CN1206745C - Ion salt dyestuff used as heat emission or electric charge transferring layer in organic LED - Google Patents

Ion salt dyestuff used as heat emission or electric charge transferring layer in organic LED Download PDF

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CN1206745C
CN1206745C CNB001189956A CN00118995A CN1206745C CN 1206745 C CN1206745 C CN 1206745C CN B001189956 A CNB001189956 A CN B001189956A CN 00118995 A CN00118995 A CN 00118995A CN 1206745 C CN1206745 C CN 1206745C
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ionizable
electric charge
ion
organic
charge
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CN1288266A (en
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K·肖德鲁迪斯
D·B·米特兹
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Core Usa Second LLC
GlobalFoundries Inc
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International Business Machines Corp
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    • 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)

Abstract

The invention modifies and converts neutral dye molecules to ionic salts (D-A<+> X<-> or DA<-> X<+>), and employs them as emitting or charge transport layers in organic light emitting diodes (OLED). This is achieved by attaching ionizable substituents (A) on the dye molecule during initial synthesis, and then reacting it with an appropriate agent that contains charge balancing ions (X). These ionic compounds can be deposited as amorphous films using conventional evaporation techniques. They are thermally stable to crystallization. OLED devices incorporating such dye salts for emitting layers exhibit superior efficiencies and durability.

Description

Make the ion salt dyestuff that heat emission and charge transport layer are used in the Organic Light Emitting Diode
The present invention relates to Organic Light Emitting Diode, more particularly, the present invention relates in Organic Light Emitting Diode (OLED), be used as the heat-staple of emission layer or charge transport layer and be generally amorphous film.These films are to prepare with the dyestuff that produces the ion salt analog from modification.
Organic Light Emitting Diode (OLED) is owing to the internal potential that they are used in the Display Technique field has attracted to note widely.Shown several model machine displays, but also do not had extensive use, this is because exist and their stability and the cause of relevant some problems of durability.
The reason that the OLED device quality descends is the chemical change (as oxidation) of organic layer, and also having a reason is physical change (as crystallization).When carrying out deposit by the physical vapor deposition process, many emissions that come in handy or charge transport material have formed polycrystalline film.These films comprise granule boundary, and these granule boundaries may play luminescence queenching point.For fear of this problem occurring, a good alternative of the film of deposit amorphous (vitreousness) device manufacturing seemingly.Yet most of non-polymer organic dyestuff glass are heat-labile, and will produce crystallization when being activated voltage in device, make component failure.
In traditional OLED device, the organic dyestuff of emission (D) in general is neutral molecule, only by weak van der Waals interaction and other interaction of molecules.Because these interactional character are very weak, thus the heating of initial amorphouse film (Jiao Erre when driving element for example, perhaps, the steady heating during deposit) cause rearranging of molecule easily, cause crystallization or germination.
Many researchers have realized that the crystallisation problems of this film in the OLED devices field.The effort of synthetic amorphous dyestuff mainly concentrates on the thermally-stabilised amorphous polymer aspect that solves them.Another kind of solution route is at synthetic big, symmetry, rigidity and fine and close molecule, and these molecules have bigger thermal resistance (seeing people's such as Naito physical chemistry magazine, the 101st volume, the 2350th page, 1997 years).A kind of scheme that can replace be based in the low-molecular-weight structure that defines the volution center of introducing (see people such as Salveck " synthetic metal ", the 91st volume, the 209th page, 1997).
Modification dyestuff of the present invention is so that form the ion salt derivative.Such derivative is used as emission layer or charge transport layer in Organic Light Emitting Diode (OLED).This modification relates to the ionizable substituent combination between initial synthesis phase, and then forms ion salt.Use this ion salt dyestuff can improve durability and the performance of OLED, this is because the film of evaporation is cause amorphous, heat-staple, can also anti-recrystallizing in the ordinary course of things.The preliminary device exhibits of using a kind of test compounds to constitute goes out excellent efficient.
Fig. 1 a represents single neutral AEQT molecule.
Fig. 1 b represents the AEQT2HCl chloride salt of Ionized AEQT molecule.
Fig. 2 is the powder x-ray diffraction curve of AEQT2HCl film 1 and AEQT2HCl film 2.
Fig. 3 a is scanning electron microscopy (SEM) image of AEQT2HCl film.
Fig. 3 b is scanning electron microscopy (SEM) image of AEQT film.
Fig. 4 a is the constructed profile of OLED device, has wherein added the AEQT2HCl dye salt as emission layer.
Fig. 4 b is the schematic bottom view of substrate, expresses 4 device regions.
Fig. 5 a is that the electricity of OLED device shown in Figure 4 causes the curve chart of brightness with respect to driving voltage.
Fig. 5 b is the curve chart of the electric current of OLED device shown in Figure 4 with respect to driving voltage.
Fig. 5 c is the curve chart that the electricity of OLED device shown in Figure 4 causes the brightness spectrum.
Fig. 6 is 4 the substituting group De perylene derivatives that comprise through modification.
The present invention is converted to ion salt with a kind of dyestuff, and uses ion salt as emission layer in the OLED device or charge transport layer.Carry out modification for Oligopoly thiophene dyestuff, make it comprise two ethylamino end groups (ionizable substituting group) based on the tetrad thiophene oligomers.In Fig. 1 a, can see [5,5 -two (amino-ethyl)-2,2 ': 5 ', 2 ": 5 ", 2 -four thiophene (AEQT)] and the expression of a signal of molecule.By the reaction of AEQT and hydrochloric acid (HCl), neutral amino (NH 2) become (NH that has positive charge 3 +).For balancing charge, the anion (Cl of two chlorine -) and corresponding ammonium cation (NH 3 +) the formation ionic bond.The chloride salt C that finally obtains 20H 22S 4N 2Cl 2Or AEQT2HCl (Fig. 1 b) is exactly the compound as emission layer in the OLED device.
Become film that the low temperature method of various cheapnesss, for example spin coating or thermal evaporation are arranged this deposition of materials.In this case, can use a kind of thermal ablation technology (disclose this technology in people's such as Chondroudis the U.S. Patent application of sequence number as the common unexamined of No.09/192130, this application transfers the common assignee with the application) of single source to come deposit to be generally amorphous film.The powder x-ray diffraction curve of the film of deposit (shown in label among Fig. 2 1) almost is undistinguishable like this, and this shows it is the film of an amorphous or superfine microparticle shape.Behind 90 ℃ and 135 ℃ of thermal annealings, obtain same curve.Can guess, this be because: the molecule in the salt be through strong ionic interaction and by van der waals force interactional.
Expect that this stronger combination can hinder dye molecule during the deposit of film and rearrange after this.In order to compare evaporation AEQT dyestuff under the situation that does not make AEQT dyestuff conversion salify.Shown in the label among Fig. 22, this film is crystallization, and is complete ordering, even also be like this under the condition that does not have annealing.In fact, the trial of using this film to make OLED is failed.This is because the particle properties of these crystalline film determines that the metal electrode of top can not cover these crystalline film fully, has therefore produced uneven electric field and has made the device electrical short.
In order to confirm that further method of the present invention provides the ability of amorphouse film, use scanning electron microscopy (SEM) to study the morphological properties of film.Shown in Fig. 3 a, the AEQT2HCl film has the structure of meticulous extremely uniformly graininess (＜about 50nm), and this is desirable for device.On the other hand, the AEQT film has extremely irregular surface, and big particle (being about 500nm) is arranged, and this makes them be not suitable for the manufacturing (Fig. 3 b) of device.
In Fig. 4, express the structure of use according to a kind of typical OLED device of the dye salt of the present invention's preparation.Use the level and smooth quartz substrate 1 of optical grade as substrate.Transparent anode comprises the thick indium tin oxide of 1500 dusts (ITO) layer 2, and layer 2 is on the substrate evaporated on top.Then, evaporate the thick silicon dioxide layer 3 of one deck 1200 dusts, thereby defined 4 device regions 4 (shown in Fig. 4 b) at the top of ITO layer 2 by contact mask.Then, use the thermal ablation deposition techniques emission layer 5 (2400 dust) in single source, said emission layer 5 is by C 20H 22S 4N 2Cl 2Salt is formed.Subsequent, make sample 90 ℃ of following thermal annealings 15 minutes, and 135 ℃ of annealing 2 minutes down.
Subsequent, the thin layer 6 of thermal deposition electron transporting agent OXD7 (300 dust) is finished this device by the thermal deposition negative electrode at last.Negative electrode is made up of magnesium silver alloy (25: 1) 7, and it provides low work function negative electrode, is covered to suppress air oxidation by the fine silver 8 of 1200 dusts.The deposit of OXD7 and negative electrode is finished in vacuum system by thermal evaporation.
When the two ends at device add voltage 9, under normal luminescent condition and under the room temperature, observe green electroluminescence brightness easily.In Fig. 5, express the device feature data of this device.Though be not optimum state, this device shows the high efficiency of low conducting voltage (less than 9 volts) and 0.25lm/W.
The efficient very low (10 of the device that the former work of the film, semiconductor film of relating to persons Oligopoly thiophenes such as Noda obtains -4To 10 -8Lm/W), its reason is that these films are complete ordering and are crystallizations.Reduce crystallization by the tetrad thiophene that uses triphenylamine to replace, obtained higher efficient 0.03lm/W (see people such as Nod " advanced material ", the 9th volume, 720 pages, 1997).But the efficient of these reports all is lower than the efficient of device exhibits made in accordance with the present invention.
More than all be for illustrative description of the present invention for the description of device.This technology can be generalized to the hole and the electron supplying layer of OLED device, and said this device comprises the organic molecule that is similar to those molecules of finding in emission layer, and these molecules are easy to crystallization.In typical OLED device, perhaps use single charge transport layer (carrying out the conveying in electronics or hole), perhaps utilize the conveying in electronics and hole to inject with the electric charge of strengthening in organic emission layer.
Add up to, the present invention does not use neutral dye molecule (D), but between its synthesis phase the modification dyestuff, comprising ionizable substituting group (A), thereby obtain (D-A).Then, by applying the ion salt (DA of the synthetic dyeing of suitable reactant that comprises charge balance ion (X) +X -Or DA -X +).When with the form of ion salt deposit film forming, ion salt is amorphous in the ordinary course of things, and the crystalline film of this and neutral dye is opposite.In addition, even being heated to higher temperature, the film of ion salt still remains amorphous (showing Heat stability is good).Use these ion salt as the emission layer in the OLED device, they are more effective and more durable than the device of corresponding neutral dye.
By modification (DA +X -) component of dye salt can design various alternatives.Most important modification is suitably to select different dyestuff (D), and this dyestuff has defined the emission characteristic (color, intensity) of device.Possible candidate object for example comprises: diphenyl acetylene derivatire, thioxanthones, cumarin, rhodamine, He perylene family, the present invention are intended to comprise all such derivatives.So just device can be produced, and full color demonstration can be implemented with different colours.
Other factors that can modification comprise uses different ion substituent (A) and charge balance ion (X).Charge balance ion can be organic body or inorganic body.The number that is fixed to the ion substituent (A) on the molecule also is very important in the glass formation character of final film.Owing to believe that the ionic forces that exists is can not produce crystallization in salt,, just can form the film of better heat stability by using the ion substituent (A) of greater number.Fig. 6 has provided an example, and Qi Zhong De perylene derivative modification to be comprising 4 substituting groups, thereby forms a kind of (D-A + 4) X - 4Salt.
Should be appreciated that above description is just for explanation of the present invention.The common technique personnel of this area can design various replacements and improvement not departing under the condition of the present invention.Therefore, the present invention is intended to comprise all such replacement and the improvement in the scope that drops on described claims.

Claims (22)

1, a kind of electroluminescent device, it comprises: anode, negative electrode and be located at said anode and said negative electrode between emission layer, said emission layer includes the organic dye salt material, and this organic dyestuff salt material comprises containing and is ionized with the ionizable substituting group that carries electric charge with in order to the organic dyestuff of the counter ion of the said electric charge of balance.
2, the device of claim 1 is characterized in that: said organic dyestuff salt material is emitted in the fluorescence of visible-range.
3, the device of claim 1 is characterized in that: said organic dyestuff is selected from: the derivative of tolans, thioxanthones, cumarin, perylene, pyrene, oxadiazole, Oligopoly thiophene, low polyphenylene, phenylene vinylidene, thiophene ethenylidene and their mixture.
4, the device of claim 1 is characterized in that; Said organic dyestuff is the tetrad thiophene derivant.
5, the device of claim 1 is characterized in that: said ionizable substituting group is selected from following functional group: amino-, hydroxyl-, oxo-, nitro-, sulfo group-, carboxyl-and phospho-.
6, the device of claim 1 is characterized in that: said ionizable substituting group is an alkylamine.
7, the device of claim 1 is characterized in that; Said ionizable substituting group is an aminoethane.
8, the device of claim 1 is characterized in that: said counter ion is selected from: halide, alkali metal cation and alkaline earth metal cation.
9, the device of claim 1, it is characterized in that: said opposite ion is a kind of organic ion, and this organic ion comprises the ionizable form of one or more following functional groups: amino-, hydroxyl-, oxo-, nitro-, sulfo group-, carboxyl-, phospho-.
10, the electroluminescent device of claim 1 is characterized in that: said counter ion is inorganic.
11, the device of claim 1 is characterized in that: said ionizable substituent said electric charge is a positive charge.
12, the device of claim 1 is characterized in that: said ionizable substituent said electric charge is a negative electrical charge.
13, a kind of electroluminescent device, it comprises: anode, negative electrode, emission layer and close said emission layer and at least one layer charge transfer layer between said anode and said negative electrode, and said charge transport layer comprises a kind of organic dyestuff salt material, and this organic dyestuff salt material comprises comprising and is ionized with the ionizable substituting group that carries electric charge with in order to the organic dyestuff of the counter ion of the said electric charge of balance.
14, the device of claim 13 is characterized in that: said charge transport layer comprises and is selected from following molecule: diphenyl acetylene derivatire, thioxanthones, cumarin, perylene, pyrene, oxadiazole, Oligopoly thiophene, low polyphenylene, phenylene vinylidene, thiophene ethenylidene and their mixture.
15, the device of claim 13 is characterized in that: said ionizable substituting group is selected from following functional group: amino-, hydroxyl-, oxo-, nitro-, sulfo group-, carboxyl-and phospho-.
16, the device of claim 13 is characterized in that: said ionizable substituting group is an alkylamine.
17, the device of claim 13 is characterized in that; Said ionizable substituting group is an aminoethane.
18, the device of claim 13 is characterized in that: said counter ion is selected from: halide, alkali metal cation and alkaline earth metal cation.
19, the device of claim 13, it is characterized in that: said opposite ion is a kind of organic ion, and this organic ion comprises the ionizable form of one or more following functional groups: amino-, hydroxyl-, oxo-, nitro-, sulfo group-, carboxyl-, phospho-.
20, the electroluminescent device of claim 13 is characterized in that: said counter ion is inorganic.
21, the device of claim 13 is characterized in that: said ionizable substituent said electric charge is a positive charge.
22, the device of claim 13 is characterized in that: said ionizable substituent said electric charge is a negative electrical charge.
CNB001189956A 1999-09-15 2000-09-12 Ion salt dyestuff used as heat emission or electric charge transferring layer in organic LED Expired - Fee Related CN1206745C (en)

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US09/396,324 1999-09-15
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
US09/396324 1999-09-15

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CN1206745C true CN1206745C (en) 2005-06-15

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JP2002100482A (en) * 2000-09-20 2002-04-05 Mitsubishi Chemicals Corp Organic electroluminescence element
DE10207859A1 (en) 2002-02-20 2003-09-04 Univ Dresden Tech Doped organic semiconductor material and process for its production
US6876143B2 (en) * 2002-11-19 2005-04-05 John James Daniels Organic light active devices and methods for fabricating the same
ATE450587T1 (en) * 2002-03-09 2009-12-15 Cdt Oxford Ltd POLYMERIZABLE 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
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
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
ES2486890B1 (en) * 2013-02-18 2016-04-20 Universitat De València Electroluminescent layer for an optoelectronic device
CN107108461B (en) * 2014-11-06 2020-04-28 浦项工科大学校产学协力团 Perovskite nanocrystal particle and photoelectric element using same

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US5853906A (en) * 1997-10-14 1998-12-29 Xerox Corporation Conductive polymer compositions and processes thereof
JP3748491B2 (en) * 1998-03-27 2006-02-22 出光興産株式会社 Organic electroluminescence device
JPH11279426A (en) * 1998-03-31 1999-10-12 Idemitsu Kosan Co Ltd Rhodamine-based coloring matter, color-changing membrane and organic electroluminescence device
DE19837390A1 (en) * 1998-08-18 2000-02-24 Max Planck Gesellschaft New complexes of conjugated organic polymer with ionic side chains and ionic surfactant are used as electroluminescent material, e.g. in opto-electronic device, including blue luminescent diode

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