JPH0532966A - Organic electrolytically luminescent element - Google Patents
Organic electrolytically luminescent elementInfo
- Publication number
- JPH0532966A JPH0532966A JP3189789A JP18978991A JPH0532966A JP H0532966 A JPH0532966 A JP H0532966A JP 3189789 A JP3189789 A JP 3189789A JP 18978991 A JP18978991 A JP 18978991A JP H0532966 A JPH0532966 A JP H0532966A
- Authority
- JP
- Japan
- Prior art keywords
- chemical
- compound
- organic
- polycyclic aromatic
- condensed polycyclic
- 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
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims description 47
- -1 polycyclic aromatic compounds Chemical class 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical class 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 24
- 238000002347 injection Methods 0.000 abstract description 19
- 239000007924 injection Substances 0.000 abstract description 19
- OUEIPKXVZRHNIB-UHFFFAOYSA-N 1-(3-pyren-1-ylpropyl)pyrene Chemical group C1=C2C(CCCC=3C4=CC=C5C=CC=C6C=CC(C4=C65)=CC=3)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 OUEIPKXVZRHNIB-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 39
- 230000005525 hole transport Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- 239000003086 colorant Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 239000007772 electrode material Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 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 1
- QSXAGJHVLNEABN-UHFFFAOYSA-N 1-(3-phenanthren-1-ylpropyl)phenanthrene Chemical compound C1=CC2=CC=CC=C2C2=C1C(CCCC=1C3=C(C4=CC=CC=C4C=C3)C=CC=1)=CC=C2 QSXAGJHVLNEABN-UHFFFAOYSA-N 0.000 description 1
- HIOZPFGGCXEPAP-UHFFFAOYSA-N 1-propylpyrene Chemical compound C1=C2C(CCC)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HIOZPFGGCXEPAP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FLGMAMYMYDIKLE-UHFFFAOYSA-N chloro hypochlorite;phosphane Chemical compound P.ClOCl FLGMAMYMYDIKLE-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000007935 neutral effect Effects 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
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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 light emitting material which is excellent in film forming property and can exhibit sufficient brightness.
【０００２】[0002]
【従来の技術】近年、情報機器の多様化にともなって、
ＣＲＴ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。2. Description of the Related Art In recent years, with the diversification of information equipment,
There is an increasing need for a flat display device that consumes less power and occupies less space than a CRT. As such flat display elements, there are liquid crystals, plasma displays, and the like. Recently, however, attention has been paid to EL elements that are light-emitting and have a clear display.
【０００３】ここで、上記ＥＬ素子は、構成する材料に
より、無機ＥＬ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。これに対し、上記有機
ＥＬ素子は、電極から注入された電荷が発光体中で再結
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ＥＬ素子
は、これからの表示素子として非常に有望である。ここ
で、有機ＥＬ素子は、一般に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
と電極注入電極との間に、発光層と電子輸送層とが形成
された構造（ＳＨ−Ｂ構造）〕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〕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ＩＴＯ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型の性質、
電子輸送層は、ｎ型の性質を有する材料が用いられる。
上記発光層は、上記ＳＨ−Ａ構造では、ｎ型の性質、Ｓ
Ｈ−Ｂ構造では、Ｐ型の性質、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（又は、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。The EL element can be roughly classified into an inorganic EL element and an organic EL element, depending on the constituent materials, and the inorganic EL element has already been put into practical use. However, the driving method of the above-mentioned inorganic EL is so-called collision excitation type light emission in which electrons accelerated by application of a high electric field collide and excite light emission centers to emit light, and therefore, it is necessary to drive at a high voltage. Therefore, there is a problem that the cost of the peripheral device is increased. On the other hand, since the organic EL element is so-called injection type light emission in which the charges injected from the electrodes are recombined in the light emitting body to emit light, it can be driven at a low voltage. Moreover, there is an advantage that an arbitrary luminescent color can be easily obtained by changing the molecular structure of the organic compound. Therefore, the organic EL element is very promising as a display element in the future. Here, the organic EL 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 injection electrode and an electrode). Structure in which a light emitting layer and an electron transport layer are formed between the injection electrodes (SH-B structure)] Three-layer structure [Hole transport layer, light emitting layer, and electrons between the hole injection electrode and the electron injection electrode] And a transport layer is formed]. An electrode material having a large work function such as gold or ITO is used as the hole injecting electrode, and an electrode material having a small work function such as Mg is used as the electron injecting electrode. An organic material is used for the hole transport layer, the light emitting layer, and the electron transport layer, and the hole transport layer has a P-type property,
A material having an n-type property is used for the electron transport layer.
In the SH-A structure, the light emitting layer has an n-type property, S
A material having a P-type property is used in the H-B structure, and a material having a property close to neutrality is used 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 in the light emitting layer to emit light. .
【０００４】[0004]
【発明が解決しようとする課題】上記有機ＥＬ素子に用
いる有機発光材料は、置換基を変える等により、材料の
性質を変更させ、任意の発光色を得ることが可能である
など、材料設計の自由度が大きい。従って、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。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
であり、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等が提案されている
が、いずれも製膜性に劣り、満足な輝度と安定性とを得
られるには至らない。The organic light-emitting material used for the above-mentioned organic EL element has a material designing property such that the property of the material can be changed by changing the substituent and the like to obtain an arbitrary emission color. Greater freedom. Therefore, in theory,
It is possible to emit all colors from blue to red, and various stable light-emitting materials that actually emit green, yellow, and orange have been proposed. 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 element or an organic EL element. Although 4,4-tetraphenyl-1,3 butadiene derivative, styrylbenzene derivative, and the like have been proposed, none of them has a poor film-forming property, so that satisfactory brightness and stability cannot be obtained.
【０００５】このように青色発光する材料の成功は、例
えば、ＥＬ素子による色の三原色（青、赤、緑）を使用
した、フルカラーディスプレイの開発につながる。本発
明は、上記問題に鑑み青色発光し且つ製膜性に優れ、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 success of the material that emits blue light in this way leads to the development of a full-color display using, for example, the three primary colors (blue, red, and green) of colors of EL elements. In view of the above problems, an object of the present invention is to provide an electroluminescent device using a light emitting material that emits blue light, is excellent in film forming property, and can obtain sufficient brightness and stability.
【０００６】[0006]
【課題を解決するための手段】上記目的を達成するため
に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解発光素子におい
て、前記有機発光層に複数の縮合多環芳香族を有した化
合物を用いることを特徴とする。In order to achieve the above object, in an electroluminescent device having a hole injecting electrode, an electron injecting electrode, and an organic light emitting layer provided between these electrodes, a plurality of organic light emitting layers are provided in the organic light emitting layer. The compound having a condensed polycyclic aromatic group of 1 is used.
【０００７】前記縮合多環芳香族として２〜５個のベン
ゼン環が縮合した縮合多環芳香族を用いることができ
る。前記複数の縮合多環芳香族を有した化合物が前記化
１に示される化合物である。但し、前記化１中、Ａｒ1
〜Ａｒn として、縮合多環芳香族を、Ｒとして２箇所以
上縮合多環芳香族によって置換された化合物を用いるこ
とができる。As the condensed polycyclic aromatic, a condensed polycyclic aromatic in which 2 to 5 benzene rings are condensed can be used. The compound having a plurality of condensed polycyclic aromatic compounds is the compound represented by Chemical Formula 1 above. However, in the above chemical formula 1 , Ar 1
As to Ar n, a condensed polycyclic aromatic, it is possible to use a compound substituted by a condensed polycyclic aromatic least two places as R.
【０００８】前記化１中Ａｒ1 〜Ａｒn は、前記化２〜
化６に示す群から選択され、前記Ｒはアルキル鎖、置換
ベンゼン、複素環、から選択される。前記アルキル鎖と
して前記化７に示される化合物を、前記置換ベンゼンと
して前記化８に示される化合物を、前記複素環として前
記化９に示される化合物を用いることができる。In the above chemical formula 1, Ar 1 to Ar n are the chemical formulas 2 to 2.
Is selected from the group represented by Chemical formula 6, wherein R is selected from an alkyl chain, a substituted benzene, and a heterocycle. As the alkyl chain, the compound shown in Chemical formula 7 can be used, as the substituted benzene, the compound shown in Chemical formula 8 can be used, and as the heterocycle, the compound shown in Chemical formula 9 can be used.
【０００９】[0009]
【作用】前記縮合多環芳香族を有する化合物は、製膜性
に優れており、有機発光層に用いた場合、良好な有機Ｅ
Ｌ素子を形成することができる。しかも、長期間保存或
いは、駆動させた場合であっても、結晶が析出されにく
く、輝度の低下も従来の青色有機ＥＬ素子と比較して改
善されている。The compound having a condensed polycyclic aromatic compound has excellent film-forming properties and, when used in an organic light-emitting layer, a good organic E
An L element can be formed. In addition, even if it is stored or driven for a long period of time, crystals are less likely to be deposited, and the reduction in brightness is improved as compared with the conventional blue organic EL element.
【００１０】また、発光ピーク波長は、縮合多環芳香族
のベンゼン環が増えるほど長波長側にシフトする。４３
０ｎｍ〜５２０ｎｍの、ほぼ青色の発光を呈するのは、
ベンゼン環２〜５個からなる縮合多環芳香族を有した化
合物である。The emission peak wavelength shifts to the longer wavelength side as the number of condensed polycyclic aromatic benzene rings increases. 43
The emission of almost blue light of 0 nm to 520 nm is
It is a compound having a condensed polycyclic aromatic group consisting of 2 to 5 benzene rings.
【００１１】[0011]
〔実施例１〕図１は、本発明第一実施例に係る電界発光
素子の断面図である。以下この図に基づいて説明を行
う。ガラス基板１上には、インジウム−スズ酸化物（Ｉ
ＴＯ）から成るホール注入電極が２と、ジアミン（下記
化１０で示す）からなる有機ホール輸送層３と、１，３
−Ｂｉｓ（１−ｐｙｒｅｎｙｌ）ｐｒｏｐａｎｅ（株式
会社 同仁化学研究所製）から成る有機発光層４と、オ
キサジアゾール誘導体（下記化１１で示す）からなる電
子輸送層５と、ＭｇとＡｇが１０：１の比率で混合され
た電子注入電極６とが順に形成されている。尚、上記
１，３−Ｂｉｓ（１−ｐｙｒｅｎｙｌ）ｐｒｏｐａｎｅ
は、以下ＰＣＰ3 と称し、下記化１２に示す。[Embodiment 1] FIG. 1 is a sectional view of an electroluminescent device according to a first embodiment of the present invention. Hereinafter, description will be given based on this figure. On the glass substrate 1, indium-tin oxide (I
A hole injecting electrode 2 made of TO), an organic hole transport layer 3 made of diamine (shown below in Chemical Formula 10), 1, 3
An organic light emitting layer 4 made of —Bis (1-pyrenyl) propane (manufactured by Dojindo Laboratories Ltd.), an electron transport layer 5 made of an oxadiazole derivative (shown in Chemical Formula 11 below), and Mg and Ag are 10: Electron injection electrodes 6 mixed at a ratio of 1 are sequentially formed. The 1,3-Bis (1-pyrenyl) propane described above is used.
Is hereinafter referred to as PCP 3, and is shown in Chemical formula 12 below.
【００１２】[0012]
【化１０】 [Chemical 10]
【００１３】[0013]
【化１１】 [Chemical 11]
【００１４】[0014]
【化１２】 [Chemical 12]
【００１５】ここで上記構造の電界発光素子は、以下の
ようにして作成した。ガラス基板上にインジウム−スズ
酸化物（ＩＴＯ）からなるホール注入電極２が形成され
た基板上を中性洗剤中で２０分間、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
で上記基板を煮沸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（６００Å）を形成した後、この有機ホール
輸送層３上に有機発光層４であるＰＣＰ3 を１００Åの
厚さに蒸着した。更に、この上に電子輸送層５としてオ
キサジアゾール誘導体を３００Åの厚さに蒸着した。最
後に、電子輸送層５の上にＭｇとＡｇとを１０：１の比
率で共蒸着して、電子注入電極６を形成して、３層構造
（ＤＨ）の有機電界発光素子を作成した。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, the electroluminescent device having the above structure was prepared as follows. The substrate on which the hole injecting electrode 2 made of indium-tin oxide (ITO) was formed on the glass substrate was ultrasonically cleaned in a neutral detergent for 20 minutes, in acetone for 20 minutes, and in ethanol for 20 minutes. . Next, the substrate was put in boiling ethanol for about 1 minute, taken out, and immediately blown dry. Then, a diamine is vacuum-deposited on the hole injecting electrode 2 to form an organic hole transport layer 3 (600 Å), and the organic light emitting layer 4 of PCP 3 having a thickness of 100 Å is formed on the organic hole transport layer 3. It was vapor-deposited. Further, an oxadiazole derivative was vapor-deposited thereon as an electron transport layer 5 to a thickness of 300Å. Finally, Mg and Ag were co-evaporated on the electron transport layer 5 at a ratio of 10: 1 to form the electron injection electrode 6, thereby forming an organic electroluminescence device having a three-layer structure (DH). It should be noted that in the above vapor deposition, the degree of vacuum was 1 × 10 −6 Torr and the substrate temperature was 20
C., and the vapor deposition rate of the organic layer was 2Å / sec.
【００１６】上記のように作成した有機電界発光素子を
以下（Ａ1 ）素子と称する。
〔実施例２〕有機発光層４として、１，３−Ｂｉｓ（１
−ｐｈｅｎａｎｔｈｒｙｌ）ｐｒｏｐａｎｅ（下記化１
３に示す）を用いる以外は、実施例１と同様に有機電界
素子を作成した。以下この素子を（Ａ2 ）素子と称す
る。The organic electroluminescent device produced as described above is hereinafter referred to as (A 1 ) device. Example 2 As the organic light emitting layer 4, 1,3-Bis (1
-Phenanthryl) propane (Chemical formula 1 below
3) was used, and an organic electric field element was produced in the same manner as in Example 1. Hereinafter, this element is referred to as an (A 2 ) element.
【００１７】[0017]
【化１３】 [Chemical 13]
【００１８】尚、上記有機発光層４に用いられた発光材
料１，３−Ｂｉｓ（１−ｐｈｅｎａｎｔｈｒｙｌ）ｐｒ
ｏｐａｎｅは、Zeitschrift f ▲ｕ▼ r Physikalische
Chemie Neue Folge , Bd. 101, S. 267-276 (1976) 記
載の合成方法を用いて合成される。
〔比較例〕有機発光層４の材料として１，１，４，４−
テトラフェニル−１，３−ブタジエン（下記化１４に示
す）を用いる他は、上記実施例１の電界発光素子と同様
に有機電界発光素子を作成した。このように作成した比
較例有機電界素子を以下（Ｂ）素子と称する。The light emitting material 1,3-Bis (1-phenanthryl) pr used in the organic light emitting layer 4 is used.
Opane is Zeitschrift f ▲ u ▼ r Physikalische
It is synthesized using the synthesis method described in Chemie Neue Folge, Bd. 101, S. 267-276 (1976). [Comparative Example] 1,1,4,4-as the material of the organic light emitting layer 4
An organic electroluminescent device was prepared in the same manner as the electroluminescent device of Example 1 except that tetraphenyl-1,3-butadiene (shown in Chemical Formula 14 below) was used. The comparative organic electric field device thus prepared is hereinafter referred to as (B) device.
【００１９】[0019]
【化１４】 [Chemical 14]
【００２０】〔実験１〕上記実施例（Ａ1 ）素子、（Ａ
2 ）素子と比較例（Ｂ）素子とについて発光ピーク波
長、輝度、発光寿命を測定した。ＥＬ発光は、それぞれ
の素子のホール注入電極２側をプラスのバイアス、電子
注入電極５をマイナスのバイアスに印加し、回折格子分
光器（ＪＡＳＣＯ Ｇ−１０）により分光し、フォトカ
ウンター（浜松ホトニクス）で各々の単色光の強度を測
定して波長を求めた。その結果、（Ａ1 ）素子は、５０
０ｎｍ、（Ａ2 ）素子は４８０ｎｍ、（Ｂ）素子は４６
０ｎｍといずれも青色発光を呈した。尚、（Ａ1 ）素子
のスペクトルデータを図２に示す。[Experiment 1] Element (A 1 ) of the above embodiment, (A
2 ) The emission peak wavelength, luminance, and emission life of the device and the device of Comparative Example (B) were measured. For EL light emission, a positive bias is applied to the hole injection electrode 2 side of each element and a negative bias is applied to the electron injection electrode 5, and light is dispersed by a diffraction grating spectroscope (JASCO G-10), and a photo counter (Hamamatsu Photonics) is used. The wavelength of each monochromatic light was measured by measuring the intensity. As a result, the (A 1 ) element is 50
0 nm, (A 2 ) element is 480 nm, (B) element is 46 nm
All emitted blue light at 0 nm. The spectrum data of the (A 1 ) element is shown in FIG.
【００２１】又、輝度と発光寿命については以下のよう
な結果となった。
（Ａ1 ）素子は駆動電圧２３Ｖ、電流密度１８０ｍＡ／
ｃｍ2の条件下で、８００ｃｄ／ｍ2 の輝度が確認で
き、電流密度３０ｍＡ／ｃｍ2 で定電流連続駆動させる
と、３時間発光が確認できた。
（Ａ2 ）素子は駆動電圧２０Ｖ、電流密度１５０ｍＡ／
ｃｍ2の条件下で、６００ｃｄ／ｍ2 の輝度が確認で
き、電流密度３０ｍＡ／ｃｍ2 で定電流連続駆動させる
と、約２時間発光が確認できた。The following results were obtained regarding the brightness and the light emission lifetime. (A 1 ) element has a driving voltage of 23 V and a current density of 180 mA /
under the conditions of cm 2, 800 cd / m brightness of 2 can be confirmed, the constant current to continuously driven at a current density of 30 mA / cm 2, 3 hours luminescence was confirmed. (A 2 ) element has a driving voltage of 20 V and a current density of 150 mA /
under the conditions of cm 2, 600 cd / m brightness of 2 can be confirmed, the constant current to continuously driven at a current density of 30 mA / cm 2, about 2 hours emission was confirmed.
【００２２】（Ｂ）素子は駆動電圧１０Ｖ、電流密度１
００ｍＡ／ｃｍ2の条件下で、７００ｃｄ／ｍ2 の輝度
が確認でき、電流密度３０ｍＡ／ｃｍ2 で定電流連続駆
動させると、１０分間で発光が起こらなくなった。
上記結果により、本発明の実施例の方が安定な発光が得
られることがわかった。これは、発光材料の製膜性の良
さに起因していると思われる。
〔実施例３〕有機発光層４の材料として下記化１５〜化
１９に示す化合物を用いる他は、上記実施例１の電界発
光素子と同様に有機電界発光素子を作成した。このよう
に作成した有機電界発光素子を、以下夫々（Ａ3 ）素子
〜（Ａ7 ）素子と称する。(B) Element has a driving voltage of 10 V and a current density of 1
Under the conditions of 00mA / cm 2, confirmed luminance of 700 cd / m 2, the constant current to continuously driven at a current density of 30 mA / cm 2, emission is no longer occur in 10 minutes. From the above results, it was found that more stable light emission was obtained in the example of the present invention. This is considered to be due to the good film forming property of the light emitting material. Example 3 An organic electroluminescent device was prepared in the same manner as the electroluminescent device of Example 1 except that the compounds shown in Chemical formulas 15 to 19 below were used as the material for the organic luminescent layer 4. Such an organic electroluminescent device was prepared in the following referred to as respectively (A 3) elements ~ (A 7) elements.
【００２３】[0023]
【化１５】 [Chemical 15]
【００２４】[0024]
【化１６】 [Chemical 16]
【００２５】[0025]
【化１７】 [Chemical 17]
【００２６】[0026]
【化１８】 [Chemical 18]
【００２７】[0027]
【化１９】 [Chemical 19]
【００２８】尚、前記化１５、化１６、化１７に示され
た有機発光層に用いられた発光材料は、上記実施例２の
発光材料と同様に合成することができる。前記化１８に
示される化合物は、Wrutz-Fittig反応を用いることで合
成できる。尚、下記化２０に合成経路を示す。The light-emitting materials used in the organic light-emitting layer shown in Chemical formulas 15, 15, and 17 can be synthesized in the same manner as the light-emitting material of Example 2 above. The compound represented by the chemical formula 18 can be synthesized by using the Wrutz-Fittig reaction. The synthetic route is shown in Chemical Formula 20 below.
【００２９】[0029]
【化２０】 [Chemical 20]
【００３０】前記化１９に示される化合物については、
以下のように合成を行った。
（化１９の合成法）１−Ｎａｐｈｔｈｏｉｃ ａｃｉｄ
（ａ）をエタノールでエステル化した後、ヒドラジン１
水和物（８０％）と、エステル（ｂ）を反応させて、ヒ
ドラジド（ｃ）を合成した。The compound represented by the chemical formula 19 is as follows:
The synthesis was carried out as follows. (Synthesis Method of Chemical Formula 19) 1-Naphthoic acid
After esterification of (a) with ethanol, hydrazine 1
The hydrate (80%) was reacted with the ester (b) to synthesize the hydrazide (c).
【００３１】一方、１−Ｎａｐｈｔｈｏｉｃ ａｃｉｄ
（ａ）を塩化チオニル（ＳＯＣｌ3 ）と反応させ、酸塩
化物（ｄ）を合成した。次に、ヒドラジド（ｃ）と酸塩
化物（ｄ）を脱水ピリジン中に入れ、Ｎ2 雰囲気下、非
水系で還流を１時間３０分行った。生成物（ｅ）を水中
で沈澱させた後、吸引濾過を行った。生成物（ｅ）は、
トルエンで再結晶して、精製した（収率５０％）。On the other hand, 1-Naphthoic acid
The acid chloride (d) was synthesized by reacting (a) with thionyl chloride (SOCl 3 ). Next, the hydrazide (c) and the acid chloride (d) were put into dehydrated pyridine and refluxed for 1 hour and 30 minutes in a non-aqueous system under a N 2 atmosphere. The product (e) was precipitated in water and suction filtered. The product (e) is
It was recrystallized from toluene and purified (yield 50%).
【００３２】生成物（ｅ）は、オキソ塩化リン中に入
れ、Ｎ2 雰囲気下、非水系で還流を１晩行った。オキサ
ジアゾール環を有する化合物（ｆ）は、トルエンで再結
晶を行い生成した（収率４０％）。上記反応経路を下記
化２１に示す。The product (e) was placed in phosphorus oxochloride and refluxed overnight in a non-aqueous system under N 2 atmosphere. The compound (f) having an oxadiazole ring was produced by recrystallization from toluene (yield 40%). The above reaction route is shown in Chemical Formula 21 below.
【００３３】[0033]
【化２１】 [Chemical 21]
【００３４】〔実験２〕上記実施例（Ａ3 ）素子〜（Ａ
7 ）素子についてそれぞれ、ＥＬ発光ピーク波長、輝
度、発光色についての測定結果が表１に示されている。[Experiment 2] Devices (A 3 ) to (A 3 ) of the above embodiment
7 ) Table 1 shows the measurement results of the EL emission peak wavelength, luminance, and emission color of each element.
【００３５】[0035]
【表１】 [Table 1]
【００３６】上記表１から明らかなように、（Ａ3 ）素
子〜（Ａ7 ）素子は、青色或いは、青紫色の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
（Ａ 3 ）素子〜（Ａ7 ）素子は優れた耐久性を有してい
る。As is clear from Table 1, (A3) Element
Child ~ (A7) The device is a blue or bluish purple EL emission
It was confirmed that there is a high brightness. Also
(A 3) Element ~ (A7) The element has excellent durability
It
【００３７】[0037]
【発明の効果】以上説明したように、本発明の有機発光
材料を用いることによって、青色発光の有機電界素子を
提供することができ、且つ、製膜性に優れているため、
発光時に発光材料が短時間で析出することなく安定な青
色発光を得ることができた。さらに、本発明の発光材料
のケイ光波長は、主として、ベンゼン環の数によってコ
ントロールできるので、青色発光を呈する発光材料の材
料設計をより簡易行うことができる。As described above, by using the organic light emitting material of the present invention, it is possible to provide a blue light emitting organic electroluminescent element and it is excellent in film forming property.
It was possible to obtain stable blue light emission without depositing the light emitting material in a short time during light emission. Furthermore, since the fluorescent wavelength of the luminescent material of the present invention can be controlled mainly by the number of benzene rings, the material design of the luminescent material that emits blue light can be more easily performed.
【図１】本発明の一実施例の有機発光素子の断面図であ
る。FIG. 1 is a cross-sectional view of an organic light emitting device according to an embodiment of the present invention.
【図２】（Ａ1 ）素子のＥＬ発光波長のスペクトルデー
タを示す図である。FIG. 2 is a diagram showing spectrum data of EL emission wavelength of the (A 1 ) element.
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 有機電子輸送層 ６ 電子注入電極 1 glass substrate 2-hole injection electrode 3 Organic hole transport layer 4 Organic light emitting layer 5 Organic electron transport layer 6 Electron injection electrode
───────────────────────────────────────────────────── フロントページの続き (72)発明者 黒木 和彦 守口市京阪本通２丁目18番地 三洋電機株 式会社内 ─────────────────────────────────────────────────── ─── Continued front page (72) Inventor Kazuhiko Kuroki 2-18 Keihanhondori, Moriguchi-shi Sanyo Electric Co., Ltd. Inside the company
Claims (5)
ら両電極間に設けられた有機発光層とを有する電解発光
素子において、前記有機発光層に複数の縮合多環芳香族
を有した化合物を用いることを特徴とする有機電界発光
素子。1. An electrolytic light-emitting device having a hole injecting electrode, an electron injecting electrode, and an organic light emitting layer provided between the two electrodes, wherein the organic light emitting layer comprises a compound having a plurality of condensed polycyclic aromatic compounds. An organic electroluminescent device characterized by being used.
ン環が縮合した縮合多環芳香族であることを特徴とする
請求項１記載の有機電界発光素子。2. The organic electroluminescent device according to claim 1, wherein the condensed polycyclic aromatic compound is a condensed polycyclic aromatic compound in which 2 to 5 benzene rings are condensed.
物が下記化１に示される化合物であることを特徴とする
請求項２記載の有機電界発光素子。 【化１】 但し、前記化１中、Ａｒ1 〜Ａｒn は、縮合多環芳香族
であり、Ｒは、２箇所以上縮合多環芳香族によって置換
された化合物である。3. The organic electroluminescent device according to claim 2, wherein the compound having a plurality of condensed polycyclic aromatic compounds is a compound represented by the following chemical formula 1. [Chemical 1] However, in Chemical Formula 1, Ar 1 to Ar n are condensed polycyclic aromatic compounds, and R is a compound substituted by two or more condensed polycyclic aromatic compounds.
に示す群から選択され、前記Ｒはアルキル鎖、置換ベン
ゼン、複素環、から選択されることを特徴とする請求項
３記載の有機電界発光素子。 【化２】 【化３】 【化４】 【化５】 【化６】 4. Ar 1 to Ar n are the following Chemical formulas 2 to 6
The organic electroluminescence device according to claim 3, wherein R is selected from the group consisting of alkyl chains, substituted benzenes, and heterocycles. [Chemical 2] [Chemical 3] [Chemical 4] [Chemical 5] [Chemical 6]
合物であり、前記置換ベンゼンが下記化８に示される化
合物であり、前記複素環が下記化９に示される化合物で
あることを特徴とする請求項４記載の有機電界発光素
子。 【化７】 【化８】 【化９】 5. The compound wherein the alkyl chain is a compound represented by the following chemical formula 7, the substituted benzene is a compound represented by the following chemical formula 8, and the heterocycle is a compound represented by the following chemical formula 9. The organic electroluminescent element according to claim 4. [Chemical 7] [Chemical 8] [Chemical 9]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18978991A JP3162741B2 (en) | 1991-07-30 | 1991-07-30 | Organic electroluminescent device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18978991A JP3162741B2 (en) | 1991-07-30 | 1991-07-30 | Organic electroluminescent device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0532966A true JPH0532966A (en) | 1993-02-09 |
| JP3162741B2 JP3162741B2 (en) | 2001-05-08 |
Family
ID=16247233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18978991A Expired - Fee Related JP3162741B2 (en) | 1991-07-30 | 1991-07-30 | Organic electroluminescent device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3162741B2 (en) |
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|---|---|---|---|---|
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| US6203933B1 (en) | 1995-05-17 | 2001-03-20 | Tdk Corporation | Organic EL element |
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| JP3162741B2 (en) | 2001-05-08 |
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