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

Abstract

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

Description

Technical Field

[0001] The present invention relates to a compound of formula (I) and its use 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 Technology

[0002] Organic electronic devices, such as organic light-emitting diodes (OLEDs), are self-emissive, possessing wide viewing angles, excellent contrast ratios, rapid response times, high brightness, superior operating voltage characteristics, and excellent color reproduction. A typical OLED comprises 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. In this regard, the HTL, EML, and ETL are thin films formed from organic compounds.

[0003] When a voltage is applied to the anode and cathode, holes injected from the anode move to the EML via the HTL, while electrons injected from the cathode move to the EML via the ETL. Holes and electrons recombine in the EML to generate excitons. Light emission occurs when the excitons transition from the excited state to the ground state. The injection and flow of holes and electrons should be balanced to ensure that OLEDs with this structure exhibit excellent efficiency and / or long lifetime.

[0004] The performance of organic light-emitting diodes can be affected by the characteristics of the semiconductor layer, and in this regard, by the characteristics of the metal complexes also contained in the semiconductor layer.

[0005] There remains a need to improve the performance of organic semiconductor materials, semiconductor layers, and their organic electronic devices, particularly by improving the properties of the compounds contained therein to achieve improved operating voltage, improved efficiency, improved lifetime, and / or improved voltage stability over time. Furthermore, there remains a need to improve the LUMO level, improve the dipole moment, and / or improve thermal properties compared to comparative examples, especially improving thermal stability and / or processability 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 Selected from formula (IV)

[0014] (IV),

[0015] The asterisk "*" indicates the position of the union.

[0016] 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,

[0017] Where R 1 and R 2 One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, SF5 or CN;

[0018] R 3 and R 4 It is independently selected from H, D, halogen, F, CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, SF5 or CF3;

[0019] 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,

[0020] Where R 5 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;

[0021] X a1 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 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 this specification, unless otherwise defined, “partially fluorinated” means a C1 to C8 alkyl group in which only some of the hydrogen atoms are replaced by fluorine atoms.

[0027] In this specification, unless otherwise defined, "perfluorinated" refers to a C1 to C8 alkyl group in which all hydrogen atoms are replaced by fluorine atoms.

[0028] In this specification, unless otherwise defined, “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 themselves may 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, and the heteroaryl group itself may be substituted by one or more aryl and / or heteroaryl groups.

[0031] In this specification, unless otherwise defined, "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, the 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 alkyl groups can be methyl groups, ethyl groups, propyl groups, isopropyl groups, butyl groups, isobutyl groups, sec-butyl groups, tert-butyl groups, pentyl groups, and hexyl groups.

[0033] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane by formally isolating a hydrogen atom from the ring atoms contained in the respective cycloalkane. Examples of such cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, adamantyl, and the like.

[0034] The term "heteroatom" 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 multivalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, and S; more preferably, it is selected from N, P, O, and S.

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

[0036] Similarly, heteroaryl is particularly well understood as a group derived by formally isolating a cyclic hydrogen atom from a heterocyclic aromatic ring in a compound containing at least one heterocyclic aromatic ring.

[0037] Heterocyclic alkyl groups are particularly well understood as groups derived by formally isolating a cyclic hydrogen atom from a saturated cyclic alkyl ring in a compound containing at least one saturated cyclic alkyl ring.

[0038] The terms "fused aryl ring" or "condensed aryl ring" are understood to refer to two aryl rings that share at least two common sp... 2 When carbon atoms are hybridized, they are considered to be either fused or condensed.

[0039] The term "six-membered ring" should be understood as a ring formed by six atoms. The ring-forming atoms of a "six-membered ring" can bond with other atoms outside the ring, such as hydrogen atoms.

[0040] The term "pentacyclic ring" should be understood as a ring formed by five atoms. The ring-forming atoms of a "pentacyclic ring" can bond with other atoms outside the ring, such as hydrogen atoms.

[0041] In this manual, a single key refers to a direct key.

[0042] The terms "without," "containing," and "not including" do not exclude impurities that may be present in the compound prior to deposition. Impurities have no technical effect on the objectives of this invention.

[0043] The term "contact sandwich" refers to a three-layer arrangement in which the middle layer is in direct contact with the 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 supplying electrons when an electric field is applied, and due to the conductivity characteristics based on the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0052] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductivity of 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] An asterisk "*" indicates a binding position.

[0054] Beneficial effects

[0055] Surprisingly, it has been found that the organic compound of formula (I) of the present invention solves the fundamental problem of the invention by making the device superior in all respects to organic electroluminescent devices known in the art, particularly in terms of operating voltage, efficiency, and / or lifetime, and especially in terms of operating voltage, efficiency, and voltage stability over time. It has also been surprisingly found that, compared to comparative examples, the compound of formula (I) can have improved LUMO energy levels, improved dipole moments, and / or improved thermal properties, particularly improved thermal stability and / or processability at elevated temperatures.

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

[0057] The thermal stability of the compound according to formula (I), as determined by TGA 5%, and the volatility, as determined by the standard starting temperature, are within the range required for mass production.

[0058] Surprisingly, it was found that the LUMO energy level is within the range required for effective hole injection and / or hole generation.

[0059] Compound 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] The asterisk "*" indicates the position of the union.

[0070] 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 Mixed aromatics,

[0071] Where R 1 and R 2 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;

[0072] R 3 and R 4 It is independently selected from H, D, halogen, F, CN, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl or CF3;

[0073] 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 Mixed aromatics,

[0074] Where R 5 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;

[0075] X a1 Selected from N or CR a4 ;

[0076] 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,

[0077] Where R a1 R a2 Ra3 and R a4 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, the SF5 group may be excluded for compounds of formula (I).

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

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

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

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

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

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

[0086] According to one embodiment, the 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 position of the union.

[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 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, and 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 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 Selected from 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 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 them is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and

[0106] Optional R of compounds 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 position of the union.

[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 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 and D;

[0120] R 5 Independently selected from substituted or unsubstituted C6 aryl groups or substituted or unsubstituted C4 to C5 heteroaryl groups.

[0121] Where R 5 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 Selected from 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 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 them is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and

[0126] Optional R of compounds of formula (I) a2 and R a3 Do not select CN.

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

[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 position of the union.

[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 Mixed aromatics,

[0137] Where R 1 and R 2 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 It is 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 Mixed aromatics,

[0140] Where R 5 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 Selected from 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 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 them 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 Choose the same.

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

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

[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 position of the union.

[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 Mixed aromatics,

[0157] Where R 1 and R 2 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 Mixed aromatics,

[0160] Where R 5 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 Selected from 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 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 them is selected from partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F or CN; and

[0165] When the aromatic carbon is directly bonded to the sp2-hybridized cyclic nitrogen atom, the CN group does not bond 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) contains fewer than nine CN groups, preferably fewer than eight CN groups, more preferably more than one CN group and fewer than six CN groups, and more than two CN groups and fewer than five CN groups.

[0167] According to one embodiment of the present 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 invention, when calculated in the gas phase using the packages ORCA V5.0.3 (Max Planck Institute for 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, 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, and most preferably in the range of ≤-5.15 eV to ≥-5.70 eV.

[0169] R 1 and R 2

[0170] According to one implementation scheme, R 1 and R 2 It 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 Mixed aromatic compounds.

[0171] According to one implementation scheme, R 1 and R 2 It 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 18Mixed aromatic compounds.

[0172] According to one implementation scheme, R 1 and R 2 It 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 12 Aryl, substituted or unsubstituted C3 to C 12 Mixed aromatic compounds.

[0173] According to one implementation scheme, the substituent R 1 and R 2 It can be 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 groups.

[0174] According to one implementation scheme, the substituent R 1 and R 2 It can be 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.

[0175] According to one implementation scheme, the substituent R 1 and R 2 It can be 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.

[0176] According to one implementation scheme, R 1 and R 2 One or more substituents may be independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3 or CN.

[0177] According to one implementation scheme, R 1 and R 2 One or more substituents may be independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3 or CN.

[0178] According to one implementation scheme, R 1 and R 2 One or more substituents on the surface can be independently selected from D, CF3, and CN.

[0179] R 1 and R 2 Substituents on

[0180] According to one implementation plan, R1 and R 2 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 implementation plan, R 1 and R 2 One or more substituents are independently selected from D, CF3, halogens, F, and CN.

[0182] According to one implementation plan, R 1 and R 2 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 implementation plan, R 1 and R 2 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 implementation plan, R 1 and R 2 One or more substituents are independently selected from D, CF3, and CN.

[0185] R 3 and R 4

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

[0187] According to one implementation scheme, the substituent R 3 and R 4 It can be preferably selected independently from H, D, CN, and CF3.

[0188] According to one implementation scheme, the substituent R 3 and R 4 It can be further preferred to select independently from H or D.

[0189] R 5

[0190] According to one implementation scheme, R 5 Selected from H, D, halogens, 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 Mixed aromatic compounds.

[0191] According to one implementation scheme, R 5 Selected from H, D, halogens, F, CN, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 18 aryl or substituted or unsubstituted C3 to C 18 Mixed aromatic compounds.

[0192] According to one implementation scheme, R 5 Selected from H, D, halogens, F, CN, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 12 aryl or substituted or unsubstituted C3 to C 12 Mixed aromatic compounds.

[0193] According to one implementation scheme, R 5 Selected from H, D, halogens, F, CN, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, substituted or unsubstituted C6 to C 10 Aryl or substituted or unsubstituted C3 to C9 heteroaryl groups.

[0194] According to one implementation scheme, 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 aryl or substituted or unsubstituted C3 to C5 heteroaryl.

[0195] According to one implementation scheme, the substituent R 5 It can be independently selected from H, D, CN, CF3, substituted or unsubstituted C6 aryl, substituted or unsubstituted C4 to C5 heteroaryl.

[0196] According to one implementation scheme, the substituent R 5 Preferably, the components are independently selected from H, D, CN, substituted or unsubstituted C6 aryl groups or substituted or unsubstituted C4 to C5 heteroaryl groups.

[0197] According to one implementation scheme, the substituent R 5 It can be further preferred that the components are independently selected from substituted or unsubstituted C6 aryl groups or substituted or unsubstituted C4 to C5 heteroaryl groups.

[0198] According to one implementation plan, R 5 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.

[0199] According to one implementation plan, R5 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 implementation plan, R 5 One or more substituents are preferably selected independently from D, CF3 or CN.

[0201] R 5 Substituents on

[0202] According to one implementation scheme, R 5 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 implementation scheme, R 5 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 implementation scheme, R 5 One or more substituents are independently selected from D, CF3, and CN.

[0205] According to one implementation scheme, when the aromatic carbon is directly bonded to the sp2-hybridized cyclic nitrogen atom, R 5 One or more substituents CN on the compound do not selectively bind to the aromatic carbon. This can further improve the stability of compounds of formula (I) or (VII).

[0206] Formula (VIa)

[0207] According to one implementation scheme, the substituent R 5 Optional (VIa):

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

[0209] in

[0210] X b1 Selected from N or CR b1 ,

[0211] X b2 Selected from N or CR b2 ,

[0212] X b3 Selected from N or CR b3 ,

[0213] X b4 Selected from N or CRb4 ,

[0214] X b5 Selected from 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 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 implementation scheme, the substituent R 5 Optional (VIa):

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

[0219] in

[0220] X b1 Selected from N or CR b1 ,

[0221] X b2 Selected from N or CR b2 ,

[0222] X b3 Selected from N or CR b3 ,

[0223] X b4 Selected from N or CR b4 ,

[0224] X b5 Selected from N or CR b5 ,

[0225] R b1 To R b5 Preferably, the components are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, halogens, F, or CN.

[0226] According to one implementation scheme, the substituent R 5 Optional (VIa):

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

[0228] in

[0229] X b1 Selected from N or CR b1 ,

[0230] X b2 Selected from N or CR b2 ,

[0231] X b3 Selected from N or CR b3 ,

[0232] X b4 Selected from N or CR b4 ,

[0233] X b5 Selected from N or CR b5 ,

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

[0235] According to one implementation of equation (VIa), where R bn When the value is N, then the adjacent R bm It is not a CN group, where n = 1 to 5 and m = 1 to 5.

[0236] According to one implementation scheme, the substituent R 5 Optional (VIa):

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

[0238] in

[0239] X b1 Selected from N or CR b1 ,

[0240] X b2 Selected from N or CR b2 ,

[0241] X b3 Selected from N or CR b3 ,

[0242] X b4 Selected from N or CR b4 ,

[0243] X b5 Selected from 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 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] Where R bn When the value is N, then the adjacent R bm It is not a CN group, where n = 1 to 5 and m = 1 to 5.

[0247] Formula (VIb)

[0248] According to one implementation scheme, the substituent R 5 Optional self-form (VIb):

[0249] (VIb), where “*” indicates the binding position, and

[0250] in

[0251] X b4 Selected from 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 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 R is preferred. 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 is more preferably... 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 implementation scheme, the substituent R 5 Optional self-formula (VIc):

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

[0259] in

[0260] X b4 Selected from 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 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 an embodiment of formula (VIc), wherein R is preferred. 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 an embodiment of formula (VIc), wherein R is more preferably preferred. 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 implementation scheme, the substituent R 5 Optional Self-Form (VId):

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

[0268] in

[0269] X b4 Selected from 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 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 an embodiment of formula (VId), wherein R is preferred. b1 and / or R b4 Selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, halogens, F, or CN.

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

[0274] Formula (VIe)

[0275] According to one implementation scheme, the substituent R 5 Optional (VIe):

[0276] (VIe), where "*" 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 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 an embodiment of formula (VIe), wherein R is preferred. 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 an embodiment of formula (VIe), wherein R is more preferably preferred. 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 implementation scheme, the substituent R 5 Optional self-form (VIf):

[0284] (VIf), where "*" indicates the join 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 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 an embodiment based on formula (VIf), where R is preferred 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 an embodiment based on formula (VIf), wherein R is more preferably preferred. b1 R b2 and R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

[0290] Formula (VIg)

[0291] According to one implementation scheme, the substituent R 5 Optional (VIg):

[0292] (VIg), where “*” indicates the binding position, and

[0293] in

[0294] 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,

[0295] Where R b1 and R b4 One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0296] According to an embodiment of formula (VIg), wherein R is preferred. 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.

[0297] According to an embodiment of formula (VIg), wherein R is more preferably preferred. b1 and R b4 At least one of them is selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3 or CN.

[0298] R a1 To R a4

[0299] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4If 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 R among them 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 C4 alkyl. 24 Aryl, substituted or unsubstituted C3 to C 24 Heteroaryl, halogen, F, CN; and R among them 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 C4 alkyl. 18 Aryl, substituted or unsubstituted C3 to C 18 Heteroaryl, halogen, F, CN; and R among them 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 C4 alkyl. 12 Aryl, substituted or unsubstituted C3 to C 12 Heteroaryl, halogen, F, CN, and R among them 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 C4 alkyl. 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), and (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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), and (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 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), and (IId) a1 To R a4 If present, it is independently selected from H, D, CF3, halogens, F, and CN. And R is among them. a1 To R a4 At least one of them is selected from CF3, halogen, F, CN.

[0308] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 C4 alkyl. 24 Aryl, substituted or unsubstituted C3 to C 24 heteroaryl, CN; and R in it 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 C4 alkyl. 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, CN; and R in it 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 C4 alkyl. 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, CN; and R in it 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 C4 alkyl. 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If present, it 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), and (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 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), and (IId) a1 To R a4 If it exists, it is independently selected from H, D, CF3, and CN. And R is among them. a1 To R a4 At least one of them is selected from CF3 and CN.

[0317] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a2 and R a3 If present, CN is not selected. This can further improve the stability of compounds of formula I or V.

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

[0319] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 One or more substituents, if present, are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, halogen, F, CN.

[0322] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 One or more substituents, if present, are independently selected from D, partially fluorinated C1 to C4 alkyl or perfluorinated C1 to C4 alkyl, CF3, halogen, F, CN.

[0323] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 One or more substituents on the surface, if present, are independently selected from D, CF3, halogens, F, and CN.

[0324] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 One or more substituents, if present, are independently selected from D, partially fluorinated C1 to C8 alkyl or perfluorinated C1 to C8 alkyl, CF3, CN.

[0325] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 One or more substituents on the surface, 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 implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 One or more substituents on the surface, if present, are independently selected from D, CF3, and CN.

[0327] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If any one of them is present, it is independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, CN.

[0328] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If any one of them is present, it is independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3.

[0329] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If at least one of them exists, it is independently selected from CF3.

[0330] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If any two of them are present, they are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3, halogens, F, or CN.

[0331] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If any two of them are present, they are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3 or CN.

[0332] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If any two of them are present, they are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3.

[0333] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If any two of them are present, they are independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3.

[0334] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If any two of them are present, they are independently selected from partially fluorinated or perfluorinated C1 to C4 alkyl groups, CF3.

[0335] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) a1 To R a4 If at least two of them exist, they are independently selected from CF3.

[0336] R b1 To R b5

[0337] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If present, halogen or F is not selected.

[0338] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If present, then halogen or F is not chosen, and R... b1 To R b5 One or more substituents are not chosen to be halogens or F. This can further improve the stability of compounds of formula I or V.

[0339] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b2 To R b3 If it exists, then CN will not be selected.

[0340] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If present, it is 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 C3 to C 30 heteroaryl, halogen, F, CN.

[0341] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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 C4 alkyl. 24 Aryl, substituted or unsubstituted C3 to C 24 heteroaryl, halogen, F, CN.

[0342] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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 C4 alkyl. 18 Aryl, substituted or unsubstituted C3 to C 18 heteroaryl, halogen, F, CN.

[0343] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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 C4 alkyl. 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, halogen, F, CN.

[0344] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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 C4 alkyl. 10 Aryl, substituted or unsubstituted C3 to C9 heteroaryl, halogen, F, CN.

[0345] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5If 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, halogen, F, CN.

[0346] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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, and CN.

[0347] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If present, it is 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 C3 to C 30 Mixed aryl, CN.

[0348] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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 C4 alkyl. 24 Aryl, substituted or unsubstituted C3 to C 24 Mixed aryl, CN.

[0349] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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 C4 alkyl. 18 Aryl, substituted or unsubstituted C3 to C 18 Mixed aryl, CN.

[0350] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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 C4 alkyl. 12 Aryl, substituted or unsubstituted C3 to C 12 Mixed aryl, CN.

[0351] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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 C4 alkyl. 10 Aryl, substituted or unsubstituted C3 to C9 heteroaryl, CN.

[0352] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and 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, and CN.

[0353] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If any one of them is present, it is independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl, CF3, CN.

[0354] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If any one of them is present, it is independently selected from partially fluorinated or perfluorinated C1 to C8 alkyl groups, CF3.

[0355] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If at least one of them exists, it is independently selected from CF3.

[0356] R b1 To R b5 Substituents on

[0357] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 At least one or more substituents on the molecule, if present, are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, and CN.

[0358] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 At least one or more substituents on the molecule, if present, are independently selected from D, partially fluorinated C1 to C8 alkyl, perfluorinated C1 to C8 alkyl, CF3, halogen, F, and CN.

[0359] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 At least one or more substituents on the surface, if present, are independently selected from D, partially fluorinated C1 to C4 alkyl, perfluorinated C1 to C4 alkyl, CF3, halogen, F, and CN.

[0360] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If present, at least one or more substituents on the surface are independently selected from D, CF3, halogens, F, and CN.

[0361] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If present, at least one or more substituents on the alkyl group are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, and CN.

[0362] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If present, at least one or more substituents on the alkyl group are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, and CN.

[0363] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If present, at least one or more substituents on the surface are independently selected from D, partially fluorinated C1 to C4 alkyl groups, perfluorinated C1 to C4 alkyl groups, CF3, and CN.

[0364] According to one implementation scheme, R in equations I, V, VIa, VIb, VIc, VId, VIe, VIf, and VIg b1 To R b5 If any one or more substituents are present, they are independently selected from D, CF3, and CN.

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

[0366] According to one implementation scheme, R in formula I a1 To R a4 R in equation (VIa) b1 To R b5 R in equation (VIb) b1 To R b3 R in equation (VIc) b1 To R b2 R in equation (VId) b1 R in equation (Vie) b1 To R b4 R in equation (VIf) b1 R b and R b4 R in equation (VIg) b1 and R b4 Halogen or F is not selected; and R in formula I is preferred. a1 To R a4 R in equation (VIa) b1 To R b5 R in equation (VIb) b1 To R b3 R in equation (VIc) b1 To R b2 R in equation (VId) b1 R in equation (Vie) b1 To R b4 R in equation (VIf) b1 R b and R b4 R in equation (VIg) b1 and Rb4 Do not choose halogen or F, and R a1 To R a4 R b1 To R b5 One or more substituents on it are not selected from halogens or F.

[0367] According to one implementation scheme, R in equation (II) a2 To R a3 R in equations (VIa), (VIb), and (VIe) b2 To R b3 , and R in equations (VIc) and (VIf) b2 Do not select CN.

[0368] R a1 To R a4 / R 3 R 4 R 5

[0369] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) 3 R 4 R 5 and R a1 To R a4 If present, it cannot be a halogen or F.

[0370] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) 3 R 4 R 5 and R a1 To R a4 If present, it cannot be halogen or F and R 1 R 2 R 5 and R a1 To R a4 One or more substituents on it cannot be halogens or F.

[0371] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) 3 R 4 R 5 and R a1 To R a4 If present, it cannot be a halogen or F, and R b1 To Rb5 It cannot be halogen or F.

[0372] According to one implementation scheme, R in equations (I), (VII), (II), (IIa), (IIb), (IIc), (IId), (IIe), and (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 it cannot be halogens or F, and R b1 To R b5 It cannot be halogen or F, and R b1 To R b5 One or more substituents on it cannot be halogens or F.

[0373] According to one embodiment, the compound contains 2 to 6 CN groups, preferably 3 to 6 CN groups, more preferably 4 to 6 CN groups, thereby maintaining a suitable evaporation temperature for the manufacture of OLEDs.

[0374] R 5 Specific groups

[0375] According to one implementation scheme, R 5 Choose from groups represented by B1 to B163:

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382] , where “*” indicates the binding position.

[0383] According to a preferred embodiment, R 5 Selected from B1 to B124. According to a more preferred embodiment, wherein R... 5 Selected from B1 to B45. According to a preferred embodiment, where 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 Optional formula (V):

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

[0387] Equation (II) of HetAr

[0388] According to one implementation scheme, equation II is selected from equation 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 one or even a more preferred embodiment, formula II is selected from formula IId.

[0395] (IId)

[0396] According to one or even a more preferred embodiment, formula II is selected from formula IIe.

[0397] (IIe).

[0398] According to an optimal implementation scheme, Equation II is selected from Equation IIf

[0399] (IIf),

[0400] The expression IIf can be partially or fully deuterated.

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

[0402]

[0403]

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

[0405] Preferably, formulas (IIa), (IIb), (IIc), (IId), (IIe), and (IIf) are partially or fully deuterated, and even more preferably, formula (IIf) is partially or fully deuterated.

[0406] HetAr

[0407] According to one embodiment of the compound of formula (I), wherein HetAr is selected from groups 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), for HetAr, it is suitable to use groups represented by C90 to C109.

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

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

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

[0417] According to one implementation, HetAr is selected from C1 to C89. According to another implementation, 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 Choose the same.

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

[0421] According to one implementation scheme, HetAr is selected from formula II. (II), and R 5 Selected from formula VIA (VIa), of which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0422] According to one implementation scheme, HetAr is selected from formula II. (II), and formula VIa is selected from formula VIb. (VIb); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0423] According to one implementation scheme, HetAr is selected from formula II. (II), and formula VIA is selected from formula VIc. (VIc); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0424] According to one implementation scheme, equation II is selected from equation IIa. (IIa), and R 5 Selected from formula VIA (VIa); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0425] According to one implementation scheme, equation II is selected from equation IIa. (IIa) and formula VIa is selected from formula VIb. (VIb); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0426] According to one implementation scheme, equation II is selected from equation IIa. (IIa) and R 5 Selected from formula VIc (VIc); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0427] According to one implementation scheme, equation II is selected from equation IIa. (IIa) and R 5 Selected from VId (VId); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0428] According to one implementation scheme, Equation II is selected from Equation IIb. (IIb) and R 5 Selected from formula VIA (VIa); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0429] According to one implementation scheme, Equation II is selected from Equation IIb. (IIb) and formula VIa is selected from formula VIb. (VIb); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0430] According to one implementation scheme, Equation II is selected from Equation IIb. (IIb) and R 5 Selected from formula VIc (VIc); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0431] According to one implementation scheme, Equation II is selected from Equation IIb. (IIb) and R 5 Selected from VId (VId); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0432] According to one implementation scheme, Equation II is selected from Equation IIb. (IIb) and formula VIa is selected from formula VIe, for (VIe); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0433] According to one implementation scheme, Equation II is selected from Equation IIc. (IIc) and R 5 Selected from formula VIA (VIa); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0434] According to one implementation scheme, Equation II is selected from Equation IIc. (IIc) and formula VIA is selected from formula VIb. (VIb); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0435] According to one implementation scheme, Equation II is selected from Equation IIc. (IIc) and R 5 Selected from formula VIc (VIc); among which R is preferred 3 and R 4Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0436] According to one implementation scheme, Equation II is selected from Equation IIc. (IIc) and R 5 Selected from VId (VId); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0437] According to one implementation scheme, Equation II is selected from Equation IIc. (IIc) and formula VIa is selected from VIe, for (VIe); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0438] According to one implementation scheme, equation II is selected from equation IId. (IId) and R 5 Selected from formula VIA (VIa); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0439] According to one implementation scheme, equation II is selected from equation IId. (IId) and formula VIA is selected from formula VIb. (VIb); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0440] According to one implementation scheme, equation II is selected from equation IId. (IId) and R 5 Selected from formula VIc (VIc); among which R is preferred3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0441] According to one implementation scheme, equation II is selected from equation IId. (IId) and R 5 Selected from VId (VId), of which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0442] According to one implementation scheme, equation II is selected from equation IId. (IId) and formula VIa is selected from VIe, for (VIe); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0443] According to one implementation scheme, equation II is selected from equation IId. (IId) and formula VIA is selected from VIf (VIf); where R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0444] According to one implementation scheme, equation II is selected from equation IIe. (IIe) and R 5 Selected from formula VIA (VIa); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0445] According to one implementation scheme, equation II is selected from equation IIe. (IIe) and formula VIa is selected from VIb, for (VIb); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0446] According to one implementation scheme, equation II is selected from equation IIe. (IIe) and R 5 Selected from formula VIc (VIc); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0447] According to one implementation scheme, equation II is selected from equation IIe. (IIe) and R 5 Selected from VId (VId); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0448] According to one implementation scheme, equation II is selected from equation IIe. (IIe) and formula VIa is selected from VIe, for (VIe); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0449] According to one implementation scheme, equation II is selected from equation IIe. (IIe) and formula VIa is selected from VIf, for (VIf); where R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0450] According to one implementation scheme, equation II is selected from equation IIe. (IIe) and formula VIa is selected from VIg, for (VIg); among which R is preferred 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0451] According to one implementation scheme, Equation II is selected from Equation IIf (IIf) and R 5 Selected from formula VIA (VIa), where HetAr can be partially or fully deuterated; wherein R is preferred. 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0452] According to one implementation scheme, Equation II is selected from Equation IIf (IIf) and formula VIa is selected from VIb, for (VIb), wherein HetAr can be partially or fully deuterated; wherein R is preferred. 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0453] According to one implementation scheme, Equation II is selected from Equation IIf (IIf) and R 5 Selected from formula VIc (VIc); where HetAr can be partially or fully deuterated; where R is preferred. 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0454] According to one implementation scheme, Equation II is selected from Equation IIf (IIf) and R 5 Selected from formula VIc (VId); where HetAr can be partially or fully deuterated; where R is preferred. 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0455] According to one implementation scheme, Equation II is selected from Equation IIf (IIf) and the formula VIa is selected from VIe, for (VIe), wherein HetAr can be partially or fully deuterated; wherein R is preferred. 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0456] According to one implementation scheme, Equation II is selected from Equation IIf (IIf) and the formula VIA is selected from VIf, for (VIf), where HetAr can be partially or fully deuterated; wherein R is preferred. 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0457] According to one implementation scheme, Equation II is selected from Equation IIf (IIf) and the formula VIa is selected from VIg, for (VIg), where HetAr can be partially or fully deuterated; wherein R is preferred. 3 and R 4 Independently selected from H and D, and A 1 and A 2 Selected from The asterisk "*" indicates the position of the combination.

[0458] According to one implementation scheme, 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 equations (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf):

[0463]

[0464]

[0465] The asterisk "*" indicates the binding position, and in which

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

[0467] X a1 Selected from 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 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 them 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 Mixed aromatics,

[0472] Where R 5 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 and D;

[0479] X a1 Selected from 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 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 Mixed aromatics,

[0484] Where R 5 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 position of the combination.

[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 and D;

[0492] X a1 Selected from 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 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 Mixed aromatics,

[0497] Where R 5 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 position of the combination.

[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 and D;

[0505] X a1 Selected from 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 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 Mixed aromatics,

[0510] Where R 5 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 position of the combination.

[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 formula IIc

[0516] (IIc)

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

[0518] X a1 Selected from 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 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 Mixed aromatics,

[0523] Where R 5 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 position of the combination.

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

[0526] (VII)

[0527] in

[0528] HetAr selected (IId)

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

[0530] X a1 Selected from 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 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 Mixed aromatics,

[0535] Where R 5 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 position of the combination.

[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 formula IIe

[0541] ( IIe ),

[0542] R 3 and R 4 Selected from H and 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 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 Mixed aromatics,

[0547] Where R 5 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 position of the combination.

[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 equations (II), (IIa), (IIb), (IIc), (IId), (IIe), and (IIf):

[0553]

[0554]

[0555] The asterisk "*" indicates the binding position, and in which

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

[0557] Xa1 Selected from 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 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 them 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 Selected from N or CR b1 ,

[0564] X b2 Selected from N or CR b2 ,

[0565] X b3 Selected from N or CR b3 ,

[0566] X b4 Selected from N or CR b4 ,

[0567] X b5 Selected from 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 One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, or CN.

[0570] And the asterisk "*" indicates the position of the combination.

[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 formula IIf

[0575] (IIf),

[0576] The expression IIf can be partially or fully deuterated;

[0577] R 3 and R 4 Selected from H and 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 Mixed aromatics,

[0579] Where R 5 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 position of the combination.

[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 and D,

[0587] Xa1 Selected from 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 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 Selected from N or CR b1 ,

[0595] X b2 Selected from N or CR b2 ,

[0596] X b3 Selected from N or CR b3 ,

[0597] X b4 Selected from N or CR b4 ,

[0598] X b5 Selected from 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 One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, CN,

[0601] And the asterisk "*" indicates the position of the combination.

[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 and D,

[0608] X a1 Selected from 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 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 Selected from N or CR b1 ,

[0616] X b2 Selected from N or CR b2 ,

[0617] X b3 Selected from N or CR b3 ,

[0618] X b4 Selected from N or CR b4 ,

[0619] X b5 Selected from N or CR b5 ,

[0620] 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,

[0621] Where R b1 To R b5 One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, CN,

[0622] And the asterisk "*" indicates the position of the combination.

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

[0624] (VII)

[0625] in

[0626] HetAr is selected from formula IIb

[0627] (IIb),

[0628] R 3 and R 4 Selected from H and D,

[0629] X a1 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 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 Selected from N or CR b1 ,

[0637] X b2 Selected from N or CR b2 ,

[0638] X b3 Selected from N or CR b3 ,

[0639] X b4 Selected from N or CR b4 ,

[0640] X b5 Selected from 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 b5One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, CN,

[0643] And the asterisk "*" indicates the position of the combination.

[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 formula IIc

[0648] (IIc)

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

[0650] X a1 Selected from 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 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 Selected from N or CR b1 ,

[0658] Xb2 Selected from N or CR b2 ,

[0659] X b3 Selected from N or CR b3 ,

[0660] X b4 Selected from N or CR b4 ,

[0661] X b5 Selected from 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 One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, CN,

[0664] And the asterisk "*" indicates the position of the combination.

[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 formula IId

[0669] (IId),

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

[0671] X a1 Selected from 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 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 Selected from N or CR b1 ,

[0679] X b2 Selected from N or CR b2 ,

[0680] X b3 Selected from N or CR b3 ,

[0681] X b4 Selected from N or CR b4 ,

[0682] X b5 Selected from 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 One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, CN,

[0685] And the asterisk "*" indicates the position of the combination.

[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 formula IIe

[0690] ( IIe ),

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

[0692] X a1 Selected from 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 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 Selected from N or CR b1 ,

[0700] X b2 Selected from N or CR b2 ,

[0701] X b3 Selected from N or CR b3 ,

[0702] X b4 Selected from N or CR b4 ,

[0703] X b5 Selected from 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 One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, CN,

[0706] And the asterisk "*" indicates the position of the combination.

[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 formula IIf

[0711] (IIf),

[0712] The expression IIf can be partially or fully deuterated;

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

[0714] R 5 Selected from Via

[0715] (VIa),

[0716] in

[0717] X b1 Selected from N or CR b1 ,

[0718] X b2 Selected from 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 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,

[0723] Where R b1 To R b5 One or more substituents are independently selected from D, partially fluorinated C1 to C8 alkyl groups, perfluorinated C1 to C8 alkyl groups, CF3, CN,

[0724] And the asterisk "*" indicates the position of the combination.

[0725] Compound of formula (I)

[0726] According to one embodiment of the present invention, the compound of formula (I) is selected from the compounds represented by 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 present invention, the compound of formula (I) is selected from compounds represented by I-1 to I-40:

[0734]

[0735]

[0736]

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

[0738] According to one embodiment, the compound of formula (I) is selected from I-41 to I-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 I-1, I-12, I-24, I-27, I-30, I-34, I-38 and I-39:

[0743]

[0744] According to a 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 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 transport matrix compound, wherein the compound of formula (I) is preferably a compound of formula (VII).

[0749] According to one implementation, 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 comprising a compound according to formula (VII), wherein the compound according to formula (VII) is preferably selected from compounds I-1 to I-40.

[0751] In cases where the organic semiconductor layer contains a compound according to the invention, the term "compound of formula (I)" in this application text shall also be intended to include 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 terms "substantially non-luminescent" or "non-luminescent" mean that the contribution of a compound or layer to the visible emission spectrum of a device is less than 10%, preferably less than 5%. The visible emission spectrum refers to the emission spectrum with wavelengths ranging from approximately ≥380 nm to approximately ≤780 nm.

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

[0755] Organic electronic devices

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

[0757] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is disposed 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 implementation, 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 base plate.

[0761] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one organic semiconductor layer, and at least one photoactive layer; wherein the at least one organic semiconductor layer is disposed 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 disposed between the anode layer and the at least one photoactive layer.

[0762] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, a first photoactive layer, a second photoactive layer, and 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 disposed 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 disposed in direct contact with the anode layer, and wherein the p-type charge generation layer is disposed 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 includes 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 to be 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 contains 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, the organic electronic device includes 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 to be 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, 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.

[0765] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least two photoactive layers, and 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 disposed 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 disposed in direct contact with the anode layer, and wherein the p-type charge generation layer is disposed 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 includes 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 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 includes 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 includes 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, and 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 base plate.

[0770] According to one 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 emitting layer, preferably a light-emitting layer.

[0772] According to one implementation, 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 an organic semiconductor layer according to the invention.

[0777] Essentially covalent matrix compounds

[0778] The organic semiconductor layer may also comprise a covalent matrix compound, also known 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 substantially of covalently bonded C, H, O, N, and S, and optionally additionally comprises 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 is selected from an organic compound consisting substantially of covalently bonded C, H, O, N, S, and optionally additionally comprises 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 are essentially covalent matrix compounds that can be used as hole injection layers.

[0781] In one embodiment, the substantially covalent matrix compound contains no metal atoms and the majority of its framework atoms are selected from C, O, S, and N. Alternatively, the substantially covalent matrix compound contains no metal atoms and the majority of its framework atoms are 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 ≥450 g / mol and ≤1500 g / mol, more preferably ≥500 g / mol and ≤1000 g / mol, additionally preferably ≥550 g / mol and ≤900 g / mol, and even more preferably ≥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 contains no metal and / or ionic bonds.

[0785] Compounds of formula (VIII) or compounds of formula (IX)

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

[0787] (VIII), (IX),

[0788] in:

[0789] T 1 T 2 T 3 T 4 and T 5 It can be independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably single bond or phenylene group;

[0790] T 6 It can be phenylene oxide, biphenylene oxide, terphenylene oxide, or naphthylene oxide;

[0791] Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be independently selected from substituted or unsubstituted C6 to C6. 20 aryl or substituted or unsubstituted C3 to C 20Heteroarylene, 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 triphenylidene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[b,f]-anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthone, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azaheptanyl, substituted or unsubstituted dibenzo[b,f]azaheptanyl, substituted or unsubstituted 9,9'- Spirodi[fluorene], substituted or unsubstituted spiro[fluorene-9,9'-xanton]; or substituted or unsubstituted aromatic fused ring systems comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted hetero 5-membered rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings, substituted or unsubstituted fluorene; or fused ring systems comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, wherein the rings may be selected from: (i) heterocyclic unsaturated 5 to 7-membered rings, (ii) aromatic heterocyclic 5 to 6-membered rings, (iii) non-heterocyclic unsaturated 5 to 7-membered rings, (iv) aromatic non-heterocyclic 6-membered rings;

[0792] Among them, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents may be the same or different from those selected from: 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 1. Substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted branched 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 C6... 18 Aryl, unsubstituted C3 to C 18 A heteroaryl fused ring system comprising 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are 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 It can be selected from H, D, straight-chain alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 1 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms, alkenyl or ynyl groups having 2 to 6 carbon atoms, C6 to C 18 Aryl or C3 to C 18 Mixed aromatic compounds.

[0794] According to one implementation scheme, where T 1 T 2 T 3 T 4 and T 5 It can be independently selected from single bonds, phenylene groups, biphenylene groups, or terphenylene groups. According to one embodiment, T... 1 T 2 T 3 T 4 and T 5 It can be independently selected from phenylene, biphenylene, or terphenylene, and T 1 T 2 T 3 T 4 and T 5 One of them is a single bond. According to one implementation, where T... 1 T 2 T 3 T 4 and T 5 It can be independently selected from phenylene group or biphenylene group, and T 1 T 2 T 3 T 4 and T 5 One of them is a single bond. According to one implementation, where T... 1 T 2 T 3 T 4 and T 5 It can be independently selected from phenylene group or biphenylene group, and T 1 T 2 T 3 T 4 and T 5 Two of them are single bonds.

[0795] According to one implementation scheme, where T 1 T 2 and T 3 It can be independently selected from phenylene groups, and T 1 T 2 and T 3 One of them is a single bond. According to one implementation, where T... 1T 2 and T 3 It can be independently selected from phenylene groups, and T 1 T 2 and T 3 The two in it are single bonds.

[0796] According to one implementation scheme, where T 6 It can be phenylene oxide, biphenylene oxide, or terphenylene oxide. According to one embodiment, where T... 6 It can be a benzene group. According to one embodiment, where T... 6 It can be a biphenyl group. According to one embodiment, where T... 6 It can be a triphenylene group.

[0797] According to one implementation scheme, where Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Can be selected independently 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), where

[0803] An asterisk "*" indicates a binding position.

[0804] According to one implementation scheme, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be selected independently from K1 to K15; or selected from K1 to K10 and K13 to K15.

[0805] According to one implementation scheme, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It 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 this range is available, the standard starting temperature can be within a range particularly suitable for mass production.

[0807] "Matrix compounds of formula (VIII) or formula (IX)" may also be called "hole transport compounds".

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

[0809] According to one embodiment of the electronic device, the matrix compound of formula (VIII) or formula (IX) may 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 include other layers in addition to those already mentioned above. Exemplary embodiments of each layer 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 (OLEDs). 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 base plate.

[0824] Anode layer

[0825] The anode layer can be formed by deposition or sputtering of the material used to form the anode layer. The material used to form the anode layer can be a high work function material to facilitate hole injection. The anode material can also be selected from low work function materials (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, 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 positioned 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 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 invention, the first anode sublayer is formed by depositing a 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 zinc indium oxide, more preferably indium tin oxide.

[0835] According to one embodiment of the 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 can be formed by sputtering a transparent conductive oxide.

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

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

[0839] According to one embodiment of the 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 can be formed by sputtering 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 disposed between the second and third anode sublayers.

[0843] Hole transport layer

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

[0845] Hole transport layers (HTLs) can be formed on high-intensity interphase (HILs) via vacuum deposition, spin coating, slot die coating, printing, casting, and Langmuir-Blodgett (LB) deposition. When forming HTLs via vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for HIL formation. However, the conditions for vacuum or solution deposition can vary depending on the compound used to form the HTL.

[0846] HTLs can be formed from any compound commonly used to form HTLs. 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 HTLs 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(naphthyl-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine compounds, such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA). In these compounds, TCTA is capable of transporting holes and inhibiting exciton diffusion into the EML.

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

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

[0849] According to one embodiment of the 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 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 HTL can be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, even more preferably about 20 nm to about 190 nm, even more preferably about 40 nm to about 180 nm, even more preferably about 60 nm to about 170 nm, even more preferably about 80 nm to about 160 nm, even more preferably about 100 nm to about 160 nm, even more preferably about 110 nm to about 140 nm.

[0852] When the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without substantial damage to the driving voltage.

[0853] Electron blocking layer

[0854] The function of an electron blocking layer (EBL) is to prevent electrons from transferring from the emissive layer to the hole transport layer, thereby confining electrons within the emissive layer. This improves efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer contains a triarylamine compound. The LUMO level of the triarylamine compound can be closer to the vacuum level than the LUMO level of the hole transport layer. Compared to the HOMO level of the hole transport layer, the electron blocking layer can have a HOMO level further away from the vacuum level. The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0855] If an electron blocking layer has a high triplet energy level, it can 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 higher luminous efficiency from the phosphorescent emitting layer. The triplet control layer is selected from triarylamine compounds whose triplet energy level is higher than that of the phosphorescent emitter in the adjacent emitting layer. Suitable compounds for triplet control layers, particularly triarylamine compounds, are described in EP 2 722 908 A1.

[0857] Photoactive Alpha Layer (PAL)

[0858] The photoactive layer converts electric current into photons or vice versa. PALs can be formed on HTLs via vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When using vacuum deposition or spin coating to form PALs, the deposition and coating conditions can be similar to those for HIL formation. 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 emissive layer (EML) or an absorbent layer.

[0859] Emissive Layer (EML)

[0860] EMLs can be formed on HTLs via vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When using vacuum deposition or spin coating to form EMLs, the deposition and coating conditions can be similar to those for HIL formation. However, the deposition and coating conditions can 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 contain the compound of formula (I).

[0862] The luminescent layer (EML) can be formed by a combination of a host and a luminescent dopant. Examples of hosts include: Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 4,4',4''-tris(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-bis-2-naphthylanthracene (TBADN), stilbeneyl arylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazolic acid)zinc (Zn(BTZ)2).

[0863] The luminescent dopant can be a phosphorescent or fluorescent luminescent material. Phosphorescent luminescent materials and those emitting light via thermally activated delayed fluorescence (TADF) are preferred due to their higher efficiency. The luminescent material can be a small molecule or a polymer.

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

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

[0866] Examples of phosphorescent blue emitting electron dopants include F₂Irpic, (F₂ppy)₂Ir(tmd), and Ir(dfppz)₃, and terfluorene. Examples of fluorescent blue emitting electron dopants include 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetratert-butylperylene (TBPe).

[0867] Based on 100 parts by weight of the host, the amount of luminescent dopant can range from about 0.01 parts by weight to about 50 parts by weight. 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 thickness of the EML is within this range, the EML can exhibit excellent luminescence without substantial impairment of the driving voltage.

[0868] Hole blocking layer (HBL)

[0869] Hole blocking layers (HBLs) can be formed on EMLs using methods such as vacuum deposition, spin coating, slot die coating, printing, casting, and LB deposition to prevent holes from diffusing into the ETL. When the EML contains phosphorescent dopants, the HBL can also have triplet exciton blocking functionality.

[0870] HBL can also be called auxiliary ETL or a-ETL.

[0871] When using vacuum deposition or spin coating to form HBLs, the deposition and coating conditions can be similar to those for forming HILs. However, the deposition and coating conditions can vary depending on the compound used to form the HBL. Any compound commonly used to form HBLs can be used. Examples of compounds used to form HBLs include diazole derivatives, triazole derivatives, phenanthrene-rhein derivatives, and azazine derivatives, preferably triazine or pyrimidine derivatives.

[0872] The thickness of the HBL can be in the 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 can have excellent hole blocking properties without substantial damage to the 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 invention, the electron transport layer may further comprise an azazine compound, preferably a triazine compound.

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

[0877] The thickness of the ETL can range from about 15 nm to about 50 nm, for example, from about 20 nm to about 40 nm. When the thickness of the ETL is within this range, the ETL can have satisfactory electron injection properties without substantial impairment of the driving voltage.

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

[0879] Electron Injection Layer (EIL)

[0880] Optional electron transport layers (EILs) that facilitate electron injection from the cathode can be formed on the electron transport layer (ETL), preferably directly on the electron transport layer. Examples of materials used for forming EILs include lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li₂O, BaO, Ca, Ba, Yb, and Mg, which are known in the art. The deposition and coating conditions for forming EILs are similar to those for forming HILs, but the deposition and coating conditions may vary depending on the materials used to form the EILs.

[0881] The thickness of the EIL can range from about 0.1 nm to about 10 nm, for example, from about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL can have satisfactory electron injection properties without substantial impairment of the driving voltage.

[0882] Charge generation layer

[0883] 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 an organic semiconductor layer according to the present invention, and wherein the charge generation layer is disposed between 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 an organic semiconductor layer according to the present invention, and 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 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 an organic semiconductor layer according to the present invention, and wherein the charge generation layer is disposed between two photoactive layers.

[0886] The charge generation layer may also 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 can range from about 0.5 nm to about 15 nm, for example, from about 1 nm to about 10 nm. When the thickness of the n-type charge generation layer is within this range, the EIL can have satisfactory electron injection properties without substantial impairment of the driving voltage.

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

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

[0891] cathode layer

[0892] The cathode layer is formed on an ETL or optionally an EIL. The cathode layer can be formed of a metal, alloy, 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 can 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, it can be transparent or translucent even if the cathode layer is formed of metal or 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 diode (OLED)

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

[0897] According to one embodiment, the organic light-emitting device includes 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 includes 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 includes 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 disposed 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: a substrate arranged adjacent to an anode layer, an anode layer arranged adjacent to a hole injection layer, a hole injection layer arranged adjacent to a first hole transport layer, a first hole transport layer arranged adjacent to a first electron blocking layer, a first electron blocking layer arranged adjacent to a first light-emitting layer, a first light-emitting layer arranged adjacent to a first electron transport layer, a first electron transport layer arranged adjacent to an n-type charge generation layer, an n-type charge generation layer arranged adjacent to a p-type charge generation layer, a p-type charge generation layer arranged adjacent to a second hole transport layer, a second hole transport layer arranged adjacent to a second electron blocking layer, a second electron blocking layer arranged adjacent to 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.

[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] Methods for manufacturing organic light-emitting devices

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

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

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

[0908] According to various embodiments of the present invention, OLED layers can be provided on a substrate or on a top layer, or arranged between the aforementioned 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) comprising 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 on a substrate (110).

[0910] According to one aspect, an OLED may include the following layer structure: a substrate is arranged adjacent to an anode layer, an anode layer is arranged adjacent to a hole injection layer, a hole injection layer is arranged adjacent to a first hole transport layer, a first hole transport layer is arranged adjacent to a first electron blocking layer, a first electron blocking layer is arranged adjacent to a first light-emitting layer, a first light-emitting layer is arranged adjacent to a first electron transport layer, a first electron transport layer is arranged adjacent to an n-type charge generation layer, an n-type charge generation layer is arranged adjacent to a p-type charge generation layer, a p-type charge generation layer is arranged adjacent to a second hole transport layer, a second hole transport layer is arranged adjacent to a second electron blocking layer, a 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] Methods for manufacturing organic electronic devices

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

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

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

[0916] Suitable deposition methods include:

[0917] - Deposition via vacuum thermal evaporation;

[0918] - Deposition via solution processing, preferably the processing being selected from spin coating, printing, casting; and / or

[0919] - Slit-type die coating.

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

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

[0922] - A second deposition source to release essentially covalent matrix compounds;

[0923] The method includes the step of forming a hole injection layer; wherein, for organic light-emitting diodes (OLEDs):

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

[0925] According to various embodiments of the present invention, the method may further include forming at least one layer selected from the group consisting of: 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 invention, the method may further include a step for forming an organic light-emitting diode (OLED), wherein

[0927] - Form an anode layer on the substrate.

[0928] - A hole injection layer containing a compound of formula (I) is formed on the anode layer.

[0929] - A hole transport layer is formed on the hole injection layer of the compound containing formula (I).

[0930] - Form a light-emitting layer on the hole transport layer.

[0931] - An electron transport layer is formed on the light-emitting layer, and optionally a hole blocking layer is formed on the light-emitting layer.

[0932] - and finally form the cathode layer,

[0933] - An optional hole-blocking layer is formed sequentially between the first anode layer and the light-emitting layer.

[0934] - An optional electron injection layer is formed between the electron transport layer and the cathode layer.

[0935] According to various implementation schemes, an OLED may have the following layer structure, wherein the layers have the following order:

[0936] The 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, a light-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, the electronic device comprising at least one organic light-emitting device according to any embodiment described throughout this application, preferably, the electronic device comprising an organic light-emitting diode as described throughout this application. More preferably, the electronic device is a display device.

[0938] In the following sections, embodiments will be described in more detail. However, the invention is not limited to the embodiments described below. Exemplary aspects will now be referred to in detail. Attached Figure Description

[0939] In the described embodiments, the components mentioned above, as well as the claimed components and the components used according to the invention, have no particular exceptions in terms of their size, shape, material selection, and technical concept, thus allowing the application of selection criteria known in the relevant field without restriction.

[0940] Further details, features, and advantages of the invention are disclosed in the dependent claims and the following description of the various accompanying drawings, which illustrate preferred embodiments of the invention by way of example. However, any embodiment does not necessarily represent the full scope of the invention, and therefore the scope of the invention is to be interpreted with reference to the claims and this document. It should be understood that the foregoing general description and the following detailed description are merely exemplary and explanatory, and are intended to provide further explanation of the claimed invention.

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

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

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

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

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

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

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

[0948] The accompanying drawings will now be illustrated in more detail with reference to examples. However, the invention is not limited to the drawings below.

[0949] In this document, when a first element is referred to as being formed or arranged "on" or "above" a second element, the first element may be arranged directly on the second element, or one or more other elements may be arranged therebetween. When a first element is referred to as being "directly" formed or arranged "on" or "above" a second element, no other elements are arranged therebetween.

[0950] Figure 1 This 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 contain 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 This 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, and a hole injection layer (HIL) 130 that may contain a compound of formula (I). The HIL 130 is disposed on the anode layer 120. A photoactive layer (PAL) 170 and a cathode layer 190 are disposed on the HIL 130.

[0952] Figure 3 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate 110, an anode layer 120, and a hole injection layer (HIL) 130 that may contain a compound of formula (I). The HIL 130 is disposed on the 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 the HIL 130. Instead of a single electron transport layer 160, an electron transport layer stack (ETL) may optionally be used.

[0953] Figure 4 This 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 The OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 that may contain 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 This 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 comprise a compound of formula (I).

[0956] Figure 6 This 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 comprise a compound of formula (I).

[0957] Figure 7This 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 contain 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 contain a compound of formula (I). The hole injection layer may contain a compound of formula (I). The anode layer may contain a first anode sublayer, a second anode sublayer, and optionally a third anode sublayer.

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

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

[0960] synthesis

[0961] The present invention is further illustrated by the following embodiments, which are merely exemplary and not restrictive.

[0962]

[0963] Intermediate (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 trimethylchlorosilane 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, then gradually heated to room temperature. The reaction was quenched with dilute sulfuric acid. The organic and aqueous layers were separated, and the aqueous phase was extracted with diethyl ether. The combined organic layers were dried with sodium sulfate, and the solvent was evaporated. The crude orange solid was crystallized from dichloromethane / methanol in a 1:1 ratio to give the pure product.

[0965] Intermediate (4)

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

[0967] Intermediate (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 cooling the reaction to room temperature and then cooling in a refrigerator, the precipitate was filtered off and washed with cold dichloromethane. The product was ready for use without further purification.

[0969] Intermediate (6)

[0970] A flask equipped with a magnetic stirrer and 4 equivalents of malononitrile was evacuated and filled with an inert gas. After adding DME, the solution was cooled to 0°C, and 6 equivalents of sodium hydride were added over 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 diatomaceous earth filter with a silica gel liner on top. After grinding 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 to obtain the pure product.

[0971] Quinone (7)

[0972] A flask equipped with a magnetic stirrer was placed into intermediate (6), evacuated, and rinsed 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 at a DCM / HOAc ratio of 4:1. After stirring at room temperature for 1 hour and then 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 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 moments, LUMO, and HOMO levels of the molecular structure were determined by applying the hybrid functional B3LYP and the 6-31G* basis set from the optimized geometry obtained by applying the functional BP86 and Def2-SVP basis set 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 a deuterium atom (D), the mass of that particular atom was designated as 2.00141 amu (atomic mass units).

[0975] Melting point

[0976] The melting point (Tm) was determined as the peak temperature based on the DSC curve measured by TGA-DSC as described above or a separate DSC measurement (MettlerToledo DSC822e, where the sample was heated from room temperature to complete melting at a heating rate of 10 K / min under a pure nitrogen flow. Samples of 4 to 6 mg were placed in a 40 µL covered Mettler Toledo aluminum dish with a <1 mm hole punched in the cover).

[0977] Glass transition temperature

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

[0979] Thermogravimetric analysis

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

[0981] The TGA 5% value can be determined by heating 9 to 11 mg of sample in an open 100 µL aluminum dish at a heating rate of 10 K / min in a thermogravimetric analyzer under a nitrogen flow rate of 20 mL / min in the equilibrium zone and 30 mL / min in the oven zone.

[0982] The TGA 5% value can provide an indirect measure of a compound's volatility and / or decomposition temperature. In a first-order approximation, a higher TGA 5% value indicates lower volatility and / or a higher decomposition temperature.

[0983] According to one embodiment, the TGA 5% value of the compound of formula (I) is selected in the range of ≥280°C and ≤420°C; preferably ≥290°C and ≤410°C, and even more preferably ≥295°C and ≤410°C.

[0984] Standard starting temperature

[0985] Standard starting temperature (T) RO The concentration was determined by loading 100 mg of the compound into a VTE source. As a VTE source, a point source of organic materials provided by Kurt J. Lesker Company (www.Lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com) can be used. In amounts less than 10 mg... -5 The VTE source was heated at a constant rate of 15 K / min under a pressure of millibars, and the internal temperature of the source was measured using thermocouples. The evaporation of the compound was detected using a QCM detector, which detected the deposition of the compound on a quartz crystal of the detector. The deposition rate on the quartz crystal was measured in μg / s. To determine the standard onset temperature, the deposition rate was 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 was heated and cooled three times, and only the results from the second and third runs were used to determine the standard onset temperature.

[0986] To effectively control the evaporation rate of organic compounds, a standard starting temperature can be within the range of 185°C to 280°C. If the standard starting temperature is below 185°C, evaporation may be too rapid and therefore difficult to control. If the standard starting temperature is above 280°C, the evaporation rate may be too low, which could 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 a compound's volatility. The higher the standard onset temperature, the lower the compound's volatility.

[0988] dipole moment

[0989] The dipole moment of a molecule containing N atoms It is given by the following formula:

[0990]

[0991] in and This represents the partial charge and position of atom i in the molecule. The dipole moment is obtained by optimizing the geometry at the same theoretical level. The geometry of the molecular structure is optimized in the gas phase using hybrid functionals B3LYP and 6-31G* basis sets (package ORCA V5.0.3 (Max Planck Institute für Kohlenforschung, Kaiser Wilhelm Platz1, 45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67, 50677Köln, Germany)). If more than one conformation is feasible, the conformation with the lowest total energy is selected to determine the structure and electronic parameters of the molecule.

[0992] Measurement of UV-Vis absorption in solution

[0993] The experimental absorption spectra were recorded using a Thermo Fisher Evolution Pro UV-Vis spectrophotometer. For sample preparation, the material was weighed into an aluminum crucible and then placed into a 25 mL volumetric flask. The readability of the mass change on the relevant microbalance was within the range of 1–2 µg. The volumetric flask was then filled to the mark with dichloromethane (spectral grade, according to the manufacturer's instructions, transmittance ≥90% at λ≥248 nm), and shaken until the material was completely dissolved, yielding a concentration of 10. -4 mol / L~10 -5 A mol / L solution was prepared. For measurements, 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, which was measured immediately before the measurement, was subtracted from all spectra.

[0994] Measurement of light absorption rate of organic semiconductor layer

[0995] A 35 nm thick mixed film of N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9'-spirodi[fluorene]-2-amine and p-type dopant was prepared by thermal evaporation on a quartz substrate (EN08, ≥99.98% SiO2, GVB GmbH) according to Table 2, 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 using a Filmetrics F10-RT spectrometer in the spectral range of 380 nm to 1050 nm. An empty quartz substrate was used as the reflectance standard. Absorbance was automatically calculated by subtracting the reflectance and transmittance values ​​from 100%.

[0996] Calculated absorption area or maximum absorption capacity

[0997] All calculations were performed using the 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 levels of the molecular structure were determined by applying the hybrid functionals B3LYP and 6-31G* basis sets to the optimized geometry obtained by applying the functionals BP86 and Def2-SVP basis sets in the gas phase. TD-DFT calculations were then performed using the optimized geometry obtained therefrom, applying the hybrid functionals PBE0 and Def2-SVP basis sets in the gas phase and including the first 30 singlet transitions. The calculated singlet transitions were used to calculate the absorption spectra by applying Gaussian fitting (λ = 215 nm to 850 nm), excluding transitions below 350 nm.

[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] Ten mg of the compound was placed in a 2 cm Ah03 crucible and mounted 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, Typ 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 and turbomolecular pumps. The combination of the nitrogen inlet and pump valves allowed pressures from 1e2 mbar to 1e-6 mbar, with a standard operating pressure of 1e-4 mbar and 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 / min. The compound was completely evaporated and detected by the QCM. The frequency shift of the QCM during the entire heating period corresponds to a 100% mass loss.

[1002] The reference temperature for the dopant material is taken at a mass loss of 5%, because 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 doped material according to Formula I

[1005]

[1006] As is evident from Table 1, the compounds of the present invention exhibit higher HV-TGA5% values, and therefore evaporate at higher temperatures. Thus, the high HV-TGA5% of the compounds of the present invention can be advantageous in minimizing or avoiding tool contamination during, for example, the manufacture of organic electroluminescent devices.

[1007] Table 2

[1008]

[1009]

[1010]

[1011]

[1012]

[1013]

[1014]

[1015]

[1016]

[1017]

[1018] Table 2 shows the LUMO level, HOMO level, dipole moment, and band gap between the LUMO and HOMO levels for the comparative compounds and the compounds of the present invention.

[1019] Table 2b: Absorption performance of the comparative compound and the compound of the present invention

[1020]

[1021]

[1022]

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

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

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

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

[1027] Therefore, the compound may be advantageous in providing organic electronic devices or display devices with improved display brightness, or in improving the lifespan of the display when using lower current densities.

[1028] In addition, high efficiency, such as current efficiency and external quantum efficiency, can help reduce power consumption and improve battery life, especially in mobile devices.

[1029] General steps for manufacturing OLEDs

[1030] Fabrication of OLED devices containing a hole injection layer comprising the compound of the present invention

[1031] For the embodiments and comparative examples according to the present invention in Table IX, a glass substrate having an anode layer comprising a first anode sublayer of 10 nm ITO, a second anode sublayer of 120 nm Ag, and a third anode sublayer of 8 nm ITO was cut to a size of 100 mm × 100 mm × 0.7 mm, ultrasonically washed with water for 60 minutes, and then ultrasonically washed with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, followed by plasma treatment, as shown in Table 2, to prepare the anode layer. The plasma treatment was carried out in an atmosphere containing 97.6 vol% nitrogen and 2.4 vol% oxygen.

[1032] Then, N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine (N-5), which serves as the hole transport matrix compound, is vacuum deposited with 2% by weight of the compound of the present invention or comparative compound listed in Table 2 as a dopant, thereby forming a hole injection layer (HIL) with a thickness of 10 nm according to Table 4.

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

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

[1035] Then, a 19 nm thick emissive layer (EML) 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-anthrayl] [2457172-82-4] as the EML host and 1 vol% of 5H,9H-[1]benzothiopheno[2′,3′:5,6][1,4]azaboroxane[2,3,4-kl]azaboroxane, 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl] [2482607-57-6].

[1036] Then, a hole-blocking layer with a thickness of 5 nm was formed on the EML by depositing the compound 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluorene-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 HBL by co-depositing compound 6,6'-(naphthalene-1,2-dimethylbis(4,1-phenyleneyl))bis(2,4-diphenyl-1,3,5-triazine) (N-15) and LiQ in a 50:50 weight ratio.

[1038] Then, in 10 -7 Yb was evaporated at a rate of 0.01 Å / s to 1 Å / s under millibars, thereby forming 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 under millibars 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-carbazole-3-yl)phenyl)-9H-fluorene-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] Fabrication of OLED devices containing a p-type charge generation layer comprising the compound of the present invention

[1046] For the embodiments and comparative examples according to the present invention in Table IX, a glass substrate having an anode layer comprising a first anode sublayer of 10 nm ITO, a second anode sublayer of 120 nm Ag, and a third anode sublayer of 8 nm ITO was cut to a size of 100 mm × 100 mm × 0.7 mm, ultrasonically washed with water for 60 minutes, and then ultrasonically washed with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, followed by plasma treatment (see Table 4) to prepare the anode layer. The plasma treatment was carried out in an atmosphere containing 97.6 vol% nitrogen and 2.4 vol% oxygen.

[1047] Then, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine (N-1), which serves as the first hole transport matrix compound, is vacuum deposited with 2 wt% of 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-trimethylenetri(cyanomethyl))tri(2,3,5,6-tetrafluorobenzonitrile) (N-2) 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-carbazole-3-yl)phenyl)-9H-fluorene-2-amine (N-1) was vacuum deposited to form a first hole transport layer with a thickness of 29 nm.

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

[1050] Then, a first luminescent layer (EML1) with a thickness of 19 nm was formed on 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-anthrayl] [2457172-82-4] as the EML host and 1 vol% of 5H,9H-[1]benzothiopheno[2′,3′:5,6][1,4]azaboroxane[2,3,4-kl]azaboroxane, 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl] [2482607-57-6].

[1051] Then, a first electron transport layer (ETL1) with a thickness of 7.5 nm is formed on the first luminescent layer by depositing 2,2'-(1,3-phenyleneyl)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-deposition of 98 vol% of 2,2'-(1,3-phenyleneyl)bis[9-phenyl-1,10-phenanthroline (N-4) and 2 vol% of Yb.

[1053] Then, a first p-type charge-generating layer (p-CGL) with a thickness of 10 nm is 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 compound of the present invention 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-carbazole-2-amine (N-5).

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

[1056] Then, a second luminescent layer (EML2) with a thickness of 19 nm was formed on 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-anthrayl] [2457172-82-4] as the EML host and 1 vol% of 5H,9H-[1]benzothiopheno[2′,3′:5,6][1,4]azaboroxane[2,3,4-kl]azaboroxane, 2,7,11-tris(1,1-dimethylethyl)-5,9-bis[4-(1,1-dimethylethyl)phenyl] [2482607-57-6].

[1057] Then, a first hole-blocking layer (HBL1) with a thickness of 5 nm was formed on EML2 by depositing the compound 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluorene-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 HBL by co-depositing compound 6,6'-(naphthalene-1,2-dimethylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine) (N-15) and LiQ in a 50:50 weight ratio.

[1059] Then, in 10 -7 Yb was evaporated at a rate of 0.01 Å / s to 1 Å / s under millibars, thereby forming 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 under millibars 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-carbazole-3-yl)phenyl)-9H-fluorene-2-amine} was vacuum deposited on the cathode layer to form a capping layer with a thickness of 75 nm.

[1062] To evaluate the performance of the invention relative to the prior art, current efficiency was measured at 20°C. The current-voltage characteristics were determined using a Keithley 2635 source measurement unit by applying a voltage in V and measuring the current flowing through the device under test in mA. The voltage applied to the device varied in 0.1 V increments within the range of 0 V to 10 V. Similarly, the luminance-voltage characteristics and CIE coordinates were measured in cd / m² at various voltage values ​​using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungs stelle (DAkkS)). 2 The brightness was determined by interpolating the brightness-voltage and current-voltage characteristics at 15 mA / cm². 2 The CD / A efficiency under these conditions.

[1063] In bottom-emitting devices, emission is predominantly Lambertian and quantized as a percentage of external quantum efficiency (EQE). To determine the efficiency EQE (in %), a calibrated photodiode at 15 mA / cm² was used. 2 The light output of the measuring device.

[1064] In top-emitting devices, emission is forward-oriented, non-Lambertian, and 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 / cm². 2 The light output of the measuring device.

[1065] The device lifetime LT was measured using a Keithley 2400 source meter under ambient conditions (20°C) and 10 mA / cm². 2 or 30 mA / cm 2 The measurements were taken and recorded in hours.

[1066] The brightness of the device was measured using a calibrated photodiode. Lifetime LT was defined as the time until the brightness of the device decreased to 97% of its initial value.

[1067] The increment ∆U of the operating voltage is used as a measure of the device's operating voltage stability. During the LT measurement, this increment is determined by subtracting the operating voltage one hour after the device starts operating from the operating voltage after 100 hours.

[1068] ∆U=[U(100h) - U(1h)].

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

[1070] Technical effects of the present invention

[1071] Table 4

[1072]

[1073] Compared to a comparative OLED (Comparative Example 1), the OLED containing the compound of the present invention, according to an embodiment of the present invention (Example 1 of the present invention), exhibits a lower operating voltage.

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

[1075] Compared to a comparative OLED (Comparative Example 1), the OLED comprising the compound of the present invention, according to an embodiment of the present invention (Example 1 of the present invention), exhibits higher current efficiency and external quantum efficiency.

[1076] High efficiency, such as external quantum efficiency and current efficiency, can help reduce power consumption and improve battery life, especially in mobile devices.

[1077] Compared to a comparative OLED (Comparative Example 1), the OLED containing the compound of the present invention, according to an embodiment of the present invention (Example 1 of the present invention), exhibits a lower operating voltage increase over time.

[1078] Low voltage, when increased over time, can lead to improved long-term stability of electronic devices.

[1079] Compared to a comparative OLED (Comparative Example 1), the OLED containing the compound of the present invention, according to an embodiment of the present invention (Example 1 of the present invention), exhibits a longer lifetime.

[1080] Longer lifespan can lead to improved long-term stability of electronic devices.

[1081] Table 5

[1082]

[1083] Compared to the comparative OLED (Comparative Example 2), the OLED containing the compound of the present invention, according to an embodiment of the present invention (Example 2 of the present invention), exhibits a lower operating voltage.

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

[1085] Compared to the comparative OLED (Comparative Example 2), the OLED containing the compound of the present invention, according to the embodiment of the present invention (Example 2 of the present invention), exhibits higher current efficiency and external quantum efficiency.

[1086] High efficiency, such as external quantum efficiency and current efficiency, can help reduce power consumption and improve battery life, especially in mobile devices.

[1087] Compared to the comparative OLED (Comparative Example 2), the OLED containing the compound of the present invention, according to an embodiment of the present invention (Example 2 of the present invention), exhibits a lower operating voltage increase over time.

[1088] Low voltage, when increased over time, can lead to improved long-term stability of electronic devices.

[1089] Compared to the comparative OLED (Comparative Example 2), the OLED containing the compound of the present invention, according to the embodiment of the present invention (Example 2 of the present invention), exhibits a longer lifetime.

[1090] Longer lifespan can lead to improved long-term stability of electronic devices.

[1091] The specific combinations of elements and features in the detailed embodiments described above are merely exemplary; these teachings are interchangeable and substituted with other teachings herein and in the series / applications incorporated by reference. As those skilled in the art will recognize, variations, modifications, and other embodiments described herein can be conceived without departing from the spirit and scope of the claimed invention. Therefore, the above description is by way of 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 forms “a” or “an” do not exclude plural indicators. The fact that specific measures are enumerated in dissimilar dependent claims does not imply that combinations of these measures have not been advantageously chosen. The scope of the invention is defined by the claims and their equivalents. Furthermore, the reference numerals used in the specification and claims are not intended to limit the scope of the claimed invention.

Claims

1. A compound, wherein the compound is selected from the compounds represented by I-1 to I-53: 。 2. An organic semiconductor layer, wherein the organic semiconductor layer comprises the compound according to claim 1.

3. The organic semiconductor layer according to claim 2, wherein the organic semiconductor layer comprises: the compound according to claim 1 and a hole transport matrix compound.

4. The organic semiconductor layer according to claim 2, wherein the organic semiconductor layer is a hole injection layer or a p-type charge generation layer.

5. An organic electronic device, wherein the organic electronic device comprises the organic semiconductor layer according to claim 2.

6. The organic electronic device of claim 5, 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 of claim 2, 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.

7. A display device comprising the organic electronic device according to claim 5.

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