JPH09194832A - Organic led element - Google Patents
Organic led elementInfo
- Publication number
- JPH09194832A JPH09194832A JP2303796A JP2303796A JPH09194832A JP H09194832 A JPH09194832 A JP H09194832A JP 2303796 A JP2303796 A JP 2303796A JP 2303796 A JP2303796 A JP 2303796A JP H09194832 A JPH09194832 A JP H09194832A
- Authority
- JP
- Japan
- Prior art keywords
- organic led
- led element
- light emitting
- polyazomethine
- 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
- 229920000343 polyazomethine Polymers 0.000 claims abstract description 18
- 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 abstract description 4
- 238000002347 injection Methods 0.000 abstract description 4
- 239000007924 injection Substances 0.000 abstract description 4
- 150000004866 oxadiazoles Chemical class 0.000 abstract description 4
- 238000004544 sputter deposition Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 abstract description 2
- 238000001771 vacuum deposition Methods 0.000 abstract 1
- 239000010408 film Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000007740 vapor deposition Methods 0.000 description 5
- KLCLIOISYBHYDZ-UHFFFAOYSA-N 1,4,4-triphenylbuta-1,3-dienylbenzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)=CC=C(C=1C=CC=CC=1)C1=CC=CC=C1 KLCLIOISYBHYDZ-UHFFFAOYSA-N 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 3
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- -1 aromatic tertiary amine Chemical class 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- DGBWPZSGHAXYGK-UHFFFAOYSA-N perinone Chemical class C12=NC3=CC=CC=C3N2C(=O)C2=CC=C3C4=C2C1=CC=C4C(=O)N1C2=CC=CC=C2N=C13 DGBWPZSGHAXYGK-UHFFFAOYSA-N 0.000 description 2
- 239000012780 transparent material Substances 0.000 description 2
- YLYPIBBGWLKELC-RMKNXTFCSA-N 2-[2-[(e)-2-[4-(dimethylamino)phenyl]ethenyl]-6-methylpyran-4-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC(=C(C#N)C#N)C=C(C)O1 YLYPIBBGWLKELC-RMKNXTFCSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 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
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010409 thin film Substances 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
Landscapes
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
- Led Devices (AREA)
Abstract
Description
【発明の詳細な説明】Detailed Description of the Invention
【０００１】[0001]
【発明の属する技術分野】本発明は注入型エレクトロル
ミネセンス（ＥＬ）とも称され、有機薄膜状としたＥＬ
物質に電子、正孔を注入し、再結合させることで発光を
行う有機ＬＥＤ素子に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention is also called injection electroluminescence (EL) and is an organic thin film EL.
The present invention relates to an organic LED element that emits light by injecting electrons and holes into a substance and recombining them.
【０００２】[0002]
【従来の技術】有機ＬＥＤ素子の構成の例を示すものが
図１０及び図１１であり、先ず、図１０に示す有機ＬＥ
Ｄ素子９０においては、基板９１、陽極９２、正孔注入
輸送層９３、発光層９４、電子注入輸送層９５、陰極９
６の順に各層が積層され構成されている。2. Description of the Related Art FIGS. 10 and 11 show examples of the structure of an organic LED element. First, the organic LE shown in FIG.
In the D element 90, the substrate 91, the anode 92, the hole injecting and transporting layer 93, the light emitting layer 94, the electron injecting and transporting layer 95, and the cathode 9
Each layer is laminated in the order of 6.
【０００３】上記有機ＬＥＤ素子９０を形成するときに
は、先ず、ガラスなど透明部材による基板９１上に透明
電極であるＩＴＯを陽極９２として蒸着、スパッタリン
グなどで成膜し、この陽極９２上に、Ｎ，Ｎ′―ジフェ
ニル―Ｎ，Ｎ′―ビス（３―メチルフェニル）―１，
１′―ビフェニル―４，４′―ジアミン（以下にＴＰＤ
と称する）を正孔注入輸送層９３として蒸着などにより
成膜する。When forming the organic LED element 90, first, ITO, which is a transparent electrode, is formed as a positive electrode 92 on a substrate 91 made of a transparent material such as glass by vapor deposition, sputtering, or the like, and N, N is formed on the positive electrode 92. N'-diphenyl-N, N'-bis (3-methylphenyl) -1,
1'-biphenyl-4,4'-diamine (hereinafter TPD
Is referred to as a hole injecting and transporting layer 93.
【０００４】次いで、前記正孔注入輸送層９３上に、１
―［４―Ｎ，Ｎ―ビス（ｐ―メトキシフェニル）アミノ
スチリル］ナフタレンを発光層９４として成膜し、この
発光層９４上に、２―（４―ビフェニリル）―５―（４
―ｔ―ブチルフェニル）―１，３，４―オキサジアゾー
ルを電子注入輸送層９５として成膜し、最後にＭｇとＡ
ｇとの合金を陰極９６として蒸着し成膜する。Then, 1 is formed on the hole injecting and transporting layer 93.
-[4-N, N-bis (p-methoxyphenyl) aminostyryl] naphthalene is formed as a light emitting layer 94, and 2- (4-biphenylyl) -5- (4
-T-Butylphenyl) -1,3,4-oxadiazole is formed as an electron injecting and transporting layer 95, and finally Mg and A
An alloy with g is deposited as a cathode 96 to form a film.
【０００５】また、図１１に示す有機ＬＥＤ素子８０に
おいては、基板８１、陽極８２、正孔注入輸送層８３、
発光層８４、陰極８５の各層で構成されるものであり、
上記と同様に基板８１に成膜された陽極８２上には、
１，１―ビス（４―ジ―ｐ―トリルアミノフェニル）シ
クロヘキサンなどの芳香族３級アミンが正孔注入輸送層
８３として蒸着により成膜されている。In the organic LED element 80 shown in FIG. 11, the substrate 81, the anode 82, the hole injecting and transporting layer 83,
The light emitting layer 84 and the cathode 85,
On the anode 82 formed on the substrate 81 in the same manner as described above,
An aromatic tertiary amine such as 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane is deposited as the hole injecting and transporting layer 83 by vapor deposition.
【０００６】次いで、前記正孔注入輸送層８３上に、ト
リス（８―キノリノール）アルミニウムなどの有機蛍光
体を発光層８４として成膜し、更に、前記発光層８４上
には前述と同様な金属、合金、金属化合物により陰極８
５が蒸着などにより成膜されている。Next, an organic phosphor such as tris (8-quinolinol) aluminum is formed as a light emitting layer 84 on the hole injecting and transporting layer 83, and a metal similar to the above is formed on the light emitting layer 84. , Alloy, metal compound cathode 8
5 is formed by vapor deposition or the like.
【０００７】[0007]
【発明が解決しようとする課題】しかしながら、従来の
この種の有機ＬＥＤ素子に用いられているＴＰＤなどの
化合物は時間の経過と共に再結晶化を生じ、ＬＥＤ素子
にピンホール、或いは、ショートを発生させる問題点が
あった。これは、これらの化合物の融点が低く、素子製
作中の処理熱や、素子駆動中の発熱により熱的な劣化が
進行するからである。However, the compound such as TPD used in the conventional organic LED device of this type recrystallizes with the passage of time, and pinholes or short circuits are generated in the LED device. There was a problem that caused it. This is because the melting points of these compounds are low, and thermal deterioration progresses due to heat of processing during device fabrication and heat generated during device driving.
【０００８】また、生産面からは、例えば発光層などは
溶剤に希釈してのスピンコートによる成膜方法とするこ
とがコスト、生産性の面から好ましいが、上記に説明し
た従来の低分子からなる正孔注入輸送層９３、８３で
は、発光材料を希釈する溶剤で溶けるのでスピンコート
などは行えず、蒸着など高コストで低生産性の成膜方法
を採用せざるを得ないものとなり、結果として有機ＬＥ
Ｄ素子がコストアップする問題点を生じ、これらの点の
解決が課題とされるものとなっている。From the viewpoint of production, for example, it is preferable from the viewpoint of cost and productivity that the light emitting layer and the like be formed into a film by spin coating with dilution in a solvent. In the hole injecting and transporting layers 93 and 83, the light emitting material is dissolved in a solvent that dilutes it, so spin coating cannot be performed, and a high cost and low productivity film forming method such as vapor deposition must be adopted. As an organic LE
The D element has a problem that the cost is increased, and the solution of these points becomes an issue.
【０００９】[0009]
【課題を解決するための手段】本発明は、前記した従来
の課題を解決するための具体的な手段として、下記、一
般式（１）で表されるポリアゾメチンを含有することを
特徴とする有機ＬＥＤ素子を提供することで課題を解決
するものである。The present invention is characterized by containing polyazomethine represented by the following general formula (1) as a specific means for solving the above-mentioned conventional problems. The problem is solved by providing an organic LED element.
【化２】 Embedded image
【００１０】[0010]
【発明の実施の形態】つぎに、本発明を図に示す第１〜
第４の実施形態に基づいて詳細に説明する。尚、以下の
説明では理解を容易とするために、有機ＬＥＤ素子を形
成するための各層において、同一機能を有する層に対し
ては同一符号を付して説明し、成膜方法など、説明が重
複する部分に対しては一部その説明を省略する。BEST MODE FOR CARRYING OUT THE INVENTION Next, the present invention will be described with reference to FIG.
A detailed description will be given based on the fourth embodiment. In addition, in order to facilitate understanding in the following description, in each layer for forming the organic LED element, the layer having the same function is denoted by the same reference numeral, and the film forming method and the like will be described. Description of some of the overlapping portions will be omitted.
【００１１】図１に符号１０で示すものは本発明に係る
有機ＬＥＤ素子の第１の実施形態であり、この第１の実
施形態における有機ＬＥＤ素子１０は、基板１と、陽極
２と、正孔注入輸送層３と、発光層４と、電子注入輸送
層５と、陰極６との各層で構成されている。A reference numeral 10 in FIG. 1 is a first embodiment of the organic LED element according to the present invention. The organic LED element 10 in the first embodiment has a substrate 1, an anode 2 and a positive electrode. The hole injecting and transporting layer 3, the light emitting layer 4, the electron injecting and transporting layer 5, and the cathode 6 are formed.
【００１２】ここで、前記基板１はガラス、樹脂など透
明部材で形成されるものであり、前記陽極２はＩＴＯな
ど透明な導電膜を前記基板１上に蒸着、スパッタリング
などで成膜したものであり、これらの層１、２は従来例
で説明したものと同様にして形成されるものである。The substrate 1 is formed of a transparent material such as glass or resin, and the anode 2 is formed by depositing a transparent conductive film such as ITO on the substrate 1 by vapor deposition or sputtering. The layers 1 and 2 are formed in the same manner as described in the conventional example.
【００１３】そして、本発明では前記陽極２上にポリア
ゾメチンによる正孔注入輸送層３を成膜する。この正孔
注入輸送層３の成膜方法としては、Ｈ2 Ｎ―Ｒ1 ―ＮＨ
2 と、ＯＨＣ―Ｒ2 ―ＣＨＯとをモノマーとし、ｍ―ク
レゾール、ベンゼンなどの有機溶媒中で重合し、得られ
たポリアゾメチンをスピンコート、ディップコートなど
の湿式による成膜法で陽極２上に成膜し、その後に不活
性ガスの雰囲気中で略３００℃で加熱することにより高
分子のポリアゾメチン膜を得る第一方式。In the present invention, the hole injecting and transporting layer 3 made of polyazomethine is formed on the anode 2. The hole injecting and transporting layer 3 may be formed by using H 2 N—R 1 —NH
2 and OHC-R 2 -CHO as monomers, polymerized in an organic solvent such as m-cresol or benzene, and the obtained polyazomethine is formed on the anode 2 by a wet film-forming method such as spin coating or dip coating. The first method in which a high molecular weight polyazomethine film is obtained by forming a film on the substrate and then heating at about 300 ° C. in an atmosphere of an inert gas.
【００１４】または、Ｈ2 Ｎ―Ｒ1 ―ＮＨ2 と、ＯＨＣ
―Ｒ2 ―ＣＨＯとをモノマーとし、これらを１０-4〜１
０-5Torrの真空下で共蒸着し、これを不活性ガスの雰囲
気中で、略３００℃で加熱することにより高分子のポリ
アゾメチン膜を得る第二方式の何れの手段によっても良
いものである。Alternatively, H 2 N--R 1 --NH 2 and OHC
—R 2 —CHO as a monomer, and these are 10 −4 to 1
Any method of the second method for obtaining a polyazomethine polymer film by co-deposition under a vacuum of 0 -5 Torr and heating this at about 300 ° C. in an atmosphere of an inert gas may be used. is there.
【００１５】以上のようにして得られた正孔注入輸送層
３上には、クマリン６、ＤＣＭ１、或いは、図２に構造
式を示すテトラフェニルブタジエンなどの発光材料を蒸
着して発光層４を成膜し、前記発光層４上には図３に構
造式を示すオキサジアゾール誘導体、或いは、図４に構
造式を示すジフェノキノン誘導体など電子輸送材料を蒸
着し電子注入輸送層５を成膜し、更に前記電子注入輸送
層５上にはＭｇ：Ａｇ、Ａｌ、Ａｌ：Ｌｉなど陰極材料
を蒸着して陰極６を形成し、有機ＬＥＤ素子１０を完成
する。On the hole injecting and transporting layer 3 obtained as described above, a light emitting material such as coumarin 6, DCM 1 or tetraphenylbutadiene having a structural formula shown in FIG. A film is formed, and an electron transporting material such as an oxadiazole derivative having a structural formula shown in FIG. 3 or a diphenoquinone derivative having a structural formula shown in FIG. Further, a cathode material such as Mg: Ag, Al, Al: Li is vapor-deposited on the electron injecting and transporting layer 5 to form a cathode 6, thereby completing the organic LED element 10.
【００１６】尚、前記正孔注入輸送層３までを上記の第
１の実施形態と同一の工程で成膜し、図５に構造式を示
す８―ヒドロキシキノリン・アルミニウム錯体、或い
は、図６に構造式を示すペリノン誘導体などの発光材料
を蒸着して発光層４を成膜し、この発光層４上に上記Ｍ
ｇ：Ａｇなどの陰極６を形成して、図７に第２の実施形
態として示すように電子注入輸送層５を省略した有機Ｌ
ＥＤ素子２０としても良いものである。It is to be noted that the layers up to the hole injecting and transporting layer 3 are formed in the same process as in the first embodiment, and the 8-hydroxyquinoline aluminum complex whose structural formula is shown in FIG. A light emitting material such as a perinone derivative having a structural formula is vapor-deposited to form a light emitting layer 4, and the above M is formed on the light emitting layer 4.
g: an organic L in which a cathode 6 of Ag or the like is formed and the electron injecting and transporting layer 5 is omitted as shown in FIG. 7 as a second embodiment.
The ED element 20 is also good.
【００１７】次いで、上記の構成とした本発明の有機Ｌ
ＥＤ素子１０、２０の作用及び効果について説明する。
先ず第一には、本発明により前記正孔注入輸送層３が高
分子のポリアゾメチン膜で形成されたことで、この正孔
注入輸送層３は耐熱性に優れるものとなり、以後に行わ
れる工程での処理熱や素子駆動中の発熱による熱的な劣
化を防止する。Next, the organic L of the present invention having the above structure
The operation and effect of the ED elements 10 and 20 will be described.
First, since the hole injecting and transporting layer 3 is formed of a polymer polyazomethine film according to the present invention, the hole injecting and transporting layer 3 has excellent heat resistance. It is possible to prevent thermal deterioration due to processing heat in the above and heat generated while driving the element.
【００１８】また、第二には、前記正孔注入輸送層３を
高分子のポリアゾメチン膜としたことで、この正孔注入
輸送層３自体が上記第一方式で説明したようにスピンコ
ートなどの湿式の成膜法で形成可能となり、生産工程が
簡略化されると共に、続いて行われる発光層４の成膜が
湿式で行われた場合にも耐溶剤性に優れ、溶解などを生
じないものとすることができる。Secondly, since the hole injecting and transporting layer 3 is a high molecular weight polyazomethine film, the hole injecting and transporting layer 3 itself is spin-coated as described in the first method. Can be formed by the wet film forming method, and the production process is simplified, and even if the film formation of the light emitting layer 4 that is subsequently performed is wet, it has excellent solvent resistance and does not cause dissolution or the like. Can be one.
【００１９】図８に示すものは、本発明の第３実施形態
の有機ＬＥＤ素子３０であり、この第３実施形態では、
上記第１の実施形態中で第一方式として説明した、Ｈ2
Ｎ―Ｒ1 ―ＮＨ2 と、ＯＨＣ―Ｒ2 ―ＣＨＯとをモノマ
ーとし、ｍ―クレゾール、ベンゼンなどの有機溶媒中で
重合して得られるポリアゾメチン中にクマリン６、ＤＣ
Ｍ１、或いは、テトラフェニルブタジエン（図２参照）
などの発光材料を混和し、これをスピンコートなど湿式
法で陽極２上に成膜し、加熱処理を行うことで発光層４
を得るものである。FIG. 8 shows an organic LED element 30 according to the third embodiment of the present invention. In the third embodiment,
H 2 described as the first method in the first embodiment is used.
Coumarin 6, DC in polyazomethine obtained by polymerizing N—R 1 —NH 2 and OHC—R 2 —CHO as monomers in an organic solvent such as m-cresol or benzene
M1 or tetraphenyl butadiene (see Figure 2)
And the like are mixed, a wet method such as spin coating is used to form a film on the anode 2, and heat treatment is performed to form the light emitting layer 4
Is what you get.
【００２０】尚、前記発光層４を形成するに当たって
は、上記第１の実施形態中で第二方式として説明したよ
うに、陽極２上にＨ2 Ｎ―Ｒ1 ―ＮＨ2 と、ＯＨＣ―Ｒ
2 ―ＣＨＯとのモノマーと、クマリン６、ＤＣＭ１、テ
トラフェニルブタジエンなど発光材料を共蒸着し、加熱
することで発光層４を得るものとしても良い。In forming the light emitting layer 4, H 2 N—R 1 —NH 2 and OHC—R 2 are formed on the anode 2 as described as the second method in the first embodiment.
The light emitting layer 4 may be obtained by co-evaporating a monomer such as 2- CHO and a light emitting material such as coumarin 6, DCM1, and tetraphenyl butadiene and heating.
【００２１】そして、前記発光層４上には、第１の実施
形態と同様にオキサジアゾール誘導体（図３参照）、或
いは、ジフェノキノン誘導体（図４参照）などの電子輸
送材料を蒸着し電子注入輸送層５を成膜し、更に前記電
子注入輸送層５上にはＭｇ：Ａｇなどの陰極材料を蒸着
して陰極６を形成し、有機ＬＥＤ素子３０を形成するも
のである。このときに、前記電子注入輸送層５を省略
し、前記発光層４上に陰極６を直接に成膜して、図９に
示すように第４の実施形態の有機ＬＥＤ素子４０として
も良いものである。Then, as in the first embodiment, an electron transporting material such as an oxadiazole derivative (see FIG. 3) or a diphenoquinone derivative (see FIG. 4) is vapor-deposited on the light emitting layer 4 to inject electrons. The transport layer 5 is formed, and a cathode material such as Mg: Ag is vapor-deposited on the electron injecting and transporting layer 5 to form the cathode 6, thereby forming the organic LED element 30. At this time, the electron injecting and transporting layer 5 may be omitted, and the cathode 6 may be directly formed on the light emitting layer 4 to form the organic LED element 40 of the fourth embodiment as shown in FIG. Is.
【００２２】このように、発光層４を高分子のポリアゾ
メチン膜としたことでも、前の第１、第２の実施形態で
説明したのと同様に、この発光層４はスピンコートなど
の湿式の成膜法で形成可能となり、生産工程が簡略化さ
れると共に、続いて行われる工程での処理熱や、完成後
の素子駆動中の発熱による熱的な劣化を防止できるもの
となる。As described above, even if the light emitting layer 4 is a high molecular weight polyazomethine film, the light emitting layer 4 is wet-coated by spin coating or the like, as described in the first and second embodiments. The film can be formed by the film forming method described above, the production process can be simplified, and thermal deterioration due to heat of processing in the subsequent process and heat generated during device driving after completion can be prevented.
【００２３】[0023]
【発明の効果】以上に説明したように本発明により、有
機ＬＥＤ素子の正孔注入輸送層または発光層に、―(―
Ｒ1 ―ＣＨ＝Ｎ―Ｒ2 ―Ｎ＝ＣＨ―)― の一般式で表さ
れるポリアゾメチンを用いるものとしたことで、耐熱性
に優れる正孔注入輸送層または発光層とし、生産工程中
における処理熱、或いは、完成後の駆動時の発熱によっ
ても熱的な劣化を生じないものとし、この種の有機ＬＥ
Ｄ素子の寿命の延長を可能として、信頼性の向上に極め
て優れた効果を奏するものである。As described above, according to the present invention, the hole injecting / transporting layer or the light emitting layer of the organic LED element is
By using polyazomethine represented by the general formula of R 1 —CH═N—R 2 —N═CH —) —, a hole injecting and transporting layer or a light emitting layer having excellent heat resistance can be obtained. It is assumed that thermal deterioration does not occur due to the processing heat in the above, or the heat generated during driving after completion.
This makes it possible to extend the life of the D element and has an extremely excellent effect of improving reliability.
【００２４】また、上記構成としたことで、上記ポリア
ゾメチンで形成される正孔注入輸送層または発光層自体
をスピンコートなど湿式で成膜可能として生産工程を簡
素化すると共に、正孔注入輸送層を上記ポリアゾメチン
で形成する場合には、そのポリアゾメチンの優れた耐溶
剤性により、後に行われる発光層も湿式で成膜可能とし
て、有機ＬＥＤ素子の生産工程を簡素化するものとし
て、以て、この種の有機ＬＥＤ素子の生産性の向上とコ
ストダウンとに極めて優れた効果を奏するものである。Further, with the above structure, the hole injecting and transporting layer formed of the polyazomethine or the light emitting layer itself can be formed into a film by a wet method such as spin coating, and the production process can be simplified, and the hole injecting and transporting can be performed. When the layer is formed from the above polyazomethine, the excellent solvent resistance of the polyazomethine allows the light emitting layer to be formed later to be wet film-formed, thereby simplifying the production process of the organic LED element. Thus, it is possible to achieve an extremely excellent effect in improving the productivity and reducing the cost of this type of organic LED element.
【図１】 本発明に係る有機ＬＥＤ素子の第１の実施形
態を示す説明図である。FIG. 1 is an explanatory view showing a first embodiment of an organic LED element according to the present invention.
【図２】 本発明に係る有機ＬＥＤ素子の発光材料であ
るテトラフェニルブタジエンを示す構造式である。FIG. 2 is a structural formula showing tetraphenylbutadiene which is a light emitting material of an organic LED element according to the present invention.
【図３】 本発明に係る有機ＬＥＤ素子の電子輸送材料
であるオキサジアゾール誘導体を示す構造式である。FIG. 3 is a structural formula showing an oxadiazole derivative which is an electron transport material of the organic LED element according to the present invention.
【図４】 本発明に係る有機ＬＥＤ素子の電子輸送材料
であるジフェノキノン誘導体を示す構造式である。FIG. 4 is a structural formula showing a diphenoquinone derivative which is an electron transport material of an organic LED element according to the present invention.
【図５】 本発明に係る有機ＬＥＤ素子の発光材料であ
る８―ヒドロキシキノリン・アルミニウム錯体を示す構
造式である。FIG. 5 is a structural formula showing an 8-hydroxyquinoline / aluminum complex which is a light emitting material of the organic LED element according to the present invention.
【図６】 本発明に係る有機ＬＥＤ素子の発光材料であ
るペリノン誘導体を示す構造式である。FIG. 6 is a structural formula showing a perinone derivative which is a light emitting material of an organic LED element according to the present invention.
【図７】 同じく本発明に係る有機ＬＥＤ素子の第２の
実施形態を示す説明図である。FIG. 7 is an explanatory view showing a second embodiment of the organic LED element according to the present invention.
【図８】 同じく本発明に係る有機ＬＥＤ素子の第３の
実施形態を示す説明図である。FIG. 8 is an explanatory view showing a third embodiment of an organic LED element according to the present invention.
【図９】 同じく本発明に係る有機ＬＥＤ素子の第４の
実施形態を示す説明図である。FIG. 9 is an explanatory view showing a fourth embodiment of the organic LED element according to the present invention.
【図１０】 従来例を示す説明図である。FIG. 10 is an explanatory diagram showing a conventional example.
【図１１】 別の従来例を示す説明図である。FIG. 11 is an explanatory diagram showing another conventional example.
１０、２０、３０、４０……有機ＬＥＤ素子 １……基板 ２……陽極 ３……正孔注入輸送層 ４……発光層 ５……電子注入輸送層 ６……陰極 10, 20, 30, 40 ... Organic LED element 1 ... Substrate 2 ... Anode 3 ... Hole injecting / transporting layer 4 ... Emitting layer 5 ... Electron injecting / transporting layer 6 ... Cathode
Claims (3)
を含有することを特徴とする有機ＬＥＤ素子。 【化１】 1. An organic LED device comprising a polyazomethine represented by the general formula (1). Embedded image
孔注入輸送層に用いたことを特徴とする請求項１記載の
有機ＬＥＤ素子。2. The organic LED device according to claim 1, wherein the polyazomethine of the general formula (1) is used in a hole injecting and transporting layer.
光層に用いたことを特徴とする請求項１記載の有機ＬＥ
Ｄ素子。3. The organic LE according to claim 1, wherein the polyazomethine of the general formula (1) is used in a light emitting layer.
D element.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2303796A JPH09194832A (en) | 1996-01-17 | 1996-01-17 | Organic led element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2303796A JPH09194832A (en) | 1996-01-17 | 1996-01-17 | Organic led element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH09194832A true JPH09194832A (en) | 1997-07-29 |
Family
ID=12099278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2303796A Pending JPH09194832A (en) | 1996-01-17 | 1996-01-17 | Organic led element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH09194832A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011102330A1 (en) | 2010-02-18 | 2011-08-25 | 綜研化学株式会社 | Novel polyazomethine |
| JP5665772B2 (en) * | 2010-01-29 | 2015-02-04 | 綜研化学株式会社 | New azomethine oligomer |
-
1996
- 1996-01-17 JP JP2303796A patent/JPH09194832A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5665772B2 (en) * | 2010-01-29 | 2015-02-04 | 綜研化学株式会社 | New azomethine oligomer |
| WO2011102330A1 (en) | 2010-02-18 | 2011-08-25 | 綜研化学株式会社 | Novel polyazomethine |
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