JPH04363891A - Electroluminescence element - Google Patents
Electroluminescence elementInfo
- Publication number
- JPH04363891A JPH04363891A JP3222793A JP22279391A JPH04363891A JP H04363891 A JPH04363891 A JP H04363891A JP 3222793 A JP3222793 A JP 3222793A JP 22279391 A JP22279391 A JP 22279391A JP H04363891 A JPH04363891 A JP H04363891A
- Authority
- JP
- Japan
- Prior art keywords
- oxadiazole
- electroluminescent device
- formula
- rings
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000005401 electroluminescence Methods 0.000 title abstract 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims abstract description 49
- -1 oxadiazole compound Chemical class 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims description 20
- 238000002347 injection Methods 0.000 claims description 14
- 239000007924 injection Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 abstract description 40
- 239000000463 material Substances 0.000 abstract description 13
- 239000012044 organic layer Substances 0.000 abstract description 2
- 238000004020 luminiscence type Methods 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000004866 oxadiazoles Chemical class 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical class C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、製膜性に優れ且つ十分
な輝度を発揮しうる発光材料を用いた電界発光素子に関
する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electroluminescent device using a luminescent material that has excellent film formability and can exhibit sufficient brightness.
【０００２】0002
【従来の技術】近年、情報機器の多様化に伴って、ＣＲ
Ｔより低消費電力で空間占有容積が少ない平面表示素子
のニーズが高まっている。このような平面表示素子とし
ては、液晶、プラズマディスプレイ等があるが、特に最
近は、発光型で表示が鮮明なＥＬ素子が注目されている
。[Background Art] In recent years, with the diversification of information equipment, CR
There is a growing need for a flat display element that consumes less power and occupies less space. Such flat display elements include liquid crystal displays, plasma displays, and the like, but recently, EL elements that are light-emitting and display clearly have been attracting attention.
【０００３】ここで、上記ＥＬ素子は構成する材料によ
り、無機ＥＬ素子と有機ＥＬ素子とに大別することがで
き、無機ＥＬ素子は既に実用化されている。しかしなが
ら、上記無機ＥＬの駆動方式は、高電界の印加によって
加速された電子が、発光中心を衝突励起して発光させる
という所謂衝突励起型発光であるため、高電圧で駆動す
る必要がある。このため、周辺機器の高コスト化を招来
するという課題を有していた。[0003] The above-mentioned EL elements can be roughly classified into inorganic EL elements and organic EL elements, depending on the materials of their construction, and inorganic EL elements have already been put into practical use. However, the driving method of the inorganic EL is so-called collision excitation type light emission in which electrons accelerated by the application of a high electric field collide and excite a luminescent center to emit light, so it is necessary to drive it at a high voltage. For this reason, there was a problem in that the cost of peripheral equipment increased.
【０００４】これに対し、上記有機ＥＬ素子は、有機発
光層を挟んで仕事関数の異なる対向電極が配置された構
造であり、陽極から注入されたホールと陰極から注入さ
れた電子とが発光層中で再結合して、発光層のケイ光と
同一波長の光を発するという所謂注入型発光である。し
たがって、低電圧で駆動することができ、且つ発光層の
材料を変更することにより任意の発光色を得ることが可
能である。On the other hand, the organic EL device described above has a structure in which opposing electrodes with different work functions are arranged with an organic light-emitting layer sandwiched between them, and holes injected from the anode and electrons injected from the cathode are transferred to the light-emitting layer. This is so-called injection-type light emission in which the light is recombined inside and emits light of the same wavelength as the fluorescence of the light-emitting layer. Therefore, it is possible to drive with a low voltage, and by changing the material of the light-emitting layer, it is possible to obtain any luminescent color.
【０００５】加えて、上記有機ＥＬ素子に用いる有機化
合物は、置換基を変える等によってその性質が異なるた
め、無機化合物よりも材料設計の自由度が大きい。した
がって、分子の電子状態を考慮しつつ有機化合物の分子
構造を変更することによって、任意の発光材料を得るこ
とができるものと考えられる。したがって、理論上は、
青色から赤色までの全ての色を発光させることが可能で
あり、実際に、緑色、黄色、橙色を発光させる安定な発
光材料は種々提案されている。[0005] In addition, the organic compounds used in the organic EL elements have different properties due to changes in substituents, etc., and therefore have a greater degree of freedom in material design than inorganic compounds. Therefore, it is considered that any luminescent material can be obtained by changing the molecular structure of an organic compound while taking into consideration the electronic state of the molecule. Therefore, in theory,
It is possible to emit light in all colors from blue to red, and in fact, various stable light-emitting materials that emit green, yellow, and orange light have been proposed.
【０００６】[0006]
【発明が解決しようとする課題】しかしながら、青色を
安定且つ高輝度で発光させる発光材料は、無機ＥＬ素子
、有機ＥＬ素子を問わず、未だ開発されていない現状に
ある。例えば、有機ＥＬ素子における青色の発光材料と
しては、１，１，４，４，−テトラフェニル−１，３−
ブタジエン誘導体やスチリルベンゼン誘導体が提案され
ているが、何れも製膜性に劣り、満足な輝度と安定性と
を得られるには到らない。[Problems to be Solved by the Invention] However, a light-emitting material that emits blue light stably and with high brightness has not yet been developed, regardless of whether it is an inorganic EL device or an organic EL device. For example, as a blue light emitting material in an organic EL element, 1,1,4,4,-tetraphenyl-1,3-
Although butadiene derivatives and styrylbenzene derivatives have been proposed, both have poor film-forming properties and cannot achieve satisfactory brightness and stability.
【０００７】本発明はかかる現状に鑑みてなされたもの
であり、青色発光において十分な輝度と安定性とを得る
ことができる発光材料を用いた電界発光素子を提供する
ことを目的とする。The present invention has been made in view of the current situation, and it is an object of the present invention to provide an electroluminescent device using a luminescent material that can obtain sufficient brightness and stability in blue light emission.
【０００８】[0008]
【課題を解決するための手段】本発明は、上記目的を達
成するために、請求項１の発明は、ホール注入電極と、
電子注入電極と、これら両電極間に設けられた有機発光
層とを有する電界発光素子において、前記有機発光層に
は、複数のオキサジアゾール環を有するオキサジアゾー
ル系化合物が用いられていることを特徴とする。[Means for Solving the Problems] In order to achieve the above object, the invention of claim 1 provides a hole injection electrode,
In an electroluminescent device having an electron injection electrode and an organic light emitting layer provided between these two electrodes, the organic light emitting layer includes an oxadiazole compound having a plurality of oxadiazole rings. It is characterized by
【０００９】請求項２の発明は、請求項１記載の電界発
光素子において、複数のオキサジアゾール環を有するオ
キサジアゾール系化合物が、オキサジアゾール環の間に
ベンゼン環を一つ有する化合物であることを特徴とする
。請求項３の発明は、請求項１記載の電界発光素子にお
いて、複数のオキサジアゾール環を有するオキサジアゾ
ール系化合物が、オキサジアゾール環の間にベンゼン環
を二つ有する化合物であることを特徴とする。The invention according to claim 2 is the electroluminescent device according to claim 1, in which the oxadiazole compound having a plurality of oxadiazole rings is a compound having one benzene ring between the oxadiazole rings. characterized by something. The invention according to claim 3 provides that in the electroluminescent device according to claim 1, the oxadiazole-based compound having a plurality of oxadiazole rings is a compound having two benzene rings between the oxadiazole rings. Features.
【００１０】請求項４の発明は、請求項１記載の電界発
光素子において、複数のオキサジアゾール環を有するオ
キサジアゾール系化合物が、オキサジアゾール環の間に
アルキル鎖を有する化合物であることを特徴とする。請
求項５の発明は、請求項２記載の電界発光素子において
、複数のオキサジアゾール環の数が２であり、ベンゼン
環のオルト位（１，２位）、メタ位（１，３位）、パラ
位（１，４位）がオキサジアゾール環によって置換され
ていることを特徴とする。The invention according to claim 4 is the electroluminescent device according to claim 1, wherein the oxadiazole compound having a plurality of oxadiazole rings is a compound having an alkyl chain between the oxadiazole rings. It is characterized by The invention according to claim 5 is the electroluminescent device according to claim 2, wherein the number of the plurality of oxadiazole rings is 2, and the ortho position (1, 2 position) and meta position (1, 3 position) of the benzene ring. , is characterized in that the para positions (1, 4 positions) are substituted with an oxadiazole ring.
【００１１】請求項６の発明は、請求項５記載の電界発
光素子において、前記２か所をオキサジアゾール環によ
って置換されたベンゼン環が、更にもう１か所オキサジ
アゾール環によって置換されていることを特徴とする。
請求項７の発明は、請求項２記載の電界発光素子におい
て、複数のオキサジアゾール環の数が３であり、ベンゼ
ン環の１，３，５位がオキサジアゾール環によって置換
されていることを特徴とする。[0011] The invention according to claim 6 is the electroluminescent device according to claim 5, wherein the benzene ring substituted at two positions with an oxadiazole ring is further substituted at one position with an oxadiazole ring. It is characterized by the presence of The invention according to claim 7 is the electroluminescent device according to claim 2, wherein the number of the plurality of oxadiazole rings is 3, and the 1, 3, and 5 positions of the benzene ring are substituted with the oxadiazole ring. It is characterized by
【００１２】請求項８の発明は、請求項３記載の電界発
光素子において、複数のオキサジアゾール環の数が２で
あり、前記２個のベンゼン環からなるビフェニル基の４
，４´位又は、２，２´位が２個のオキサジアゾール環
によって置換されていることを特徴とする。請求項９の
発明は、請求項４記載の電界発光素子において、複数の
オキサジアゾール環の数が２であり、前記アルキル鎖の
炭素数が１〜６であることを特徴とする。The invention according to claim 8 is the electroluminescent device according to claim 3, wherein the number of the plurality of oxadiazole rings is 2, and the biphenyl group consisting of the two benzene rings has 4
, 4' or 2,2' positions are substituted with two oxadiazole rings. According to a ninth aspect of the invention, in the electroluminescent device according to the fourth aspect, the number of the plurality of oxadiazole rings is 2, and the number of carbon atoms in the alkyl chain is 1 to 6.
【００１３】請求項１０の発明は、請求項１記載の電界
発光素子において、オキサジアゾール系化合物が、前記
化１〜１４に示す群から選択されることを特徴とする。
尚、上記Ｒ，Ｒ１ ，Ｒ２ ，Ｒ３ は、Ｈ，ＣＨ３
，Ｃ２ Ｈ５ ，Ｃ３ Ｈ７ ，（ＣＨ３ ）３ Ｃ，
ＯＣＨ３ ，ＯＣ２ Ｈ５ ，ＮＨ２ ，Ｎ（ＣＨ３
）２ ，Ｎ（Ｃ２ Ｈ５ ）２ ，ＣＮ，フェニル（前
記化１５に示す），及びシクロヘキシル（前記化１６に
示す）からなる群から選択される。[0013] The invention according to claim 10 is characterized in that in the electroluminescent device according to claim 1, the oxadiazole compound is selected from the group shown in formulas 1 to 14 above. In addition, the above R, R1, R2, R3 are H, CH3
, C2 H5 , C3 H7 , (CH3 )3 C,
OCH3 ,OC2 H5 ,NH2 ,N(CH3
)2, N(C2H5)2, CN, phenyl (shown in Chemical Formula 15 above), and cyclohexyl (shown in Chemical Formula 16 above).
【００１４】上記Ｒ´は、Ｈ，ＣＨ３ ，Ｃ２ Ｈ５
，ＯＣＨ３ ，ＯＣ２ Ｈ５ ，Ｎ（ＣＨ３ ）２ 及
びオキサジアゾール環から成る群から選択される。[0014] The above R' is H, CH3, C2 H5
, OCH3 , OC2 H5 , N(CH3 )2 and an oxadiazole ring.
【００１５】[0015]
【作用】前記複数のオキサジアゾール環を有するオキサ
ジアゾール系化合物は、実験より、製膜性が優れ、且つ
上記オキサジアゾール系化合物を有機発光層に用いた電
界発光素子は、長期間保存或いは作動させた場合であっ
ても結晶が析出せず、輝度が低下しないことが確認され
た。加えて、オキサジアゾール系化合物を有機発光層に
用いた電界発光素子は、４５０〜５３４ｎｍの範囲にピ
ークを有する青色の発光であることが確認された。これ
らのことから、高輝度の青色発光を長期間維持すること
が可能となる。[Function] Experiments have shown that the oxadiazole compound having a plurality of oxadiazole rings has excellent film forming properties, and the electroluminescent device using the oxadiazole compound in the organic luminescent layer can be stored for a long period of time. It was also confirmed that even when the device was operated, crystals did not precipitate and the brightness did not decrease. In addition, it was confirmed that an electroluminescent device using an oxadiazole compound in an organic light emitting layer emits blue light having a peak in the range of 450 to 534 nm. For these reasons, it becomes possible to maintain high-intensity blue light emission for a long period of time.
【００１６】そして、このようなことは、２層構造（Ｓ
Ｈ−Ａ構造、ＳＨ−Ｂ構造）、３層構造に関わらず発揮
しうる。ここで、上記オキサジアゾール系化合物は、一
般に、下記化１７或いは化１８に示すような方法で合成
する。尚、反応時間については、各々の化合物により異
なっている。[0016] And, this kind of thing is caused by a two-layer structure (S
H-A structure, SH-B structure), and 3-layer structure. Here, the above-mentioned oxadiazole compound is generally synthesized by the method shown in Chemical Formula 17 or Chemical Formula 18 below. Note that the reaction time differs depending on each compound.
【００１７】[0017]
【化１７】[Chemical formula 17]
【００１８】[0018]
【化１８】[Chemical formula 18]
【００１９】但し、上記Ａｒは、下記化１９〜化２４か
ら成る群から選択される。However, the above Ar is selected from the group consisting of the following formulas 19 to 24.
【００２０】[0020]
【化１９】[Chemical formula 19]
【００２１】[0021]
【化２０】[C20]
【００２２】[0022]
【化２１】[C21]
【００２３】[0023]
【化２２】[C22]
【００２４】[0024]
【化２３】[C23]
【００２５】[0025]
【化２４】[C24]
【００２６】[0026]
（第１実施例）本発明の第１実施例を、図１に基づいて
以下に説明する。図１は本発明の第１実施例に係る電界
発光素子の断面図であり、ガラス基板１上には、インジ
ウム−スズ酸化物（ＩＴＯ）から成るホール注入電極（
陽極）２と、ジアミン（下記化２５に示す）からなる有
機ホール輸送層３（厚み：６００Å）と、オキサジアゾ
ール誘導体（下記化２６に示す）から成る有機発光層４
（厚み：４００Å）と、ＭｇとＡｇとが１０：１の比率
で混合された電子注入電極（陰極）５（厚み：２０００
Å）とが、順に形成されている。(First Embodiment) A first embodiment of the present invention will be described below with reference to FIG. FIG. 1 is a cross-sectional view of an electroluminescent device according to a first embodiment of the present invention. On a glass substrate 1, a hole injection electrode (
an anode) 2, an organic hole transport layer 3 (thickness: 600 Å) made of diamine (shown in Chemical Formula 25 below), and an organic light emitting layer 4 made of an oxadiazole derivative (shown in Chemical Formula 26 below).
(Thickness: 400 Å) and electron injection electrode (cathode) 5 (Thickness: 2000 Å) made of a mixture of Mg and Ag at a ratio of 10:1.
Å) are formed in this order.
【００２７】[0027]
【化２５】[C25]
【００２８】[0028]
【化２６】[C26]
【００２９】ここで、上記構造の電界発光素子を、以下
のようにして作製した。先ず、ガラス基板１上にインジ
ウム−スズ酸化物（ＩＴＯ）からなるホール注入電極２
が形成された基板を中性洗剤により洗浄した後、アセト
ン中で２０分間、エタノール中で約２０分間超音波洗浄
をした。次いで、上記基板を沸騰したエタノール中に約
１分間入れ、取り出した後、すぐに送風乾燥を行った。
この後、上記ホール注入電極２上に、ジアミンを真空蒸
着して有機ホール輸送層３を形成した後、この有機ホー
ル輸送層３上に、オキサジアゾール誘導体を真空蒸着し
て、有機発光層４を形成した。しかる後、有機発光層４
上に、ＭｇとＡｇとを１０：１の比率で共蒸着して、電
子注入電極５を形成して、ＳＨ−Ａ構造の有機電界発光
素子を作製した。尚、上記蒸着はいずれも、真空度１×
１０−６Ｔｏｒｒ、基板温度２０℃、有機層の蒸着速度
２Å／ｓｅｃという条件下で行った。Here, an electroluminescent device having the above structure was manufactured as follows. First, a hole injection electrode 2 made of indium-tin oxide (ITO) is placed on a glass substrate 1.
The substrate on which was formed was washed with a neutral detergent, and then subjected to ultrasonic cleaning in acetone for 20 minutes and in ethanol for about 20 minutes. Next, the substrate was placed in boiling ethanol for about 1 minute, taken out, and immediately air-dried. Thereafter, diamine is vacuum-deposited on the hole-injection electrode 2 to form an organic hole-transporting layer 3, and then an oxadiazole derivative is vacuum-deposited on the organic hole-transporting layer 3 to form an organic light-emitting layer 4. was formed. After that, the organic light emitting layer 4
Mg and Ag were co-evaporated thereon at a ratio of 10:1 to form an electron injection electrode 5, thereby producing an organic electroluminescent device with an SH-A structure. In addition, the above vapor deposition was performed at a vacuum degree of 1×
The deposition was carried out under the conditions of 10-6 Torr, a substrate temperature of 20° C., and an organic layer deposition rate of 2 Å/sec.
【００３０】ところで、上記オキサジアゾールは、以下
に示すように、オキサジアゾールの前駆体の合成、オキ
サジアゾールの合成という工程を経て作成した。
１．オキサジアゾールの前駆体の合成
先ず、３つ口フラスコ（容量：５００ｍｌ）にＩｓｏｐ
ｈｔｈａｌｉｃ Ｄｉｈｙｄｒａｚｉｄｅ を１２．３
７ｇ（６３．７ｍｍｏｌ）装填し、さらに脱水ピリジン
１００ｍｌを入れる。次に、上記口部に冷却管を装着し
てフラスコ内にＮ２ ガスを導入し、フラスコ内をＮ２
雰囲気として、ピリジンを還流させる。この状態で、
滴下ロートより４− ｔｅｒｔ−Ｂｕｔｙｌｂｅｎｚｏ
ｙｌ ｃｈｌｏｒｉｄｅ２４．３７ｇ（１２５．７ｍｍ
ｏｌ）を３０分かけて滴下させる。滴下終了後、１０時
間還流を続ける。反応が終了したら、蒸留により、ピリ
ジンを反応系より除去する。反応物はよく水洗し、真空
デシケータ中で真空乾燥を行う。これにより、オキサジ
アゾール前駆体が作成される。上記反応を下記化２７に
示す。By the way, the above oxadiazole was produced through the steps of synthesizing an oxadiazole precursor and synthesizing oxadiazole, as shown below. 1. Synthesis of oxadiazole precursor First, in a three-necked flask (capacity: 500 ml),
hthalic Dihydrazide 12.3
7 g (63.7 mmol) was loaded, and further 100 ml of dehydrated pyridine was added. Next, a cooling pipe is attached to the above mouth and N2 gas is introduced into the flask.
The atmosphere is refluxing pyridine. In this state,
Add 4-tert-Butylbenzo from the dropping funnel.
yl chloride24.37g (125.7mm
ol) was added dropwise over 30 minutes. After the dropwise addition is complete, reflux is continued for 10 hours. After the reaction is completed, pyridine is removed from the reaction system by distillation. The reaction product is thoroughly washed with water and vacuum dried in a vacuum desiccator. This creates an oxadiazole precursor. The above reaction is shown below.
【００３１】[0031]
【化２７】[C27]
【００３２】２．オキサジアゾールの合成３つ口フラス
コ（容量：５００ｍｌ）に上記オキサジアゾール前駆体
１０ｇを入れ、さらにオキソ塩化リン（ＰＯＣｌ３ ）
１００ｍｌを入れる。次に、上記口部に冷却管を装着し
て、オキソ塩化リンを７時間還流させる。反応終了後、
オキソ塩化リンを蒸留により反応系外へ除去する。反応
系に残った残留オキソ塩化リンを水と反応させながら、
反応物を良く水洗する。反応物は、真空デシケータ中で
真空乾燥させる。これにより、オキサジアゾールが合成
される。尚、このオキサジアゾールは、昇華精製により
精製を行う。この場合の精製収率は３０％であった。上
記反応を下記化２８に示す。2. Synthesis of oxadiazole 10 g of the above oxadiazole precursor was placed in a three-neck flask (capacity: 500 ml), and phosphorous chloride (POCl3) was added.
Add 100ml. Next, a cooling pipe is attached to the mouth part, and the oxophosphorus chloride is refluxed for 7 hours. After the reaction is complete,
Oxophosphorous chloride is removed from the reaction system by distillation. While reacting the residual oxochloride phosphorus remaining in the reaction system with water,
Wash the reaction product thoroughly with water. The reactants are vacuum dried in a vacuum desiccator. As a result, oxadiazole is synthesized. Note that this oxadiazole is purified by sublimation purification. The purification yield in this case was 30%. The above reaction is shown below.
【００３３】[0033]
【化２８】[C28]
【００３４】尚、上記オキサジアゾールの元素分析を行
ったので、その結果を下記に示す。尚、括弧内は、理論
値である。
Ｈ：６．３５％（６．３２％）
Ｃ：７５．３７％（７５．２９％）
Ｎ：１１．６３％（１１．７１％）
また、融点は２４２℃であった。The above oxadiazole was subjected to elemental analysis, and the results are shown below. Note that the values in parentheses are theoretical values. H: 6.35% (6.32%) C: 75.37% (75.29%) N: 11.63% (11.71%) Moreover, the melting point was 242°C.
【００３５】このようにして作製した有機ＥＬ素子を、
以下（Ａ）素子と称する。
〔実験〕上記（Ａ）素子のホール注入電極２側にプラス
のバイアスを印加したところ、波長４６５ｎｍをピーク
とする青色のＥＬ発光を得ることができた。また、駆動
電圧１７Ｖ、電流密度６３ｍＡ／ｃｍ２ という条件下
で、６００ｃｄ／ｍ２ という高輝度が確認された。[0035] The organic EL device thus produced was
Hereinafter, it will be referred to as (A) element. [Experiment] When a positive bias was applied to the hole injection electrode 2 side of the above device (A), blue EL emission with a peak wavelength of 465 nm could be obtained. Furthermore, under the conditions of a driving voltage of 17 V and a current density of 63 mA/cm2, a high luminance of 600 cd/m2 was confirmed.
【００３６】（第２実施例）有機発光層４の材料として
下記化２９〜化３７に示すオキサジアゾール誘導体を用
いる他は、上記第１実施例の電界発光素子と同様の構造
である。尚、有機発光層４は真空蒸着法にて形成し、且
つその厚みは４００Åである。(Second Embodiment) The electroluminescent device has the same structure as the electroluminescent device of the first embodiment, except that the oxadiazole derivatives shown below are used as materials for the organic light emitting layer 4. Note that the organic light emitting layer 4 is formed by a vacuum evaporation method, and has a thickness of 400 Å.
【００３７】[0037]
【化２９】[C29]
【００３８】[0038]
【化３０】[C30]
【００３９】[0039]
【化３１】[Chemical formula 31]
【００４０】[0040]
【化３２】[C32]
【００４１】[0041]
【化３３】[Chemical formula 33]
【００４２】[0042]
【化３４】[C34]
【００４３】[0043]
【化３５】[C35]
【００４４】[0044]
【化３６】[C36]
【００４５】[0045]
【化３７】[C37]
【００４６】このようにして作製した有機ＥＬ素子を、
以下それぞれ（Ｂ１）素子〜（Ｂ９ ）素子と称する。
（実験）上記（Ｂ１ ）素子〜（Ｂ９ ）素子に用いた
オキサジアゾールの蛍光（ＰＬ）と、ＥＬ波長と、輝度
と、電圧と、電流密度と、発光色とを調べたので、その
結果を表１に示す。[0046] The organic EL device thus produced was
Hereinafter, they will be referred to as elements (B1) to (B9), respectively. (Experiment) The fluorescence (PL), EL wavelength, brightness, voltage, current density, and emission color of the oxadiazole used in the above (B1) to (B9) devices were investigated, and the results were are shown in Table 1.
【００４７】[0047]
【表１】[Table 1]
【００４８】上記表１から明らかなように、（Ｂ１ ）
素子〜（Ｂ９ ）素子は青色或いは青緑色のＥＬ発光で
あり、且つ高輝度を有していることが確認された。また
、図示はしないが、（Ｂ１ ）素子〜（Ｂ９ ）素子は
優れた耐久性を有していることも実験により確認してい
る。
尚、上記実施例では、オキサジアゾール環の間にアルキ
ル鎖を有する化合物について炭素数が３の化合物のみ結
果が記述されているが、他に炭素数が１〜６についても
同様の好結果が得られる。ただし、炭素数が７以上にな
ると化合物の合成上の問題や、電界発光素子を作成する
上で真空蒸着を行う際に、化合物が飛びにくいといった
問題が生じる。As is clear from Table 1 above, (B1)
It was confirmed that the elements ~(B9) emitted blue or blue-green EL light and had high brightness. Although not shown, it has also been confirmed through experiments that elements (B1) to (B9) have excellent durability. In addition, in the above examples, results are described only for compounds having an alkyl chain between oxadiazole rings and having 3 carbon atoms, but similar good results were also obtained for compounds having 1 to 6 carbon atoms. can get. However, if the number of carbon atoms is 7 or more, problems arise in the synthesis of the compound and in that the compound is difficult to fly off when performing vacuum deposition to create an electroluminescent device.
【００４９】（第３実施例）
〔実施例１〕有機発光層４の材料として、下記化３８に
示すオキサジアゾール誘導体を用い、且つ有機発光層４
の厚みを１００Åとすると共に、図２に示すように有機
発光層４と電子注入電極５との間に前記オキサジアゾー
ル誘導体（前記化２７に示すもの）からなる有機電子輸
送層６（厚み：３００Å）を形成するという有機３層構
造とする他は、上記第１実施例と同様の構造である。(Third Example) [Example 1] As the material of the organic light emitting layer 4, an oxadiazole derivative shown in the following chemical formula 38 was used, and the organic light emitting layer 4
The thickness is 100 Å, and as shown in FIG. 2, an organic electron transport layer 6 (thickness: The structure is the same as that of the first embodiment, except that it has an organic three-layer structure of 300 Å).
【００５０】[0050]
【化３８】[C38]
【００５１】このようにして作製した有機ＥＬ素子を、
以下（Ｃ１ ）素子と称する。
〔実施例２〕有機発光層４の材料として、下記化３９、
化４０に示すオキサジアゾール誘導体を用いる他は、上
記実施例１と同様の構造である。[0051] The organic EL device thus produced was
Hereinafter, it will be referred to as the (C1) element. [Example 2] As the material of the organic light emitting layer 4, the following chemical formula 39,
The structure is the same as in Example 1 above, except that the oxadiazole derivative shown in Chemical Formula 40 is used.
【００５２】[0052]
【化３９】[C39]
【００５３】[0053]
【化４０】[C40]
【００５４】このようにして作製した有機ＥＬ素子を、
以下（Ｃ２ ）素子、（Ｃ３ ）素子と称する。
〔実験〕上記実施例（Ｃ１ ）素子〜（Ｃ３ ）素子に
ついて、オキサジアゾールの蛍光（ＰＬ）と、ＥＬ波長
と、輝度と、電圧と、電流密度と、発光色とを調べたの
で、その結果を表２に示す。[0054] The organic EL device thus produced was
Hereinafter, they will be referred to as (C2) element and (C3) element. [Experiment] Fluorescence (PL) of oxadiazole, EL wavelength, brightness, voltage, current density, and luminescent color were investigated for the devices of Examples (C1) to (C3) above. The results are shown in Table 2.
【００５５】尚、ＥＬ波長については、ホール注入電極
２側にプラスのバイアスを印加して測定を行った。The EL wavelength was measured by applying a positive bias to the hole injection electrode 2 side.
【００５６】[0056]
【表２】[Table 2]
【００５７】表２に示されたように極めて高い輝度を得
ることができるのは、有機３層構造とすることにより、
電荷キャリヤと励起子とを有機発光層４内に確実に閉じ
込めることができるということに起因するものと考えら
れる。
（第４実施例）
〔実施例１〕有機発光層４の厚みを５００Åとし、且つ
電子輸送層６の厚みを４００Åとすると共に、図３に示
すようにホール輸送層を形成しないＳＨ−Ｂ構造とする
他は、上記第３実施例の実施例１と同様の構造である。As shown in Table 2, it is possible to obtain extremely high brightness due to the organic three-layer structure.
This is thought to be due to the fact that charge carriers and excitons can be reliably confined within the organic light emitting layer 4. (Fourth Example) [Example 1] SH-B structure in which the organic light emitting layer 4 has a thickness of 500 Å, the electron transport layer 6 has a thickness of 400 Å, and no hole transport layer is formed as shown in FIG. Other than this, the third embodiment has the same structure as the first embodiment of the third embodiment.
【００５８】このようにして作製した有機ＥＬ素子を、
以下（Ｄ１ ）素子と称する。
〔実施例２〕有機発光層４の厚みを５００Åとし、且つ
電子輸送層６の厚みを４００Åとすると共に、図３に示
すようにホール輸送層を形成しないＳＨ−Ｂ構造とする
他は、上記第３実施例の実施例２の（Ｃ２ ）素子と同
様の構造である。[0058] The organic EL device produced in this way was
Hereinafter, it will be referred to as the (D1) element. [Example 2] The above except that the organic light-emitting layer 4 had a thickness of 500 Å, the electron transport layer 6 had a thickness of 400 Å, and the SH-B structure without a hole transport layer was used as shown in FIG. It has a structure similar to the (C2) element of Example 2 of the third example.
【００５９】このようにして作製した有機ＥＬ素子を、
以下（Ｄ２ ）素子と称する。
〔実験〕上記（Ｄ１ ）素子及び（Ｄ２ ）素子のホー
ル注入電極２側にプラスのバイアスを印加したところ、
それぞれ、波長４８６ｎｍをピークとする青色のＥＬ発
光、５３４ｎｍをピークとする青緑色のＥＬ発光を得る
ことができた。[0059] The organic EL device thus produced was
Hereinafter, it will be referred to as the (D2) element. [Experiment] When a positive bias was applied to the hole injection electrode 2 side of the above (D1) and (D2) elements,
It was possible to obtain blue EL emission with a peak wavelength of 486 nm and blue-green EL emission with a peak wavelength of 534 nm, respectively.
【００６０】また、（Ｄ１ ）素子は、駆動電圧１８Ｖ
、電流密度３００ｍＡ／ｃｍ２ という条件下で、２０
８０ｃｄ／ｍ２ の輝度が認められた。更に、（Ｄ２
）素子は、駆動電圧１７Ｖ、電流密度２００ｍＡ／ｃｍ
２ という条件下で、２１００ｃｄ／ｍ２ の輝度が認
められた。
以上の如く本発明は、２層構造（ＳＨ−Ａ構造、ＳＨ−
Ｂ構造）、３層構造の有機電界発光素子に関わらず適応
しうる。Further, the (D1) element has a driving voltage of 18V.
, under the condition of current density 300mA/cm2, 20
A brightness of 80 cd/m2 was observed. Furthermore, (D2
) The device has a driving voltage of 17V and a current density of 200mA/cm.
2, a brightness of 2100 cd/m2 was observed. As described above, the present invention has two-layer structures (SH-A structure, SH-
Structure B) is applicable regardless of the three-layer structure of the organic electroluminescent device.
【００６１】尚、本発明に用いるオキサジアゾール系化
合物としては、上記実施例のものに限定されるものでは
ない。The oxadiazole compounds used in the present invention are not limited to those in the above examples.
【００６２】[0062]
【発明の効果】以上説明したように本発明によれば、４
５０〜５３４ｎｍの範囲にピークを有する青色発光の電
界発光素子を提供でき、且つ有機発光層の製膜性が優れ
ている。したがって、電界発光素子を長期間にわたって
青色発光させることができるという効果を奏する。[Effects of the Invention] As explained above, according to the present invention, 4
It is possible to provide an electroluminescent device that emits blue light having a peak in the range of 50 to 534 nm, and the film-forming property of the organic light emitting layer is excellent. Therefore, it is possible to cause the electroluminescent element to emit blue light for a long period of time.
【図面の簡単な説明】[Brief explanation of drawings]
【図１】本発明の第１実施例に係るＳＨ−Ａ構造の有機
電界発光素子の断面図である。FIG. 1 is a sectional view of an organic electroluminescent device with an SH-A structure according to a first embodiment of the present invention.
【図２】本発明の第３実施例に係る有機３層構造の有機
電界発光素子の断面図である。FIG. 2 is a cross-sectional view of an organic electroluminescent device with an organic three-layer structure according to a third embodiment of the present invention.
【図３】本発明の第４実施例に係るＳＨ−Ｂ構造の有機
電界発光素子の断面図である。FIG. 3 is a cross-sectional view of an organic electroluminescent device with an SH-B structure according to a fourth embodiment of the present invention.
１ ガラス基板 ２ ホール注入電極 ３ 有機ホール輸送層 ４ 有機発光層 ５ 電子注入電極 ６ 有機電子輸送層 1 Glass substrate 2 Hole injection electrode 3. Organic hole transport layer 4 Organic light emitting layer 5 Electron injection electrode 6 Organic electron transport layer
Claims (10)
これら両電極間に設けられた有機発光層とを有する電界
発光素子において、前記有機発光層には、複数のオキサ
ジアゾール環を有するオキサジアゾール系化合物が用い
られていることを特徴とする電界発光素子。Claim 1: A hole injection electrode, an electron injection electrode,
In an electroluminescent device having an organic luminescent layer provided between these two electrodes, an oxadiazole compound having a plurality of oxadiazole rings is used in the organic luminescent layer. Light emitting element.
るオキサジアゾール系化合物が、オキサジアゾール環の
間にベンゼン環を一つ有する化合物であることを特徴と
する請求項１記載の電界発光素子。2. The electroluminescent device according to claim 1, wherein the oxadiazole compound having a plurality of oxadiazole rings is a compound having one benzene ring between oxadiazole rings. .
るオキサジアゾール系化合物が、オキサジアゾール環の
間にベンゼン環を二つ有する化合物であることを特徴と
する請求項１記載の電界発光素子。3. The electroluminescent device according to claim 1, wherein the oxadiazole compound having a plurality of oxadiazole rings is a compound having two benzene rings between the oxadiazole rings. .
るオキサジアゾール系化合物が、オキサジアゾール環の
間にアルキル鎖を有する化合物であることを特徴とする
請求項１記載の電界発光素子。4. The electroluminescent device according to claim 1, wherein the oxadiazole compound having a plurality of oxadiazole rings is a compound having an alkyl chain between the oxadiazole rings.
２であり、ベンゼン環のオルト位（１，２位）、メタ位
（１，３位）、パラ位（１，４位）がオキサジアゾール
環によって置換されていることを特徴とする請求項２記
載の電界発光素子。5. The number of the plurality of oxadiazole rings is 2, and the ortho positions (1, 2 positions), meta positions (1, 3 positions), and para positions (1, 4 positions) of the benzene ring are oxadiazole rings. 3. The electroluminescent device according to claim 2, wherein the electroluminescent device is substituted with a diazole ring.
って置換されたベンゼン環が、更にもう１か所オキサジ
アゾール環によって置換されていることを特徴とする請
求項５記載の電界発光素子。6. The electroluminescent device according to claim 5, wherein the benzene ring substituted at two positions with an oxadiazole ring is further substituted at one position with an oxadiazole ring.
３であり、ベンゼン環の１，３，５位がオキサジアゾー
ル環によって置換されていることを特徴とする請求項２
記載の電界発光素子。7. Claim 2, wherein the number of the plurality of oxadiazole rings is 3, and the 1, 3, and 5 positions of the benzene ring are substituted with the oxadiazole ring.
The electroluminescent device described above.
２であり、前記２個のベンゼン環からなるビフェニル基
の４，４´位又は、２，２´位がオキサジアゾール環に
よって置換されていることを特徴とする請求項３記載の
電界発光素子。8. The number of the plurality of oxadiazole rings is 2, and the 4,4'-position or the 2,2'-position of the biphenyl group consisting of the two benzene rings is substituted with the oxadiazole ring. The electroluminescent device according to claim 3, characterized in that:
２であり、前記アルキル鎖の炭素数が１〜６であること
を特徴とする請求項４記載の電界発光素子。9. The electroluminescent device according to claim 4, wherein the number of the plurality of oxadiazole rings is 2, and the number of carbon atoms in the alkyl chain is 1 to 6.
下記化１〜１４に示す群から選択されることを特徴とす
る請求項１記載の電界発光素子。 【化１】 【化２】 【化３】 【化４】 【化５】 【化６】 【化７】 【化８】 【化９】 【化１０】 【化１１】 【化１２】 【化１３】 【化１４】 尚、上記Ｒ，Ｒ１ ，Ｒ２ ，Ｒ３ は、Ｈ，ＣＨ３
，Ｃ２ Ｈ５ ，Ｃ３ Ｈ７ ，（ＣＨ３ ）３ Ｃ，
ＯＣＨ３ ，ＯＣ２ Ｈ５ ，ＮＨ２ ，Ｎ（ＣＨ３
）２ ，Ｎ（Ｃ２ Ｈ５ ）２ ，ＣＮ，フェニル（下
記化１５に示す），及びシクロヘキシル（下記化１６に
示す）からなる群から選択される。 上記Ｒ´は、Ｈ，ＣＨ３ ，Ｃ２ Ｈ５ ，ＯＣＨ３
，ＯＣ２ Ｈ５ ，Ｎ（ＣＨ３ ）２ 及びオキサジア
ゾール環から成る群から選択される。 【化１５】 【化１６】10. The oxadiazole compound is
The electroluminescent device according to claim 1, characterized in that the electroluminescent device is selected from the group shown in the following chemical formulas 1 to 14. [Formula 1] [Formula 2] [Formula 3] [Formula 4] [Formula 5] [Formula 6] [Formula 7] [Formula 8] [Formula 9] [Formula 10] [Formula 11] [Formula 12] [Formula 1] 13] [Chemical 14] The above R, R1, R2, R3 are H, CH3
, C2 H5 , C3 H7 , (CH3 )3 C,
OCH3 ,OC2 H5 ,NH2 ,N(CH3
)2, N(C2H5)2, CN, phenyl (shown in Chemical Formula 15 below), and cyclohexyl (shown in Chemical Formula 16 below). The above R' is H, CH3, C2 H5, OCH3
, OC2 H5 , N(CH3 )2 and an oxadiazole ring. [Chemical formula 15] [Chemical formula 16]
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3222793A JP2721441B2 (en) | 1991-02-27 | 1991-09-03 | EL device |
| US07/840,174 US5382477A (en) | 1991-02-27 | 1992-02-24 | Organic electroluminescent element and process for producing the same |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3290591 | 1991-02-27 | ||
| JP3-32905 | 1991-02-27 | ||
| JP3222793A JP2721441B2 (en) | 1991-02-27 | 1991-09-03 | EL device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04363891A true JPH04363891A (en) | 1992-12-16 |
| JP2721441B2 JP2721441B2 (en) | 1998-03-04 |
Family
ID=26371508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3222793A Expired - Fee Related JP2721441B2 (en) | 1991-02-27 | 1991-09-03 | EL device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2721441B2 (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05255664A (en) * | 1992-03-12 | 1993-10-05 | Fuji Electric Co Ltd | Luminescent element of organic thin film |
| US5986121A (en) * | 1995-07-17 | 1999-11-16 | Chisso Corporation | Silacyclopentadiene derivatives and an organic electroluminescent element obtained by using the silacyclopentadiene derivative |
| US6376694B1 (en) | 1998-07-09 | 2002-04-23 | Chisso Corporation | Silole derivatives and organic electroluminescent element containing the same |
| US6436559B1 (en) | 1999-11-12 | 2002-08-20 | Canon Kabushiki Kaisha | Organic luminescence device |
| US6461749B2 (en) | 2000-03-31 | 2002-10-08 | Canon Kabushiki Kaisha | Organic boron compound, process for producing the compound and organic luminescence device using the compound |
| US6617053B2 (en) | 2000-08-04 | 2003-09-09 | Chisso Corporation | Organic electroluminescent device containing dithiafulvene derivative |
| US6696182B2 (en) | 2000-09-07 | 2004-02-24 | Chisso Corporation | Organic electroluminescent device comprising dipyridylthiophene derivative |
| US6902832B2 (en) | 2000-07-07 | 2005-06-07 | Chisso Corporation | Charge-transporting material containing diazapentacene derivative, luminescent material, and organic electroluminescent element employing these |
| LT5444B (en) | 2005-12-30 | 2007-10-25 | Vilniaus Universitetas | Non-polymeric compounds with charge carrier transport properties and organic electroluminescence element |
| US7662487B2 (en) | 2005-09-09 | 2010-02-16 | Idemitsu Kosan Co., Ltd. | Azaaromatic compounds having azafluoranthene skeletons and organic electroluminescent devices made by using the same |
| LT5783B (en) | 2009-12-11 | 2011-10-25 | Vilniaus Universitetas, , | Organic iridium complexes, method of preparation thereof and organic electroluminescent element |
| JP2012056953A (en) * | 2004-03-25 | 2012-03-22 | Hodogaya Chem Co Ltd | Compound having oxadiazole ring structure substituted with pyridyl group and organic electroluminescent device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7629060B2 (en) | 2002-11-26 | 2009-12-08 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, and display and illuminator |
-
1991
- 1991-09-03 JP JP3222793A patent/JP2721441B2/en not_active Expired - Fee Related
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05255664A (en) * | 1992-03-12 | 1993-10-05 | Fuji Electric Co Ltd | Luminescent element of organic thin film |
| US5986121A (en) * | 1995-07-17 | 1999-11-16 | Chisso Corporation | Silacyclopentadiene derivatives and an organic electroluminescent element obtained by using the silacyclopentadiene derivative |
| US6051319A (en) * | 1995-07-17 | 2000-04-18 | Chisso Corporation | Silacyclopentadiene derivatives and an organic electroluminescent element obtained by using the silacyclopentadiene derivative |
| US6376694B1 (en) | 1998-07-09 | 2002-04-23 | Chisso Corporation | Silole derivatives and organic electroluminescent element containing the same |
| US6436559B1 (en) | 1999-11-12 | 2002-08-20 | Canon Kabushiki Kaisha | Organic luminescence device |
| US6461749B2 (en) | 2000-03-31 | 2002-10-08 | Canon Kabushiki Kaisha | Organic boron compound, process for producing the compound and organic luminescence device using the compound |
| US6902832B2 (en) | 2000-07-07 | 2005-06-07 | Chisso Corporation | Charge-transporting material containing diazapentacene derivative, luminescent material, and organic electroluminescent element employing these |
| US6617053B2 (en) | 2000-08-04 | 2003-09-09 | Chisso Corporation | Organic electroluminescent device containing dithiafulvene derivative |
| US6696182B2 (en) | 2000-09-07 | 2004-02-24 | Chisso Corporation | Organic electroluminescent device comprising dipyridylthiophene derivative |
| JP2012056953A (en) * | 2004-03-25 | 2012-03-22 | Hodogaya Chem Co Ltd | Compound having oxadiazole ring structure substituted with pyridyl group and organic electroluminescent device |
| US7662487B2 (en) | 2005-09-09 | 2010-02-16 | Idemitsu Kosan Co., Ltd. | Azaaromatic compounds having azafluoranthene skeletons and organic electroluminescent devices made by using the same |
| LT5444B (en) | 2005-12-30 | 2007-10-25 | Vilniaus Universitetas | Non-polymeric compounds with charge carrier transport properties and organic electroluminescence element |
| LT5783B (en) | 2009-12-11 | 2011-10-25 | Vilniaus Universitetas, , | Organic iridium complexes, method of preparation thereof and organic electroluminescent element |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2721441B2 (en) | 1998-03-04 |
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