JPH03152184A - El element of organic thin film - Google Patents
El element of organic thin filmInfo
- Publication number
- JPH03152184A JPH03152184A JP1288824A JP28882489A JPH03152184A JP H03152184 A JPH03152184 A JP H03152184A JP 1288824 A JP1288824 A JP 1288824A JP 28882489 A JP28882489 A JP 28882489A JP H03152184 A JPH03152184 A JP H03152184A
- Authority
- JP
- Japan
- Prior art keywords
- thin film
- organic
- conductive thin
- diphenoquinone
- film layer
- 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.)
- Pending
Links
- 239000010409 thin film Substances 0.000 title claims abstract description 73
- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical class C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 claims abstract description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- QDRFIDSUGRGGAY-UHFFFAOYSA-N 4-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-2,6-dimethylcyclohexa-2,5-dien-1-one Chemical compound C1=C(C)C(=O)C(C)=CC1=C1C=C(C)C(=O)C(C)=C1 QDRFIDSUGRGGAY-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002542 deteriorative effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 5
- 230000006866 deterioration Effects 0.000 description 4
- 230000007423 decrease Effects 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- XFYQEBBUVNLYBR-UHFFFAOYSA-N 12-phthaloperinone Chemical class C1=CC(N2C(=O)C=3C(=CC=CC=3)C2=N2)=C3C2=CC=CC3=C1 XFYQEBBUVNLYBR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000000855 fermentation Methods 0.000 description 2
- 230000004151 fermentation Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- JCXLYAWYOTYWKM-UHFFFAOYSA-N (2,3,4-triphenylcyclopenta-1,3-dien-1-yl)benzene Chemical compound C1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JCXLYAWYOTYWKM-UHFFFAOYSA-N 0.000 description 1
- UBZVRROHBDDCQY-UHFFFAOYSA-N 20749-68-2 Chemical compound C1=CC(N2C(=O)C3=C(C(=C(Cl)C(Cl)=C3C2=N2)Cl)Cl)=C3C2=CC=CC3=C1 UBZVRROHBDDCQY-UHFFFAOYSA-N 0.000 description 1
- HDGAYMVNWSXKLI-UHFFFAOYSA-N 6-amino-2-methylbenzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(N(C)C2=O)=O)=C3C2=CC=CC3=C1N HDGAYMVNWSXKLI-UHFFFAOYSA-N 0.000 description 1
- CNUWYNDMLFVRBU-UHFFFAOYSA-N 6-methoxy-2-methylbenzo[de]isoquinoline-1,3-dione Chemical compound O=C1N(C)C(=O)C2=CC=CC3=C2C1=CC=C3OC CNUWYNDMLFVRBU-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 238000005566 electron beam evaporation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は平面光源やデイスプレィに使用される有機酵ｖ
ａＥＬ素子に関するものである。[Detailed Description of the Invention] [Industrial Application Field] The present invention is directed to organic fermentation v.
This relates to aEL elements.
［従来の技術］
有機物質を原料としたＥＬ（電界発光）素子は、安価な
大面積フルカラー表示素子を実現するものとして注目を
集めている。例えばアントラセンやペリレン等の縮合多
環芳香族系を原料としてＬＢ法や真空蒸着法等で薄膜化
した直流駆動の有機薄膜Ｅｌ素子が製造され、その発光
特性が研究されている。しかし、従来の有機酵１１１Ｅ
Ｌ素子は駆動電圧が高く、かつその発光輝度・効率が無
ｔｉ薄膜ＥＬ素子のそれと比べて低かった。また、発光
特性の劣化も著しく、実用レベルのものはできなかった
。[Prior Art] EL (electroluminescent) devices using organic materials as raw materials are attracting attention as they can realize inexpensive large-area full-color display devices. For example, DC-driven organic thin-film El elements have been manufactured using condensed polycyclic aromatic systems such as anthracene and perylene as raw materials and made into thin films by the LB method, vacuum evaporation method, etc., and their light-emitting characteristics have been studied. However, conventional organic fermentation 111E
The driving voltage of the L element was high, and its luminance and efficiency were lower than those of the Ti-free thin film EL element. In addition, the luminescence properties deteriorated significantly, making it impossible to achieve a practical level.
ところが、最近、有Ｉｌ薄膜を３層構造にした新しいタ
イプの有機薄膜ＥＬ素子が報告され、強い関心を集めて
いる（ジャパニーズ・ジャーナル・オブ・アプライド・
フィジックス、２７巻、７１３ページ、１９８８年参照
）。報告によれば、この有機薄膜ＥＬ素子は、第２図に
示すように、強い蛍光を発する１２−フタロペリノン誘
導体を有機蛍光体薄膜層２４に、アミン系有機材料を有
機正孔伝導性薄膜層２３に、ざらにペリレン誘導体を有
機電子伝導性薄膜層２５に使用して３層構造とし、これ
らを透明電極２２および背面電極２６で挟むことにより
、明るい黄色発光を得たことが報告されている。However, recently, a new type of organic thin film EL device with a three-layer structure of Il-containing thin films has been reported and is attracting strong interest (Japanese Journal of Applied Technology).
Physics, vol. 27, p. 713, 1988). According to reports, as shown in FIG. 2, this organic thin film EL device uses a 12-phthaloperinone derivative that emits strong fluorescence as an organic phosphor thin film layer 24 and an amine-based organic material as an organic hole conductive thin film layer 23. Furthermore, it has been reported that bright yellow light emission was obtained by using a perylene derivative in the organic electronic conductive thin film layer 25 to form a three-layer structure and sandwiching these between the transparent electrode 22 and the back electrode 26.
この素子は、約３０ Ｖの直流電圧印加で５００ ｃｄ
／ｍ２以上の輝度を１ｑでいるので実用レベルに近い性
能を持っている。This element produces 500 cd when a DC voltage of about 30 V is applied.
Since it has a luminance of more than /m2 in 1q, it has performance close to the practical level.
［発明が解決しようとする課題］
前述したように、有機蛍光体薄膜、有機正孔伝導性薄膜
および有機電子伝導性薄膜が３層積層した！ｆ４造を有
する新しい有機薄膜ＥＬ素子は、最大発光輝度が５００
ｃｄ／ｍ２以上の明るい黄色発光を示す。この素子は
電流駆動型であるために、上記の輝度を得るためには１
００ｍＡ／ ｃｍ２以上の電流を流さなければならない
。[Problems to be Solved by the Invention] As mentioned above, three layers of an organic phosphor thin film, an organic hole conductive thin film, and an organic electron conductive thin film are laminated! The new organic thin film EL element with f4 structure has a maximum luminance of 500
It emits bright yellow light of cd/m2 or more. Since this element is a current drive type, in order to obtain the above brightness, it is necessary to
A current of 00mA/cm2 or more must flow.
しかし、従来使用していた有機物の電子伝導性薄ｌ１層
では、安定して充分電流を流すことができなかった。こ
れは通電とともに電子伝導性薄膜層が劣化し、その結果
、電子が有機蛍光体薄膜層に注入されにくくなるためで
ある。また、電力損（ジュール熱）の増大により劣化速
度が加速され、素子の発光効率の低下を招いていた。更
に、電子伝導性薄膜層の材料の還元電位が非常に大きい
ために（約−１，５Ｖ）、背面電極からの電子注入効率
が低かった。However, with the conventionally used thin electronically conductive 11 layer of organic material, it was not possible to flow a sufficient current stably. This is because the electron conductive thin film layer deteriorates as electricity is applied, and as a result, it becomes difficult for electrons to be injected into the organic phosphor thin film layer. Furthermore, the rate of deterioration was accelerated due to an increase in power loss (Joule heat), leading to a decrease in the luminous efficiency of the device. Furthermore, the electron injection efficiency from the back electrode was low because the reduction potential of the material of the electron-conducting thin film layer was very high (approximately -1.5 V).
本発明は、以上述べたような従来の事情に鑑みてなされ
たもので、素子発光効率が更に向上し、かつ発光輝度の
劣化速度が低下した有機薄膜ＥＬ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 conventional circumstances as described above, and an object of the present invention is to provide an organic thin film EL device in which the device luminous efficiency is further improved and the rate of deterioration of luminance is reduced.
［ｖＲ題を解決するための手段］
本発明は、少なくとも一方が透明な一対の電極間に、有
機正孔伝導性薄膜、有機蛍光体薄膜および有機電子伝導
性薄膜が順次積層された有機薄膜ＥＬ素子において、有
機電子伝導性薄膜の主成分が一般式［■コニ
・・・［Ｉコ
（式中、Ｒ１−Ｒ４はそれぞれ同一もしくは異なる基で
あって、アルキル基、アリル基、アルコキシル基または
ハロゲン原子を示す）で表されるジフェノキノン誘導体
であることを特徴とする有機薄膜ＥＬ素子である。[Means for solving the vR problem] The present invention provides an organic thin film EL in which an organic hole conductive thin film, an organic phosphor thin film, and an organic electron conductive thin film are sequentially laminated between a pair of electrodes, at least one of which is transparent. In the device, the main component of the organic electronically conductive thin film is of the general formula [■Coni... This is an organic thin film EL device characterized by being a diphenoquinone derivative represented by (indicating an atom).
本発明は、有機電子伝導性薄膜層として、特定のジフェ
ノキノン誘導体を用いると優れた特性を示す有機薄膜Ｅ
Ｌ素子が得られるという知見に基づいてなされたもので
ある。The present invention provides an organic thin film E which exhibits excellent properties when a specific diphenoquinone derivative is used as an organic electronically conductive thin film layer.
This was done based on the knowledge that an L element can be obtained.
本発明の有機薄膜ＥＬ素子は、第１図に示すように、背
面電極１６であるＩｎ電極と有機蛍光体薄膜層１４との
間に電子伝導性薄膜層としてジフェノキノン誘導体薄膜
層１５を形成し、Ｉｎ電極からの電子注入効率および電
子伝導性薄膜層内の輸送効率を高めている。As shown in FIG. 1, the organic thin film EL device of the present invention has a diphenoquinone derivative thin film layer 15 formed as an electron conductive thin film layer between an In electrode serving as a back electrode 16 and an organic phosphor thin film layer 14, This improves the electron injection efficiency from the In electrode and the transport efficiency within the electron conductive thin film layer.
なお、透明電極１２としては、通常用いられるものであ
ればいずれでもよく、例えばＩＴＯ，５ｎ０２ ：Ｓ
ｂ、ＺｎＯ：Ａｆ 、Ａｕ等が挙げられる。The transparent electrode 12 may be made of any commonly used material, such as ITO, 5n02:S
b, ZnO:Af, Au, etc.
また、背面電極１６には、Ｉ ｎ、Ｍｇ：Ａｇ等が使わ
れる。Further, for the back electrode 16, In, Mg:Ag, or the like is used.
本発明の電子伝導性薄膜に用いられるジフェノキノン誘
導体の具体的な例としては、２，６−シメチルー２°、
６°−ジ−ｔ−ブチルジフェノキノン、２，２°。Specific examples of diphenoquinone derivatives used in the electron conductive thin film of the present invention include 2,6-dimethyl-2°,
6°-di-t-butyldiphenoquinone, 2,2°.
６．６°−テトラ−１−ブチルジフェノキノン、２．２
’。6.6°-tetra-1-butyldiphenoquinone, 2.2
'.
６．６°−テトラメチルジフェノキノンなどがあるが、
この限りではない。6.6°-Tetramethyldiphenoquinone, etc.
This is not the case.
また、本発明に用いられる有機蛍光体の具体的な例とし
ては、トリス（８−ヒドロキシキノリン〉アルミニウム
、１２−フタロペリノン、８，９，１０．１１−テトラ
クロロ−１２−フタロペリノン、１，２，３．４−テト
ラフェニルシクロペンタジェン、ナフタルイミド、４−
７ミノナフタルイミド、Ｎ−メチル−４−アミノナフタ
ルイミド、トエチルー４−アミノナフタルイミド、トプ
ロピルー４−アミノナフタルイミド、Ｎ−ｎ−ブチル−
４−７ミノナフタルイミド、４−アセチルアミノナフタ
ルイミド、Ｎ−メチル−４−アセチルアミノナフタルイ
ミド、Ｎ−エチル−４−アセチルアミノナフタルイミド
、Ｎ−ｎ−ブチル−４−アセチルアミノナフタルイミド
、Ｎ−メチル−４−メトキシナフタルイミド、Ｎ−エチ
ル−４−メトキシナフタルイミド、Ｎ−プロピル−４−
メトキシナフタルイミド、Ｎ−ｎ−ブチル−４−メトキ
シナフタルイミド、トメチル−４−エトキシナフタルイ
ミド、Ｎ−エチル−４−エトキシナフタルイミド、Ｎ−
プロピル−４−エトキシナフタルイミド、Ｎ−ｎ−ブチ
ル−４−エトキシナフタルイミド、Ｎ−（２，４−キシ
リル）−４−アミノナフタルイミド、Ｎ−ブチル−４−
ブチルアミノナフタルイミドなどがあるが、この限りで
はない。Further, specific examples of the organic phosphor used in the present invention include tris(8-hydroxyquinoline>aluminum, 12-phthaloperinone, 8,9,10, 11-tetrachloro-12-phthaloperinone, 1,2, 3.4-tetraphenylcyclopentadiene, naphthalimide, 4-
7 Minonaphthalimide, N-methyl-4-aminonaphthalimide, toethyl-4-aminonaphthalimide, topropyl-4-aminonaphthalimide, N-n-butyl-
4-7 minonaphthalimide, 4-acetylaminonaphthalimide, N-methyl-4-acetylaminonaphthalimide, N-ethyl-4-acetylaminonaphthalimide, N-n-butyl-4-acetylaminonaphthalimide, N -Methyl-4-methoxynaphthalimide, N-ethyl-4-methoxynaphthalimide, N-propyl-4-
Methoxynaphthalimide, N-n-butyl-4-methoxynaphthalimide, tomethyl-4-ethoxynaphthalimide, N-ethyl-4-ethoxynaphthalimide, N-
Propyl-4-ethoxynaphthalimide, N-n-butyl-4-ethoxynaphthalimide, N-(2,4-xylyl)-4-aminonaphthalimide, N-butyl-4-
Examples include, but are not limited to, butylaminonaphthalimide.
本発明による有ｉ薄ＩＩＩＥＬ素子は、従来の有機薄膜
ＥＬ素子に比べて発光効率は２から３倍改善された。ま
た、従来よりも発光効率が改善されただけ、ジュール熱
の発生量が少なくなり、この結果、素子発熱に伴う発光
特性の劣化も少なくなった。The thin III EL device according to the present invention has improved luminous efficiency by two to three times compared to the conventional organic thin film EL device. Furthermore, as the luminous efficiency is improved over the conventional one, the amount of Joule heat generated is reduced, and as a result, the deterioration of the luminous properties due to element heat generation is also reduced.
このように、本発明で重要な点は、電子伝導性薄膜層に
用いる材料の主成分がジフェノキノン誘導体である点で
あり、電子伝導性薄膜層以外の素子を構成する材料につ
いては限定されない。As described above, an important point in the present invention is that the main component of the material used for the electron conductive thin film layer is a diphenoquinone derivative, and there are no limitations on the materials constituting the element other than the electron conductive thin film layer.
［作用］
３層構造の有機薄膜ＥＬ素子の発光メカニズムは次のよ
うであると考えられている。即ち、ＩＴＯなどの正孔注
入電極から正孔伝導性薄膜層に正孔が注入され、その層
を伝導して有機蛍光体薄膜層に正孔が注入される。一方
、仕事関数の低い金属を主体とした電子注入電極から電
子が有機電子伝導性薄膜層に注入され、その層を伝導し
て有機蛍光体薄膜層に電子が注入される。注入された電
子は有機蛍光体薄膜層を伝導し、正孔伝導性薄膜層との
界面で正孔と再結合して一重項励起子を生成する。この
結果、有機蛍光体層より発光が生じる。[Operation] The light emission mechanism of the three-layer organic thin film EL device is thought to be as follows. That is, holes are injected from a hole injection electrode such as ITO into the hole-conducting thin film layer, and are conducted through the layer to be injected into the organic phosphor thin film layer. On the other hand, electrons are injected into the organic electronically conductive thin film layer from an electron injection electrode mainly made of a metal with a low work function, and are conducted through the layer to be injected into the organic phosphor thin film layer. The injected electrons are conducted through the organic phosphor thin film layer and recombined with holes at the interface with the hole-conducting thin film layer to generate singlet excitons. As a result, light is emitted from the organic phosphor layer.
３層構造の有機１１１１ＥＬ素子の発光効率を向上させ
るには、電荷注入効率、電荷の輸送効率、励起子生成お
よび発光遷移確率を高めることが重要である。特に素子
の印加電圧が高くなると、有機蛍光体薄膜層と正孔伝導
性薄膜層の界面での電子と正孔の再結合、即ち励起子生
成効率が低下するので、低電圧で電子の注入および輸送
効率を改善させることが重要である。従来の３層構造の
素子で特に問題であった点は、通電とともに有機電子伝
導性薄膜層が劣化し、その結果、電子の注入および輸送
効率が低下したことである。その結果、電子伝導性薄膜
層の抵抗が増大し、駆動電圧の上昇およびジュール熱の
増大などの問題を引き起こしていた。また、有機電子伝
導性薄膜層の材料の還元電位が非常に大きく、背面電極
からの電子注入効率が低いために、−重環励起子の生成
効率が低く、発光効率が低くなっていた。In order to improve the luminous efficiency of a three-layer organic 1111EL element, it is important to increase charge injection efficiency, charge transport efficiency, exciton generation, and luminescence transition probability. In particular, as the voltage applied to the device increases, the recombination of electrons and holes at the interface between the organic phosphor thin film layer and the hole-conducting thin film layer, that is, the exciton generation efficiency, decreases. It is important to improve transport efficiency. A particular problem with conventional three-layer devices is that the organic electron-conducting thin film layer deteriorates with electricity, resulting in a decrease in electron injection and transport efficiency. As a result, the resistance of the electron-conductive thin film layer increases, causing problems such as an increase in driving voltage and an increase in Joule heat. Furthermore, the reduction potential of the material of the organic electron conductive thin film layer is very high and the efficiency of electron injection from the back electrode is low, resulting in low -heavy ring exciton production efficiency and low luminous efficiency.
本発明において、有機電子伝導性薄膜層１層の主成分と
して、−形成［Ｉ］で示さりるジフェノキノン誘導体を
用いると、該薄膜層の劣化が防止されると共に、還元電
位も小さいので（約−０，５Ｖ）、特性の優れた素子が
得られる。In the present invention, when a diphenoquinone derivative represented by -formation [I] is used as the main component of one organic electronically conductive thin film layer, deterioration of the thin film layer is prevented and the reduction potential is small (approximately -0.5V), an element with excellent characteristics can be obtained.
［実施例コ 以下、本発明の実施例について詳細に説明する。[Example code] Examples of the present invention will be described in detail below.
実施例１
有機蛍光体としてトリス（８−ヒドロキシキノリン〉ア
ルミニウムを用いた。第１図に示すように、ガラス基板
１１上にＩＴＯ透明電極１２を形成してから、有機正孔
伝導性薄膜層１３として１，１−ビス（４−Ｎ、Ｎ−ジ
トリルアミノフェニル）シクロヘキサンを５００人、真
空蒸着法で形成した。その後、有機蛍光体薄膜層１４を
５００人の膜厚で、１０−６ ＴＯｒｒ以下の真空中で
蒸着して形成した。さらに、有機電子伝導性薄膜層とし
て還元電位が−０，４８（Ｖ ＶＳ、 ５ＣＥ）であ
る２、２°、６，６°−テトラメチルジフェノキノンを
５００人の膜厚で、１Ｏ−６Ｔｏｒｒ以下の真空中で蒸
着して形成した。最後にＩｎの背面金属電極１６を電子
ビーム蒸着法で１５００人形成して有機薄膜ＥＬ素子が
完成する。Example 1 Tris(8-hydroxyquinoline)aluminum was used as an organic phosphor. As shown in FIG. 1, an ITO transparent electrode 12 was formed on a glass substrate 11, and then an organic hole-conducting thin film layer 13 1,1-bis(4-N,N-ditolylaminophenyl)cyclohexane was formed using a vacuum evaporation method using 500 layers of 1,1-bis(4-N,N-ditolylaminophenyl)cyclohexane.Thereafter, an organic phosphor thin film layer 14 was formed with a thickness of 500 layers at 10-6 Torr. 2,2°,6,6°-tetramethyldiphenoquinone having a reduction potential of −0,48 (V VS, 5CE) was used as an organic electronically conductive thin film layer. was deposited to a thickness of 500 in a vacuum of 1O-6 Torr or less.Finally, a back metal electrode 16 of In was formed by electron beam evaporation to a thickness of 1500 to complete an organic thin film EL device.
この素子の発光特性を乾燥窒素中で測定したところ、約
８■の直流電圧の印加で、３００ ｃｄ／ｍ２の緑色発
光が得られた。従来の素子に比べ、発光輝度・効率が２
から３倍改善されている。この有機薄膜Ｅ［素子を電流
密度０．５ ｍＡ／Ｃｍ２の状態でエージング試験をし
たところ、輝度半減時間は５００時間以上であった。従
来の素子では１００から３００時間であった。When the light emitting characteristics of this device were measured in dry nitrogen, green light emission of 300 cd/m2 was obtained by applying a DC voltage of about 8 cm. Compared to conventional elements, luminance and efficiency are 2.
This is an improvement of 3 times since. When this organic thin film E device was subjected to an aging test at a current density of 0.5 mA/Cm2, the luminance half-life was over 500 hours. In conventional devices, the time was 100 to 300 hours.
実施例２
有機蛍光体としてＮ−（２，４−キシリル）−４−アミ
ノナフタルイミドを用いた以外は、実施例１と同様にし
て有機薄膜ＥＬ素子を作製・評価した。約１０Ｖの直流
電圧の印加で２００ ｃｄ／ｍ２の黄色発光が得られ、
実施例１と同様な結果が得られた。Example 2 An organic thin film EL device was produced and evaluated in the same manner as in Example 1, except that N-(2,4-xylyl)-4-aminonaphthalimide was used as the organic phosphor. A yellow luminescence of 200 cd/m2 was obtained by applying a DC voltage of about 10V,
Similar results to Example 1 were obtained.
［発明の効果１
以上説明したように、本発明によれば発光特性および信
頼性が大幅に改善された有機薄１１ＷＥＬ素子が提供さ
れる。[Effect of the Invention 1] As explained above, according to the present invention, an organic thin 11WEL element with significantly improved light emitting characteristics and reliability is provided.
このように、本発明により有１１薄膜ＥＬ素子を実用レ
ベルまで引き上げることができ、その工業的価値は高い
。As described above, the present invention makes it possible to raise the thin-film EL device to a practical level, and its industrial value is high.
第１図は本発明の有機薄膜ＥＬ素子の概略断面図、第２
図は従来例による３層構造の有機薄膜ＥＬ素子の概略断
面図である。
１１．２１．・・・ガラス基板
１２．２２．・・・透明電極
１３．２３・・・有機正孔伝導性薄膜層１４、２４．・
・・有機蛍光体薄膜層
１５・・・ジフェノキノン誘導体薄膜層１６、２６・・
・背面電極
２５・・・有機電子伝導性薄膜層FIG. 1 is a schematic cross-sectional view of the organic thin film EL device of the present invention, and FIG.
The figure is a schematic cross-sectional view of a conventional three-layer organic thin film EL element. 11.21. ...Glass substrate 12.22. ...Transparent electrode 13.23...Organic hole conductive thin film layer 14, 24.・
・・Organic phosphor thin film layer 15 ・Diphenoquinone derivative thin film layer 16, 26 ・・
・Back electrode 25...Organic electron conductive thin film layer
Claims (1)
正孔伝導性薄膜、有機蛍光体薄膜および有機電子伝導性
薄膜が順次積層された有機薄膜ＥＬ素子において、有機
電子伝導性薄膜の主成分が一般式： ▲数式、化学式、表等があります▼ （式中、Ｒ＾１〜Ｒ＾４はそれぞれ同一もしくは異なる
基であつて、アルキル基、アリル基、アルコキシル基ま
たはハロゲン原子を示す）で表されるジフエノキノン誘
導体であることを特徴とする有機薄膜ＥＬ素子。(1) In an organic thin film EL element in which an organic hole conductive thin film, an organic phosphor thin film, and an organic electron conductive thin film are sequentially laminated between a pair of electrodes, at least one of which is transparent, the main component of the organic electron conductive thin film is is the general formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. An organic thin film EL device characterized by being a diphenoquinone derivative represented by the following formula.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1288824A JPH03152184A (en) | 1989-11-08 | 1989-11-08 | El element of organic thin film |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1288824A JPH03152184A (en) | 1989-11-08 | 1989-11-08 | El element of organic thin film |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03152184A true JPH03152184A (en) | 1991-06-28 |
Family
ID=17735214
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1288824A Pending JPH03152184A (en) | 1989-11-08 | 1989-11-08 | El element of organic thin film |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03152184A (en) |
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