JPH04184892A - Electroluminescent element - Google Patents
Electroluminescent elementInfo
- Publication number
- JPH04184892A JPH04184892A JP2314840A JP31484090A JPH04184892A JP H04184892 A JPH04184892 A JP H04184892A JP 2314840 A JP2314840 A JP 2314840A JP 31484090 A JP31484090 A JP 31484090A JP H04184892 A JPH04184892 A JP H04184892A
- Authority
- JP
- Japan
- Prior art keywords
- light emitting
- emitting device
- substituted
- layer
- 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.)
- Granted
Links
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 57
- 239000010410 layer Substances 0.000 abstract description 45
- 239000000203 mixture Substances 0.000 abstract description 2
- 238000001771 vacuum deposition Methods 0.000 abstract description 2
- 238000010030 laminating Methods 0.000 abstract 1
- 239000002356 single layer Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000010409 thin film Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 description 25
- 239000000758 substrate Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- -1 aromatic tertiary amines Chemical class 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 229910001316 Ag alloy Inorganic materials 0.000 description 2
- 229910000861 Mg alloy Inorganic materials 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
- 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 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920005596 polymer binder Polymers 0.000 description 2
- 239000002491 polymer binding agent Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- GGNDPFHHUHTCIO-UHFFFAOYSA-N 1h-benzimidazole;perylene-3,4,9,10-tetracarboxylic acid Chemical compound C1=CC=C2NC=NC2=C1.C1=CC=C2NC=NC2=C1.C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O GGNDPFHHUHTCIO-UHFFFAOYSA-N 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino 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
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000019646 color tone Nutrition 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 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
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 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
- 125000002887 hydroxy group Chemical group [H]O* 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
- 239000011133 lead Substances 0.000 description 1
- 238000004020 luminiscence type Methods 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
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002102 polyvinyl toluene Polymers 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl 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
- 238000012827 research and development Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 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
- 125000006617 triphenylamine group Chemical group 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。[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. The present invention relates to an electroluminescent device that, unlike lamps or light emitting diodes, enables the realization of large-area planar light emitters.
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、
駆動に２００■以上の高い交流電界を必要とすること、
製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。Electroluminescent elements differ in their luminescence excitation mechanisms; (1) intrinsic electroluminescent elements, which excite a luminescent body by local movement of electrons and holes within the luminescent layer, and emit light only in an alternating electric field;
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 device is generally made of ZnS with Mn and Cu.
The luminescent material is an inorganic compound added with
Requiring a high alternating current electric field of 200μ or more for driving;
It 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。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.
特開昭５９−１９４３９３、米国特許４，５３９，５０
７、特開昭６３−２９５６９５、米国特許４，７２０，
４３２及び特開昭６３−２６４６９２には、陽極、有機
質ホール注入輸送帯、有機質電子注入性発光体および陰
極から成る電界発光素子が開示されており、これらに使
用される材料としては、例えば、有機質ホール注入輸送
用材料としては芳香族三級アミンが、また、有機質電子
注入性発光材料としては、アルミニウムトリスオキシン
等が代表的な例としてあげられる。JP 59-194393, U.S. Patent No. 4,539,50
7, Japanese Patent Application Publication No. 63-295695, U.S. Patent No. 4,720,
432 and JP-A No. 63-264692 disclose an electroluminescent device consisting of an anode, an organic hole injection transport band, an organic electron-injecting luminescent material, and a cathode. Materials used for these devices include, for example, organic Typical examples include aromatic tertiary amines as hole injection and transport materials, and aluminum trisoxine as organic electron injection luminescent materials.
また、Ｊｐｎ、Ｊｏｕｒｎａｌ ｏｆ Ａｐｐｌｉｅｄ
Ｐｈｙｓｉｃｄ、ｖｏｌ。Also, Jpn, Journal of Applied
Physicd, vol.
２７、ｐ７１３−７１５には陽極、有機質ホール輸送層
、発光層、有機質電子輸送層および陰極から成る電界発
光素子が報告されており、これらに使用される材料とし
ては、有機質ホール輸送材料としてはＮ。27, p. 713-715, an electroluminescent device consisting of an anode, an organic hole transport layer, a light emitting layer, an organic electron transport layer, and a cathode is reported, and the materials used for these include N as the organic hole transport material. .
Ｎ′−ジフェニル−Ｎ、Ｎ’−ビス（３−メチルフェニ
ル）−１゜１′−ビフェニル−４，４′−ジアミンが、
また、有機質電子輸送材料としては、３，４，９．１０
−ペリレンテトラカルボン酸ビスベンズイミダゾールが
また発光材料としてはフタロペリノンが例示されている
。N'-diphenyl-N,N'-bis(3-methylphenyl)-1゜1'-biphenyl-4,4'-diamine,
In addition, as organic electron transport materials, 3, 4, 9.10
-perylenetetracarboxylic acid bisbenzimidazole and phthaloperinone are exemplified as luminescent materials.
これらの例は有機化合物を、ホール輸送材料、発光材料
、電子輸送材料として用いるためには、これらの有機化
合物の各種特性を探求し、かかる特性を効果的に組み合
わせて電界発光素子とする必要性を意味し、換言すれば
広い範囲の有機化合物の研究開発が必要であることを示
している。These examples demonstrate that in order to use organic compounds as hole-transporting materials, luminescent materials, and electron-transporting materials, it is necessary to explore various properties of these organic compounds and effectively combine these properties to create electroluminescent devices. In other words, it shows that research and development of a wide range of organic compounds is necessary.
さらに、上記の例を含め有機化合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の歴史も浅く、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、フルカラー
デイスプレーへの応用を考えた場合の青、緑および赤の
発光色相を精密に選択できるための発光波長の多様化あ
るいは耐久性の向上など多くの課題を抱えているのが実
情である。Furthermore, research on carrier injection electroluminescent devices using organic compounds as light emitters, including the examples mentioned above, has a short history, and research into materials and device development has not yet been sufficiently conducted. However, there are many issues to be solved, such as further improvement in brightness, diversification of emission wavelengths to enable precise selection of blue, green, and red emission hues when considering application to full-color displays, and improvement of durability. The reality is that there are.
本発明は上記従来技術の実情に鑑みてなされたものであ
り、その目的は発光波長に多様性があり、種々の発光色
相を呈すると共に耐久性に優れた電界発光素子を提供す
ることにある。The present invention has been made in view of the above-mentioned state of the prior art, and its purpose is to provide an electroluminescent element that has diversity in emission wavelength, exhibits various emission hues, and has excellent durability.
本発明者らは、上記課題を解決するための発光層の構成
要素について鋭意検討した結果、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（Ｉ）で表わさ
れる有機化合物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。As a result of intensive studies on the constituent elements of a light-emitting layer to solve the above problems, the present inventors found that an electroluminescent layer composed of an anode, a cathode, and one or more organic compound layers sandwiched between the anode and cathode. An electroluminescent device in which at least one of the organic compound layers is a layer containing an organic compound represented by the following general formula (I) as a component is effective for solving the above problem. This discovery led to the completion of the present invention.
（式中、Ｘ、 Ａｒ、、Ａｒ２、Ｒ，及びＲ２は以下の
基を示す。(In the formula, X, Ar, Ar2, R, and R2 represent the following groups.
Ａｒ□、Ａｒ、、Ａｒ、：置換もしくは未置換の炭素環
式芳香環、置換もしくは未置換の複素
環式芳香環
Ｒ工ｌＲ２ｙＲｉ ：水素原子、置換もしくは未置換の
アルキル基、置換もしくは未置換
の炭素環式芳香環、置換もしくは
未置換の複素環式芳香環）
一般式（１）において、Ｒ工、Ｒ２、Ｒ１として用いら
れるアルキル基は、好ましくはＣ工〜Ｃ２゜とりわけ０
１〜０１□の直鎖または分岐鎖のアルキル基である。Ar□, Ar, Ar,: substituted or unsubstituted carbocyclic aromatic ring, substituted or unsubstituted heterocyclic aromatic ring Carbocyclic aromatic ring, substituted or unsubstituted heterocyclic aromatic ring) In the general formula (1), the alkyl group used as R, R2, R1 is preferably C to C2, especially 0
It is a straight chain or branched alkyl group of 1 to 01□.
また、一般式（１）において、Ａｒ１、Ａｒ、、Ｒ１，
Ｒ２゜Ｒ３として用いられる炭素環式あるいは複素環式
芳香環の例としては、フェニル、ナフチル、アントリル
、アセナフチニル、フルオレニル、フェンナントリル、
ピリジル、ピリミジル、フラニル、ピロリル、チオフェ
ニル、キノリル、ベンゾフラニル、ベンゾチオフェニル
、インドリル、カルバゾリル、ベンゾオキサシリル、キ
ノキサリル等が挙げられる。Furthermore, in general formula (1), Ar1, Ar, , R1,
Examples of carbocyclic or heterocyclic aromatic rings used as R2゜R3 include phenyl, naphthyl, anthryl, acenaphthynyl, fluorenyl, phenanthryl,
Examples include pyridyl, pyrimidyl, furanyl, pyrrolyl, thiophenyl, quinolyl, benzofuranyl, benzothiophenyl, indolyl, carbazolyl, benzoxacylyl, quinoxalyl, and the like.
また一般式（１）におけるＡｒｉ、 Ａｒ２、Ａｒ、の
置換基としては以下のものを挙げることができる。Further, as substituents for Ari, Ar2, and Ar in general formula (1), the following can be mentioned.
（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Ｃ工〜Ｃ２゜とりわけＣ
１〜Ｃ工２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、水酸基、シアノ基、Ｃ８〜Ｃ
１２のアルコキシ基、フェニル基またはハロゲン原子、
Ｃ工〜ＣＡＲのアルキル基若しくは０１〜ｃ１□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 C to C2, especially C
A linear or branched alkyl group having 1 to 2 carbon atoms, and these alkyl groups further include a hydroxyl group, a cyano group, a C8 to
12 alkoxy groups, phenyl groups or halogen atoms,
It may contain a phenyl group substituted with an alkyl group of C to CAR or an alkoxy group of 01 to c1□.
（３）アリール基：フェニル基、ナフチル基、アントリ
ル基、ピリジン基、フラニル基、チオフェニル基等であ
り、これらのアリール基は、更にＣ工〜Ｃ１□のアルキ
ル基、Ｃニーｃｉｚのアルコキシ基、Ｃ２〜０１□のア
ルキルアミノ基、ジアルキルアミノ基、シアノ基、ハロ
ゲン原子、フェニル基で置換されていても良い。(3) Aryl group: phenyl group, naphthyl group, anthryl group, pyridine group, furanyl group, thiophenyl group, etc.; It may be substituted with a C2-01□ alkylamino group, dialkylamino group, cyano group, halogen atom, or phenyl group.
（４）アルコキシ基（−０Ｒ１）；Ｒ１は（２）で定義
したアルキル基を表わす。(4) Alkoxy group (-0R1); R1 represents the alkyl group defined in (2).
（５）アリールオキシ基；アリール基としては、（３）
で定義したアリール基を表わす。(5) Aryloxy group; As an aryl group, (3)
represents an aryl group defined in
（６）アルキルチオ基（−５Ｒ１）；Ｒ’は（２）で定
義したアルキル基を表わす。(6) Alkylthio group (-5R1); R' represents the alkyl group defined in (2).
（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あ
られす。またピペリジル基、モルホリル基のように、Ｒ
２とＲ３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
環を形成しても良い。An acyl group such as an alkyl group, an acetyl group, or a benzoyl group defined in (2) or an aryl group defined in (3) is used. Also, like piperidyl group and morpholyl group, R
2 and R3 may form a ring together with the nitrogen atom. Furthermore, a ring may be formed jointly with a carbon atom on an aryl group, as in the case of a eurolidyl group.
アルコキシカルボニル基（−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。Alkoxycarbonyl group (-COOR');R' is (2
) represents an alkyl group defined in (3) or an aryl group defined in (3).
（８）アシル基（−ＣＯＲ’）、Ｘ ）Ｌｔ ホー＋
）Ｉ、’基（−５ｏ、 Ｒ’ ）、た意味を表わす。但
しＲ２及びＲ３においてアリール基上の炭素原子と共同
で環を形成する場合を除く。(8) Acyl group (-COR'),
) I, ' group (-5o, R'), represents the meaning. However, this excludes the case where R2 and R3 jointly form a ring with the carbon atoms on the aryl group.
（９）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。(9) Alkylene dioxy group or alkylene dithio group such as methylene dioxy group or methylene dithio group.
次に本発明で使用される一般式（１）で表される化合物
の具体例を示すが１本発明はこれらに限定されるもので
はない。Next, specific examples of the compound represented by the general formula (1) used in the present invention will be shown, but the present invention is not limited thereto.
ｒｔ
Ｅｔ
■
Ｅｔ
しに
Ｉ
しＩＸ
本発明における電界発光素子は、以上で説明した有機化
合物を真空蒸着法、溶液塗布等により、有機化合物全体
で２癖より小さい厚み、さらに好ましくは、０．０５．
〜０．５−の厚みに薄膜化することにより有機化合物層
を形成し、陽極及び陰極で挾持することにより構成され
る。rt Et ■ Et Shini I Shi IX The electroluminescent device of the present invention is produced by applying the organic compound described above by vacuum evaporation, solution coating, etc. so that the total thickness of the organic compound as a whole is less than 0.05 mm, more preferably 0.05 mm. ．．
It is constructed by forming an organic compound layer by thinning it to a thickness of ~0.5 - and sandwiching it between an anode and a cathode.
以下、図面に沿って本発明を更に詳細に説明する。Hereinafter, the present invention will be explained in more detail along the drawings.
第１図は本発明の電界発光素子の代表的な例であって、
基板上に陽極、発光層及び陰極を順次設けた構成のもの
である。FIG. 1 shows a typical example of the electroluminescent device of the present invention,
It has a structure in which an anode, a light emitting layer, and a cathode are sequentially provided on a substrate.
第１図に係る電界発光素子は使用する化合物が単一でホ
ール輸送性、電子輸送性、発光性の特性を有する場合あ
るいは各々の特性を有する化合物を混合して使用する場
合に特に有用である。The electroluminescent device shown in FIG. 1 is particularly useful when a single compound is used that has hole-transporting properties, electron-transporting properties, and luminescent properties, or when a mixture of compounds having each of these properties is used. .
第２図はホール輸送性化合物と電子輸送性化合物との組
み合わせにより発光層を形成したものである。この構成
は有機化合物の好ましい特性を組み合わせるものであり
、ホール輸送性あるいは電子輸送性の優れた化合物を組
み合わせることにより電極からのホールあるいは電子の
注入を円滑に行ない発光特性の優れた素子を得ようとす
るものである。なお、このタイプの電界発光素子の場合
、組み合わせる有機化合物によって発光物質が異なるた
め、どちらの化合物が発光するかは一義的に定めること
はできない。FIG. 2 shows a light-emitting layer formed by a combination of a hole-transporting compound and an electron-transporting compound. This configuration combines the favorable properties of organic compounds, and by combining compounds with excellent hole transport properties or electron transport properties, it is possible to smoothly inject holes or electrons from the electrodes to obtain an element with excellent light emitting properties. That is. Note that in the case of this type of electroluminescent device, since the light-emitting substances differ depending on the organic compounds used in combination, it is not possible to unambiguously determine which compound emits light.
第３図は、ホール輸送性化合物１発光性化合物、電子輸
送性化合物の組み合わせにより発光層を形成するもので
あり、これは上記の機能分離の考えをさらに進めたタイ
プのものと考えることができる。Figure 3 shows a light-emitting layer formed by a combination of a hole-transporting compound, a luminescent compound, and an electron-transporting compound, and this can be considered to be a type that further advances the above idea of functional separation. .
このタイプの電界発光素子はホール輸送性、電子輸送性
及び発光性の各特性を適合した化合物を適宜組み合わせ
ることによって得ることができるので、化合物の対象範
囲が極めて広くなるため。This type of electroluminescent device can be obtained by appropriately combining compounds that have hole-transporting properties, electron-transporting properties, and luminescent properties, so the range of compounds that can be used is extremely wide.
その選定が容易となるばかりでなく、発光波長を異にす
る種々の化合物が使用できるので、素子の発光色相が多
様化するといった多くの利点を有する。It not only makes selection easy, but also allows the use of various compounds with different emission wavelengths, which has many advantages, such as diversifying the emission hues of the device.
本発明の化合物はいずれも発光特性の優れた化金物であ
り必要により第１図、第２図及び第３図の様な構成をと
ることができる。All of the compounds of the present invention are metal compounds with excellent luminescent properties, and can have structures as shown in FIGS. 1, 2, and 3, if necessary.
また本発明においては、前記一般式（１）におけるＡｒ
、Ｒ□、Ｒｚあるいは置換基の種類を適宜選定すること
によりホール輸送性の優れた化合物あるいは電子輸送性
の優れた化合物の両者の提供を可能とする。Further, in the present invention, Ar in the general formula (1)
, R□, Rz, or the type of substituent, it is possible to provide both a compound with excellent hole transport properties and a compound with excellent electron transport properties.
従って、第２図及び第３図の構成の場合、発光層形成成
分として、前記一般式（１）で示される化合物の２種類
以上用いても良い。Therefore, in the case of the configurations shown in FIGS. 2 and 3, two or more types of compounds represented by the general formula (1) may be used as components for forming the light emitting layer.
本発明においては、発光層形成成分として前記一般式（
１）で示される化合物を用いるものであるが、必要に応
じて、ホール輸送性化合物として芳香族第三級アミンあ
るいはＮ、Ｎ’−ジフェニル−Ｎ、Ｎ’−ビス（３−メ
チルフェニル）−１，１’−ビフェニル−４，４′−ジ
アミン等を、また電子輸送性化合物として、アルミニウ
ムトリスオキシン、またはべりレンチトラカルボン酸誘
導体等を用いることができる。In the present invention, the above general formula (
The compound shown in 1) is used, but if necessary, aromatic tertiary amine or N,N'-diphenyl-N,N'-bis(3-methylphenyl)- 1,1'-biphenyl-4,4'-diamine and the like can be used, and as an electron transporting compound, aluminum trisoxine or a perylentitracarboxylic acid derivative can be used.
本発明の電界発光素子は発光層に電気的にバイアスを付
与し発光させるものであるが、わずかなピンホールによ
って短絡をおこし素子として機能しなくなる場合もある
ので、発光層の形成には皮膜形成性に優れた化合物を併
用することが望ましい。更にこのような皮膜形成性に優
れた化合物とたとえばポリマー結合剤を組み合わせて発
光層を形成することもできる。この場合に使用できるポ
リマー結合剤としては、ポリスチレン、ポリビニルトル
エン、ポリ−Ｎ−ビニルカルバゾール、ポリメチルメタ
クリレート、ポリメチルアクリレート、ポリエステル、
ポリカーボネート、ポリアミド等を挙げることができる
。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。The electroluminescent device of the present invention emits light by applying an electrical bias to the light-emitting layer, but a slight pinhole may cause a short circuit and cause the device to no longer function, so film formation is necessary to form the light-emitting layer. It is desirable to use compounds with excellent properties. Furthermore, a light-emitting layer can be formed by combining such a compound with excellent film-forming properties with, for example, a polymer binder. Polymer binders that can be used in this case include polystyrene, polyvinyltoluene, poly-N-vinylcarbazole, polymethyl methacrylate, polymethyl acrylate, polyester,
Examples include polycarbonate and polyamide. In addition, in order to improve the charge injection efficiency from the electrode,
It is also possible to separately provide a charge injection transport layer between the electrodes.
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（ＳｎＯ□）、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。The anode materials include nickel, gold, platinum, palladium, alloys of these, metals with large work functions such as tin oxide (SnO□), 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.
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、アルミニウム、或いはこれ
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。On the other hand, as the cathode material, silver, tin, lead, magnesium, manganese, aluminum, or an alloy thereof, which has a small work function, is used. It is desirable that at least one of the materials used for the anode and the cathode be sufficiently transparent in the emission wavelength region of the device. Specifically, it is desirable to have a light transmittance of 80% or more.
本発明においては、透明陽極を透明基板上に形成し、第
１図〜第３図の様な構成とすることが好ましいが、場合
によってはその逆の構成をとっても良い。また透明基板
としてはガラス、プラスチックフィルム等が使用できる
。In the present invention, it is preferable to form a transparent anode on a transparent substrate and have a structure as shown in FIGS. 1 to 3, but the opposite structure may be used depending on the case. Moreover, glass, plastic film, etc. can be used as the transparent substrate.
また、本発明においては、この様にして得られた電界発
光素子の安定性の向上、特に大気性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。In addition, in the present invention, in order to improve the stability of the electroluminescent device obtained in this way, and in particular to protect it from atmospheric moisture, it is possible to provide a separate protective layer, or to place the entire device in a cell and use silicone. It is also possible to enclose oil or the like.
以下実施例に基いて、本発明をより具体的に説明する。 The present invention will be described in more detail below based on Examples.
実施例１
ガラス基板上に大きさ３ｍｍ Ｘ ３■璽、厚さ５００
人の酸化錫インジウム（ＩＴＯ）による陽極を形成し、
その上に下記構造式（ａ）で示されるトリフェニルアミ
ン誘導体からなるホール輸送層５００人、前記化合物Ｎ
α２からなる発光層１１００人、銀／マグネシウム合金
（銀７．７原子パーセント、純度９９．９％）からなる
陰極１５００人を各々真空蒸着により形成し、第２図に
示すような素子を作製した。蒸着時の真空度は約６ Ｘ
１０−’ Ｔｏｒｒ、基板温度は室温である。このよ
うにして作製した素子の陽極及び陰極にリード線を介し
て直流電源を接続し、電圧を印加したところ明瞭な発光
が長時間にわたって確認された。Example 1 Size: 3 mm x 3 squares, thickness: 500 mm on a glass substrate
Forming an anode with human indium tin oxide (ITO),
On top of that, 500 hole transport layers made of a triphenylamine derivative represented by the following structural formula (a), and the compound N
A light emitting layer of 1,100 layers made of α2 and a cathode of 1,500 layers made of silver/magnesium alloy (7.7 atomic percent silver, purity 99.9%) were each formed by vacuum evaporation to produce a device as shown in Figure 2. . The degree of vacuum during deposition is approximately 6X
10-' Torr, and the substrate temperature was room temperature. When a direct current power source was connected to the anode and cathode of the device thus fabricated via lead wires and a voltage was applied, clear light emission was observed for a long period of time.
この例より本発明で用いる前記化合物Ｎα２は、電子輸
送性発光材料として機能したことが理解される。From this example, it is understood that the compound Nα2 used in the present invention functioned as an electron transporting luminescent material.
実施例２
発光物質として化合物Ｎα３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６
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。Example 2 A light emitting device was produced in the same manner as in Example 1 except that compound Nα3 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 side6.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恥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 3 A light emitting device was produced in the same manner as in Example 1 except that Compound 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４
発光物質として化合物Ｎｃｉ５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 4 Example 1 except that compound Nci5 was used as the luminescent material
A light emitting device was produced in the same manner as above. 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＆９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 &9 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６
発光物質として化合物Ｎ（１１５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 6 A light emitting device was produced in the same manner as in Example 1 except that Compound N (115 was used as the light emitting substance).The obtained light emitting device emitted clear light when a positive bias voltage was applied to the anode side. presented.
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７
発光物質として化合物勲１３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 7 A light emitting device was produced in the same manner as in Example 1 except that Compound 13 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８
発光物質として化合物Ｎ１１７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 8 Example 1 except that compound N117 was used as the luminescent material
A light emitting device was produced in the same manner as above. 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９
発光物質として化合物Ｎｎ２２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 9 Example 1 except that compound Nn22 was used as the luminescent material
A light emitting device was produced in the same manner as above. 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１０
発光物質として化合物＆２５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 10 A light emitting device was produced in the same manner as in Example 1 except that Compound &25 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１１
発光物質として化合物＆３４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 11 A light emitting device was produced in the same manner as in Example 1 except that Compound &34 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１２
発光物質として化合物勲３７を用いた以外は実施例Ｉ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 12 A light-emitting device was produced in the same manner as in Example I except that Compound 37 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１３
発光物質として化合物＆５０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 13 A light emitting device was produced in the same manner as in Example 1 except that Compound &50 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１４
発光物質として化合物Ｎａ４２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 14 Example 1 except that compound Na42 was used as the luminescent substance
A light emitting device was produced in the same manner as above. 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１５
発光物質として化合物Ｎｎ４４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 15 Example 1 except that compound Nn44 was used as the luminescent material
A light emitting device was produced in the same manner as above. 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１６
発光物質として化合物＆４６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 16 A light emitting device was produced in the same manner as in Example 1 except that Compound &46 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１７
発光物質として化合物Ｎｃ４１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 17 Example 1 except that compound Nc41 was used as the luminescent material
A light emitting device was produced in the same manner as above. 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１８
発光物質として化合物嵐４０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 18 A light emitting device was produced in the same manner as in Example 1 except that Compound Arashi 40 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１９
発光物質として化合物Ｎｎ４４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 19 Example 1 except that compound Nn44 was used as the luminescent material
A light emitting device was produced in the same manner as above. 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２０
発光物質として化合物嵐４３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 20 A light emitting device was produced in the same manner as in Example 1 except that Compound Arashi 43 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２１
発光物質として化合物ＮＱ４５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 21 Example 1 except that compound NQ45 was used as the luminescent material
A light emitting device was produced in the same manner as above. 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２２
発光物質として化合物＆４７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 22 A light emitting device was produced in the same manner as in Example 1 except that Compound &47 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２３
ガラス基板上に大きさ３ｍｍ Ｘ ３＋＋ｍ、厚さ５０
０人の酸化錫インジウム（ＩＴＯ）による陽極を形成し
、その上に前記化合物魔１からなる発光層９５０人、下
記構造式（ｂ）で示されるオキシジアゾール誘導体から
なる電子輸送層５００人、銀／マグネシラム合金（銀７
．７原子パーセント、純度９９．９％）からなる陰極１
４００人を各々真空蒸着により形成し、第２図に示すよ
うな素子を作製した。蒸着時の真空度は約１Ｘ １０−
’Ｔｏｒｒ、基板温度は室温である。このようにして作
製した素子の陽極及び陰極にリード線を介して直流電源
を接続し、電圧を印加したところ明瞭な発光が長時間に
わたって確認された。Example 23 Size: 3 mm x 3++ m, thickness: 50 mm on a glass substrate
Form an anode made of indium tin oxide (ITO), on which a light-emitting layer of 950 layers made of the compound 1, an electron transport layer of 500 layers made of an oxydiazole derivative represented by the following structural formula (b), Silver/magnesilum alloy (Silver 7
．． 7 atomic percent, purity 99.9%)
400 layers were each formed by vacuum evaporation to produce a device as shown in FIG. The degree of vacuum during vapor deposition is approximately 1X 10-
'Torr, the substrate temperature is room temperature. When a direct current power source was connected to the anode and cathode of the device thus fabricated via lead wires and a voltage was applied, clear light emission was observed for a long period of time.
この例より、化合物Ｎα１は、ホール輸送性発光材料と
して機能したことがわかる。This example shows that the compound Nα1 functioned as a hole-transporting luminescent material.
実施例２４
発光物質として化合物魔８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 24 A light emitting device was produced in the same manner as in Example 1 except that Compound 8 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２５
発光物質として化合物Ｎ１１１８を用い、発光層の膜厚
を１０００人にした以外は、実施例２３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 25 A light-emitting device was produced in the same manner as in Example 23, except that compound N1118 was used as the light-emitting substance and the thickness of the light-emitting layer was 1000 mm. 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２６
発光物質として化合物Ｎ１１３４を用い、発光層の膜厚
を９２０人にした以外は、実施例２３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 26 A light emitting device was produced in the same manner as in Example 23, except that Compound N1134 was used as the light emitting substance and the thickness of the light emitting layer was 920 mm. 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２７
発光物質として化合物Ｎｎ４ｇを用い、発光層の膜厚を
９００人にした以外は、実施例２３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 27 A light emitting device was produced in the same manner as in Example 23, except that 4 g of the compound Nn was used as the light emitting substance and the thickness of the light emitting layer was 900 mm. 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２８
発光物質として化合物ＮＱ４９を用いた以外は、実施例
２７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 28 A light emitting device was produced in the same manner as in Example 27 except that compound NQ49 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２９
発光物質として化合物＆６１を用い、発光層の膜厚を１
０００人にした以外は、実施例２３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 29 Compound &61 was used as a luminescent substance, and the thickness of the luminescent layer was 1
A light emitting device was produced in the same manner as in Example 23 except that the number of people was 1,000. 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３０
発光物質として化合物＆６２を用いた以外は、実施例２
９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 30 Example 2 except that compound &62 was used as the luminescent substance
A light emitting device was produced in the same manner as in Example 9. 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３１
ガラス基板上に大きさ３ｍｍＸ３ｍｍ、厚さ５００人の
酸化錫インジウム（ＩＴＯ）による陽極を形成し、その
上に前記化合物翫１０からなる発光層１０００人、銀／
マグネシウム合金（銀７．７原子パーセント、純度９９
．９％）からなる陰極１５００人を各々真空蒸着により
形成し、第１図に示すような素子を作製した。蒸着時の
真空度は約Ｉ Ｘ １０−＠Ｔｏｒｒ、基板温度は室温
である。このようにして作製した素子の陽極及び陰極に
リード線を介して直流電源を接続し、電圧を印加したと
ころ明瞭な発光が長時間にわたって確認された。Example 31 An anode made of indium tin oxide (ITO) having a size of 3 mm x 3 mm and a thickness of 500 mm was formed on a glass substrate, and a light-emitting layer of 1000 mm and silver/
Magnesium alloy (7.7 atomic percent silver, purity 99
．． A device as shown in FIG. 1 was fabricated by forming 1,500 cathodes each consisting of 9% (9%) by vacuum evaporation. The degree of vacuum during vapor deposition was approximately I x 10-@Torr, and the substrate temperature was room temperature. When a direct current power source was connected to the anode and cathode of the device thus fabricated via lead wires and a voltage was applied, clear light emission was observed for a long period of time.
実施例３２
発光物質として化合物ＮＱ２１を用い、発光層の膜厚を
１０５０人にした以外は、実施例３１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 32 A light-emitting device was produced in the same manner as in Example 31, except that Compound NQ21 was used as the light-emitting substance and the thickness of the light-emitting layer was 1050 nm. 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３３
発光物質として化合物Ｎ１１３３を用いた以外は、実施
例３１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 33 A light emitting device was produced in the same manner as in Example 31 except that compound N1133 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３４
発光物質として化合物Ｎα５１を用い、発光層の膜厚を
１０５０人にした以外は、実施例３１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 34 A light-emitting device was produced in the same manner as in Example 31, except that the compound Nα51 was used as the light-emitting substance and the thickness of the light-emitting layer was 1050 nm. 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３５
発光物質として化合物ＮＱ６３を用い、発光層の膜厚を
９００人にした以外は、実施例３１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 35 A light emitting device was produced in the same manner as in Example 31, except that compound NQ63 was used as the light emitting substance and the thickness of the light emitting layer was 900 mm. 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.
本発明の電界発光素子は有機化合物層の構成材料として
前記一般式（１）で示される化合物を用いたことから、
低い開動電圧でも長期間にわたって輝度の高い発光を得
ることが出来ると共に種々の色調を呈することが可能と
なる６
また素子の作成も真空蒸着法等により容易に行なえるの
で安価で大面積の素子を効率よく生産できる等の利点を
有する。Since the electroluminescent device of the present invention uses the compound represented by the general formula (1) as a constituent material of the organic compound layer,
It is possible to obtain high-brightness light emission for a long period of time even at a low operating voltage, and it is also possible to exhibit various color tones.6 Furthermore, since the device can be easily fabricated using vacuum evaporation methods, it is possible to create a large-area device at low cost. It has advantages such as efficient production.
第１図〜第３図は、本発明に係る電界発光素子の模式断
面図である。
特許出願人 株式会社 リ コ −1 to 3 are schematic cross-sectional views of an electroluminescent device according to the present invention. Patent applicant Rico Co., Ltd. −
Claims (3)
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）で表わされる有機化合物を構成成分
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、Ｘ、Ａｒ＿１，Ａｒ＿２，Ｒ＿１及びＲ＿２は
以下の基を示す。 ▲数式、化学式、表等があります▼ Ａｒ＿１，Ａｒ＿２，Ａｒ＿３：置換もしくは未置換の
炭素環式芳香環、置換もしくは未置換の複素 環式芳香環 Ｒ＿１，Ｒ＿２，Ｒ＿３：水素原子、置換もしくは未置
換のアルキル基、置換もしくは未置換 の炭素環式芳香環、置換もしくは未置換の複素環式芳香
環）(1) In an electroluminescent device composed of an anode and a cathode, and one or more organic compound layers sandwiched between them, at least one of the organic compound layers is represented by the following general formula (I). An electroluminescent device characterized by having a layer containing an organic compound as a constituent component. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, X, Ar_1, Ar_2, R_1 and R_2 represent the following groups. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ Ar_1, Ar_2, Ar_3: Substituted or unsubstituted Carbocyclic aromatic ring, substituted or unsubstituted heterocyclic aromatic ring R_1, R_2, R_3: hydrogen atom, substituted or unsubstituted alkyl group, substituted or unsubstituted carbocyclic aromatic ring, substituted or unsubstituted heterocyclic aromatic ring)
原子である請求項（１）の電界発光素子。(2) The electroluminescent device according to claim (1), wherein in general formula (I), R_1 and R_2 are hydrogen atoms.
＾２が置換もしくは未置換のフェニル基である請求項（
１）又は請求項（２）の電界発光素子。(3) In general formula (I), Ar^1 and/or Ar
Claim (2) wherein ^2 is a substituted or unsubstituted phenyl group (
1) or the electroluminescent device according to claim (2).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2314840A JP2913116B2 (en) | 1990-11-20 | 1990-11-20 | EL device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2314840A JP2913116B2 (en) | 1990-11-20 | 1990-11-20 | EL device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04184892A true JPH04184892A (en) | 1992-07-01 |
| JP2913116B2 JP2913116B2 (en) | 1999-06-28 |
Family
ID=18058238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2314840A Expired - Lifetime JP2913116B2 (en) | 1990-11-20 | 1990-11-20 | EL device |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2913116B2 (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08295655A (en) * | 1995-03-01 | 1996-11-12 | Takasago Internatl Corp | Triphenylamine derivative, charge transport material and photosensitizer for electrophotograph using the same |
| JPH10255979A (en) * | 1997-03-06 | 1998-09-25 | Minolta Co Ltd | Organic electroluminescent element |
| JP2001521053A (en) * | 1997-10-23 | 2001-11-06 | イシス イノベイション リミテッド | Light emitting dendrimer and light emitting device |
| US6680131B1 (en) * | 1999-07-30 | 2004-01-20 | Sony Corporation | Organic electroluminescent device |
| WO2006000388A1 (en) * | 2004-06-26 | 2006-01-05 | Merck Patent Gmbh | Organic electroluminescent device |
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