JP2001307885A - Organic el element organic and organic el display - Google Patents
Organic el element organic and organic el displayInfo
- Publication number
- JP2001307885A JP2001307885A JP2001042102A JP2001042102A JP2001307885A JP 2001307885 A JP2001307885 A JP 2001307885A JP 2001042102 A JP2001042102 A JP 2001042102A JP 2001042102 A JP2001042102 A JP 2001042102A JP 2001307885 A JP2001307885 A JP 2001307885A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- organic
- unsubstituted
- general formula
- group
- 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
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 25
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims abstract description 21
- 239000010410 layer Substances 0.000 claims description 117
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- -1 8-quinolinolate compound Chemical class 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 238000002347 injection Methods 0.000 claims description 15
- 239000007924 injection Substances 0.000 claims description 15
- 125000003277 amino group Chemical group 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 125000002524 organometallic group Chemical group 0.000 claims description 12
- 239000010409 thin film Substances 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 8
- 239000002356 single layer Substances 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- 229910005965 SO 2 Inorganic materials 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 13
- 229910052733 gallium Inorganic materials 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 238000005215 recombination Methods 0.000 description 5
- 230000006798 recombination Effects 0.000 description 5
- 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 5
- 230000000903 blocking effect Effects 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BKMIWBZIQAAZBD-UHFFFAOYSA-N diindenoperylene Chemical group C12=C3C4=CC=C2C2=CC=CC=C2C1=CC=C3C1=CC=C2C3=CC=CC=C3C3=CC=C4C1=C32 BKMIWBZIQAAZBD-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical class C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- DTZWGKCFKSJGPK-VOTSOKGWSA-N (e)-2-(2-methyl-6-(2-(1,1,7,7-tetramethyl-1,2,3,5,6,7-hexahydropyrido[3,2,1-ij]quinolin-9-yl)vinyl)-4h-pyran-4-ylidene)malononitrile Chemical compound O1C(C)=CC(=C(C#N)C#N)C=C1\C=C\C1=CC(C(CCN2CCC3(C)C)(C)C)=C2C3=C1 DTZWGKCFKSJGPK-VOTSOKGWSA-N 0.000 description 1
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 1
- HAXBIWFMXWRORI-UHFFFAOYSA-N Benzo[k]fluoranthene Chemical class C1=CC(C2=CC3=CC=CC=C3C=C22)=C3C2=CC=CC3=C1 HAXBIWFMXWRORI-UHFFFAOYSA-N 0.000 description 1
- 229910021583 Cobalt(III) fluoride Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229910002601 GaN Inorganic materials 0.000 description 1
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001454 anthracenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Chemical class CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- YCYBZKSMUPTWEE-UHFFFAOYSA-L cobalt(ii) fluoride Chemical compound F[Co]F YCYBZKSMUPTWEE-UHFFFAOYSA-L 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- AJNVQOSZGJRYEI-UHFFFAOYSA-N digallium;oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Ga+3].[Ga+3] AJNVQOSZGJRYEI-UHFFFAOYSA-N 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000002259 gallium compounds Chemical class 0.000 description 1
- 229910001195 gallium oxide Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 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 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は有機ＥＬ素子（有機
エレクトロルミネッセンス素子）に関し、さらに詳述す
ると、発光効率に優れ、輝度、色度の良好な赤色有機Ｅ
Ｌ素子及びそれを用いた有機ＥＬディスプレイに関す
る。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic EL device (organic electroluminescence device). More specifically, the present invention relates to a red organic EL device having excellent luminous efficiency, good luminance and good chromaticity.
The present invention relates to an L element and an organic EL display using the same.
【０００２】[0002]
【従来の技術】従来、有機ＥＬ素子、特に赤色有機ＥＬ
素子においては、実用レベルの輝度を得るために、一般
的に使用されている蛍光量子収率の高い下記一般式
［ａ］ （Ｑ）3−Ａｌ … ［ａ］ ［一般式［ａ］中のＱは、置換若しくは未置換の８−キ
ノリノラート配位子を表す。］の発光性有機アルミニウ
ム錯体や、下記一般式［ｂ］2. Description of the Related Art Conventionally, organic EL devices, especially red organic EL devices
In the device, in order to obtain a practical level of luminance, the following general formula [a] (Q) 3- Al... [A], which is generally used and has a high fluorescence quantum yield, is used. Q represents a substituted or unsubstituted 8-quinolinolate ligand. A luminous organoaluminum complex represented by the following general formula [b]:
【化１６】 ［一般式［ｂ］中のＡ1〜Ａ4は、それぞれ独立に炭素数
６〜１８のアリール基を表す。Ｒ1〜Ｒ8は、それぞれ独
立に水素原子、ハロゲン原子、アルキル基、アルコキシ
基、アリール基又はアミノ基を表す。］の芳香族アミン
誘導体をホストとし、これに赤色材料をドーピングした
ものを発光層としていた。Embedded image [A1 to A4 in the general formula [b] each independently represent an aryl group having 6 to 18 carbon atoms. R1 to R8 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group or an amino group. The above-described aromatic amine derivative was used as a host, and a material obtained by doping this with a red material was used as a light emitting layer.
【０００３】例えば、C.W.Tang:“An Overview of Orga
nic Electroluminescent Materialsand Devices”,SID
96DIGEST.,14.1,pp.181-184(1996)に記載の有機ＥＬ素
子では、発光性有機アルミニウム錯体である下記化合物
４For example, CWTang: “An Overview of Orga
nic Electroluminescent Materials and Devices ”, SID
96DIGEST., 14.1, pp. 181-184 (1996), the following compound 4 which is a luminescent organic aluminum complex is used.
【化１７】 のトリス（８−キノリノラート）アルミニウムをホスト
とし、これに赤色発光材料のＤＣＪＴをドープすること
により発光層としている。また、特開平１０−７２５８
１では、前記一般式［ｂ］に示した芳香族アミン誘導体
をホストとし、これに赤色発光材料をドープすることに
より発光層としている。Embedded image Of tris (8-quinolinolato) aluminum as a host, and doped with DCJT as a red light-emitting material to form a light-emitting layer. Further, Japanese Patent Application Laid-Open No. 10-7258
In No. 1, a light emitting layer is obtained by doping a red light emitting material with the aromatic amine derivative represented by the general formula [b] as a host.
【０００４】ところで、実用的観点から、現状の有機Ｅ
Ｌ素子は長寿命化、熱的安定性が必須であり、そのため
に陽極とホール輸送層との間に、高耐熱化用ホール注入
層を使用していた。しかし、これにより寿命特性が向上
する反面、発光層へのホール注入特性が悪化していた。
その結果、発光層での再結合収率が低下し、十分な発光
効率が得られなかった。さらに、印加電圧の関係で電子
が発光層から漏れるという問題、つまりキャリアバラン
スが変化し、ホール輸送層そのものが発光することによ
り色合いが変化するという問題があった。By the way, from a practical point of view, the current organic E
The L element is required to have a long life and thermal stability. Therefore, a hole injection layer for increasing heat resistance is used between the anode and the hole transport layer. However, while this improves the life characteristics, the hole injection characteristics into the light emitting layer have deteriorated.
As a result, the recombination yield in the light emitting layer was reduced, and sufficient luminous efficiency was not obtained. Further, there is a problem that electrons leak from the light emitting layer due to the applied voltage, that is, the carrier balance changes, and the color tone changes due to the light emission of the hole transport layer itself.
【０００５】ここで、従来の有機ＥＬ素子について図面
を参照しながら説明する。図５は有機ＥＬ素子の断面図
である。図５において従来の有機ＥＬ素子は、ガラス基
板１上にＩＴＯ（インジウム−スズ酸化物）からなる陽
極（透明電極）２を形成し、この上にホール注入層３、
ホール輸送層４、発光層５、電子輸送層６などの有機Ｅ
Ｌ層及び陰極７等を形成することにより構成されてい
る。ここで発光層５には、蛍光量子収率の高い発光性有
機アルミニウム錯体（一般式［ａ］）をホストとし、こ
れに赤色材料がドープされている。また、このとき電子
輸送層６として電子輸送性のある発光性有機アルミニウ
ム錯体（一般式［ａ］）を用いることもある。Here, a conventional organic EL device will be described with reference to the drawings. FIG. 5 is a sectional view of the organic EL element. Referring to FIG. 5, a conventional organic EL element has an anode (transparent electrode) 2 made of ITO (indium-tin oxide) formed on a glass substrate 1, and a hole injection layer 3 is formed thereon.
Organic E such as hole transport layer 4, light emitting layer 5, electron transport layer 6, etc.
It is constituted by forming an L layer, a cathode 7 and the like. Here, the light emitting layer 5 is made of a light emitting organic aluminum complex (general formula [a]) having a high fluorescence quantum yield as a host, which is doped with a red material. At this time, a luminescent organic aluminum complex (general formula [a]) having an electron transporting property may be used as the electron transporting layer 6.
【０００６】[0006]
【発明が解決しようとする課題】従来、高耐熱化用ホー
ル注入層を使用していることから、寿命特性が向上する
反面、発光層へのホール注入特性が悪化していた。この
ことは発光層におけるホール−電子の再結合収率の低下
を招き、十分な発光効率が得られないという問題を引き
起こしていた。さらには、電圧増加に伴って電子が発光
層から漏れ出し、ホール輸送層そのものが発光すること
により色合いが変化するという問題もあった。よって、
従来の素子構成では、発光効率に優れ、高輝度でかつ常
時色度の安定した有機ＥＬデバイスを提供することがで
きなかった。これは、発光層へのホール注入特性が低
く、また電圧が増加すると電子輸送性が変化し、本来発
光層で起きるべきホール−電子の再結合が、ホール輸送
層中で起きてしまうからであった。Conventionally, the use of a hole injection layer for increasing the heat resistance has led to an improvement in the life characteristics, but a deterioration in the hole injection characteristics to the light emitting layer. This causes a decrease in the hole-electron recombination yield in the light-emitting layer, causing a problem that sufficient luminous efficiency cannot be obtained. Further, there is also a problem that electrons leak from the light emitting layer with an increase in voltage, and the color is changed by the light emission of the hole transport layer itself. Therefore,
With the conventional element configuration, it has not been possible to provide an organic EL device having excellent luminous efficiency, high luminance and stable chromaticity at all times. This is because the hole injection characteristics into the light emitting layer are low, and the electron transport property changes when the voltage increases, and the hole-electron recombination that should occur in the light emitting layer occurs in the hole transport layer. Was.
【０００７】本発明は、前述した事情に鑑みてなされた
もので、発光効率に優れ、輝度、色度の良好な赤色有機
ＥＬ素子を提供することを目的とする。The present invention has been made in view of the above circumstances, and has as its object to provide a red organic EL device having excellent luminous efficiency, good luminance and good chromaticity.
【０００８】[0008]
【課題を解決するための手段】本発明は、前記目的を達
成するため、下記（１）〜（１５）に示す有機ＥＬ素子
及び有機ＥＬディスプレイを提供する。In order to achieve the above object, the present invention provides an organic EL device and an organic EL display shown in the following (1) to (15).
【０００９】（１）互いに対向する陽極と陰極間に、少
なくとも単層又は複数層の有機薄膜よりなる発光層を備
えた有機ＥＬ素子において、下記一般式［１］(1) An organic EL device having a light-emitting layer composed of at least a single layer or a plurality of organic thin films between an anode and a cathode facing each other, wherein the following general formula [1]
【化１８】 ［一般式［１］中のＲ1〜Ｒ28は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｙ1〜Ｙ4は、それぞれ独立にＯ、Ｓ、ＳＯ
2、Ｃ＝Ｏ、ＣＨ2Ｏ、ＣＨ2ＯＣＨ2、又は、置換若しく
は未置換のアルキレン基を表す。Ｒ1〜Ｒ4、Ｒ5〜Ｒ8
は、互いに結合して飽和若しくは不飽和の５員環又は６
員環を形成してもよい。］で示される芳香族アミン誘導
体と、下記一般式［２］Embedded image [In the general formula [1], R 1 to R 28 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, Represents an unsubstituted amino group. Y1 to Y4 are each independently O, S, SO
2, C = O, CH 2 O, CH 2 OCH 2, or a substituted or unsubstituted alkylene group. R1 ~ R4, R5 ~ R8
Are bonded to each other to form a saturated or unsaturated 5-membered ring or 6
A member ring may be formed. An aromatic amine derivative represented by the following general formula [2]:
【化１９】 ［一般式［２］中のＸ1〜Ｘ20は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｘ1〜Ｘ20は、互いに結合して飽和若しく
は不飽和の５員環又は６員環を形成してもよい。］で示
されるジベンゾ｛［ｆ，ｆ’］−４，４’，７，７’−
テトラフェニル｝ジインデノ［１，２，３−ｃｄ：
１’，２’，３’−ｌｍ］ペリレン誘導体とを混合させ
た少なくとも１層の発光層を有していることを特徴とす
る有機ＥＬ素子。Embedded image [X 1 to X 20 in the general formula [2] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group. Represents an unsubstituted amino group. X1 to X20 may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. Dibenzo} [f, f ']-4,4', 7,7'-
Tetraphenyl dienedeno [1,2,3-cd:
[1 ', 2', 3'-lm] An organic EL device comprising at least one light-emitting layer mixed with a perylene derivative.
【００１０】（２）互いに対向する陽極と陰極間に、少
なくとも単層又は複数層の有機薄膜よりなる発光層を備
えた有機ＥＬ素子において、下記一般式［４］(2) An organic EL device having a light emitting layer composed of at least a single layer or a plurality of organic thin films between an anode and a cathode facing each other, wherein the following general formula [4]
【化２０】 ［一般式［４］中のＲ1〜Ｒ28は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｙ1〜Ｙ4は、それぞれ独立にＯ、Ｓ、ＳＯ
2、Ｃ＝Ｏ、ＣＨ2Ｏ、ＣＨ2ＯＣＨ2、又は、置換若しく
は未置換のアルキレン基を表す。Ｒ1〜Ｒ4、Ｒ5〜Ｒ8
は、互いに結合して飽和若しくは不飽和の５員環又は６
員環を形成してもよい。］で示される芳香族アミン誘導
体と、前記一般式［２］で示されるジベンゾ｛［ｆ，
ｆ’］−４，４’，７，７’−テトラフェニル｝ジイン
デノ［１，２，３−ｃｄ：１’，２’，３’−ｌｍ］ペ
リレン誘導体とを混合させた少なくとも１層の発光層を
有していることを特徴とする有機ＥＬ素子。Embedded image [R 1 to R 28 in the general formula [4] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, Represents an unsubstituted amino group. Y1 to Y4 are each independently O, S, SO
2, C = O, CH 2 O, CH 2 OCH 2, or a substituted or unsubstituted alkylene group. R1 ~ R4, R5 ~ R8
Are bonded to each other to form a saturated or unsaturated 5-membered ring or 6
A member ring may be formed. An aromatic amine derivative represented by the general formula [2];
f ′]-4,4 ′, 7,7′-tetraphenyldienedeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative and at least one layer of light emission An organic EL device comprising a layer.
【００１１】（３）互いに対向する陽極と陰極間に、少
なくとも単層又は複数層の有機薄膜よりなる発光層を備
えた有機ＥＬ素子において、下記一般式［５］(3) An organic EL device having a light emitting layer composed of at least a single layer or a plurality of organic thin films between an anode and a cathode facing each other, wherein the following general formula [5]
【化２１】 ［一般式［５］中のＲ1〜Ｒ28は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｘ1〜Ｘ8は、置換若しくは未置換の炭素数
１〜２０のアルキル基、又は、置換若しくは未置換の炭
素数６〜１６のアリール基を表す。Ｒ1〜Ｒ4、Ｒ5〜Ｒ8
は、互いに結合して飽和若しくは不飽和の５員環又は６
員環を形成してもよい。］で示される芳香族アミン誘導
体と、前記一般式［２］で示されるジベンゾ｛［ｆ，
ｆ’］−４，４’，７，７’−テトラフェニル｝ジイン
デノ［１，２，３−ｃｄ：１’，２’，３’−ｌｍ］ペ
リレン誘導体とを混合させた少なくとも１層の発光層を
有していることを特徴とする有機ＥＬ素子。Embedded image [R 1 to R 28 in the general formula [5] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted Represents an unsubstituted amino group. X1 to X8 represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 16 carbon atoms. R1 ~ R4, R5 ~ R8
Are bonded to each other to form a saturated or unsaturated 5-membered ring or 6
A member ring may be formed. An aromatic amine derivative represented by the general formula [2];
f ′]-4,4 ′, 7,7′-tetraphenyldienedeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative and at least one layer of light emission An organic EL device comprising a layer.
【００１２】（４）互いに対向する陽極と陰極間に、少
なくとも単層又は複数層の有機薄膜よりなる発光層を備
えた有機ＥＬ素子において、下記一般式［６］(4) An organic EL device having a light-emitting layer composed of at least a single layer or a plurality of organic thin films between an anode and a cathode facing each other, the following general formula [6]
【化２２】 ［一般式［６］中のＲ1〜Ｒ28は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｒ1〜Ｒ4、Ｒ5〜Ｒ8は、互いに結合して飽
和若しくは不飽和の５員環又は６員環を形成してもよ
い。］で示される芳香族アミン誘導体と、前記一般式
［２］で示されるジベンゾ｛［ｆ，ｆ’］−４，４’，
７，７’−テトラフェニル｝ジインデノ［１，２，３−
ｃｄ：１’，２’，３’−ｌｍ］ペリレン誘導体とを混
合させた少なくとも１層の発光層を有していることを特
徴とする有機ＥＬ素子。Embedded image [R 1 to R 28 in the general formula [6] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, Represents an unsubstituted amino group. R1 to R4 and R5 to R8 may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. An aromatic amine derivative represented by the general formula [2] and a dibenzo {[f, f ']-4,4',
7,7'-Tetraphenyldienedeno [1,2,3-
cd: 1 ′, 2 ′, 3′-lm] An organic EL device having at least one light-emitting layer mixed with a perylene derivative.
【００１３】（５）一般式［２］のジベンゾ｛［ｆ，
ｆ’］−４，４’，７，７’−テトラフェニル｝ジイン
デノ［１，２，３−ｃｄ：１’，２’，３’−ｌｍ］ペ
リレン誘導体が下記式［２ａ］で示される化合物である
ことを特徴とする（１）〜（４）の有機ＥＬ素子。(5) The dibenzo {[f,
f ′]-4,4 ′, 7,7′-Tetraphenyl {diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative represented by the following formula [2a] The organic EL device according to any one of (1) to (4), wherein
【化２３】 Embedded image
【００１４】（６）一般式［２］のジベンゾ｛［ｆ，
ｆ’］−４，４’，７，７’−テトラフェニル｝ジイン
デノ［１，２，３−ｃｄ：１’，２’，３’−ｌｍ］ペ
リレン誘導体が下記式［２ｂ］で示される化合物である
ことを特徴とする（１）〜（４）の有機ＥＬ素子。(6) Dibenzo {[f,
f ′]-4,4 ′, 7,7′-tetraphenyl {diindeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative represented by the following formula [2b] The organic EL device according to any one of (1) to (4), wherein
【化２４】 Embedded image
【００１５】（７）一般式［１］、［４］、［５］又は
［６］の芳香族アミン誘導体をホストとし、これに一般
式［２］のジベンゾ｛［ｆ，ｆ’］−４，４’，７，
７’−テトラフェニル｝ジインデノ［１，２，３−ｃ
ｄ：１’，２’，３’−ｌｍ］ペリレン誘導体がドープ
されており、ドープ比率が１〜１０％であることを特徴
とする（１）〜（６）の有機ＥＬ素子。(7) An aromatic amine derivative represented by the general formula [1], [4], [5] or [6] is used as a host, and the dibenzo {[f, f ']-4 represented by the general formula [2] is added thereto. , 4 ', 7,
7'-tetraphenyldienedeno [1,2,3-c
d: 1 ', 2', 3'-lm] The organic EL device of (1) to (6), wherein the perylene derivative is doped, and the doping ratio is 1 to 10%.
【００１６】（８）電子注入層又は電子輸送層が、下記
一般式［３］(8) When the electron injecting layer or the electron transporting layer has the following general formula [3]
【化２５】 ［一般式［３］中のＭは金属原子を表す。Ｒ1〜Ｒ6は、
それぞれ独立に水素原子、ハロゲン原子、置換若しくは
未置換のアルキル基、置換若しくは未置換のアルコキシ
基、置換若しくは未置換のアリール基、置換若しくは未
置換のアリールオキシ基、置換若しくは未置換のシクロ
アルキル基又はシアノ基を表す。Ｌは、ハロゲン原子、
置換若しくは未置換のアルコキシ基、置換若しくは未置
換のアリールオキシ基、置換若しくは未置換のアルキル
基、置換若しくは未置換のアリールオキシ基又は置換若
しくは未置換のシクロアルキル基を有する配位子を表
す。］で示される有機金属錯体を含むことを特徴とする
（１）〜（７）の有機ＥＬ素子。Embedded image [M in the general formula [3] represents a metal atom. R1 to R6 are
Each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group Or a cyano group. L is a halogen atom,
A ligand having a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted cycloalkyl group. ] The organic EL device according to any one of (1) to (7), comprising the organic metal complex represented by the formula (1).
【００１７】（９）一般式［３］の有機金属錯体におい
てＲ4がアリール基であることを特徴とする（８）の有
機ＥＬ素子。(9) The organic EL device according to (8), wherein R4 in the organometallic complex represented by the general formula [3] is an aryl group.
【００１８】（１０）一般式［３］の有機金属錯体が下
記式［３ａ］で示される化合物であることを特徴とする
（９）の有機ＥＬ素子。(10) The organic EL device according to (9), wherein the organometallic complex represented by the general formula [3] is a compound represented by the following formula [3a].
【化２６】 Embedded image
【００１９】（１１）一般式［３］の有機金属錯体が下
記式［３ｂ］で示される化合物であることを特徴とする
（９）の有機ＥＬ素子。(11) The organic EL device according to (9), wherein the organometallic complex represented by the general formula [3] is a compound represented by the following formula [3b].
【化２７】 Embedded image
【００２０】（１２）電子注入層又は電子輸送層が、一
般式［３］で示される有機金属錯体を複数種含むことを
特徴とする（８）〜（１１）の有機ＥＬ素子。(12) The organic EL device according to any one of (8) to (11), wherein the electron injection layer or the electron transport layer contains a plurality of kinds of the organometallic complexes represented by the general formula [3].
【００２１】（１３）電子注入層又は電子輸送層が、前
記式［３ａ］で示される化合物及び前記式［３ｂ］で示
される化合物を含むことを特徴とする（１２）の有機Ｅ
Ｌ素子。(13) The organic E of (12), wherein the electron injecting layer or the electron transporting layer contains a compound represented by the formula [3a] and a compound represented by the formula [3b].
L element.
【００２２】（１４）電子注入層又は電子輸送層が、下
記一般式［ａ］ （Ｑ）3−Ａｌ … ［ａ］ ［一般式［ａ］中のＱは、置換若しくは未置換の８−キ
ノリノラート配位子を表す。］で示される発光性有機ア
ルミニウム錯体を含むことを特徴とする（１）〜（１
３）の有機ＥＬ素子。(14) When the electron injecting layer or the electron transporting layer has the following general formula [a] (Q) 3- Al ... [a] [Q in the general formula [a] is a substituted or unsubstituted 8-quinolinolate Represents a ligand. (1) to (1)
3) The organic EL device.
【００２３】（１５）前記（１）〜（１４）の有機ＥＬ
素子を搭載したことを特徴とする有機ＥＬディスプレ
イ。(15) The organic EL of the above (1) to (14)
An organic EL display comprising an element.
【００２４】本発明は、発光層において、一般式
［１］、［４］、［５］、［６］で示される芳香族アミ
ン誘導体と、一般式［２］で示される赤色発光材料のジ
ベンゾ｛［ｆ，ｆ’］−４，４’，７，７’−テトラフ
ェニル｝ジインデノ［１，２，３−ｃｄ：１’，２’，
３’−ｌｍ］ペリレン誘導体とを混合させることによっ
て、より良好なホール輸送性能（電子ブロック性能）を
持たせることや、赤色発光材料の濃度消光などを適度に
抑制させることができ、その結果、発光効率に優れ、輝
度、色度の良好な赤色有機ＥＬ素子を得ることができ
る。According to the present invention, in the light emitting layer, an aromatic amine derivative represented by the general formula [1], [4], [5], or [6] and a red light emitting material dibenzo represented by the general formula [2] are used. {[F, f ′]-4,4 ′, 7,7′-tetraphenyl} diindeno [1,2,3-cd: 1 ′, 2 ′,
By mixing with a 3'-lm] perylene derivative, it is possible to obtain better hole transport performance (electron blocking performance) and moderately suppress concentration quenching of the red light emitting material. A red organic EL device having excellent luminous efficiency, good luminance, and good chromaticity can be obtained.
【００２５】また、緑色発光材料として長寿命特性を有
する前記芳香族アミン誘導体と、非結晶材料の前記ジベ
ンゾ｛［ｆ，ｆ’］−４，４’，７，７’−テトラフェ
ニル｝ジインデノ［１，２，３−ｃｄ：１’，２’，
３’−ｌｍ］ペリレン誘導体とを使用していることから
も、さらに寿命特性の向上が図れる。Further, the aromatic amine derivative having a long life characteristic as a green light emitting material and the dibenzo {[f, f ']-4,4', 7,7'-tetraphenyl} diindeno [ 1,2,3-cd: 1 ', 2',
The use of [3′-lm] perylene derivative can further improve the life characteristics.
【００２６】さらに、電子注入層あるいは電子輸送層に
一般式［３］で示される有機金属錯体を複数種含有させ
ると、輝度を高く保持することができる。すなわち、電
子注入層あるいは電子輸送層において上記有機金属錯体
を１種類だけ使用した場合は、高温下で長時間使用する
と薄膜の凝集や結晶化が進行し、電子注入特性あるいは
電子輸送特性が低下する傾向がある。これに対し、上記
有機金属錯体を２種類以上含有させると非晶質性（アモ
ルファス性）が高くなるため、長時間使用しても凝集、
結晶化が生じにくく、そのため電子注入特性あるいは電
子輸送特性の低下を抑制することができる。Further, when a plurality of kinds of the organometallic complexes represented by the general formula [3] are contained in the electron injecting layer or the electron transporting layer, high brightness can be maintained. That is, when only one kind of the organometallic complex is used in the electron injecting layer or the electron transporting layer, when used at a high temperature for a long time, the aggregation and crystallization of the thin film progresses, and the electron injecting property or the electron transporting property deteriorates. Tend. On the other hand, when two or more of the above-mentioned organometallic complexes are contained, the amorphous property (amorphous property) becomes high, so that even when used for a long time, aggregation,
Crystallization hardly occurs, and therefore, a decrease in electron injection characteristics or electron transport characteristics can be suppressed.
【００２７】[0027]
【発明の実施の形態】次に、本発明の実施形態について
図面を参照して詳細に説明する。図１は本発明の一実施
形態を示す有機ＥＬ素子の概略断面図である。図１にお
いてこの有機ＥＬ素子は、ガラス基板１上にＩＴＯ（イ
ンジウム−スズ酸化物）からなる陽極（透明電極）２を
形成し、この上にホール注入層３、ホール輸送層４、発
光層５、電子輸送層６などの有機ＥＬ層及び陰極７等を
形成することにより構成されている。素子には耐熱性を
持たせるため、ホール注入層３として高耐熱化用ホール
注入層を設けてある。Next, an embodiment of the present invention will be described in detail with reference to the drawings. FIG. 1 is a schematic sectional view of an organic EL device showing one embodiment of the present invention. In FIG. 1, the organic EL device has an anode (transparent electrode) 2 made of ITO (indium-tin oxide) formed on a glass substrate 1, and a hole injection layer 3, a hole transport layer 4, and a light emitting layer 5 formed thereon. , An organic EL layer such as an electron transport layer 6, a cathode 7, and the like. In order to impart heat resistance to the device, a hole injection layer for increasing heat resistance is provided as the hole injection layer 3.
【００２８】ここで、本発明の素子において発光層５に
対し、一般式［１］の芳香族アミン誘導体と、赤色発光
材料である一般式［２］のジベンゾ｛［ｆ，ｆ’］−
４，４’，７，７’−テトラフェニル｝ジインデノ
［１，２，３−ｃｄ：１’，２’，３’−ｌｍ］ペリレ
ン誘導体とを混合させて使用する。このとき、ジベンゾ
｛［ｆ，ｆ’］−４，４’，７，７’−テトラフェニ
ル｝ジインデノ［１，２，３−ｃｄ：１’，２’，３’
−ｌｍ］ペリレン誘導体のドープ量は蒸着レートで制御
しており、色素自体の濃度消光を抑制するために、ドー
プ量は前記芳香族アミン誘導体に対して１〜１０％程度
にするのが好ましい。Here, in the device of the present invention, the light emitting layer 5 and the aromatic amine derivative of the general formula [1] and the dibenzo {[f, f ']-
A 4,4 ′, 7,7′-tetraphenyl dienedeno [1,2,3-cd: 1 ′, 2 ′, 3′-lm] perylene derivative is used as a mixture. At this time, dibenzo {[f, f ']-4,4', 7,7'-tetraphenyl} diindeno [1,2,3-cd: 1 ', 2', 3 '
The doping amount of the [−lm] perylene derivative is controlled by the deposition rate, and the doping amount is preferably about 1 to 10% based on the aromatic amine derivative in order to suppress the concentration quenching of the dye itself.
【００２９】ところで、本発明の一般式［１］で示され
る化合物は公知の方法で合成することができる。例え
ば、アントラセン誘導体、アントラキノン誘導体等に、
置換若しくは未置換のアミン誘導体と、炭酸カリウム、
炭酸ナトリウム、水酸化カリウム、水酸化ナトリウム等
とを、ベンゼン、トルエン又はキシレン等の溶媒下で反
応させることにより合成することができる。触媒とし
て、銅粉、塩化第一銅、スズ、塩化第一スズ、ピリジン
等がある。また、本発明の一般式［２］で示される化合
物も公知の方法で合成することができる。例えば、ベン
ゾ［ｋ］フルオランテン誘導体を塩化アルミニウム／塩
化ナトリウム、フッ化コバルト、トリフルオロ酢酸タリ
ウム等の存在下で反応させることにより合成することが
できる。The compound represented by the general formula [1] of the present invention can be synthesized by a known method. For example, anthracene derivatives, anthraquinone derivatives, etc.
A substituted or unsubstituted amine derivative, potassium carbonate,
It can be synthesized by reacting sodium carbonate, potassium hydroxide, sodium hydroxide or the like in a solvent such as benzene, toluene or xylene. Catalysts include copper powder, cuprous chloride, tin, stannous chloride, pyridine and the like. Further, the compound represented by the general formula [2] of the present invention can also be synthesized by a known method. For example, it can be synthesized by reacting a benzo [k] fluoranthene derivative in the presence of aluminum chloride / sodium chloride, cobalt fluoride, thallium trifluoroacetate or the like.
【００３０】次に、電子輸送層６に対し、一般式［３］
で示されるイオン化ポテンシャルの大きい有機金属錯体
を使用することにより、電子輸送層におけるホールブロ
ック性能をさらに大きくすることができる。一般式
［３］で示される電子輸送材料は、公知の方法で合成す
ることができる。例えば、ガリウム化合物と一般式
［３］の括弧内及びＬの配位子残基を有する化合物を原
料として合成することができる。すなわち、アルキルガ
リウム、ガリウムアルコキシド、ハロゲン化ガリウム、
窒化ガリウム、酸化ガリウム等に、一般式［３］の括弧
内の配位子として８−ヒドロキシキノリン、２−メチル
−８−ヒドロキシキノリン等のキノリン残基を２配位、
Ｌの配位子としてハロゲン原子、置換若しくは未置換の
アルコキシ基、アリールオキシ基、アルキル基を有する
残基を１配位、メタノール、エタノールベンゼン、トル
エン、テトラヒドロフラン等の溶媒下で反応させる。Next, with respect to the electron transport layer 6, a general formula [3]
By using the organometallic complex having a large ionization potential represented by (1), the hole blocking performance in the electron transport layer can be further increased. The electron transporting material represented by the general formula [3] can be synthesized by a known method. For example, it can be synthesized using a gallium compound and a compound having a ligand residue in parentheses and L in the general formula [3] as raw materials. That is, alkyl gallium, gallium alkoxide, gallium halide,
Gallium nitride, gallium oxide, or the like is coordinated with a quinoline residue such as 8-hydroxyquinoline or 2-methyl-8-hydroxyquinoline as a ligand in parentheses in the general formula [3],
A residue having a halogen atom, a substituted or unsubstituted alkoxy group, an aryloxy group, or an alkyl group as a ligand of L is reacted in one coordination under a solvent such as methanol, ethanolbenzene, toluene, and tetrahydrofuran.
【００３１】以下、本発明について実施例を参照して説
明するが、本発明の要旨を変更しない限り、本発明は以
下の実施例に限定されるものではない。Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited to the following examples unless the gist of the present invention is changed.
【００３２】（実施例１）本実施例の有機ＥＬ素子は、
発光層５として下記化合物１(Example 1) The organic EL device of this example is
Compound 1 shown below as light emitting layer 5
【化２８】 の芳香族アミン誘導体に、下記化合物２Embedded image To the following aromatic amine derivatives:
【化２９】 のジベンゾテトラフェニルペリフランテンを蒸着レート
比で２．５％ドープした。電子輸送層６については、下
記化合物３Embedded image Of dibenzotetraphenylperiflanthene at a deposition rate of 2.5%. Regarding the electron transport layer 6, the following compound 3
【化３０】 のガリウム金属錯体を成膜することにより作製した。そ
の結果、電流効率６ｃｄ／Ａ以上（〜１，０００ｃｄ／
ｍ2）、最高輝度３８，０００ｃｄ／ｍ2の実用レベルの
赤色発光が得られた。また、この素子は色度安定性も良
好で、印加電圧に伴う色合いの変化が小さかった。Embedded image Was prepared by forming a gallium metal complex into a film. As a result, the current efficiency was 6 cd / A or more (up to 1,000 cd / A).
m 2 ) and a practical level of red light emission with a maximum luminance of 38,000 cd / m 2 . In addition, this element had good chromaticity stability and little change in hue with applied voltage.
【００３３】ここで図２に、本発明素子の印加電圧に伴
う色合いの変化を従来素子と比較して示す。図中横軸は
印加電圧（Ｖ）を示し、縦軸はＣＩＥ色度座標のＸ又は
Ｙ座標を示してある。これより、本発明素子は色度Ｘに
おいて、従来素子に比べ印加電圧が増加しても色合いの
変化が抑えられているのが判る。Here, FIG. 2 shows a change in color tone according to the applied voltage of the device of the present invention in comparison with the conventional device. In the figure, the horizontal axis indicates the applied voltage (V), and the vertical axis indicates the X or Y coordinate of the CIE chromaticity coordinates. From this, it can be seen that in the device of the present invention, in the chromaticity X, the change in color tone is suppressed even when the applied voltage is increased as compared with the conventional device.
【００３４】さらに、本発明素子に関しては寿命特性が
向上しており、５ｍＡ／ｃｍ2の定電流駆動において良
好な結果が得られている。図３に本発明素子の素子寿命
特性を示す。図中横軸は駆動時間（Ｈｒ）を示し、縦軸
は相対輝度を示してある。これより、本発明素子は、
３，０００時間経過しても初期輝度の９０％以上を維持
するほどの寿命特性であることが判る。また、ダークス
ポット（非発光部）もほとんど観察されなかった。Further, the life characteristics of the device of the present invention are improved, and good results are obtained at a constant current drive of 5 mA / cm 2 . FIG. 3 shows the element life characteristics of the element of the present invention. In the figure, the horizontal axis represents the driving time (Hr), and the vertical axis represents the relative luminance. Thus, the element of the present invention
It can be seen that the life characteristics are such that 90% or more of the initial luminance is maintained even after 3,000 hours. Also, almost no dark spots (non-light emitting portions) were observed.
【００３５】（比較例１）特開平１０−７２５８１で
は、発光層として前記化合物１の芳香族アミン誘導体
に、赤色発光材料を重量比で１％添加することにより、
実施例１とほぼ同レベルの最大発光効率４ｌｍ／Ｗ、最
高輝度３８，０００ｃｄ／ｍ2の赤色発光が得られてい
る。しかしながら、この素子の寿命は短く、３ｍＡ／ｃ
ｍ2の連続発光で、１，０００時間程度しか安定な発光
は確認されておらず、実用化は困難である。(Comparative Example 1) In Japanese Patent Application Laid-Open No. H10-72581, 1% by weight of a red light-emitting material was added to the aromatic amine derivative of the compound 1 as a light-emitting layer.
Red light emission with a maximum luminous efficiency of 4 lm / W and a maximum luminance of 38,000 cd / m 2 , almost the same level as in Example 1, was obtained. However, the lifetime of this device is short and 3 mA / c
With continuous light emission of m 2 , stable light emission has been confirmed for only about 1,000 hours, and practical use is difficult.
【００３６】（比較例２）特開平１０−３３０２９５で
は、発光層として前記化合物２のジベンゾテトラフェニ
ルペリフランテンを単独で用いた場合、１５Ｖの直流電
圧の印加で輝度１，２５０ｃｄ／ｍ2の赤色発光が得ら
れている。また、４，４’−ビス〔Ｎ−フェニル−Ｎ−
（１”−ナフチル）アミノ〕ビフェニルに、前記化合物
２のジベンゾテトラフェニルペリフランテンを重量比で
５％添加することにより、１５Ｖの直流電圧の印加で輝
度２，６５０ｃｄ／ｍ2の赤色発光が得られている。し
かしながら、何れの例も本発明の素子に比べると非常に
輝度が低く、実用化は困難である。(Comparative Example 2) In JP-A-10-330295, when the dibenzotetraphenylperiflanthene of the compound 2 was used alone as the light emitting layer, a luminance of 1,250 cd / m 2 was obtained by applying a DC voltage of 15V. Red light emission is obtained. Further, 4,4′-bis [N-phenyl-N-
By adding 5% by weight of dibenzotetraphenylperiflanthene of the compound 2 to (1 "-naphthyl) amino] biphenyl, red light emission with a luminance of 2,650 cd / m 2 is obtained by applying a DC voltage of 15 V. However, the brightness of each of the examples is much lower than that of the device of the present invention, and practical use is difficult.
【００３７】（比較例３）特開平１１−２３３２６１で
は、発光層として前記化合物４のトリス（８−キノリノ
ラート）アルミニウムに、前記化合物２のジベンゾテト
ラフェニルペリフランテンを重量比で８％添加すること
により、印加電圧９．７Ｖで約５２ｃｄ／ｍ2の赤色発
光が得られている。この素子における２，７００時間の
連続一定電流動作後の輝度は、３０ｃｄ／ｍ2までに減
衰している。よって、本発明の素子に比べると非常に輝
度が低く、寿命も短いことから、実用化は困難である。COMPARATIVE EXAMPLE 3 In JP-A-11-233261, 8% by weight of dibenzotetraphenylperiflanthene of Compound 2 was added to tris (8-quinolinolate) aluminum of Compound 4 as a light emitting layer. As a result, red light emission of about 52 cd / m 2 was obtained at an applied voltage of 9.7 V. The luminance of this device after continuous operation at a constant current for 2,700 hours has attenuated to 30 cd / m 2 . Therefore, since the luminance is very low and the life is short as compared with the device of the present invention, it is difficult to put the device to practical use.
【００３８】（比較例４）特開平１０−８８１２１で
は、一般式［３］に示す金属錯体を発光層あるいは電子
注入層として用いている。例えば、前記化合物３のガリ
ウム金属錯体を電子注入層として用いた場合、直流電圧
８Ｖで輝度１，５０００ｃｄ／ｍ2、発光効率２．３５
ｌｍ／Ｗの青緑色発光が得られている。しかしながら、
本発明では一般式［３］に示す金属錯体を赤色素子の電
子輸送層として用いることにより、高輝度、高効率、長
寿命及び色度安定性をさらに向上させている。Comparative Example 4 In JP-A-10-88121, the metal complex represented by the general formula [3] is used as a light emitting layer or an electron injection layer. For example, when the gallium metal complex of the compound 3 is used as the electron injection layer, the luminance is 1,5000 cd / m 2 at a DC voltage of 8 V, and the luminous efficiency is 2.35.
Blue light emission of lm / W was obtained. However,
In the present invention, high brightness, high efficiency, long life and chromaticity stability are further improved by using the metal complex represented by the general formula [3] as the electron transport layer of the red element.
【００３９】（比較例５）特許公報第２８２８８２１号
では、発光層にペリノン誘導体、電子輸送層にガリウム
金属錯体であるトリス（２−メチル−８−キノリノラー
ト）ガリウムを用いた素子について開示している。この
素子は、１６Ｖの直流電圧の印加で輝度８５０ｃｄ／ｍ
2の黄色発光が確認されており、発光寿命は４日間であ
る。したがって、本発明の素子に比べると非常に輝度が
低く、寿命も極めて短い。Comparative Example 5 Japanese Patent Publication No. 2828821 discloses a device using a perinone derivative for a light emitting layer and a gallium metal complex tris (2-methyl-8-quinolinolate) gallium for an electron transport layer. . This element has a luminance of 850 cd / m when a DC voltage of 16 V is applied.
2. Yellow light emission was confirmed, and the light emission lifetime was 4 days. Therefore, the luminance is very low and the life is extremely short as compared with the device of the present invention.
【００４０】（実施例２）電子輸送層６として、前記化
合物４のトリス（８−キノリノラート）アルミニウムを
使用する以外は、実施例１と同様の方法で有機ＥＬ素子
を作製した。この有機ＥＬ素子の陽極２と陰極７の間に
直流電圧を印加したところ、電流効率５ｃｄ／Ａ以上
（〜１，０００ｃｄ／ｍ2）、最高輝度３５，０００ｃ
ｄ／ｍ2の赤色発光が得られた。(Example 2) An organic EL device was manufactured in the same manner as in Example 1 except that tris (8-quinolinolate) aluminum of the compound 4 was used as the electron transporting layer 6. When a DC voltage was applied between the anode 2 and the cathode 7 of this organic EL device, the current efficiency was 5 cd / A or more (up to 1,000 cd / m 2 ) and the maximum luminance was 35,000 c.
Red light emission of d / m 2 was obtained.
【００４１】（実施例３）発光層５として、前記化合物
１の芳香族アミン誘導体に、前記式［２ｂ］のジベンゾ
［ｆ，ｆ’］ジインデノ［１，２，３−ｃｄ：１’，
２’，３’−ｌｍ］ペリレン誘導体を使用する以外は、
実施例１と同様の方法で有機ＥＬ素子を作製した。この
有機ＥＬ素子の陽極２と陰極７の間に直流電圧を印加し
たところ、電流効率５ｃｄ／Ａ以上（〜１，０００ｃｄ
／ｍ2）、最高輝度３３，０００ｃｄ／ｍ2の赤色発光が
得られた。Example 3 As the light-emitting layer 5, an aromatic amine derivative of the compound 1 was added to the dibenzo [f, f '] diindeno [1,2,3-cd: 1 ′,
2 ′, 3′-lm] perylene derivatives,
An organic EL device was manufactured in the same manner as in Example 1. When a DC voltage was applied between the anode 2 and the cathode 7 of this organic EL device, the current efficiency was 5 cd / A or more (up to 1,000 cd / A).
/ M 2 ) and red light emission with a maximum luminance of 33,000 cd / m 2 was obtained.
【００４２】（実施例４）本実施例の有機ＥＬ素子は、
発光層５として前記化合物１の芳香族アミン誘導体に、
前記式［２ｂ］の化合物を蒸着レート比で２．５％ドー
プした。電子輸送層６については、前記式［３ａ］のガ
リウム金属錯体を成膜することにより作製した。この有
機ＥＬ素子の陽極２と陰極７の間に直流電圧を印加した
ところ、電流効率６．８ｃｄ／Ａ以上（〜１，０００ｃ
ｄ／ｍ2）、最高輝度４５，０００ｃｄ／ｍ2の赤色発光
が得られた。(Example 4) The organic EL device of this example is
As the light emitting layer 5, the aromatic amine derivative of the compound 1
The compound of the formula [2b] was doped at a deposition rate of 2.5%. The electron transport layer 6 was produced by forming a gallium metal complex of the formula [3a]. When a DC voltage was applied between the anode 2 and the cathode 7 of this organic EL element, the current efficiency was 6.8 cd / A or more (up to 1,000 c / A).
d / m 2 ) and red light emission with a maximum luminance of 45,000 cd / m 2 was obtained.
【００４３】（実施例５）電子輸送層６について、前記
式［３ａ］及び式［３ｂ］のガリウム金属錯体を混合し
て成膜すること以外は、実施例４と同様の方法で有機Ｅ
Ｌ素子を作製した。式［３ａ］のガリウム金属錯体：式
［３ｂ］のガリウム金属錯体の混合比は重量比で９：１
とした。この有機ＥＬ素子の陽極２と陰極７の間に直流
電圧を印加したところ、電流効率６．６ｃｄ／Ａ以上
（〜１，０００ｃｄ／ｍ2）、最高輝度４３，０００ｃ
ｄ／ｍ2の赤色発光が得られた。(Example 5) The organic E layer was formed in the same manner as in Example 4, except that the electron transport layer 6 was formed by mixing the gallium metal complexes of the formulas [3a] and [3b].
An L element was produced. The mixing ratio of the gallium metal complex of the formula [3a]: gallium metal complex of the formula [3b] is 9: 1 by weight.
And When a DC voltage was applied between the anode 2 and the cathode 7 of this organic EL device, the current efficiency was 6.6 cd / A or more (up to 1,000 cd / m 2 ), and the maximum luminance was 43,000 c.
Red light emission of d / m 2 was obtained.
【００４４】（実施例６）電子輸送層６について、前記
化合物３のガリウム金属錯体を成膜すること以外は、実
施例４と同様の方法で有機ＥＬ素子を作製した。この有
機ＥＬ素子の陽極２と陰極７の間に直流電圧を印加した
ところ、電流効率６ｃｄ／Ａ以上（〜１，０００ｃｄ／
ｍ2）、最高輝度３８，０００ｃｄ／ｍ2の赤色発光が得
られた。Example 6 An organic EL device was manufactured in the same manner as in Example 4 except that the gallium metal complex of the compound 3 was formed on the electron transport layer 6. When a DC voltage was applied between the anode 2 and the cathode 7 of the organic EL device, the current efficiency was 6 cd / A or more (up to 1,000 cd / A).
m 2 ) and red light emission with a maximum luminance of 38,000 cd / m 2 was obtained.
【００４５】（実施例７）本実施例の有機ＥＬ素子は、
発光層５として前記化合物１の芳香族アミン誘導体に、
前記式［２ａ］の化合物を蒸着レート比で２．５％ドー
プした。電子輸送層６については、前記式［３ａ］のガ
リウム金属錯体を成膜することにより作製した。この有
機ＥＬ素子の陽極２と陰極７の間に直流電圧を印加した
ところ、電流効率６．５ｃｄ／Ａ以上（〜１，０００ｃ
ｄ／ｍ2）、最高輝度４２，０００ｃｄ／ｍ2の赤色発光
が得られた。(Embodiment 7) The organic EL device of this embodiment is
As the light emitting layer 5, the aromatic amine derivative of the compound 1
The compound of the formula [2a] was doped at a deposition rate of 2.5%. The electron transport layer 6 was produced by forming a gallium metal complex of the formula [3a]. When a DC voltage was applied between the anode 2 and the cathode 7 of the organic EL device, the current efficiency was 6.5 cd / A or more (up to 1,000 c / A).
d / m 2 ) and red light emission with a maximum luminance of 42,000 cd / m 2 was obtained.
【００４６】（実施例８）電子輸送層６について、前記
式［３ａ］及び式［３ｂ］のガリウム金属錯体を混合し
て成膜すること以外は、実施例７と同様の方法で有機Ｅ
Ｌ素子を作製した。式［３ａ］のガリウム金属錯体：式
［３ｂ］のガリウム金属錯体の混合比は重量比で９：１
とした。この有機ＥＬ素子の陽極２と陰極７の間に直流
電圧を印加したところ、電流効率６．４ｃｄ／Ａ以上
（〜１，０００ｃｄ／ｍ2）、最高輝度４１，０００ｃ
ｄ／ｍ2の赤色発光が得られた。Example 8 An organic E layer was formed in the same manner as in Example 7, except that the electron transport layer 6 was formed by mixing the gallium metal complexes of the formulas [3a] and [3b].
An L element was produced. The mixing ratio of the gallium metal complex of the formula [3a]: gallium metal complex of the formula [3b] is 9: 1 by weight.
And When a DC voltage was applied between the anode 2 and the cathode 7 of this organic EL device, the current efficiency was 6.4 cd / A or more (up to 1,000 cd / m 2 ), and the maximum luminance was 41,000 c.
Red light emission of d / m 2 was obtained.
【００４７】（実施例９）電子輸送層６について、前記
化合物３のガリウム金属錯体を成膜すること以外は、実
施例７と同様の方法で有機ＥＬ素子を作製した。この有
機ＥＬ素子の陽極２と陰極７の間に直流電圧を印加した
ところ、電流効率５．８ｃｄ／Ａ以上（〜１，０００ｃ
ｄ／ｍ2）、最高輝度３７，０００ｃｄ／ｍ2の赤色発光
が得られた。Example 9 An organic EL device was manufactured in the same manner as in Example 7, except that a gallium metal complex of the compound 3 was formed on the electron transport layer 6. When a DC voltage was applied between the anode 2 and the cathode 7 of the organic EL device, the current efficiency was 5.8 cd / A or more (up to 1,000 c / A).
d / m 2 ) and red light emission with a maximum luminance of 37,000 cd / m 2 was obtained.
【００４８】実施例１、４〜８の有機ＥＬ素子の特性を
表１に示す。Table 1 shows the characteristics of the organic EL devices of Examples 1, 4 to 8.
【表１】 [Table 1]
【００４９】（実施例１０）本実施例の有機ＥＬ素子
は、発光層５として前記化合物１の芳香族アミン誘導体
に、前記化合物２のジベンゾテトラフェニルペリフラン
テンを蒸着レート比で２．５％ドープした。電子輸送層
６については、前記式［３ａ］のガリウム金属錯体を成
膜することにより作製した。Example 10 In the organic EL device of this example, the light emitting layer 5 was prepared by adding the aromatic amine derivative of the compound 1 and the dibenzotetraphenylperiflanthene of the compound 2 at a deposition rate of 2.5%. Doped. The electron transport layer 6 was produced by forming a gallium metal complex of the formula [3a].
【００５０】ここで図４に、実施例１０の素子のＬ−Ｖ
特性及びＪ−Ｖ特性を従来素子と比較して示す。従来素
子は、発光層５として前記化合物４のトリス（８−キノ
リノラート）アルミニウムに下記化合物５の赤色ドーパ
ント（ＤＣＭ）をドープし、電子輸送層６については前
記化合物４のトリス（８−キノリノラート）アルミニウ
ムを成膜したものである。図４より、実施例１０の素子
は、従来の赤色素子よりも低電圧化が可能であることが
わかる。FIG. 4 shows the LV of the device of the tenth embodiment.
The characteristics and the JV characteristics are shown in comparison with the conventional device. In the conventional device, the light emitting layer 5 is obtained by doping the tris (8-quinolinolate) aluminum of the compound 4 with a red dopant (DCM) of the following compound 5, and the electron transporting layer 6 is formed of the tris (8-quinolinolate) aluminum of the compound 4 Is formed. FIG. 4 shows that the device of Example 10 can be operated at a lower voltage than the conventional red device.
【化３１】 Embedded image
【００５１】以上説明した本実施例によれば、発光層に
おいて、特定の芳香族アミン誘導体と、赤色発光材料で
ある特定のジベンゾ｛［ｆ，ｆ’］−４，４’，７，
７’−テトラフェニル｝ジインデノ［１，２，３−ｃ
ｄ：１’，２’，３’−ｌｍ］ペリレン誘導体とを混合
させることにより、発光層においてより良好なホール輸
送性能（電子ブロック性能）を持たせることができる。
この結果、発光層へのホール注入特性が上がり、発光層
でのホール−電子の再結合収率が向上し、高輝度が得ら
れる。また、発光層自身が電子ブロック層の働きもする
ので、電子が発光層を抜けることなく、色純度も向上す
る。さらに、比較的に長寿命特性を有するトリフェニル
ジアミン誘導体と非結晶材料のジベンゾ｛［ｆ，ｆ’］
−４，４’，７，７’−テトラフェニル｝ジインデノ
［１，２，３−ｃｄ：１’，２’，３’−ｌｍ］ペリレ
ン誘導体とを組み合わせることにより、格段に寿命特性
が向上する。According to the present embodiment described above, the specific aromatic amine derivative and the specific dibenzo {[f, f ']-4,4', 7,
7'-tetraphenyldienedeno [1,2,3-c
[d: 1 ', 2', 3'-lm] perylene derivative, the light emitting layer can have better hole transport performance (electron blocking performance).
As a result, the property of injecting holes into the light emitting layer is improved, the recombination yield of hole-electrons in the light emitting layer is improved, and high luminance is obtained. Further, since the light emitting layer itself also functions as an electron blocking layer, electrons do not pass through the light emitting layer, and the color purity is improved. Furthermore, a triphenyldiamine derivative having relatively long life characteristics and a non-crystalline material dibenzo {[f, f ']
By combining with a -4,4 ', 7,7'-tetraphenyldienedeno [1,2,3-cd: 1', 2 ', 3'-lm] perylene derivative, the life characteristics are remarkably improved. .
【００５２】また、電子輸送層としてイオン化ポテンシ
ャルの大きい有機金属錯体を用いることにより、本発明
の発光層のイオン化ポテンシャルに対し、電子輸送層の
イオン化ポテンシャルを大きくすることができる。その
結果、電子輸送層へのホール漏れを制御できるので、発
光層でのホール−電子の再結合収率はさらに向上する。Further, by using an organic metal complex having a large ionization potential as the electron transport layer, the ionization potential of the electron transport layer can be made larger than that of the light emitting layer of the present invention. As a result, hole leakage to the electron transport layer can be controlled, so that the hole-electron recombination yield in the light emitting layer is further improved.
【００５３】本発明は前記実施例に限定されるものでは
なく、例えば一般式［１］に示す芳香族アミン誘導体
と、一般式［２］に示す赤色発光材料であるジベンゾ
｛［ｆ，ｆ’］−４，４’，７，７’−テトラフェニ
ル｝ジインデノ［１，２，３−ｃｄ：１’，２’，３’
−ｌｍ］ペリレン誘導体とを混合させた発光層におい
て、一般式［２］のジベンゾ｛［ｆ，ｆ’］−４，
４’，７，７’−テトラフェニル｝ジインデノ［１，
２，３−ｃｄ：１’，２’，３’−ｌｍ］ペリレン誘導
体のドープ量の異なる発光層を２層以上設けることも可
能である。また、このときのドープ量も１〜１０％の範
囲内に設定するのが好ましい。The present invention is not limited to the above embodiments. For example, an aromatic amine derivative represented by the general formula [1] and a dibenzo {[f, f '] which is a red light emitting material represented by the general formula [2] may be used. ] -4,4 ', 7,7'-tetraphenyldienedeno [1,2,3-cd: 1', 2 ', 3'
[Lm] perylene derivative in a light-emitting layer mixed with dibenzo {[f, f ']-4,
4 ', 7,7'-tetraphenyldienedeno [1,
[2,3-cd: 1 ', 2', 3'-lm] It is also possible to provide two or more light emitting layers with different doping amounts of perylene derivatives. Further, the doping amount at this time is also preferably set in the range of 1 to 10%.
【００５４】[0054]
【発明の効果】本発明は、以上のように構成され機能す
るので、従来に比べて、発光効率に優れ、輝度、色度の
良好な赤色有機ＥＬ素子を得ることができる。また、寿
命特性も格段に向上するので、長期的信頼性の高い有機
ＥＬディスプレイを提供することができる。Since the present invention is constructed and functions as described above, a red organic EL device having excellent luminous efficiency, good luminance and good chromaticity can be obtained as compared with the prior art. In addition, the life characteristics are significantly improved, so that an organic EL display having high long-term reliability can be provided.
【図１】本発明の一実施形態を示す有機ＥＬ素子の概略
断面図である。FIG. 1 is a schematic sectional view of an organic EL device showing one embodiment of the present invention.
【図２】本発明素子の印加電圧に伴う色合いの変化を従
来素子と比較して示すグラフである。FIG. 2 is a graph showing a change in color tone according to an applied voltage of the device of the present invention, as compared with a conventional device.
【図３】本発明素子の素子寿命特性を示すグラフであ
る。FIG. 3 is a graph showing element life characteristics of the element of the present invention.
【図４】実施例１０の素子のＬ−Ｖ特性及びＪ−Ｖ特性
を従来素子と比較して示すグラフである。FIG. 4 is a graph showing LV characteristics and JV characteristics of a device of Example 10 in comparison with a conventional device.
【図５】従来の有機ＥＬ素子の概略断面図である。FIG. 5 is a schematic sectional view of a conventional organic EL element.
１ ガラス基板 ２ 陽極 ３ ホール注入層 ４ ホール輸送層 ５ 発光層 ６ 電子輸送層 ７ 陰極 DESCRIPTION OF SYMBOLS 1 Glass substrate 2 Anode 3 Hole injection layer 4 Hole transport layer 5 Light emitting layer 6 Electron transport layer 7 Cathode
Claims (15)
とも単層又は複数層の有機薄膜よりなる発光層を備えた
有機ＥＬ素子において、下記一般式［１］ 【化１】 ［一般式［１］中のＲ1〜Ｒ28は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｙ1〜Ｙ4は、それぞれ独立にＯ、Ｓ、ＳＯ
2、Ｃ＝Ｏ、ＣＨ2Ｏ、ＣＨ2ＯＣＨ2、又は、置換若しく
は未置換のアルキレン基を表す。Ｒ1〜Ｒ4、Ｒ5〜Ｒ8
は、互いに結合して飽和若しくは不飽和の５員環又は６
員環を形成してもよい。］で示される芳香族アミン誘導
体と、下記一般式［２］ 【化２】 ［一般式［２］中のＸ1〜Ｘ20は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｘ1〜Ｘ20は、互いに結合して飽和若しく
は不飽和の５員環又は６員環を形成してもよい。］で示
されるジベンゾ｛［ｆ，ｆ’］−４，４’，７，７’−
テトラフェニル｝ジインデノ［１，２，３−ｃｄ：
１’，２’，３’−ｌｍ］ペリレン誘導体とを混合させ
た少なくとも１層の発光層を有していることを特徴とす
る有機ＥＬ素子。1. An organic EL device comprising a light-emitting layer comprising at least a single layer or a plurality of organic thin films between an anode and a cathode facing each other, comprising an organic EL device represented by the following general formula [1]: [In the general formula [1], R 1 to R 28 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, Represents an unsubstituted amino group. Y1 to Y4 are each independently O, S, SO
2, C = O, CH 2 O, CH 2 OCH 2, or a substituted or unsubstituted alkylene group. R1 ~ R4, R5 ~ R8
Are bonded to each other to form a saturated or unsaturated 5-membered ring or 6
A member ring may be formed. And an aromatic amine derivative represented by the following general formula [2]: [X 1 to X 20 in the general formula [2] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group. Represents an unsubstituted amino group. X1 to X20 may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. Dibenzo} [f, f ']-4,4', 7,7'-
Tetraphenyl dienedeno [1,2,3-cd:
[1 ', 2', 3'-lm] An organic EL device comprising at least one light-emitting layer mixed with a perylene derivative.
とも単層又は複数層の有機薄膜よりなる発光層を備えた
有機ＥＬ素子において、下記一般式［４］ 【化３】 ［一般式［４］中のＲ1〜Ｒ28は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｙ1〜Ｙ4は、それぞれ独立にＯ、Ｓ、ＳＯ
2、Ｃ＝Ｏ、ＣＨ2Ｏ、ＣＨ2ＯＣＨ2、又は、置換若しく
は未置換のアルキレン基を表す。Ｒ1〜Ｒ4、Ｒ5〜Ｒ8
は、互いに結合して飽和若しくは不飽和の５員環又は６
員環を形成してもよい。］で示される芳香族アミン誘導
体と、下記一般式［２］ 【化４】 ［一般式［２］中のＸ1〜Ｘ20は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｘ1〜Ｘ20は、互いに結合して飽和若しく
は不飽和の５員環又は６員環を形成してもよい。］で示
されるジベンゾ｛［ｆ，ｆ’］−４，４’，７，７’−
テトラフェニル｝ジインデノ［１，２，３−ｃｄ：
１’，２’，３’−ｌｍ］ペリレン誘導体とを混合させ
た少なくとも１層の発光層を有していることを特徴とす
る有機ＥＬ素子。2. An organic EL device comprising a light-emitting layer comprising at least a single layer or a plurality of organic thin films between an anode and a cathode facing each other, wherein the organic EL device has the following general formula [4]: [R 1 to R 28 in the general formula [4] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, Represents an unsubstituted amino group. Y1 to Y4 are each independently O, S, SO
2, C = O, CH 2 O, CH 2 OCH 2, or a substituted or unsubstituted alkylene group. R1 ~ R4, R5 ~ R8
Are bonded to each other to form a saturated or unsaturated 5-membered ring or 6
A member ring may be formed. And an aromatic amine derivative represented by the following general formula [2]: [X 1 to X 20 in the general formula [2] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group. Represents an unsubstituted amino group. X1 to X20 may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. Dibenzo} [f, f ']-4,4', 7,7'-
Tetraphenyl dienedeno [1,2,3-cd:
[1 ', 2', 3'-lm] An organic EL device comprising at least one light-emitting layer mixed with a perylene derivative.
とも単層又は複数層の有機薄膜よりなる発光層を備えた
有機ＥＬ素子において、下記一般式［５］ 【化５】 ［一般式［５］中のＲ1〜Ｒ28は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｘ1〜Ｘ8は、置換若しくは未置換の炭素数
１〜２０のアルキル基、又は、置換若しくは未置換の炭
素数６〜１６のアリール基を表す。Ｒ1〜Ｒ4、Ｒ5〜Ｒ8
は、互いに結合して飽和若しくは不飽和の５員環又は６
員環を形成してもよい。］で示される芳香族アミン誘導
体と、下記一般式［２］ 【化６】 ［一般式［２］中のＸ1〜Ｘ20は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｘ1〜Ｘ20は、互いに結合して飽和若しく
は不飽和の５員環又は６員環を形成してもよい。］で示
されるジベンゾ｛［ｆ，ｆ’］−４，４’，７，７’−
テトラフェニル｝ジインデノ［１，２，３−ｃｄ：
１’，２’，３’−ｌｍ］ペリレン誘導体とを混合させ
た少なくとも１層の発光層を有していることを特徴とす
る有機ＥＬ素子。3. An organic EL device comprising a light emitting layer composed of at least a single layer or a plurality of organic thin films between an anode and a cathode facing each other, wherein the organic compound has the following general formula [5]: [R 1 to R 28 in the general formula [5] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted Represents an unsubstituted amino group. X1 to X8 represent a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 16 carbon atoms. R1 ~ R4, R5 ~ R8
Are bonded to each other to form a saturated or unsaturated 5-membered ring or 6
A member ring may be formed. And an aromatic amine derivative represented by the following general formula [2]: [X 1 to X 20 in the general formula [2] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group. Represents an unsubstituted amino group. X1 to X20 may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. Dibenzo} [f, f ']-4,4', 7,7'-
Tetraphenyl dienedeno [1,2,3-cd:
[1 ', 2', 3'-lm] An organic EL device comprising at least one light-emitting layer mixed with a perylene derivative.
とも単層又は複数層の有機薄膜よりなる発光層を備えた
有機ＥＬ素子において、下記一般式［６］ 【化７】 ［一般式［６］中のＲ1〜Ｒ28は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｒ1〜Ｒ4、Ｒ5〜Ｒ8は、互いに結合して飽
和若しくは不飽和の５員環又は６員環を形成してもよ
い。］で示される芳香族アミン誘導体と、下記一般式
［２］ 【化８】 ［一般式［２］中のＸ1〜Ｘ20は、それぞれ独立に水素
原子、ハロゲン原子、置換若しくは未置換のアルキル
基、置換若しくは未置換のアルコキシ基、置換若しくは
未置換のアリール基、又は、置換若しくは未置換のアミ
ノ基を表す。Ｘ1〜Ｘ20は、互いに結合して飽和若しく
は不飽和の５員環又は６員環を形成してもよい。］で示
されるジベンゾ｛［ｆ，ｆ’］−４，４’，７，７’−
テトラフェニル｝ジインデノ［１，２，３−ｃｄ：
１’，２’，３’−ｌｍ］ペリレン誘導体とを混合させ
た少なくとも１層の発光層を有していることを特徴とす
る有機ＥＬ素子。4. An organic EL device comprising a light-emitting layer comprising at least a single layer or a plurality of organic thin films between an anode and a cathode facing each other, wherein the organic EL device has the following general formula [6]: [R 1 to R 28 in the general formula [6] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, Represents an unsubstituted amino group. R1 to R4 and R5 to R8 may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. And an aromatic amine derivative represented by the following general formula [2]: [X 1 to X 20 in the general formula [2] are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group. Represents an unsubstituted amino group. X1 to X20 may combine with each other to form a saturated or unsaturated 5- or 6-membered ring. Dibenzo} [f, f ']-4,4', 7,7'-
Tetraphenyl dienedeno [1,2,3-cd:
[1 ', 2', 3'-lm] An organic EL device comprising at least one light-emitting layer mixed with a perylene derivative.
−４，４’，７，７’−テトラフェニル｝ジインデノ
［１，２，３−ｃｄ：１’，２’，３’−ｌｍ］ペリレ
ン誘導体が下記式［２ａ］で示される化合物であること
を特徴とする請求項１〜４のいずれか１項に記載の有機
ＥＬ素子。 【化９】 5. A dibenzo {[f, f ′] of the general formula [2]
The -4,4 ', 7,7'-tetraphenyldienedeno [1,2,3-cd: 1', 2 ', 3'-lm] perylene derivative is a compound represented by the following formula [2a]. The organic EL device according to claim 1, wherein: Embedded image
−４，４’，７，７’−テトラフェニル｝ジインデノ
［１，２，３−ｃｄ：１’，２’，３’−ｌｍ］ペリレ
ン誘導体が下記式［２ｂ］で示される化合物であること
を特徴とする請求項１〜４のいずれか１項に記載の有機
ＥＬ素子。 【化１０】 6. A dibenzo {[f, f ′] of the general formula [2]
The -4,4 ', 7,7'-tetraphenyldiindeno [1,2,3-cd: 1', 2 ', 3'-lm] perylene derivative is a compound represented by the following formula [2b] The organic EL device according to claim 1, wherein: Embedded image
［６］の芳香族アミン誘導体をホストとし、これに一般
式［２］のジベンゾ｛［ｆ，ｆ’］−４，４’，７，
７’−テトラフェニル｝ジインデノ［１，２，３−ｃ
ｄ：１’，２’，３’−ｌｍ］ペリレン誘導体がドープ
されており、ドープ比率が１〜１０％であることを特徴
とする請求項１〜６のいずれか１項に記載の有機ＥＬ素
子。7. An aromatic amine derivative represented by the general formula [1], [4], [5] or [6] is used as a host, and a dibenzo {[f, f ′]-4, 4 ', 7,
7'-tetraphenyldienedeno [1,2,3-c
The organic EL according to any one of claims 1 to 6, wherein the organic EL is doped with a d: 1 ', 2', 3'-lm] perylene derivative and has a doping ratio of 1 to 10%. element.
式［３］ 【化１１】 ［一般式［３］中のＭは金属原子を表す。Ｒ1〜Ｒ6は、
それぞれ独立に水素原子、ハロゲン原子、置換若しくは
未置換のアルキル基、置換若しくは未置換のアルコキシ
基、置換若しくは未置換のアリール基、置換若しくは未
置換のアリールオキシ基、置換若しくは未置換のシクロ
アルキル基又はシアノ基を表す。Ｌは、ハロゲン原子、
置換若しくは未置換のアルコキシ基、置換若しくは未置
換のアリールオキシ基、置換若しくは未置換のアルキル
基、置換若しくは未置換のアリールオキシ基又は置換若
しくは未置換のシクロアルキル基を有する配位子を表
す。］で示される有機金属錯体を含むことを特徴とする
請求項１〜７のいずれか１項に記載の有機ＥＬ素子。8. An electron injecting layer or an electron transporting layer represented by the following general formula [3]: [M in the general formula [3] represents a metal atom. R1 to R6 are
Each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted cycloalkyl group Or a cyano group. L is a halogen atom,
A ligand having a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryloxy group, or a substituted or unsubstituted cycloalkyl group. The organic EL device according to any one of claims 1 to 7, comprising an organometallic complex represented by the following formula:
4がアリール基であることを特徴とする請求項８に記載
の有機ＥＬ素子。9. An organic metal complex represented by the general formula [3]:
9. The organic EL device according to claim 8, wherein 4 is an aryl group.
［３ａ］で示される化合物であることを特徴とする請求
項９に記載の有機ＥＬ素子。 【化１２】 10. The organic EL device according to claim 9, wherein the organometallic complex represented by the general formula [3] is a compound represented by the following formula [3a]. Embedded image
［３ｂ］で示される化合物であることを特徴とする請求
項９に記載の有機ＥＬ素子。 【化１３】 11. The organic EL device according to claim 9, wherein the organometallic complex represented by the general formula [3] is a compound represented by the following formula [3b]. Embedded image
［３］で示される有機金属錯体を複数種含むことを特徴
とする請求項８〜１１のいずれか１項に記載の有機ＥＬ
素子。12. The organic EL according to claim 8, wherein the electron injection layer or the electron transport layer contains a plurality of types of the organometallic complexes represented by the general formula [3].
element.
［３ａ］で示される化合物及び下記式［３ｂ］で示され
る化合物を含むことを特徴とする請求項１２に記載の有
機ＥＬ素子。 【化１４】 【化１５】 13. The organic EL device according to claim 12, wherein the electron injecting layer or the electron transporting layer contains a compound represented by the following formula [3a] and a compound represented by the following formula [3b]. Embedded image Embedded image
般式［ａ］ （Ｑ）3−Ａｌ … ［ａ］ ［一般式［ａ］中のＱは、置換若しくは未置換の８−キ
ノリノラート配位子を表す。］で示される発光性有機ア
ルミニウム錯体を含むことを特徴とする請求項１〜１３
のいずれか１項に記載の有機ＥＬ素子。14. An electron injecting layer or an electron transporting layer according to the following general formula [a] (Q) 3 -Al... [A] wherein Q in general formula [a] is a substituted or unsubstituted 8-quinolinolate compound. Represents a ligand. A luminescent organic aluminum complex represented by the formula:
The organic EL device according to any one of the above.
の有機ＥＬ素子を搭載したことを特徴とする有機ＥＬデ
ィスプレイ。15. An organic EL display, comprising the organic EL element according to claim 1.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001042102A JP3688207B2 (en) | 2000-02-18 | 2001-02-19 | Organic EL device and organic EL display |
| US09/932,194 US6689493B2 (en) | 2000-02-18 | 2001-08-17 | Organic electroluminescent element and organic electroluminescent display |
| EP01119918.9A EP1235466B1 (en) | 2001-02-19 | 2001-08-17 | Organic electroluminescent element and organic electroluminescent display |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000040925 | 2000-02-18 | ||
| JP2000-40925 | 2000-02-18 | ||
| JP2001042102A JP3688207B2 (en) | 2000-02-18 | 2001-02-19 | Organic EL device and organic EL display |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2001307885A true JP2001307885A (en) | 2001-11-02 |
| JP3688207B2 JP3688207B2 (en) | 2005-08-24 |
Family
ID=26585641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001042102A Expired - Lifetime JP3688207B2 (en) | 2000-02-18 | 2001-02-19 | Organic EL device and organic EL display |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3688207B2 (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005068366A (en) * | 2003-08-27 | 2005-03-17 | Toyo Ink Mfg Co Ltd | Material for organic electroluminescent element and organic electroluminescent element |
| WO2007052759A1 (en) | 2005-11-07 | 2007-05-10 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
| WO2007061063A1 (en) | 2005-11-28 | 2007-05-31 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| WO2007099983A1 (en) | 2006-02-28 | 2007-09-07 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device using fluoranthene derivative and indenoperylene derivative |
| WO2007105448A1 (en) | 2006-02-28 | 2007-09-20 | Idemitsu Kosan Co., Ltd. | Naphthacene derivative and organic electroluminescent device using same |
| US7402344B2 (en) | 2003-03-24 | 2008-07-22 | Sony Corporation | Organic electroluminescent devices and aminostyrylnaphthalene compounds |
| JP2008187185A (en) * | 2002-12-31 | 2008-08-14 | Eastman Kodak Co | Efficient electroluminescence device |
| WO2008111554A1 (en) | 2007-03-09 | 2008-09-18 | Idemitsu Kosan Co., Ltd. | Organic el device and display |
| KR100910150B1 (en) | 2008-04-02 | 2009-08-03 | (주)그라쎌 | Novel organic light emitting compound and organic light emitting device employing the same as light emitting material |
| WO2020039708A1 (en) | 2018-08-23 | 2020-02-27 | 国立大学法人九州大学 | Organic electroluminescence element |
-
2001
- 2001-02-19 JP JP2001042102A patent/JP3688207B2/en not_active Expired - Lifetime
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008187185A (en) * | 2002-12-31 | 2008-08-14 | Eastman Kodak Co | Efficient electroluminescence device |
| US7524991B2 (en) | 2003-03-24 | 2009-04-28 | Sony Corporation | Organic electroluminescent devices, aminostyrylnaphthalene compounds and synthesis intermediates thereof, and production processes of the same |
| US7402344B2 (en) | 2003-03-24 | 2008-07-22 | Sony Corporation | Organic electroluminescent devices and aminostyrylnaphthalene compounds |
| JP2005068366A (en) * | 2003-08-27 | 2005-03-17 | Toyo Ink Mfg Co Ltd | Material for organic electroluminescent element and organic electroluminescent element |
| WO2007052759A1 (en) | 2005-11-07 | 2007-05-10 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent element |
| KR101364423B1 (en) | 2005-11-07 | 2014-02-17 | 이데미쓰 고산 가부시키가이샤 | Organic electroluminescent element |
| JP5280687B2 (en) * | 2005-11-07 | 2013-09-04 | 出光興産株式会社 | Organic electroluminescence device |
| WO2007061063A1 (en) | 2005-11-28 | 2007-05-31 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device |
| WO2007099983A1 (en) | 2006-02-28 | 2007-09-07 | Idemitsu Kosan Co., Ltd. | Organic electroluminescent device using fluoranthene derivative and indenoperylene derivative |
| WO2007105448A1 (en) | 2006-02-28 | 2007-09-20 | Idemitsu Kosan Co., Ltd. | Naphthacene derivative and organic electroluminescent device using same |
| US8278819B2 (en) | 2007-03-09 | 2012-10-02 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device and display |
| WO2008111554A1 (en) | 2007-03-09 | 2008-09-18 | Idemitsu Kosan Co., Ltd. | Organic el device and display |
| KR100910150B1 (en) | 2008-04-02 | 2009-08-03 | (주)그라쎌 | Novel organic light emitting compound and organic light emitting device employing the same as light emitting material |
| WO2020039708A1 (en) | 2018-08-23 | 2020-02-27 | 国立大学法人九州大学 | Organic electroluminescence element |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3688207B2 (en) | 2005-08-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6689493B2 (en) | Organic electroluminescent element and organic electroluminescent display | |
| JP3987256B2 (en) | Organic electroluminescence device | |
| EP0786925B1 (en) | White light-emitting electroluminescent devices | |
| US7026480B2 (en) | Organometallic light-emitting material | |
| TW546851B (en) | Organic light-emitting device having a color-neutral dopant in a hole-transport layer and/or in an electron-transport layer | |
| EP1642951A2 (en) | Iridium-based luminescent compounds having phenylpyridine moieties with organosilicon group, and organic electroluminescence devices using the compounds as colour-emitting materials | |
| KR100681027B1 (en) | Electroluminescent Devices and Electron Transfer Compounds | |
| KR101494789B1 (en) | Organci emitting material and organic light emitting device using thereof | |
| KR20030014927A (en) | Blue light-emitting compound and display device adopting light-emitting compound as color-developing substance | |
| KR101989667B1 (en) | Organic electroluminescent devices | |
| JP3688207B2 (en) | Organic EL device and organic EL display | |
| KR100525409B1 (en) | organic electroluminescence device | |
| KR100854880B1 (en) | Dynaphthopyrene compound and organic EL element and organic EL display using same | |
| US20030099861A1 (en) | Efficient red organic electroluminescent devices | |
| KR20010082752A (en) | Organic EL device and organic EL display | |
| US6322909B1 (en) | Organic electroluminescent device comprising a squarylium compound | |
| CN113248504A (en) | Electron transport material, preparation method thereof and organic light-emitting diode | |
| EP1235466A2 (en) | Organic electroluminescent element and organic electroluminescent display | |
| JP4631600B2 (en) | Organic electroluminescence device | |
| JP2008205254A (en) | Organic electroluminescence device | |
| KR19990086810A (en) | High melting point complex and organic light emitting device comprising the same | |
| KR101916867B1 (en) | Blue phosphorescent compound and Organic electroluminescent device using the same | |
| JP3338164B2 (en) | Organic electroluminescent device | |
| US20040185298A1 (en) | Red-emitting organic electroluminescent elements | |
| KR100546590B1 (en) | Green organic light emitting diode |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20040316 |
|
| A711 | Notification of change in applicant |
Free format text: JAPANESE INTERMEDIATE CODE: A711 Effective date: 20040316 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20040720 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20041020 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20041021 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20041025 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20041214 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050310 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20050510 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20050607 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 3688207 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20080617 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090617 Year of fee payment: 4 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090617 Year of fee payment: 4 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090617 Year of fee payment: 4 |
|
| R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090617 Year of fee payment: 4 |
|
| R360 | Written notification for declining of transfer of rights |
Free format text: JAPANESE INTERMEDIATE CODE: R360 |
|
| R371 | Transfer withdrawn |
Free format text: JAPANESE INTERMEDIATE CODE: R371 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20090617 Year of fee payment: 4 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100617 Year of fee payment: 5 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110617 Year of fee payment: 6 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110617 Year of fee payment: 6 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120617 Year of fee payment: 7 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130617 Year of fee payment: 8 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130617 Year of fee payment: 8 |
|
| S111 | Request for change of ownership or part of ownership |
Free format text: JAPANESE INTERMEDIATE CODE: R313111 |
|
| S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130617 Year of fee payment: 8 |
|
| R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |
