JPH0711243A - Organic thin film light-emitting element - Google Patents
Organic thin film light-emitting elementInfo
- Publication number
- JPH0711243A JPH0711243A JP5205464A JP20546493A JPH0711243A JP H0711243 A JPH0711243 A JP H0711243A JP 5205464 A JP5205464 A JP 5205464A JP 20546493 A JP20546493 A JP 20546493A JP H0711243 A JPH0711243 A JP H0711243A
- Authority
- JP
- Japan
- Prior art keywords
- light emitting
- injection layer
- group
- organic thin
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000010409 thin film Substances 0.000 title claims description 40
- 238000002347 injection Methods 0.000 claims abstract description 120
- 239000007924 injection Substances 0.000 claims abstract description 120
- 239000000126 substance Substances 0.000 claims abstract description 84
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 41
- 125000003118 aryl group Chemical group 0.000 claims abstract description 41
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 19
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000003577 thiophenes Chemical class 0.000 claims description 50
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 18
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical class C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 claims description 16
- -1 aluminum quinolinol Chemical compound 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- 125000005504 styryl group Chemical group 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 174
- 239000010408 film Substances 0.000 description 101
- 239000000758 substrate Substances 0.000 description 50
- 238000007740 vapor deposition Methods 0.000 description 48
- 238000010438 heat treatment Methods 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 25
- 239000011521 glass Substances 0.000 description 13
- 229910000846 In alloy Inorganic materials 0.000 description 11
- 229910000861 Mg alloy Inorganic materials 0.000 description 10
- 101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 150000004866 oxadiazoles Chemical class 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 238000005215 recombination Methods 0.000 description 5
- 230000006798 recombination Effects 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005566 electron beam evaporation Methods 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 238000005266 casting Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 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 3
- 239000012044 organic layer Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- NQFDVAFUBOXJQM-UHFFFAOYSA-N 1h-quinolin-2-one;zinc Chemical compound [Zn].C1=CC=C2NC(=O)C=CC2=C1 NQFDVAFUBOXJQM-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
Abstract
Description
【０００１】[0001]
【産業上の利用分野】この発明は各種表示装置の発光源
として用いる有機薄膜発光素子に係り、特に素子の発光
層に用いられる発光物質に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic thin film light emitting device used as a light emitting source of various display devices, and more particularly to a light emitting substance used for a light emitting layer of the device.
【０００２】[0002]
【従来の技術】従来のブラウン管に代わるフラットディ
スプレイの需要の急増に伴い、各種表示素子の開発及び
実用化が精力的に進められている。エレクトロルミネセ
ンス素子（以下ＥＬ素子とする）もこうしたニ−ズに即
するものであり、特に全固体の自発発光素子として、他
のディスプレイにはない高解像度及び高視認性により注
目を集めている。現在、実用化されているものは、発光
層にＺｎＳ／Ｍｎ系を用いた無機材料からなるＥＬ素子
である。しかるに、この種の無機ＥＬ素子は発光に必要
な駆動電圧が１００Ｖ以上と高いため駆動方法が複雑と
なり製造コストが高いといった問題点がある。また、青
色発光の効率が低いため、フルカラ−化が困難である。
これに対して、有機材料を用いた薄膜発光素子は、発光
に必要な駆動電圧が大幅に低減でき、かつ各種発光材料
の適用によりフルカラ−化の可能性を充分に持つことか
ら、近年研究が活発化している。2. Description of the Related Art With the rapid increase in demand for flat displays replacing conventional cathode ray tubes, various display elements have been vigorously developed and put into practical use. Electroluminescence devices (hereinafter referred to as EL devices) are also suitable for such needs, and as an all-solid-state spontaneous light-emitting device, they are particularly attracting attention due to their high resolution and high visibility that other displays do not have. . At present, what has been put into practical use is an EL element made of an inorganic material using a ZnS / Mn system in the light emitting layer. However, this type of inorganic EL element has a problem that the driving method is complicated and the manufacturing cost is high because the driving voltage required for light emission is as high as 100 V or more. In addition, since the efficiency of blue light emission is low, it is difficult to achieve full color.
On the other hand, thin-film light-emitting devices using organic materials can drastically reduce the driving voltage required for light emission, and have the potential for full colorization by the application of various light-emitting materials. It is becoming active.
【０００３】特に、電極／正孔注入層／発光層／電極か
らなる積層型において、発光物質にトリス（８−ヒドロ
キシキノリン）アルミニウムを、正孔注入物質に１，１
−ビス（４−Ｎ，Ｎ−ジトリルアミノフェニル）シクロ
ヘキサンを用いることにより、１０Ｖ以下の印加電圧で
１０００ｃｄ／ｍ2 以上の輝度が得られたという報告が
なされて以来開発に拍車がかけられた（Appl.Phys.Let
t. 51,913,(1987))。In particular, in the laminated type composed of electrode / hole injection layer / light emitting layer / electrode, tris (8-hydroxyquinoline) aluminum is used as the light emitting substance and 1,1 as the hole injection substance.
Since the use of -bis (4-N, N-ditolylaminophenyl) cyclohexane gave a brightness of 1000 cd / m 2 or more at an applied voltage of 10 V or less, the development was spurred. (Appl.Phys.Let
t. 51 , 913, (1987)).
【０００４】[0004]
【発明が解決しようとする課題】この様に、有機材料を
用いた薄膜発光素子は低電圧駆動やフルカラ−化の可能
性等を強く示唆しているものの、性能面で解決しなけれ
ばならない課題が多く残されている。約１万時間の長時
間駆動に伴う特性劣化の問題は乗り越えなければならな
い課題である。また有機層の膜厚が１μｍ以下であるた
めに、成膜性が良好でピンホール等の電気的欠陥がな
く、電子，正孔の輸送能力に優れた有機材料の開発、有
機層への電荷の注入性に優れる電極材料の選択等があ
る。As described above, although the thin film light emitting device using an organic material strongly suggests the possibility of low voltage driving and full colorization, the problem to be solved in terms of performance. There are many left. The problem of characteristic deterioration due to long-time driving of about 10,000 hours is a problem that must be overcome. In addition, since the thickness of the organic layer is 1 μm or less, film formation is good, there are no electrical defects such as pinholes, and the development of organic materials with excellent electron and hole transporting capacity, charge to the organic layer There is a selection of an electrode material having excellent injectability of
【０００５】さらには量産性の観点から大量製造が可能
で安価な有機材料の開発や素子形成方法の改良等も重要
な課題である。この発明は上述の点に鑑みてなされその
目的は、新規な発光層を開発することにより、高輝度で
あるうえに成膜性が良好で均一発光性に優れる有機薄膜
発光素子を提供することにある。Further, from the viewpoint of mass productivity, the development of inexpensive organic materials that can be mass-produced and the improvement of the element forming method are important issues. The present invention has been made in view of the above points, and an object thereof is to provide an organic thin film light emitting device having high brightness, good film formability and excellent uniform light emission by developing a novel light emitting layer. is there.
【０００６】[0006]
【課題を解決するための手段】上述の目的は第一の発明
によれば正極と負極とからなる一対の電極と、その間に
挟まれた発光層と電荷注入層を有し、電荷注入層は正孔
注入層と電子注入層のうちの少なくとも一つからなり、
発光層はキノリノール系錯体の主発光物質と、下記一般
式（Ｉ）で表されるチオフェン誘導体の副発光物質とか
らなるとすることにより達成される。According to the first aspect of the present invention, the above-mentioned object has a pair of electrodes consisting of a positive electrode and a negative electrode, a light emitting layer and a charge injection layer sandwiched therebetween, and the charge injection layer is At least one of a hole injection layer and an electron injection layer,
The light emitting layer is achieved by comprising a main light emitting substance of a quinolinol complex and a sub light emitting substance of a thiophene derivative represented by the following general formula (I).
【０００７】[0007]
【化８】 [Chemical 8]
【０００８】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれ水素原子，アルキル基，アリール基，シアノ基
または複素環基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10
はそれぞれ水素原子，ハロゲン原子．アルキル基，アル
コキシ基またはアリール基、ｍは１または２、ｌとｎは
それぞれ０または１でｍ＋ｌ＋ｎ＝１ないし４の整数を
表す。〕 第二の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は正孔注入層と電子注入層のうちの少なくとも一
つからなり、発光層は下記一般式（Ｉ）で表されるチオ
フェン誘導体からなるとすることにより達成される。[In the formula (I), R 1 , R 2 , R 3 and R 4 are a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 and R 8 respectively. , R 9 , R 10
Are hydrogen atom and halogen atom, respectively. An alkyl group, an alkoxy group or an aryl group, m is 1 or 2, l and n are 0 or 1, and m + 1 + n = 1 is an integer of 1 to 4. According to the second invention, it has a pair of electrodes consisting of a positive electrode and a negative electrode, a light emitting layer and a charge injection layer sandwiched therebetween, and the charge injection layer is at least the hole injection layer and the electron injection layer. The light emitting layer is made of a single material, and is achieved by using a thiophene derivative represented by the following general formula (I).
【０００９】[0009]
【化９】 [Chemical 9]
【００１０】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれ水素原子，アルキル基，アリール基，シアノ基
または複素環基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、
Ｒ10、はそれぞれ水素原子，ハロゲン原子．アルキル
基，アルコキシ基またはアリール基、ｍは２、ｌとｎは
それぞれ１を表す。〕 第三の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は正孔注入層と電子注入層のうちの少なくとも正
孔注入層からなり、発光層は下記一般式（Ｉ）で表され
るチオフェン誘導体からなるとすることにより達成され
る。[In the formula (I), R 1 , R 2 , R 3 and R 4 are a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 and R 8 respectively. , R 9 ,
R 10 is a hydrogen atom or a halogen atom, respectively. An alkyl group, an alkoxy group or an aryl group, m is 2, and 1 and n are 1 respectively. According to the third invention, it has a pair of electrodes consisting of a positive electrode and a negative electrode, a light emitting layer and a charge injection layer sandwiched therebetween, and the charge injection layer is at least a hole injection layer or an electron injection layer. This is achieved by comprising a hole injection layer and forming the light emitting layer from a thiophene derivative represented by the following general formula (I).
【００１１】[0011]
【化１０】 [Chemical 10]
【００１２】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれ水素原子，アルキル基，アリール基，シアノ基
または複素環基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10
はそれぞれ水素原子．ハロゲン原子．アルキル基，アル
コキシ基またはアリール基を表すとともに、Ｒ1 、
Ｒ2 、Ｒ3 、Ｒ4 の内の一つ以上の基が水素原子，シア
ノ基から選ばれるかまたはＲ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ
9 、Ｒ10の内の一つ以上の基がハロゲン原子．アルコキ
シ基から選ばれる。ｍは１または２、ｌとｎはそれぞれ
０または１でｍ＋ｌ＋ｎ＝１ないし３の整数である。〕 第四の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は正孔注入層と電子注入層のうちの少なくとも正
孔注入層からなり、発光層は下記一般式（Ｉ）で表され
るチオフェン誘導体からなるとすることにより達成され
る。[In the formula (I), R 1 , R 2 , R 3 and R 4 are a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 and R 8 respectively. , R 9 , R 10
Are hydrogen atoms. Halogen atom. Represents an alkyl group, an alkoxy group or an aryl group, and R 1 ,
At least one of R 2 , R 3 and R 4 is selected from a hydrogen atom and a cyano group, or R 5 , R 6 , R 7 , R 8 and R 4
9 , one or more of R 10 are halogen atoms. Selected from alkoxy groups. m is 1 or 2, l and n are 0 or 1, respectively, and are integers of m + l + n = 1 to 3. According to the fourth invention, a pair of electrodes consisting of a positive electrode and a negative electrode, a light emitting layer and a charge injection layer sandwiched therebetween are provided, and the charge injection layer is at least one of a hole injection layer and an electron injection layer. This is achieved by comprising a hole injection layer and forming the light emitting layer from a thiophene derivative represented by the following general formula (I).
【００１３】[0013]
【化１１】 [Chemical 11]
【００１４】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれアルキル基，アリール基、または複素環基、Ｒ
5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10はそれぞれ水素原
子．アルキル基またはアリール基を表すとともに、
Ｒ5 、Ｒ7 、Ｒ9 の内に相互に異なる基が一つ以上含ま
れるかまたはＲ6 、Ｒ8 、Ｒ10の内に相互に異なる基が
一つ以上含まれる。ｍは１または２、ｌとｎはそれぞれ
０または１でｍ＋ｌ＋ｎ＝１ないし３の整数である。〕 第五の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は電子注入層であり、発光層は一般式（Ｉ）で表
されるチオフェン誘導体からなるとすることにより達成
される。[In the formula (I), R 1 , R 2 , R 3 and R 4 are each an alkyl group, an aryl group, or a heterocyclic group, R
5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each a hydrogen atom. While representing an alkyl group or an aryl group,
One or more groups different from each other are contained in R 5 , R 7 and R 9 or one or more groups different from each other are contained in R 6 , R 8 and R 10 . m is 1 or 2, l and n are 0 or 1, respectively, and are integers of m + l + n = 1 to 3. According to the fifth invention, a pair of electrodes consisting of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween are provided, the charge injection layer is an electron injection layer, and the light emitting layer is represented by the general formula ( It is achieved by comprising a thiophene derivative represented by I).
【００１５】[0015]
【化１２】 [Chemical 12]
【００１６】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれ水素原子，アルキル基，アリール基，シアノ基
または複素環基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10
はそれぞれ水素原子．ハロゲン原子．アルキル基，アル
コキシ基またはアリール基を表す。ｍは１または２、ｌ
とｎはそれぞれ０または１でｍ＋ｌ＋ｎ＝１ないし３の
整数である。〕 第六の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は正孔注入層と電子注入層のうちの少なくとも一
つからなり、発光層は一般式（Ｉ）で表されるチオフェ
ン誘導体と、一般式（II）で示されるジスチリルベンゼ
ン誘導体からなるものであるとすることにより達成され
る。[In the formula (I), R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 and R 8 , R 9 , R 10
Are hydrogen atoms. Halogen atom. Represents an alkyl group, an alkoxy group or an aryl group. m is 1 or 2, l
And n are 0 or 1, respectively, and are integers of m + 1 + n = 1 to 3. According to the sixth invention, a pair of electrodes composed of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween are provided, and the charge injection layer is at least a hole injection layer or an electron injection layer. The light-emitting layer is composed of one, and is achieved by including the thiophene derivative represented by the general formula (I) and the distyrylbenzene derivative represented by the general formula (II).
【００１７】[0017]
【化１３】 [Chemical 13]
【００１８】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれアルキル基，アリール基または複素環基、
Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10、はそれぞれ水素
原子，アルキル基またはアリール基、ｍは１または２、
ｌとｎはそれぞれ０または１を表す。〕[In the formula (I), R 1 , R 2 , R 3 and R 4 are each an alkyl group, an aryl group or a heterocyclic group,
R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each a hydrogen atom, an alkyl group or an aryl group, and m is 1 or 2,
l and n represent 0 or 1, respectively. ]
【００１９】[0019]
【化１４】 [Chemical 14]
【００２０】〔Ｒ11，Ｒ12，Ｒ13，Ｒ14はフェニル基，
ハロゲン化フェニル基，シアノ化フェニル基，ニトロ化
フェニル基，アルキル化フェニル基，アルコキシ化フェ
ニル基、Ｒ15，Ｒ16, Ｒ17はそれぞれ水素原子，ハロゲ
ン原子，シアノ基，ニトロ基，アルキル基，アルコキシ
基またはアリール基を示す。〕 キノリノール系錯体にはアルミキノリノール，亜鉛キノ
リノール等の金属キノリノール錯体が含まれる。[R 11 , R 12 , R 13 and R 14 are phenyl groups,
Halogenated phenyl group, cyanated phenyl group, nitrated phenyl group, alkylated phenyl group, alkoxylated phenyl group, R 15 , R 16 and R 17 are each a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group, An alkoxy group or an aryl group is shown. The quinolinol-based complex includes a metal quinolinol complex such as aluminum quinolinol and zinc quinolinol.
【００２１】一般式（Ｉ）のチオフェン誘導体の具体例
が表１，表２，表３，表４，表５の化学式Ｉ−１ないし
化学式Ｉ−２５に示される。上記の表のうち、表１，表
２，表３は一般式（Ｉ）のＲ1 ないしＲ10の基を示し、
表４，表５は一般式（Ｉ）の添字ｌ，ｍ，ｎを示す。第
一，第二，第三，第四，第五，第六の各発明に適合する
チオフェン誘導体は化学式Ｉ−１ないし化学式Ｉ−２５
の中から選定される。Specific examples of the thiophene derivative of the general formula (I) are shown in chemical formulas I-1 to I-25 in Table 1, Table 2, Table 3, Table 4 and Table 5. In the above table, Table 1, Table 2 and Table 3 show the groups R 1 to R 10 of the general formula (I),
Tables 4 and 5 show the subscripts l, m and n of the general formula (I). The thiophene derivatives suitable for the first, second, third, fourth, fifth and sixth inventions are represented by the chemical formula I-1 to the chemical formula I-25.
Selected from among.
【００２２】一般式（II）で示されるジスチリルベンゼ
ン誘導体の具体例が表６，表７に示される。Specific examples of the distyrylbenzene derivative represented by the general formula (II) are shown in Tables 6 and 7.
【００２３】[0023]
【表１】 [Table 1]
【００２４】[0024]
【表２】 [Table 2]
【００２５】[0025]
【表３】 [Table 3]
【００２６】[0026]
【表４】 [Table 4]
【００２７】[0027]
【表５】 [Table 5]
【００２８】[0028]
【表６】 [Table 6]
【００２９】[0029]
【表７】 [Table 7]
【００３０】[0030]
【作用】キノリノール錯体またはジスチリルベンゼン誘
導体は電子と正孔の再結合により励起発光する。この物
質の蛍光収率は高く、発光輝度は高い。キノリノール錯
体またはジスチリルベンゼン誘導体は本発明のチオフェ
ン誘導体よりも短波長の発光を示し、且つチオフェン誘
導体のような低分子化合物と混合されたときに結晶化し
難く良好な成膜性が得られる。[Function] The quinolinol complex or the distyrylbenzene derivative emits light upon excitation by recombination of electrons and holes. This substance has a high fluorescence yield and a high emission brightness. The quinolinol complex or the distyrylbenzene derivative emits light at a shorter wavelength than the thiophene derivative of the present invention, and when mixed with a low molecular weight compound such as a thiophene derivative, it is difficult to crystallize and a good film-forming property is obtained.
【００３１】チオフェン誘導体はキノリノール錯体また
はジスチリルベンゼン誘導体からの遷移エネルギにより
励起発光する。チオフェン誘導体の蛍光収率は高く、電
荷の輸送性能も高い。キノリノール錯体またはジスチリ
ルベンゼン誘導体を主発光物質とし、一般式（Ｉ）のチ
オフェン誘導体を副発光物質とするときはチオフェン誘
導体からの蛍光と、主発光物質の蛍光によりそれぞれの
発光色とは異なる発光色を得ることができる。The thiophene derivative is excited to emit light by the transition energy from the quinolinol complex or the distyrylbenzene derivative. The fluorescence yield of the thiophene derivative is high, and the charge transport performance is also high. When the quinolinol complex or the distyrylbenzene derivative is used as the main luminescent substance and the thiophene derivative of the general formula (I) is used as the secondary luminescent substance, the luminescence from the thiophene derivative and the luminescence of the main luminescent substance are different from each other. You can get the color.
【００３２】一般式（Ｉ）のチオフェン誘導体は電子と
正孔の再結合によるエネルギにより励起発光することも
できこの際の蛍光収率は高く発光輝度も高い。一般式
（Ｉ）のチオフェン誘導体は結晶化し難い物質であり良
好な成膜性が得られる。The thiophene derivative of the general formula (I) can also be excited to emit light by energy due to recombination of electrons and holes, and at this time, the fluorescence yield is high and the emission brightness is also high. The thiophene derivative represented by the general formula (I) is a substance that is difficult to crystallize, and has good film-forming properties.
【００３３】[0033]
【実施例】次にこの発明の実施例を図面に基づいて説明
する。図１はこの発明の一実施例に係る有機薄膜発光素
子を示す断面図である。図２はこの発明の異なる一実施
例に係る有機薄膜発光素子を示す断面図である。Embodiments of the present invention will now be described with reference to the drawings. FIG. 1 is a sectional view showing an organic thin film light emitting device according to an embodiment of the present invention. FIG. 2 is a sectional view showing an organic thin film light emitting device according to another embodiment of the present invention.
【００３４】図３はこの発明のさらに異なる一実施例に
係る有機薄膜発光素子を示す断面図である。１は絶縁性
基板、２は正極、３は正孔注入層、４は発光層、５は電
子注入層、６は負極である。絶縁性基板１は素子の支持
体でガラス，樹脂等を用いる。発光面となるときは透明
な材料を用いる。FIG. 3 is a sectional view showing an organic thin film light emitting device according to another embodiment of the present invention. 1 is an insulating substrate, 2 is a positive electrode, 3 is a hole injection layer, 4 is a light emitting layer, 5 is an electron injection layer, and 6 is a negative electrode. The insulating substrate 1 is made of glass, resin or the like as a support for the element. A transparent material is used for the light emitting surface.
【００３５】正極２は金，ニッケル等の半透膜やインジ
ウムスズ酸化物（ＩＴＯ），酸化スズ（ＳｎＯ2 ）等の
透明導電膜からなり抵抗加熱蒸着、電子ビ−ム蒸着、ス
パッタ法により形成する。該正極２は、透明性を持たせ
るために、１０〜２００ｎｍの厚さにすることが望まし
い。正孔注入層３は正孔を効率良く輸送し、且つ注入す
ることが必要で発光した光の発光極大領域においてでき
るだけ透明であることが望ましい。成膜方法としてスピ
ンコ−ト、キャスティング、ＬＢ法、抵抗加熱蒸着、電
子ビ−ム蒸着等があるが抵抗加熱蒸着が一般的である。
膜厚は１０ないし５００ｎｍであり、好適には２０ない
し８０ｎｍである。正孔注入物質としてはヒドラゾン化
合物，ピラゾリン化合物，スチルベン化合物，アミン系
化合物，非晶質Ｓｉ系物質等あるいはこれらの混合物，
積層体等が用いられる。代表的な正孔注入物質が化学式
（Ｖ−１）ないし化学式（Ｖ−６）に示される。The positive electrode 2 is made of a semi-permeable film of gold, nickel or the like or a transparent conductive film of indium tin oxide (ITO), tin oxide (SnO 2 ) or the like and is formed by resistance heating vapor deposition, electron beam vapor deposition, or sputtering. To do. The positive electrode 2 preferably has a thickness of 10 to 200 nm in order to have transparency. The hole injection layer 3 is required to efficiently transport and inject holes, and it is desirable that the hole injection layer 3 be as transparent as possible in the emission maximum region of the emitted light. The film forming method includes spin coating, casting, LB method, resistance heating evaporation, electron beam evaporation and the like, but resistance heating evaporation is common.
The film thickness is 10 to 500 nm, preferably 20 to 80 nm. As the hole injecting substance, a hydrazone compound, a pyrazoline compound, a stilbene compound, an amine compound, an amorphous Si compound, etc., or a mixture thereof,
A laminated body or the like is used. Typical hole-injecting substances are represented by chemical formulas (V-1) to (V-6).
【００３６】[0036]
【化１５】 [Chemical 15]
【００３７】発光層４は正孔注入層または正極から注入
された正孔と、負極または電子注入層より注入された電
子の再結合により効率良く発光を行う。成膜方法はスピ
ンコ−ト、キャスティング、ＬＢ法、抵抗加熱蒸着、電
子ビ−ム蒸着等があるが抵抗加熱蒸着が一般的である。
膜厚は１０ないし５００ｎｍであるが好適には２０ない
し８０ｎｍである。The light emitting layer 4 efficiently emits light by recombination of holes injected from the hole injection layer or the positive electrode and electrons injected from the negative electrode or the electron injection layer. Film forming methods include spin coating, casting, LB method, resistance heating evaporation, electron beam evaporation and the like, but resistance heating evaporation is common.
The film thickness is 10 to 500 nm, but preferably 20 to 80 nm.
【００３８】電子注入層５は電子を効率良く発光層に注
入することが望ましい。成膜方法はスピンコ−ト、キャ
スティング、ＬＢ法、抵抗加熱蒸着、電子ビ−ム蒸着等
があるが抵抗加熱蒸着が一般的である。膜厚は１０ない
し５００ｎｍであるが好適には２０ないし８０ｎｍであ
る。電子注入物質としてはオキサジアゾール誘導体，ペ
リレン誘導体，ｎ−ＧａＡｓ，ｎ−ＺｎＳｅ等あるいは
これらの混合物，積層体が用いられる。代表的な電子注
入物質が化学式（VI−１）ないし化学式（VI−４）に示
される。It is desirable that the electron injection layer 5 efficiently injects electrons into the light emitting layer. Film forming methods include spin coating, casting, LB method, resistance heating evaporation, electron beam evaporation and the like, but resistance heating evaporation is common. The film thickness is 10 to 500 nm, but preferably 20 to 80 nm. As the electron injecting substance, an oxadiazole derivative, a perylene derivative, n-GaAs, n-ZnSe, or the like, or a mixture or laminated body thereof is used. Typical electron injecting substances are represented by chemical formulas (VI-1) to (VI-4).
【００３９】[0039]
【化１６】 [Chemical 16]
【００４０】負極６は電子を効率良く有機層に注入する
ことが必要である。成膜方法としては抵抗加熱蒸着，電
子ビーム蒸着，スパッタ法が用いられる。負極６用材料
としては、仕事関数の小さいＭｇ，Ａｇ，Ｉｎ，Ｃａ，
Ａｌ等およびこれらの合金，積層体等が用いられる。 実施例１ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図１に示すように正孔注入層３、発光層４を順次成膜し
た。成膜に際して、真空槽内圧は８×１０-4Ｐａとし
た。正孔注入層には化学式（Ｖ−１）に示されるテトラ
フェニルベンジジン誘導体を用い、ボート温度２３０℃
にて成膜速度０．２ｎｍ／ｓとして６０ｎｍ厚さに形成
した。続けて発光層として化学式（VII −１）に示され
るアルミキノリール錯体を用いボ−ト温度約２３０℃に
て加熱すると同時に化学式Ｉ−１のチオフェン誘導体を
ボ−ト温度約２３０℃にて加熱し混合比率２０：１にな
るように成膜速度を約０．２ｎｍ／ｓとして６０ｎｍ厚
さに形成した。この後、基板を真空槽から取り出し、直
径５ｍｍのドットパタ−ン用ステンレス製マスクを取り
つけ、新たに抵抗加熱蒸着装置内に載置し負極６として
Ｍｇ／Ｉｎアロイ（１０：１の重量比率）を１００ｎ
ｍ厚さに形成した。The negative electrode 6 needs to efficiently inject electrons into the organic layer. As a film forming method, resistance heating evaporation, electron beam evaporation, or sputtering method is used. As the material for the negative electrode 6, Mg, Ag, In, Ca, which has a small work function,
Al and the like, alloys of these and laminated bodies are used. Example 1 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm is used as a substrate, and the substrate is placed in a resistance heating vapor deposition apparatus, and as shown in FIG. 1, the hole injection layer 3 and the light emitting layer 4 are sequentially arranged. A film was formed. During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. A tetraphenylbenzidine derivative represented by the chemical formula (V-1) is used for the hole injection layer, and the boat temperature is 230 ° C.
At a film forming speed of 0.2 nm / s, a film having a thickness of 60 nm was formed. Subsequently, using the aluminum quinolyl complex represented by the chemical formula (VII-1) as a light emitting layer, the thiophene derivative of the chemical formula I-1 is heated at a boat temperature of about 230 ° C. at the same time as heating at a boat temperature of about 230 ° C. Then, the film forming rate was set to about 0.2 nm / s so that the mixing ratio was 20: 1, and the film was formed to a thickness of 60 nm. After that, the substrate was taken out from the vacuum chamber, a stainless mask for dot pattern having a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition apparatus and Mg / In alloy (10: 1 weight ratio) was used as the negative electrode 6. 100n
It was formed to a thickness of m.
【００４１】[0041]
【化１７】 [Chemical 17]
【００４２】上記実施例１において、該化合物からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度１
０００ｃｄ／ｍ2 以上で黄色（発光中心波長５８０〜５
９０ｎｍ）の均一な発光が得られた。また発光層を含む
有機蒸着積層膜は大気中に保存しても結晶化せず安定で
あった。 実施例２ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図１に示すように正孔注入層３、発光層４を順次成膜し
た。成膜に際して、真空槽内圧は８×１０-4Ｐａとし
た。正孔注入層には化学式（Ｖ−２）に示される化合物
を用い、ボート温度２３０℃にて成膜速度０．２ｎｍ／
ｓとして６０ｎｍ厚さに形成した。続けて発光層として
化学式（VII −１）に示されるアルミキノリール錯体を
用いボ−ト温度約２３０℃にて加熱すると同時に化学式
Ｉ−３で示されるチオフェン誘導体をボ−ト温度約２３
０℃にて加熱し混合比率２０：１になるように成膜速度
を約０．２ｎｍ／ｓとして６０ｎｍ厚さに形成した。こ
の後、基板を真空槽から取り出し、直径５ｍｍのドット
パタ−ン用ステンレス製マスクを取りつけ、新たに抵抗
加熱蒸着装置内に載置し負極６として Ｍｇ／Ｉｎアロ
イ（１０：１の重量比率）を１００ｎｍ厚さに形成し
た。In Example 1, the light emitting layer made of the compound was a uniform vapor deposition film, and when a DC voltage was applied to the organic thin film light emitting device having a diameter of 5 mm, the maximum brightness was 1
Yellow above 000 cd / m 2 (emission center wavelength 580-5
A uniform emission of 90 nm) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere. Example 2 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm is used as a substrate, and the substrate is placed in a resistance heating vapor deposition apparatus, and the hole injection layer 3 and the light emitting layer 4 are sequentially placed as shown in FIG. A film was formed. During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. The compound represented by the chemical formula (V-2) is used for the hole injection layer, and the film formation rate is 0.2 nm / at a boat temperature of 230 ° C.
s was formed to a thickness of 60 nm. Subsequently, the aluminum quinolyl complex represented by the chemical formula (VII-1) is used as a light emitting layer and heated at a boat temperature of about 230 ° C., and at the same time, the thiophene derivative represented by the chemical formula I-3 is heated at a boat temperature of about 23 ° C.
The film was formed at a thickness of 60 nm by heating at 0 ° C. and a film formation rate of about 0.2 nm / s so that the mixing ratio was 20: 1. After that, the substrate was taken out from the vacuum chamber, a stainless mask for dot pattern having a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition apparatus and Mg / In alloy (10: 1 weight ratio) was used as the negative electrode 6. It was formed to a thickness of 100 nm.
【００４３】上記実施例２において、該化合物からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度１
０００ｃｄ／ｍ2 以上で橙色（発光中心波長５９０〜６
００ｎｍ）の均一な発光が得られた。また発光層を含む
有機蒸着積層膜は大気中に保存しても結晶化せず安定で
あった。 実施例３ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図２に示すように発光層４、電子注入層５を順次成膜し
た。成膜に際して、真空槽内圧は８×１０-4Ｐａとし
た。発光層には化学式（Ｉ−５）に示されるチオフェン
誘導体を用い、ボート温度２５０℃にて成膜速度０．２
ｎｍ／ｓとして６０ｎｍ厚さに形成した。続いて電子注
入層５として化学式VI−４に示すオキサジアゾール誘導
体を用い、ボート温度２３０℃にて成膜速度０．２ｎｍ
／ｓとして６０ｎｍ厚さに形成した。この後、基板を真
空槽から取り出し、直径５ｍｍのドットパタ−ンからな
るステンレス製マスクを取りつけ、新たに抵抗加熱蒸着
装置内に載置し負極６として Ｍｇ／Ｉｎアロイ（１
０：１の重量比率）を１００ｎｍ厚さに形成した。In Example 2, the light emitting layer made of the compound was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Orange above 000 cd / m 2 (emission center wavelength 590 to 6
A uniform emission of 100 nm) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere. Example 3 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm was used as a substrate, the substrate was placed in a resistance heating vapor deposition apparatus, and a light emitting layer 4 and an electron injection layer 5 were sequentially formed as shown in FIG. Filmed During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. The thiophene derivative represented by the chemical formula (I-5) is used for the light emitting layer, and the film formation rate is 0.2 at a boat temperature of 250 ° C.
The thickness is 60 nm and the thickness is 60 nm. Subsequently, the oxadiazole derivative represented by the chemical formula VI-4 was used as the electron injection layer 5, and the film formation rate was 0.2 nm at a boat temperature of 230 ° C.
/ S to a thickness of 60 nm. After that, the substrate was taken out from the vacuum chamber, a stainless mask made of a dot pattern with a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition device and the negative electrode 6 was made of Mg / In alloy (1
A weight ratio of 0: 1) was formed to a thickness of 100 nm.
【００４４】上記実施例３において、該化合物からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度１
００ｃｄ／ｍ2 以上で黄色（発光中心波長５８０〜５９
０ｎｍ）の均一な発光が得られた。また発光層を含む有
機蒸着積層膜は大気中に保存しても結晶化せず安定であ
った。 実施例４ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図３に示すように正孔注入層３、発光層４、電子注入層
５を順次成膜した。成膜に際して、真空槽内圧は８×１
０-4Ｐａとした。正孔注入層には化学式（Ｖ−１）に示
されるテトラフェニルベンジジン誘導体を用い、ボート
温度２３０℃にて成膜速度０．２ｎｍ／ｓとして６０ｎ
ｍ厚さに形成した。続けて発光層として前記化学式（Ｉ
−１３）に示されるチオフェン誘導体をボ−ト温度約２
５０℃にて加熱し、成膜速度を約０．２ｎｍ／ｓとして
３０ｎｍ厚さに形成した。さらに続けて電子注入層５と
して化学式VI−４に示すオキサジアゾール誘導体を用
い、ボ−ト温度約２３０℃にて加熱し、成膜速度を約
０．２ｎｍ／ｓとして６０ｎｍ厚さに形成した。この
後、基板を真空槽から取り出し、直径５ｍｍのドットパ
タ−ン用ステンレス製マスクを取りつけ、新たに抵抗加
熱蒸着装置内に載置し負極６として Ｍｇ／Ｉｎアロイ
（１０：１の重量比率）を１００ｎｍ厚さに形成した。In Example 3, the light emitting layer made of the compound was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Yellow above 100 cd / m 2 (emission center wavelength 580 to 59
A uniform emission of 0 nm) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere. Example 4 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm was used as a substrate, and the substrate was placed in a resistance heating vapor deposition apparatus, and as shown in FIG. 3, the hole injection layer 3, the light emitting layer 4, the electron The injection layer 5 was sequentially formed. When forming a film, the internal pressure of the vacuum chamber is 8 × 1
It was set to 0 −4 Pa. A tetraphenylbenzidine derivative represented by the chemical formula (V-1) is used for the hole injection layer, and the film formation rate is 0.2 nm / s at a boat temperature of 230 ° C. and 60 n.
It was formed to a thickness of m. Then, as a light emitting layer, the chemical formula (I
The thiophene derivative shown in -13) is used at a boat temperature of about 2
It was heated at 50 ° C. to form a film having a thickness of 30 nm at a film forming rate of about 0.2 nm / s. Subsequently, the oxadiazole derivative represented by the chemical formula VI-4 was used as the electron injection layer 5 and heated at a boat temperature of about 230 ° C. to form a film having a thickness of 60 nm at a film forming rate of about 0.2 nm / s. . After that, the substrate was taken out from the vacuum chamber, a stainless mask for dot pattern having a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition apparatus and Mg / In alloy (10: 1 weight ratio) was used as the negative electrode 6. It was formed to a thickness of 100 nm.
【００４５】上記実施例４において、該化合物からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度１
００ｃｄ／ｍ2 以上で黄色（発光中心波長５８０〜５９
０ｎｍ）の均一な発光が得られた。また発光層を含む有
機蒸着積層膜は大気中に保存しても結晶化せず安定であ
った。 実施例５ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図２に示すように発光層４、電子注入層５を順次成膜し
た。成膜に際して、真空槽内圧は８×１０-4Ｐａとし
た。発光層には化学式（Ｉ−２２）に示されるチオフェ
ン誘導体を用い、ボート温度２５０℃にて成膜速度０．
２ｎｍ／ｓとして６０ｎｍ厚さに形成した。続いて電子
注入層５として化学式VI−１に示す化合物を用い、ボー
ト温度２３０℃にて成膜速度０．２ｎｍ／ｓとして６０
ｎｍ厚さに形成した。この後、基板を真空槽から取り出
し、直径５ｍｍのドットパタ−ンからなるステンレス製
マスクを取りつけ、新たに抵抗加熱蒸着装置内に載置し
負極６として Ｍｇ／Ｉｎアロイ（１０：１の重量比
率）を１００ｎｍ厚さに形成した。In Example 4, the light emitting layer made of the compound was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Yellow above 100 cd / m 2 (emission center wavelength 580 to 59
A uniform emission of 0 nm) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere. Example 5 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm was used as a substrate, and the substrate was placed in a resistance heating vapor deposition apparatus, and a light emitting layer 4 and an electron injection layer 5 were sequentially formed as shown in FIG. Filmed During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. The thiophene derivative represented by the chemical formula (I-22) is used for the light emitting layer, and the film forming rate is 0.1 at a boat temperature of 250 ° C.
It was formed to a thickness of 60 nm at 2 nm / s. Subsequently, the compound represented by the chemical formula VI-1 was used as the electron injection layer 5, and the boat temperature was 230 ° C. and the film formation rate was 0.2 nm / s.
nm thickness. After that, the substrate was taken out from the vacuum chamber, a stainless mask made of a dot pattern with a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition apparatus and the negative electrode 6 was Mg / In alloy (weight ratio of 10: 1). Was formed to a thickness of 100 nm.
【００４６】上記実施例５において、該化合物からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度１
００ｃｄ／ｍ2 以上で橙色（中心波長５９０〜６００ｎ
ｍ）の均一な発光が得られた。また発光層を含む有機蒸
着積層膜は大気中に保存しても結晶化せず安定であっ
た。 実施例６ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図３に示すように正孔注入層３、発光層４、電子注入層
５を順次成膜した。成膜に際して、真空槽内圧は８×１
０-4Ｐａとした。正孔注入層には化学式（Ｖ−２）に示
される化合物を用い、ボート温度２３０℃にて成膜速度
０．２ｎｍ／ｓとして６０ｎｍ厚さに形成した。続けて
発光層として前記化学式（Ｉ−２３）に示されるチオフ
ェン誘導体をボ−ト温度約２５０℃にて加熱し、成膜速
度を約０．２ｎｍ／ｓとして３０ｎｍ厚さに形成した。
さらに続けて電子注入層として化学式VI−１に示す化合
物を用い、ボ−ト温度約２３０℃にて加熱し、成膜速度
を約０．２ｎｍ／ｓとして６０ｎｍ厚さに形成した。こ
の後、基板を真空槽から取り出し、直径５ｍｍのドット
パタ−ン用ステンレス製マスクを取りつけ、新たに抵抗
加熱蒸着装置内に載置し負極６として Ｍｇ／Ｉｎアロ
イ（１０：１の重量比率）を１００ｎｍ厚さに形成し
た。In Example 5, the light emitting layer made of the compound was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Orange color (center wavelength 590-600n) at 00 cd / m 2 or more
A uniform light emission of m) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere. Example 6 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm was used as a substrate, and the substrate was placed in a resistance heating vapor deposition apparatus, and as shown in FIG. 3, the hole injection layer 3, the light emitting layer 4, and the electron. The injection layer 5 was sequentially formed. When forming a film, the internal pressure of the vacuum chamber is 8 × 1
It was set to 0 −4 Pa. The hole injection layer was formed using a compound represented by the chemical formula (V-2) at a boat temperature of 230 ° C. and a film formation rate of 0.2 nm / s to a thickness of 60 nm. Subsequently, the thiophene derivative represented by the chemical formula (I-23) was heated as a light emitting layer at a boat temperature of about 250 ° C. to form a film having a thickness of 30 nm at a film forming rate of about 0.2 nm / s.
Further, subsequently, the compound represented by the chemical formula VI-1 was used as an electron injection layer and heated at a boat temperature of about 230 ° C. to form a film having a thickness of 60 nm at a film forming rate of about 0.2 nm / s. After that, the substrate was taken out from the vacuum chamber, a stainless mask for dot pattern having a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition apparatus and Mg / In alloy (10: 1 weight ratio) was used as the negative electrode 6. It was formed to a thickness of 100 nm.
【００４７】上記実施例６において、該化合物からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度１
００ｃｄ／ｍ2 以上で橙色（発光中心波長５９０〜６０
０ｎｍ）の均一な発光が得られた。また発光層を含む有
機蒸着積層膜は大気中に保存しても結晶化せず安定であ
った。In Example 6, the light emitting layer made of the compound was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Orange color above 00 cd / m 2 (emission center wavelength 590 to 60
A uniform emission of 0 nm) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere.
【００４８】以上の結果が表８に纏めて示される。The above results are summarized in Table 8.
【００４９】[0049]
【表８】 [Table 8]
【００５０】実施例７ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図２に示すように発光層４、電子注入層５を順次成膜し
た。成膜に際して、真空槽内圧は８×１０-4Ｐａとし
た。発光層には前記化学式（II−１）に示されるジスチ
リルベンゼン誘導体を用い、ボート温度３００℃にて加
熱すると同時に前記化学式（Ｉ−１）に示されるチオフ
ェン誘導体を用い、ボート温度２６０℃にて加熱し混合
比率を２０対１になるようにし成膜速度０．２ｎｍ／ｓ
として６０ｎｍ厚さに形成した。続いて電子注入層５と
して化学式（VI−４）に示すオキサジアゾール誘導体を
用い、ボート温度２３０℃にて成膜速度０．２ｎｍ／ｓ
として６０ｎｍ厚さに形成した。この後、基板を真空槽
から取り出し、直径５ｍｍのドットパタ−ンからなるス
テンレス製マスクを取りつけ、新たに抵抗加熱蒸着装置
内に載置し負極６として Ｍｇ／Ｉｎアロイ（１０：１
の重量比率）を１００ｎｍ厚さに形成した。Example 7 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm was used as a substrate, and the substrate was placed in a resistance heating vapor deposition apparatus, and the light emitting layer 4 and the electron injection layer 5 were placed as shown in FIG. Were sequentially formed. During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. For the light emitting layer, the distyrylbenzene derivative represented by the chemical formula (II-1) is used, and the thiophene derivative represented by the chemical formula (I-1) is used at the same time as heating at a boat temperature of 300 ° C. And heat it so that the mixing ratio becomes 20: 1, and the film formation rate is 0.2 nm / s.
To a thickness of 60 nm. Subsequently, the oxadiazole derivative represented by the chemical formula (VI-4) is used as the electron injection layer 5, and the film formation rate is 0.2 nm / s at a boat temperature of 230 ° C.
To a thickness of 60 nm. After that, the substrate was taken out from the vacuum chamber, a stainless mask made of a dot pattern having a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition apparatus and the negative electrode 6 was made of Mg / In alloy (10: 1).
Was formed to a thickness of 100 nm.
【００５１】上記実施例７において、該化合物からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度２
００ｃｄ／ｍ2 以上で黄色（中心波長５６０〜５８０ｎ
ｍ）の均一な発光が得られた。また発光層を含む有機蒸
着積層膜は大気中に保存しても結晶化せず安定であっ
た。 実施例８ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図３に示すように正孔注入層３、発光層４、電子注入層
５を順次成膜した。成膜に際して、真空槽内圧は８×１
０-4Ｐａとした。正孔注入層には化学式（Ｖ−１）に示
されるテトラフェニルベンジジン誘導体を用い、ボート
温度３２０℃にて成膜速度０．２ｎｍ／ｓとして６０ｎ
ｍ厚さに形成した。続けて発光層として前記化学式（II
−２）に示されるジスチリルベンゼン誘導体をボ−ト温
度３２０℃にて加熱すると同時に前記化学式（Ｉ−３）
で示されるチオフェン誘導体をボート温度２９０℃にて
加熱し混合比率２０対１になるようにするとともに成膜
速度０．２ｎｍ／ｓとして６０ｎｍ厚さに形成した。さ
らに続けて電子注入層として化学式（VI−４）に示すオ
キサジアゾール誘導体を用い、ボ−ト温度約２３０℃に
て加熱し、成膜速度を約０．２ｎｍ／ｓとして６０ｎｍ
厚さに形成した。この後、基板を真空槽から取り出し、
直径５ｍｍのドットパタ−ン用ステンレス製マスクを取
りつけ、新たに抵抗加熱蒸着装置内に載置し負極６とし
て Ｍｇ／Ｉｎアロイ（１０：１の重量比率）を１００
ｎｍ厚さに形成した。In Example 7, the light emitting layer made of the compound was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Yellow (center wavelength 560 to 580n at 00 cd / m 2 or more)
A uniform light emission of m) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere. Example 8 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm is used as a substrate, and the substrate is placed in a resistance heating vapor deposition apparatus, and as shown in FIG. 3, the hole injection layer 3, the light emitting layer 4, and the electron. The injection layer 5 was sequentially formed. When forming a film, the internal pressure of the vacuum chamber is 8 × 1
It was set to 0 −4 Pa. A tetraphenylbenzidine derivative represented by the chemical formula (V-1) is used for the hole injection layer, and the film formation rate is 0.2 nm / s at a boat temperature of 320 ° C. and 60 n.
It was formed to a thickness of m. Then, the above chemical formula (II
-2) is heated at a boat temperature of 320 ° C, and at the same time, the above-mentioned chemical formula (I-3)
The thiophene derivative represented by 1 was heated at a boat temperature of 290 ° C. so that the mixing ratio was 20: 1, and the thickness was 60 nm at a film forming rate of 0.2 nm / s. Further, subsequently, an oxadiazole derivative represented by the chemical formula (VI-4) is used as an electron injection layer and heated at a boat temperature of about 230 ° C., and a film formation rate of about 0.2 nm / s is set to 60 nm.
Formed to a thickness. After this, remove the substrate from the vacuum chamber,
A stainless mask with a diameter of 5 mm for dot pattern was attached, and it was newly placed in a resistance heating vapor deposition apparatus, and Mg / In alloy (weight ratio of 10: 1) of 100 was used as the negative electrode 6.
nm thickness.
【００５２】上記実施例８において、該誘導体からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度２
００ｃｄ／ｍ2 以上で黄色（発光中心波長５７０〜５８
０ｎｍ）の均一な発光が得られた。また発光層を含む有
機蒸着積層膜は大気中に保存しても結晶化せず安定であ
った。 実施例９ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図２に示すように発光層４、電子注入層５を順次成膜し
た。成膜に際して、真空槽内圧は８×１０-4Ｐａとし
た。発光層には前記化学式（II−７）に示されるジスチ
リルベンゼン誘導体を用い、ボート温度２８０℃にて加
熱すると同時に前記化学式（Ｉ−４）に示されるチオフ
ェン誘導体を用い、ボート温度２５０℃にて加熱し混合
比率を２０対１になるようにし成膜速度０．２ｎｍ／ｓ
として６０ｎｍ厚さに形成した。続いて電子注入層５と
して化学式（VI−４）に示すオキサジアゾール誘導体を
用い、ボート温度２３０℃にて成膜速度０．２ｎｍ／ｓ
として６０ｎｍ厚さに形成した。この後、基板を真空槽
から取り出し、直径５ｍｍのドットパタ−ンからなるス
テンレス製マスクを取りつけ、新たに抵抗加熱蒸着装置
内に載置し負極６として Ｍｇ／Ｉｎアロイ（１０：１
の重量比率）を１００ｎｍ厚さに形成した。In Example 8, the light emitting layer made of the derivative was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Yellow above 00 cd / m 2 (emission center wavelength 570 to 58
A uniform emission of 0 nm) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere. Example 9 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm was used as a substrate, and the substrate was placed in a resistance heating vapor deposition apparatus, and a light emitting layer 4 and an electron injection layer 5 were sequentially formed as shown in FIG. Filmed During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. For the light emitting layer, the distyrylbenzene derivative represented by the chemical formula (II-7) was used, and the thiophene derivative represented by the chemical formula (I-4) was used at the same time as heating at a boat temperature of 280 ° C. And heat it so that the mixing ratio becomes 20: 1, and the film formation rate is 0.2 nm / s.
To a thickness of 60 nm. Subsequently, the oxadiazole derivative represented by the chemical formula (VI-4) is used as the electron injection layer 5, and the film formation rate is 0.2 nm / s at a boat temperature of 230 ° C.
To a thickness of 60 nm. After that, the substrate was taken out from the vacuum chamber, a stainless mask made of a dot pattern having a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition apparatus and the negative electrode 6 was made of Mg / In alloy (10: 1).
Was formed to a thickness of 100 nm.
【００５３】上記実施例９において、該誘導体からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度２
００ｃｄ／ｍ2 以上で橙色（中心波長５８０〜５９０ｎ
ｍ）の均一な発光が得られた。また発光層を含む有機蒸
着積層膜は大気中に保存しても結晶化せず安定であっ
た。 実施例１０ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図３に示すように正孔注入層３、発光層４、電子注入層
５を順次成膜した。成膜に際して、真空槽内圧は８×１
０-4Ｐａとした。正孔注入層には化学式（Ｖ−２）に示
される化合物を用い、ボート温度２３０℃にて成膜速度
０．２ｎｍ／ｓとして６０ｎｍ厚さに形成した。続けて
発光層として前記化学式（II−１１）に示されるジスチ
リルベンゼン誘導体をボ−ト温度２７０℃にて加熱する
と同時に前記化学式（Ｉ−２３）で示されるチオフェン
誘導体をボート温度３１０℃にて加熱し混合比率２０対
１になるようにするとともに成膜速度０．２ｎｍ／ｓと
して６０ｎｍ厚さに形成した。さらに続けて電子注入層
として化学式（VI−４）に示すオキサジアゾール誘導体
を用い、ボ−ト温度約２３０℃にて加熱し、成膜速度を
約０．２ｎｍ／ｓとして６０ｎｍ厚さに形成した。この
後、基板を真空槽から取り出し、直径５ｍｍのドットパ
タ−ン用ステンレス製マスクを取りつけ、新たに抵抗加
熱蒸着装置内に載置し負極６としてＭｇ／Ｉｎアロイ
（１０：１の重量比率）を１００ｎｍ厚さに形成した。In Example 9, the light emitting layer made of the derivative was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Orange at 00cd / m 2 or more (center wavelength 580~590n
A uniform light emission of m) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere. Example 10 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm was used as a substrate, and the substrate was placed in a resistance heating vapor deposition apparatus. As shown in FIG. 3, the hole injection layer 3, the light emitting layer 4, and the electron were formed. The injection layer 5 was sequentially formed. When forming a film, the internal pressure of the vacuum chamber is 8 × 1
It was set to 0 −4 Pa. The hole injection layer was formed using a compound represented by the chemical formula (V-2) at a boat temperature of 230 ° C. and a film formation rate of 0.2 nm / s to a thickness of 60 nm. Subsequently, as the light emitting layer, the distyrylbenzene derivative represented by the chemical formula (II-11) is heated at a boat temperature of 270 ° C., and the thiophene derivative represented by the chemical formula (I-23) is heated at a boat temperature of 310 ° C. The film was heated to a mixing ratio of 20: 1 and formed to a thickness of 60 nm at a film forming rate of 0.2 nm / s. Subsequently, the oxadiazole derivative represented by the chemical formula (VI-4) is used as the electron injection layer, and heated at a boat temperature of about 230 ° C. to form a film having a film formation rate of about 0.2 nm / s and a thickness of 60 nm. did. After that, the substrate was taken out of the vacuum chamber, a stainless mask for dot pattern having a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition apparatus and Mg / In alloy (weight ratio of 10: 1) was used as the negative electrode 6. It was formed to a thickness of 100 nm.
【００５４】上記実施例１０において、該誘導体からな
る発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有
機薄膜発光素子に直流電圧を印加したところ、最高輝度
２００ｃｄ／ｍ2 以上で赤色（発光中心波長６００〜６
１０ｎｍ）の均一な発光が得られた。また発光層を含む
有機蒸着積層膜は大気中に保存しても結晶化せず安定で
あった。 比較例１ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図２に示すように発光層４、電子注入層５を順次成膜し
た。成膜に際して、真空槽内圧は８×１０-4Ｐａとし
た。発光層には前記化学式（II−１）に示されるジスチ
リルベンゼン誘導体を用い、ボート温度３００℃にて加
熱し成膜速度０．２ｎｍ／ｓとして６０ｎｍ厚さに形成
した。続いて電子注入層５として化学式（VI−４）に示
すオキサジアゾール誘導体を用い、ボート温度２３０℃
にて成膜速度０．２ｎｍ／ｓとして６０ｎｍ厚さに形成
した。この後、基板を真空槽から取り出し、直径５ｍｍ
のドットパタ−ンからなるステンレス製マスクを取りつ
け、新たに抵抗加熱蒸着装置内に載置し負極６としてＭ
ｇ／Ｉｎアロイ（１０：１の重量比率）を１００ｎｍ厚
さに形成した。In Example 10, the light emitting layer made of the derivative was a uniform vapor deposition film, and when a DC voltage was applied to the organic thin film light emitting device having a diameter of 5 mm, a red (light emission) light with a maximum brightness of 200 cd / m 2 or more was obtained. Center wavelength 600-6
A uniform emission of 10 nm) was obtained. Further, the organic vapor deposition laminated film including the light emitting layer was stable without being crystallized even when stored in the atmosphere. Comparative Example 1 A glass of 50 mm square provided with ITO having a film thickness of about 100 nm was used as a substrate, and the substrate was placed in a resistance heating vapor deposition apparatus, and a light emitting layer 4 and an electron injection layer 5 were sequentially formed as shown in FIG. Filmed During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. For the light emitting layer, the distyrylbenzene derivative represented by the chemical formula (II-1) was used and heated at a boat temperature of 300 ° C. to form a film having a film thickness of 0.2 nm / s and a thickness of 60 nm. Subsequently, an oxadiazole derivative represented by the chemical formula (VI-4) is used as the electron injection layer 5, and the boat temperature is 230 ° C.
At a film forming speed of 0.2 nm / s, a film having a thickness of 60 nm was formed. After that, the substrate is taken out from the vacuum chamber and the diameter is 5 mm.
Attach the stainless steel mask consisting of the dot pattern, and place it in the new resistance heating vapor deposition device to set M as the negative electrode 6.
A g / In alloy (10: 1 weight ratio) was formed to a thickness of 100 nm.
【００５５】上記比較例１において、該化合物からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度１
００ｃｄ／ｍ2 以上で緑色（中心波長５００〜５１０ｎ
ｍ）の発光が得られた。しかし発光層を含む有機蒸着積
層膜は大気中に保存した際に一日後に結晶を生じた。 比較例２ 膜厚約１００ｎｍのＩＴＯを設けた５０ｍｍ角のガラス
を基板とし該基板を抵抗加熱蒸着装置内に載置し、前記
図２に示すように発光層４、電子注入層５を順次成膜し
た。成膜に際して、真空槽内圧は８×１０-4Ｐａとし
た。発光層には前記化学式（Ｉ−１）に示されるチオフ
ェン誘導体を用い、ボート温度２７０℃にて加熱し成膜
速度０．２ｎｍ／ｓとして６０ｎｍ厚さに形成した。続
いて電子注入層５として化学式（VI−４）に示すオキサ
ジアゾール誘導体を用い、ボート温度２３０℃にて成膜
速度０．２ｎｍ／ｓとして６０ｎｍ厚さに形成した。こ
の後、基板を真空槽から取り出し、直径５ｍｍのドット
パタ−ンからなるステンレス製マスクを取りつけ、新た
に抵抗加熱蒸着装置内に載置し負極６として Ｍｇ／Ｉ
ｎアロイ（１０：１の重量比率）を１００ｎｍ厚さに形
成した。In Comparative Example 1, the light emitting layer made of the compound was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Green above 100 cd / m 2 (center wavelength 500 to 510 n
Light emission of m) was obtained. However, the organic vapor-deposited laminated film including the light emitting layer produced crystals after one day when stored in the atmosphere. Comparative Example 2 A 50 mm square glass substrate provided with ITO having a film thickness of about 100 nm was used as a substrate, and the substrate was placed in a resistance heating vapor deposition apparatus, and a light emitting layer 4 and an electron injection layer 5 were sequentially formed as shown in FIG. Filmed During film formation, the internal pressure of the vacuum chamber was 8 × 10 −4 Pa. For the light emitting layer, the thiophene derivative represented by the chemical formula (I-1) was used and heated at a boat temperature of 270 ° C. to form a film having a thickness of 60 nm at a film forming rate of 0.2 nm / s. Subsequently, the oxadiazole derivative represented by the chemical formula (VI-4) was used as the electron injection layer 5 at a boat temperature of 230 ° C. at a film formation rate of 0.2 nm / s to a thickness of 60 nm. After that, the substrate was taken out of the vacuum chamber, a stainless mask made of a dot pattern with a diameter of 5 mm was attached, and the substrate was newly placed in a resistance heating vapor deposition device to form Mg / I as the negative electrode 6.
An n-alloy (10: 1 weight ratio) was formed to a thickness of 100 nm.
【００５６】上記比較例２において、該化合物からなる
発光層は均一な蒸着膜となり、かつ該直径５ｍｍの有機
薄膜発光素子に直流電圧を印加したところ、最高輝度１
００ｃｄ／ｍ2 以上で黄色（中心波長５６０〜５８０ｎ
ｍ）の発光が得られた。しかし発光層を含む有機蒸着積
層膜は大気中に保存した際に一日後に結晶を生じた。実
施例７以降の結果が表９に纏めて示される。In Comparative Example 2, the light emitting layer made of the compound was a uniform vapor deposition film, and a direct current voltage was applied to the organic thin film light emitting device having a diameter of 5 mm.
Yellow (center wavelength 560 to 580n at 00 cd / m 2 or more)
Light emission of m) was obtained. However, the organic vapor-deposited laminated film including the light emitting layer produced crystals after one day when stored in the atmosphere. The results after Example 7 are summarized in Table 9.
【００５７】[0057]
【表９】 [Table 9]
【００５８】[0058]
【発明の効果】第一の発明によれば正極と負極とからな
る一対の電極と、その間に挟まれた発光層と電荷注入層
を有し、電荷注入層は正孔注入層と電子注入層のうちの
少なくとも一つからなり、発光層はキノリノール系錯体
の主発光物質と、下記一般式（Ｉ）で表されるチオフェ
ン誘導体の副発光物質とからなるとするので、キノリノ
ール錯体は電子と正孔の再結合により発光する際の蛍光
収率が高く、またチオフェン誘導体はキノリノール錯体
からの遷移エネルギにより蛍光を発する際の蛍光収率が
高い。またキノリノール錯体はチオフェン誘導体のよう
な低分子化合物と混合されたときに結晶化し難い性質を
有する。このようにして高輝度で均一発光性に優れる有
機薄膜発光素子が得られる。According to the first invention, it has a pair of electrodes consisting of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween, and the charge injection layer is a hole injection layer and an electron injection layer. The quinolinol complex is composed of at least one of the above, and the luminescent layer is composed of a main luminescent substance of a quinolinol-based complex and a sub-luminescent substance of a thiophene derivative represented by the following general formula (I). The fluorescence yield is high when emitting light due to recombination of the thiophene derivative, and the thiophene derivative has a high fluorescence yield when emitting fluorescence due to the transition energy from the quinolinol complex. Further, the quinolinol complex has a property that it is difficult to crystallize when mixed with a low molecular weight compound such as a thiophene derivative. In this way, an organic thin film light emitting device having high brightness and excellent in uniform light emission can be obtained.
【００５９】[0059]
【化１８】 [Chemical 18]
【００６０】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれ水素原子，アルキル基，アリール基，シアノ基
または複素環基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10
はそれぞれ水素原子，ハロゲン原子．アルキル基，アル
コキシ基またはアリール基、ｍは１または２、ｌとｎは
それぞれ０または１でｍ＋ｌ＋ｎ＝１ないし４の整数を
表す。〕 第二の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は正孔注入層と電子注入層のうちの少なくとも一
つからなり、発光層は下記一般式（Ｉ）で表されるチオ
フェン誘導体からなるとするので、チオフェン誘導体の
高い蛍光収率と非結晶性により高輝度で均一発光性に優
れる有機薄膜発光素子が得られる。[In the formula (I), R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 and R 8 , R 9 , R 10
Are hydrogen atom and halogen atom, respectively. An alkyl group, an alkoxy group or an aryl group, m is 1 or 2, l and n are 0 or 1, and m + 1 + n = 1 is an integer of 1 to 4. According to the second invention, it has a pair of electrodes consisting of a positive electrode and a negative electrode, a light emitting layer and a charge injection layer sandwiched therebetween, and the charge injection layer is at least the hole injection layer and the electron injection layer. Since the light emitting layer is composed of one, the light emitting layer is made of a thiophene derivative represented by the following general formula (I). Therefore, an organic thin film light emitting device having high luminance and excellent uniform light emitting property due to the high fluorescence yield and non-crystallinity of the thiophene derivative can get.
【００６１】[0061]
【化１９】 [Chemical 19]
【００６２】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれ水素原子，アルキル基，アリール基，シアノ基
または複素環基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、
Ｒ10、はそれぞれ水素原子，ハロゲン原子．アルキル
基，アルコキシ基またはアリール基、ｍは２、ｌとｎは
それぞれ１を表す。〕 第三の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は正孔注入層と電子注入層のうちの少なくとも正
孔注入層からなり、発光層は下記一般式（Ｉ）で表され
るチオフェン誘導体からなるとするので、チオフェン誘
導体の高い蛍光収率と非結晶性により高輝度で均一発光
性に優れる有機薄膜発光素子が得られる。[In the formula (I), R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 and R 8 , R 9 ,
R 10 is a hydrogen atom or a halogen atom, respectively. An alkyl group, an alkoxy group or an aryl group, m is 2, and 1 and n are 1 respectively. According to the third invention, it has a pair of electrodes consisting of a positive electrode and a negative electrode, a light emitting layer and a charge injection layer sandwiched therebetween, and the charge injection layer is at least a hole injection layer or an electron injection layer. Since the light emitting layer is composed of a hole injecting layer and the light emitting layer is composed of a thiophene derivative represented by the following general formula (I), the organic thin film light emission is excellent in high brightness and uniform light emitting property due to the high fluorescence yield and amorphousness of the thiophene derivative. The device is obtained.
【００６３】[0063]
【化２０】 [Chemical 20]
【００６４】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれ水素原子，アルキル基，アリール基，シアノ基
または複素環基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10
はそれぞれ水素原子．ハロゲン原子．アルキル基，アル
コキシ基またはアリール基を表すとともに、Ｒ1 、
Ｒ2 、Ｒ3 、Ｒ4 の内の一つ以上の基が水素原子，シア
ノ基から選ばれるかまたはＲ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ
9 、Ｒ10の内の一つ以上の基がハロゲン原子．アルコキ
シ基から選ばれる。ｍは１または２、ｌとｎはそれぞれ
０または１でｍ＋ｌ＋ｎ＝１ないし３の整数である。〕 第四の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は正孔注入層と電子注入層のうちの少なくとも正
孔注入層からなり、発光層は下記一般式（Ｉ）で表され
るチオフェン誘導体からなるとするので、チオフェン誘
導体の高い蛍光収率と非結晶性により高輝度で均一発光
性に優れる有機薄膜発光素子が得られる。[In the formula (I), R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 and R 8 , R 9 , R 10
Are hydrogen atoms. Halogen atom. Represents an alkyl group, an alkoxy group or an aryl group, and R 1 ,
At least one of R 2 , R 3 and R 4 is selected from a hydrogen atom and a cyano group, or R 5 , R 6 , R 7 , R 8 and R 4
9 , one or more of R 10 are halogen atoms. Selected from alkoxy groups. m is 1 or 2, l and n are 0 or 1, respectively, and are integers of m + l + n = 1 to 3. According to the fourth invention, a pair of electrodes consisting of a positive electrode and a negative electrode, a light emitting layer and a charge injection layer sandwiched therebetween are provided, and the charge injection layer is at least one of a hole injection layer and an electron injection layer. Since the light emitting layer is composed of a hole injecting layer and the light emitting layer is composed of a thiophene derivative represented by the following general formula (I), the organic thin film light emission is excellent in high brightness and uniform light emitting property due to the high fluorescence yield and amorphousness of the thiophene derivative. The device is obtained.
【００６５】[0065]
【化２１】 [Chemical 21]
【００６６】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれアルキル基，アリール基、または複素環基、Ｒ
5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10はそれぞれ水素原
子．アルキル基またはアリール基を表すとともに、
Ｒ5 、Ｒ7 、Ｒ9 の内に相互に異なる基が一つ以上含ま
れるかまたはＲ6 、Ｒ8 、Ｒ10の内に相互に異なる基が
一つ以上含まれる。ｍは１または２、ｌとｎはそれぞれ
０または１でｍ＋ｌ＋ｎ＝１ないし３の整数である。〕 第五の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は電子注入層であり、発光層は一般式（Ｉ）で表
されるチオフェン誘導体からなるとするので、チオフェ
ン誘導体の高い蛍光収率と非結晶性により高輝度で均一
発光性に優れる有機薄膜発光素子が得られる。[In the formula (I), R 1 , R 2 , R 3 and R 4 are each an alkyl group, an aryl group, or a heterocyclic group, R
5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each a hydrogen atom. While representing an alkyl group or an aryl group,
One or more groups different from each other are contained in R 5 , R 7 and R 9 or one or more groups different from each other are contained in R 6 , R 8 and R 10 . m is 1 or 2, l and n are 0 or 1, respectively, and are integers of m + l + n = 1 to 3. According to the fifth invention, a pair of electrodes consisting of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween are provided, the charge injection layer is an electron injection layer, and the light emitting layer is represented by the general formula ( Since it is composed of the thiophene derivative represented by I), an organic thin film light emitting device having high luminance and excellent uniform light emitting property can be obtained due to the high fluorescence yield and non-crystallinity of the thiophene derivative.
【００６７】[0067]
【化２２】 [Chemical formula 22]
【００６８】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれ水素原子，アルキル基，アリール基，シアノ基
または複素環基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10
はそれぞれ水素原子．ハロゲン原子．アルキル基，アル
コキシ基またはアリール基を表す。ｍは１または２、ｌ
とｎはそれぞれ０または１でｍ＋ｌ＋ｎ＝１ないし３の
整数である。〕 第六の発明によれば正極と負極とからなる一対の電極
と、その間に挟まれた発光層と電荷注入層を有し、電荷
注入層は正孔注入層と電子注入層のうちの少なくとも一
つからなり、発光層は一般式（Ｉ）で表されるチオフェ
ン誘導体と、一般式（II）で示されるジスチリルベンゼ
ン誘導体からなるものであるとするので、ジスチリルベ
ンゼン誘導体は電子と正孔の再結合により発光する際の
蛍光収率が高く、またチオフェン誘導体はジスチリルベ
ンゼン誘導体からの遷移エネルギにより蛍光を発する際
の蛍光収率が高い。またジスチリルベンゼン誘導体はチ
オフェン誘導体のような低分子化合物と混合されたとき
に結晶化し難い性質を有する。このようにして高輝度で
均一発光性に優れる有機薄膜発光素子が得られる。[In the formula (I), R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 and R 8 , R 9 , R 10
Are hydrogen atoms. Halogen atom. Represents an alkyl group, an alkoxy group or an aryl group. m is 1 or 2, l
And n are 0 or 1, respectively, and are integers of m + 1 + n = 1 to 3. According to the sixth invention, a pair of electrodes composed of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween are provided, and the charge injection layer is at least a hole injection layer or an electron injection layer. It is assumed that the light-emitting layer is composed of one and the thiophene derivative represented by the general formula (I) and the distyrylbenzene derivative represented by the general formula (II). The fluorescence yield when emitting light due to recombination of holes is high, and the fluorescence yield of the thiophene derivative when emitting fluorescence due to the transition energy from the distyrylbenzene derivative is high. Further, the distyrylbenzene derivative has a property that it is difficult to crystallize when mixed with a low molecular weight compound such as a thiophene derivative. In this way, an organic thin film light emitting device having high brightness and excellent in uniform light emission can be obtained.
【００６９】[0069]
【化２３】 [Chemical formula 23]
【００７０】〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 は
それぞれアルキル基，アリール基または複素環基、
Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10、はそれぞれ水素
原子，アルキル基またはアリール基、ｍは１または２、
ｌとｎはそれぞれ０または１を表す。〕[In the formula (I), R 1 , R 2 , R 3 and R 4 are each an alkyl group, an aryl group or a heterocyclic group,
R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are each a hydrogen atom, an alkyl group or an aryl group, and m is 1 or 2,
l and n represent 0 or 1, respectively. ]
【００７１】[0071]
【化２４】 [Chemical formula 24]
【００７２】〔Ｒ11，Ｒ12，Ｒ13，Ｒ14はフェニル基，
ハロゲン化フェニル基，シアノ化フェニル基，ニトロ化
フェニル基，アルキル化フェニル基，アルコキシ化フェ
ニル基、Ｒ15，Ｒ16, Ｒ17はそれぞれ水素原子，ハロゲ
ン原子，シアノ基，ニトロ基，アルキル基，アルコキシ
基またはアリール基を示す。〕[R 11 , R 12 , R 13 and R 14 are phenyl groups,
Halogenated phenyl group, cyanated phenyl group, nitrated phenyl group, alkylated phenyl group, alkoxylated phenyl group, R 15 , R 16 and R 17 are each a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group, An alkoxy group or an aryl group is shown. ]
【図１】この発明の一実施例に係る有機薄膜発光素子を
示す断面図FIG. 1 is a sectional view showing an organic thin film light emitting device according to an embodiment of the present invention.
【図２】この発明の異なる一実施例に係る有機薄膜発光
素子を示す断面図FIG. 2 is a cross-sectional view showing an organic thin film light emitting device according to another embodiment of the present invention.
【図３】この発明のさらに異なる一実施例に係る有機薄
膜発光素子を示す断面図FIG. 3 is a sectional view showing an organic thin film light emitting device according to another embodiment of the present invention.
１ 絶縁性基板 ２ 正極 ３ 正孔注入層 ４ 発光層 ５ 電子注入層 ６ 負極 1 Insulating Substrate 2 Positive Electrode 3 Hole Injection Layer 4 Light Emitting Layer 5 Electron Injection Layer 6 Negative Electrode
Claims (11)
間に挟まれた発光層と電荷注入層を有し、 電荷注入層は正孔注入層と電子注入層のうちの少なくと
も一つからなり、 発光層はキノリノール系錯体の主発光物質と、一般式
（Ｉ）で表されるチオフェン誘導体の副発光物質とから
なることを特徴とする有機薄膜発光素子。 【化１】 〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 はそれぞれ水素
原子，アルキル基，アリール基，シアノ基または複素環
基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10はそれぞれ水
素原子，ハロゲン原子．アルキル基，アルコキシ基また
はアリール基、ｍは１または２、ｌとｎはそれぞれ０ま
たは１でｍ＋ｌ＋ｎ＝１ないし４の整数を表す。〕1. A pair of electrodes consisting of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween, wherein the charge injection layer comprises at least one of a hole injection layer and an electron injection layer. The organic thin-film light emitting device, wherein the light emitting layer comprises a main light emitting substance of a quinolinol-based complex and a sub light emitting substance of a thiophene derivative represented by the general formula (I). [Chemical 1] [In the formula (I), R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 , R 8 and R 9 , R 10 are a hydrogen atom and a halogen atom, respectively. An alkyl group, an alkoxy group or an aryl group, m is 1 or 2, l and n are 0 or 1, and m + 1 + n = 1 is an integer of 1 to 4. ]
間に挟まれた発光層と電荷注入層を有し、 電荷注入層は正孔注入層と電子注入層のうちの少なくと
も一つからなり、 発光層は一般式（Ｉ）で表されるチオフェン誘導体から
なることを特徴とする有機薄膜発光素子。 【化２】 〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 はそれぞれ水素
原子，アルキル基，アリール基，シアノ基または複素環
基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10、はそれぞれ
水素原子，ハロゲン原子．アルキル基，アルコキシ基ま
たはアリール基、ｍは２、ｌとｎはそれぞれ１を表
す。〕2. A pair of electrodes consisting of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween, wherein the charge injection layer comprises at least one of a hole injection layer and an electron injection layer. The organic thin film light emitting device, wherein the light emitting layer is made of a thiophene derivative represented by the general formula (I). [Chemical 2] [In the formula (I), R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 , R 8 and R 9 , R 10 are a hydrogen atom and a halogen atom, respectively. An alkyl group, an alkoxy group or an aryl group, m is 2, and 1 and n are 1 respectively. ]
間に挟まれた発光層と電荷注入層を有し、 電荷注入層は正孔注入層と電子注入層のうちの少なくと
も正孔注入層からなり、 発光層は一般式（Ｉ）で表されるチオフェン誘導体から
なることを特徴とする有機薄膜発光素子。 【化３】 〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 はそれぞれ水素
原子，アルキル基，アリール基，シアノ基または複素環
基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10はそれぞれ水
素原子．ハロゲン原子．アルキル基，アルコキシ基また
はアリール基を表すとともに、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4
の内の一つ以上の基が水素原子，シアノ基から選ばれる
かまたはＲ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10の内の一
つ以上の基がハロゲン原子．アルコキシ基から選ばれ
る。ｍは１または２、ｌとｎはそれぞれ０または１でｍ
＋ｌ＋ｎ＝１ないし３の整数である。〕3. A pair of electrodes consisting of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween, wherein the charge injection layer is at least a hole injection layer or an electron injection layer. An organic thin film light emitting device comprising a layer, the light emitting layer comprising a thiophene derivative represented by the general formula (I). [Chemical 3] [In the formula (I), R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 , R 8 and R 9 , R 10 are each a hydrogen atom. Halogen atom. Represents an alkyl group, an alkoxy group, or an aryl group, and R 1 , R 2 , R 3 , R 4
One or more groups are hydrogen atom, one or more groups halogen atoms of the or R 5, R 6, R 7 , R 8, R 9, R 10 are selected from cyano group of the. Selected from alkoxy groups. m is 1 or 2, l and n are 0 or 1, respectively and m
+ L + n = 1 is an integer of 1 to 3. ]
間に挟まれた発光層と電荷注入層を有し、 電荷注入層は正孔注入層と電子注入層のうちの少なくと
も正孔注入層からなり、 発光層は一般式（Ｉ）で表されるチオフェン誘導体から
なることを特徴とする有機薄膜発光素子。 【化４】 〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 はそれぞれアル
キル基，アリール基、または複素環基、Ｒ5 、Ｒ6 、Ｒ
7 、Ｒ8 、Ｒ9 、Ｒ10はそれぞれ水素原子．アルキル基
またはアリール基を表すとともに、Ｒ5 、Ｒ7 、Ｒ9 の
内に相互に異なる基が一つ以上含まれるかまたはＲ6 、
Ｒ8 、Ｒ10の内に相互に異なる基が一つ以上含まれる。
ｍは１または２、ｌとｎはそれぞれ０または１でｍ＋ｌ
＋ｎ＝１ないし３の整数である。〕4. A pair of electrodes composed of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween, wherein the charge injection layer is at least a hole injection layer or an electron injection layer. An organic thin film light emitting device comprising a layer, the light emitting layer comprising a thiophene derivative represented by the general formula (I). [Chemical 4] [In the formula (I), R 1 , R 2 , R 3 and R 4 are each an alkyl group, an aryl group or a heterocyclic group, R 5 , R 6 and R 4
7 , R 8 , R 9 , and R 10 are each a hydrogen atom. Represents an alkyl group or an aryl group, and contains one or more groups different from each other among R 5 , R 7 , and R 9 , or R 6 ,
One or more groups different from each other are included in R 8 and R 10 .
m is 1 or 2, l and n are 0 or 1, respectively, and m + 1
+ N is an integer of 1 to 3. ]
間に挟まれた発光層と電荷注入層を有し、 電荷注入層は電子注入層であり、 発光層は一般式（Ｉ）で表されるチオフェン誘導体から
なることを特徴とする有機薄膜発光素子。 【化５】 〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 はそれぞれ水素
原子，アルキル基，アリール基，シアノ基または複素環
基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10はそれぞれ水
素原子．ハロゲン原子．アルキル基，アルコキシ基また
はアリール基を表す。ｍは１または２、ｌとｎはそれぞ
れ０または１でｍ＋ｌ＋ｎ＝１ないし３の整数であ
る。〕5. A pair of electrodes consisting of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween, the charge injection layer is an electron injection layer, and the light emitting layer is represented by the general formula (I). An organic thin film light emitting device comprising a thiophene derivative represented. [Chemical 5] [In the formula (I), R 1 , R 2 , R 3 and R 4 are each a hydrogen atom, an alkyl group, an aryl group, a cyano group or a heterocyclic group, R 5 , R 6 , R 7 , R 8 and R 9 , R 10 are each a hydrogen atom. Halogen atom. Represents an alkyl group, an alkoxy group or an aryl group. m is 1 or 2, l and n are 0 or 1, respectively, and are integers of m + l + n = 1 to 3. ]
間に挟まれた発光層と電荷注入層を有し、 電荷注入層は正孔注入層と電子注入層のうちの少なくと
も一つからなり、 発光層は一般式（Ｉ）で表されるチオフェン誘導体と、
一般式（II）で示されるジスチリルベンゼン誘導体から
なるものであることを特徴とする有機薄膜発光素子。 【化６】 〔式（Ｉ）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｒ4 はそれぞれアル
キル基，アリール基または複素環基、Ｒ5 、Ｒ6 、
Ｒ7 、Ｒ8 、Ｒ9 、Ｒ10、はそれぞれ水素原子，アルキ
ル基またはアリール基、ｍは１または２、ｌとｎはそれ
ぞれ０または１を表す。〕 【化７】 〔Ｒ11，Ｒ12，Ｒ13，Ｒ14はフェニル基，ハロゲン化フ
ェニル基，シアノ化フェニル基，ニトロ化フェニル基，
アルキル化フェニル基，アルコキシ化フェニル基、
Ｒ15，Ｒ16, Ｒ17はそれぞれ水素原子，ハロゲン原子，
シアノ基，ニトロ基，アルキル基，アルコキシ基または
アリール基を示す。〕6. A pair of electrodes consisting of a positive electrode and a negative electrode, and a light emitting layer and a charge injection layer sandwiched therebetween, wherein the charge injection layer comprises at least one of a hole injection layer and an electron injection layer. And the light emitting layer comprises a thiophene derivative represented by the general formula (I),
An organic thin film light emitting device comprising a distyrylbenzene derivative represented by the general formula (II). [Chemical 6] [In the formula (I), R 1 , R 2 , R 3 and R 4 are each an alkyl group, an aryl group or a heterocyclic group, R 5 , R 6 and
R 7 , R 8 , R 9 , and R 10 each represent a hydrogen atom, an alkyl group or an aryl group, m represents 1 or 2, and l and n each represent 0 or 1. ] [Chemical 7] [R 11 , R 12 , R 13 and R 14 are a phenyl group, a halogenated phenyl group, a cyanated phenyl group, a nitrated phenyl group,
Alkylated phenyl group, alkoxylated phenyl group,
R 15 , R 16, and R 17 are a hydrogen atom, a halogen atom, and
A cyano group, a nitro group, an alkyl group, an alkoxy group or an aryl group is shown. ]
はアルミキノリノール錯体であることを特徴とする有機
薄膜発光素子。7. The organic thin film light emitting device according to claim 1, wherein the main light emitting substance is an aluminum quinolinol complex.
般式（Ｉ）で示されるチオフェン誘導体はＲ1 、Ｒ2 、
Ｒ3 、Ｒ4 がフェニル基、Ｒ5 、Ｒ6 、Ｒ7、Ｒ8 、Ｒ
9 、Ｒ10が水素原子、ｌ＝ｍ＝ｎ＝１であることを特徴
とする有機薄膜発光素子。8. The device according to claim 1 or 6, wherein the thiophene derivative represented by the general formula (I) is R 1 , R 2 ,
R 3 and R 4 are phenyl groups, R 5 , R 6 , R 7 , R 8 and R
9. An organic thin film light emitting device, wherein R and R 10 are hydrogen atoms and l = m = n = 1.
般式（Ｉ）で示されるチオフェン誘導体はＲ1 、Ｒ2 、
Ｒ3 、Ｒ4 がトリル基、Ｒ5 、Ｒ6 、Ｒ7 、Ｒ8 、
Ｒ9 、Ｒ10が水素原子、ｌ＝ｍ＝ｎ＝１であることを特
徴とする有機薄膜発光素子。9. The device according to claim 1 or 6, wherein the thiophene derivative represented by the general formula (I) is R 1 , R 2 ,
R 3 and R 4 are tolyl groups, R 5 , R 6 , R 7 , and R 8 ,
An organic thin film light emitting device, wherein R 9 and R 10 are hydrogen atoms, and 1 = m = n = 1.
（II）で示されるジスチリルベンゼン誘導体はＲ11、Ｒ
12、Ｒ13、Ｒ14がフェニル基、Ｒ15、Ｒ16、Ｒ 17が水素
原子、二つのスチリル基が配位するフェニレン基がパラ
配位であることを特徴とする有機薄膜発光素子。10. The device according to claim 6, wherein the general formula
The distyrylbenzene derivative represented by (II) is R11, R
12, R13, R14Is a phenyl group, R15, R16, R 17Is hydrogen
Atom, a phenylene group with two styryl groups coordinated
An organic thin film light emitting device characterized by being coordinated.
（II）で示されるジスチリルベンゼン誘導体はＲ11、Ｒ
12、Ｒ13、Ｒ14がトリル基、Ｒ15、Ｒ16、Ｒ17が水素原
子、二つのスチリル基が配位するフェニレン基がメタ配
位であることを特徴とする有機薄膜発光素子。11. The device according to claim 6, wherein the distyrylbenzene derivative represented by the general formula (II) is R 11 or R
An organic thin-film light emitting device characterized in that 12 , R 13 and R 14 are tolyl groups, R 15 , R 16 and R 17 are hydrogen atoms, and a phenylene group in which two styryl groups are coordinated is a metacoordination.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5205464A JPH0711243A (en) | 1993-04-28 | 1993-08-20 | Organic thin film light-emitting element |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10161993 | 1993-04-28 | ||
| JP5-101619 | 1993-04-28 | ||
| JP5205464A JPH0711243A (en) | 1993-04-28 | 1993-08-20 | Organic thin film light-emitting element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0711243A true JPH0711243A (en) | 1995-01-13 |
Family
ID=26442479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5205464A Pending JPH0711243A (en) | 1993-04-28 | 1993-08-20 | Organic thin film light-emitting element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0711243A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0960927A2 (en) * | 1998-05-18 | 1999-12-01 | Sony Corporation | Organic electroluminescent device |
| EP1411563A3 (en) * | 2002-10-15 | 2005-08-17 | MERCK PATENT GmbH | Use of poly-3,3"-dialkyl-2,2':5',2"-terthiophenes as charge transport materials |
-
1993
- 1993-08-20 JP JP5205464A patent/JPH0711243A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0960927A2 (en) * | 1998-05-18 | 1999-12-01 | Sony Corporation | Organic electroluminescent device |
| EP0960927A3 (en) * | 1998-05-18 | 2000-03-22 | Sony Corporation | Organic electroluminescent device |
| US6312838B1 (en) | 1998-05-18 | 2001-11-06 | Sony Corporation | Organic electroluminescent device |
| EP1411563A3 (en) * | 2002-10-15 | 2005-08-17 | MERCK PATENT GmbH | Use of poly-3,3"-dialkyl-2,2':5',2"-terthiophenes as charge transport materials |
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