JP2974845B2 - Organic electroluminescence device - Google Patents
Organic electroluminescence deviceInfo
- Publication number
- JP2974845B2 JP2974845B2 JP4064291A JP6429192A JP2974845B2 JP 2974845 B2 JP2974845 B2 JP 2974845B2 JP 4064291 A JP4064291 A JP 4064291A JP 6429192 A JP6429192 A JP 6429192A JP 2974845 B2 JP2974845 B2 JP 2974845B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- chemical formula
- embedded image
- transport layer
- substituent
- 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
- 238000005401 electroluminescence Methods 0.000 title claims description 12
- 239000000126 substance Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 14
- 150000002894 organic compounds Chemical class 0.000 claims description 14
- -1 coumarin compound Chemical class 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 9
- 229960000956 coumarin Drugs 0.000 claims description 9
- 235000001671 coumarin Nutrition 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 2
- 239000010409 thin film Substances 0.000 description 16
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- 238000000295 emission spectrum Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000006617 triphenylamine group Chemical group 0.000 description 3
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000001771 vacuum 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
- Luminescent Compositions (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明はエレクトロルミネッセン
ス素子に関し、特に陽極、有機化合物からなる正孔輸送
層、有機化合物からなる発光層、有機化合物からなる電
子輸送層及び陰極が順に積層された有機エレクトロルミ
ネッセンス素子、並びにかかる有機エレクトロルミネッ
センス素子において上記電子輸送層を有さない有機エレ
クトロルミネッセンス素子に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an electroluminescent device, and more particularly to an organic electroluminescent device in which an anode, a hole transporting layer made of an organic compound, a light emitting layer made of an organic compound, an electron transporting layer made of an organic compound, and a cathode are stacked in this order. The present invention relates to a luminescent device and an organic electroluminescent device having no electron transport layer in such an organic electroluminescent device.
【０００２】[0002]
【従来の技術】この種の有機エレクトロルミネッセンス
素子として、図１に示すように、陰極である金属電極１
と陽極である透明電極２との間に、互いに積層された有
機蛍光体薄膜（発光層）３及び有機正孔輸送層４が配さ
れた２層構造のものが知れている。図２に示すように、
金属電極１と透明電極２との間に互いに積層された有機
電子輸送層５、発光層３及び有機正孔輸送層４が配され
た３層構造のものが知れている。ここで、有機正孔輸送
層４は陽極から正孔を注入させ易くする機能と電子をブ
ロックする機能とを有し、有機電子輸送層５は陰極から
電子を注入させ易くする機能を有している。2. Description of the Related Art As this kind of organic electroluminescent element, as shown in FIG.
There is known a two-layer structure in which an organic phosphor thin film (light emitting layer) 3 and an organic hole transport layer 4 which are laminated on each other are disposed between a transparent electrode 2 which is an anode. As shown in FIG.
There is known a three-layer structure in which an organic electron transporting layer 5, a light emitting layer 3, and an organic hole transporting layer 4 are laminated between a metal electrode 1 and a transparent electrode 2. Here, the organic hole transport layer 4 has a function of facilitating the injection of holes from the anode and a function of blocking electrons, and the organic electron transport layer 5 has a function of facilitating the injection of electrons from the cathode. I have.
【０００３】これら有機エレクトロルミネッセンス素子
において、透明電極２の外側にはガラス基板６が配され
ている。金属電極１から注入された電子と透明電極２か
ら注入された正孔との再結合によって、励起子が生じ、
この励起子が放射失活する過程で光を放ち、この光が透
明電極２及びガラス板６を介して外部に放出される。In these organic electroluminescent elements, a glass substrate 6 is arranged outside the transparent electrode 2. The exciton is generated by the recombination of the electrons injected from the metal electrode 1 and the holes injected from the transparent electrode 2,
The excitons emit light in the process of radiation deactivation, and the light is emitted to the outside via the transparent electrode 2 and the glass plate 6.
【０００４】[0004]
【発明が解決しようとする課題】しかしながら、例え
ば、テトラフェニルブタジエン化合物からなる蛍光体の
発光層を有し青色で比較的高輝度発光が得られる有機エ
レクトロルミネッセンス素子であっても、輝度について
充分満足なものではなかった。また、蛍光体の結晶化が
速く、陰極金属を成膜し難い等素子作成上問題があっ
た。However, for example, even an organic electroluminescent device having a phosphor light emitting layer made of a tetraphenylbutadiene compound and capable of obtaining relatively high-luminance emission in blue has a satisfactory luminance. It was not something. In addition, there was a problem in element fabrication such as the crystallization of the phosphor was fast and it was difficult to form a cathode metal.
【０００５】本発明は、上述した従来の要望を満たすべ
くなされたものであって、有機蛍光体を効率良く高輝度
にて発光させることができ長寿命の有機エレクトロルミ
ネッセンス素子を提供することを目的とする。The present invention has been made to satisfy the above-mentioned conventional needs, and has as its object to provide a long-life organic electroluminescent device capable of efficiently emitting organic phosphors with high luminance. And
【０００６】[0006]
【課題を解決するための手段】本発明によるエレクトロ
ルミネッセンス素子は、陽極、有機化合物からなる正孔
輸送層、有機化合物からなる発光層、有機化合物からな
る電子輸送層及び陰極が順に積層された有機エレクトロ
ルミネッセンス素子であって、前記電子輸送層が下記化
学式１で示されるクマリン化合物According to the present invention, there is provided an electroluminescent device comprising an anode, a hole transport layer comprising an organic compound, a light emitting layer comprising an organic compound, an electron transport layer comprising an organic compound, and a cathode. An electroluminescent device, wherein the electron transport layer is a coumarin compound represented by the following chemical formula 1.
【０００７】[0007]
【化１】 Embedded image
【０００８】｛上記化学式１中、Ｒ1及びＲ2は、それぞ
れ独立に、水素原子、ハロゲン原子、メチル基、エチル
基、置換基を有していても良いフェニル基、若しくはシ
アノ基を表し、場合によりＲ1とＲ2とは結合して環を形
成してもよく、Ｘ及びＹは、それぞれ独立に、下記化学
式２In the above formula 1, R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a phenyl group which may have a substituent, or a cyano group; Optionally, R 1 and R 2 may combine to form a ring, and X and Y are each independently represented by the following chemical formula 2
【０００９】[0009]
【化２】 Embedded image
【００１０】（上記化学式２中、Ｒ3及びＲ4は、それぞ
れ独立に水素原子、炭素数１〜１６のアルキル基、置換
基を有していても良いフェニル基、炭素数１〜８のアル
キルアミノアルキル基、若しくは炭素数１〜８のアルコ
キシアルキル基を表す）で示される官能基、炭素数１〜
５のアルコキシ基、ハロゲン原子、水酸基又は下記化学
式３で表されるクマリン誘導体のアミノ基(In the above chemical formula 2, R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 16 carbon atoms, a phenyl group which may have a substituent, an alkyl group having 1 to 8 carbon atoms. An aminoalkyl group or an alkoxyalkyl group having 1 to 8 carbon atoms)
An alkoxy group, a halogen atom, a hydroxyl group, or an amino group of a coumarin derivative represented by the following chemical formula 3
【００１１】[0011]
【化３】 Embedded image
【００１２】（上記化学式３中、Ｒ1及びＲ2は、それぞ
れ独立に、水素原子、ハロゲン原子、メチル基、エチル
基、置換基を有していても良いフェニル基、若しくはシ
アノ基を表し、又はＲ1とＲ2とは結合して芳香環を形成
する炭素原子を示す）を表わし、Ｚは−Ｏ−，−Ｓ−，
又は−ＮＨ−を表す｝からなることを特徴とする。ま
た、本発明によるエレクトロルミネッセンス素子は、陽
極、有機化合物からなる正孔輸送層、有機化合物からな
る発光層及び陰極が順に積層された有機エレクトロルミ
ネッセンス素子であって、前記発光層が下記化学式１で
示されるクマリン化合物(In the above chemical formula 3, R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a phenyl group which may have a substituent, or a cyano group; Or R 1 and R 2 represent a carbon atom which forms an aromatic ring by bonding), and Z is -O-, -S-,
Or｝ representing -NH-. The electroluminescent device according to the present invention is an organic electroluminescent device in which an anode, a hole transport layer made of an organic compound, a light emitting layer made of an organic compound, and a cathode are sequentially stacked, wherein the light emitting layer is represented by the following chemical formula 1. Coumarin compounds shown
【００１３】[0013]
【化１】 Embedded image
【００１４】｛上記化学式１中、Ｒ1及びＲ2は、それぞ
れ独立に、水素原子、ハロゲン原子、メチル基、エチル
基、置換基を有していても良いフェニル基、若しくはシ
アノ基を表し、場合によりＲ1とＲ2とは結合して環を形
成してもよく、Ｘ及びＹは、それぞれ独立に、下記化学
式２In the above chemical formula 1, R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a phenyl group which may have a substituent, or a cyano group; Optionally, R 1 and R 2 may combine to form a ring, and X and Y are each independently represented by the following chemical formula 2
【００１５】[0015]
【化２】 Embedded image
【００１６】（上記化学式２中、Ｒ3及びＲ4は、それぞ
れ独立に水素原子、炭素数１〜１６のアルキル基、置換
基を有していても良いフェニル基、炭素数１〜８のアル
キルアミノアルキル基、若しくは炭素数１〜８のアルコ
キシアルキル基を表す）で示される官能基、炭素数１〜
５のアルコキシ基、ハロゲン原子、水酸基又は下記化学
式３で表されるクマリン誘導体のアミノ基(In the above formula 2, R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 16 carbon atoms, a phenyl group which may have a substituent, an alkyl group having 1 to 8 carbon atoms. An aminoalkyl group or an alkoxyalkyl group having 1 to 8 carbon atoms)
An alkoxy group, a halogen atom, a hydroxyl group, or an amino group of a coumarin derivative represented by the following chemical formula 3
【００１７】[0017]
【化３】 Embedded image
【００１８】（上記化学式３中、Ｒ1及びＲ2は、それぞ
れ独立に、水素原子、ハロゲン原子、メチル基、エチル
基、置換基を有していても良いフェニル基、若しくはシ
アノ基を表し、又はＲ1とＲ2とは結合して芳香環を形成
する炭素原子を示す）を表わし、Ｚは−Ｏ−，−Ｓ−，
又は−ＮＨ−を表す｝からなることを特徴とする。(In the above formula 3, R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a phenyl group which may have a substituent, or a cyano group; Or R 1 and R 2 represent a carbon atom which forms an aromatic ring by bonding), and Z is -O-, -S-,
Or｝ representing -NH-.
【００１９】[0019]
【作用】本発明によれば、効率良く高輝度で発光させる
ことができる有機エレクトロルミネッセンス素子が得ら
れる。According to the present invention, an organic electroluminescence device capable of efficiently emitting light with high luminance can be obtained.
【００２０】[0020]
【実施例】以下、本発明を図に基づいて詳細に説明す
る。本発明の有機エレクトロルミネッセンス素子は、図
１及び２に示した構造の有機エレクトロルミネッセンス
素子と同様であって、図２に示すように、一対の金属陰
極１と透明陽極２との間に電子輸送層５、発光層３及び
正孔輸送層４を順に成膜した構造を有する。または、図
１に示ように、一対の金属陰極１と透明陽極２との間に
発光層３及び正孔輸送層４を薄膜として積層、成膜した
構造でも良い。いずれの場合でも、電極１，２について
一方が透明であればよい。例えば陰極１には、アルミニ
ウム、マグネシウム、インジウム、銀又は各々の合金等
の仕事関数が小さな金属からなり厚さが約 100〜5000Å
程度のものを用い得る。また、例えば陽極２には、イン
ジウムすず酸化物（以下、ＩＴＯともいう）等の仕事関
数の大きな導電性材料からなり厚さが1000〜3000Å程度
で、又は金で厚さが 800〜1500Å程度のものを用い得
る。なお、金を電極材料として用いた場合には、電極は
半透明の状態となる。DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS The present invention will be described below in detail with reference to the drawings. The organic electroluminescent device of the present invention is the same as the organic electroluminescent device having the structure shown in FIGS. 1 and 2, and as shown in FIG. It has a structure in which a layer 5, a light emitting layer 3, and a hole transport layer 4 are sequentially formed. Alternatively, as shown in FIG. 1, a structure in which a light emitting layer 3 and a hole transport layer 4 are laminated and formed as a thin film between a pair of metal cathodes 1 and a transparent anode 2 may be used. In any case, one of the electrodes 1 and 2 only needs to be transparent. For example, the cathode 1 is made of a metal having a small work function, such as aluminum, magnesium, indium, silver or an alloy thereof, and has a thickness of about 100 to 5000 mm.
Some may be used. Further, for example, the anode 2 is made of a conductive material having a large work function such as indium tin oxide (hereinafter, also referred to as ITO) and has a thickness of about 1000 to 3000 mm, or gold having a thickness of about 800 to 1500 mm. Can be used. When gold is used as an electrode material, the electrode is in a translucent state.
【００２１】図２に示すように有機正孔輸送層４には、
例えば下記化学式４のトリフェニルアミン誘導体、更に
下記化学式５〜１５のＣＴＭ（Carrier Transmitting M
aterials）として知られる化合物を用い得る。As shown in FIG. 2, the organic hole transport layer 4 has
For example, a triphenylamine derivative represented by the following chemical formula 4 and a CTM (Carrier Transmitting M) represented by the following chemical formulas 5 to 15
Compounds known as aterials) may be used.
【００２２】[0022]
【化４】 Embedded image
【００２３】[0023]
【化５】 Embedded image
【００２４】[0024]
【化６】 Embedded image
【００２５】[0025]
【化７】 Embedded image
【００２６】[0026]
【化８】 Embedded image
【００２７】[0027]
【化９】 Embedded image
【００２８】[0028]
【化１０】 Embedded image
【００２９】[0029]
【化１１】 Embedded image
【００３０】[0030]
【化１２】 Embedded image
【００３１】[0031]
【化１３】 Embedded image
【００３２】[0032]
【化１４】 Embedded image
【００３３】[0033]
【化１５】 Embedded image
【００３４】図２に示すように発光層３としては、テト
ラフェニルブタジエン化合物を含む蛍光体薄膜が好まし
く用いられる。かかる発光層３の膜厚は１μｍ以下に設
定される。発光層３としては、下記化学式１６〜２５の
化合物も用いられる。As shown in FIG. 2, as the light emitting layer 3, a phosphor thin film containing a tetraphenylbutadiene compound is preferably used. The thickness of the light emitting layer 3 is set to 1 μm or less. As the light emitting layer 3, compounds of the following chemical formulas 16 to 25 are also used.
【００３５】[0035]
【化１６】 Embedded image
【００３６】[0036]
【化１７】 Embedded image
【００３７】[0037]
【化１８】 Embedded image
【００３８】[0038]
【化１９】 Embedded image
【００３９】[0039]
【化２０】 Embedded image
【００４０】[0040]
【化２１】 Embedded image
【００４１】[0041]
【化２２】 Embedded image
【００４２】[0042]
【化２３】 Embedded image
【００４３】[0043]
【化２４】 Embedded image
【００４４】[0044]
【化２５】 Embedded image
【００４５】図２に示すように電子輸送層５としては、
化学式１で示される一般式の化合物が用いられる。ま
た、化学式１なる一般式の化合物は、図１に示す電子輸
送層５を有さない有機エレクトロルミネッセンス素子の
場合、発光層３として用いることもできる。すなわち、
有機エレクトロルミネッセンス素子において、電子輸送
層５または発光層３は、下記化学式１で示されるクマリ
ン化合物As shown in FIG. 2, as the electron transport layer 5,
A compound of the general formula represented by Chemical Formula 1 is used. Further, the compound of the general formula represented by the chemical formula 1 can be used as the light emitting layer 3 in the case of an organic electroluminescence device having no electron transport layer 5 shown in FIG. That is,
In the organic electroluminescence device, the electron transport layer 5 or the light emitting layer 3 is made of a coumarin compound represented by the following chemical formula 1.
【００４６】[0046]
【化１】 Embedded image
【００４７】｛上記化学式１中、Ｒ1及びＲ2は、それぞ
れ独立に、水素原子、ハロゲン原子、メチル基、エチル
基、置換基を有していても良いフェニル基、若しくはシ
アノ基を表し、場合によりＲ1とＲ2とは結合して環を形
成してもよく、Ｘ及びＹは、それぞれ独立に、下記化学
式２In formula 1, R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a phenyl group which may have a substituent, or a cyano group; Optionally, R 1 and R 2 may combine to form a ring, and X and Y are each independently represented by the following chemical formula 2
【００４８】[0048]
【化２】 Embedded image
【００４９】（上記化学式２中、Ｒ3及びＲ4は、それぞ
れ独立に水素原子、炭素数１〜１６のアルキル基、置換
基を有していても良いフェニル基、炭素数１〜８のアル
キルアミノアルキル基、若しくは炭素数１〜８のアルコ
キシアルキル基を表す）で示される官能基、炭素数１〜
５のアルコキシ基、ハロゲン原子、水酸基又は下記化学
式３で表されるクマリン誘導体のアミノ基(In the above chemical formula 2, R 3 and R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 16 carbon atoms, a phenyl group which may have a substituent, an alkyl group having 1 to 8 carbon atoms. An aminoalkyl group or an alkoxyalkyl group having 1 to 8 carbon atoms)
An alkoxy group, a halogen atom, a hydroxyl group, or an amino group of a coumarin derivative represented by the following chemical formula 3
【００５０】[0050]
【化３】 Embedded image
【００５１】（上記化学式３中、Ｒ1及びＲ2は、それぞ
れ独立に、水素原子、ハロゲン原子、メチル基、エチル
基、置換基を有していても良いフェニル基、若しくはシ
アノ基を表し、又はＲ1とＲ2とは結合して芳香環を形成
する炭素原子を示す）を表わし、Ｚは−Ｏ−，−Ｓ−，
又は−ＮＨ−を表す｝から形成される。以下、本発明で
用いられるクマリン化合物の具体例を化学式２６〜４３
に示すが、本発明はこれに限定されるものではない。(In the above chemical formula 3, R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a phenyl group which may have a substituent, or a cyano group; Or R 1 and R 2 represent a carbon atom which forms an aromatic ring by bonding), and Z is -O-, -S-,
Or formed from｝ representing —NH—. Hereinafter, specific examples of the coumarin compound used in the present invention are shown in Chemical Formulas 26 to 43.
However, the present invention is not limited to this.
【００５２】[0052]
【化２６】 Embedded image
【００５３】[0053]
【化２７】 Embedded image
【００５４】[0054]
【化２８】 Embedded image
【００５５】[0055]
【化２９】 Embedded image
【００５６】[0056]
【化３０】 Embedded image
【００５７】[0057]
【化３１】 Embedded image
【００５８】[0058]
【化３２】 Embedded image
【００５９】[0059]
【化３３】 Embedded image
【００６０】[0060]
【化３４】 Embedded image
【００６１】[0061]
【化３５】 Embedded image
【００６２】[0062]
【化３６】 Embedded image
【００６３】[0063]
【化３７】 Embedded image
【００６４】[0064]
【化３８】 Embedded image
【００６５】[0065]
【化３９】 Embedded image
【００６６】[0066]
【化４０】 Embedded image
【００６７】[0067]
【化４１】 Embedded image
【００６８】[0068]
【化４２】 Embedded image
【００６９】[0069]
【化４３】 Embedded image
【００７０】［実施例１］電子輸送層として、膜厚100
Åの上記化学式２６のクマリン化合物の薄膜を用いた図
２の如き構造の電界発光素子を作製した。有機正孔輸送
層には、膜厚500Åの上記化学式４のトリフェニルアミ
ン誘導体の薄膜を用いた。Example 1 As an electron transport layer, a film having a thickness of 100
An electroluminescent device having a structure as shown in FIG. 2 using a thin film of the coumarin compound represented by the above-mentioned chemical formula 26 was prepared. For the organic hole transport layer, a thin film of the triphenylamine derivative of the above formula 4 having a thickness of 500 ° was used.
【００７１】発光層として、膜厚200Åの下記化学式４
４のテトラフェニルブタジエンの薄膜を用いた。As a light emitting layer, the following chemical formula 4 having a thickness of 200 °
A thin film of tetraphenylbutadiene No. 4 was used.
【００７２】[0072]
【化４４】 Embedded image
【００７３】陰極である金属電極には、膜厚1100Åのマ
グネシウム−銀合金の薄膜を用いた。陽極である透明電
極には、膜厚1500ÅのＩＴＯの薄膜を用いた。以上の構
成の電界発光素子の各薄膜は、真空蒸着法によって、真
空度１．０×１０-5Torr以下、蒸着速度4.0Å／秒の条
件下で成膜した。A magnesium-silver alloy thin film having a thickness of 1100 ° was used for the metal electrode serving as the cathode. As the transparent electrode serving as the anode, a thin film of ITO having a thickness of 1500 ° was used. Each thin film of the electroluminescent device having the above configuration was formed by a vacuum deposition method under the conditions of a degree of vacuum of 1.0 × 10 −5 Torr or less and a deposition rate of 4.0 ° / sec.
【００７４】この電界発光素子の発光特性を図３に示
す。比較例として、図３に、電子輸送層を用いない、図
１の如き従来構造の電界発光素子の発光特性を示す。こ
の素子の有機正孔輸送層、有機発光層、陰極金属の各薄
膜は、上記実施例と同時に、同一膜厚により成膜した。FIG. 3 shows the light emission characteristics of this electroluminescent device. As a comparative example, FIG. 3 shows the emission characteristics of the electroluminescent device having the conventional structure as shown in FIG. 1 without using the electron transport layer. Each thin film of the organic hole transport layer, the organic light emitting layer, and the cathode metal of this device was formed with the same film thickness as in the above-described embodiment.
【００７５】図３において、実線は、電子輸送層として
上記化学式２６のクマリン化合物の薄膜を用いた本実施
例の、電流密度に対しての発光輝度及び発光効率の変化
を示し、破線は、電子輸送層を用いない上記比較例の、
電流密度に対しての発光輝度及び発光効率の変化を示
す。上記の如く作製された実施例の電界発光素子におい
ては、両電極間に１８Ｖ印加時に、0.38A/cm2の電流が
流れ、波長４６５nmにピークをもつ発光スペクトル（色
純度は、ＣＩＥ色度座標（1931）でＸ＝0.1551，Ｙ＝0.
2077）で1890cd/m2の青色発光を得た。In FIG. 3, the solid line shows the change in the light emission luminance and the light emission efficiency with respect to the current density in the present example using the coumarin compound thin film of the above formula 26 as the electron transport layer. In the comparative example without using the transport layer,
5 shows changes in light emission luminance and light emission efficiency with respect to current density. In the electroluminescent device of the embodiment fabricated as described above, when 18 V is applied between both electrodes, a current of 0.38 A / cm 2 flows, and an emission spectrum having a peak at a wavelength of 465 nm (color purity is measured by CIE chromaticity coordinates) (1931) where X = 0.1551, Y = 0.
2077), and emitted blue light of 1890 cd / m 2 .
【００７６】また、比較例の電界発光素子においては、
両電極間に１８Ｖ印加時に、０．３０A/cm2の電流が流
れ、波長４５５nmにピークをもつ発光スペクトル（色純
度は、ＣＩＥ色度座標（1931)でＸ＝0.1483，Ｙ＝0.152
4）で150cd/m2の青色発光を得た。また、図３に示すよ
うに、比較例の従来の電界発光素子と、本実施例の電子
輸送層を用いた素子との、発光輝度107cd/m2における発
光効率を比較すると、従来のものが発光効率0.01 lm/W
であるに対し、本実施例のものは発光効率0.22 lm/Wで
あり、従来の素子より２０倍以上発光効率が向上してい
る。In the electroluminescent device of the comparative example,
When a voltage of 18 V is applied between both electrodes, a current of 0.30 A / cm 2 flows, and an emission spectrum having a peak at a wavelength of 455 nm (color purity: X = 0.1483, Y = 0.152 in CIE chromaticity coordinates (1931))
In 4), blue light emission of 150 cd / m 2 was obtained. Further, as shown in FIG. 3, when the luminous efficiency at a luminance of 107 cd / m 2 of the conventional electroluminescent device of the comparative example and the device using the electron transport layer of the present example are compared, Luminous efficiency 0.01 lm / W
On the other hand, the device of this embodiment has a luminous efficiency of 0.22 lm / W, which is more than 20 times higher than that of the conventional device.
【００７７】［実施例２］発光層として、膜厚500Åの
上記化学式２６のクマリン化合物の薄膜を用いた。有機
正孔輸送層には膜厚500Åの上記化学式４のトリフェニ
ルアミン誘導体を用いた。陰極である金属電極には、膜
厚1100Åのマグネシウム−銀合金の薄膜を用いた。陽極
である透明電極には、膜厚1500ÅのＩＴＯの薄膜を用い
た。Example 2 As a light emitting layer, a thin film of the coumarin compound represented by the above formula 26 having a film thickness of 500 ° was used. For the organic hole transport layer, a triphenylamine derivative of the above formula 4 having a film thickness of 500 ° was used. A magnesium-silver alloy thin film having a thickness of 1100 mm was used for the metal electrode serving as the cathode. As the transparent electrode serving as the anode, a thin film of ITO having a thickness of 1500 ° was used.
【００７８】以上の電界発光素子の各薄膜は、真空蒸着
法によって、真空度1.0×10-5Torr以下、蒸着速度4.0Å
／秒の条件下で成膜された。この電界発光素子の両電極
間に１９Ｖ印加すると、0.23A/cm2の電流が流れ、波長5
05nmにピークをもつ発光スペクトル（色純度は、ＣＩＥ
色度座標（1931）で、Ｘ＝0.2702，Ｙ＝0.5376）で600c
d／ｍ2の青緑色の発光を得た。Each thin film of the above-mentioned electroluminescent device is formed by vacuum deposition at a degree of vacuum of 1.0 × 10 −5 Torr or less and a deposition rate of 4.0 ° C.
/ Sec. When a voltage of 19 V is applied between both electrodes of the electroluminescent device, a current of 0.23 A / cm 2 flows, and a wavelength of 5
Emission spectrum with a peak at 05 nm (color purity: CIE
600c at chromaticity coordinates (1931), X = 0.2702, Y = 0.5376)
A blue-green emission of d / m 2 was obtained.
【００７９】[0079]
【発明の効果】以上説明したように、本発明による有機
エレクトロルミネッセンス素子においては、有機化合物
からなり互いに積層された電子輸送層、発光層及び正孔
輸送層が陰極及び陽極間に配された構成の有機エレクト
ロルミネッセンス素子であって、電子輸送層（電子輸送
層を有さない場合は発光層）が、上記化学式１のクマリ
ン化合物を含む薄膜からなるので、効率良く高輝度で長
期間に亘って発光させることができる。As described above, the organic electroluminescence device according to the present invention has a structure in which an electron transport layer, a light emitting layer and a hole transport layer, which are made of an organic compound and are laminated, are arranged between a cathode and an anode. Wherein the electron transport layer (the light-emitting layer in the case where the electron transport layer is not provided) is a thin film containing the coumarin compound of the above formula 1, so that it can be efficiently used with high luminance for a long period of time. It can emit light.
【図１】 有機エレクトロルミネッセンス素子の概略構
造図である。FIG. 1 is a schematic structural diagram of an organic electroluminescence element.
【図２】 有機エレクトロルミネッセンス素子の概略構
造図である。FIG. 2 is a schematic structural view of an organic electroluminescence element.
【図３】 有機エレクトロルミネッセンス素子の発光特
性を示すグラフである。FIG. 3 is a graph showing light emission characteristics of the organic electroluminescence element.
１ 金属電極（陰極） ２ 透明電極（陽極） ３ 発光層 ４ 有機正孔輸送層 ５ 有機電子輸送層 ６ ガラス基板 Reference Signs List 1 metal electrode (cathode) 2 transparent electrode (anode) 3 light emitting layer 4 organic hole transport layer 5 organic electron transport layer 6 glass substrate
───────────────────────────────────────────────────── フロントページの続き (72)発明者 山村 重夫 東京都北区志茂３丁目26番８号 (58)調査した分野(Int.Cl.6，ＤＢ名) C09K 11/06 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Shigeo Yamamura 3-26-8 Shimo, Kita-ku, Tokyo (58) Field surveyed (Int.Cl. 6 , DB name) C09K 11/06 CA (STN) REGISTRY (STN)
Claims (2)
有機化合物からなる発光層、有機化合物からなる電子輸
送層及び陰極が順に積層された有機エレクトロルミネッ
センス素子であって、前記電子輸送層が下記化学式１で
示されるクマリン化合物 【化１】 ｛上記化学式１中、Ｒ1及びＲ2は、それぞれ独立に、水
素原子、ハロゲン原子、メチル基、エチル基、置換基を
有していても良いフェニル基、若しくはシアノ基を表
し、場合によりＲ1とＲ2とは結合して環を形成してもよ
く、Ｘ及びＹは、それぞれ独立に、下記化学式２ 【化２】 （上記化学式２中、Ｒ3及びＲ4は、それぞれ独立に水素
原子、炭素数１〜１６のアルキル基、置換基を有してい
ても良いフェニル基、炭素数１〜８のアルキルアミノア
ルキル基、若しくは炭素数１〜８のアルコキシアルキル
基を表す）で示される官能基、炭素数１〜５のアルコキ
シ基、ハロゲン原子、水酸基又は下記化学式３で表され
るクマリン誘導体のアミノ基 【化３】 （上記化学式３中、Ｒ1及びＲ2は、それぞれ独立に、水
素原子、ハロゲン原子、メチル基、エチル基、置換基を
有していても良いフェニル基、若しくはシアノ基を表
し、又はＲ1とＲ2とは結合して芳香環を形成する炭素原
子を示す）を表わし、Ｚは−Ｏ−，−Ｓ−，又は−ＮＨ
−を表す｝からなることを特徴とする有機エレクトロル
ミネッセンス素子。1. An anode, a hole transport layer comprising an organic compound,
An organic electroluminescence device in which a light-emitting layer made of an organic compound, an electron transport layer made of an organic compound, and a cathode are sequentially stacked, wherein the electron transport layer is a coumarin compound represented by the following chemical formula 1. 中 In the above chemical formula 1, R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a phenyl group which may have a substituent, or a cyano group; 1 and R 2 may be bonded to each other to form a ring, and X and Y each independently represent the following chemical formula 2: (In the above chemical formula 2, R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 16 carbon atoms, a phenyl group which may have a substituent, or an alkylaminoalkyl group having 1 to 8 carbon atoms. Or a C1-C8 alkoxyalkyl group), a C1-C5 alkoxy group, a halogen atom, a hydroxyl group, or an amino group of a coumarin derivative represented by the following chemical formula 3: (In Formula 3, R 1 and R 2 represent each independently a hydrogen atom, a halogen atom, a methyl group, an ethyl group, phenyl group which may have a substituent, or a cyano group, or R 1 And R 2 represent a carbon atom which forms an aromatic ring by bonding), and Z represents —O—, —S—, or —NH
An organic electroluminescence device comprising:｝ representing-.
有機化合物からなる発光層及び陰極が順に積層された有
機エレクトロルミネッセンス素子であって、前記発光層
が下記化学式１で示されるクマリン化合物 【化１】 ｛上記化学式１中、Ｒ1及びＲ2は、それぞれ独立に、水
素原子、ハロゲン原子、メチル基、エチル基、置換基を
有していても良いフェニル基、若しくはシアノ基を表
し、場合によりＲ1とＲ2とは結合して環を形成してもよ
く、Ｘ及びＹは、それぞれ独立に、下記化学式２ 【化２】 （上記化学式２中、Ｒ3及びＲ4は、それぞれ独立に水素
原子、炭素数１〜１６のアルキル基、置換基を有してい
ても良いフェニル基、炭素数１〜８のアルキルアミノア
ルキル基、若しくは炭素数１〜８のアルコキシアルキル
基を表す）で示される官能基、炭素数１〜５のアルコキ
シ基、ハロゲン原子、水酸基又は下記化学式３で表され
るクマリン誘導体のアミノ基 【化３】 （上記化学式３中、Ｒ1及びＲ2は、それぞれ独立に、水
素原子、ハロゲン原子、メチル基、エチル基、置換基を
有していても良いフェニル基、若しくはシアノ基を表
し、又はＲ1とＲ2とは結合して芳香環を形成する炭素原
子を示す）を表わし、Ｚは−Ｏ−，−Ｓ−，又は−ＮＨ
−を表す｝からなることを特徴とする有機エレクトロル
ミネッセンス素子。2. An anode, a hole transport layer comprising an organic compound,
An organic electroluminescence device in which a light emitting layer made of an organic compound and a cathode are sequentially laminated, wherein the light emitting layer is a coumarin compound represented by the following chemical formula 1. 中 In the above chemical formula 1, R 1 and R 2 each independently represent a hydrogen atom, a halogen atom, a methyl group, an ethyl group, a phenyl group which may have a substituent, or a cyano group; 1 and R 2 may be bonded to each other to form a ring, and X and Y each independently represent the following chemical formula 2: (In the above chemical formula 2, R 3 and R 4 are each independently a hydrogen atom, an alkyl group having 1 to 16 carbon atoms, a phenyl group which may have a substituent, or an alkylaminoalkyl group having 1 to 8 carbon atoms. Or a C1-C8 alkoxyalkyl group), a C1-C5 alkoxy group, a halogen atom, a hydroxyl group, or an amino group of a coumarin derivative represented by the following chemical formula 3: (In Formula 3, R 1 and R 2 represent each independently a hydrogen atom, a halogen atom, a methyl group, an ethyl group, phenyl group which may have a substituent, or a cyano group, or R 1 And R 2 represent a carbon atom forming an aromatic ring by bonding), and Z represents —O—, —S—, or —NH
An organic electroluminescence device comprising:｝ representing-.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4064291A JP2974845B2 (en) | 1992-03-21 | 1992-03-21 | Organic electroluminescence device |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4064291A JP2974845B2 (en) | 1992-03-21 | 1992-03-21 | Organic electroluminescence device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05263074A JPH05263074A (en) | 1993-10-12 |
| JP2974845B2 true JP2974845B2 (en) | 1999-11-10 |
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ID=13253990
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|---|---|---|---|
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|---|---|---|---|---|
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1992
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