳原子数1～12，可以列举例如二乙基磷酸酰胺基、苯基磷酸酰胺基等)、羟基、巯基、卤原子(例如氟原子、氯原子、溴原子、碘原子)、氰基、磺基、羧基、硝基、异羟肟酸基、亚磺基、肼基、亚氨基、杂环基(优选碳原子数1～30、更优选碳原子数1～12，例如为含有氮原子、氧原子、硫原子作为杂原子的基团，具体可以列举例如咪唑基、吡啶基、喹啉基、呋喃基、噻吩基、哌啶基、吗啉基、苯并噁唑基、苯并咪唑基、苯并噻唑基、咔唑基、苯并呋喃基、二苯并呋喃基、苯并苯硫基、二苯并苯硫基等)、甲硅烷基(优选碳原子数3～40、更优选碳原子数3～30、特别优选碳原子数3～24，可以列举例如三甲基甲硅烷基、三苯基甲硅烷基等)等。这些取代基可以进一步被取代。另外，取代基为二个以上时，可以相同或不同。
上述中，优选烷基、烯基、芳基、芳氨基、咔唑基、咔唑基芳基、二苯并呋喃基芳基、二苯并苯硫基芳基。
作为L1表示的取代或未取代的2价的连接基团，可以列举例如：取代或未取代的亚烷基、取代或未取代的环碳原子数6～50的亚芳基、取代或未取代的环原子数5～50的杂环基。
作为取代或未取代的亚烷基的例子，可以列举：从碳原子数1～20的下述烷基中进一步除去一个氢原子而得到的2价基团。
甲基、乙基、异丙基、叔丁基、正辛基、正癸基、正十六烷基、环丙基、环戊基、环己基。
作为它们的取代基，可以列举例如：上述烷基、后述的芳基或者杂环基等。
作为取代或未取代的环碳原子数6～50的亚芳基的例子，可以列举：从下述芳基中进一步除去一个氢原子而得到的2价基团。
苯基、1-萘基、2-萘基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基、1-并四苯基、2-并四苯基、9-并四苯基、1-芘基、2-芘基、4-芘基、2-联苯基、3-联苯基、4-联苯基、对三联苯-4-基、对三联苯-3-基、对三联苯-2-基、间三联苯-4-基、间三联苯-3-基、间三联苯-2-基、邻甲苯基、间甲苯基、对甲苯基、对叔丁基苯基、对(2-苯基丙基)苯基、3-甲基-2-萘基、4-甲基-1-萘基、4’-甲基联苯基、4”-叔丁基-对三联苯4-基、1-
基、2-基、6-基、苯基-1-萘基、苯基-2-萘基、萘基-1-萘基、萘基-2-萘基。
作为它们的取代基，可以列举例如：上述烷基、芳基或者后述的杂环基等。
作为取代或未取代的环原子数5～50的杂环基的例子，可以列举从下述1价的亚杂环基中进一步除去一个氢原子而得到的2价的基团。
咪唑基、吡啶基、喹啉基、呋喃基、噻吩基、哌啶基、吗啉基、苯并噁唑基、苯并咪唑基、苯并噻唑基、咔唑基、苯并呋喃基、二苯并呋喃基、苯并苯硫基、二苯并苯硫基。
作为它们的取代基，可以列举例如：上述烷基、芳基或者杂环基等。
另外，可以是组合有上述的亚芳基、杂环基、单键、及亚烷基等的2价基团2个以上的基团、具有芴结构的基团。例如可以列举如下基团。
特别优选为下述的2价基团。
另外，本发明的稠环芳烃衍生物不具有蒽环。在此不具有蒽环，是指L1或者L2不具有蒽基、亚蒽基等。不代表并四苯或并五苯等在稠环中含有蒽骨架的化合物。
m、n分别独立地表示1～13的整数。本发明中优选Ra及Rb全部为氢原子的情况。
本发明的稠环芳烃衍生物中，下述所示的苯并[g]
的10位的反应性高。
因此，本发明的稠环芳烃衍生物优选为在上述10位上结合的由下述式(2)表示的化合物。
(Ra、Rb、m以及n与上述式(1)同样。L2表示与式(1)的L1同样的基团)。
本发明的稠环芳烃衍生物的具体例子如下所示。
本发明的稠环芳烃衍生物，例如可以通过使具有上述L1结构的二卤素化合物与将参照下述文献合成的苯并[g]
进行硼氢化而得到的中间体反应来合成。
[Synthesis 2001，No.6,841-844]
[J.Org.Chem.2005，70，3511-3517]
[Journal of the American Chemical Society 96：14 July 10，1974，4617-4622]
本发明的稠环芳烃衍生物可以作为有机EL元件用材料、特别是其发光材料适宜使用。
本发明的有机EL元件，具有阳极和阴极以及在所述阳极及阴极之间夹持的包含发光层的1层以上的有机薄膜层，有机薄膜层的至少一层含有上述本发明的化合物。
作为本发明的有机EL元件的代表结构，可以列举：
(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/电子障壁层/发光层/阴极
(7)阳极/有机半导体层/发光层/附着改善层/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
(9)阳极/绝缘层/发光层/绝缘层/阴极
(10)阳极/无机半导体层/绝缘层/发光层/绝缘层/阴极
(11)阳极/有机半导体层/绝缘层/发光层/绝缘层/阴极
(12)阳极/绝缘层/空穴注入层/空穴传输层/发光层/绝缘层/阴极
(13)阳极/绝缘层/空穴注入层/空穴传输层/发光层/电子注入层/阴极
等，但并不限于这些。它们之中优选使用通常(8)的结构。
图1中表示(8)的结构。该有机EL元件由阳极10以及阴极20、和在其之间夹持的空穴注入层30、空穴传输层32、发光层34、电子注入层36构成。空穴注入层30、空穴传输层32、发光层34、电子注入层36相当于多个有机薄膜层。这些有机薄膜层30、32、34、36中的至少一层含有本发明的化合物。
本发明的有机EL元件中，本发明的化合物可以用于上述的任意有机薄膜层，但优选用于发光层。本发明的化合物在各有机薄膜层中可以单独使用，也可以与其他化合物混合使用，本发明的元件中，优选发光层含有本发明的化合物作为主体材料，并含有荧光性掺杂物和磷光性掺杂物中的至少一种。
本发明中，优选发光层实质上由本发明的化合物以及上述掺杂物构成。
另外，有机薄膜层中本发明的化合物的含量优选为30～100摩尔％。
以下对有机EL元件的各部件进行说明。
有机EL元件通常在基板上制作，基板支撑有机EL元件。优选使用平滑的基板。在通过该基板而射出光时，优选基板为透光性、且波长400～700nm可见光区域的光的透光率为50％以上。
作为这样的透光性基板，可适宜使用例如玻璃板、合成树脂板等。作为玻璃板，可以列举：钠钙玻璃、含钡·锶玻璃、铅玻璃、铝硅酸玻璃、硼硅酸玻璃、钡硼硅酸玻璃、石英等的板。另外，作为合成树脂板，可以列举：聚碳酸酯树脂、丙烯酸树脂、聚对苯二甲酸乙二醇酯树脂、聚醚硫化物树脂、聚砜树脂等的板。
阳极将空穴注入到空穴注入层、空穴传输层或发光层中，且具有4.5eV以上的功函数是有效的。作为阳极材料的具体例子，可以列举：氧化铟锡(ITO)、氧化铟与氧化锌的混合物、ITO与氧化铈的混合物(ITCO)、氧化铟与氧化锌的混合物和氧化铈的混合物(IZCO)、氧化铟与氧化铈的混合物(ICO)、氧化锌与氧化铝的混合物(AZO)、氧化锡(NESA)、金、银、铂、铜等。
阳极可以通过蒸镀法或溅射法等由这些电极物质来形成。
从阳极射出来自发光层的发光时，阳极对于发光的透光率优选为大于10％。另外，阳极的方块电阻优选为数百Ω/□以下。
阳极的膜厚也根据材料而不同，但通常为10nm～1μm、优选为10～200nm。
发光层具有以下功能。
(i)注入功能：可以在施加电场时由阳极或空穴注入层注入空穴、并且可以由阴极或电子注入层注入电子的功能；
(ii)传输功能：通过电场的力使注入的电荷(电子和空穴)移动的功能；
(iii)发光功能：使电子与空穴复合、并将其与发光联系的功能。
作为形成发光层的方法，可以应用例如蒸镀法、旋涂法、LB法等公知的方法。发光层特别优选分子堆积膜。分子堆积膜，是使气相状态的材料化合物沉淀而形成的膜、或使溶液状态或液相状态的材料化合物固化而形成的膜，通常该分子堆积膜，可以根据凝聚结构、高次结构的不同、或由此引起的功能上的不同，与通过LB法形成的薄膜(分子累积膜)进行区分。
另外，在将树脂等粘结剂与材料化合物溶解在溶剂中而形成溶液后，利用旋涂法等将其薄膜化，由此可以形成发光层。
作为可以在发光层中使用的发光材料，可以列举例如：蒽、萘、菲、芘、并四苯、晕苯、
、荧光素、苝、酞苝(フタロペリレン)、萘并苝、紫环酮、二苯代酚酞、萘并紫环酮、二苯基丁二烯、四苯基丁二烯、邻吡喃酮、噁二唑、醛连氮、二苯并噁唑啉、联苯乙烯、吡嗪、环戊二烯、喹啉金属络合物、氨基喹啉金属络合物、苯并喹啉金属络合物、亚胺、二苯乙烯、乙烯基蒽、二氨基咔唑、吡喃、噻喃、多甲川、份菁、咪唑螯合化8-羟基喹啉酮(oxinoid)、喹吖啶酮、红荧烯及它们的衍生物和荧光色素等，但并不限于这些。
作为可以在发光层中使用的主体材料的具体例子，可以列举由下述(i)～(ix)表示的化合物。
由下述式(i)表示的非对称蒽。
(式中，Ar001为取代或未取代的环碳原子数10～50的缩合芳基。Ar002为取代或未取代的环碳原子数6～50的芳基。X001～X003分别独立地为取代或未取代的环碳原子数6～50的芳基、取代或未取代的环原子数5～50的芳香族杂环基、取代或未取代的碳原子数1～50的烷基、取代或未取代的碳原子数1～50的烷氧基、取代或未取代的碳原子数6～50的芳烷基、取代或未取代的环原子数5～50的芳氧基、取代或未取代的环原子数5～50的芳硫基、取代或未取代的碳原子数1～50的烷氧羰基、羧基、卤素原子、氰基、硝基、羟基。a、b和c分别为0～4的整数。n为1～3的整数。另外，当n为2以上时，[]内可以相同或不同。)
由下述式(ii)表示的非对称单蒽衍生物。
(式中，Ar003和Ar004分别独立地为取代或未取代的环碳原子数6～50的芳香族环基，m和n分别为1～4的整数。其中，m＝n＝1且Ar003和Ar004在苯环上的结合位置为左右对称型时，Ar003和Ar004可以不同，m或n为2～4的整数时，m与n为不同的整数。
R001～R010分别独立地为氢原子、取代或未取代的环碳原子数6～50的芳香族环基、取代或未取代的环原子数5～50的芳香族杂环基、取代或未取代的碳原子数1～50的烷基、取代或未取代的环烷基、取代或未取代的碳原子数1～50的烷氧基、取代或未取代的碳原子数6～50的芳烷基、取代或未取代的环原子数5～50的芳氧基、取代或未取代的环原子数5～50的芳硫基、取代或未取代的碳原子数1～50的烷氧羰基、取代或未取代的甲硅烷基、羧基、卤素原子、氰基、硝基、羟基。)
由下述式(iii)表示的非对称芘衍生物。
[式中，Ar005和Ar006分别为取代或未取代的环碳原子数6～50的芳基。L001和L002分别为取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚芴基、或者取代或未取代的亚二苯并硅杂环戊二烯基(dibenzosilolylene)。
m为0～2的整数，n为1～4的整数，s为0～2的整数，t为0～4的整数。另外，L001或Ar005在芘的1～5位的任一位置上结合，L002或Ar006在芘的6～10位的任一位置上结合。其中，n+t为偶数时，Ar005、Ar006、L001、L002满足下述(1)或(2)。
(1)Ar005≠Ar006和/或L001≠L002(在此，≠表示为不同结构的基团。)
(2)Ar005＝Ar006且L001＝L002时
(2-1)m≠s和/或n≠t、或者
(2-2)m＝s且n＝t时
(2-2-1)L001和L002或芘分别在Ar005和Ar006上的不同结合位置上结合，或(2-2-2)L001和L002或芘分别在Ar005和Ar006上的相同结合位置上结合时，不存在L001和L002或者Ar005和Ar006在芘中的取代位置为1位和6位、或者2位和7位的情况。]
由下述式(iv)表示的非对称蒽衍生物。
(式中，A001和A002分别独立地为取代或未取代的环碳原子数10～20的稠合芳香族环基。
Ar007和Ar008分别独立地为氢原子、或者取代或未取代的环碳原子数6～50的芳香族环基。
R011～R020分别独立地为氢原子、取代或未取代的环碳原子数6～50的芳香族环基、取代或未取代的环原子数5～50的芳香族杂环基、取代或未取代的碳原子数1～50的烷基、取代或未取代的环烷基、取代或未取代的碳原子数1～50的烷氧基、取代或未取代的碳原子数6～50的芳烷基、取代或未取代的环原子数5～50的芳氧基、取代或未取代的环原子数5～50的芳硫基、取代或未取代的碳原子数1～50的烷氧羰基、取代或未取代的甲硅烷基、羧基、卤素原子、氰基、硝基或羟基。
Ar007、Ar008、R019和R020分别可以为多个，在邻接的基团之间可以形成饱和或不饱和的环状结构。
其中，在式(iv)中，不存在在中心的蒽的9位和10位上相对于该蒽上所示的X-Y轴为对称型的基团结合的情况。)
由下述式(v)表示的蒽衍生物。
(式中，R021～R030分别独立地表示氢原子、烷基、环烷基、可取代的芳基、烷氧基、芳氧基、烷氨基、烯基、芳氨基或可取代的杂环基团，a和b分别表示1～5的整数，它们为2以上时，R021之间或R022之间各自可以相同或不同，另外，R021之间或R022之间可以结合形成环，R023与R024、R025与R026、R027与R028、R029与R030也可以互相结合形成环。L003表示单键、-O-、-S-、-N(R)-(R为烷基或可取代的芳基)、亚烷基或者亚芳基。)
由下述式(vi)表示的蒽衍生物。
(式中，R031～R040分别独立地表示氢原子、烷基、环烷基、芳基、烷氧基、芳氧基、烷氨基、芳氨基或可取代的杂环基，c、d、e和f分别表示1～5的整数，它们为2以上时，R031之间、R032之间、R036之间或R037之间各自可以相同或不同，另外，R031之间、R032之间、R033之间或R037之间可以结合形成环，R033与R034、R039与R040也可以互相结合形成环。L004表示单键、-O-、-S-、-N(R)-(R为烷基或可取代的芳基)、亚烷基或者亚芳基。)
由下述式(vii)表示的螺环芴衍生物。
(式中，A005～A008分别独立地为取代或未取代的联苯基或者取代或未取代的萘基。)
由下述式(viii)表示的含稠环化合物。
(式中，A011～A013与上述式(1)的L1表示同样的2价基团，A014～A016与式(1)的Ra表示同样的取代基。R041～R043分别独立地为氢原子、碳原子数1～6的烷基、碳原子数3～6环烷基、碳原子数1～6的烷氧基、碳原子数5～18的芳氧基、碳原子数7～18的芳烷氧基、碳原子数5～16的芳氨基、硝基、氰基、碳原子数1～6的酯基或卤原子，A011～A016中至少一个为具有3环以上的稠环芳烃的基团。)
由下述式(ix)表示的芴化合物。
(式中，R051和R052表示氢原子、取代或未取代的烷基、取代或未取代的芳烷基、取代或未取代的芳基、取代或未取代的杂环基、取代氨基、氰基或卤原子。在不同的芴基上结合的R051之间、R052之间可以相同或不同，在相同的芴基上结合的R051和R052可以相同或不同。R053和R054表示氢原子、取代或未取代的烷基、取代或未取代的芳烷基、取代或未取代的芳基或者取代或未取代的杂环基，在不同的芴基上结合的R053之间、R054之间可以相同或不同，在相同的芴基上结合的R053和R054可以相同或不同。Ar011和Ar012表示苯环合计为3个以上的取代或未取代的稠合多环芳基、或以苯环与杂环合计为3个以上的取代或未取代的碳与芴基结合的稠合多环杂环基，Ar011和Ar012可以相同或不同。n表示1至10的整数。)
作为使用磷光性掺杂物时的主体化合物的具体例子，可以列举：咔唑衍生物、三唑衍生物、噁唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳基链烷衍生物、吡唑啉衍生物、吡唑啉酮衍生物、苯二胺衍生物、芳胺衍生物、氨基取代查尔酮衍生物、苯乙烯基蒽衍生物、芴酮衍生物、腙衍生物、二苯乙烯衍生物、硅氮烷衍生物、芳香族叔胺衍生物、苯乙烯基胺衍生物、芳香族二亚甲基(ヅメチリデイン)类化合物、卟啉类衍生物、蒽醌二甲烷衍生物、蒽酮衍生物、二苯醌衍生物、噻喃二氧化物衍生物、碳二亚胺衍生物、亚芴基甲烷衍生物、二苯乙烯基吡嗪衍生物、萘苝等杂环四羧酸酐、酞菁衍生物、8-羟基喹啉衍生物的金属络合物或金属酞菁、以苯并噁唑或苯并噻唑作为配位体的金属络合物中代表的各种金属络合物聚硅烷类化合物、聚(N-乙烯基咔唑)衍生物、苯胺类共聚物、噻吩低聚物、聚噻吩等导电性高分子低聚物、聚噻吩衍生物、聚亚苯衍生物、聚苯乙炔衍生物、聚芴衍生物等高分子化合物等。主体化合物可以单独使用，也可以并用2种以上。
作为具体例子，可以列举以下的化合物。
本发明的有机EL元件中，优选发光层中含有本发明的发光材料作为主体、且至少含有磷光性掺杂物和荧光性掺杂物中的至少一种。另外，可以在含有本发明的化合物的发光层上层压含有这些掺杂物的发光层。
磷光掺杂物为可以由三线态激子发光的化合物，只要由三线态激子进行发光，则没有特别限制，优选为含有选自Ir、Ru、Pd、Pt、Os和Re中的至少一种金属的金属络合物。优选为卟啉金属络合物或邻位金属化金属络合物。磷光性化合物可以单独使用，也可以并用2种以上。
作为卟啉金属络合物，优选为卟啉铂络合物。
作为形成邻位金属化金属络合物的配位体可以为各种，但作为优选的配位体，可以列举：具有苯基吡啶骨架、联吡啶基骨架或邻菲咯啉骨架的化合物、或者2-苯基吡啶衍生物、7，8-苯并喹啉衍生物、2-(2-噻吩基)吡啶衍生物、2-(1-萘基)吡啶衍生物、2-苯基喹啉衍生物等。这些配位体可以根据需要具有取代基。特别是引入有氟化合物、三氟甲基的化合物优选作为蓝色系掺杂物。另外作为辅助配位体，可以具有乙酰丙酮化物、苦味酸等除了上述配位体以外的配位体。
作为这样的金属络合物的具体例子，可以列举以下所示的化合物。另外，在本发明中，优选与特别在红色区域发光的磷光性掺杂物组合。但并不限定于这些，根据所要求的发光颜色、元件性能、使用的主体化合物来选择适当的络合物。
作为磷光性掺杂物在发光层中的含量，没有特别的限制，可以根据目的来进行适宜选择，例如为0.1～70质量％，优选为1～30质量％。当磷光性化合物的含量不足0.1质量％时，发光微弱，不能充分地发挥其含有效果，当超过70质量％时，被称为浓度消光的现象变显著，可能元件性能降低。
作为荧光性掺杂物，优选从胺类化合物、芳香族化合物、三(8-羟基喹啉)铝络合物等螯合络合物、香豆素衍生物、四苯基丁二烯衍生物、二苯乙烯基亚芳基衍生物、噁二唑衍生物等中，根据所要求的发光颜色来选择化合物，进一步优选苯乙烯基胺化合物、苯乙烯基二胺化合物、芳胺化合物、芳二胺化合物。另外，也优选不是胺化合物的稠合多环芳香族化合物。这些荧光性掺杂物可以单独使用也可以多种组合使用。
作为荧光性掺杂物在发光层中的含量，没有特别的限制，可以根据目的来进行适宜选择，例如为0.1～70质量％，优选为1～30质量％。
作为苯乙烯基胺化合物及苯乙烯基二胺化合物，优选为由下述式(A)表示的化合物。
(式中，Ar101为p价基团，为苯基、萘基、联苯基、三联苯基、均二苯乙烯基、二苯乙烯芳基对应的p价基团。Ar102以及Ar103分别为碳原子数6～20的芳烃基，Ar101、Ar102以及Ar103可以被取代。Ar101～Ar103中的任一个由苯乙烯基取代。进一步优选Ar102或者Ar103中的至少一个由苯乙烯基取代。p为1～4的整数，优选为1～2的整数)。
在此，作为碳原子数6～20的芳烃基，可以列举：苯基、萘基、蒽基、菲基、三联苯基等。
作为芳基胺化合物及芳基二胺化合物，优选为由下述式(B)表示的化合物。
(式中，Ar111为q价的取代或未取代的环碳原子数5～40的芳基，Ar112、Ar113分别为取代或未取代的环碳原子数5～40的芳基。q为1～4的整数，优选为1～2的整数)。
在此，作为环碳原子数5～40的芳基，可以列举例如：苯基、萘基、蒽基、菲基、芘基、晕苯基、联苯基、三联苯基、吡咯基、呋喃基、苯硫基、苯并苯硫基、噁二唑基、二苯基蒽基、吲哚基、咔唑基、吡啶基、苯并喹啉基、荧蒽基、苊并荧蒽基、二苯乙烯基、苝基、基、苉基、苯并菲基、玉红省基、苯并蒽基、苯基蒽基、二蒽基，优选为萘基、蒽基、
基、芘基。
Ar111优选为上述q价基团，另外，Ar111为2价时，优选为由下述式(C)、(D)表示的基团，更优选为由式(D)表示的基团。
(式(C)中，r为1～3的整数)。
另外，作为在上述芳基中取代的优选取代基，可以列举：碳原子数1～6的烷基(乙基、甲基、异丙基、正丙基、仲丁基、叔丁基、戊基、己基、环戊基、环己基等)、碳原子数1～6的烷氧基(乙氧基、甲氧基、异丙氧基、正丙氧基、仲丁氧基、叔丁氧基、戊氧基、己氧基、环戊氧基、环己氧基等)、环碳原子数5～40的芳基、由环碳原子数5～40的芳基取代的氨基、具有环碳原子数5～40的芳基的酯基、具有碳原子数1～6的烷基的酯基、氰基、硝基、卤原子等。
发光层根据需要可以含有空穴传输材料、电子传输材料、聚合物粘合剂。
发光层的膜厚优选为5～50nm，更优选为7～50nm，最优选为10～50nm。不足5nm时，存在发光层形成变困难、色度的调节变困难的可能，当超过50nm时，驱动电压可能上升。
空穴注入层以及空穴传输层是有助于向发光层中的空穴注入、并传输至发光区域的层，空穴迁移率大，离子化能量小，通常为5.5eV以下。作为这样的空穴注入层以及空穴传输层的材料，优选以更低的电场强度将空穴传输至发光层的材料，另外，如果空穴的迁移率在例如104～106V/cm的电场施加时如果为10-4cm2/V·秒以上，则优选。
作为空穴注入层以及空穴传输层的材料，没有特别的限制，以往，可以从在光传导材料中作为空穴的电荷传输材料惯用的材料、或用于有机EL元件的空穴注入层以及空穴传输层的公知材料中选择任意的材料来使用。
在空穴注入层以及空穴传输层中，可以使用例如由下述式表示的芳胺衍生物。
Ar211～Ar213、Ar221～Ar223以及Ar203～Ar208分别为取代或未取代的环碳原子数6～50的芳烃基、或者取代或未取代的环原子数5～50的芳香族杂环基。a～c以及p～r分别为0～3的整数。Ar203与Ar204、Ar205与Ar206、Ar207与Ar208分别可以互相连接而形成饱和或不饱和的环。
作为取代或未取代的环碳原子数6～50的芳香族环基的例子，可以列举：苯基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基、1-并四苯基、2-并四苯基、9-并四苯基、1-芘基、2-芘基、4-芘基、2-联苯基、3-联苯基、4-联苯基、对三联苯-4-基、对三联苯-3-基、对三联苯-2-基、间三联苯-4-基、间三联苯-3-基、间三联苯-2-基、邻甲苯基、间甲苯基、对甲苯基、对叔丁基苯基、对(2-苯基丙基)苯基、3-甲基-2-萘基、4-甲基-1-萘基、4-甲基-1-蒽基、4’-甲基联苯基、4”-叔丁基-对三联苯4-基。
作为取代或未取代的环原子数5～50的芳香族杂环基的例子，可以列举：1-吡咯基、2-吡咯基、3-吡咯基、吡嗪基、2-吡啶基、3-吡啶基、4-吡啶基、1-吲哚基、2-吲哚基、3-吲哚基、4-吲哚基、5-吲哚基、6-吲哚基、7-吲哚基、1-异吲哚基、2-异吲哚基、3-异吲哚基、4-异吲哚基、5-异吲哚基、6-异吲哚基、7-异吲哚基、2-呋哺基、3-呋喃基、2-苯并呋喃基、3-苯并呋喃基、4-苯并呋喃基、5-苯并呋喃基、6-苯并呋喃基、7-苯并呋喃基、1-异苯并呋喃基、3-异苯并呋喃基、4-异苯并呋喃基、5-异苯并呋喃基、6-异苯并呋喃基、7-异苯并呋喃基、喹啉基、3-喹啉基、4-喹啉基、5-喹啉基、6-喹啉基、7-喹啉基、8-喹啉基、1-异喹啉基、3-异喹啉基、4-异喹啉基、5-异喹啉基、6-异喹啉基、7-异喹啉基、8-异喹啉基、2-喹喔啉基、5-喹喔啉基、6-喹喔啉基、1-咔唑基、2-咔唑基、3-咔唑基、4-咔唑基、9-咔唑基、1-菲啶基、2-菲啶基、3-菲啶基、4-菲啶基、6-菲啶基、7-菲啶基、8-菲啶基、9-菲啶基、10-菲啶基、1-吖啶基、2-吖啶基、3-吖啶基、4-吖啶基、9-吖啶基、1，7-菲绕啉-2-基、1，7-菲绕啉-3-基、1，7-菲绕啉-4-基、1，7-菲绕啉-5-基、1，7-菲绕啉-6-基、1，7-菲绕啉-8-基、1，7-菲绕啉-9-基、1，7-菲绕啉-10-基、1，8-菲绕啉-2-基、1，8-菲绕啉-3-基、1，8-菲绕啉-4-基、1，8-菲绕啉-5-基、1，8-菲绕啉-6-基、1，8-菲绕啉-7-基、1，8-菲绕啉-9-基、1，8-菲绕啉-10-基、1，9-菲绕啉-2-基、1，9-菲绕啉-3-基、1，9-菲绕啉-4-基、1，9-菲绕啉-5-基、1，9-菲绕啉-6-基、1，9-菲绕啉-7-基、1，9-菲绕啉-8-基、1，9-菲绕啉-10-基、1，10-菲绕啉-2-基、1，10-菲绕啉-3-基、1，10-菲绕啉-4-基、1，10-菲绕啉-5-基、2，9-菲绕啉-1-基、2，9-菲绕啉-3-基、2，9-菲绕啉-4-基、2，9-菲绕啉-5-基、2，9-菲绕啉-6-基、2，9-菲绕啉-7-基、2，9-菲绕啉-8-基、2，9-菲绕啉-10-基、2，8-菲绕啉-1-基、2，8-菲绕啉-3-基、2，8-菲绕啉-4-基、2，8-菲绕啉-5-基、2，8-菲绕啉-6-基、2，8-菲绕啉-7-基、2，8-菲绕啉-9-基、2，8-菲绕啉-10-基、2，7-菲绕啉-1-基、2，7-菲绕啉-3-基、2，7-菲绕啉-4-基、2，7-菲绕啉-5-基、2，7-菲绕啉-6-基、2，7-菲绕啉-8-基、2，7-菲绕啉-9-基、2，7-菲绕啉-10-基、1-吩嗪基、2-吩嗪基、1-吩噻嗪基、2-吩噻嗪基、3-吩噻嗪基、4-吩噻嗪基、10-吩噻嗪基、1-吩噁嗪基、2-吩噁嗪基、3-吩噁嗪基、4-吩噁嗪基、10-吩噁嗪基、2-噁唑基、4-噁唑基、5-噁唑基、2-噁二唑基、5-噁二唑基、3-呋咱基、2-噻吩基、3-噻吩基、2-甲基吡咯-1-基、2-甲基吡咯-3-基、2-甲基吡咯-4-基、2-甲基吡咯-5-基、3-甲基吡咯-1-基、3-甲基吡咯-2-基、3-甲基吡咯-4-基、3-甲基吡咯-5-基、2-叔丁基吡咯-4-基、3-(2-苯基丙基)吡咯-1-基、2-甲基-1-吲哚基、4-甲基-1-吲哚基、2-甲基-3-吲哚基、4-甲基-3-吲哚基、2-叔丁基-1-吲哚基、4-叔丁基-1-吲哚基、2-叔丁基-3-吲哚基、4-叔丁基-3-吲哚基等。
另外，在空穴注入层以及空穴传输层中，可以使用由下述式表示的化合物。
Ar231～Ar234分别为取代或未取代的环碳原子数6～50的芳烃基、或者取代或未取代的环原子数5～50的芳香族杂环基。L是连接基团，为单键、取代或未取代的环碳原子数6～50的芳烃基、或者取代或未取代的环原子数5～50的芳香族杂环基。x为0～5的整数。Ar232与Ar233可以互相连接而形成饱和或不饱和的环。
在此，作为取代或未取代的环碳原子数6～50的芳烃基、以及取代或未取代的环原子数5～50的芳香族杂环基的具体例子，可以列举与上述芳香族胺衍生物同样的基团。
另外，作为空穴注入层以及空穴传输层的材料的具体例子，可以列举：三唑衍生物、噁二唑衍生物、咪唑衍生物、聚芳基链烷衍生物、吡唑啉衍生物及吡唑啉酮衍生物、苯二胺衍生物、芳胺衍生物、氨基取代查尔酮衍生物、噁唑衍生物、苯乙烯基蒽衍生物、芴酮衍生物、腙衍生物、二苯乙烯衍生物、硅氮烷衍生物、苯胺类共聚物、导电性高分子低聚物(特别是噻吩低聚物)等。
作为空穴注入层以及空穴传输层的材料，可以使用上述的材料，但优选为卟啉化合物、芳香族叔胺化合物和苯乙烯基胺化合物，特别优选使用芳香族叔胺化合物。
另外，优选使用在分子内具有2个稠环芳烃的化合物、例如4，4’-双(N-(1-萘)-N-苯氨基)二苯(以下简单记为NPD)；或三苯胺单元连接成3个星爆(star burst)型的4，4’，4”-三(N-(3-甲基苯)-N-苯氨基)三苯胺(以下简单记为MTDATA)等。
除此之外，也可以使用由下述式表示的含氮杂环衍生物。
式中，R201～R206分别表示取代或未取代的烷基、取代或未取代的芳基、取代或未取代的芳烷基、取代或未取代的杂环基中的任一种。R201与R202、R203与R204、R205与R206、R201与R206、R202与R203、或者R204与R205可以形成稠合环。
另外，也可以使用下述式的化合物。
R211～R216为取代基，优选各自为氰基、硝基、磺酰基、羰基、三氟甲基、卤素等吸电子基团。
另外，也可以使用p型Si、p型SiC等无机化合物作为空穴注入层以及空穴传输层的材料。
空穴注入层以及空穴传输层可以通过将上述化合物由真空蒸镀法、旋涂法、流延法、LB法等公知的方法进行薄膜化来形成。作为空穴注入层以及空穴传输层的膜厚没有特别的限制，通常为5nm～5μm。空穴注入层以及空穴传输层可以通过由上述材料的一种或二种以上构成的一层来构成，也可以是将由不同的化合物构成的多个空穴注入层以及空穴传输层进行层压而成的层。
有机半导体层是有助于向发光层中注入空穴或者注入电子的层，优选为具有10-10S/cm以上的导电率的层。作为这样的有机半导体层的材料，可以使用含噻吩低聚物或含芳胺低聚物等导电性低聚物、含芳胺树枝状高分子等导电性树枝状高分子等。
电子注入层以及电子传输层是有助于向发光层中注入电子、且传输至发光区域的层，电子迁移率大。另外，附着改善层是由与阴极的附着特别好的材料构成的电子注入层中的一种。
电子传输层在5nm～5μm的膜厚中进行适宜选择，但膜厚特别厚时，为了避免电压上升，在104～106V/cm的电场施加时电子迁移率优选为10-5cm2/Vs以上。
作为电子注入层以及电子传输层中使用的材料，优选为8-羟基喹啉或其衍生物的金属络合物、或噁二唑衍生物。作为上述8-羟基喹啉或其衍生物的金属络合物的具体例子，可以列举：含有喔星(一般为8-喹啉或8-羟基喹啉)的螯合物的金属螯合喔星化合物、例如三(8-喹啉)铝。
作为噁二唑衍生物，可以列举由下式表示的电子传递化合物。
(式中，Ar301、Ar302、Ar303、Ar305、Ar306以及Ar309分别表示取代或未取代的芳基。另外，Ar304、Ar307、Ar308分别表示取代或未取代的亚芳基)。
在此，作为芳基，可以列举：苯基、联苯基、蒽基、苝基、芘基等。另外，作为亚芳基，可以列举：亚苯基、亚萘基、亚联苯基、亚蒽基、亚苝基、亚芘基等。另外，作为取代基，可以列举：碳原子数为1～10的烷基、碳原子数为1～10的烷氧基或氰基等。该电子传递化合物优选为薄膜形成性的物质。
作为上述电子传递性化合物的具体例子，可以列举下述物质。
(Me表示甲基，tBu表示叔丁基)。
另外，作为电子注入层以及电子传输层中使用的材料，也可以使用由下式(E)～(J)表示的化合物。
由
表示的含氮杂环衍生物，
(式(E)以及(F)中，A311～A313分别为氮原子或碳原子。
Ar311为取代或未取代的环碳原子数6～60的芳基、或者取代或未取代的环原子数3～60的杂芳基，Ar311，为取代或未取代的环碳原子数6～60的亚芳基、或者取代或未取代的环原子数3～60的杂亚芳基，Ar312为氢原子、取代或未取代的环碳原子数6～60的芳基、取代或未取代的环原子数3～60的杂芳基、取代或未取代的碳原子数1～20烷基、或者取代或未取代的碳原子数1～20的烷氧基。其中Ar311和Ar312中的任一个为取代或未取代的环碳原子数10～60的稠环基、或者取代或未取代的环原子数3～60的单杂稠环基。
L311、L312和L313分别为单键、取代或未取代的环碳原子数6～60的亚芳基、取代或未取代的环原子数3～60的杂亚芳基、或者取代或未取代的亚芴基。
R以及R311分别为氢原子、取代或未取代的环碳原子数6～60的芳基、取代或未取代的环原子数3～60的杂芳基、取代或未取代的碳原子数1～20的烷基、或者取代或未取代的碳原子数1～20的烷氧基，n为0～5的整数。当n为2以上时，多个R可以相同或不同，另外，由相邻接的R基团之间结合，可以形成碳环式脂肪族环或碳环式芳香族环)。
由HAr-L314-Ar321-Ar322 (G)
表示的含氮杂环衍生物，
(式中，HAr为可具有取代基的碳原子数3～40的含氮杂环，L314为单键、可具有取代基的碳原子数6～60的亚芳基、可具有取代基的原子数3～60的杂亚芳基或者可具有取代基的亚芴基，Ar321为可具有取代基的碳原子数6～60的2价的芳香族烃基，Ar322为可具有取代基的碳原子数6～60的芳基或者可具有取代基的原子数3～60的杂芳基)。
由
表示的硅杂环戊二烯衍生物，
(式中，X301以及Y301分别为碳原子数1～6的饱和或者不饱和的烃基、烷氧基、链烯氧基、炔氧基、羟基、取代或未取代的芳基、取代或未取代的杂环、或者X与Y键合形成饱和或不饱和的环的结构，R301～R304分别为氢、卤素原子、烷基、烷氧基、芳氧基、全氟烷基、全氟烷氧基、氨基、烷基羰基、芳基羰基、烷氧基羰基、芳氧基羰基、偶氮基、烷基羰氧基、芳基羰氧基、烷氧基羰氧基、芳氧基羰氧基、亚硫酰基、磺酰基、磺胺酰基、甲硅烷基、氨基甲酰基、芳基、杂环基、烯基、炔基、硝基、甲酰基、亚硝基、甲酰氧基、异氰基、氰酸酯基、异氰酸酯基、硫氰酸酯基、异硫氰酸酯基或氰基。这些基团可以被取代。另外，相邻接的基团可以形成取代或未取代的稠合环)。
由
表示的硼烷衍生物，
(式中，R321～R328以及Z322分别表示氢原子、饱和或不饱和的烃基、芳香族烃基、杂环基、取代氨基、取代硼基、烷氧基或芳氧基，X302、Y302以及Z321分别表示饱和或不饱和的烃基、芳香族烃基、杂环基、取代氨基、烷氧基或者芳氧基，Z321与Z322可以相互键合形成稠环，n表示1～3的整数，当n或者(3-n)为2以上时，R321～R328、X302、Y302、Z322及Z321可以相同或不同。其中，不包括：n为1、且X、Y以及R322为甲基、R328为氢原子或取代硼基的化合物；以及n为3、Z321为甲基的化合物)。
由
表示的镓络合物，
[式中，Q301和Q302分别表示由下述式(K)表示的配位体，L315为卤原子、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、取代或未取代的杂环基、-OR(R为氢原子、取代或未取代的烷基、取代或未取代的环烷基、取代或未取代的芳基、取代或未取代的杂环基)或者-O-Ga-Q303(Q304)(Q303和Q304，与Q301和Q302相同)表示的配位体。]
[式中，环A301和A302分别为可具有取代基的互相缩合而成的6元芳环结构。]
该金属络合物作为n型半导体的性质强，电子注入能力大。另外，络合物形成时的生成能量也低，因此，形成的金属络合物的金属与配位体之间的结合性也变牢固，作为发光材料的荧光量子效率也变大。
列举形成式(K)的配位体的环A301和A302的取代基的具体例子时，有：氯、溴、碘、氟等卤素原子、甲基、乙基、丙基、丁基、仲丁基、叔丁基、戊基、己基、庚基、辛基、硬质基、三氯甲基等取代或未取代的烷基、苯基、萘基、联苯基、蒽基、菲基、芴基、芘基、3-甲基苯基、3-甲氧基苯基、3-氟苯基、3-三氯甲基苯基、3-三氟甲基苯基、3-硝基苯基等取代或未取代的芳基、甲氧基、正丁氧基、叔丁氧基、三氯甲氧基、三氟乙氧基、五氟丙氧基、2，2，3，3-四氟丙氧基、1，1，1，3，3，3-六氟-2-丙氧基、6-(全氟乙基)己氧基等取代或未取代的烷氧基、苯氧基、对硝基苯氧基、对叔丁基苯氧基、3-氟苯氧基、五氟苯基、3-三氟甲基苯氧基等取代或未取代的芳氧基、甲硫基、乙硫基、叔丁硫基、己硫基、辛硫基、三氟甲硫基等取代或未取代的烷硫基、苯硫基、对硝基苯硫基、对叔丁基苯硫基、3-氟苯硫基、五氟苯硫基、3-三氟甲基苯硫基等取代或未取代的芳硫基、氰基、硝基、氨基、甲基氨基、二乙基氨基、乙基氨基、二乙基氨基、二丙基氨基、二丁基氨基、二苯基氨基等单或二取代氨基、双(乙酰氧甲基)氨基、双(乙酰氧乙基)氨基、双(乙酰氧丙基)氨基、双(乙酰氧丁基)氨基等酰氨基、羟基、硅氧基、酰基、氨基甲酰基、甲基氨基甲酰基、二甲基氨基甲酰基、乙基氨基甲酰基、二乙基氨基甲酰基、丙基氨基甲酰基、丁基氨基甲酰基、苯基氨基甲酰基等取代或未取代的氨基甲酰基、羧酸基、磺酸基、酰亚胺基、环戊基、环己基等环烷基、吡啶基、吡嗪基、嘧啶基、哒嗪基、三嗪基、吲哚基、喹啉基、吖啶基、吡咯烷基、二噁烷基、哌啶基、吗啉烷基(モルフオリジニル)、哌嗪基、咔唑基、呋喃基、噻吩基、噁唑基、噁二唑基、苯并噁唑基、噻唑基、噻二唑基、苯并噻唑基、三唑基、咪唑基、苯并咪唑基等杂环基等。另外，以上的取代基之间也可以结合来进一步形成6元芳环或杂环。
有机EL元件的优选形式中，在传输电子的区域或阴极与有机层的界面区域上含有还原性掺杂物。在此，还原性掺杂物定义为可以还原电子传输性化合物的物质。因此，只要是具有一定还原性的物质，则可以使用各种物质，例如，可以适宜使用选自碱金属、碱土类金属、稀土类金属、碱金属的氧化物、碱金属的卤化物、碱土类金属的氧化物、碱土类金属的卤化物、稀土类金属的氧化物或稀土类金属的卤化物、碱金属的碳酸盐、碱土类金属的碳酸盐、稀土类金属的碳酸盐、碱金属的有机络合物、碱土类金属的有机络合物、稀土类金属的有机络合物中的至少一种物质。
另外，更具体而言，作为优选的还原性掺杂物，可以列举：选自Na(功函数：2.36eV)、K(功函数：2.28eV)、Rb(功函数：2.16eV)和Cs(功函数：1.95eV)中的至少一种碱金属、或选自Ca(功函数：2.9eV)、Sr(功函数：2.0～2.5eV)和Ba(功函数：2.52eV)中的至少一种碱土类金属。特别优选功函数为2.9eV以下的物质。它们之中，更优选的还原性掺杂物为选自K、Rb和Cs中的至少一种碱金属，进一步优选为Rb或Cs，最优选为Cs。这些碱金属，还原能力特别高，通过向电子注入域中添加较少量，就可以实现在有机EL元件中的发光亮度的提高和长寿命化。另外，作为功函数为2.9eV以下的还原性掺杂物，也优选它们2种以上的碱金属的组合，特别优选含有Cs的组合，例如Cs和Na、Cs和K、Cs和Rb、或Cs和Na和K的组合。通过组合含有Cs，可以有效发挥还原能力，通过向电子注入域中的添加，实现有机EL元件中的发光亮度的提高和长寿命化。
阴极与有机层之间可以进一步设置由绝缘体或半导体构成的电子注入层。利用这样的层，可以有效防止电流的泄漏，使电子注入性提高。电子注入层如果是绝缘性薄膜，则由于形成更匀质的薄膜，因此可以使暗斑等像素缺陷减少。
作为绝缘体，优选使用选自碱金属硫属化合物、碱土类金属硫属化合物、碱金属的卤化物和碱土类金属的卤化物中的至少一种金属化合物。电子注入层如果由这些碱金属硫属化合物等构成，则可以进一步使电子注入性提高，因此优选。具体而言，作为优选的碱金属硫属化合物，可以列举例如：Li2O、K2O、Na2S、Na2Se和Na2O。作为优选的碱土类金属硫属化合物，可以列举例如：CaO、BaO、SrO、BeO、BaS和CaSe。另外，作为优选的碱金属的卤化物，可以列举例如：LiF、NaF、KF、CsF、LiCl、KCl和NaCl等。另外，作为优选的碱土类金属的卤化物，可以列举例如：CaF2、BaF2、SrF2、MgF2和BeF2等氟化物、或氟化物以外的卤化物。
另外，作为构成电子注入层的半导体，可以列举：含有Ba、Ca、Sr、Yb、Al、Ga、In、Li、Na、Cd、Mg、Si、Ta、Sb和Zn中的至少一种元素的氧化物、氮化物或氧氮化物等的单独一种或二种以上的组合。另外，构成电子注入层的无机化合物，优选为微晶或非晶质的绝缘性薄膜。
作为阴极，可以使用将功函数小(例如4eV以下)的金属、合金、电传导性化合物及它们的混合物作为电极物质的阴极。作为这样的电极物质的具体例子，可以列举：钠、钠-钾合金、镁、锂、铯、镁·银合金、铝/氧化铝、Al/Li2O、Al/LiO、Al/LiF、铝·锂合金、铟、稀土类金属等。
该阴极，可以通过蒸镀或溅射等由这些电极物质来制成。
从阴极射出来自发光层的发光时，阴极对于发光的透光率优选为大于10％。另外，作为阴极的方块电阻优选为数百Ω/□以下，膜厚通常为10nm～1μm、优选为50～200nm。
通常，由于有机EL元件在超薄膜上施加电场，因此容易产生因泄漏或短路引起的像素缺陷。为了防止该问题，优选在一对电极间插入绝缘性的薄膜层。
作为用于绝缘层的材料，可以列举例如：氧化铝、氟化锂、氧化锂、氟化铯、氧化铯、氧化镁、氟化镁、氧化钙、氟化钙、氮化铝、氧化钛、氧化硅、氧化锗、氮化硅、氮化硼、氧化钼、氧化钌、氧化钒等。也可以使用它们的混合物或层压物。
关于制作有机EL元件的方法，例如可以利用上述材料和方法由阳极起依次形成必要的层，最后形成阴极。另外，也可以从阴极到阳极、以相反的顺序来制作有机EL元件。
以下，对于在透光性基板上依次设置有阳极/空穴注入层/发光层/电子注入层/阴极的结构的有机EL元件的制造例进行说明。
首先，通过蒸镀法或溅射法，在透光性基板上形成由阳极材料构成的薄膜，得到阳极。接着，在该阳极上设置空穴注入层。空穴注入层的形成，可以通过真空蒸镀法、旋涂法、流延法、LB法等方法来进行，但从容易得到匀质的膜、且难以产生针孔等方面考虑，优选通过真空蒸镀法来形成。通过真空蒸镀法形成空穴注入层的情况下，该蒸镀条件根据使用的化合物(空穴注入层的材料)、作为目标的空穴注入层的结构等而不同，通常优选在蒸镀源温度50～450℃、真空度10-7～10-3Torr、蒸镀速度0.01～50nm/秒、基板温度-50～300℃下适宜选择。
接着，在空穴注入层上设置发光层。发光层的形成，也可以通过真空蒸镀法、溅射法、旋涂法、流延法等方法将发光材料薄膜化，由此来形成，但从容易得到匀质的膜、且难以产生针孔等方面考虑，优选通过真空蒸镀法来形成。通过真空蒸镀法形成发光层的情况下，该蒸镀条件根据使用的化合物而不同，通常可以从与空穴注入层的形成相同的条件范围中进行选择。
然后，在发光层上设置电子注入层。此时与空穴注入层、发光层同样，从需要得到匀质的膜考虑，优选通过真空蒸镀法来形成。蒸镀条件可以从与空穴注入层、发光层同样的条件范围中进行选择。
最后，可以层压阴极来得到有机EL元件。阴极可以利用蒸镀法、溅射法形成。但是，为了保护底层的有机物层免受制膜时的损伤，优选真空蒸镀法。
以上有机EL元件的制造，优选通过一次抽真空连续进行，从阳极到阴极来制造。
有机EL元件的各层的形成方法没有特别的限定。含有本发明化合物的有机薄膜层，可以通过基于真空蒸镀法、分子束蒸镀法(MBE法)、或将本发明化合物溶解于溶剂中得到的溶液的浸渍法、旋涂法、流延法、刮棒涂布法、辊涂法等涂布法的公知方法来形成。
实施例
以下，通过实施例对本发明进行更加具体的说明。
合成例1
通过下述反应合成苯并[g]
。
(A-1)9-(2-甲酰基苯基)菲的合成
在氩气氛围下，在烧瓶中投入9-溴菲25.7g、2-甲酰基苯基硼酸16.5g、四(三苯基膦)钯(0)2.31g，加入二甲氧基乙烷(DME)340mL、2M碳酸钠水溶液170mL，加热回流搅拌8小时。冷却至室温后，除去水层。用水、饱和食盐水洗涤有机层后，用硫酸镁进行干燥。过滤除去硫酸镁后，将有机层浓缩。通过硅胶色谱法将残渣进行精制，得到作为目标的9-(2-甲酰基苯基)菲25.0g(收率89％)。
(A-2)9-[1-(2-甲氧基乙烯基)苯基]菲的合成
在氩气氛围下，投入9-(2-甲酰基苯基)菲25.0g、甲氧基甲基三苯基氯化鏻33.4g、四氢呋喃(THF)300mL，室温下搅拌过程中，加入叔丁氧基钾11.9g。室温下搅拌2小时后，加入水200mL。用乙醚提取反应溶液，除去水层。用水、饱和食盐水洗涤有机层后，用硫酸镁进行干燥。过滤除去硫酸镁后，将有机层浓缩。通过硅胶色谱法将残渣进行精制，得到作为目标的9-[1-(2-甲氧基乙烯基)苯基]菲24.0g(收率87％)。
(A-3)苯并[g]
的合成
投入9-[1-(2-甲氧基乙烯基)苯基]菲24.0g、二氯甲烷100mL，室温下搅拌过程中，用巴士吸管滴加甲磺酸6滴。室温下持续搅拌8小时。反应结束后加入10％碳酸钾水溶液100mL。除去水层。用水、饱和食盐水洗涤有机层后，用硫酸镁进行干燥。过滤除去硫酸镁后，将有机层浓缩。通过硅胶色谱法将残渣进行精制，得到作为目标的苯并[g]
5.21g(收率25％)。
合成例2
由苯并[g]
合成作为本发明化合物的中间体的苯并[g]
-10-硼酸。
(B-1)10-溴苯并[g]
的合成
在烧瓶中投入苯并[g]
5.21g、N，N-二甲基甲酰胺50mL，再加入N-溴代琥珀酰亚胺4.00g的N，N-二甲基甲酰胺10mL溶液。在80℃下加热搅拌8小时。冷却至室温后，将反应溶液注入到水200mL中。过滤得到析出的固体，用水、甲醇洗涤。将所得到的固体用硅胶色谱法进行精制，得到10-溴苯并[g]
5.87g(收率88％)。
(B-2)苯并[g]
-10-硼酸的合成
在氩气氛围下，在烧瓶中投入10-溴苯并[g]
5.87g，加入脱水乙醚200mL、脱水甲苯200mL。将反应溶液冷却至-40℃，加入1.6M正丁基锂的己烷溶液11mL，升温至0℃，搅拌1小时。将反应溶液冷却至-60℃，滴加硼酸三异丙酯7.72g的脱水乙醚10mL溶液。将反应溶液升温至室温的同时持续搅拌5小时。加入10％盐酸水溶液100mL，搅拌1小时。除去水层。用水、饱和食盐水洗涤有机层后，用硫酸镁进行干燥。过滤除去硫酸镁后，将有机层浓缩。将所得到的固体用己烷洗涤，得到作为目标的苯并[g]-10-硼酸3.18g(收率60％)。
[稠环芳烃衍生物的合成]
实施例1
通过下述反应来合成下述化合物1。
在氩气氛围下，投入苯并[g]
-10-硼酸7.72g、1，4-二溴苯2.36g、四(三苯基膦)钯(0)0.462g、甲苯(toluene)80mL、2M碳酸钠水溶液40mL，回流搅拌8小时。冷却至室温后，用甲苯提取反应溶液。除去水层。用水、饱和食盐水洗涤有机层后，用硫酸镁进行干燥。过滤除去硫酸镁后，将有机层浓缩。通过硅胶色谱法将残渣进行精制，得到白色结晶5.04g。该物质经质谱分析结果证明为目标物，相对于分子量630.23为m/z＝630。
实施例2
通过下述反应来合成下述化合物2。
在实施例1中，使用4，4’-二溴联苯代替1，4-二溴苯，通过同样的方法进行合成。该物质经质谱分析结果证明为目标物，相对于分子量706.27为m/z＝706。
实施例3
通过下述反应来合成下述化合物3。
在化合物1的合成中，使用由已知方法合成的2，7-二溴-9，9-二甲基芴代替1，4-二溴苯，通过同样的方法进行合成。该物质经质谱分析结果证明为目标物，相对于分子量746.30为m/z＝746。
实施例4
通过下述反应来合成下述化合物4。
在化合物1的合成中，使用1，4-二溴萘代替1，4-二溴苯，通过同样的方法进行合成。该物质经质谱分析结果证明为目标物，相对于分子量680.25为m/z＝680。
实施例5
通过下述反应来合成下述化合物5。
在实施例1的合成中，使用2，6-二溴萘代替1，4-二溴苯，通过同样的方法进行合成。该物质经质谱分析结果证明为目标物，相对于分子量680.25为m/z＝680。
·有机EL元件的制作
实施例6
将25mm×75mm×1.1mm厚的带ITO透明电极(阳极)的玻璃基板(ジオマテイク公司制)在异丙醇中进行超声波清洗5分钟，之后，进行UV臭氧清洗30分钟。将清洗后的带透明电极线的玻璃基板安装在真空蒸镀装置的基板支架上，首先，在形成透明电极线的一侧的面上覆盖所述透明电极，使膜厚60nm的下述化合物A-1成膜。A-1成膜后，在该A-1膜上使膜厚20nm的下述化合物A-2成膜。
接着，在该A-2膜上以膜厚40nm使本发明的化合物1与苯乙烯基胺衍生物D-1以40∶2的膜厚比进行成膜，得到蓝色系发光层。
在该膜上通过蒸镀以膜厚20nm使下述化合物Alq成膜作为电子传输层。之后，使LiF以膜厚1nm成膜。在该LiF膜上使金属Al蒸镀150nm，形成金属阴极，从而形成有机EL发光元件。
实施例7-10
除了使用表1所示的化合物2-5代替化合物1之外，与实施例6同样操作，制作有机EL元件。
比较例1
除了使用下述化合物B代替化合物1之外，与实施例6同样操作，制作有机EL元件。
测定由上述各例子制作的有机EL元件的10mA/cm2驱动时的元件性能以及对于初期1000cd/m2的半衰期。将结果示于表1。
另外，发光效率，是在元件上施加规定的电压并测定此时的电流值时，同时用亮度计(ミノルタ公司制造的分光亮度放射计CS-1000)测定发光亮度值而算出。
表1
| 主体 | 掺杂物 | 电压(V) | 发光效率(cd/A) | 发光颜色 | 寿命(小时) | |
| 实施例6 | 化合物1 | D-1 | 6.5 | 6.5 | 蓝色 | 6000 |
| 实施例7 | 化合物2 | D-1 | 6.6 | 6.5 | 蓝色 | 7000 |
| 实施例8 | 化合物3 | D-1 | 6.5 | 6.3 | 蓝色 | 5500 |
| 实施例9 | 化合物4 | D-1 | 6.7 | 6.7 | 蓝色 | 8000 |
| 实施例10 | 化合物5 | D-1 | 6.7 | 6.7 | 蓝色 | 8000 |
| 比较例1 | 化合物B | D-1 | 7.0 | 6.0 | 蓝色 | 4000 |
实施例11
将25mm×75mm×1.1mm厚的带ITO透明电极的玻璃基板(ジオマテイク公司制)在异丙醇中进行超声波清洗5分钟，之后，进行UV臭氧清洗30分钟。
将清洗后的带透明电极线的玻璃基板安装在真空蒸镀装置的基板支架上，首先，在形成透明电极线的一侧的面上覆盖所述透明电极，使膜厚50nm的4，4’-双[N-(1-萘基)-N-苯基氨基]联苯膜(以下简略记为“NPD膜”)利用电阻加热蒸镀进行成膜。该NPD膜作为空穴注入/传输层起作用。
接着，在该NPD膜上利用电阻加热蒸镀以膜厚40nm使化合物1进行成膜。同时将下述所示的PQIr(acac)作为磷光性掺杂物以成为发光层全体的5质量％来进行蒸镀。该膜作为磷光发光层起作用。
接着，在该磷光发光层上利用电阻加热蒸镀使下述化合物I成膜，使厚度为10nm。该化合物I的膜作为空穴障壁层起作用。
在该膜上使膜厚30nm的三(8-羟基喹啉)铝(Alq3)络合物成膜。其作为电子传输层起作用。
之后，使作为还原性掺杂物的Li(Li源：サエスゲツタ一公司制)和Alq进行二次蒸镀，形成Alq:Li膜(膜厚0.5nm)作为电子注入层。
在该Alq:Li膜上使金属Al蒸镀，形成金属阴极(膜厚150nm)，从而形成有机EL元件。
实施例12-15
除了使用表2所示的化合物2-5代替化合物1之外，与实施例11同样操作，制作有机EL元件。
比较例2
除了使用下述化合物C代替化合物1之外，与实施例11同样操作，制作有机EL元件。
测定由实施例11-15以及比较例2制作的有机EL元件的10mA/cm2驱动时的元件性能以及对于初期1000cd/m2的半衰期。将结果示于表2。
另外，EQE(外部量子效率)可以由从发光光谱算出的光子数和驱动时的电流密度求出。
表2
| 主体 | 掺杂物 | 元件性能EQE(％) | 寿命(小时) | |
| 实施例11 | 化合物1 | PQIr(acac) | 18.3 | 30000 |
| 实施例12 | 化合物2 | PQIr(acac) | 18.4 | 30000 |
| 实施例13 | 化合物3 | PQIr(acac) | 18.4 | 25000 |
| 实施例14 | 化合物4 | PQIr(acac) | 18.3 | 30000 |
| 实施例15 | 化合物5 | PQIr(acac) | 18.3 | 30000 |
| 比较例2 | 化合物C | PQIr(acac) | 18.2 | 3000 |
实施例16
通过下述反应来合成下述化合物6。
在化合物1的合成(实施例1)中，使用N-苯基-3，6-二溴咔唑代替1，4-二溴苯，通过同样的方法进行合成。该物质经质谱分析结果证明为目标物，相对于分子量795.29为m/z＝795。
实施例17
通过下述反应来合成下述化合物7。
在氩气氛围下，投入苯并[g]
-10-硼酸11.6g、1，4-二溴苯2.36g、四(三苯基膦)钯(0)0.693g、甲苯120mL、2M碳酸钠水溶液60mL，回流搅拌8小时。冷却至室温后，用甲苯提取反应溶液。除去水层，用水、饱和食盐水洗涤有机层后，用硫酸镁进行干燥。过滤除去硫酸镁后，将有机层浓缩。通过硅胶色谱法将残渣进行精制，得到白色结晶5.54g。该物质经质谱分析结果证明为目标物，相对于分子量906.33为m/z＝906。
实施例18
通过下述反应来合成下述化合物8。
在化合物1的合成(实施例1)中，使用1，8-二溴二苯并呋喃代替1，4-二溴苯，通过同样的方法进行合成。该物质经质谱分析结果证明为目标物，相对于分子量720.25为m/z＝720。
实施例19-21
除了使用表3所示的由实施例16-18制备的化合物6-8代替化合物1之外，与实施例11同样操作，制作有机EL元件。测定由实施例19-21制作的有机EL元件的10mA/cm2驱动时的元件性能以及对于初期1000cd/m2的半衰期。将结果示于表3。
另外，EQE(外部量子效率)可以由从发光光谱算出的光子数和驱动时的电流密度求出。
表3
| 主体 | 掺杂物 | 元件性能EQE(％) | 寿命(小时) | |
| 实施例19 | 化合物6 | PQIr(acac) | 18.0 | 20000 |
| 实施例20 | 化合物7 | PQIr(acac) | 18.2 | 25000 |
| 实施例21 | 化合物8 | PQIr(acac) | 18.4 | 26000 |
产业上利用的可能性
本发明的稠环芳烃衍生物适宜作为有机EL元件用材料、特别是作为发光材料。
本发明的有机EL元件，可以适宜使用于平面发光体或显示器的背灯等光源、手机、PDA、汽车导航、车的仪表盘等显示部分、照明等。
在此引用本说明书中记载的文献内容。
Claims (12)
1.一种稠环芳烃衍生物，其由下述式(1)表示，
式(1)中，Ra及Rb分别表示氢原子或者取代基，m、n分别独立地表示1～13的整数，m、n为2以上时，Ra、Rb可分别相同或不同，L1表示单键或者取代或未取代的2价连接基团，其中，式(1)的稠环芳烃衍生物不具有蒽环。
2.根据权利要求1所述的稠环芳烃衍生物，其由下述式(2)表示，
式(2)中，Ra及Rb分别表示氢原子或者取代基，m、n分别独立地表示1～13的整数，m、n为2以上时，Ra、Rb可分别相同或不同，L2表示单键或者取代或未取代的2价连接基团，其中，式(2)的稠环芳烃衍生物不具有蒽环。
3.根据权利要求1或2所述的稠环芳烃衍生物，其中，L1或L2为取代或未取代的环碳原子数6～50的亚芳基。
4.一种有机电致发光元件用材料，其中，含有权利要求1～3中任一项所述的稠环芳烃衍生物。
5.根据权利要求4所述的有机电致发光元件用发光材料，其为发光材料。
6.一种有机电致发光元件，其中，具有阳极和阴极以及在所述阳极及阴极之间夹持的包含发光层的1层以上的有机薄膜层，
所述有机薄膜层的至少一层含有权利要求1～3中任一项所述的化合物。
7.根据权利要求6所述的有机电致发光元件，其中，所述发光层含有所述稠环芳烃衍生物。
8.根据权利要求7所述的有机电致发光元件，其中，所述发光层含有所述稠环芳烃衍生物作为主体材料。
9.根据权利要求6～8中任一项所述的有机电致发光元件，其中，所述发光层还含有荧光性掺杂物和磷光性掺杂物中的至少一种。
10.根据权利要求9所述的有机电致发光元件，其中，所述荧光性掺杂物为芳基胺化合物。
11.根据权利要求9所述的有机电致发光元件，其中，所述荧光性掺杂物为苯乙烯基胺化合物。
12.根据权利要求9所述的有机电致发光元件，其中，所述磷光性掺杂物为金属络合化合物。
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- 2008-11-10 CN CN200880116295A patent/CN101861291A/zh active Pending
- 2008-11-10 KR KR1020107010623A patent/KR101353635B1/ko active IP Right Grant
- 2008-11-10 US US12/743,173 patent/US8222637B2/en active Active
- 2008-11-10 JP JP2009541127A patent/JPWO2009063833A1/ja active Pending
- 2008-11-10 EP EP08849197A patent/EP2216313B1/en active Active
- 2008-11-13 TW TW097143876A patent/TW200932706A/zh unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114478154A (zh) * | 2022-02-25 | 2022-05-13 | 西安欧得光电材料有限公司 | 一种苉的工业合成方法 |
| CN114478154B (zh) * | 2022-02-25 | 2023-11-21 | 西安欧得光电材料有限公司 | 一种苉的工业合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPWO2009063833A1 (ja) | 2011-03-31 |
| WO2009063833A1 (ja) | 2009-05-22 |
| EP2216313B1 (en) | 2013-02-20 |
| US8222637B2 (en) | 2012-07-17 |
| KR20100088612A (ko) | 2010-08-09 |
| EP2216313A4 (en) | 2011-10-19 |
| TW200932706A (en) | 2009-08-01 |
| EP2216313A1 (en) | 2010-08-11 |
| KR101353635B1 (ko) | 2014-01-20 |
| US20100320451A1 (en) | 2010-12-23 |
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