WO2022122607A1 - An ink system and a method for inkjet printing - Google Patents
An ink system and a method for inkjet printing Download PDFInfo
- Publication number
- WO2022122607A1 WO2022122607A1 PCT/EP2021/084307 EP2021084307W WO2022122607A1 WO 2022122607 A1 WO2022122607 A1 WO 2022122607A1 EP 2021084307 W EP2021084307 W EP 2021084307W WO 2022122607 A1 WO2022122607 A1 WO 2022122607A1
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- WIPO (PCT)
- Prior art keywords
- film
- compounds
- derivatives
- range
- ink system
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 31
- 238000007641 inkjet printing Methods 0.000 title claims description 16
- 239000000463 material Substances 0.000 claims abstract description 133
- 239000000203 mixture Substances 0.000 claims abstract description 65
- 238000009472 formulation Methods 0.000 claims abstract description 46
- 238000004090 dissolution Methods 0.000 claims abstract description 33
- 239000003960 organic solvent Substances 0.000 claims abstract description 27
- 229920000642 polymer Polymers 0.000 claims description 56
- 239000002904 solvent Substances 0.000 claims description 45
- 238000001035 drying Methods 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 239000008204 material by function Substances 0.000 claims description 15
- 239000002346 layers by function Substances 0.000 claims description 13
- 238000007639 printing Methods 0.000 claims description 12
- 150000003384 small molecules Chemical class 0.000 claims description 8
- 239000000412 dendrimer Substances 0.000 claims description 5
- 229920000736 dendritic polymer Polymers 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 100
- 125000003118 aryl group Chemical group 0.000 description 69
- -1 rare earths Chemical class 0.000 description 48
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- 125000004432 carbon atom Chemical group C* 0.000 description 34
- 150000003254 radicals Chemical class 0.000 description 30
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- 238000002347 injection Methods 0.000 description 28
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- 239000002019 doping agent Substances 0.000 description 15
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- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- BUAWIRPPAOOHKD-UHFFFAOYSA-N pyrene-1,2-diamine Chemical class C1=CC=C2C=CC3=C(N)C(N)=CC4=CC=C1C2=C43 BUAWIRPPAOOHKD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000005029 thianthrenes Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/52—Electrically conductive inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/40—Ink-sets specially adapted for multi-colour inkjet printing
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
-
- 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
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
Definitions
- the present invention lies in the field of inkjet printing and relates to an ink system.
- the present invention also relates to an inkjet printing method with the application of the mentioned ink system.
- the present invention further relates to a method for producing functional layers of organic light emitting diodes (OLEDs) and a method for producing OLEDs, in particular full color OLED displays by conducting the mentioned inkjet printing method.
- OLEDs organic light emitting diodes
- OLED - organic light emitting diode - displays are extremely thin, lightweight and energy-efficient. They deliver a perfect image from every viewing angle with extraordinary color brilliance and very high contrast. Due to the low energy consumption, small OLED displays are well suited for use in portable devices, like smartphones, digital frames, and digital cameras. OLED displays are suitable for televisions, monitors, large-area video walls, and in automotive applications. Flexible or rollable displays for everyone are not a dream of the future, but already under development.
- OLED displays consist of arrays of individually-controlled light emitting elements or pixels. For full color displays, each pixel will consist of red, green and blue (RGB) sub-pixels, that can be individually controlled in order to collectively produce the desired image.
- RGB red, green and blue
- each pixel consists of RGB OLED subpixels and the total light output of each device contributes directly to the final image without modification, in the latter case, three white OLED subpixels are combined with three color filters.
- the basic OLED cell structure forming the RGB OLEDS generally consists of organic semiconductor molecules deposited between conducting electrodes on a substrate of glass or flexible film.
- an OLED stack comprises a plurality of functional organic layers including a hole injection layer, a hole transport layer, an emitting layer, and an electron transport layer, and an electron injection layer. All of these layers are situated between an anode and a cathode.
- Substrate can be plastic, glass, or metal foil
- Foundation of the OLED can be plastic, glass, or metal foil
- Anode may or may not be transparent depending on the type of OLED
- HIL Hole Injection Layer
- HTL Hole Transport Layer
- Emissive Layer The heart of the device and where light is made, the emissive layer consists of a color defining emitter doped into a host. This is the layer where the electrical energy is directly converted into light.
- Electron Transport Layer Supports the transport of electrons across it so they can reach the emissive layer.
- Electron Injection Layer EIL- This layer receives electrons from the cathode and injects them deeper into the device.
- Cathode may or may not be transparent depending on the type of OLED
- the side-by-side approach provides the better power consumption efficiency.
- This approach requires the fabrication of RGB OLEDs side-by-side on the same substrate. Since organic semiconductors are generally not amenable with photolithographic processes due to their easy damage by solvents, fabricating OLEDs of different materials on the same substrate can only be done by their thermal deposition of OLED materials using shadow masks, or in the case of polymers and solution-processable small molecule materials, via printing-based techniques, such as inkjet printing.
- Display manufacturers have great interest in OLED for display application.
- they are interested in inkjet printed OLEDs for its high potential for high performance and potential low manufacture cost.
- the advantage of using inkjet printing technique is the highly precise position, ink volume control and its potentially high throughput for mass production.
- a maximum number of inks are printed in the same cycle of manufacturing, e.g. all the three emissive layer materials (inks) are printed and dried at the same time.
- an improved method is applied. Specifically, as depicted below, one ink (ink A in pixel A) is printed firstly and dried by vacuum drying to form film. Then another ink (ink B in pixel B) is printed and dried by vacuum drying.
- the problem for this approach can be that still the film in pixel A is affected by the vapor of solvent during printing or drying as shown in Fig. 2.
- the present application relates to an ink system, comprising or consisting of the following components: a) a first formulation comprising at least one first film-forming organic functional material and at least one first organic solvent, b) a second formulation comprising at least one second film-forming organic functional material and at least one second organic solvent, characterized in that
- the first film-forming organic functional material has a dissolution time of more than 15 minutes, preferably more than 30 minutes and more preferably more than 60 minutes, in the second organic solvent, wherein the dissolution time is determined at room temperature and at a concentration of 7 g/L of the first film-forming organic functional material in the second organic solvent.
- the ink system of the present application further comprises a third formulation comprising at least one third film-forming organic functional material and at least one third organic solvent, wherein the third organic solvent is different from the first and second organic solvent, and the first and second film-forming organic functional materials both have a dissolution time of more than 15 minutes, preferably more than 30 minutes and more preferably more than 60 minutes in the third solvent, wherein the dissolution time is determined at room temperature and at a concentration of 7 g/L.
- the present invention furthermore relates to a method for inkjet printing, comprising or consisting of the following steps: a) providing a substrate, b) printing the first formulation of the ink system of Claim 1 into the first type of pixel, c) drying the first formulation in the first type of pixel, d) printing the second formulation of the ink system of Claim 1 into the second type of pixel, and e) drying the second formulation in the second type of pixel,
- the present invention further relates to a method for producing functional layers of organic light emitting diode (OLED), wherein the functional layers are produced by conducting the inkjet printing method according to the present invention or a combination of said inkjet printing method and other film forming techniques like vacuum evaporation/deposition.
- OLED organic light emitting diode
- the present application also relates to a method for producing an OLED, comprising or consisting of the following steps: a) providing a pair of electrodes, b) providing functional layers between the electrodes, wherein at least one functional layer is produced by conducting the inkjet printing method of the present invention.
- the profile of the first type of pixel maintains smooth and uniform during the printing and drying process of the second formulation. Consequently, the printing yield and efficiency can be increased. Furthermore, with the application of the method according to the present application, the obtained functional layers of the organic light emitting diode (OLED) possess long lifetimes.
- the first formulation, the second formulation and optionally the third formulation are different in that the solvents are different from each other.
- the term “at least” is understood as one, two, three, four, five and more.
- the term film-forming organic functional material denotes, inter alia, organic conductors, organic semiconductors, organic fluorescent compounds, organic phosphorescent compounds, organic light-absorbent compounds, organic light-sensitive compounds, organic photosensitisation agents and other organic photoactive compounds.
- organic functional material furthermore encompasses organometallic complexes of transition metals, rare earths, lanthanides and actinides.
- the film-forming organic functional material is preferably selected from the group consisting of fluorescent emitters, phosphorescent emitters, host materials, matrix materials, exciton-blocking materials, electron-transport materials, electron-injection materials, hole-transport materials, hole-injection materials, n-dopants, p-dopants, wide-band-gap materials, electron-blocking materials and hole-blocking materials.
- Preferred embodiments of film-forming organic functional materials are furthermore disclosed in detail in WO 2011 /076314 A1.
- the film-forming organic functional material is an organic semiconductor selected from the group consisting of holeinjecting, hole-transporting, emitting, electron-transporting and electroninjecting materials.
- the film-forming organic functional material can be a compound having a low molecular weight, a polymer, an oligomer or a dendrimer, where the filmforming organic functional material may also be in the form of a mixture.
- the formulations according to the present invention may comprise two or more different compounds having a low molecular weight, one compound having a low molecular weight and one polymer or two polymers (blend).
- the film-forming organic functional materials are frequently described via the properties of the frontier orbitals, which are described in greater detail below.
- Molecular orbitals in particular also the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LIIMO), their energy levels and the energy of the lowest triplet state Ti or of the lowest excited singlet state Si of the materials can be estimated based on quantumchemical calculations.
- HOMO highest occupied molecular orbital
- LIIMO lowest unoccupied molecular orbital
- their energy levels and the energy of the lowest triplet state Ti or of the lowest excited singlet state Si of the materials can be estimated based on quantumchemical calculations.
- a geometry optimisation is carried out using the "Ground State/Semi-empirical/Default Spin/AM1 /Charge 0/Spin Singlet" method.
- An energy calculation is subsequently carried out on the basis of the optimised geometry.
- the "TD-SCF/DFT/Default Spin/B3PW91" method with the "6-31 G(d)" base set (charge 0, spin singlet) is used here.
- the geometry is optimised via the "Ground State/Hartree-Fock/Default Spin/LanL2MB/Charge O/Spin Singlet” method.
- the energy calculation is carried out analogously to the above-described method for the organic substances, with the difference that the "LanL2DZ" base set is used for the metal atom and the "6-31 G(d)" base set is used for the ligands.
- the energy calculation gives the HOMO energy level HEh or LIIMO energy level LEh in hartree units.
- the HOMO and LIIMO energy levels in electron volts calibrated with reference to cyclic voltammetry measurements are determined therefrom as follows:
- these values are to be regarded as HOMO and LIIMO energy levels respectively of the materials.
- the lowest triplet state Ti is defined as the energy of the triplet state having the lowest energy which arises from the quantum-chemical calculation described.
- the lowest excited singlet state Si is defined as the energy of the excited singlet state having the lowest energy which arises from the quantumchemical calculation described.
- a hole-injection material has a HOMO level which is in the region of or above the level of the anode, i.e. in general is at least -5.3 eV.
- hole-transport materials are capable of transporting holes, i.e. positive charges, which are generally injected from the anode or an adjacent layer, for example a hole-injection layer.
- a hole-transport material generally has a high HOMO level of preferably at least -5.4 eV.
- phenylenediamine derivatives (US 3615404), arylamine derivatives (US 3567450), amino-substituted chaicone derivatives (US 3526501 ), styrylanthracene derivatives (JP-A-56-46234), polycyclic aromatic compounds (EP 1009041 ), polyarylalkane derivatives (US 3615402), fluorenone derivatives (JP-A-54-110837), hydrazone derivatives (US 3717462), acylhydrazones, stilbene derivatives (JP-A-61-210363), silazane derivatives (US 4950950), polysilanes (J P-A-2 -204996), aniline copolymers (J P-A-2 -282263), thiophene oligomers (JP Heisei 1 (1989) 211399), polythiophenes, poly(N-vinylcarbazol
- arylamine dendrimers JP Heisei 8 (1996) 193191
- monomeric triarylamines US 3180730
- triarylamines containing one or more vinyl radicals and/or at least one functional group containing active hydrogen US 3567450 and US 3658520
- tetraaryldiamines the two tertiary amine units are connected via an aryl group.
- More triarylamino groups may also be present in the molecule.
- Phthalocyanine derivatives, naphthalocyanine derivatives, butadiene derivatives and quinoline derivatives such as, e.g. dipyrazino[2,3-f:2’,3’-h]quinoxalinehexacarbonitrile, are also suitable.
- triarylamine compounds of the formulae (TA-1 ) to (TA-12) which are disclosed in EP 1162193 B1 , EP 650955 B1 , Synth. Metals 1997, 91 (1-3), 209, DE 19646119 A1 , WO 2006/122630 A1 , EP 1860097 A1 , EP 1834945 A1 , JP 08053397 A, US 6251531 B1 , US 2005/0221124, JP 08292586 A, US 7399537 B2, US 2006/0061265 A1 , EP 1 661888 and WO 2009/041635.
- the said compounds of the formulae (TA-1 ) to (TA-12) may also be substituted: formula TA-3 formula TA-4 formula TA-5 formula TA-6
- arylamines and heterocycles which are generally employed as holeinjection and/or hole-transport materials preferably result in a HOMO in the polymer of greater than -5.8 eV (vs. vacuum level), particularly preferably greater than -5.5 eV.
- LIIMO lowest unoccupied molecular orbital
- Particularly suitable compounds for electron-transporting and electroninjecting layers are metal chelates of 8-hydroxyquinoline (for example LiQ, AIQ3, GaQs, MgQ2, ZnQ2, InQs, ZrQ4), BAIQ, Ga oxinoid complexes, 4-azaphenanthren-5-ol-Be complexes (US 5529853 A, cf. formula ET-1 ), butadiene derivatives (US 4356429), heterocyclic optical brighteners (US 4539507), benzimidazole derivatives (US 2007/0273272 A1 ), such as, for example, TPBI (US 5766779, cf.
- 1 ,3,5-triazines for example spirobifluorenyltriazine derivatives (for example in accordance with DE 102008064200), pyrenes, anthracenes, tetracenes, fluorenes, spirofluorenes, dendrimers, tetracenes (for example rubrene derivatives), 1 ,10- phenanthroline derivatives (JP 2003-115387, JP 2004-311184, JP 2001- 267080, WO 02/043449), silacyclopentadiene derivatives (EP 1480280, EP 1478032, EP 1469533), borane derivatives, such as, for example, tri- arylborane derivatives containing Si (US 2007/0087219 A1 , cf.
- spirobifluorenyltriazine derivatives for example in accordance with DE 102008064200
- pyrenes for example in accordance with DE 1020080
- formula ET-3 pyridine derivatives (JP 2004-200162), phenanthrolines, especially 1 ,10- phenanthroline derivatives, such as, for example, BCP and Bphen, also several phenanthrolines connected via biphenyl or other aromatic groups (US 2007-0252517 A1 ) or phenanthrolines connected to anthracene (US 2007- 0122656 A1 , cf. formulae ET-4 and ET-5).
- phenanthrolines especially 1 ,10- phenanthroline derivatives, such as, for example, BCP and Bphen, also several phenanthrolines connected via biphenyl or other aromatic groups (US 2007-0252517 A1 ) or phenanthrolines connected to anthracene (US 2007- 0122656 A1 , cf. formulae ET-4 and ET-5).
- heterocyclic organic compounds such as, for example, thiopyran dioxides, oxazoles, triazoles, imidazoles or oxadiazoles.
- heterocyclic organic compounds such as, for example, thiopyran dioxides, oxazoles, triazoles, imidazoles or oxadiazoles.
- five-membered rings containing N such as, for example, oxazoles, preferably 1 ,3,4-oxadiazoles, for example compounds of the formulae ET-6, ET-7, ET-8 and ET-9, which are disclosed, inter alia, in US 2007/0273272 A1 ; thiazoles, oxadiazoles, thiadiazoles, triazoles, inter alia, see US 2008/0102311 A1 and Y.A. Levin, M.S.
- organic compounds such as fluorenones, fluorenylidenemethanes, perylenetetracarbonic acids, anthraquinonedimethanes, diphenoquinones, anthrones and anthraquinonediethylenediamines and derivatives thereof.
- the compounds which are able to generate electron-injection and/or electron-transport properties preferably result in an LUMO of less than -2.5 eV (vs. vacuum level), particularly preferably less than -2.7 eV.
- the present formulations may comprise emitters.
- emitter denotes a material which, after excitation, which can take place by transfer of any type of energy, allows a radiative transition into a ground state with emission of light.
- two classes of emitters are known, namely fluorescent and phosphorescent emitters.
- fluorescent emitter denotes materials or compounds in which a radiative transition from an excited singlet state into the ground state takes place.
- phosphorescent emitter preferably denotes luminescent materials or compounds which contain transition metals. Emitters are frequently also called dopants if the dopants cause the properties described above in a system.
- a dopant in a system comprising a matrix material and a dopant is taken to mean the component whose proportion in the mixture is the smaller.
- a matrix material in a system comprising a matrix material and a dopant is taken to mean the component whose proportion in the mixture is the greater.
- the term phosphorescent emitter can also be taken to mean, for example, phosphorescent dopant.
- Compounds which are able to emit light include, inter alia, fluorescent emitters and phosphorescent emitters. These include, inter alia, compounds containing stilbene, stilbenamine, styrylamine, coumarine, rubrene, rhodamine, thiazole, thiadiazole, cyanine, thiophene, paraphenylene, perylene, phtalocyanine, porphyrin, ketone, quinoline, imine, anthracene and/or pyrene structures. Particular preference is given to compounds which are able to emit light from the triplet state with high efficiency, even at room temperature, i.e. exhibit electrophosphorescence instead of electrofluorescence, which frequently causes an increase in the energy efficiency.
- Suitable for this purpose are firstly compounds which contain heavy atoms having an atomic number of greater than 36. Preference is given to compounds which contain d- or f-transition metals which satisfy the above- mentioned condition. Particular preference is given here to corresponding compounds which contain elements from group 8 to 10 (Ru, Os, Rh, Ir, Pd, Pt).
- Suitable functional compounds here are, for example, various complexes, as described, for example, in WO 02/068435 A1 , WO 02/081488 A1 , EP 1239526 A2 and WO 2004/026886 A2.
- Preferred compounds which can serve as fluorescent emitters are described by way of example below.
- Preferred fluorescent emitters are selected from the class of the monostyrylamines, the distyrylamines, the tristyrylamines, the tetrastyrylamines, the styrylphosphines, the styryl ethers and the arylamines.
- a monostyrylamine is taken to mean a compound which contains one substituted or unsubstituted styryl group and at least one, preferably aromatic, amine.
- a distyrylamine is taken to mean a compound which contains two substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
- a tristyrylamine is taken to mean a compound which contains three substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
- a tetrastyrylamine is taken to mean a compound which contains four substituted or unsubstituted styryl groups and at least one, preferably aromatic, amine.
- the styryl groups are particularly preferably stilbenes, which may also be further substituted.
- Corresponding phosphines and ethers are defined analogously to the amines.
- An arylamine or an aromatic amine in the sense of the present invention is taken to mean a compound which contains three substituted or unsubstituted aromatic or heteroaromatic ring systems bonded directly to the nitrogen.
- At least one of these aromatic or heteroaromatic ring systems is preferably a condensed ring system, preferably having at least 14 aromatic ring atoms.
- Preferred examples thereof are aromatic anthracenamines, aromatic anthracenediamines, aromatic pyrenamines, aromatic pyrenediamines, aromatic chrysenamines or aromatic chrysenediamines.
- An aromatic anthracenamine is taken to mean a compound in which one diarylamino group is bonded directly to an anthracene group, preferably in the 9-position.
- An aromatic anthracene-diamine is taken to mean a compound in which two diarylamino groups are bonded directly to an anthracene group, preferably in the 2,6- or 9,10-position.
- Aromatic pyrenamines, pyrenediamines, chrysenamines and chrysenediamines are defined analogously thereto, where the diarylamino groups are preferably bonded to the pyrene in the 1 -position or in the 1 ,6-position.
- fluorescent emitters are selected from indenofluorenamines or indenofluorenediamines, which are described, inter alia, in WO 2006/122630; benzoindenofluorenamines or benzoindenofluorenediamines, which are described, inter alia, in WO 2008/006449; and dibenzoindeno- fluorenamines or dibenzoindenofluorenediamines, which are described, inter alia, in WO 2007/140847.
- Examples of compounds from the class of the styrylamines which can be employed as fluorescent emitters are substituted or unsubstituted tristilben- amines or the dopants described in WO 2006/000388, WO 2006/058737, WO 2006/000389, WO 2007/065549 and WO 2007/115610.
- Distyrylbenzene and distyrylbiphenyl derivatives are described in US 5121029. Further styrylamines can be found in US 2007/0122656 A1 .
- Particularly preferred styrylamine compounds are the compounds of the formula EM-1 described in US 7250532 B2 and the compounds of the formula EM-2 described in DE 10 2005 058557 A1 : formula EM-1 formula EM-2
- triarylamine compounds are compounds of the formulae EM-3 to EM-15 disclosed in CN 1583691 A, JP 08/053397 A and US 6251531 B1 , EP 1957606 A1 , US 2008/0113101 A1 , US 2006/210830 A, WO 2008/006449 and DE 102008035413 and derivatives thereof: formula EM-5 formula EM-6 formula EM-9 formula EM-10 formula EM-15
- Further preferred compounds which can be employed as fluorescent emitters are selected from derivatives of naphthalene, anthracene, tetracene, benzanthracene, benzophenanthrene (DE 10 2009 005746), fluorene, fluoranthene, periflanthene, indenoperylene, phenanthrene, perylene (US 2007/0252517 A1 ), pyrene, chrysene, decacyclene, coronene, tetra- phenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene, rubrene, coumarine (US 4769292, US 6020078, US 2007/0252517 A1 ), pyran, oxazole, benzoxazole, benzothiazole, benzimidazole, pyrazine, cinnamic acid esters, diketopyrrolopyrrol
- 9,10- substituted anthracenes such as, for example, 9,10-diphenylanthracene and 9,10-bis(phenylethynyl)anthracene.
- 1,4-Bis(9’-ethynylanthracenyl)benzene is also a preferred dopant.
- DMQA N,N’-dimethylquinacridone
- thiopyran polymethine
- pyrylium and thiapyrylium salts periflanthene and indenoperylene.
- Blue fluorescent emitters are preferably polyaromatic compounds, such as, for example, 9,10-di(2-naphthylanthracene) and other anthracene derivatives, derivatives of tetracene, xanthene, perylene, such as, for example, 2,5,8, 11 -tetra-f-butylperylene, phenylene, for example 4,4’-bis(9-ethyl-3- carbazovinylene)-1 ,1 ’-biphenyl, fluorene, fluoranthene, arylpyrenes (US 2006/0222886 A1 ), arylenevinylenes (US 5121029, US 5130603), bis- (azinyl)imine-boron compounds (US 2007/0092753 A1 ), bis(azinyl)methene compounds and carbostyryl compounds.
- polyaromatic compounds such as, for example, 9,10-di(2-naphthylanth
- Ar 1 , Ar 2 , Ar 3 are on each occurrence, identically or differently, an aryl or heteroaryl group having 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1 , with the proviso that Ar 2 does not stand for anthracene, naphthacene or pentacene;
- R 3 is on each occurrence, identically or differently, H, D or an aliphatic or aromatic hydrocarbon radical having 1 to 20 C atoms;
- Ar 1 is on each occurrence, identically or differently, an aryl or heteroaryl group having 6 to 18 aromatic ring atoms, which may be substituted by one or more radicals R 1 ;
- Ar 2 is on each occurrence, identically or differently, an aryl or heteroaryl group having 6 aromatic ring atoms, which may be substituted by one or more radicals R 2 ;
- R 5 is on each occurrence, identically or differently, H, D, F or an aliphatic, aromatic or heteroaromatic organic radical having 1 to 20 C atoms, in which, in addition, one or more H atoms may be replaced by D or F; two or more substituents R 5 here may be linked to one another and may form a ring; where at least one of the two groups Ar 1 must contain 10 or more aromatic ring atoms; and where, if one of the two groups Ar 1 is a phenyl group, the other of the two groups Ar 1 must not contain more than 14 aromatic ring atoms.
- Ar 1 stands on each occurrence, identically or differently, for an aryl or heteroaryl group having 6 to 18 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 , wherein at least one of the groups Ar 1 in formula (1 ) has 10 or more aromatic ring atoms;
- Ar 2 stands on each occurrence, identically or differently, for an aryl or heteroaryl group having 6 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 ;
- Ar 3 , Ar 4 stand on each occurrence, identically or differently, for an aromatic or heteroaromatic ring systems having 5 to 25 aromatic ring atoms, which may in each case be substituted by one or more radicals R 1 ;
- R 3 stands on each occurrence, identically or differently, for H, D, F, Cl, Br, I, CN, a straight-chain alkyl, alkoxy or thioalkyl groups having 1 to 20 C atoms or branched or cyclic alkyl, alkoxy or thioalkyl groups having 3 to 20 C atoms, where in each case one or more non-adjacent CH 2 groups may be replaced by SO, SO 2 , O, S and where one or more H atoms may be replaced by D, F, Cl, Br or I, or an aromatic or heteroaromatic ring system having 5 to 24 C atoms;
- Ar 5 is an aromatic or heteroaromatic ring system having 5 to 24 aromatic ring atoms, preferably 5 to 18 aromatic ring atoms, which may in each case also be substituted by one or more radicals R 3 ;
- n is an integer from 1 to 20; wherein if n is equal to 1 and at least one of the group Ar 3 or Ar 4 stands for
- Preferred compounds which can serve as phosphorescent emitters are described below by way of example.
- Examples of phosphorescent emitters are revealed by WO 00/70655, WO 01/41512, WO 02/02714, WO 02/15645, EP 1191613, EP 1191612, EP 1191614 and WO 2005/033244.
- all phosphorescent complexes as are used in accordance with the prior art for phosphorescent OLEDs and as are known to the person skilled in the art in the area of organic electroluminescence are suitable, and the person skilled in the art will be able to use further phosphorescent complexes without inventive step.
- Phosphorescent metal complexes preferably contain Ir, Ru, Pd, Pt, Os or Re, more preferably Ir.
- Preferred ligands are 2-phenylpyridine derivatives, 7,8-benzoquinoline derivatives, 2-(2-thienyl)pyridine derivatives, 2-(1-naphthyl)pyridine derivatives, 1 -phenylisoquinoline derivatives, 3-phenylisoquinoline derivatives or 2-phenylquinoline derivatives. All these compounds may be substituted, for example by fluoro, cyano and/or trifluoromethyl substituents for blue.
- Auxiliary ligands are preferably acetylacetonate or picolinic acid. In particular, complexes of Pt or Pd with tetradentate ligands of the formula
- EM-16 are suitable formula EM-16
- suitable are complexes of trivalent lanthanides, such as, for example, Tb 3+ and Eu 3+ (J. Kido et al. Appt. Phys. Lett. 65 (1994), 2124, Kido et al. Chem. Lett.
- Particularly preferred compounds which are used as phosphorescent dopants are, inter alia, the compounds of the formula EM-17 described, inter alia, in US 2001/0053462 A1 and Inorg. Chem. 2001 , 40(7), 1704-1711 , JACS 2001 , 123(18), 4304-4312, and derivatives thereof.
- formula EM-17 Derivatives are described in US 7378162 B2, US 6835469 B2 and JP 2003/253145 A.
- Quantum dots can likewise be employed as emitters, these materials being disclosed in detail in WO 2011 Z076314 A1.
- Compounds which are employed as host materials, in particular together with emitting compounds, include materials from various classes of substances.
- Host materials generally have larger band gaps between HOMO and LUMO than the emitter materials employed.
- preferred host materials exhibit properties of either a hole- or electron-transport material.
- host materials can have both electron- and hole-transport properties.
- Host materials are in some cases also called matrix material, in particular if the host material is employed in combination with a phosphorescent emitter in an OLED.
- Particularly preferred compounds which can serve as host materials or cohost materials are selected from the classes of the oligoarylenes, comprising anthracene, benzanthracene and/or pyrene, or atropisomers of these compounds.
- An oligoarylene in the sense of the present invention is intended to be taken to mean a compound in which at least three aryl or arylene groups are bonded to one another.
- Preferred host materials are selected, in particular from compounds of the formula (H-1 )
- the group Ar 5 particularly preferably stands for anthracene, and the groups Ar 4 and Ar 6 are bonded in the 9- and 10-position, where these groups may optionally be substituted.
- at least one of the groups Ar 4 and/or Ar 6 is a condensed aryl group selected from 1 - or 2-naphthyl, 2-, 3- or 9-phenanthrenyl or 2-, 3-, 4-, 5-, 6- or 7-benzanthracenyl.
- Anthracene-based compounds are described in US 2007/0092753 A1 and US 2007/0252517 A1 , for example 2-(4-methyl- phenyl)-9, 10-di-(2-naphthyl)anthracene, 9-(2-naphthyl)-10-(1 , 1 ’-biphenyl)- anthracene and 9,10-bis[4-(2,2-diphenylethenyl)phenyl]anthracene, 9,10- diphenylanthracene, 9,10-bis(phenylethynyl)anthracene and 1 ,4-bis(9’- ethynylanthracenyl)benzene.
- TNB 4,4’-bis[N-(1 -naphthyl)-N-(2-naphthyl)amino]biphenyl.
- Metal-oxinoid complexes such as LiQ or AIQ3, can be used as co-hosts.
- compounds which can be employed as host or matrix include materials which are employed together with phosphorescent emitters.
- CBP N,N-biscarbazolylbiphenyl
- carbazole derivatives for example in accordance with WO 2005/039246, US 2005/0069729, JP 2004/288381 , EP 1205527 or WO 2008/086851
- azacarbazoles for example in accordance with EP 1617710, EP 1617711 , EP 1731584 or JP 2005/347160
- ketones for example in accordance with WO 2004/093207 or in accordance with DE 102008033943
- phosphine oxides, sulfoxides and sulfones for example in accordance with WO 2005/003253
- oligophenylenes for example in accordance with US 2005/0069729)
- bipolar matrix materials for example in accordance with WO 2007/137725
- silanes for example in accordance with WO 2005/111172
- Preferred tetraaryl-Si compounds are disclosed, for example, in US 2004/0209115, US 2004/0209116, US 2007/0087219 A1 and in H. Gilman, E.A. Zuech, Chemistry & Industry (London, United Kingdom), 1960, 120.
- Particularly preferred compounds from group 4 for the preparation of the matrix for phosphorescent dopants are disclosed, inter alia, in DE 102009022858, DE 102009023155, EP 652273 B1 , WO 2007/063754 and WO 2008/056746, where particularly preferred compounds are described by the formulae H-22 to H-25.
- film-forming functional compounds which can be employed in accordance with the present invention, and which can serve as host material, especial preference is given to substances which contain at least one nitrogen atom.
- These preferably include aromatic amines, triazine derivatives and carbazole derivatives.
- carbazole derivatives in particular exhibit surprisingly high efficiency.
- Triazine derivatives result in unexpectedly long lifetimes of the electronic devices.
- a plurality of different matrix materials as a mixture, in particular at least one electron-conducting matrix material and at least one hole-conducting matrix material.
- n-Dopants herein are taken to mean reducing agents, i.e. electron donors.
- N compounds for example WO 2012/175535 A1 , WO 2012/175219 A1
- naphthylenecarbodiimides for example WO 2012/16
- the formulations may comprise a wide-band-gap material as the film-forming functional material.
- Wide-band-gap material is taken to mean a material in the sense of the disclosure content of US 7,294,849. These systems exhibit particularly advantageous performance data in electroluminescent devices.
- the compound employed as wide-band-gap material can preferably have a band gap of 2.5 eV or more, preferably 3.0 eV or more, particularly preferably 3.5 eV or more.
- the band gap can be calculated, inter alia, by means of the energy levels of the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LIIMO).
- the formulations may comprise a hole-blocking material (HBM) as the film-forming functional material.
- HBM hole-blocking material
- a hole-blocking material denotes a material which prevents or minimises the transmission of holes (positive charges) in a multilayer system, in particular if this material is arranged in the form of a layer adjacent to an emission layer or a hole-conducting layer.
- a hole-blocking material has a lower HOMO level than the holetransport material in the adjacent layer.
- Hole-blocking layers are frequently arranged between the light-emitting layer and the electron-transport layer in OLEDs.
- advantageous hole-blocking materials are metal complexes (US 2003/0068528), such as, for example, bis(2-methyl-8-quinolinolato)(4- phenylphenolato)aluminium(lll) (BAIQ). Fac-tris(1 -phenylpyrazolato-N,C2)- iridium(lll) (Ir(ppz)s) is likewise employed for this purpose (US 2003/0175553 A1 ). Phenanthroline derivatives, such as, for example, BCP, or phthalimides, such as, for example, TMPP, can likewise be employed.
- the formulations may comprise an electron-blocking material (EBM) as the film-forming functional material.
- EBM electron-blocking material
- An electron-blocking material denotes a material which prevents or minimises the transmission of electrons in a multilayer system, in particular if this material is arranged in the form of a layer adjacent to an emission layer or an electron-conducting layer. In gen- eral, an electron-blocking material has a higher LIIMO level than the electron-transport material in the adjacent layer.
- advantageous electron-blocking materials are transitionmetal complexes, such as, for example, lr(ppz)s (US 2003/0175553).
- the electron-blocking material can preferably be selected from amines, tri- arylamines and derivatives thereof.
- the functional compounds which can be employed as the filmforming organic functional materials in the formulations preferably have, if they are low-molecular-weight compounds, a molecular weight of ⁇ 3,000 g/mol, more preferably ⁇ 2,000 g/mol and most preferably ⁇ 1 ,000 g/mol.
- particularly preferred functional compounds which can be employed as filmforming organic functional material in the formulations are those which have a glass-transition temperature of > 70°C, preferably > 100°C, more preferably > 125°C and most preferably > 150°C, determined in accordance with DIN 51005.
- the formulations may also comprise polymers as the film-forming organic functional materials.
- the compounds described above as film-forming organic functional materials which frequently have a relatively low molecular weight, can also be mixed with a polymer. It is likewise possible to incorporate these compounds covalently into a polymer. This is possible, in particular, with compounds which are substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid ester, or by reactive, polymerizable groups, such as olefins or oxetanes. These can be used as monomers for the production of corresponding oligomers, dendrimers or polymers.
- the oligomerisation or polymerisation here preferably takes place via the halogen functionality or the boronic acid functionality or via the polymerizable group. It is furthermore possible to crosslink the polymers via groups of this type.
- the compounds and polymers according to the invention can be employed as crosslinked or noncrosslinked layer.
- Polymers which can be employed as film-forming organic functional materials frequently contain units or structural elements which have been described in the context of the compounds described above, inter alia those as disclosed and extensively listed in WO 02/077060 A1 , in WO 2005/014689 A2 and in WO 2011/076314 A1 .
- the functional materials can originate, for example, from the following classes:
- Group 1 structural elements which are able to generate hole-injection and/or hole-transport properties
- Group 2 structural elements which are able to generate electroninjection and/or electron-transport properties
- Group 3 structural elements which combine the properties described in relation to groups 1 and 2;
- Group 4 structural elements which have light-emitting properties, in particular phosphorescent groups
- Group 5 structural elements which improve the transition from the so-called singlet state to the triplet state
- Group 6 structural elements which influence the morphology or also the emission colour of the resultant polymers
- Group 7 structural elements which are typically used as backbone.
- the structural elements here may also have various functions, so that a clear assignment need not be advantageous.
- a structural element of group 1 may likewise serve as backbone.
- the polymer having hole-transport or hole-injection properties employed as the film-forming organic functional material, containing structural elements from group 1 may preferably contain units which correspond to the holetransport or hole-injection materials described above.
- group 1 is, for example, triarylamines, benzidines, tetraaryl-para-phenylenediamines, carbazoles, azulenes, thiophenes, pyrroles and furanes and derivatives thereof and further O-, S- or N-containing heterocycles having a high HOMO.
- arylamines and heterocycles preferably have a HOMO of above -5.8 eV (against vacuum level), particularly preferably above -5.5 eV.
- Ar 2 is, in each case identically or differently for different recurring units, a monocyclic or polycyclic aryl group, which may optionally be substituted;
- Ar 3 is, in each case identically or differently for different recurring units, a monocyclic or polycyclic aryl group, which may optionally be substituted; m is 1 , 2 or 3.
- HTP-1 which are selected from the group consisting of units of the formulae HTP-1 A to HTP-1 C:
- R a is on each occurrence, identically or differently, H, a substituted or unsubstituted aromatic or heteroaromatic group, an alkyl, cycloalkyl, alkoxy, aralkyl, aryloxy, arylthio, alkoxycarbonyl, silyl or carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group; r is 0, 1 , 2, 3 or 4, and s is 0, 1 , 2, 3, 4 or 5.
- T 1 and T 2 are selected independently from thiophene, selenophene, thieno- [2,3-b]thiophene, thieno[3,2-b]thiophene, dithienothiophene, pyrrole and aniline, where these groups may be substituted by one or more radicals R b ;
- R° and R 00 are each independently H or an optionally substituted carbyl or hydrocarbyl group having 1 to 40 carbon atoms, which may optionally be substituted and may optionally contain one or more heteroatoms;
- Ar 7 and Ar 8 represent, independently of one another, a monocyclic or polycyclic aryl or heteroaryl group, which may optionally be substituted and may optionally be bonded to the 2,3-position of one or both adjacent thiophene or selenophene groups; c and e are, independently of one another, 0, 1 , 2, 3 or 4, where 1 ⁇ c + e ⁇ 6; d and f are, independently of one another, 0, 1 , 2, 3 or 4.
- Preferred examples of polymers having hole-transport or hole-injection properties are described, inter alia, in WO 2007/131582 A1 and WO 2008/009343 A1 .
- the polymer having electron-injection and/or electron-transport properties employed as the film-forming organic functional material, containing structural elements from group 2, may preferably contain units which correspond to the electron-injection and/or electron-transport materials described above.
- Further preferred structural elements of group 2 which have electron-injection and/or electron-transport properties are derived, for example, from pyridines, pyrimidines, pyridazines, pyrazines, oxadiazoles, quinolines, quinoxalines and phenazines and derivatives thereof, but also triarylboranes or further O-, S- or N-containing heterocycles having a low LIIMO level.
- These structural elements of group 2 preferably have an LIIMO of below -2.7 eV (against vacuum level), particularly preferably below -2.8 eV.
- the film-forming organic functional material can preferably be a polymer which contains structural elements from group 3, where structural elements which improve the hole and electron mobility (i.e. structural elements from groups 1 and 2) are connected directly to one another. Some of these structural elements can serve as emitters here, where the emission colours may be shifted, for example, into the green, red or yellow. Their use is therefore advantageous, for example, for the generation of other emission colours or a broad-band emission by polymers which originally emit in blue.
- the polymer having light-emitting properties employed as the film-forming organic functional material, containing structural elements from group 4 may preferably contain units which correspond to the emitter materials described above. Preference is given here to polymers containing phosphorescent groups, in particular the emitting metal complexes described above which contain corresponding units containing elements from groups 8 to 10 (Ru, Os, Rh, Ir, Pd, Pt).
- the polymer employed as the film-forming organic functional material containing units of group 5 which improve the transition from the so-called singlet state to the triplet state can preferably be employed in support of phosphorescent compounds, preferably the polymers containing structural elements of group 4 described above.
- a polymeric triplet matrix can be used here. Suitable for this purpose are, in particular, carbazole and connected carbazole dimer units, as described, for example, in DE 10304819 A1 and DE 10328627 A1 . Also suitable for this purpose are ketone, phosphine oxide, sulfoxide, sulfone and silane derivatives and similar compounds, as described, for example, in DE 10349033 A1.
- preferred structural units can be derived from compounds which have been described above in connection with the matrix materials employed together with phosphorescent compounds.
- the further film-forming organic functional material is preferably a polymer containing units of group 6 which influence the morphology and/or the emission colour of the polymers.
- these are those which have at least one further aromatic or another conjugated structure which do not count amongst the above-mentioned groups. These groups accordingly have only little or no effect on the chargecarrier mobilities, the non-organometallic complexes or the singlet-triplet transition.
- Structural units of this type are able to influence the morphology and/or the emission colour of the resultant polymers. Depending on the structural unit, these polymers can therefore also be used as emitters.
- aromatic structural elements having 6 to 40 C atoms or also tolan, stilbene or bisstyrylarylene derivative units, each of which may be substituted by one or more radicals.
- Particular preference is given here to the use of groups derived from 1 ,4-phenylene, 1 ,4-naphthylene, 1 ,4- or 9,10-anthrylene, 1 ,6-, 2,7- or 4,9- pyrenylene, 3,9- or 3,10-perylenylene, 4,4'-biphenylene, 4,4"-terphenylylene, 4,4'-bi-1 ,1 '-naphthylylene, 4,4‘-tolanylene, 4,4'-stilbenylene or 4,4"- bisstyrylarylene derivatives.
- the polymer employed as the film-forming organic functional material preferably contains units of group 7, which preferably contain aromatic structures having 6 to 40 C atoms which are frequently used as backbone.
- 4,5-dihydropyrene derivatives 4,5,9, 10-tetra- hydropyrene derivatives, fluorene derivatives, which are disclosed, for example, in US 5962631 , WO 2006/052457 A2 and WO 2006/118345 A1 , 9,9-spirobifluorene derivatives, which are disclosed, for example, in WO 2003/020790 A1 , 9,10-phenanthrene derivatives, which are disclosed, for example, in WO 2005/104264 A1 , 9,10-dihydrophenanthrene derivatives, which are disclosed, for example, in WO 2005/014689 A2, 5,7-dihydro- dibenzoxepine derivatives and cis- and trans-indenofluorene derivatives, which are disclosed, for example, in WO 2004/041901 A1 and WO 2004/113412 A2, and binaphthylene derivatives, which are disclosed, for example, in WO 2006/0638
- group 7 which are selected from fluorene derivatives, which are disclosed, for example, in US 5,962,631 , WO 2006/052457 A2 and WO 2006/118345 A1 , spirobifluorene derivatives, which are disclosed, for example, in WO 2003/020790 A1 , benzofluorene, dibenzofluorene, benzothiophene and dibenzofluorene groups and derivatives thereof, which are disclosed, for example, in WO 2005/056633 A1 , EP 1344788 A1 and WO 2007/043495 A1.
- X is halogen
- R° and R 00 are each, independently, H or an optionally substituted carbyl or hydrocarbyl group having 1 to 40 carbon atoms, which may optionally be substituted and may optionally contain one or more heteroatoms; g is in each case, independently, 0 or 1 and h is in each case, independently, 0 or 1 , where the sum of g and h in a sub-unit is preferably 1 ; m is an integer > 1 ; Ar 1 and Ar 2 represent, independently of one another, a monocyclic or polycyclic aryl or heteroaryl group, which may optionally be substituted and may optionally be bonded to the 7,8-position or the 8,9-position of an indeno- fluorene group; and a and b are, independently of one another, 0 or 1 .
- this group preferably represents a spirobifluorene.
- recurring units of the formula PB-1 which are selected from the group consisting of units of the formulae PB-1 A to PB-1 E: formula PB-1 C where R c has the meaning described above for formula PB-1 , r is 0, 1 , 2, 3 or 4, and R e has the same meaning as the radical R c .
- L is H, halogen or an optionally fluorinated, linear or branched alkyl or alkoxy group having 1 to 12 C atoms and preferably stands for H, F, methyl, i-propyl, t-butyl, n-pentoxy or trifluoromethyl;
- L' is an optionally fluorinated, linear or branched alkyl or alkoxy group having 1 to 12 C atoms and preferably stands for n-octyl or n-octyloxy.
- polymers which contain more than one of the structural elements of groups 1 to 7 described above. It may furthermore be provided that the polymers preferably contain more than one of the structural elements from one group described above, i.e. comprise mixtures of structural elements selected from one group.
- polymers which, besides at least one structural element which has light-emitting properties (group 4), preferably at least one phosphorescent group, additionally contain at least one further structural element of groups 1 to 3, 5 or 6 described above, where these are preferably selected from groups 1 to 3.
- the proportion of the various classes of groups, if present in the polymer can be in broad ranges, where these are known to the person skilled in the art. Surprising advantages can be achieved if the proportion of one class present in a polymer, which is in each case selected from the structural elements of groups 1 to 7 described above, is preferably in each case > 5 mol%, particularly preferably in each case > 10 mol%.
- the polymers may contain corresponding groups. It may preferably be provided that the polymers contain substituents, so that on average at least 2 non-aromatic carbon atoms, particularly preferably at least 4 and especially preferably at least 8 non-aromatic carbon atoms are present per recurring unit, where the average relates to the number average. Individual carbon atoms here may be replaced, for example, by O or S. However, it is possible for a certain proportion, optionally all recurring units, to contain no substituents which contain non-aromatic carbon atoms. Short-chain substituents are preferred here, since long-chain substituents can have adverse effects on layers which can be obtained using organic functional materials.
- the substituents preferably contain at most 12 carbon atoms, preferably at most 8 carbon atoms and particularly preferably at most 6 carbon atoms in a linear chain.
- the polymer employed in accordance with the invention as the film-forming organic functional material can be a random, alternating or regioregular copolymer, a block copolymer or a combination of these copolymer forms.
- the polymer employed as the film-forming organic functional material can be a non-conjugated polymer having side chains, where this embodiment is particularly important for phosphorescent OLEDs based on polymers.
- phosphorescent polymers can be obtained by free-radical copolymerisation of vinyl compounds, where these vinyl compounds contain at least one unit having a phosphorescent emitter and/or at least one charge-transport unit, as is disclosed, inter alia, in US 7250226 B2. Further phosphorescent polymers are described, inter alia, in JP 2007/ 211243 A2, JP 2007/197574 A2, US 7250226 B2 and JP 2007/059939 A.
- the non-conjugated polymers contain backbone units, which are connected to one another by spacer units.
- Examples of such triplet emitters which are based on non-conjugated polymers based on backbone units are disclosed, for example, in DE 102009023154.
- the non-conjugated polymer can be designed as fluorescent emitter.
- Preferred fluorescent emitters which are based on non-conjugated polymers having side chains contain anthracene or benzanthracene groups or derivatives of these groups in the side chain, where these polymers are disclosed, for example, in JP 2005/108556, JP 2005/285661 and JP 2003/338375.
- These polymers can frequently be employed as electron- or hole-transport materials, where these polymers are preferably designed as non-conjugated polymers.
- the functional compounds employed as the film-forming organic functional materials in the formulations preferably have, in the case of polymeric compounds, a molecular weight M w of > 10,000 g/mol, more preferably > 25,000 g/mol and most preferably > 50,000 g/mol.
- the molecular weight M w of the polymers here is preferably in the range from 10,000 to 2,000,000 g/mol, more preferably in the range from 25,000 to 1 ,000,000 g/mol and most preferably in the range from 50,000 to 500,000 g/mol.
- the formulations according to the invention may comprise all film-forming organic functional materials which are necessary for the production of the respective functional layer of the electronic device. If, for example, a holetransport, hole-injection, electron-transport or electron-injection layer is built up precisely from one functional compound, the formulation comprises precisely this compound as organic functional material. If an emission layer comprises, for example, an emitter in combination with a matrix or host material, the formulation comprises, as organic functional material, precisely the mixture of emitter and matrix or host material, as described in greater detail elsewhere in the present application.
- the formulation according to the present invention may comprise further additives and processing assistants.
- additives and processing assistants include, inter alia, surface-active substances (surfactants), lubricants and greases, additives which modify the viscosity, additives which increase the conductivity, dispersants, hydrophobizing agents, adhesion promoters, flow improvers, antifoams, deaerating agents, diluents, which may be reactive or unreactive, fillers, assistants, processing assistants, dyes, pigments, stabilisers, sensitizers, nanoparticles and inhibitors.
- surfactants surface-active substances
- lubricants and greases additives which modify the viscosity
- additives which increase the conductivity additives which increase the conductivity
- dispersants hydrophobizing agents
- adhesion promoters adhesion promoters
- flow improvers antifoams
- deaerating agents deaerating agents
- diluents which may be reactive or unre
- the at least one first film-forming organic functional material, the at least one second film-forming organic functional material and optionally the at least one third film-forming organic functional material are different from each other.
- the first film-forming organic functional material is a polymer
- the second film-forming organic functional material is a compound having a low molecular weight, and vice versa.
- the first solvent of the first ink, the second solvent of the second ink and optionally the third solvent of the third ink are different from each other and are preferably organic solvents which include inter alia, ketones, ethers, esters, amides such as di-C-i-2-alkylform- amides, sulfur compounds, nitro compounds, hydrocarbons, halogenated hydrocarbons (e.g. chlorinated hydrocarbons), aromatic or heteroaromatic hydrocarbons (e.g. naphthalene derivatives) and halogenated aromatic or heteroaromatic hydrocarbons.
- organic solvents which include inter alia, ketones, ethers, esters, amides such as di-C-i-2-alkylform- amides, sulfur compounds, nitro compounds, hydrocarbons, halogenated hydrocarbons (e.g. chlorinated hydrocarbons), aromatic or heteroaromatic hydrocarbons (e.g. naphthalene derivatives) and halogenated aromatic or heteroaromatic hydrocarbons
- the first, second and optionally third solvents can be chosen from one of the following groups: substituted and non-substituted aromatic or linear ethers such as 3-phenoxytoluene or anisole; substituted or nonsubstituted arene derivatives such as cyclohexylbenzene; substituted or nonsubstituted indanes such as hexamethylindane; substituted and nonsubstituted aromatic or linear ketones such as dicyclohexylmethanone; substituted and non-substituted heterocycles such as pyrrolidinones, pyridines, pyrazines; other fluorinated or chlorinated aromatic hydrocarbons, substituted or non-substituted naphthalenes such as alkyl substituted naphthalenes, such as 1 -ethyl naphthalene.
- substituted and non-substituted aromatic or linear ethers such as 3-phenoxytoluene or ani
- Particularly preferred first, second and optionally third solvents are, for example, 1 -ethyl-naphthalene, 2-ethylnaphthalene, 2-propylnaphthalene, 2- (l-methylethyl)-naphthalene, 1 -(1 -methylethyl)-naphthalene, 2- butylnaphthalene, 1 ,6-dimethylnaphthalene, 2,2'-dimethylbiphenyl, 3,3'- dimethylbiphenyl, 1 -acetylnaphthalene, 1 ,2,3,4-tetramethylbenzene, 1 ,2,3,5- tetramethylbenzene, 1 ,2,4,5-tetramethylbenzene, 1 ,2,4-trichlorobenzene, 1 ,2-dihydronaphthalene, 1 ,2-dimethylnaphthalene, 1 ,3-benzodioxole, 1 ,3
- the first, second and optionally third solvent have a boiling point in the range from 100 to 400°C, preferably in the range from 200 to 350°C, more preferably in the range from 225 to 325°C and most preferably in the range from 250 to 300°C.
- the first, second and optional third film-forming organic functional materials have respectively a solubility in the corresponding organic solvents which is > 5 g/l, preferably > 10 g/l.
- the content of the at least one first, second or optional third film-forming organic functional materials in the corresponding formulations are respectively in the range from 0.001 to 20 weight-%, preferably in the range from 0.01 to 10 weight-%, more preferably in the range from 0.1 to 5 weight- % and most preferably in the range from 0.3 to 5 weight-%, based on the total weight of the formulation.
- first, second or optional third formulations of the present invention have respectively a viscosity preferably in the range from 0.8 to 50 mPa s, more preferably in the range from 1 to 40 mPa s, and most preferably in the range from 2 to 15 mPa s.
- the viscosity of the formulations and solvents according to the present invention is measured with a 1 ° cone-plate rotational rheometer of the type Discovery AR3 (Thermo Scientific). The equipment allows a precise control of the temperature and sheer rate. The measurement of the viscosity is carried out at a temperature of 25.0°C (+/- 0.2°C) and a sheer rate of 500 s’ 1 . Each sample is measured three times and the obtained measured values are averaged.
- the first, second or optional third formulations of the present invention have respectively a surface tension preferably in the range from 10 to 70 mN/m, more preferably in the range from 15 to 50 mN/m and most preferably in the range from 20 to 40 mN/m.
- the first, second or optional third organic solvents comprise respectively a surface tension in the range from 15 to 70 mN/m, more preferably in the range from 10 to 50 mN/m and most preferably in the range from 20 to 40 mN/m.
- the surface tension can be measured using a FTA (First Ten Angstrom) 1000 contact angle goniometer at 20°C. Details of the method are available from First Ten Angstrom as published by Roger P. Woodward, Ph.D.
- the pendant drop method can be used to determine the surface tension.
- This measurement technique dispenses a drop from a needle in a bulk liquid or gaseous phase.
- the shape of the drop results from the relationship between the surface-tension, gravity and density differences.
- the surface tension is calculated from the shadow image of a pendant drop using http://www.kruss.de/services/education- theory/glossary/drop-shape-analysis.
- the standard operating procedure includes the determination of the surface tension of each formulation using a fresh disposable drop dispensing system (syringe and needle). Each drop is measured over the duration of one minute with sixty measurements which are later on averaged. For each formulation three drops are measured. The final value is averaged over said measurements.
- the tool is regularly cross-checked against various liquids having well known surface tensions.
- the first solvent, the second solvent and optionally the third solvent are different from each other and may be selected from the solvents listed in the following Table 1 or mixtures thereof.
- the solvents of the first, second and third solvents may be a mixture of solvents, wherein the main solvent is as described above, and the remaining solvents are commonly used co-solvents for the main solvent.
- the first film-forming organic functional material in the second solvent has a dissolution time of more than 15 minutes, preferably of more than 30 minutes, more preferably of more than 60 minutes.
- the dissolution time of the first filmforming organic functional material in the second solvent is determined by performing ISO norm 7579:2009, which describes solubility determination by photometric or gravimetric methods.
- ISO norm 7579:2009 describes solubility determination by photometric or gravimetric methods.
- the photometric technique is recommended here.
- Dissolution tests as described in the following were performed. The experiment was designed with particular focus on ease of reproducibility.
- the material(s) to be analyzed i.e. the first film-forming material
- a solvent or a preformed solvent mixture (the second solvent) was then added to the solid mixture at once, calculated to reach a final concentration of 7 g/L.
- the mixture was stirred at 600 rpm using a magnetic stirrer and at room temperature (25°C) until complete dissolution, which was judged by visual inspection of the mixture.
- the mixture can additionally be examined under illumination perpendicular to the line of sight to help identify undissolved particles.
- “Time of dissolution”, also sometimes referred to as “dissolution time” toiss mentioned in this application was measured using a chronometer and quantifies the time between addition of the solvent and beginning of stirring until the disappearance of the last pieces of material into solution. The dissolution rate is determined by dividing 7 g/L by the time until full dissolution was obtained (the “dissolution time”).
- the substrate used in the inkjet printing method may be made of any suitable materials commonly used in the field of inkjet printing.
- the substrate used should be a transparent material selected from the group comprising glass, plastic, metal foil or flexible film.
- the printing is conducted on a substrate, on which all or a subset of subpixels have been deposited.
- the drying of the printed pixel is conducted by commonly used drying methods, comprising vacuum drying under reduced pressure.
- Alternative drying methods include thermal evaporation of the solvent, hot-air or infrared drying and others.
- the drying is conducted at room temperature or from about 0°C to about 50°C.
- the drying is conducted at a pressure of 1013 mbar or lower, preferably under 1 mbar.
- the second formulation is printed to the second subpixel adjacent to the first subpixel.
- the functional layers of the OLED are selected from the group comprising Hole Injection Layer (HIL), Hole Transport Layer (HTL), Emissive Layer (EML), Electron Transport Layer (ETL), Electron Injection Layer (EIL) or their combination.
- HIL Hole Injection Layer
- HTL Hole Transport Layer
- ETL Emissive Layer
- ETL Electron Transport Layer
- EIL Electron Injection Layer
- the functional layers consist of HIL, HTL and EML, which are successively provided on the substrate.
- the OLED is a full-color OLED.
- HTL hole-transport material
- polymer P1 polymer P1
- the target concentration of the dissolution experiment was 7 g/l.
- the solvents were classified according to their dissolution time toiss at 25°C and characterized by a dissolution type as shown in the following Tables 3a and 3b.
- Table 3a Dissolution types
- Table 3b Corresponding dissolution times
- a small molecule blend SM-1 as described in device fabrication example of WO 2017/102048 A1 was used.
- the target concentration of the dissolution experiment was 7 g/l.
- the solvents were classified according to their dissolution time toiss at 25°C and characterized by a dissolution type as shown in Table 4a below using the classification explained in Table 3b above.
- a small molecule blend SM-2 was used consisting of a 95/5 (weight/weight) mixture of a host H1 and an emitter E1 .
- the structure of H1 is given below, the emitter used was a material as described in the device fabrication example of WO 2018/007421 A1 as D2.
- the target concentration of the dissolution experiment was 7 g/l.
- the solvents were classified according to their dissolution time toiss at 25°C and characterized by a dissolution type as shown in Table 5a below using the classification explained in Table 3b above.
- a pixelated substrate with adjacent first pixels and second pixels is provided.
- the first ink comprising polymer P1 from a 20 mg/mL ink with 3-Phenoxy- toluene as first solvent is inkjet printed in first pixels.
- the substrate was subjected to drying at room temperature and at reduced pressure of 10’ 5 mBar.
- the second ink comprising an ink with 20 mg/mL SM-2 in 3- Phenoxytoluene (3-PT) is inkjet printed in second pixels.
- the substrate was subjected to drying at room temperature and at reduced pressure of 10’ 5 mBar.
- the profile of the first pixel before and after printing the second ink were characterized by a profile-meter.
- Alpha-step D120 from KLA-Tencor Corporation with a 2 pm stylus was used to measure the film profiles.
- Example 4 is repeated, but the second ink was replaced by 20 mg/mL SM-2 in Menthylisovalerate, and the drying of the second ink was conducted at room temperature and at reduced pressure of 10’ 5 mBar.
- Example 4 is repeated, but the second ink was replaced by 20 mg/mL SM-2 in 2-Phenoxyethanol (2-PEN), and the drying of the second ink was conducted at room temperature and at reduced pressure of 10’ 5 mBar.
- Example 6 is repeated, but the second ink was replaced by 20 mg/mL SM-1 in 2-Phenoxyethanol (2-PEN), and the drying of the second ink was conducted at room temperature and at reduced pressure of 10’ 5 mBar. Comparative Example 1
- a pixelated substrate with adjacent first pixels and second pixels is provided.
- the first ink comprising SM-1 from a 20 mg/mL ink with 3-Phenoxytoluene as first solvent is inkjet printed in first pixels.
- the substrate was subjected to drying at room temperature and at reduced pressure of 10’ 5 mBar.
- the second ink comprising an ink with 20 mg/mL SM-2 in 3-Phenoxytoluene (3- PT) is inkjet printed in second pixels.
- the substrate was subjected to drying at room temperature and at pressure of 10’ 5 mBar.
- the profile of the first pixel before and after printing the second ink were characterized by a profilemeter Alpha-step D120 from KLA-Tencor Corporation with a 2 pm stylus was used to measure the film profiles.
- the profile of the first pixel maintained smooth, stable and uniform before and after drying the second ink.
Abstract
Description
Claims
Priority Applications (3)
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KR1020237022897A KR20230114756A (en) | 2020-12-08 | 2021-12-06 | Ink Systems and Methods for Inkjet Printing |
JP2023533715A JP2023552761A (en) | 2020-12-08 | 2021-12-06 | Methods for ink-based and inkjet printing |
CN202180081990.4A CN116635491A (en) | 2020-12-08 | 2021-12-06 | Ink system and method for inkjet printing |
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EP20212464 | 2020-12-08 | ||
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