GB2356738A - Ionic salt dyes as amorphous, thermally stable emitting and charge transport layers in organic light emitting diodes - Google Patents
Ionic salt dyes as amorphous, thermally stable emitting and charge transport layers in organic light emitting diodes Download PDFInfo
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- GB2356738A GB2356738A GB0018081A GB0018081A GB2356738A GB 2356738 A GB2356738 A GB 2356738A GB 0018081 A GB0018081 A GB 0018081A GB 0018081 A GB0018081 A GB 0018081A GB 2356738 A GB2356738 A GB 2356738A
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- organic dye
- counterion
- ionizable substituent
- charge transport
- amorphous
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- 150000003839 salts Chemical class 0.000 title claims description 22
- 239000000975 dye Substances 0.000 title description 21
- -1 phenylene vinylenes Chemical class 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 239000000463 material Substances 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 5
- JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical class C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical group CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 4
- 125000000524 functional group Chemical group 0.000 claims 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims 4
- TWVGAEQMWFGWDX-UHFFFAOYSA-N acetylene;thiophene Chemical class C#C.C=1C=CSC=1 TWVGAEQMWFGWDX-UHFFFAOYSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 2
- 150000004291 polyenes Chemical class 0.000 claims 2
- 239000010408 film Substances 0.000 description 23
- 239000010410 layer Substances 0.000 description 17
- 238000000151 deposition Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000000137 annealing Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 238000002679 ablation Methods 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007496 glass forming Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
-
- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Nanotechnology (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Composite Materials (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Description
2356738 Ionic Salt Dyes as Amorphous, Thermally Stable Emitting and Charge
Transport Layers in Organic Light Emitting Diodes
FIELD OF THE INVENTION
This invention relates to organic light emitting diodes and, more particularly, to thermally stable, nominally amorphous films for use as emitting layers or charge transport layers in organic light emitting diodes (OLEDs). Such films are prepared from dyes that are modified to result in ionic salt analogues.
BACKGROUND OF THE INVENTION is organic light emitting diodes (OLED's) have attracted broad attention due to their potential for use in display technologies. A few prototype displays have been demonstrated but their widespread use has not occurred because of problems associated with their operational stability and durability.
The degradation of OLED devices has been attributed to chemical changes of the organic layers, such as oxidation, and also to physical changes such as crystallization. Many potentially useful emitting or charge -transporting materials form polycrystalline films when deposited by physical vapor deposition. Such films contain grain boundaries that can act as luminescence quenching sites. To avoid such a problem, deposition of amorphous (glassy state) thin films seems to be a good alternative approach for device fabrication. However, most nonpolymeric organic dye glasses are thermally unstable and crystallize when subjected to driving voltages in a device, causing device failure.
In traditional OLED devices, the emitting organic dye molecules (D) are generally neutral molecules which interact through weak van der Waals interactions. Because of the weak nature of these interactions, heating of the initially amorphous films (for example joule heating when the device is driven, or even heating during deposition) easily causes rearrangement of the molecules, leading to crystallization and grain growth.
The film crystallization problem has been identified by many researchers in the OLED device field. Efforts to synthesize amorphous dyes have been mainly focused on dissolving them in thermally stable amorphous 2 polymers. A second approach is aimed at synthesizing large, symmetric, rigid and dense molecules that will be more heat-resistive (see Naito et al., J. Physical Chemistry, Vol 101, p. 2350 (1997)). An alternative approach is based on the introduction of spiro centers into defined low molecular weight structures (see Salbeck et al., Synthetic Metals, Vol. 91, p. 209 (1997)).
SUMMARY OF THE INVENTION
The invention modifies dyes so as to form ionic salt derivatives.
Such derivatives are used as emitting or charge transport layers in organic light emitting diodes (OLED Is). The modification involves attachment of ionizable substituents during initial synthesis, followed by formation of an ionic salt. An improvement of the OLED's durability and performance is results from use of such ionic dye salts, since the evaporated films are nominally amorphous, thermally stable and resist further crystallization.
Preliminary devices built using a test compound exhibit superior efficiency.
BRIEF DESCRIPTION OF THE DRAWINGS
Fig. la illustrates a single neutral AEQT molecule.
Fig. ib illustrates the AEQT-2HC1 chloride salt of an ionized AEQT molecule.
Fig. 2. is a powder X-ray diffraction pattern of an A-EQT-2HC1 film 1 and of an AEQT film 2.
Fig. 3a is a scanning electron microscope (SEM) picture of an AEQT-2HC1 film.
Fig. 3b is a scanning electron microscope (SEM) picture of an A.EQT film.
Fig. 4a is a schematic cross-section of an OLED device incorporating an AEQT-2HC1 dye salt as the emitting layer.
Fig. 4b is a schematic bottom view of a substrate showing four device areas.
3 Fig. 5a is a plot of e lectro luminescence versus drive voltage for the OLED device shown in Fig. 4.
Fig. 5b is a plot of current versus drive voltage for the OLED device shown in Fig. 4.
Fig. Sc is a plot of the electroluminescence spectrum for the OLED device shown in Fig. 4.
Fig. 6. is a perylene derivative modified to contain four substituents.
DETAILED DESCRIPTION OF THE INVENTION is The invention converts a dye into an ionic salt and uses the salt as an emitting or charge transport layer in an OLED DEVICE. An oligothiophene dye, based on a quaterthiophene oligomer was modified to include two ethylamino terminal groups (ionizable substituents). A schematic representation of the [5,51 1 1 -bis(aminoethyl) -2,21:5',2'':5' t 21 1 1 - quaterthiophene (AEQT) I molecule can be seen in Fig. Ia. By reacting AEQT with hydrochloric acid (HC1), the neutral amino groups (-NH2) become positively charged (-NH3'). To balance the charge, two chloride anions (Cl-) form ionic bonds with the corresponding ammonium cations (-NH3+). The resulting chloride salt C2oH22S4N2Cl2 or AEQT-2HC1 (Fig. 1b) is the compound used as an emitting layer in an OLED DEVICE.
Deposition of the material as a thin film is accomplished by various inexpensive, low temperature methods such as spin-coating, or thermal evaporation. In this case a single-source, thermal ablation technique was employed for the deposition of nominally amorphous thin films. The powder X-ray diffraction pattern (as shown at 1 in Fig 2) of an as-deposited films wis almost featureless, indicating an amorphous or very fine grained film.
The same pattern was obtained after thermal annealing at 901C and 135'C.
Presumably, this is because the molecules in the salt interact via strong ionic interactions, as well as through van der Waals forces.
The stronger bonding is expected to impede rearrangement of the dye molecules during and after thin film deposition. For comparison, the AEQT dye was evaporated without converting it to a salt. As shown at 2 in Fig.
2, the film is crystalline and well ordered, even without annealing. In fact, attempts to make OLEDs using such films failed. This was due to the 4 granular nature of these crystalline f ilms which could not be properly covered with a top metal electrode, thereby producing inhomogeneous, f ields and electrically shorted devices.
To further establish the ability of the method of the invention to provide amorphous films, scanning electron microscopy (SEM) was used to study the morphological properties of the films. As shown, in Fig. 3a, AEQT-2HC1 films have a very homogeneous and fine grained k -50 nm) structure that is ideal for devices. on the other hand, AEQT films have very irregular surfaces with big grain sizes (-500 nm), making them inappropriate for device fabrication (Fig. 3b).
The structure of a typical OLED DEVICE using a dye salt, as prepared in accord with the invention, is shown in Fig. 4. As a substrate, an optically smooth quartz substrate I was used. A transparent anode comprised a 1500 Angstroms thick layer 2 of indium tin oxide (ITO), that was evapgrated on top of the substrate. A 1200 Angstroms thick silicon dioxide layer 3 was then evaporated through a contact mask in order to define four device areas 4 on top of the ITO layer 2 (shown in Fig. 4b). The emitting layer 5, consisting of the C20H22S4NCl, salt, was deposited next using the single source thermal ablation technique (2400 Angstroms). This was followed by thermal annealing of the samples at 900C for 15 minutes and at 1350C for 2 minutes.
Next a thin layer of the electron transporting agent OXD7 6 was thermally deposited (300 Angstroms) and finally, the device was completed by thermally depositing the cathode. The latter consisted of a magnesiumsilver alloy (25:1) 7, which provides for a low work-function cathode, capped by 1200 Angstroms of pure silver 8 to inhibit air oxidation. The deposition of the OXD7 and of the cathode were performed in a vacuum system by thermal evaporation.
When a voltage 9 is applied across the device, green electroluminescence is readily observed under normal lighting conditions and at room temperature. Device characterization data of this device is shown in Fig. 5. Although unoptimized, the device exhibits low turn-on voltages (less than 9 V) and a high efficiency of 0.25 lm/W.
Previous work by Noda et al. on thin semiconducting f ilms of oligothiophenes yielded devices with inferior efficiencies (10' to 10' lm/W) due to the fact that such films were well ordered and crystalline. By using triphenyl-amino substituted quaterthiophenes to reduce crystallinity, higher efficiencies of 0.03 lm/W were obtained (see Noda et al., Adv.
Materials, Vol. 9, p 720 (1997)). Those reported efficiencies are lower, however, than the efficiencies exhibited by devices made in accord with the invention hereof.
The foregoing device description is only illustrative of the invention. The technique can be extended to hole and electron transport layers of an OLED DEVICE which includes similar organic molecules to those found in the emitting layer and which are also prone to crystallization. In typical OLED devices, either a single charge transport layer is used (electron or hole transporting) or both may be used to enhance charge injection into the organic emission layer.
In summary, instead of using a neutral dye molecule (D), the invention modifies a dye during its synthesis to contain ionizable substituents (A) to give (D-A). An ionic salt (DA X- or DA- X) of the dye is then synthesized by application of an appropriate reactant which contains charge balancing ions (X). When deposited in the form of films, the ionic salts are typically amorphous as opposed to the crystalline f ilms of the neutral dye. In addition, the ionic salt f ilms remain amorphous even when heated to higher temperatures (indicating thermal stability). These ionic salts are used as the emitting layer in OLED devices, which are more efficient and robust than the corresponding neutral dye devices.
Various alternatives can be devised by modifying the components of the (DA X-) dye salt. The most important modification is the appropriate selection of different dyes (D) that define the emission properties of the device (color, intensity). Potential candidates, for example, include derivatives of the tolan, thioxanthone, coumarin, rhodamine and perylene families and the present invention is intended to embrace all such alternatives. This allows preparation of devices with different colors and enables realization of a full color display.
Other factors that can be modified include the use of different ionic substituents (A) and charge balancing ions (X). The charge balancing ion can be either an organic or an inorganic entity. The number of ionic substituents (A) attached to a molecule is also important in the glass forming properties of the resulting films. Since it is believed that the ionic forces present in the salt are responsible for the lack of crystallinity, then by using a larger number of ionic substituents (A), 6 more thermally stable films can be formed. An example is given Fig. 6, in which a perylene derivative has been modified to contain four substituents, to form a (D-A4) X-4 salt.
It should be understood that the foregoing description is only illustrative of the invention. Various alternatives and modifications can be devised by those skilled in the art without departing from the invention. Accordingly, the present invention is intended to embrace all such alternatives, modifications and variances which fall within the scope of the appended claims.
7
Claims (1)
1. An electrolumine scent device comprising: an anode, a cathode and an emitting layer disposed between said anode and said cathode, said emitting layer comprising an organic dye salt material that includes an organic dye containing an ionizable substituent and a counterion to balance a charge of the organic dye.
2. The device of claim 1 wherein said organic dye salt material fluoresces in the visible range.
3. The device of claim 1 wherein said organic dye is selected from the group consisting of: derivatives of tolan, thioxanthone, coumarin, perylene, pyrene, oxadiazole, polyenes, oligothiophenes, oligophenylenes, phenylene vinylenes, thiophene vinylenes and mixtures thereof.
4. The device of claim 1 wherein said organic dye is cluaterthiophene.
5. The device of claim 1 wherein said ionizable substituent is selected from functional groups consisting of: amino-, hydroxy-, oxo-, nitro-, sulfo-, carboxy-, phospho-. 6. The device of claim 1 wherein said ionizable substituent is an 25 alkylamine. 7. The device of claim 1 wherein said ionizable substituent is ethylamine. 8. The device of claim 1 wherein said counterion is selected from the group 30 consisting of: halides, alkali metal cations, alkaline earth cations. 9. The device of claim 1 wherein said counterion is an organic ion containing an ionized form of one or more following functional groups: amino-, hydroxy-, oxo-, nitro-, sulfo-, carboxy-, phospho-. 35 10. An electroluminescent device comprising: an anode, a cathode, an emitting layer, and at least one charge transport layer disposed adjacent to said emitting layer and between said anode and said cathode and comprising an organic dye salt material that includes an organic dye containing an ionizable substituent and a counterion to balance a charge of 40 the organic dye.
8 11. The device of claim 10 wherein said charge transport layer includes molecules selected from the group consisting of: derivatives of tolan, thioxanthone, coumarin, perylene, pyrene, oxadiazole, polyenes, oligothiophenes, oligophenylenes, phenylene vinylenes, thiophene vinylenes and mixtures thereof.
12. The device of claim 10 wherein said ionizable substituent is selected from functional groups consisting of: amino-, hydroxy-, oxo-, nitro-, sulfo-, carboxy-, phospho-.
13. The device of claim 10 wherein said ionizable substituent is an alkylamine.
14. The device of claim 10 wherein said ionizable substituent is is ethylamine.
15. The device of claim 10 wherein said counterion is selected from the group consisting of: halides, alkali metal cations, alkaline earth cations.
16. The device of claim 10 wherein said counterion is an organic ion containing the ionized form of one or more of the following functional groups: amino-, hydroxy-, oxo-, nitro-, sulfo-, carboxy-, phospho-.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/396,324 US6730416B1 (en) | 1999-07-08 | 1999-09-15 | Ionic salt dyes as amorphous, thermally stable emitting and charge transport layers in organic light emitting diodes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB0018081D0 GB0018081D0 (en) | 2000-09-13 |
| GB2356738A true GB2356738A (en) | 2001-05-30 |
| GB2356738B GB2356738B (en) | 2004-03-17 |
Family
ID=23566771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB0018081A Expired - Fee Related GB2356738B (en) | 1999-09-15 | 2000-07-25 | Ionic salt dyes as amorphous, thermally stable emitting and charge transport layers in organic light emitting diodes |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JP3459006B2 (en) |
| KR (1) | KR100371951B1 (en) |
| CN (1) | CN1206745C (en) |
| BR (1) | BR0004230B1 (en) |
| GB (1) | GB2356738B (en) |
| TW (1) | TW456158B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008113753A1 (en) * | 2007-03-16 | 2008-09-25 | Basf Se | Method for the production of rylene tetracarboxylic acid diimides the imide nitrogens of which carry hydrogen atoms and the use thereof |
| US7858967B2 (en) | 2002-02-20 | 2010-12-28 | Novaled Ag | Doped semiconductor material and process for production thereof |
| EP2958403A4 (en) * | 2013-02-18 | 2016-11-09 | Uni De Valéncia | ELECTROLUMINESCENT LAYER FOR OPTOELECTRONIC DEVICE |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002100482A (en) * | 2000-09-20 | 2002-04-05 | Mitsubishi Chemicals Corp | Organic electroluminescent device |
| US6876143B2 (en) * | 2002-11-19 | 2005-04-05 | John James Daniels | Organic light active devices and methods for fabricating the same |
| US7829203B2 (en) * | 2002-03-09 | 2010-11-09 | Cdt Oxford Limited | Polymerisable compositions and organic light-emitting devices containing them |
| JP3825344B2 (en) | 2002-03-15 | 2006-09-27 | 富士写真フイルム株式会社 | Organic EL element and organic EL display |
| KR101311933B1 (en) | 2009-12-29 | 2013-09-27 | 제일모직주식회사 | Conductive polymer, conductive polymer composition, film and opto-electronic device using thereof |
| JP5677036B2 (en) * | 2010-11-08 | 2015-02-25 | キヤノン株式会社 | Organic light emitting device |
| TWI518143B (en) * | 2011-03-31 | 2016-01-21 | Sumitomo Chemical Co | Dye with salt |
| JP6094058B2 (en) * | 2012-05-22 | 2017-03-15 | 日立化成株式会社 | Organic electronic material, ink composition, organic electronic element, organic electroluminescent element, and photoelectric conversion element |
| CN107108461B (en) * | 2014-11-06 | 2020-04-28 | 浦项工科大学校产学协力团 | Perovskite nanocrystalline particles and optoelectronic devices using the same |
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|---|---|---|---|---|
| EP0910100A2 (en) * | 1997-10-14 | 1999-04-21 | Xerox Corporation | Conductive polymer compositions and processes thereof |
| JPH11279426A (en) * | 1998-03-31 | 1999-10-12 | Idemitsu Kosan Co Ltd | Rhodamine dye, color conversion film and organic electroluminescence device |
| JPH11283750A (en) * | 1998-03-27 | 1999-10-15 | Idemitsu Kosan Co Ltd | Organic electroluminescence device |
| WO2000011105A1 (en) * | 1998-08-18 | 2000-03-02 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Complexes of conjugated polyelectrolytes for optoelectronic applications |
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2000
- 2000-07-25 GB GB0018081A patent/GB2356738B/en not_active Expired - Fee Related
- 2000-08-14 TW TW089116356A patent/TW456158B/en not_active IP Right Cessation
- 2000-09-04 KR KR10-2000-0051979A patent/KR100371951B1/en not_active Expired - Fee Related
- 2000-09-12 CN CNB001189956A patent/CN1206745C/en not_active Expired - Fee Related
- 2000-09-14 JP JP2000279995A patent/JP3459006B2/en not_active Expired - Fee Related
- 2000-09-15 BR BRPI0004230-7A patent/BR0004230B1/en not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0910100A2 (en) * | 1997-10-14 | 1999-04-21 | Xerox Corporation | Conductive polymer compositions and processes thereof |
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| Appl. Phys. Lett. Vol. 76, No. 1 January 2000, pages 58-60 K. Chondroudis and D.B. Mitzi * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7858967B2 (en) | 2002-02-20 | 2010-12-28 | Novaled Ag | Doped semiconductor material and process for production thereof |
| WO2008113753A1 (en) * | 2007-03-16 | 2008-09-25 | Basf Se | Method for the production of rylene tetracarboxylic acid diimides the imide nitrogens of which carry hydrogen atoms and the use thereof |
| EP2958403A4 (en) * | 2013-02-18 | 2016-11-09 | Uni De Valéncia | ELECTROLUMINESCENT LAYER FOR OPTOELECTRONIC DEVICE |
Also Published As
| Publication number | Publication date |
|---|---|
| GB0018081D0 (en) | 2000-09-13 |
| KR100371951B1 (en) | 2003-02-14 |
| KR20010050326A (en) | 2001-06-15 |
| GB2356738B (en) | 2004-03-17 |
| JP2001126874A (en) | 2001-05-11 |
| CN1288266A (en) | 2001-03-21 |
| TW456158B (en) | 2001-09-21 |
| CN1206745C (en) | 2005-06-15 |
| JP3459006B2 (en) | 2003-10-20 |
| BR0004230A (en) | 2001-04-10 |
| BR0004230B1 (en) | 2010-09-21 |
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| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 20160725 |