EP4635271A1 - Organic electroluminescent device, semiconducting material, semiconducting layer, compound, electronic device and display device - Google Patents

Organic electroluminescent device, semiconducting material, semiconducting layer, compound, electronic device and display device

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Publication number
EP4635271A1
EP4635271A1 EP23821632.9A EP23821632A EP4635271A1 EP 4635271 A1 EP4635271 A1 EP 4635271A1 EP 23821632 A EP23821632 A EP 23821632A EP 4635271 A1 EP4635271 A1 EP 4635271A1
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EP
European Patent Office
Prior art keywords
unsubstituted
substituted
alkyl
partially
alkoxy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
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EP23821632.9A
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German (de)
French (fr)
Inventor
Qiang Huang
Johannes Scholz
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NovaLED GmbH
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NovaLED GmbH
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Publication date
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Publication of EP4635271A1 publication Critical patent/EP4635271A1/en
Pending legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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
    • H10K50/16—Electron transporting 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]
    • H10K50/19—Tandem OLEDs
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • 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
    • H10K71/30—Doping active layers, e.g. electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—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

Definitions

  • Organic electroluminescent device semiconducting material, semiconducting layer, compound, electronic device and display device
  • the present invention relates to an organic electroluminescent device, to a semiconducting material, to a semiconducting layer, to an electronic device to a compound and to a display device.
  • Organic electronic devices such as organic light-emitting diodes OLEDs, which are selfemitting devices, have a wide viewing angle, excellent contrast, quick response, high brightness, excellent operating voltage characteristics, and color reproduction.
  • Atypical OLED comprises an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode, which are sequentially stacked on a substrate.
  • the HTL, the EML, and the ETL are thin films formed from organic compounds.
  • Performance of an organic light emitting diode may be affected by characteristics of an organic semiconductor layer comprised therein, and among them, may be affected by characteristics of an organic material of the organic semiconductor layer.
  • An aspect of the present invention provides an organic electroluminescent device comprising an anode layer, a cathode layer, a first emission layer, a second emission layer, a first charge generation layer, and a first electron transport layer, wherein
  • the first charge generation layer is arranged between the first emission layer and the second emission layer;
  • the first electron transport layer is arranged between the first emission layer and the second emission layer;
  • the first charge generation layer comprises a first n-type charge generation layer and a first p-type charge generation layer;
  • the first n-type charge generation layer is closer to the anode layer than the first p-type charge generation layer and the first p-type charge generation layer is closer to the cathode layer than the first n-type charge generation layer;
  • the first electron transport layer is arranged in direct contact with the first n-type charge generation layer
  • the first electron transport layer is free of 8-hydroxyquinoIinolato-lithium
  • the first n-type charge generation layer comprises a metal dopant and the metal dopant is Yb;
  • the first n-type charge generation layer comprises a compound of formula (I) wherein in formula (I) - Ar is selected from substituted or unsubstituted C 6 to C 24 aryl or substituted or unsubstituted Cb to C_> 4 heteroaryl;
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to alkyl, substituted or unsubstituted C 6 to C 24 aryl or substituted or unsubstituted C1 to G 4 heteroaryl, CN, halogen, F, C1 to C 16 alkoxy, C :i to C1 ⁇ > branched alkyd.
  • C 3 to C1& cyclic alkyl C 3 to C 16 branched alkoxy, C 3 to C1& cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C», alkoxy, partially or perdeuterated C1 to C1o allyl, partially or perdeuterated Cj to C1o alkoxy, or PX(R 8 ) a wherein.
  • R 8 is independently selected from C 6 to C J2 aryl, C 3 to C 12 heteroaryl, C1 to C1o alkyl, C1 to C16 alkoxy, partially or perfluorinated Ct to C1o alkyl, partially or perfluorinated C1 to C1o alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C1o alkoxy; and X 1 is selected from 0, S or Se, preferably O; and
  • - L is selected from substituted or unsubstituted C 6 to C 24 aryl, substituted or unsubstituted C 2 to C 24 heteroaryl.
  • Another aspect of the present invention provides a display device comprising the organic electroluminescent dewce according to the present invention.
  • Another aspect of the present invention provides a compound of formula (M1) or of formula (M2) wherein in formula (M1)
  • R’ to R7 are independently selected from H, D, substituted or unsubstituted C1 to C1o alkyl, substituted or unsubstituted C 6 to C1 4 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F, C1 to C1o alkoxy, C s to C1o branched alkyl, C 3 to C 16 cyclic alkyfo C1 to C1o branched alkoxy, C 3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16, alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C1& alkyl, partially or perdeuterated C1 to C1*> alkoxy, or PX'(R K L wherein R 8 is independently selected from C 6 to C 12 aryl, C 3 to C 12 heteroaryl, G to C1& alkyl, C1 to C16
  • R Lb , R Lb , Irffrand R Lb are independently selected from H, D, substituted or unsubstituted C1 to CH. alkyd, substituted or unsubstituted C1 to C1 4 aryl or substituted or unsubstituted C1 to C1 4 heteroaryl, CN, halogen, F, C1 to C 16 alkoxy, C 3 to C 16 branched alkyl, C 3 to C16 cyclic alkyl, C 3 to C16 branched alkoxy, C 3 to C 16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C* alkoxy, or PX’fRrfh wherein R 8 is independently selected from C1 to C t2 aryl, C 3 to C 12 heteroaryl, C1 to C18 al
  • - Ar is selected from substituted or unsubstituted C1 to C 24 aryl or substituted or unsubstituted C1 to C 24 heteroaryl; wherein in formula (M2)
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C1B alkyl, substituted or unsubstituted C6 to C1 4 aryl or substituted or unsubstituted C1 to C1 4 heteroaryl, CN, halogen, F.
  • C1 to C16 alkoxy C 1 to C1o branched alkyl, C1 to C1o cyclic alkyl, C1 to C16 branched alkoxy, C 3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX’(R 8 ) a wherein R 8 is independently selected from C1 to C1 a aryl, C 3 to C1- heteroaiyl.
  • - Ar is selected from substituted or unsubstituted C6 to aryl or substituted or unsubstituted C1 to C 24 heteroaryl;
  • - L is selected from substituted or unsubstituted C6 to C1 4 aryl, substituted or unsubstituted C to C 24 heteroaryl.
  • Another aspect of the present invention provides a semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
  • Another aspect of the present invention provides a semiconducting layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (Ml) or (M2).
  • Another aspect of the present invention provides an electronic device comprising an semiconductor layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
  • the electronic device is an organic electronic device.
  • the electronic device comprises an electroluminescent device, an organic light emitting diode (OLED). a light emitting device, thin film transistor, a battery, a display device or an organic photovoltaic cell (OPV).
  • OLED organic light emitting diode
  • OLED organic photovoltaic cell
  • Another aspect of the present invention provides a display device comprising an organic electronic; device comprising a semiconductor layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
  • substituted refers to one substituted with a deuterium, C1 to C 12 alkyl and Q to C1 2 alkoxy.
  • aryl substituted refers to a substitution with one or more aryl groups, which themselves may be substituted with one or more aiyd and/or heteroaryl groups.
  • heteroaryl substituted refers to a substitution with one or more heteroaryl groups, which themselves may be substituted with one or more aryl and/or heteroaryl groups. > ,
  • an "alkyl group” refers to a saturated aliphatic hydrocarbyl group.
  • the alkyl group may be a C1 to C 12 alkyl group. More specifically, the alkyl group may be a C 1 to C M alkyl group or a C 1 to C6 alkyl group.
  • a C1 to C 4 alkyl group includes 1 to 4 carbons in alkyl chain, and may be selected from methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl.
  • alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, a hexyl group.
  • cycloalkyl refers to saturated hydrocarbyl groups derived from a cycloalkane by formal abstraction of one hydrogen atom from a ring atom comprised in the corresponding cycloalkane.
  • examples of the cycloalkyl group maybe a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, an adamantly group and the like.
  • hetero is understood the way that at least one carbon atom, in a structure which may be formed by covalently bound carbon atoms, is replaced by another polyvalent atom.
  • the heteroatoms are selected from B, Si, N, P, 0, S; more preferably from N, P, O, S.
  • aryl group refers to a hydrocarbyl group which can be created by formal abstraction of one hydrogen atom from an aromatic ring in the corresponding aromatic hydrocarbon.
  • Aromatic hydrocarbon refers to a hydrocarbon which contains at least one aromatic ring or aromatic ring system.
  • Aromatic ring or aromatic ring system refers to a planar ring or ring system of covalently bound carbon atoms, wherein the planar ring or ring system comprises a conjugated system of delocalized electrons fulfilling Huckel’s rule.
  • aiyl groups include monocyclic groups like phenyl or tolyl, polycyclic groups which comprise more aromatic rings linked by single bonds, like biphenylyl, and polycyclic groups comprising fused rings, like naphthyl or fluoren-2-yl.
  • heteroaryl it is especially where suitable understood a group derived by formal abstraction of one ring hydrogen from a heterocyclic aromatic ring in a compound comprising at least one such ring.
  • heterocycloalkyl it is especially where suitable understood a group derived by formal abstraction of one ring hydrogen from a saturated cycloalkyl ring in a compound comprising at least one such ring.
  • fused aryl rings or “condensed aryl rings” is understood the way that two aryl rings are considered fused or condensed when they share at least two common spa-hybridized carbon atoms
  • the single bond refers to a direct bond.
  • contacting sandwiched refers to an arrangement of three layers whereby the layer in the middle is in direct contact with the two adjacent layers.
  • light-absorbing layer and “light absorption layer” are used synonymously.
  • light-emitting layer “light emission layer” and “emission layer” are used synonymously.
  • hole characteristics refer to an ability to donate an electron to form a hole when an electric field is applied and that a hole formed in the anode may be easily injected into the emission layer and transported in the emission layer due to conductive characteristics according to a highest occupied molecular orbital (HOMO) level.
  • HOMO highest occupied molecular orbital
  • electron characteristics refer to an ability to accept an electron when an electric field is applied and that electrons formed in the cathode may be easily injected into the emission layer and transported in the emission layer due to conductive characteristics according to a lowest unoccupied molecular orbital (LUMO) level.
  • LUMO lowest unoccupied molecular orbital
  • a multi-stack OLED comprising an n-type charge generation layer comprising Ytterbium as metal dopant a compound comprising a imidazo[i,5-a]pyridine group and a phenanthroline group as the host (matrix) in direct contact with a LiQ-free electron transport layer has an reduced voltage rise over time.
  • n-CGL matrix for Ytterbium and an LiQ-free ETL contacting directiy said n-CGL results synergistically in an improved voltage increase over time of a multi-stack OLED.
  • the thickness of the first n-type charge generation layer may be in the range from 0.5 nm to 50 nm; alternatively in the range from 1 nm to about 40 nm; or alternatively in the range of 2 nm to 30 nm; or alternatively 5 nm to 15 nm.
  • the first charge generation layer comprises a first n-type charge generation layer and a first p- type charge generation layer.
  • the first n-type charge generation layer comprises a compound of formula (I)
  • the compound of formula (I) is present in the first n-type charge generation layer in an amount of >0.1 preferably ⁇ 1 preferably >2 wt.-X, more preferably s*3 wt.-%, more preferably >5 Wt-9Q more preferably >8 wt.-%, more preferably te2O wt.-%, more preferably >30 wt.-%, more preferably >40 more preferably >50 wt.- %, based on the total weight of the first n-type charge generation layer.
  • the metal dopant is present in the first n-type charge generation layer in amount of 599.9 wt.-%, preferably 599 more preferably ⁇ 98 more preferably ⁇ 97 more preferably ⁇ 95 wl.-%, more preferably ⁇ 92 wt.-%, more preferably ⁇ 80 wt.-%, more preferably ⁇ 70 more preferably ⁇ 60 wt,-%, more preferably ⁇ 55 wt.- %, more preferably ⁇ 50 wt.-%, based on the total weight of the first n-tjpe charge generation layer.
  • the compound of formula (I) is present in the first n-type charge generation layer in an amount of > 50 wt.-% to ⁇ 99.9 wt.-%, preferably >50 wt.-% to ⁇ 99 wt.- %, more preferably >50 wt.-% to ⁇ 98 more preferably >50 wt.-% to ⁇ 97 wt-% to, based on the total weight of the first n-type charge generation layer.
  • the metal dopant is present in the first n-type charge generation layer in amount of >0.1 wt.-% to ⁇ 50 preferably >1 wt.-% to ⁇ 50 wt.-%, more preferably
  • the first n-type charge generation layer is non-emissive.
  • the term "essentially non-emissive” or “non- emissive” means that the contribution of the compound or layer to the visible emission spectrum from the device is less than 10 %, preferably less than 5 % relative to the visible emission spect-um.
  • the visible emission spectrum is an emission spectrum with a wavelength of about > 380 nm to about ⁇ 780mm.
  • the metal dopant in terms of the present disclosure may be a redox n-dopant.
  • a redox n-dopant it is understood a compound which, if embedded into an electron transport matrix, improves, in comparison with the neat matrix under the same physical conditions, the electronic properties of the formed organic material, in particular in terms of electron injection, electron generation and/or electron conductivity.
  • the redox n-dopant is non-emissive.
  • embedded into an electron transport matrix means the redox n-dopant forms a mixture with the electron transport matrix.
  • Ar is selected from substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C24 heteroaryl.
  • Ar is selected from substituted or unsubstituted C 6 to C18 aryl or substituted or unsubstituted C 2 to Cfe heteroaryl. According to an embodiment, Ar is selected from substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C 2 to C1 2 heteroaryl.
  • Ar is selected from substituted or unsubstituted C6 to C1o aryl or substituted or unsubstituted C 2 to C 10 heteroaryl.
  • Ar is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl.
  • Ar is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein the heteroaryl is a six-member ring.
  • Ar is selected from the group consisting of substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, and substituted or unsubstituted quinolinyl.
  • Ar maybe unsubstituted or substituted with one or more substituents.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C20 heteroaryl, C1 to C 1 6 alkyl.
  • C1 tot C16 alkoxy C 3 to CK, branched alkyl, C 3 to C16 cyclic alkyl, C 3 to C , 6 branched alkoxy, C 3 to C1 6 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C1& alkoxy, partially or perdeuterated C1 to C1& alkyl, partially or perdeuterated C1 to C16.
  • R 8 is independently selected from C6 to C12 aryl, C 3 to C1 2 heteroaryl, C1 to C16 allyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C1& alkyl, partially or perfluorinated C1 to C1 « alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X ! is selected from O, S or Se, preferably 0.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C1g aryl, substituted or unsubstituted C 3 to C 2 0 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, C 3 to C16 branched alkoxy, C 3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C1 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, PX1R 8 )2 halogen, F or CN, wherein R 8 is independently selected from C6 to C 12 aryl, C 3 to C 12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C20 heteroaryl, C1 to C 16 ally‘I s C 3 to C1& branched alkyl, C 3 to C16 cyclic altyl, partially or perfluorinated C 1 to C16 alkyl, partially or perdeuterated C to C16 alky l, PX‘(R H ).
  • R s is independently selected from C 6 to C a aryl, C 3 to C 12 heteroaiyl, C 1 to CH, alkyl, C» to C16 alkoxy; partially or perfluorinated C1 to C16 alkyd, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to 0,6 alkyl, partially or perdeuterated C1 to C16 alkoxy ; and X 1 is selected from O, S or Se, preferably 0.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C20 heteroaryl, C1 to C « alkyl, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C1& alkyl, partially or perdeuterated C1 to Cfe alkyl, PX’(R8), halogen, F or CN, wherein R 8 is independently selected from C6 to C 12 aryl, C 3 to C 12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C» to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X 1 is selected from D, substituted or unsubsti
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaiyl, C 1 to C16 all ⁇ l, C 3 to branched alkyl, C 3 to C18 cyclic alkyl, partially or perfluorinated C1 to C16 alkyd, partially or perdeuterated C1 to C1 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to 0,8 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C 1 to C16 alkyl, C 3 to 0,6 branched alkyl, C 3 to C1& cyclic alkyl, partially or perfluorinated C1 to C 16 alkyl, partially or perdeuterated C1 to C1, alkyl, halogen, F or CN.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C w aryl, substituted or unsubstituted C 3 to C 14 heteroaiyl, C1 to C 10 0lkyl, C 3 to C 10 branched alkyl, C 3 to C1 0 cyclic alkyl, partially or perfluorinated C1 to C 10 alkyl, partially or perdeuterated C1 to C TO alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C 12 aryl, substituted or unsubstituted C 3 to C 14 heteroaryl, C1 to C 10 alkyl, C 3 to C 10 branched alkyl.
  • the one or more substituents on Ar are independently selected from D. substituted or unsubstituted Cfe to C 10 axyl, substituted or unsubstituted C 3 to C 12 heeteroaryl, C1 to C6 alkyl, C 3 to C 6 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C» to C6 alkyl, partially or perdeuterated C1 to C6, alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C 6 to C J0 aryl, substituted or unsubstituted C 3 to C12 heteroaryl.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C M aryl, substituted or unsubstituted C 3 to C16 heteroaryl, C 1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C 1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C 10 aryl, substituted or unsubstituted C 3 to C10 heteroaryl, C 3 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C 3 to C 4 alkyl, halogen, F or CN.
  • the one or more substituents 011 Ar are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstfluted C 3 to C 5 heteroa ryl, C 3 to C , alky l, C 3 to C 4 branched alkyl, C 3 to C ⁇ > cyclic alkyl, partially or perfluorinated C1 to C 4 alyl, partially or perdeuterated C 3 to C 4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar. if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C 3 to C 5 heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to C6 cyclic alkyl , partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C 1 to C 4 alkyl, halogen, F or CN.
  • Ar is selected from the following Di to D19 shown in Table 1
  • R 9 , R 10 and R 11 are independently selected from H, C1 to C 16 alkyl, C1 to C 16 alkoxy, C6 to C18 aryl, C 3 to C 20 heteroaryl, perfluorinated C1 to C 16 , alkyl, perfluorinated C1 to C 16 > alkoxy, wherein R 9 and R 19 may be linked via a single bond er a heteroatom to form a ring, wherein the asterisk denotes the binding position,
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 1( , alkyl, substituted or unsubstituted C 6 to C24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F, C 3 to C 16 branched alkyl, C 3 to C 16 cyclic alkyl, partially or perfluorinated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkyl, or PX ⁇ R®) 2 wherein R 8 is independently selected from C6 to C 12 aryl, C 3 to C 12 heteroaryl, C1 to C 16 alkyl, C1 to C 16 alkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to C 16 alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy; and
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F.
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 16 alkyl, substituted or unsubstituted C6 to C16 aryl or substituted or unsubstituted C2 to C 24 hcteroaryl, halogen, F.
  • R 1 to R 7 are independently selected from. H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C 2 to C24 heteroaryl, halogen.
  • R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C 2 to C18 eteroaryl, CN, halogen, Cl, F.
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C& to C18 aryl or substituted or unsubstituted C 2 to C18 heteroaryl, halogen.
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to G alkyl, substituted or unsubstituted C6 to C 32 aryl or substituted or unsubstituted C 2 to C 12 heteroaryl, CN, halogen, Cl, F.
  • R1 to R 7 are independently selected from H, D, substituted or unsubstituted C r to G alkyl, substituted or unsubstituted G to C1a aryl or substituted or unsubstituted C 2 to C1a heteroaryl, halogen.
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstiteted C 1 to C 4 alkyl, substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C1 to C 10 heteroaryl, CN, halogen, Cl, F.
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted C1 to C 10 aryl or substituted or unsubstituted G to C1o heteroaryl, halogen.
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted C t . aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, CN, halogen, Cl, F.
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted G aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, halogen.
  • R 1 to R 7 offormula fl may be independently unsubstituted or substituted with one or more substituents.
  • the one or more substituents on R* to R 7 are independently selected from D, C1 to C18 aryl, C 3 to C 20 heteroaryl, C 1 to C16 alkyl, C 1 to C16 alkoxy, C, to C1 6 branched alkyl, C3 to C1 6 cyclic alkyl, C 3 to C tf , branched alkoxy , C1 to C 16 cyclic alkoxy, partially or perfluorinated C1 to Cn, alkyl, partially or perfluorinated C1 to C1, alkoxy, partially or perdeuterated C1 to Clh alkyl, partially or perdeuterated C1 to C16> alkoxy, halogen, F, CN or PX'(R H ) 2; wherein R K is independently selected from C 6 to C 12 an ).
  • R 1 to R 7 are independently selected from D, substituted or unsubstituted C6, to C 13 aryl, substituted or unsubstituted C 3 to C20 heteroaryl, C ( to C 16 alkyl, C 3 to C16 branched alkyl, C1 to C 16 cyclic alkyl, partially or perfluorinated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkyl, PX'(R 8 ) 2 , halogen, F
  • the one or more substituents on R 1 to R 7 are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted G to Go heteroaryl, C1 to C 16 alkyl, C 3 to C 16 branched alkyl, C 3 to CM cyclic alkyl, partially or perfluorinated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkyl, halogen, F or CN.
  • the one or more substituents on R* to R 7 are independently selected from D, substituted or unsubstituted C6 to C t2 aryl, substituted or unsubstituted C 3 to C1 4 heteroaryl, C1 to C10 alkyl, C 3 to C10 branched alkyl, C1 to C1o cyclic alkyl, partially or perfluorinated C1 to C10 alkyl, partially or perdeuterated C1 to C1o alkyl, halogen, F or CN.
  • the one or more substituents on R‘ to R 7 are independently selected from D, substituted or unsubstituted C6 to C 10 aryl, substituted or unsubstituted C 3 to C1., hcteroaryl, C1 to C (! alkyl, C 3 to Ct, branched alkyl, C1 to C1, cyclic alkyl, partially or perfluorinated C1 to C h alkyd, partially or perdeuterated C1 to C1 alkyl, halogen, F or CN.
  • the one or more substituents on R 1 to R are independently selected from D, substituted or unsubstituted C6 to C 1O aryl, substituted or unsubstituted C 3 to C 1 0 heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, For CN.
  • the one or more substituents on R 1 to R 7 are independently selected from D, substituted or unsubstituted C 6 aryl, substituted or unsubstituted C 3 to C 5 heteroaryl, C1 to C 4 alkyl, C1 to C 4 branched alkyl, C 3 to G cyclic alkyl, partial!)- or perfluorinated C1 to C1 alkyd, partially or perdeuterated C1 to C1 alkyl, halogen, F or CN.
  • L is selected from substituted or unsubstituted C 6 to C1 « aryl, substituted or unsubstituted C1 to C18 hcteroaryl. According to an embodiment, L is selected from substituted or unsubstituted C 6 to C 12 aryl or substituted or unsubstituted C 2 to C 12 heteroaryl.
  • L is selected from substituted or unsubstituted C1 to C10 aryl or substituted or unsubstituted C 2 to C1 ⁇ > heteroaiyl.
  • L is selected from substituted or unsubstituted C 6 to C10 and or substituted or unsubstituted C 3 to C 5 heteroaryl.
  • L is selected from substituted or unsubstituted C 6 to C w aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein heteroaryl is a six-member ring.
  • L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl.
  • L is selected from substituted or unsubstituted phenyl and substituted or unsubstituted naphthyl.
  • L is selected from substituted phenyl, unsubstituted phenyl and unsubstituted naphthyl
  • L may be independently unsubstituted or substituted with one or more substituents.
  • the one or more substituents on L are independently selected from D, C6 to C18 aryl, C 3 to C 20 heteroaryl, C1 to 0 ⁇ alkyl, C ( to C16 alkoxy, C 3 to C16 branched alkyl, C 3 to C1& cyclic alkyl, C 3 to C16 branched alkoxy, C 3 to C16, cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C 1 to C1o alkoxy, partially or perdeuterated C1 to C 1 6 alkyl, partially or perdeuterated C1 to C16 alkoxy, halogen, F, CN or PX 3 (R 8 ) 2 , wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R 8 is independently selected from C 6 to C 12 aryl, C 3 to C1a heteroaryl, C1 to C «>
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C1 to C 20 heteroaryl, C1 to C 1 6, alkyl, C1 to C1-> alkoxy, C 3 to C1 b branched alkyl, C 3 to C1t, cyclic alkyl, C 3 to CK, branched alkoxy, C1 to CK, cyclic alkoxy, partially or perfluorinated C1 to C1 classroom alkyl, partially or perfluorinated C ( to C1o alkoxy, partially or perdeuterated C-.
  • R 8 is independently selected from C1, to aryl, C 3 to C 12 heteroaryl, C1 to alkyl, C1 to C 16 alkoxy, partially or perfluorinated C1 to C 1 6 alkyl, partially or perfluorinated C1 to C 16 alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy; and X* is selected from 0, S or Se, preferably O.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cj, to C18 aryl, substituted or unsubstituted C 3 to C 2O heteroaryl, Ct to C 16 alkyl, C 3 to C 16 branched alkyl, C 3 to C 16 cyclic alkyl, partially or perfluorinated C1 to C 16 alkyl, partially or perdeuterated C1 to C lft alkyl, PX‘(R 8 ) 2 , halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R 8 is independently selected from Cg to C 12 aryl, C 3 to C 12 heteroaiyl, C 1 to C 16 alkyl, Ct to C 16 alkoxy, partially or perfluorinated C 1 to C M alkyl, partially or perfluorinated C1 to C 16 alkoxy, partially
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cg to C18 aryl, substituted or unsubstituted C 3 to C20 heteroaiyl, C 1 to C 16 alkyl, C 3 to C 16 branched alkyl, C 3 to C 16 cyclic alkyl, partially or perfluorinated C1 to C 16 alkyl, partially or perdeuterated Cl ft) C 16 allyl, halogen, F or
  • R 8 is independently selected from C6 to C 52 aryl, C 3 to C 12 heteroaryl, C1to C 16 alkyl, C1 to C 16 alkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated Cj to C 16 alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C1 P alkoxy; and X* is selected from O, S or Se, preferably O.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cg to C1 H ary] , substituted or unsubstituted C :! to C a > heteroaiyl, Ct to C 16 alkyl, C 3 to C 16 branched alkyl, C 3 to C 16 cyclic alkyl, partially or perfluorinated C 1 to C 16 alkyl, partially or perdeuterated C t to C 16 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cg to C 16 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C 16 alkyl, C 3 to C 16 branched alkyl, C 3 to C 16 cyclic alkyl, partially or perfluorinated C1 to C 16 alkyl, partially or perdeuterated Cito C 16 alkyl, halogen. F or CN.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cg to C1 2 aryl, substituted or unsubstituted C 3 to C14 heteroaryl, C1 to C 10 alkyl, C 3 to C M branched alkyl, C 3 to C 10 cyclic alkyl, partially or perfluorinated C1 to C10 alkyl, partially or perdeuterated C1 to C 10 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted C 6 to C ia aryl, substituted or unsubstituted C 3 to C14 heteroaiyl, C1 to C 10 alkyl, C 3 to C 10 branched alkyl, C 3 to C 1O cyclic allqfl, partially or perfluorinated C1 to C 1 , alkyl, partially or perdeuterated C1 to C1 ⁇ > alkyl, halogen, F or CN.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cg to C 10 aryl, substituted or unsubstituted C 3 to C 16 heteroaryl, (A to C 6 alkyl, C 3 to Cg branched alkyl, C 3 to Cg cyclic alkyl, partially or perfluorinated C1 to C 6 alkyl, partially or perdeulcrated C1 to C1 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cg to C 10 aryl, substituted or unsubstituted C 3 to C12 heteroaryl, C1 to Cg alkyl, C 3 to Cg branched alkyl, C 3 to Cg cyclic alkyl, partially or perfluorinated C1 to Cg alkyl, partially or perdeuterated C1 to Cg alkyl, halogen, F or ON,
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cg to C 1O aryl, substituted or unsubstituted C 3 to C10 heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to Cg cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted C1, to C 1( , aryl, substituted or unsubstituted C 3 to C 10 heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to Cg cyclic allyl, partially or perfluorinated C1 to C, alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, For CN.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cg aryl, substituted or unsubstituted C 3 to C s heteroaryl, C1 to C 4 alkyd, C 13 to C 4 branched alky], C 3 to Cg cyclic alky l, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on L are independently selected from D, substituted or unsubstituted Cg aryl, substituted or unsubstituted C 3 to C s heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to Cg cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN.
  • L is selected from the following moieties E1 to E33 shown in Table 2a.
  • L is selected from the following moieties E1 to E34 shown in Table 2a.
  • X 2 is selected from O or S, preferably O;
  • R 1 -- and R ,: ⁇ are independently selected from H, C1 to C16 alkyl. C1 to C16 alkoxy, Q, to C18 aryl, C 3 to C20 heteroaryl, perfluorinated C1 to C16 alkyl, perfluorinated C1 to C16 alkoxy; and the asterisk denotes the binding position.
  • L is selected from the following moieties E1 to E33 shown in
  • X 2 is selected from 0 or S, preferably 0;
  • R12 and R‘ 13 are independently selected from H, C1 to C16 alkyl. C1 to C16 alkoxy , C6 to C18 aryl, C 3 to C20 heteroaryl, perfluorinated C1 to C16 alfcfl, perfluorinated C1 to C16 alkoxy; and the asterisk “ " denotes the binding position.
  • L is selected from the moieties E1 to E30. According to an embodiment, L is selected from the moieties E1 to E24.
  • L is selected from the moieties E1 to E23.
  • L is selected from the moieties E1 to E5, and E8 to E23.
  • L is selected from the moieties Ei to E5, E8 to E13 and E16.
  • L is selected from the moieties E1 to E5, E11 and E16.
  • L is selected from the moieties E1 to E5 and E16.
  • L is selected from the moieties E1 to Eg, Eu and E16.
  • L is selected from the moieties E2 to E3, E11 and E16.
  • L is selected from the moieties E2 to E3 and E16.
  • the compound of formula (I) has a LUMO energy level when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase ⁇ -1.3 eV, preferably ⁇ -1.35 eV, and more preferably of ⁇ -1,4 eV..
  • the compound of formula (I) has a LUMO energy level when calculated with the program package TURBOMOLE V6.5 (TURBO MOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase of > -2.5 eV, preferably of > -2.0 eV, more preferably > -1.9 eV, even more preferably ⁇ -1.85 eV, and most preferably > -1.8 eV.
  • TURBOMOLE V6.5 TURBO MOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany
  • the compound of formula (I) has a LUMO energy level when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE C1mbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31C1* basis set in the gas phase in the range of > -2.5 eV and ⁇ -1.3 eV, preferably of > -2.0 eV to ⁇ -1.35 eV, more preferably > -1.9 eV to ⁇ -1.4 eV, even more preferably > -1.85 eV to ⁇ -1.4 eV and most preferably a -1.8 eV to s -1.4 eV.
  • TURBOMOLE V6.5 TURBOMOLE C1mbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany
  • the compound of formula (I) has a molecular weight in the range of ⁇ 400 g/mol to ⁇ 2000 g/mol, preferably 2415 g/mol to S1500 g/mol, more preferably 3:430 g/mol to ⁇ 1000 g/mol, and most preferably >440 g/mol to ⁇ 900 g/mol.
  • R* to R 7 are independently selected from H , or D; L is selected from substituted or unsubstituted C1, to C1H aryl, substituted or unsifostituted C a to C18 heteroaryl.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C (1 to Cfo aryl, substituted or unsubstituted C a to C18 heteroaryl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independentlyselected from H, or D;
  • L is selected from substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C a to C18 heteroaryl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted C1> to C18 aryl, substituted or unsubstituted C 3 to C16 heteroaryl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2- quinoline group or an unsubstituted phenyl.
  • R* to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted Ct, to (fo aryl or substituted or unsubstituted C a to C12 heteroaryl.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C1, to C la aryl or substituted or unsubstituted C a to (to heteroaryl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 to (to aryl or substituted or unsubstituted C a to C12 heteroaryl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C 2 to C12 heteroaryl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2- quinoline group or an unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C 2 to C 10 heteroaryl.
  • R 1 to R" are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C 6 to C16 aryl or substituted or unsubstituted CL to C10 heteroaryl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 arc independently selected from H, or D;
  • L is selected from substituted or unsubstituted C 6 to C 10 aryl or substituted or unsubstituted C 2 to C K) heteroaryl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C 2 to C 10 heteroaryl;
  • Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2- quinoline group or an unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; Lis selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl.
  • R‘ to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C* aryl or substituted or unsubstituted C 3 to C 5 heteroaryl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C ⁇ , aryl or substituted or unsubstituted C 3 to C 5 heteroaryl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; Lis selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl' Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2- quinoline group or an unsubstituted phenyl.
  • R’ to R 7 are independently selected from H, or D; Lis selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein heteroaryl is a six-member ring.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C h aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein heteroaryl is a six-member ring;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C ( , aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein heteroaryl is a six-member ring;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C b ary] or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein heteroaryl is a six-member ring;
  • Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, orb; L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, pjTazinyl, pyrimidyl, triazinyl.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R1 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl;
  • Ar is selected from a substituted or unsubstituted 2- pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R' to R’ are independently selected from H, or D;
  • L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl;
  • Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R" are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl; Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from E1 to E5, and E8 to E23.
  • R 1 to R 7 are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R‘ to R 7 are independently selected from H, or D; L is selected from E1 to Eg, and E8 to E23; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23.
  • R 1 to R 7 are independently selected from H, or D; L is selected from Ea, E3, E8, Eg, Eu, E14 and E15; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from Ez, E3, E8, Eg, Eu, E14 and E15; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R* to R 7 are independently selected from H, or D; L is selected from E2, E3, E8, E9, Eu, E14 and E15; Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; L is selected from E2 to E3, and E1i.
  • R 1 to R 7 are independently selected from H, or D; L is selected from E2 to E3, and E1i; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • L is selected from E2 to E3, and E1l;
  • Ar is selected from a substituted or unsubstituted 2- pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R are independently selected from H, or D; L is selected from E2 to E3. and E11; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • the compound of formula (I) is selected from the compound of formula (II) wherein
  • Ar is selected from substituted or unsubstituted C 6 to C 24 aryl or substituted or unsubstituted
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C 1 to C1 alkyl, substituted or unsubstituted C6, to C 24 aryl or substituted or unsubstituted C 2 to C24 heteroaryl, CN, halogen, F, C1 to (fo alkoxy, C 3 to C 1 6 branched alkyl, C 3 to C16, cyclic alkyl , C 3 to C1 ( , branched alkoxy, C 3 to C 16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PXrfRbfr wherein R 8 is independently selected from C 6 to C 12 aryl, C 3 to C 12 heteroaryl, C1 to C16, alkyl, C1 to CK alk
  • the compound of formula (I) is selected from the compound of formula (III) wherein Ar is selected from substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl; wherein formula (III) can be undeuterated, partially deuterated or folly deuterated.
  • the compound of formula (I) is selected from the compound of formula (IVa) or (IVb)
  • Ar is selected from substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C24 heteroaryl; wherein formula (IVa) or (IVb) can be undeuterated, partially deuterated or fully deuterated.
  • the compound of formula (I) is selected from the compound of formula (Va). (Vb). (Vc) or (Vd)
  • R 15 and R 16 are independently of each other selected from H, D, substituted or unsubstituted C1 to C1g alkyl, substituted or unsubstituted C® to C 24 aryl or substituted or unsubstituted G to C24 heteroaryl, CN. halogen.
  • R 8 is independently selected from C1, to Ce aryl, G to C 12 heteroaryl, C1 to C1® alkyl, C1 to C1® alkoxy, partially or perfluorinated C1 to C1® alkyl, partially or perfluorinated C1 to C1® alkoxy, partially or perdeuterated C1 to C1® alkyl, partially or perdeuterated C1 to C1® alkoxy, or PX*(R 8 )-, wherein R 8 is independently selected from C1, to Ce aryl, G to C 12 heteroaryl, C1 to C1® alkyl, C1 to C1® alkoxy, partially or perfluorinated C1 to C1® alkyl, partially or perfluorinated C1 to C1® alkoxy, partially or perdeuterated C1 to C1® alkyl, partially or perdeuterated C1 to C16 alkoxy; and X 1 is selected from 0, S
  • the one more substituents on R 15 an d R’ 6 are independently selected from D, C® to C18 aryl, C 3 to C 20 heteroaryl, C1 to C1® alkyl, C1 to Cm alkoxy, C 3 to C* branched alkyl, C 3 to C16 cyclic alkyl, C 3 to C16 branched alkoxy, C 3 to C1® cyclic alkoxy, partially or perfluorinated C1 to C1® alkyl, partially or perfluorinated C1 to C1® alkoxy, partially or perdeuterated C1 to C1® alkyl, partially or perdeuterated C1 to C1® alkoxy, halogen, F, CN or PX 1 (R 8 ) 2 , wherein R 8 is independently selected from C1> to C1a aryl, C 3 to C J2 heteroaryl, C1 to C1® alkyl, C1 to C1® alkoxy, partially or
  • R 15 to R* 6 are independently selected from D, substituted or unsubstituted C® to C18 aryl, substituted or unsubstituted C 3 to C 2O heteroaryl, C1 to C16 alkyl, C 3 to C1® branched alkyl, C 3 to C1® cyclic alkyl, partially or perfluorinated Ct to C1® alkyl, partially or perdeuterated C1 to C1® alkyl, PX «(R S )2, halogen, F or CN, wherein R® is independently selected from C® to C 12 aryl, C 3 to C1 2 heteroaryl , C1 to C1® alkyl, C1 to ⁇ C1® alkojy, partially or perfluorinated C1 to C1® allyl, partially or perfluorinated Ct to C1® alkoxy, partially or perdeuterated C1 to C1® allyl
  • R1 to R1 6 wherein one or more substituents on R1 to R1 6 , if present, are independently selected from D, substituted or unsubstituted C® to C18 aryl, substituted or unsubstituted C 3 to C 2() heteroaryl, C1 to CKJ alkyl, C 3 to C16 branched alkyl, C 3 to C 1 6, cyclic alkyl, partially or perfluorinated C1 to C1a alkyl, partially or perdeuterated C1 to C 1( , alkyl , halogen, F or CN.
  • substituents on R’5 to R 16 are independently selected from D, substituted or unsubstituted C6 to C ffl aryl, substituted or unsubstituted C 3 to C1 4 heteroaryl, Q to C1 O alkyl, C 3 to C1 0 branched alkyl, G 3 to C10 cyclic alkyl, partially or perfluorinated Octo C 10 alkyl, partially or perdeuterated C 1 to C 10 , alkyd, halogen, F or CN.
  • substituents on R’s to R 16 are independently selected from D, substituted or unsubstituted C6 to C I0 aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C 3 to C6 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkyl, halogen, For CN.
  • R 3 s to R 16 wherein one or more substituents on R 3 s to R 16 , if present, are independently selected from D, substituted or unsubstituted C6 to C !fi aryl, substituted or unsubstituted C 3 to C 10 heteroaryl, C1 to C 4 allyl, C 3 to C 4 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C 1 to C 4 allyl, halogen, F or CN.
  • substituents on R n to R’ 6 are independently selected from D, substituted or unsubstituted Ct, aryl, substituted or unsubstituted C 3 to C s heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to C fo cyclic alkyd, partially or perfluorinated C1 to C 4 alkyd, partially or perdeuterated C : to C 4 alkyl, halogen, F or CN.
  • the compound of formula (I) is selected from the compound of formula (Afra), (Aflb) , (Vic) or (Wd):
  • R’s and R 16 are independently of each other selected from wherein formula (Via) or (Vid) can be undeuterated, partially deuterated or fully deuterated.
  • the compound of formula (I) may be selected from the following compounds I-i to I-298 shown in Table 3.
  • the compound of formula (I) may be selected from the following compounds I-i to I-150, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
  • the compound of formula (I) is selected from the compounds shown in Table 4.
  • the compound of formula (I) is selected from the compounds shown in Table 5.
  • the compound of formula (I) is selected from the compounds shown in Table 6.
  • the compound of formula (I) is selected from the compounds shown in Table 7.
  • Table 7 wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
  • the compound of formula (I) is selected from the compounds shown in Table 7b.
  • Table 8 wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
  • the first electron transport layer is in direct contact with the first emission layer.
  • the first electron transport layer is closer to the anode layer than any other electron transport layer within the organic electroluminescent device.
  • the first electron transport layer which is in direct contact with the first n-type charge generation layer is the electron transport layer closest to the anode layer.
  • the first electron transport layer is arranged between the first emission layer and the first charge generation layer.
  • the thickness of the first electron transport layer may be in the range from 0.5 nm to 50 nm; alternatively in the range from 1 nm to about 40 nm; or alternatively in the range of 2 nm to 30 nm.
  • the first electron tr ansport layer is non- emissive.
  • the term “essentially non-emissive” or “non- emissive” means that the contribution of the compound or layer to the visible emission spectrum from the device is less than 10 %, preferably less than 5 % relative to the visible emission spectrum.
  • the visible emission spectrum is an emission spectrum with a wavelength of about a 380 nm to about ⁇ 780 nm.
  • the first electron transport layer is free of 8-hydroxyquinolinolato-lithium.
  • the first electron transport layer is free of a lithium metal complex.
  • the electron transport compound may ha ve a molecular weight in the range of >400 g/mol to ⁇ 2000 g/mol, preferably >415 g/mol to ⁇ 1500 g/mol, more preferably >430 g/mol to ⁇ 1000 g/mol, and most preferably 2440 g/mol to ⁇ 900 g/mol.
  • the first electron transport layer comprises an electron transport compound, wherein the electron transport compound comprises 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings, and optionally 9 aromatic or heteroaromatic rings, wherein one or more of the aromatic or heteroaromatic rings may be substituted with Cl to C4 alkyl.
  • an aromatic, respectively heteroaromatic ring is a single aromatic ring, for example a 6-membered aromatic ring such as phenyl, a 6-membered heteroaromatic ring such as pyridyl, a 5-membered heteroaromatic ring such as pyrrolyl etc.
  • each ring is considered as a single ring in this regard.
  • naphthalene comprises two aromatic rings.
  • the electron transport compound may comprise at least one heteroaromatic ring, optionally 1 to 5 heteroaromatic rings, optionally 1 to 4 heteroaromatic rings, optionally 1 to 3 heteroaromatic rings, and optionally 1 or 2 heteroaromatic rings.
  • the aromatic or heteroaromatic rings of the electron transport compound may be 6-membered rings.
  • the heteroaromatic rings of the electron transport compound may be a N-containing heteroaromatic ring, optionally all of the heteroaromatic rings are N-containing heteroaromatic rings, optionally all of the heteroaromatic rings heteroaromatic rings contain N as the only type of heteroatom.
  • the electron transport compound may comprise at least one six-member heteroaromatic ring containing one to three N-atoms in each heteroaromatic ring, optionally one to three 6- membered heteroaromatic rings containing one to three N-atoms in each heteroaromatic ring, respectively.
  • the at least one 6-membered heteroaromatic ring comprised in the electron transport compound may be an azine.
  • the at least one 6-membered heteroaromatic ring comprised in the electron transport compound may be triazine, diazine, pyrazine, pyrimidine pyridine preferably triazine.
  • the heteroaromatic rings may be separated from each other by at least on aromatic ring which is free of a heteroatom.
  • heteroatoms in the heteroaromatic rings of the electron transport compound are bound into the molecular structure of the electron transport compound by at least one double bond.
  • the compound comprising at least one nitrogen atom in a six-member aromatic ring in the electron transport layer is selected from formula (xxa) or formula (xxb) shown in Table 9.
  • Ar 1 is a substituted or unsubstituted C 3 to C 40 heteroaromatic ring system comprising at least one nitrogen atom
  • Ar is substituted or unsubstituted C 3 to C 40 heteroaromatic ring system comprising at least one nitrogen atom
  • the substituents on Ari and Ar n are, identically or differently on each occurrence, D, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R a
  • Ar Ia , Ar lb , Ar lc , Ar Ila , and Ar nb are, identically or differently on each occurrence, H, D, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R 8 ; wherein at least one of Ari a , Ar lb , Ar Ie in formula (xxa)
  • an aromatic or heteroaromatic ring system is intended to be taken to mean a system which does not necessarily contain only one aryl or one heteroaryl group or only aryl or heteroaryl groups, but instead in which a plurality of aryl or heteroaryl groups may also be interrupted by a short non-aromatic unit (preferably less than 10 percent of the atoms other than H), such as, for example, an spa-hybridised C1 N or O atom.
  • systems such as 9, 9 '-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, benzophenone, etc., are also intended to be taken to mean aromatic ring systems for the purposes of this invention.
  • aromatic or heteroaromatic ring system is taken to mean systems in which a plurality of aryl or heteroaryl groups are linked to one another by single bonds, for example biphenyl, terphenyl or bipyridine.
  • Ar 1 is selected from pyrazine, pyridine, pyrimidine, or triazine, phenanthroline.
  • Ar is selected from pyrazine, pyridine, pyrimidine, or triazine, phenanthroline.
  • Ar 1 in formula (xxa) or (xxxa) is selected from pyrazine, pyridine, pyrimidine, triazine, phenanthroline; or Ar 1 in formula (xxa) or (xxxa) and Ar 11 in formula (xxb) or (xxxb) are independently of each other selected from pyrazine, pyridine, pyrimidine, triazine, or phenanthroline.
  • the compound comprising at least one nitrogen atom in a six-member aromatic ring in the electron transport layer is selected from formula (xxxa) or formula (xxxb): wherein
  • Z Ia is selected from N or CH
  • Z ,b is selected from N or CH
  • Z ,c is selected from N or CH
  • Z Ila is selected from N or CH
  • Z !lb is selected from N or CH
  • Z I1C is selected from N or CH, wherein in formula (XXxa) at least one of Z la , Z ,b and Z' c is selected from N, wherein in formula (XXxb) at least one of Z Ia , Z ib , Z ,c , Z ila , Z IIb , and Z llc is selected from N, wherein Ar Ia , Ar Ib , Ar lc , Ar IIa and Ar IIb are identically or differently on each occurrence, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R a ; wherein ArHs a divalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R®, wherein RHs on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(R b )
  • an aromatic or heteroaromatic ring system is intended to be taken to mean a system which does not necessarily contain only aryl or heteroaryl groups, but instead in which a plurality of aryl or heteroaryl groups may also be interrupted by a short non-aromatic unit (preferably less than 10 percent of the atoms other than H), such as, for example, an spMiybridised C1 X or O atom.
  • a short non-aromatic unit preferably less than 10 percent of the atoms other than H
  • systems such as 9,9'- spirobifluorene, 9,9-diarylfluorenc, triaiylaminc, diaryl ether, stilbene, benzophenone, etc., are also intended to be taken to mean aromatic ring systems for the purposes of this invention.
  • an aromatic or heteroaromatic ring system is taken to mean systems in which a plurality of aryl or heteroaryl groups are linked to one another by single bonds, for example biphenyl, ter
  • the first electron transport layer comprises an electron transport compound, wherein the electron transport compound is selected from 2-([i s i'-biphcnyl]-3-yl)- 4-(2',6'-diphenyl-[j,i , :4' ] i"rterphenyl]-4-yl)-6-phcnyl-i,3,5-triazine J 2,2’-(1,3-
  • the electron transport compound is selected from 2-([i s i'-biphcnyl]-3-yl)- 4-(2',6'-diphenyl-[j,i , :4' ] i"rterphenyl]-4-yl)-6-phcnyl-i,3,5-triazine J 2,2’-(1,3-
  • the electron transport compound has a LUMO energy level when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by apphing the hybrid functional B3LYP with a 6-31G" basis set in the gas phase of ⁇ -1.50 eV, preferably ⁇ -1.55 eV, preferably ⁇ -1.60 eV, and most preferably ⁇ -1.65 eV.
  • TURBOMOLE V6.5 TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany
  • the electron transport compound has a LUMO energy lex-el when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase in the range of £ -2.5 eV to ⁇ -1.5 eV, preferably £ -2.0 eV to ⁇ -1.5 eV, more preferably > -1.95 eV to ⁇ -1.55 eV, even more preferably > -1.90 eV to ⁇ -1.6 eV, even more preferably ⁇ -1.90 eV to ⁇ -1.65 eV, and most preferably > -1.87 eV to ⁇ - 1.65 eV.
  • TURBOMOLE V6.5 TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to ⁇ 4.0 D; alternatively > o D to ⁇ 3.7 D; alternatively > o D to ⁇ 3.5 D; alternatively a o D to ⁇ 3.0 D; alternatively > o D to ⁇ 2.7 D; alternatively > o D to ⁇ 2.5 D; alternatively > o D to ⁇ 2.0 D; alternatively > o D to ⁇ 1.5 D; alternatively > o D to ⁇ 1.0 D.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to s 3.7 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6"3iG* basis set in the gas phase is in the range of £ -1.90 eV and s -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of a o D to ⁇ 3.7 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated uith the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV and ⁇ -1.65 eV,
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to ⁇ 3.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.90 eV and ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of a o D to ⁇ 3.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH. Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV to ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to ⁇ 3.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, C1ermany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.90 eV and ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of a o D to ⁇ 3.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated ⁇ with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of a -1.87 eV to ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of > 0 D to ⁇ 2.7 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of 2 -1.90 eV and ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of 20 D to ⁇ 2.7 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, C16rmany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV to ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of 2 o D to ⁇ 2.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYF with a 6-31G* basis set in the gas phase is in the range of 2 -1.90 eV and ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of 2 o D to ⁇ 2.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, C16rmany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of 2 -1.87 eV to s -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of 20 D to ⁇ 2.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, C16rmany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.90 eV and ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of 2 o D to ⁇ 2.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE C1mbH, Litzenhardtstrasse 19, 76135 Düsseldorf, C16rmany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of 2 -1.87 eV to ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > 0 D to s 1.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LXP with a 6-31G 1 basis set in the gas phase is in the range of > -1.90 eV and ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to ⁇ 1.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV to ⁇ -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of > 0 D to s 1.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of a -1.90 eV and -s -1.65 eV.
  • the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > 0 D to ⁇ 1.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV to ⁇ -1.65 eV.
  • the unit for the dipole moment “Debye” is abbreviated with the symbol “D”.
  • of a molecule containing N atoms is given by: where qt and r t are the partial charge and position of atom i in the molecule.
  • the dipole moment is determined by a semi-empirical molecular orbital method.
  • the geometries of the molecular structures are optimized using the hybrid functional B3LYP with the 6-31G ; basis set in the gas phase as implemented in the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany). If more than one conformation is viable, the conformation with the lowest total energy is selected to determine the bond lengths of the molecules.
  • the organic electroluminescent device according to the invention may comprise besides the first electron transport layer one or more further electron transport layer.
  • a further electron transport layer does not have to be free of 8-Hydroxyquinolinolato-lithium.
  • a further electron transport layer which is closest to the cathode preferably contains 8-Hydroxyquinolinolato-lithium, i.e. the electron transport layer which is not interrelated to a charge generation layer.
  • the electron transport layer may be the inventive organic semiconductor layer comprising the inventive compound represented by the general Formula (I) as defined herein.
  • the OLED may comprise an electron transport layer or a n electron transport layer stack comprising at least a first electron transport layer and at least a second electron transport layer.
  • the injection and transport of the electrons may be controlled, and the holes may be efficiently blocked.
  • the OLED may have long lifetime.
  • the one or more further electron transport layer(s) of the organic electroluminescent device may comprise the compound represented by general formula (xxxa) or formula (xxxb) as defined above as the organic electron transport matrix (ETM) material.
  • the electron transport layer may comprise, besides or instead of the compound represented by the general Formula (I), further ETM materials known in the art.
  • the electron transport layer may comprise as the only electron transport matrix material the compound represented by general Formula (I).
  • the inventive organic electronic device comprises more than one electron transport layers
  • the compound represented by the general Formula (I) may be comprised in only one of the electron transport layers, in more than one of the electron transport layers or in all of th e electron transport layers.
  • the electron transport layer may comprise, besides the ETM material, at least one additive as defined below.
  • the electron transport layer may comprise one or more n-tipe dopants.
  • the additive may be an n-type dopant.
  • the additive can be alkali metal, alkali metal compound, alkaline earth metal, alkaline earth metal compound, transition metal, transition metal compound or a rare earth metal.
  • the metal can be one selected from a group consisting of Li, Na, K, Rb, C 6 , Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb.
  • the t-type dopant can be one selected from a group consisting of C 6 , K, Rb, Mg, Na, Ca, Sr, Eu and Yb.
  • the alkali metal compound may be 8- Hydroxyquinolinolato-lithium (LiQ), Lithium tetra(iH-pyrazol-i-yl)borate or Lithium 2- (diphenylphosphoiyl)phenolate.
  • Suitable compounds for the ETM (which may be used in addition to the inventive compound represented by the general Formula (I) as defined above) are not particularly limited.
  • the electron transport matrix compounds consist of covalently bound atoms.
  • the electron transport matrix compound comprises a conjugated system of at least 6, more preferably of at least to delocalized electrons.
  • the conjugated system of delocalized electrons may be comprised in aromatic or heteroaromatic structural moieties, as disclosed e.g. in documents EP 1 970 371 Al or WO 2013/079217 Ai.
  • an organic electroluminescent device comprising an anode layer, a cathode layer, a first emission layer and a second emission layer, a first charge generation layer , a first electron transport layer, wherein the first charge generation layer is arranged between the first emission layer and the second emission layer, wherein the first charge generation layer comprises a first n-type ch arge generation layer and a firstp-type charge generation layer, wherein the first n-type charge generation layer is doser to the anode layer than the first p- type charge generation layer, wherein the first p-tvpe charge generation layer is closer to the cathode layer than the first n- type charge generation layer, wherein the first electron transport layer is arranged in direct contact with the first n-type charge generation layer, and wherein the first n-type charge generation layer comprises a metal dopant and a compound of formula (I)
  • Ar is selected from substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C24 heteroaryl, wherein one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C 16 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C16 alkyl, Cito C1c alkoxy, C 3 to C 16 branched alkyl, C 3 to C 16 cyclic alkyl, C 3 to C1 ⁇ branched alkoxy, C 3 to C 16 cyclic alkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C 1 to C 16 alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy, PX'(R 8 ) 2 , halogen, F or CN, wherein the substituents may be
  • R* to R 7 are independently selected from H, D, substituted or unsubstituted C 1 to C 16 alkyl, substituted or unsubstituted C ⁇ to C 24 aryl or substituted or unsubstitated C 2 to C24 heteroaryl, CN, halogen, F C1 to C 16 alkyl.
  • C1 to C 16 alkoxy C 3 to C 16 branched alkyl, C, to C 16 cyclic alkyl, C 3 to C 16 branched alkoxy, C 3 to C 16 cyclic alkoxy, partially or perfluorinated C1 to C 16 alkyl , partially or perfluorinated C 1 to C 16 alkoxy, partially or perdeuterated C to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy, or PX1(R 8 ) a wherein R 8 is independently selected from C ⁇ to C a aryl, C 3 to C )2 heteroaiyl, C to C 16 alkyl, C to C 16 alkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to C 16 alkoxy, partially or perdeuterated C 1 to C 16 alkyl, partially or perdeuterated C1 to C 1( , alkoxy; and X 1 is selected from 0, S or Se,
  • the organic electronic device may comprise, besides the layers already mentioned above, further layers. Exemplary embodiments of respective layers are described in the following:
  • the substrate may be any substrate that is commonly used in manufacturing of, electronic devices, such as organic light-emitting diodes. If light is to be emitted through the substrate, the substrate shall be a transparent or semitransparent material, for example a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate maybe both a transparent as well as a non-transparent material, for example a glass substrate, a plastic substrate, a metal substrate or a silicon substrate.
  • Either a first electrode or a second electrode comprised in the inventive organic electronic device may be an anode electrode.
  • the anode electrode may be formed by depositing or sputtering a material that is used to form the anode electrode.
  • the material used to form the anode electrode may be a high work-function material, so as to facilitate hole injection.
  • the anode material may also be selected from a low work function material (i.e. aluminum).
  • the anode electrode may be a transparent or reflective electrode.
  • Transparent conductive oxides such as indium tin oxide (ITO), indium zinc oxide (IZO), tin-dioxide (SnO2), aluminum zinc oxide (A1ZO) and zinc oxide (ZnO), may be used to form the anode electrode.
  • the anode electrode may also be formed using metals, typically silver (Ag), gold (Au), or metal alloys.
  • a hole injection layer may be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, or the like.
  • the deposition conditions may vary according t) the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL.
  • conditions for vacuum deposition may include a deposition temperature of ioo° C to 500° C1 a pressure of 10-8 to 10-3 Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm/sec.
  • coating conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL.
  • the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm, and a thermal treatment temperature of about 8o° C to about 200° C. Thermal treatment removes a solvent after the coating is performed.
  • the HIL may be formed of any compound that is commonly used to form a HIL.
  • examples of compounds that may be used to form the HIL include a phthalocyanine compound, such as copper phthalocyanine (CuPc), 4,4’,4"-tris (3-methylphenylphenylamino) triphenylamine (m- MTDATA), TDATA, 2T-NATA, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA), and polyaniline)/poly(4-styrenesulfonate (PANI/PSS).
  • CuPc copper phthalocyanine
  • m- MTDATA 4,4’,4"-tris (3-methylphenylphenylamino) triphenylamine
  • the HIL may comprise or consist of p-type dopant and the p-type dopant may be selected from tetrafluoro-tetracyanoquinonedimethane (F4TCNQ), 2,2'-(perfluoronaphthalen-2,6- diylidene) dimalononitrile or 2,2',2"-(cyclopropane-i,2,3-triylidene)tris(2-(p- cyanotetrafluorophenyljacetonitrile) but not limited hereto.
  • F4TCNQ tetrafluoro-tetracyanoquinonedimethane
  • F4TCNQ tetrafluoro-tetracyanoquinonedimethane
  • 2,2'-(perfluoronaphthalen-2,6- diylidene) dimalononitrile dimalononitrile
  • the HIL may be selected from a hole-transporting matrix compound doped with a p-type dopant
  • a-NPD doped with 2 J 2'-(perfluoronaphthalen-2,6-diylidene) dimalononitrile The p- type dopant concentrations can be selected from 1 to 20 wt.-%, more preferably from 3 wt.-% to 10 wt.-%.
  • the thickness of the HIL may be in the range from about 1 nm to about too nm, and for example, from about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injecting characteristics, without a substantial penalty in driving voltage.
  • a hole transport layer may be formed on the HIL by vacuum deposition, spin coating, slot-die coating, printing, casting, Langmuir-Blodgett (LB) deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL, However, the conditions for the vacuum or solution deposition may vary, according to the compound that is used to form the HTL.
  • the HTL may be formed of any compound that is commonly used to form a HTL.
  • Compounds that can be suitably used are disclosed for example in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010 and incorporated by reference.
  • Examples of the compound that may be used to form the HTL are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl- [i,i-biphenyl]-4,4' -diamine (TPD), or N,N'-di(naphthalen-i-yl)-N,N'“ciiphenyl benzidine (alpha-NPD); and triphenylamine-based compound, such as 4,4',4"-tris(N- carbazolyl)triphenylamine (TCTA).
  • TCTA can transport holes and inhibit excitons from being diffused into the EML.
  • the thickness of the HTL may be in the range of about 5 ran to about 250 run, preferably, about 10 nm to about 200 ran, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, further about 120 nm to about 140 nm.
  • a preferred thickness of the HTL may be 170 nm to 200mm.
  • the HTL may have excellent hole transporting characteristics, without a substantial penalty in driving voltage.
  • an electron blocking layer is to prevent electrons from being transferred from an emission layer to the hole transport layer and thereby confine electrons to the emission layer. Thereby, efficiency, operating voltage and/or lifetime are improved.
  • the electron blocking layer comprises a triarylamine compound.
  • the triarylamine compound may have a LUMO level doser to vacuum level than the LUMO level of the hole transport layer.
  • the electron blocking layer may have a HOMO level that is further away from vacuum level compared to the HOMO lev el of the hole transport layer.
  • the thickness of the electron blocking layer may be selected between 2 and 20 nm,
  • the electron blocking layer has a high triplet level, it may also be described as triplet control layer.
  • the function of the triplet control layer is to reduce quenching of triplets if a phosphorescent green or blue emission layer is used, Thereby, higher efficiency of light emission from a phosphorescent emission layer can be achieved.
  • the triplet control layer is selected from triarylamine compounds with a triplet level above the triplet level of the phosphorescent emiter in the adjacent emission layer. Suitable compounds for the triplet control layer, in particular the triarylamine compounds, are described in EP 2 722908 Ai.
  • Emission layer Emission layer
  • the EML may be formed on the HTL by' vacuum deposition, spin coating, dot-die coat-ing, printing, casting, LB deposition, or the like.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the EML.
  • the emission layer does not comprise the compound of Formula (J).
  • the emission layer (EML) may be formed of a combination of a host and an emitter dopant.
  • Example of the host are Alq3, 4,4'-N,N'-dicarbazole-biphenj’l (CBP), poly(n-vinylcarbazole) (PVK), 9JO-di(naphthalene-2-j’l)anthracene (ADN), 4,4',4’'-tris(carbazol-9-yl)- triphenylamine(TCTA), i,3,5-tris(N-phcnylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl- 9,io-di-2-naphthylanthracenee (TBADN), distyrylarylene (DSA) and bis(2-(2- hydroxyphenyl)benzo-thiazolate)zinc (Zn(BTZ)2).
  • red emiter dopants examples include PtOEP, Ir(piq)3, and Btp21r(acac), but are not limited thereto. These compounds are phosphorescent emiters, however, fluorescent red emitter dopants could also be used.
  • Examples of phosphorescent blue emitter dopants are F2lrpic, (F2ppy)2lr(tmd) and Ir(dfppz)3 and ter-fluorene.
  • phosphorescent blue emitter dopants are F2lrpic, (F2ppy)2lr(tmd) and Ir(dfppz)3 and ter-fluorene.
  • 4.4'-bis(4-diphenyl amiostyryDbiphenyl (DPAVBi), 2,5,8,] i-tetra- tert -butyl perylene (TBPe) are examples of fluorescent blue emiter dopants.
  • the amount of the emitter dopant may be in the range from about 0.01 to about 50 parts by weight, based on 100 parts by weight o f the host.
  • the emission layer may consist of a light-emitting polymer.
  • the EML may have a thickness of about 10 nm to about 100 nm, for example, from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML may have excellent light emission, without a substantial penalty in driving voltage.
  • HBL Hole blocking layer
  • a hole blocking layer may be formed on the EML, by using vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like, in order to prevent the diffusion of holes into the ETL.
  • the HBL may have also a triplet exciton blocking function.
  • the hole blocking layer may be the inventive organic semiconductor layer comprising or consisting of the inventive compound represented by the general Formula (1) as defined above.
  • the HBL may also be named auxiliary ETL or a-ETL.
  • the conditions for deposition and coating may be similar to those for the formation of the HIL However, the conditions for deposition and coating may vary, according to the compound that is used to form the HBL. Any compound that is commonly used to form a HBL may be used. Examples of compounds for forming the HBL include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.
  • the HBL may have a thickness in the range from about 5 rnn to about loo nm, for example, from about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL may have excellent hole-blocking properties, without a substantial penalty in dining voltage.
  • the hole blocking layer may also be described as a-ETL or auxiliary ETL.
  • Electron injection layer (EIL)
  • An optional EIL which may facilitates injection of electrons from the cathode, may be formed on the ETL, preferably directly on the electron transport layer.
  • materials for forming the EIL include lithium 8-hydroxyquinolinolate (LiQ), LiF, NaCl, CsF, LisO, BaO, Ca, Ba, Yb, Mg which are known in the art.
  • Deposition and coating conditions for forming the EIL are similar to those for formation of the HIL, although the deposition and coating conditions may vary, according to the material that is used to form the EIL.
  • the thickness of the EIL may be in the range from about 0.1 nm to about 10 nm, for example, in the range from about 0.511m to about 9 nm. When the thickness of the EIL is within this range, the EIL may have satisfactory electron-injecting properties, without a substantial penalty in driving voltage.
  • the cathode electrode is formed on the EIL if present.
  • the cathode electrode may be formed of a metal, an alloy, an electrically conductive compound, or a mixture thereof.
  • the cathode electrode may have a low work function.
  • the cathode electrode may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like.
  • the cathode electrode may be formed of a transparent conductive oxide, such as ITO or IZO.
  • the thickness of the cathode electrode may be in the range from about 5 nm to about 1000 nm, for example, in the range from about 10 nm to about 100 nm.
  • the cathode electrode may be transparent or semitransparent even if formed from a metal or metal alloy.
  • the cathode electrode is not part of an electron injection layer or the electron transport layer.
  • the first charge generation layer comprises a p- type and an n-type charge generation layer.
  • An interlayer may be arranged between the p-type charge generation layer and the n- type charge generation layer.
  • the charge generation layer is a pn junction joining an n-frpe charge generation layer (electron generating layer) and a hole generating layer.
  • the n-side of the pn junction generates electrons and injects them into the layer which is adjacent in the direction to the anode.
  • the p-side of the p-n junction generates holes and injects them into the layer which is adjacent in the direction to the cathode.
  • Suitable matrix materials for the hole generating layer may be materials conventionally used as hole injection and/or hole transport matrix materials.
  • p-type dopant used for the hole generating layer can employ conventional materials.
  • the p-type dopant can be one selected from a group consisting of tetrafluore-7,7,8,8-tetracyanoquinodimethanc (F4- TCNQ), derivatives of tetracyanoquinodimcthane, radialene derivatives, iodine, FeClg, FeEg, and SbCfo.
  • the host can be one selected from a group consisting of N,N'-di(naphthalen- i-yl)-N,N-diphenyl-benzidine (NPB), N,N'-diphenyl-N,N’-bis(3-methylphenyl)-i,i-biphenj-l- 4,4’-diamine (TPD) and N,N',N'-tetranaphthyl-benzidine (TNB).
  • the p-type charge generation layer may consist of CNHAT.
  • the organic electroluminescent device further comprises a layer selected from hole injection layer, hole transport layer, electron blocking layer, a holeblocking layer, an electron transport layer, and an electron injection layer.
  • the organic electroluminescent device further comprises a hole injection layer, a first hole transport layer, a second hole transport layer, first electron blocking layer, second electron blocking layer, optionally a first hole blocking layer, optionally a second hole blocking layer, a second electron transport layer, and an electron injection layer.
  • the organic electroluminescent device comprises an anode layer (120), a hole injection layer (130), a first hole transport layer (141), a first electron blocking layer (142), a first emission layer (145), a first optional hole blocking layer(i47), and a first electron transport layer (149), wherein the first electron transport layer (149) is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex, wherein the first electron transport layer (149) is preferably in direct contact with the first emission layer (145), a first charge generation layer (16O) disposed over the first electron transport layer (149), wherein the first charge generation layer (160) comprises a first n-type charge generation layer (161), and a first p-type charge generation layer (162), wherein the first n-typc charge generation layer (161) comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterb
  • the organic electroluminescent device further comprises a third emission layer, a second electron transport layer, and a second charge generation layer, wherein the third emission layer is arranged between the second charge generation and the cathode layer, wherein the second charge generation layer is arranged between the first charge generation layer and the cathode layer, and between the second emission layer and the third emission layer wherein the second charge generation layer comprises a second n-type charge generation layer and second p-type charge generation layer, wherein the second n-tvpe charge generation layer is arranged closer to the anode layer than the second p-ripe charge generation layer, wherein the second p-type charge generation layer is arranged closer to the cathode layer than the second n-type charge generation layer, wherein the second electron transport layer is arranged between the second emission layer and the third emission layer, wherein the second electron transport layer is in direct contact with the second n-type charge generation layer, wherein wherein the second n-type charge generation layer comprises a metal dopant and a
  • the organic electroluminescent device comprises an anode layer (120), a hole injection layer (130), a hole transport layer (141), a first electron blocking layer (142), a first emission layer (145), a first optional hole blocking layer (147)?
  • first electron transport layer (149) wherein the first electron transport layer (149) is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex, wherein the first electron transport layer (149) is preferably in direct contact with the first emission layer (145), a first charge generation layer (160) disposed o ⁇ er the first electron transport layer (149), wherein the first charge generation layer (160) comprises a first n-type charge generation layer (161), and a first p-type charge generation layer (162), wherein the first n-type charge generation layer (161) comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (149) is in direct contact with the first n-type charge generation layer (261) , a second hole transport layer (241), and a second electron blocking layer (242), a second emission layer (245), a second optional hole blocking
  • an organic electroluminescent device the method using: at least one deposition source, preferably two deposition sources and more preferred at least three deposition sources.
  • the methods for deposition that can be suitable comprise: deposition via vacuum thermal evaporation; deposition via solution processing, preferably the processing is selected from spincoating, printing, casting; and/or slot-die coating.
  • OLED organic light-emitting diode
  • the method may farther include forming on the anode electrode, an emission layer and at least one layer selected from the group consisting of forming a hole injection layer, forming a hole transport layer, or forming a hole blocking layer, between the anode electrode and the first electron transport layer.
  • the method may further include the steps for forming an organic light-emitting diode (OLED), wherein on a substrate a first anode electrode is formed, on the first anode electrode an emission layer is formed, on the emission layer an electron transport layer stack is formed, optionally a hole blocking layer is formed on the emission layer and an organic semiconductor layer is formed, and finally a cathode electrode is formed, optional a hole injection layer, a hole transport layer, and a hole blocking layer, formed in that order between the first anode electrode and the emission layer, optional an electron injection layer is formed between the organic semiconductor layer and the cathode electrode.
  • OLED organic light-emitting diode
  • the method may further comprise forming an electron injection layer on the organic semiconductor layer.
  • the OLED may not comprise an electron injection layer.
  • an electronic device comprising at least one organic light emitting derice according to any embodiment described throughout this application, preferably, the electronic device comprises the organic light emitting diode in one of embodiments described throughout this application. More preferably, the electronic derice is a display device.
  • the organic electronic device according to the invention comprising an organic semiconductor layer comprising a compound according to Formula (I) may further comprise a layer comprising a radialene compound and/or a quinodimethane compound.
  • the radialene compound and/or the quinodimethane compound may be substituted with one or more halogen atoms and/or with one or more electron withdrawing groups.
  • Electron withdrawing groups can be selected from nitrile groups, halogenated alkyl groups, alternatively from perhalogenated alkyl groups, alternatively from perfluorinated alkyl groups.
  • Other examples of electron withdrawing groups may be acyl, sulfonyl groups or phosphoryl groups.
  • acyl groups, sulfonyl groups and/or phosphoryl groups may comprise halogenated and/or perhalogenated hydrocarbyl.
  • the perhalogenated hydrocarbyl may be a perfluorinated hydrocarbyl.
  • Examples of a perfluorinated hydrocarbyl can be perfluormethyl, perfluorethyl, perfluorpropyl, perfluorisopropyl, perfluorobutyl, perfluorophenyl, perfluorotolyl; examples of sulfonyl groups comprising a halogenated hydrocarbyl may be trifluoromethylsulfonyl, pentafluoroethylsulfonyl, pentafluorophcnylsulfony], heptafluoropropylsufonyl, nonafluorobutylsulfonyl, and like.
  • the radialene and/or the quinodimethane compound may be comprised in a hole injection, hole transporting and/or a hole generation layer.
  • the radialene compound may have Formula (XX) and/or the quinodimethane compound may have Formula (XXIa) or (XXIb): wherein (as an exception different to the description above) R’, R 2 , R3, R4 R 5 , R 6 , Rr, R®, R 11 , R 12 R‘5, R 16 , R 2 °, R 21 are independently selected from above mentioned electron withdrawing groups and R 9 , R 10 , Rfo R 1 '*, Ro, R 18 , R19 R 22 , R 2 ® and R 24 are independently selected from H, halogen and above mentioned electron withdrawing groups.
  • the organic semiconductor layer comprising compound of formula (1) is adjacent to a layer comprising a compound of formula (XX), (XXIa) or (XXIb).
  • the organic semiconductor layer comprising compound of formula (I) is in direct contact to a layer comprising a compound of formula (XX), (XXIa) or (XXIb).
  • the present invention relates to a compound of formula (M1) or of formula (M2) wherein in formula (M1)
  • R 8 is independently selected from G to C1 2 aryl, C 3 to C12 heteroaryl, C1 to C 16 alkyl, C1 to C 16 alkoxy, partially or perfluorinated C1 to C 1 6 alkyl, partially or perfluorinated C1 to C1» alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy; and
  • X 1 is selected from O, S or Se, preferably 0;
  • Rto R Lb , R ⁇ and R Ld are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl , substituted or unsubstituted C1 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F, C 1 to C 16 alkoxy, C 3 to C 16 branched alkyl, C 3 to C 16 cyclic alkyl, C 3 to C16 branched alkoxy, C 3 to C 16 cyclic alkoxy, partially or perfluorinated C1 to C1& alkyl, partially or perfluorinated C1 to C 16 alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy, or PX’CR 8 ) wherein R 8 is independently selected from C6 to C 12 aryl, C 3 to C1 2 heteroaryl, C1 to C 16 allyl, C1 to C1
  • - Ar is selected from substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C24 heteroaryl; wherein in formula (M2)
  • R 2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C 16 alkyl, substituted or unsubstituted G to C1 4 aryl or substituted or unsubstituted C1 to C 24 heteroaryl, CN, halogen, F, C1 to C 16 alkoxy, C 3 to C 16 branched alkyl, C3 to C 16 cyclic alkyl, C 3 to C 16 branched alkoxy, C 3 to C 16 cyclic alkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to C 16 alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkoxy, or PX 1 (R 8 ) 2 wherein R 8 is independently selected from C 6 to C1 2 aryl, C 3 to C1 2 heteroaryl, C1 to C 16 alkyl, C1 to C 16 alkoxy, partially or
  • - Ar is selected from substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaiyl;
  • - L is selected from substituted or unsubstituted C 6 to C 24 aryl, substituted or unsubstituted C 2 to C 24 heteroaryl.
  • the compound of formula (M1) may be a compound of formula (M3) and the compound of formula (M2) may be a compound of formula (M4)
  • R* to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C1 to C 24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C 3 to C16 branched alkyl, C 3 to C 16 cyclic alkyl. C 3 to C1,-, branched alkoxy, C 3 to C» cyclic alkoxy, partially or perfluorinated C1 to C18 alkyl, partially or perfluorinated C> to C1o alkoxy, partially or perdeuterated C.
  • R 8 is independently selected from C 6 to C 12 aryl, C 3 to C 12 heteroaryl, C1 to C16 alkyl, C1 to C1 ⁇ . alkoxy, partially or perfluorinated C ⁇ to C1o alkyd, partially or perfluorinated C1 to C1o alkoxy, partially or perdeuterated C1 to C 16 alky l, partially or perdeuterated C 1 to C ,6 alkoxy; and X 1 is selected from O. S or Se, preferably O; and
  • R Lb , R Lb , Rtoand JR 14 are independently selected from H, D, substituted or unsubstituted C1 to C1o alkyd, substituted or unsubstituted C 6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C 3 to C 16 branched alkyl, C 3 to C 10 cyclic alkyl, C, to C16 branched alkoxy, C 3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C18 alkyl, partially or perfluorinated C1 to C1* alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX I (R 8 ) 2 wherein R 8 is independently selected from C1> to C !2 aryl, C 3 to C12 heteroaryl, C1 to C16 alk
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C1 to C 24 heteroaryl, CN, halogen, F, C1 to C1& alkoxy, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, C 3 to C 1 6 branched alkoxy, C 3 to C18 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to CK, alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX1(R8)2 wherein R 8 is independently selected from Crfo C 12 aryl.
  • C 3 to C 12 heteroaryl C1 to C10 alkyl, C1 to C1 6 alkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C1 6 alkyl, partially or perdeuterated C1 to C16 alkoxy; and
  • X’ is selected from O, S or Se, preferably 0; and
  • - L is selected from substituted or unsubstituted C6 to C 24 aryl, substituted or unsubstituted C 2 to C 64 heteroaryl.
  • R 1 to R ' are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C 6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C* alkyl, or PX1(R 8 )2 wherein R 8 is independently selected from C6 to C1 a aryl, C 3 to C1 2 heteroaryl, C1 to C16 alkyl.
  • C1 to CK alkoxy, partially or perfluorinated C1 to C18 alkyl, partially or perfluorinated C1 to Cm alkoxy, partially or perdeuterated C1 to Cm alkyl, partially or perdeuterated C1 to C16 alkoxy; and X 1 is selected from O, S or Se, preferably O,
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 1 6 alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F.
  • R 1 to R ⁇ are independently selected from H, D, substituted or unsubstituted C 1 to C16> alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, halogen, F.
  • R 1 to R ⁇ are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C 6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, F.
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C 2 to C18 heteroaryl, CN, halogen, Cl, F.
  • R 1 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C6 to Ca aryl or substituted or unsubstituted C 2 to C18 heteroaryl, F.
  • R‘ to R 7 are independently selected from H, D, substituted or unsubstituted C 1 to C6 alkyl, substituted or unsubstituted C6, to C1 2 aryl or substituted or unsubstituted C 2 to C 12 heteroaryl, CN, halogen, Cl, F.
  • R 1 to R' are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C12 aryl or substituted or unsubstituted C 2 to C 12 heteroaryl, F.
  • R 1 to R" arc independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted C6 to C1o aryl or substituted or unsubstituted C 2 to C 10 heteroaryl, CN, halogen, Cl, F.
  • R’ to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C 2 to C1 ( , heteroaryl, F.
  • R‘ to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, CN, halogen, Cl, F.
  • R* to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, F.
  • R J to R 7 are independently selected from H, D.
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C lh alkyl, substituted or unsubstituted Ct, to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F, C 3 to C ( 6 branched alkyl, C 3 to C lt -, cyclic alky l, partially or perfluorinated C 1 to C 1( , alkyd, partially or perdcuterated C1 to Ctft alkyd, or PX’(R 8 ) a wherein R 8 is independently selected from C c , to C 12 aryl, C ;j to C 12 heteroaryl.
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C® alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F.
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, halogen, F.
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted Ct, to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, F,
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C1 2 alkyl, substituted or unsubstituted C1 to C1 « aryl or substituted or unsubstituted C 2 to heteroaryl, CN, halogen, Cl, F.
  • R 2 to R" are independently selected from H, D, substituted or unsubstituted C1 to C 12 alkyl, substituted or unsubstituted C ( , to C1 » aryl or substituted or unsubstituted C ; to CJS heteroaryl, F.
  • R 2 to R 7 are independently selected from H. D, substituted or unsubstituted C1 to C 6 alkyl, substituted or unsubstituted C6, to C 12 aryl or substituted or unsubstituted C 2 to C 1 heteroaryl, CN, halogen, Cl, F.
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted C 6 to C J0 aryl or substituted or unsubstituted C 2 to C16 heteroaryl, CN, halogen, Cl, F.
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted C6 to C1 0 aryl or substituted or unsubstituted C 2 to C1o heteroaiyl, F.
  • R 2 to R 7 are independently selected from H, D, substituted or unsubstituted Cj to C 4 alkyl, substituted or unsubstituted C fi aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, CN, halogen, Cl, F.
  • R 2 to R" are independently selected from H, D, substituted or unsubstituted C1 to C 4 alkyl, substituted or unsubstituted C1, aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, F.
  • R 2 to R ⁇ are independently selected from H, D.
  • R 1 to R 7 in formulas (M1) and (M3), respectively R 2 to R 7 in formulas (M2) and (M4), may be independently unsubstituted or substituted with one or more substituents.
  • the one or more substituents on R> to R 7 in formulas (M1) and (M3), respectively R a to R 7 in formulas (M2) and (M4), if present, are independently selected from D, Ct, to C18 aryl, C3 to C 20 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, C 3 to C* branched alkoxy, C 3 to C 16 , cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C 1 to C16 alkoxy, partially or perdeuterated C.
  • R 8 is independently selected from C ( , to C 12 aryl, C.,.
  • R 1 to R'in formulas (M1) and (M3), respectively R 2 to R 7 in formulas (Ma) and (M4), if present, are independently selected from D.
  • R 8 is independently selected from C6 to Cfo aryl, C 3 to C 12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to Cfo alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X 1 is selected from O, S or Se, preferably 0.
  • the one or more substituents on R 1 to R 7 in formulas (M1) and (M3), respectively R 2 to R 7 in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted Ct, to 0,8 aryl, substituted or unsubstituted C 3 to C 2O heteroaryl, C1 to C 16 , alkyl, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C1 ft alkyl, partially or perdeuterated 0, to C16 alkyl, halogen, F or CN.
  • the one or more substituents on R 1 to R’ in formulas (M1) and (M3), respectively R a to R 7 in formulas (M2) and (M4X if present, are independently selected from D, substituted or unsubstituted C6 to C1 2 aryl, substituted or unsubstituted C 3 to C 14 heteroaryl, C1 to C 10 alkyl, C 3 to C10 branched alkyl, C 3 to C 10 cyclic alkyl, partially or perfluorinated C1 to Cur alkyl, partially or perdeuterated C1 to C 10 allgl, halogen, For CN.
  • the one or more substituents on R1 to R' in formulas (Mt) and (M3), respectively R 2 to R 7 in formulas (Ma) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 aryl, substituted or unsubstituted C 3 to C12 heteroaryl, C 1 to C1 alkyl, C 3 to C 6 branched alkyl, C 3 to C 6 cyclic alkyd , partially or perfluorinated C1 to C 6 alkyl, partially or perdeuterated C1 to Cf, alkyl, halogen, For CN.
  • the one or more substituents on R 1 to R 7 in formulas (M1) and (M3), respectively R 2 to R 7 in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C 6 to C1o aryl, substituted or unsubstituted C 3 to C 10 heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN.
  • the one or more substituents on R 1 to R 7 in formulas (M1) and (M3), respectively R 2 to R 7 in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C1 to C 5 heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C s to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN.
  • R L , R Lb , Rteand R R L a d re independently selected from H, D, and substituted or unsubstituted C1 to C16 alkyl.
  • Rte R Lb , R Lb ,and R 1 - 4 are independently selected from H, D, and substituted or unsubstituted C1 to C 12 alkyl.
  • R L a R Lb , Rfoand R Ld are independently selected from H, D, and substituted or unsubstituted C1 to C1, alkyl.
  • Rte R Lb are independently selected from H, D. and substituted or unsubstituted C1 to C 4 alkyl.
  • Rte Rte, Rteand R Ld are independently selected from H, D, and substituted or unsubstituted C1 alkyl.
  • the one or more substituents on R Lb , Rte Rfoand R M in formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C1& alkyl.
  • R 8 is independently selectedfrom C1> to C1 2 aryl, C 3 to C1 2 heteroaryl, C1 to alkyl, C1 to C1& alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C18 alkyl, partially or perdeuterated C1 to C1& alkoxy; and X 1 is selected from 0, S or Se, preferably O.
  • the one or more substituents on Rte Rtb, Rfoand R Lb in formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C1> to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C16 alkyl, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alky l, partially or perdeuterated C1 to C1d alkyl, halogen, For CN.
  • the one or more substituents on R Lb , R Lb , R 1x ,and R Lb in formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C1> to C12 aryl, substituted or unsubstituted C 3 to C M heteroaryl, C1 to C m alky l, C :; to C10 branched alkyl, C 3 to C1o cyclic alkyl, partially or perfluorinated C1 to C1o alkyl, partially or perdeuterated C1 to C1o alky l, halogen, F or CN.
  • the one or more substituents on Rte Ri> Rfoand R L m formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C1s to C10 aryl substituted or unsubstituted C 3 to C12 heteroaryl, C1 to C1> alkyl, C 3 to C6 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C1 to C1 alkyl, partially or perdeuterated C1 to C6 alkyl, halogen, F or CN.
  • the one or more substituents on R 1 - 3 , R Lb , RLC and RM in formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C 6 to C1o aryl, substituted or unsubstituted C 3 to C1o heteroaryl, C1 to C 4 allyl, C 3 to C 4 branched alkyl, C 3 to C 6 cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C1 alkyl, halogen, F or CN.
  • the one or more substituents on R Lb , R Lb , R'riand R Lb in formulas (M1) and (M3), if present, are independently selected from D. substituted or unsubstituted C1, aryl, substituted or unsubstituted C 3 to C 5 heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to C 6 cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN.
  • L is selected from substituted or unsubstituted Ct, to C1 « and, substituted or unsubstituted C 2 to C1& heteroaryl.
  • L is selected from substituted or unsubstituted C6 to C 12 aryl or substituted or unsubstituted C 2 to C12 heteroaryl.
  • L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted Cb to C JO heteroaryl.
  • L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl.
  • L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C 3 to C 3 heteroaryk wherein heteroaryl is a six-member ring.
  • L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, tnazinjl.
  • L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl
  • L is selected from substituted phenyl, unsubstituted phenyl or unsubstituted naphthyl.
  • L in formulas (Ma) and (M4) may be independently unsubstituted or substituted with one or more substituents
  • the one or more substituents on L in formulas (M2) and (M4) are independently selected from D, C 16 to C18 aryl, C 3 to C 20 heteroaryl.
  • X 1 is selected from O, S or Se, preferably O.
  • the one or more substituents on L in formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted C 6 to aryl, substituted or unsubstituted C 3 to Cfr heteroaryl, C1 to alkyl, C1 to C w alkoxy, C 3 to C 16 branched alkyl, C 3 to C16 cyclic alkyl, C 3 to C16, branched alkoxy, C 3 to CH, cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C ( to C t 6 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, PX ⁇ R 8 ) ⁇ , halogen, F or CN, wherein R 8 is independently selected from C6 to C 12 aryl, C 3 to Ce heteroaryl, C1 to C16 alkyl, C1 to
  • the one or more substituents on L in formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted C& to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C16 alkyl, C 3 to Cfr branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C1& alkyl, partially or perdeuterated C I to C16 alkyl, PX ⁇ R 8 ) ⁇ halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R 8 is independently selected from C6 to C 12 aryl, C 3 to C ia heteroaryl, C1 to Cn, alkyl, C ( to C l() alkoxy, partially or perfluorinated C 1 to C16, alkyl, partially or perfluorinated C1
  • the one or more substituents on L in formulas (Ma) and (M4) are independently selected from D, substituted or unsubstituted C6 to C1 s aryl, substituted or unsubstituted C 3 to Cao heteroaryl, C1 to C ⁇ alkyl, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyd, partially or perfluorinated C1 to C1& alky I, partially or perdeuterated C 1 to C16 alkyl, PX‘(R 8 ) 2 , halogen, F or CN, wherein R 8 is independently selected from C 6 to Cu aryl, C 3 to C12 heteroaryl, C1 to C ⁇ alkyl, C 1 to C16 alkoxy, partially or perfluorinated C1 to C16, alkyl, partially or perfluorinated C1 to C16, alkox, , partially or perdeuterated C> to C16 alky l,
  • the one or more substituents on L in formulas (Ma) and (M4) are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C 1 to C® alkyl, C 3 to C16 branched alkyl, C 3 to CH, cyclic alkyl, partially or perfluorinated Cj to C1 ⁇ > alkyd, partially or perdeuterated C1 to C K , alkyl, halogen, F or CN.
  • the one or more substituents on L in formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted C6 to C1 2 aryl, 6 substituted or unsubstituted C t to C1 4 heteroaryl, C1 to CK, alkyl, C 3 to C 10 branched alkyl, C 3 to C1o cyclic alkyl, partially or perfluorinated C1 to C 10 alkyl, partially' or perdeuterated C1 to C 10) alkyl, halogen, F or CN, wherein the substituents may be linked ⁇ ia a single bond or a heteroatom to form a ring.
  • L in formulas (M2) and (M4) is selected from the moieties Ei to E30.
  • L in formulas (M2) and (M4) is selected from the moieties Ei to E5, and E8 to E23.
  • L in formulas (Ma) and (M4) is selected from the moieties E1 to Eg, E8 to E13 and E16.
  • L in formulas (Ma) and (M4) is selected from the moieties Ei to E5, E11 and E16.
  • L in formulas (M2) and (M4) is selected from the moieties Ei to E5 and E16.
  • L in formulas (M2) and (M4) is selected from the moieties Ei to E3, E11 and E16.
  • L in formulas (M2) and (M4) is selected from the moieties E2 to E3, E1i and E16.
  • L in formulas (M2) and (M4) is selected from the moieties Ea to E3 and E16.
  • Ar of formulas ( M1) and (M3) Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 to C 2 ⁇ aryl or substituted or unsubstituted C 2 to C 24 heteroaryl.
  • Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 to C16 aryl or substituted or unsubstituted C 2 to C16 heteroaryl.
  • Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C 6 to C 12 aryl or substituted or unsubstituted C 2 to Cfo heteroaryl.
  • Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C 2 to C JO heteroaryl.
  • Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl.
  • Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein the heteroaiyl is a six-member ring.
  • Ar of formulas (M1) and (Mg) is selected from the group consisting of substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, and substituted or unsubstituted quinolinyl.
  • Ar of formulas (M1) and (M3) may be unsubstituted or substituted with one or more substituents.
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C 6 to C16 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, C 3 to C1& branched alkyl, C 3 to C16 cyclic alkyl, C 3 to C16 branched alkoxy, C 3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C 1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C> to C16 alkoxy, PX‘(R 8 ) 2!
  • R 8 is independently selected from Ca to C 12 aryl, C 3 to C Ja heteroaryl, C1 to C16 alkyl, C1 to C 1o alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to Cm alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X 1 is selected from O, S or Se, preferably 0.
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C, to C16 aryl, substituted or unsubstituted C 3 to C a ® heteroaryl, C1 to Cm.
  • R® is independently selected from C6 to C B aryl, C 3 to C 12 heteroaryl, Ck to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to Ch alky!, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C1r> alkyl, partially or perdeuterated C1 to Cto alkoxy; and > is selected from
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to Cj* alkyl, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C 1 to C16 alkyl, PXrfR 8 ) 2, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R 8 is independently selected from C 6 to C1 2 aryl, C 3 to C12 heteroaryl, C1 to C 1 6 alkyl, C1 to C ⁇ alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 al
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C ;1 to C 2O heteroaryl, C1 to C16 alkyl, C 3 to C lf > branched alkyl, C 3 to CK, cyclic alkyl, partially or perfluorinated C1 to C1 ⁇ , alkyd, partially or perdeuterated C1 to C16 alkyl, PX1(R), halogen, F or ON, wherein R 8 is independently selected from C& to C 12 aryl, C 3 to C18 heteroaryl, C1 to C 16 > alkyl, C L to C 16 alkoxy, partially or perfluorinated C1 to C lt , alkyd, partially or perfluorinated C ( to C16 alkoxy, partially or perdeuterated C 5 to C lb alkyl
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C20 heteroaryl, Ct to C16 alkyl, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C1& alkyl, C 3 to C16 branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, halogen, F or CN.
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C6 to C1 0 aryl, substituted or unsubstituted C 3 to C M heteroaryl, C 1 to C 10 alkyl, C 3 to C 10 branched alkyl, C 3 to CH. cyclic alkyl, partially or perfluorinated C1 to C 10 alkyl, partially or perdeuterated C1 to C 10 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar are independently selected from D, substituted or unsubstituted C6 to C 12 aryl, substituted or unsubstituted C 3 to C 14 heteroaryl, C 1 to C 10 alkyl ; C3 to branched alkyl, 0 ⁇ to C10 cyclic alkyd, partially or perfluorinated C1 to C1o alkj 1, partially or perdeuterated C1 to C1o alkyl, halogen, F or CN.
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C6 to C 10 aryl, substituted or unsubstituted C 3 to C12 heteroaryl, C1 to C6 alkyl, C 3 to C6, branched alkyl, C 3 to G cyclic alkyl, partially or perfluorinated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C6 to C1o aryl, substituted or unsubstituted C 3 to C 12 heteroaryl, C1 to C6 alkyl, G to Q branched alkyl, C 3 to C6 cyclic alkyl , partially or perfluorinated C1 to Cg alkyl, partially or perdeuterated C1 to Ci alkyl, halogen, F or CN.
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted G to C J0 aryl, substituted or unsubstituted C 3 to C 10 heteroaryl, C1 to C1 alkyd, C 3 to C1 branched alky l, C 3 to C6 cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar of formulas (M1) and (M3) are independently selected from D, substituted or unsubstituted C1 to C1o aryl, substituted or unsubstituted C 3 to C1o heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C1 to G cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN.
  • the one or more substituents on Ar of formulas (M1) and (Mg), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C 3 to C 5 heteroaryl, C1 to C1 alkyl, C3 to C 4 branched alkyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN.
  • Ar of formulas (M1) and (M3) is selected from the following D1 to Dip shown in Table 1 Ar of formula (M2) and (M4)
  • Ar of formulas (Ma) and (M4) is selected from substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C1 4 heteroaryl.
  • Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C 2 to C18 heteroaryl.
  • Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted C6 to C 12 aryl or substituted or unsubstituted G to C1 2 heteroaryl.
  • Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted C6 to C1o aryl or substituted or unsubstituted C1 to C16 heteroaryl.
  • Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted Cfe aryl or substituted or unsubstituted C 3 to C 5 heteroaryl.
  • Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C 3 to C 5 heteroaiyl, wherein the heteroaiyl is a six-member ring.
  • Ar is selected from the group consisting of substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, and substituted or unsubstituted quinolinyl.
  • Ar of formulas (M2) and (M4) may be unsubstituted or substituted with one or more substituents.
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted G to C18 aryl, substituted or unsubstituted C 3 to C20 heteroaryl, C1 to C 13 alkyl, C1 to C 16 alkoxy, C 3 to C16 branched alkyl, C 3 to C 16 cyclic alkyl, C 3 to Cm branched alkoxy, C 3 to C 16 cyclic alkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R 8 is independently selected from C1, to C 12
  • the one or more substituents on Ar of formulas (Ma) and (M4) are independently selected from D, substituted or unsubstituted C () to C1B aryl, substituted or unsubstituted C 3 to C1o heteroaryl, C1 to C1t, alkyl, C1 to C1* alkoxy, C 3 to C16 branched alkyl, C 3 to C lt , cyclic alkyl, C ( to C1 ⁇ > branched alkoxy, C 3 to Cw c Cy1c6lic alkoxy, partially or perfluorinated to C1r> alky], partially or perfluorinated C1 to C1& alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy.
  • R 8 is independently selected from C1 to C1 2 aryl, C 3 to C 12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to Cm alkoxy; and X' is selected from O, S or Se, preferably O.
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted C 6 to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C1& alkyl, C 3 to C1& branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C1& alkyl, PX‘(R®) 2 , halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R 8 is independently selected from G to C1 2 aryl, C 3 to C1 2 heteroaryl, C1 to C l( , alky l, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorin
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted C 6 to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C16 alkyd, C1 to C lt , branched alky ] , C 3 to C1* cyclic alky l, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyd, PX 1 (R 8 ) 2 , halogen, F or CN, wherein R a is independently selected from C1 to C 12 aryl, C 3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C1* alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C 16 alkyl
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C16 alkyl, C 3 to C t 6 branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16, alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C 3 to C 20 heteroaryl, C1 to C16 alkyl, C 3 to C16 branched alkyl, C 3 to C18 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, halogen, F or CN.
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted C 6 to C 12 aryl, substituted or unsubstituted (fl to C l4 heteroaryl, C1 to C1o alkyl, C 3 to C I0 branched alkyl, C 3 to C16 cyclic alkyl, partially or perfluorinated C1 to C1o alkyl, partially or perdeuterated C1 to C1o alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted G to C 12 aryl, substituted or unsubstituted C 3 to C )4 heteroaryl, C1 to C1o alkyl, C 3 to C1o branched alkyl, C 3 to C1o cyclic alkyl, partially or perfluorinated C1 to C1o alkyl, partially or perdeuterated C1 to C1o alkyl, halogen, F or CN.
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted G to C1o aryl, substituted or unsubstituted C 3 to C1 a heteroaryl, C1 to C 6 alkyl, C 3 to G branched alkyl, C 3 to C1 cyclic alkyl, partially or perfluorinated C1 to C1 alkyl, partially or perdeuterated C1 to G alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted G to C 10 aryl, substituted or unsubstituted C 3 to C1y heteroaryl, C1 to C1 alkyl, C 3 to G branched alkyl, C 3 to G cyclic alkyl, partially or perfluorinated C1 to C& alkyl, partially or perdeuterated C1 to G alkyl, halogen, F or CN.
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted G to C1o aryl, substituted or unsubstituted G to C 10 heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to G cyclic alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN, wherein the substituents may be linked ria a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar of formulas (Ma) and (M4) are independently selected from D, substituted or unsubstituted G to C 10 aryl, substituted or unsubstituted C 3 to C1o heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched alkyl, C 3 to C1 cy devis alkyl, partially or perfluorinated C1 to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN.
  • the one or more substituents on Ar of formulas (M2) and (M4) are independently selected from D, substituted or unsubstituted C1 aryl substituted or unsubstituted C 3 to C1 heteroaryl, C1 to C. ⁇ alkyl, C 3 to C 4 branched alkyl, C 3 to C1 cyclic alky l, partially or perfluorinated C1 to C 4 allyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN, wherein the substituents maybe linked ria a single bond or a heteroatom to form a ring.
  • the one or more substituents on Ar of formulas (Ma) and (M4) are independently selected from D, substituted or unsubstituted G aryl, substituted or unsubstituted C 3 to C s heteroaryl, C1 to C 4 alkyl, C 3 to C 4 branched allyl, C 3 to C6 cyclic alkyl, partially or perfluorinated C ( to C 4 alkyl, partially or perdeuterated C1 to C 4 alkyl, halogen, F or CN.
  • Ar of formulas (M2) and (M4) is selected from the following Di to D19 shoum in Table 1
  • R 2 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C® aryl, substituted or unsubstituted C 2 to C® heteroaryl.
  • R 1 to R 7 are independently selected from H, or D;
  • Rfr, Rfr, Rfoand R M are independently selected from H, D, substituted or unsubstituted C1 to C® alkyl, substituted or unsubstituted Cg to C 24 aryl or substituted or unsubstituted C 2 to C S4 heteroaryl, CN, halogen, F, C 3 to C® branched alkyl, C 3 to C® cyclic alkyl, partially or perfluorinated C1 to C® alkyd, partially or perdeuterated C1 to C® alkyl, or PX’CR 8 )® wherein R 8 is independently selected from C6 to C® aryl, C 3 to C t2 heteroaryl, Ci to C® alkyl, C1 to C1G alkoxy, partially or perfluorinated C1 to C® alkyd, partially or pci-fluorinated C1 to
  • R a to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to Gia aiyl, substituted or unsubstituted C 2 to C18 heteroaryl; and in formula (Ma) Ar is selected from a substituted or unsubstituted pjridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • R b , R Lb , Rfoand R Ixi are independently selected from H, D, substituted or unsubstituted C1 to C® alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F, C 3 to C16 branched alkyl, C 3 to C® cyclic alkyl, partially or perfluorinated C1 to C® alkyl, partially or perdeuterated C1 to G® alkyl, or PX'(R 8 ) S wherein R 8 is independently selected from Ge to C® aryl, C 3 to C ia heteroaryl, C 1 to C® alkyl, C1 to C !6 alkoxy, partially or perfluorinated C1 to C® alkyl, partially or perfluorinated C1
  • R 2 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 to C® aryl, substituted or unsubstituted C 3 to C 16 heteroaryl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R’ to R 7 are independently selected from H, or D;
  • R ta , R Lb , Rfoand R Lb are independently selected from H, D, substituted or unsubstituted C1 to C lfi alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F, C 3 to C 16 branched alkyl, C 3 to C 16 cyclic alkyl, partially or perfluorinated C1 to C 16 alkyl, partially or perdeuterated Q to C 16 alkyl, or PX 1 (R 8 ) 2 wherein R 8 is independently selected from C6 to C12 aryl, C 3 to C 12 heteroaryl, C 4 to C 16 alkyl, C1 to C 16 alkoxy, partially or perfluorinated C1 to C 16 alkyl, partially or perfluorinated C1 to
  • R 2 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 to C 16 aryl, substituted or unsubstituted C 2 to Cts heteroaiyl;
  • Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R’ to R 7 are independently selected from H, or D;
  • R 1 - 3 , R li , Rfoancl R Lb are independently selected from H, D, substituted or unsubstituted C> to C 16 alkyl, substituted or unsubstituted C b to C 24 aryl or substituted or unsubstituted C 2 to C24 heteroaryl, CN, halogen, F, C 3 to C 16 branched alkyl, C 3 to C 16 cyclic alkyl, partially or perfluorinated C1 to C 16 alkyl, partially or perdeuterated C1 to C 16 alkyl, or PX‘(R 8 ) 2 wherein R 8 is independently selected from C 6 to C1 a aryl, C 3 to C i2 heteroaiyl, C1 to C 16 alkyl, C1 to C 16 alkoxy, partially or perfluorinated C1 to C 16 alkyl,
  • R 2 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C ia aryl or substituted or unsubstituted C 2 to C t2 heteroaryl
  • R’ to R 7 are independently selected from H, or D;
  • R Lb , R J - b , Rfoand R 1 -* 1 are independently selected from H, D, substituted or unsubstituted C1 to C 16 alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C J4 heteroaryl, CN, halogen, F.
  • R ? to R" are independently selected from H, or D;
  • L is selected from substituted or unsubstituted Cb to C J2 aryl or substituted or unsubstituted C 2 to C >2 heteroaiyl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted 01 unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • R Lb , R Lb , R ⁇ .and R ljd are independently selected from H, D, substituted or unsubstituted C> to C16 alkyl, substituted or unsubstituted C h to C 24 ary] or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 to CA aryl or substituted or unsubstituted C 2 to Cj 2 heteroaryl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • R u “, R tb , R Lc ,and R Lb are independently selected from H, D, substituted or unsubstituted C 1 to 0,6 alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F;
  • in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C 6 to C ia aryl or substituted or unsubstituted C 2 to C 12 heteroaryl;
  • Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • R 1 ⁇ , R Ib , R Lb ,and R ,J are independently selected from H, D, substituted or unsubstituted C1 to C t 6 alkyl, substituted or unsubstituted C6 to C 24 aryl or substituted or unsubstituted C 2 to C 24 heteroaryl, CN, halogen, F;
  • in formula (M1) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C m aryl or substituted or unsubstituted C 2 to C1 ⁇ > heteroaryl.
  • R 1 to R 7 are independently selected from H, or D; R Lb , R Lb , R Lb ,and R 1 ⁇ are independently selected from H, D, and substituted or unsubstituted C1 to CK, alkyl.
  • R 2 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 to C «> aryl or substituted or unsubstituted C 2 to C t0 heteroaryl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R are independently selected from H, or D;
  • R 1 - 3 , R Lh , R Lb ,and R k) are independently selected from H, D. and substituted or unsubstituted C 1 to C S 6 alkyl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted Cb to C M aryl or substituted or unsubstituted C 2 to C1 O heteroaryl' and in formula (Ma) Ar i s selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • R Lb , R Lb , Rfoand R w are independently selected from H, D, and substituted or unsubstituted C1 to C16 alkyl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R a to Rt are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C I0 aiyl or substituted or unsubstituted C 2 to C 10 heteroaryl; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R' to R 7 are independently selected from H, or D;
  • R 1 - 1 , R Lb , Rfoand R Lb are independently selected from H, D, and substituted or unsubstituted C1 to Cfo alkyl;
  • Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted C 6 to C10 aryl or substituted or unsubstituted C 3 to C s heteroaryl.
  • R 1 to R 7 are independently selected from H, or D; RM, R Lb , R ix ,and R ⁇ 3 are independently selected from H, D, and substituted or unsubstituted C> to alkyl.
  • R 2 to R ⁇ are independently selected from H, or D;
  • L is selected from substituted or unsubstituted Cg to C 1O aryl or substituted or unsubstituted C :1 to C 5 heteroaryl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R’ to R 7 are independently selected from H, or D;
  • Rfr, R te ,and Rfr are independently selected from H, D, and substituted or unsubstituted C> to Cia alkyl;
  • Ar is selected from a substituted or un substituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 7 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl
  • R 1 to R 7 are independently selected from H, or D;
  • R 1 *, R Lb , R :x ,and R iid are independently selected from H, D, and substituted or unsubstituted C1 to C l3 alkyl;
  • R iid are independently selected from H, D, and substituted or unsubstituted C1 to C l3 alkyl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R a to R' arc independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 to C lo aryl or substituted or unsubstituted C 3 to C s heteroaryl;
  • Ar is selected from a:i unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R‘ to R 7 are independently selected from H, or D;
  • R kl , R 1h , R'qand R Ix! are independently selected from H, D, and substituted or unsubstituted C1 to C1 2 alkyd;
  • Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted Cg to C1o,aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein heteroaryl is a six-member ring.
  • R* to R 7 are independently selected from H, or D;
  • R 1 - 3 , R Lb , R Lb ,and R IzI are independently selected from H, D, and substituted or unsubstituted C1 to Ca alkyl.
  • R- to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted Ch to C (1 , aryl, or substituted or unsubstituted C ( to C-, hetcroaryl, wherein heteroaryl is a six-member ring;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • R’foand R IJ are independently selected from H, D, and substituted or unsubstituted C1 to C* alkyl;
  • in formula (M1) /Xr is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R z to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 to C1 0 aryl or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein heteroaryl is a six-member ring;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D; RM, R Lb , Rfoand R ⁇ * are independently selected from H, D, and substituted or unsubstituted C1 to C 6 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R z to R ⁇ are independently selected from H, or D;
  • L is selected from substituted or unsubstituted C6 aryl, substituted or unsubstituted naphthyl, or substituted or unsubstituted C 3 to C 5 heteroaryl, wherein heteroaryl is a six-member ring;
  • Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R" are independently selected from H, or D;
  • Rfo, R Lb , Rfoand R ⁇ are independently selected from H, D, and substituted or unsubstituted C1 to Cg alkyl;
  • in formula (M1) Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 2 to fo are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl.
  • R 1 to R 7 are independently selected from H, or D; Rfo R Lb , Rfoand R 1 ⁇ are independently selected from H, D, and substituted or unsubstituted C1 to C6 alkyl.
  • R 2 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, p ⁇ Tazinyl, pyrimidyl, triazinyl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R’ to R 7 are independently selected from H, or D;
  • R i a , R L ⁇ R'qand R Lib are independently selected from H, D, and substituted or unsubstituted C1 to C f , alkyl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D;
  • L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R7 are independently selected from H, or D;
  • Rfo, R Lb , R’frand R Lb are independently selected from H, D, and substituted or unsubstituted C1 to Cb alkyl;
  • in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, pjTazinyl, pyrimidyl, triazinyl; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R’ to R 7 are independently selected from H, or D;
  • R ⁇ ', R tb , R ix ,and R Lbl are independently selected from H, D, and substituted or unsubstituted C1 to C b alkyl;
  • R Lbl are independently selected from H, D, and substituted or unsubstituted C1 to C b alkyl;
  • Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl.
  • R‘ to R 7 are independently selected from H, or D; Rto R 1 *, Rfoand R ⁇ are independently selected from H, D, and substituted or unsubstituted C1 to C 4 alkyl.
  • R 2 to R 7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R' are independently selected from H, or D;
  • R Lb , R Lb , Rfoand R Lb are independently selected from H, D, and substituted or unsubstituted C1 to C 4 alkyl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 2 to R? are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; and in formula (Ma) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R* to R? are independently selected from H, or D;
  • Rfr*, R Lb , Rte and R 1 ⁇ are independently selected from H, D, and substituted or unsubstituted C1 to C « alkyl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 2 to W are independently selected from H, or D;
  • L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl;
  • Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R a to R ? are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23.
  • R* to R? are independently selected from H, or D;
  • R u ', R 1 b , R Lb ,and R 1 ⁇ are independently selected from H, D, and substituted or unsubstituted C1 to C 3 alkyl.
  • R 2 to R? are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R? are independently selected from H, or D;
  • R 1 - 3 , R t , R ⁇ and R Lb are independently selected from H, D, and substituted or unsubstituted C1 to C 3 alkyl;
  • Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl
  • R 2 to R ⁇ are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2- quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R? are independently selected from H, or D: R u , R Lb .
  • R L ’ b ,and R 1 - 4 are independently selected from H, D, and substituted or unsubstituted C 1 to C 3 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • R Lb , R Lb , R I - c ,and R w are independently selected from H, D, and substituted or unsubstituted Ch to C 3 alkyl;
  • R w is independently selected from H, D, and substituted or unsubstituted Ch to C 3 alkyl;
  • Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; Lis selected from E1 to Eg, and E8 to E23.
  • R' to R 7 are independently selected from H, or D;
  • R Lb , R'- 1 ’, Rfoand R Lb are independently selected from H, D, and substituted or unsubstituted C1 to C 2 allyl.
  • R 2 to R 7 are independently selected from H, or D; L is selected from Ea, E3, E8, Eg, Eu, E14 and E15; and in formula (Ma) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • R 1 - 3 , R Lb , R’frand R w are independently selected from H, D, and substituted or unsubstituted Ch to C 2 alkyl;
  • in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; Lis selected from E2, E3, E8, E9, E1i, Ei4,Eig, and E16; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R ⁇ are independently selected from H, or D; RM, R 1 * R Lb ,and R 1 * 1 are independently selected from H, D, and substituted or unsubstituted C ( to C 2 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • R- to R" are independently selected from H, or D;
  • L is selected from E2, E3, E8, Eg, E1i, Ei4,Eig;
  • Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R" are independently selected from H, or D;
  • R'A R Lb , R’frand R 1 ⁇ are independently selected from H, D, and substituted or unsubstituted C1 to C 2 alkyl;
  • in formula (M1) Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; L is selected from Ea to E3, E1i, and E16.
  • R 2 to R 7 are independently selected from H, or D; R ⁇ 1 , R Lb , R Lb ,and R w are independently selected from H, D, and substituted or unsubstituted C1 alkyl.
  • R z to R 7 are independently selected from H, or D; L is selected from E2 to E3, E11, E16; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl .
  • R> to R" are independently selected from H, or D;
  • R’A R Lb , R ⁇ , and R Lb are independently selected from H, D, and substituted or unsubstituted C1 alkyd ;
  • in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
  • R 2 to R 7 are independently selected from H, or D; L is selected from E2 to E3, E1i, and E16; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2- quinoline group, or substituted or unsubstituted phenyl.
  • R 1 to R 7 are independently selected from H, or D;
  • R 13 , R Lb , Rfoand R 1 ⁇ are independently selected from H, D, and substituted or unsubstituted C1 alkyl;
  • Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
  • Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • R 1 to R ⁇ are independently selected from H, or D;
  • R Ul , R 1b , Rfoand R 1/I are independently selected from H, D, and substituted or unsubstituted C1 alkyd;
  • Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
  • the compound of formulas (M1) to (M4) may be selected from the compounds I-i to I-298 shown in Table 3 above, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
  • the compound of formulas (M1) to (M4) maybe selected from the compounds shown in Table 4 above, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
  • the compound of formulas (M1 ) to (M4) may be selected from the compounds shown in Table 5 above, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
  • the compound of formulas (M1) to (M4) may be selected from the compounds shown in Table
  • the compound of formulas (M i) to (M4) may be selected from the compounds shown in Table
  • the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 13
  • the respective compound can be undeuterated, partially deuterated or folly deuterated.
  • the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 14
  • the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 15
  • the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 16
  • the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 17
  • the compound of formula (I) is selected from the compounds shown in Table 18.
  • Table J8 wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
  • the compound of formulas (M1) to (M4) may be selected from the compounds I-125, 1-126, 1- 151, 1-2 and I-152
  • Another aspect of the present invention provides a semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
  • Another aspect of the present invention provides a semiconducting layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
  • Another aspect of the present invention provides an electronic device comprising an semiconductor layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
  • the electronic device is an organic electronic device.
  • the electronic device comprises an electroluminescent device, an organic light emitting diode (OLED), a light emitting device, thin film transistor, a battery, a display device or an organic photovoltaic cell (OPV).
  • OLED organic light emitting diode
  • OLED organic photovoltaic cell
  • Another aspect of the present invention provides a display device comprising an organic electronic device comprising a semiconductor layer comprising the semiconducting materia] comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
  • FIG. 1 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
  • FIG. 2 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
  • FIG. 3 is a schematic sectional xiew of an organic electroluminescent device according to an exemplary embodiment of the present invention.
  • FIG. 4 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
  • first element when a first element is referred to as being formed or disposed "on” or “onto” a second element, the first element can be disposed directly on the second element, or one or more other elements may be disposed there between.
  • first element when referred to as being formed or disposed "directly on” or “directly onto” a second element, no other elements are disposed there between.
  • Fig. i is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
  • the organic electroluminescent device too includes an anode layer (ANO) 120, a first emission layer (EML1) 145, and a first electron transport layer (ETLi) 149, wherein the first electron transport layer (ETLi) 149 is free of 8-Hydroxyquinolinolato4ithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
  • ANO anode layer
  • EML1 first emission layer
  • ETLi first electron transport layer
  • the organic electroluminescent device further comprises a first charge generation layer (CGLi) 160 disposed over the first electron transport layer (ETLi) 149, wherein the first charge generation layer (CGLi) 160 comprises a first n-type charge generation layer (n-CGLi) 161, and a first p-type charge generation layer (p-CGLi) 162, wherein the first n-tjpe charge generation layer (n-CGLi) 161 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (ETLi) 149 is in direct contact with the first n-type charge generation layer (n-CGLi) 161.
  • the first charge generation layer (CGLi) 160 comprises a first n-type charge generation layer (n-CGLi) 161, and a first p-type charge generation layer (p-CGLi) 162, wherein the first n-tjpe charge generation layer (n-C
  • the organic electroluminescent device 100 farther comprises a second emission layer (EML2) 245, and a cathode layer (CAT) 190.
  • EML2 second emission layer
  • CAT cathode layer
  • Fig. 2 is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
  • the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a first hole transport layer (HTLi) 141, a first electron blocking layer (EBL1) 142, a first emission layer (EMLi) 145, a first optional hole blocking layer (HBLi) 147, and a first electron transport layer (ETLi) 149, wherein the first electron transport layer (ETLi) 149 is free of 8-Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
  • ANO anode layer
  • HIL hole injection layer
  • HTLi hole transport layer
  • EBL1 first electron blocking layer
  • EBLi emission layer
  • HBLi first optional hole blocking layer
  • ETLi electron transport layer
  • the organic electroluminescent device further comprises a first charge generation layer (CGLi) 160 disposed over the first electron transport layer (ETLi) 149, wherein the first charge generation layer (CGLi) 160 comprises a first n-type charge generation layer (n-CGLi) 161, and a first p-type charge generation layer (p-CGLi) 162, wherein the first n-type charge generation layer (n-CGLi) 161 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (ETLi) 149 is in direct contact with the first n-tjpc charge generation layer (n-CGLi) 161.
  • the organic electroluminescent device 100 further comprises a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242.
  • the organic electroluminescent device too further comprises a second emission layer (EML2) 245.
  • EML2 second emission layer
  • the organic electroluminescent device 100 further comprises a second optional hole blocking layer (HBL2) 247, an electron transport layer (ETL) 148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.
  • HBL2 hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • CAT cathode layer
  • Fig. 3 is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
  • the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a hole transport layer (HTL1) 141, a first electron blocking layer (EBLi) 142, and a first emission layer (EMLi) 145.
  • ANO anode layer
  • HIL hole injection layer
  • HTL1 hole transport layer
  • EBLi first electron blocking layer
  • EMLi first emission layer
  • the organic electroluminescent device 100 further comprises a first optional hole blocking layer (HBLi) 147.
  • HBLi hole blocking layer
  • the organic electroluminescent device 100 further comprises a first electron transport layer (ETLi) 149, wherein the first electron transport layer (ETLi) 149 is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
  • ETLi first electron transport layer
  • the organic electroluminescent device further comprises a first charge generation layer (CGLi) 160 disposed over the first electron transport layer (ETLi) 149, wherein the first charge generation layer (CC1Li) 160 comprises a first n-type charge generation layer (n-CGLi) 161, and a first p-type charge generation layer (p-CGLi) 162, wherein the first n-type charge generation layer (n-CGLi) 161 comprises a compound offbrmula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (ETLi) 149 is in direct contact with the first n-type charge generation layer (n-CGLi) 161.
  • the first charge generation layer (CC1Li) 160 comprises a first n-type charge generation layer (n-CGLi) 161, and a first p-type charge generation layer (p-CGLi) 162, wherein the first n-type charge generation layer (n-
  • the organic electroluminescent device 100 further comprises a second hole transport layer (HTL2) 241, and a second electron blocking layer (EBL2) 242.
  • HTL2 second hole transport layer
  • EBL2 second electron blocking layer
  • the organic electroluminescent device 100 further comprises a second emission layer (EML2) 245.
  • EML2 second emission layer
  • the organic electroluminescent device 100 further comprises a second optional hole blocking layer (HBLa) 247.
  • HLB hole blocking layer
  • the organic electroluminescent device 100 further comprises a second electron transport layer (ETL2) 249, wherein the second electron transport layer (ETL2) 249 is free of 8- Hydroxj-quinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
  • ETL2 second electron transport layer
  • the organic electroluminescent device further comprises a second charge generation layer (CGLa) 260 disposed over the second electron transport layer (ETLa) 249, wherein the second charge generation layer (CGL2) 260 comprises a second n-type charge generation layer (n- CGL2) 261, and a first p-type charge generation layer (p-CGL2) 262, wherein the second n- type charge generation layer (n-CGL2) 261 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the second electron transport layer (ETLi) 249 is in direct contact with the second n-type charge generation layer (n-CGLa) 261, wherein the second n-type charge generation layer (n-CGL2) 261 can be selected the same or different than the first n-type charge generation layer (n-CC1Li) 161, and wherein the second p-type charge generation layer (p-CGL2) 262 can be selected the same or different than the first
  • the organic electroluminescent device 100 further comprises a third hole transport layer (HTL3) 341, and a third electron blocking layer (EBL3) 342.
  • HTL3 hole transport layer
  • EBL3 third electron blocking layer
  • the organic electroluminescent device 100 further comprises a third emission layer (EML3) 345.
  • EML3 third emission layer
  • the organic electroluminescent device 100 further comprises a third optional hole blocking ayer (HBL3) 347> an electron transport layer (ETL)148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.
  • HBL3 hole blocking ayer
  • ETL electron transport layer
  • EIL electron injection layer
  • CAT cathode layer
  • Fig, 4 is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
  • the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a hole transport layer (HTLi) 141, a first electron blocking layer (EBL1) 142, a first emission layer (EML1) 145.
  • ANO anode layer
  • HIL hole injection layer
  • HTLi hole transport layer
  • EBL1 first electron blocking layer
  • EML1 emission layer
  • the organic electroluminescent device 100 further comprises a first optional hole blocking layer (HBLi) 147.
  • HBLi hole blocking layer
  • the organic electroluminescent device 100 further comprises a first electron transport layer (ETLi) 149, wherein the first electron transport layer (ETLi) 149 is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
  • ETLi first electron transport layer
  • the organic electroluminescent device further comprises a first charge generation layer (CGL) 160 disposed over the first electron transport layer (ETLi) 149, wherein the first charge generation layer (CC1Li) 160 comprises a first n-type charge generation layer (n-CGL) 161, and a first p-type charge generation layer (p-CGL) 162, wherein the first n-type charge generation layer (n-CGL) 161 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (ETLi) 149 is in direct contact nnth the first n-type charge generation layer (n-CGL) 161.
  • CGL first charge generation layer
  • CTLi first electron transport layer
  • the organic electroluminescent device 100 further comprises a second hole transport layer (HTL2) 241, and a second electron blocking layer (EBL2) 242.
  • HTL2 second hole transport layer
  • EBL2 second electron blocking layer
  • the organic electroluminescent device 100 further comprises a second emission layer (EMLa) 245.
  • the organic electroluminescent device 100 further comprises a second optional hole blocking layer (HBL2) 247.
  • HBL2 hole blocking layer
  • the organic electroluminescent device 100 farther comprises a second electron transport layer (ETLs) 2,49, wherein the second electron transport layer (ETL2) 249 is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
  • ETLs second electron transport layer
  • the organic electroluminescent device further comprises a charge generation layer (CC1L) 260 disposed over the second electron transport layer (ETL2) 249, wherein the second charge generation layer (CGL2) 260 comprising a second n-type charge generation layer (n-CGL) 261, and a second p-type charge generation layer (p-CGL) 262, wherein the second n-type charge generation layer (n-CGL) 261 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Yterbium, and wherein the second electron transport layer (ETL2) 249 is in direct contact wth the second n-type charge generation layer (n-CGLa) 261, wherein the second n-type charge generation layer (n-CGL2) 261 can be selected the same or different than the first n-type charge generation layer (n-CGLi) 161, and wherein the second p-type charge generation layer (p-CGLa) 262 can be selected the same or different than the first
  • the organic electroluminescent device 100 farther comprises a third hole transport layer (HTL3) 341, and a third electron blocking layer (EBL3) 342.
  • HTL3 hole transport layer
  • EBL3 third electron blocking layer
  • the organic electroluminescent device 100 further comprises a third emission layer (EML3) 345-
  • the organic electroluminescent device 100 farther comprises a third optional hole blocking layer (HBL3) 347.
  • HBL3 hole blocking layer
  • the organic electroluminescent deuce too further comprises a third electron transport layer (ETL3) 349, wherein the third electron transport layer (ETL3) 349 is free of 8- Hydroxwquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
  • ETL3 third electron transport layer
  • the organic electroluminescent device further comprises a charge generation layer (CGL3) 360 disposed over the third electron transport layer (ETL3) 349, wherein the third charge generation layer (CC1L3) 360 comprising a third n-typc charge generation layer (n-CGL.3) 361, and a third p-type charge generation layer (p-CGLg) 362, wherein the third n-t ⁇ pe charge generation layer (n-CC1Lg) 361 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the third transport layer (ETL3) 349 is in direct contact with the third n-type charge generation layer (n-CC1Lg) 361, wherein the third n-type charge generation layer (n-CGLg) 361 can be selected the same or different than the first n-type charge generation layer (n-CGLi) 161, and wherein the third p- type charge generation layer (p-CGLg) 362 can be selected the
  • the organic electroluminescent device 100 further comprises a fourth hole transport layer (HTL4) 441, and a fourth electron blocking layer (EBL4) 442,
  • the organic electroluminescent device 100 farther comprises a fourth emission layer (EML4) 345-
  • the organic electroluminescent device 100 farther comprises a fourth optional hole blocking layer (HBL4) 447, an electron transport layer (ETL) 148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.
  • HBL4 hole blocking layer
  • ETL electron transport layer
  • EIL electron injection layer
  • CAT cathode layer
  • a sealing layer may further be formed on the cathode electrodes 190, in order to seal the OLEDs 100.
  • various other modifications may be applied thereto.
  • the invention is furthermore illustrated by the following examples which are illustrative only and non-binding.
  • the sublimation apparatus consist of an inner glass tube consisting of bulbs with a diameter of 3 cm which are placed inside a glass tube with a diameter of 3.5 cm.
  • the sublimation apparatus is placed inside a tube oven (Creaphys DSU 05/2.1).
  • the sublimation apparatus is evacuated via a membrane pump (Pfeiffer Vacuum MVP 055- 3C) and a turbo pump (Pfeiffer Vacuum THM071 YP).
  • the pressure is measured between the sublimation apparatus and the turbo pump using a pressure gauge (Pfeiffer Vacuum PKR 251).
  • the temperature is increased in increments of 10 to 30 K till the compound starts to be deposited in the harvesting zone of the sublimation apparatus.
  • the temperature is further increased in increments of 10 to 30 K till a sublimation rate is achieved where the compound in the source is visibly depleted over 30 min to 1 hour and a substantial amount of compound has accumulated in the harvesting zone.
  • the sublimation temperature also named T M) bi, is the temperature inside the sublimation apparatus at which the compound is deposited in the harvesting zone at a visible rate and is measured in degree Celsius.
  • the term “sublimation” may refer to a transfer from solid state to gas phase or from liquid state to gas phase.
  • the decomposition temperature also named Td ec , is determined in degree C6lsius.
  • the decomposition temperature is measured by loading a sample of 9 to n mg into a Metler Toledo 100 pL aluminum pan without lid under nitrogen in a Mettler Toledo TGA-DSC imachine. The following heating program was used: 25°C isothermal for 3 min; 25°C to 6oo°C with 10 K/min.
  • the decomposition temperature was determined based on the onset of the decomposition in TGA.
  • the LUMO energy level and the dipole moment are calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Düsseldorf, Germany).
  • the optimized geometries and the HOMO and LUMP energy levels of the molecular structures are determined by applying the hybrid functional B3LYP with a 6 ⁇ 31G* basis set in the gas phase. If more than one conformation is viable, the conformation with the lowest total energy is selected.
  • a glass substrate with an anode layer comprising a first anode sub-layer of 10 nm ITO, a second anode sub-layer of 120 nm Ag and a third anode sub-layer of 8 nm ITO was cut to a size of too mm x 100 mm x 0.7 mm, ultrasonically washed with water for 60 minutes and then with isopropanol for 20 minutes.
  • the liquid film was removed in a nitrogen stream, followed by plasma treatment, see Table 12, to prepare the anode layer.
  • the plasma treatment was performed in an atmosphere comprising 97.6 voI.-% nitrogen and 2.4 voh-% oxygen.
  • N-([1,1'-bipheiiyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H- fluoren-2-amine was vacuum deposited with 2 wt.-% 2,2’ , 2"-(cyclopropane-1,2,3- triylidenc)tris(2-(p-cyanotetrafluorophenyl)acetonilrile)to form a hole injection layer havng a thickness 10 nm.
  • N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N“(4-(9-phenyl-9H-carbazol-3-yI)plienyl)-9H- fluoren-2 -amine was vacuum deposited, to form a first hole transport layer havng a thickness of 29 nm
  • N-([i,i'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenvlsilyl)phenyl)-9H-fluoren-2-amine was vacuum deposited on the HTL, to form an electron blocking layer (EBL) having a thickness of 5 nm.
  • EBL electron blocking layer
  • the first electron transporting layer (ETL1) having a thickness of 15 nm is formed on first emission layer by depositing a compound according Table 12.
  • the first electron transporting layer is free of 8-Hydroxyquinolinolato-lithium.
  • an n-type CGL having a thickness of 8 nm is formed on the ETLi by co-depositing 90.1 wt.-% of an electron transport compound (ETM of n-CGL) according to Table 12 and 9.9 wt.- % Yb.
  • ETM electron transport compound
  • a p-type CGL having a thickness of 10 nm is formed on the n-type CGL by co-depositing N-(fi,i’-bipheny!]-4-yl)-9,9-dimethj'l-N-(4-(9-phenyl-9H-carbaZol-3-yl)phenyl)-9H-fluoren- 2-amine with 10 wt% 2,2',2"-(cyclopropane-i,2,3-triylidene)tris(2-(p- cyanotetrafluorophenyl)acetonitrile) as organic p-dopant.
  • a second hole transport layer having a thickness of 45 nm is formed on the first p-type CGL by depositing N-([i,i'-biphenj'l]-4-yl)-9,9-dimetliyl-N-(4-(9-phcnyl-9H-carbazol-3- yl)phenyl)-9H-fluoren-2-amine.
  • a second electron blocking layer having a thickness of 5 nm is formed on the second hole transport layer by depositing N-([i,i'-biphenyl]-4-yl)-9,9-diphenyl-N-(4- (triphenylsilyl)phenyl)-9H-fluoren-2-amine.
  • Yb was evaporated at a rate of 0.01 to 11/s at io ⁇ 7 mbar to. form, an electron injection layer with a thickness of 1 nm on the electron transporting layer.
  • Ag/Mg (1:8 wt%) is evaporated at a rate of 0.01 to 1 A/s at io -7 mbar to form a cathode with a thickness of 13 nm.
  • N-( ⁇ [i,i-‘biphenyl]-4-yl)-9,9,dimethyl-N-(4-(g-phenyl-9H-carbazoI-3-yl)phcnyD-9H- fluoren-2 -amine ⁇ was vacuum deposited on the cathode layer to form a capping layer with a thickness of 75 nm.
  • the current efficiency is measured at 20°C.
  • the current-voltage characteristic is determined using a Keithley 2635 source measure unit, by sourcing a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device is varied in steps of 0.1V in the range between oV and 10V.
  • the luminance-voltage characteristics and CIE coordinates are determined by measuring the luminance in cd/m 2 using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Ak relie istsstelle (DAkkS)) for each of the voltage values.
  • the cd/ A efficiency at 15 mA/cma is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.
  • the emission is predominately Lambertian and quantified in percent external quantum efficiency (EQE).
  • EQE percent external quantum efficiency
  • the emission is forward directed, non-Lambertian and also highly dependent on the mircocavity. Therefore, the efficiency EQE will be higher compared to bottom emission derices.
  • the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA/cm 2 .
  • Lifetime IT of the device is measured at ambient conditions (2O°C) and 30 mA/cm 2 , using a Keithley 2400 sourcemeter, and recorded in hours.
  • the brightness of the device is measured using a calibrated photo diode.
  • the lifetime LT is defined as the time till the brightness of the device is reduced to 97 % of its initial value.
  • the increase in operating voltage AU is used as a measure of the operational voltage stability of the device. This increase is determined during the LT measurement and by subtracting the operating voltage after 1 hour after the start of operation of the device from the operating voltage after 100 hours.
  • Comparative device Ci comprises an electron transport layer contacting the n-type charge generation layer containing 8-Hydroxyquinolinolato-lithium (LiQ) and compound ET-i, and an n-type charge generation layer containing compound C-4.
  • the comparative device C2 comprises an electron transport layer contacting the n-type charge generation layer containing 8-Hydroxyquinolinolato-lithium (LiQ) and compound ET-i, and an n-type charge generation layer containing compound I-i.
  • the comparative device C3 comprises an electron transport layer contacting the n-type charge generation layer containing 8-Hydroxyquinolinolato-lithium (LiQ) and compound ET-i, and an n-type charge generation layer containing compound I- 2.
  • the comparative device C4 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-i and in contrast to comparative device Ci does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and an n-type charge generation layer containing compound ET-2.
  • the compound ET-2 contains two phenthroline groups.
  • the comparative device C5 comprises an electron transport layer contacting the n-type charge generation layer containing the compound C-2 and does not contain 8-Hydroxyquinolinolato- lithium (LiQ),, and an n-type charge generation layer containing compound C-2.
  • the compound C-2 contains a pyrazine group and a imidazo[i,5-a]pyridine group.
  • the comparative device C6 comprises an electron transport layer contacting the n-type charge generation layer containing the compound C-3 and does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and an n-type charge generation layer containing compound C-3.
  • the compound C-3 contains a dibenzoacridine group and a imidazo[i,s-a]pyridine group.
  • the comparative device Cy comprises an electron transport layer contacting the n-type charge generation layer containing the compound C-4 and does not contain 8-Hydroxyquinolmolato- lithium (LiQ), and an n-type charge generation layer containing compound C-4.
  • the compound C-4 contains a dibenzoacridinc group and a substituted imidazo[i,5-a] group.
  • the comparative device C8 comprises an electron transport layer contacting the n-type charge generation layer containing the compound C-i and the electron transport layer does not contain 8-HydroxyquinoEnolato-lithium (LiQ), and an n-type charge generation layer containing compound C-i.
  • the compound C-i contains one phenthroline group.
  • the inventive device II comprises an electron transport layer contacting the Ji-type charge generation layer containing the compound ET-i, and in contrast to comparative device Cg the electron transport layer does not contain 8-Hydroxyquinolinolato-lithtain (LiQ), and the n- type charge generation layer containing compound ET-3.
  • the compound ET-3 contains a phenthroline group and a substituted imidazo[i,5-a] group.
  • the inventive device I2 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-i, and in contrast to comparative device C3 the electron transport layer does not contain 8-Hydroxyquinolmolato-lithium (LiQ), and the n- type charge generation layer containing compound I-2.
  • the compound 1-2 contains a phenthroline group and a substituted imidazo[i,5-a] group.
  • the inventive device I3 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-2 instead of the compound ET-i according to inventive device Ii, and the electron transport layer does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
  • the inventive device I4 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-5 instead of the compound ET-i according to inventive derice Ii, and the electron transport layer does not contain 8-HydroxyquinoIinolato- lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
  • the inventive derice I5 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-4 instead of the compound ET-i according to inventive device II, and the electron transport layer does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
  • the organic electroluminescent derice comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-6 instead of the compound ET-i according to inventive device Ii, and the electron transport layer does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
  • the inventive derice I7 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-3 instead of the compound ET-i according to inventive derice II, and the electron transport layer does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
  • the inventive derice 18 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-7 instead of the compound ET-i according to inventive device U, and the electron transport layer does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and the n-hpe charge generation layer containing compound ET-3.
  • the inventive derice I9 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-i, and in contrast to comparative device C3 the electron transport layer does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and the n- type charge generation layer containing compound I-126.
  • the compound I-126 contains a phenthroline group and a substituted imidazo[i,5-a] group.
  • the inventive derice I10 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-1, and in contrast to comparative device C3 the electron transport layer does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and the n-type charge generation layer containing compound I-151.
  • the compound I-151 contains a phenthroline group and a substituted imidazo[i ; 5-a] group.
  • the inventive device In comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-i, and in contrast to comparative device C3 the electron transport layer does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and the n- type charge generation layer containing compound I-125.
  • the compound I-125 contains a phenthroline group and a substituted imidazo[i,5-a] group.
  • the inventive device I3 or I4 respectively differs from the comparative device C3 or C4, respectively in that the inventive detice I3 or Iq, respectively does not contain Hydroxyquinolinolatodithium in the electron transport layer contacting the n-type charge generation layer.
  • the inventive device II to In does not comprise Hydroxyquinolinolato-lithium in the electron transport layer contacting the n-type charge generation layer.
  • the comparative devices Ci to C5 contains Hydroxyquinolinolato-lithium in the electron transport layer contacting the n-type charge generation layer.
  • inventive devices exhibit a remarkable lower voltage rise over time compared to the comparative derices Ci to C4. At the same time the operational voltage is still low, and the current efficiency is still very high.
  • inventive device II to In and the comparative devices C5 to C9 all does not comprise Hydroxyquinolmolato-Iithium in the electron transport layer contacting the n-type charge generation layer.
  • an inventive device comprising a compound of formula (I) in the n-type charge generation layer, and an electron transport layer contacting the n-type charge generation layer which is free of Hydroxyquinolinolato-lithium exhibit a remarkable low voltage rise over time, and at the same time a low operational voltage and a high current efficiency.
  • a low operating voltage may be important for the battery life of organic electronic devices, in particular mobile deuces.
  • a high efficiency may be beneficial for reduced power consumption and improved battery life, in particular in mobile deuces.
  • a low voltage rise over time may result in improved long-term stability of electronic devices.

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Abstract

The present invention relates to an organic electroluminescent device comprising an anode layer, a cathode layer, a first emission layer, a second emission layer, a first charge generation layer, and a first electron transport layer; and to a display device comprising the same.

Description

Invention Title
Organic electroluminescent device, semiconducting material, semiconducting layer, compound, electronic device and display device
Technical Field
The present invention relates to an organic electroluminescent device, to a semiconducting material, to a semiconducting layer, to an electronic device to a compound and to a display device.
Background Art
Organic electronic devices, such as organic light-emitting diodes OLEDs, which are selfemitting devices, have a wide viewing angle, excellent contrast, quick response, high brightness, excellent operating voltage characteristics, and color reproduction. Atypical OLED comprises an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode, which are sequentially stacked on a substrate. In this regard, the HTL, the EML, and the ETL are thin films formed from organic compounds.
When a voltage is applied to the anode and the cathode, holes injected from the anode move to the EML, via the HTL, and electrons injected from the cathode move to the EML, via the ETL. The holes and electrons recombine in the EML to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted. The injection and flow of holes and electrons should be balanced, so that an OLED having the above-described structure has excellent efficiency and/ or a long lifetime.
Performance of an organic light emitting diode (organic electroluminescent device) may be affected by characteristics of an organic semiconductor layer comprised therein, and among them, may be affected by characteristics of an organic material of the organic semiconductor layer.
Particularly, development of an organic semiconductor layer arrangement being capable of improving electron transport, electron injection and electron generation properties is needed. Thereby, operating voltage in OLEDs may be reduced. Lower operating voltage is important for reduced power consumption and improved battery life, esp. of mobile devices.
Further, development of an organic electronic device with improved efficiency is needed. Increased efficiency is important for reducing power consumption and increasing battery life, for example of a mobile display device.
There remains a need to improve the performance of organic electroluminescent devices, in particular to achieve a multi-stack OLED with a low operational voltage, high efficiency and a low voltage rise over time. Furthermore, there remains a need to improve the properties of compounds for organic electronic devices, in particular to achieve a compound with suitable thermal properties for mass production under vacuum thermal conditions,
DISCLOSURE
An aspect of the present invention provides an organic electroluminescent device comprising an anode layer, a cathode layer, a first emission layer, a second emission layer, a first charge generation layer, and a first electron transport layer, wherein
- the first charge generation layer is arranged between the first emission layer and the second emission layer;
- the first electron transport layer is arranged between the first emission layer and the second emission layer;
- the first charge generation layer comprises a first n-type charge generation layer and a first p-type charge generation layer;
» the first n-type charge generation layer is closer to the anode layer than the first p-type charge generation layer and the first p-type charge generation layer is closer to the cathode layer than the first n-type charge generation layer;
- the first electron transport layer is arranged in direct contact with the first n-type charge generation layer;
- the first electron transport layer is free of 8-hydroxyquinoIinolato-lithium;
-the first n-type charge generation layer comprises a metal dopant and the metal dopant is Yb;
- the first n-type charge generation layer comprises a compound of formula (I) wherein in formula (I) - Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted Cb to C_>4 heteroaryl;
- R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C1 to G4 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C:i to C1<> branched alkyd. C3 to C1& cyclic alkyl, C3 to C16 branched alkoxy, C3 to C1& cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C», alkoxy, partially or perdeuterated C1 to C1o allyl, partially or perdeuterated Cj to C1o alkoxy, or PX(R8)a wherein. R8 is independently selected from C6 to CJ2 aryl, C3 to C12 heteroaryl, C1 to C1o alkyl, C1 to C16 alkoxy, partially or perfluorinated Ct to C1o alkyl, partially or perfluorinated C1 to C1o alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C1o alkoxy; and X1 is selected from 0, S or Se, preferably O; and
- L is selected from substituted or unsubstituted C6 to C24 aryl, substituted or unsubstituted C2 to C24 heteroaryl.
Another aspect of the present invention provides a display device comprising the organic electroluminescent dewce according to the present invention.
Another aspect of the present invention provides a compound of formula (M1) or of formula (M2) wherein in formula (M1)
- R’ to R7 are independently selected from H, D, substituted or unsubstituted C1 to C1o alkyl, substituted or unsubstituted C6 to C14 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to C1o alkoxy, Cs to C1o branched alkyl, C3 to C16 cyclic alkyfo C1 to C1o branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16, alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C1& alkyl, partially or perdeuterated C1 to C1*> alkoxy, or PX'(RKL wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, G to C1& alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C1s alkyl, partially or perfluorinated C1 to alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C18 alkoxy; and X1 is selected from 0, S or Se, preferably O; and
- RLb, RLb, Irffrand RLb are independently selected from H, D, substituted or unsubstituted C1 to CH. alkyd, substituted or unsubstituted C1 to C14 aryl or substituted or unsubstituted C1 to C14 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C* alkoxy, or PX’fRrfh wherein R8 is independently selected from C1 to Ct2 aryl, C3 to C12 heteroaryl, C1 to C18 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C1& alkyl, partially or perfluorinated C1 to C1& alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably O;
- Ar is selected from substituted or unsubstituted C1 to C24 aryl or substituted or unsubstituted C1 to C24 heteroaryl; wherein in formula (M2)
- R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C1B alkyl, substituted or unsubstituted C6 to C14 aryl or substituted or unsubstituted C1 to C14 heteroaryl, CN, halogen, F. C1 to C16 alkoxy, C1 to C1o branched alkyl, C1 to C1o cyclic alkyl, C1 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX’(R8)a wherein R8 is independently selected from C1 to C1a aryl, C3 to C1- heteroaiyl. C1 to C16 alkyl, C1 to C1& alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to CK, alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy ; and X1 is selected from 0, S or Se, preferably O; and
- Ar is selected from substituted or unsubstituted C6 to aryl or substituted or unsubstituted C1 to C24 heteroaryl;
- L is selected from substituted or unsubstituted C6 to C14 aryl, substituted or unsubstituted C to C24 heteroaryl.
Another aspect of the present invention provides a semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
Another aspect of the present invention provides a semiconducting layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (Ml) or (M2).
Another aspect of the present invention provides an electronic device comprising an semiconductor layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2). According to an embodiment of the present invention, the electronic device is an organic electronic device.
According to an embodiment, the electronic device comprises an electroluminescent device, an organic light emitting diode (OLED). a light emitting device, thin film transistor, a battery, a display device or an organic photovoltaic cell (OPV).
Another aspect of the present invention provides a display device comprising an organic electronic; device comprising a semiconductor layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
It should be noted that throughout the application and the claims any generic labeling, such as Rn, Ar or L always refer to the same moieties, unless otherwise noted.
In the present specification, when a definition is not otherwise provided, "substituted" refers to one substituted with a deuterium, C1 to C12 alkyl and Q to C12 alkoxy.
However, in the present specification “aryl substituted” refers to a substitution with one or more aryl groups, which themselves may be substituted with one or more aiyd and/or heteroaryl groups.
Correspondingly, in the present specification “heteroaryl substituted” refers to a substitution with one or more heteroaryl groups, which themselves may be substituted with one or more aryl and/or heteroaryl groups. > ,
In the present specification, when a definition is not otherwise provided, an "alkyl group" refers to a saturated aliphatic hydrocarbyl group. The alkyl group may be a C1 to C12 alkyl group. More specifically, the alkyl group may be a C1 to CM alkyl group or a C1 to C6 alkyl group. For example, a C1 to C4 alkyl group includes 1 to 4 carbons in alkyl chain, and may be selected from methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, and tert-butyl. Specific examples of the alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an iso-butyl group, a tert-butyl group, a pentyl group, a hexyl group.
The term “cycloalkyl” refers to saturated hydrocarbyl groups derived from a cycloalkane by formal abstraction of one hydrogen atom from a ring atom comprised in the corresponding cycloalkane. Examples of the cycloalkyl group maybe a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, an adamantly group and the like.
The term “hetero” is understood the way that at least one carbon atom, in a structure which may be formed by covalently bound carbon atoms, is replaced by another polyvalent atom. Preferably, the heteroatoms are selected from B, Si, N, P, 0, S; more preferably from N, P, O, S.
In the present specification, "aryl group" refers to a hydrocarbyl group which can be created by formal abstraction of one hydrogen atom from an aromatic ring in the corresponding aromatic hydrocarbon. Aromatic hydrocarbon refers to a hydrocarbon which contains at least one aromatic ring or aromatic ring system. Aromatic ring or aromatic ring system refers to a planar ring or ring system of covalently bound carbon atoms, wherein the planar ring or ring system comprises a conjugated system of delocalized electrons fulfilling Huckel’s rule. Examples of aiyl groups include monocyclic groups like phenyl or tolyl, polycyclic groups which comprise more aromatic rings linked by single bonds, like biphenylyl, and polycyclic groups comprising fused rings, like naphthyl or fluoren-2-yl.
Analogously, under heteroaryl, it is especially where suitable understood a group derived by formal abstraction of one ring hydrogen from a heterocyclic aromatic ring in a compound comprising at least one such ring.
Under heterocycloalkyl, it is especially where suitable understood a group derived by formal abstraction of one ring hydrogen from a saturated cycloalkyl ring in a compound comprising at least one such ring.
The term, “fused aryl rings” or “condensed aryl rings” is understood the way that two aryl rings are considered fused or condensed when they share at least two common spa-hybridized carbon atoms
In the present specification, the single bond refers to a direct bond.
In the context of the present invention, “different” means that the compounds do not have an identical chemical structure.
The term “free off, “does not contain”, “does not comprise” does not exdude impurities which may be present in the compounds prior to deposition. Impurities have no technical effect with respect to the object achieved by the present invention.
The term “contacting sandwiched” refers to an arrangement of three layers whereby the layer in the middle is in direct contact with the two adjacent layers.
The terms “light-absorbing layer” and “light absorption layer” are used synonymously.
The terms “light-emitting layer”, “light emission layer” and “emission layer” are used synonymously.
The terms “OLED”, “organic light-emitting diode” and “organic light-emitting device” are used synonymously. In the specification, hole characteristics refer to an ability to donate an electron to form a hole when an electric field is applied and that a hole formed in the anode may be easily injected into the emission layer and transported in the emission layer due to conductive characteristics according to a highest occupied molecular orbital (HOMO) level.
In addition, electron characteristics refer to an ability to accept an electron when an electric field is applied and that electrons formed in the cathode may be easily injected into the emission layer and transported in the emission layer due to conductive characteristics according to a lowest unoccupied molecular orbital (LUMO) level.
Advantageous Effects
It was surprisingly found that a multi-stack OLED comprising an n-type charge generation layer comprising Ytterbium as metal dopant a compound comprising a imidazo[i,5-a]pyridine group and a phenanthroline group as the host (matrix) in direct contact with a LiQ-free electron transport layer has an reduced voltage rise over time.
Especially, the use of a compound comprising a imidazofej5-alpyridine group and phenanthroline group as n-CGL matrix for Ytterbium and an LiQ-free ETL contacting directiy said n-CGL results synergistically in an improved voltage increase over time of a multi-stack OLED.
First charge generation lay er
The thickness of the first n-type charge generation layer may be in the range from 0.5 nm to 50 nm; alternatively in the range from 1 nm to about 40 nm; or alternatively in the range of 2 nm to 30 nm; or alternatively 5 nm to 15 nm.
The first charge generation layer comprises a first n-type charge generation layer and a first p- type charge generation layer. The first n-type charge generation layer comprises a compound of formula (I)
According to an embodiment, the compound of formula (I) is present in the first n-type charge generation layer in an amount of >0.1 preferably ≥1 preferably >2 wt.-X, more preferably s*3 wt.-%, more preferably >5 Wt-9Q more preferably >8 wt.-%, more preferably te2O wt.-%, more preferably >30 wt.-%, more preferably >40 more preferably >50 wt.- %, based on the total weight of the first n-type charge generation layer. According to an embodiment, the metal dopant is present in the first n-type charge generation layer in amount of 599.9 wt.-%, preferably 599 more preferably <98 more preferably <97 more preferably <95 wl.-%, more preferably <92 wt.-%, more preferably <80 wt.-%, more preferably <70 more preferably <60 wt,-%, more preferably <55 wt.- %, more preferably <50 wt.-%, based on the total weight of the first n-tjpe charge generation layer.
According to an embodiment, the compound of formula (I) is present in the first n-type charge generation layer in an amount of > 50 wt.-% to <99.9 wt.-%, preferably >50 wt.-% to <99 wt.- %, more preferably >50 wt.-% to <98 more preferably >50 wt.-% to < 97 wt-% to, based on the total weight of the first n-type charge generation layer.
According to an embodiment, the metal dopant is present in the first n-type charge generation layer in amount of >0.1 wt.-% to <50 preferably >1 wt.-% to <50 wt.-%, more preferably
22 wt.-% to <50 wt.-%, more preferably >3 wt.-% to <50 wt.-%, based on the total weight of the first n-type charge generation layer.
According to one embodiment of the present invention the first n-type charge generation layer is non-emissive.
In the context of the present specification the term "essentially non-emissive” or “non- emissive” means that the contribution of the compound or layer to the visible emission spectrum from the device is less than 10 %, preferably less than 5 % relative to the visible emission spect-um. The visible emission spectrum is an emission spectrum with a wavelength of about > 380 nm to about < 780mm.
The metal dopant in terms of the present disclosure may be a redox n-dopant. Under a redox n-dopant, it is understood a compound which, if embedded into an electron transport matrix, improves, in comparison with the neat matrix under the same physical conditions, the electronic properties of the formed organic material, in particular in terms of electron injection, electron generation and/or electron conductivity. Preferably, the redox n-dopant is non-emissive.
In the context of the present invention “embedded into an electron transport matrix” means the redox n-dopant forms a mixture with the electron transport matrix.
Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl.
According to an embodiment. Ar is selected from substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C2 to Cfe heteroaryl. According to an embodiment, Ar is selected from substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C2 to C12 heteroaryl.
According to an embodiment, Ar is selected from substituted or unsubstituted C6 to C1o aryl or substituted or unsubstituted C2 to C10 heteroaryl.
According to an embodiment, Ar is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl.
According to an embodiment, Ar is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-member ring.
According to an embodiment, Ar is selected from the group consisting of substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, and substituted or unsubstituted quinolinyl.
Ar maybe unsubstituted or substituted with one or more substituents.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl. C1 tot C16 alkoxy, C3 to CK, branched alkyl, C3 to C16 cyclic alkyl, C3 to C , 6 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C1& alkoxy, partially or perdeuterated C1 to C1& alkyl, partially or perdeuterated C1 to C16. alkoxy, PX‘(RR)a, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, •wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 allyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C1& alkyl, partially or perfluorinated C1 to C1« alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X! is selected from O, S or Se, preferably 0.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C1g aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C1 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, PX1R8)2 halogen, F or CN, wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16, alkyl, partially or perfluorinated C1 to C1(1 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X’ is selected from O, S or Se, preferably O. According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 ally‘Is C3 to C1& branched alkyl, C3 to C16 cyclic altyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C to C16 alky l, PX‘(RH).;, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein Rs is independently selected from C6 to Ca aryl, C3 to C12 heteroaiyl, C1 to CH, alkyl, C» to C16 alkoxy; partially or perfluorinated C1 to C16 alkyd, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to 0,6 alkyl, partially or perdeuterated C1 to C16 alkoxy ; and X1 is selected from O, S or Se, preferably 0.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C« alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C1& alkyl, partially or perdeuterated C1 to Cfe alkyl, PX’(R8), halogen, F or CN, wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C» to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably 0.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaiyl, C1 to C16 all^l, C3 to branched alkyl, C3 to C18 cyclic alkyl, partially or perfluorinated C1 to C16 alkyd, partially or perdeuterated C1 to C1 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to 0,8 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl, C3 to 0,6 branched alkyl, C3 to C1& cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C1, alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to Cw aryl, substituted or unsubstituted C3 to C14 heteroaiyl, C1 to C10 0lkyl, C3 to C10 branched alkyl, C3 to C10 cyclic alkyl, partially or perfluorinated C1 to C10 alkyl, partially or perdeuterated C1 to CTO alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C3 to C14 heteroaryl, C1 to C10 alkyl, C3 to C10 branched alkyl. C3 to cyclic alkyl, partially or perfluorinated C1 to C10 alkyl, partially or perdeute rated C> to C10 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D. substituted or unsubstituted Cfe to C10 axyl, substituted or unsubstituted C3 to C12 heeteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C» to C6 alkyl, partially or perdeuterated C1 to C6, alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to CJ0 aryl, substituted or unsubstituted C3 to C12 heteroaryl. C1 to C6 alkyl, Ca to C6 branched alkyl, C8 to C6 cyclic alkyl, partially or perfluorinated C! to C6 alkyl, partially or perdeuterated C3 to C6 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar , if presen t, are independently selected from D, substituted or unsubstituted C6 to CM aryl, substituted or unsubstituted C3 to C16 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C10 aryl, substituted or unsubstituted C3 to C10 heteroaryl, C3 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C3 to C4 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents 011 Ar, if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstfluted C3 to C5 heteroa ryl, C3 to C , alky l, C3 to C4 branched alkyl, C3 to C<> cyclic alkyl, partially or perfluorinated C1 to C4 alyl, partially or perdeuterated C3 to C4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar. if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl , partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN.
According to an embodiment, Ar is selected from the following Di to D19 shown in Table 1
Table 1:
In D] to D19, R9, R10 and R11 are independently selected from H, C1 to C16 alkyl, C1 to C16 alkoxy, C6 to C18 aryl, C3 to C20 heteroaryl, perfluorinated C1 to C16, alkyl, perfluorinated C1 to C16> alkoxy, wherein R9 and R19 may be linked via a single bond er a heteroatom to form a ring, wherein the asterisk denotes the binding position,
R1 to R" of formula (I)
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C1(, alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, or PX<R®)2 wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C 16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X* is selected from O, S or Se, preferably O,
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F.
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C16 aryl or substituted or unsubstituted C2 to C24 hcteroaryl, halogen, F.
According to an embodiment, R1 to R7 are independently selected from. H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, halogen. According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C2 to C18 eteroaryl, CN, halogen, Cl, F.
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C& to C18 aryl or substituted or unsubstituted C2 to C18 heteroaryl, halogen.
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to G alkyl, substituted or unsubstituted C6 to C32 aryl or substituted or unsubstituted C2 to C12 heteroaryl, CN, halogen, Cl, F.
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted Cr to G alkyl, substituted or unsubstituted G to C1a aryl or substituted or unsubstituted C2 to C1a heteroaryl, halogen.
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstiteted C1 to C4 alkyl, substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C1 to C10 heteroaryl, CN, halogen, Cl, F.
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C1 to C10 aryl or substituted or unsubstituted G to C1o heteroaryl, halogen.
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted Ct. aryl or substituted or unsubstituted C3 to C5 heteroaryl, CN, halogen, Cl, F.
According to an embodiment, R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted G aryl or substituted or unsubstituted C3 to C5 heteroaryl, halogen.
Substituents on R1 to R7 offormula fl) R1 to R7 may be independently unsubstituted or substituted with one or more substituents.
According to an embodiment, the one or more substituents on R* to R7, if present, are independently selected from D, C1 to C18 aryl, C3 to C20 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, C, to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to Ctf, branched alkoxy , C1 to C16 cyclic alkoxy, partially or perfluorinated C1 to Cn, alkyl, partially or perfluorinated C1 to C1, alkoxy, partially or perdeuterated C1 to Clh alkyl, partially or perdeuterated C1 to C16> alkoxy, halogen, F, CN or PX'(RH)2; wherein RK is independently selected from C6 to C12 an ). C3 to Ct2 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16, alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeute rated C1 to C16 alkoxy; and X1 is selected from 0, S or Se, preferably 0, According to an embodiment, the one or more substituents on R1 to R7, if present, are independently selected from D, substituted or unsubstituted C6, to C13 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C( to C16 alkyl, C3 to C16 branched alkyl, C1 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, PX'(R8)2, halogen, F or CN, wherein RH is independently selected from C(1 to C12 aryl, C3 to C2 heteroaryl, C1 to C18 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C1„ alkyl, partially or perdeuterated C1 to C M alkoxy ; and X1 is selected from 0, S or Se, preferably 0.
According to an embodiment, the one or more substituents on R1 to R7, if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted G to Go heteroaryl, C1 to C16 alkyl, C3 to C16 branched alkyl, C3 to CM cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on R* to R7, if present, are independently selected from D, substituted or unsubstituted C6 to Ct2 aryl, substituted or unsubstituted C3 to C14 heteroaryl, C1 to C10 alkyl, C3 to C10 branched alkyl, C1 to C1o cyclic alkyl, partially or perfluorinated C1 to C10 alkyl, partially or perdeuterated C1 to C1o alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on R‘ to R7, if present, are independently selected from D, substituted or unsubstituted C6 to C10 aryl, substituted or unsubstituted C3 to C1., hcteroaryl, C1 to C(! alkyl, C3 to Ct, branched alkyl, C1 to C1, cyclic alkyl, partially or perfluorinated C1 to Ch alkyd, partially or perdeuterated C1 to C1 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on R1 to R", if present, are independently selected from D, substituted or unsubstituted C6 to C1O aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, For CN. According to an embodiment, the one or more substituents on R1 to R7, if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C1 to C4 branched alkyl, C3 to G cyclic alkyl, partial!)- or perfluorinated C1 to C1 alkyd, partially or perdeuterated C1 to C1 alkyl, halogen, F or CN.
LofformulaXI)
According to an embodiment, L is selected from substituted or unsubstituted C6 to C1« aryl, substituted or unsubstituted C1 to C18 hcteroaryl. According to an embodiment, L is selected from substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C2 to C12 heteroaryl.
According to an embodiment, L is selected from substituted or unsubstituted C1 to C10 aryl or substituted or unsubstituted C2 to C1<> heteroaiyl.
According to an embodiment, L is selected from substituted or unsubstituted C6 to C10 and or substituted or unsubstituted C3 to C5 heteroaryl.
According to an embodiment, L is selected from substituted or unsubstituted C6 to C w aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein heteroaryl is a six-member ring.
According to an embodiment, L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl.
According to an embodiment, L is selected from substituted or unsubstituted phenyl and substituted or unsubstituted naphthyl.
According to an embodiment, L is selected from substituted phenyl, unsubstituted phenyl and unsubstituted naphthyl
Substitwntspn Lyri foinuilalD
L may be independently unsubstituted or substituted with one or more substituents.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, C6 to C18 aryl, C3 to C20 heteroaryl, C1 to 0^ alkyl, C( to C16 alkoxy, C3 to C16 branched alkyl, C3 to C1& cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16, cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C1o alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, halogen, F, CN or PX3(R8)2, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from C6 to C12 aryl, C3 to C1a heteroaryl, C1 to C«> alkyl, C1 to C1& alkoxy, partially or perfluorinated C1 to C1& alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably O.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C1 to C20 heteroaryl, C1 to C16, alkyl, C1 to C1-> alkoxy, C3 to C1b branched alkyl, C3 to C1t, cyclic alkyl, C3 to CK, branched alkoxy, C1 to CK, cyclic alkoxy, partially or perfluorinated C1 to C1„ alkyl, partially or perfluorinated C( to C1o alkoxy, partially or perdeuterated C-. to C1b alkyl, partialh or perdeuterated C1 to C1b alkoxy, PX1R8).^ halogen, F or CN, wherein R8 is independently selected from C1, to aryl, C3 to C12 heteroaryl, C1 to alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X* is selected from 0, S or Se, preferably O.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted Cj, to C18 aryl, substituted or unsubstituted C3 to C2O heteroaryl, Ct to C16 alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to Clft alkyl, PX‘(R8)2, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from Cg to C12 aryl, C3 to C12 heteroaiyl, C1 to C16 alkyl, Ct to C16 alkoxy, partially or perfluorinated C1 to C M alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C1&alkyl, partially or perdeuterated C1 to C16 alkoxy; and X5 is selected from Q, S or Se, preferably O.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted Cg to C18 aryl, substituted or unsubstituted C3 to C20 heteroaiyl, C1 to C16 alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated Cl ft) C16 allyl, halogen, F or
CN, wherein R8 is independently selected from C6 to C52 aryl, C3 to C12 heteroaryl, C1to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated Cj to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C1P alkoxy; and X* is selected from O, S or Se, preferably O.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted Cg to C1H ary] , substituted or unsubstituted C:! to Ca> heteroaiyl, Ct to C16 alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated Ct to C16 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted Cg to C16 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated Cito C16 alkyl, halogen. F or CN.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted Cg to C12 aryl, substituted or unsubstituted C3 to C14 heteroaryl, C1 to C10 alkyl, C3 to CM branched alkyl, C3 to C10 cyclic alkyl, partially or perfluorinated C1 to C10 alkyl, partially or perdeuterated C1 to C10 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted C6 to Cia aryl, substituted or unsubstituted C3 to C14 heteroaiyl, C1 to C10 alkyl, C3 to C10 branched alkyl, C3 to C1O cyclic allqfl, partially or perfluorinated C1 to C1, alkyl, partially or perdeuterated C1 to C1<> alkyl, halogen, F or CN. According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted Cg to C10 aryl, substituted or unsubstituted C3 to C16 heteroaryl, (A to C6 alkyl, C3 to Cg branched alkyl, C3 to Cg cyclic alkyl, partially or perfluorinated C1 to C6 alkyl, partially or perdeulcrated C1 to C1 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted Cg to C10 aryl, substituted or unsubstituted C3 to C12 heteroaryl, C1 to Cg alkyl, C3 to Cg branched alkyl, C3 to Cg cyclic alkyl, partially or perfluorinated C1 to Cg alkyl, partially or perdeuterated C1 to Cg alkyl, halogen, F or ON,
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted Cg to C1O aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to Cg cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted C1, to C1(, aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to Cg cyclic allyl, partially or perfluorinated C1 to C, alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, For CN.
According to an embodiment, the one or more substituents on L, if present, are independently selected from D, substituted or unsubstituted Cg aryl, substituted or unsubstituted C3 to Cs heteroaryl, C1 to C4 alkyd, C13 to C4 branched alky], C3 to Cg cyclic alky l, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on L, if present , are independently selected from D, substituted or unsubstituted Cg aryl, substituted or unsubstituted C3 to Cs heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to Cg cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN.
According to an embodiment, L is selected from the following moieties E1 to E33 shown in Table 2a.
According to an embodiment, L is selected from the following moieties E1 to E34 shown in Table 2a.
Table aa:
wherein in E1 to E34
X2 is selected from O or S, preferably O;
R1-- and R,:< are independently selected from H, C1 to C16 alkyl. C1 to C16 alkoxy, Q, to C18 aryl, C3 to C20 heteroaryl, perfluorinated C1 to C16 alkyl, perfluorinated C1 to C16 alkoxy; and the asterisk denotes the binding position.
According to an embodiment, L is selected from the following moieties E1 to E33 shown in
Table 2b. wherein in E1 to E33
X2 is selected from 0 or S, preferably 0;
R12 and R‘13 are independently selected from H, C1 to C16 alkyl. C1 to C16 alkoxy, C6 to C18 aryl, C3 to C20 heteroaryl, perfluorinated C1 to C16 alfcfl, perfluorinated C1 to C16 alkoxy; and the asterisk “ " denotes the binding position.
According to an embodiment, L is selected from the moieties E1 to E30. According to an embodiment, L is selected from the moieties E1 to E24.
According to an embodiment, L is selected from the moieties E1 to E23.
According to an embodiment, L is selected from the moieties E1 to E5, and E8 to E23.
According to an embodiment, L is selected from the moieties Ei to E5, E8 to E13 and E16.
According to an embodiment, L is selected from the moieties E1 to E5, E11 and E16.
According to an embodiment, L is selected from the moieties E1 to E5 and E16.
According to an embodiment, L is selected from the moieties E1 to Eg, Eu and E16.
According to an embodiment, L is selected from the moieties E2 to E3, E11 and E16.
According to an embodiment, L is selected from the moieties E2 to E3 and E16.
Properties of the compound of formula (I)
According to an embodiment, the compound of formula (I) has a LUMO energy level when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase < -1.3 eV, preferably < -1.35 eV, and more preferably of < -1,4 eV..
According to an embodiment, the compound of formula (I) has a LUMO energy level when calculated with the program package TURBOMOLE V6.5 (TURBO MOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase of > -2.5 eV, preferably of > -2.0 eV, more preferably > -1.9 eV, even more preferably^ -1.85 eV, and most preferably > -1.8 eV.
According to an embodiment, the compound of formula (I) has a LUMO energy level when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE C1mbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31C1* basis set in the gas phase in the range of > -2.5 eV and < -1.3 eV, preferably of > -2.0 eV to < -1.35 eV, more preferably > -1.9 eV to < -1.4 eV, even more preferably > -1.85 eV to < -1.4 eV and most preferably a -1.8 eV to s -1.4 eV.
According to an embodimerrt , the compound of formula (I) has a molecular weight in the range of ≥400 g/mol to <2000 g/mol, preferably 2415 g/mol to S1500 g/mol, more preferably 3:430 g/mol to <1000 g/mol, and most preferably >440 g/mol to <900 g/mol.
Specific embodiments of the compound of formula (I) According to an embodiment, in formula (I) R* to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C1, to C1H aryl, substituted or unsifostituted Ca to C18 heteroaryl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C(1 to Cfo aryl, substituted or unsubstituted Ca to C18 heteroaryl; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independentlyselected from H, or D; L is selected from substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted Ca to C18 heteroaryl; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C1> to C18 aryl, substituted or unsubstituted C3 to C16 heteroaryl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2- quinoline group or an unsubstituted phenyl.
According to an embodiment, in formula (I) R* to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted Ct, to (fo aryl or substituted or unsubstituted Ca to C12 heteroaryl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C1, to Cla aryl or substituted or unsubstituted Ca to (to heteroaryl; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to (to aryl or substituted or unsubstituted Ca to C12 heteroaryl; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C2 to C12 heteroaryl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2- quinoline group or an unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C2 to C10 heteroaryl.
According to an embodiment, in formula (I) R1 to R" are independently selected from H, or D;
L is selected from substituted or unsubstituted C6 to C16 aryl or substituted or unsubstituted CL to C10 heteroaryl; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 arc independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C2 to CK) heteroaryl; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C2 to C10 heteroaryl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2- quinoline group or an unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; Lis selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl.
According to an embodiment, in formula (I) R‘ to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C* aryl or substituted or unsubstituted C3 to C5 heteroaryl; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C<, aryl or substituted or unsubstituted C3 to C5 heteroaryl; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; Lis selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl' Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2- quinoline group or an unsubstituted phenyl.
According to an embodiment, in formula (I) R’ to R7 are independently selected from H, or D; Lis selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein heteroaryl is a six-member ring.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted Ch aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein heteroaryl is a six-member ring; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C(, aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein heteroaryl is a six-member ring; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted Cb ary] or substituted or unsubstituted C3 to C5 heteroaryl, wherein heteroaryl is a six-member ring; Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, orb; L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, pjTazinyl, pyrimidyl, triazinyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl; Ar is selected from a substituted or unsubstituted 2- pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (1) R' to R’ are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (T) R1 to R" are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl; Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl. According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D;
L is selected from E1 to E5, and E8 to E23.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R‘ to R7 are independently selected from H, or D; L is selected from E1 to Eg, and E8 to E23; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from Ea, E3, E8, Eg, Eu, E14 and E15; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from Ez, E3, E8, Eg, Eu, E14 and E15; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R* to R7 are independently selected from H, or D; L is selected from E2, E3, E8, E9, Eu, E14 and E15; Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from E2 to E3, and E1i.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D; L is selected from E2 to E3, and E1i; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R7 are independently selected from H, or D;
L is selected from E2 to E3, and E1l; Ar is selected from a substituted or unsubstituted 2- pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formula (I) R1 to R” are independently selected from H, or D; L is selected from E2 to E3. and E11; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, the compound of formula (I) is selected from the compound of formula (II) wherein
Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted
C2 to C24 heteroaryl,
R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C1 alkyl, substituted or unsubstituted C6, to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to (fo alkoxy, C3 to C16 branched alkyl, C3 to C16, cyclic alkyl , C3 to C1(, branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PXrfRbfr wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16, alkyl, C1 to CK alkoxy, partially or perfluorinated C1 to CK alky l, partially or perfluorinated C1 to CK alkoxy, partially or perdeuterated C1 to CK alkyl, partially or perdeuterated C1 to CK alkoxy; and X1 is selected from O, S or Se, preferably O; wherein formula (II) can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formula (I) is selected from the compound of formula (III) wherein Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2to C24 heteroaryl; wherein formula (III) can be undeuterated, partially deuterated or folly deuterated.
According to an embodiment, the compound of formula (I) is selected from the compound of formula (IVa) or (IVb)
Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl; wherein formula (IVa) or (IVb) can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formula (I) is selected from the compound of formula (Va). (Vb). (Vc) or (Vd)
wherien
R15 and R16 are independently of each other selected from H, D, substituted or unsubstituted C1 to C1g alkyl, substituted or unsubstituted C® to C24 aryl or substituted or unsubstituted G to C24 heteroaryl, CN. halogen. F, C1 to C1® alkoxy, C3 to branched alkyl, C3 to C1® cyclic alkyl, C3 to C16 branched alkoxy, C3 to C1® cyclic alkoxy, partially or perfluorinated C1 to C1® alkyl, partially or perfluorinated C1 to C1® alkoxy, partially or perdeuterated C1 to C1® alkyl, partially or perdeuterated C1 to C1® alkoxy, or PX*(R8)-, wherein R8 is independently selected from C1, to Ce aryl, G to C12 heteroaryl, C1 to C1® alkyl, C1 to C1® alkoxy, partially or perfluorinated C1 to C1® alkyl, partially or perfluorinated C1 to C1® alkoxy, partially or perdeuterated C1 to C1® alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from 0, S or Se, preferably 0; wherein formula (Va) to (Vd) can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the one more substituents on R15 an d R’6, if present, are independently selected from D, C® to C18 aryl, C3 to C20 heteroaryl, C1 to C1® alkyl, C1 to Cm alkoxy, C3 to C* branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C1® cyclic alkoxy, partially or perfluorinated C1 to C1® alkyl, partially or perfluorinated C1 to C1® alkoxy, partially or perdeuterated C1 to C1® alkyl, partially or perdeuterated C1 to C1® alkoxy, halogen, F, CN or PX1(R8)2, wherein R8 is independently selected from C1> to C1a aryl, C3 to CJ2 heteroaryl, C1 to C1® alkyl, C1 to C1® alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C1® alkoxy, partially or perdeuterated C1 to C1® alkyl, partially or perdeuterated C1 to C1® alkoxy; and X* is selected from 0, S or Se, preferably O,
According to an embodiment, wherein one or more substituents on R15 to R*6, if present, are independently selected from D, substituted or unsubstituted C® to C18 aryl, substituted or unsubstituted C3 to C2O heteroaryl, C1 to C16 alkyl, C3 to C1® branched alkyl, C3 to C1® cyclic alkyl, partially or perfluorinated Ct to C1® alkyl, partially or perdeuterated C1 to C1® alkyl, PX«(RS)2, halogen, F or CN, wherein R® is independently selected from C® to C12 aryl, C3 to C12 heteroaryl , C1 to C1® alkyl, C1 to^ C1® alkojy, partially or perfluorinated C1 to C1® allyl, partially or perfluorinated Ct to C1® alkoxy, partially or perdeuterated C1 to C1® allyl, partially or perdeuterated C1 to C1® alkoxy; and X1 is selected from 0, S or Se, preferably O.
According to an embodiment, wherein one or more substituents on R1 to R16, if present, are independently selected from D, substituted or unsubstituted C® to C18 aryl, substituted or unsubstituted C3 to C2() heteroaryl, C1 to CKJ alkyl, C3 to C16 branched alkyl, C3 to C16, cyclic alkyl, partially or perfluorinated C1 to C1a alkyl, partially or perdeuterated C1 to C1(, alkyl , halogen, F or CN.
According to an embodiment, wherein one or more substituents on R’5 to R16, if present, are independently selected from D, substituted or unsubstituted C6 to Cffl aryl, substituted or unsubstituted C3 to C14 heteroaryl, Q to C1O alkyl, C3 to C10 branched alkyl, G3 to C10 cyclic alkyl, partially or perfluorinated Octo C10 alkyl, partially or perdeuterated C1 to C10, alkyd, halogen, F or CN.
According to an embodiment, wherein one or more substituents on R’s to R16, if present, are independently selected from D, substituted or unsubstituted C6 to CI0 aryl, substituted or unsubstituted C3 to C12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkyl, halogen, For CN.
According to an embodiment, wherein one or more substituents on R3s to R16, if present, are independently selected from D, substituted or unsubstituted C6 to C!fi aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to C4 allyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 allyl, halogen, F or CN.
According to an embodiment, wherein one or more substituents on Rn to R’6, if present, are independently selected from D, substituted or unsubstituted Ct, aryl, substituted or unsubstituted C3 to Cs heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to Cfo cyclic alkyd, partially or perfluorinated C1 to C4 alkyd, partially or perdeuterated C: to C4 alkyl, halogen, F or CN.
According to an embodiment, the compound of formula (I) is selected from the compound of formula (Afra), (Aflb) , (Vic) or (Wd):
R’s and R16 are independently of each other selected from wherein formula (Via) or (Vid) can be undeuterated, partially deuterated or fully deuterated.
The compound of formula (I) may be selected from the following compounds I-i to I-298 shown in Table 3.
Table 3:
wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
The compound of formula (I) may be selected from the following compounds I-i to I-150, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formula (I) is selected from the compounds shown in Table 4.
Table 4:
wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formula (I) is selected from the compounds shown in Table 5.
Table 5 wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formula (I) is selected from the compounds shown in Table 6.
Table 6: wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formula (I) is selected from the compounds shown in Table 7.
Table 7: wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formula (I) is selected from the compounds shown in Table 7b.
Table 7b:
wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
Table 8: wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
Erst electron transport layer
According to an embodiment, the first electron transport layer is in direct contact with the first emission layer.
According to an embodiment, the first electron transport layer is closer to the anode layer than any other electron transport layer within the organic electroluminescent device. According to an embodiment, the first electron transport layer which is in direct contact with the first n-type charge generation layer is the electron transport layer closest to the anode layer.
According to an embodiment, the first electron transport layer is arranged between the first emission layer and the first charge generation layer.
The thickness of the first electron transport layer may be in the range from 0.5 nm to 50 nm; alternatively in the range from 1 nm to about 40 nm; or alternatively in the range of 2 nm to 30 nm.
According to one embodiment of the present invention the first electron tr ansport layer is non- emissive.
In the context of the present specification the term “essentially non-emissive” or “non- emissive” means that the contribution of the compound or layer to the visible emission spectrum from the device is less than 10 %, preferably less than 5 % relative to the visible emission spectrum. The visible emission spectrum is an emission spectrum with a wavelength of about a 380 nm to about < 780 nm.
The first electron transport layer is free of 8-hydroxyquinolinolato-lithium.
According to an embodiment, the first electron transport layer is free of a lithium metal complex.
According to an embodiment, the first electron transport layer is free of a metal complex.
According to one embodiment, the first electron transport layer comprises an electron transport compound.
The electron transport compound may ha ve a molecular weight in the range of >400 g/mol to ≤2000 g/mol, preferably >415 g/mol to <1500 g/mol, more preferably >430 g/mol to <1000 g/mol, and most preferably 2440 g/mol to <900 g/mol.
According to an embodiment, the first electron transport layer comprises an electron transport compound, wherein the electron transport compound comprises 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings, and optionally 9 aromatic or heteroaromatic rings, wherein one or more of the aromatic or heteroaromatic rings may be substituted with Cl to C4 alkyl. In this regard, an aromatic, respectively heteroaromatic ring is a single aromatic ring, for example a 6-membered aromatic ring such as phenyl, a 6-membered heteroaromatic ring such as pyridyl, a 5-membered heteroaromatic ring such as pyrrolyl etc. In a system of condensed (hetero)aromatic rings, each ring is considered as a single ring in this regard. For example, naphthalene comprises two aromatic rings.
The electron transport compound may comprise at least one heteroaromatic ring, optionally 1 to 5 heteroaromatic rings, optionally 1 to 4 heteroaromatic rings, optionally 1 to 3 heteroaromatic rings, and optionally 1 or 2 heteroaromatic rings.
The aromatic or heteroaromatic rings of the electron transport compound may be 6-membered rings.
The heteroaromatic rings of the electron transport compound may be a N-containing heteroaromatic ring, optionally all of the heteroaromatic rings are N-containing heteroaromatic rings, optionally all of the heteroaromatic rings heteroaromatic rings contain N as the only type of heteroatom.
The electron transport compound may comprise at least one six-member heteroaromatic ring containing one to three N-atoms in each heteroaromatic ring, optionally one to three 6- membered heteroaromatic rings containing one to three N-atoms in each heteroaromatic ring, respectively.
The at least one 6-membered heteroaromatic ring comprised in the electron transport compound may be an azine. The at least one 6-membered heteroaromatic ring comprised in the electron transport compound may be triazine, diazine, pyrazine, pyrimidine pyridine preferably triazine.
If the electron transport compound comprises two or more heteroaromatic rings, the heteroaromatic rings may be separated from each other by at least on aromatic ring which is free of a heteroatom.
In an embodiment, the heteroatoms in the heteroaromatic rings of the electron transport compound are bound into the molecular structure of the electron transport compound by at least one double bond.
According to an embodiment, wherein the compound comprising at least one nitrogen atom in a six-member aromatic ring in the electron transport layer is selected from formula (xxa) or formula (xxb) shown in Table 9.
Table 9: wherein Ar1 is a substituted or unsubstituted C3 to C40 heteroaromatic ring system comprising at least one nitrogen atom, wherein Ar” is substituted or unsubstituted C3 to C40 heteroaromatic ring system comprising at least one nitrogen atom, wherein the substituents on Ari and Arn are, identically or differently on each occurrence, D, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals Ra; wherein ArIa, Arlb, Arlc, ArIla, and Arnb are, identically or differently on each occurrence, H, D, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R8; wherein at least one of Aria, Arlb, ArIe in formula (xxa) and in case of formula (xxb) at least one of
Ari®, ArIb, Ar,Ia, and Arnb is independently selected from a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals Ra; wherein Arids a divalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals Ra; wherein Ra is on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Rb)2, N(Ar,s)2, B(Ar“)a, C(=O)Arls, P(=Y)(RC)2, SOO)Arls, S(=O)aArls, CRb=CRbAr“, ON, NO2, Si(Rb)3, B(ORb)a, BCR^a, B(N(RI>)2)2, OSO2Rh, a substituted or unsubstituted straight-chain Ci to C20 alkyl, a substituted or unsubstitutedstraight-chain G, to C2O alkenyl, a substituted or unsubstituted straight-chain Cj to C20 alkynyl, a substituted or unsubstituted straight-chain C1 to Cao alkoxy, a substituted or unsubstituted straight-chain C1 to C2O thioalkoxy, substituted or unsubstituted branched C3 to C20 alkyl, a substituted or unsubstituted branched C3 to C20 alkenyl, a substituted or unsubstituted branched C3 to CM a substituted or unsubstituted branched C3 to C2() alkynyl, a substituted or unsubstituted branched C3 to C20 alkoxy or a substituted or unsubstituted C , to C20 branched thioalkoxy, substituted or unsubstituted cyclic C3 to C40 alkyl, substituted or unsubstituted cyclic C3 to C40 alkenyl, substituted or unsubstituted cyclic C3 to C41) alkinyl, substituted or unsubstituted cyclic C3 to C40 alkoxy or substituted or unsubstituted cyclic C3 to C4O thioalkoxy;substituted or unsubstituted heterocyclic C3 to C40, alkyl, substituted or unsubstituted heterocyclic C3 to C40, alkenyl, substituted or unsubstituted heterocyclic C3 to C40 alkynyl, substituted or unsubstituted heterocycMc C3 to (fro alkoxy or substituted or unsubstituted heterocyclic C3 to C4<. thioalkoxy; wherein the one or more substituents, if present, is selected from Rb, where one or more non- adjaccnt CH., groups is optionally replaced by R’C=CRfl, C=C1 Si(Rh)a, Ge(R!’)2, Sn(Rb)2, C=O, C=S, C=Se, C=NRb, P(=O)(Rh), SO, S02, NRb, 0, S or C0NRh and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NOa, or an aromatic or heteroaromatic ring system hating 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals Rfr or an aryloxy or heteroaiyloxy group hating 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals Rb, or a combination of these systems; two or more adjacent substituents R3 here optionally forms a mono- or polycyclic, aliphatic or aromatic ringsystem with one another; wherein Ar,s is on each occurrence, identically or differently, an aromatic or heteroaromatic ring system hating 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals Rb; two radicals Ar 18 here which are bonded to the same nitrogen, phosphorus or boron atom may also be linked to one another by a single bond or a bridge selected from B(Rb), C(Rs)a, Si(Rb)2, C=0, C=NRb, C=C(Rb)2, 0, S, S=0, S02, N(Rb), P(Rb) and P(=W; wherein Rh is on each occurrence, identically or differently, H, D or a C1 to Cfe aliphatic hydrocarbyl, a Cj to Cso aryl and/or C1 to C20 heteroaryl, in which, in addition, H atoms is optionally replaced by Dor F; two or more adjacent substituents Rbhere may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; wherein Y is selected from 0, S or Se, preferably 0, and Rc is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to Cft alkyl, C1 to (fr alkoxy, partially or perfluorinated C> to C6 alkyl, partially or perfluorinated Cj to C<, alkoxy, partially or perdeuterated C1 to Cft alkyd, partially or perdeuterated C1 to C* alkoxy;
For the purposes of this invention, an aromatic or heteroaromatic ring system is intended to be taken to mean a system which does not necessarily contain only one aryl or one heteroaryl group or only aryl or heteroaryl groups, but instead in which a plurality of aryl or heteroaryl groups may also be interrupted by a short non-aromatic unit (preferably less than 10 percent of the atoms other than H), such as, for example, an spa-hybridised C1 N or O atom. Thus, for example, systems such as 9, 9 '-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, benzophenone, etc., are also intended to be taken to mean aromatic ring systems for the purposes of this invention. Likewise, an aromatic or heteroaromatic ring system is taken to mean systems in which a plurality of aryl or heteroaryl groups are linked to one another by single bonds, for example biphenyl, terphenyl or bipyridine.
According to one embodiment, Ar1 is selected from pyrazine, pyridine, pyrimidine, or triazine, phenanthroline.
According to one embodiment, Ar" is selected from pyrazine, pyridine, pyrimidine, or triazine, phenanthroline. According to one embodiment, Ar1 in formula (xxa) or (xxxa) is selected from pyrazine, pyridine, pyrimidine, triazine, phenanthroline; or Ar1 in formula (xxa) or (xxxa) and Ar11 in formula (xxb) or (xxxb) are independently of each other selected from pyrazine, pyridine, pyrimidine, triazine, or phenanthroline.
According to an embodiment, wherein the compound comprising at least one nitrogen atom in a six-member aromatic ring in the electron transport layer is selected from formula (xxxa) or formula (xxxb): wherein
ZIa is selected from N or CH,
Z,b is selected from N or CH,
Z,c is selected from N or CH,
ZIla is selected from N or CH,
Z!lb is selected from N or CH, and
ZI1C is selected from N or CH, wherein in formula (XXxa) at least one of Zla, Z,b and Z'c is selected from N, wherein in formula (XXxb) at least one of ZIa, Zib, Z,c, Zila, ZIIb, and Zllc is selected from N, wherein ArIa, ArIb, Arlc, ArIIa and ArIIb are identically or differently on each occurrence, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals Ra; wherein ArHs a divalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R®, wherein RHs on each occurrence, identically or differently, H, D, F, Cl, Br, I, CHO, N(Rb)2, NfAr'fo, B(Ar1s C(=O)Ar‘y P(=Y)(R<fo, S(=O)fry SfoOWy CRb=CRbAr'\ CN, NO., Si(Rb)3, B(ORh)., B(Rb)_>, B(N(Rb)2), OSO.R1’, a substituted or unsuhstituted straight-chain C1 to C20 alkyl, a substituted or unsubstitutedstraight-chain C1 to C20 alkenyl, a substituted or unsubstituted straight-chain C1 to Cfo, alkynyl, a substituted or unsubstituted straight-chain C1 to C20 alkoxy, a substituted or unsubstituted straight-chain C1 to C20 thioalkoxy, substituted or unsubstituted branched C3 to C20 alkyl, a substituted or unsubstituted branched C3 to C20 alkenyl, a substituted or unsubstituted branched C3 to C20 a substituted or unsubstituted branched C3 to C2I) alkynyl, a substituted or unsubstituted branched C3 to C20 alkoxy or a substituted or unsubstituted branched C3 to C20 thioalkoxy, substituted or unsubstituted cyclic C3 to C40 alkyl, substituted or unsubstituted cyclic C3 to C40 alkenyl, substituted or unsubstituted cyclic C3 to C4O alkinyl, substituted or unsubstituted cyclic C:1 to C.u> alkoxy or substituted or unsubstituted cyclic C;! to C4(> thioalkoxy;substituted or unsubstituted heterocyclic C3 to C4O alkyl, substituted or unsubstituted heterocyclic C3 to C40 alkenyl, substituted or unsubstituted heterocyclic C3 to C40 alkynyl, substituted or unsubstituted heterocyclic C3 to C4O alkoxy or substituted or unsubstituted heterocyclic C3 to C4O thioalkoxy; wherein the one or more substituents, if present, is selected from Rb, where one or more non- adjacent CH2 groups is optionally replaced by RbC=CRb, OC1 Si(Rb)2, C16(Rb)2, Sn(Rb)2j C=0, C=S, C=Se, C=NRb, P(=O)(Rb), SO, S02, NRb, 0, S or CONR1* and where one or more H atoms is optionally replaced by D, F, Cl, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals R6, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals Rb, or a combination of these systems; two or more adjacent substituents Ra here optionally forms a mono- or polycyclic, aliphatic or aromatic ring system with one another; wherein Ar'tis on each occurrence, identically or differently, an aromatic or heteroaromatic ring system hating 5 to 30 aromatic ring atoms, which is optionally substituted by one or more radicals Rb; two radicals Arohere which are bonded to the same nitrogen, phosphorus or boron atom may also be linked to one another by a single bond or a bridge selected from B(Rb), C(Rb)a, Si(Rb)a, C=0, CteNRh, C=C(Rbk O, S, S=0, S02, N(Rb), P(Rb) and P(=Y)fo; wherein Rb is on each occurrence, identically or differently, H, D or a C1 to C2O aliphatic hydrocarbyl, a C1 to C20 aryl and/or C1 to C20 heteroaryl, in which, in addition, H atoms is optionally replaced by D or F; two or more adjacent substituents Rb here may also form a mono- or polycyclic, aliphatic or aromatic ring system with one another; wherein Y is selected from O, S or Se, preferably 0, and Rc is independently selected from C6 to C12 aryl, C3 to Ci2 heteroaryl, C1 to Cg alkyl, G, to C* alkoxy, partially or perfluorinated Ct to Cfi alkyl, partially or perfluorinated C1 to C6 alkoxy, partially or perdeuterated C1 to Ct, alkyl, partially or perdeuterated C1 to C6 alkoxy.
For the purposes of this invention, an aromatic or heteroaromatic ring system is intended to be taken to mean a system which does not necessarily contain only aryl or heteroaryl groups, but instead in which a plurality of aryl or heteroaryl groups may also be interrupted by a short non-aromatic unit (preferably less than 10 percent of the atoms other than H), such as, for example, an spMiybridised C1 X or O atom. Thus, for example, systems such as 9,9'- spirobifluorene, 9,9-diarylfluorenc, triaiylaminc, diaryl ether, stilbene, benzophenone, etc., are also intended to be taken to mean aromatic ring systems for the purposes of this invention. Likewise, an aromatic or heteroaromatic ring system is taken to mean systems in which a plurality of aryl or heteroaryl groups are linked to one another by single bonds, for example biphenyl, terphenyl or bipyridine.
According to an embodiment, the first electron transport layer comprises an electron transport compound, wherein the electron transport compound is selected from 2-([isi'-biphcnyl]-3-yl)- 4-(2',6'-diphenyl-[j,i,:4']i"rterphenyl]-4-yl)-6-phcnyl-i,3,5-triazineJ 2,2’-(1,3-
Phenylene)bis[g-phenyl-i,io-phenanthroline], 2-(4-(i-(pyridin-2-yl)imidazo[i,5-a]pyTidin-3- yl)phenyl)-i,io-phenanthrolines 3-(3-(9,iO“diphenylanthracen-2-yl)phenyl)-i-(pyridin-2- yl)im.idazo[i,s-a]pyridine, 2,4-diphenyl-6-(3"-(3,5,6-triphenylpyrazin-2-yl)-[i,i,:3',i”- terphenyl]-3-yl)-i,3,5-triazine, 2-(3'-(9,9-dimethyl-9H-fluoren-2--yl)-[i,i’“biphenyl]-3-yl)- 4,6-diphenyI-i,3>5-triazine, 2,4-diphenyl-6-(4',5’,6'-tripheiiyl-[l,i’:2',l'':3'’,i''':3'",i"'’- quinquephenyl]-3""-yl)-i}3,5-triazine; 2-phenyl-4-(3-(pyridin-4-yl)phenyl)-6-(3-(3,5,6- triphenylpyrazin-2-yl)phenyl)pyrimidine; (3-(10-(3-(2,6“diphenylpyrimidin-4- yl)phenyl)anthracen-9-yl)phenyl)dimethylphosphine . oxide.
According to one embodiment, wherein the electron transport compound has a LUMO energy level when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by apphing the hybrid functional B3LYP with a 6-31G" basis set in the gas phase of < -1.50 eV, preferably < -1.55 eV, preferably < -1.60 eV, and most preferably < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a LUMO energy lex-el when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase in the range of £ -2.5 eV to < -1.5 eV, preferably £ -2.0 eV to < -1.5 eV, more preferably > -1.95 eV to ≤ -1.55 eV, even more preferably > -1.90 eV to < -1.6 eV, even more preferably ≥ -1.90 eV to ≤ -1.65 eV, and most preferably > -1.87 eV to < - 1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to < 4.0 D; alternatively > o D to < 3.7 D; alternatively > o D to < 3.5 D; alternatively a o D to < 3.0 D; alternatively > o D to < 2.7 D; alternatively > o D to < 2.5 D; alternatively > o D to < 2.0 D; alternatively > o D to < 1.5 D; alternatively > o D to < 1.0 D.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to s 3.7 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6"3iG* basis set in the gas phase is in the range of £ -1.90 eV and s -1.65 eV. According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of a o D to <3.7 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated uith the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV and < -1.65 eV,
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to < 3.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.90 eV and < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of a o D to < 3.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH. Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV to < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to < 3.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, C1ermany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.90 eV and < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of a o D to < 3.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated ■with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of a -1.87 eV to < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of > 0 D to < 2.7 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of 2 -1.90 eV and < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of 20 D to < 2.7 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, C16rmany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV to < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of 2 o D to < 2.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYF with a 6-31G* basis set in the gas phase is in the range of 2 -1.90 eV and < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of 2 o D to < 2.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, C16rmany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of 2 -1.87 eV to s -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of 20 D to < 2.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, C16rmany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.90 eV and < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of 2 o D to < 2.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE C1mbH, Litzenhardtstrasse 19, 76135 Karlsruhe, C16rmany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of 2 -1.87 eV to < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > 0 D to s 1.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LXP with a 6-31G 1 basis set in the gas phase is in the range of > -1.90 eV and < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > o D to < 1.5 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV to < -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31C1* basis set in the gas phase in the range of > 0 D to s 1.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of a -1.90 eV and -s -1.65 eV.
According to an embodiment, wherein the electron transport compound has a molecular dipole moment calculated by the TURBOMOLE V6.5 program package using hybrid functional B3LYP and Gaussian 6-31G* basis set in the gas phase in the range of > 0 D to < 1.0 D; and the LUMO energy level of the electron transport compound of the first electron transport layer when calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase is in the range of > -1.87 eV to < -1.65 eV.
The unit for the dipole moment “Debye” is abbreviated with the symbol “D”. In this regard, the dipole moment |/z| of a molecule containing N atoms is given by: where qt and rt are the partial charge and position of atom i in the molecule. The dipole moment is determined by a semi-empirical molecular orbital method. The geometries of the molecular structures are optimized using the hybrid functional B3LYP with the 6-31G ; basis set in the gas phase as implemented in the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). If more than one conformation is viable, the conformation with the lowest total energy is selected to determine the bond lengths of the molecules.
Further electron transport layers (not the first electron transport layer)
The organic electroluminescent device according to the invention may comprise besides the first electron transport layer one or more further electron transport layer. Such a further electron transport layer does not have to be free of 8-Hydroxyquinolinolato-lithium. In particular, a further electron transport layer which is closest to the cathode preferably contains 8-Hydroxyquinolinolato-lithium, i.e. the electron transport layer which is not interrelated to a charge generation layer.
In accordance with one preferred embodiment of the invention, the electron transport layer may be the inventive organic semiconductor layer comprising the inventive compound represented by the general Formula (I) as defined herein.
According to various embodiments the OLED may comprise an electron transport layer or a n electron transport layer stack comprising at least a first electron transport layer and at least a second electron transport layer.
By suitably adjusting energy levels of particular layers of the ETL, the injection and transport of the electrons may be controlled, and the holes may be efficiently blocked. Thus, the OLED may have long lifetime.
The one or more further electron transport layer(s) of the organic electroluminescent device may comprise the compound represented by general formula (xxxa) or formula (xxxb) as defined above as the organic electron transport matrix (ETM) material. The electron transport layer may comprise, besides or instead of the compound represented by the general Formula (I), further ETM materials known in the art. Likewise, the electron transport layer may comprise as the only electron transport matrix material the compound represented by general Formula (I). In case that the inventive organic electronic device comprises more than one electron transport layers, the compound represented by the general Formula (I) may be comprised in only one of the electron transport layers, in more than one of the electron transport layers or in all of th e electron transport layers. In accordance with the invention, the electron transport layer may comprise, besides the ETM material, at least one additive as defined below.
Further, the electron transport layer may comprise one or more n-tipe dopants. The additive may be an n-type dopant. The additive can be alkali metal, alkali metal compound, alkaline earth metal, alkaline earth metal compound, transition metal, transition metal compound or a rare earth metal. In another embodiment, the metal can be one selected from a group consisting of Li, Na, K, Rb, C6, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. In another embodiment, the t-type dopant can be one selected from a group consisting of C6, K, Rb, Mg, Na, Ca, Sr, Eu and Yb. In an embodiment the alkali metal compound may be 8- Hydroxyquinolinolato-lithium (LiQ), Lithium tetra(iH-pyrazol-i-yl)borate or Lithium 2- (diphenylphosphoiyl)phenolate. Suitable compounds for the ETM (which may be used in addition to the inventive compound represented by the general Formula (I) as defined above) are not particularly limited. In one embodiment, the electron transport matrix compounds consist of covalently bound atoms. Preferably, the electron transport matrix compound comprises a conjugated system of at least 6, more preferably of at least to delocalized electrons. In one embodiment, the conjugated system of delocalized electrons may be comprised in aromatic or heteroaromatic structural moieties, as disclosed e.g. in documents EP 1 970 371 Al or WO 2013/079217 Ai.
Specific embodiments of the organic electroluminescent device according to the invention
According to an embodiment, wherein an organic electroluminescent device is provide, comprising an anode layer, a cathode layer, a first emission layer and a second emission layer, a first charge generation layer , a first electron transport layer, wherein the first charge generation layer is arranged between the first emission layer and the second emission layer, wherein the first charge generation layer comprises a first n-type ch arge generation layer and a firstp-type charge generation layer, wherein the first n-type charge generation layer is doser to the anode layer than the first p- type charge generation layer, wherein the first p-tvpe charge generation layer is closer to the cathode layer than the first n- type charge generation layer, wherein the first electron transport layer is arranged in direct contact with the first n-type charge generation layer, and wherein the first n-type charge generation layer comprises a metal dopant and a compound of formula (I)
Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, wherein one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C16 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl, Cito C1c alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C1© branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, PX'(R8)2, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X" is selected from 0, S or Se, preferably O,
R* to R7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C© to C24 aryl or substituted or unsubstitated C2 to C24 heteroaryl, CN, halogen, F C1 to C16 alkyl. C1 to C16 alkoxy, C3 to C16 branched alkyl, C, to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl , partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX1(R8)a wherein R8 is independently selected from C© to Ca aryl, C3 to C)2 heteroaiyl, C to C16 alkyl, C to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C1(, alkoxy; and X1 is selected from 0, S or Se, preferably O, wherein one or more substituents on R' to R7, if present, are independently selected from D, C© to C16 aryl, C3 to C2O heteroaryl, C to C16 alkyl, C to C16 alkoxy, C3 to C!6 branched alkyl, C3 to C16 cyclic alkyl, C3 to CI(1 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C to C16 alkoxy, partially or perdeuterated C to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, halogen, F, CN or PX'fR8)^ wherein R8 is independently selected from Ct> to C)a aryl, C3 to C12 heteroaryl, C to C16 alkyl, C to C10 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from 0, S or Se, preferably O, wherein L is selected from substituted or unsubstituted C© to C24 aryl, substituted or unsubstituted C2 to C24 heteroaryl, wherein one or more substituents on L, if present, are independently selected from D, C© to C16 aryl, C3 to C20 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, C3 to Cj© branched alkyl, C3 to C16 cyclic alkyl, C3 to C16, branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C 1 to C16 allyl, partial])- or perfluorinated C to C16 alkoxy, partially or perdeuterated C to C16 alkyl, partially or perdeuterated Ci to C16 alkoxy, halogen, F, CN or PXrfR8)^ wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from C© to C16 aryl, C3 to CH heteroaryl, C to C16 alkyl, C:1 to C16 alkoxy, partially or perfluorinated C1 to C1& alkyl, partially or perfluorinated C1 to C16 alkoxy partially- or perdeuterated C1 to C1, alkyl , partially or perdcuterated C1 to C K, alkoxy; and X1 is selected from O, S or Se, preferably 0, wherein formula (I) can be undeuterated, partially deuterated or fully deuterated, wherein the metal dopant is selected from Ytterbium; wherein the first electron transport layer is free of 8-Hydroxyquinolinolato-h‘thium.
Further layers
In accordance with the invention, the organic electronic device may comprise, besides the layers already mentioned above, further layers. Exemplary embodiments of respective layers are described in the following:
Substrate
The substrate may be any substrate that is commonly used in manufacturing of, electronic devices, such as organic light-emitting diodes. If light is to be emitted through the substrate, the substrate shall be a transparent or semitransparent material, for example a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate maybe both a transparent as well as a non-transparent material, for example a glass substrate, a plastic substrate, a metal substrate or a silicon substrate.
Anode electrode
Either a first electrode or a second electrode comprised in the inventive organic electronic device may be an anode electrode. The anode electrode may be formed by depositing or sputtering a material that is used to form the anode electrode. The material used to form the anode electrode may be a high work-function material, so as to facilitate hole injection. The anode material may also be selected from a low work function material (i.e. aluminum). The anode electrode may be a transparent or reflective electrode. Transparent conductive oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin-dioxide (SnO2), aluminum zinc oxide (A1ZO) and zinc oxide (ZnO), may be used to form the anode electrode. The anode electrode may also be formed using metals, typically silver (Ag), gold (Au), or metal alloys.
Hole injection layer
A hole injection layer (HIL) may be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot-die coating, Langmuir-Blodgett (LB) deposition, or the like. When the HIL is formed using vacuum deposition, the deposition conditions may vary according t) the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL. In general, however, conditions for vacuum deposition may include a deposition temperature of ioo° C to 500° C1 a pressure of 10-8 to 10-3 Torr (1 Torr equals 133.322 Pa), and a deposition rate of 0.1 to 10 nm/sec. When the HIL is formed using spin coating or printing, coating conditions may vary according to the compound that is used to form the HIL, and the desired structure and thermal properties of the HIL. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm, and a thermal treatment temperature of about 8o° C to about 200° C. Thermal treatment removes a solvent after the coating is performed.
The HIL may be formed of any compound that is commonly used to form a HIL. Examples of compounds that may be used to form the HIL include a phthalocyanine compound, such as copper phthalocyanine (CuPc), 4,4’,4"-tris (3-methylphenylphenylamino) triphenylamine (m- MTDATA), TDATA, 2T-NATA, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA), and polyaniline)/poly(4-styrenesulfonate (PANI/PSS).
The HIL may comprise or consist of p-type dopant and the p-type dopant may be selected from tetrafluoro-tetracyanoquinonedimethane (F4TCNQ), 2,2'-(perfluoronaphthalen-2,6- diylidene) dimalononitrile or 2,2',2"-(cyclopropane-i,2,3-triylidene)tris(2-(p- cyanotetrafluorophenyljacetonitrile) but not limited hereto. The HIL may be selected from a hole-transporting matrix compound doped with a p-type dopant Typical examples of known doped hole transport materials are: copper phthalocyanine (CuPc), which HOMO level is approximately -5.2 eV, doped with tetrafluoro-tetracyanoquinonedimethane (F4TCNQ), which LUMO level is about -5.2 eV; zinc phthalocyanine (ZnPc) (HOMO = -5.2 eV) doped with F4TCNQ; a-NPD (NjN'-BisCnaphthalen-i-yll-N.N'-bisCphenyD-benzidine) doped with F4TCNQ. a-NPD doped with 2J2'-(perfluoronaphthalen-2,6-diylidene) dimalononitrile. The p- type dopant concentrations can be selected from 1 to 20 wt.-%, more preferably from 3 wt.-% to 10 wt.-%.
The thickness of the HIL may be in the range from about 1 nm to about too nm, and for example, from about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injecting characteristics, without a substantial penalty in driving voltage.
Hole transport layer
A hole transport layer (HTL) may be formed on the HIL by vacuum deposition, spin coating, slot-die coating, printing, casting, Langmuir-Blodgett (LB) deposition, or the like. When the HTL is formed by vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL, However, the conditions for the vacuum or solution deposition may vary, according to the compound that is used to form the HTL.
The HTL may be formed of any compound that is commonly used to form a HTL. Compounds that can be suitably used are disclosed for example in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010 and incorporated by reference. Examples of the compound that may be used to form the HTL are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl- [i,i-biphenyl]-4,4' -diamine (TPD), or N,N'-di(naphthalen-i-yl)-N,N'“ciiphenyl benzidine (alpha-NPD); and triphenylamine-based compound, such as 4,4',4"-tris(N- carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and inhibit excitons from being diffused into the EML.
The thickness of the HTL may be in the range of about 5 ran to about 250 run, preferably, about 10 nm to about 200 ran, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 160 nm, further about 100 nm to about 160 nm, further about 120 nm to about 140 nm. A preferred thickness of the HTL may be 170 nm to 200mm.
When the thickness of the HTL is within this range, the HTL may have excellent hole transporting characteristics, without a substantial penalty in driving voltage.
Electron blocking layer
The function of an electron blocking layer (EBL) is to prevent electrons from being transferred from an emission layer to the hole transport layer and thereby confine electrons to the emission layer. Thereby, efficiency, operating voltage and/or lifetime are improved. Typically, the electron blocking layer comprises a triarylamine compound. The triarylamine compound may have a LUMO level doser to vacuum level than the LUMO level of the hole transport layer. The electron blocking layer may have a HOMO level that is further away from vacuum level compared to the HOMO lev el of the hole transport layer. The thickness of the electron blocking layer may be selected between 2 and 20 nm,
If the electron blocking layer has a high triplet level, it may also be described as triplet control layer.
The function of the triplet control layer is to reduce quenching of triplets if a phosphorescent green or blue emission layer is used, Thereby, higher efficiency of light emission from a phosphorescent emission layer can be achieved. The triplet control layer is selected from triarylamine compounds with a triplet level above the triplet level of the phosphorescent emiter in the adjacent emission layer. Suitable compounds for the triplet control layer, in particular the triarylamine compounds, are described in EP 2 722908 Ai.
Emission layer (EML)
The EML may be formed on the HTL by' vacuum deposition, spin coating, dot-die coat-ing, printing, casting, LB deposition, or the like. When the EML is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL. However, the conditions for deposition and coating may vary, according to the compound that is used to form the EML.
It may be provided that the emission layer does not comprise the compound of Formula (J). The emission layer (EML) may be formed of a combination of a host and an emitter dopant. Example of the host are Alq3, 4,4'-N,N'-dicarbazole-biphenj’l (CBP), poly(n-vinylcarbazole) (PVK), 9JO-di(naphthalene-2-j’l)anthracene (ADN), 4,4',4’'-tris(carbazol-9-yl)- triphenylamine(TCTA), i,3,5-tris(N-phcnylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl- 9,io-di-2-naphthylanthracenee (TBADN), distyrylarylene (DSA) and bis(2-(2- hydroxyphenyl)benzo-thiazolate)zinc (Zn(BTZ)2).
The emitter dopant maybe a phosphorescent or fluorescent emitter. Phosphorescent emiters and emiters which emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emiter may be a small molecule or a polymer.
Examples of red emiter dopants are PtOEP, Ir(piq)3, and Btp21r(acac), but are not limited thereto. These compounds are phosphorescent emiters, however, fluorescent red emitter dopants could also be used.
Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.
Examples of phosphorescent blue emitter dopants are F2lrpic, (F2ppy)2lr(tmd) and Ir(dfppz)3 and ter-fluorene. 4.4'-bis(4-diphenyl amiostyryDbiphenyl (DPAVBi), 2,5,8,] i-tetra- tert -butyl perylene (TBPe) are examples of fluorescent blue emiter dopants.
The amount of the emitter dopant may be in the range from about 0.01 to about 50 parts by weight, based on 100 parts by weight o f the host. Alternatively, the emission layer may consist of a light-emitting polymer. The EML may have a thickness of about 10 nm to about 100 nm, for example, from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML may have excellent light emission, without a substantial penalty in driving voltage.
Hole blocking layer (HBL)
A hole blocking layer (HBL) may be formed on the EML, by using vacuum deposition, spin coating, slot-die coating, printing, casting, LB deposition, or the like, in order to prevent the diffusion of holes into the ETL. When the EML comprises a phosphorescent dopant, the HBL may have also a triplet exciton blocking function. The hole blocking layer may be the inventive organic semiconductor layer comprising or consisting of the inventive compound represented by the general Formula (1) as defined above.
The HBL may also be named auxiliary ETL or a-ETL.
When the HBL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for the formation of the HIL However, the conditions for deposition and coating may vary, according to the compound that is used to form the HBL. Any compound that is commonly used to form a HBL may be used. Examples of compounds for forming the HBL include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives.
The HBL may have a thickness in the range from about 5 rnn to about loo nm, for example, from about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL may have excellent hole-blocking properties, without a substantial penalty in dining voltage.
The hole blocking layer may also be described as a-ETL or auxiliary ETL.
Electron injection layer (EIL)
An optional EIL, which may facilitates injection of electrons from the cathode, may be formed on the ETL, preferably directly on the electron transport layer. Examples of materials for forming the EIL include lithium 8-hydroxyquinolinolate (LiQ), LiF, NaCl, CsF, LisO, BaO, Ca, Ba, Yb, Mg which are known in the art. Deposition and coating conditions for forming the EIL are similar to those for formation of the HIL, although the deposition and coating conditions may vary, according to the material that is used to form the EIL.
The thickness of the EIL may be in the range from about 0.1 nm to about 10 nm, for example, in the range from about 0.511m to about 9 nm. When the thickness of the EIL is within this range, the EIL may have satisfactory electron-injecting properties, without a substantial penalty in driving voltage.
Cathode electrode
The cathode electrode is formed on the EIL if present. The cathode electrode may be formed of a metal, an alloy, an electrically conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode electrode may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), or the like. Alternatively, the cathode electrode may be formed of a transparent conductive oxide, such as ITO or IZO.
The thickness of the cathode electrode may be in the range from about 5 nm to about 1000 nm, for example, in the range from about 10 nm to about 100 nm. When the thickness of the cathode electrode is in the range from about 5 nm to about 50 nm, the cathode electrode may be transparent or semitransparent even if formed from a metal or metal alloy.
It is to be understood that the cathode electrode is not part of an electron injection layer or the electron transport layer.
Charge generation layer/hole generating layer The first charge generation layer (CGL) comprises a p- type and an n-type charge generation layer. An interlayer may be arranged between the p-type charge generation layer and the n- type charge generation layer.
Topically, the charge generation layer is a pn junction joining an n-frpe charge generation layer (electron generating layer) and a hole generating layer. The n-side of the pn junction generates electrons and injects them into the layer which is adjacent in the direction to the anode. Analogously, the p-side of the p-n junction generates holes and injects them into the layer which is adjacent in the direction to the cathode.
Charge generating layers are used in tandem and stacked devices, for example, in tandem or stacked 0 LEDs comprising, between two electrodes, two or more emission layers. In a tandem or stacked OLED comprising two emission layers, the n-type charge generation layer- provides electrons for the first light emission layer arranged near the anode, while the hole generating layer prorides holes to the second light emission layer arranged between the first emission layer and the cathode.
Suitable matrix materials for the hole generating layer may be materials conventionally used as hole injection and/or hole transport matrix materials. Also, p-type dopant used for the hole generating layer can employ conventional materials. For example, the p-type dopant can be one selected from a group consisting of tetrafluore-7,7,8,8-tetracyanoquinodimethanc (F4- TCNQ), derivatives of tetracyanoquinodimcthane, radialene derivatives, iodine, FeClg, FeEg, and SbCfo. Also, the host can be one selected from a group consisting of N,N'-di(naphthalen- i-yl)-N,N-diphenyl-benzidine (NPB), N,N'-diphenyl-N,N’-bis(3-methylphenyl)-i,i-biphenj-l- 4,4’-diamine (TPD) and N,N',N'-tetranaphthyl-benzidine (TNB). The p-type charge generation layer may consist of CNHAT.
Organic electroluminescent derice
According to an embodiment, the organic electroluminescent device further comprises a layer selected from hole injection layer, hole transport layer, electron blocking layer, a holeblocking layer, an electron transport layer, and an electron injection layer.
According to an embodiment, the organic electroluminescent device further comprises a hole injection layer, a first hole transport layer, a second hole transport layer, first electron blocking layer, second electron blocking layer, optionally a first hole blocking layer, optionally a second hole blocking layer, a second electron transport layer, and an electron injection layer.
According to an embodiment , the organic electroluminescent device comprises an anode layer (120), a hole injection layer (130), a first hole transport layer (141), a first electron blocking layer (142), a first emission layer (145), a first optional hole blocking layer(i47), and a first electron transport layer (149), wherein the first electron transport layer (149) is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex, wherein the first electron transport layer (149) is preferably in direct contact with the first emission layer (145), a first charge generation layer (16O) disposed over the first electron transport layer (149), wherein the first charge generation layer (160) comprises a first n-type charge generation layer (161), and a first p-type charge generation layer (162), wherein the first n-typc charge generation layer (161) comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (149) is in direct contact with the first n-type charge generation layer (161), a second hole transport layer (241), a second electron blocking layer (242), a second emission layer (245), a second optional hole blocking layer (247), an electron transport layer (148), an electron injection layer (180), and a cathode layer (190).
According to an embodiment , the organic electroluminescent device further comprises a third emission layer, a second electron transport layer, and a second charge generation layer, wherein the third emission layer is arranged between the second charge generation and the cathode layer, wherein the second charge generation layer is arranged between the first charge generation layer and the cathode layer, and between the second emission layer and the third emission layer wherein the second charge generation layer comprises a second n-type charge generation layer and second p-type charge generation layer, wherein the second n-tvpe charge generation layer is arranged closer to the anode layer than the second p-ripe charge generation layer, wherein the second p-type charge generation layer is arranged closer to the cathode layer than the second n-type charge generation layer, wherein the second electron transport layer is arranged between the second emission layer and the third emission layer, wherein the second electron transport layer is in direct contact with the second n-type charge generation layer, wherein wherein the second n-type charge generation layer comprises a metal dopant and a compound of formula (I), wherein R‘ to R7; L and Ar may be selected as defined above; wherein the compound of formula (I) in the first and second n-type charge generation layer and the compound of formula (I) is selected the same or different preferably the same, wherein the metal dopant is Ytterbium; and wherein the second electron transport layer is free of 8-Hydroxyquinolinolato-lithium.
According to an embodiment , the organic electroluminescent device comprises an anode layer (120), a hole injection layer (130), a hole transport layer (141), a first electron blocking layer (142), a first emission layer (145), a first optional hole blocking layer (147)? a first electron transport layer (149), wherein the first electron transport layer (149) is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex, wherein the first electron transport layer (149) is preferably in direct contact with the first emission layer (145), a first charge generation layer (160) disposed o\ er the first electron transport layer (149), wherein the first charge generation layer (160) comprises a first n-type charge generation layer (161), and a first p-type charge generation layer (162), wherein the first n-type charge generation layer (161) comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (149) is in direct contact with the first n-type charge generation layer (261) , a second hole transport layer (241), and a second electron blocking layer (242), a second emission layer (245), a second optional hole blocking layer (247), a second electron transport layer (249k wherein the second electron transport layer (ETL2) 249 is free of 8-Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex, wherein the second electron transport layer (249) is preferably in direct contact with the second emission layer (245), a second charge generation layer (260) disposed over the second electron transport layer (249), wherein the second charge generation layer (CC1La) 260 comprises a second n-type charge generation layer (n-CGLa) 261, and a first p-type charge generation layer (p-CGL2) 262, wherein the second n-type charge generation layer (n-CGLa) 261 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the second electron transport layer (ETLi) 249 is in direct contact with the second n- type charge generation layer (n-CGL2) 261, wherein the second n-type charge generation layer (n-CGLa) 261 can be selected the same or different than the first n-type charge generation layer (n-CGLi) 161, and wherein the second p-type charge generation layer (p-CC1L.2) 262 can be selected the same or different than the first p-type charge generation layer (p-CGLi) 161, a third hole transport layer (341), and a third electron blocking layer (342), a third emission layer (345)- a third optional hole blocking layer (347), an electron transport layer (148), an electron injection layer (180), and a cathode layer (190).
Jfreparationm^
According to another aspect of the present invention, there is provided a method of manufacturing an organic electroluminescent device (OLED), the method using: at least one deposition source, preferably two deposition sources and more preferred at least three deposition sources.
The methods for deposition that can be suitable comprise: deposition via vacuum thermal evaporation; deposition via solution processing, preferably the processing is selected from spincoating, printing, casting; and/or slot-die coating.
According to various embodiments of the present invention, there is provided a method using: a first deposition source to release the compound of Formula (I) according to the invention, and a second deposition source to release Yb; the method comprising the steps of forming the organic semiconductor layer; whereby for an organic light-emitting diode (OLED) : the organic semiconductor layer is formed by releasing the compound of Formula (I) according to the invention from the first deposition source and Yb from the second deposition source.
According to various embodiments of the present invention, the method may farther include forming on the anode electrode, an emission layer and at least one layer selected from the group consisting of forming a hole injection layer, forming a hole transport layer, or forming a hole blocking layer, between the anode electrode and the first electron transport layer.
According to various embodiments of the present invention, the method may further include the steps for forming an organic light-emitting diode (OLED), wherein on a substrate a first anode electrode is formed, on the first anode electrode an emission layer is formed, on the emission layer an electron transport layer stack is formed, optionally a hole blocking layer is formed on the emission layer and an organic semiconductor layer is formed, and finally a cathode electrode is formed, optional a hole injection layer, a hole transport layer, and a hole blocking layer, formed in that order between the first anode electrode and the emission layer, optional an electron injection layer is formed between the organic semiconductor layer and the cathode electrode.
According to various embodiments of the present invention, the method may further comprise forming an electron injection layer on the organic semiconductor layer. However, according to various embodiments of the OLED of the present invention, the OLED may not comprise an electron injection layer.
According to another aspect of the invention, it is provided an electronic device comprising at least one organic light emitting derice according to any embodiment described throughout this application, preferably, the electronic device comprises the organic light emitting diode in one of embodiments described throughout this application. More preferably, the electronic derice is a display device.
In one embodiment, the organic electronic device according to the invention comprising an organic semiconductor layer comprising a compound according to Formula (I) may further comprise a layer comprising a radialene compound and/or a quinodimethane compound.
In one embodiment, the radialene compound and/or the quinodimethane compound may be substituted with one or more halogen atoms and/or with one or more electron withdrawing groups. Electron withdrawing groups can be selected from nitrile groups, halogenated alkyl groups, alternatively from perhalogenated alkyl groups, alternatively from perfluorinated alkyl groups. Other examples of electron withdrawing groups may be acyl, sulfonyl groups or phosphoryl groups.
Alternatively, acyl groups, sulfonyl groups and/or phosphoryl groups may comprise halogenated and/or perhalogenated hydrocarbyl. In one embodiment, the perhalogenated hydrocarbyl may be a perfluorinated hydrocarbyl. Examples of a perfluorinated hydrocarbyl can be perfluormethyl, perfluorethyl, perfluorpropyl, perfluorisopropyl, perfluorobutyl, perfluorophenyl, perfluorotolyl; examples of sulfonyl groups comprising a halogenated hydrocarbyl may be trifluoromethylsulfonyl, pentafluoroethylsulfonyl, pentafluorophcnylsulfony], heptafluoropropylsufonyl, nonafluorobutylsulfonyl, and like. In one embodiment, the radialene and/or the quinodimethane compound may be comprised in a hole injection, hole transporting and/or a hole generation layer.
In one embodiment, the radialene compound may have Formula (XX) and/or the quinodimethane compound may have Formula (XXIa) or (XXIb): wherein (as an exception different to the description above) R’, R2, R3, R4 R5, R6, Rr, R®, R11, R12 R‘5, R16, R2°, R21 are independently selected from above mentioned electron withdrawing groups and R9, R10, Rfo R1'*, Ro, R18, R19 R22, R2® and R24 are independently selected from H, halogen and above mentioned electron withdrawing groups.
According to one embodiment of the present invention, the organic semiconductor layer comprising compound of formula (1) is adjacent to a layer comprising a compound of formula (XX), (XXIa) or (XXIb).
According to one embodiment of the present invention, the organic semiconductor layer comprising compound of formula (I) is in direct contact to a layer comprising a compound of formula (XX), (XXIa) or (XXIb).
Compound of formula (M1) or (M2)
According to one aspect, the present invention relates to a compound of formula (M1) or of formula (M2) wherein in formula (M1)
- R' to R? are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted G to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C:. to C16 cyclic alky l, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C18 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX’fR8)2 wherein R8 is independently selected from G to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C1» alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably 0; and
- Rto RLb, R^and RLd are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl , substituted or unsubstituted C1 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C1& alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX’CR8) wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 allyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from 0, S or Se, preferably 0;
- Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl; wherein in formula (M2)
- R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted G to C14 aryl or substituted or unsubstituted C1 to C24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX1(R8)2 wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy ; and X1 is selected from 0, S or Se, preferably O; and
- Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaiyl;
- L is selected from substituted or unsubstituted C6 to C24 aryl, substituted or unsubstituted C2 to C24 heteroaryl.
The compound of formula (M1) may be a compound of formula (M3) and the compound of formula (M2) may be a compound of formula (M4)
wherein in formula (Mg)
- R* to R7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C1 to C24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl. C3 to C1,-, branched alkoxy, C3 to C» cyclic alkoxy, partially or perfluorinated C1 to C18 alkyl, partially or perfluorinated C> to C1o alkoxy, partially or perdeuterated C. to C16 alky l, partially or perdeuterated C1 to Clt-. alkoxy, or PX'(RH)2 wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C1<. alkoxy, partially or perfluorinated C< to C1o alkyd, partially or perfluorinated C1 to C1o alkoxy, partially or perdeuterated C1 to C16 alky l, partially or perdeuterated C1 to C ,6 alkoxy; and X1 is selected from O. S or Se, preferably O; and
- RLb, RLb, Rtoand JR14 are independently selected from H, D, substituted or unsubstituted C1 to C1o alkyd, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C10 cyclic alkyl, C, to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C18 alkyl, partially or perfluorinated C1 to C1* alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PXI(R8)2 wherein R8 is independently selected from C1> to C!2 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C1& alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably O; wherein in formula (M4)
- R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C1 to C24 heteroaryl, CN, halogen, F, C1 to C1& alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C18 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to CK, alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX1(R8)2 wherein R8 is independently selected from Crfo C12 aryl. C3 to C12 heteroaryl, C1 to C10 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X’ is selected from O, S or Se, preferably 0; and - L is selected from substituted or unsubstituted C6 to C24 aryl, substituted or unsubstituted C2 to C64 heteroaryl.
R tojfr of for^
According to an embodiment, in formula (M1) or (M3) R1 to R ' are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C* alkyl, or PX1(R8)2 wherein R8 is independently selected from C6 to C1a aryl, C3 to C12 heteroaryl, C1 to C16 alkyl. C1 to CK, alkoxy, partially or perfluorinated C1 to C18 alkyl, partially or perfluorinated C1 to Cm alkoxy, partially or perdeuterated C1 to Cm alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably O,
According to an embodiment, in formula (M1) or (M3) R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F.
According to an embodiment, in formula (M1) or (M3) R1 to R~ are independently selected from H, D, substituted or unsubstituted C1 to C16> alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, halogen, F.
According to an embodiment, in formula (M1) or (M3) R1 to R~ are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, F.
According to an embodiment, in formula (M1) or (M3) R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C2 to C18 heteroaryl, CN, halogen, Cl, F.
According to an embodiment, in formula (M1) or (M3) R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C6 to Ca aryl or substituted or unsubstituted C2 to C18 heteroaryl, F.
According to an embodiment, in formula (M1) or (M3) R‘ to R7 are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6, to C12 aryl or substituted or unsubstituted C2 to C12 heteroaryl, CN, halogen, Cl, F.
According to an embodiment, in formula (M1) or (M3) R1 to R' are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C12 aryl or substituted or unsubstituted C2 to C12 heteroaryl, F.
According to an embodiment, in formula (M1) or (M3) R1 to R" arc independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C1o aryl or substituted or unsubstituted C2 to C10 heteroaryl, CN, halogen, Cl, F. According to an embodiment, in formula (M1) or (M3) R’ to R7 are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C2 to C1(, heteroaryl, F.
According to an embodiment, in formula (M1) or (M3) R‘ to R7 are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, CN, halogen, Cl, F.
According to an embodiment, in formula (M1) or (M3) R* to R7 are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, F.According to an embodiment, in formula (M1) or (M3) RJ to R7 are independently selected from H, D.
R2 to R7 of formula andXM4)
According to an embodiment, in formula (Ma) or (M4) R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to Clh alkyl, substituted or unsubstituted Ct, to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C3 to C(6 branched alkyl, C3 to C lt-, cyclic alky l, partially or perfluorinated C1 to C1(, alkyd, partially or perdcuterated C1 to Ctft alkyd, or PX’(R8)a wherein R8 is independently selected from Cc, to C12 aryl, C;j to C12 heteroaryl. C1 to C1(, alkyd, C1 to C alkoxy, partially or perfluorinated C1 to C16 alkyd, partially or perfluorinated C1 to alkoxy, partially or perdeuterated C1 to C16 alkyd, partially or perdeuterated C1 to alkoxy; and X1 is selected from O, S or Se, preferably O,
According to an embodiment, in formula (M2) or (M4) R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C® alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F.
According to an embodiment, in formula (M2) or (M4) R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, halogen, F.
According to an embodiment, in formula (Ma) or (M4) R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted Ct, to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, F,
According to an embodiment, in formula (M2) or (M4) R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C1 to C1« aryl or substituted or unsubstituted C2 to heteroaryl, CN, halogen, Cl, F.
According to an embodiment, in formula (M2) or (M4) R2 to R" are independently selected from H, D, substituted or unsubstituted C1 to C12 alkyl, substituted or unsubstituted C(, to C1« aryl or substituted or unsubstituted C; to CJS heteroaryl, F. According to an embodiment, in formula (M2) or (M4) R2 to R7 are independently selected from H. D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6, to C12 aryl or substituted or unsubstituted C2 to C1 heteroaryl, CN, halogen, Cl, F.
According to an embodiment, in formula (Ma) or (M4) R2 to R” are independently selected from H, D, substituted or unsubstituted C1 to Cft alkyl, substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C2 to Cfo heteroaryl, F.
According to an embodiment, in formula (M2) or (M4) R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to CJ0 aryl or substituted or unsubstituted C2 to C16 heteroaryl, CN, halogen, Cl, F.
According to an embodiment, in formula (M2) or (M4) R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C2 to C1o heteroaiyl, F.
According to an embodiment, in formula (M2) or (M4) R2 to R7 are independently selected from H, D, substituted or unsubstituted Cj to C4 alkyl, substituted or unsubstituted Cfi aryl or substituted or unsubstituted C3 to C5 heteroaryl, CN, halogen, Cl, F.
According to an embodiment, in formula (M2) or (M4) R2 to R" are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C1, aryl or substituted or unsubstituted C3 to C5 heteroaryl, F.
According to an embodiment, in formula (M2) or (M4) R2 to R~ are independently selected from H, D.
Substituents on R1 to R7 of form ulas (M1) to (M4)
R1 to R7 in formulas (M1) and (M3), respectively R2 to R7 in formulas (M2) and (M4), may be independently unsubstituted or substituted with one or more substituents.
According to an embodiment, the one or more substituents on R> to R7 in formulas (M1) and (M3), respectively Ra to R7 in formulas (M2) and (M4), if present, are independently selected from D, Ct, to C18 aryl, C3 to C20 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C* branched alkoxy, C3 to C16, cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C. to C16, alkyl, partially or perdeuterated C1 to C16 alkoxy, halogen, F, CN or PN1(R8)_., wherein R8 is independently selected from C(, to C12 aryl, C.,. to C12 heteroaiyl, C1 to C16 alkyl , C1 to C16 alkoxy, partially or perfluorinated C1 to C16.allyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably 0, According to an embodiment, the one or more substituents on R1 to R'in formulas (M1) and (M3), respectively R2 to R7 in formulas (Ma) and (M4), if present, are independently selected from D. substituted or unsubstituted C6, to C18 and, substituted or unsubstituted C3 to C20 heteroaryl, C1 to Cfo alkyl, C3 to Cfo branched alkyl, C3 to Cfo cyclic alkyl, partially or perfluorinated C1 to C1 alkyl, partially or perdeuterated C1 to C16 alkyl, PX’(R8)2, halogen, F or CN, wherein R8 is independently selected from C6 to Cfo aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to Cfo alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably 0.
According to an embodiment, the one or more substituents on R1 to R7in formulas (M1) and (M3), respectively R2 to R7 in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted Ct, to 0,8 aryl, substituted or unsubstituted C3 to C2O heteroaryl, C1 to C16, alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C1ft alkyl, partially or perdeuterated 0, to C16 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on R1 to R’ in formulas (M1) and (M3), respectively Ra to R7 in formulas (M2) and (M4X if present, are independently selected from D, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C3 to C14 heteroaryl, C1 to C10 alkyl, C3 to C10 branched alkyl, C3 to C10 cyclic alkyl, partially or perfluorinated C1 to Cur alkyl, partially or perdeuterated C1 to C10 allgl, halogen, For CN.
According to an embodiment, the one or more substituents on R1 to R' in formulas (Mt) and (M3), respectively R2 to R7 in formulas (Ma) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C10 aryl, substituted or unsubstituted C3 to C12 heteroaryl, C1 to C1 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyd , partially or perfluorinated C1 to C6 alkyl, partially or perdeuterated C1 to Cf, alkyl, halogen, For CN.
According to an embodiment, the one or more substituents on R1 to R7 in formulas (M1) and (M3), respectively R2 to R7 in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C1o aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on R1 to R7 in formulas (M1) and (M3), respectively R2 to R7 in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C1 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated Cs to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN.
RfrJ^R^
According to an embodiment, in formula (M1) or (M3) RLa, RLb, Rfoand RLb are independently selected from H, D. substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C3 to 0,6 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, or PX1(R8)2 wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from 0, S or Se, preferably O,
According to an embodiment, in formula (M1) or (M3) Rte RLb, RLcand R1^ are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyd, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F.
According to an embodiment, in formula (M1) or (M3) RL, RLb, Rteand R RL adre independently selected from H, D, and substituted or unsubstituted C1 to C16 alkyl.
According to an embodiment, in formula (M1) or (M3) Rte RLb, RLb,and R1-4 are independently selected from H, D, and substituted or unsubstituted C1 to C12 alkyl.
According to an embodiment, in formula (M1) or (M3) RLa RLb, Rte, and RLb are independently selected from H, D, and substituted or unsubstituted C1 to Cg alkyl.
According to an embodiment, in formula (M1) or (M3) RL a RLb, Rfoand RLd are independently selected from H, D, and substituted or unsubstituted C1 to C1, alkyl.
According to an embodiment, in formula (M1) or (M3) Rte RLb, Rteand RLd are independently selected from H, D. and substituted or unsubstituted C1 to C4 alkyl.
According to an embodiment, in formula (M1) or (M3) RU1, RLb, Rteand RLd are independently selected from H, D, and substituted or unsubstituted C1 to C3 alkyl.
According to an embodiment, in formula (M1) or (M3) R1-3, RLd, Rteand RLd are independently selected from H, D, and substituted or unsubstituted C1 to C1 alkyl.
According to an embodiment, in formula (M1) or (M3) Rte Rte, Rteand RLd are independently selected from H, D, and substituted or unsubstituted C1 alkyl.
Substituents on Rte RLb, Rteand R1-11 of formula (M1) or (M3)
R13, RLb, Rteand RLd in formulas (M1) and (M3), may be independently unsubstituted or substituted with one or more substituents.
According to an embodiment, the one or more substituents on RU1, Rte RK,and RLd in formulas (M1) and (M3), if present, are independently selected from D, C1, to C1H aryl, C3to C20 heteroaryl, C1 to C ,(, alkyl, C1 to C16 alkoxy’, C3 to C16 branched alkyl, C16 to C16 cyclic alky l, C1 to C16 branched alkoxy, C3 to C16 cy clic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, halogen, F, CN or PX1(R8)2, wherein R8 is independently selected from C1 to C12. aryl, C3 to C12 heteroaryl, C1 to C16 alky], C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to CC1 alkoxy, partially or perdeuterated C1 to C16, alkyd, partially or perdeuterated C1 to C16 alkoxy: and X1 is selected from 0, S or Se, preferably O.
According to an embodiment, the one or more substituents on RLb, Rte Rfoand RM in formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C1& alkyl. C1 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, PX1(R8)2 halogen, F or CN, wherein R8 is independently selectedfrom C1> to C12 aryl, C3 to C12 heteroaryl, C1 to alkyl, C1 to C1& alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C18 alkyl, partially or perdeuterated C1 to C1& alkoxy; and X1 is selected from 0, S or Se, preferably O.
According to an embodiment, the one or more substituents on Rte Rtb, Rfoand RLb in formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C1> to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alky l, partially or perdeuterated C1 to C1d alkyl, halogen, For CN.
According to an embodiment, the one or more substituents on RLb, RLb, R1x,and RLb in formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C1> to C12 aryl, substituted or unsubstituted C3 to CM heteroaryl, C1 to Cm alky l, C:; to C10 branched alkyl, C3 to C1o cyclic alkyl, partially or perfluorinated C1 to C1o alkyl, partially or perdeuterated C1 to C1o alky l, halogen, F or CN.
According to an embodiment, the one or more substituents on Rte Ri> Rfoand RLm formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C1s to C10 aryl substituted or unsubstituted C3 to C12 heteroaryl, C1 to C1> alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C1 alkyl, partially or perdeuterated C1 to C6 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on R1-3, RLb, RLC and RM in formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C1o aryl, substituted or unsubstituted C3 to C1o heteroaryl, C1 to C4 allyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C1 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on RLb, RLb, R'riand RLb in formulas (M1) and (M3), if present, are independently selected from D. substituted or unsubstituted C1, aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN. L of formulas M(2) and (M4)
According to an embodiment, in formulas M(2) and (M4), L is selected from substituted or unsubstituted Ct, to C1« and, substituted or unsubstituted C2 to C1& heteroaryl.
According to an embodiment, in formulas M(2) and (M4), L is selected from substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C2 to C12 heteroaryl.
According to an embodiment, in formulas M(2) and (M4), L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted Cb to CJO heteroaryl.
According to an embodiment, in formulas M(2) and (M4), L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C3 to C5 heteroaryl.
According to an embodiment, in formulas M(2) and (M4), L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C3 to C3 heteroaryk wherein heteroaryl is a six-member ring.
According to an embodiment, in formulas M(2) and (M4), L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, tnazinjl.
According to an embodiment, in formulas M(2) and (M4), L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl
According to an embodiment, in formulas M(2) and (M4), L is selected from substituted phenyl, unsubstituted phenyl or unsubstituted naphthyl.
Substituents on L of formulas (M2) and (M4)
L in formulas (Ma) and (M4) may be independently unsubstituted or substituted with one or more substituents,
According to an embodiment, the one or more substituents on L in formulas (M2) and (M4), if present, are independently selected from D, C16 to C18 aryl, C3 to C20 heteroaryl. C1 to C16 alkyl, C1 to C16 alkoxy, C1 to C» branched alkyl, C3 to C16 cyclic alkyl, C1 to C16 branched alkoxy, C3 to C16, cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16, alkyl, partially or perdeuterated C1 to C16 alkoxy, halogen, F. CN or PX1(R8), wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from C1 to C12 aryl, C3 to heteroaryl. C1 to C16 alkyl, C1 to C16, alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably O. According to an embodiment, the one or more substituents on L in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to aryl, substituted or unsubstituted C3 to Cfr heteroaryl, C1 to alkyl, C1 to Cw alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C16, branched alkoxy, C3 to CH, cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C( to Ct6 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, PX^R8)^, halogen, F or CN, wherein R8 is independently selected from C6 to C12 aryl, C3 to Ce heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C.& alkyl, partially or perfluorinated C1 to C« alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to 0,6 alkoxy; and X* is selected from O, S or Se, preferably O.
According to an embodiment, the one or more substituents on L in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C& to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl, C3 to Cfr branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C1& alkyl, partially or perdeuterated CI to C16 alkyl, PX^R8)^ halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from C6 to C12 aryl, C3 to Cia heteroaryl, C1 to Cn, alkyl, C( to Cl() alkoxy, partially or perfluorinated C1 to C16, alkyl, partially or perfluorinated C1 to C16, alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16, alkoxy; and X1 is selected from 0, S or Se, preferably 0.
According to an embodiment, the one or more substituents on L in formulas (Ma) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C1s aryl, substituted or unsubstituted C3 to Cao heteroaryl, C1 to C^ alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyd, partially or perfluorinated C1 to C1& alky I, partially or perdeuterated C1 to C16 alkyl, PX‘(R8)2, halogen, F or CN, wherein R8 is independently selected from C6 to Cu aryl, C3 to C12 heteroaryl, C1 to C^ alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16, alkyl, partially or perfluorinated C1 to C16, alkox, , partially or perdeuterated C> to C16 alky l, partially or perde 11 terated C1 to C16t alkoxy’; and X1 is selected from 0, S or Se, preferably’ 0.
According to an embodiment, the one or more substituents on L in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C2O heteroaryl, C1 to C16 alkyl, C3 to Cw branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to 0,6 alkyl, partially or perdeuterated C1 to C16 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on L in formulas (Ma) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C® alkyl, C3 to C16 branched alkyl, C3 to CH, cyclic alkyl, partially or perfluorinated Cj to C1<> alkyd, partially or perdeuterated C1 to CK, alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on L in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C12 aryl, 6 substituted or unsubstituted Ct to C14 heteroaryl, C1 to CK, alkyl, C3 to C10 branched alkyl, C3 to C1o cyclic alkyl, partially or perfluorinated C1 to C10 alkyl, partially' or perdeuterated C1 to C10) alkyl, halogen, F or CN, wherein the substituents may be linked \ia a single bond or a heteroatom to form a ring.
According to an embodiment, tire one or more substituents on L in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C3 to C14 heteroaryl, C1 to C10 alkyl, C3 to Clf> branched alkyl, C3 to CK, cyclic allcyl. partially or perfluorinated C1 to C10 alkyd, partially or perdeuterated C1 to C1O alkyd, halogen, F or CN.
According to an embodiment, the one or more substituents on L in formulas (Ma) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C10 aryl, substituted or unsubstituted C3 to C12 heteroaryl, C1 to Cf, alkyl, C3 to Cb branched alkyd, C3 to C6 cyclic alkyl, partially' or perfluorinated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkyl, halogen, F or CN, wherein the substituents may be linked ria a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on L in formulas (Ma) and (M4), if present, are independently selected from D, substituted or unsubstituted Ch to C10 aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to Ch alkyl. C3 to C6, branched alkyd, C5 to C6 cyclic alkyl, partially or perfluorinated C1 to C6, alkyl, partialy or perdeuterated Ch to Q. alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on L in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C10 aryl, substituted or unsubstitured C3 to C10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C:i to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated Cf to C4 alkyl, halogen, F or CN, wherein the substituents maybe linked ria a single bond or a heteroatoni to form a ring.
According to an embodiment, the one or more substituents on L in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to CK > aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to C4 alkyd, C3 to C4 branched alkyl, C3 to C6 cyclic alkyd, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen. F or CN.
According to an embodiment, the one or more substituents on L in formulas (M2) and (M4), if present, arc independently selected from D, substituted or unsubstituted C6 aryd, substituted or unsubstituted C1 to C5 heteroand, C1 to C4 alkyd, C3 to C4 branched alkyl, C , to C1, cyclic alkyd, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyd, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on L in formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted Ch and, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to Ct, cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN.
According to an embodiment, L in formulas (M2) and (M4) is selected from the following moieties E1 to E34 shown in in Table 2 a above.
According to an embodiment, L in formulas (M2) and (M4) is selected from the following moieties E1 to E33 shown in in Table 2b above.
According to an embodiment, L in formulas (M2) and (M4) is selected from the moieties Ei to E30.
According to an embodiment, L in formulas (M2) and (M4) is selected from the moieties E1 to E24.
According to an embodiment, L in formulas (M2) and (M4)is selected from the moieties Ei to E23.
According to an embodiment, L in formulas (M2) and (M4) is selected from the moieties Ei to E5, and E8 to E23.
According to an embodiment, L in formulas (Ma) and (M4) is selected from the moieties E1 to Eg, E8 to E13 and E16.
According to an embodiment, L in formulas (Ma) and (M4) is selected from the moieties Ei to E5, E11 and E16.
According to an embodiment, L in formulas (M2) and (M4)is selected from the moieties Ei to E5 and E16.
According to an embodiment, L in formulas (M2) and (M4) is selected from the moieties Ei to E3, E11 and E16.
According to an embodiment, L in formulas (M2) and (M4) is selected from the moieties E2 to E3, E1i and E16.
According to an embodiment, L in formulas (M2) and (M4)is selected from the moieties Ea to E3 and E16.
Ar of formulas ( M1) and (M3) Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 to C2< aryl or substituted or unsubstituted C2 to C24 heteroaryl.
According to an embodiment, Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 to C16 aryl or substituted or unsubstituted C2 to C16 heteroaryl.
According to an embodiment, Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C2 to Cfo heteroaryl.
According to an embodiment, Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C2 to CJO heteroaryl.
According to an embodiment, Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl.
According to an embodiment, Ar of formulas (M1) and (M3) is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaiyl is a six-member ring.
According to an embodiment, Ar of formulas (M1) and (Mg)is selected from the group consisting of substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, and substituted or unsubstituted quinolinyl.
Ar of formulas (M1) and (M3) may be unsubstituted or substituted with one or more substituents.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C16 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, C3 to C1& branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C> to C16 alkoxy, PX‘(R8)2! halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from Ca to C12 aryl, C3 to CJa heteroaryl, C1 to C16 alkyl, C1 to C1o alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to Cm alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably 0.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C, to C16 aryl, substituted or unsubstituted C3 to Ca® heteroaryl, C1 to Cm. alkyl, C1 to Cm, alkoxy-, C3 to Cm branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluormated C1 to C16 alkyl, partially or perfluorinated C1 to CS6 alkoxy, partially or perdeuterated C1 to alkyl, partially or perdeuterated C1to Crf alkojqy PXrfWfo halogen, F or CN, wherein R® is independently selected from C6 to CB aryl, C3 to C12 heteroaryl, Ck to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to Ch alky!, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C1r> alkyl, partially or perdeuterated C1 to Cto alkoxy; and > is selected from O, S or Se, preferably O.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to Cj* alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, PXrfR8) 2, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C^ alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C* alkoxy; and X1 is selected from 0, S or Se, preferably 0.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C;1 to C2O heteroaryl, C1 to C16 alkyl, C3 to Clf> branched alkyl, C3 to CK, cyclic alkyl, partially or perfluorinated C1 to C1<, alkyd, partially or perdeuterated C1 to C16 alkyl, PX1(R), halogen, F or ON, wherein R8 is independently selected from C& to C12 aryl, C3 to C18 heteroaryl, C1 to C16> alkyl, CL to C16 alkoxy, partially or perfluorinated C1 to Clt, alkyd, partially or perfluorinated C( to C16 alkoxy, partially or perdeuterated C5 to Clb alkyl, partially or perdeuterated C1 to C1t, alkoxy; and Xs is selected from 0, S or Se, preferably O.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, Ct to C16 alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C1& alkyl, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C10 aryl, substituted or unsubstituted C3 to CM heteroaryl, C1 to C10 alkyl, C3 to C10 branched alkyl, C3 to CH. cyclic alkyl, partially or perfluorinated C1 to C10 alkyl, partially or perdeuterated C1 to C10 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring. According to an embodiment, the one or more substituents on Ar, if present, are independently selected from D, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C3 to C14 heteroaryl, C1 to C 10 alkyl ; C3 to branched alkyl, 0^ to C10 cyclic alkyd, partially or perfluorinated C1 to C1o alkj 1, partially or perdeuterated C1 to C1o alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C10 aryl, substituted or unsubstituted C3 to C12 heteroaryl, C1 to C6 alkyl, C3 to C6, branched alkyl, C3 to G cyclic alkyl, partially or perfluorinated C1 to C6 alkyl, partially or perdeuterated C1 to C6 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C1o aryl, substituted or unsubstituted C3 to C12 heteroaryl, C1 to C6 alkyl, G to Q branched alkyl, C3 to C6 cyclic alkyl , partially or perfluorinated C1 to Cg alkyl, partially or perdeuterated C1 to Ci alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted G to CJ0 aryl, substituted or unsubstituted C3 to C10 heteroaryl, C1 to C1 alkyd, C3 to C1 branched alky l, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted C1 to C1o aryl, substituted or unsubstituted C3 to C1o heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C1 to G cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (M3), if present, are independently selected from D, substituted or unsubstituted G aryl, substituted or unsubstituted C3 to G heteroaryl, C1 to G alkyl, C3 to C4 branched alkyl, C3 G cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar of formulas (M1) and (Mg), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C1 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN.
According to an embodiment, Ar of formulas (M1) and (M3) is selected from the following D1 to Dip shown in Table 1 Ar of formula (M2) and (M4)
Ar of formulas (Ma) and (M4) is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C14 heteroaryl.
According to an embodiment, Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C2 to C18 heteroaryl.
According to an embodiment, Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted G to C12 heteroaryl.
According to an embodiment, Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted C6 to C1o aryl or substituted or unsubstituted C1 to C16 heteroaryl.
According to an embodiment, Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted Cfe aryl or substituted or unsubstituted C3 to C5 heteroaryl.
According to an embodiment, Ar of formulas (M2) and (M4) is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaiyl, wherein the heteroaiyl is a six-member ring.
According to an embodiment, Ar is selected from the group consisting of substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, and substituted or unsubstituted quinolinyl.
Substituents on Ar of formula (M2) and (M4)
Ar of formulas (M2) and (M4) may be unsubstituted or substituted with one or more substituents.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted G to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C13 alkyl, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to Cm branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, PX1(R8)2, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from C1, to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyd, partially or perfluorinated C1 to Cm alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from 0, S or Se, preferably 0. According to an embodiment, the one or more substituents on Ar of formulas (Ma) and (M4), if present, are independently selected from D, substituted or unsubstituted C() to C1B aryl, substituted or unsubstituted C3 to C1o heteroaryl, C1 to C1t, alkyl, C1 to C1* alkoxy, C3 to C16 branched alkyl, C3 to Clt, cyclic alkyl, C( to C1<> branched alkoxy, C3 to Cw c Cy1c6lic alkoxy, partially or perfluorinated to C1r> alky], partially or perfluorinated C1 to C1& alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy. PX1(R8)2, halogen, F or CN, wherein R8 is independently selected from C1 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to Cm alkoxy; and X' is selected from O, S or Se, preferably O.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C1& alkyl, C3 to C1& branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C1& alkyl, PX‘(R®)2, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring, wherein R8 is independently selected from G to C12 aryl, C3 to C12 heteroaryl, C1 to Cl(, alky l, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C18 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from 0, S or Se, preferably O.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyd, C1 to Clt, branched alky ] , C3 to C1* cyclic alky l, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyd, PX1(R8)2, halogen, F or CN, wherein Ra is independently selected from C1 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C1* alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C1& alkoxy; and X1 is selected from O, S or Se, preferably O. According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl, C3 to Ct6 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16, alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C18 aryl, substituted or unsubstituted C3 to C20 heteroaryl, C1 to C16 alkyl, C3 to C16 branched alkyl, C3 to C18 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted (fl to Cl4 heteroaryl, C1 to C1o alkyl, C3 to CI0 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C1o alkyl, partially or perdeuterated C1 to C1o alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted G to C12 aryl, substituted or unsubstituted C3 to C)4 heteroaryl, C1 to C1o alkyl, C3 to C1o branched alkyl, C3 to C1o cyclic alkyl, partially or perfluorinated C1 to C1o alkyl, partially or perdeuterated C1 to C1o alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted G to C1o aryl, substituted or unsubstituted C3 to C1a heteroaryl, C1 to C6 alkyl, C3 to G branched alkyl, C3 to C1 cyclic alkyl, partially or perfluorinated C1 to C1 alkyl, partially or perdeuterated C1 to G alkyl, halogen, F or CN, wherein the substituents may be linked via a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted G to C10 aryl, substituted or unsubstituted C3 to C1y heteroaryl, C1 to C1 alkyl, C3 to G branched alkyl, C3 to G cyclic alkyl, partially or perfluorinated C1 to C& alkyl, partially or perdeuterated C1 to G alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted G to C1o aryl, substituted or unsubstituted G to C10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to G cyclic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be linked ria a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar of formulas (Ma) and (M4), if present, are independently selected from D, substituted or unsubstituted G to C10 aryl, substituted or unsubstituted C3 to C1o heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C1 cy clic alkyl, partially or perfluorinated C1 to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN.
According to an embodiment, the one or more substituents on Ar of formulas (M2) and (M4), if present, are independently selected from D, substituted or unsubstituted C1 aryl substituted or unsubstituted C3 to C1 heteroaryl, C1 to C.} alkyl, C3 to C4 branched alkyl, C3 to C1 cyclic alky l, partially or perfluorinated C1 to C4 allyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents maybe linked ria a single bond or a heteroatom to form a ring.
According to an embodiment, the one or more substituents on Ar of formulas (Ma) and (M4), if present, are independently selected from D, substituted or unsubstituted G aryl, substituted or unsubstituted C3 to Cs heteroaryl, C1 to C4 alkyl, C3 to C4 branched allyl, C3 to C6 cyclic alkyl, partially or perfluorinated C( to C4 alkyl, partially or perdeuterated C1 to C4 alkyl, halogen, F or CN.
According to an embodiment, Ar of formulas (M2) and (M4) is selected from the following Di to D19 shoum in Table 1
Specific embodiments of the compound of formulas (M 1) to (M4)
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C® aryl, substituted or unsubstituted C2 to C® heteroaryl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; Rfr, Rfr, Rfoand RM are independently selected from H, D, substituted or unsubstituted C1 to C® alkyl, substituted or unsubstituted Cg to C24 aryl or substituted or unsubstituted C2 to CS4 heteroaryl, CN, halogen, F, C3 to C® branched alkyl, C3 to C® cyclic alkyl, partially or perfluorinated C1 to C® alkyd, partially or perdeuterated C1 to C® alkyl, or PX’CR8)® wherein R8 is independently selected from C6 to C® aryl, C3 to Ct2 heteroaryl, Ci to C® alkyl, C1 to C1G alkoxy, partially or perfluorinated C1 to C® alkyd, partially or pci-fluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C® alkyl, partially or perdeuterated C5 to C!(J alkoxy; and X1 is selected from 0, S or Se, preferably 0.
According to an embodiment, in formulas (M2) and (M4) Ra to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to Gia aiyl, substituted or unsubstituted C2 to C18 heteroaryl; and in formula (Ma) Ar is selected from a substituted or unsubstituted pjridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; Rb, RLb, Rfoand RIxi are independently selected from H, D, substituted or unsubstituted C1 to C® alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C3 to C16 branched alkyl, C3 to C® cyclic alkyl, partially or perfluorinated C1 to C® alkyl, partially or perdeuterated C1 to G® alkyl, or PX'(R8)S wherein R8 is independently selected from Ge to C® aryl, C3 to Cia heteroaryl, C1 to C® alkyl, C1 to C!6 alkoxy, partially or perfluorinated C1 to C® alkyl, partially or perfluorinated C1 to C1b alkoxy, partially or perdeuterated Cr to C® alkyl, partially or perdeuterated C5 to C® alkoxy; and X3 is selected from O, S or Se, preferably O; and in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C® aryl, substituted or unsubstituted C3 to C16 heteroaryl; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R’ to R7 are independently selected from H, or D; Rta, RLb, Rfoand RLb are independently selected from H, D, substituted or unsubstituted C1 to Clfi alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated Q to C16 alkyl, or PX1(R8)2 wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C4 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated Cj to C16 alkoxy; and X1 is selected from O, S or Se, preferably O; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2- quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C16 aryl, substituted or unsubstituted C2 to Cts heteroaiyl; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (Mi) and (M3) R’ to R7 are independently selected from H, or D; R1-3, Rli, Rfoancl RLb are independently selected from H, D, substituted or unsubstituted C> to C16 alkyl, substituted or unsubstituted Cb to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, partially or perfluorinated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkyl, or PX‘(R8)2 wherein R8 is independently selected from C6 to C1a aryl, C3 to Ci2 heteroaiyl, C1 to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from 0, 8 or Se, preferably O; and in formula (M1) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to Cia aryl or substituted or unsubstituted C2 to Ct2 heteroaryl
According to an embodiment, in formulas (M1) and (M3) R’ to R7 are independently selected from H, or D; RLb, RJ-b, Rfoand R1-*1 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to CJ4 heteroaryl, CN, halogen, F.
According to an embodiment, in formulas (M2) and (M4) R? to R" are independently selected from H, or D; L is selected from substituted or unsubstituted Cb to CJ2 aryl or substituted or unsubstituted C2 to C>2 heteroaiyl; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted 01 unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; RLb, RLb, R^.and Rljd are independently selected from H, D, substituted or unsubstituted C> to C16 alkyl, substituted or unsubstituted Ch to C24 ary] or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F; and in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to CA aryl or substituted or unsubstituted C2 to Cj2 heteroaryl; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; Ru“, Rtb, RLc,and RLb are independently selected from H, D, substituted or unsubstituted C1 to 0,6 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to Cia aryl or substituted or unsubstituted C2 to C12 heteroaryl; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; R1^, RIb, RLb,and R,J are independently selected from H, D, substituted or unsubstituted C1 to Ct6 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F; and in formula (M1) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to Cm aryl or substituted or unsubstituted C2 to C1<> heteroaryl. According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; RLb, RLb, RLb,and R1^ are independently selected from H, D, and substituted or unsubstituted C1 to CK, alkyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C«> aryl or substituted or unsubstituted C2 to Ct0 heteroaryl; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R” are independently selected from H, or D; R1-3, RLh, RLb,and Rk) are independently selected from H, D. and substituted or unsubstituted C1 to CS6 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted Cb to CM aryl or substituted or unsubstituted C2 to C1O heteroaryl' and in formula (Ma) Ar i s selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; RLb, RLb, Rfoand Rw are independently selected from H, D, and substituted or unsubstituted C1 to C16 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (Ma) and (M4) Ra to Rt are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to CI0 aiyl or substituted or unsubstituted C2 to C10 heteroaryl; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R' to R7 are independently selected from H, or D; R1-1, RLb, Rfoand RLb are independently selected from H, D, and substituted or unsubstituted C1 to Cfo alkyl; and in formula (M1) Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C3 to Cs heteroaryl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; RM, RLb, Rix,and R^3 are independently selected from H, D, and substituted or unsubstituted C> to alkyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R~ are independently selected from H, or D; L is selected from substituted or unsubstituted Cg to C1O aryl or substituted or unsubstituted C:1 to C5 heteroaryl; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl. According to an embodiment, in formulas (M1) and (M3) R’ to R7 are independently selected from H, or D; Rfr, Rte,and Rfr are independently selected from H, D, and substituted or unsubstituted C> to Cia alkyl; and in formula (M1) Ar is selected from a substituted or un substituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R7 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C3 to C5 heteroaryl; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; R1*, RLb, R:x,and Riid are independently selected from H, D, and substituted or unsubstituted C1 to Cl3 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) Ra to R' arc independently selected from H, or D; L is selected from substituted or unsubstituted C6 to Clo aryl or substituted or unsubstituted C3 to Cs heteroaryl; and in formula (M2) Ar is selected from a:i unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R‘ to R7 are independently selected from H, or D; Rkl, R1h, R'qand RIx! are independently selected from H, D, and substituted or unsubstituted C1 to C12 alkyd; and in formula (M1) Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted Cg to C1o,aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein heteroaryl is a six-member ring.
According to an embodiment, in formulas (M1) and (M3) R* to R7 are independently selected from H, or D; R1-3, RLb, RLb,and RIzI are independently selected from H, D, and substituted or unsubstituted C1 to Ca alkyl.
According to an embodiment, in formulas (M2) and (M4) R- to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted Ch to C(1, aryl, or substituted or unsubstituted C( to C-, hetcroaryl, wherein heteroaryl is a six-member ring; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl. According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; RLb, RLb>, R’foand RIJ are independently selected from H, D, and substituted or unsubstituted C1 to C* alkyl; and in formula (M1) /Xr is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) Rz to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted C6 to C10 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein heteroaryl is a six-member ring; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; RM, RLb, Rfoand R^* are independently selected from H, D, and substituted or unsubstituted C1 to C6 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (Ma) and (M4) Rz to R~ are independently selected from H, or D; L is selected from substituted or unsubstituted C6 aryl, substituted or unsubstituted naphthyl, or substituted or unsubstituted C3 to C5 heteroaryl, wherein heteroaryl is a six-member ring; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R" are independently selected from H, or D; Rfo, RLb, Rfoand R^ are independently selected from H, D, and substituted or unsubstituted C1 to Cg alkyl; and in formula (M1) Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to fo are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl. According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; Rfo RLb, Rfoand R1^ are independently selected from H, D, and substituted or unsubstituted C1 to C6 alkyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, p\Tazinyl, pyrimidyl, triazinyl; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R’ to R7 are independently selected from H, or D; Ri a, RL\ R'qand RLib are independently selected from H, D, and substituted or unsubstituted C1 to Cf, alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; Rfo, RLb, R’frand RLb are independently selected from H, D, and substituted or unsubstituted C1 to Cb alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; 1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, pjTazinyl, pyrimidyl, triazinyl; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R’ to R7 are independently selected from H, or D; R^', Rtb, Rix,and RLbl are independently selected from H, D, and substituted or unsubstituted C1 to Cb alkyl; and in formula (M1) Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl.
According to an embodiment, in formulas (M1) and (M3) R‘ to R7 are independently selected from H, or D; Rto R1*, Rfoand R^ are independently selected from H, D, and substituted or unsubstituted C1 to C4 alkyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (Mi) and (M3) R1 to R' are independently selected from H, or D; RLb, RLb, Rfoand RLb are independently selected from H, D, and substituted or unsubstituted C1 to C4 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (Ma) and (M4) R2 to R? are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; and in formula (Ma) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R* to R? are independently selected from H, or D; Rfr*, RLb, Rte and R1^ are independently selected from H, D, and substituted or unsubstituted C1 to C« alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to W are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) Ra to R? are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23.
According to an embodiment, in formulas (M1) and (M3) R* to R? are independently selected from H, or D; Ru', R1 b, RLb,and R1^ are independently selected from H, D, and substituted or unsubstituted C1 to C3 alkyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R? are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R? are independently selected from H, or D; R1-3, Rt, R^and RLb are independently selected from H, D, and substituted or unsubstituted C1 to C3 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl
According to an embodiment, in formulas (Ma) and (M4) R2 to R~ are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2- quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R? are independently selected from H, or D: Ru , RLb. RL’b,and R1-4 are independently selected from H, D, and substituted or unsubstituted C1 to C3 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from E1 to E5, and E8 to E23; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; RLb, RLb, RI-c,and Rw are independently selected from H, D, and substituted or unsubstituted Ch to C3 alkyl; and in formula (M1) Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; Lis selected from E1 to Eg, and E8 to E23.
According to an embodiment, in formulas (M1) and (M3) R' to R7 are independently selected from H, or D; RLb, R'-1’, Rfoand RLb are independently selected from H, D, and substituted or unsubstituted C1 to C2 allyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from Ea, E3, E8, Eg, Eu, E14 and E15; and in formula (Ma) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; R1-3, RLb, R’frand Rw are independently selected from H, D, and substituted or unsubstituted Ch to C2 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (Ma) and (M4) R2 to R7 are independently selected from H, or D; Lis selected from E2, E3, E8, E9, E1i, Ei4,Eig, and E16; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R~ are independently selected from H, or D; RM, R1* RLb,and R1*1 are independently selected from H, D, and substituted or unsubstituted C( to C2 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R- to R" are independently selected from H, or D; L is selected from E2, E3, E8, Eg, E1i, Ei4,Eig; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R" are independently selected from H, or D; R'A RLb, R’frand R1^ are independently selected from H, D, and substituted or unsubstituted C1 to C2 alkyl; and in formula (M1) Ar is selected from an unsubstituted 2- pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from Ea to E3, E1i, and E16.
According to an embodiment, in formulas (M1) and (M3) R2 to R7 are independently selected from H, or D; R^1, RLb, RLb,and Rw are independently selected from H, D, and substituted or unsubstituted C1 alkyl.
According to an embodiment, in formulas (M2) and (M4) Rz to R7 are independently selected from H, or D; L is selected from E2 to E3, E11, E16; and in formula (M2) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl .
According to an embodiment, in formulas (M1) and (M3) R> to R" are independently selected from H, or D; R’A RLb, R^, and RLb are independently selected from H, D, and substituted or unsubstituted C1 alkyd ; and in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M2) and (M4) R2 to R7 are independently selected from H, or D; L is selected from E2 to E3, E1i, and E16; and in formula (M2) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2- quinoline group, or substituted or unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R7 are independently selected from H, or D; R13, RLb, Rfoand R1^ are independently selected from H, D, and substituted or unsubstituted C1 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl. According to an embodiment, in formulas (M2) and (M4) R® to R? are independently selected from H, or D; L is selected from Ea to E3, En, and E16; and in formula (M2) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl.
According to an embodiment, in formulas (M1) and (M3) R1 to R~ are independently selected from H, or D; RUl, R1b, Rfoand R1/I are independently selected from H, D, and substituted or unsubstituted C1 alkyd; and in formula (M1) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl. The compound of formulas (M1) to (M4) may be selected from the compounds I-i to I-298 shown in Table 3 above, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
The compound of formulas (M1) to (M4) maybe selected from the compounds shown in Table 4 above, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
The compound of formulas (M1 ) to (M4) may be selected from the compounds shown in Table 5 above, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
The compound of formulas (M1) to (M4) may be selected from the compounds shown in Table
6 above, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
The compound of formulas (M i) to (M4) may be selected from the compounds shown in Table
7 above, wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 13
Table 13
OS I
wherein the respective compound can be undeuterated, partially deuterated or folly deuterated.
According to an embodiment, the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 14
Table 14
wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 15
Table 15:
wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 16
Table 16:
wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formulas (M1) to (M4) is selected from the compounds shown in Table 17
Table 17:
wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
According to an embodiment, the compound of formula (I) is selected from the compounds shown in Table 18.
Table J8: wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
The compound of formulas (M1) to (M4) may be selected from the compounds I-125, 1-126, 1- 151, 1-2 and I-152
wherein the respective compound can be undeuterated, partially deuterated or fully deuterated.
Another aspect of the present invention provides a semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
Another aspect of the present invention provides a semiconducting layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
Another aspect of the present invention provides an electronic device comprising an semiconductor layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
According to an embodiment of the present invention, the electronic device is an organic electronic device. According to an embodiment, the electronic device comprises an electroluminescent device, an organic light emitting diode (OLED), a light emitting device, thin film transistor, a battery, a display device or an organic photovoltaic cell (OPV).
Another aspect of the present invention provides a display device comprising an organic electronic device comprising a semiconductor layer comprising the semiconducting materia] comprising at least on compound selected from the group of compounds of formula (M1) or (M2).
Hereinafter, the embodiments are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following examples. Reference will now be made in detail to the exemplary aspects.
Description of the Drawings
The aforementioned components, as well as the claimed components and the components to be used in accordance with the invention in the described embodiments, are not subject to any special exceptions with respect to their size, shape, material selection and technical concept such that the selection criteria known in the pertinent field can be applied without limitations.
Additional details, characteristics and advantages of the object of the invention are disclosed in the dependent claims and the following description of the respective figures which in an exemplar)' fashion show preferred embodiments according to the invention. Any embodiment does not necessarily represent the full scope of the invention, however, and reference is made therefore to the claims and herein for interpreting the scope of the invention. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are intended to provide further explanation of the present invention as claimed.
FIG. 1 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
FIG. 2 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
FIG. 3 is a schematic sectional xiew of an organic electroluminescent device according to an exemplary embodiment of the present invention.
FIG. 4 is a schematic sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.
Hereinafter, the figures are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following figures. Herein, when a first element is referred to as being formed or disposed "on" or “onto” a second element, the first element can be disposed directly on the second element, or one or more other elements may be disposed there between. When a first element is referred to as being formed or disposed "directly on" or “directly onto” a second element, no other elements are disposed there between.
Fig. i is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
Referring to Fig. i the organic electroluminescent device too includes an anode layer (ANO) 120, a first emission layer (EML1) 145, and a first electron transport layer (ETLi) 149, wherein the first electron transport layer (ETLi) 149 is free of 8-Hydroxyquinolinolato4ithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
The organic electroluminescent device further comprises a first charge generation layer (CGLi) 160 disposed over the first electron transport layer (ETLi) 149, wherein the first charge generation layer (CGLi) 160 comprises a first n-type charge generation layer (n-CGLi) 161, and a first p-type charge generation layer (p-CGLi) 162, wherein the first n-tjpe charge generation layer (n-CGLi) 161 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (ETLi) 149 is in direct contact with the first n-type charge generation layer (n-CGLi) 161.
The organic electroluminescent device 100 farther comprises a second emission layer (EML2) 245, and a cathode layer (CAT) 190.
Fig. 2 is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
Referring to Fig. 2 the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a first hole transport layer (HTLi) 141, a first electron blocking layer (EBL1) 142, a first emission layer (EMLi) 145, a first optional hole blocking layer (HBLi) 147, and a first electron transport layer (ETLi) 149, wherein the first electron transport layer (ETLi) 149 is free of 8-Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
The organic electroluminescent device further comprises a first charge generation layer (CGLi) 160 disposed over the first electron transport layer (ETLi) 149, wherein the first charge generation layer (CGLi) 160 comprises a first n-type charge generation layer (n-CGLi) 161, and a first p-type charge generation layer (p-CGLi) 162, wherein the first n-type charge generation layer (n-CGLi) 161 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (ETLi) 149 is in direct contact with the first n-tjpc charge generation layer (n-CGLi) 161. The organic electroluminescent device 100 further comprises a second hole transport layer (HTL2) 241, a second electron blocking layer (EBL2) 242.
The organic electroluminescent device too further comprises a second emission layer (EML2) 245.
The organic electroluminescent device 100 further comprises a second optional hole blocking layer (HBL2) 247, an electron transport layer (ETL) 148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.
Fig. 3 is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
Referring to Fig. 3 the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a hole transport layer (HTL1) 141, a first electron blocking layer (EBLi) 142, and a first emission layer (EMLi) 145.
The organic electroluminescent device 100 further comprises a first optional hole blocking layer (HBLi) 147.
The organic electroluminescent device 100 further comprises a first electron transport layer (ETLi) 149, wherein the first electron transport layer (ETLi) 149 is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
The organic electroluminescent device further comprises a first charge generation layer (CGLi) 160 disposed over the first electron transport layer (ETLi) 149, wherein the first charge generation layer (CC1Li) 160 comprises a first n-type charge generation layer (n-CGLi) 161, and a first p-type charge generation layer (p-CGLi) 162, wherein the first n-type charge generation layer (n-CGLi) 161 comprises a compound offbrmula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (ETLi) 149 is in direct contact with the first n-type charge generation layer (n-CGLi) 161.
The organic electroluminescent device 100 further comprises a second hole transport layer (HTL2) 241, and a second electron blocking layer (EBL2) 242.
The organic electroluminescent device 100 further comprises a second emission layer (EML2) 245.
The organic electroluminescent device 100 further comprises a second optional hole blocking layer (HBLa) 247.
The organic electroluminescent device 100 further comprises a second electron transport layer (ETL2) 249, wherein the second electron transport layer (ETL2) 249 is free of 8- Hydroxj-quinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
The organic electroluminescent device further comprises a second charge generation layer (CGLa) 260 disposed over the second electron transport layer (ETLa) 249, wherein the second charge generation layer (CGL2) 260 comprises a second n-type charge generation layer (n- CGL2) 261, and a first p-type charge generation layer (p-CGL2) 262, wherein the second n- type charge generation layer (n-CGL2) 261 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the second electron transport layer (ETLi) 249 is in direct contact with the second n-type charge generation layer (n-CGLa) 261, wherein the second n-type charge generation layer (n-CGL2) 261 can be selected the same or different than the first n-type charge generation layer (n-CC1Li) 161, and wherein the second p-type charge generation layer (p-CGL2) 262 can be selected the same or different than the first p-type charge generation layer (p-CGLi) 161.
The organic electroluminescent device 100 further comprises a third hole transport layer (HTL3) 341, and a third electron blocking layer (EBL3) 342.
The organic electroluminescent device 100 further comprises a third emission layer (EML3) 345.
The organic electroluminescent device 100 further comprises a third optional hole blocking ayer (HBL3) 347> an electron transport layer (ETL)148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.
Fig, 4 is a schematic sectional view of an organic electroluminescent device 100, according to one exemplary embodiment of the present invention.
Referring to Fig. 4 the organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a hole transport layer (HTLi) 141, a first electron blocking layer (EBL1) 142, a first emission layer (EML1) 145.
The organic electroluminescent device 100 further comprises a first optional hole blocking layer (HBLi) 147.
The organic electroluminescent device 100 further comprises a first electron transport layer (ETLi) 149, wherein the first electron transport layer (ETLi) 149 is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
The organic electroluminescent device further comprises a first charge generation layer (CGL) 160 disposed over the first electron transport layer (ETLi) 149, wherein the first charge generation layer (CC1Li) 160 comprises a first n-type charge generation layer (n-CGL) 161, and a first p-type charge generation layer (p-CGL) 162, wherein the first n-type charge generation layer (n-CGL) 161 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the first electron transport layer (ETLi) 149 is in direct contact nnth the first n-type charge generation layer (n-CGL) 161.
The organic electroluminescent device 100 further comprises a second hole transport layer (HTL2) 241, and a second electron blocking layer (EBL2) 242.
The organic electroluminescent device 100 further comprises a second emission layer (EMLa) 245.
The organic electroluminescent device 100 further comprises a second optional hole blocking layer (HBL2) 247.
The organic electroluminescent device 100 farther comprises a second electron transport layer (ETLs) 2,49, wherein the second electron transport layer (ETL2) 249 is free of 8- Hydroxyquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
The organic electroluminescent device further comprises a charge generation layer (CC1L) 260 disposed over the second electron transport layer (ETL2) 249, wherein the second charge generation layer (CGL2) 260 comprising a second n-type charge generation layer (n-CGL) 261, and a second p-type charge generation layer (p-CGL) 262, wherein the second n-type charge generation layer (n-CGL) 261 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Yterbium, and wherein the second electron transport layer (ETL2) 249 is in direct contact wth the second n-type charge generation layer (n-CGLa) 261, wherein the second n-type charge generation layer (n-CGL2) 261 can be selected the same or different than the first n-type charge generation layer (n-CGLi) 161, and wherein the second p-type charge generation layer (p-CGLa) 262 can be selected the same or different than the first p-type charge generation layer (p-CGLi) 161.
The organic electroluminescent device 100 farther comprises a third hole transport layer (HTL3) 341, and a third electron blocking layer (EBL3) 342.
The organic electroluminescent device 100 further comprises a third emission layer (EML3) 345-
The organic electroluminescent device 100 farther comprises a third optional hole blocking layer (HBL3) 347.
The organic electroluminescent deuce too further comprises a third electron transport layer (ETL3) 349, wherein the third electron transport layer (ETL3) 349 is free of 8- Hydroxwquinolinolato-lithium, preferably free of a lithium organic metal complex, and more preferably free of a lithium metal complex.
The organic electroluminescent device further comprises a charge generation layer (CGL3) 360 disposed over the third electron transport layer (ETL3) 349, wherein the third charge generation layer (CC1L3) 360 comprising a third n-typc charge generation layer (n-CGL.3) 361, and a third p-type charge generation layer (p-CGLg) 362, wherein the third n-t\pe charge generation layer (n-CC1Lg) 361 comprises a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from Ytterbium, and wherein the third transport layer (ETL3) 349 is in direct contact with the third n-type charge generation layer (n-CC1Lg) 361, wherein the third n-type charge generation layer (n-CGLg) 361 can be selected the same or different than the first n-type charge generation layer (n-CGLi) 161, and wherein the third p- type charge generation layer (p-CGLg) 362 can be selected the same or different than the first p-type charge generation layer (p-CGLi) 161.
The organic electroluminescent device 100 further comprises a fourth hole transport layer (HTL4) 441, and a fourth electron blocking layer (EBL4) 442,
The organic electroluminescent device 100 farther comprises a fourth emission layer (EML4) 345-
The organic electroluminescent device 100 farther comprises a fourth optional hole blocking layer (HBL4) 447, an electron transport layer (ETL) 148, an electron injection layer (EIL) 180, and a cathode layer (CAT) 190.
While not shown in Fig. 1, Fig. 2, Fig. 3 and Fig. 4, a sealing layer may further be formed on the cathode electrodes 190, in order to seal the OLEDs 100. In addition, various other modifications may be applied thereto.
Hereinafter, the embodiments are illustrated in more detail with reference to examples. However, the present disclosure is not limited to the following examples.
Detailed description
The invention is furthermore illustrated by the following examples which are illustrative only and non-binding.
Sublimation temperature
Under nitrogen in a glovebox, 0.5 to 5 g compound are loaded into the evaporation source of a sublimation apparatus. The sublimation apparatus consist of an inner glass tube consisting of bulbs with a diameter of 3 cm which are placed inside a glass tube with a diameter of 3.5 cm. The sublimation apparatus is placed inside a tube oven (Creaphys DSU 05/2.1). The sublimation apparatus is evacuated via a membrane pump (Pfeiffer Vacuum MVP 055- 3C) and a turbo pump (Pfeiffer Vacuum THM071 YP). The pressure is measured between the sublimation apparatus and the turbo pump using a pressure gauge (Pfeiffer Vacuum PKR 251). When the pressure has been reduced to lo-s mbar, the temperature is increased in increments of 10 to 30 K till the compound starts to be deposited in the harvesting zone of the sublimation apparatus. The temperature is further increased in increments of 10 to 30 K till a sublimation rate is achieved where the compound in the source is visibly depleted over 30 min to 1 hour and a substantial amount of compound has accumulated in the harvesting zone.
The sublimation temperature, also named TM)bi, is the temperature inside the sublimation apparatus at which the compound is deposited in the harvesting zone at a visible rate and is measured in degree Celsius.
In the context of the present invention, the term “sublimation “ may refer to a transfer from solid state to gas phase or from liquid state to gas phase.
Decomposition temperature
The decomposition temperature, also named Tdec, is determined in degree C6lsius.
The decomposition temperature is measured by loading a sample of 9 to n mg into a Metler Toledo 100 pL aluminum pan without lid under nitrogen in a Mettler Toledo TGA-DSC imachine. The following heating program was used: 25°C isothermal for 3 min; 25°C to 6oo°C with 10 K/min.
The decomposition temperature was determined based on the onset of the decomposition in TGA.
Calculated LUMP and dipole moment
The LUMO energy level and the dipole moment are calculated with the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometries and the HOMO and LUMP energy levels of the molecular structures are determined by applying the hybrid functional B3LYP with a 6~31G* basis set in the gas phase. If more than one conformation is viable, the conformation with the lowest total energy is selected.
Materials for first n-type charge generation layer are shown in Table 10:
Table 10:
Materials for first electron transport layer are Table 11
General procedure for fabrication of OLEDs
For the examples according to the invention and comparative examples in Table 12, a glass substrate with an anode layer comprising a first anode sub-layer of 10 nm ITO, a second anode sub-layer of 120 nm Ag and a third anode sub-layer of 8 nm ITO was cut to a size of too mm x 100 mm x 0.7 mm, ultrasonically washed with water for 60 minutes and then with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, followed by plasma treatment, see Table 12, to prepare the anode layer. The plasma treatment was performed in an atmosphere comprising 97.6 voI.-% nitrogen and 2.4 voh-% oxygen.
Then N-([1,1'-bipheiiyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H- fluoren-2-amine was vacuum deposited with 2 wt.-% 2,2’,2"-(cyclopropane-1,2,3- triylidenc)tris(2-(p-cyanotetrafluorophenyl)acetonilrile)to form a hole injection layer havng a thickness 10 nm.
Then N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N“(4-(9-phenyl-9H-carbazol-3-yI)plienyl)-9H- fluoren-2 -amine was vacuum deposited, to form a first hole transport layer havng a thickness of 29 nm Then N-([i,i'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenvlsilyl)phenyl)-9H-fluoren-2-amine was vacuum deposited on the HTL, to form an electron blocking layer (EBL) having a thickness of 5 nm.
Then 97 wt.-% H09 (Sun Fine Chemicals, Korea) as EML host and 3 wt.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant were deposited on the EBL, to form a first blueemitting emission layer (EML) with a thickness of 20 nm.
Then, the first electron transporting layer (ETL1) having a thickness of 15 nm is formed on first emission layer by depositing a compound according Table 12. The first electron transporting layer is free of 8-Hydroxyquinolinolato-lithium.
Then an n-type CGL having a thickness of 8 nm is formed on the ETLi by co-depositing 90.1 wt.-% of an electron transport compound (ETM of n-CGL) according to Table 12 and 9.9 wt.- % Yb.
Then a p-type CGL having a thickness of 10 nm is formed on the n-type CGL by co-depositing N-(fi,i’-bipheny!]-4-yl)-9,9-dimethj'l-N-(4-(9-phenyl-9H-carbaZol-3-yl)phenyl)-9H-fluoren- 2-amine with 10 wt% 2,2',2"-(cyclopropane-i,2,3-triylidene)tris(2-(p- cyanotetrafluorophenyl)acetonitrile) as organic p-dopant.
Then a second hole transport layer having a thickness of 45 nm is formed on the first p-type CGL by depositing N-([i,i'-biphenj'l]-4-yl)-9,9-dimetliyl-N-(4-(9-phcnyl-9H-carbazol-3- yl)phenyl)-9H-fluoren-2-amine.
Then a second electron blocking layer having a thickness of 5 nm is formed on the second hole transport layer by depositing N-([i,i'-biphenyl]-4-yl)-9,9-diphenyl-N-(4- (triphenylsilyl)phenyl)-9H-fluoren-2-amine.
Then 97 wt.-% H09 (Sun Fine Chemicals, Korea) as EML host and 3 wt.-% BD200 (Sun Fine Chemicals, Korea) as fluorescent blue dopant were deposited on the second EBL, to form a second blue-emiting EML with a thickness of 19 nm.
Then 2-(3'-(9J9-dimethyl-9H-fluoren-2-yl)-[i,i'-biphenyl]-3-yl)-456-diphenyl-i,3,5-triazine was vacuum deposited to form a second hole blocking layer having a thickness of 5 nm is formed on the second blue-emitting EML.
Then, 50 wt.-% 4M4-(4-(4,6-diphenyl-i,3,5-triazin-2-y])phenyl)naphthalen-i-yl)-[i,i’- biphenyH-4-carbonitrile and 50 wt.-% LiQ were vacuum deposited on the second hole blocking layer to form a second electron transport layer having a thickness of 31 nm.
Then Yb was evaporated at a rate of 0.01 to 11/s at io~7 mbar to. form, an electron injection layer with a thickness of 1 nm on the electron transporting layer. Ag/Mg (1:8 wt%) is evaporated at a rate of 0.01 to 1 A/s at io-7 mbar to form a cathode with a thickness of 13 nm.
Then, N-({[i,i-‘biphenyl]-4-yl)-9,9,dimethyl-N-(4-(g-phenyl-9H-carbazoI-3-yl)phcnyD-9H- fluoren-2 -amine} was vacuum deposited on the cathode layer to form a capping layer with a thickness of 75 nm.
To assess the performance of the inventive examples compared to the prior art, the current efficiency is measured at 20°C. The current-voltage characteristic is determined using a Keithley 2635 source measure unit, by sourcing a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device is varied in steps of 0.1V in the range between oV and 10V. Likewise, the luminance-voltage characteristics and CIE coordinates are determined by measuring the luminance in cd/m2 using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)) for each of the voltage values. The cd/ A efficiency at 15 mA/cma is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.
In bottom emission devices, the emission is predominately Lambertian and quantified in percent external quantum efficiency (EQE). To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA/cma.
In top emission devices, the emission is forward directed, non-Lambertian and also highly dependent on the mircocavity. Therefore, the efficiency EQE will be higher compared to bottom emission derices. To determine the efficiency EQE in % the light output of the device is measured using a calibrated photodiode at 15 mA/cm2.
Lifetime IT of the device is measured at ambient conditions (2O°C) and 30 mA/cm2, using a Keithley 2400 sourcemeter, and recorded in hours.
The brightness of the device is measured using a calibrated photo diode. The lifetime LT is defined as the time till the brightness of the device is reduced to 97 % of its initial value.
The increase in operating voltage AU is used as a measure of the operational voltage stability of the device. This increase is determined during the LT measurement and by subtracting the operating voltage after 1 hour after the start of operation of the device from the operating voltage after 100 hours.
AIHU100 h)- U(ih)].
The smaller the value of AU the better is the operating voltage stability.
Technical Effect of the invention
Table 12:
Comparative device Ci comprises an electron transport layer contacting the n-type charge generation layer containing 8-Hydroxyquinolinolato-lithium (LiQ) and compound ET-i, and an n-type charge generation layer containing compound C-4.
The comparative device C2 comprises an electron transport layer contacting the n-type charge generation layer containing 8-Hydroxyquinolinolato-lithium (LiQ) and compound ET-i, and an n-type charge generation layer containing compound I-i.
The comparative device C3 comprises an electron transport layer contacting the n-type charge generation layer containing 8-Hydroxyquinolinolato-lithium (LiQ) and compound ET-i, and an n-type charge generation layer containing compound I- 2.
The comparative device C4 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-i and in contrast to comparative device Ci does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and an n-type charge generation layer containing compound ET-2. The compound ET-2 contains two phenthroline groups.
The comparative device C5 comprises an electron transport layer contacting the n-type charge generation layer containing the compound C-2 and does not contain 8-Hydroxyquinolinolato- lithium (LiQ),, and an n-type charge generation layer containing compound C-2. The compound C-2 contains a pyrazine group and a imidazo[i,5-a]pyridine group.
The comparative device C6 comprises an electron transport layer contacting the n-type charge generation layer containing the compound C-3 and does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and an n-type charge generation layer containing compound C-3. The compound C-3 contains a dibenzoacridine group and a imidazo[i,s-a]pyridine group.
The comparative device Cy comprises an electron transport layer contacting the n-type charge generation layer containing the compound C-4 and does not contain 8-Hydroxyquinolmolato- lithium (LiQ), and an n-type charge generation layer containing compound C-4. The compound C-4 contains a dibenzoacridinc group and a substituted imidazo[i,5-a] group.
The comparative device C8 comprises an electron transport layer contacting the n-type charge generation layer containing the compound C-i and the electron transport layer does not contain 8-HydroxyquinoEnolato-lithium (LiQ), and an n-type charge generation layer containing compound C-i. The compound C-i contains one phenthroline group. The inventive device II comprises an electron transport layer contacting the Ji-type charge generation layer containing the compound ET-i, and in contrast to comparative device Cg the electron transport layer does not contain 8-Hydroxyquinolinolato-lithtain (LiQ), and the n- type charge generation layer containing compound ET-3. The compound ET-3 contains a phenthroline group and a substituted imidazo[i,5-a] group.
The inventive device I2 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-i, and in contrast to comparative device C3 the electron transport layer does not contain 8-Hydroxyquinolmolato-lithium (LiQ), and the n- type charge generation layer containing compound I-2. The compound 1-2 contains a phenthroline group and a substituted imidazo[i,5-a] group.
The inventive device I3 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-2 instead of the compound ET-i according to inventive device Ii, and the electron transport layer does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
The inventive device I4 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-5 instead of the compound ET-i according to inventive derice Ii, and the electron transport layer does not contain 8-HydroxyquinoIinolato- lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
The inventive derice I5 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-4 instead of the compound ET-i according to inventive device II, and the electron transport layer does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
In inventive device 16, the organic electroluminescent derice comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-6 instead of the compound ET-i according to inventive device Ii, and the electron transport layer does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
The inventive derice I7 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-3 instead of the compound ET-i according to inventive derice II, and the electron transport layer does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and the n-type charge generation layer containing compound ET-3.
The inventive derice 18 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-7 instead of the compound ET-i according to inventive device U, and the electron transport layer does not contain 8-Hydroxyquinolinolato- lithium (LiQ), and the n-hpe charge generation layer containing compound ET-3.
The inventive derice I9 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-i, and in contrast to comparative device C3 the electron transport layer does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and the n- type charge generation layer containing compound I-126. The compound I-126 contains a phenthroline group and a substituted imidazo[i,5-a] group.The inventive derice I10 comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-1, and in contrast to comparative device C3 the electron transport layer does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and the n-type charge generation layer containing compound I-151. The compound I-151 contains a phenthroline group and a substituted imidazo[i;5-a] group.
The inventive device In comprises an electron transport layer contacting the n-type charge generation layer containing the compound ET-i, and in contrast to comparative device C3 the electron transport layer does not contain 8-Hydroxyquinolinolato-lithium (LiQ), and the n- type charge generation layer containing compound I-125. The compound I-125 contains a phenthroline group and a substituted imidazo[i,5-a] group.
In the comparative example Ci and C5, compound ET-2 is used in the n-type charge generation layer. In comparative example C5, the electron transport layer contacting the n-type charge generation layer does not contain Hydroxyquinolinolato-lithium (LiQ) in contrast to comparative example Ci. However, it is apparent that the voltage rise over time is still very high.
In the comparative device Ci and C5, compound C-4 is used in the n-type charge generation layer. In comparative example C5, the electron transport layer contacting the n-type charge generation layer does not contain Hydroxyquinolinolatoditliium (LiQ) in contrast t> comparative example Ci. However, it is apparent that the voltage rise over time is still ven’ high.
The inventive device I3 or I4, respectively differs from the comparative device C3 or C4, respectively in that the inventive detice I3 or Iq, respectively does not contain Hydroxyquinolinolatodithium in the electron transport layer contacting the n-type charge generation layer.
The inventive device II to In does not comprise Hydroxyquinolinolato-lithium in the electron transport layer contacting the n-type charge generation layer.
The comparative devices Ci to C5 contains Hydroxyquinolinolato-lithium in the electron transport layer contacting the n-type charge generation layer.
The inventive devices ll to In further differ from the comparative derice Ci to C4 in that the inventive devices II to Ill contain a compound according to formula (I) in the n-type charge generation layer.
It is apparent that all inventive devices exhibit a remarkable lower voltage rise over time compared to the comparative derices Ci to C4. At the same time the operational voltage is still low, and the current efficiency is still very high. The inventive device II to In and the comparative devices C5 to C9, all does not comprise Hydroxyquinolmolato-Iithium in the electron transport layer contacting the n-type charge generation layer.
The inventive devices h to ludiffer from the comparative device C5 to Cp in that the inventive devices II to In contain a compound according to formula (I) in the n-type charge generation layer.
It is apparent that all inventive devices exhibit a lower voltage rise over time compared to the comparative devices C5 to C9. At the same time the operational voltage is still low, and the current efficiency is still very high.
Thus, an inventive device comprising a compound of formula (I) in the n-type charge generation layer, and an electron transport layer contacting the n-type charge generation layer which is free of Hydroxyquinolinolato-lithium exhibit a remarkable low voltage rise over time, and at the same time a low operational voltage and a high current efficiency.
A low operating voltage may be important for the battery life of organic electronic devices, in particular mobile deuces.
A high efficiency may be beneficial for reduced power consumption and improved battery life, in particular in mobile deuces.
A low voltage rise over time may result in improved long-term stability of electronic devices.
Table 2 : Properties of compounds of formula (M) and compa rative example 1
As materials for organic electronics are typically purified by sublimation, a large offset between decomposition and sublimation temperature TdeC-TSUbi are highly desirable. Thereby, a high sublimation rate may be achievable which may be beneficial for the mass production under vacuum thermal evaporation conditions.
The particular combinations of elements and features in the above detailed embodiments areexemplary only; the interchanging and substitution of these teachings with other teachings in this and the patents/applications incorporated by reference are also expressly contemplated. As those skilled in the art will recognize, variations, modifications, and other implementations of what is described herein can occur to: those of ordinary skill in the art without departing from the spirit and the scope of the invention as claimed. Accordingly, the foregoing description is by way of example only and is not intended as limiting. In the claims, the word "comprising" does not exclude other elements or steps, and the indefinite article "a" or "an" does not exclude a plurality- The mere fact that certain measures are recited in mutually different dependent claims does not indicate that a combination of these measured cannot be used to advantage. The invention's scope is defined in the following claims and the equivalents thereto. Furthermore, reference signs used in the description and claims do not limit the scope of the invention as claimed.

Claims

Claims i. An organic electroluminescent device comprising an anode layer, a cathode layer, a first emission layer, a second emission layer, a first charge generation layer, and a first electron transport layer, wherein
- the first charge generation layer is arranged between the first emission layer and the second emission layer;
- the first electron transport layer is arranged between the first emission layer and the second emission layer;
- the first charge generation layer comprises a first n-type charge generation layer and a first p-type charge generation layer;
- the first n-type charge generation layer is doser to the anode layer than the first p- type charge generation layer and the first p-type charge generation layer is closer to the cathode layer than the first n-type charge generation layer;
- the first electron transport layer is arranged in direct contact with the first n-type charge generation layer;
- the first electron transport layer is free of 8-hydroxyquinolinolato-lithium;
- the first n-type charge generation layer comprises a metal dopant and the metal dopant is Yb;
- the first n-type charge genera tion layer comprises a compound of formula (I) wherein in formula (I)
- Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl; - R1 to R" are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to CK, branched alkyl, C3 to C1 cyclic alkyl, C3 to Cto branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfl uorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX‘(R8)a wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to 0,6 alkyl, C1 to GW alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy; and X1 is selected from O, S or Se, preferably 0; and
- L is selected from substituted or unsubstituted C6 to C24 aryl, substituted or unsubstituted C2 to C24 heteroaryl. The organic electroluminescent device according to claim 1, wherein Ar is selected from substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C2 to C12 heteroaryl, The organic electroluminescent device according to claim 1 or 2, wherein Ar is selected from the group consisting of substituted or unsubstituted phenyl or substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidyl, substituted or unsubstituted triazinyl, and substituted or unsubstituted quinolinyl. The organic electroluminescent device according to any of the preceding claims, wherein R1 to R7 are independently selected from the group consisting of H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C14 and or substituted or unsubstituted C2 to C12 heteroaryl, and halogen. The organic electroluminescent device according to any of the preceding claims, wherein R1 to R7 are independently selected from the group consisting of H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, and halogen. The organic electroluminescent device according to any of the preceding claims, wherein L is selected from the group consisting of substituted or unsubstituted C6 to C12 aryl or substituted or unsubstituted C2 to C12 heteroaryl. The organic electroluminescent device according to any of the preceding claims, wherein L is selected from the group consisting of substituted or unsubstituted phenyl. The organic electroluminescent device according to any of the preceding claims, wherein the compound of formula (I) has a LUMO energy lev el when calculated with the program package TURBOMOLE V6.5 by applying the hybrid functional B3LYP with a 6-31G* basis set in the gas phase in the range of ≥ -1.8 eV to < -1.4 eV. The organic electroluminescent device according to any of the preceding claims, wherein the compound of formula (I) has a molecular weight in the range of >400 g/mol to M2000 g/mol. The organic electroluminescent device according to any of the preceding claims, wherein the first electron transport layer is closer to the anode layer than any other electron transport layer within the organic electroluminescent device. The organic electroluminescent device according to any of the preceding claims, wherein the first electron transport layer is in direct contact with the first emission layer. The organic electroluminescent device according to any of the preceding claims, wherein the first electron transport layer is free of a metal complex. The organic electroluminescent device according to any of the preceding claims, wherein the first electron transport layer comprises an electron transport compound, wherein
- the electron transport compound has a molecular weight in the range of MOO g/mol to <2000 g/mol; and
- electron transport compound may comprise at least one N-containing heteroaromatic ring. The organic electroluminescent device according to any of the preceding claims, wherein the organic electroluminescent device further comprises a hole injection layer, a first hole transport layer, a second hole transport layer, first electron bloclang layer, second electron blocking layer, optionally a first hole blocking layer, optionally a second hole blocking layer, a second electron transport layer, and an electron injection layer. Display device comprising the organic electroluminescent device according to any of the preceding claims. A compound of formula (M1) or of formula (M2)
wherein in formula (M1)
- R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to CJb cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C1ts alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16, alkoxy, or PX’(R8)2 wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to C16 alitogy partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to Cm alkoxy, partially or perdcuterated C1 to C16 alkyl, partially or perdeuterated C1 to C1* alkoxy; and X* is selected from 0, S or Se, preferably O; and
- Rto Rtb, RLb,and RLb are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C6 to CS4 aryl or substituted or unsubstituted Cato C34 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated Ca to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C2 to C16 alkoxy, or PX’(R8)2 wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C2 to Cm alkyl, C1 to C16 alkoxy, partially or perfluorinated Ca to C16 alkyl, partially or perfluorinated C2 to C16 alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C2 to C16 alkoxy; and X1 is selected from 0, S or Se, preferably O;
- Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to Ca4 heteroaryl; wherein in formula (M2)
- R2 to R" are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, substituted or unsubstituted C(, to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to C)(, alkoxy, C.s to CK, branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C^ cyclic alkoxy, partially or perfluorinated C1 to C1fi alkyd , partially or perfluorinated C1 to C1& alkoxy, partially or perdcuterated C2 to Ci6 alkyl, partially or perdeuterated C1 to CM alkoxy, or PX^R8^ wherein R8 is independently selected from C(, to CM aryl, C3 to CM heteroaryl, C1 to CM alkyl, C1 to C1& alkoxy, partially or perfluorinated Ct to C16 alkyl, partially or perfluorinated Ct to C1t> alkoxy, partially or perdeuterated C1 to C1b alkyl, partially or perdeuterated C1 to C1t> alkoxy; and X1 is selected from 0, S or Se, preferably 0; and
- Ar is selected from substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl;
- L is selected from substituted or unsubstituted C6 to C24 aryl, substituted or unsubstituted C2 to C24 heteroaryl. The compound according to claim 16, wherein the compound is selected from formula (M3) or formula (M4) wherein in formula (M3)
- R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C1s alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C1& cyclic alkoxy, partially or perfluorinated C1 to C1« alkyl, partially or perfluorinated C1 to C1& alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C1 to C16 alkoxy, or PX*(R8)ss wherein R8 is independently selected from C6 to Ct2 aryl, C3 to C1B heteroaryl, Ch to C16 alkyl, C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to C1t, alkyd, partially or perdeuterated C1 alkoxy; and X’ is selected from O, S or Se, preferably O; and
- R' y Ru\ Rb ,and R1x! are independently selected from H, D, substituted or unsubstituted C1 to C1t. alkyl, substituted or unsubstituted C1> to CM aryl or substituted or unsubstituted C2 to C14 heteroaryl, CN, halogen, F, C1 to Clt, alkoxy, C1 to C16 branched alkyl, C3 to C* cyclic alkyl, C3 to C16 branched alkoxy, C3 to C1t, cyclic alkoxy, partially or perfluorinated C1 to Clb alkyl, partially or perfluorinated CL to C16 alkoxy, partially or perdeuterated C1 to CM alkyl, partially or perdeuterated C1 to C* alkoxy, or PX‘(R8)2 wherein R8 is independently selected from C6 to C12 aryl, C3 to Cw heteroaryl, C1 to CJ6 alkyl. C1 to C16 alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to CB alkoxy, partially or perdeuterated C( to Clf, alky l, partially or perdeuterated C1 to C1(, alkoxy; and X1 is selected from O, S or Se, preferably O; wherein in formula (M4)
- R2 to R" are independently selected from H, D, substituted or unsubstituted C1 to Cm alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, CN, halogen, F, C1 to C16 alkoxy, C3 to C16 branched alkyl, C3 to C16 cyclic alkyl, C3 to C16 branched alkoxy, C3 to C16 cyclic alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to C16 alkoxy, partially or perdeuterated C1 to Cm alkyl, partially or perdeuterated Cr to C16 alkoxy, or PX’fR8^ wherein R8 is independently selected from C6 to C12 aryl, C3 to C12 heteroaryl, C1 to C16 alkyl, C1 to Cm alkoxy, partially or perfluorinated C1 to C16 alkyl, partially or perfluorinated C1 to Cm alkoxy, partially or perdeuterated C1 to C16 alkyl, partially or perdeuterated C3 to Cm alkoxy; and X1 is selected from O, S or Se, preferably 0; and
- L is selected from substituted or unsubstituted C6 to C24 aryl, substituted or unsubstituted C2 to C24 heteroaryl.18. The compound according to claim 16 or 17, wherein in formula (M1) or (M3) R1 to R7 are independently selected from H, D, substituted or unsubstituted C1 to C^ alkyl, substituted or unsubstituted Ct, to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl; and wherein in formula (Ma) or (M4)
R2 to R7 are independently selected from H, D, substituted or unsubstituted C1 to Cm alkyl, substituted or unsubstituted C6 to C24 aryl or substituted or unsubstituted C2 to C24 heteroaryl, The compound according to any one of the claims 16 to 17, wherein RLb, RLb, Rfoand R1^ of formula (M1) or (M3) are independently selected from H, D, substituted or unsubstituted C1 to C16 alkyl, and wherein L of formula (M2) or (M4) is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridinyl, pyrazinyl, pyrimidyl, triazinyl. The compound according to any one of the claims 16 to 18, wherein RLb, RLb, Rfoand RLb of formula (M1) or (M3) are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, and wherein L of formula (M2) or (M4) is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl. The compound according to any one of the claims 16 to 19, wherein R’ to R7 in formulas (M1) and (M3) are independently selected from H, or D; RLb, R1*, Rfoand RLb are independently selected from H, D, and substituted or unsubstituted C1 to Clt, alkyl; and in formula (M1) Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl; and in formulas (Ma) and (M4) R2 to R are independently selected from H, or D; L is selected from substituted or unsubstituted Ch to CIO and or substituted or unsubstituted C3 to C5 heteroaryl. The compound according to any one of the claims 16 to 20, wherein in formulas (M1) and (M3) R1 to R? are independently selected from H, or D; R1-3, RLb, Rfoand RLd are independently selected from H, D, and substituted or unsubstituted C1 to C4 alkyl; and in formula (M1) Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl; and in formulas (M2) and (M4) R2 to R? are independently selected from H, or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; and in formula (Ma) Ar is selected from a substituted or unsubstituted 2- pyridine group or a substituted or unsubstituted 2-quinoline group, or substituted or unsubstituted phenyl. The compound according to any one of the claims 16 to 21, wherein the compound is selected from I-2. 1-78, 1-126, J-148, 1-150, 1-151, I-152, 1-158, 1-159, 1-160, I-163, 1-167, I-169, 1- 188 1-226, 1-227, 1-294, 1-S95, 1-296, 1-297, and 1-298
23 - The compound according to any one of the claims 16 to 22, wherein the compound is selected from 1-125, I-126, 1-151, 1-2, and I-152
wherein the respective compound can be undeuterated, partially deuterated or fully deuterated. A semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2) according to any of the claims 16 to 23. A semiconducting layer comprising the semiconducting material according to claim 24. An electronic device comprising a semiconductor layer according to claim 25. The electronic device according to claim 26, wherein the electronic device is an organic electronic device. The electronic device according to claim 26 or 27, wherein the electronic derive comprises an electroluminescent derice, an organic light emitting diode (OLED), a light emitting device, thin film transistor, a battery, a display device or an organic photovoltaic cell (OPV). A display device comprising an organic electronic device comprising a semiconductor layer comprising the semiconducting material comprising at least on compound selected from the group of compounds of formula (M1) or (M2) according to any of the claims 16 to 23.
EP23821632.9A 2022-12-15 2023-12-11 Organic electroluminescent device, semiconducting material, semiconducting layer, compound, electronic device and display device Pending EP4635271A1 (en)

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TWI584513B (en) 2011-11-30 2017-05-21 諾瓦發光二極體有限公司 Display
EP3828951A1 (en) * 2019-11-27 2021-06-02 Novaled GmbH Organic electronic device and display device comprising the organic electronic device as well as organic compounds for use in organic electronic devices

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