EP4635271A1 - Dispositif électroluminescent organique, matériau semi-conducteur, couche semi-conductrice, composé, dispositif électronique et dispositif d'affichage - Google Patents

Dispositif électroluminescent organique, matériau semi-conducteur, couche semi-conductrice, composé, dispositif électronique et dispositif d'affichage

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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
Authority
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
Application number
EP23821632.9A
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German (de)
English (en)
Inventor
Qiang Huang
Johannes Scholz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NovaLED GmbH
Original Assignee
NovaLED GmbH
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Filing date
Publication date
Application filed by NovaLED GmbH filed Critical NovaLED GmbH
Publication of EP4635271A1 publication Critical patent/EP4635271A1/fr
Pending legal-status Critical Current

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Classifications

    • 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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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant une couche d'anode, une couche de cathode, une première couche d'émission, une seconde couche d'émission, une première couche de génération de charge et une première couche de transport d'électrons ; et un dispositif d'affichage le comprenant.
EP23821632.9A 2022-12-15 2023-12-11 Dispositif électroluminescent organique, matériau semi-conducteur, couche semi-conductrice, composé, dispositif électronique et dispositif d'affichage Pending EP4635271A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP22213851.3A EP4387412B1 (fr) 2022-12-15 2022-12-15 Dispositif électroluminescent organique et dispositif d'affichage comprenant le dispositif électroluminescent organique
PCT/EP2023/085115 WO2024126373A1 (fr) 2022-12-15 2023-12-11 Dispositif électroluminescent organique, matériau semi-conducteur, couche semi-conductrice, composé, dispositif électronique et dispositif d'affichage

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EP4635271A1 true EP4635271A1 (fr) 2025-10-22

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EP22213851.3A Active EP4387412B1 (fr) 2022-12-15 2022-12-15 Dispositif électroluminescent organique et dispositif d'affichage comprenant le dispositif électroluminescent organique
EP23821632.9A Pending EP4635271A1 (fr) 2022-12-15 2023-12-11 Dispositif électroluminescent organique, matériau semi-conducteur, couche semi-conductrice, composé, dispositif électronique et dispositif d'affichage

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EP (2) EP4387412B1 (fr)
KR (1) KR20250123757A (fr)
CN (1) CN119896076A (fr)
TW (1) TW202442094A (fr)
WO (1) WO2024126373A1 (fr)

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Publication number Priority date Publication date Assignee Title
DE102007012794B3 (de) 2007-03-16 2008-06-19 Novaled Ag Pyrido[3,2-h]chinazoline und/oder deren 5,6-Dihydroderivate, deren Herstellungsverfahren und diese enthaltendes dotiertes organisches Halbleitermaterial
TWI584513B (zh) 2011-11-30 2017-05-21 諾瓦發光二極體有限公司 顯示器
EP3828951A1 (fr) * 2019-11-27 2021-06-02 Novaled GmbH Dispositif électronique organique et dispositif d'affichage comprenant le dispositif électronique organique ainsi que des composés organiques destinés à être utilisés dans des dispositifs électroniques organiques

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WO2024126373A1 (fr) 2024-06-20
KR20250123757A (ko) 2025-08-18
EP4387412B1 (fr) 2025-04-09
CN119896076A (zh) 2025-04-25
EP4387412A1 (fr) 2024-06-19
TW202442094A (zh) 2024-10-16

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