JP3354248B2 - EL device - Google Patents
EL deviceInfo
- Publication number
- JP3354248B2 JP3354248B2 JP31562293A JP31562293A JP3354248B2 JP 3354248 B2 JP3354248 B2 JP 3354248B2 JP 31562293 A JP31562293 A JP 31562293A JP 31562293 A JP31562293 A JP 31562293A JP 3354248 B2 JP3354248 B2 JP 3354248B2
- Authority
- JP
- Japan
- Prior art keywords
- light emitting
- emitting layer
- injection electrode
- organic
- embedded image
- 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.)
- Expired - Fee Related
Links
- 239000000463 material Substances 0.000 claims description 29
- 238000002347 injection Methods 0.000 claims description 26
- 239000007924 injection Substances 0.000 claims description 26
- 150000004696 coordination complex Chemical class 0.000 claims description 11
- 239000002019 doping agent Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000001704 evaporation Methods 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims 1
- 239000010410 layer Substances 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 6
- 239000003446 ligand Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- -1 4-hydroxyacr Idine metal complex Chemical class 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- 229910017911 MgIn Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- HOYZEVWRZVPHEL-UHFFFAOYSA-N acridin-4-ol Chemical compound C1=CC=C2N=C3C(O)=CC=CC3=CC2=C1 HOYZEVWRZVPHEL-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は、ホール注入電極と電子
注入電極との間に、少なくとも有機発光層を有する電界
発光素子に関し、詳しくはその有機発光層の改良に関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electroluminescent device having at least an organic light emitting layer between a hole injection electrode and an electron injection electrode, and more particularly to an improvement in the organic light emitting layer.
【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
近は自己発光型で、表示が鮮明な電界発光素子が注目さ
れている。2. Description of the Related Art In recent years, with the diversification of information devices, CR
There is an increasing need for a flat display element that consumes less power and has a smaller space occupation volume than T. As such a flat display element, there are a liquid crystal, a plasma display, and the like. In particular, recently, a self-luminous electroluminescent element with a clear display has attracted attention.
【０００３】ここで上記電界発光素子は、構成する材料
により無機電界発光素子と有機電界発光素子とに大別す
ることができ、無機電界発光素子はすでに実用化されて
いる。しかしながら、上記無機電界発光素子の駆動方式
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、高電圧で駆動させる必要がある。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。これに対し、上記有機電界発光素子は電極から
注入された電荷（ホールおよび電子）が発光体中心で再
結合して発光するという、所謂「注入型発光」であるた
め、低電圧で駆動することができる。しかも、有機化合
物の分子構造を変更することによって理論的には、任意
の発光色を容易に得ることができるといった利点もあ
る。従って、有機電界発光素子はこれからの表示素子と
して非常に有望である。[0003] The above-mentioned electroluminescent devices can be roughly classified into inorganic electroluminescent devices and organic electroluminescent devices depending on the constituent materials, and inorganic electroluminescent devices have already been put into practical use. However, the driving method of the inorganic electroluminescent element is a so-called “collision excitation type light emission” in which accelerated electrons collide with a light emission center and emit light when a high electric field is applied.
Therefore, it is necessary to drive at a high voltage. For this reason, there has been a problem that the cost of peripheral devices is increased. On the other hand, the organic electroluminescent element is a so-called “injection type light emission” in which charges (holes and electrons) injected from an electrode are recombined at the center of the light emitting body, so that it is driven at a low voltage. Can be. In addition, by changing the molecular structure of the organic compound, theoretically, there is also an advantage that an arbitrary emission color can be easily obtained. Therefore, the organic electroluminescent device is very promising as a future display device.
【０００４】ここで有機電界発光素子は一般的に２層構
造〔ホール注入電極と電子注入電極との間に、ホール輸
送層と発光層とが形成された構造（ＳＨ−Ａ構造）、ま
たはホール注入電極と電子注入電極との間に、発光層と
電子輸送層とが形成された構造（ＳＨ−Ｂ構造）〕、あ
るいは３層構造〔ホール注入電極と電子注入電極との間
に、ホール輸送層と発光層と電子輸送層とが形成された
構造（ＤＨ構造）〕のような素子構造を有している。上
記ホール注入電極としては、金やインジウム−スズ酸化
物のような仕事関数の大きな電極材料を用い、上記電子
注入電極としては、Ｍｇのような仕事関数の小さな電極
材料を用いる。また、上記ホール輸送層、発光層、電子
輸送層には有機材料が用いられ、ホール輸送層はｐ型半
導体の性質、電子輸送層はｎ型半導体の性質を有する材
料が用いられている。上記発光層は、上記ＳＨ−Ａ構造
ではｎ型半導体の性質、ＳＨ−Ｂ構造ではｐ型半導体の
性質、ＤＨ構造では中性に近い性質を有する材料が用い
られる。いずれにしてもホール注入電極から注入された
ホールと電子注入電極から注入された電子が、発光層と
ホール（または電子）輸送層の界面及び発光層内で再結
合して発光するという原理である。Here, the organic electroluminescent device generally has a two-layer structure (a structure in which a hole transport layer and a light emitting layer are formed between a hole injection electrode and an electron injection electrode (SH-A structure), or a hole. A structure in which a light emitting layer and an electron transport layer are formed between an injection electrode and an electron injection electrode (SH-B structure)] or a three-layer structure [hole transport between the hole injection electrode and the electron injection electrode] (DH structure) in which a layer, a light emitting layer and an electron transport layer are formed]. An electrode material having a large work function such as gold or indium-tin oxide is used as the hole injection electrode, and an electrode material having a small work function such as Mg is used as the electron injection electrode. An organic material is used for the hole transport layer, the light emitting layer, and the electron transport layer. A material having the property of a p-type semiconductor is used for the hole transport layer, and a material having the property of an n-type semiconductor is used for the electron transport layer. The light emitting layer is made of a material having the property of an n-type semiconductor in the SH-A structure, the property of a p-type semiconductor in the SH-B structure, and the property close to neutral in the DH structure. In any case, the principle is that holes injected from the hole injection electrode and electrons injected from the electron injection electrode recombine at the interface between the light emitting layer and the hole (or electron) transport layer and within the light emitting layer to emit light. .
【０００５】[0005]
【発明が解決しようとする課題】上記したように、有機
電界発光素子では、発光層に用いられる有機発光材料の
分子構造を変化させることにより、理論的には素子の発
光色としては青色から赤色まで全ての発光色をだすこと
が可能である。しかしながら、有機電界発光素子の実用
化を考えると、単に所望の発光色が得られることだけで
なく、素子の発光寿命や、輝度について考える必要があ
る。As described above, in an organic electroluminescent device, the emission color of the device is theoretically changed from blue to red by changing the molecular structure of the organic light emitting material used for the light emitting layer. It is possible to emit all colors up to. However, considering the practical use of the organic electroluminescent device, it is necessary to consider not only the desired emission color but also the emission life and brightness of the device.
【０００６】現在、赤色〜橙色の領域の発光を呈する発
光材料については、幾つかの発光材料が知られている
が、素子を作製した場合、素子の発光寿命が長く且つ高
輝度な発光を呈するものがないというのが実状であっ
た。特に赤色については色の三原色（青、赤、緑）の一
色であり、発光寿命が長くしかも高輝度な発光を呈する
材料の提供は、有機電界発光素子を用いたフルカラーデ
ィスプレイの実施に繋がる。At present, some light emitting materials emitting light in the red to orange region are known. However, when the device is manufactured, the light emitting life of the device is long and the device emits light with high luminance. The reality was that there was nothing. In particular, red is one of the three primary colors (blue, red, and green), and providing a material that emits light with a long luminous life and high luminance leads to the implementation of a full-color display using an organic electroluminescent element.
【０００７】本発明は上記現状に鑑み行われたものであ
り、新たな発光材料を用いることにより、輝度が高くし
かも発光寿命の長い赤色〜橙色の発光を呈する有機電界
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 above situation, and provides an organic electroluminescent element which emits red to orange light with high luminance and a long light-emitting life by using a new light-emitting material. Aim.
【０００８】[0008]
【課題を解決するための手段】上記目的を達成するため
に、本発明は、ホール注入電極と電子注入電極との間
に、少なくとも有機発光層を有する電界発光素子におい
て、前記有機発光層は、母材とドーパントとを含み、母
材としては上記化１のＡｌｑ 3 又は上記化２のＢｅＢｑ 2
が用いられ、ドーパントとしては４−Ｈｙｄｒｏｘｙａ
ｃｒｉｄｉｎｅ金属錯体が用いられているともに、当該
有機発光層は、母材とドーパントとを共蒸着する共蒸着
法にて形成されたものであることを特徴とする。 In order to achieve the above object, the present invention provides an electroluminescent device having at least an organic light emitting layer between a hole injection electrode and an electron injection electrode . A base material and a dopant;
As the material, Alq 3 of the above formula 1 or BeBq 2 of the above formula 2
Is used, and 4-Hydroxya is used as a dopant.
cridine metal complex is used,
The organic light emitting layer is co-deposited by co-evaporating the base material and the dopant.
It is characterized by being formed by a method.
【０００９】ここで、前記４−Ｈｙｄｒｏｘｙａｃｒｉ
ｄｉｎｅ金属錯体が上記化３又は上記化４に示す化合物
であることを特徴とする。 [0009] Here, the 4-hydroxyacryl is used.
a compound in which the din metal complex is represented by the above formula 3 or 4
It is characterized by being.
【００１０】[0010]
【作用】本発明の発光材料に用いた４−Ｈｙｄｒｏｘｙ
ａｃｒｉｄｉｎｅ金属錯体は、配位子部分が発光するも
のであり、配位子のπ電子共役系は発光色に大きな影響
を与える。４−Ｈｙｄｒｏｘｙａｃｒｉｄｉｎｅ金属錯
体の配位子のπ電子系は長く広がっているため、π電子
が安定化した状態にあり、波長の長い赤色発光を呈した
ものと考えられる。The 4-hydroxy used in the light emitting material of the present invention.
The ligand metal complex emits light at the ligand portion, and the π-electron conjugated system of the ligand has a great effect on the emission color. Since the π-electron system of the ligand of the 4-hydroxyacrylidine metal complex has been extended for a long time, it is considered that the π-electrons are in a stabilized state and emit red light with a long wavelength.
【００１１】また、この４−Ｈｙｄｒｏｘｙａｃｒｉｄ
ｉｎｅ金属錯体は製膜後の結晶化が起こりにくい材料で
ある。製膜後に結晶化が起こると、発光が起こらなくな
り、素子の寿命を低下させることになので、製膜後に結
晶化しにくい材料を用いることによって素子の長寿命化
を図ることができる。また、４−Ｈｙｄｒｏｘｙａｃｒ
ｉｄｉｎｅ金属錯体は、キャリア輸送性が高く、量子収
率も高い化合物である。従って、素子を作製し、発光さ
せた場合発光効率の高い素子を作製することができる。
発光効率を高めることによって、例えば、同じ輝度を得
るために、より低い電流密度、低い電圧で素子を駆動す
ればよく、発光時に素子にかかる負担が軽減され、素子
の長寿命化を図ることができる。また、高輝度な発光を
得ることができる。Further, the 4-hydroxyacid
The ine metal complex is a material that does not easily crystallize after film formation. When crystallization occurs after film formation, light emission does not occur and the life of the element is shortened. Therefore, by using a material that is difficult to crystallize after film formation, the life of the element can be extended. Also, 4-hydroxyacr
Idine metal complex is a compound having high carrier transportability and high quantum yield. Therefore, when an element is manufactured and emitted light, an element with high luminous efficiency can be manufactured.
By increasing the luminous efficiency, for example, in order to obtain the same luminance, the element only needs to be driven at a lower current density and a lower voltage, so that the load on the element during light emission is reduced and the life of the element can be extended. it can. Further, high-luminance light emission can be obtained.
【００１２】さらに、４−Ｈｙｄｒｏｘｙａｃｒｉｄｉ
ｎｅ金属錯体を発光層のドーパントとして用い、母材と
の組み合わせることによって、橙色の発光を得ることが
できた。Furthermore, 4-hydroxyacrylidi
By using the ne metal complex as a dopant for the light emitting layer and combining it with a base material, orange light emission could be obtained.
【００１３】[0013]
【実施例】（参考例１） 図１は、本発明の一例にかかる実施例１の電界発光素子
の断面図である。図１に示すように、本実施例の電界発
光素子は、ガラス基板１上に、ホール注入電極２と、有
機ホール輸送層３と、有機発光層４と、電子注入電極５
とが順に積層されたかたちで形成されている。Example ( Reference Example 1 ) FIG. 1 is a cross-sectional view of an electroluminescent device of Example 1 according to an example of the present invention. As shown in FIG. 1, the electroluminescent device of the present embodiment has a hole injection electrode 2, an organic hole transport layer 3, an organic light emitting layer 4, and an electron injection electrode 5 on a glass substrate 1.
And are sequentially stacked.
【００１４】上記電界発光素子において、ホール注入電
極２の材料としては、インジウム−スズ酸化物（ＩＴ
Ｏ）、有機ホール輸送層３の材料としては下記化５に示
すジアミン誘導体（ＴＰＤ）、有機発光層４の材料とし
ては下記化６に示す４−Ｈｙｄｒｏｘｙａｃｒｉｄｉｎ
ｅ亜鉛錯体（以下Ｚｎ（ａｃ）2と称す）、電子注入電
極５の材料としてはＭｇＩｎ合金が用いられている。In the above electroluminescent device, the material of the hole injection electrode 2 is indium-tin oxide (IT
O), the material of the organic hole transport layer 3 is a diamine derivative (TPD) shown in the following chemical formula 5, and the material of the organic light emitting layer 4 is 4-hydroxyacridin in the following chemical formula 6
As a material for the e-zinc complex (hereinafter referred to as Zn (ac) 2 ) and the electron injection electrode 5, an MgIn alloy is used.
【００１５】[0015]
【化５】 Embedded image
【００１６】[0016]
【化６】 Embedded image
【００１７】ここで上記電界発光素子は、以下のように
して作製した。ガラス基板１上にホール注入電極となる
ＩＴＯの薄膜が形成された基板を用意し、この基板を中
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２０分間超音波洗浄を行った。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ＩＴＯから
なるホール注入電極２上にＴＰＤを真空蒸着して、有機
ホール輸送層３を形成した。続いて、この有機ホール輸
送層３上にＺｎ（ａｃ）2 を真空蒸着して有機発光層４
を形成し、さらにその上にＭｇとＩｎとを１０対１の割
合で共蒸着することにより、電子注入電極５を形成し
た。Here, the electroluminescent device was manufactured as follows. A substrate on which a thin film of ITO serving as a hole injection electrode was formed on a glass substrate 1 was prepared, and the substrate was washed with a neutral detergent, and then subjected to ultrasonic cleaning in acetone for 20 minutes and in ethanol for 20 minutes. . Next, the substrate was put into boiling ethanol for about 1 minute, and immediately after being taken out, it was blow-dried. Then, TPD was vacuum-deposited on the hole injection electrode 2 made of ITO to form an organic hole transport layer 3. Subsequently, Zn (ac) 2 is vacuum-deposited on the organic hole transport layer 3 to form an organic light emitting layer 4.
Was formed thereon, and Mg and In were co-evaporated thereon at a ratio of 10: 1 to form an electron injection electrode 5.
【００１８】尚、これらの蒸着はいずれも真空度１×１
０-6Ｔｏｒｒ、基板温度２０℃、有機層の蒸着速度２Å
／ｓｅｃという条件下でおこなった。ところで、上記Ｚ
ｎ（ａｃ）2 は以下に示すような方法で合成をおこなっ
た。 （Ｚｎ（ａｃ）2 の合成方法）先ず、４−Ｈｙｄｒｏｘ
ｙａｃｒｉｄｉｎｅを１ｇ（５．１２ｍｍｏｌ）とエタ
ノール３０ｍｌを２つ口フラスコにいれ加温した。酢酸
亜鉛０．５６ｇ（２．５６ｍｍｏｌ）をメタノール２０
ｍｌに溶解させ、上記した４−Ｈｙｄｒｏｘｙａｃｒｉ
ｄｉｎｅのエタノール溶液中に滴下ロートを用いて滴下
すると、橙色の沈澱が析出した。この反応液を２時間還
流させた後、自然冷却させ、沈澱物を吸引ろ過した。得
られた沈澱物をよく乾燥させた後、トレインサブリメー
ション法を用いた昇華精製装置（H.J.Wagner,R.O.Loutf
y, and C.K.Hsiao ; J. Mater. Sci. 17, 2718 (198
2))）で精製した。得られた微結晶には赤色の螢光（ピ
ーク波長６６２ｎｍ）が確認された。Each of these depositions was performed at a vacuum degree of 1 × 1.
0 -6 Torr, substrate temperature 20 ° C, deposition rate of organic layer 2Å
/ Sec. By the way, Z
n (ac) 2 was synthesized by the following method. (Synthesis method of Zn (ac) 2 ) First, 4-Hydrox
1 g (5.12 mmol) of yacridine and 30 ml of ethanol were placed in a two-necked flask and heated. 0.56 g (2.56 mmol) of zinc acetate was added to methanol 20
dissolved in the above-mentioned 4-hydroxyacrylic solution.
When the mixture was dropped into the ethanol solution of dine using a dropping funnel, an orange precipitate was deposited. The reaction solution was refluxed for 2 hours, allowed to cool naturally, and the precipitate was suction-filtered. After the obtained precipitate is thoroughly dried, a sublimation purification device (HJWagner, ROLoutf) using a train sublimation method is used.
y, and CKHsiao; J. Mater.Sci. 17, 2718 (198
2))). Red fluorescence (peak wavelength 662 nm) was confirmed in the obtained microcrystals.
【００１９】このように作製した素子を、以下（ａ1）
素子と称する。 （実施例１） 発光層の材料として、母材に上記化１に示すＡｌｑ3を
用い、ドーパントとしてＺｎ（ａｃ）2を用いた以外
は、参考例１と同様に素子の作製を行った。尚、Ｚｎ
（ａｃ）2はＡｌｑ3に対して、２重量％添加した。The device fabricated in this manner is represented by the following (a 1 )
It is called an element. Example 1 An element was manufactured in the same manner as in Reference Example 1 , except that Alq 3 shown in Chemical formula 1 was used as a base material and Zn (ac) 2 was used as a dopant as a material of a light emitting layer. Incidentally, Zn
(Ac) 2 was added at 2% by weight to Alq 3 .
【００２０】このように作製した素子を、以下（ａ2 ）
素子と称する。The device fabricated in this manner is represented by the following (a 2 )
It is called an element.
【００２１】[0021]
【００２２】（実施例２） 母材として上記化２に示すＢｅＢｑ2を用いた以外は、
上記実施例１と同様に素子を作製した。このようにして
作製した素子を、以下（ａ3）素子と称する。[0022] except for using (Example 2) BeBq 2 shown in the above-described chemical formula 2 as a base material,
An element was produced in the same manner as in Example 1 above. The device manufactured in this manner is hereinafter referred to as (a 3 ) device.
【００２３】[0023]
【００２４】（比較例１） 発光層の材料として、下記化７に示すペリレン誘導体を
用いる以外は、上記参考例１と同様の素子の作製を行っ
た。(Comparative Example 1) An element was produced in the same manner as in Reference Example 1 except that a perylene derivative represented by the following formula 7 was used as a material for the light emitting layer.
【００２５】[0025]
【化７】 Embedded image
【００２６】このように作製した素子を、以下（Ｘ1）
素子と称する。 （比較例２） 発光層の材料として、下記化８に示すフタロぺリノン誘
導体を用いた以外は、上記参考例１と同様に素子を作製
した。（但し、本比較例に用いたフタロぺリノン誘導体
は、メトキシ基をメタ位に有するものと、パラ位に有す
るものとの混合物である。）The device fabricated in this manner is represented by the following (X 1 )
It is called an element. (Comparative Example 2) A device was manufactured in the same manner as in Reference Example 1 except that a phthaloperinone derivative represented by Chemical Formula 8 below was used as a material for the light emitting layer. (However, the phthaloperinone derivative used in this comparative example is a mixture of one having a methoxy group at the meta position and one having a methoxy group at the para position.)
【００２７】[0027]
【化８】 Embedded image
【００２８】このように作製した素子を、以下（Ｘ2）
素子と称する。 （実験） 上記参考例及び実施例の（ａ1）〜（ａ3）素子、比較例
の（Ｘ1）、（Ｘ2）素子を用いて、発光輝度と発光寿命
を測定したので、下記の表１にその結果を示す。The device fabricated in this manner is represented by the following formula (X 2 )
It is called an element. (Experiment) The emission luminance and emission life were measured using the (a 1 ) to (a 3 ) elements of the above reference examples and examples, and the (X 1 ) and (X 2 ) elements of the comparative examples. Table 1 shows the results.
【００２９】[0029]
【表１】 [Table 1]
【００３０】上記したように、（ａ 2 ）、（ａ3）素子
は、Ｚｎ（ａｃ）2をドーパントとし、母材と組み合わ
せることによって、発光輝度も高く、発光寿命の長い、
橙色の発光を得ることができた。 （その他の事項） 発光層に用いる４−Ｈｙｄｒｏｘｙａｃｒｉｄｉｎｅ
金属錯体は、上記実施例に用いた金属錯体に限ることな
く、配位子と金属が３対１の４−Ｈｙｄｒｏｘｙａｃｒ
ｉｄｉｎｅ金属錯体、或いは、中心金属が亜鉛以外に、
周期率表の２族、３族の金属である４−Ｈｙｄｒｏｘｙ
ａｃｒｉｄｉｎｅ金属錯体を用いることができる。上
記実施例では、ＳＨ−Ａ構造の電界発光素子について記
載を行ったが、本発明はこの素子構造に限定する必要は
なく、ＳＨ−Ｂ構造、ＤＨ構造等の発光層にも同様に用
いることができるのは無論である。As described above , the (a 2 ) and (a 3 ) elements have high emission luminance and long emission life by combining Zn (ac) 2 with a base material.
Orange light emission was obtained. (Other Matters) 4-Hydroxyacryline used for the light emitting layer
The metal complex is not limited to the metal complex used in the above-described embodiment, but may be 4-hydroxyacr in which the ligand and the metal are 3 to 1.
Idine metal complex or the central metal is other than zinc,
4-Hydroxy which is a metal belonging to Group 2 or 3 of the periodic table
Acridine metal complexes can be used. In the above embodiment, the description has been given of the electroluminescent device having the SH-A structure. However, the present invention is not limited to this device structure, and may be similarly used for the light emitting layer having the SH-B structure, the DH structure, or the like. Of course you can.
【００３１】[0031]
【発明の効果】以上説明したように、本発明によれば、
４−Ｈｙｄｒｏｘｙａｃｒｉｄｉｎｅ金属錯体を有機発
光層の発光材料として用いることにより、発光寿命が長
く、しかも発光輝度の高い赤色〜橙色発光を呈する電界
発光素子を提供することができた。As described above, according to the present invention,
By using the 4-hydroxyacridine metal complex as the light emitting material of the organic light emitting layer, an electroluminescent device having a long light emitting life and exhibiting red to orange light with high light emission luminance could be provided.
【図１】本発明の一例に係る実施例１の電界発光素子で
ある。FIG. 1 is an electroluminescent device of Example 1 according to an example of the present invention.
２ ホール注入電極 ３ 有機発光層 ５ 電子注入電極 2 hole injection electrode 3 organic light emitting layer 5 electron injection electrode
フロントページの続き (72)発明者 藤井 孝則 守口市京阪本通２丁目５番５号 三洋電 機株式会社内 (72)発明者 柴田 賢一 守口市京阪本通２丁目５番５号 三洋電 機株式会社内 (56)参考文献 特開 平２−8287（ＪＰ，Ａ) 特開 平５−331460（ＪＰ，Ａ) 特開 平５−105872（ＪＰ，Ａ) (58)調査した分野(Int.Cl.7，ＤＢ名) H05B 33/14 C09K 11/06 Continued on the front page (72) Inventor Takanori Fujii 2-5-5 Keihanhondori, Moriguchi City Inside Sanyo Electric Machinery Co., Ltd. (72) Inventor Kenichi Shibata 2-5-5 Keihanhondori, Moriguchi City Sanyo Electric Machinery Stock In-company (56) References JP-A-2-8287 (JP, A) JP-A-5-331460 (JP, A) JP-A-5-105872 (JP, A) (58) Fields investigated (Int. . 7, DB name) H05B 33/14 C09K 11/06
Claims (2)
に、少なくとも有機発光層を有する電界発光素子におい
て、前記有機発光層は、母材とドーパントとを含み、母
材としては下記化１のＡｌｑ 3 又は下記化２のＢｅＢｑ 2
が用いられ、ドーパントとしては４−Ｈｙｄｒｏｘｙａ
ｃｒｉｄｉｎｅ金属錯体が用いられているともに、当該
有機発光層は、母材とドーパントとを共蒸着する共蒸着
法にて形成されたものであることを特徴とする電界発光
素子。 【化１】 【化２】 1. An electroluminescent device having at least an organic light emitting layer between a hole injection electrode and an electron injection electrode, wherein the organic light emitting layer contains a base material and a dopant,
As the material, Alq 3 of the following formula 1 or BeBq 2 of the following formula 2
Is used, and 4-Hydroxya is used as a dopant.
cridine metal complex is used,
The organic light emitting layer is co-deposited by co-evaporating the base material and the dopant.
Electroluminescence characterized by being formed by a method
element. Embedded image Embedded image
ｅ金属錯体が下記化３又は下記化４に示す化合物である
ことを特徴とする請求項1に記載の電界発光素子。 【化３】 【化４】 2. The 4-hydroxyacidin
The e metal complex is a compound represented by the following chemical formula 3 or 4
2. The electroluminescent device according to claim 1, wherein: Embedded image Embedded image
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31562293A JP3354248B2 (en) | 1993-12-15 | 1993-12-15 | EL device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP31562293A JP3354248B2 (en) | 1993-12-15 | 1993-12-15 | EL device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07166159A JPH07166159A (en) | 1995-06-27 |
| JP3354248B2 true JP3354248B2 (en) | 2002-12-09 |
Family
ID=18067586
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP31562293A Expired - Fee Related JP3354248B2 (en) | 1993-12-15 | 1993-12-15 | EL device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3354248B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2930056B2 (en) * | 1997-05-30 | 1999-08-03 | 日本電気株式会社 | Organic electroluminescent device material and organic electroluminescent device using the same |
-
1993
- 1993-12-15 JP JP31562293A patent/JP3354248B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07166159A (en) | 1995-06-27 |
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