JPH03168294A - Electric field luminescent element - Google Patents
Electric field luminescent elementInfo
- Publication number
- JPH03168294A JPH03168294A JP1307577A JP30757789A JPH03168294A JP H03168294 A JPH03168294 A JP H03168294A JP 1307577 A JP1307577 A JP 1307577A JP 30757789 A JP30757789 A JP 30757789A JP H03168294 A JPH03168294 A JP H03168294A
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- light emitting
- emitting device
- organic compound
- 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
- 230000005684 electric field Effects 0.000 title abstract description 7
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 24
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 5
- 239000000470 constituent Substances 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- -1 (substituted) amino Chemical group 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 21
- 239000000758 substrate Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 6
- 238000000151 deposition Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 230000008021 deposition Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- DNTVTBIKSZRANH-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(3-methylphenyl)aniline Chemical compound CC1=CC=CC(C=2C(=CC=C(N)C=2)C=2C=CC(N)=CC=2)=C1 DNTVTBIKSZRANH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- AMHYMSLSONPSHL-XOHWUJONSA-N ethyl (z)-4-[4-[(z)-4-ethoxy-4-oxobut-2-enoyl]-3-ethylpiperazin-1-yl]-4-oxobut-2-enoate Chemical compound CCOC(=O)\C=C/C(=O)N1CCN(C(=O)\C=C/C(=O)OCC)C(CC)C1 AMHYMSLSONPSHL-XOHWUJONSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000002541 furyl group Chemical group 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
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011135 tin Substances 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
- 238000002834 transmittance Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Landscapes
- Electroluminescent Light Sources (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は発光性物質からなる発光層を有し、電界を印加
することにより電気エネルギーを直接光エネルギーに変
換でき、従来の白熱灯、蛍光灯あるいは発光ダイオード
等とは異なり大面積の面状発光体の実現を可能にする電
界発光素子に関する．〔従来の技術〕
電界発光素子はその発光励起機構の違いから，（１）発
光層内での電子や正孔の局所的な移動により発光体を励
起し、交流電界でのみ発光する真性電界発光素子と，（
２）電極からの電子と正孔の注入とその発光層内での再
結合により発光体を励起し、直流電界で作動するキャリ
ア注入型電界発光素子の二つに分けられる。（１）の真
性電界発光型の発光素子は一般にＺｎＳにＭｎ，Ｃｕ等
を添加した無機化合物を発光体とするものであるが、廃
動に２００ｖ以上の高い交換電界を必要とすること，′
Ｉ５造コストが高いこと、輝度や耐久性も不十分である
等の多くの問題点を有する。[Detailed Description of the Invention] [Industrial Application Field] The present invention has a light-emitting layer made of a light-emitting substance, and can directly convert electrical energy into light energy by applying an electric field. This paper relates to electroluminescent devices that, unlike lamps or light emitting diodes, enable the realization of large-area planar light emitters. [Prior art] Electroluminescent devices differ in their emission excitation mechanisms; (1) intrinsic electroluminescence, which excites a luminescent material by local movement of electrons and holes within the luminescent layer and emits light only in an alternating electric field; element and (
2) Carrier injection type electroluminescent devices that excite a luminescent material by injecting electrons and holes from an electrode and recombining them within a luminescent layer, and operate in a DC electric field. (1) Intrinsic electroluminescence type light emitting elements generally use an inorganic compound such as ZnS with Mn, Cu, etc. added as a light emitting body, but require a high exchange electric field of 200 V or more for decommissioning.
I5 has many problems such as high manufacturing cost and insufficient brightness and durability.
（２）のキャリア注入型電界発光素子は発光層として薄
膜状有機化合物を用いるようになってから高輝度のもの
が得られるようになった。たとえば、特開昭５９−１９
４３９３及び米国特許４，７２０，４３２には緑色発光
素子が、Ｊｐｎｊｏｕｒｎａｌ ｏｆ Ａｐｐｌｉｅｄ
Ｐｈｙｓｉｃｓ，ｖｏ１．２７，Ｐ７１３−７１５に
は黄色発光素子が開示されており、これらは通常、１０
０ｖ以下の直流電界下で高輝度の発光をする．
しかし，上記の例を含め、有機物を発光体とするキャリ
ア注入型電界発光素子はその研究も浅く、未だその材料
研究やデバイス化への研究が充分になされているとは言
えず、現状では更なる輝度の向上、発光波長のコントロ
ール、耐久性の向上など，多くの課題をかかえているの
が実情である。The carrier injection type electroluminescent device (2) has become capable of achieving high luminance since thin film-like organic compounds have been used as the light emitting layer. For example, JP-A-59-19
4393 and U.S. Pat. No. 4,720,432, green light emitting devices are disclosed
Physics, vol. 27, pages 713-715 discloses yellow light emitting devices, which typically have 10
Emit high-intensity light under a DC electric field of 0V or less. However, research on carrier-injection electroluminescent devices that use organic substances as light emitters, including the examples mentioned above, is still limited, and it cannot be said that sufficient research into materials and device development has been carried out. The reality is that there are many challenges to be solved, such as improving brightness, controlling the emission wavelength, and improving durability.
本発明は上記の実情に鑑みてなされたものであり，その
目的は発光性能が長時間に亘って持続する耐久性に優れ
た電界発光素子を提供することにある．
〔課題を解決するための手段〕
本発明者らは、上記課題を解決するための発光層の構成
要素につい鋭意検討した結果，陽極および陰極と，これ
らの間に挾持された一層または複数層の有機化合物層よ
り構成される電界発光素子において、前記有機化合物層
のうち少なくとも一層が、下記一般式ＣＩ）又は一般式
（ＩＩ）で表わされる有機化合物のいずれか一方を構成
或分とする層であることを特徴とする電界発光素子が、
上記課題に対し、有効であることを見い出し、本発明を
完成するに至った．
（式中、８１〜ＲＬ（ｌは各々独立に水素原子、ハロゲ
ン原子、置換または未置換のアルキル基、置換または未
置換のアリール基，アルコキシ基，置換または未置換の
アミノ基、シアノ基等を表わし、Ｒ１，Ｒ， ，Ｒ，
，Ｒ４及びＲ， ，Ｒ， ，Ｒ， ，Ｒ，は互いに隣り
あう置換基と環を形戊してもよい。）
Ｃ式中、８１〜Ｒエ．は各々独立に水素原子，ハロゲン
原子、置換又は未置換のアルキル基，置換または未置換
のアリール基，アルコキシ基、置換または未置換のアミ
ノ基，シアノ基等をあらわし、ＲよｔＬｙＲ３ｔＬ及び
Ｒ， ，Ｒ， ，Ｒ， ，Ｒ．。は互いに隣？合う置換
基と環を形威してもよい．）ここで、一般式（１）又は
一般式（ＩＩ）におけるＲエ〜Ｒｌｌとしては、以下の
ものをあげることができる。The present invention has been made in view of the above-mentioned circumstances, and its purpose is to provide an electroluminescent element with excellent durability and whose luminous performance continues for a long time. [Means for Solving the Problem] As a result of intensive study on the constituent elements of the light-emitting layer to solve the above-mentioned problem, the present inventors found that an anode, a cathode, and one or more layers sandwiched between the anode and the cathode. In an electroluminescent device composed of an organic compound layer, at least one of the organic compound layers is a layer containing either one of the organic compounds represented by the following general formula CI) or the general formula (II). An electroluminescent device is characterized by
We have found that this is effective in solving the above problems, and have completed the present invention. (In the formula, 81 to RL (l each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, an alkoxy group, a substituted or unsubstituted amino group, a cyano group, etc.) Representation, R1,R, ,R,
, R4 and R, , R, , R, , R, may form a ring with adjacent substituents. ) In formula C, 81 to Rd. each independently represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, an alkoxy group, a substituted or unsubstituted amino group, a cyano group, etc.; R, ,R, ,R. . are next to each other? You may formulate matching substituents and rings. ) Here, examples of R to Rll in the general formula (1) or the general formula (II) include the following.
（１）ハロゲン原子、トリフルオロメチル基、シアノ基
、ニトロ基
（２）アルキル基；好ましくは０１〜０２。とりわけＣ
ｌ２の直鎖または分岐鎖のアルキル基であり、これらの
アルキル基は更にハロゲン原子、水酸基，シアノ基、Ｃ
エ〜Ｃ１．のアルコキシ基、フェニル基またはハロゲン
原子、Ｃ１一Ｃ１■のアルキル基若しくはＣ１〜Ｃエ．
のアルコキシ基で置換されたフェニル基を含有しても良
い。(1) Halogen atom, trifluoromethyl group, cyano group, nitro group (2) Alkyl group; preferably 01-02. Especially C
12 is a linear or branched alkyl group, and these alkyl groups further contain a halogen atom, a hydroxyl group, a cyano group, a C
E~C1. an alkoxy group, a phenyl group or a halogen atom, a C1-C1■ alkyl group or a C1-Cd.
may contain a phenyl group substituted with an alkoxy group.
（３）アリール基：炭素環式あるいは複素環式芳香環で
あり、フェニル、ナフチル、アントリル，アセナフテニ
ル，フルオレニル、フェナントリル、インデニル、ビレ
ニル、ビリジル、ピリミジル、フラニル、ピロニル、チ
オフェニル、キノリル、ペンゾフラニル、ペンゾチオフ
ェニル、インドリル、カルバゾリル、ペンゾオキサゾリ
ル、キノキサリル、ペンゾイミダゾリル、ピラゾリル、
ジベンゾフラニル、ジベンジチオフェニル等を示し、こ
れらのアリール基は更にハロゲン原子，水酸基、シアノ
基，ニトロ基、アルキル基、アルコキシ基，アミノ基等
で置換されていてもよい。(3) Aryl group: A carbocyclic or heterocyclic aromatic ring, such as phenyl, naphthyl, anthryl, acenaphthenyl, fluorenyl, phenanthryl, indenyl, birenyl, biridyl, pyrimidyl, furanyl, pyronyl, thiophenyl, quinolyl, penzofuranyl, penzo Thiophenyl, indolyl, carbazolyl, penzoxazolyl, quinoxalyl, penzimidazolyl, pyrazolyl,
Dibenzofuranyl, dibendithiophenyl, etc. are shown, and these aryl groups may be further substituted with a halogen atom, hydroxyl group, cyano group, nitro group, alkyl group, alkoxy group, amino group, etc.
（４）アルコキシ基（−ＯＲ’）：Ｒ’は（２）で定義
したアルキル基を表わす。(4) Alkoxy group (-OR'): R' represents the alkyl group defined in (2).
（５）アリールオキシ基：アリール基は（３）で定義し
た基を示す。(5) Aryloxy group: The aryl group represents the group defined in (3).
（６）アルキルチオ基（−ＳＲ３）：Ｒ３は（２）で定
義したアルキル基を表わす．
（２）で定義したアルキル基、アセチル基、ベンゾイル
基等のアシル基または（３）で定義したアリール基を表
わし、またビペリジル基、モルホリル基のように、Ｒ４
とＲｓが窒素原子と共同で環を形成しても良い．またユ
ロリジル基のようにアリール基上の炭素原子と共同で環
を形威しても良い．
（８）アルコキシ力ルボニル基（−ＣＯＯＲ’ ） ：
Ｒ”は（２）で定義したアルキル基または（３）で定
義したアリール基を表わす。(6) Alkylthio group (-SR3): R3 represents the alkyl group defined in (2). It represents an acyl group such as an alkyl group, an acetyl group, or a benzoyl group as defined in (2), or an aryl group as defined in (3), and also represents an aryl group such as a biperidyl group or a morpholyl group.
and Rs may form a ring together with the nitrogen atom. Alternatively, a ring may be formed jointly with the carbon atom on the aryl group, as in the case of the eurolidyl group. (8) Alkoxy carbonyl group (-COOR'):
R'' represents an alkyl group defined in (2) or an aryl group defined in (3).
（９）アシル基（−ＣＯＯＲ” ）、スルホニル基（−
Ｓｏ， Ｒ’ ）、義した意味を表わす。但しＲ４及び
ＲＳにおいてアリール基上の炭素原子と共同で環を形或
する場合を除く．
（１０）メチレンジオキシ基またはメチレンジチオ基等
のアルキレンジオキシ基またはアルキレンジチオ基
以下に、前記一般式（１）及び一般式（ＩＩ）で示され
る化合物の代表例を示す．
〔一般式（０の化合物の代表例〕
〔一般式（ｎ）の化合物の代表例〕
本発明における電界発光素子は以上で説明した化合物を
真空蒸着法、溶液塗布法等により薄膜化し，陽極及び陰
極で挾持することにより構威される．その際、化合物中
に添加物として他の物質を複数種添加することもできる
。また，電極からの電荷注入効率を向上させるために、
電荷注入輸送層を電極との間に別に設けることも可能で
ある．陽極材料としてはニッケル、金、白金、パラジウ
ムやこれらの合金或いは酸化錫（Ｓｎ０よ）、酸化錫イ
ンジウム（ＩＴＯ）、沃化銅などの仕事関数の大きな金
属やそれらの合金、化合物、更にはポリ（３−メチルチ
オフェン）、ポリピロール等の導電性ポリマーなどを用
いることができる。一方，陰極材料としては、仕事関数
の小さな銀、錫、鉛，マグネシウム，マンガン，アル旦
二ウム．７１Ｊ，いはこれらの合金が用いられる．陽極
及び陰極として用いる材料のうち少なくとも一方は，素
子の発光波長領域において十分透明であることが望まし
い．具体的には８０％以上の光透過率を有することが望
ましい．
第１図に本発明に係る電界発光素子の代表的な構成例を
示す．
第１図において、１は基板、２．４は電極、３ａは発光
層、３ｂは電子輸送層、３ｃは正孔輸送層である。(9) Acyl group (-COOR"), sulfonyl group (-
So, R'), expresses a defined meaning. However, this excludes the case where R4 and RS form a ring jointly with the carbon atom on the aryl group. (10) Alkylene dioxy group or alkylene dithio group such as methylene dioxy group or methylene dithio group Representative examples of the compounds represented by the general formula (1) and general formula (II) are shown below. [Representative examples of compounds of general formula (0)] [Representative examples of compounds of general formula (n)] The electroluminescent device of the present invention is made by forming the above-described compound into a thin film by vacuum evaporation method, solution coating method, etc., and forming an anode and It is constructed by sandwiching it between the cathodes.At this time, it is also possible to add multiple types of other substances as additives to the compound.Also, in order to improve the efficiency of charge injection from the electrodes,
It is also possible to separately provide a charge injection transport layer between the electrodes. The anode materials include nickel, gold, platinum, palladium, alloys of these, metals with large work functions such as tin oxide (Sn0), indium tin oxide (ITO), copper iodide, their alloys and compounds, and even polyester. (3-methylthiophene), a conductive polymer such as polypyrrole, etc. can be used. On the other hand, examples of cathode materials include silver, tin, lead, magnesium, manganese, and aldanium, which have small work functions. 71J or an alloy of these is used. It is desirable that at least one of the materials used for the anode and cathode be sufficiently transparent in the emission wavelength range of the device. Specifically, it is desirable to have a light transmittance of 80% or more. Figure 1 shows a typical configuration example of an electroluminescent device according to the present invention. In FIG. 1, 1 is a substrate, 2.4 is an electrode, 3a is a light emitting layer, 3b is an electron transport layer, and 3c is a hole transport layer.
第１図（ａ）は、基板１上に電極２を設け、電極２上に
発光層３ａを単独で設け、その上に電極を設けた構戊の
ものである。第１図（ｂ）は、第１図（ａ）において電
極２と発光Ｎ３ａの間に正孔輸送層３ｃを設けたもので
あり、第１図（ｃ）は、第１図（ａ）において発光層３
ａと電極４の間に電子輸送１３ｂを設けたものである．
第ｌ図（ｄ）は、第１図（ｃ）において電極２と発光層
３ａとの間に正孔輸送Ｎ３ｃを設けた構成のものである
．
本発明の電界発光素子は以上の各層をガラス等の透明基
板上に順次積層されて素子として構成されるわけである
が、素子の安定性の向上、特に大気中の水分に対する保
護のために、別に保護層を設けたり、素子全体をセル中
に入れ、シリコンオイル等を封入するようにしても良い
。FIG. 1(a) shows a structure in which an electrode 2 is provided on a substrate 1, a light-emitting layer 3a is provided solely on the electrode 2, and an electrode is provided thereon. FIG. 1(b) shows a hole transport layer 3c provided between the electrode 2 and the light emitting layer 3a in FIG. 1(a), and FIG. 1(c) shows the same as in FIG. 1(a). Luminous layer 3
An electron transport 13b is provided between a and the electrode 4.
FIG. 1(d) shows a configuration in which a hole transport N3c is provided between the electrode 2 and the light emitting layer 3a in FIG. 1(c). The electroluminescent device of the present invention is constructed by sequentially laminating the above layers on a transparent substrate such as glass. A separate protective layer may be provided, or the entire device may be placed in a cell and silicone oil or the like may be sealed therein.
以下、実施例により本発明を更に詳細に説明する．
実施例１
陽極として厚さ５００入のインジウムースズ酸化物（Ｉ
ＴＯ）の薄膜の形成されたガラス基板（ＨＯＹＡＪＪ）
を中性洗浄により洗浄し、次いでエタノール中で約ＩＯ
分間超音波洗浄した。これを沸騰したエタノール中に約
１分間入れ、取り出した後、すぐに送風乾燥を行った．
つぎにガラス基板上に化合物隘（１ ）−１を加熱温度
が設定され、蒸着速度の制御できる抵抗加熱源で蒸着し
て蛍光性有機化合物層（発光層）を形成した．すなわち
、化合物Ｎα（１ ）−１を含んだタンタル製ボートを
温度コントローラーにより制御し，蒸着速度が２人／Ｓ
となるように保った．蒸着時の真空度は０，７ Ｘ １
０−″’ｔｏｒｒ．基板温度は２０℃であった． ＩＴ
Ｏ上に生或した蒸着層の膜厚は８００ Ａであった。Hereinafter, the present invention will be explained in more detail with reference to Examples. Example 1 Indium-tin oxide (I
Glass substrate on which a thin film of TO) is formed (HOYAJJ)
was washed with a neutral wash and then washed with about IO in ethanol.
Ultrasonic cleaning was performed for 1 minute. This was placed in boiling ethanol for about 1 minute, and after being taken out, it was immediately blown dry.
Next, a fluorescent organic compound layer (light-emitting layer) was formed by vapor-depositing Compound (1)-1 on the glass substrate using a resistance heating source whose heating temperature was set and the vapor deposition rate could be controlled. That is, a tantalum boat containing the compound Nα(1)-1 was controlled by a temperature controller, and the deposition rate was 2 persons/S.
I kept it so that The degree of vacuum during vapor deposition is 0.7 x 1
0-'''torr. The substrate temperature was 20°C. IT
The thickness of the vapor deposited layer formed on the O was 800 Å.
次に発光層上に、膜厚１５００入のＭｇ−Ａｇによる陰
極を蒸着した．このようにして得られた発光素子に外部
電源を接続して、電流を流したところ、陽極側にプラス
のバイアス電圧を印加した場合に、明瞭な発光が確認さ
れた。また素子は湿度を十分に陰極した状態において空
気中で作動させることが可能であった。Next, a cathode made of Mg-Ag with a film thickness of 1500 μm was deposited on the light-emitting layer. When an external power source was connected to the light emitting device thus obtained and a current was passed through it, clear light emission was observed when a positive bias voltage was applied to the anode side. Furthermore, the device could be operated in air with sufficient humidity.
実施例２
発光物質として、化合物ＮＱ（Ｉ）−２を用いた以外は
実施例１と同様にして発光素子を作製した。得られた発
光素子は陽極側にプラスのバイアス電圧を印加した場合
に明瞭な発光を呈した。Example 2 A light emitting device was produced in the same manner as in Example 1 except that compound NQ(I)-2 was used as the light emitting substance. The obtained light emitting device exhibited clear light emission when a positive bias voltage was applied to the anode side.
更に、この発光素子は湿度を十分に除去した状態におい
て空気中で作動させることが可能であった。Furthermore, this light emitting device could be operated in air with sufficient humidity removed.
実施例３
発光物質として、化合物Ｎａ（ｎ ）−ｔを用いた以外
は実施例ｌと同様にして発光素子を作製した。得られた
発光素子は陽極側のプラスのバイアス電圧を印加した場
合に明瞭な発光を呈した。Example 3 A light emitting device was produced in the same manner as in Example 1 except that the compound Na(n)-t was used as the light emitting substance. The obtained light emitting device exhibited clear light emission when a positive bias voltage on the anode side was applied.
更に、この発光素子は湿度を十分に除去した状態におい
て空気中で作動させることが可能であった。Furthermore, this light emitting device could be operated in air with sufficient humidity removed.
実施例４
発光物質として、化合物ＮＱ（ＩＩ）−２を用いた以外
は実施例ｌと同様にして発光素子を作製した。得られた
発光素子は陽極側にプラスのバイアス電圧を印加した場
合に明瞭な発光を呈した。Example 4 A light emitting device was produced in the same manner as in Example 1 except that compound NQ(II)-2 was used as the light emitting substance. The obtained light emitting device exhibited clear light emission when a positive bias voltage was applied to the anode side.
更に、この発光素子は湿度を十分に除去した状態におい
て空気中で作動させることが可能であった。Furthermore, this light emitting device could be operated in air with sufficient humidity removed.
実施例５
発光物質として、化合物ＮＱ（ＩＩ）−３を用いた以外
は実施例１と同様にして発光素子を作製した。得られた
発光素子は陽極側にプラスのバイアス電圧を印加した場
合に明瞭な発光を呈した。Example 5 A light emitting device was produced in the same manner as in Example 1 except that compound NQ(II)-3 was used as the light emitting substance. The obtained light emitting device exhibited clear light emission when a positive bias voltage was applied to the anode side.
更に，この発光素子は湿度を十分に除去した状態におい
て空気中で作動させることが可能であった．
実施例６
陽極として、インジウムースズ酸化物（ＩＴＯ）ガラス
（ＨＯＹＡＩ）を中性洗浄により洗浄し、次いでエタノ
ール中で約１０分間超音波洗浄した．これを沸騰したエ
タノール中に約１分間入れ、取り出した後、すぐに送風
乾燥を行った．つぎにガラス基板上に正孔輸送能を有す
る有機化合物であるＮ，Ｎ’−ジフェニルーＮ，Ｎ’−
（３−メチルフェニル）−１，１’−ビフェニル−４，
４′−ジアミン（ＴＰＯ）を，加熱温度が設定され、蒸
着速度を制御できる抵抗加熱源で蒸着して正孔輸送能を
有する有機化合物層（正孔輸送Ｎ）を形或した。すなわ
ち、ＴＰＤを含んだタンタル製ボートを温度コントロー
ラーにより２００℃に制御し、蒸着速度が２Ａ／ｓとな
るように保った。蒸着時の真空度は０．７Ｘ １０−’
ｔｏｒｒ．基板温度は２０℃であった。Furthermore, this light-emitting device could be operated in air with sufficient humidity removed. Example 6 As an anode, indium-tin oxide (ITO) glass (HOYAI) was cleaned by neutral cleaning and then ultrasonically cleaned in ethanol for about 10 minutes. This was placed in boiling ethanol for about 1 minute, and after being taken out, it was immediately blown dry. Next, N,N'-diphenyl N,N'- which is an organic compound with hole transport ability was placed on the glass substrate.
(3-methylphenyl)-1,1'-biphenyl-4,
4'-diamine (TPO) was deposited using a resistance heating source whose heating temperature was set and the deposition rate could be controlled to form an organic compound layer having hole transporting ability (hole transporting N). That is, a tantalum boat containing TPD was controlled at 200° C. using a temperature controller, and the deposition rate was maintained at 2 A/s. The degree of vacuum during vapor deposition is 0.7X 10-'
torr. The substrate temperature was 20°C.
ＩＴＯ上に生或した蒸着層の膜厚は６００Ａであった。The thickness of the vapor deposited layer formed on the ITO was 600A.
つぎに、前記正孔輸送層上に化合物Ｎα（Ｉ）−３の蛍
光性有機化合物を加熱温度が設定され蒸着速度の制御で
きる抵抗加熱源で蒸着して蛍光性化合物層を形威した．
膜厚は７００Ａであった．次に、この蛍光性化合物層の
上に膜厚ｔｓｏｏ人のＭｇ−Ａｇによる陰極を蒸着した
。このようにして得られた発光素子に外部電源を接続し
て、電流を流したところ、陽極側にプラスのバイアス電
圧を印加した場合に、明瞭な発光が確認された．また素
子は湿度を十分に除去した状態において空気中で作動さ
せることが可能であった．
実施例７
蛍光性有機化合物として、化合物Ｎｃｉ（１）−４を用
いた以外は実施例６と同様にして発光素子を作製した．
得られた発光素子は陽極側にプラスのバイアス電圧を印
加した場合に明瞭な発光を呈した。Next, a fluorescent organic compound of the compound Nα(I)-3 was deposited on the hole transport layer using a resistance heating source whose heating temperature was set and the deposition rate could be controlled to form a fluorescent compound layer.
The film thickness was 700A. Next, on this fluorescent compound layer, a cathode made of Mg--Ag was deposited to a thickness of 100 mL. When an external power source was connected to the light emitting device obtained in this way and a current was passed through it, clear light emission was observed when a positive bias voltage was applied to the anode side. Furthermore, the device could be operated in air with sufficient humidity removed. Example 7 A light emitting device was produced in the same manner as in Example 6 except that compound Nci(1)-4 was used as the fluorescent organic compound.
The obtained light emitting device exhibited clear light emission when a positive bias voltage was applied to the anode side.
更に、この発光素子は湿度を十分に除去した状態におい
て空気中で作動させることが可能であった．
実施例８
蛍光性有機化合物として、化合物Ｎａ（１）−５を用い
た以外は実施例６と同様にして発光素子を作製した．得
られた発光素子は陽極側にプラスのバイアス電圧を印加
した場合に明瞭な発光を呈した．更にこの発光素子は湿
度を十分に除去した状態において空気中で作動させるこ
とが可能であった，実施例９
蛍光性有機化合物として、化合物＆（ｎ）−４を用いた
以外は実施例６と同様にして発光素子を作製した。得ら
れた発光素子は陽極側にプラスのバイアス電圧を印加し
た場合に明瞭な発光を呈した，更にこの発光素子は湿度
を十分に除去した状態において空気中で作動させること
が可能であった実施例１０
蛍光性有機化合物として、化合物ｋ（ＩＩ）−５を用い
た以外は実施例６と同様にして発光素子を作製した。得
られた発光素子は陽極側にプラスのバイアス電圧を印加
した場合に明瞭な発光を呈した。Furthermore, this light-emitting device could be operated in air with sufficient humidity removed. Example 8 A light emitting device was produced in the same manner as in Example 6 except that the compound Na(1)-5 was used as the fluorescent organic compound. The obtained light-emitting device emitted clear light when a positive bias voltage was applied to the anode side. Furthermore, this light-emitting element could be operated in air with sufficient humidity removed.Example 9 Same as Example 6 except that compound &(n)-4 was used as the fluorescent organic compound. A light emitting device was produced in the same manner. The obtained light-emitting device exhibited clear light emission when a positive bias voltage was applied to the anode side.Furthermore, this light-emitting device could be operated in air with sufficient humidity removed. Example 10 A light emitting device was produced in the same manner as in Example 6 except that compound k(II)-5 was used as the fluorescent organic compound. The obtained light emitting device exhibited clear light emission when a positive bias voltage was applied to the anode side.
更に、この発光素子は湿度を十分に除去した状態におい
て空気中で作動させることが可能であった．
実施例１１
蛍光性有機化合物として、化合物ＮＧ（ＩＩ）−６を用
いた以外は実施例６と同様にして発光素子を作製した．
得られた発光素子は陽極側にプラスのバイアス電圧を印
加した場合に明瞭な発光を呈した．更に，この発光素子
は湿度を十分に除去した状態において空気中で作動させ
ることが可能であった．
実施例１２
蛍光性有機化合物として，化合物ＮＱ（ＩＩ）−７を用
いた以外は実施例６と同様にして発光素子を作製した．
得られた発光素子は陽極側にプラスのバイアス電圧を印
加した場合に明瞭な発光を呈した。Furthermore, this light-emitting device could be operated in air with sufficient humidity removed. Example 11 A light emitting device was produced in the same manner as in Example 6 except that compound NG(II)-6 was used as the fluorescent organic compound.
The obtained light-emitting device emitted clear light when a positive bias voltage was applied to the anode side. Furthermore, this light-emitting device could be operated in air with sufficient humidity removed. Example 12 A light emitting device was produced in the same manner as in Example 6 except that compound NQ(II)-7 was used as the fluorescent organic compound.
The obtained light emitting device exhibited clear light emission when a positive bias voltage was applied to the anode side.
更に、この発光素子は湿度を十分に除去した状態におい
て空気中で作動させることが可能であった．
実施例１３
蛍光性有機化合物として、化合物ＮＱ（Ｕ）−８を用い
た以外は実施例６と同様にして発光素子を作製した．得
られた発光素子は陽極側にプラスのバイアス電圧を印加
した場合に明瞭な発光を呈した。Furthermore, this light-emitting device could be operated in air with sufficient humidity removed. Example 13 A light emitting device was produced in the same manner as in Example 6 except that compound NQ(U)-8 was used as the fluorescent organic compound. The obtained light emitting device exhibited clear light emission when a positive bias voltage was applied to the anode side.
更に、この発光素子は湿度を十分に除去した状態におい
て空気中で作動させることが可能であった，
実施例１４
蛍光性有機化合物として、化合物＆ （ＩＩ ）−９を
用いた以外は実施例６と同様にして発光素子を作製した
．得られた発光素子は陽極側にプラスのバイアス電圧を
印加した場合に明瞭な発光を呈した。Furthermore, this light emitting device could be operated in air with sufficient humidity removed. Example 14 Example 6 except that compound &(II)-9 was used as the fluorescent organic compound. A light emitting device was fabricated in the same manner. The obtained light emitting device exhibited clear light emission when a positive bias voltage was applied to the anode side.
更に、この発光素子は湿度を十分に除去した場合におい
て空気中で作動させることが可能であった。Furthermore, this light emitting device could be operated in air if sufficient humidity was removed.
実施例１５
蛍光性有機化合物として、化合物＆（ｎ）−１０を用い
た以外は実施例６と同様にして発光素子を作製した．得
られた発光素子は陽極側にプラスのバイアス電圧を印加
した場合に明瞭な発光を呈した．更に、この発光素子は
湿度を十分に除去した状態において空気中で作動させる
ことが可能であった．
〔発明の効果〕
本発明の電界発光素子は前記構成からなるので、発光性
能が長時間に亘って持続し耐久性に優れたものである．Example 15 A light emitting device was produced in the same manner as in Example 6 except that the compound &(n)-10 was used as the fluorescent organic compound. The obtained light-emitting device emitted clear light when a positive bias voltage was applied to the anode side. Furthermore, this light-emitting device could be operated in air with sufficient humidity removed. [Effects of the Invention] Since the electroluminescent device of the present invention has the above-mentioned configuration, its luminous performance is maintained over a long period of time and it is excellent in durability.
第１ｒＩＩ（ａ）〜第１図（ｄ）は本発明の代表的な電
界発光素子の模式断面図である．
ｌ・・・基板、
２，４・・・電極、
３ａ・・・発光層、
３ｂ・・・電子輸
送層，
３ｃ・・・正孔輸送層．1rII(a) to 1(d) are schematic cross-sectional views of typical electroluminescent devices of the present invention. 1...Substrate, 2,4...Electrode, 3a...Light emitting layer, 3b...Electron transport layer, 3c...Hole transport layer.
Claims (1)
層または複数層の有機化合物層より構成される電界発光
素子において、前記有機化合物層のうち少なくとも一層
が、下記一般式（Ｉ）又は一般式（II）で表わされる有
機化合物のいずれか一方を構成成分とする層であること
を特徴とする電界発光素子。 ▲数式、化学式、表等があります▼ （式中、Ｒ＿２〜Ｒ＿２＿０は各々独立に水素原子、ハ
ロゲン原子、置換または未置換のアルキル基、置換また
は未置換のアリール基、アルコキシ基、置換または未置
換のアミノ基、シアノ基等を表わし、Ｒ＿１，Ｒ＿２，
Ｒ＿３，Ｒ＿４及びＲ＿６，Ｒ＿７，Ｒ＿８，Ｒ＿９は
互いに隣りあう置換基と環を形成してもよい。） ▲数式、化学式、表等があります▼ （式中、Ｒ＿２〜Ｒ＿１＿３は各々独立に水素原子、ハ
ロゲン原子、置換又は未置換のアルキル基、置換または
未置換のアリール基、アルコキシ基、置換または未置換
のアミノ基、シアノ基等をあらわし、Ｒ＿２，Ｒ＿２，
Ｒ＿３，Ｒ＿４及びＲ＿７，Ｒ＿８，Ｒ＿９，Ｒ＿１＿
０は互いに隣り合う置換基と環を形成してもよい。）(1) In an electroluminescent device composed of an anode, a cathode, and one or more organic compound layers sandwiched between them, at least one of the organic compound layers is formed by the following general formula (I) or the general An electroluminescent device characterized by being a layer containing one of the organic compounds represented by formula (II) as a constituent component. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_2 to R_2_0 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, an alkoxy group, a substituted or unsubstituted represents an amino group, a cyano group, etc., and R_1, R_2,
R_3, R_4 and R_6, R_7, R_8, R_9 may form a ring with adjacent substituents. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R_2 to R_1_3 each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, an alkoxy group, a substituted or unsubstituted Representing a substituted amino group, cyano group, etc., R_2, R_2,
R_3, R_4 and R_7, R_8, R_9, R_1_
0 may form a ring with adjacent substituents. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1307577A JPH03168294A (en) | 1989-11-29 | 1989-11-29 | Electric field luminescent element |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1307577A JPH03168294A (en) | 1989-11-29 | 1989-11-29 | Electric field luminescent element |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03168294A true JPH03168294A (en) | 1991-07-22 |
Family
ID=17970753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1307577A Pending JPH03168294A (en) | 1989-11-29 | 1989-11-29 | Electric field luminescent element |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03168294A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003044877A2 (en) * | 2001-11-16 | 2003-05-30 | Cdt Oxford Limited | Light emitting device and compounds for use therein |
| KR100389195B1 (en) * | 2000-12-08 | 2003-06-27 | (주)신화엔지니어링종합건축사사무소 | Blue light emitting organic electroluminescnt device using tetrahydrochrysene as light emitting material |
| JP2008156261A (en) * | 2006-12-22 | 2008-07-10 | Univ Nagoya | Cross-linked stilbene derivative and organic electric field light-emitting device by using the same |
| US20090230854A1 (en) * | 2008-03-14 | 2009-09-17 | Myeong-Suk Kim | Indeno indene-based compound, organic light emitting device comprising the same, and method of manufacturing the organic light emitting device |
| JP2011184309A (en) * | 2010-03-04 | 2011-09-22 | Institute Of Physical & Chemical Research | Method for producing fused ring compound and new compound |
| JP2014058516A (en) * | 2012-09-17 | 2014-04-03 | Samsung Display Co Ltd | Condensed-cyclic compound and organic light-emitting element |
-
1989
- 1989-11-29 JP JP1307577A patent/JPH03168294A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100389195B1 (en) * | 2000-12-08 | 2003-06-27 | (주)신화엔지니어링종합건축사사무소 | Blue light emitting organic electroluminescnt device using tetrahydrochrysene as light emitting material |
| WO2003044877A2 (en) * | 2001-11-16 | 2003-05-30 | Cdt Oxford Limited | Light emitting device and compounds for use therein |
| WO2003044877A3 (en) * | 2001-11-16 | 2003-10-30 | Cdt Oxford Ltd | Light emitting device and compounds for use therein |
| US7723553B2 (en) | 2001-11-16 | 2010-05-25 | Cdt Oxford Limited | Light emitting device and compounds for use therein |
| JP2008156261A (en) * | 2006-12-22 | 2008-07-10 | Univ Nagoya | Cross-linked stilbene derivative and organic electric field light-emitting device by using the same |
| US20090230854A1 (en) * | 2008-03-14 | 2009-09-17 | Myeong-Suk Kim | Indeno indene-based compound, organic light emitting device comprising the same, and method of manufacturing the organic light emitting device |
| JP2011184309A (en) * | 2010-03-04 | 2011-09-22 | Institute Of Physical & Chemical Research | Method for producing fused ring compound and new compound |
| JP2014058516A (en) * | 2012-09-17 | 2014-04-03 | Samsung Display Co Ltd | Condensed-cyclic compound and organic light-emitting element |
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