WO1995017018A1 - Elektrolumineszierende anordnungen - Google Patents
Elektrolumineszierende anordnungen Download PDFInfo
- Publication number
- WO1995017018A1 WO1995017018A1 PCT/EP1994/004076 EP9404076W WO9517018A1 WO 1995017018 A1 WO1995017018 A1 WO 1995017018A1 EP 9404076 W EP9404076 W EP 9404076W WO 9517018 A1 WO9517018 A1 WO 9517018A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- liquid
- crystalline
- charge transport
- layers
- transport compounds
- Prior art date
Links
- 239000010410 layer Substances 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000012044 organic layer Substances 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims description 6
- 150000003643 triphenylenes Chemical class 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 150000004074 biphenyls Chemical class 0.000 claims description 2
- 150000004866 oxadiazoles Chemical class 0.000 claims description 2
- 150000002918 oxazolines Chemical class 0.000 claims description 2
- 150000002979 perylenes Chemical class 0.000 claims description 2
- 150000004032 porphyrins Chemical class 0.000 claims description 2
- 150000001911 terphenyls Chemical class 0.000 claims description 2
- 150000004867 thiadiazoles Chemical class 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- 150000001629 stilbenes Chemical class 0.000 claims 1
- 235000021286 stilbenes Nutrition 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
- 239000011521 glass Substances 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- ZXYHFBOHVNFGHI-UHFFFAOYSA-N 1,2,3,4,5,6-hexapentoxytriphenylene Chemical group CCCCCOC1=C(OCCCCC)C(OCCCCC)=C2C3=C(OCCCCC)C(OCCCCC)=CC=C3C3=CC=CC=C3C2=C1OCCCCC ZXYHFBOHVNFGHI-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- WGXGKXTZIQFQFO-CMDGGOBGSA-N ethenyl (e)-3-phenylprop-2-enoate Chemical compound C=COC(=O)\C=C\C1=CC=CC=C1 WGXGKXTZIQFQFO-CMDGGOBGSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 238000000819 phase cycle Methods 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 0 *c(c(*)c1)cc(c2cc(*)c3*)c1c1c4c2c3c(cc(*)c(*)c2)c2c4cc(*)c1* Chemical compound *c(c(*)c1)cc(c2cc(*)c3*)c1c1c4c2c3c(cc(*)c(*)c2)c2c4cc(*)c1* 0.000 description 1
- CAPKORCSQASWEB-UHFFFAOYSA-N 1-(3,6,7,10,11-pentapentoxytriphenylen-2-yl)butan-1-one Chemical group C1=C(C(=O)CCC)C(OCCCCC)=CC2=C(C=C(C(OCCCCC)=C3)OCCCCC)C3=C(C=C(OCCCCC)C(OCCCCC)=C3)C3=C21 CAPKORCSQASWEB-UHFFFAOYSA-N 0.000 description 1
- KNEJSELDOYMNMV-UHFFFAOYSA-N 2,3,6,7,10,11-hexabutoxytriphenylene Chemical group C12=CC(OCCCC)=C(OCCCC)C=C2C2=CC(OCCCC)=C(OCCCC)C=C2C2=C1C=C(OCCCC)C(OCCCC)=C2 KNEJSELDOYMNMV-UHFFFAOYSA-N 0.000 description 1
- -1 Emitter dyes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
Definitions
- An electroluminescent (EL) arrangement is characterized in that it emits light under current flow when an electrical voltage is applied.
- Such arrangements have long been known in the art under the name “light emitting diodes” (LEDs).
- the emission of light comes about by the fact that positive charges (“holes”, holes) and negative charges (“electrons”, electrons) combine while emitting light.
- the LEDs commonly used in technology all consist predominantly of inorganic semiconductor materials.
- EL arrangements have been known for some years, the essential components of which are organic materials.
- organic EL arrangements usually contain one or more layers of organic charge transport compounds.
- the basic structure is shown in Figure 1.
- the numbers 1 to 10 mean:
- an EL arrangement consists of two electrodes, between which there is an organic layer that fulfills all functions, including the emission of light.
- organic layer that fulfills all functions, including the emission of light.
- the invention now relates to electroluminescent arrangements with one or more organic layers which contain at least one layer or one or more liquid-crystalline charge transport compounds.
- organic layers correspond to layers 3 to 7 in FIG. 1; when setting up the EL arrangement, e.g. the electron conductor layer and the electron-injecting layer can be dispensed with.
- the EL arrangement would then e.g. consist of layers 3 to 5.
- charge transport compounds are understood to mean all liquid-crystalline compounds which in some way transport charges (holes and / or electrons). This also explicitly includes those compounds which are components of the emitter layer, that is to say photoluminescent materials, such as e.g. Fluorescent dyes. Liquid crystalline photoconductors are e.g. described in European patent applications 527 376 AI and P 93104832.6.
- the charge transport compounds according to the invention can be low-molecular (“monomeric") liquid-crystalline compounds, oligomers, oligomer mixtures, polymers or polymer networks and mixtures of the compounds mentioned.
- liquid-crystalline charge transport compounds are discotically liquid-crystalline compounds from the series of triphenylenes, phthalocyanines, tricycloquinazolines, perylenes, peryleneimides, decacyclenes or porphyrins, and also calamitically liquid-crystalline from the series of oxadiazoles, thiadiazoles, biphenyls, ilipenyls, ilipenyls , Terphenyls, quaterphenyls or oxazolines.
- the liquid-crystalline charge transport compounds are preferably used for layers 4 and 6 or 3 and 7. They are particularly well suited for this because of their high charge carrier mobility in the liquid-crystalline phase.
- the liquid-crystalline charge transport compounds are particularly preferred in the molecular order present in a liquid-crystalline phase used. This order can be set, for example, by heating the sample. This order can be fixed, for example in the case of polymers which do not crystallize but solidify in a glass-like manner, by freezing into the glass state. It is also possible to fix the liquid-crystalline order by crosslinking in accordance with the method described in German patent application P 4339711.5.
- those layers which do not contain any liquid-crystalline charge-transporting compounds are produced in the customary manner, for example by vapor deposition of low molecular charge transport compounds or by pouring or spinning on solutions of low molecular charge transport compounds in a polymeric binder or directly from solutions of polymeric charge transport compounds or their precursors.
- Layers in which the components of the individual layers are thermally or particularly preferably crosslinked with actinic radiation are particularly preferred. This can e.g. similar to the methods described in German patent applications P 4325885.9 and P 4339711.5.
- the liquid-crystalline charge transport compound is then in the isotropic phase, i.e. e.g. poured as a thin melt.
- the glass plates can have other layers (e.g. orientation layers), which, however, must be thermally so stable that they are not destroyed when the liquid-crystalline charge transport compound, which may be hot, is filled.
- Networked layers as in the German
- Patent application P 4325885.9 are generally suitable.
- liquid crystalline charge transport bond expediently applied to the substrate from solution, for example by casting or spin coating; application in bulk is of course also possible with a sufficiently low melting point.
- the liquid-crystalline order can generally be set by simply heating the sample to convert it to the isotropic state and then cooling it to form the liquid-crystalline phase.
- the liquid-crystalline order can be frozen in the glass state by quenching or fixed by crosslinking (see also German patent application P 43 39 711.5).
- the layers which contain one or more of the liquid-crystalline compounds according to the invention can additionally contain one or more auxiliaries.
- auxiliaries e.g. non-liquid crystalline charge transport compounds, e.g. Emitter dyes, or polymerization initiators and leveling agents, as are known to the person skilled in the art from coating technology.
- FIG. 2 A diagram of the arrangement is shown in FIG. 2, the designations are explained in the following text:
- a solution of 50 mg oxadiazole and 100 mg poly [cinnamic acid vinyl ester] in 1070 mg toluene was first spun onto a glass substrate ("1") vapor-coated with aluminum (20 nm, "2" in FIG. 2). The layer was then crosslinked by exposure to an HBO lamp for five minutes (* 3'1.
- the cavity of the resulting arrangement was finally filled with hexapentyloxytriphenylene at 130 ° C ("7").
- the electroluminescence of this probe was observed at 80 ° C. At this temperature, hexapentyloxytriphenylene is present in the liquid-crystalline DO phase. The light emitted was orange-red at a voltage of 150 V.
- Hexapentyloxytriphenylene (phase sequence k 69 ° C Dho 122 ° C i) is diffused into a cell (see FIG. 3) at a temperature of 130 ° C.
- the cell consists of a cross-shaped arrangement of two electrodes on glass substrates (see FIG. 3), one of which consists of transparent indium tin oxide (ITO) and the other of aluminum (thickness: 60 nm).
- the active area is approximately 2 mm x 2 mm with a thickness of approximately 1.3 ⁇ m.
- the two electrodes After the cell has been filled, the two electrodes are contacted with a conductive two-component adhesive. After applying a voltage of 69 V (positive to ITO) at a temperature of 80 ° C, the arrangement lights up bluish. The emission can be clearly seen in a dark room. Even after a few hours of lighting, no decrease in brightness is discernible.
- the substance 2 capable of forming liquid-crystalline phases is allowed to diffuse into a cell (see FIG. 3) at a temperature of 120 ° C.
- the phase sequence is g34 ° Ck66 ° Cnl02 ° Ci.
- the cell consists of a cross-shaped arrangement of two electrodes, one of which consists of transparent indium-tin oxide and the other of aluminum (thickness: 60 nm).
- the active area is approximately 2 mm x 2 mm with a thickness of approximately 3.0 ⁇ m.
- the two electrodes are contacted with a conductive two-component adhesive. After applying a DC voltage of 200 V (positive to ITO) at a temperature of 85 ° C, the arrangement lights up bluish.
- Figure 3 mean: 1 glass, 2 aluminum, 3 ITO and 4 glue.
- 2,3,6,7, 10, 11-Hexabutyl-oxytriphenylene is allowed to flow into a cell analogous to Example 2 at a temperature of 155 ° C., after contacting as described in Example 2, the cell is adjusted to adjust the isotropic phase up to heated to a temperature of 155 ° C and cooled to 118 ° C after a waiting time of 5 minutes at a cooling rate of 1 K / min.
- a DC voltage of 45 V ITO electrode positive, aluminum electrode negative, the arrangement lights up orange. No light emission can be observed at a voltage of 5 V.
- the isotropic phase is adjusted by heating to a temperature of 120 ° C., and after a waiting time of 5 minutes, the mixture is cooled to 60 ° C. at a cooling rate of 1 K / min.
- a DC voltage of 40 V, ITO electrode positive, aluminum electrode negative is applied, the arrangement lights up orange. At a voltage of 5 V, no light emission can be observed.
- the isotropic phase is adjusted by heating to a temperature of 120 ° C., and after a waiting time of 5 minutes, the mixture is cooled to 20 ° C. at a cooling rate of 1 K / min.
- a DC voltage of 65 V ITO electrode positive, aluminum electrode negative, the arrangement lights up orange. No light emission can be observed at a voltage of 5 V.
- the isotropic phase is set at a temperature of 150 ° C. and after a waiting time of 5 minutes, the mixture is cooled to 100 ° C. at a cooling rate of 1 K / min.
- a DC voltage of 50 V ITO electrode positive, aluminum electrode negative, the arrangement lights up orange. At a voltage of 5 V, no light emission can be observed.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019960703226A KR960706693A (ko) | 1993-12-18 | 1994-12-08 | 전계 발광 장치(electroluminescent devices) |
EP95903326A EP0734592A1 (de) | 1993-12-18 | 1994-12-08 | Elektrolumineszierende anordnungen |
JP7516507A JPH09506646A (ja) | 1993-12-18 | 1994-12-08 | エレクトロルミネセンス装置 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4343412.6 | 1993-12-18 | ||
DE4343412A DE4343412A1 (de) | 1993-12-18 | 1993-12-18 | Elektrolumineszierende Anordnungen |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995017018A1 true WO1995017018A1 (de) | 1995-06-22 |
Family
ID=6505488
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1994/004076 WO1995017018A1 (de) | 1993-12-18 | 1994-12-08 | Elektrolumineszierende anordnungen |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0734592A1 (de) |
JP (1) | JPH09506646A (de) |
KR (1) | KR960706693A (de) |
CN (1) | CN1137841A (de) |
DE (1) | DE4343412A1 (de) |
WO (1) | WO1995017018A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0847228A2 (de) * | 1996-12-09 | 1998-06-10 | Toyo Ink Manufacturing Co., Ltd. | Stoff für organische Elektrolumineszensvorrichtung, und deren Verwendung |
EP0915144A1 (de) * | 1997-11-04 | 1999-05-12 | Dai Nippon Printing Co., Ltd. | Fluoreszent flüssigkristall Ladungstransportmaterial |
WO2001029908A1 (de) * | 1999-10-21 | 2001-04-26 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Transparente organische elektrolumineszenzanordnungen |
DE10257711B4 (de) | 2001-12-27 | 2019-09-26 | Merck Patent Gmbh | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19715054A1 (de) * | 1997-04-11 | 1998-10-15 | Bosch Gmbh Robert | Elektrolumineszierendes Bauelement |
JPH11273859A (ja) * | 1998-03-24 | 1999-10-08 | Sony Corp | 有機電界発光素子及びその製造方法 |
JP2001089681A (ja) * | 1999-09-21 | 2001-04-03 | Canon Inc | ディスコチック液晶化合物及びそれを用いた有機エレクトロルミネセンス素子 |
JP4558153B2 (ja) * | 2000-07-27 | 2010-10-06 | 三星モバイルディスプレイ株式會社 | 有機エレクトロルミネッセンス素子 |
JP2002343572A (ja) * | 2001-03-14 | 2002-11-29 | Canon Inc | ポルフィリン誘導体化合物を用いた発光素子および表示装置 |
CN100433235C (zh) * | 2005-12-20 | 2008-11-12 | 陕西科技大学 | 一种分立式结构的场致发射显示器件 |
JP5543891B2 (ja) * | 2010-09-30 | 2014-07-09 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光表示装置の製造方法及び有機電界発光表示装置 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1987000343A1 (en) * | 1985-06-28 | 1987-01-15 | Ksv-Chemicals Oy | Film aggregate and new compounds therefor |
EP0527376A1 (de) * | 1991-08-10 | 1993-02-17 | BASF Aktiengesellschaft | Organische Photoleiter mit flüssigkristallinen Eigenschaften |
EP0563768A1 (de) * | 1992-04-03 | 1993-10-06 | BASF Aktiengesellschaft | Organische Photoleiter mit flüssigkristallinen Eigenschaften |
-
1993
- 1993-12-18 DE DE4343412A patent/DE4343412A1/de not_active Withdrawn
-
1994
- 1994-12-08 EP EP95903326A patent/EP0734592A1/de not_active Withdrawn
- 1994-12-08 CN CN94194540A patent/CN1137841A/zh active Pending
- 1994-12-08 KR KR1019960703226A patent/KR960706693A/ko not_active Application Discontinuation
- 1994-12-08 WO PCT/EP1994/004076 patent/WO1995017018A1/de not_active Application Discontinuation
- 1994-12-08 JP JP7516507A patent/JPH09506646A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1987000343A1 (en) * | 1985-06-28 | 1987-01-15 | Ksv-Chemicals Oy | Film aggregate and new compounds therefor |
EP0527376A1 (de) * | 1991-08-10 | 1993-02-17 | BASF Aktiengesellschaft | Organische Photoleiter mit flüssigkristallinen Eigenschaften |
EP0563768A1 (de) * | 1992-04-03 | 1993-10-06 | BASF Aktiengesellschaft | Organische Photoleiter mit flüssigkristallinen Eigenschaften |
Non-Patent Citations (2)
Title |
---|
D. ADAM ET AL.: "Transient photoconductivity in a discotic liquid crystal", PHYSICAL REVIEW LETTERS, vol. 70, no. 4, 25 January 1993 (1993-01-25), NEW YORK US, pages 457 - 460 * |
H. SUZUKI ET AL.: "Electroluminescent devices based on Poly(methylphenylsilane)", ADVANCED MATERIALS, vol. 5, no. 10, October 1993 (1993-10-01), WEINHEIM, DE, pages 743 - 746 * |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0847228A2 (de) * | 1996-12-09 | 1998-06-10 | Toyo Ink Manufacturing Co., Ltd. | Stoff für organische Elektrolumineszensvorrichtung, und deren Verwendung |
EP0847228A3 (de) * | 1996-12-09 | 1998-09-02 | Toyo Ink Manufacturing Co., Ltd. | Stoff für organische Elektrolumineszensvorrichtung, und deren Verwendung |
US6150042A (en) * | 1996-12-09 | 2000-11-21 | Toyo Ink Manufacturing Co., Ltd. | Material for organoelectro-luminescence device and use thereof |
US6245449B1 (en) | 1996-12-09 | 2001-06-12 | Toyo Ink Manufacturing Co., Ltd. | Material for organoelectroluminescence device and use thereof |
EP1191020A2 (de) * | 1996-12-09 | 2002-03-27 | Toyo Ink Manufacturing Co., Ltd. | Material für eine organische Elektrolumineszenzvorrichtung und seine Verwendung |
EP1191020A3 (de) * | 1996-12-09 | 2003-01-15 | Toyo Ink Manufacturing Co., Ltd. | Material für eine organische Elektrolumineszenzvorrichtung und seine Verwendung |
EP0915144A1 (de) * | 1997-11-04 | 1999-05-12 | Dai Nippon Printing Co., Ltd. | Fluoreszent flüssigkristall Ladungstransportmaterial |
WO2001029908A1 (de) * | 1999-10-21 | 2001-04-26 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Transparente organische elektrolumineszenzanordnungen |
DE10257711B4 (de) | 2001-12-27 | 2019-09-26 | Merck Patent Gmbh | Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen |
Also Published As
Publication number | Publication date |
---|---|
DE4343412A1 (de) | 1995-06-22 |
EP0734592A1 (de) | 1996-10-02 |
CN1137841A (zh) | 1996-12-11 |
JPH09506646A (ja) | 1997-06-30 |
KR960706693A (ko) | 1996-12-09 |
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