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

Abstract

The invention relates to an organic light-emitting device. The organic light-emitting device comprises an anode layer, a cathode layer, a first light-emitting layer, a second light-emitting layer, a first charge generation layer and a first electron transport layer, the invention also relates to a display device comprising the organic electroluminescent device.

Description

Technical Field

[0001] The invention relates to an organic electroluminescent device, a semiconductor material, a semiconductor layer, an electronic device, a compound and a display device. Background Art

[0002] Organic electronic devices, such as organic light-emitting diodes (OLEDs), which are self-luminous devices, have wide viewing angles, excellent contrast, fast response, high brightness, excellent operating voltage characteristics, and color reproducibility. A typical OLED includes an anode, a hole transport layer HTL, an emission layer EML, an electron transport layer ETL, and a cathode stacked sequentially on a substrate. In this regard, HTL, EML, and ETL are thin films formed of organic compounds.

[0003] When voltage is applied to the anode and cathode, holes injected from the anode move toward the EML through the HTL, and electrons injected from the cathode move toward the EML through the ETL. Holes and electrons recombine in the EML to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted. The injection and flow of holes and electrons should be balanced so that the OLED having the above structure has excellent efficiency and / or long life.

[0004] The performance of an organic light emitting diode (organic electroluminescent device) may be affected by the characteristics of an organic semiconductor layer included therein, and in particular, may be affected by the characteristics of an organic material of the organic semiconductor layer.

[0005] In particular, it is desirable to develop an organic semiconductor layer arrangement that can improve electron transport, electron injection and electron generation properties. Thus, the operating voltage in OLEDs can be reduced. Lower operating voltage is important for reducing power consumption and improving battery life, especially for mobile devices.

[0006] Furthermore, there is a need to develop organic electronic devices with improved efficiency. Improving efficiency is important for reducing power consumption and increasing battery life, for example, for mobile display devices.

[0007] There remains a need to improve the performance of organic electroluminescent devices, in particular to achieve multi-stack OLEDs with low operating voltage, high efficiency and low voltage rise over time.

[0008] Furthermore, there remains a need to improve the properties of compounds for use in organic electronic devices, in particular to achieve compounds with thermal properties suitable for mass production under vacuum thermal conditions. Summary of the invention

[0009] One aspect of the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising an anode layer, a cathode layer, a first light-emitting layer, a second light-emitting layer, a first charge generation layer and a first electron transport layer,

[0010] in

[0011] - the first charge generation layer is arranged between the first light-emitting layer and the second light-emitting layer;

[0012] - the first electron transport layer is arranged between the first light-emitting layer and the second light-emitting layer;

[0013] - the first charge generation layer comprises a first n-type charge generation layer and a first p-type charge generation layer;

[0014] - 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;

[0015] - the first electron transport layer is arranged in direct contact with the first n-type charge generation layer;

[0016] - the first electron transport layer does not contain 8-hydroxyquinolate lithium;

[0017] - the first n-type charge generation layer comprises a metal dopant and the metal dopant is Yb;

[0018] - the first n-type charge generation layer comprises a compound of formula (I):

[0019]

[0020] Wherein in formula (I),

[0021] -Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 heteroaryl;

[0022] -R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and

[0023] -L is selected from substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C2 to C 24 Heteroaryl.

[0024] Another aspect of the present invention provides a display device, which includes the organic electroluminescent device according to the present invention.

[0025] Another aspect of the present invention provides a compound of formula (M1) or formula (M2):

[0026]

[0027] In formula (M1),

[0028] -R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and

[0029] -R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X1 Selected from O, S or Se, preferably O;

[0030] -Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 heteroaryl;

[0031] Wherein in formula (M2),

[0032] -R 2 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and

[0033] -Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 heteroaryl;

[0034] -L is selected from substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C2 to C 24 Heteroaryl.

[0035] Another aspect of the present invention provides a semiconductor material, which comprises at least one compound selected from the compounds of formula (M1) or formula (M2).

[0036] Another aspect of the present invention provides a semiconductor layer, wherein the semiconductor layer comprises a semiconductor material, wherein the semiconductor material comprises at least one compound selected from the compound of formula (M1) or formula (M2).

[0037] Another aspect of the present invention provides an electronic device, comprising a semiconductor layer, wherein the semiconductor layer comprises a semiconductor material, wherein the semiconductor material comprises at least one compound selected from the compound of formula (M1) or formula (M2).

[0038] According to one embodiment of the present invention, the electronic device is an organic electronic device.

[0039] According to one embodiment, the electronic device comprises an electroluminescent device, an organic light emitting diode (OLED), a light emitting device, a thin film transistor, a battery, a display device or an organic photovoltaic cell (OPV).

[0040] Another aspect of the present invention provides a display device, which includes an organic electronic device, wherein the organic electronic device includes a semiconductor layer, the semiconductor layer includes a semiconductor material, and the semiconductor material includes at least one compound selected from the compound of formula (M1) or formula (M2).

[0041] It should be noted that throughout the application and claims, unless otherwise indicated, any general designation such as R n , Ar or L always refer to the same moiety.

[0042] In this specification, when no definition is provided otherwise, "substituted" refers to deuterium, C1 to C 12 Alkyl and C1 to C 12 Alkoxy substitution.

[0043] However, in the present specification, "aryl substituted" means substituted by one or more aryl groups, which may themselves be substituted by one or more aryl and / or heteroaryl groups.

[0044] Accordingly, in this specification, "heteroaryl substituted" means substituted by one or more heteroaryl groups, which may themselves be substituted by one or more aryl and / or heteroaryl groups.

[0045] In this specification, when no definition is provided otherwise, "alkyl group" refers to a saturated aliphatic hydrocarbon group. The alkyl group can be C1 to C 12 More specifically, the alkyl group may be C1 to C 10 An alkyl group or a C1 to C6 alkyl group. For example, a C1 to C4 alkyl group includes 1 to 4 carbons in the alkyl chain and can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0046] Specific examples of the alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group.

[0047] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane by formally taking away a hydrogen atom from a ring atom contained in the corresponding cycloalkane. Examples of the cycloalkyl group may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, an adamantyl group, etc.

[0048] The term "hetero" is to be understood as a structure that can be formed by covalently bonded carbon atoms in which at least one carbon atom is replaced by another polyvalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, S; more preferably, N, P, O, S.

[0049] In this specification, "aryl group" refers to a hydrocarbon group that can be generated by formally taking a hydrogen atom from an aromatic ring in a corresponding aromatic hydrocarbon. Aromatic hydrocarbon refers to a hydrocarbon containing 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 contains a conjugated system of delocalized electrons that satisfies Huckel's rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl, polycyclic groups containing more aromatic rings connected by single bonds, such as biphenyl, and polycyclic groups containing fused rings, such as naphthyl or fluorene-2-yl.

[0050] Similarly, heteroaryl is understood, where appropriate, in particular as a radical which is derived by formally abstracting a ring hydrogen from this ring in compounds which contain at least one heterocyclic aromatic ring.

[0051] Heterocycloalkyl is understood, where appropriate, in particular as a radical which is derived by formal abstraction of a ring hydrogen from a saturated cycloalkyl ring in compounds which contain at least one saturated cycloalkyl ring.

[0052] The term "fused aryl ring" or "condensed aryl ring" is to be understood as when two aryl rings share at least two common sp2 hybridized carbon atoms, they are considered to be fused or condensed.

[0053] In this specification, a single bond means a direct bond.

[0054] In the context of the present invention, "different" means that the compounds do not have the same chemical structure.

[0055] The terms "does not contain", "does not contain", "does not include" do not exclude impurities that may be present in the compound before deposition. Impurities have no technical impact on the purpose to be achieved by the present invention.

[0056] The term "sandwiched in contact" refers to an arrangement of three layers wherein a middle layer is in direct contact with two adjacent layers.

[0057] The terms "light absorbing layer" and "light absorbing layer" are used synonymously.

[0058] The terms "light emitting layer", "light emitting layer" and "emissive layer" are used synonymously.

[0059] The terms "OLED," "organic light emitting diode," and "organic light emitting device" are used synonymously.

[0060] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and according to the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to the conductive characteristics.

[0061] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and according to the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to conductive properties.

[0062] Beneficial Effects

[0063] Surprisingly, it was found that a multi-stack OLED comprising an n-type charge generation layer comprising ytterbium as a metal dopant, a compound comprising imidazo[1,5-a]pyridine groups and phenanthroline groups as a host (matrix) and in direct contact with an electron transport layer that does not contain LiQ has a reduced voltage rise over time.

[0064] In particular, the use of compounds containing imidazo[1,5-a]pyridine and phenanthroline groups as n-CGL hosts for ytterbium and the use of LiQ-free ETLs directly contacting the n-CGL synergistically improve the voltage rise over time of multi-stack OLEDs.

[0065] First charge generation layer

[0066] The thickness of the first n-type charge generation layer may be in the range of 0.5 nm to 50 nm; or in the range of 1 nm to about 40 nm; or in the range of 2 nm to 30 nm; or 5 nm to 15 nm.

[0067] 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):

[0068]

[0069] According to one embodiment, based on the total weight of the first n-type charge generation layer, the amount of the compound of formula (I) present in the first n-type charge generation layer is ≥0.1% by weight, preferably ≥1% by weight, preferably ≥2% by weight, more preferably ≥3% by weight, more preferably ≥5% by weight, more preferably ≥8% by weight, more preferably ≥20% by weight, more preferably ≥30% by weight, more preferably ≥40% by weight, more preferably ≥50% by weight.

[0070] According to one embodiment, based on the total weight of the first n-type charge generation layer, the amount of the metal dopant present in the first n-type charge generation layer is ≤99.9 wt%, preferably ≤99 wt%, more preferably ≤98 wt%, more preferably ≤97 wt%, more preferably ≤95 wt%, more preferably ≤92 wt%, more preferably ≤80 wt%, more preferably ≤70 wt%, more preferably ≤60 wt%, more preferably ≤55 wt%, more preferably ≤50 wt%.

[0071] According to one embodiment, based on the total weight of the first n-type charge generation layer, the amount of the compound of formula (I) present in the first n-type charge generation layer is ≥50 wt% to ≤99.9 wt%, preferably ≥50 wt% to ≤99 wt%, more preferably ≥50 wt% to ≤98 wt%, and more preferably ≥50 wt% to ≤97 wt%.

[0072] According to one embodiment, based on the total weight of the first n-type charge generation layer, the amount of the metal dopant present in the first n-type charge generation layer is ≥0.1 wt% to ≤50 wt%, preferably ≥1 wt% to ≤50 wt%, more preferably ≥2 wt% to ≤50 wt%, more preferably ≥3 wt% to ≤50 wt%.

[0073] According to one embodiment of the present invention, the first n-type charge generation layer is non-luminescent.

[0074] In the context of this specification, the term "substantially non-luminescent" or "non-luminescent" means that the contribution of a compound or layer to the visible luminescence spectrum from a device is less than 10%, preferably less than 5%, relative to the visible luminescence spectrum. The visible luminescence spectrum is the luminescence spectrum with a wavelength of about ≥380nm to about ≤780nm.

[0075] The metal dopant may be a redox n-type dopant for the purposes of the present disclosure. A redox n-type dopant is understood to be a compound which, when embedded in an electron transport matrix, improves the electronic properties of the organic material formed, in particular in terms of electron injection, electron generation and / or electron conductivity, compared to the pure matrix under the same physical conditions. Preferably, the redox n-type dopant is non-luminescent.

[0076] In the context of the present invention, "embedded in the electron transport matrix" means that the redox n-type dopant forms a mixture with the electron transport matrix.

[0077] Ar of formula (I)

[0078] Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 Heteroaryl.

[0079] According to one embodiment, Ar is selected from substituted or unsubstituted C6 to C 18 Aryl or substituted or unsubstituted C2 to C 18 Heteroaryl.

[0080] According to one embodiment, Ar is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl.

[0081] According to one embodiment, Ar is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl.

[0082] According to one embodiment, Ar is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl.

[0083] According to one embodiment, Ar is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring.

[0084] According to one embodiment, Ar is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl and substituted or unsubstituted quinolyl.

[0085] Substituents on Ar of formula (I)

[0086] Ar may be unsubstituted or substituted with one or more substituents.

[0087] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents can be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0088] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0089] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents can be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0090] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0091] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0092] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN.

[0093] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0094] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN.

[0095] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0096] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN.

[0097] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0098] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0099] According to one embodiment, one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or heteroatom to form a ring.

[0100] According to one embodiment, one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0101] According to one embodiment, Ar is selected from the following D1 to D19 shown in Table 1.

[0102] Table 1:

[0103]

[0104] In D1 to D19, R 9 , R 10 and R 11 Independently selected from H, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C6 to C 18 Aryl, C3 to C 20Heteroaryl, perfluorinated C1 to C 16 Alkyl, perfluorinated C1 to C 16 Alkoxy, where R 9 and R 10 The rings may be formed by single bonds or heteroatom linkages, wherein the asterisk "*" indicates the binding site.

[0105] R of formula (I) 1 To R 7

[0106] According to one embodiment, R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0107] According to one embodiment, R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F.

[0108] According to one embodiment, R 1 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C 16 Alkyl, substituted or unsubstituted C6 to C 24Aryl or substituted or unsubstituted C2 to C 24 Heteroaryl, halogen, F.

[0109] According to one embodiment, R 1 To R 7 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 C2 to C 24 Heteroaryl, halogen.

[0110] According to one embodiment, R 1 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 Aryl or substituted or unsubstituted C2 to C 18 Heteroaryl, CN, halogen, Cl, F.

[0111] According to one embodiment, R 1 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 Aryl or substituted or unsubstituted C2 to C 18 Heteroaryl, halogen.

[0112] According to one embodiment, R 1 To R 7 are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl, CN, halogen, Cl, F.

[0113] According to one embodiment, R 1 To R 7 are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl, halogen.

[0114] According to one embodiment, R 1 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl, CN, halogen, Cl, F.

[0115] According to one embodiment, R 1 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl, halogen.

[0116] According to one embodiment, R 1 To R 7 Independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, CN, halogen, Cl, F.

[0117] According to one embodiment, R 1 To R 7 Independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, halogen.

[0118] R of formula (I) 1 To R 7 Substituents on

[0119] R 1 To R 7 may independently be unsubstituted or substituted with one or more substituents.

[0120] According to one embodiment, R 1 To R 7 The one or more substituents on the 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, halogen, F, CN or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0121] According to one embodiment, R 1 To R 7 The one or more substituents on the 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0122] According to one embodiment, R 1 To R 7 The one or more substituents on the 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN.

[0123] According to one embodiment, R 1 To R 7 The one or more substituents on the 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN.

[0124] According to one embodiment, R 1 To R 7 The one or more substituents on the 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN.

[0125] According to one embodiment, R 1 To R 7 The one or more substituents on the 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0126] According to one embodiment, R 1 To R 7 The one or more substituents on (if present) are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0127] L in formula (I)

[0128] According to one embodiment, L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C18 Heteroaryl.

[0129] According to one embodiment, L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl.

[0130] According to one embodiment, L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl.

[0131] According to one embodiment, L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C3 to C5 heteroaryl.

[0132] According to one embodiment, L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring.

[0133] According to one embodiment, L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazinyl.

[0134] According to one embodiment, L is selected from substituted or unsubstituted phenyl and substituted or unsubstituted naphthyl.

[0135] According to one embodiment, L is selected from substituted phenyl, unsubstituted phenyl and unsubstituted naphthyl.

[0136] Substituents on L of formula (I)

[0137] L may independently be unsubstituted or substituted with one or more substituents.

[0138] According to one embodiment, one or more substituents on L (if present) are independently selected from D, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C16 Alkoxy, halogen, F, CN or PX 1 (R 8 )2, wherein the substituents may be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0139] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0140] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents can be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0141] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0142] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0143] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN.

[0144] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0145] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN.

[0146] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0147] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN.

[0148] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0149] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0150] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or heteroatom to form a ring.

[0151] According to one embodiment, one or more substituents on L (if present) are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0152] According to one embodiment, L is selected from the following moieties E1 to E33 shown in Table 2a.

[0153] According to one embodiment, L is selected from the following moieties E1 to E34 shown in Table 2a.

[0154] Table 2a:

[0155]

[0156]

[0157] Among them, in E1 to E34,

[0158] X 2 Selected from O or S, preferably O;

[0159] R 12 and R 13 Independently selected from H, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, perfluorinated C1 to C 16 Alkyl, perfluorinated C1 to C 16 alkoxy; and

[0160] Asterisk "*" indicates the binding position.

[0161] According to one embodiment, L is selected from the following moieties E1 to E33 shown in Table 2b.

[0162] Table 2b:

[0163]

[0164]

[0165] Among them, in E1 to E33,

[0166] X 2 Selected from O or S, preferably O;

[0167] R 12 and R 13 Independently selected from H, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, perfluorinated C1 to C 16 Alkyl, perfluorinated C1 to C 16 alkoxy; and

[0168] Asterisk "*" indicates the binding position.

[0169] According to one embodiment, L is selected from the moieties E1 to E30.

[0170] According to one embodiment, L is selected from the moieties E1 to E24.

[0171] According to one embodiment, L is selected from the moieties E1 to E23.

[0172] According to one embodiment, L is selected from the moieties E1 to E5 and E8 to E23.

[0173] According to one embodiment, L is selected from the moieties E1 to E5, E8 to E13 and E16.

[0174] According to one embodiment, L is selected from the moieties E1 to E5, E11 and E16.

[0175] According to one embodiment, L is selected from the moieties E1 to E5 and E16.

[0176] According to one embodiment, L is selected from the moieties E1 to E3, E11 and E16.

[0177] According to one embodiment, L is selected from the moieties E2 to E3, E11 and E16.

[0178] According to one embodiment, L is selected from the moieties E2 to E3 and E16.

[0179] Properties of the compounds of formula (I)

[0180] According to one embodiment, when using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the LUMO energy level of the compound of formula (I) is ≤-1.3 eV, preferably ≤-1.35 eV, and more preferably ≤-1.4 eV.

[0181] According to one embodiment, when using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the LUMO energy level of the compound of formula (I) is ≥-2.5 eV, preferably ≥-2.0 eV, more preferably ≥-1.9 eV, even more preferably ≥-1.85 eV, and most preferably ≥-1.8 eV.

[0182] According to one embodiment, when using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the LUMO energy level of the compound of formula (I) is in the range of ≥-2.5 eV and ≤-1.3 eV, preferably ≥-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 ≥-1.8 eV to ≤-1.4 eV.

[0183] According to one embodiment, the molecular weight of the compound of formula (I) is 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, most preferably ≥440 g / mol to ≤900 g / mol.

[0184] Specific embodiments of the compound of formula (I)

[0185] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C 18 Heteroaryl.

[0186] According to one embodiment, in formula (I), R1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C 18 Heteroaryl; Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0187] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C 18 Heteroaryl; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0188] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C 18 Heteroaryl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0189] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl.

[0190] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl; Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0191] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0192] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0193] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl.

[0194] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl; Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0195] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0196] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0197] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl.

[0198] According to one embodiment, in formula (I), R 1 To R7 Independently selected from H or D; L is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl; Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0199] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl; Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl group.

[0200] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl; Ar is selected from unsubstituted 2-pyridine group or unsubstituted 2-quinoline group or unsubstituted phenyl group.

[0201] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring.

[0202] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring; Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0203] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring; Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl.

[0204] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0205] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazinyl.

[0206] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazinyl; Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.

[0207] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazinyl; Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl.

[0208] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazinyl; Ar is selected from unsubstituted 2-pyridine group or unsubstituted 2-quinoline group or unsubstituted phenyl.

[0209] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted phenyl.

[0210] According to one embodiment, in formula (I), R 1 To R 7 are independently selected from H or D; L is selected from substituted or unsubstituted phenyl; Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.

[0211] According to one embodiment, in formula (I), R 1 To R 7 are independently selected from H or D; L is selected from substituted or unsubstituted phenyl; Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl.

[0212] According to one embodiment, in formula (I), R 1To R 7 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.

[0213] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from E1 to E5 and E8 to E23.

[0214] According to one embodiment, in formula (I), 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 a substituted or unsubstituted phenyl group.

[0215] According to one embodiment, in formula (I), 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 a substituted or unsubstituted phenyl group.

[0216] According to one embodiment, in formula (I), 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 an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0217] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from E1 to E5 and E8 to E23.

[0218] According to one embodiment, in formula (I), R 1 To R 7 are independently selected from H or D; L is selected from E2, E3, E8, E9, E11, E14 and E15; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0219] According to one embodiment, in formula (I), R 1 To R 7 are independently selected from H or D; L is selected from E2, E3, E8, E9, E11, E14 and E15; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0220] According to one embodiment, in formula (I), R 1 To R 7 are independently selected from H or D; L is selected from E2, E3, E8, E9, E11, E14 and E15; Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0221] According to one embodiment, in formula (I), R 1 To R 7 Independently selected from H or D; L is selected from E2 to E3 and E11.

[0222] According to one embodiment, in formula (I), R 1 To R 7 are independently selected from H or D; L is selected from E2 to E3 and E11; Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0223] According to one embodiment, in formula (I), R 1 To R 7 independently selected from H or D; L is selected from E2 to E3 and E11; Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0224] According to one embodiment, in formula (I), R 1 To R 7 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 group.

[0225] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (II):

[0226]

[0227] in

[0228] Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 Heteroaryl,

[0229] R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O;

[0230] Wherein formula (II) may be undeuterated, partially deuterated or fully deuterated.

[0231] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (III):

[0232]

[0233] in

[0234] Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 heteroaryl;

[0235] Wherein formula (III) may be undeuterated, partially deuterated or fully deuterated.

[0236] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (IVa) or formula (IVb):

[0237]

[0238] Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 heteroaryl;

[0239] Wherein Formula (IVa) or Formula (IVb) may be undeuterated, partially deuterated or fully deuterated.

[0240] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (Va), formula (Vb), formula (Vc) or formula (Vd):

[0241]

[0242] in

[0243] R 15 and R 16 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O;

[0244] Wherein Formula (Va) to Formula (Vd) may be undeuterated, partially deuterated or fully deuterated.

[0245] According to one embodiment, R 15 and R 16The one or more substituents on the 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, halogen, F, CN or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0246] According to one embodiment, R 15 To R 16 The one or more substituents on the 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0247] According to one embodiment, R 15 To R 16 The one or more substituents on the 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN.

[0248] According to one embodiment, R 15 To R 16 The one or more substituents on the 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN.

[0249] According to one embodiment, R 15 To R 16 The one or more substituents on the 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN.

[0250] According to one embodiment, R 15 To R 16The one or more substituents on the 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0251] According to one embodiment, R 15 To R 16 The one or more substituents on (if present) are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0252] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VIa), formula (VIb), formula (VIc) or formula (VId):

[0253]

[0254] R 15 and R 16 independently selected from

[0255] Wherein Formula (VIa) or Formula (VId) may be undeuterated, partially deuterated or fully deuterated.

[0256] The compound of formula (I) may be selected from the following compounds I-1 to I-298 shown in Table 3.

[0257] Table 3:

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293]

[0294] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0295] The compound of formula (I) may be selected from the following compounds I-1 to I-150, wherein each compound may be undeuterated, partially deuterated or fully deuterated.

[0296] According to one embodiment, the compound of formula (I) is selected from the compounds shown in Table 4.

[0297] Table 4:

[0298]

[0299]

[0300]

[0301] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0302] According to one embodiment, the compound of formula (I) is selected from the compounds shown in Table 5.

[0303] Table 5:

[0304]

[0305]

[0306] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0307] According to one embodiment, the compound of formula (I) is selected from the compounds shown in Table 6.

[0308] Table 6:

[0309]

[0310]

[0311] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0312] According to one embodiment, the compound of formula (I) is selected from the compounds shown in Table 7.

[0313] Table 7:

[0314]

[0315]

[0316] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0317] According to one embodiment, the compound of formula (I) is selected from the compounds shown in Table 7b.

[0318] Table 7b:

[0319]

[0320]

[0321] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0322] Table 8:

[0323]

[0324] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0325] First electron transport layer

[0326] According to one embodiment, the first electron transport layer is in direct contact with the first light emitting layer.

[0327] According to one embodiment, the first electron transport layer is closer to the anode layer than any other electron transport layer in the organic electroluminescent device.

[0328] According to one embodiment, the first electron transport layer in direct contact with the first n-type charge generation layer is the electron transport layer closest to the anode layer.

[0329] According to one embodiment, the first electron transport layer is arranged between the first light emitting layer and the first charge generating layer.

[0330] The thickness of the first electron transport layer may be in the range of 0.5 nm to 50 nm; or in the range of 1 nm to about 40 nm; or in the range of 2 nm to 30 nm.

[0331] According to one embodiment of the present invention, the first electron transport layer is non-emissive.

[0332] In the context of this specification, the term "substantially non-luminescent" or "non-luminescent" means that the contribution of a compound or layer to the visible luminescence spectrum from a device is less than 10%, preferably less than 5%, relative to the visible luminescence spectrum. The visible luminescence spectrum is the luminescence spectrum with a wavelength of about ≥380nm to about ≤780nm.

[0333] The first electron transport layer does not contain 8-hydroxyquinolate lithium.

[0334] 8-Hydroxyquinoline Lithium

[0335] According to one embodiment, the first electron transport layer does not contain a lithium metal complex.

[0336] According to one embodiment, the first electron transport layer is free of metal complexes.

[0337] According to one embodiment, the first electron transport layer comprises an electron transport compound.

[0338] The molecular weight of the electron transport compound may be 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, most preferably ≥440 g / mol to ≤900 g / mol.

[0339] According to one embodiment, the first electron transport layer comprises an electron transport compound, wherein the electron transport compound comprises 8 to 13 aromatic or heteroaromatic rings, optionally 8 to 11 aromatic or heteroaromatic rings, optionally 9 to 11 aromatic or heteroaromatic rings, optionally 9 aromatic or heteroaromatic rings, wherein one or more of the aromatic or heteroaromatic rings can be replaced by C1 to C4 alkyl. In this regard, the aromatic or heteroaromatic ring is a single aromatic ring, such as a 6-membered aromatic ring such as phenyl, a 6-membered heteroaromatic ring such as pyridyl, a 5-membered heteroaromatic ring such as pyrrolyl, etc. In this regard, in a condensed (hetero) aromatic ring system, each ring is considered a monocyclic ring. For example, naphthalene comprises two aromatic rings.

[0340] 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, optionally 1 or 2 heteroaromatic rings.

[0341] The aromatic or heteroaromatic ring of the electron transport compound may be a 6-membered ring.

[0342] The heteroaromatic rings of the electron transport compound may be N-containing heteroaromatic rings, optionally all heteroaromatic rings are N-containing heteroaromatic rings, optionally all heteroaromatic rings contain N as the only heteroatom type.

[0343] The electron transport compound may comprise at least one six-membered heteroaromatic ring containing one to three N atoms in each heteroaromatic ring, and optionally one to three six-membered heteroaromatic rings containing one to three N atoms in each heteroaromatic ring.

[0344] The at least one 6-membered heteroaromatic ring contained in the electron transport compound may be azine. The at least one 6-membered heteroaromatic ring contained in the electron transport compound may be triazine, diazine, pyrazine, pyrimidine, pyridine, preferably triazine.

[0345] If the electron transport compound comprises two or more heteroaromatic rings, the heteroaromatic rings may be separated from each other by at least one aromatic ring containing no heteroatoms.

[0346] In one embodiment, the heteroatom in the heteroaromatic ring of the electron transport compound is bonded to the molecular structure of the electron transport compound through at least one double bond.

[0347] According to one embodiment, the compound containing at least one nitrogen atom in a six-membered aromatic ring in the electron transport layer is selected from Formula (xxa) or Formula (xxb) shown in Table 9.

[0348] Table 9:

[0349]

[0350] Among them, Ar I is a substituted or unsubstituted C3 to C 40 Heteroaromatic ring systems,

[0351] Among them, Ar II is a substituted or unsubstituted C3 to C 40 Heteroaromatic ring systems,

[0352] Among them, Ar I and Ar II The substituents on D are, identically or differently on each occurrence, D, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be replaced in each case by one or more radicals R a replace;

[0353] Among them, Ar Ia ,Ar Ib ,Ar Ic ,Ar IIa and Ar IIb is, identically or differently on each occurrence, H, D, a monovalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms which may be replaced in each case by one or more radicals Ra replace;

[0354] Wherein, in formula (xxa), Ar Ia ,Ar Ib ,Ar Ic At least one of, and in the case of formula (xxb),

[0355] Ar Ia ,Ar Ib ,Ar IIa and Ar IIb at least one of the groups R, independently selected from monovalent aromatic or heteroaromatic ring systems having 5 to 60 aromatic ring atoms, which can in each case be replaced by one or more radicals R a replace;

[0356] Among them, Ar L is a divalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R a replace;

[0357] Where R a is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(R b )2、N(Ar 1s )2、B(Ar 1s )2、C(=O)Ar 1s , P(=Y)(R c )2、S(=O)Ar 1s 、S(=O)2Ar 1s , CR b =CR b Ar 1s 、CN、NO2、Si(R b )3、B(OR b )2、B(R b )2. B(N(R b )2)2、OSO2R b , substituted or unsubstituted straight chain C1 to C 20 Alkyl, substituted or unsubstituted straight chain C1 to C 20 Alkenyl, substituted or unsubstituted straight chain C1 to C 20 Alkynyl, substituted or unsubstituted straight chain C1 to C 20 Alkoxy, substituted or unsubstituted straight chain C1 to C 20 Thioalkoxy, substituted or unsubstituted branched C3 to C 20 Alkyl, substituted or unsubstituted branched C3 to C 20 Alkenyl, substituted or unsubstituted branched C3 to C20 Substituted or unsubstituted branched C3 to C 20 Alkynyl, substituted or unsubstituted branched C3 to C 20 Alkoxy or substituted or unsubstituted C3 to C 20 Branched chain thioalkoxy, substituted or unsubstituted cyclic C3 to C 40 Alkyl, substituted or unsubstituted cyclic C3 to C 40 Alkenyl, substituted or unsubstituted cyclic C3 to C 40 Alkynyl, substituted or unsubstituted cyclic C3 to C 40 Alkoxy or substituted or unsubstituted cyclic C3 to C 40 Thioalkoxy; substituted or unsubstituted heterocyclic C3 to C 40 Alkyl, substituted or unsubstituted heterocyclic C3 to C 40 Alkenyl, substituted or unsubstituted heterocyclic C3 to C 40 Alkynyl, substituted or unsubstituted heterocyclic C3 to C 40 Alkoxy or substituted or unsubstituted heterocyclic C3 to C 40 wherein one or more substituents (if present) are selected from R b , wherein one or more non-adjacent CH2 groups are optionally replaced by R b C=CR b 、C≡C、Si(R b )2、Ge(R b )2、Sn(R b )2. C=O, C=S, C=Se, C=NR b ,P(=O)(R b )、SO、SO2、NR b , O, S or CONR b and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2 or in each case by one or more radicals R b A substituted aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, or optionally substituted by one or more radicals R b Substituted aryloxy or heteroaryloxy groups having 5 to 60 aromatic ring atoms, or combinations of these systems; two or more adjacent substituents R a These optionally form with one another a monocyclic or polycyclic aliphatic or aromatic ring system;

[0358] Among them, Ar 1s is, identically or differently on each occurrence, optionally substituted by one or more radicals R b Substituted aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms; two groups Ar bonded to the same nitrogen, phosphorus or boron atom 1sIt can also be selected from B(R b )、C(R b )2、Si(R b )2. C=O, C=NR b , C=C(R b )2, O, S, S=O, SO2, N(R b )、P(R b ) and P(=Y)R c The bridging groups are connected to each other;

[0359] Where R b H, D or C1 to C, identically or differently on each occurrence 20 Aliphatic hydrocarbon group, C1 to C 20 Aryl and / or C1 to C 20 heteroaryl, in which the H atoms are additionally optionally replaced by D or F; two or more adjacent substituents R b This can also form monocyclic or polycyclic aliphatic or aromatic ring systems with one another;

[0360] wherein Y is selected from O, S or Se, preferably O, and R c Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially fluorinated or perfluorinated C1 to C6 alkyl, partially fluorinated or perfluorinated C1 to C6 alkoxy, partially deuterated or perdeuterated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkoxy.

[0361] For the purposes of the present invention, an aromatic or heteroaromatic ring system is intended to be taken as meaning a system which does not necessarily contain only one aryl or one heteroaryl group or only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be interrupted by short non-aromatic units (preferably less than 10% non-H atoms), for example sp 3 The aromatic ring systems are interrupted by hybridized C, N or O atoms. Thus, for the purposes of the present invention, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, benzophenone, etc. are also intended to be regarded as meaning aromatic ring systems. Likewise, an aromatic or heteroaromatic ring system is regarded as meaning a system in which a plurality of aryl or heteroaryl groups are linked to one another by single bonds, for example biphenyl, terphenyl or bipyridine.

[0362] According to one embodiment, Ar I Selected from pyrazine, pyridine, pyrimidine or triazine, phenanthroline.

[0363] According to one embodiment, Ar II Selected from pyrazine, pyridine, pyrimidine or triazine, phenanthroline.

[0364] According to one embodiment, Ar in formula (xxa) or formula (xxxa) I is selected from pyrazine, pyridine, pyrimidine, triazine, phenanthroline; or Ar in formula (xxa) or formula (xxxa) I and Ar in formula (xxb) or formula (xxxb) II are independently selected from pyrazine, pyridine, pyrimidine, triazine or phenanthroline.

[0365] According to one embodiment, the compound containing at least one nitrogen atom in a six-membered aromatic ring in the electron transport layer is selected from formula (xxxa) or formula (xxxb):

[0366]

[0367] in

[0368] Z Ia is selected from N or CH,

[0369] Z Ib is selected from N or CH,

[0370] Z Ic is selected from N or CH,

[0371] Z IIa is selected from N or CH,

[0372] Z IIb is selected from N or CH, and

[0373] Z IIc is selected from N or CH,

[0374] In formula (XXxa), Z Ia , Z Ib and Z Ic At least one of which is selected from N,

[0375] In formula (XXxb), Z Ia , Z Ib , Z Ic , Z IIa , Z IIb and Z IIc At least one of which is selected from N,

[0376] Among them, Ar Ia ,Ar Ib ,Ar Ic ,Ar IIa and Ar IIb is, 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 replaced by one or more radicals Ra replace;

[0377] Among them, Ar L is a divalent aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which is optionally substituted by one or more radicals R a replace,

[0378] Where R a is, identically or differently on each occurrence, H, D, F, Cl, Br, I, CHO, N(R b )2、N(Ar 1s )2、B(Ar 1s )2、C(=O)Ar 1s , P(=Y)(R c )2、S(=O)Ar 1s 、S(=O)2Ar 1s , CR b =CR b Ar 1s 、CN、NO2、Si(R b )3、B(OR b )2、B(R b )2. B(N(R b )2)2、OSO2R b , substituted or unsubstituted straight chain C1 to C 20 Alkyl, substituted or unsubstituted straight chain C1 to C 20 Alkenyl, substituted or unsubstituted straight chain C1 to C 20 Alkynyl, substituted or unsubstituted straight chain C1 to C 20 Alkoxy, substituted or unsubstituted straight chain C1 to C 20 Thioalkoxy, substituted or unsubstituted branched C3 to C 20 Alkyl, substituted or unsubstituted branched C3 to C 20 Alkenyl, substituted or unsubstituted branched C3 to C 20 Substituted or unsubstituted branched C3 to C 20 Alkynyl, substituted or unsubstituted branched C3 to C 20 Alkoxy or substituted or unsubstituted branched C3 to C 20 Thioalkoxy, substituted or unsubstituted cyclic C3 to C 40 Alkyl, substituted or unsubstituted cyclic C3 to C 40 Alkenyl, substituted or unsubstituted cyclic C3 to C 40 Alkynyl, substituted or unsubstituted cyclic C3 to C 40 Alkoxy or substituted or unsubstituted cyclic C3 to C 40 Thioalkoxy; substituted or unsubstituted heterocyclic C3 to C 40Alkyl, substituted or unsubstituted heterocyclic C3 to C 40 Alkenyl, substituted or unsubstituted heterocyclic C3 to C 40 Alkynyl, substituted or unsubstituted heterocyclic C3 to C 40 Alkoxy or substituted or unsubstituted heterocyclic C3 to C 40 Thioalkoxy;

[0379] wherein one or more substituents (if present) are selected from R b , wherein one or more non-adjacent CH2 groups are optionally replaced by R b C=CR b 、C≡C、Si(R b )2、Ge(R b )2、Sn(R b )2. C=O, C=S, C=Se, C=NR b ,P(=O)(R b )、SO、SO2、NR b , O, S or CONR b and wherein one or more H atoms are optionally replaced by D, F, Cl, Br, I, CN or NO2 or in each case by one or more radicals R b A substituted aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, or optionally substituted by one or more radicals R b Substituted aryloxy or heteroaryloxy groups having 5 to 60 aromatic ring atoms, or combinations of these systems; two or more adjacent substituents R a These optionally form with one another a monocyclic or polycyclic aliphatic or aromatic ring system;

[0380] Among them, Ar 1s is, identically or differently on each occurrence, optionally substituted by one or more radicals R b Substituted aromatic or heteroaromatic ring system having 5 to 30 aromatic ring atoms; two groups Ar bonded to the same nitrogen, phosphorus or boron atom 1s It can also be selected from B(R b )、C(R b )2、Si(R b )2. C=O, C=NR b , C=C(R b )2, O, S, S=O, SO2, N(R b )、P(R b ) and P(=Y)R c The bridging groups are connected to each other;

[0381] Where R b H, D or C1 to C, identically or differently on each occurrence20 Aliphatic hydrocarbon group, C1 to C 20 Aryl and / or C1 to C 20 heteroaryl, in which the H atoms are additionally optionally replaced by D or F; two or more adjacent substituents R b This can also form monocyclic or polycyclic aliphatic or aromatic ring systems with one another;

[0382] wherein Y is selected from O, S or Se, preferably O, and R c Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, partially fluorinated or perfluorinated C1 to C6 alkyl, partially fluorinated or perfluorinated C1 to C6 alkoxy, partially deuterated or perdeuterated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkoxy.

[0383] For the purposes of the present invention, an aromatic or heteroaromatic ring system is intended to be regarded as meaning a system which does not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups may also be interrupted by short non-aromatic units (preferably less than 10% non-H atoms), for example sp 3 The aromatic ring systems are interrupted by hybridized C, N or O atoms. Thus, for the purposes of the present invention, systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ether, stilbene, benzophenone, etc. are also intended to be regarded as meaning aromatic ring systems. Likewise, an aromatic or heteroaromatic ring system is regarded as meaning a system in which a plurality of aryl or heteroaryl groups are linked to one another by single bonds, for example biphenyl, terphenyl or bipyridine.

[0384] According to one embodiment, the first electron transport layer comprises an electron transport compound, wherein the electron transport compound is selected from 2-([1,1'-biphenyl]-3-yl)-4-(2',6'-diphenyl-[1,1':4',1"-terphenyl]-4-yl)-6-phenyl-1,3,5-triazine, 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline], 2-(4-(1-(pyridin-2-yl)imidazo[1,5-a]pyridin-3-yl)phenyl)-1,10-phenanthroline, 3-(3-(9,10-diphenylanthracen-2-yl)phenyl)-1-(pyridin-2-yl)imidazo[1,5-a]pyridine, 2,4-diphenyl-6-(3"-(3,5,6-triphenylpyrazine- 2-(3'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-1,3,5-triazine, 2-(3'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, 2,4-diphenyl-6-(4',5',6'-triphenyl-[1,1':2',1": 3",1"':3"',1""-pentaphenyl]-3""-yl)-1,3,5-triazine; 2-phenyl-4-(3-(pyridin-4-yl)phenyl)-6-(3-(3,5,6-triphenylpyrazin-2-yl)phenyl)pyrimidine; (3-(10-(3-(2,6-diphenylpyrimidin-4-yl)phenyl)anthracen-9-yl)phenyl)dimethylphosphine oxide.

[0385] According to one embodiment, when using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the LUMO energy level of the electron transport compound is ≤-1.50 eV, preferably ≤-1.55 eV, preferably ≤-1.60 eV, and most preferably ≤-1.65 eV.

[0386] According to one embodiment, when using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase for calculation, the LUMO energy level of the electron transport compound is 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.

[0387] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and Gaussian 6-31G* basis set is in the range of ≥0D to ≤4.0D; or ≥0D to ≤3.7D; or ≥0D to ≤3.5D; or ≥0D to ≤3.0D; or ≥0D to ≤2.7D; or ≥0D to ≤2.5D; or ≥0D to ≤2.0D; or ≥0D to ≤1.5D; or ≥0D to ≤1.0D.

[0388] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤3.7D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.90eV to ≤-1.65eV.

[0389] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤3.7D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.87eV to ≤-1.65eV.

[0390] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤3.5D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.90eV to ≤-1.65eV.

[0391] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤3.5D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.87eV to ≤-1.65eV.

[0392] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤3.0D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.90eV to ≤-1.65eV.

[0393] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤3.0D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.87eV to ≤-1.65eV.

[0394] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤2.7D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.90eV to ≤-1.65eV.

[0395] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤2.7D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.87eV to ≤-1.65eV.

[0396] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤2.5D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.90eV to ≤-1.65eV.

[0397] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤2.5D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.87eV to ≤-1.65eV.

[0398] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤2.0D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.90eV to ≤-1.65eV.

[0399] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤2.0D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.87eV to ≤-1.65eV.

[0400] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤1.5D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.90eV to ≤-1.65eV.

[0401] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤1.5D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.87eV to ≤-1.65eV.

[0402] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤1.0D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.90eV to ≤-1.65eV.

[0403] According to one embodiment, the molecular dipole moment of the electron transport compound calculated by the TURBOMOLE V6.5 program package in the gas phase using the hybrid functional B3LYP and the Gaussian 6-31G* basis set is in the range of ≥0D to ≤1.0D; and when calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase, the LUMO energy level of the electron transport compound of the first electron transport layer is in the range of ≥-1.87eV to ≤-1.65eV.

[0404] The unit of dipole moment is "Debye", abbreviated to "D". In this context, the dipole moment of a molecule containing N atoms is It is derived from the following formula:

[0405]

[0406] where q i and is the partial charge and position of atom i in the molecule. The dipole moment is determined by semi-empirical molecular orbital method. As implemented in the program package TURBOMOLE V6.5 (TURBOMOLE Co., Ltd., Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), the geometry of the molecular structure is optimized using hybrid functional B3LYP and 6-31G* basis set in the gas phase. If more than one conformation is feasible, the conformation with the lowest total energy is selected to determine the bond length of the molecule.

[0407] Additional electron transport layer (not the first electron transport layer)

[0408] In addition to the first electron transport layer, the organic electroluminescent device according to the present invention may also comprise one or more additional electron transport layers. Such additional electron transport layers do not necessarily contain 8-hydroxyquinoline lithium. In particular, the additional electron transport layer closest to the cathode preferably contains 8-hydroxyquinoline lithium, i.e. an electron transport layer not associated with the charge generation layer.

[0409] According to a preferred embodiment of the present invention, the electron transport layer may be an organic semiconductor layer of the present invention comprising the compound of the present invention represented by the general formula (I) as defined herein.

[0410] According to various embodiments, an OLED may include an electron transport layer or an electron transport layer stack including at least a first electron transport layer and at least a second electron transport layer.

[0411] By properly adjusting the energy level of a specific ETL layer, the injection and transport of electrons can be controlled, and holes can be effectively blocked. As a result, OLEDs can have a long lifespan.

[0412] One or more additional electron transport layers of the organic electroluminescent device may contain a compound represented by the general formula (xxxa) or formula (xxxb) as defined above as an organic electron transport matrix (ETM) material. In addition to or instead of the compound represented by the general formula (I), the electron transport layer may also contain other ETM materials known in the art. Similarly, the electron transport layer may contain a compound represented by the general formula (I) as the only electron transport matrix material. In the case where the organic electronic device of the present invention comprises more than one electron transport layer, the compound represented by the general formula (I) may be contained only in one electron transport layer, in more than one electron transport layer, or in all electron transport layers. According to the present invention, in addition to the ETM material, the electron transport layer may also contain at least one additive as defined below.

[0413] In addition, the electron transport layer may further include one or more n-type dopants. The additive may be an n-type dopant. The additive may be an alkali metal, an alkali metal compound, an alkaline earth metal, an alkaline earth metal compound, a transition metal, a transition metal compound, or a rare earth metal. In another embodiment, the metal may be one selected from the group consisting of Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, La, Ce, Sm, Eu, Tb, Dy, and Yb. In another embodiment, the n-type dopant may be one selected from the group consisting of Cs, K, Rb, Mg, Na, Ca, Sr, Eu, and Yb. In one embodiment, the alkali metal compound may be 8-hydroxyquinoline lithium (LiQ), lithium tetrakis (1H-pyrazol-1-yl) borate, or 2-(diphenylphosphoryl) phenolate lithium. There is no particular limitation on compounds suitable for ETM (which may be used together with the compounds of the present invention represented by the general formula (I) as defined above). In one embodiment, the electron transport matrix compound consists of covalently bonded atoms. Preferably, the electron transport matrix compound comprises a conjugated system of at least 6, more preferably at least 10 delocalized electrons. In one embodiment, the conjugated system of delocalized electrons may be contained in an aromatic or heteroaromatic moiety, as disclosed in, for example, documents EP 1 970 371 A1 or WO 2013 / 079217 A1.

[0414] Specific embodiments of the organic electroluminescent device according to the present invention

[0415] According to one embodiment, an organic electroluminescent device is provided, wherein the organic electroluminescent device comprises an anode layer, a cathode layer, a first light-emitting layer and a second light-emitting layer, a first charge generation layer, and a first electron transport layer.

[0416] wherein the first charge generating layer is arranged between the first light emitting layer and the second light emitting layer,

[0417] wherein the first charge generation layer comprises a first n-type charge generation layer and a first p-type charge generation layer,

[0418] wherein the first n-type charge generation layer is closer to the anode layer than the first p-type charge generation layer,

[0419] wherein the first p-type charge generation layer is closer to the cathode layer than the first n-type charge generation layer,

[0420] wherein the first electron transport layer is arranged in direct contact with the first n-type charge generation layer, and

[0421] The first n-type charge generation layer comprises a metal dopant and a compound of formula (I):

[0422]

[0423] Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 Heteroaryl,

[0424] wherein one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents can be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O,

[0425] R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O,

[0426] Where R 1 To R 7 The one or more substituents on the 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, halogen, F, CN or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy;

[0427] And X 1 is selected from O, S or Se, preferably O,

[0428] wherein L is selected from substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C2 to C 24 Heteroaryl,

[0429] wherein one or more substituents on L (if present) are independently selected from D, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, halogen, F, CN or PX 1 (R 8 )2, wherein the substituents may be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O,

[0430] wherein formula (I) may be undeuterated, partially deuterated or fully deuterated,

[0431] wherein the metal dopant is selected from ytterbium;

[0432] The first electron transport layer does not contain 8-hydroxyquinoline lithium.

[0433] Other layers

[0434] According to the present invention, in addition to the layers mentioned above, the organic electronic device may further comprise other layers. Exemplary embodiments of the various layers are described below:

[0435] Base

[0436] The substrate can be any substrate commonly used in the manufacture of electronic devices such as organic light emitting diodes. If light is to be emitted through the substrate, the substrate should be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be either a transparent material or an opaque material, such as a glass substrate, a plastic substrate, a metal substrate or a silicon substrate.

[0437] Anode electrode

[0438] The first electrode or the second electrode included in the organic electronic device of the present invention can be an anode electrode. The anode electrode can be formed by depositing or sputtering a material for forming the anode electrode. The material for forming the anode electrode can be a high work function material to promote hole injection. The anode material can also be selected from a low work function material (i.e., aluminum). The anode electrode can 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 (AlZO) and zinc oxide (ZnO) can be used to form the anode electrode. The anode electrode can also be formed using a metal, typically silver (Ag), gold (Au) or a metal alloy.

[0439] Hole injection layer

[0440] The hole injection layer (HIL) can be formed on the anode by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When the HIL is formed using vacuum deposition, the deposition conditions may vary according to the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, in general, the conditions for vacuum deposition may include a deposition temperature of 100° C. to 500° C., a ... -8 Support up to 10 -3 Torr pressure (1 Torr equals 133.322 Pa) and a deposition rate of 0.1 nm / s to 10 nm / s.

[0441] When the HIL is formed using spin coating or printing, the coating conditions may vary according to the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80° C. to about 200° C. After coating, the heat treatment removes the solvent.

[0442] The HIL may be formed of any compound commonly used to form a HIL. Examples of the compound that can be used to form the HIL include phthalocyanine compounds 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 / camphorsulfonic acid (Pani / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS).

[0443] The HIL may include or consist of a p-type dopant, and the p-type dopant may be selected from tetrafluoro-tetracyanoquinodimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile or 2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile), but is not limited thereto. The HIL may be selected from a hole transport host compound doped with a p-type dopant. Typical examples of known doped hole transport materials include copper phthalocyanine (CuPc), which has a HOMO level of about -5.2 eV. , doped with tetrafluoro-tetracyanoquinodimethane (F4TCNQ), whose LUMO energy level is about -5.2eV; zinc phthalocyanine (ZnPc) (HOMO = -5.2eV), which is doped with F4TCNQ; α-NPD (N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-benzidine), which is doped with F4TCNQ. α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diylidene) dimalononitrile. The p-type dopant concentration can be selected from 1 wt% to 20 wt%, more preferably 3 wt% to 10 wt%.

[0444] The thickness of the HIL may be within a range of about 1 nm to about 100 nm, and for example, within a range of about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injection characteristics without substantially deteriorating driving voltage.

[0445] Hole transport layer

[0446] The hole transport layer (HTL) can be formed on the HIL by vacuum deposition, spin coating, slot die coating, printing, casting, Langmuir-Blodgett (LB) deposition, etc. When the HTL is formed by vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for forming the HIL. However, the conditions for vacuum deposition or solution deposition may vary depending on the compound used to form the HTL.

[0447] The HTL can be formed of any compound commonly used to form the HTL. Compounds that can be appropriately used are disclosed in, for example, Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, and are incorporated by reference. Examples of compounds that can 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-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine-based compounds, such as 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and inhibit the diffusion of excitons into the EML.

[0448] The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, further preferably about 20 nm to about 190 nm, further preferably about 40 nm to about 180 nm, further preferably about 60 nm to about 170 nm, further preferably about 80 nm to about 160 nm, further preferably about 100 nm to about 160 nm, further preferably about 120 nm to about 140 nm. The preferred thickness of the HTL may be 170 nm to 200 nm.

[0449] When the thickness of the HTL is within this range, the HTL may have excellent hole transport characteristics without substantially deteriorating driving voltage.

[0450] Electron blocking layer

[0451] The function of the electron blocking layer (EBL) is to prevent electrons from being transferred from the light-emitting layer to the hole transport layer, and thereby confine the electrons to the light-emitting layer. Thereby improving efficiency, operating voltage and / or lifespan. Typically, the electron blocking layer comprises a triarylamine compound. Compared with the LUMO energy level of the hole transport layer, the triarylamine compound may have a LUMO energy level that is closer to the vacuum energy level. Compared with the HOMO energy level of the hole transport layer, the electron blocking layer may have a HOMO energy level that is further away from the vacuum energy level. The thickness of the electron blocking layer may be selected between 2nm and 20nm.

[0452] If the electron blocking layer has a high triplet energy level, it may also be described as a triplet controlling layer.

[0453] The function of the triplet control layer is to reduce the quenching of the triplet state when using a phosphorescent green or blue emitting layer. Thus, a higher luminous efficiency of the phosphorescent emitting layer can be achieved. The triplet control layer is selected from triarylamine compounds whose triplet energy level is higher than the triplet energy level of the phosphorescent emitter in the adjacent emitting layer. Suitable compounds for triplet control layers, in particular triarylamine compounds, are described in EP 2 722 908 A1.

[0454] Emitting Layer (EML)

[0455] The EML can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the EML is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for forming the HIL. However, the conditions for deposition and coating may vary depending on the compound used to form the EML.

[0456] The light-emitting layer may not contain the compound of formula (I).

[0457] The light-emitting layer (EML) may be formed of a combination of a host and a light-emitting dopant. Examples of the host are Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4"-tri(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tri(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0458] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emitter may be a small molecule or a polymer.

[0459] Examples of red emitter dopants are PtOEP, Ir(piq)3 and Btp2Ir(acac), but are not limited thereto. These compounds are phosphorescent emitters, however, fluorescent red emitter dopants may also be used.

[0460] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy=phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[0461] Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd) and Ir(dfppz)3 and trifluorene. 4,4'-bis(4-diphenylaminophenylvinyl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe) are examples of fluorescent blue emitter dopants.

[0462] The amount of the luminophore dopant may be in the range of about 0.01 to about 50 parts by weight relative to 100 parts by weight of the host. Alternatively, the luminescent layer may be composed of a luminescent polymer. The thickness of the EML may be about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML may have excellent luminescence without causing substantial damage to the driving voltage.

[0463] Hole Blocking Layer (HBL)

[0464] The hole blocking layer (HBL) can be formed on the EML by using vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. to prevent holes from diffusing into the ETL. When the EML contains a phosphorescent dopant, the HBL may also have a triplet exciton blocking function. The hole blocking layer may be an organic semiconductor layer of the present invention comprising or consisting of the compound of the present invention represented by the general formula (1) as defined above.

[0465] HBL may also be referred to as auxiliary ETL or a-ETL.

[0466] When the HBL is formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for forming the HIL. However, the conditions for deposition and coating may vary depending on the compound used to form the HBL. Any compound commonly used to form the HBL may be used. Examples of compounds used to form the HBL include Oxadiazole derivatives, triazole derivatives and phenanthroline derivatives.

[0467] The thickness of the HBL may be within a range of about 5 nm to about 100 nm, for example, 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 substantially compromising driving voltage.

[0468] The hole blocking layer may also be described as an a-ETL or auxiliary ETL.

[0469] Electron injection layer (EIL)

[0470] An optional EIL that can facilitate electron injection from the cathode can be formed on the ETL, preferably directly on the electron transport layer. Examples of materials for forming the EIL include 8-hydroxyquinoline lithium (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, Mg known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL, but the deposition and coating conditions may vary depending on the material for forming the EIL.

[0471] The thickness of the EIL may be within a range of about 0.1 nm to about 10 nm, for example, within a range of about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL may have satisfactory electron injection properties without substantially deteriorating driving voltage.

[0472] Cathode electrode

[0473] The cathode electrode is formed on the EIL (if present). The cathode electrode may be formed of a metal, an alloy, a conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode electrode may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode may be formed of a transparent conductive oxide such as ITO or IZO.

[0474] The thickness of the cathode electrode may be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode electrode is in the range of about 5 nm to about 50 nm, the cathode electrode may be transparent or translucent even if it is formed of a metal or a metal alloy.

[0475] It is to be understood that the cathode electrode is not part of the electron injection layer or the electron transport layer.

[0476] Charge generation layer / hole generation layer

[0477] The first charge generation layer (CGL) includes a p-type charge generation layer and an n-type charge generation layer. An intermediate layer may be disposed between the p-type charge generation layer and the n-type charge generation layer.

[0478] Typically, the charge generation layer is a pn junction connecting an n-type charge generation layer (electron generation layer) and a hole generation layer. The n-side of the pn junction generates electrons and injects them into the adjacent layer in the direction of the anode. Similarly, the p-side of the pn junction generates holes and injects them into the adjacent layer in the direction of the cathode.

[0479] Charge generation layers are used in tandem and stacked devices, for example in tandem or stacked OLEDs comprising two or more light-emitting layers between two electrodes. In a tandem or stacked OLED comprising two light-emitting layers, an n-type charge generation layer provides electrons to a first light-emitting layer arranged near the anode, while a hole generation layer provides holes to a second light-emitting layer arranged between the first light-emitting layer and the cathode.

[0480] Suitable host materials for the hole generation layer may be materials conventionally used as hole injection and / or hole transport host materials. In addition, conventional materials may be used as p-type dopants for the hole generation layer. For example, the p-type dopant may be one selected from the group consisting of tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ), tetracyanoquinodimethane derivatives, radialene derivatives, iodine, FeCl3, FeF3, and SbCl5. In addition, the host may be one selected from the group consisting of N,N'-di(naphthalene-1-yl)-N,N-diphenyl-benzidine (NPB), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1-biphenyl-4,4'-diamine (TPD), and N,N',N'-tetranaphthyl-benzidine (TNB). The p-type charge generation layer may be composed of CNHAT.

[0481] Organic electroluminescent devices

[0482] According to one embodiment, the organic electroluminescent device further comprises a layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

[0483] According to one embodiment, the organic electroluminescent device further comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a first electron blocking layer, a second electron blocking layer, an optional first hole blocking layer, an optional second hole blocking layer, a second electron transport layer and an electron injection layer.

[0484] According to one embodiment, an 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 light-emitting layer (145); an optional first hole blocking layer (147); and a first electron transport layer (149), wherein the first electron transport layer (149) does not contain 8-hydroxyquinoline lithium, preferably does not contain a lithium organic metal complex, and more preferably does not contain a lithium metal complex, wherein the first electron transport layer (149) is preferably in direct contact with the first light-emitting layer (145); a first charge generation layer (160) disposed on 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 (161); a second hole transport layer (241); a second electron blocking layer (242); a second light-emitting layer (245); an optional second hole blocking layer (247); an electron transport layer (148); an electron injection layer (180); and a cathode layer (190).

[0485] According to one embodiment, the organic electroluminescent device further comprises a third light-emitting layer, a second electron transport layer and a second charge generation layer.

[0486] wherein the third light emitting layer is arranged between the second charge generating layer and the cathode layer,

[0487] wherein the second charge generation layer is arranged between the first charge generation layer and the cathode layer and between the second light emitting layer and the third light emitting layer,

[0488] wherein the second charge generation layer comprises a second n-type charge generation layer and a second p-type charge generation layer,

[0489] wherein the second n-type charge generation layer is arranged closer to the anode layer than the second p-type charge generation layer,

[0490] wherein the second p-type charge generation layer is arranged closer to the cathode layer than the second n-type charge generation layer,

[0491] wherein the second electron transport layer is arranged between the second light-emitting layer and the third light-emitting layer,

[0492] wherein the second electron transport layer is in direct contact with the second n-type charge generation layer,

[0493] in

[0494] wherein the second n-type charge generation layer comprises a metal dopant and a compound of formula (I),

[0495]

[0496] Where R 1 To R 7 , L and Ar may be selected as defined above;

[0497] wherein the compound of formula (I) in the first n-type charge generation layer and the compound of formula (I) in the second n-type charge generation layer are selected to be the same or different, preferably the same;

[0498] wherein the metal dopant is ytterbium; and

[0499] The second electron transport layer does not contain 8-hydroxyquinoline lithium.

[0500] According to one embodiment, the organic electroluminescent device comprises: an anode layer (120); a hole injection layer (130); a hole transport layer (141); a first electron blocking layer (142); a first light-emitting layer (145); an optional first hole blocking layer (147); a first electron transport layer (149), wherein the first electron transport layer (149) does not contain 8-hydroxyquinoline lithium, preferably does not contain a lithium organic metal complex, and more preferably does not contain a lithium metal complex, wherein the first electron transport layer (149) is preferably in direct contact with the first light-emitting layer (145); a first charge generation layer (160) disposed on the first electron transport layer (149), wherein the first electron The 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 light-emitting layer (245); an optional second hole blocking layer (247); a second electron transport layer (249), wherein the second electron transport layer (ETL2) 249 does not contain 8-hydroxyquinoline lithium, preferably does not contain lithium an organic metal complex, more preferably free of lithium metal complexes, wherein the second electron transport layer (249) is preferably in direct contact with the second light-emitting layer (245); a second charge generation layer (260) disposed on the second electron transport layer (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 (ETL1) 249 is in direct contact with the second light-emitting layer (245); and A second n-type charge generation layer (n-CGL2) 261 is in direct contact, wherein the second n-type charge generation layer (n-CGL2) 261 can be selected to be the same as or different from the first n-type charge generation layer (n-CGL1) 161, and wherein the second p-type charge generation layer (p-CGL2) 262 can be selected to be the same as or different from the first p-type charge generation layer (p-CGL1) 161; and a third hole transport layer (341) and a third electron blocking layer (342), a third light-emitting layer (345), an optional third hole blocking layer (347), an electron transport layer (148), an electron injection layer (180) and a cathode layer (190).

[0501] Preparation of organic electroluminescent devices

[0502] According to another aspect of the present invention, there is provided a method for manufacturing an organic electroluminescent device (OLED), the method using:

[0503] - At least one deposition source, preferably two deposition sources, and more preferably at least three deposition sources.

[0504] Suitable deposition methods may include:

[0505] -Deposition by vacuum thermal evaporation;

[0506] - deposition by solution processing, preferably selected from spin coating, printing, casting; and / or

[0507] -Slot die coating.

[0508] According to various embodiments of the present invention, there is provided a method, the method using:

[0509] a first deposition source for releasing a compound of formula (I) according to the invention, and

[0510] - a second deposition source for releasing Yb;

[0511] The method comprises the steps of forming an organic semiconductor layer; wherein for an organic light emitting diode (OLED):

[0512] - the organic semiconductor layer is formed by releasing the compound of formula (I) according to the present invention from the first deposition source and releasing Yb from the second deposition source.

[0513] According to various embodiments of the present invention, the method may further include forming a light-emitting layer on the anode electrode, and forming at least one layer selected from the following group between the anode electrode and the first electron transport layer: forming a hole injection layer, forming a hole transport layer, or forming a hole blocking layer.

[0514] According to various embodiments of the present invention, the method may further include the step of forming an organic light emitting diode (OLED), wherein

[0515] - forming a first anode electrode on the substrate,

[0516] - forming a light emitting layer on the first anode electrode,

[0517] - forming an electron transport layer stack on the light-emitting layer, optionally forming a hole blocking layer on the light-emitting layer and forming an organic semiconductor layer,

[0518] -Finally, the cathode electrode is formed,

[0519] - forming an optional hole injection layer, a hole transport layer and a hole blocking layer in sequence between the first anode electrode and the light-emitting layer,

[0520] - forming an optional electron injection layer between the organic semiconductor layer and the cathode electrode.

[0521] According to various embodiments of the present invention, the method may further include forming an electron injection layer on the organic semiconductor layer. However, according to various embodiments of the OLED of the present invention, the OLED may not include an electron injection layer.

[0522] According to another aspect of the present invention, an electronic device is provided, the electronic device comprising at least one organic light emitting device according to any embodiment described in the entire application, preferably, the electronic device comprises an organic light emitting diode in one of the embodiments described in the entire application. More preferably, the electronic device is a display device.

[0523] In one embodiment, the organic electronic device according to the present 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.

[0524] In one embodiment, the radialene compound and / or the quinodimethane compound can be substituted by one or more halogen atoms and / or one or more electron withdrawing groups. The electron withdrawing group can be selected from a nitrile group, a halogenated alkyl group, or a fully halogenated alkyl group, or a fully fluorinated alkyl group. Other examples of electron withdrawing groups can be acyl, sulfonyl or phosphoryl groups.

[0525] Alternatively, the acyl group, sulfonyl group and / or phosphoryl group may comprise a halogenated and / or perhalogenated hydrocarbon group. In one embodiment, the perhalogenated hydrocarbon group may be a perfluorinated hydrocarbon group. Examples of perfluorinated hydrocarbon groups may be perfluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluorobutyl, perfluorophenyl, perfluorotolyl; Examples of sulfonyl groups comprising halogenated hydrocarbon groups may be trifluoromethylsulfonyl, pentafluoroethylsulfonyl, pentafluorophenylsulfonyl, heptafluoropropylsulfonyl, nonafluorobutylsulfonyl, etc.

[0526] In one embodiment, the radialene compound and / or the quinodimethane compound may be included in the hole injection layer, the hole transport layer, and / or the hole generation layer.

[0527] In one embodiment, the radialene compound may have formula (XX) and / or the quinodimethane compound may have formula (XXIa) or formula (XXIb):

[0528]

[0529] where (as an exception to the above description) R 1 , R2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 11 , R 12 , R 15 , R 16 , R 20 , R 21 are independently selected from the above electron withdrawing groups, and R 9 , R 10 , R 13 , R 14 , R 17 , R 18 , R 19 , R 22 , R 23 and R 24 Independently selected from H, halogen and the above-mentioned electron withdrawing groups.

[0530] According to one embodiment of the present invention, the organic semiconductor layer comprising the compound of formula (I) is adjacent to the layer comprising the compound of formula (XX), formula (XXIa) or formula (XXIb).

[0531] According to one embodiment of the present invention, the organic semiconductor layer comprising the compound of formula (I) is in direct contact with the layer comprising the compound of formula (XX), formula (XXIa) or formula (XXIb).

[0532] Compounds of formula (M1) or formula (M2)

[0533] According to one aspect, the present invention relates to a compound of formula (M1) or formula (M2):

[0534]

[0535] In formula (M1),

[0536] -R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and

[0537] -R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O;

[0538] -Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 heteroaryl;

[0539] Wherein in formula (M2),

[0540] -R 2 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and

[0541] -Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24heteroaryl;

[0542] -L is selected from substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C2 to C 24 Heteroaryl.

[0543] 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),

[0544]

[0545] In formula (M3),

[0546] -R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and

[0547] -R La , R Lb , R Lc and R Ldindependently selected from H, D, substituted or unsubstituted C1 to C 16 Alkyl, substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O;

[0548] In formula (M4),

[0549] -R 2 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and

[0550] -L is selected from substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C2 to C 24 Heteroaryl.

[0551] R of formula (M1) and formula (M3) 1 To R 7

[0552] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1Selected from O, S or Se, preferably O.

[0553] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F.

[0554] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 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 C2 to C 24 Heteroaryl, halogen, F.

[0555] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 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 C2 to C 24 Heteroaryl, F.

[0556] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 Aryl or substituted or unsubstituted C2 to C 18 Heteroaryl, CN, halogen, Cl, F.

[0557] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 Aryl or substituted or unsubstituted C2 to C 18 Heteroaryl, F.

[0558] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl, CN, halogen, Cl, F.

[0559] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl, F.

[0560] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl, CN, halogen, Cl, F.

[0561] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl, F.

[0562] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 Independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, CN, halogen, Cl, F.

[0563] According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 is independently selected from H, D, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 aryl group or a substituted or unsubstituted C3 to C5 heteroaryl group, or F. According to one embodiment, in formula (M1) or formula (M3), R 1 To R 7 Independently selected from H, D.

[0564] R of formula (M2) and formula (M4) 2 To R 7

[0565] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0566] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F.

[0567] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 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 C2 to C 24 Heteroaryl, halogen, F.

[0568] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C 16Alkyl, substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 Heteroaryl, F.

[0569] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 Aryl or substituted or unsubstituted C2 to C 18 Heteroaryl, CN, halogen, Cl, F.

[0570] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 Aryl or substituted or unsubstituted C2 to C 18 Heteroaryl, F.

[0571] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl, CN, halogen, Cl, F.

[0572] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl, F.

[0573] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl, CN, halogen, Cl, F.

[0574] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl, F.

[0575] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 Independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, CN, halogen, Cl, F.

[0576] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 Independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, F.

[0577] According to one embodiment, in formula (M2) or formula (M4), R 2 To R 7 Independently selected from H, D.

[0578] R in formula (M1) to formula (M4) 1 To R 7 Substituents on

[0579] R in formula (M1) and formula (M3) 1 To R 7 Or R in formula (M2) and formula (M4) 2 To R 7 Each may independently be unsubstituted or substituted with one or more substituents.

[0580] According to one embodiment, R in formula (M1) and formula (M3) 1 To R 7 Or R in formula (M2) and formula (M4) 2 To R 7 The one or more substituents on the 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, halogen, F, CN or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0581] According to one embodiment, R in formula (M1) and formula (M3) 1 To R 7 Or R in formula (M2) and formula (M4) 2 To R 7 The one or more substituents on the 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0582] According to one embodiment, R in formula (M1) and formula (M3) 1 To R 7 Or R in formula (M2) and formula (M4) 2 To R 7 The one or more substituents on the 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN.

[0583] According to one embodiment, R in formula (M1) and formula (M3) 1 To R 7 Or R in formula (M2) and formula (M4) 2 To R 7 The one or more substituents on the 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN.

[0584] According to one embodiment, R in formula (M1) and formula (M3) 1 To R 7 Or R in formula (M2) and formula (M4) 2 To R 7 The one or more substituents on the 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN.

[0585] According to one embodiment, R in formula (M1) and formula (M3) 1 To R 7 Or R in formula (M2) and formula (M4) 2To R 7 The one or more substituents on the 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0586] According to one embodiment, R in formula (M1) and formula (M3) 1 To R 7 Or R in formula (M2) and formula (M4) 2 To R 7 The one or more substituents on (if present) are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0587] R of formula (M1) or formula (M3) La , R Lb , R Lc and R Ld

[0588] According to one embodiment, in formula (M1) or formula (M3), R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0589] According to one embodiment, in formula (M1) or formula (M3), R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F.

[0590] According to one embodiment, in formula (M1) or formula (M3), R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 16 alkyl.

[0591] According to one embodiment, in formula (M1) or formula (M3), R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 12 alkyl.

[0592] According to one embodiment, in formula (M1) or formula (M3), R La , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 to C8 alkyl.

[0593] According to one embodiment, in formula (M1) or formula (M3), R La , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 to C6 alkyl.

[0594] According to one embodiment, in formula (M1) or formula (M3), R La , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 to C4 alkyl.

[0595] According to one embodiment, in formula (M1) or formula (M3), R La, R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 to C3 alkyl.

[0596] According to one embodiment, in formula (M1) or formula (M3), R La , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 to C2 alkyl.

[0597] According to one embodiment, in formula (M1) or formula (M3), R La , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 alkyl.

[0598] R of formula (M1) or formula (M3) La , R Lb , R Lc and R Ld Substituents on

[0599] R in formula (M1) and formula (M3) La , R Lb , R Lc and R Ld may independently be unsubstituted or substituted with one or more substituents.

[0600] According to one embodiment, R in formula (M1) and formula (M3) La , R Lb , R Lc and R Ld The one or more substituents on the 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, halogen, F, CN or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0601] According to one embodiment, R in formula (M1) and formula (M3) La , R Lb , R Lc and R Ld The one or more substituents on the 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0602] According to one embodiment, R in formula (M1) and formula (M3) La , R Lb , R Lc and R Ld The one or more substituents on the 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN.

[0603] According to one embodiment, R in formula (M1) and formula (M3) La , R Lb , R Lc and R Ld The one or more substituents on the 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN.

[0604] According to one embodiment, R in formula (M1) and formula (M3) La , R Lb , R Lc and R Ld The one or more substituents on the 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN.

[0605] According to one embodiment, R in formula (M1) and formula (M3) La , R Lb , R Lc and R Ld The one or more substituents on the 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0606] According to one embodiment, R in formula (M1) and formula (M3)La , R Lb , R Lc and R Ld The one or more substituents on (if present) are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0607] L in formula (M2) and formula (M4)

[0608] According to one embodiment, in formula (M2) and formula (M4), L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C 18 Heteroaryl.

[0609] According to one embodiment, in formula (M2) and formula (M4), L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl.

[0610] According to one embodiment, in formula (M2) and formula (M4), L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl.

[0611] According to one embodiment, in formula (M2) and formula (M4), L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C3 to C5 heteroaryl.

[0612] According to one embodiment, in formula (M2) and formula (M4), L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring.

[0613] According to one embodiment, in formula (M2) and formula (M4), L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazinyl.

[0614] According to one embodiment, in Formula (M2) and Formula (M4), L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl.

[0615] According to one embodiment, in Formula (M2) and Formula (M4), L is selected from substituted phenyl, unsubstituted phenyl or unsubstituted naphthyl.

[0616] Substituents on L in Formula (M2) and Formula (M4)

[0617] L in formula (M2) and formula (M4) may independently be unsubstituted or substituted with one or more substituents.

[0618] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, C6 to C 18 Aryl, C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, halogen, F, CN or PX 1 (R 8 )2, wherein the substituents may be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0619] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0620] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents can be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1Selected from O, S or Se, preferably O.

[0621] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0622] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0623] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN.

[0624] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0625] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN.

[0626] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0627] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN.

[0628] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0629] According to one embodiment, one or more substituents on L in formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0630] According to one embodiment, one or more substituents on L in Formula (M2) and Formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0631] According to one embodiment, one or more substituents on L in Formula (M2) and Formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0632] According to one embodiment, L in formula (M2) and formula (M4) is selected from the following moieties E1 to E34 shown in Table 2a above.

[0633] According to one embodiment, L in formula (M2) and formula (M4) is selected from the following moieties E1 to E33 shown in Table 2b above.

[0634] According to one embodiment, L in formula (M2) and formula (M4) is selected from moieties E1 to E30.

[0635] According to one embodiment, L in formula (M2) and formula (M4) is selected from moieties E1 to E24.

[0636] According to one embodiment, L in formula (M2) and formula (M4) is selected from moieties E1 to E23.

[0637] According to one embodiment, L in formula (M2) and formula (M4) is selected from moieties E1 to E5 and E8 to E23.

[0638] According to one embodiment, L in formula (M2) and formula (M4) is selected from moieties E1 to E5, E8 to E13 and E16.

[0639] According to one embodiment, L in formula (M2) and formula (M4) is selected from the moieties E1 to E5, E11 and E16.

[0640] According to one embodiment, L in formula (M2) and formula (M4) is selected from moieties E1 to E5 and E16.

[0641] According to one embodiment, L in formula (M2) and formula (M4) is selected from the moieties E1 to E3, E11 and E16.

[0642] According to one embodiment, L in formula (M2) and formula (M4) is selected from the moieties E2 to E3, E11 and E16.

[0643] According to one embodiment, L in formula (M2) and formula (M4) is selected from moieties E2 to E3 and E16.

[0644] Ar of formula (M1) and formula (M3)

[0645] Ar in formula (M1) and formula (M3) is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 Heteroaryl.

[0646] According to one embodiment, Ar of formula (M1) and formula (M3) is selected from substituted or unsubstituted C6 to C 18 Aryl or substituted or unsubstituted C2 to C 18 Heteroaryl.

[0647] According to one embodiment, Ar of formula (M1) and formula (M3) is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl.

[0648] According to one embodiment, Ar of formula (M1) and formula (M3) is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl.

[0649] According to one embodiment, Ar of formula (M1) and formula (M3) is selected from a substituted or unsubstituted C6 aryl group or a substituted or unsubstituted C3 to C5 heteroaryl group.

[0650] According to one embodiment, Ar of formula (M1) and formula (M3) is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring.

[0651] According to one embodiment, Ar of formula (M1) and formula (M3) is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl and substituted or unsubstituted quinolyl.

[0652] Substituents on Ar of Formula (M1) and Formula (M3)

[0653] Ar of formula (M1) and formula (M3) may be unsubstituted or substituted with one or more substituents.

[0654] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents can be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0655] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0656] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents can be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0657] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0658] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0659] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN.

[0660] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0661] According to one embodiment, the one or more substituents on Ar (if present) are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN.

[0662] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0663] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN.

[0664] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0665] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0666] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0667] According to one embodiment, one or more substituents on Ar of formula (M1) and formula (M3), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0668] According to one embodiment, Ar of Formula (M1) and Formula (M3) is selected from the following D1 to D19 shown in Table 1.

[0669] Ar of formula (M2) and formula (M4)

[0670] Ar in formula (M2) and formula (M4) is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 Heteroaryl.

[0671] According to one embodiment, Ar of formula (M2) and formula (M4) is selected from substituted or unsubstituted C6 to C 18 Aryl or substituted or unsubstituted C2 to C 18 Heteroaryl.

[0672] According to one embodiment, Ar of formula (M2) and formula (M4) is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl.

[0673] According to one embodiment, Ar of formula (M2) and formula (M4) is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 Heteroaryl.

[0674] According to one embodiment, Ar of formula (M2) and formula (M4) is selected from a substituted or unsubstituted C6 aryl group or a substituted or unsubstituted C3 to C5 heteroaryl group.

[0675] According to one embodiment, Ar of formula (M2) and formula (M4) is selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring.

[0676] According to one embodiment, Ar is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazinyl and substituted or unsubstituted quinolyl.

[0677] Substituents on Ar of Formula (M2) and Formula (M4)

[0678] Ar of formula (M2) and formula (M4) may be unsubstituted or substituted with one or more substituents.

[0679] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents can be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0680] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0681] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, wherein the substituents can be connected by single bonds or heteroatoms to form a ring, wherein R 8 Independently selected from C6 to C 12 Aryl, C3 to C12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0682] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, PX 1 (R 8 )2, halogen, F or CN, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O.

[0683] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0684] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 20 Heteroaryl, C1 to C 16 Alkyl, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, halogen, F or CN.

[0685] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN, wherein the substituents may be connected via a single bond or a heteroatom to form a ring.

[0686] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 14 Heteroaryl, C1 to C 10 Alkyl, C3 to C 10 Branched alkyl, C3 to C 10 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 10 Alkyl, partially deuterated or fully deuterated C1 to C 10 Alkyl, halogen, F or CN.

[0687] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0688] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, C1 to C6 alkyl, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C6 alkyl, partially deuterated or perdeuterated C1 to C6 alkyl, halogen, F or CN.

[0689] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0690] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 to C 10 Aryl, substituted or unsubstituted C3 to C 10 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0691] According to one embodiment, one or more substituents on Ar of formula (M2) and formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN, wherein the substituents may be connected by a single bond or a heteroatom to form a ring.

[0692] According to one embodiment, one or more substituents on Ar of Formula (M2) and Formula (M4), if present, are independently selected from D, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, C1 to C4 alkyl, C3 to C4 branched alkyl, C3 to C6 cyclic alkyl, partially fluorinated or perfluorinated C1 to C4 alkyl, partially deuterated or perdeuterated C1 to C4 alkyl, halogen, F or CN.

[0693] According to one embodiment, Ar of Formula (M2) and Formula (M4) is selected from the following D1 to D19 shown in Table 1.

[0694] Specific embodiments of the compounds of formula (M1) to formula (M4)

[0695] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C 18 Heteroaryl.

[0696] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X1 Selected from O, S or Se, preferably O.

[0697] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C 18 heteroaryl; and in formula (M2), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0698] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and in formula (M1), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0699] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C 18 heteroaryl; and in formula (M2), Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0700] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and in formula (M1), Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0701] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C2 to C 18 heteroaryl; and in formula (M2), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0702] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkyl, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0703] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl.

[0704] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld independently selected from H, D, substituted or unsubstituted C1 to C 16Alkyl, substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 Heteroaryl, CN, halogen, F.

[0705] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 heteroaryl; and in formula (M2), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0706] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld 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 C2 to C 24 heteroaryl, CN, halogen, F; and in formula (M1), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0707] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 heteroaryl; and in formula (M2), Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0708] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld 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 C2 to C 24heteroaryl, CN, halogen, F; and in formula (M1), Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0709] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 heteroaryl; and in formula (M2), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0710] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld 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 C2 to C 24 heteroaryl, CN, halogen, F; and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0711] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 16 alkyl.

[0712] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10heteroaryl; and in formula (M2), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0713] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 16 and in formula (M1), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0714] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 to C 10 heteroaryl; and in formula (M2), Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0715] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 16 and in formula (M1), Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0716] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C2 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 group.

[0717] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; RLa , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 16 and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0718] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C3 to C5 heteroaryl.

[0719] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 12 alkyl.

[0720] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C3 to C5 heteroaryl; and in formula (M2), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0721] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 12 and in formula (M1), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0722] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10aryl or substituted or unsubstituted C3 to C5 heteroaryl; and in formula (M2), Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0723] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 12 and in formula (M1), Ar is selected from a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0724] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C3 to C5 heteroaryl; and in formula (M2), Ar is selected from an unsubstituted 2-pyridine group, an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0725] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 12 and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0726] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring.

[0727] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and RLd Independently selected from H, D and substituted or unsubstituted C1 to C8 alkyl.

[0728] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Ar is selected from a substituted or unsubstituted C3 to C5 heteroaryl group, wherein the heteroaryl group is a six-membered ring; and in formula (M2), Ar is selected from a substituted or unsubstituted pyridine group, a substituted or unsubstituted quinoline group, or a substituted or unsubstituted phenyl group.

[0729] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C8 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0730] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 Ar is selected from a substituted or unsubstituted C3 to C5 heteroaryl group, wherein the heteroaryl group is a six-membered ring; and in formula (M2), Ar is selected from a substituted or unsubstituted 2-pyridine group, a substituted or unsubstituted 2-quinoline group, or a substituted or unsubstituted phenyl group.

[0731] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld independently selected from H, D and substituted or unsubstituted C1 to C8 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl group.

[0732] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7Independently selected from H or D; L is selected from substituted or unsubstituted C6 aryl, substituted or unsubstituted naphthyl or substituted or unsubstituted C3 to C5 heteroaryl, wherein the heteroaryl is a six-membered ring; and in formula (M2), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0733] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld is independently selected from H, D and a substituted or unsubstituted C1 to C8 alkyl group; and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0734] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 is independently selected from H or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazinyl. According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 to C6 alkyl.

[0735] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazine; and in formula (M2), Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.

[0736] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld independently selected from H, D and substituted or unsubstituted C1 to C6 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0737] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazine; and in formula (M2), Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl.

[0738] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld independently selected from H, D and substituted or unsubstituted C1 to C6 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl group.

[0739] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazine; and in formula (M2), Ar is selected from unsubstituted 2-pyridine group or unsubstituted 2-quinoline group or unsubstituted phenyl.

[0740] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and a substituted or unsubstituted C1 to C6 alkyl group; and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0741] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 Independently selected from H or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl.

[0742] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; RLa , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 to C4 alkyl.

[0743] According to one embodiment, in formula (M2) and formula (M4), 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 substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl.

[0744] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C4 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0745] According to one embodiment, in formula (M2) and formula (M4), 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 substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl.

[0746] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld independently selected from H, D and substituted or unsubstituted C1 to C4 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl group.

[0747] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 are independently selected from H or D; L is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl; Ar is selected from unsubstituted 2-pyridine group or unsubstituted 2-quinoline group or unsubstituted phenyl.

[0748] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 Independently selected from H or D; L is selected from E1 to E5 and E8 to E23.

[0749] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 to C3 alkyl.

[0750] According to one embodiment, in formula (M2) and formula (M4), 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 a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0751] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C3 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0752] According to one embodiment, in formula (M2) and formula (M4), 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 a substituted or unsubstituted 2-pyridine group or a substituted or unsubstituted 2-quinoline group or a substituted or unsubstituted phenyl group.

[0753] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ldindependently selected from H, D and substituted or unsubstituted C1 to C3 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl group.

[0754] According to one embodiment, in formula (M2) and formula (M4), 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 group.

[0755] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld is independently selected from H, D and a substituted or unsubstituted C1 to C3 alkyl group; and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0756] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 Independently selected from H or D; L is selected from E1 to E5 and E8 to E23.

[0757] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 to C2 alkyl.

[0758] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 are independently selected from H or D; L is selected from E2, E3, E8, E9, E11, E14 and E15; and in formula (M2), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group.

[0759] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , RLc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C2 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0760] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 are independently selected from H or D; L is selected from E2, E3, E8, E9, E11, E14, E15 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 a substituted or unsubstituted phenyl group.

[0761] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld independently selected from H, D and substituted or unsubstituted C1 to C2 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl group.

[0762] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 are independently selected from H or D; L is selected from E2, E3, E8, E9, E11, E14, E15; and in formula (M2), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0763] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and a substituted or unsubstituted C1 to C2 alkyl group; and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0764] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 Independently selected from H or D; L is selected from E2 to E3, E11 and E16.

[0765] According to one embodiment, in formula (M1) and formula (M3), R 2 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld Independently selected from H, D and substituted or unsubstituted C1 alkyl.

[0766] According to one embodiment, in formula (M2) and formula (M4), R 2 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 a substituted or unsubstituted phenyl group.

[0767] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted pyridine group or substituted or unsubstituted quinoline group or substituted or unsubstituted phenyl group.

[0768] According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7 are independently selected from H or D; L is selected from E2 to E3, E11 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 a substituted or unsubstituted phenyl group.

[0769] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld is independently selected from H, D and substituted or unsubstituted C1 alkyl; and in formula (M1), Ar is selected from substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl. According to one embodiment, in formula (M2) and formula (M4), R 2 To R 7are independently selected from H or D; L is selected from E2 to E3, E11 and E16; and in formula (M2), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0770] According to one embodiment, in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 alkyl; and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group.

[0771] Compounds of Formula (M1) to Formula (M4) may be selected from Compounds I-1 to I-298 shown in Table 3 above, wherein each compound may be undeuterated, partially deuterated, or fully deuterated.

[0772] Compounds of Formula (M1) to Formula (M4) may be selected from the compounds shown in Table 4 above, wherein each compound may be undeuterated, partially deuterated, or fully deuterated.

[0773] Compounds of Formula (M1) to Formula (M4) may be selected from the compounds shown in Table 5 above, wherein each compound may be undeuterated, partially deuterated, or fully deuterated.

[0774] Compounds of Formula (M1) to Formula (M4) may be selected from the compounds shown in Table 6 above, wherein each compound may be undeuterated, partially deuterated, or fully deuterated.

[0775] Compounds of Formula (M1) to Formula (M4) may be selected from the compounds shown in Table 7 above, wherein each compound may be undeuterated, partially deuterated, or fully deuterated.

[0776] According to one embodiment, the compounds of Formula (M1) to Formula (M4) are selected from the compounds shown in Table 13.

[0777] Table 13

[0778]

[0779]

[0780]

[0781]

[0782]

[0783]

[0784]

[0785]

[0786]

[0787]

[0788]

[0789]

[0790]

[0791]

[0792]

[0793]

[0794]

[0795]

[0796]

[0797]

[0798]

[0799]

[0800]

[0801] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0802] According to one embodiment, the compounds of Formula (M1) to Formula (M4) are selected from the compounds shown in Table 14.

[0803] Table 14

[0804]

[0805]

[0806]

[0807] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0808] According to one embodiment, the compounds of Formula (M1) to Formula (M4) are selected from the compounds shown in Table 15.

[0809] Table 15:

[0810]

[0811]

[0812]

[0813] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0814] According to one embodiment, the compounds of Formula (M1) to Formula (M4) are selected from the compounds shown in Table 16.

[0815] Table 16:

[0816]

[0817]

[0818]

[0819] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0820] According to one embodiment, the compounds of Formula (M1) to Formula (M4) are selected from the compounds shown in Table 17.

[0821] Table 17:

[0822]

[0823]

[0824] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0825] According to one embodiment, the compound of formula (I) is selected from the compounds shown in Table 18.

[0826] Table 18:

[0827]

[0828] The various compounds may be undeuterated, partially deuterated or fully deuterated.

[0829] The compounds of formula (M1) to formula (M4) can be selected from compounds I-125, I-126, I-151, I-2 and I-152:

[0830]

[0831] Each of the compounds may be undeuterated, partially deuterated, or fully deuterated.

[0832] Another aspect of the present invention provides a semiconductor material, which comprises at least one compound selected from the compounds of formula (M1) or formula (M2).

[0833] Another aspect of the present invention provides a semiconductor layer, wherein the semiconductor layer comprises a semiconductor material, wherein the semiconductor material comprises at least one compound selected from the compound of formula (M1) or formula (M2).

[0834] Another aspect of the present invention provides an electronic device, comprising a semiconductor layer, wherein the semiconductor layer comprises a semiconductor material, wherein the semiconductor material comprises at least one compound selected from the compound of formula (M1) or formula (M2).

[0835] According to one embodiment of the present invention, the electronic device is an organic electronic device.

[0836] According to one embodiment, the electronic device comprises an electroluminescent device, an organic light emitting diode (OLED), a light emitting device, a thin film transistor, a battery, a display device or an organic photovoltaic cell (OPV).

[0837] Another aspect of the present invention provides a display device, which includes an organic electronic device, wherein the organic electronic device includes a semiconductor layer, the semiconductor layer includes a semiconductor material, and the semiconductor material includes at least one compound selected from the compound of formula (M1) or formula (M2).

[0838] The embodiments are illustrated in more detail below with reference to the examples. However, the present disclosure is not limited to the following examples. Reference will now be made in detail to the exemplary aspects. BRIEF DESCRIPTION OF THE DRAWINGS

[0839] The above-mentioned components in the described embodiments as well as the components claimed and used according to the invention do not have any special exceptions in terms of their size, shape, material selection and technical concept, so that the selection criteria known in the relevant field can be applied without restriction.

[0840] Other details, features and advantages of the purpose of the present invention are disclosed in the dependent claims and the following corresponding drawings, which illustrate preferred embodiments according to the present invention in an exemplary manner. However, any embodiment may not necessarily represent the full scope of the present invention, so reference is made to the claims and this document to interpret the scope of the present invention. It should be understood that the above general description and the following detailed description are only exemplary and illustrative, and are intended to further illustrate the invention claimed.

[0841] Figure 1 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0842] Figure 2 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0843] Figure 3 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0844] Figure 4 is a schematic cross-sectional view of an organic electroluminescent device according to an exemplary embodiment of the present invention.

[0845] The accompanying drawings are described in more detail below with reference to embodiments. However, the present disclosure is not limited to the following drawings.

[0846] In this document, when a first element is referred to as being formed or disposed "on" or "over" a second element, the first element may be disposed directly on the second element, or one or more other elements may be disposed between them. When a first element is referred to as being "formed or disposed directly on" or "formed or disposed directly onto" a second element, no other elements are disposed between them.

[0847] Figure 1 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0848] refer to Figure 1 The organic electroluminescent device 100 includes an anode layer (ANO) 120, a first light-emitting layer (EML1) 145 and a first electron transport layer (ETL1) 149, wherein the first electron transport layer (ETL1) 149 does not contain 8-hydroxyquinoline lithium, preferably does not contain a lithium organic metal complex, and more preferably does not contain a lithium metal complex.

[0849] The organic electroluminescent device also includes a first charge generation layer (CGL1) 160 disposed on the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 includes a first n-type charge generation layer (n-CGL1) 161 and a first p-type charge generation layer (p-CGL1) 162, wherein the first n-type charge generation layer (n-CGL1) 161 includes a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from ytterbium, and wherein the first electron transport layer (ETL1) 149 is in direct contact with the first n-type charge generation layer (n-CGL1) 161.

[0850] The organic electroluminescent device 100 further includes a second light emitting layer (EML2) 245 and a cathode layer (CAT) 190 .

[0851] Figure 2 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0852] refer to Figure 2 The organic electroluminescent device 100 includes an anode layer (ANO) 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL1) 141, a first electron blocking layer (EBL1) 142, a first light-emitting layer (EML1) 145, an optional first hole blocking layer (HBL1) 147 and a first electron transport layer (ETL1) 149, wherein the first electron transport layer (ETL1) 149 does not contain 8-hydroxyquinolinol lithium, preferably does not contain a lithium organic metal complex, and more preferably does not contain a lithium metal complex.

[0853] The organic electroluminescent device also includes a first charge generation layer (CGL1) 160 disposed on the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 includes a first n-type charge generation layer (n-CGL1) 161 and a first p-type charge generation layer (p-CGL1) 162, wherein the first n-type charge generation layer (n-CGL1) 161 includes a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from ytterbium, and wherein the first electron transport layer (ETL1) 149 is in direct contact with the first n-type charge generation layer (n-CGL1) 161.

[0854] The organic electroluminescent device 100 further includes a second hole transport layer (HTL2) 241 and a second electron blocking layer (EBL2) 242.

[0855] The organic electroluminescent device 100 further includes a second light emitting layer (EML2) 245.

[0856] The organic electroluminescent device 100 further comprises an optional second hole blocking layer (HBL2) 247 , an electron transport layer (ETL) 148 , an electron injection layer (EIL) 180 , and a cathode layer (CAT) 190 .

[0857] Figure 3 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0858] refer to Figure 3 The organic electroluminescent device 100 includes an anode layer (ANO) 120 , a hole injection layer (HIL) 130 , a hole transport layer (HTL1 ) 141 , a first electron blocking layer (EBL1 ) 142 , and a first emission layer (EML1 ) 145 .

[0859] The organic electroluminescent device 100 further comprises an optional first hole blocking layer (HBL1) 147 .

[0860] The organic electroluminescent device 100 further comprises a first electron transport layer (ETL1) 149, wherein the first electron transport layer (ETL1) 149 does not contain 8-hydroxyquinolate lithium, preferably does not contain a lithium organic metal complex, and more preferably does not contain a lithium metal complex.

[0861] The organic electroluminescent device also includes a first charge generation layer (CGL1) 160 disposed on the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 includes a first n-type charge generation layer (n-CGL1) 161 and a first p-type charge generation layer (p-CGL1) 162, wherein the first n-type charge generation layer (n-CGL1) 161 includes a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from ytterbium, and wherein the first electron transport layer (ETL1) 149 is in direct contact with the first n-type charge generation layer (n-CGL1) 161.

[0862] The organic electroluminescent device 100 further includes a second hole transport layer (HTL2) 241 and a second electron blocking layer (EBL2) 242.

[0863] The organic electroluminescent device 100 further includes a second light emitting layer (EML2) 245.

[0864] The organic electroluminescent device 100 further comprises an optional second hole blocking layer (HBL2) 247 .

[0865] The organic electroluminescent device 100 further comprises a second electron transport layer (ETL2) 249, wherein the second electron transport layer (ETL2) 249 does not contain 8-hydroxyquinolate lithium, preferably does not contain a lithium organic metal complex, and more preferably does not contain a lithium metal complex.

[0866] The organic electroluminescent device also includes a second charge generation layer (CGL2) 260 disposed on the second electron transport layer (ETL2) 249, wherein the second charge generation layer (CGL2) 260 includes 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 includes a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from ytterbium, and wherein the second electron transport layer (ETL1) 249 is in direct contact with the second n-type charge generation layer (n-CGL2) 261, wherein the second n-type charge generation layer (n-CGL2) 261 can be selected to be the same as or different from the first n-type charge generation layer (n-CGL1) 161, and wherein the second p-type charge generation layer (p-CGL2) 262 can be selected to be the same as or different from the first p-type charge generation layer (p-CGL1) 161.

[0867] The organic electroluminescent device 100 further includes a third hole transport layer (HTL3) 341 and a third electron blocking layer (EBL3) 342.

[0868] The organic electroluminescent device 100 further includes a third light emitting layer (EML3) 345.

[0869] The organic electroluminescent device 100 further includes an optional third hole blocking layer (HBL3) 347 , an electron transport layer (ETL) 148 , an electron injection layer (EIL) 180 , and a cathode layer (CAT) 190 .

[0870] Figure 4 is a schematic cross-sectional view of an organic electroluminescent device 100 according to an exemplary embodiment of the present invention.

[0871] refer to Figure 4 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 (EBL1 ) 142 , and a first emission layer (EML1 ) 145 .

[0872] The organic electroluminescent device 100 further comprises an optional first hole blocking layer (HBL1) 147 .

[0873] The organic electroluminescent device 100 further comprises a first electron transport layer (ETL1) 149, wherein the first electron transport layer (ETL1) 149 does not contain 8-hydroxyquinolate lithium, preferably does not contain a lithium organic metal complex, and more preferably does not contain a lithium metal complex.

[0874] The organic electroluminescent device also includes a first charge generation layer (CGL) 160 disposed on the first electron transport layer (ETL1) 149, wherein the first charge generation layer (CGL1) 160 includes 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 includes a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from ytterbium, and wherein the first electron transport layer (ETL1) 149 is in direct contact with the first n-type charge generation layer (n-CGL) 161.

[0875] The organic electroluminescent device 100 further includes a second hole transport layer (HTL2) 241 and a second electron blocking layer (EBL2) 242.

[0876] The organic electroluminescent device 100 further includes a second light emitting layer (EML2) 245.

[0877] The organic electroluminescent device 100 further comprises an optional second hole blocking layer (HBL2) 247 .

[0878] The organic electroluminescent device 100 further comprises a second electron transport layer (ETL2) 249, wherein the second electron transport layer (ETL2) 249 does not contain 8-hydroxyquinolate lithium, preferably does not contain a lithium organic metal complex, and more preferably does not contain a lithium metal complex.

[0879] The organic electroluminescent device also includes a charge generation layer (CGL) 260 disposed on the second electron transport layer (ETL2) 249, wherein the second charge generation layer (CGL2) 260 includes 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 includes a compound of formula (I) and a metal dopant, wherein the metal dopant is selected from ytterbium, and wherein the second electron transport layer (ETL2) 249 is in direct contact with the second n-type charge generation layer (n-CGL2) 261, wherein the second n-type charge generation layer (n-CGL2) 261 can be selected to be the same as or different from the first n-type charge generation layer (n-CGL1) 161, and wherein the second p-type charge generation layer (p-CGL2) 262 can be selected to be the same as or different from the first p-type charge generation layer (p-CGL1) 161.

[0880] The organic electroluminescent device 100 further includes a third hole transport layer (HTL3) 341 and a third electron blocking layer (EBL3) 342.

[0881] The organic electroluminescent device 100 further includes a third light emitting layer (EML3) 345.

[0882] The organic electroluminescent device 100 further comprises an optional third hole blocking layer (HBL3) 347 .

[0883] The organic electroluminescent device 100 further comprises a third electron transport layer (ETL3) 349, wherein the third electron transport layer (ETL3) 349 does not contain 8-hydroxyquinolate lithium, preferably does not contain a lithium organic metal complex, and more preferably does not contain a lithium metal complex.

[0884] The organic electroluminescent device also includes a charge generation layer (CGL3) 360 disposed on the third electron transport layer (ETL3) 349, wherein the third charge generation layer (CGL3) 360 includes a third n-type charge generation layer (n-CGL3) 361 and a third p-type charge generation layer (p-CGL3) 362, wherein the third n-type charge generation layer (n-CGL3) 361 includes 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-CGL3) 361, wherein the third n-type charge generation layer (n-CGL3) 361 can be selected to be the same as or different from the first n-type charge generation layer (n-CGL1) 161, and wherein the third p-type charge generation layer (p-CGL3) 362 can be selected to be the same as or different from the first p-type charge generation layer (p-CGL1) 161.

[0885] The organic electroluminescent device 100 further includes a fourth hole transport layer (HTL4) 441 and a fourth electron blocking layer (EBL4) 442 .

[0886] The organic electroluminescent device 100 further includes a fourth light emitting layer (EML4) 345.

[0887] The organic electroluminescent device 100 further includes an optional fourth hole blocking layer (HBL4) 447 , an electron transport layer (ETL) 148 , an electron injection layer (EIL) 180 , and a cathode layer (CAT) 190 .

[0888] Despite Figure 1 , Figure 2 , Figure 3 and Figure 4 Although not shown in the figure, a sealing layer may be additionally formed on the cathode electrode 190 to seal the OLED 100. In addition, various other modifications may be applied thereto.

[0889] The embodiments are illustrated in more detail below with reference to Examples. However, the present disclosure is not limited to the following Examples. DETAILED DESCRIPTION

[0890] The present invention is further illustrated by the following examples, which are intended to be illustrative only and not limiting.

[0891] Sublimation temperature

[0892] In a glove box, 0.5 g to 5 g of the compound were placed in the evaporation source of a sublimation apparatus under nitrogen. The sublimation apparatus consisted of an inner glass tube consisting of a 3 cm diameter bulb placed in a 3.5 cm diameter glass tube. The sublimation apparatus was placed in a tubular oven (Creaphys DSU 05 / 2.1). The sublimation apparatus was evacuated by a diaphragm pump (Pfeiffer Vacuum MVP 055-3C) and a turbo pump (Pfeiffer Vacuum THM071 YP). The pressure between the sublimation apparatus and the turbo pump was measured using a pressure gauge (Pfeiffer Vacuum PKR 251). When the pressure dropped to 10 -5 The temperature is increased in increments of 10 K to 30 K at 100 mbar until the compound begins to precipitate in the collecting region of the sublimation apparatus. The temperature is further increased in increments of 10 K to 30 K until a sublimation rate is reached where the compound in the evaporation source is significantly depleted within 30 minutes to 1 hour and a significant amount of the compound has accumulated in the collecting region.

[0893] Sublimation temperature is also called T 升华 , is the temperature within the sublimation apparatus at which the compound is deposited in the collection zone at an appreciable rate and is measured in degrees Celsius.

[0894] In the context of the present invention, the term "sublimation" may refer to a transition from a solid to a gas phase or from a liquid to a gas phase.

[0895] Decomposition temperature

[0896] Decomposition temperature is also called T 分解 , measured in degrees Celsius.

[0897] Decomposition temperature was measured in a Mettler Toledo TGA-DSC1 machine by loading 9 to 11 mg of sample into a Mettler Toledo 100 μL uncovered aluminum pan under nitrogen. The following heating program was used: isothermal heating at 25°C for 3 minutes; heating from 25°C to 600°C at 10 K / min.

[0898] The decomposition temperature was determined based on the decomposition onset in TGA.

[0899] Calculated LUMO and dipole moment

[0900] The LUMO energy level and dipole moment were calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometry of the molecular structure and the HOMO and LUMO energy levels were determined by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase. If more than one conformation is feasible, the conformation with the lowest total energy is selected.

[0901] The materials used for the first n-type charge generation layer are shown in Table 10:

[0902] Table 10:

[0903]

[0904]

[0905] The materials used for the first electron transport layer are shown in Table 11.

[0906] Table 11:

[0907]

[0908]

[0909] General procedure for manufacturing OLED

[0910] For the embodiments and comparative examples according to the present invention in Table 12, a glass substrate having an anode layer comprising a first anode sublayer of 10 nm ITO, a second anode sublayer of 120 nm Ag, and a third anode sublayer of 8 nm ITO was cut into a size of 100 mm × 100 mm × 0.7 mm, ultrasonically cleaned with water for 60 minutes, and then ultrasonically cleaned with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, and then plasma treated, see Table 12, to prepare the anode layer. The plasma treatment was carried out in an atmosphere comprising 97.6% by volume nitrogen and 2.4% by volume oxygen.

[0911] Then, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluoren-2-amine and 2 wt% of 2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) were vacuum deposited to form a hole injection layer with a thickness of 10 nm.

[0912] Then, N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine was vacuum deposited to form a first hole transport layer having a thickness of 29 nm.

[0913] Then, N-([1,1′-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluoren-2-amine was vacuum deposited on the HTL to form a 5 nm thick electron blocking layer (EBL).

[0914] Then, 97 wt % of H09 (Sun Fine Chemicals, Korea) as an EML host and 3 wt % of BD200 (Sun Fine Chemicals, Korea) as a fluorescent blue dopant were deposited on the EBL to form a first blue emission layer (EML) with a thickness of 20 nm.

[0915] Then, a first electron transport layer (ETL1) having a thickness of 15 nm was formed on the first light emitting layer by depositing the compound according to Table 12. The first electron transport layer did not contain 8-hydroxyquinolinolithium.

[0916] Then, an n-type CGL having a thickness of 8 nm was formed on the ETL1 by co-depositing 90.1 wt % of the electron transport compound according to Table 12 (ETM of n-CGL) and 9.9 wt % of Yb.

[0917] Then, a p-type CGL with a thickness of 10 nm was formed on the n-type CGL by co-depositing N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine and 10 wt% of 2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile) as an organic p-type dopant.

[0918] Then, a second hole transport layer was formed on the first p-type CGL with a thickness of 45 nm by depositing N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine.

[0919] Then, a second electron blocking layer with a thickness of 5 nm was formed on the second hole transport layer by depositing N-([1,1′-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluoren-2-amine.

[0920] Then, 97 wt % of H09 (Sun Fine Chemicals, Korea) as an EML host and 3 wt % of BD200 (Sun Fine Chemicals, Korea) as a fluorescent blue dopant were deposited on the second EBL to form a second blue light-emitting EML with a thickness of 19 nm.

[0921] Then, 2-(3′-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was vacuum deposited to form a second hole blocking layer with a thickness of 5 nm on the second blue light-emitting EML.

[0922] Then, 50 wt % of 4′-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalen-1-yl)-[1,1′-biphenyl]-4-carbonitrile and 50 wt % of LiQ were vacuum deposited on the second hole blocking layer to form a second electron transport layer with a thickness of 31 nm.

[0923] Then, at 10 -7 mbar to Yb is evaporated at a rate of , to form an electron injection layer with a thickness of 1 nm on the electron transport layer.

[0924] In 10 -7 mbar to Ag / Mg (1:8 wt %) was evaporated at a rate of 1:1 to form a cathode with a thickness of 13 nm.

[0925] Then, N-({[1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine} was vacuum deposited on the cathode layer to form a capping layer with a thickness of 75 nm.

[0926] In order to evaluate the performance of the inventive examples compared to the prior art, the current efficiency was measured at 20°C. The current-voltage characteristic line was determined by providing a voltage (in V) and measuring the current (in mA) flowing through the device under test using a Keithley 2635 source measurement unit. The voltage applied to the device varied in steps of 0.1 V in the range between 0 V and 10 V. Similarly, the luminous density (in cd / m2) was measured for each voltage value using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2The luminous density-voltage characteristic line and CIE coordinates are determined by interpolating the luminous density-voltage and current-voltage characteristic lines respectively. 2 cd / A efficiency under .

[0927] In bottom-emitting devices, the emission is primarily Lambertian and is quantified as the external quantum efficiency (EQE) percentage. To determine the EQE efficiency (in %), a calibrated photodiode was used at 15 mA / cm 2 The light output of the device was measured.

[0928] In a top-emitting device, the emission is forward, non-Lambertian, and also highly dependent on the microcavity. Therefore, the efficiency EQE will be higher compared to a bottom-emitting device. To determine the EQE efficiency (in %), a calibrated photodiode was used at 15 mA / cm 2 The light output of the device was measured.

[0929] At ambient conditions (20°C) and 30mA / cm 2 The device lifetime LT was measured using a Keithley 2400 source meter and recorded in hours.

[0930] The brightness of the device is measured using a calibrated photodiode. The lifetime LT is defined as the time until the brightness of the device drops to 97% of its initial value.

[0931] The operating voltage increase ΔU is used as a measure of the operating voltage stability of the device. This increase is determined during the LT measurement by subtracting the operating voltage after 1 hour from the operating voltage after 100 hours after the device has started operating.

[0932] ΔU=[U(100h)-U(1h)].

[0933] The smaller the ΔU value is, the better the operating voltage stability is.

[0934] Technical Effects of the Invention

[0935] Table 12:

[0936]

[0937] Comparative device C1 includes an electron transport layer in contact with an n-type charge generation layer and the n-type charge generation layer includes compound C-4, the electron transport layer including 8-hydroxyquinolate lithium (LiQ) and compound ET-1.

[0938] Comparative device C2 includes an electron transport layer in contact with an n-type charge generation layer and the n-type charge generation layer includes Compound I-1, the electron transport layer includes 8-hydroxyquinolate lithium (LiQ) and Compound ET-1.

[0939] Comparative device C3 includes an electron transport layer in contact with an n-type charge generation layer, and the n-type charge generation layer includes Compound I-2, the electron transport layer including 8-hydroxyquinolate lithium (LiQ) and Compound ET-1.

[0940] Comparative device C4 comprises an electron transport layer in contact with an n-type charge generation layer and an n-type charge generation layer comprising compound ET-2, the electron transport layer comprising compound ET-1 and, in contrast to comparative device C1, no 8-hydroxyquinolate lithium (LiQ). Compound ET-2 comprises two phenanthroline groups.

[0941] Comparative device C5 comprises an electron transport layer in contact with an n-type charge generation layer comprising compound C-2, and the n-type charge generation layer comprising compound C-2, wherein the electron transport layer does not contain 8-hydroxyquinolate lithium (LiQ). Compound C-2 comprises a pyrazine group and an imidazo[1,5-a]pyridine group.

[0942] Comparative device C6 comprises an electron transport layer in contact with an n-type charge generation layer comprising compound C-3, and the n-type charge generation layer comprising compound C-3, wherein the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ). Compound C-3 comprises a dibenzoacridine group and an imidazo[1,5-a]pyridine group.

[0943] Comparative device C7 comprises an electron transport layer in contact with an n-type charge generation layer comprising compound C-4, and the n-type charge generation layer comprising compound C-4, wherein the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ). Compound C-4 comprises a dibenzoacridine group and a substituted imidazo[1,5-a] group.

[0944] Comparative device C8 includes an electron transport layer in contact with an n-type charge generation layer including compound C-1 and the n-type charge generation layer including compound C-1, and the electron transport layer does not contain 8-hydroxyquinolate lithium (LiQ). Compound C-1 contains one phenanthroline group.

[0945] Inventive device I1 comprises an electron transport layer in contact with an n-type charge generation layer and an n-type charge generation layer comprising compound ET-3, wherein the electron transport layer comprises compound ET-1 and, in contrast to comparative device C3, the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ). Compound ET-3 comprises a phenanthroline group and a substituted imidazo[1,5-a] group.

[0946] Inventive device I2 comprises an electron transport layer in contact with an n-type charge generation layer and an n-type charge generation layer comprising compound I-2, wherein the electron transport layer comprises compound ET-1 and, in contrast to comparative device C3, the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ). Compound I-2 comprises a phenanthroline group and a substituted imidazo[1,5-a] group.

[0947] Inventive device I3 comprises an electron transport layer in contact with an n-type charge generation layer and the n-type charge generation layer comprising compound ET-3, wherein the electron transport layer comprises compound ET-2 instead of compound ET-1 according to inventive device I1, and the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ).

[0948] Inventive device I4 comprises an electron transport layer in contact with an n-type charge generation layer and an n-type charge generation layer comprising compound ET-3, wherein the electron transport layer comprises compound ET-5 instead of compound ET-1 according to inventive device I1, and the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ).

[0949] Inventive device I5 comprises an electron transport layer in contact with an n-type charge generation layer and an n-type charge generation layer comprising compound ET-3, wherein the electron transport layer comprises compound ET-4 instead of compound ET-1 according to inventive device I1, and the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ).

[0950] In the inventive device I6, the organic electroluminescent device comprises an electron transport layer in contact with the n-type charge generation layer and the n-type charge generation layer comprising compound ET-3, wherein the electron transport layer comprises compound ET-6 instead of compound ET-1 according to the inventive device I1, and the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ).

[0951] Inventive device I7 comprises an electron transport layer in contact with the n-type charge generation layer and the n-type charge generation layer comprising compound ET-3, wherein the electron transport layer comprises compound ET-3 instead of compound ET-1 according to inventive device I1, and the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ).

[0952] Inventive device I8 comprises an electron transport layer in contact with an n-type charge generation layer and an n-type charge generation layer comprising compound ET-3, wherein the electron transport layer comprises compound ET-7 instead of compound ET-1 according to inventive device I1, and the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ).

[0953] Inventive device I9 comprises an electron transport layer in contact with an n-type charge generation layer and an n-type charge generation layer comprising compound I-126, wherein the electron transport layer comprises compound ET-1 and, in contrast to comparative device C3, the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ). Compound I-126 comprises a phenanthroline group and a substituted imidazo[1,5-a] group.

[0954] Inventive device I10 comprises an electron transport layer in contact with an n-type charge generation layer and an n-type charge generation layer comprising compound I-151, wherein the electron transport layer comprises compound ET-1 and, in contrast to comparative device C3, the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ). Compound I-151 comprises a phenanthroline group and a substituted imidazo[1,5-a] group.

[0955] Inventive device I11 comprises an electron transport layer in contact with an n-type charge generation layer and an n-type charge generation layer comprising compound I-125, wherein the electron transport layer comprises compound ET-1 and, in contrast to comparative device C3, the electron transport layer does not contain 8-hydroxyquinoline lithium (LiQ). Compound I-125 comprises a phenanthroline group and a substituted imidazo[1,5-a] group.

[0956] In Comparative Examples C1 and C5, compound ET-2 was used in the n-type charge generation layer. In contrast to Comparative Example C1, the electron transport layer in contact with the n-type charge generation layer in Comparative Example C5 did not contain lithium hydroxyquinoline (LiQ). However, it is clear that the voltage increase over time is still very high.

[0957] In Comparative devices C1 and C5, compound C-4 is used in the n-type charge generation layer. In contrast to Comparative Example C1, the electron transport layer in contact with the n-type charge generation layer in Comparative Example C5 does not contain lithium hydroxyquinoline (LiQ). However, it is clear that the voltage increase over time is still very high.

[0958] The difference between the inventive device I3 or I4 and the comparative device C3 or C4, respectively, is that the inventive device I3 or I4, respectively, does not contain lithium hydroxyquinoline in the electron transport layer in contact with the n-type charge generation layer.

[0959] Inventive devices I1 to I11 do not contain lithium quinolate in the electron transport layer in contact with the n-type charge generation layer.

[0960] Comparative devices C1 to C5 contain lithium quinolate in the electron transport layer in contact with the n-type charge generation layer.

[0961] Inventive devices I1 to I11 also differ from comparative devices C1 to C4 in that inventive devices I1 to I11 contain a compound according to formula (I) in the n-type charge generation layer.

[0962] It is clear that all inventive devices show a significantly lower voltage rise over time compared to comparative devices C1 to C4. At the same time, the operating voltage remains low and the current efficiency remains very high.

[0963] Inventive devices I1 to I11 and comparative devices C5 to C9 do not contain lithium quinolate in the electron transport layer in contact with the n-type charge generation layer.

[0964] The inventive devices I1 to I11 differ from the comparative devices C5 to C9 in that the inventive devices I1 to I11 contain a compound according to formula (I) in the n-type charge generation layer.

[0965] It is clear that all inventive devices show a lower voltage rise over time than comparative devices C5 to C9. At the same time, the operating voltage remains low and the current efficiency remains very high.

[0966] Thus, the inventive device comprising the compound of formula (I) in the n-type charge generation layer and containing no lithium hydroxyquinoline in the electron transport layer in contact with the n-type charge generation layer exhibits significantly low voltage rise over time, while exhibiting low operating voltage and high current efficiency.

[0967] Low operating voltage can be important to the battery life of organic electronic devices, especially mobile devices.

[0968] High efficiency can be beneficial in reducing power consumption and improving battery life, especially in mobile devices.

[0969] The low voltage increase over time can improve the long-term stability of electronic devices.

[0970] Table 2: Properties of the compound of formula (M) and Comparative Example 1

[0971]

[0972]

[0973] Since organic electronic materials are usually purified by sublimation, the offset between the decomposition temperature and the sublimation temperature T 分解 -T 升华 Therefore, high sublimation rates can be achieved, which can be beneficial for mass production under vacuum thermal evaporation conditions.

[0974] The specific combination of elements and features in the embodiments described in detail above is exemplary only; it is also explicitly contemplated to interchange and replace these teachings with other teachings in this application and the patents / applications incorporated by reference. As will be appreciated by those skilled in the art, those of ordinary skill in the art will be able to think of changes, modifications and other embodiments of the contents described herein without departing from the spirit and scope of the claimed invention. Therefore, the above description is exemplary only and is not intended to be limiting. In the claims, the words "comprise", "include" do not exclude other elements or steps, and the indefinite article "one" or "a kind" does not exclude multiple or multiple. The fact that certain measures are described in different dependent claims does not mean that a combination of these measures cannot be used to advantage. The scope of the invention is defined in the claims and their equivalents. In addition, the figure marks used in the specification and claims do not limit the scope of the claimed invention.

Claims

1. An organic electroluminescent device, comprising an anode layer, a cathode layer, a first light-emitting layer, a second light-emitting layer, a first charge generation layer and a first electron transport layer, in - the first charge generation layer is arranged between the first light-emitting layer and the second light-emitting layer; - the first electron transport layer is arranged between the first light-emitting layer and the second light-emitting 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 does not contain 8-hydroxyquinolate lithium; - the first n-type charge generation layer comprises a metal dopant and the metal dopant is Yb; - the first n-type charge generation layer comprises a compound of formula (I): Wherein in formula (I), -Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 heteroaryl; -R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and -L is selected from substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C2 to C 24 Heteroaryl.

2. The organic electroluminescent device according to claim 1, wherein Ar is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl.

3. The organic electroluminescent device according to claim 1 or 2, wherein Ar is selected from substituted or unsubstituted phenyl or substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted triazine and substituted or unsubstituted quinolyl.

4. An organic electroluminescent device according to any one of the preceding claims, wherein R 1 To R 7 are independently selected from H, D, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl and halogen.

5. An organic electroluminescent device according to any one of the preceding claims, wherein R 1 To R 7 Independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 aryl or substituted or unsubstituted C3 to C5 heteroaryl and halogen.

6. An organic electroluminescent device according to any one of the preceding claims, wherein L is selected from substituted or unsubstituted C6 to C 12 Aryl or substituted or unsubstituted C2 to C 12 Heteroaryl.

7. An organic electroluminescent device according to any one of the preceding claims, wherein L is selected from substituted or unsubstituted phenyl groups.

8. An organic electroluminescent device according to any one of the preceding claims, wherein the LUMO energy level of the compound of formula (I) is in the range of ≥-1.8 eV to ≤-1.4 eV when calculated using the program package TURBOMOLE V6.5 by applying the hybrid functional B3LYP with the 6-31G* basis set in the gas phase.

9. The organic electroluminescent device according to any of the preceding claims, wherein the molecular weight of the compound of formula (I) is in the range of ≧400 g / mol to ≦2000 g / mol.

10. An organic electroluminescent device according to any preceding claim, wherein the first electron transport layer is closer to the anode layer than any other electron transport layer in the organic electroluminescent device.

11. An organic electroluminescent device according to any one of the preceding claims, wherein the first electron transport layer is in direct contact with the first light-emitting layer.

12. An organic electroluminescent device according to any one of the preceding claims, wherein the first electron transport layer is free of metal complexes.

13. An organic electroluminescent device according to any one of the preceding claims, wherein the first electron transport layer comprises an electron transport compound, in - the molecular weight of the electron transport compound is in the range of ≥400 g / mol to ≤2000 g / mol; and The -electron transport compound may comprise at least one N-containing heteroaromatic ring.

14. The organic electroluminescent device according to any one of the preceding claims, wherein the organic electroluminescent device further comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a first electron blocking layer, a second electron blocking layer, an optional first hole blocking layer, an optional second hole blocking layer, a second electron transport layer and an electron injection layer.

15. A display device comprising an organic electroluminescent device according to any one of the preceding claims.

16. A compound of formula (M1) or formula (M2), In formula (M1), -R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and -R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O; -Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 heteroaryl; Wherein in formula (M2), -R 2 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and -Ar is selected from substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C2 to C 24 heteroaryl; -L is selected from substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C2 to C 24 Heteroaryl.

17. The compound according to claim 16, wherein the compound is selected from formula (M3) or formula (M4), In formula (M3), -R 1 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and -R La , R Lb , R Lc and R Ld 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 Selected from O, S or Se, preferably O; In formula (M4), -R 2 To R 7 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 C2 to C 24 Heteroaryl, CN, halogen, F, C1 to C 16 Alkoxy, C3 to C 16 Branched alkyl, C3 to C 16 Cyclic alkyl, C3 to C 16 Branched chain alkoxy, C3 to C 16 Cyclic alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy, or PX 1 (R 8 )2, where R 8 Independently selected from C6 to C 12 Aryl, C3 to C 12 Heteroaryl, C1 to C 16 Alkyl, C1 to C 16 Alkoxy, partially fluorinated or perfluorinated C1 to C 16 Alkyl, partially fluorinated or perfluorinated C1 to C 16 Alkoxy, partially deuterated or fully deuterated C1 to C 16 Alkyl, partially deuterated or fully deuterated C1 to C 16 Alkoxy; and X 1 is selected from O, S or Se, preferably O; and -L is selected from substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C2 to C 24 Heteroaryl.

18. The compound according to claim 16 or 17, wherein in formula (M1) or (M3), R 1 To R 7 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 C2 to C 24 heteroaryl; and Wherein in formula (M2) or formula (M4), R 2 To R 7 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 C2 to C 24 Heteroaryl.

18. The compound according to any one of claims 16 to 17, wherein R of formula (M1) or formula (M3) La , R Lb , R Lc and R Ld independently selected from H, D, substituted or unsubstituted C1 to C 16 Alkyl, wherein L of formula (M2) or formula (M4) is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridyl, pyrazinyl, pyrimidinyl, triazinyl.

19. The compound according to any one of claims 16 to 18, wherein R of formula (M1) or formula (M3) La , R Lb , R Lc and R Ld are independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, and wherein L of formula (M2) or formula (M4) is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl.

20. The compound according to any one of claims 16 to 19, wherein R in formula (M1) and formula (M3) 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld are independently selected from H, D and substituted or unsubstituted C1 to C 16 alkyl; and in formula (M1), Ar is selected from an unsubstituted 2-pyridine group or an unsubstituted 2-quinoline group or an unsubstituted phenyl group; and In formula (M2) and formula (M4), R 2 To R 7 independently selected from H or D; L is selected from substituted or unsubstituted C6 to C 10 aryl or substituted or unsubstituted C3 to C5 heteroaryl.

21. The compound according to any one of claims 16 to 20, wherein in formula (M1) and formula (M3), R 1 To R 7 independently selected from H or D; R La , R Lb , R Lc and R Ld is independently selected from H, D and a substituted or unsubstituted C1 to C4 alkyl group; and in formula (M1), Ar is selected from a substituted or unsubstituted pyridine group or a substituted or unsubstituted quinoline group or a substituted or unsubstituted phenyl group; and In formula (M2) and formula (M4), 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 substituted or unsubstituted 2-pyridine group or substituted or unsubstituted 2-quinoline group or substituted or unsubstituted phenyl.

22. The compound of any one of claims 16 to 21, wherein the compound is selected from 1-2, 1-78, 1-126, 1-148, 1-150, 1-151, 1-152, 1-158, 1-159, 1-160, 1-163, 1-167, 1-169, 1-188, 1-226, 1-227, 1-294, 1-295, 1-296, 1-297 and 1-298:

23. The compound according to any one of claims 16 to 22, wherein the compound is selected from 1-125, 1-126, 1-151, 1-2 and 1-152: Each of the compounds may be undeuterated, partially deuterated, or fully deuterated.

24. A semiconductor material comprising at least one compound selected from the compounds of formula (M1) or formula (M2) according to any one of claims 16 to 23.

25. A semiconductor layer comprising the semiconductor material according to claim 24.

26. An electronic device comprising the semiconductor layer according to claim 25.

27. The electronic device of claim 26, wherein the electronic device is an organic electronic device.

28. The electronic device of claim 26 or 27, wherein the electronic device comprises an electroluminescent device, an organic light emitting diode (OLED), a light emitting device, a thin film transistor, a battery, a display device, or an organic photovoltaic cell (OPV).

29. A display device, comprising an organic electronic device, wherein the organic electronic device comprises a semiconductor layer, the semiconductor layer comprises a semiconductor material, the semiconductor material comprises at least one compound selected from the compound of formula (M1) or formula (M2) according to any one of claims 16 to 23.

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