US20220352468A1 - Organic electroluminescent device emitting visible light - Google Patents

Organic electroluminescent device emitting visible light Download PDF

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US20220352468A1
US20220352468A1 US17/762,194 US202017762194A US2022352468A1 US 20220352468 A1 US20220352468 A1 US 20220352468A1 US 202017762194 A US202017762194 A US 202017762194A US 2022352468 A1 US2022352468 A1 US 2022352468A1
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deuterium
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Hamed SHARIFIDEHSARI
Federico Koch
Georgios LIAPTSIS
Jaime Leganes CARBALLO
Christian KASPAREK
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Samsung Display Co Ltd
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Samsung Display Co Ltd
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Assigned to SAMSUNG DISPLAY CO., LTD. reassignment SAMSUNG DISPLAY CO., LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CYNORA GMBH
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    • H10K85/30—Coordination compounds
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    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H10K50/121—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants for assisting energy transfer, e.g. sensitization
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
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    • 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
    • H10K50/135—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising mobile ions
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    • H10K50/30—Organic light-emitting transistors

Definitions

  • the present invention relates to organic electroluminescent devices comprising a light-emitting layer B comprising a host material H B , a thermally activated delayed fluorescence (TADF) material E B , and a depopulation agent S B .
  • TADF thermally activated delayed fluorescence
  • Organic electroluminescent devices containing one or more light-emitting layers based on organics such as, e.g., organic light emitting diodes (OLEDs), light emitting electrochemical cells (LECs) and light-emitting transistors gain increasing importance.
  • OLEDs organic light emitting diodes
  • LOCs light emitting electrochemical cells
  • OLEDs are promising devices for electronic products such as e.g. screens, displays and illumination devices.
  • organic electroluminescent devices based on organics are often rather flexible and producible in particularly thin layers.
  • the OLED-based screens and displays already available today bear particularly beneficial brilliant colors, contrasts and are comparably efficient with respect to their energy consumption.
  • a central element of an organic electroluminescent device for generating light is a light-emitting layer placed between an anode and a cathode.
  • a voltage (and current) is applied to an organic electroluminescent device, holes and electrons are injected from an anode and a cathode, respectively, to the light-emitting layer.
  • a hole transport layer is located between light-emitting layer and the anode
  • an electron transport layer is located between light-emitting layer and the cathode.
  • the different layers are sequentially disposed.
  • Excitons of high energy are then generated by recombination of the holes and the electrons.
  • the decay of such excited states e.g., singlet states such as S1 and/or triplet states such as T1 to the ground state (S0) desirably leads to light emission.
  • an organic electroluminescent device comprises one or more host compounds and one or more emitter compounds as dopants.
  • an organic electroluminescent device's light-emitting layer comprising one thermally activated delayed fluorescence (TADF) material, a depopulation agent and a host material provides an organic electroluminescent device having good lifetime and quantum yields and exhibiting emission in the visible.
  • TADF thermally activated delayed fluorescence
  • an organic electroluminescent device which comprises a light-emitting layer B comprising:
  • the lowermost excited singlet state of the host material H B is higher in energy than the lowermost excited singlet state of the thermally activated delayed fluorescence (TADF) material E B .
  • TADF thermally activated delayed fluorescence
  • the lowermost excited singlet state of the host material H B is higher in energy than the lowermost excited singlet state of the depopulation agent S B .
  • the lowermost excited singlet state of the TADF material E B is lower in energy than the lowermost excited singlet state of the depopulation agent S B .
  • the highest occupied molecular orbital of the TADF material E B (E HOMO (E B )) is higher in energy than the highest occupied molecular orbital of the host material H B (E HOMO (H B )) (i.e. the TADF material E B acts as the main hole transport material).
  • the highest occupied molecular orbital of the depopulation agent S B (E HOMO (S B )) is higher in energy than the highest occupied molecular orbital of the TADF material E B (E HOMO (E B )).
  • the energy difference between E HOMO (S B ) ⁇ E HOMO (E B ) is at least 0.2 eV and not more than 0.8 eV, in particular at least 0.25 eV and not more than 0.55 eV.
  • the highest occupied molecular orbital of the host material H B (E HOMO (H B )) is higher in energy than the highest occupied molecular orbital of the TADF material E B (E HOMO (E B )) (i.e. the host material H B acts as the main hole transport material).
  • the highest occupied molecular orbital of the depopulation agent S B (E HOMO (S B )) is higher in energy than the highest occupied molecular orbital of the host material H B (E HOMO (H B ))
  • the energy difference between E HOMO (S B ) ⁇ E HOMO (H B ) is at least 0.2 eV and not more than 0.8 eV, in particular at least 0.25 eV and not more than 0.55 eV.
  • the energy difference between E HOMO (S B ) ⁇ E HOMO (E B ) is at least 0.15 eV, at least 0.16 eV, at least 0.17 eV, at least 0.18 eV, at least 0.19 eV, at least 0.20 eV, at least 0.21 eV, at least 0.22 eV, at least 0.23 eV, at least 0.24 eV, or at least 0.25 eV.
  • the energy difference between E HOMO (S B ) ⁇ E HOMO (E B ) is not more than 0.8 eV, not more than 0.75 eV, not more than 0.70 eV, not more than 0.65 eV, not more than 0.60 eV, or not more than 0.55 eV.
  • the highest occupied molecular orbital of the host material H B is equal in energy than the highest occupied molecular orbital of the TADF material E B .
  • the highest occupied molecular orbital of the depopulation agent S B (E HOMO (S B )) is higher in energy than the highest occupied molecular orbital of the host material H B (E HOMO (H B )) and/or the highest occupied molecular orbital of the TADF material E B (E HOMO (E B )).
  • the energy difference between E HOMO (S B ) ⁇ E HOMO (H B ) and/or the energy difference between E HOMO (S B ) ⁇ E HOMO (E B ) is at least 0.2 eV and not more than 0.8 eV, in particular at least 0.25 eV and not more than 0.55 eV.
  • the energy difference between E HOMO (S B ) ⁇ E HOMO (H B ) is at least 0.15 eV, at least 0.16 eV, at least 0.17 eV, at least 0.18 eV, at least 0.19 eV, at least 0.20 eV, at least 0.21 eV, at least 0.22 eV, at least 0.23 eV, at least 0.24 eV, or at least 0.25 eV.
  • the energy difference between E HOMO (S B ) ⁇ E HOMO (H B ) is not more than 0.8 eV, not more than 0.75 eV, not more than 0.70 eV, not more than 0.65 eV, not more than 0.60 eV, or not more than 0.55 eV.
  • TADF material and “TADF emitter” and “TADF emitters” may be understood interchangeably.
  • emitter emitter compound or the like
  • E B a TADF material of the present invention
  • a TADF material is characterized in that it exhibits a ⁇ E ST value, which corresponds to the energy difference between the lowermost excited singlet state (S1) and the lowermost excited triplet state (T1), of less than 0.4 eV, preferably less than 0.3 eV, more preferably less than 0.2 eV.
  • the TADF material E B is characterized in that it has a ⁇ E ST value, which corresponds to the energy difference between S1 E and T1 E , of less than 0.4 eV.
  • the TADF material E B is characterized in that it has a ⁇ E ST value of less than 0.3 eV, less than 0.2 eV.
  • mass ratio of TADF material E B to the depopulation agent S B (E B S B ) is >1.
  • the mass ratio E B :S B is in the range of from 1.5:1 to 30:1, in the range of from 2:1 to 25:1, or in the range of from 3:1 to 20:1.
  • the mass ratio E B :S B is in the range of (approximately) 20:1, 15:1, 12:1, 10:1, 8:1, 5:1, or 4:1.
  • organic electroluminescent device and opto-electronic light-emitting devices may be understood in the broadest sense as any device comprising a light-emitting layer B comprising a host material H B , a TADF material E B and a depopulation agent S B .
  • the light-emitting layer B may also comprise more than one TADF materials E B and/or more than one depopulation agent S B each having the properties as described herein.
  • the light-emitting layer B comprises at least one TADF material E B and at least one depopulation agent S B each having the properties as described herein.
  • the light-emitting layer B comprises one TADF material E B and one depopulation agent S B each having the properties as described herein.
  • organic electroluminescent device and opto-electronic light-emitting devices may be understood in the broadest sense as any device comprising a light-emitting layer B comprising a host material H B , a TADF material E B and a depopulation agent S B .
  • the organic electroluminescent device is a device selected from the group consisting of an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), and a light-emitting transistor.
  • OLED organic light emitting diode
  • LEC light emitting electrochemical cell
  • the organic electroluminescent device is an organic light emitting diode (OLED).
  • OLED organic light emitting diode
  • the organic electroluminescent device as a whole may be intransparent, semi-transparent or (essentially) transparent.
  • the term “layer” as used in the context of the present invention preferably is a body that bears an extensively planar geometry.
  • the light-emitting layer B preferably bears a thickness of not more than 1 mm, more preferably not more than 0.1 mm, even more preferably not more than 10 ⁇ m, even more preferably not more than 1 ⁇ m, in particular not more than 0.1 ⁇ m.
  • the light-emitting layer B will typically be incorporated in the organic electroluminescent device of the present invention.
  • such organic electroluminescent device comprises at least the following layers: at least one light-emitting layer B, at least one anode layer A and at least one cathode layer C.
  • the anode layer A contains at least one component selected from the group consisting of indium tin oxide, indium zinc oxide, PbO, SnO, graphite, doped silicium, doped germanium, doped GaAs, doped polyaniline, doped polypyrrole, doped polythiophene, and mixtures of two or more thereof.
  • the cathode layer C contains at least one component selected from the group consisting of Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd, LiF, Ca, Ba, Mg, and mixtures or alloys of two or more thereof.
  • the light-emitting layer B is located between an anode layer A and a cathode layer C.
  • the general set-up is preferably A-B-C. This does of course not exclude the presence of one or more optional further layers. These can be present at each side of A, of B and/or of C.
  • the organic electroluminescent device comprises at least the following layers:
  • the organic electroluminescent device when the organic electroluminescent device is an OLED, it may optionally comprise the following layer structure:
  • anode layer A exemplarily comprising indium tin oxide (ITO); HTL) a hole transport layer HTL; B) a light-emitting layer B according to present invention as described herein; ETL) an electron transport layer ETL; and C) a cathode layer, exemplarily comprising Al, Ca and/or Mg.
  • ITO indium tin oxide
  • HTL hole transport layer
  • HTL hole transport layer
  • ETL an electron transport layer
  • a cathode layer exemplarily comprising Al, Ca and/or Mg.
  • the order of the layers herein is A-HTL-B-ETL-C.
  • the organic electroluminescent device may optionally comprise one or more protective layers protecting the device from damaging exposure to harmful species in the environment including, exemplarily moisture, vapor and/or gases.
  • the anode layer A is located on the surface of a substrate.
  • the substrate may be formed by any material or composition of materials. Most frequently, glass slides are used as substrates. Alternatively, thin metal layers (e.g., copper, gold, silver or aluminum films) or plastic films or slides may be used. This may allow a higher degree of flexibility.
  • the anode layer A is mostly composed of materials allowing to obtain an (essentially) transparent film. As at least one of both electrodes should be (essentially) transparent in order to allow light emission from the OLED, either the anode layer A or the cathode layer C transparent.
  • the anode layer A comprises a large content or even consists of transparent conductive oxides (TCOs).
  • Such anode layer A may exemplarily comprise indium tin oxide, aluminum zinc oxide, fluor tin oxide, indium zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, wolfram oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrol and/or doped polythiophene.
  • the anode layer A (essentially) consists of indium tin oxide (ITO) (e.g., (InO 3 ) 0.9 (SnO 2 ) 0.1 ).
  • ITO indium tin oxide
  • TCOs transparent conductive oxides
  • HIL hole injection layer
  • the HIL may facilitate the injection of quasi charge carriers (i.e., holes) in that the transport of the quasi charge carriers from the TCO to the hole transport layer (HTL) is facilitated.
  • the hole injection layer may comprise poly-3,4-ethylendioxy thiophene (PEDOT), polystyrene sulfonate (PSS), MoO 2 , V 2 O 5 , CuPC or CuI, in particular a mixture of PEDOT and PSS.
  • the hole injection layer (HIL) may also prevent the diffusion of metals from the anode layer A into the hole transport layer (HTL).
  • the HIL may exemplarily comprise PEDOT:PSS (poly-3,4-ethylendioxy thiophene:polystyrene sulfonate), PEDOT (poly-3,4-ethylendioxy thiophene), mMTDATA (4,4′,4′′-tris[phenyl(m-tolyl)amino]triphenylamine), Spiro-TAD (2,2′,7,7′-tetrakis(n,n-diphenylamino)-9,9′-spirobifluorene), DNTPD (N1,N1′-(biphenyl-4,4′-diyl)bis(N1-phenyl-N4,N4-di-m-tolylbenzene-1,4-diamine), NPB (N,N′-nis-(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4
  • HTL hole transport layer
  • EML emitting layer
  • EBL electron blocking layer
  • hole transport compounds bear comparably high energy levels of their triplet states T1.
  • the hole transport layer may comprise a star-shaped heterocycle such as tris(4-carbazoyl-9-ylphenyl)amine (TCTA), poly-TPD (poly(4-butylphenyl-diphenyl-amine)), [alpha]-NPD (poly(4-butylphenyl-diphenyl-amine)), TAPC (4,4′-cyclohexyliden-bis[N,N-bis(4-methylphenyl)benzenamine]), 2-TNATA (4,4′,4′′-tris[2-naphthyl(phenyl)-amino]triphenylamine), Spiro-TAD, DNTPD, NPB, NPNPB, MeO-TPD, HAT-CN and/or TrisPcz (9,9′-diphenyl-6-(9-phenyl-9H-carbazol-3-yl)-9H,9′H-3,3′-bicarbazole).
  • TCTA tris(4
  • the HTL may comprise a p-doped layer, which may be composed of an inorganic or organic dopant in an organic hole-transporting matrix.
  • Transition metal oxides such as vanadium oxide, molybdenum oxide or tungsten oxide may exemplarily be used as inorganic dopant.
  • Tetrafluorotetracyanoquinodimethane F4-TCNQ
  • copper-pentafluorobenzoate Cu(I)pFBz
  • transition metal complexes may exemplarily be used as organic dopant.
  • the EBL may exemplarily comprise mCP (1,3-bis(carbazol-9-yl)benzene), TCTA, 2-TNATA, mCBP (3,3-di(9H-carbazol-9-yl)biphenyl), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole, tris-Pcz, CzSi (9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9
  • the depopulation agent S B is selected from the group consisting of a fluorescence emitter and an organic TADF emitter, whereas the organic TADF emitter is characterized in that it has a ⁇ E ST value, which corresponds to the energy difference between S1 S and T1 S , of less than 0.4 eV.
  • the depopulation agent S B is an organic TADF emitter or a combination of two or more organic TADF emitters. In a preferred embodiment, the depopulation agent S B is an organic TADF emitter.
  • the depopulation agent S B is a TADF material, i.e., one or more TADF emitter. Accordingly in an embodiment of the present invention, the depopulation agent S B is characterized in that it has a ⁇ E ST value, which corresponds to the energy difference between S1 S and T1 S , of less than 0.4 eV. In a preferred embodiment of the present invention, the depopulation agent S B is characterized in that it has a ⁇ E ST value of less than 0.3 eV, less than 0.2 eV, less than 0.1 eV, or even less than 0.05 eV.
  • the TADF material E B and the depopulation agent S B are both organic TADF emitters.
  • the lowermost excited triplet state energy level T1 E of the TADF material E B is between 2.2 eV and 3.5 eV, preferably between 2.3 eV and 3.2 eV, more preferably between 2.4 eV and 3.1 eV or even between 2.5 eV and 3.0 eV.
  • the emission layer B comprises at least one host material H B , the TADF material E B and the depopulation agent S B .
  • the light-emitting layer B comprises 39.8-98%, more preferably 57-93%, even more preferably 74-87% by weight of the host compound H B .
  • the light-emitting layer B comprises 0.1-50%, more preferably 0.5-40%, even more preferably 1-30% by weight of the TADF material E B .
  • the light-emitting layer B comprises 0.1-10%, more preferably 0.5-8%, even more preferably 1-5% by weight of the depopulation agent S B .
  • the TADF material E B is an organic TADF emitter or a combination of two or more organic TADF emitters
  • the depopulation agent S B is an organic TADF emitter, wherein the light-emitting layer B comprises 0.1-10%, more preferably 0.5-8%, even more preferably 1-5% by weight of the depopulation agent S B .
  • the depopulation agent S B is a NRCT emitter, wherein the light-emitting layer B comprises 0.1-10%, more preferably 0.5-8%, even more preferably 1-5% by weight of the depopulation agent S B .
  • the depopulation agent S B is a fluorescence emitter, wherein the light-emitting layer B comprises 0.1-10%, more preferably 0.5-8%, even more preferably 1-5% by weight of the depopulation agent S B .
  • the TADF material E B is an organic TADF emitter, wherein the light-emitting layer B comprises 1-50%, more preferably 5-40%, even more preferably 10-30% by weight of the TADF material E B .
  • the TADF material E B is a NRCT emitter, wherein the light-emitting layer B comprises 0.1-10%, more preferably 0.5-5%, even more preferably 1-3% by weight of the TADF material E B .
  • the light-emitting layer B comprises up to 93% by weight of one or more further host compounds H B2 differing from H B .
  • the light-emitting layer B comprises up to 93% by weight of one or more solvents.
  • the light-emitting layer B comprises (or consists of):
  • the contents of (i) to (v) sum up to 100% by weight.
  • the depopulation agent S B and the TADF material E B are each independently from each other a NRCT emitter, wherein the light-emitting layer B comprises (or consists of):
  • the depopulation agent S B is an organic TADF emitter and the TADF material E B is a NRCT emitter, wherein the light-emitting layer B comprises (or consists of):
  • the depopulation agent S B is a NRCT emitter and the TADF material E B is an organic TADF emitter, wherein the light-emitting layer B comprises (or consists of):
  • the depopulation agent S B is a fluorescence emitter and the TADF material E B is a NRCT emitter, wherein the light-emitting layer B comprises (or consists of):
  • the depopulation agent S B is a fluorescence emitter and the TADF material E B is an organic TADF emitter, wherein the light-emitting layer B comprises (or consists of):
  • the host material H B and/or the optionally present further host compound H B2 may be selected from the group consisting of CBP (4,4′-Bis-(N-carbazolyl)-biphenyl), mCP, mCBP Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), CzSi, Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), DPEPO (bis[2-(diphenylphosphino)phenyl] ether oxide), 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl
  • the emission layer B comprises the TADF material E B and the depopulation agent S B (which is exemplarily a second TADF material S B ), and hole-dominant host H B selected from the group consisting of CBP, mCP, mCBP, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzofuran-2-yl)phenyl]-9H-carbazole, 9-[3-(dibenzothiophen-2-yl)phenyl]-9H-carbazole, 9-[3,5-bis(2-dibenzofuranyl)phenyl]-9H-carbazole and 9-[3,5-bis(2-dibenzothiophenyl)phenyl]-9H-carbazole.
  • the designation of the colors of emitted and/or absorbed light is as follows:
  • violet wavelength range of >380-420 nm
  • deep blue wavelength range of >420-470 nm
  • sky blue wavelength range of >470-500 nm
  • green wavelength range of >500-560 nm
  • yellow wavelength range of >560-580 nm
  • orange wavelength range of >580-620 nm
  • red wavelength range of >620-800 nm.
  • emitter compounds such colors refer to the emission maximum ⁇ max PMMA of a poly(methyl methacrylate) (PMMA) film with typically 1-10% by weight of the emitter. Therefore, exemplarily, a deep blue emitter has an emission maximum ⁇ max PMMA in the range of from 420 to 470 nm, a sky blue emitter has an emission maximum ⁇ max PMMA in the range of from 470 to 500 nm, a green emitter has an emission maximum ⁇ max PMMA in a range of from 500 to 560 nm, a red emitter has an emission maximum ⁇ max PMMA in a range of from 620 to 800 nm.
  • PMMA poly(methyl methacrylate)
  • the organic electroluminescent device exhibits green emission.
  • the organic electroluminescent device exhibits blue emission.
  • the organic electroluminescent device exhibits red emission.
  • the organic electroluminescent device exhibits an emission maximum k max (D) of 440 to 560 nm.
  • the organic electroluminescent device exhibits an emission maximum k max (D) of 440 to 470 nm.
  • the organic electroluminescent device exhibits an emission maximum k max (D) of 510 to 550 nm.
  • a Near-range-charge-transfer (NRCT) emitter in the context of the present invention is any emitter that has an emission spectrum, which exhibits a full width at half maximum (FWHM) of less than or equal to 0.25 eV (s 0.25 eV), measured with 1% by weight of NRCT emitter in PMMA at room temperature (RT).
  • FWHM full width at half maximum
  • the each spectral property determined herein is determined at a content of 1% by weight of the respective emitter in PMMA at room temperature (RT).
  • the FWHM is determined at a content of 1% by weight of the respective emitter in PMMA at room temperature (RT).
  • a NRCT emitter in the context of the present invention is any emitter that has an emission spectrum, which exhibits a FWHM of ⁇ 0.24 eV, more preferably ⁇ 0.23 eV, even more preferably ⁇ 0.22 eV, ⁇ 0.21 eV or ⁇ 0.20 eV, measured with 1% by weight of NRCT emitter in PMMA at room temperature (RT).
  • an emitter exhibits a FWHM of ⁇ 0.19 eV, ⁇ 0.19 eV, ⁇ 0.18 eV, ⁇ 0.17 eV, ⁇ 0.16 eV, ⁇ 0.15 eV, ⁇ 0.14 eV, ⁇ 0.13 eV, ⁇ 0.12 eV, or ⁇ 0.11 eV.
  • Typical NRCT emitters are described in literature by Hatakeyama et al. (Advanced Materials, 2016, 28(14):2777-2781, DOI: 10.1002/adma.201505491) to show a delayed component in the time-resolved photoluminescence spectrum and exhibits a near-range HOMO-LUMO separation as described.
  • the emitters shown in Hatakeyama et al. may be NRCT emitters, which are also TADF emitters in the sense of the present invention.
  • Typical NRCT emitters only show one emission band in the emission spectrum, wherein typical fluorescence emitters display several distinct emission bands due to vibrational progression.
  • the TADF material E B and/or the depopulation agent S B is a NRCT emitter. In one embodiment of the invention, the TADF material E B and the depopulation agent S B are both each a NRCT emitter. In another embodiment of the invention, the TADF material E B is no NRCT emitter. In this case, the TADF material E B is an emitter which shows TADF properties, but not the properties of a NRCT emitter as defined herein. In further embodiment of the invention, the depopulation agent S B is no NRCT emitter. In this case, the depopulation agent S B is an emitter which does not have the properties of a NRCT emitter as defined herein.
  • the depopulation agent S B is a fluorescent emitter. In one embodiment of the invention, the depopulation agent S B is a fluorescent emitter which is no NRCT emitter. In further embodiment of the invention, neither the TADF material E B nor the depopulation agent S B are NRCT emitters.
  • An NRCT emitter may, in each context of the present invention, optionally each be a boron containing NRCT emitter, in particular a blue boron containing NRCT emitter.
  • the TADF material E B is a NRCT emitter.
  • the TADF material E B and/or the depopulation agent S B is a boron containing NRCT emitter.
  • the TADF material E B and the depopulation agent S B is a boron containing NRCT emitter.
  • the TADF material E B is a boron containing NRCT emitter.
  • the TADF material E B is a blue boron containing NRCT emitter.
  • a NRCT emitter comprises or consists of a polycyclic aromatic compound.
  • TADF material E B and/or the depopulation agent S B comprises or consists of a polycyclic aromatic compound.
  • the emission spectrum of a film with 1% by weight of the TADF material E B has a full width at half maximum (FWHM), which is smaller than 0.2 eV.
  • the TADF material E B is a boron containing emitter with an emission spectrum of a film with 1% by weight of the TADF material E B , which has a full width at half maximum (FWHM), which is smaller than 0.2 eV.
  • FWHM full width at half maximum
  • the TADF material E B is a blue boron containing emitter with an emission spectrum of a film with 1% by weight of the TADF material E B , which has a full width at half maximum (FWHM), which is smaller than 0.2 eV.
  • FWHM full width at half maximum
  • the TADF material E B comprises or consists of a polycyclic aromatic compound with an emission spectrum of a film with 1% by weight of the TADF material E B , which has a full width at half maximum (FWHM), which is smaller than 0.2 eV.
  • FWHM full width at half maximum
  • the TADF material E B comprises or consists of a polycyclic aromatic compound according to formula (1) or (2) or a specific example described in US-A 2015/236274. US-A 2015/236274 also describes examples for synthesis of such compounds.
  • the TADF material E B comprises or consists of a structure according to Formula I:
  • n 0 or 1.
  • X 1 is N or B.
  • X 2 is N or B.
  • X 3 is N or B.
  • W is selected from the group consisting of Si(R 3 ) 2 , C(R 3 ) 2 and BR 3 .
  • each of R 1 , R 2 and R 3 is independently from each other selected from the group consisting of: C 1 -C 5 -alkyl, which is optionally substituted with one or more substituents R 6 ; C 6 -C 60 -aryl, which is optionally substituted with one or more substituents R 6 ; and C 3 -C 57 -heteroaryl, which is optionally substituted with one or more substituents R 6 ;
  • each of R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , and R XI is independently from another selected from the group consisting of: hydrogen, deuterium, N(R 5 ) 2 , OR 5 , Si(R 5 ) 3 , B(OR 5 ) 2 , OSO 2 R 5 ,
  • R 5 is at each occurrence independently from another selected from the group consisting of: hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 5 -alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F; C 1 -C 5 -alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F; C 1 -C 5 -thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkynyl, wherein optionally one or more hydrogen atoms are independently from each
  • R 6 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, OPh, CF 3 , CN, F, C 1 -C 5 -alkyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F; C 1 -C 5 -alkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F; C 1 -C 5 -thioalkoxy, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkenyl, wherein optionally one or more hydrogen atoms are independently from each other substituted by deuterium, CN, CF 3 , or F; C 2 -C 5 -alkynyl, wherein optionally one or more hydrogen atoms are independently from each other
  • two or more of the substituents selected from the group consisting of R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , and R XI that are positioned adjacent to another may each form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with another.
  • At least one of X 1 , X 2 and X 3 is B and at least one of X 1 , X 2 and X 3 is N.
  • At least one substituent selected from the group consisting of R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , and R XI optionally forms a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more substituents of the same group that is/are positioned adjacent to the at least one substituent.
  • At least one of X 1 , X 2 and X 3 is B and at least one of X 1 , X 2 and X 3 is N.
  • each of R 1 and R 2 is each independently from each other selected from the group consisting of
  • C 1 -C 5 -alkyl which is optionally substituted with one or more substituents R 6 ;
  • C 6 -C 30 -aryl which is optionally substituted with one or more substituents R 6 ;
  • C 3 -C 30 -heteroaryl which is optionally substituted with one or more substituents R 6 .
  • R 1 and R 2 is each independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 ,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 , and Ph;
  • each of R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , and R XI is independently from another selected from the group consisting of: hydrogen, deuterium, halogen, Me, i Pr, t Bu, CN, CF 3 ,
  • each of R I , R II , R III , R IV , R V , R VI , R VII , R VIII , R IX , R X , and R XI is independently from another selected from the group consisting of: hydrogen, deuterium, halogen, Me, i Pr, t Bu, CN, CF 3 ,
  • the depopulation agent S B is a near-range-charge-transfer (NRCT) emitter.
  • NRCT near-range-charge-transfer
  • a NRCT material shows a delayed component in the time-resolved photoluminescence spectrum and exhibits a near-range HOMO-LUMO separation as described by Hatakeyama et al. (Advanced Materials, 2016, 28(14):2777-2781, DOI: 10.1002/adma.201505491).
  • the depopulation agent S B is a boron containing NRCT emitter.
  • the depopulation agent S B is a blue boron containing NRCT emitter.
  • the depopulation agent S B comprises or consists of a polycyclic aromatic compound.
  • the emission spectrum of a film with 1% by weight of the depopulation agent S B has a full width at half maximum (FWHM), which is smaller than 0.2 eV.
  • the depopulation agent S B is a boron containing emitter with an emission spectrum of a film with 1% by weight of the depopulation agent S B , which has a full width at half maximum (FWHM), which is smaller than 0.2 eV.
  • FWHM full width at half maximum
  • the depopulation agent S B is a blue boron containing emitter with an emission spectrum of a film with 1% by weight of the depopulation agent S B , which has a full width at half maximum (FWHM), which is smaller than 0.2 eV.
  • FWHM full width at half maximum
  • the depopulation agent S B comprises or consists of a polycyclic aromatic compound with an emission spectrum of a film with 1% by weight of, the depopulation agent S B , which has a full width at half maximum (FWHM), which is smaller than 0.2 eV.
  • FWHM full width at half maximum
  • the depopulation agent S B comprises or consists of a polycyclic aromatic compound according to formula (1) or (2) or a specific example described in US-A 2015/236274. US-A 2015/236274 also describes examples for synthesis of such compounds.
  • the depopulation agent S B comprises or consists of a structure according to Formula I.
  • the TADF material E B and/or the depopulation agent S B is a blue boron-containing NRCT emitter selected from the following group:
  • the TADF material E B and/or the depopulation agent S B is a green boron-containing NRCT emitter selected from the following group:
  • the TADF material E B and/or the depopulation agent S B is an organic TADF material.
  • organic emitter or organic material means that the emitter or material (predominantly) consists of the elements hydrogen (H), carbon (C), nitrogen (N), boron (B), silicon (Si) and optionally fluorine (F), optionally bromine (Br) and optionally oxygen (O). Particularly preferably, it does not contain any transition metals.
  • the TADF material E B is an organic TADF material.
  • the depopulation agent S B is an organic emitter.
  • the TADF material E B and the depopulation agent S B are both organic TADF materials.
  • the TADF material E B and/or the depopulation agent S B is an organic TADF material, which is chosen from molecules of a structure of Formula I-TADF
  • R 1 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, C 1 -C 5 -alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium, and C 6 -C 18 -aryl, which is optionally substituted with one or more substituents R 6 ;
  • R 2 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, C 1 -C 5 -alkyl, wherein one or more hydrogen atoms are optionally substituted by deuterium, and C 6 -C 18 -aryl, which is optionally substituted with one or more substituents R 6 ;
  • R a , R 3 and R 4 is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, N(R 5 ) 2 , OR 5 , SR 5 , Si(R 5 ) 3
  • the substituents R a , R 3 , R 4 or R 5 at each occurrence independently from each other may optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more other substituents R a , R 3 , R 4 or R 5 .
  • the substituents R d at each occurrence independently from each other may optionally form a mono- or polycyclic, aliphatic, aromatic and/or benzo-fused ring system with one or more other substituents R d .
  • Z is a direct bond at each occurrence.
  • the TADF material E B is an organic TADF material, which is chosen from molecules of a structure of Formula I-TADF.
  • the TADF material E B comprises at least one triazine structure according to Formula IIa.
  • the TADF material E B is an organic TADF material, which is chosen from molecules of a structure of Formula II-TADF
  • R a is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 ,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .
  • R d is at each occurrence independently from another selected from the group consisting of hydrogen, deuterium, Me, i Pr, t Bu, CN, CF 3 ,
  • Ph which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyridinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; pyrimidinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; carbazolyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; triazinyl, which is optionally substituted with one or more substituents independently from each other selected from the group consisting of Me, i Pr, t Bu, CN, CF 3 and Ph; and N(Ph) 2 .
  • X is CN
  • the TADF material E B is chosen from a structure of Formula III:
  • R a , X and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula IIIa:
  • R a , X and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula IIIa-1:
  • R a , X and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula IIIa-2:
  • R a , X and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula IIIb:
  • R a and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula IIIa-1:
  • R a and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula IIIc:
  • R a and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula IIId:
  • R a and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula IV:
  • R a , R 1 and X are defined as above.
  • E B is chosen from molecules of a structure of Formula IVa:
  • R a , R 1 and X are defined as above.
  • E B is chosen from molecules of a structure of Formula IVb:
  • R a and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula V:
  • R a , R 1 and X are defined as above.
  • E B is chosen from molecules of a structure of Formula Va:
  • R a , R 1 and X are defined as above.
  • E B is chosen from molecules of a structure of Formula Vb:
  • R a and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula VI:
  • R a , R 1 and X are defined as above.
  • E B is chosen from molecules of a structure of Formula Via:
  • R a , R 1 and X are defined as above.
  • E B is chosen from molecules of a structure of Formula VIb:
  • R a and R 1 are defined as above.
  • E B is chosen from molecules of a structure of Formula VII:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula VIIa:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula VIIb:
  • R a is defined as above.
  • E B is chosen from molecules of a structure of Formula VIII:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula VIIIa:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula VIIIb:
  • R a is defined as above.
  • E B is chosen from molecules of a structure of Formula IX:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula IXa:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula IXb:
  • R a is defined as above.
  • E B is chosen from molecules of a structure of Formula X:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula Xa:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula Xb:
  • R a is defined a s above.
  • E B is chosen from molecules of a structure of Formula XI:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula XIa:
  • R a and X are defined as above.
  • E B is chosen from molecules of a structure of Formula XIb:
  • R a is defined as above.
  • E B is chosen from molecules of a structure of Formula XII:
  • R a , X and R d are defined as above.
  • E B is chosen from molecules of a structure of Formula XIIa:
  • R a , X and R d are defined as above.
  • E B is chosen from molecules of a structure of Formula XIIb:
  • R a , X and R d are defined as above.
  • a coupling reaction preferably a palladium catalyzed coupling reaction.
  • second reactant E2 preferably Ar E WG-Br is used. Reaction conditions of such palladium catalyzed coupling reactions are known the person skilled in the art, e.g. from WO 2017/005699, and it is known that the reacting groups of E1 and E2 can be interchanged to optimize the reaction yields.
  • the molecules according to Formula I-TADF are obtained via the reaction of a nitrogen heterocycle in a nucleophilic aromatic substitution with the aryl halide, preferably aryl fluoride, or aryl dihalide, preferably aryl difluoride, E3.
  • Typical conditions include the use of a base, such as tribasic potassium phosphate or sodium hydride, for example, in an aprotic polar solvent, such as dimethyl sulfoxide (DMSO) or N,N-dimethylformamide (DMF), for example.
  • the donor molecule E6 is a 3,6-substituted carbazole (e.g., 3,6-dimethylcarbazole, 3,6 diphenylcarbazole, 3,6-di-tert-butylcarbazole), a 2,7-substituted carbazole (e.g., 2,7 dimethylcarbazole, 2,7-diphenylcarbazole, 2,7-di-tert-butylcarbazole), a 1,8-substituted carbazole (e.g., 1,8-dimethylcarbazole, 1,8-diphenylcarbazole, 1,8-di-tert-butylcarbazole), a 1 substituted carbazole (e.g., 1-methylcarbazole, 1-phenylcarbazole, 1-tert-butylcarbazole), a 2 substituted carbazole (e.g., 2-methylcarbazole, 2-phenylcarbazole, 2-
  • halogen-substituted carbazole particularly 3-bromocarbazole, can be used as E6.
  • a boronic acid ester functional group or boronic acid functional group may be exemplarily introduced at the position of the one or more halogen substituents, which was introduced via E6, to yield the corresponding carbazol-3-ylboronic acid ester or carbazol-3-ylboronic acid, e.g., via the reaction with bis(pinacolato)diboron (CAS No. 73183-34-3).
  • one or more substituents R a may be introduced in place of the boronic acid ester group or the boronic acid group via a coupling reaction with the corresponding halogenated reactant R a -Hal, preferably R a —Cl and R a —Br.
  • one or more substituents R a may be introduced at the position of the one or more halogen substituents, which was introduced via D-H, via the reaction with a boronic acid of the substituent R a [R a —B(OH) 2 ] or a corresponding boronic acid ester.
  • An alternative synthesis route comprises the introduction of a nitrogen heterocycle via copper- or palladium-catalyzed coupling to an aryl halide or aryl pseudohalide, preferably an aryl bromide, an aryl iodide, aryl triflate or an aryl tosylate.
  • the depopulation agent S B is a fluorescence emitter, in particular a blue fluorescence emitter.
  • the depopulation agent S B is a blue fluorescence emitter selected from the following group:
  • the depopulation agent S B is a blue fluorescence emitter selected from the following group:
  • Depopulation Agent S B is a Triplet-Triplet Annihilation (TTA) Fluorescence Emitter
  • the depopulation agent S B is a triplet-triplet annihilation (TTA) emitter.
  • TTA triplet-triplet annihilation
  • S B is a blue TTA emitter selected from the following group:
  • the Depopulation Agent S B is a Green Fluorescence Emitter
  • the depopulation agent S B is a fluorescence emitter, in particular a green fluorescence emitter.
  • the depopulation agent S B is a fluorescence emitter selected from the following group:
  • the device has an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 380 to 800 nm, in particular between 485 nm and 590 nm, preferably between 505 nm and 565 nm, even more preferably between 515 nm and 545 nm.
  • Depopulation Agent S B is a Red Fluorescence Emitter
  • the depopulation agent S B is a fluorescence emitter, in particular a red fluorescence emitter.
  • the depopulation agent S B is a fluorescence emitter selected from the following group:
  • the depopulation agent S B is a phosphorescence emitter.
  • the device has an emission peak in the visible or nearest ultraviolet range, i.e., in the range of a wavelength of from 380 to 800 nm, in particular between 590 nm and 690 nm, preferably between 610 nm and 665 nm, even more preferably between 620 nm and 640 nm.
  • Orbital and excited state energies can be determined either by means of experimental methods known to the person skilled in the art. Experimentally, the energy of the highest occupied molecular orbital E HOMO is determined by methods known to the person skilled in the art from cyclic voltammetry measurements with an accuracy of 0.1 eV. The energy of the lowest unoccupied molecular orbital E LUMO is calculated as E HOMO +E gap , where E gap is determined as follows:
  • E gap is determined as the energy at which the excitation and emission spectra of a film with 1% by weight of emitter in PMMA cross, unless stated otherwise.
  • E gap is determined as the energy at which the excitation and emission spectra of a film with 10% by weight of emitter in PMMA cross, unless stated otherwise.
  • E gap For emitter compounds, e.g., NRCT emitters and fluorescence emitters, E gap and thus the energy of the first excited singlet state S1 is determined in the same way, unless stated otherwise.
  • the energy of the first excited triplet state T1 is determined from the onset of the time-gated emission spectrum at 77 K, typically with a delay time of 1 ms and an integration time of 1 ms, if not otherwise stated measured in a film of poly(methyl methacrylate) (PMMA) with 10% by weight of host.
  • PMMA poly(methyl methacrylate)
  • the energy of the first excited triplet state T1 is determined from the onset of the time-gated emission spectrum at 77 K, typically with a delay time of 1 ms and an integration time of 1 ms, if not otherwise stated measured in a film of poly(methyl methacrylate) (PMMA) with 1% by weight of emitter.
  • PMMA poly(methyl methacrylate)
  • the energy of the first excited triplet state T1 is determined from the onset of the time-gated emission spectrum at 77 K, typically with a delay time of 1 ms and an integration time of 1 ms, if not otherwise stated measured in a film of poly(methyl methacrylate) (PMMA) with 10% by weight of TADF compound.
  • PMMA poly(methyl methacrylate)
  • the energy of the first excited triplet state T1 is determined from the onset of the time-gated emission spectrum at 77 K, typically with a delay time of 1 ms and an integration time of 1 ms.
  • any electron transporter may be used.
  • compounds poor of electrons such as, e.g., benzimidazoles, pyridines, triazoles, oxadiazoles (e.g., 1,3,4-oxadiazole), phosphinoxides and sulfone, may be used.
  • an electron transporter ETM D may also be a star-shaped heterocycle such as 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)phenyl (TPBi).
  • the ETM D may exemplarily be NBphen (2,9-bis(naphthalen-2-yl)-4,7-diphenyl-1, 10-phenanthroline), Alq3 (Aluminum-tris(8-hydroxyquinoline)), TSPO1 (diphenyl-4-triphenylsilylphenyl-phosphinoxide), BPyTP2 (2,7-di(2,2′-bipyridin-5-yl)triphenyle), Sif87 (dibenzo[b,d]thiophen-2-yltriphenylsilane), Sif88 (dibenzo[b,d]thiophen-2-yl)diphenylsilane), BmPyPhB (1,3-bis[3,5-di(pyridin-3-yl)phenyl]benzene) and/or BTB (4,4′-bis-[2-(4,6-diphenyl-1,3,5-triazinyl)]-1,1′-bi
  • a cathode layer C Adjacent to the electron transport layer (ETL), a cathode layer C may be located.
  • the cathode layer C may comprise or may consist of a metal (e.g., Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, LiF, Ca, Ba, Mg, In, W, or Pd) or a metal alloy.
  • the cathode layer C may also consist of (essentially) intransparent metals such as Mg, Ca or Al.
  • the cathode layer C may also comprise graphite and or carbon nanotubes (CNTs).
  • the cathode layer C may also consist of nanoscale silver wires.
  • An OLED may further, optionally, comprise a protection layer between the electron transport layer (ETL) D and the cathode layer C (which may be designated as electron injection layer (EIL)).
  • This layer may comprise lithium fluoride, caesium fluoride, silver, Liq (8-hydroxyquinolinolatolithium), Li 2 O, BaF 2 , MgO and/or NaF.
  • a further embodiment of the present invention relates to an OLED, which exhibits an external quantum efficiency at 1000 cd/m 2 of more than 10%, more preferably of more than 12%, more preferably of more than 15%, even more preferably of more than 17% or even more than 20% and/or exhibits an emission maximum between 490 nm and 570 nm, preferably between 500 nm and 560 nm, more preferably between 510 nm and 550 nm, even more preferably between 520 nm and 540 nm and/or exhibits a LT80 value at 500 cd/m 2 of more than 3000 h, preferably more than 6000 h, more preferably more than 12000 h, even more preferably more than 22500 h or even more than 30000 h.
  • a further embodiment of the present invention relates to an OLED, which exhibits an external quantum efficiency at 1000 cd/m 2 of more than 10%, more preferably of more than 12%, more preferably of more than 15%, even more preferably of more than 17% or even more than 20% and/or exhibits an emission maximum between 420 nm and 500 nm, preferably between 430 nm and 490 nm, more preferably between 440 nm and 480 nm, even more preferably between 450 nm and 470 nm and/or exhibits a LT80 value at 500 cd/m 2 of more than 100 h, preferably more than 200 h, more preferably more than 400 h, even more preferably more than 750 h or even more than 1000 h.
  • a further embodiment of the present invention relates to an OLED, which emits light at a distinct color point.
  • the OLED emits light with a narrow emission band (small full width at half maximum (FWHM)).
  • FWHM full width at half maximum
  • the OLED according to the invention emits light with a FWHM of the main emission peak of below 0.43 eV, more preferably of below 0.39 eV, even more preferably of below 0.35 eV or even below 0.31 eV.
  • the depopulation agent S B is a NRCT emitter and the OLED according to the invention emits light with a FWHM of the main emission peak of below 0.25 eV, more preferably of below 0.23 eV, even more preferably of below 0.21 eV or even below 0.20 eV.
  • UHD Ultra High Definition
  • typically top-emitting (top-electrode is transparent) devices are used, whereas test devices as used throughout the present application represent bottom-emitting devices (bottom-electrode and substrate are transparent).
  • the CIEy color coordinate of a blue device can be reduced by up to a factor of two, when changing from a bottom- to a top-emitting device, while the CIEx remains nearly unchanged (Okinaka et al. doi:10.1002/sdtp.10480).
  • a further embodiment of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.02 and 0.30, preferably between 0.03 and 0.25, more preferably between 0.05 and 0.20 or even more preferably between 0.08 and 0.18 or even between 0.10 and 0.15 and/or a CIEy color coordinate of between 0.00 and 0.45, preferably between 0.01 and 0.30, more preferably between 0.02 and 0.20 or even more preferably between 0.03 and 0.15 or even between 0.04 and 0.10.
  • UHD Ultra High Definition
  • top-emitting devices typically top-emitting (top-electrode is transparent) devices are used, whereas test devices as used throughout the present application represent bottom-emitting devices (bottom-electrode and substrate are transparent).
  • the CIEy color coordinate of a blue device can be reduced by up to a factor of two, when changing from a bottom- to a top-emitting device, while the CIEx remains nearly unchanged (Okinaka et al. doi:10.1002/sdtp.10480).
  • a further embodiment of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.06 and 0.34, preferably between 0.07 and 0.29, more preferably between 0.09 and 0.24 or even more preferably between 0.12 and 0.22 or even between 0.14 and 0.19 and/or a CIEy color coordinate of between 0.75 and 1.20, preferably between 0.76 and 1.05, more preferably between 0.77 and 0.95 or even more preferably between 0.78 and 0.90 or even between 0.79 and 0.85.
  • UHD Ultra High Definition
  • top-emitting devices typically top-emitting (top-electrode is transparent) devices are used, whereas test devices as used throughout the present application represent bottom-emitting devices (bottom-electrode and substrate are transparent).
  • the CIEy color coordinate of a blue device can be reduced by up to a factor of two, when changing from a bottom- to a top-emitting device, while the CIEx remains nearly unchanged (Okinaka et al. doi:10.1002/sdtp.10480).
  • a further embodiment of the present invention relates to an OLED, whose emission exhibits a CIEx color coordinate of between 0.60 and 0.88, preferably between 0.61 and 0.83, more preferably between 0.63 and 0.78 or even more preferably between 0.66 and 0.76 or even between 0.68 and 0.73 and/or a CIEy color coordinate of between 0.25 and 0.70, preferably between 0.26 and 0.55, more preferably between 0.27 and 0.45 or even more preferably between 0.28 and 0.40 or even between 0.29 and 0.35.
  • aryl and “aromatic” may be understood in the broadest sense as any mono-, bi- or polycyclic aromatic moieties. If not otherwise indicated, an aryl may also be optionally substituted by one or more substituents which are exemplified further throughout the present application. For example, an aryl may be a phenyl, naphthalene or anthracene. In a preferred embodiment, an aryl residue is a phenyl residue. If not otherwise 5 indicated, an aryl may also be optionally substituted by one or more substituents which are exemplified further throughout the present application. Accordingly, the term “arylene” refers to a divalent residue that bears two binding sites to other molecular structures and thereby serving as a linker structure.
  • heteroaryl and “heteroaromatic” may be understood in the broadest sense as any mono-, bi- or polycyclic heteroaromatic moieties that include at least one heteroatom, in particular which bear from one to three heteroatoms per aromatic ring.
  • a heteroaromatic residue may be selected from the group consisting of carbazol, triazine (e.g., 1,3,5-triazine), dibezothiophene, dibenzofurane, pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, pyrazole, pyridine, pyrazine and pyrimidine, and the like.
  • heteroaromatic residue is carbazol or 1,3,5-triazine.
  • a heteroaryl may also be optionally substituted by one or more substituents which are exemplified further throughout the present application. Accordingly, the term “heteroarylene” refers to a divalent residue that bears two binding sites to other molecular structures and thereby serving as a linker structure.
  • alkyl may be understood in the broadest sense as both, linear or branched chain alkyl residue. Preferred alkyl residues are those containing from one to fifteen carbon atoms (C 1 -C 15 -alkyl). Exemplarily, an alkyl residue may be methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, and the like. If not otherwise indicated, an alkyl may also be optionally substituted by one or more substituents which are exemplified further throughout the present application. Accordingly, the term “alkylene” refers to a divalent residue that bears two binding sites to other molecular structures and thereby serving as a linker structure.
  • substitution means a residue selected from the group consisting of C 1 -C 20 -alkyl, C 7 -C 19 -alkaryl, and C 6 -C 18 -aryl. Accordingly, preferably, no charged moiety, more preferably no functional group is present in such substitution.
  • any of the layers of the various embodiments may be deposited by any suitable method.
  • the layers in the context of the present invention, including the light-emitting layer B may optionally be prepared by means of liquid processing (also designated as “film processing”, “fluid processing”, “solution processing” or “solvent processing”). This means that the components comprised in the respective layer are applied to the surface of a part of a device in liquid state.
  • the layers in the context of the present invention, including the light-emitting layer B may be prepared by means of spin-coating. This method well-known to those skilled in the art allows obtaining thin and (essentially) homogeneous layers.
  • the layers in the context of the present invention may be prepared by other methods based on liquid processing such as, e.g., casting (e.g., drop-casting) and rolling methods, and printing methods (e.g., inkjet printing, gravure printing, blade coating). This may optionally be carried out in an inert atmosphere (e.g., in a nitrogen atmosphere).
  • liquid processing such as, e.g., casting (e.g., drop-casting) and rolling methods, and printing methods (e.g., inkjet printing, gravure printing, blade coating).
  • This may optionally be carried out in an inert atmosphere (e.g., in a nitrogen atmosphere).
  • the layers in the context of the present invention may be prepared by any other method known in the art, including but not limited to vacuum processing methods well-known to those skilled in the art such as, e.g., thermal (co-)evaporation, organic vapor phase deposition (OVPD), and deposition by organic vapor jet printing (OVJP).
  • vacuum processing methods well-known to those skilled in the art such as, e.g., thermal (co-)evaporation, organic vapor phase deposition (OVPD), and deposition by organic vapor jet printing (OVJP).
  • the solutions including the components of the layers may further comprise a volatile organic solvent.
  • Such volatile organic solvent may optionally be one selected from the group consisting of tetrahydrofuran, dioxane, chlorobenzene, diethylene glycol diethyl ether, 2-(2-ethoxyethoxy)ethanol, gamma-butyrolactone, N-methyl pyrrolidinon, ethoxyethanol, xylene, toluene, anisole, phenetol, acetonitrile, tetrahydrothiophene, benzonitrile, pyridine, trihydrofuran, triarylamine, cyclohexanone, acetone, propylene carbonate, ethyl acetate, benzene and PGMEA (propylen glycol monoethyl ether acetate).
  • the layer may subsequently be dried and/or hardened by any means of the art, exemplarily at ambient conditions, at increased temperature (e.g., about 50° C. or about 60° C.) or at diminished pressure.
  • an organic electroluminescent device may exemplarily be an essentially white organic electroluminescent device or a blue organic electroluminescent device.
  • exemplary such white organic electroluminescent device may comprise at least one (deep) blue emitter compound (e.g., TADF material E B ) and one or more emitter compounds emitting green and/or red light. Then, there may also optionally be energy transmittance between two or more compounds as described above.
  • the organic electroluminescent device as a whole may also form a thin layer of a thickness of not more than 5 mm, more than 2 mm, more than 1 mm, more than 0.5 mm, more than 0.25 mm, more than 100 ⁇ m, or more than 10 ⁇ m.
  • An organic electroluminescent device may be a small-sized (e.g., having a surface not larger than 5 mm 2 , or even not larger than 1 mm 2 ), medium-sized (e.g., having a surface in the range of 0.5 to 20 cm 2 ), or a large-sized (e.g., having a surface larger than 20 cm 2 ).
  • An organic electroluminescent device e.g., an OLED according to the present invention may optionally be used for generating screens, as large-area illuminating device, as luminescent wallpaper, luminescent window frame or glass, luminescent label, luminescent poser or flexible screen or display.
  • an organic electroluminescent device e.g., an OLED
  • an OLED organic electroluminescent device
  • the present invention further relates to a method for generating light of a desired wavelength range, comprising the step of providing an organic electroluminescent device according to any the present invention.
  • a further aspect of the present invention relates to a method for generating light of a desired wavelength range, comprising the steps of
  • a further aspect of the present invention relates to a process of making the organic electroluminescent devices by assembling the elements described above.
  • the present invention also relates to a method for generating blue, green, yellow, orange, red or white light, in particular blue or white light by using said organic electroluminescent device.
  • the invention is illustrated by the examples and claims.
  • Cyclic voltammograms of solutions having concentration of 10-3 mol/l of the organic molecules in dichloromethane or a suitable solvent and a suitable supporting electrolyte e.g. 0.1 mol/l of tetrabutylammonium hexafluorophosphate
  • the measurements are conducted at room temperature and under nitrogen atmosphere with a three-electrode assembly (Working and counter electrodes: Pt wire, reference electrode: Pt wire) and calibrated using FeCp 2 /FeCp 2 + as internal standard.
  • HOMO data was corrected using ferrocene as internal standard against SCE.
  • BP86 BP86 functional and the resolution of identity approach (RI).
  • Excitation energies are calculated using the (BP86) optimized structures employing Time-Dependent DFT (TD-DFT) methods.
  • Orbital and excited state energies are calculated with the B3LYP functional.
  • Def2-SVP basis sets and a m4-grid for numerical integration were used.
  • the Turbomole program package was used for all calculations.
  • Stock solution 1 10 mg of sample (organic TADF material or host material) is dissolved in 1 ml of solvent.
  • Stock solution 2 10 mg of PMMA is dissolved in 1 ml solvent.
  • the solvent is typically selected from toluene, chlorobenzene, dichloromethane and chloroform.
  • An Eppendorf pipette is used to add 1 ml of stock solution 1 to 9 ml of stock solution 2 to achieve a 10% by weight of sample in PMMA.
  • the photophysical properties of host material can be characterized in neat films of host material.
  • Stock solution 1 10 mg of sample (fluorescence emitters and NRCT emitters) is dissolved in 1 ml of solvent.
  • Stock solution 1a 9 ml of solvent is added to 1 ml of stock solution 1.
  • Stock solution 2 10 mg of PMMA is dissolved in 1 ml solvent.
  • the solvent is typically selected from toluene, chlorobenzene, dichloromethane and chloroform.
  • An Eppendorf pipette is used to add 1 ml of stock solution 1 to 9.9 ml of stock solution 2 to achieve a 1% by weight of sample in PMMA.
  • the photophysical properties of fluorescence emitters can be characterized in solution, wherein a concentration of 0.001 mg/ml of fluorescence emitter in solution is used.
  • Apparatus Spin150, SPS euro. Program: 1) 3 s at 400 U/min; 20 s at 1000 U/min at 1000 Upm/s. 3) 10 s at 4000 U/min at 1000 Upm/s. After coating, the films are dried at 70° C. for 1 min.
  • Steady-state emission spectroscopy is recorded using a Horiba Scientific, Modell FluoroMax-4 equipped with a 150 W Xenon-Arc lamp, excitation- and emissions monochromators and a Hamamatsu R928 photomultiplier and a time-correlated single-photon counting option. Emissions and excitation spectra are corrected using standard correction fits.
  • Excited state lifetimes are determined employing the same system using the TCSPC method with FM-2013 equipment and a Horiba Yvon TCSPC hub.
  • NanoLED 370 (wavelength: 371 nm, puls duration: 1.1 ns)
  • NanoLED 290 (wavelength: 294 nm, puls duration: ⁇ 1 ns)
  • SpectraLED 310 (wavelength: 314 nm)
  • SpectraLED 355 (wavelength: 355 nm).
  • Emission maxima are given in nm, quantum yields CD in % and CIE coordinates as x,y values.
  • OLED devices comprising organic molecules according to the invention can be produced. If a layer contains more than one compound, the weight-percentage of one or more compounds is given in %. The total weight-percentage values amount to 100%, thus if a value is not given, the fraction of this compound equals to the difference between the given values and 100%.
  • the not fully optimized OLEDs are characterized using standard methods and measuring electroluminescence spectra, the external quantum efficiency (in %) in dependency on the intensity, calculated using the light detected by the photodiode, and the current.
  • the OLED device lifetime is extracted from the change of the luminance during operation at constant current density, which is given in mA/cm 2 .
  • the LT50 value corresponds to the time, where the measured luminance decreased to 50% of the initial luminance
  • analogously LT80 corresponds to the time point, at which the measured luminance decreased to 80% of the initial luminance
  • LT97 to the time point, at which the measured luminance decreased to 97% of the initial luminance etc.
  • LT95 values at 1200 cd/m 2 are determined using the following equation:
  • L 0 denotes the initial luminance at the applied current density.
  • the values correspond to the average of several pixels (typically two to eight), the standard deviation between these pixels is given.
  • the results show the data series for one OLED pixel.
  • Example C1 10 100 nm Al Al 9 2 nm Liq Liq 8 20 nm NBPhen NBPhen 7 10 nm HBL1 HBL1 6 50 nm Depopulation Agent selected from TADF1 (20%): light- Depopulation Agents 1 to 7 (each mCBP (80%) emitting 1% by weight or 5% by weight): layer B TADF1 (20% by weight): add up to a total of 100% by weight, based on the light-emitting layer B of mCBP (i.e., 79% by weight or 75% by weight, respectively) 5 10 nm mCBP mCBP 4 10 nm TCTA TCTA 3 50 nm NPB NPB 2 5 nm HAT-CN HAT-CN 1 50 nm ITO ITO substrate glass glass glass
  • the emitting layer of Comparative device C1 only contains TADF1 and mCBP
  • the external quantum efficiency (FOE) at 1000 cd/m 2 is 16% and the lifetime LT95 at 1200 cd/m 2 value was determined to be 490 h.
  • the emission maximum is at 520 nm at 10 mA/cm 2 .
  • the corresponding CIFx value is 0.306 and CIFy is 0.604.
  • Device D1 comprises the same layer arrangement as device D1, except that the emitting layer contains TADF1, mCBP and Depopulation Agent 1 with either 1% by weight or 5% by weight.
  • the concentration by weight of TADF1 is always set to 20% by weight, wherein the concentration of mCBP is either 79% by weight, in case the Depopulation Agent is used with 1% by weight or 75% by weight, in case the Depopulation Agent is used with 5% by weight.
  • Device D2 is prepared in the same manner as device D1, unless changing the Depopulation Agent 1 to Depopulation Agent 2.
  • Device D3 is prepared in the same manner as device D1, unless changing the Depopulation Agent 1 to Depopulation Agent 3.
  • Device D4 is prepared in the same manner as device D1, unless changing the Depopulation Agent 1 to Depopulation Agent 4.
  • Device D5 is prepared in the same manner as device D1, unless changing the Depopulation Agent 1 to Depopulation Agent 5.
  • Device D6 is prepared in the same manner as device D1, unless changing the Depopulation Agent 1 to Depopulation Agent 6.
  • Device D7 is prepared in the same manner as device D1, unless changing the Depopulation Agent 1 to Depopulation Agent 7.
  • a depopulation agent may lead to an increasing lifetime in a device according to the present invention, while the EQE is at least similar, often increased.
  • the emitted color/emission maximum wavelength typically remains in an at least similar range.
  • a significant enhanced LT95 at 1200 cd/m 2 can be observed compared to the comparative example C1 without a Depopulation Agent and compared to example D7, as the relative lifetime LT95 at 1200 cd/m 2 is enhanced by at least 30% and up to more than 300%.

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