WO2013149958A1 - Use of a semiconducting compound in an organic light emitting device - Google Patents
Use of a semiconducting compound in an organic light emitting device Download PDFInfo
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- WO2013149958A1 WO2013149958A1 PCT/EP2013/056785 EP2013056785W WO2013149958A1 WO 2013149958 A1 WO2013149958 A1 WO 2013149958A1 EP 2013056785 W EP2013056785 W EP 2013056785W WO 2013149958 A1 WO2013149958 A1 WO 2013149958A1
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- electron transporting
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Classifications
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- 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
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Definitions
- OLEDs organic light emitting diodes
- An OLED comprises a sequence of thin layers substantially made of organic materials between two electrodes.
- the layers typically have a thickness in the range of 1 nm to 5 ⁇ ,
- the layers are usually formed either in vacuum by means of vapor deposition or from a solution, for example by means of spin-coating or printing.
- OLEDs emit light after the injection of charge carriers in a light emitting layer in the form of electrons from the cathode side and in form of holes from the anode side.
- the charge carrier injection is effected on the basis of an applied external voltage, the subsequent formation of excitons in a light emitting zone and the radiative recombination of those excitons.
- At least one of the electrodes is transparent or semitransparent, in the majority of cases in the form of a transparent oxide, such as indium tin oxide ( ⁇ ), or a thin metal layer.
- Flat displays based on OLEDs can be realized both as a passive matrix and as an active matrix.
- the image is generated by for example, the lines being successively selected and an image information item selected on the columns being represented.
- Such displays are restricted to a size of approximately 100 lines for technical construction reasons.
- OLED layer stacks used for displays are described by Dua et al (DOI: 10.1002/adfm.201 100943).
- Duan shows blue OLEDs and white OLEDs. He modified the devices with one light emitting layer to a double and triple light emitting layer, achieving a longer lifetime at the cost of a more complex device stack.
- Other state-of-the art stacks are disclosed in US6878469 B2, WO 2009/107596 Al and US 2008/0203905.
- OLEDs have also been used for lighting, currently available products have efficiency for warm-white of up to 45 lm/W.
- Formula 1 wherein each of R 1 , R 2 , R 1 , R 2 is independently selected from H, Ci-C 6 alkyl, Cj-C 6 haloalkyl and Cg-Cio aryl or both substituents on the same aromatic ring of the xanthenc skeleton are hydrocarbyl groups linked with each other to form together an anelated divalent C 2 -C i o hydrocarbyl group;
- X and X ' are independently selected from C and N,
- the electronic device is an organic light emitting device.
- the electronic device further comprises a second electron transporting layer between the first electron transporting layer and the first electrode.
- the emitting layer, the first electron transporting layer, and the second electron transporting layer form a consecutive sequence of layers with direct contact between the layers.
- the second electron transporting layer comprises at least 2 different compounds, one of them serving as an electron transporting matrix and another one serving as an electrical dopant.
- An electrical dopant is a compound improving electrical properties of the matrix in a device, especially its conductivity and/or its charge injection properties.
- the second electron transporting layer comprises an electron transporting matrix and an electrical dopant.
- the electron transporting matrix in the second electron transporting layer comprises compoimd of formula 1.
- the first electron transporting layer comprises an electrical dopant.
- Table 1 summarizes results from device experiments described in more detail in examples, shows that for the use in electron transporting layers of electronic devices, reasonable selection must be done from the compounds generally proposed for the OLED use in the above mentioned previous art document CN101440082A.
- Formula 1 compounds offer high glass transition temperatures resulting in high thermal stability of the device.
- FIG. 2 shows a schematic illustration of a device in which the present invention can be incorporated.
- FIG. 3 shows ⁇ NMR spectrum of the inventive compound C3
- FIG. 4 shows ⁇ NMR spectrum of the inventive compound CI
- FIG. 5 shows 1H NMR spectrum of the inventive compound C2
- FIG. 6 shows H NMR spectrum of the comparative compound El
- FIG. 8 shows 1H NMR spectrum, of the inventive compound C6
- FIG. 9 shows 1H NMR spectrum of the inventive compound C4
- FIG. 10 shows ⁇ NMR spectrum of the inventive compound C5
- FIG. 11 shows the current density versus applied bias for the inventive and comparative examples.
- FIG. 12 shows the luminance intensity density versus applied bias for the inventive and comparative examples.
- Fig. 1 shows a stack of anode (10), organic semiconducting layer (11) comprising the light emitting layer, electron transporting layer (ETL) (12), and cathode (13). Other layers can be inserted between those depicted, as explained herein.
- Fig. 2 shows a stack of an anode (20), a hole injecting and transporting layer (21), a hole transporting layer (22) which can also aggregate the function of electron blocking, a light emitting layer (23), an ETL (24), and a cathode (25). Other layers can be inserted between those depicted, as explained herein.
- the wording "device” comprises the organic light emitting diode. Material properties - energy levels
- IP ionization potentials
- UPS ultraviolet photo spectroscopy
- the substrate can be flexible or rigid, transparent, opaque, reflective, or translucent.
- the substrate should be transparent or translucent if the light generated by the OLED is to be transmitted through the substrate (bottom emitting).
- the substrate may be opaque if the light generated by the OLED is to be emitted in the direction opposite of the substrate, the so called top-emitting type.
- the OLED can also be transparent.
- the substrate can be either arranged adjacent to the cathode or anode.
- Electrodes are the anode and the cathode, they must provide a certain amount of conductivity, being preferentially conductors.
- the "first electrode” is the cathode.
- At least one of the electrodes must be semi-transparent or transparent to enable the light transmission to the outside of the device.
- Typical electrodes are layers or a stack of layer, comprising metal and/or transparent conductive oxide.
- Other possible electrodes are made of thin busbars (e.g. a thin metal grid) wherein the spaces between the busbars is filled (coated) with a transparent material with a certain conductivity, such as graphene, carbon nanotubes, doped organic semiconductors, etc. ⁇
- the anode is the electrode closest to the substrate, which is called non-inverted structure.
- the cathode is the electrode closest to the substrate, which is called inverted structure.
- Typical materials for the Anode are ITO and Ag.
- Typical materials for the cathode are Mg:Ag (10 vol.% of Mg), Ag, ITO, Al. Mixtures and multilayer are also possible.
- the cathode comprises a metal selected from Ag, Al, Mg, Ba, Ca, Yb, In, Zn, Sn,
- Sm, Bi, Eu, Li more preferably from Al, Mg, Ca, Ba and even more preferably selected from
- a cathode comprising an alloy of Mg and Ag.
- HTL Hole-Transporting Layer
- the HTL is comprised between the anode and the LEL or between the hole generating side of a CGL and the LEL.
- the HTL can be mixed with another material, for example a p-dopant, in which case it is said the HTL is p- doped.
- the HTL can be comprised by several layers, which can have different compositions. P-doping the HTL lowers its resistivity and avoids the respective power loss due to the otherwise high resistivity of the undoped semiconductor.
- the doped HTL can also be used as optical spacer, because it can be made very thick, up to 1000 nra or more without significant increase in resistivity.
- HIL Hole-Injecting Layer
- the HIL is a very thin layer ( ⁇ 10 nm).
- the hole injection layer can be a pure layer of p-dopant and can be about 1 nm thick.
- an HIL may not be necessary, since the injection function is already provided by the HTL.
- the light emitting layer must comprise at least one emission material and can optionally comprise additional layers. If the LEL comprises a mixture of two or more materials the charge carrier injection can occur in different materials for instance in a material which is not the emitter, or the charge carrier injection can also occur directly into the emitter. Many ⁇ different energy transfer processes can occur inside the LEL or adjacent LELs leading to different types of emission. For instance excitons can be formed in a host material and then be transferred as singlet or triplet excitons to an emitter material which can be singlet or triplet emitter which then emits light. A mixture of different types of emitter can be provided for higher efficiency. Mixed light can be realized by using emission from an emitter host and an emitter dopant.
- Blocking layers can be used to improve the confinement of charge carriers in the LEL, these blocking layers are further explained in US 7,074,500 B2.
- ETL Electron-Transporting Layer
- the ETL is comprised between the cathode and the LEL or between the electron generating side of a CGL and the LEL.
- the ETL can be mixed with an electrical n-dopant, in which case it is said the ETL is n- doped.
- the ETL can be comprised by several layers, which can have different compositions. Electrical n -doping the ETL lowers its resistivity and/or improves its ability to inject electrons into an adjacent layer and avoids the respective power loss due to the otherwise high resistivity (and/or bad injection ability) of the undoped semiconductor.
- the doped ETL can also be used as optical spacer, because it can be made very thick, up to 1000 ran or more without significant increase in resistivity.
- the present invention also employs a compound according to formula 1 in the ETL, which compound can be used in combination with other materials, in the whole layer or in a sublayer of the ETL.
- ETLl comprises 2 layers, the first ETL (ETLl) and the second ETL (ETL2), ETLl is closer to the LEL than the ETL2.
- ETLl comprises the compound according to formula 1, even more preferably consists only of material according to formula 1.
- ETLl is closer to the substrate than ETL2.
- the ETL2 comprises a compound according to formula 1.
- the ETL2 is electrically doped.
- ETLl and ETL2 comprise the same compound according to formula 1.
- EIL Electron-Injecting Layer
- CGL Charge generation layer
- the OLED can comprise a CGL which can be used in conjunction with an electrode as inversion contact, or as connecting unit in stacked OLEDs.
- a CGL can have the most different configurations and names, examples are pn-j unction, connecting unit, tunnel junction, etc. Best examples are pn junctions as disclosed ie US 2009/0045728 Al, US 2010/0288362 AL Metal layers and or insulating layers can also be used.
- the OLED comprises two or more LELs separated by CGLs
- the OLED is named a stacked OLED, otherwise it is named a single unit OLED
- the group of layers between two closest CGLs or between one of the electrodes and the closest CGL is named a electroluminescent unit (ELU). Therefore a stacked OLED can be described as anode/E LU i / ⁇ C G Lx ELU : + ⁇ ⁇ ⁇ /cathode, wherein x is a positive integer and each CGLx or each ELUi + x can be equal or different.
- the CGL can also be formed by the adjacent layers of two ELUs as disclosed in US2009/0009072 AL Further stacked OLEDs are explained e.g. in US 2009/0045728 Al, US 2010/0288362 Al, and references therein. Deposition of Organic Layers
- Any organic semiconducting layers of the inventive display can be deposited by known techniques, such as vacuum thermal evaporation (VTE), organic vapour phase deposition, laser induced thermal transfer, spin coating, blade coating, slot dye coating, Inkjet printing, etc.
- VTE vacuum thermal evaporation
- a preferred method for preparing the OLED according to the invention is vacuum thermal evaporation.
- the ETL is formed by evaporation.
- the ETL is formed by co-evaporation of the electron transporting matrix (ETM) and the additional material.
- the additional material may be mixed homogeneously in the ETL.
- the additional material has a concentration variation in the ETL, wherein the concentration changes in the direction of the thickness of the stack of layers. It is also foreseen that the ETL is stractured in sub-layers, wherein some but not all of these sub-layers comprise the additional material. Electrical doping
- the present invention can be used in addition or in combination with electrical doping of organic semiconducting layers.
- OLEDs comprising electrically doped layers.
- the electrical doping means improving of electrical properties, especially the conductivity and/or injection ability of a doped layer in comparison with neat charge-transporting matrix without a dopant.
- hole transport layers are doped with a suitable acceptor material (p -doping) or electron transport layers with a donor material (n-doping), respectively.
- p -doping acceptor material
- n-doping donor material
- the redox doping increases the density of charge carriers of a semiconducting matrix in comparison with the charge carrier density of the undoped matrix.
- doped charge-carrier transport layers p-doping of the hole transport layer by admixture of acceptor-like molecules, n-doping of the electron transport layer by admixture of donor-like molecules
- organic light-emitting diodes is, e.g., described in US 2008/203406 and US 5,093,698.
- US2008227979 discloses in detail the charge-transfer doping of organic transport materials, with inorganic and with organic dopants. Basically, an effective electron transfer occurs from the dopant to the matrix increasing the Fermi level of the matrix.
- the LUMO energy level of the dopant is preferably more negative than the HOMO energy level of the matrix or at least slightly more positive, not more than 0.5 eV, to the HOMO energy level of the matrix.
- the HOMO energy level of the dopant is preferably more positive than the LUMO energy level of the matrix or at least slightly more negative, not lower than 0.5 eV, to the LUMO energy level of the matrix. It is further more desired that the energy level difference for energy transfer from dopant to matrix is smaller than + 0.3 eV.
- CuPc copperphthalocyanine
- F4TCNQ tetrafiuoro- tetracyanoquinonedimethane
- ZnPc zincphthalocyanine
- a-NPD ⁇ , ⁇ '- Bisfnaphthalen- 1 -yl)-N,N'-bis(phenyl
- Typical examples of known redox doped electron transport materials are: fullerene C60 doped with acridine orange base (AOB); perylene-3 ,4,9, 10-tetracarboxylic-3 ,4,9, 10-dianhydride (PTCDA) doped with leuco crystal violet; 2,9 - di (phenanthren-9-yl) - 4,7 - diphenyl - 1,10 - phenanthroline doped with tctrakis ( 1 ,3,4,6,7,8 - hexahydro - 2H - pyrimido [ 1 ,2 - a] pyrimidinato) ditung-sten (II) (W 2 (hpp) 4 ); naphthalene tetracarboxylic acid di -anhydride (NTCDA) doped with 3,6-bis-(dimethyl amino)-acridinc; NTCDA doped with bis(ethylene- dithio) tetrathiafulvalenc
- n-dopants having relative molecular weight above 200, wherein a diffusion of the dopant into adjacent layers is substantially suppressed.
- Most preferred n-dopants in the electrically doped semiconducting material according to the invention are strongly reducing metal complexes like W (hpp) 4 , having their redox potential, measured by cyclic voltammetry (CV) in TUF vs. Fc+/Fc standard, below (in other words, more negative than) ⁇ - 2.0 V.
- Preferred ETL matrix compounds of the present invention are:
- the target compound was yielded as a white solid 44.4 g (61 %).
- methanesulfonic acid (7.7 mL, 11.40 g, 4.0 eq, 1 18.6 mmol) was added in one portion to a mixture of naphthalen- 1 -ol (17.06 g, 4.0 eq, 118.3 mmol) and 2,7- dibromo-9H-fluoren-9-one (10.00 g, 1.0 eq, 29.6 mmol).
- the mixture was heated to 150°C over 21 hours maintaining the argon atmosphere. After cooling down to room temperature water (200 mL) and dichloromethane (500 mL) were added, the layers were separated and the organic layer was washed with water (Ix 100 mL) and dried over magnesium sulphate.
- R 1 , R 2 , R l , R 2 being another moiety than hydrogen or anelated benzo-ring
- R 1 , R 2 , R l , R 2 being another moiety than hydrogen or anelated benzo-ring
- R 1 , R 2 , R l , R 2 being another moiety than hydrogen or anelated benzo-ring
- R 1 , R 2 , R l , R 2 being another moiety than hydrogen or anelated benzo-ring
- naphthalen-2-yl- boronic acid 15.2 g (2.0 eq, 88.38 mmol)
- the grayish solid obtained after work up was additionally triturated in hot ethylacetate (100 mL), methanol (100 mL) and dichloromethane (200 mL) subsequently. After filtration the solid was solved in toluene and filtered over Celite. Evaporation of the solvent lead to a precipitate. It was filtered and dried in vacuum. The product was obtained as yellowish solid.
- the grayish solid obtained after work up was additionally filtered through a pad of Celite with hot chloroform. After evaporation of the solvents, the solid was triturated with hot ethylacetate, filtered and dried under reduced pressure. The product was obtained as white solid.
- a bottom emitting blue OLED was fabricated on a glass substrate coated with patterned ITO (90 run thickness), with the following layer sequence:
- a-NPD p-doped ,N'-Bis(naphthalen- 1 -yl)-N,N'-bis(phenyl)-benzidine
- PD2 p-doped ,N'-Bis(naphthalen- 1 -yl)-N,N'-bis(phenyl)-benzidine
- TCTA undoped 4,4',4"-tris(carbazol-9-yl)-triphenylamine
- TCTA emitter layer with TPBl:Firpic (molar ratio 4:1) with thickness of 15 nm.
- TPBI is l ,3,5-tris(l-phenyl-lH-benzimidazol-2-yl)benzene and Firpic is bis(3,5- difluoro-2-(2-p Tidyl-(2-carboxypyridyl)iridium(IIi);
- the device was encapsulated with a glass cover containing getter.
- the voltage at 10 mA cm 2 is 4.0 V and the device achieves 1000 cd/m 2 at a voltage of 4.3 V,
- Example 2 A second OLED was fabricated as in example 1, except that the compound CI was replaced by compound C2.
- the voltage at 10 mA/cm 2 is 4.3 V and the device achieves 1000 cd/m 2 at a voltage of 4.8 V.
- a third OLED was fabricated as in example 1, except that the compound CI was replaced by compound C3.
- the voltage at 10 mA cm is 4.0 V and the device achieves 1000 cd/m at a voltage of 4.2 V.
- a comparative OLED was fabricated as in example 1, except that the compound CI was replaced by 2,7-di(naphthalen- 1 -yl)spiro[fIuorene-9,9'-xanthene] (El).
- the voltage at 10 mA/cm 2 is 5.8 V and the device achieves 1000 cd/m 2 at a voltage of 6.5 V, which is considerably higher than for the examples according to the invention.
- An additional comparative OLED was fabricated as in example 1 , except that the compound CI was replaced by 2,7-diphcnylspiro[fluorene-9,9'-xanfhene] (E3).
- the voltage at 10 mA/cm is 5.0 V and the device achieves 1000 cd/m at a voltage of 5.6 V, which is considerably higher than for the examples according to the invention.
- Fig. 11 shows the current density versus the applied bias of above described devices.
- (1) refers to compound CI
- (2) refers to compound El
- (3) refers to compound C2
- (4) refers to compound C3
- (5) refers to compound E3. It can be seen that there is a dramatic difference in the current magnitude between the inventive compounds CI, C2, C3 on one side and comparative compounds El and E3 on the other side, of more than one order of magnitude, in the range of typical operating voltages.
- Fig. 12 shows the density of the luminous intensity versus the applied bias of above described devices.
- (1) refers to compoimd CI
- (2) refers to compound El
- (3) refers to compound C2,
- the working and comparative examples were repeated with the same arrangement with the TPBI blocking layer having thickness 10 nm.
- the results are summarized in Table 1.
- the inventive compounds clearly show an unexpected advantage over comparative compounds which either have structural similarity or equal LUMOs or even both.
- the similar LUMO levels should make the inventive and comparative compounds similarly dopable.
- the inventive compounds show UEexpectedly good dopability in comparison with the structurally as well as functionally (in terms of the LUMO level) closest comparative compounds.
- the practical applicability of this surprising finding was successfully demonstrated through improved performance of OLED devices comprising inventive compounds.
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CN104167498A (en) * | 2014-08-21 | 2014-11-26 | 上海道亦化工科技有限公司 | Organic light-emitting device |
WO2015197156A1 (en) * | 2014-06-25 | 2015-12-30 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
EP2963697A1 (en) | 2014-06-30 | 2016-01-06 | Novaled GmbH | Electrically doped organic semiconducting material and organic light emitting device comprising it |
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Also Published As
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KR102156221B1 (en) | 2020-09-15 |
KR20150002740A (en) | 2015-01-07 |
EP2834321B1 (en) | 2017-05-17 |
CN104321406A (en) | 2015-01-28 |
EP2834321A1 (en) | 2015-02-11 |
US20150115241A1 (en) | 2015-04-30 |
CN104321406B (en) | 2017-06-16 |
TW201400468A (en) | 2014-01-01 |
JP2015518653A (en) | 2015-07-02 |
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