Compounds of formula (I) and their use in organic electronic devices

Abstract

The present invention relates to a compound and use thereof in an organic electronic device, an organic semiconductor layer comprising the compound, an organic electronic device comprising the organic semiconductor layer, and a display device comprising the organic electronic device.

Description

Technical Field

[0001] The present invention relates to a compound of formula (I) and use thereof in an organic electronic device, an organic semiconductor layer comprising the compound of formula (I), an organic electronic device comprising the organic semiconductor layer, and a display device comprising the organic electronic device. Background Art

[0002] Organic electronic devices, such as organic light-emitting diodes (OLEDs), are self-luminous devices that offer wide viewing angles, excellent contrast, a fast response time, high brightness, superior operating voltage characteristics, and excellent color reproduction. A typical OLED consists of an anode, a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode, which are sequentially stacked on a substrate. The HTL, EML, and ETL are thin films formed from organic compounds.

[0003] When voltage is applied to the anode and cathode, holes injected from the anode move through the HTL to the EML, while electrons injected from the cathode move through the ETL to the EML. 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 must be balanced to ensure that OLEDs with this structure have excellent efficiency and / or a long lifetime.

[0004] The performance of the organic light emitting diode may be affected by the characteristics of the semiconductor layer, and among others, may be affected by the characteristics of the metal complex also contained in the semiconductor layer.

[0005] There is still a need to improve the performance of organic semiconductor materials, semiconductor layers and organic electronic devices thereof, in particular to achieve improved operating voltage, improved efficiency, improved lifetime and / or improved voltage stability over time by improving the properties of the compounds contained therein. In addition, there is still a need to improve the LUMO energy level, improve the dipole moment and / or improve the thermal properties compared to comparative examples, in particular to improve the thermal stability and / or processing properties at elevated temperatures. Summary of the Invention

[0006] One aspect of the present invention provides a compound of formula (I):

[0007] (I),

[0008] in

[0009] HetAr is selected from formula (II):

[0010] (II),

[0011] A 1 Selected from formula (III):

[0012] (III),

[0013] A 2 is selected from formula (IV)

[0014] (IV),

[0015] wherein the asterisk "*" indicates the position of bonding,

[0016] R 1 and R 2 are independently selected from CN, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, substituted or unsubstituted C6 to C 30 aryl, substituted or unsubstituted C2 to C 30 heteroaryl, SF5,

[0017] wherein one or more substituents on R 1 and R 2 are independently selected from D, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, halogen, F, SF5, or CN;

[0018] R 3 and R 4 are independently selected from H, D, halogen, F, CN, partially fluorinated Ci to C4 alkyl, perfluorinated Ci to C4 alkyl, SF5, or CF3;

[0019] R 5 is independently selected from H, D, halogen, F, CN, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, substituted or unsubstituted C6 to C 30 aryl, or substituted or unsubstituted C2 to C 30 heteroaryl, SF5,

[0020] wherein one or more substituents on R 5 are independently selected from D, partially fluorinated Ci to Cs alkyl, or perfluorinated Ci to Cs alkyl, CF3, halogen, F, CN, SF5;

[0021] X a1 is selected from N or CR a4 ;

[0022] R a1 , R a2 , R a3 and R a4independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN, SF5,

[0023] where R a1 、R a2 、R a3 and R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, SF5;

[0024] where R a1 、R a2 、R a3 and R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN or SF5.

[0025] It should be noted that throughout the application and claims, any R 1 、R 2 、R 3 、R 4 、R 5 、R a1 、R a2 、R a3 and R a4 Etc. always refers to the same part unless otherwise noted.

[0026] In the present specification, when no definition is otherwise provided, "partially fluorinated" refers to a C1 to C8 alkyl group in which only a part of hydrogen atoms are replaced by fluorine atoms.

[0027] In the present specification, when no definition is otherwise provided, "perfluorinated" refers to a C1 to C8 alkyl group in which all hydrogen atoms are replaced by fluorine atoms.

[0028] In the present specification, when no definition is otherwise provided, "substituted" means substituted with deuterium, D, halogen, F, CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, or CF.

[0029] However, in this 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.

[0030] Accordingly, in this specification, "heteroaryl-substituted" means substituted by one or more aryl groups, which heteroaryl group may itself be substituted by one or more aryl and / or heteroaryl groups.

[0031] In this specification, when no definition is provided otherwise, "alkyl group" refers to a saturated aliphatic hydrocarbon group. The alkyl group can be a C1 to C8 alkyl group. More specifically, the alkyl group can be a C1 to C6 alkyl group or a C1 to C4 alkyl group. For example, a C1 to C4 alkyl group contains 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.

[0032] 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 sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group.

[0033] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane by formally separating 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, and the like.

[0034] The term "hetero" is understood to mean that in a structure that can be formed by covalently bonded carbon atoms, at least one carbon atom is replaced by another polyvalent atom. Preferably, the heteroatom can be selected from B, Si, N, P, O, S; more preferably, from N, P, O, S.

[0035] In this specification, "aryl group" refers to a hydrocarbon group that can be produced by formally separating a hydrogen atom from the aromatic ring of the corresponding aromatic hydrocarbon. Aromatic hydrocarbon refers to a hydrocarbon containing at least one aromatic ring or aromatic ring system. An 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 includes a conjugated system of delocalized electrons that satisfies Hückel's rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl, polycyclic groups comprising multiple aromatic rings connected by single bonds, such as biphenyl, and polycyclic groups comprising fused rings, such as naphthyl or fluoren-2-yl.

[0036] Similarly, heteroaryl is understood in particular to be a radical which is derived by formally separating a ring hydrogen from a heteroaromatic ring in compounds which contain at least one heteroaromatic ring.

[0037] Heterocycloalkyl is particularly suitably understood to be a radical which is derived by formally separating a ring hydrogen from a saturated cycloalkyl ring in a compound which contains at least one saturated cycloalkyl ring.

[0038] The term "fused aryl ring" or "condensed aryl ring" is understood to mean when two aryl rings share at least two common sp 2 When carbon atoms are hybridized, they are said to be fused or condensed.

[0039] The term "six-membered ring" is understood to mean a ring formed by 6 atoms. The ring atoms of the "six-membered ring" may be bonded to other atoms outside the ring, such as hydrogen atoms.

[0040] The term "five-membered ring" is understood to mean a ring formed by 5 atoms. The ring atoms of the "five-membered ring" may be bonded to other atoms outside the ring, such as hydrogen atoms.

[0041] In this specification, a single bond refers to a direct bond.

[0042] The terms "without", "not containing", "not comprising" do not exclude impurities that may be present in the compound before deposition. Impurities have no technical effect on the purpose to be achieved by the present invention.

[0043] The term "sandwiched in contact" refers to a three-layer arrangement in which the middle layer is in direct contact with two adjacent layers.

[0044] The terms "light absorbing layer" and "light-absorbing layer" are used synonymously.

[0045] The terms "light-emitting layer", "light-emitting layer" and "light-emitting layer" are used synonymously.

[0046] The terms “p-type charge generation layer,” “p-CGL,” and “hole generation layer” are used synonymously.

[0047] The terms “n-type charge generation layer,” “n-CGL,” and “electron generation layer” are used synonymously.

[0048] The terms "OLED," "organic light emitting diode," and "organic light emitting device" are used synonymously.

[0049] The terms "anode," "anode layer," and "anode electrode" are used synonymously.

[0050] The terms "cathode," "cathode layer," and "cathode electrode" are used synonymously.

[0051] In this specification, hole characteristics refer to the ability to form holes by donating electrons when an electric field is applied, and 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 according to the highest occupied molecular orbital (HOMO) energy level.

[0052] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductive properties 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.

[0053] Asterisk "*" indicates the binding position.

[0054] Beneficial effects

[0055] Surprisingly, it has been found that the organic compounds according to formula (I) of the present invention solve the underlying problem of the present invention by making the devices superior in various aspects to organic electroluminescent devices known in the art, in terms of operating voltage, efficiency and / or lifetime, in particular in terms of operating voltage, efficiency and voltage stability over time. It has also been surprisingly found that the compounds of formula (I) can have improved LUMO energy levels, improved dipole moments and / or improved thermal properties, in particular improved thermal stability and / or processing properties at elevated temperatures, compared to the comparative examples.

[0056] The compound of formula (I) exhibits good thermal properties, such as evaporation temperature, for good fabrication of OLED devices. When used as a p-type dopant in OLED devices, it exhibits good performance, such as low operating voltage, low increase in operating voltage over time, high efficiency, and long lifetime. In addition, the compound of formula (I) exhibits low mass loss during heating, thereby avoiding tool contamination during the fabrication of organic electronic devices.

[0057] The thermal stability of the compound according to formula (I) as measured by TGA 5% and the volatility as measured by standard onset temperature may be within the range required for mass production.

[0058] Surprisingly, it was found that the LUMO energy level can be in the range required for efficient hole injection and / or hole generation.

[0059] Compounds of formula (I)

[0060] According to one embodiment of the present invention, the compound of formula (I) is represented by the following formula:

[0061] (I),

[0062] in

[0063] HetAr is selected from formula (II):

[0064] (II),

[0065] A 1 Selected from formula (III):

[0066] (III),

[0067] A 2 Selected from formula (IV)

[0068] (IV),

[0069] wherein the asterisk "*" indicates the position of bonding,

[0070] R 1 and R 2 are independently selected from the group consisting of CN, partially fluorinated C1to C8alkyl, perfluorinated C1to C8alkyl, CF3, substituted or unsubstituted C6to C 30 aryl, substituted or unsubstituted C2to C 30 heteroaryl,

[0071] wherein one or more substituents on R 1 and R 2 are independently selected from the group consisting of D, partially fluorinated C1to C8alkyl, perfluorinated C1to C8alkyl, CF3, halogen, F or CN;

[0072] R 3 and R 4 are independently selected from the group consisting of H, D, halogen, F, CN, partially fluorinated C1to C4alkyl, perfluorinated C1to C4alkyl or CF3;

[0073] R 5 is independently selected from the group consisting of H, D, halogen, F, CN, partially fluorinated C1to C8alkyl, perfluorinated C1to C8alkyl, CF3, substituted or unsubstituted C6to C 30 aryl or substituted or unsubstituted C2to C 30 heteroaryl,

[0074] wherein one or more substituents on R 5 are independently selected from the group consisting of D, partially fluorinated C1to C8alkyl or perfluorinated C1to C8alkyl, CF3, halogen, F, CN;

[0075] X a1 is selected from N or CR a4 ;

[0076] R a1 , R a2 , R a3 and R a4 are independently selected from the group consisting of H, D, substituted or unsubstituted C1to C8alkyl, partially fluorinated C1to C8alkyl, perfluorinated C1to C8alkyl, CF3, substituted or unsubstituted C6to C 30 aryl, substituted or unsubstituted C2to C 30 heteroaryl, halogen, F, CN, SF5,

[0077] wherein R a1 , R a2 , Ra3 and R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, SF5;

[0078] where R a1 、R a2 、R a3 and R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN or SF5.

[0079] According to one embodiment, for compounds of formula (I), the SF5 group may be excluded.

[0080] According to one embodiment, compounds of formula (I) comprising more than one pyridine group may be excluded.

[0081] According to one embodiment, compounds of formula (I) comprising more than two pyridine groups may be excluded.

[0082] According to one embodiment, compounds of formula (I) comprising more than one aromatic diazine group may be excluded.

[0083] According to one embodiment, compounds of formula (I) comprising more than one aromatic triazine group may be excluded.

[0084] According to one embodiment, compounds of formula (I) comprising more than one aromatic diazine group, comprising an aromatic triazine group and comprising more than one pyridine group may be excluded.

[0085] According to one embodiment, wherein R of the compound of formula (I) a2 and R a3 Do not select CN.

[0086] According to one embodiment, wherein R of the compound of formula (I) a2 Do not select CN.

[0087] According to one embodiment of the present invention, the compound of formula (I) is represented by the following formula:

[0088] (I),

[0089] in

[0090] HetAr is selected from formula (II):

[0091] (II),

[0092] A 1Selected from formula (III):

[0093] (III),

[0094] A 2 Selected from formula (IV)

[0095] (IV),

[0096] The asterisk "*" indicates the binding position.

[0097] R 1 and R 2 independently selected from CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl,

[0098] where R 1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3 or CN;

[0099] R 3 and R 4 Independently selected from H, D, CN, CF3;

[0100] R 5 independently selected from H, D, CN, substituted or unsubstituted C6 aryl or substituted or unsubstituted C4 to C5 heteroaryl,

[0101] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN;

[0102] X a1 Select N or CR a4 ;

[0103] R a1 、R a2 、R a3 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0104] where R a1 、R a2 、R a3 and Ra4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN;

[0105] where R a1 、R a2 、R a3 and R a4 At least one of the following is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and

[0106] The optional R of the compound of formula (I) a2 and R a3 Do not select CN.

[0107] According to one embodiment of the present invention, the compound of formula (I) is represented by the following formula:

[0108] (I),

[0109] in

[0110] HetAr is selected from formula (II):

[0111] (II),

[0112] A 1 Selected from formula (III):

[0113] (III),

[0114] A 2 Selected from formula (IV)

[0115] (IV),

[0116] The asterisk "*" indicates the binding position.

[0117] R 1 and R 2 independently selected from CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C4 to C5 heteroaryl,

[0118] where R 1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3 or CN;

[0119] R 3 and R 4 independently selected from H, D;

[0120] R 5 independently selected from substituted or unsubstituted C6 aryl or substituted or unsubstituted C4 to C5 heteroaryl,

[0121] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN;

[0122] X a1 Select N or CR a4 ;

[0123] R a1 、R a2 、R a3 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0124] where R a1 、R a2 、R a3 and R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN;

[0125] where R a1 、R a2 、R a3 and R a4 At least one of the following is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and

[0126] The optional R of the compound of formula (I) a2 and R a3 Do not select CN.

[0127] According to one embodiment, there is provided a compound of formula (I):

[0128] (I), where

[0129] HetAr is selected from formula (II):

[0130] (II),

[0131] A 1Selected from formula (III):

[0132] (III),

[0133] A 2 Selected from formula (IV)

[0134] (IV),

[0135] The asterisk "*" indicates the binding position.

[0136] R 1 and R 2 independently selected from CN, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl,

[0137] where R 1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN;

[0138] R 3 and R 4 Independently selected from H, D, halogen, F, CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl or CF3;

[0139] R 5 independently selected from H, D, halogen, F, CN, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0140] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN;

[0141] X a1 Select N or CR a4 ;

[0142] R a1 、R a2 、R a3 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0143] where R a1 、R a2 、R a3 and R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN;

[0144] where R a1 、R a2 、R a3 and R a4 At least one of the following is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and wherein HetAr and R 5 Select Same.

[0145] According to one embodiment of formula (I), wherein when the aromatic carbon is directly bonded to an sp2 hybridized ring nitrogen atom, the CN group is not bonded to said aromatic carbon atom.

[0146] According to one embodiment, the compound of formula (I) is represented by:

[0147] (I),

[0148] in

[0149] HetAr is selected from formula (II):

[0150] (II),

[0151] A 1 Selected from formula (III):

[0152] (III),

[0153] A 2 Selected from formula (IV)

[0154] (IV),

[0155] The asterisk "*" indicates the binding position.

[0156] R 1 and R 2 independently selected from CN, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C30 heteroaryl,

[0157] where R 1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN;

[0158] R 3 and R 4 Independently selected from H, D, halogen, F, CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl or CF3;

[0159] R 5 independently selected from H, D, halogen, F, CN, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0160] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN;

[0161] X a1 Select N or CR a4 ;

[0162] R a1 、R a2 、R a3 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0163] where R a1 、R a2 、R a3 and R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN;

[0164] where R a1 、R a2 、R a3 and R a4 At least one of the following is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and

[0165] wherein when the aromatic carbon is directly bonded to an sp2 hybridized ring nitrogen atom, the CN group is not bonded to the aromatic carbon atom; and optionally R a2 Not selected from CN.

[0166] According to one embodiment of the present invention, the compound of formula (I) comprises less than nine CN groups, preferably less than eight CN groups, further preferably more than one CN group and less than 6 CN groups, more than two CN groups and less than 5 CN groups.

[0167] According to one embodiment of the invention, the compound of formula (I) contains ≥6 F and ≤24 F groups, preferably ≥8 F and ≤18 F atoms.

[0168] According to one embodiment of the present invention, the calculated LUMO of the compound of formula (I) is in the range of ≤-5.00 eV to ≥-5.75 eV, preferably in the range of ≤-5.05 eV to ≥-5.75 eV; even more preferably in the range of ≤-5.10 eV to ≥-5.70 eV, most preferably in the range of ≤-5.15 eV to ≥-5.70 eV, when calculated using the program packages ORCA V5.0.3 (Max Planck Institute für Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Köln, Germany) by applying the hybrid functional B3LYP and 6-31G* basis set in the gas phase.

[0169] R 1 and R 2

[0170] According to one embodiment, wherein R 1 and R 2 Can be independently selected from CN, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C3 to C 24 Heteroaryl.

[0171] According to one embodiment, wherein R 1 and R 2 Can be independently selected from CN, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18heteroaryl.

[0172] According to one embodiment, one or more substituents on R 1 and R 2 may be independently selected from CN, partially fluorinated C1to C4alkyl or perfluorinated C1to C4alkyl, CF3, substituted or unsubstituted C6to C 12 aryl, substituted or unsubstituted C3to C 12 heteroaryl.

[0173] According to one embodiment, one or more substituents on R 1 and R 2 may be independently selected from CN, partially fluorinated C1to C4alkyl, perfluorinated C1to C4alkyl, CF3, substituted or unsubstituted C6aryl, substituted or unsubstituted C3to C5heteroaryl. 10 aryl or substituted or unsubstituted C3to C9heteroaryl.

[0174] According to one embodiment, one or more substituents on R 1 and R 2 may be independently selected from CN, partially fluorinated C1to C4alkyl, perfluorinated C1to C4alkyl, CF3, substituted or unsubstituted C6aryl, substituted or unsubstituted C3to C5heteroaryl.

[0175] According to one embodiment, one or more substituents on R 1 and R 2 may be independently selected from CN, partially fluorinated C1to C4alkyl, perfluorinated C1to C4alkyl, CF3, substituted or unsubstituted C6aryl, substituted or unsubstituted C3to C5heteroaryl.

[0176] According to one embodiment, one or more substituents on R 1 and R 2 may be independently selected from D, partially fluorinated C1to C8alkyl, perfluorinated C1to C8alkyl, CF3or CN.

[0177] According to one embodiment, one or more substituents on R 1 and R 2 may be independently selected from D, partially fluorinated C1to C4alkyl, perfluorinated C1to C4alkyl, CF3or CN.

[0178] According to one embodiment, one or more substituents on R 1 and R 2 may be independently selected from D, CF3, CN.

[0179] R 1 and R 2 may be independently selected from D, CF3, CN.

[0180] According to one embodiment, R1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0181] According to one embodiment, R 1 and R 2 The one or more substituents are independently selected from D, CF3, halogen, F, CN.

[0182] According to one embodiment, R 1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN.

[0183] According to one embodiment, R 1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN.

[0184] According to one embodiment, R 1 and R 2 The one or more substituents are independently selected from D, CF3, and CN.

[0185] R 3 and R 4

[0186] According to one embodiment, the substituent R 3 and R 4 It may be independently selected from H, D, CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl or CF3.

[0187] According to one embodiment, the substituent R 3 and R 4 Preferably, they are independently selected from H, D, CN, and CF3.

[0188] According to one embodiment, the substituent R 3 and R 4 It may further be preferably independently selected from H or D.

[0189] R 5

[0190] According to one embodiment, wherein R 5 selected from H, D, halogen, F, CN, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 24 Aryl or substituted or unsubstituted C3 to C24 heteroaryl.

[0191] According to one embodiment, wherein R 5 is selected from H, D, halogen, F, CN, partially fluorinated Ci to C4alkyl or perfluorinated Ci to C4alkyl, CF3, substituted or unsubstituted C6to C 18 aryl or substituted or unsubstituted C3to C9heteroaryl. 18 heteroaryl.

[0192] According to one embodiment, wherein R 5 is selected from H, D, halogen, F, CN, partially fluorinated Ci to C4alkyl or perfluorinated Ci to C4alkyl, CF3, substituted or unsubstituted C6to C 12 aryl or substituted or unsubstituted C3to C9heteroaryl. 12 heteroaryl.

[0193] According to one embodiment, wherein R 5 is selected from H, D, halogen, F, CN, partially fluorinated Ci to C4alkyl or perfluorinated Ci to C4alkyl, CF3, substituted or unsubstituted C6to C 10 aryl or substituted or unsubstituted C3to C9heteroaryl.

[0194] According to one embodiment, wherein R 5 is selected from H, D, halogen, F, CN, partially fluorinated Ci to C4alkyl or perfluorinated Ci to C4alkyl, CF3, substituted or unsubstituted C6to C

[0195] According to one embodiment, the substituents R 5 may independently be selected from H, D, CN, CF3, substituted or unsubstituted C6aryl, substituted or unsubstituted C4to C5heteroaryl.

[0196] According to one embodiment, the substituents R 5 may preferably independently be selected from H, D, CN, substituted or unsubstituted C6aryl or substituted or unsubstituted C4to C5heteroaryl.

[0197] According to one embodiment, the substituents R 5 may further preferably independently be selected from substituted or unsubstituted C6aryl or substituted or unsubstituted C4to C5heteroaryl.

[0198] According to one embodiment, R 5 one or more substituents on R

[0199] According to one embodiment, R5 The one or more substituents are preferably independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3 or CN.

[0200] According to one embodiment, R 5 The one or more substituents on are further preferably independently selected from D, CF3 or CN.

[0201] R 5 Substituents on

[0202] According to one embodiment, wherein R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0203] According to one embodiment, wherein R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN.

[0204] According to one embodiment, wherein R 5 The one or more substituents are independently selected from D, CF3, and CN.

[0205] According to one embodiment, when the aromatic carbon is directly bonded to an sp2 hybridized ring nitrogen atom, R 5 The one or more CN substituents on the formula (I) or (VII) are not selectively bound to the aromatic carbon.

[0206] Formula (VIa)

[0207] According to one embodiment, wherein the substituent R 5 Can be selected from formula (VIa):

[0208] (VIa), wherein "*" indicates the binding position, and

[0209] in

[0210] X b1 Select N or CR b1 ,

[0211] X b2 Select N or CR b2 ,

[0212] X b3 Select N or CR b3 ,

[0213] X b4 Select N or CRb4 ,

[0214] X b5 Select N or CR b5 ,

[0215] R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, halogen, F or CN,

[0216] where R b1 to R b5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN.

[0217] According to one embodiment, wherein the substituent R 5 Can be selected from formula (VIa):

[0218] (VIa), wherein "*" indicates the binding position, and

[0219] in

[0220] X b1 Select N or CR b1 ,

[0221] X b2 Select N or CR b2 ,

[0222] X b3 Select N or CR b3 ,

[0223] X b4 Select N or CR b4 ,

[0224] X b5 Select N or CR b5 ,

[0225] R b1 to R b5 Preferably they are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN.

[0226] According to one embodiment, wherein the substituent R 5 Can be selected from formula (VIa):

[0227] (VIa), wherein "*" indicates the binding position, and

[0228] in

[0229] X b1 Select N or CR b1 ,

[0230] X b2 Select N or CR b2 ,

[0231] X b3 Select N or CR b3 ,

[0232] X b4 Select N or CR b4 ,

[0233] X b5 Select N or CR b5 ,

[0234] R b1 to R b5 More preferably, they are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

[0235] According to one embodiment of formula (VIa), wherein when R bn When it is N, the adjacent R bm Not a CN group, wherein n=1 to 5, wherein m=1 to 5.

[0236] According to one embodiment, wherein the substituent R 5 Can be selected from formula (VIa):

[0237] (VIa), wherein "*" indicates the binding position, and

[0238] in

[0239] X b1 Select N or CR b1 ,

[0240] X b2 Select N or CR b2 ,

[0241] X b3 Select N or CR b3 ,

[0242] X b4 Select N or CR b4 ,

[0243] X b5 Select N or CR b5 ,

[0244] R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, halogen, F or CN,

[0245] where R b1 to R b5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN;

[0246] When R bn When it is N, the adjacent R bm Not a CN group, wherein n=1 to 5, wherein m=1 to 5.

[0247] Formula (VIb)

[0248] According to one embodiment, wherein the substituent R 5 Can be selected from formula (VIb):

[0249] (VIb), wherein "*" indicates the binding position, and

[0250] in

[0251] X b4 Select N or CR b4 ,

[0252] R b1 to R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0253] where R b1 to R b3 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0254] According to one embodiment of formula (VIb), wherein preferably R b1 to R b4At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN.

[0255] According to one embodiment of formula (VIb), wherein R b1 to R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

[0256] Formula (VIc)

[0257] According to one embodiment, wherein the substituent R 5 Can be selected from formula (VIc):

[0258] (VIc), where "*" indicates the binding position, and

[0259] in

[0260] X b4 Select N or CR b4 ,

[0261] R b1 、R b2 、R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0262] where R b1 and R b2 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0263] According to one embodiment according to formula (VIc), wherein preferably R b1 、R b2 and R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN.

[0264] According to one embodiment according to formula (VIc), wherein more preferably R b1 and R b2 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

[0265] Formula (VId)

[0266] According to one embodiment, wherein the substituent R 5 Can be selected from formula (VId):

[0267] (VId), where "*" indicates the binding position, and

[0268] in

[0269] X b4 Select N or CR b4 ,

[0270] R b1 and R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0271] where R b1 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0272] According to one embodiment according to formula (VId), wherein preferably R b1 and / or R b4 Selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN.

[0273] According to one embodiment according to formula (VId), wherein more preferably R b1 Selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

[0274] Formula (VIe)

[0275] According to one embodiment, wherein the substituent R 5 Can be selected from formula (VIe):

[0276] (VIe), wherein "*" indicates the binding position, and

[0277] in

[0278] R b1 to R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30Heteroaryl, halogen, F, CN,

[0279] where R b1 to R b4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0280] According to one embodiment according to formula (VIe), wherein preferably R b1 to R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN.

[0281] According to one embodiment according to formula (VIe), wherein more preferably R b1 to R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

[0282] Formula (VIf)

[0283] According to one embodiment, wherein the substituent R 5 Can be selected from formula (VIf):

[0284] (VIf), where "*" indicates the binding position, and

[0285] in

[0286] R b1 、R b2 and R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0287] where R b1 、R b2 and R b4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0288] According to one embodiment according to formula (VIf), wherein preferably R b1 、R b2 and R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN.

[0289] According to one embodiment according to formula (VIf), wherein more preferably R b1 b2 and R b4 are each independently selected from the group consisting of H, D, substituted or unsubstituted Ci to Cs alkyl, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, substituted or unsubstituted C6 to C

[0290] formula (VIg)

[0291] According to one embodiment, wherein the substituents R 5 may be selected from formula (VIg):

[0292] (VIg), wherein "*" denotes the position of the binding, and

[0293] wherein

[0294] R b1 and R b4 are each independently selected from the group consisting of H, D, substituted or unsubstituted Ci to Cs alkyl, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, substituted or unsubstituted C6 to C 30 aryl, substituted or unsubstituted C2 to C 30 heteroaryl, halogen, F, CN,

[0295] wherein one or more substituents on R b1 and R b4 are independently selected from the group consisting of D, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, halogen, F, CN.

[0296] According to one embodiment according to formula (VIg), wherein preferably R b1 and R b4 are each independently selected from the group consisting of H, D, substituted or unsubstituted Ci to Cs alkyl, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, halogen, F, or CN.

[0297] According to one embodiment according to formula (VIg), wherein more preferably R b1 and R b4 are each independently selected from the group consisting of H, D, substituted or unsubstituted Ci to Cs alkyl, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, or CN.

[0298] R a1 to R a4

[0299] According to one embodiment, wherein R a1 to R a4 ​If present, it is independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C3 to C 30 heteroaryl, halogen, F, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0300] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C3 to C 24 heteroaryl, halogen, F, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0301] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, halogen, F, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated CF3, halogen, F, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0302] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, halogen, F, CN, and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0303] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 10 aryl, substituted or unsubstituted C3 to C9 heteroaryl, halogen, F, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0304] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, halogen, F, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0305] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId) a1 to R a4If present, it is independently selected from H, D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, halogen, F, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0306] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId) a1 to R a4 If present, it is independently selected from H, D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN. And wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0307] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId) a1 to R a4 If present, it is independently selected from H, D, CF3, halogen, F, CN. And wherein R a1 to R a4 At least one of them is selected from CF3, halogen, F, CN.

[0308] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C3 to C 30 Heteroaryl, CN; R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN.

[0309] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C3 to C 24 heteroaryl, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN.

[0310] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN.

[0311] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN.

[0312] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 10 aryl, substituted or unsubstituted C3 to C9 heteroaryl, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN.

[0313] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, CN; and wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN.

[0314] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 If present, is independently selected from H, D, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, CN and wherein R a1 to R a4 At least one of them is selected from partially fluorinated CF3 and CN.

[0315] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId) a1 to R a4 If present, it is independently selected from H, D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN. And wherein R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN.

[0316] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId) a1 to R a4 If present, it is independently selected from H, D, CF3, CN. And wherein R a1 to R a4 At least one of them is selected from CF3, CN.

[0317] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a2 and R a3 If present, CN is not selected. Thus, the stability of the compound of formula I or V can be further improved.

[0318] R a2 and R a3 / R a1 and R a4 Different definitions

[0319] According to one embodiment, R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a2 and R a3 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, and R a1 and R a4 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN.

[0320] R a1 to R a4 Substituents on

[0321] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 The one or more substituents on are, if present, independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0322] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 The one or more substituents on are, if present, independently selected from D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0323] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 The one or more substituents on are, if present, independently selected from D, CF3, halogen, F, CN.

[0324] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 The one or more substituents on are, if present, independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN.

[0325] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 The one or more substituents on R, if present, are independently selected from D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, CN.

[0326] According to one embodiment, wherein R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 The one or more substituents on are, if present, independently selected from D, CF3, CN.

[0327] According to one embodiment, R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 At least one of, if present, is independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, CN.

[0328] According to one embodiment, R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 At least one of, if present, is independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3.

[0329] According to one embodiment, R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 At least one of, if present, is independently selected from CF3.

[0330] According to one embodiment, R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 At least two of , if present, are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN.

[0331] According to one embodiment, R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 At least two of , if present, are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

[0332] According to one embodiment, R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 At least two of the alkyl groups, if present, are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3.

[0333] According to one embodiment, R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) a1 to R a4 At least two of the alkyl groups, if present, are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3.

[0334] According to one embodiment, at least two of R a1 to R a4 are, if present, independently selected from the group consisting of partially or perfluorinated Ci to C4alkyl, CF3.

[0335] According to one embodiment, at least two of R a1 to R a4 are, if present, independently selected from the group consisting of CF3.

[0336] R b1 to R b5

[0337] According to one embodiment, at least two of R b1 to R b5 are, if present, not selected from the group consisting of halogen or F.

[0338] According to one embodiment, at least two of R b1 to R b5 are, if present, not selected from the group consisting of halogen or F, and one or more substituents on R b1 to R b5 are, if present, not selected from the group consisting of halogen or F. Thereby, the stability of the compound of formula I or V can be further improved.

[0339] According to one embodiment, at least two of R b2 to R b3 are, if present, not selected from CN.

[0340] According to one embodiment, at least two of R b1 to R b5 are, if present, independently selected from the group consisting of H, D, substituted or unsubstituted Ci to Csalkyl, partially fluorinated Ci to Csalkyl, perfluorinated Ci to Csalkyl, CF3, substituted or unsubstituted C6to C 30 aryl, substituted or unsubstituted C3to C 30 heteroaryl, halogen, F, CN.

[0341] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 24 Aryl, substituted or unsubstituted C3 to C 24 Heteroaryl, halogen, F, CN.

[0342] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 18 Aryl, substituted or unsubstituted C3 to C 18 Heteroaryl, halogen, F, CN.

[0343] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 Heteroaryl, halogen, F, CN.

[0344] According to one embodiment, wherein R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 10 aryl, substituted or unsubstituted C3 to C9 heteroaryl, halogen, F, CN.

[0345] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5if present, is independently selected from H, D, substituted or unsubstituted C1to C4alkyl, partially fluorinated C1to C4alkyl, perfluorinated C1to C4alkyl, CF3, substituted or unsubstituted C6aryl, substituted or unsubstituted C3to C5heteroaryl, halogen, F, CN.

[0346] According to one embodiment, R in formula I, V, Via, VIb, VIc, VId, VIe, VIf, VIg is b1 to R b5 if present, is independently selected from H, D, substituted or unsubstituted C1to C4alkyl, partially fluorinated C1to C4alkyl, perfluorinated C1to C4alkyl, CF3, substituted or unsubstituted C6aryl, substituted or unsubstituted C3to C5heteroaryl, CN.

[0347] According to one embodiment, R in formula I, V, Via, VIb, VIc, VId, VIe, VIf, VIg is b1 to R b5 if present, is independently selected from H, D, substituted or unsubstituted C1to C8alkyl, partially fluorinated C1to C8alkyl, perfluorinated C1to C8alkyl, CF3, substituted or unsubstituted C6to C 30 aryl, substituted or unsubstituted C3to C 30 heteroaryl, CN.

[0348] According to one embodiment, R in formula I, V, Via, VIb, VIc, VId, VIe, VIf, VIg is b1 to R b5 if present, is independently selected from H, D, substituted or unsubstituted C1to C4alkyl, partially fluorinated C1to C4alkyl, perfluorinated C1to C4alkyl, CF3, substituted or unsubstituted C6to C 24 aryl, substituted or unsubstituted C3to C 24 heteroaryl, CN.

[0349] According to one embodiment, R in formula I, V, Via, VIb, VIc, VId, VIe, VIf, VIg is b1 to R b5 if present, is independently selected from H, D, substituted or unsubstituted C1to C4alkyl, partially fluorinated C1to C4alkyl, perfluorinated C1to C4alkyl, CF3, substituted or unsubstituted C6to C 18 aryl, substituted or unsubstituted C3to C 18 heteroaryl, CN.

[0350] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 Heteroaryl, CN.

[0351] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 10 aryl, substituted or unsubstituted C3 to C9 heteroaryl, CN.

[0352] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 If present, it is independently selected from H, D, substituted or unsubstituted C1 to C4 alkyl, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl, CN.

[0353] According to one embodiment, R in formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 At least one of, if present, is independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, CN.

[0354] According to one embodiment, R in formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 At least one of, if present, is independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3.

[0355] According to one embodiment, R in formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 At least one of, if present, is independently selected from CF3.

[0356] R b1 to R b5 Substituents on

[0357] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 The at least one or more substituents on are, if present, independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0358] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 The at least one or more substituents on are, if present, independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0359] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 The at least one or more substituents on are, if present, independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0360] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 The at least one or more substituents on are, if present, independently selected from D, CF3, halogen, F, CN.

[0361] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 The at least one or more substituents on are, if present, independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, CN.

[0362] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 The at least one or more substituents on are, if present, independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, CN.

[0363] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 The at least one or more substituents on are, if present, independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, CN.

[0364] According to one embodiment, R in Formula I, V, VIa, VIb, VIc, VId, VIe, VIf, VIg b1 to R b5 The at least one or more substituents on are, if present, independently selected from D, CF3, CN.

[0365] R a1 to R a4 and R b1 to R b5

[0366] According to one embodiment, wherein R in Formula I a1 to R a4 , R in formula (VIa) b1 to R b5 , R in formula (VIb) b1 to R b3 , R in formula (VIc) b1 to R b2 , R in formula (VId) b1 , R in formula (Vie) b1 to R b4 , R in formula (VIf) b1 、R b and R b4 , R in formula (VIg) b1 and R b4 , do not select halogen or F; and preferably R in formula I a1 to R a4 , R in formula (VIa) b1 to R b5 , R in formula (VIb) b1 to R b3 , R in formula (VIc) b1 to R b2 , R in formula (VId) b1 , R in formula (Vie) b1 to R b4 , R in formula (VIf) b1 、R b and R b4 , R in formula (VIg) b1 and Rb4 halogen or F is not selected, and R a1 to R a4 , R b1 to R b5 one or more substituents on R

[0367] According to one embodiment, R a2 to R a3 R b2 to R b3 , and R b2 in formula (VIc) and (VIf) is not CN.

[0368] R a1 to R a4 / R 3 , R 4 , R 5

[0369] According to one embodiment, R 3 , R 4 , R 5 and R a1 to R a4 cannot be halogen or F if present.

[0370] According to one embodiment, R 3 , R 4 , R 5 and R a1 to R a4 cannot be halogen or F if present and R 1 , R 2 , R 5 and R a1 to R a4 cannot be halogen or F.

[0371] According to one embodiment, R 3 , R 4 , R 5 and R a1 to R a4 cannot be halogen or F if present and R b1 to Rb5 It cannot be halogen or F.

[0372] According to one embodiment, R in formula (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), (IIf) 3 、R 4 、R 5 and R a1 to R a4 If present, it cannot be a halogen or F, and R 1 、R 2 、R 5 and R a1 to R a4 One or more substituents on the b1 to R b5 It cannot be halogen or F, and R b1 to R b5 One or more substituents on α cannot be halogen or F.

[0373] According to one embodiment, the compound comprises 2 to 6 CN groups, preferably 3 to 6 CN groups, more preferably 4 to 4 CN groups, so as to maintain a moderate evaporation temperature for the production of OLEDs.

[0374] R 5 Specific groups

[0375] According to one embodiment, wherein R 5 Selected from the group represented by B1 to B163:

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382] Wherein “*” indicates the binding position.

[0383] According to a preferred embodiment, wherein R 5 is selected from B1 to B124. According to a more preferred embodiment, wherein R 5 According to a most preferred embodiment, wherein R 5 Selected from B1 to B17.

[0384] A 1 and A 2

[0385] According to one embodiment of the compound of formula (I), wherein A 1 and A 2 Can be selected from formula (V):

[0386] (V), where the asterisk “*” indicates the binding position.

[0387] Formula (II) of HetAr

[0388] According to one embodiment, formula II is selected from formula IIa

[0389] (IIa).

[0390] According to a preferred embodiment, formula II is selected from formula IIb

[0391] (IIb).

[0392] According to a more preferred embodiment, formula II is selected from formula IIc

[0393] (IIc)

[0394] According to an even more preferred embodiment, formula II is selected from formula IId

[0395] (IId)

[0396] According to an even more preferred embodiment, formula II is selected from formula IIe

[0397] (IIe).

[0398] According to a most preferred embodiment, formula II is selected from formula IIf

[0399] (IIf),

[0400] The compounds of formula IIf may also be partially deuterated or fully deuterated.

[0401] According to one embodiment of the compound of formula (I), wherein formula (II) is selected from formula (IIa), (IIb), (IIc), (IId), (IIe) and (IIf):

[0402]

[0403]

[0404] , where “*” indicates the binding position,

[0405] And preferably, formula (IIa), (IIb), (IIc), (IId), (IIe) and (IIf) are partially deuterated or fully deuterated, and further preferably, formula (IIf) is partially deuterated or fully deuterated.

[0406] HetAr

[0407] According to one embodiment of the compound of formula (I), wherein HetAr is selected from the group represented by C1 to C112:

[0408]

[0409]

[0410]

[0411]

[0412] , where “*” indicates the binding position.

[0413] According to one embodiment of the compound of formula (I), wherein for HetAr, a group represented by C90 to C109 is suitably used.

[0414] According to one embodiment of the compound of formula (I), wherein for HetAr, a group represented by C28 to C89 is preferred.

[0415] According to one embodiment of the compound of formula (I), wherein for HetAr, a group represented by C11 to C27 is more preferred.

[0416] According to one embodiment of the compound of formula (I), wherein for HetAr, the groups represented by C1 to C10 are most preferred.

[0417] According to one embodiment, HetAr is selected from C1 to C89. According to another embodiment, HetAr is selected from C1 to C27.

[0418] HetAr / R 5

[0419] According to one embodiment of the compound of formula (I), wherein HetAr and R 5 Select Same.

[0420] HetAr / R 5 / A 1 and A 2

[0421] According to one embodiment, HetAr is selected from the group consisting of formula II (II), and R 5 Selected from Formula VIa (VIa), wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0422] According to one embodiment, HetAr is selected from the group consisting of formula II (II), and Formula VIa is selected from Formula VIb (VIb); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0423] According to one embodiment, HetAr is selected from the group consisting of formula II (II), and Formula VIa is selected from Formula VIc (VIc); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0424] According to one embodiment, formula II is selected from formula IIa (IIa), and R 5 Selected from Formula VIa (VIa); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0425] According to one embodiment, formula II is selected from formula IIa (IIa) and Formula VIa is selected from Formula VIb (VIb); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0426] According to one embodiment, formula II is selected from formula IIa (IIa) and R 5 Selected from Formula VIc (VIc); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0427] According to one embodiment, formula II is selected from formula IIa (IIa) and R 5 Selected from formula VId (VId); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0428] According to one embodiment, formula II is selected from formula IIb (IIb) and R 5 Selected from Formula VIa (VIa); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0429] According to one embodiment, formula II is selected from formula IIb (IIb) and Formula VIa is selected from Formula VIb (VIb); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0430] According to one embodiment, formula II is selected from formula IIb (IIb) and R 5 Selected from Formula VIc (VIc); wherein R 3 and R 4 Independently selected from H, D, and A 1and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0431] According to one embodiment, formula II is selected from formula IIb (IIb) and R 5 Selected from formula VId (VId); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0432] According to one embodiment, formula II is selected from formula IIb (IIb) and Formula VIa is selected from Formula VIe, (VIe); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0433] According to one embodiment, formula II is selected from formula IIc (IIc) and R 5 Selected from Formula VIa (VIa); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0434] According to one embodiment, formula II is selected from formula IIc (IIc) and Formula VIa is selected from Formula VIb (VIb); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0435] According to one embodiment, formula II is selected from formula IIc (IIc) and R 5 Selected from Formula VIc (VIc); wherein R 3 and R 4are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0436] According to one embodiment, formula II is selected from formula IIc (IIc) and R 5 Selected from formula VId (VId); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0437] According to one embodiment, formula II is selected from formula IIc (IIc) and Formula VIa is selected from VIe, (VIe); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0438] According to one embodiment, formula II is selected from formula IId (IId) and R 5 Selected from Formula VIa (VIa); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0439] According to one embodiment, formula II is selected from formula IId (IId) and Formula VIa is selected from Formula VIb (VIb); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0440] According to one embodiment, formula II is selected from formula IId (IId) and R 5 Selected from Formula VIc (VIc); wherein R3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0441] According to one embodiment, formula II is selected from formula IId (IId) and R 5 Selected from formula VId (VId), wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0442] According to one embodiment, formula II is selected from formula IId (IId) and Formula VIa is selected from VIe, (VIe); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0443] According to one embodiment, formula II is selected from formula IId (IId) and Formula VIa is selected from VIf (VIf); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0444] According to one embodiment, formula II is selected from formula IIe (IIe) and R 5 Selected from Formula VIa (VIa); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0445] According to one embodiment, formula II is selected from formula IIe (IIe) and Formula VIa is selected from VIb, (VIb); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0446] According to one embodiment, formula II is selected from formula IIe (IIe) and R 5 Selected from Formula VIc (VIc); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0447] According to one embodiment, formula II is selected from formula IIe (IIe) and R 5 Selected from formula VId (VId); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0448] According to one embodiment, formula II is selected from formula IIe (IIe) and Formula VIa is selected from VIe, (VIe); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0449] According to one embodiment, formula II is selected from formula IIe (IIe) and Formula VIa is selected from VIf, (VIf); wherein R 3 and R 4 are independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0450] According to one embodiment, formula II is selected from formula IIe (IIe) and Formula VIa is selected from VIg, (VIg); wherein R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0451] According to one embodiment, formula II is selected from formula IIf (IIf) and R 5 Selected from Formula VIa (VIa), wherein HetAr may be partially deuterated or fully deuterated; wherein preferably R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0452] According to one embodiment, formula II is selected from formula IIf (IIf) and Formula VIa is selected from VIb, (VIb), wherein HetAr may be partially deuterated or fully deuterated; wherein preferably R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0453] According to one embodiment, formula II is selected from formula IIf (IIf) and R 5 Selected from Formula VIc (VIc); wherein HetAr may be partially deuterated or fully deuterated; wherein preferably R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0454] According to one embodiment, formula II is selected from formula IIf (IIf) and R 5 Selected from Formula VIc (VId); wherein HetAr may be partially deuterated or fully deuterated; wherein preferably R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0455] According to one embodiment, formula II is selected from formula IIf (IIf) and Formula VIa is selected from VIe, (VIe), wherein HetAr may be partially deuterated or fully deuterated; wherein preferably R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0456] According to one embodiment, formula II is selected from formula IIf (IIf) and Formula VIa is selected from VIf, (VIf), wherein HetAr may be partially deuterated or fully deuterated; wherein preferably R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0457] According to one embodiment, formula II is selected from formula IIf (IIf) and Formula VIa is selected from VIg, (VIg), wherein HetAr may be partially deuterated or fully deuterated; wherein preferably R 3 and R 4 Independently selected from H, D, and A 1 and A 2 Selected from , where the asterisk “*” indicates the binding position.

[0458] According to one embodiment, wherein R 5 Same as HetAr.

[0459] Compound of formula (VII)

[0460] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII):

[0461] (VII), where

[0462] HetAr is selected from the group consisting of formula (II), (IIa), (IIb), (IIc), (IId), (IIe) and (IIf):

[0463]

[0464]

[0465] , where the asterisk "*" indicates the binding position, and where

[0466] R 3 and R 4 Selected from H, D;

[0467] X a1 Select N or CR a4 ;

[0468] R a1 to R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, halogen, F or CN,

[0469] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0470] R a1 to R a4 At least one of which is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3 or CN;

[0471] R 5 selected from H, D, CN, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0472] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3 or CN.

[0473] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0474] (VII)

[0475] in

[0476] HetAr is selected from Formula II

[0477] (II)

[0478] R 3 and R 4 Selected from H, D;

[0479] X a1 Select N or CR a4 ;

[0480] R a1 to R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0481] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0482] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0483] R 5 selected from H, D, CN, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0484] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0485] And the asterisk "*" indicates the binding position.

[0486] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0487] (VII)

[0488] in

[0489] HetAr is selected from Formula IIa

[0490] (IIa)

[0491] R 3 and R 4 Selected from H, D;

[0492] X a1 Select N or CR a4 ;

[0493] R a1 、R a2 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, CN,

[0494] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0495] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0496] R 5 selected from H, D, CN, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0497] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0498] And the asterisk "*" indicates the binding position.

[0499] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0500] (VII)

[0501] in

[0502] HetAr is selected from Formula IIb

[0503] (IIb),

[0504] R 3 and R4 Selected from H, D;

[0505] X a1 Select N or CR a4 ,

[0506] R a1 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, CN,

[0507] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0508] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN.

[0509] R 5 selected from H, D, CN, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0510] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0511] And the asterisk "*" indicates the binding position.

[0512] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0513] (VII)

[0514] in

[0515] HetAr is selected from the group consisting of formula IIc

[0516] (IIc)

[0517] R 3 and R 4 Selected from H, D;

[0518] X a1 Select N or CR a4 ,

[0519] R a1 to R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0520] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0521] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0522] R 5 selected from H, D, CN, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0523] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0524] And the asterisk "*" indicates the binding position.

[0525] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0526] (VII)

[0527] in

[0528] HetAr is selected from (IId)

[0529] R 3 and R 4 Selected from H, D;

[0530] X a1 Select N or CR a4 ;

[0531] R a1 、R a2 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN,

[0532] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0533] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0534] R 5 selected from H, D, CN, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0535] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0536] And the asterisk "*" indicates the binding position.

[0537] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0538] (VII)

[0539] in

[0540] HetAr is selected from the group consisting of formula IIe

[0541] ( IIe ),

[0542] R 3 and R 4 Selected from H, D;

[0543] R a1 and R a4independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, CN,

[0544] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0545] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0546] R 5 selected from H, D, CN, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0547] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0548] And the asterisk "*" indicates the binding position.

[0549] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII):

[0550] (VII),

[0551] in

[0552] HetAr is selected from the group consisting of formula (II), (IIa), (IIb), (IIc), (IId), (IIe) and (IIf):

[0553]

[0554]

[0555] , where the asterisk "*" indicates the binding position, and where

[0556] R 3 and R 4 Selected from H, D;

[0557] Xa1 Select N or CR a4 ;

[0558] R a1 to R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, halogen, F or CN,

[0559] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0560] R a1 to R a4 At least one of which is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3 or CN;

[0561] R 5 Selected from formula (VIa)

[0562] (VIa), where

[0563] X b1 Select N or CR b1 ,

[0564] X b2 Select N or CR b2 ,

[0565] X b3 Select N or CR b3 ,

[0566] X b4 Select N or CR b4 ,

[0567] X b5 Select N or CR b5 ,

[0568] R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl or CN,

[0569] where Rb1 to R b5 The one or more substituents on are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3 or CN,

[0570] And the asterisk "*" indicates the binding position.

[0571] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0572] (VII)

[0573] in

[0574] HetAr is selected from the formula IIf

[0575] (IIf),

[0576] wherein Formula IIf may be partially deuterated or fully deuterated;

[0577] R 3 and R 4 Selected from H, D,

[0578] R 5 selected from H, D, CN, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl,

[0579] where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0580] And the asterisk "*" indicates the binding position.

[0581] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0582] (VII)

[0583] in

[0584] HetAr is selected from Formula II

[0585] (II)

[0586] R 3 and R 4 Selected from H, D,

[0587] Xa1 Select N or CR a4 ,

[0588] R a1 to R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, CN,

[0589] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0590] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0591] R 5 Selected from Formula VIa

[0592] (VIa)

[0593] in

[0594] X b1 Select N or CR b1 ,

[0595] X b2 Select N or CR b2 ,

[0596] X b3 Select N or CR b3 ,

[0597] X b4 Select N or CR b4 ,

[0598] X b5 Select N or CR b5 ,

[0599] R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, CN,

[0600] where R b1 to R b5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, CN,

[0601] And the asterisk "*" indicates the binding position.

[0602] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0603] (VII)

[0604] in

[0605] HetAr is selected from Formula IIa

[0606] (IIa)

[0607] R 3 and R 4 Selected from H, D,

[0608] X a1 Select N or CR a4 ,

[0609] R a1 、R a2 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, CN,

[0610] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0611] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0612] R 5 Selected from Formula VIa

[0613] (VIa)

[0614] in

[0615] Xb1 is selected from N or CR b1 ,

[0616] X b2 is selected from N or CR b2 ,

[0617] X b3 is selected from N or CR b3 ,

[0618] X b4 is selected from N or CR b4 ,

[0619] X b5 is selected from N or CR b5 ,

[0620] R b1 and R b5 are independently selected from H, D, substituted or unsubstituted C1to C8alkyl, partially fluorinated C1to C8alkyl, perfluorinated C1to C8alkyl, CF3, substituted or unsubstituted C6to C 30 aryl, substituted or unsubstituted C2to C 30 heteroaryl, CN,

[0621] wherein one or more substituents on R b1 and R b5 are independently selected from D, partially fluorinated C1to C8alkyl, perfluorinated C1to C8alkyl, CF3, CN,

[0622] and wherein the asterisk "*" indicates the position of the binding.

[0623] According to one embodiment, the compound of formula (I) is selected from a compound of formula (VII)

[0624] (VII)

[0625] wherein

[0626] HetAr is selected from formula IIb

[0627] (IIb),

[0628] R 3 and R 4 are selected from H, D,

[0629] X a1 is selected from N or CR a4 ,

[0630] R a1 and R a4independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, CN,

[0631] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0632] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0633] R 5 Selected from Formula VIa

[0634] (VIa)

[0635] in

[0636] X b1 Select N or CR b1 ,

[0637] X b2 Select N or CR b2 ,

[0638] X b3 Select N or CR b3 ,

[0639] X b4 Select N or CR b4 ,

[0640] X b5 Select N or CR b5 ,

[0641] R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, CN,

[0642] where R b1 to R b5The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, CN,

[0643] And the asterisk "*" indicates the binding position.

[0644] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0645] (VII)

[0646] in

[0647] HetAr is selected from the group consisting of formula IIc

[0648] (IIc)

[0649] R 3 and R 4 Selected from H, D,

[0650] X a1 Select N or CR a4 ,

[0651] R a1 to R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, CN,

[0652] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0653] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0654] R 5 Selected from Formula VIa

[0655] (VIa)

[0656] in

[0657] X b1 Select N or CR b1 ,

[0658] Xb2 Select N or CR b2 ,

[0659] X b3 Select N or CR b3 ,

[0660] X b4 Select N or CR b4 ,

[0661] X b5 Select N or CR b5 ,

[0662] R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, CN,

[0663] where R b1 to R b5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, CN,

[0664] And the asterisk "*" indicates the binding position.

[0665] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0666] (VII)

[0667] in

[0668] HetAr is selected from the group consisting of formula IId

[0669] (IId),

[0670] R 3 and R 4 Selected from H, D,

[0671] X a1 Select N or CR a4 ,

[0672] R a1 、R a2 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, CN,

[0673] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0674] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0675] R 5 Selected from Formula VIa

[0676] (VIa)

[0677] in

[0678] X b1 Select N or CR b1 ,

[0679] X b2 Select N or CR b2 ,

[0680] X b3 Select N or CR b3 ,

[0681] X b4 Select N or CR b4 ,

[0682] X b5 Select N or CR b5 ,

[0683] R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, CN,

[0684] where R b1 to R b5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, CN,

[0685] And the asterisk "*" indicates the binding position.

[0686] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0687] (VII)

[0688] in

[0689] HetAr is selected from the group consisting of formula IIe

[0690] ( IIe ),

[0691] R 3 and R 4 Selected from H, D,

[0692] X a1 Select N or CR a4 ,

[0693] R a1 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, CN,

[0694] where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0695] R a1 to R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN;

[0696] R 5 Selected from Formula VIa

[0697] (VIa)

[0698] in

[0699] X b1 Select N or CR b1 ,

[0700] X b2 Select N or CR b2 ,

[0701] X b3 Select N or CR b3 ,

[0702] X b4 Select N or CR b4 ,

[0703] X b5 Select N or CR b5 ,

[0704] R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, CN,

[0705] where R b1 to R b5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, CN,

[0706] And the asterisk "*" indicates the binding position.

[0707] According to one embodiment, the compound of formula (I) is selected from the compounds of formula (VII)

[0708] (VII)

[0709] in

[0710] HetAr is selected from the formula IIf

[0711] (IIf),

[0712] wherein Formula IIf may be partially deuterated or fully deuterated;

[0713] R 3 and R 4 Selected from H, D,

[0714] R 5 Selected from Via

[0715] (VIa),

[0716] in

[0717] X b1 Select N or CR b1 ,

[0718] X b2 Select N or CR b2 ,

[0719] X b3 selected from N or CR b3 ,

[0720] X b4 selected from N or CR b4 ,

[0721] X b5 selected from N or CR b5 ,

[0722] R b1 R b5 are independently selected from H, D, substituted or unsubstituted Ci to Cs alkyl, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, substituted or unsubstituted C6 to C 30 aryl, substituted or unsubstituted C2 to C 30 heteroaryl, CN,

[0723] wherein one or more substituents on R b1 R b5 are independently selected from D, partially fluorinated Ci to Cs alkyl, perfluorinated Ci to Cs alkyl, CF3, CN,

[0724] and wherein the asterisk "*" indicates the position of bonding.

[0725] compound of formula (I)

[0726] According to one embodiment of the application, the compound of formula (I) is selected from the group consisting of compounds I-1 to I-53:

[0727]

[0728]

[0729]

[0730]

[0731]

[0732] According to one embodiment, the compound of formula (I) is selected from I-1 to I-52.

[0733] According to one embodiment of the application, the compound of formula (I) is selected from the group consisting of compounds I-1 to I-40:

[0734]

[0735]

[0736]

[0737] According to one embodiment, compounds 1-4, 1-8 and 1-14 are less preferred. According to one embodiment, compounds 1-4, 1-8 and 1-14 may be excluded.

[0738] According to one embodiment, the compound of formula (I) is selected from 1-41 to 1-52.

[0739] According to a preferred embodiment, the compound of formula (I) is selected from I-1, I-6, I-10, I-12, I-16, I-18 to I-30 and I-32 to I-40:

[0740]

[0741]

[0742] According to a more preferred embodiment, the compound of formula (I) is selected from 1-1, 1-12, 1-24, 1-27, 1-30, 1-34, 1-38 and 1-39:

[0743]

[0744] According to a most preferred embodiment, the compound of formula (I) is selected from I-1, I-24, I-27, I-30, I-34 and I-39:

[0745]

[0746] Organic semiconductor layer

[0747] Another aspect of the present invention relates to an organic semiconductor layer, comprising a compound of formula (I), wherein the compound of formula (I) is preferably a compound of formula (VII).

[0748] According to one embodiment, the organic semiconductor layer comprises a compound of formula (I) and a hole-transporting matrix compound, and wherein the compound of formula (I) is preferably a compound of formula (VII).

[0749] According to one embodiment, the organic semiconductor layer is a hole injection layer or a p-type charge generation layer.

[0750] Furthermore, the present invention relates to an organic semiconductor layer, wherein the organic semiconductor layer comprises a compound according to formula (VII), the compound according to formula (VII) being preferably selected from compounds I-1 to 1-40.

[0751] In case the organic semiconductor layer comprises a compound according to the invention, in the context of this application the term "compound of formula (I)" shall also be intended to comprise a composition comprising at least one compound according to the invention as described above.

[0752] According to one embodiment of the present invention, the organic semiconductor layer and / or the compound of formula (I) does not emit light.

[0753] In the context of this specification, the term "substantially non-emissive" or "non-emissive" means that a compound or layer contributes less than 10%, and preferably less than 5%, to the visible emission spectrum of a device. The visible emission spectrum refers to the emission spectrum in the wavelength range of approximately 380 nm or more to approximately 780 nm or less.

[0754] According to one embodiment of the present invention, the at least one organic semiconductor layer may further comprise at least one matrix compound, also referred to as covalent matrix compound or substantially covalent matrix compound.

[0755] Organic electronic devices

[0756] Another aspect of the present invention relates to an organic electronic device, wherein the organic electronic device comprises an organic semiconductor layer comprising a compound of formula (I), and wherein the compound of formula (I) is preferably a compound of formula (VII).

[0757] According to one embodiment, the organic electronic device comprises an anode layer, a cathode layer and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is arranged between the anode layer and the cathode layer, and wherein the at least one organic semiconductor layer is an organic semiconductor layer according to the present invention.

[0758] According to one embodiment, at least one organic semiconductor layer is a hole injection layer and / or a p-type charge generation layer.

[0759] According to one embodiment, the hole injection layer is in direct contact with the anode layer.

[0760] According to one embodiment, the hole injection layer is in direct contact with the anode layer, and the anode layer is in direct contact with the substrate, wherein the substrate is selected from a glass substrate, a plastic substrate, a metal substrate or a backplane.

[0761] According to one embodiment, the organic electronic device comprises an anode layer, a cathode layer and at least one organic semiconductor layer and at least one photoactive layer; wherein the at least one organic semiconductor layer is arranged between the anode layer and the cathode layer, and wherein the at least one organic semiconductor layer is an organic semiconductor layer according to the present invention; wherein the at least one organic semiconductor layer is arranged between the anode layer and the at least one photoactive layer.

[0762] According to one embodiment, the organic electronic device comprises an anode layer, a cathode layer, a first photoactive layer, a second photoactive layer, at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is an organic semiconductor layer according to the present invention, wherein the at least one organic semiconductor layer is arranged between the anode layer and the cathode layer, wherein the at least one organic semiconductor layer is a hole injection layer and / or a p-type charge generation layer, wherein the hole injection layer is arranged in direct contact with the anode layer, and wherein the p-type charge generation layer is arranged between the first photoactive layer and the second photoactive layer, wherein the hole injection layer is closer to the anode layer than the p-type charge generation layer.

[0763] According to one embodiment, the organic electronic device comprises an anode layer, a cathode layer, a first photoactive layer, a second photoactive layer, a hole injection layer, and a p-type charge generation layer, wherein the hole injection layer is arranged in direct contact with the anode layer, and wherein the p-type charge generation layer is arranged between the first photoactive layer and the second photoactive layer, wherein the hole injection layer is closer to the anode layer than the p-type charge generation layer, wherein the hole injection layer or the p-type charge generation layer comprises a compound of formula (I), and wherein the compound of formula (I) is preferably a compound of formula (VII), and wherein the first photoactive layer, the second photoactive layer, the hole injection layer, and the p-type charge generation layer are arranged between the anode layer and the cathode layer.

[0764] According to one embodiment, an organic electronic device comprises an anode layer, a cathode layer, a first photoactive layer, a second photoactive layer, a hole injection layer, and a p-type charge generation layer, wherein the hole injection layer is arranged in direct contact with the anode layer, and wherein the p-type charge generation layer is arranged between the first photoactive layer and the second photoactive layer, wherein the hole injection layer is closer to the anode layer than the p-type charge generation layer, wherein the hole injection layer or the p-type charge generation layer is an organic semiconductor layer according to the present invention, wherein the first photoactive layer, the second photoactive layer, the hole injection layer, and the p-type charge generation layer are arranged between the anode layer and the cathode layer.

[0765] According to one embodiment, the organic electronic device comprises an anode layer, a cathode layer, at least two photoactive layers, at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is an organic semiconductor layer according to the present invention, wherein the at least one organic semiconductor layer is arranged between the anode layer and the cathode layer, wherein the at least one organic semiconductor layer is a hole injection layer and / or a p-type charge generation layer, wherein the hole injection layer is arranged in direct contact with the anode layer, and wherein the p-type charge generation layer is arranged between the at least two photoactive layers, wherein the hole injection layer is closer to the anode layer than the p-type charge generation layer.

[0766] According to one embodiment, the organic electronic device comprises an anode layer, a cathode layer, at least two photoactive layers, a hole injection layer, and a p-type charge generation layer, wherein the hole injection layer is arranged in direct contact with the anode layer, and wherein the p-type charge generation layer is arranged between the at least two photoactive layers, wherein the hole injection layer is closer to the anode layer than the p-type charge generation layer, wherein the hole injection layer or the p-type charge generation layer comprises a compound of formula (I), wherein the at least two photoactive layers, the hole injection layer, and the p-type charge generation layer are arranged between the anode layer and the cathode layer.

[0767] According to one embodiment, the organic electronic device comprises an anode layer, a cathode layer, at least two photoactive layers, a hole injection layer, and a p-type charge generation layer, wherein the hole injection layer is arranged in direct contact with the anode layer, and wherein the p-type charge generation layer is arranged between the at least two photoactive layers, wherein the hole injection layer is closer to the anode layer than the p-type charge generation layer, wherein the hole injection layer or the p-type charge generation layer comprises a compound of formula (I), and wherein the compound of formula (I) is preferably a compound of formula (VII), wherein the at least two photoactive layers, the hole injection layer, and the p-type charge generation layer are arranged between the anode layer and the cathode layer.

[0768] According to one embodiment, the organic electronic device comprises an anode layer, a cathode layer, at least two photoactive layers, a hole injection layer, and a p-type charge generation layer, wherein the hole injection layer is arranged in direct contact with the anode layer, and wherein the p-type charge generation layer is arranged between the at least two photoactive layers, wherein the hole injection layer is closer to the anode layer than the p-type charge generation layer, wherein the hole injection layer or the p-type charge generation layer is an organic semiconductor layer according to the present invention, wherein the at least two photoactive layers, the hole injection layer, and the p-type charge generation layer are arranged between the anode layer and the cathode layer.

[0769] According to one embodiment of the present invention, the hole injection layer is in direct contact with the anode layer, and the anode layer is in direct contact with the substrate, wherein the substrate is selected from a glass substrate, a plastic substrate, a metal substrate or a backplane.

[0770] According to an embodiment of the organic electronic device of the present invention, the anode layer comprises at least a first anode sublayer and a second anode sublayer.

[0771] According to a preferred embodiment, the photoactive layer is an emissive layer, preferably a light-emitting layer.

[0772] According to one embodiment, the organic electronic device is an electroluminescent device, an organic 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).

[0773] According to a preferred embodiment, the organic electronic device is an organic electroluminescent device.

[0774] Display device

[0775] Another aspect of the present invention relates to a display device comprising an organic electronic device, wherein the organic electronic device comprises an organic semiconductor layer, wherein the organic semiconductor layer comprises a compound of formula (I), and wherein the compound of formula (I) is preferably a compound of formula (VII).

[0776] According to one embodiment, the organic electronic device comprises the organic semiconductor layer according to the present invention.

[0777] Essentially covalent matrix compound

[0778] The organic semiconductor layer may further comprise a covalent matrix compound, also referred to as a substantially covalent matrix compound. According to one embodiment, the substantially covalent matrix compound may be selected from at least one organic compound. The substantially covalent matrix may consist essentially of covalently bonded C, H, O, N, S, and may optionally further comprise covalently bonded B, P, As, and / or Se.

[0779] According to one embodiment of the organic electronic device, the organic semiconductor layer further comprises a substantially covalent matrix compound, wherein the substantially covalent matrix compound can be selected from organic compounds consisting essentially of covalently bonded C, H, O, N, S, which optionally additionally comprise covalently bonded B, P, As and / or Se.

[0780] Organometallic compounds containing carbon-metal covalent bonds, metal complexes containing organic ligands, and metal salts of organic acids are other examples of organic compounds that can be used as substantially covalent matrix compounds of the hole injection layer.

[0781] In one embodiment, the substantially covalent host compound contains no metal atoms and a majority of its backbone atoms may be selected from C, O, S, N. Alternatively, the substantially covalent host compound contains no metal atoms and a majority of its backbone atoms may be selected from C and N.

[0782] According to one embodiment, the substantially covalent matrix compound may have a molecular weight Mw of ≥400 g / mol and ≤2000 g / mol, preferably a molecular weight Mw of ≥450 g / mol and ≤1500 g / mol, further preferably a molecular weight Mw of ≥500 g / mol and ≤1000 g / mol, further preferably a molecular weight Mw of ≥550 g / mol and ≤900 g / mol, further preferably a molecular weight Mw of ≥600 g / mol and ≤800 g / mol.

[0783] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, or a diarylamine moiety, or a triarylamine moiety.

[0784] Preferably, the substantially covalent matrix compound is free of metallic and / or ionic bonds.

[0785] The compound of formula (VIII) or the compound of formula (IX)

[0786] According to another aspect of the present invention, the at least one matrix compound, also referred to as "substantially covalent matrix compound", may comprise at least one arylamine compound, diarylamine compound, triarylamine compound, compound of formula (VIII) or compound of formula (IX):

[0787] (VIII), (IX),

[0788] in:

[0789] T 1 、T 2 、T 3 、T 4 and T 5 Can be independently selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group or a naphthalene group, preferably a single bond or a phenylene group;

[0790] T 6 is a phenyl subunit, a biphenyl subunit, a terphenyl subunit or a naphthalene subunit;

[0791] Ar 1 、Ar 2 、Ar 3 、Ar 4 and Ar 5 may be independently selected from substituted or unsubstituted C6 to C 20 Aryl or substituted or unsubstituted C3 to C 20heteroarylidene, substituted or unsubstituted biphenylidene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted terphenylidene, substituted or unsubstituted tetracene, substituted or unsubstituted benzanthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepane, substituted or unsubstituted dibenzo[b,f]azepane, substituted or unsubstituted 9,9'- Spirobi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanthene]; or a substituted or unsubstituted aromatic fused ring system comprising at least three substituted or unsubstituted aromatic rings selected from: a substituted or unsubstituted non-heterocyclic ring, a substituted or unsubstituted hetero 5-membered ring, a substituted or unsubstituted 6-membered ring and / or a substituted or unsubstituted 7-membered ring, a substituted or unsubstituted fluorene; or a fused ring system comprising 2 to 6 substituted or unsubstituted 5- to 7-membered rings, wherein the rings are selected from: (i) a heterocyclic unsaturated 5- to 7-membered ring, (ii) an aromatic heterocyclic 5- to 6-membered ring, (iii) a non-heterocyclic unsaturated 5- to 7-membered ring, (iv) an aromatic non-heterocyclic 6-membered ring;

[0792] Among them, Ar 1 、Ar 2 、Ar 3 、Ar 4 and Ar 5 The substituents may be selected from the group consisting of: H, D, F, C(-O)R 2 、CN、Si(R 2 )3、P(-O)(R 2 )2、OR 2 、S(-O)R 2 、S(-O)2R 2 , substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched-chain alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms, and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 heteroaryl, a fused ring system comprising 2 to 6 unsubstituted 5- to 7-membered rings, wherein the rings may be selected from: heterocyclic unsaturated 5- to 7-membered rings, aromatic heterocyclic 5- to 6-membered rings, non-heterocyclic unsaturated 5- to 7-membered rings, and aromatic non-heterocyclic 6-membered rings,

[0793] where R 2 The alkyl radical may be selected from H, D, a linear alkyl radical having 1 to 6 carbon atoms, a branched alkyl radical having 1 to 6 carbon atoms, a cyclic alkyl radical having 3 to 6 carbon atoms, an alkenyl or alkynyl radical having 2 to 6 carbon atoms, a C6 to C 18 Aryl or C3 to C 18 Heteroaryl.

[0794] According to one embodiment, wherein T 1 、T 2 、T 3 、T 4 and T 5 Can be independently selected from a single bond, a phenylene group, a biphenylene group or a terphenylene group. According to one embodiment, wherein T 1 、T 2 、T 3 、T 4 and T 5 may be independently selected from a phenylene group, a biphenylene group or a terphenylene group, and T 1 、T 2 、T 3 、T 4 and T 5 is a single bond. According to one embodiment, wherein T 1 、T 2 、T 3 、T 4 and T 5 may be independently selected from a phenylene group or a biphenylene group, and T 1 、T 2 、T 3 、T 4 and T 5 is a single bond. According to one embodiment, wherein T 1 、T 2 、T 3 、T 4 and T 5 may be independently selected from a phenylene group or a biphenylene group, and T 1 、T 2 、T 3 、T 4 and T 5 Two of them are single bonds.

[0795] According to one embodiment, wherein T 1 、T 2 and T 3 may be independently selected from phenylene groups, and T 1 、T 2 and T 3 is a single bond. According to one embodiment, wherein T 1, T 2 and T 3 may be independently selected from phenylene, and T 1 , T 2 and T 3 two of which are single bonds.

[0796] According to one embodiment, wherein T 6 may be phenylene, biphenylene, terphenylene. According to one embodiment, wherein T 6 may be phenylene. According to one embodiment, wherein T 6 may be biphenylene. According to one embodiment, wherein T 6 may be terphenylene.

[0797] According to one embodiment, wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 may be independently selected from K1 to K16:

[0798] (K1), (K2), (K3), (K4),

[0799] (K5), (K6), (K7), (K8),

[0800] (K9), (K10), (K11),

[0801] (K12), (K13), (K14),

[0802] (K15), (K16), wherein

[0803] The asterisk “*” indicates the binding position.

[0804] According to one embodiment, wherein Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 may be independently selected from K1 to K15; or from K1 to K10 and K13 to K15.

[0805] According to one embodiment, wherein Ar 1 、Ar 2 、Ar 3 、Ar 4 and Ar 5 Can be independently selected from K1, K2, K5, K7, K9, K10, K13 to K16.

[0806] When Ar 1 、Ar 2 、Ar 3 、Ar 4 and Ar 5 When selectable within this range, the standard starting temperature can be in a range particularly suitable for mass production.

[0807] The “host compound of formula (VIII) or formula (IX)” may also be referred to as a “hole-transporting compound”.

[0808] According to one embodiment, the substantially covalent matrix compound comprises at least one naphthyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group and / or substituted fluorenyl group, wherein the substituents may be independently selected from methyl, phenyl or fluorenyl groups.

[0809] According to one embodiment of the electronic device, the host compound of formula (VIII) or formula (IX) can be selected from L1 to L21:

[0810] (L1), (L2),

[0811] (L3), (L4),

[0812] (L5), (L6),

[0813] (L7), (L8),

[0814] (L9), (L10),

[0815] (L11), (L12),

[0816] (L13), (L14),

[0817] (L15), (L16),

[0818] (L17), (L18), (L19), (L20),

[0819] (L21).

[0820] Other layers

[0821] According to the present invention, the organic electronic device may further comprise other layers in addition to the layers mentioned above. Exemplary embodiments of the various layers are described below:

[0822] base

[0823] 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 a transparent or opaque material, such as a glass substrate, a plastic substrate, a metal substrate, a silicon substrate, or a backplane.

[0824] Anode layer

[0825] The anode layer can be formed by depositing or sputtering the material for forming the anode layer. The material for forming the anode layer 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 layer can also be formed using a metal, which is typically silver (Ag), gold (Au) or a metal alloy.

[0826] According to one embodiment of the present invention, the anode layer comprises a first anode sublayer and a second anode sublayer, wherein

[0827] - the first anode sublayer comprises a first metal having a work function in the range of ≥ 4 eV and ≤ 6 eV, and

[0828] - the second anode sublayer comprises a transparent conductive oxide; and

[0829] - The second anode sublayer is arranged closer to the hole injection layer.

[0830] According to one embodiment of the present invention, the first metal of the first anode sublayer may be selected from Ag, Mg, Al, Cr, Pt, Au, Pd, Ni, Nd, Ir, preferably Ag, Au or Al, and more preferably Ag.

[0831] According to one embodiment of the present invention, the first anode sublayer has a thickness in the range of 5 nm to 200 nm, or 8 nm to 180 nm, or 8 nm to 150 nm, or 100 nm to 150 nm.

[0832] According to one embodiment of the present invention, the first anode sublayer is formed by depositing the first metal via vacuum thermal evaporation.

[0833] It should be understood that the first anode layer is not part of the substrate.

[0834] According to one embodiment of the present invention, the transparent conductive oxide of the second anode sublayer is selected from indium tin oxide or indium zinc oxide, more preferably indium tin oxide.

[0835] According to one embodiment of the present invention, the second anode sublayer may have a thickness in the range of 3 nm to 200 nm, or 3 nm to 180 nm, or 3 nm to 150 nm, or 3 nm to 20 nm.

[0836] According to one embodiment of the present invention, the second anode sublayer may be formed by sputtering of a transparent conductive oxide.

[0837] According to one embodiment of the present invention, the anode layer of the organic electronic device further comprises a third anode sublayer comprising a transparent conductive oxide, wherein the third anode sublayer is arranged between the substrate and the first anode sublayer.

[0838] According to one embodiment of the present invention, the third anodic sublayer comprises a transparent oxide, preferably selected from indium tin oxide or indium zinc oxide, more preferably indium tin oxide.

[0839] According to one embodiment of the present invention, the third anode sublayer may have a thickness in the range of 3 nm to 200 nm, or 3 nm to 180 nm, or 3 nm to 150 nm, or 3 nm to 20 nm.

[0840] According to one embodiment of the present invention, the third anode sublayer may be formed by sputtering of a transparent conductive oxide.

[0841] It should be understood that the third anode layer is not part of the substrate.

[0842] According to one embodiment of the present invention, the anode layer comprises: a first anode sublayer comprising Ag, a second anode sublayer comprising a conductive metal oxide, preferably ITO, and a third anode sublayer comprising a conductive metal oxide, preferably ITO; wherein the first anode sublayer is arranged between the second and third anode sublayers.

[0843] hole transport layer

[0844] According to one embodiment of the present invention, the organic electronic device comprises a hole transport layer, wherein the hole transport layer is arranged between the hole injection layer and the at least one first light emitting layer.

[0845] A hole transport layer (HTL) can be formed on the HIL by vacuum deposition, spin coating, slot die coating, printing, casting, Langmuir-Blodgett (LB) deposition, or the like. When the HTL is formed by vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for forming the HIL. However, the vacuum or solution deposition conditions may vary depending on the compound used to form the HTL.

[0846] The HTL can be formed from any compound commonly used to form an HTL. Suitable compounds are disclosed, for example, in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953−1010, and are incorporated herein by reference. Examples of compounds that can be used to form the HTL include 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 compounds such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA). Among these compounds, TCTA can transport holes and inhibit the diffusion of excitons into the EML.

[0847] According to one embodiment of the present invention, the hole transport layer may comprise a substantially covalent host compound as described above.

[0848] According to one embodiment of the present invention, the hole transport layer may comprise a compound of formula (VIII) or (IX) as described above.

[0849] According to one embodiment of the present invention, the hole injection layer and the hole transport layer comprise the same substantially covalent matrix compound as described above.

[0850] According to one embodiment of the present invention, the hole injection layer and the hole transport layer comprise the same compound of formula (VIII) or (IX) as described above.

[0851] 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 110 nm to about 140 nm.

[0852] When the thickness of the HTL is within this range, the HTL may have excellent hole transport characteristics without substantial deterioration in driving voltage.

[0853] electron blocking layer

[0854] 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, thereby confining the electrons to the light-emitting layer. This can improve efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer comprises a triarylamine compound. The LUMO energy level of the triarylamine compound can be closer to the vacuum energy level than the LUMO energy level of the hole transport layer. Compared to the HOMO energy level of the hole transport layer, the electron blocking layer can have a HOMO energy level that is further away from the vacuum energy level. The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0855] If the electron blocking layer has a high triplet energy level, it may also be described as a triplet control layer.

[0856] If a phosphorescent green or blue emitting layer is used, the function of the triplet control layer is to reduce triplet quenching. This allows for a higher luminous efficiency from the phosphorescent emitting layer. The triplet control layer is selected from triarylamine compounds having a triplet energy level higher than that 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.

[0857] Photoactive layer (PAL)

[0858] The photoactive layer converts current into photons or photons into current. The photoactive layer (PAL) can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When vacuum deposition or spin coating is used to form the PAL, the deposition and coating conditions can be similar to those for forming the HIL. However, the deposition and coating conditions can vary depending on the compound used to form the PAL. The photoactive layer may not contain the metal complex according to formula (I). The photoactive layer can be an emitting layer (EML) or a light absorbing layer.

[0859] Emitting Layer (EML)

[0860] The EML can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, or the like. When vacuum deposition or spin coating is used to form the EML, the deposition and coating conditions can be similar to those for forming the HIL. However, the deposition and coating conditions may vary depending on the compound used to form the EML.

[0861] According to one embodiment of the present invention, the light-emitting layer does not comprise a compound of formula (I).

[0862] The light-emitting layer (EML) can be formed from a combination of a host and an emitter dopant. Examples of hosts include Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4''-tris(carbazol-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 zinc bis(2-(2-hydroxyphenyl)benzothiazole acid) (Zn(BTZ)2).

[0863] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters emitting 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.

[0864] Examples of red emitter dopants are, but are not limited to, PtOEP, Ir(piq)3, and Btp2Ir(acac). These compounds are phosphorescent emitters, however, fluorescent red emitter dopants may also be used.

[0865] Examples of phosphorescent green emitter dopants are: Ir(ppy)3 (ppy=phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[0866] Examples of phosphorescent blue emitter dopants are: F2Irpic, (F2ppy)2Ir(tmd) and Ir(dfppz)3, and terfluorene. Examples of fluorescent blue emitter dopants are: 4,4'-bis(4-diphenylaminophenyl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe).

[0867] The amount of the luminescent dopant can range from about 0.01 parts by weight to about 50 parts by weight based on 100 parts by weight of the host. Alternatively, the luminescent layer can be composed of a luminescent polymer. The EML can have a thickness of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the EML thickness is within this range, the EML can exhibit excellent luminescence without substantially compromising the driving voltage.

[0868] Hole blocking layer (HBL)

[0869] A hole blocking layer (HBL) can be formed on the EML to prevent holes from diffusing into the ETL by using vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the EML includes a phosphorescent dopant, the HBL can also have a triplet exciton blocking function.

[0870] HBL may also be referred to as auxiliary ETL or a-ETL.

[0871] When vacuum deposition or spin coating is used to form the HBL, the deposition and coating conditions may be similar to those for forming the HIL. However, the deposition and coating conditions may vary depending on the compound used to form the HBL. Any compound commonly used to form the HBL may be used. Examples of the compound used to form the HBL include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and azine derivatives, preferably triazine or pyrimidine derivatives.

[0872] The thickness of the HBL may be in 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.

[0873] Electron Transport Layer (ETL)

[0874] The organic electronic device according to the present invention may further include an electron transport layer (ETL).

[0875] According to another embodiment of the present invention, the electron transport layer may further comprise an azine compound, preferably a triazine compound.

[0876] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organic complexes, preferably LiQ.

[0877] The thickness of the ETL may be within a range of about 15 nm to about 50 nm, for example, about 20 nm to about 40 nm. When the thickness of the ETL is within this range, the ETL may have satisfactory electron injection properties without substantially compromising driving voltage.

[0878] According to another embodiment of the present invention, the organic electronic device may further comprise a hole blocking layer and an electron transport layer, wherein the hole blocking layer and the electron transport layer comprise an azine compound. Preferably, the azine compound is a triazine compound.

[0879] Electron injection layer (EIL)

[0880] An optional EIL, which 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, and Mg, which are 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 used to form the EIL.

[0881] The thickness of the EIL may be within a range of about 0.1 nm to about 10 nm, for example, 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 compromising driving voltage.

[0882] Charge generation layer

[0883] The organic electronic device according to the present invention may further comprise a charge generation layer, wherein the charge generation layer comprises a p-type charge generation layer, wherein the p-type charge generation layer is the organic semiconductor layer according to the present invention, wherein the charge generation layer is arranged between the two photoactive layers.

[0884] The organic electronic device according to the present invention may further include a charge generation layer, wherein the charge generation layer includes a p-type charge generation layer, wherein the p-type charge generation layer is the organic semiconductor layer according to the present invention, wherein the p-type charge generation layer is arranged closer to the cathode layer.

[0885] The organic electronic device according to the present invention may further comprise a charge generation layer, wherein the charge generation layer comprises a p-type charge generation layer, wherein the p-type charge generation layer is the organic semiconductor layer according to the present invention, wherein the charge generation layer is arranged between the two photoactive layers.

[0886] The charge generation layer may further include an n-type charge generation layer, wherein the n-type charge generation layer is arranged between the p-type charge generation layer and the anode layer, and wherein the p-type charge generation layer is arranged closer to the cathode layer than the n-type charge generation layer.

[0887] Preferably, the n-type charge generation layer and the p-type charge generation layer are arranged in direct contact.

[0888] The thickness of the n-type charge generation layer may be in a range of about 0.5 nm to about 15 nm, for example, in a range of about 1 nm to about 10 nm. When the thickness of the n-type charge generation layer is within this range, the EIL may have satisfactory electron injection properties without substantially compromising driving voltage.

[0889] The n-type charge generation layer may include a metal dopant, wherein the metal dopant is selected from an alkali metal, an alkaline earth metal, or a rare earth metal.

[0890] The n-type charge generation layer may include an azine compound. According to a preferred embodiment, the nCGL may include an azine compound and a metal dopant, wherein the metal dopant is selected from an alkali metal, an alkaline earth metal, or a rare earth metal.

[0891] cathode layer

[0892] The cathode layer is formed on the ETL or the optional EIL. The cathode layer can be formed of a metal, an alloy, a conductive compound, or a mixture thereof. The cathode layer can have a low work function. For example, the cathode electrode can 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 can be formed of a transparent conductive oxide such as ITO or IZO.

[0893] The thickness of the cathode layer 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 layer is in the range of about 5 nm to about 50 nm, the cathode layer may be transparent or translucent even if it is formed of a metal or a metal alloy.

[0894] It should be understood that the cathode layer is not part of the electron injection layer or the electron transport layer.

[0895] Organic light-emitting diodes (OLEDs)

[0896] The organic electronic device according to the present invention may be an organic light-emitting device.

[0897] According to one embodiment, the organic light-emitting device comprises a substrate, an anode layer formed on the substrate, a hole injection layer comprising a compound of formula (I), a hole transport layer, a light-emitting layer, an electron transport layer and a cathode layer.

[0898] According to one embodiment, the organic light-emitting device comprises a substrate, an anode layer formed on the substrate, a hole injection layer comprising a compound of formula (I), a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer and a cathode layer.

[0899] According to one embodiment, the organic light-emitting device comprises a substrate, an anode layer formed on the substrate, a hole injection layer comprising a compound of formula (I), a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a cathode layer.

[0900] According to one embodiment, the organic light-emitting device may include a substrate, an anode layer, a hole injection layer, a first hole transport layer, a first electron blocking layer, a first electron blocking layer, a first light-emitting layer, a first electron transport layer, an n-type charge generation layer, a p-type charge generation layer, a second hole transport layer, a second electron blocking layer, a second light-emitting layer, and a cathode layer, wherein an optional hole blocking layer, an optional electron transport layer and / or an optional electron injection layer are arranged between the second light-emitting layer and the cathode layer.

[0901] The organic semiconductor layer according to the present invention may be a first hole injection layer and / or a p-type charge generation layer.

[0902] According to one embodiment, the organic light-emitting device may include the following layer structure: the substrate is arranged adjacent to the anode layer, the anode layer is arranged adjacent to the hole injection layer, the hole injection layer is arranged adjacent to the first hole transport layer, the first hole transport layer is arranged adjacent to the first electron blocking layer, the first electron blocking layer is arranged adjacent to the first light-emitting layer, the first light-emitting layer is arranged adjacent to the first electron transport layer, the first electron transport layer is arranged adjacent to the n-type charge generation layer, the n-type charge generation layer is arranged adjacent to the p-type charge generation layer, the p-type charge generation layer is arranged adjacent to the second hole transport layer, the second hole transport layer is arranged adjacent to the second electron blocking layer, the second electron blocking layer is arranged adjacent to the second light-emitting layer, and a cathode layer, wherein an optional hole blocking layer, an optional electron transport layer and / or an optional electron injection layer are arranged between the second light-emitting layer and the cathode layer.

[0903] The organic semiconductor layer according to the present invention may be a first hole injection layer and / or a p-type charge generation layer.

[0904] Method for manufacturing an organic light-emitting device

[0905] According to one aspect of the present invention, an organic light-emitting diode (OLED) is provided, comprising: a substrate; an anode layer formed on the substrate; a hole injection layer comprising a compound of formula (I), a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode layer.

[0906] According to another aspect of the present invention, an OLED is provided, comprising: a substrate; an anode layer formed on the substrate; a hole injection layer comprising a compound of formula (I), a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and a cathode layer.

[0907] According to another aspect of the present invention, an OLED is provided, comprising: a substrate; an anode layer formed on the substrate; a hole injection layer comprising a compound of formula (I), a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode layer.

[0908] According to various embodiments of the present invention, there may be provided an OLED layer arranged on a substrate or on a top layer, between the above-mentioned layers.

[0909] For example, according to Figure 3 The OLED can be formed by the following method, wherein an anode (120), a hole injection layer (130) containing a compound of formula (I), a hole transport layer (140), an electron blocking layer (145), a light-emitting layer (150), a hole blocking layer (155), an electron transport layer (160), an electron injection layer (180) and a cathode layer (190) are subsequently formed in sequence on a substrate (110).

[0910] According to one aspect, an OLED may comprise the following layer structure: a substrate is arranged adjacent to an anode layer, the anode layer is arranged adjacent to a hole injection layer, the hole injection layer is arranged adjacent to a first hole transport layer, the first hole transport layer is arranged adjacent to a first electron blocking layer, the first electron blocking layer is arranged adjacent to a first light-emitting layer, the first light-emitting layer is arranged adjacent to the first electron transport layer, the first electron transport layer is arranged adjacent to an n-type charge generation layer, the n-type charge generation layer is arranged adjacent to a p-type charge generation layer, the p-type charge generation layer is arranged adjacent to a second hole transport layer, the second hole transport layer is arranged adjacent to a second electron blocking layer, the second electron blocking layer is arranged adjacent to a second light-emitting layer, and an optional electron transport layer and / or an optional injection layer are arranged between the second light-emitting layer and the cathode layer.

[0911] The organic semiconductor layer according to the present invention may be a first hole injection layer and / or a p-type charge generation layer.

[0912] Method for manufacturing organic electronic device

[0913] The organic electronic device according to the present invention may be a light-emitting device or a photovoltaic cell, preferably a light-emitting device.

[0914] According to another aspect of the present invention, there is provided a method for manufacturing an organic electronic device, the method using:

[0915] - at least one deposition source, preferably two deposition sources, more preferably at least three deposition sources.

[0916] Suitable deposition methods include:

[0917] - Deposition via vacuum thermal evaporation;

[0918] - deposition via solution processing, preferably said processing is selected from spin coating, printing, casting; and / or

[0919] - slot-die coating.

[0920] According to various embodiments of the present application, a method is provided, said method using:

[0921] - a first deposition source to release a compound of formula (I) according to the present application, and

[0922] - a second deposition source to release a substantially covalent matrix compound;

[0923] The method comprises a step of forming a hole injection layer; wherein for an organic light emitting diode (OLED):

[0924] - the hole injection layer is formed by releasing a compound of formula (I) according to the present application from the first deposition source and releasing a substantially covalent matrix compound from the second deposition source.

[0925] According to various embodiments of the present application, the method can further comprise forming on the anode layer at least one layer selected from forming a hole transport layer or forming a hole blocking layer, and a light emitting layer between the anode layer and the first electron transport layer.

[0926] According to various embodiments of the present application, the method can further comprise steps for forming an organic light emitting diode (OLED), wherein

[0927] - forming an anode layer on a substrate,

[0928] - forming a hole injection layer comprising a compound of formula (I) on the anode layer,

[0929] - forming a hole transport layer on the hole injection layer comprising a compound of formula (I),

[0930] - forming a light emitting layer on the hole transport layer,

[0931] - forming an electron transport layer on the light emitting layer, optionally forming a hole blocking layer on the light emitting layer,

[0932] - and finally forming a cathode layer,

[0933] - forming an optional hole blocking layer sequentially between the first anode layer and the light emitting layer,

[0934] - forming an optional electron injection layer between the electron transport layer and the cathode layer.

[0935] According to various embodiments, the OLED can have the following layer structure, wherein the layers have the following order:

[0936] an anode layer, a hole injection layer comprising a compound of formula (I) according to the invention, a first hole transport layer, a second hole transport layer, an emitting layer, an optional hole blocking layer, an electron transport layer, an optional electron injection layer and a cathode layer.

[0937] According to another aspect of the present invention, an electronic device is provided, comprising at least one organic light-emitting device according to any embodiment described herein. Preferably, the electronic device comprises an organic light-emitting diode according to one of the embodiments described herein. More preferably, the electronic device is a display device.

[0938] Hereinafter, the embodiments will be illustrated in more detail with reference to the examples. However, the present invention is not limited to the following examples. Reference will now be made in detail to the exemplary aspects. BRIEF DESCRIPTION OF THE DRAWINGS

[0939] The components described above in the described embodiments as well as the components claimed and used according to the invention do not have any special exceptions with regard to their size, shape, material selection and technical concept, so that selection criteria known from the relevant field can be applied without restriction.

[0940] Further details, features, and advantages of the present invention are disclosed in the dependent claims and in the following description of the accompanying drawings, which show, by way of example, preferred embodiments according to the present invention. However, no embodiment necessarily represents the full scope of the invention, and reference is made to the claims and this text for interpretation of the scope of the invention. It should be understood that both the foregoing general description and the following detailed description are merely exemplary and explanatory and are intended to provide further explanation of the invention as claimed.

[0941] Figure 1 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention;

[0942] Figure 2 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention;

[0943] Figure 3 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention;

[0944] Figure 4 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0945] Figure 5 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0946] Figure 6 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0947] Figure 7 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0948] The following will be described in more detail with reference to the accompanying drawings. However, the present invention is not limited to the following drawings.

[0949] Herein, 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 therebetween. When a first element is referred to as being formed or disposed “directly on” or “over” a second element, no other elements are disposed therebetween.

[0950] Figure 1 1 is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment of the present invention. The organic electronic device 100 includes an anode layer 120 and an organic semiconductor layer 131 that may include a compound of formula (I). The organic semiconductor layer 131 is disposed on the anode layer 120. A cathode layer 190 is disposed on the organic semiconductor layer 131.

[0951] Figure 2 1 is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment of the present invention. Organic electronic device 100 includes a substrate 110, an anode layer 120, and a hole injection layer (HIL) 130, which may include a compound of Formula (I). HIL 130 is disposed on anode layer 120. A photoactive layer (PAL) 170 and a cathode layer 190 are disposed on HIL 130.

[0952] Figure 3 1 is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. OLED 100 includes a substrate 110, an anode layer 120, and a hole injection layer (HIL) 130, which may include a compound of Formula (I). HIL 130 is disposed on anode layer 120. A hole transport layer (HTL) 140, an emissive layer (EML) 150, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190 are disposed on HIL 130. Alternatively, a stack of electron transport layers (ETLs) may be used instead of a single electron transport layer 160.

[0953] Figure 4 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. Figure 4 and Figure 3 The difference is that Figure 4The OLED 100 includes an electron blocking layer (EBL) 145 and a hole blocking layer (HBL) 155 .

[0954] refer to Figure 4 OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 which may include a compound of formula (I), a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emissive layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190.

[0955] Figure 5 1 is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment of the present invention. The organic electronic device 100 includes a substrate 110, an anode layer 120 including a first anode sublayer 121, a second anode sublayer 122, and a third anode sublayer 123, and a hole injection layer (HIL) 130. The HIL 130 is disposed on the anode layer 120. A hole transport layer (HTL) 140, a first light emitting layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, and a cathode layer 190 are disposed on the HIL 130. The hole injection layer 130 may include a compound of formula (I).

[0956] Figure 6 1 is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment of the present invention. The organic electronic device 100 includes a substrate 110, an anode layer 120 including a first anode sublayer 121, a second anode sublayer 122, and a third anode sublayer 123, and a hole injection layer (HIL) 130. The HIL 130 is disposed on the anode layer 120. A hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, a first light emitting layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190 are disposed on the HIL 130. The hole injection layer 130 may include a compound of formula (I).

[0957] Figure 71 is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment of the present invention. The organic electronic device 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130, a first hole transport layer (HTL) 140, a first electron blocking layer (EBL1) 145, a first light-emitting layer (EML1) 150, an optional first hole blocking layer (HBL) 155, a first electron transport layer (ETL1) 160, an n-type charge generation layer (n-CGL) 185, a p-type charge generation layer (p-GCL) 135 which may include a compound of formula (I), a second hole transport layer (HTL2) 141, a second electron blocking layer (EBL2) 146, a second light-emitting layer (EML2) 151, an optional second hole blocking layer (HBL2) 156, a second electron transport layer (ETL2) 161, an electron injection layer (EIL) 180, and a cathode layer 190. The HIL may also comprise a compound of formula (I). The hole injection layer may comprise a compound of formula (I). The anode layer may comprise a first anode sublayer, a second anode sublayer, and an optional third anode sublayer.

[0958] Despite Figures 1 to 7 Although not shown in the figure, a capping layer and / or a sealing layer may be further formed on the cathode layer 190 to seal the organic electronic device 100. In addition, various other modifications may be implemented thereto.

[0959] Hereinafter, one or more exemplary embodiments of the present invention are described in detail with reference to the following examples. However, these examples are not intended to limit the purpose and scope of one or more exemplary embodiments of the present invention.

[0960] synthesis

[0961] The present invention is further illustrated by the following examples, which are intended to be illustrative only and not limiting.

[0962]

[0963] Intermediates (2)

[0964] A Schlenk flask equipped with a magnetic stirrer and diiodobenzene (1) was evacuated and filled with an inert gas. Tetrahydrofuran and 2.2 equivalents of trimethylsilyl chloride were added and the reaction mixture was cooled to -78°C. 2.2 equivalents of lithium diisopropylamine were added dropwise over 15 minutes and the solution was stirred at -78°C for 1 hour and then gradually warmed to room temperature. The reaction was quenched with dilute sulfuric acid. The organic layer and the aqueous layer were separated and the aqueous phase was extracted with diethyl ether. The combined organic layers were dried over sodium sulfate and the solvent was evaporated. The crude orange solid was crystallized from dichloromethane / methanol 1:1 to give the pure product.

[0965] Intermediates (4)

[0966] In an apparatus equipped with a magnetic stirrer, intermediate (2), 3 equivalents of pinacol ester, 10 mol % of SPhos and 4 equivalents of potassium phosphate were suspended in a mixture of 10:1 dioxane / water. Before adding 5 mol % of palladium (II) acetate, the mixture was degassed using ultrasound for 15 minutes. After stirring at reflux under an inert gas atmosphere for 45 hours, the mixture was cooled to room temperature and diluted with ethyl acetate and water. After layering, the aqueous phase was extracted with ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered through a pad of diatomaceous earth, and the solvent was evaporated. The crude product was purified by grinding in hexane overnight, filtering and washing with cooled hexane.

[0967] Intermediates (5)

[0968] Intermediate (4) was dissolved in dichloromethane at a ratio of 6 ml / g, 4 equivalents of iodine chloride were added, and the solution was stirred at 35°C for 23 hours. After the reaction was cooled to room temperature and then cooled in a refrigerator, the precipitate was filtered off and washed with cold dichloromethane. The product was used without further purification.

[0969] Intermediates (6)

[0970] A flask equipped with a magnetic stirrer and 4 equivalents of malononitrile was evacuated and filled with inert gas. After the addition of DME, the solution was cooled to 0°C and 6 equivalents of sodium hydride were added over a period of 15 minutes. The mixture was stirred at 0°C and room temperature for 15 minutes each, and intermediate (5) and Pd(PPh3)2Cl2 were added. After stirring under reflux overnight, the mixture was acidified with 1 M hydrochloric acid to precipitate the product. The crude product was filtered, washed with water, dried to constant weight, dissolved in acetone, and filtered through a pad of celite topped with silica gel. After trituration in dichloromethane, the product was cooled in a refrigerator before filtering off the mother liquor. The solid was washed with cold dichloromethane until the filtrate was clear, thereby obtaining the pure product.

[0971] Quinone (7)

[0972] A flask with a magnetic stirrer was charged with intermediate (6), evacuated and flushed with argon. After adding dichloromethane and 1.15 equivalents of PIFA, the flask was covered with aluminum foil and stirred at room temperature for three days. The solution was concentrated and acetic acid was added in a ratio of DCM / HOAc 4:1. After stirring at room temperature for 1 hour and at 10°C for 30 minutes, the product was filtered off and washed with cold dichloromethane to obtain a high-purity final product.

[0973] Calculated HOMO and LUMO

[0974] HOMO and LUMO were calculated using the program packages ORCA V5.0.3 (Max Planck Institute für Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Köln, Germany). The dipole moment, LUMO, and HOMO energy levels of the molecular structure were determined by applying the hybrid functional B3LYP and 6-31G* basis sets from the optimized geometry obtained by applying the functional BP86 and Def2-SVP basis sets in the gas phase. All calculations were performed in the gas phase. If more than one conformation was feasible, the conformation with the lowest total energy was selected. For molecules containing deuterium atoms (D), the mass of this particular atom was assigned to 2.00141 amu (atomic mass units).

[0975] Melting point

[0976] The melting point (Tm) was determined as the peak temperature of the DSC curve according to the above-mentioned TGA-DSC measurement or a separate DSC measurement (Mettler Toledo DSC822e, the sample was heated from room temperature at a heating rate of 10 K / min under a pure nitrogen flow until complete melting. An amount of 4 to 6 mg of sample was placed in a 40 μL Mettler Toledo aluminum pan with a lid and a hole of <1 mm was punched in the lid).

[0977] Glass transition temperature

[0978] The glass transition temperature (Tg) was measured as described in DIN EN ISO 11357, published in March 2010, in a Mettler Toledo DSC 822e differential scanning calorimeter under nitrogen and using a heating rate of 10 K / min.

[0979] Thermogravimetric analysis

[0980] The term "TGA5%" means the temperature at which 5% weight loss occurs during thermogravimetric analysis, measured in °C.

[0981] TGA5% values ​​can be determined by heating 9 mg to 11 mg of sample in an open 100 µL aluminum pan at a heating rate of 10 K / min in a thermogravimetric analyzer under a nitrogen flow of 20 mL / min in the equilibrium zone and 30 mL / min in the oven zone.

[0982] The TGA5% value can provide an indirect measure of a compound's volatility and / or decomposition temperature. In a first approximation, the higher the TGA5% value, the lower the volatility and / or higher the decomposition temperature of the compound.

[0983] According to one embodiment, the TGA5% value of the compound of formula (I) is selected in the range of ≥280°C and ≤420°C; preferably ≥290°C and ≤410°C, further preferably ≥295°C and ≤410°C.

[0984] Standard starting temperature

[0985] Standard starting temperature (T RO ) was determined by loading 100 mg of compound into a VTE source. As a VTE source, a point source of organic material provided by Kurt J. Lesker Company (www.Lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com) was used. -5 A VTE source is heated at a constant rate of 15 K / min under a pressure of 100 mbar, and the temperature inside the source is measured with a thermocouple. Compound evaporation is detected using a QCM detector, which measures compound deposition on the detector's quartz crystal. The deposition rate on the quartz crystal is measured in Ǻ / s. To determine the standard onset temperature, the deposition rate is plotted against the VTE source temperature. The standard onset is the temperature at which significant deposition occurs on the QCM detector. To obtain accurate results, the VTE source is heated and cooled three times, and only the results from the second and third runs are used to determine the standard onset temperature.

[0986] To effectively control the evaporation rate of organic compounds, the standard starting temperature may be in the range of 185°C to 280°C. If the standard starting temperature is lower than 185°C, evaporation may be too rapid, making it difficult to control. If the standard starting temperature is higher than 280°C, the evaporation rate may be too slow, which may result in a low cycle time and the organic compounds in the VTE source may decompose due to prolonged exposure to high temperatures.

[0987] The standard onset temperature is an indirect measure of the volatility of a compound. The higher the standard onset temperature, the lower the volatility of the compound.

[0988] dipole moment

[0989] Dipole moment of a molecule containing N atoms It is given by:

[0990]

[0991] in and is the partial charge and position of atom i in the molecule. The dipole moment is obtained from the optimized geometry at the same level of theory. The geometry of the molecular structure was optimized in the gas phase using the hybrid functional B3LYP and 6-31G* basis sets (program packages ORCA V5.0.3 (Max Planck Institute für Kohlenforschung, Kaiser Wilhelm Platz 1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677 Köln, Germany).) If more than one conformation is feasible, the conformation with the lowest total energy is selected to determine the structural and electronic parameters of the molecule.

[0992] Measurement of UV-Vis Absorption in Solutions

[0993] Experimental absorption spectra were recorded on a Thermo Fisher Evolution Pro UV-Vis spectrophotometer. For sample preparation, the material was weighed into an aluminum crucible and then placed in a 25 mL volumetric flask. The mass change readability of the associated microbalance was within the 1–2 µg range. The volumetric flask was then filled to the mark with dichloromethane (spectroscopic grade, with a transmittance of ≥90% at λ ≥ 248 nm according to the manufacturer's instructions) and shaken until the material was completely dissolved, resulting in a concentration of 10 -4 mol / L~10 -5 mol / L solution. For the measurement, the solution was placed in a standard cuvette (Hellma 110-QS: quartz, d = 10 mm, with a PTFE stopper). Spectra were recorded at an ambient temperature of 20°C with a slit width of 1 nm and a sampling interval of 1 nm. The background absorption of the pure solvent, measured immediately before the measurement using the same measurement conditions, was subtracted from all spectra.

[0994] Measurement of light absorbance of organic semiconductor layers

[0995] A 35 nm thick mixed film of N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluoren]-2-amine and a p-type dopant was deposited on a quartz substrate (EN08, ≥99.98% SiO2, GVB GmbH) by thermal evaporation according to Table 2 in a vacuum system (Cluster Tool, Sunic System Ltd.) at a deposition rate of 1 Å / s and a pressure of approximately 3e-7 mbar. The sample was stored in a glove box under a pure nitrogen atmosphere until measurement (maximum 1 hour of air exposure). Reflectance and transmittance were measured in the spectral range from 380 nm to 1050 nm using a Filmetrics F10-RT spectrometer. A blank quartz substrate was used as a reflectance standard. Absorbance was automatically calculated by subtracting the reflectance and transmittance values ​​from 100%.

[0996] Calculated absorption area or maximum absorption

[0997] All calculations were performed using the program packages ORCA version 5.0.4 (Department of theory and spectroscopy, Max Planck Institute for Kohlenforschung Kaiser Wilhelm Platz 1, 45470 Muelheim / Ruhr, Germany) and WEASEL 1.11.0 (FAccTs GmbH, Rolandstrasse 67, 50677 Köln, Germany). The LUMO and HOMO energy levels of the molecular structure were determined using the hybrid functional B3LYP and 6-31G* basis sets from the optimized geometry obtained by applying the functional BP86 and the Def2-SVP basis set in the gas phase. TD-DFT calculations were performed using the hybrid functional PBE0 and the def2-SVP basis set in the gas phase, including the first 30 singlet transitions. The calculated singlet transitions were used to calculate the absorption spectrum by applying a Gaussian fit (λ = 215 nm to 850 nm), where transitions below 350 nm were excluded.

[0998] To calculate the overall absorption in the relevant wavelength region (λ = 400 nm to 650 nm, blue and green emission), the integral below the calculated UV TDDFT spectrum was determined.

[0999] Experimental data

[1000] HV-TGA 5% mass loss temperature

[1001] 10 mg of compound was placed in a 2 cm AhO3 crucible and installed in a high vacuum thermogravimetric analysis (HV-TGA) apparatus. The HV-TGA apparatus consisted of an evaporation source (Creaphys DE-2-CF40), a thermocouple (ThermoSensor GmbH NiCr-Ni, Type K) placed inside the crucible, and a quartz crystal microbalance (QCM, Inficon 750-1000-G10, 6 MHz). The HV-TGA apparatus was part of a vacuum chamber system equipped with a vortex pump, a turbomolecular pump, a nitrogen inlet with a mass flow controller, and a progressive valve between the vortex pump and the turbomolecular pump. The combination of the nitrogen inlet and the pump valve allowed pressures from 1e2 mbar to 1e-6 mbar, while the standard operating pressure was 1e-4 mbar with a stability of + / -10%. After reaching the desired pressure, the evaporation source temperature was increased from room temperature to 600°C at a rate of 10°C / minute. The compound was completely evaporated and detected by QCM. The frequency shift of the QCM during the entire heating period corresponds to 100% mass loss.

[1002] The reference temperature of the dopant material was taken at 5% mass loss, as the obtained value most closely matches the processing temperature of the linear evaporation source in mass production.

[1003] Table 1

[1004] Reference temperature of the dopant material according to Formula I

[1005]

[1006] It is apparent from Table 1 that the compounds of the present invention exhibit higher HV-TGA5% values ​​and therefore evaporate at higher temperatures. Therefore, the high HV-TGA5% of the compounds of the present invention can be beneficial in minimizing or avoiding tool contamination during, for example, organic electroluminescent device manufacturing.

[1007] Table 2

[1008]

[1009]

[1010]

[1011]

[1012]

[1013]

[1014]

[1015]

[1016]

[1017]

[1018] Table 2 shows the LUMO energy level, HOMO energy level, dipole moment, and energy gap (energy gap) between the LUMO energy level and the HOMO energy level of the comparative compound and the compound of the present invention.

[1019] Table 2b: Absorption properties of comparative compounds and compounds of the present invention

[1020]

[1021]

[1022]

[1023] Compared with the comparative compound C1, the compound of the present invention has lower λabs(max) in the wavelength region of 300 nm to 650 nm.

[1024] Lower wavelengths in the 300 nm to 650 nm wavelength region can result in reduced external quantum efficiency, current density, and luminous flux.

[1025] Compared with the comparative compound C1, the compound of the present invention exhibits a lower absorption area in the range of 400 nm to 650 nm.

[1026] Low absorption can lead to reduced external quantum efficiency, current density, and luminous flux.

[1027] Therefore, the compound can be advantageous in providing an organic electronic device or display apparatus having improved display brightness, or can increase the lifespan of the display when a lower current density is used.

[1028] Furthermore, high efficiency, such as current efficiency and external quantum efficiency, can be beneficial for reducing power consumption and improving battery life, particularly in mobile devices.

[1029] General steps used to manufacture OLEDs

[1030] Preparation of OLED devices containing a hole injection layer comprising compounds of the present invention

[1031] For the examples and comparative examples according to the present invention listed in Table IX, glass substrates 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 were cut into a size of 100 mm × 100 mm × 0.7 mm, ultrasonically cleaned with water for 60 minutes, and then ultrasonically cleaned with isopropyl alcohol for 20 minutes. The liquid film was removed under a nitrogen stream, and then plasma treatment was performed, as shown in Table 2, to prepare the anode layer. The plasma treatment was performed in an atmosphere comprising 97.6% by volume nitrogen and 2.4% by volume oxygen.

[1032] Then, N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (N-5) as a hole transport host compound and 2 wt % of the present invention compound or comparative compound of Table 2 as a dopant were vacuum deposited to form a hole injection layer (HIL) having a thickness of 10 nm according to Table 4.

[1033] Then, N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine (N-5) was vacuum-deposited to form a hole transport layer (HTL) having a thickness of 128 nm.

[1034] Then, N,N-di([1,1′-biphenyl]-4-yl)-3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-amine (N-3) was vacuum deposited on the HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[1035] Then, an emitting layer (EML) with a thickness of 19 nm was formed on the EBL by co-depositing 99 vol% of dibenzofuran, 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthryl] [2457172-82-4] as the EML host and 1 vol% of 5H,9H-[1]benzothieno[2′,3′:5,6][1,4]azaborinano[2,3,4-kl]azaboranthracene, 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl] [2482607-57-6] as a blue dopant.

[1036] Then, a hole blocking layer with a thickness of 5 nm was formed on the EML by depositing a compound 4-([1,1′-biphenyl]-4-yl)-6-(3′-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1′-biphenyl]-4-yl)-2-phenylpyrimidine (N-14).

[1037] Then, an electron transport layer with a thickness of 31 nm was formed on the HBL by co-depositing compound 6,6′-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine) (N-15) and LiQ in a ratio of 50:50 wt %.

[1038] Then, at 10 -7 Yb was evaporated at a rate of 0.01 Å / s to 1 Å / s under a pressure of 100 mbar to form an electron injection layer (EIL) with a thickness of 1.3 nm on the electron transport layer.

[1039] In 10 -7 Ag / Mg (1.8 wt%) was evaporated at a rate of 0.01 Å / s to 1 Å / s at 100 mbar to form a cathode with a thickness of 13 nm.

[1040] 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.

[1041] Table 3

[1042] Compounds used

[1043]

[1044]

[1045] Preparation of OLED devices containing a p-type charge generation layer comprising the compounds of the present invention

[1046] For the examples and comparative examples according to the present invention listed in Table IX, glass substrates 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 were cut into a size of 100 mm × 100 mm × 0.7 mm, ultrasonically cleaned with water for 60 minutes, and then ultrasonically cleaned with isopropyl alcohol for 20 minutes. The liquid film was removed in a nitrogen stream, and then plasma treatment was performed, as shown in Table 4, to prepare the anode layer. The plasma treatment was performed in an atmosphere comprising 97.6% by volume nitrogen and 2.4% by volume oxygen.

[1047] Then, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (N-1) as a first hole transport host compound and 2 wt% of 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenetris(cyanomethylidene))tris(2,3,5,6-tetrafluorobenzonitrile) (N-2) were vacuum deposited to form a hole injection layer (pHIL) with a thickness of 10 nm.

[1048] Then, N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine (N-1) was vacuum deposited to form a first hole transport layer having a thickness of 29 nm.

[1049] Then, N,N-di([1,1′-biphenyl]-4-yl)-3′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-amine (N-3) was vacuum deposited on the HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[1050] Then, a first light-emitting layer (EML1) with a thickness of 19 nm was formed on the EBL1 by co-depositing 99 vol% of dibenzofuran, 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthryl] [2457172-82-4] as an EML host and 1 vol% of 5H,9H-[1]benzothieno[2′,3′:5,6][1,4]azaborinano[2,3,4-kl]azaboranthracene, 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl] [2482607-57-6] as a blue dopant.

[1051] Then, a first electron transporting layer (ETL1) having a thickness of 7.5 nm was formed on the first light emitting layer by depositing 2,2′-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline](N-4) according to Table 4.

[1052] Then, a first n-type charge generation layer (n-CGL1) with a thickness of 10 nm was formed on the first electron transport layer (ETL1) by co-depositing 98 vol% of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline(N-4)] and 2 vol% of Yb.

[1053] Then, a first p-type charge generation layer (p-CGL) having a thickness of 10 nm was formed on the first n-type CGL by co-depositing 90 vol% of N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (N-5) and 10 vol% of the present invention compound or comparative compound according to Table 2 as a dopant.

[1054] Then, a second hole transport layer with a thickness of 43 nm was formed on the first p-type CGL by depositing N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine (N-5).

[1055] Then, a second electron blocking layer with a thickness of 5 nm was formed on the second hole transport layer by depositing N,N-di([1,1'-biphenyl]-4-yl)-3'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine (N-3).

[1056] Then, a second light-emitting layer (EML2) with a thickness of 19 nm was formed on the EBL1 by co-depositing 99 vol% of dibenzofuran, 7-(phenyl-2,3,4,5,6-d)-1-[10-(phenyl-2,3,4,5,6-d)-9-anthryl] [2457172-82-4] as the EML host and 1 vol% of 5H,9H-[1]benzothieno[2′,3′:5,6][1,4]azaborinano[2,3,4-kl]azaboranthracene, 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl] [2482607-57-6] as a blue dopant.

[1057] Then, a first hole blocking layer (HBL1) with a thickness of 5 nm was formed on the EML2 by depositing a compound 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluoren-4-yl)-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine (N-14).

[1058] Then, a second electron transport layer (ETL2) with a thickness of 31 nm was formed on the HBL by co-depositing compound 6,6′-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine) (N-15) and LiQ in a ratio of 50:50 wt %.

[1059] Then, at 10 -7 Yb was evaporated at a rate of 0.01 Å / s to 1 Å / s under a pressure of 100 mbar to form an electron injection layer (EIL) with a thickness of 2 nm on the electron transport layer.

[1060] In 10 -7 Ag / Mg (1.8 wt%) was evaporated at a rate of 0.01 Å / s to 1 Å / s at 100 mbar to form a cathode with a thickness of 13 nm.

[1061] 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.

[1062] In order to evaluate the performance of the invention examples relative to the prior art, the current efficiency was measured at 20°C. The current-voltage characteristics were determined using a Keithley 2635 source measurement unit by providing a voltage in V and measuring the current in mA flowing through the device under test. The voltage applied to the device varied in steps of 0.1 V over a range of 0 V to 10 V. Similarly, the luminance-voltage characteristics and CIE coordinates were measured in cd / m² at each voltage value using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungs stelle (DAkkS)). 2 The luminance at 15 mA / cm is determined by interpolating the luminance-voltage and current-voltage characteristics respectively. 2 cd / A efficiency under .

[1063] In bottom-emitting devices, the emission is primarily Lambertian and is quantified as a percentage of the external quantum efficiency (EQE). To determine the efficiency EQE (in %), a calibrated photodiode was used at 15 mA / cm 2 The light output of the device was measured.

[1064] In top-emitting devices, the emission is forward-oriented, non-Lambertian, and also highly dependent on the microcavity. Therefore, the efficiency (EQE) will be higher compared to bottom-emitting devices. To determine the efficiency (EQE) in %, a calibrated photodiode was used at 15 mA / cm 2 The light output of the device was measured.

[1065] The device lifetime LT was measured using a Keithley 2400 source meter at ambient conditions (20°C) and 10 mA / cm 2 or 30 mA / cm 2 Measure and record in hours.

[1066] The device's luminance is measured using a calibrated photodiode. The lifetime (LT) is defined as the time until the device's luminance drops to 97% of its initial value.

[1067] The increase in operating voltage, ∆U, is used as a measure of the operating voltage stability of the device. During the LT measurement, this increase is determined by subtracting the operating voltage after 100 hours from the operating voltage after 1 hour of device operation.

[1068] ∆U=[U(100h) - U(1h)].

[1069] The smaller the ΔU value is, the better the operating voltage stability is.

[1070] Technical effects of the present invention

[1071] Table 4

[1072]

[1073] Compared to the comparative OLED (Comparative Example 1), the OLED according to the example of the invention (Inventive Example 1) comprising the compound of the invention exhibits a lower operating voltage.

[1074] Lower operating voltages can be important for battery life of organic electronic devices, especially mobile devices.

[1075] Compared to the comparative OLED (Comparative Example 1), the OLED according to the example of the present invention (Inventive Example 1) comprising the compound of the present invention exhibited higher current efficiency and external quantum efficiency.

[1076] High efficiency, such as external quantum efficiency and current efficiency, can be beneficial for reducing power consumption and improving battery life, especially in mobile devices.

[1077] Compared to the comparative OLED (Comparative Example 1), the OLED according to the example of the invention (Inventive Example 1) comprising the compound of the invention exhibits a lower rise in the operating voltage over time.

[1078] A lower voltage rise over time may result in improved long-term stability of the electronic device.

[1079] Compared to the comparative OLED (Comparative Example 1), the OLED according to the example of the invention (Inventive Example 1) comprising the compound of the invention exhibits a higher lifetime.

[1080] The long lifetime may lead to improved long-term stability of electronic devices.

[1081] Table 5

[1082]

[1083] Compared to the comparative OLED (Comparative Example 2), the OLED according to the example of the invention (Inventive Example 2) comprising the compound of the invention exhibits a lower operating voltage.

[1084] Lower operating voltages can be important for battery life of organic electronic devices, especially mobile devices.

[1085] Compared to the comparative OLED (Comparative Example 2), the OLED according to the example of the present invention (Inventive Example 2) comprising the compound of the present invention exhibited higher current efficiency and external quantum efficiency.

[1086] High efficiency, such as external quantum efficiency and current efficiency, can be beneficial for reducing power consumption and improving battery life, especially in mobile devices.

[1087] Compared to the comparative OLED (Comparative Example 2), the OLED according to the example of the invention (Inventive Example 2) comprising the compound of the invention exhibits a lower rise in the operating voltage over time.

[1088] A lower voltage rise over time may result in improved long-term stability of the electronic device.

[1089] Compared to the comparative OLED (Comparative Example 2), the OLED according to the example of the invention (Inventive Example 2) comprising the compound of the invention exhibits a higher lifetime.

[1090] The long lifetime may lead to improved long-term stability of electronic devices.

[1091] The specific combination of elements and features in the above detailed embodiments is exemplary only; the exchange and substitution of these teachings with other teachings in this and the patent applications incorporated by reference is also expressly contemplated. As will be appreciated by those skilled in the art, variations, variants and other embodiments described herein can be envisaged by those skilled in the art without departing from the spirit and scope of the invention as claimed. Therefore, the above description is intended to be an example only and is not intended to be limiting. In the claims, the word "comprising" does not exclude other elements or steps, and the singular form "a" or "an" does not exclude plural indicators. The fact that particular measures are listed in mutually different dependent claims does not mean that a combination of these measures has not been advantageously selected for use. The scope of the invention is defined by the claims and their equivalents. In addition, the figure marks used in the specification and claims are not used to limit the scope of the invention as claimed.

Claims

1. A compound of formula (I): (I)， in HetAr is selected from formula (II): (II), A 1 Selected from formula (III): (III), A 2 Selected from formula (IV) (IV), The asterisk "*" indicates the binding position. R 1 and R 2 independently selected from CN, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, SF5, where R 1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN or SF5; R 3 and R 4 Independently selected from H, D, halogen, F, CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, SF5 or CF3; R 5 independently selected from H, D, halogen, F, CN, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 Heteroaryl, SF5, where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, SF5; X a1 Select N or CR a4 ; R a1 、R a2 、R a3 and R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN, SF5, where R a1 、R a2 、R a3 and R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, SF5; where R a1 、R a2 、R a3 and R a4 At least one of them is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN or SF5.

2. The compound of formula (I) according to claim 1, wherein R 1 and R 2 independently selected from CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C3 to C9 heteroaryl; preferably R 1 and R 2 are independently selected from CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C3 to C5 heteroaryl; and further preferably R 1 and R 2 Independently selected from CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C4 to C5 heteroaryl.

3. A compound of formula (I) according to claim 1 or 2, wherein R 1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3 or CN; preferably wherein R 1 and R 2 The one or more substituents are independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3 or CN; further preferably R 1 and R 2 The one or more substituents are independently selected from D, CF3, and CN.

4. A compound of formula (I) according to any one of claims 1 to 3, wherein A 1 and A 2 Selected from formula (V): (V), where the asterisk "*" indicates the binding position.

5. A compound of formula (I) according to any one of claims 1 to 4, wherein R 3 and R 4 Independently selected from H, D, CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl or CF3, preferably R 3 and R 4 Independently selected from H, D, CN, CF3, and further preferably R 3 and R 4 Independently selected from H, D.

6. A compound of formula (I) according to any one of claims 1 to 5, wherein R 5 is selected from H, D, CN, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C4 to C5 heteroaryl; preferably R 5 is selected from H, D, CN, substituted or unsubstituted C6 aryl or substituted or unsubstituted C4 to C5 heteroaryl; or further preferably R 5 is selected from a substituted or unsubstituted C6 aryl group or a substituted or unsubstituted C4 to C5 heteroaryl group.

7. A compound of formula (I) according to any one of claims 1 to 6, wherein R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, halogen, F or CN; preferably R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3 or CN; and further preferably R 5 The one or more substituents are independently selected from D, CF3 or CN.

8. A compound of formula (I) according to any one of claims 1 to 7, wherein when an aromatic carbon is directly bonded to an sp2 hybridized ring nitrogen atom, a CN group is not bonded to the aromatic carbon atom.

9. A compound of formula (I) according to any one of claims 1 to 8, wherein R 5 Selected from formula (VIa): (VIa), wherein "*" indicates the binding position, and in X b1 Select N or CR b1 , X b2 Select N or CR b2 , X b3 Select N or CR b3 , X b4 Select N or CR b4 , X b5 Select N or CR b5 , R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, halogen, F or CN, where R b1 to R b5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; Preferred R b1 to R b5 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and more preferably R b1 to R b5 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

10. A compound of formula (I) according to any one of claims 1 to 9, wherein when R bn When it is N, the adjacent R bm Not a CN group, wherein n=1 to 5, wherein m=1 to 5.

11. A compound of formula (I) according to any one of claims 1 to 10, wherein R 5 Selected from formula (VIb): (VIb), wherein "*" indicates the binding position, and in X b4 Select N or CR b4 , R b1 to R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN, where R b1 to R b3 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, Preferred R b1 to R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and more preferably R b1 to R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

12. A compound of formula (I) according to any one of claims 1 to 11, wherein R 5 Selected from formula (VIc): (VIc), where "*" indicates the binding position, and in X b4 Select N or CR b4 , R b1 、R b2 and R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN, where R b1 、R b2 and R b4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, Preferred R b1 、R b2 and R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and more preferably R b1 and R b2 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

13. A compound of formula (I) according to any one of claims 1 to 12, wherein R 5 Selected from formula (VId): (VId), where "*" indicates the binding position, and in X b4 Select N or CR b4 , R b1 and R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN, where R b1 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, Preferred R b1 and R b4 independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and more preferably R b1 and R b4 Independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

14. A compound of formula (I) according to any one of claims 1 to 13, wherein R 5 Selected from formula (VIe): (VIe), wherein "*" indicates the binding position, and in R b1 to R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN, where R b1 to R b4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, Preferred R b1 to R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and more preferably R b1 to R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

15. A compound of formula (I) according to any one of claims 1 to 14, wherein R 5 Selected from formula (VIf): (VIf), where "*" indicates the binding position, and in R b1 、R b2 and R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN, where R b1 、R b2 and R b4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, Preferred R b1 、R b2 and R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and more preferably R b1 to R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

16. A compound of formula (I) according to any one of claims 1 to 15, wherein R 5 Selected from formula (VIg): (VIg), where "*" indicates the binding position, and in R b1 and R b4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 Heteroaryl, halogen, F, CN, where R b1 and R b4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN, Preferred R b1 and R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and more preferably R b1 and R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

17. A compound of formula (I) according to any one of claims 1 to 16, wherein R a1 to R a4 , R in formula (VIa) b1 to R b5 , R in formula (VIb) b1 to R b3 , R in formula (VIc) b1 to R b2 , R in formula (VId) b1 , R in formula (Vie) b1 to R b4 , R in formula (VIf) b1 、R b2 and R b4 , R in formula (VIg) b1 and R b4 , do not select halogen or F; and preferably R in formula I a1 to R a4 , R in formula (VIa) b1 to R b5 , R in formula (VIb) b1 to R b3 , R in formula (VIc) b1 to R b2 , R in formula (VId) b1 , R in formula (Vie) b1 to R b4 , R in formula (VIf) b1 、R b2 and R b4 , R in formula (VIg) b1 and R b4 , do not select halogen or F, and R a1 to R a4 、R b1 to R b5 The one or more substituents on are not selected from halogen or F.

18. A compound of formula (I) according to any one of claims 1 to 17, wherein: R in formula (II) a2 to R a3 , R in formula (VIa), (VIb), (VIe) b2 to R b3 , and R in formula (VIc) and (VIf) b2 , do not select CN.

19. A compound of formula (I) according to any one of claims 1 to 18, wherein R 5 Selected from the group represented by B1 to B163: Where "*" indicates the binding position.

20. A compound of formula (I) according to any one of claims 1 to 19, wherein formula (II) is selected from formula (IIa), (IIb), (IIc), (IId), (IIe) and (IIf): , where "*" indicates the binding position, And preferably, formula (IIa), (IIb), (IIc), (IId), (IIe) and (IIf) are partially deuterated or fully deuterated, and further preferably, formula (IIf) is partially deuterated or fully deuterated.

21. A compound of formula (I) according to any one of claims 1 to 20, wherein HetAr is selected from the group represented by C1 to C112: Where "*" indicates the binding position.

22. A compound of formula (I) according to any one of claims 1 to 21, wherein the compound of formula (I) is selected from compounds of formula (VII): (VII), in HetAr is selected from the group consisting of formula (II), (IIa), (IIb), (IIc), (IId), (IIe) and (IIf): Wherein the asterisk "*" indicates the binding position, and in R 3 and R 4 Selected from H, D; X a1 Select N or CR a4 ; R a1 to R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, halogen, F or CN, where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN; R a1 to R a4 At least one of which is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3 or CN; R 5 selected from H, D, CN, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl or substituted or unsubstituted C2 to C 30 heteroaryl, where R 5 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3 or CN.

23. A compound of formula (I) according to any one of claims 1 to 22, wherein the compound of formula (I) is selected from compounds of formula (VII): (VII), in HetAr is selected from the group consisting of formula (II), (IIa), (IIb), (IIc), (IId), (IIe) and (IIf): Wherein the asterisk "*" indicates the binding position, and in R 3 and R 4 Selected from H, D; X a1 Select N or CR a4 ; R a1 to R a4 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl, halogen, F or CN, where R a1 to R a4 The one or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN; R a1 to R a4 At least one of which is selected from partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3 or CN; R 5 Selected from formula (VIa) (VIa) in X b1 Select N or CR b1 , X b2 Select N or CR b2 , X b3 Select N or CR b3 , X b4 Select N or CR b4 , X b5 Select N or CR b5 , R b1 to R b5 independently selected from H, D, substituted or unsubstituted C1 to C8 alkyl, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, substituted or unsubstituted C6 to C 30 Aryl, substituted or unsubstituted C2 to C 30 heteroaryl or CN, where R b1 to R b5 The one or more substituents on are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3 or CN, And the asterisk "*" indicates the binding position.

24. The compound of formula (I) according to any one of the preceding claims 1 to 23, wherein the compound of formula (I) is selected from the group consisting of compounds represented by I-1 to I-53:

25. An organic semiconductor layer, wherein the organic semiconductor layer comprises a compound of formula (I) according to claims 1 to 24, and preferably comprises a compound of formula (VII).

26. The organic semiconductor layer according to claim 25, wherein the organic semiconductor layer comprises a compound of formula (I), preferably a compound of formula (VII), and a hole-transporting matrix compound. 27 . The organic semiconductor layer according to claim 25 , wherein the organic semiconductor layer is a hole injection layer or a p-type charge generation layer.

28. An organic electronic device, wherein the organic electronic device comprises the organic semiconductor layer according to claims 25 to 27.

29. An organic electronic device according to claim 28, wherein the organic electronic device comprises an anode layer, a cathode layer, a first photoactive layer, a second photoactive layer, a hole injection layer, and a p-type charge generation layer, wherein the hole injection layer is arranged in direct contact with the anode layer, and wherein the p-type charge generation layer is arranged between the first photoactive layer and the second photoactive layer, wherein the hole injection layer is closer to the anode layer than the p-type charge generation layer, wherein the hole injection layer or the p-type charge generation layer is an organic semiconductor layer according to claims 25 to 27, wherein the first photoactive layer, the second photoactive layer, the hole injection layer, and the p-type charge generation layer are arranged between the anode layer and the cathode layer. 30 . A display device comprising the organic electronic device according to claim 28 or 29 .

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