Metal complexes and semiconductor layers and electronic devices comprising metal complexes

Abstract

The present invention relates to a compound of formula (I), wherein M is a metal; L is a charge neutral ligand which is coordinated to the metal M; n is an integer selected from 1 to 4, which corresponds to the oxidation number of M; m is an integer selected from 0 to 2; R1, R2 and R3 are substituents, wherein at least one R1, R2 and / or R3 is selected from a substituted C6 to C24 aryl group, wherein at least one substituent of the substituted C6 to C24 aryl group is selected from CN or a partially or fully fluorinated Cl to C12 alkyl group. The present invention further relates to a semiconducting material comprising at least one compound of formula (I), a semiconducting layer comprising at least one compound of formula (I) and an electronic device comprising at least one compound of formula (I). Exemplary compounds are for example metal complexes of 4-(2,4-dioxopentan-3-yl)-2,3,5,6-tetrafluorobenzonitrile, for example its Fe, Al and Cu complexes.

Description

Technical Field

[0001] The present invention relates to a compound of formula (I), a semiconductor material comprising at least one compound of formula (I), a semiconductor layer comprising at least one compound of formula (I), and an electronic device comprising at least one compound of formula (I). Background Technology

[0002] As self-emissive electronic devices, such as organic light-emitting diodes (OLEDs), they possess 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 layer, a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode layer, sequentially stacked on a substrate. In this regard, HIL, 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 HIL and 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 is emitted when the excitons transition from the excited state to the ground state. The injection and flow of holes and electrons should be balanced so that OLEDs with the above structure exhibit low operating voltage, excellent efficiency, and / or long lifetime.

[0004] The performance of organic light-emitting diodes can be affected by the characteristics of the hole injection layer, which in turn can be affected by the characteristics of the hole transport compounds and metal complexes contained in the hole injection layer.

[0005] US 2015200374 A relates to a hole injection layer composed of a secondary planar mononuclear transition metal complex, such as a copper 2+ complex, which is embedded, for example, in a hole-conducting matrix.

[0006] WO16188604 A1 relates to a composition comprising at least one hole transport and / or a hole injection material and at least one metal complex as a p-type dopant.

[0007] The performance of organic light-emitting diodes can be affected by the properties of the semiconductor layer, and in particular by the properties of the metal complexes also contained in the semiconductor layer.

[0008] There is a need to improve the performance of semiconductor materials, semiconductor layers and their electronic devices, especially by improving the properties of the compounds contained therein to achieve improved operating voltage stability over time.

[0009] In addition, it is still necessary to improve the performance of electronic devices by providing hole injection layers with improved performance, especially by improving the characteristics of hole injection layers and electronic devices to improve operating voltage.

[0010] In addition, a hole injection layer is still required that can inject into adjacent layers containing compounds with HOMO energy levels far from the vacuum level.

[0011] Another objective is to provide a hole injection layer comprising a compound that can be deposited by vacuum thermal evaporation under conditions suitable for large-scale production. Summary of the Invention

[0012] One aspect of the present invention provides a compound represented by formula I:

[0013] in

[0014] M is a metal;

[0015] L is a charge-neutral ligand coordinated with metal M;

[0016] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0017] m is an integer selected from 0 to 2;

[0018] R 1 R 2 and R 3 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0019] At least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0020] The substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18Aryl groups and substituted or unsubstituted C2 to C3 groups 18 The substituents of the heteroaryl group are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0021] in

[0022] At least one R 1 R 2 and / or R 3 Selected from the replaced C6 to C 24 aryl group,

[0023] The substituted C6 to C 24 At least one substituent of the aryl group is selected from CN and partially or fully fluorinated C1 to C2 groups. 12 alkyl.

[0024] definition

[0025] It should be noted that, unless otherwise noted, any R... throughout the application and claims... 1 R 2 R 3 L and M always refer to the same part.

[0026] In this specification, unless otherwise defined, "substitution" means substitution selected from: halogens, F, Cl, CN, substituted or unsubstituted C1 to C2. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Heteroaryl groups, wherein the substituents are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3.

[0027] In this specification, "aryl group" and "aromatic ring" refer to hydrocarbon groups that can be produced by formally isolating a hydrogen atom from an aromatic ring in 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 fluorenyl.

[0028] Similarly, “heteroaryl” and “heteroaromatic” are, where appropriate, understood in particular as groups derived by formally isolating a cyclic hydrogen atom from a compound containing at least one heterocyclic aromatic ring.

[0029] The term "non-heterocyclic" is understood to refer to a ring or ring system that does not contain heteroatoms as ring members.

[0030] The term "heterocycle" is understood to refer to a heterocycle containing at least one ring with one or more heteroatoms. A heterocycle containing more than one ring means that all rings contain heteroatoms, or that at least one ring contains heteroatoms and at least one ring contains only carbon atoms and no heteroatoms. A C2 heteroaryl group means that the heteroaryl ring contains two carbon atoms and the other atoms are heteroatoms. Heterocyclic alkyl groups are particularly understood, where appropriate, as groups derived by isolating a cyclic hydrogen atom from a compound containing at least one saturated cycloalkyl ring in such a ring form.

[0031] The term "aryl" refers to an aromatic group that does not contain heteroatoms, while the term "heteroaryl" refers to an aromatic group that contains at least one heteroatom.

[0032] The term "aryl" having at least 9 carbon atoms may contain at least one fused aryl ring. The term "heteroaryl" having at least 9 atoms may contain at least one fused heteroaryl ring fused with a heteroaryl ring or fused with an aryl ring.

[0033] The terms "fused aryl ring" or "condensed aryl ring" are understood as follows: when two aryl rings share at least two common sp... 2 When carbon atoms are hybridized, they are considered to be fused or condensed.

[0034] The term "fused ring system" is understood to refer to a ring system in which two or more rings share at least two atoms.

[0035] The terms "5-membered ring, 6-membered ring, or 7-membered ring" are understood to refer to a ring containing 5, 6, or 7 atoms. The atoms may be selected from carbon and one or more heteroatoms.

[0036] In this specification, a single key refers to a direct key.

[0037] In this specification, unless otherwise defined, "replaced" means replaced by H, deuterium, Cl to C 12 Alkyl, unsubstituted C6 to C 18 aryl, , and unsubstituted C2 to C 18 Hybridized aryl groups.

[0038] In this specification, "substituted aryl" refers to, for example, a C6 to C6 group substituted with one or more substituents. 24 Aryl or C6 to C 18Aryl, wherein the substituent itself may be unsubstituted or substituted by one or more substituents.

[0039] Accordingly, in this specification, "substituted heteroaryl" refers to, for example, C2 to C3 aryl groups substituted with one or more substituents. 24 Or C2 to C 18 The heteroaryl group may be unsubstituted or substituted by one or more substituents.

[0040] In this specification, unless otherwise defined, a substituted heteroaryl group having at least two C ring atoms may be substituted with one or more substituents. For example, a substituted C2 heteroaryl group may have one or two substituents.

[0041] A substituted aryl group having at least 6 ring atoms may be substituted by 1, 2, 3, 4 or 5 substituents.

[0042] The substituted heteroaryl group may contain at least six ring atoms. A substituted heteroaryl group containing at least six ring atoms may be substituted with one, two, three, or four substituents if the heteroaryl group contains one heteroatom and five carbon atoms; or it may be substituted with one, two, or three substituents if the heteroaryl group having at least six ring atoms contains two heteroatoms and four carbon atoms; or it may be substituted with one or two substituents if the heteroaryl group having at least six ring atoms contains three heteroatoms and three carbon atoms, wherein said substituents are bonded only to carbon ring atoms.

[0043] In this specification, unless otherwise defined, "alkyl group" refers to a saturated aliphatic hydrocarbon group. Alkyl groups can be C1 to C2. 12 Alkyl groups. More specifically, the alkyl groups can be C1 to C2. 10 Alkyl groups or C1 to C6 alkyl groups. For example, C1 to C4 alkyl groups contain 1 to 4 carbons in the alkyl chain and can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and cyclohexyl.

[0044] 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, branched pentyl groups, hexyl groups, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, adamantyl groups, etc.

[0045] In this specification, unless otherwise defined, "substituted alkyl group" can refer to a straight-chain, branched, or cyclic substituted saturated aliphatic hydrocarbon group. The substituted alkyl group can be a straight-chain, branched, or cyclic C1 to C2 group. 12Alkyl groups. More specifically, the substituted alkyl groups can be straight-chain, branched, or cyclic, with substitutions from C1 to C2. 10 An alkyl group, or a straight-chain, branched, or cyclic substituted C1 to C6 alkyl group. For example, a straight-chain, branched, or cyclic substituted C1 to C4 alkyl group contains 1 to 4 carbons in the alkyl chain and is selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, and cyclohexyl. Substituents may be selected from halogens, F, Cl, CN, OCH3, and OCF3.

[0046] The term "heteroatom" is understood as the replacement of at least one carbon atom in a structure that can be formed by covalently bonded carbon atoms with another multivalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, and S; more preferably from N, P, O, and S, and most preferably from N.

[0047] In this specification, when the substituent is not named, the substituent may be H.

[0048] The term "charge neutral" means that the group L is generally electrically neutral.

[0049] In the context of this invention, "different" means that the compounds do not have the same chemical structure.

[0050] 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.

[0051] The term "contact sandwich" refers to a three-layer arrangement in which the middle layer is in direct contact with the two adjacent layers.

[0052] The terms "light-absorbing layer" and "light-absorbing layer" are used synonymously.

[0053] The terms “light-emitting layer,” “light-emitting layer,” and “emitting layer” are used synonymously.

[0054] The terms “OLED,” “organic light-emitting diode,” and “organic light-emitting device” are used synonymously.

[0055] The terms anode, anode layer, and anode electrode are used synonymously.

[0056] The term "at least two anode sublayers" is understood to refer to two or more anode sublayers, such as two or three anode sublayers.

[0057] The terms cathode, cathode layer, and cathode electrode are used synonymously.

[0058] The term "hole injection layer" is understood to refer to a layer that improves charge injection from the anode layer to other layers in an organic electronic device or from other layers in an organic electronic device to the anode.

[0059] The term "hole transport layer" is understood to refer to the layer that transports holes between the hole injection layer and other layers arranged between the hole injection layer and the cathode layer.

[0060] The operating voltage U is measured in volts.

[0061] In the context of this specification, the terms "substantially non-luminescent" or "non-luminescent" refer to the contribution of a hole injection layer of a compound of formula (I) or a compound comprising formula (I) to the visible emission spectrum of an electronic device, such as an OLED or display device, of less than 10%, preferably less than 5%, relative to that visible emission spectrum. The visible emission spectrum is an emission spectrum with wavelengths from about ≥380 nm to about ≤780 nm.

[0062] In the context of this invention, the term "sublimation" may refer to a transformation from a solid to a gaseous phase or from a liquid to a gaseous phase.

[0063] In this specification, hole characteristics refer to the ability to form holes by providing electrons when an electric field is applied, and 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 due to their conductivity.

[0064] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and based on the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to their conductivity.

[0065] The term "HOMO level" is understood to refer to the highest occupied molecular orbital and is determined in eV (electron volts).

[0066] The term "HOMO level further from the vacuum level" is understood to mean that the absolute value of the HOMO level is higher than that of the reference compound. For example, the term "far from the vacuum level than the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirodi[fluorene]-2,2',7,7'-tetramine" is understood to mean that the absolute value of the HOMO level of the matrix compound in the hole injection layer is higher than that of the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirodi[fluorene]-2,2',7,7'-tetramine.

[0067] The term "absolute value" is understood to refer to a value without a "-" sign. According to one embodiment of the invention, the HOMO energy levels of the matrix compound in the hole injection layer can be calculated using quantum mechanical methods.

[0068] Beneficial effects

[0069] Surprisingly, the electronic device of the present invention solves the fundamental problem of the invention by enabling electronic devices, such as organic light-emitting diodes, to outperform electronic devices known in the art in all respects, particularly in terms of the stability of operating voltage over time and / or lifetime.

[0070] Furthermore, it has been found that the fundamental problem of the present invention can be solved by providing compounds suitable for deposition by vacuum thermal evaporation under conditions suitable for large-scale production. In particular, the standard onset temperature of the compounds of formula (I) of the present invention is within a range suitable for large-scale production.

[0071] The compound of formula (I) is non-luminescent. In the context of this specification, the terms "substantially non-luminescent" or "non-luminescent" mean that the compound of formula (I) contributes less than 10%, preferably less than 5%, to the visible emission spectrum of an electronic device, such as an OLED or display device. The visible emission spectrum is an emission spectrum with wavelengths from about ≥380 nm to about ≤780 nm.

[0072] M of the compound of formula (I)

[0073] The term "M" indicates metal. According to one embodiment, metal M may be selected from alkali metals, alkaline earth metals, transition metals, rare earth metals, or group III to V metals, preferably metal M is selected from transition metals or group III to V metals; preferably metal M is selected from Li(I), Na(I), K(I), Cs(I), Mg(II), Ca(II), Sr(II), Ba(II), Sc(III), Y(III), Ti(IV), V(III-V), Cr(III-VI), Mn(II), Mn(III), Fe(II), Fe(III), Co(II), Co(III), Ni(II), Cu(I), Cu(II), Zn(II), Ag(I), Au(I), Au(III), Al(III), Ga(III), In(III), Sn(II), Sn(IV) or Pb(II); preferably M is selected from Cu(II), Fe(III), Co(III), Mn(III), Ir(III), Bi(III), Al(III); more preferably M is selected from Fe(III), Cu(II) and / or Al(III). The elements in Groups IV-XI are called transition metals.

[0074] The ligand L of formula (I)

[0075] The term "L" denotes a charge-neutral ligand coordinated with metal M. According to one embodiment, L is selected from H₂O, C₂ to C₃. 40Monodentate or polydentate ethers and C2 to C 40 Sulfides, C2 to C 40 Amine, C2 to C 40 Phosphine, C2 to C 20 Alkyl nitrile or C2 to C 40 Aryl nitrile, or a compound according to formula (II);

[0076] in

[0077] R 6 and R 7 Independently selected from C1 to C 20 Alkyl, C1 to C 20 Heteroalkyl, C6 to C 20 aryl, heteroaryl with 5 to 20 cyclic atoms, halogenated or perhalogenated C1 to C2 groups 20 Alkyl, halogenated or fully halogenated C1 to C2 20 Heteroalkyl, halogenated or fully halogenated C6 to C 20 aryl, a halogenated or fully halogenated heteroaryl group having 5 to 20 cyclic atoms, or at least one R 6 and R 7 Bridges connect and form 5 to 20 element rings, or two R-shaped loops. 6 and / or two Rs 7 Bridges connect and form 5 to 40-membered rings or rings containing unsubstituted elements or C1 to C2 elements. 12 Substituted phenanthroline rings of 5 to 40 members.

[0078] According to one embodiment, the ligand L in the compound of formula (I) may be selected from groups comprising:

[0079] - At least three carbon atoms, or at least four carbon atoms, and / or

[0080] - at least two oxygen atoms or one oxygen and one nitrogen atom, two to four oxygen atoms, two to four oxygen atoms and zero to two nitrogen atoms, and / or

[0081] - At least one or more groups selected from halogens, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy groups, or two or more groups selected from halogens, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy groups, or at least one or more groups selected from halogens, F, CN, substituted C1 to C6 alkyl, substituted C1 to C6 alkoxy groups, or two or more groups selected from halogens, F, CN, perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkoxy groups, or one or more groups selected from substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C6 alkoxy groups. 12 Aryl and / or substituted or unsubstituted C3 to C412 heteroaryl groups,

[0082] The substituents are selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C6 alkyl groups. 16 Alkyl, partially or perfluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 3 COOR 3 Halogen, F or CN;

[0083] Where R 3 Selectable from C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C 16 Alkyl, partially or perfluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy.

[0084] Term "n"

[0085] The term "n" is an integer selected from 1 to 4, corresponding to the oxidation number of M. According to one embodiment, "n" is an integer selected from 1, 2, and 3, corresponding to the oxidation number of M. According to one embodiment, "n" is an integer selected from 1 or 2. According to another embodiment, "n" is an integer selected from 1 or 3. According to yet another embodiment, "n" is an integer selected from 2 or 3.

[0086] Term "m"

[0087] The term "m" is an integer selected from 0 to 2, corresponding to the oxidation number of M. According to one embodiment, "m" is an integer selected from 0 or 1. According to another embodiment, "m" is an integer selected from 1 or 2. According to yet another embodiment, "m" is an integer selected from 0 or 2.

[0088] Implementation

[0089] Compounds represented by formula I can also be called metal complexes or acetylacetone metal complexes.

[0090] According to one embodiment, the compound represented by formula I:

[0091] in

[0092] M is a metal;

[0093] L is a charge-neutral ligand coordinated with metal M;

[0094] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0095] m is an integer selected from 0 to 2;

[0096] R 1 R 2 and R 3 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0097] At least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0098] The substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 The substituents of the heteroaryl group are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0099] in

[0100] At least one R 1 R 2 and / or R 3 Selected from the replaced C6 to C 24 An aryl group, wherein the substituent is selected from at least two CN substituents, at least one or two CN substituents and one, two or three CF3 substituents, one CN substituent and one, two, three or four CF3 substituents, at least one CN and / or CF3 substituent and at least one F substituent.

[0101] According to one embodiment, the compound is represented by formula I:

[0102] in

[0103] M is a metal;

[0104] L is a charge-neutral ligand coordinated with metal M;

[0105] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0106] m is 0;

[0107] R 1 R 2 and R 3 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0108] At least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0109] The substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 The substituents of the heteroaryl group are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0110] in

[0111] At least one R 1 R 2 and / or R 3 Selected from the replaced C6 to C 24 aryl groups, wherein the substituted C6 to C6 groups are substituted. 24 At least one substituent of the aryl group is selected from CN and partially or fully fluorinated C1 to C2 groups. 12 alkyl.

[0112] According to one embodiment, the compound represented by formula I:

[0113] in

[0114] M is a metal;

[0115] L is a charge-neutral ligand coordinated with metal M;

[0116] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0117] m is 0;

[0118] R 1 R 2 and R 3 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0119] At least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0120] The substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 The substituents of the heteroaryl group are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0121] in

[0122] At least one R 1 R 2 and / or R 3 Selected from the replaced C6 to C 24An aryl group, wherein the substituent is selected from at least two CN substituents, at least one or two CN substituents and one, two or three CF3 substituents, one CN substituent and one, two, three or four CF3 substituents, at least one CN and / or CF3 substituent and at least one F substituent.

[0123] According to one embodiment, the molecular weight Mw of the metal complex of formula (I) can be ≥287 g / mol and ≤2000 g / mol, preferably ≥400 g / mol and ≤1500 g / mol, even more preferably ≥580 g / mol and ≤1500 g / mol, more preferably ≥580 g / mol and ≤1400 g / mol; and even more preferably ≥580 g / mol and ≤1100 g / mol.

[0124] According to one embodiment, the compound is represented by formula I:

[0125] in

[0126] M is a metal;

[0127] L is a charge-neutral ligand coordinated with metal M;

[0128] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0129] m is an integer selected from 0 to 2;

[0130] R 1 R 2 and R 3 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy groups and substituted or unsubstituted C6 to C6 groups 24 Aryl, of which

[0131] At least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy groups and substituted or unsubstituted C6 to C6 groups 18 Aryl, of which

[0132] The substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy groups and substituted or unsubstituted C6 to C6 groups 18The substituents of the aryl group are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0133] in

[0134] At least one R 1 R 2 and / or R 3 Selected from the replaced C6 to C 24 aryl group,

[0135] The substituted C6 to C 24 At least one substituent of the aryl group is selected from CN and partially or fully fluorinated C1 to C2 groups. 12 alkyl.

[0136] According to one embodiment, the compound is represented by formula I:

[0137] in

[0138] M is a metal;

[0139] L is a charge-neutral ligand coordinated with metal M;

[0140] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0141] m is an integer selected from 0 to 2;

[0142] R 1 and R 3 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0143] The at least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0144] The substituents are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0145] R2 Independently selected from substituted or unsubstituted C1 to C1 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0146] The at least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0147] The substituents are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0148] At least one of R 1 R 2 and / or R 3 Selected from the replaced C6 to C 24 An aryl group, wherein at least one substituent is selected from C1 to C2 and partially or fully fluorinated C1 to C2 groups. 12 alkyl.

[0149] According to one embodiment, the compound is represented by formula I:

[0150] in

[0151] M is a metal;

[0152] L is a charge-neutral ligand coordinated with metal M;

[0153] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0154] m is an integer selected from 0 to 2;

[0155] R 1 and R 3 Independently selected from substituted or unsubstituted C1 to C1 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0156] The at least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0157] The substituents are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0158] R 2 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0159] The at least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0160] The substituents are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0161] Where R 1 R 2 and R 3 One of them is selected from the replaced C6 to C 24 An aryl group, wherein at least one substituent is selected from C1 to C2 and partially or fully fluorinated C1 to C2 groups. 12 alkyl.

[0162] According to one embodiment, the compound is represented by formula I:

[0163] in

[0164] M is a metal;

[0165] L is a charge-neutral ligand coordinated with metal M;

[0166] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0167] m is an integer selected from 0 to 2;

[0168] R 1 R 2 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0169] The at least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, partially or fully fluorinated C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0170] The substituents are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0171] Where R 1 Or R 2 Selected from the replaced C6 to C 24 An aryl group, wherein at least one substituent is selected from CN or CF3; and

[0172] R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl groups, wherein the substituents are selected from halogens, F, Cl, CN, and CF3.

[0173] According to one embodiment, the compound is represented by formula I:

[0174] in

[0175] M is a metal;

[0176] L is a charge-neutral ligand coordinated with metal M;

[0177] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0178] m is an integer selected from 0 to 2;

[0179] R 1 R 2 and R 3 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0180] At least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 aryl, and substituted or unsubstituted C2 to C 18 Mixed aromatics, among which

[0181] The substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 The substituents of the heteroaryl group are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0182] in

[0183] At least one R 1 R 2 and / or R 3 Selected from the replaced C6 to C 24 aryl group,

[0184] The substituted C6 to C 24 At least one substituent of the aryl group is selected from CN and partially or fully fluorinated C1 to C2 groups. 12 alkyl.

[0185] According to one embodiment, the compound is represented by formula I:

[0186] in

[0187] M is a metal;

[0188] L is a charge-neutral ligand coordinated with metal M;

[0189] n is an integer selected from 1 to 4, which corresponds to the oxidation number of M;

[0190] m is an integer selected from 0 to 2;

[0191] R 1 R 2 and R3 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which

[0192] At least one substituent is selected from halogens, F, Cl, CN, substituted or unsubstituted C1 to C2 groups. 12 Alkyl, partially or fully fluorinated C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which

[0193] The substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 The substituents of the heteroaryl group are selected from halogens, F, Cl, CN, C1 to C6 alkyl groups, CF3, OCH3, and OCF3;

[0194] in

[0195] At least one R 1 R 2 and / or R 3 Selected from the replaced C6 to C 24 aryl group,

[0196] The substituted C6 to C 24 At least one substituent of the aryl group is selected from CN and partially or fully fluorinated C1 to C2 groups. 12 alkyl;

[0197] At least one of R 1 R 2 Or R 3 It is an aryl group selected from substituted phenyl groups, wherein

[0198] - The substituted aryl group contains at least two CN substituents; or

[0199] - The substituted aryl group comprises at least two CF3 substituents; or

[0200] - The substituted aryl group comprises at least one or two CN substituents and one, two or three CF3 substituents; or

[0201] - The substituted aryl group comprises one CN substituent and one, two, three, or four CF3 substituents; or

[0202] - The substituted aryl group comprises at least one CN and / or CF3 substituent and at least one F substituent; or

[0203] - The substituted aryl group comprises at least one CN and / or CF3 substituent and one, two, three, or four F substituents; or

[0204] - The substituted aryl group comprises one or two CF3 substituents and one, two, three, or four F substituents; and

[0205] Metal M is selected from transition metals or group III to V metals; preferably, metal M is selected from Cu(II), Fe(III), Co(III), Mn(III), Ir(III), Bi(III), Al(III); more preferably, M is selected from Fe(III), Cu(II) and / or Al(III), and even more preferably, M is selected from Cu(II).

[0206] According to one implementation, R 1 R 2 and R 3 Independently selected from H, D, substituted or unsubstituted C1 alkyl, substituted C6 to C1 alkyl. 24 Aryl, and R 1 Or R 2 It is selected from substituted C6-aryl rings, wherein at least one substituent is selected from halogen, F, Cl, CN, CF3.

[0207] According to one implementation, at least one R 1 R 2 Or R 3 It is selected from the substituted C6 to C 24 aryl group, substituted C6 to C 18 aryl group, substituted C6 to C 12 An aryl group or preferably a substituted phenyl group, wherein the substituted C6 to C6 group is an aryl group. 24 The aryl group is additionally substituted by at least one substituent selected from halogen, F, Cl, CN, C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkyl, C1 to C6 alkoxy, partially or perfluorinated C1 to C6 alkoxy.

[0208] According to one implementation, at least one R 1 R 2 Or R 3 It is selected from the substituted C6 to C 24 aryl group, substituted C6 to C 18 aryl group, substituted C6 to C 12 An aryl group or preferably a substituted phenyl group, wherein the substituted C6 to C6 group is an aryl group.24 The aryl group is completely substituted by a substituent selected from halogens, F, Cl, CN, C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkyl, C1 to C6 alkoxy, and partially or perfluorinated C1 to C6 alkoxy.

[0209] According to one implementation, at least one R 1 R 2 Or R 3 It is selected from the substituted C6 to C 24 aryl group, substituted C6 to C 18 aryl group, substituted C6 to C 12 An aryl group or preferably a substituted phenyl group, wherein the substituted C6 to C6 group is an aryl group. 24 The aryl group is additionally substituted by at least one substituent selected from halogen, F, Cl, CN, CF3 or OCF3.

[0210] According to one implementation, at least one R 1 R 2 Or R 3 It is selected from the substituted C6 to C 24 aryl group, substituted C6 to C 18 aryl group, substituted C6 to C 12 An aryl group or preferably a substituted phenyl group, wherein the substituted C6 to C6 group is an aryl group. 24 The aryl group is completely substituted by a substituent selected from halogen, F, Cl, CN, CF3 or OCF3.

[0211] According to one implementation, at least one R 1 R 2 Or R 3 It is selected from the substituted C6 to C 24 aryl group, C6 to C 18 aryl group, C6 to C 12 The aryl group, or preferably a substituted phenyl group, wherein

[0212] - The substituted aryl group contains at least one or two CN substituents; or

[0213] - The substituted aryl group contains at least one or two CF3 substituents; or

[0214] - The substituted aryl group comprises at least one or two CN substituents and one, two or three CF3 substituents; or

[0215] - The substituted aryl group comprises one CN substituent and one, two, three, or four CF3 substituents; or

[0216] - The substituted aryl group comprises at least one CN and / or CF3 substituent and at least one F substituent; or

[0217] - The substituted aryl group comprises at least one CN and / or CF3 substituent and one, two, three, or four F substituents; or

[0218] - The substituted aryl group contains one or two CF3 substituents and one, two, three or four F substituents.

[0219] According to one implementation, R 1 R 2 Or R 3 Selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted C6 to C 24 aryl groups, wherein the substituted C6 to C6 groups are substituted. 24 At least one substituent of the aryl group is selected individually from F, CN, or partially or fully fluorinated C1 to C2 groups. 12 Alkyl group, preferably CF3.

[0220] According to one implementation, R 1 Selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl groups, wherein the substituted C1 to C2 groups are alkyl groups. 12 The substituents of the alkyl group are selected from F and CN, preferably C1 to C1 of the substituted group. 12 The alkyl group is CF3; R 2 Selected from the replaced C6 to C 24 An aryl group, wherein at least one substituent is selected from F, CN, or partially or fully fluorinated C1 to C2 groups. 12 Alkyl group, preferably CF3; and R 3 Selected from H, D, unsubstituted or substituted C1 to C2 12 Alkyl, preferably CF3, wherein the substituted C1 to C2 12 The alkyl substituents are selected from halogens, F, Cl, and CN.

[0221] According to one implementation, R 1 Selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl groups, wherein the substituted C1 to C2 groups are alkyl groups. 12 The substituents of the alkyl group are selected from F and CN, preferably C1 to C1 of the substituted group. 12 The alkyl group is CF3; R 2 Selected from the replaced C6 to C 24 An aryl group, wherein at least one substituent is selected from F, CN, or partially or fully fluorinated C1 to C2 groups. 12 Alkyl group, preferably CF3; and R 3Selected from unsubstituted or substituted C1 to C 12 Alkyl, preferably CF3, wherein the substituted C1 to C2 12 The alkyl substituents are selected from F, Cl, and CN, with F being preferred.

[0222] According to one implementation, R 2 Selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl groups, wherein the substituted C1 to C2 groups are alkyl groups. 12 The substituents of the alkyl group are selected from F and CN, preferably C1 to C1 of the substituted group. 12 The alkyl group is CF3; R 1 Selected from the replaced C6 to C 24 An aryl group, wherein at least one substituent is selected from F, CN, or partially or fully fluorinated C1 to C2 groups. 12 Alkyl group, preferably CF3; and R 3 Selected from H, D, unsubstituted or substituted C1 to C2 12 Alkyl, preferably CF3, wherein the substituted C1 to C2 12 The alkyl substituents are selected from halogens, F, Cl, and CN.

[0223] According to one implementation, R 2 Selected from the replaced C6 to C 24 aryl group, wherein the substituents are selected from F, CN or partially or fully fluorinated C1 to C2 groups. 12 Alkyl group, preferably CF3; R 1 Selected from H or D; and R 3 Selected from unsubstituted or substituted C1 to C 12 Alkyl group, preferably CF3, CH3 or tert-butyl.

[0224] According to one implementation, R 1 Selected from substituted phenyl groups, wherein the substituents are selected from F, CN and / or partially or fully fluorinated C1 to C2 groups. 12 Alkyl group, preferably CF3; R 2 Selected from H, D; and R 3 Selected from unsubstituted or substituted C1 to C 12 Alkyl groups, preferably CF3, CH3, or C4H9, wherein the substituted C1 to C2 groups are substituted. 12 The alkyl substituents are selected from halogens, F, Cl, and CN.

[0225] According to one implementation, R 1 R 2 Selected from H, D, unsubstituted C1 to C 12 Alkyl group, preferably CH3, or selected from substituted phenyl rings, wherein at least one substituent is selected from F, Cl, CN, CF3; wherein R1 Or R 2 It is a substituted phenyl ring having at least one, two, three, four, or five substituents, wherein the substituents are selected from F, Cl, CN, CF3, preferably F, CN, or CF3; and R 3 It is unsubstituted C1 to C 12 Alkyl group, preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, CF3, or CN.

[0226] According to one implementation, R 1 R 2 Selected from H, D, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, preferably H, D, or CH3, or selected from substituted phenyl rings, wherein at least one substituent is selected from F, Cl, CN, or CF3, preferably F, CN, or CF3; wherein R 1 Or R 2 It is a substituted phenyl ring having at least one, two, three, four, or five substituents, wherein the substituents are individually selected from F, Cl, CN, CF3, preferably F, CN, or CF3; and R 3 It is methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, CF3, or CN.

[0227] According to one implementation, R 1 R 2 Selected from H, D, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl, preferably H, D, or CH3, or selected from substituted phenyl rings, wherein at least one substituent is selected from F, CN, or CF3; wherein R 1 Or R 2 It is a substituted phenyl ring having at least one to five substituents, wherein the substituents are individually selected from groups F, CN, CF3; and R 3 The components are CH3, n-butyl, isobutyl, sec-butyl, tert-butyl, CF3, and CN, with CH3, tert-butyl, or CF3 being preferred.

[0228] According to one implementation, R 1 R 2 Selected from unsubstituted H, D, Cl to C 12 Alkyl group, preferably CH3, or a substituted phenyl ring, wherein at least one substituent is selected from F, CN, CF3; wherein R 1 Or R 2 It is a substituted phenyl ring having at least three substituents, wherein the substituents are individually selected from halogens, F, Cl, CN, CF3, preferably groups of F, CN, or CF3; and R 3 It is CH3, CF3, or CN, with CH3 or CF3 being preferred.

[0229] According to one implementation, R 1 R 2 Selected from H, D, and unsubstituted C1 to C 12 Alkyl group, preferably CH3, or a substituted phenyl ring, wherein at least one substituent is selected from F, CN, CF3; wherein R 1 Or R 2 It is a substituted phenyl ring having at least two substituents, wherein the substituents are individually selected from halogens, F, Cl, CN, CF3, preferably groups of F, CN, or CF3; and R 3 It is CH3, CF3, or CN, with CH3 or CF3 being preferred.

[0230] According to one implementation, R 1 R 2 Selected from H, D, and unsubstituted C1 to C 12 Alkyl group, preferably CH3, or a substituted phenyl ring, wherein at least one substituent is selected from F, CN, CF3; wherein R 1 Or R 2 It is a substituted phenyl ring having at least one substituent, wherein the substituent is selected individually from halogens, F, Cl, CN, CF3, preferably groups of F, CN, or CF3; and R 3 It is CH3, CF3, or CN, with CH3 or CF3 being preferred.

[0231] According to one implementation, R 1 Selected from H, D, and unsubstituted C1 to C 12 Alkyl group, preferably CH3; R 2 It is a substituted phenyl ring having at least one substituent, wherein the substituent is selected individually from halogens, F, Cl, CN, CF3, preferably groups of F, CN, or CF3; and R 3 It is CH3, CF3, or CN, with CH3, C4H9, or CF3 being preferred.

[0232] According to one implementation, R 2 Selected from H, D, and unsubstituted C1 to C 12 Alkyl group, preferably CH3; R 1 It is a substituted phenyl ring having at least one substituent, wherein the substituent is selected individually from halogens, F, Cl, CN, CF3, preferably groups of F, CN, or CF3; and R 3 It is CH3, CF3, or CN, with CH3, C4H9, or CF3 being preferred.

[0233] According to one embodiment, C6 to C 24At least one substituent on the aryl group is selected from CN and partially or fully fluorinated C1 to C8 alkyl groups, preferably CF3; more preferably CN and partially or fully fluorinated C1 to C6 alkyl groups, and even more preferably CN and partially or fully fluorinated C1 to C4 alkyl groups.

[0234] According to one embodiment, C6 to C 24 At least one substituent of the aryl group is selected from at least one F, CN, or CF3 group.

[0235] According to one implementation, R 1 R 2 R 3 It may be selected from C2 to C, whether substituted or unsubstituted. 24 heteroaryl groups or substituted or unsubstituted C2 to C3 groups 18 heteroaryl groups.

[0236] According to one implementation, R 1 R 2 and R 3 It may not be selected from substituted or unsubstituted heteroaryl groups.

[0237] According to one embodiment, formula I may not contain substituted or unsubstituted C2 to C 24 heteroaryl groups or substituted or unsubstituted C2 to C3 groups 18 heteroaryl groups.

[0238] According to one embodiment, Formula I may not contain substituted or unsubstituted heteroaryl groups.

[0239] According to one implementation, R 1 R 2 Or R 3 At least one substituted C6 to C 24 The aryl group is selected from the following formulas D1 to D19:

[0240]

[0241] The asterisk (*) indicates the binding position.

[0242] According to one embodiment, the compound represented by formula I is selected from the following formulas E1 to E38:

[0243]

[0244]

[0245]

[0246] According to one embodiment, the compound represented by Formula I is selected from the following formulas E1 to E32 and / or E33 to E38; and M is a metal; preferably M is selected from alkali metals, alkaline earth metals, transition metals, rare earth metals or group III to V metals, more preferably metal M is selected from transition metals or group III to V metals; even more preferably metal M is selected from Li(I), Na(I), K(I), Cs(I), Mg(II), Ca(II), Sr(II), Ba(II), Sc(III), Y(III), Ti(IV), V(III-V), C r(III-VI), Mn(II), Mn(III), Fe(II), Fe(III), Co(II), Co(III), Ni(II), Cu(I), Cu(II), Zn(II), Ag(I), Au(I), Au(III ), Al(III), Ga(III), In(III), Sn(II), Sn(IV) or Pb(II); it is also preferred that M is selected from Cu(II), Fe(III), Co(III), Mn(III), Ir(III), Bi(III).

[0247] According to one embodiment, the compound represented by formula I is selected from formulas E2 to E38 and M is selected from alkali metals, alkaline earth metals, transition metals or group III to V metals, more preferably metal M is selected from transition metals or group III to V metals; it is also preferred that metal M is selected from Li(I), Na(I), K(I), Cs(I), Mg(II), Ca(II), Sr(II), Ba(II), Sc(III), Y(III), Ti(IV), V(III-V), Cr(III-VI), Mn(II), Mn(III), Fe(II), Fe(III), Co(II), Co(III), Ni(II), Cu(I), Cu(II), Zn(II), Ag(I), Au(I), Au(III), Al(III), Ga(III), In(III), Sn(II), Sn(IV) or Pb(II); it is also preferred that M is selected from Cu(II), Fe(III), Co(III), Mn(III), Ir(III), Bi(III).

[0248] According to one embodiment, the compound represented by formula I is selected from formulas E2 to E38 and M is selected from Cu(II), Fe(III) and / or Al(III).

[0249] According to one embodiment, the compound represented by formula I is selected from formulas E2 to E38; and M is selected from Cu(II), Fe(III) and / or Al(III); wherein formula E1 and M = Cu(II) or Fe(III) and formula E6 and M = Fe(III) are excluded.

[0250] According to one embodiment, the compound represented by formula I is selected from formulas E2 to E38; and M is selected from Cu(II) and / or Al(III).

[0251] According to one embodiment, the compound represented by formula I is selected from the following formulas G1 to G76:

[0252]

[0253]

[0254]

[0255]

[0256]

[0257] According to one embodiment, the compound represented by formula I is selected from formulas G4 to G76, preferably G4 to G9 and G13 to G76.

[0258] Essentially covalent matrix compounds

[0259] A substantially covalent matrix compound, also known as a matrix compound, can be an organoaromatic matrix compound containing covalently bonded organic aromatic carbon atoms. A substantially covalent matrix compound can be an organic compound consisting substantially of covalently bonded C, H, O, N, and S, and optionally may also contain covalently bonded B, P, or Si. A substantially covalent matrix compound can be an organoaromatic covalently bonded compound that does not contain metal atoms, and most of its skeletal atoms are selected from C, O, S, and N, preferably from C, O, and N, wherein the majority of atoms are C atoms. Alternatively, the covalent matrix compound does not contain metal atoms and most of its skeletal atoms are selected from C and N, preferably the covalent skeletal compound does not contain metal atoms and most of its skeletal atoms are selected from C, and a minority of its skeletal atoms may be N.

[0260] According to one embodiment, the molecular weight Mw of the substantially covalent matrix compound can be ≥400 g / mol and ≤2000 g / mol, preferably ≥450 g / mol and ≤1500 g / mol, even more preferably ≥500 g / mol and ≤1000 g / mol, more preferably ≥550 g / mol and ≤900 g / mol, and even more preferably ≥600 g / mol and ≤800 g / mol.

[0261] In one embodiment, when determined under the same conditions, the HOMO level of the substantially covalent matrix compound can be more negative than the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirobis[fluorene]-2,2',7,7'-tetramine (CAS207739-72-8).

[0262] In one embodiment of the invention, the substantially covalent matrix compound may be free of alkoxy groups.

[0263] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, or a diarylamine moiety, or a triarylamine moiety.

[0264] Preferably, the substantially covalent matrix compound is free of TPD or NPB.

[0265] Preferably, the matrix compound of the hole injection layer does not contain metal and / or ionic bonds.

[0266] Compounds of formula (III) or compounds of formula (IV)

[0267] According to another aspect of the invention, the substantially covalent matrix compound may comprise: at least one arylamine compound, a diarylamine compound, a triarylamine compound, a compound of formula (III), or a compound of formula (IV):

[0268]

[0269] in:

[0270] T 1 T 2 T 3 T 4 and T 5 It is independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably single bond or phenylene group;

[0271] T 6 It is a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group;

[0272] Ar1 Ar 2 Ar 3 Ar 4 and Ar 5 Selected independently from: substituted or unsubstituted C6 to C 20 aryl, or substituted or unsubstituted C3 to C4 20 Heteroarylene groups, substituted or unsubstituted biphenylene groups, 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 triphenylene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[a]anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzo[b,f]-heptan, substituted or unsubstituted 9,9'-spiro[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-heterogeneous 5-membered 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 selected from: (i) unsaturated 5 to 7-membered heterocycles, (ii) 5 to 6-membered aromatic heterocycles, (iii) unsaturated 5 to 7-membered non-heterogeneous rings, (iv) 6-membered aromatic non-heterogeneous rings;

[0273] in

[0274] Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from H, D, F, C(-O)R, either the same or different. 2 CN, Si(R) 2 )3, P(-O)(R 2 )2, OR 2 S(-O)R 2 S(-O)2R 2Substituted 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 Heteroaryl groups are fused ring systems comprising 2 to 6 unsubstituted 5- to 7-membered rings, wherein the 5- to 7-membered rings are selected from: unsaturated 5- to 7-membered heterocycles, 5- to 6-membered aromatic heterocycles, unsaturated 5- to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles.

[0275] Where R 2 The following 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.

[0276] According to one embodiment of the electronic device, the substantially covalent matrix compound comprises a compound of formula (III) or formula (IV):

[0277]

[0278] in

[0279] 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;

[0280] T 6 It is a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group;

[0281] 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 C4 20Heteroarylene groups, substituted or unsubstituted biphenylene groups, 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 triphenylene, substituted or unsubstituted tetraphenylene, substituted or unsubstituted benzo[a]anthracene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzo[b,f]-heptan, substituted or unsubstituted 9,9'-spiro[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-heterogeneous 5-membered 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 selected from: (i) unsaturated 5 to 7-membered heterocycles, (ii) 5 to 6-membered aromatic heterocycles, (iii) unsaturated 5 to 7-membered non-heterogeneous rings, (iv) 6-membered aromatic non-heterogeneous rings;

[0282] Among them, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from the following groups, either identically or differently: H, straight-chain alkyl groups having 1 to 20 carbon atoms, branched alkyl groups having 1 to 20 carbon atoms, cyclic alkyl groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, C6 to C4... 18 Aryl, C3 to C 18 Heteroaryl groups are fused ring systems comprising 2 to 6 unsubstituted 5- to 7-membered rings selected from: unsaturated 5- to 7-membered heterocycles, 5- to 6-membered aromatic heterocycles, unsaturated 5- to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles.

[0283] Preferably, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from the following groups, either identically or differently: H, 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 alkynyl groups having 2 to 6 carbon atoms, alkoxy groups having 1 to 6 carbon atoms, C6 to C6... 18 Aryl, C3 to C18 The heteroaryl group comprises a fused ring system of 2 to 4 unsubstituted 5 to 7-membered rings, wherein the unsubstituted 5 to 7-membered rings are selected from: unsaturated 5 to 7-membered heterocycles, 5 to 6-membered aromatic heterocycles, unsaturated 5 to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles; more preferably, the substituents are selected from H, straight-chain alkyl groups having 1 to 4 carbon atoms, branched alkyl groups having 1 to 4 carbon atoms, cyclic alkyl groups having 3 to 4 carbon atoms, and / or phenyl groups.

[0284] Therefore, compounds of formula (III) or (IV) can have a standard starting temperature suitable for large-scale production.

[0285] According to one embodiment of the electronic device, the substantially covalent matrix compound comprises a compound of formula (III) or formula (IV):

[0286]

[0287] in

[0288] 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;

[0289] T 6 It is a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group;

[0290] Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Can be independently selected from: unsubstituted C6 to C 20 aryl, or unsubstituted C3 to C 20Heteroarylene, unsubstituted biphenylene, unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, unsubstituted naphthalene, unsubstituted anthracene, unsubstituted phenanthrene, unsubstituted pyrene, unsubstituted perylene, unsubstituted triphenylene, unsubstituted tetracene, unsubstituted benzanthracene, unsubstituted dibenzofuran, unsubstituted dibenzothiophene, unsubstituted xanthene, unsubstituted carbazole, substituted 9-phenylcarbazole, unsubstituted azepine, unsubstituted dibenzo[b,f]azepine, unsubstituted 9,9'-spirobi[fluorene], unsubstituted spiro[fluorene-9,9'-xanthene], or an unsubstituted aromatic fused ring system comprising at least three unsubstituted aromatic rings selected from unsubstituted non-hetero 5-membered rings, unsubstituted hetero 5-membered rings, unsubstituted 6-membered rings and / or unsubstituted 7-membered rings, unsubstituted fluorene, or a fused ring system comprising 2 to 6 unsubstituted 5 to 7-membered rings, wherein the unsubstituted 5 to 7-membered rings are selected from: (i) unsaturated 5 to 7-membered heterocycles, (ii) 5 to 6-membered aromatic heterocycles, (iii) unsaturated 5 to 7-membered non-heterocycles, (iv) 6-membered aromatic non-heterocycles.

[0291] According to one embodiment of the electronic device, wherein the substantially covalent matrix compound comprises a compound of formula (III) or formula (IV):

[0292]

[0293] wherein

[0294] T 1 , T 2 , T 3 , T 4 and T 5 may be independently selected from a single bond, phenylene, biphenylene, terphenylene or naphthylene, preferably a single bond or phenylene;

[0295] T 6 is phenylene, biphenylene, terphenylene or naphthylene;

[0296] Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 may be independently selected from: unsubstituted C6 to C 20 aryl, or unsubstituted C3 to C 20Heteroarylene, unsubstituted biphenylene, unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, unsubstituted naphthalene, unsubstituted anthracene, unsubstituted phenanthrene, unsubstituted pyrene, unsubstituted perylene, unsubstituted triphenylene, unsubstituted tetraphenylene, unsubstituted benzo[b,f]-anthracene, unsubstituted dibenzofuran, unsubstituted dibenzothiophene, unsubstituted saxon, unsubstituted carbazole, substituted 9-phenylcarbazole, unsubstituted aziridine heptane, unsubstituted dibenzo[b,f]aziridine heptane, unsubstituted 9,9'-spirodi[fluorene], unsubstituted spiro[fluorene-9,9'-saxon].

[0297] Therefore, compounds of formula (III) or (IV) can have a standard starting temperature suitable for large-scale production.

[0298] According to one implementation, where T 1 T 2 T 3 T 4 and T 5 It can be independently selected from single bonds, benzene groups, biphenylene groups, or triphenylene 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 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 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 The two in it are single bonds.

[0299] According to one implementation, where T 1 T2 and T 3 It can be independently selected from phenylene group and T 1 T 2 and T 3 One is a single bond. According to one implementation, where T... 1 T 2 and T 3 Can be independently selected from phenylene group and T 1 T 2 and T 3 The two in it are single bonds.

[0300] According to one implementation, where T 6 It can be a phenylene group, a biphenylene group, or a terphenylene group. According to one embodiment, T... 6 It can be a benzene group. According to one embodiment, T... 6 It can be a biphenyl group. According to one embodiment, wherein T... 6 It could be a triphenylene oxide.

[0301] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Can be selected independently from B1 to B16:

[0302]

[0303]

[0304] The asterisk "*" indicates the position of the combination.

[0305] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be selected independently from B1 to B15; or selected from B1 to B10 and B13 to B15.

[0306] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be independently selected from B1, B2, B5, B7, B9, B10, B13 to B16.

[0307] When selecting Ar within this range 1 Ar 2 Ar 3 Ar4 and Ar 5 At that time, the standard starting temperature can be within a range that is particularly suitable for large-scale production.

[0308] “Matrix compounds of formula (III) or (IV)” can also be called “hole transport compounds”.

[0309] According to one embodiment, the compound of formula (III) or formula (IV) may comprise an aromatic fused ring system containing at least 1 to 6 substituted or unsubstituted heteroaromatic rings.

[0310] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least 1 to 6 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings and at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings.

[0311] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least 1 to 6 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings, and at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings, and at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles, more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings and optionally at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles, and even more preferably the aromatic fused ring system containing heteroaromatic rings is unsubstituted, and optionally at least 1 to 3 unsubstituted unsaturated 5 to 7-membered heterocycles.

[0312] According to one embodiment, the compound of formula (III) or formula (IV) may contain at least 1 to 6 substituted or unsubstituted aromatic fused ring systems, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems, and even more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems.

[0313] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least 1 to 6 substituted or unsubstituted aromatic fused ring systems, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems, and even more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems comprising substituted or unsubstituted aromatic rings.

[0314] According to one embodiment, the compound of formula (III) or formula (IV) may contain at least 1 to 3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0315] According to one embodiment, the compound of formula (III) or formula (IV) may contain at least 1 to ≤3 or 2 heterocycles of substituted or unsubstituted unsaturated 7-membered rings.

[0316] According to one embodiment, the substituted or unsubstituted aromatic fused ring system of the compound of formula (III) or formula (IV) may contain at least 1 to ≤3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0317] According to one embodiment, the substituted or unsubstituted aromatic fused ring system of the matrix compound of formula (III) or (IV) may contain at least 1 to ≤3 or 2 substituted or unsubstituted unsaturated 7-membered rings of heterocyclic rings.

[0318] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least 1 to 6 substituted or unsubstituted aromatic fused ring systems, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems, and even more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein said aromatic fused ring system comprises a heterocycle of a substituted or unsubstituted unsaturated 5 to 7-membered ring.

[0319] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least 1 to 6 substituted or unsubstituted aromatic fused ring systems, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems, and even more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system comprises substituted or unsubstituted aromatic rings, and wherein the aromatic fused ring system comprises a heterocycle of a substituted or unsubstituted unsaturated 5 to 7-membered ring.

[0320] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least 1 to 6 substituted or unsubstituted aromatic fused ring systems, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems, and even more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system comprises at least 1 to 3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0321] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least 1 to 6 substituted or unsubstituted aromatic fused ring systems, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems, and even more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system comprises substituted or unsubstituted heteroaromatic rings, and wherein the aromatic fused ring system comprises at least 1 to 3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0322] According to one embodiment, the compound of formula (III) or formula (IV) may comprise:

[0323] - A substituted or unsubstituted aromatic fused ring system having at least 2 to ≤6, preferably 3 to ≤5, or 4 fused aromatic rings, wherein the rings are selected from: substituted or unsubstituted non-heteroaromatic rings, substituted or unsubstituted heterocyclic 5-membered rings, substituted or unsubstituted 6-membered rings, and / or heterocyclic rings with substituted or unsubstituted unsaturated 5- to 7-membered rings; or

[0324] - An unsubstituted aromatic fused ring system having at least 2 to 6, preferably 3 to 5, or 4 fused aromatic rings, wherein the rings are selected from: unsubstituted non-heteroaromatic rings, unsubstituted hetero 5-membered rings, unsubstituted 6-membered rings, and / or unsubstituted unsaturated 5- to 7-membered rings.

[0325] It should be noted here that the term "aromatic fused ring system" may include at least one aromatic ring and at least one substituted or unsubstituted unsaturated 5- to 7-membered ring. It should also be noted here that the substituted or unsubstituted unsaturated 5- to 7-membered ring may not be an aromatic ring.

[0326] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least 1 to ≤6, preferably 2 to ≤5, or even more preferably 3 or 4 of the substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system has:

[0327] - At least one unsaturated 5-membered ring, and / or

[0328] - At least one unsaturated 6-membered ring, and / or

[0329] - At least one unsaturated 7-membered ring; wherein preferably at least one unsaturated 5-membered ring and / or at least one unsaturated 7-membered ring contains at least 1 to 3, preferably 1, heteroatom.

[0330] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least 1 to ≤6, preferably 2 to ≤5, or even more preferably 3 or 4 of the substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring system has:

[0331] - At least one aromatic 5-membered ring, and / or

[0332] - At least one aromatic 6-membered ring, and / or

[0333] - At least one aromatic 7-membered ring; wherein preferably at least one aromatic 5-membered ring and / or at least one aromatic 7-membered ring contains at least 1 to 3, preferably 1, heteroatom;

[0334] The substituted or unsubstituted aromatic fused ring system comprises at least 1 to ≤3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles.

[0335] According to one embodiment, the compound of formula (III) or formula (IV) may comprise:

[0336] - At least 6 to 12, preferably 7 to 11, even more preferably 8 to 10, or 9 aromatic rings; and / or

[0337] - At least 4 to 11, preferably 5 to 10, more preferably 6 to 9, or even more preferably 7 or 8 non-heterotropic aromatic rings, preferably said non-heterotropic aromatic rings are aromatic C6 rings; and / or

[0338] - At least 1 to ≤4, preferably 2 or 3, aromatic 5-membered rings, preferably heteroaromatic 5-membered rings; and / or

[0339] - At least one or two unsaturated 5- or 7-membered heterocycles, preferably at least one or two unsaturated 7-membered heterocycles;

[0340] - At least 6 to 12, preferably 7 to 11, even more preferably 8 to 10, or 9 aromatic rings, wherein

[0341] At least 4 to 11, preferably 5 to 10, even more preferably 6 to 9, or more preferably 7 or 8, are non-heteroaromatic rings, and

[0342] At least 1 to 4, preferably 2 or 3, aromatic rings are heteroaromatic rings, wherein the total number of non-heteroaromatic rings and heteroaromatic rings does not exceed 12 aromatic rings; and / or

[0343] - At least 6 to 12, preferably 7 to 11, even more preferably 8 to 10, or 9 aromatic rings, wherein

[0344] At least 4 to 11, preferably 5 to 10, even more preferably 6 to 9, or more preferably 7 or 8, are non-heteroaromatic rings, and

[0345] At least 1 to 4, preferably 2 or 3, aromatic rings are heterocyclic aromatic rings, wherein the total number of non-heterocyclic and heterocyclic aromatic rings does not exceed 12 aromatic rings; and

[0346] The hole transport compound or the hole transport compound according to Formula I comprises at least 1 to ≤4, preferably 2 or 3, aromatic 5-membered rings, preferably heteroaromatic 5-membered rings, and / or

[0347] Hole transport compounds or hole transport compounds according to Formula I contain at least one or two unsaturated 5- to 7-membered heterocycles, preferably at least one or two unsaturated 7-membered heterocycles.

[0348] According to one embodiment, the compound of formula (III) or formula (IV) may contain heteroatoms, which may be selected from O, S, N, B or P, preferably selected from O, S or N.

[0349] According to one embodiment, the matrix compound of formula (III) or (IV) may comprise at least 1 to 6, preferably 2 to 5, or even more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, said aromatic fused ring system having:

[0350] - At least one aromatic 5-membered ring, and / or

[0351] - At least one aromatic 6-membered ring, and / or

[0352] - At least one aromatic 7-membered ring; wherein preferably at least one aromatic 5-membered ring and / or at least one aromatic 7-membered ring contains at least 1 to 3, preferably 1, heteroatom;

[0353] The substituted or unsubstituted aromatic fused ring system optionally comprises at least 1 to 3 or 2 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles; and the substituted or unsubstituted aromatic fused ring system comprises heteroatoms, which may be selected from O, S, N, B, P or Si, preferably selected from O, S or N.

[0354] According to one embodiment, the compound of formula (III) or formula (IV) may not contain heteroatoms that are not part of an aromatic ring and / or an unsaturated 7-membered ring, preferably the hole-transporting compound or the hole-transporting compound according to formula (I) may not contain N- atoms other than N atoms that are part of an aromatic ring or an unsaturated 7-membered ring.

[0355] According to one embodiment, the substantially covalent matrix compound comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group and / or a substituted fluorenyl group, wherein the substituent is independently selected from methyl, phenyl or fluorenyl.

[0356] According to one embodiment of the electronic device, the compound of formula (III) or formula (IV) is selected from K1 to K15:

[0357]

[0358]

[0359]

[0360] The substantially covalent matrix compound may be free of HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604, and EL-22T. The abbreviations indicate the manufacturer's name, such as Merck or Lumtec.

[0361] semiconductor materials

[0362] According to another aspect, a semiconductor material comprising at least one compound of formula I is provided. The semiconductor material may further comprise at least one substantially covalent matrix compound.

[0363] semiconductor layer

[0364] According to another aspect, the semiconductor layer comprises at least one compound of formula I.

[0365] According to one embodiment, the semiconductor layer comprising at least one compound of Formula I is a hole injection layer.

[0366] According to another embodiment, the semiconductor layer comprises a semiconductor material containing at least one compound of formula I.

[0367] electronic devices

[0368] According to another embodiment, the electronic device includes a substrate, an anode layer without sublayers or an anode layer that may contain two or more sublayers, a cathode layer, and a hole injection layer, wherein the hole injection layer contains a compound according to formula (I).

[0369] The electronic device may include at least one photoactive layer. The at least one photoactive layer may be a light-emitting layer or a light-absorbing layer, preferably a light-emitting layer.

[0370] According to another embodiment, the electronic device may have the following layer structure, wherein the layers have the following order:

[0371] The anode layer, a hole injection layer comprising a substantially covalent matrix compound and a compound of formula (I), a hole transport layer, an optional electron blocking layer, at least a first light-emitting layer, an optional hole blocking layer, an electron transport layer, an optional electron injection layer, and a cathode layer.

[0372] According to another aspect, an electronic device is provided, the electronic device comprising a semiconductor material containing a compound according to formula (I) and a semiconductor layer containing a compound according to formula (I). The electronic device may be selected from devices including light-emitting devices, thin-film transistors, batteries, display devices, or photovoltaic cells, and is preferably a light-emitting device, preferably the electronic device being part of a display device or a lighting device.

[0373] According to another aspect, an electronic device is provided that includes at least one organic light-emitting device according to any embodiment described throughout this application, preferably, the electronic device includes an organic light-emitting diode as described throughout this application. More preferably, the electronic device is a display device.

[0374] According to one embodiment of the present invention, the electronic device may include a semiconductor layer comprising a compound of formula (I) and a substantially covalent matrix compound, the matrix compound comprising at least one arylamine compound, a diarylamine compound, or a triarylamine compound, wherein in formula (I), M is selected from Li(I), Na(I), K(I), Cs(I), Mg(II), Ca(II), Sr(II), Ba(II), Sc(III), Y(III), Ti(IV), V(III-V), Cr(III-VI), Mn(II), Mn(III) The ingredients are: Fe(II), Fe(III), Co(II), Co(III), Ni(II), Cu(I), Cu(II), Zn(II), Ag(I), Au(I), Au(III), Al(III), Ga(III), In(III), Sn(II), Sn(IV) or Pb(II); preferably M is selected from Cu(II), Fe(III), Co(III), Mn(III), Ir(III), Bi(III); more preferably M is selected from Fe(III) and Cu(II); and even more preferably M is selected from Cu(II).

[0375] Anode layer

[0376] The anode layer, also known as the anode electrode, is formed by deposition or sputtering of a 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 layer 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 layer. Metals, typically silver (Ag), gold (Au), or metal alloys, can also be used to form the anode layer.

[0377] An anode layer may contain two or more anode sublayers.

[0378] According to one embodiment, the anode layer includes a first anode sublayer and a second anode sublayer, wherein the first anode sublayer is disposed closer to the substrate and the second anode sublayer is disposed closer to the cathode layer.

[0379] According to one embodiment, the anode layer may include a first anode sublayer containing or composed of Ag or Au and a second anode sublayer containing or composed of transparent conductive oxide.

[0380] According to one embodiment, the anode layer includes a first anode sublayer, a second anode sublayer, and a third anode sublayer, wherein the first anode sublayer is disposed closer to the substrate, the second anode sublayer is disposed closer to the cathode layer, and the third anode sublayer is disposed between the substrate and the first anode sublayer.

[0381] According to one embodiment, the anode layer may include a first anode sublayer containing or composed of Ag or Au, a second anode sublayer containing or composed of transparent conductive oxide, and optionally a third anode sublayer containing or composed of transparent conductive oxide. Preferably, the first anode sublayer may contain or be composed of Ag, the second anode sublayer may contain or be composed of ITO or IZO, and the third anode sublayer may contain or be composed of ITO or IZO.

[0382] Preferably, the first anode sublayer may contain Ag or be composed of Ag, the second anode sublayer may contain ITO or be composed of ITO, and the third anode sublayer may contain ITO or be composed of ITO.

[0383] Preferably, the transparent conductive oxides in the second and third anode sublayers can be the same.

[0384] According to one embodiment, the anode layer may include a first anode sublayer containing Ag or Au with a thickness of 100 to 150 nm, a second anode sublayer containing or composed of transparent conductive oxide with a thickness of 3 to 20 nm, and a third anode sublayer containing or composed of transparent conductive oxide with a thickness of 3 to 20 nm.

[0385] Hole injection layer

[0386] Hole-injected layers (HILs) can be formed on the anolyte layer through vacuum deposition, spin coating, printing, casting, slot die coating, and Langmuir-Blodgett (LB) deposition. When using vacuum deposition to form HILs, the deposition conditions can vary depending on the hole transport compound used to form the HIL and the desired structure and thermal properties of the HIL. However, generally, vacuum deposition conditions can include deposition temperatures ranging from 100°C to 350°C and pressures of 10... -8 Up to 10 -3 Torr (1 Torr equals 133.322 Pa) and deposition rates of 0.1 to 10 nm / s.

[0387] When spin coating or printing is used to form HILs, the coating conditions can vary depending on the hole transport compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C. After coating, heat treatment removes the solvent.

[0388] HIL can be formed from compounds of formula (I).

[0389] The thickness of HIL can range from about 1 nm to about 15 nm, for example from about 2 nm to about 15 nm, or from about 2 nm to about 12 nm.

[0390] When the thickness of HIL is within this range, HIL can have excellent hole injection characteristics without substantially damaging the driving voltage.

[0391] According to one embodiment of the present invention, the hole injection layer may include:

[0392] - at least about ≥0.5 wt% to about ≤30 wt%, preferably about ≥0.5 wt% to about ≤20 wt%, more preferably about ≥15 wt% to about ≤1 wt% of compounds of formula (I), and

[0393] - At least about ≥70% by weight to about ≤99.5% by weight, preferably about ≥80% by weight to about ≤99.5% by weight, more preferably about ≥85% by weight to about ≤99% by weight, of a substantially covalent matrix compound; preferably the weight percentage of the compound of formula (I) is less than the weight percentage of the substantially covalent matrix compound; wherein the weight percentage of the component is based on the total weight of the hole injection layer.

[0394] Preferably, the hole injection layer may be free of ionic liquids, metal phthalocyanines, CuPc, HAT-CN, pyrazino[2,3-f][1,10]phenanthroline-2,3-dionitrile, F4TCNQ, metal fluorides, and / or metal oxides, wherein the metal in the metal oxide is selected from Re and / or Mo. Thus, the hole injection layer can be deposited under conditions suitable for large-scale production.

[0395] According to one embodiment of the electronic device, the hole injection layer does not emit light.

[0396] It should be understood that the hole injection layer is not part of the anode layer.

[0397] Other layers

[0398] According to the present invention, in addition to the layers already mentioned above, the electronic device may also include other layers. Exemplary embodiments of each layer are described below:

[0399] base

[0400] 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 transistor backplane. Preferably, the substrate is a silicon substrate or a transistor backplane.

[0401] Hole transport layer

[0402] According to one embodiment of the electronic device, the electronic device further includes a hole transport layer, wherein the hole transport layer is disposed between the hole injection layer and the at least one light-emitting layer.

[0403] The hole transport layer may comprise a substantially covalent matrix compound. According to one embodiment, the substantially covalent matrix compound of the hole transport layer 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 also comprises covalently bonded B, P, As, and / or Se.

[0404] According to one embodiment of the electronic device, the hole transport layer comprises a substantially covalent matrix compound, wherein the substantially covalent matrix compound of the hole transport layer is selected from an organic compound consisting substantially of covalently bonded C, H, O, N, S, and optionally also comprises covalently bonded B, P, As and / or Se.

[0405] According to one embodiment, the molecular weight Mw of the substantially covalent matrix compound of the hole transport layer can be ≥400 and ≤2000 g / mol, preferably ≥450 and ≤1500 g / mol, even more preferably ≥500 and ≤1000 g / mol, more preferably ≥550 and ≤900 g / mol, and even more preferably ≥600 and ≤800 g / mol.

[0406] Preferably, the substantially covalent matrix compound of the hole injection layer and the substantially covalent matrix compound of the hole transport layer are selected to be the same.

[0407] According to one embodiment of an electronic device, the hole transport layer of the electronic device comprises a substantially covalent matrix compound, preferably the substantially covalent matrix compound of the hole injection layer and the hole transport layer is selected to be the same.

[0408] Hole transport layers (HILs) can be formed on HILs through 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 used for forming HILs. However, the conditions for vacuum or solution deposition can vary depending on the hole transport compound used to form the HTL.

[0409] The thickness of the 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 200 nm, even more preferably about 100 nm to about 180 nm, even more preferably about 110 nm to about 140 nm.

[0410] When the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without substantially damaging the driving voltage.

[0411] Electron blocking layer

[0412] The function of an electron blocking layer (EBL) is to prevent electrons from transferring from the light-emitting layer to the hole transport layer, thereby confining electrons within the light-emitting layer. This improves efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer contains a triarylamine compound.

[0413] If an electron blocking layer has a high triplet energy level, it can also be called a triplet control layer.

[0414] 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 of the phosphorescent emitting layer. The triplet control layer can be selected from triarylamine compounds, whose triplet energy levels are higher than those of the phosphorescent emitters in adjacent emitting layers.

[0415] The thickness of the electron blocking layer can be selected between 2 and 20 nm.

[0416] Photoactive Alpha Layer (PAL)

[0417] 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 forming PALs using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used for forming HILs. However, the deposition and coating conditions can vary depending on the compound used to form the PAL. It can be specified that the photoactive layer does not contain the compound of formula (I). The photoactive layer can be a light-emitting layer or a light-absorbing layer.

[0418] Emissive Layer (EML)

[0419] At least one first luminescent layer (EML), also referred to as the first light-emitting layer, can be formed on an HTL or EBL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When forming an EML using vacuum deposition or spin coating, the conditions for deposition and coating can be similar to those for forming an HIL. However, the deposition and coating conditions can vary depending on the compound used to form the EML.

[0420] According to the present invention, the electronic device preferably includes a light-emitting layer referred to as a "first light-emitting layer". However, the electronic device optionally includes two light-emitting layers, wherein the first layer is referred to as the first light-emitting layer and the second layer is referred to as the second light-emitting layer.

[0421] It can be specified that the at least one light-emitting layer, also known as the first light-emitting layer, does not contain the matrix compound of the hole injection layer.

[0422] It can be specified that the at least one light-emitting layer does not contain the compound of formula (I).

[0423] The at least one light-emitting layer (EML) may be formed by a combination of a host and a light-emitting dopant. Examples of hosts are: Alq3,4,4'-N,N'-dicarbazole biphenyl (HTC-10), 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), stilbene arylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0424] 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 high efficiency. The luminescent material can be a small molecule or a polymer.

[0425] Examples of red-emitting dopants include PtOEP, Ir(piq)3, and Btp2Ir(acac), but are not limited to these. These compounds are phosphorescent; however, fluorescent red-emitting dopants can also be used.

[0426] Examples of phosphorescent green luminescent dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2 (acac), and Ir(mpyp)3.

[0427] Examples of phosphorescent blue emitting electron dopants are F₂Irpic, (F₂ppy)₂Ir(tmd), and Ir(dfppz)₃ and trifluorene. Examples of fluorescent blue emitting electron dopants are 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetratert-butylperylene (TBPe).

[0428] Based on 100 parts by weight of the host, the amount of luminescent dopant can range from about 0.01 to about 50 parts by weight. Alternatively, the at least one luminescent layer can be composed of a luminescent polymer. The thickness of the EML can be from about 10 nm to about 100 nm, for example, from about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can exhibit excellent luminescence without substantially impairing the driving voltage.

[0429] Hole blocking layer (HBL)

[0430] 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.

[0431] HBL can also be called auxiliary ETL or a-ETL.

[0432] When forming HBLs using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used for forming HILs. However, the deposition and coating conditions can vary depending on the compound used to form the HBL. Generally, any compound used to form HBLs can be used. Examples of compounds used to form HBLs include... Diazole derivatives, triazole derivatives, phenanthrene-rhein derivatives, and triazine derivatives.

[0433] The thickness of the HBL can range from about 5 nm to about 100 nm, for example, from 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 substantially impairing the driving voltage.

[0434] Electron Transport Layer (ETL)

[0435] The organic electronic device of the present invention may also include an electron transport layer (ETL).

[0436] According to another embodiment of the invention, the electron transport layer may further comprise an azazine compound, preferably a triazine compound.

[0437] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organic complexes, preferably LiQ.

[0438] 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 substantially impairing the driving voltage.

[0439] According to another embodiment of the present invention, the 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.

[0440] Electron Injection Layer (EIL)

[0441] Optional electron-transporting layers (EILs) that facilitate electron injection from the cathode can be formed on the electron transport layer (ETL), preferably directly on it. Examples of materials used to form 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 material used to form the EIL.

[0442] 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 substantially impairing the driving voltage.

[0443] cathode layer

[0444] A cathode layer is formed on the ETL or optionally the EIL. The cathode layer can be formed of a metal, alloy, conductive compound, or mixture thereof. The cathode layer can have a low work function. For example, the cathode layer 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 layer can be formed of a transparent conductive oxide such as ITO or IZO.

[0445] The thickness of the cathode layer can range from about 5 nm to about 1000 nm, for example, from about 10 nm to about 100 nm. When the thickness of the cathode layer is in the range of about 5 nm to about 50 nm, the cathode layer can be transparent or translucent even if it is formed of metal or metal alloy.

[0446] It should be understood that the cathode layer is not part of the electron injection layer or the electron transport layer.

[0447] Manufacturing method

[0448] According to another aspect of the present invention, a method for manufacturing an organic electronic device is provided, the method using:

[0449] - At least one sedimentary source, preferably two sedimentary sources, more preferably at least three sedimentary sources.

[0450] Suitable deposition methods include:

[0451] - Deposition is performed via vacuum thermal evaporation;

[0452] - Deposition is performed via solution processing, preferably spin coating, printing, casting; and / or

[0453] - Slit-type die coating.

[0454] According to various embodiments of the present invention, a method using the following method is provided:

[0455] -The first deposition source releases matrix compounds, and

[0456] - The second deposition source releases compounds of formula (I) (also known as metal complexes).

[0457] The method includes the step of forming a hole injection layer; thus, for electronic devices:

[0458] - The cavity injection layer is formed by releasing the matrix compound according to the invention from the first deposition source and the compound of formula (I) (also called the metal complex) from the second deposition source.

[0459] The embodiments described below will be described in more detail with reference to examples. However, this disclosure is not limited to the embodiments described below. Exemplary aspects will now be referred to in detail. Attached Figure Description

[0460] The aforementioned components in the described embodiments, as well as the claimed components and components used in the present invention, are not subject to any special exceptions in terms of their size, shape, material selection, and technical concept, and therefore selection criteria known in the relevant field can be applied without restriction.

[0461] Additional details, features, and advantages of the present invention are disclosed in the dependent claims and the following description of the corresponding drawings, which illustrate preferred embodiments according to the invention in an exemplary manner. However, any embodiment is not necessarily representative of the full scope of the invention, and therefore the scope of the invention should 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.

[0462] Figure 1 This is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention;

[0463] Figure 2 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0464] Figure 3 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0465] Figure 4 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0466] Figure 5 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0467] Figure 6 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention.

[0468] Figure 1 This is a schematic cross-sectional view of an organic electronic device 101 according to an exemplary embodiment of the present invention. The organic electronic device 101 includes a substrate (110), an anode layer (120), a semiconductor layer (130) comprising a compound of formula (I), a photoactive layer (PAL) (151), and a cathode layer (190).

[0469] Figure 2 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), a semiconductor layer (130) comprising a compound of formula (I), a light-emitting layer (EML) (150), and a cathode layer (190).

[0470] 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), a semiconductor layer (130) comprising a compound of formula (I), a hole transport layer (HTL) (140), an emissive layer (EML) (150), an electron transport layer (ETL) (160), and a cathode layer (190).

[0471] Figure 4This 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), a semiconductor layer (130) comprising a compound of formula (I), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), a light-emitting layer (EML) (150), a hole blocking layer (HBL) (155), an electron transport layer (ETL) (160), an optional electron injection layer (EIL) (180), and a cathode layer (190).

[0472] Figure 5 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) including a first anode sublayer (121) and a second anode sublayer (122), a semiconductor layer (130) including a compound of formula (I), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), a light-emitting layer (EML) (150), a hole blocking layer (HBL) (155), an electron transport layer (ETL) (160), and a cathode layer (190).

[0473] Figure 6 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) comprising a first anode sublayer (121), a second anode sublayer (122), and a third anode sublayer (123), a semiconductor layer (130) comprising a compound of formula (I), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), a light-emitting layer (EML) (150), a hole blocking layer (HBL) (155), an electron transport layer (ETL) (160), and a cathode layer (190). The layers are arranged exactly in the order mentioned above.

[0474] In the above description, the method of manufacturing the organic electronic device 101 of the present invention, for example, begins on a substrate (110) on which an anode layer (120) is formed, and a semiconductor layer (130) comprising a compound of formula (I), a photoactive layer (151) and a cathode electrode 190 are formed on the anode layer (120), either in this order or in the reverse order.

[0475] In the above description, the method of manufacturing the OLED of the present invention begins with a substrate (110) on which an anode layer (120) is formed, and on the anode layer (120) a semiconductor layer (130) comprising a compound of formula (I), an optional hole transport layer (140), an optional electron blocking layer (145), a light-emitting layer (150), an optional hole blocking layer (155), an optional electron transport layer (160), an optional electron injection layer (180), and a cathode electrode 190 are formed, in exactly this order or exactly the reverse order.

[0476] The semiconductor layer (130) of the compound containing formula (I) can be a hole injection layer.

[0477] Although Figure 1 , Figure 2 , Figure 3 , Figure 4 , Figure 5 and Figure 6 Not shown, but a capping layer and / or sealing layer may also be formed on the cathode electrode 190 to seal the OLED 100. Additionally, various other modifications may be made to it.

[0478] 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.

[0479] Preparation of compounds of formula (I)

[0480] The compound of formula (I) can be prepared as follows:

[0481] Synthesis of 4-(2,4-dioxolane-3-yl)-2,3,5,6-tetrafluorobenzonitrile

[0482]

[0483] 200 mL of anhydrous glycol dimethyl ether was added to 4.68 g (195 mmol) of sodium hydride in a flame-dried Schlenk flask via a double-needle cannula. The suspension was cooled in an ice bath, and 20 mL (195 mmol) of acetylacetone was added dropwise over 30 minutes. After 10 minutes, 12.28 mL (97.4 mmol) of perfluorobenzonitrile was added over 60 minutes using a syringe. The mixture was stirred overnight at room temperature, then added to 0.5 L of water and acidified to pH 1 with concentrated hydrochloric acid. The product was extracted with ethyl acetate. The combined organic layers were washed with water, dried over magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was slurried and washed in methanol, filtered, and washed with methanol and n-hexane.

[0484] Yield: 17.8g (67%)

[0485] Synthesis of compound G10

[0486]

[0487] Dissolve 7.5 g (27.5 mmol) of 4-(2,4-dioxolane-3-yl)-2,3,5,6-tetrafluorobenzonitrile in 20 mL of THF. Add a solution of 1.48 g (9.15 mmol) of ferric chloride in 10 mL of water, and add 0.77 g (9.15 mmol) of sodium bicarbonate in portions. Add another 100 mL of water and stir the mixture overnight. After adding 50 mL of methanol, filter out the precipitate, wash with a small amount of water, and dry under vacuum overnight.

[0488] Yield: 6.9g (87%)

[0489] Synthesis of compound G11

[0490]

[0491] Dissolve 3 g (10.9 mmol) of 4-(2,4-dioxolane-3-yl)-2,3,5,6-tetrafluorobenzonitrile in a mixture of MeOH / H₂O (15 ml / 6 ml). Add 0.92 g (10.9 mmol) of sodium bicarbonate in portions, followed by a solution of 0.49 g (3.66 mmol) of aluminum trichloride in 2 ml of water. Filter off the solid formed, wash with water, and dry overnight under high vacuum.

[0492] Yield: 2.8g (92%)

[0493] Synthesis of compound G12

[0494]

[0495] 2.73 g (10 mmol) of 4-(2,4-dioxolane-3-yl)-2,3,5,6-tetrafluorobenzonitrile was dissolved in 50 mL of methanol / ethyl acetate (2:1 ratio). 1.0 g (5 mmol) of copper(II) acetate monohydrate was dissolved in 50 mL of water / acetonitrile (1:1), and the solution of 4-(2,4-dioxolane-3-yl)-2,3,5,6-tetrafluorobenzonitrile was added. The suspension was stirred at room temperature for 3 days, filtered, and washed with water / acetonitrile. The product was dried under vacuum overnight.

[0496] Yield: 2.71g (90%)

[0497] Other compounds according to the present invention can be prepared by the methods described above or by methods known in the art.

[0498] Sublimation temperature

[0499] Under nitrogen atmosphere in a glove box, 0.5 to 5 g of the compound was loaded into the evaporation source of the sublimation apparatus. The sublimation apparatus consisted of an inner glass tube, which was composed of a 3 cm diameter bulb placed inside a 3.5 cm diameter glass tube. The sublimation apparatus was placed in a tubular oven (Creaphys DSU 05 / 2.1). The sublimation apparatus was evacuated using a diaphragm pump (Pfeiffer Vacuum MVP 055-3C) and a turbine pump (Pfeiffer Vacuum THM071 YP). The pressure between the sublimation apparatus and the turbine pump was measured using a pressure gauge (Pfeiffer Vacuum PKR 251). When the pressure dropped to 10... -5 At millibars, the temperature is increased in increments of 10 to 30 K until the compound begins to deposit in the harvesting zone of the sublimation apparatus. The temperature is further increased in increments of 10 to 30 K until the sublimation rate reaches a point where the compound in the source is visibly depleted over 30 minutes to 1 hour and a significant amount of compound has accumulated in the harvesting zone. The sublimation temperature, also known as T... 升华 , is the temperature inside the sublimation apparatus, at which compounds are deposited at a visible rate in the harvesting area, and is measured in degrees Celsius.

[0500] Standard starting temperature

[0501] The standard onset temperature (T) was determined by loading 100 mg of the compound into a VTE source. RO As a VTE source, point sources of organic materials supplied by companies such as Kurt J. Lesker Company (www.lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com) can be used. In quantities less than 10... -5 The VTE source was heated at a constant rate of 15 K / min under millibar pressure, 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 angstroms per second. 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 appears on the QCM detector. For accurate results, the VTE source was heated and cooled three times, and only the results of the second and third runs were used to determine the standard onset temperature.

[0502] To achieve good control over the evaporation rate of organic compounds, a standard onset temperature can be set between 200°C and 255°C. If the standard onset temperature is below 200°C, evaporation may be too rapid and therefore difficult to control. If the standard onset temperature is above 255°C, the evaporation rate may be too low, which can lead to a low cycle time, and the organic compounds in the VTE source may decompose due to prolonged exposure to high temperatures.

[0503] 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.

[0504] General procedures for manufacturing electronic devices comprising semiconductor layers containing metal complexes and matrix compounds.

[0505] For Invention Examples 1 to 15 and Comparative Examples 1 to 9 in Table 2, a glass substrate having an anode layer comprising a first anode sublayer of 120 nm Ag, a second anode sublayer of 8 nm ITO, and a third anode sublayer of 10 nm ITO was cut to a size of 50 mm × 50 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, and then plasma treatment was performed to prepare the anode layer. The plasma treatment was performed at 75 W for 35 seconds in an atmosphere containing 97.6 vol% nitrogen and 2.4 vol% oxygen.

[0506] Then, the matrix compound and the metal complex are vacuum co-deposited onto the anode layer to form a hole injection layer (HIL) with a thickness of 10 nm. The composition of the hole injection layer is shown in Table 2. In Invention Examples 1 to 15, the compound of formula (I) was used.

[0507] The matrix compound HTM-1 has the following formula:

[0508]

[0509] Then, the matrix compound was vacuum deposited onto the HIL to form an HTL with a thickness of 123 nm. The matrix compound in the HTL was the same as that in the HIL.

[0510] Then, N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluorene-2-amine was vacuum deposited on HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0511] Then, 97 vol% H09 (Sun Fine Chemicals, Korea) as the EML host and 3 vol% BD200 (Sun Fine Chemicals, Korea) as the fluorescent blue emitting dopant were deposited on the EBL to form a blue first emitting layer (EML) with a thickness of 20 nm.

[0512] Then, a hole-blocking layer with a thickness of 5 nm is formed by depositing 2-(3'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine on the light-emitting layer EML.

[0513] Then, an electron transport layer with a thickness of 31 nm is formed on the hole blocking layer by depositing 50 wt% of 4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphth-1-yl)-[1,1'-biphenyl]-4-nitrile and 50 wt% LiQ.

[0514] Then, in 10 -7 0.01 to millibars Ag:Mg (90:10 vol%) is evaporated at a rate of 13 nm to form a cathode layer with a thickness of 13 nm on the electron transport layer.

[0515] Then, HTM-1 is deposited on the cathode layer to form a capping layer with a thickness of 75 nm.

[0516] By encapsulating the device with a glass substrate, the OLED stack is protected from environmental conditions. This creates a cavity containing a getter material for further protection.

[0517] To evaluate the performance of the invention compared to existing technologies, current efficiency was measured at 20°C. Using a Keithley 2635 source measurement unit, the current-voltage characteristics were determined 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 0.1V increments within the range of 0V to 10V. Similarly, measurements were taken in cd / m² at each voltage value using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 The luminance was measured to determine the luminance-voltage characteristics and CIE coordinates. The luminance-voltage and current-voltage characteristics at 10 mA / cm² were determined by interpolating them separately. 2 The CD / A efficiency under these conditions.

[0518] The device lifetime LT under environmental conditions (20°C) and 30 mA / cm 2 The measurements were taken using a Keithley 2400 source meter and recorded in hours.

[0519] The luminance of the device is measured using a calibrated photodiode. Lifetime LT is defined as the time until the luminance of the device drops to 97% of its initial value.

[0520] To determine the voltage stability U(100h)-(1h) over time, a voltage of 30 mA / cm² was applied to the device. 2 The current density was measured. The operating voltage was measured after 1 hour and 100 hours, and the voltage stability over the 1-hour to 100-hour period was calculated.

[0521] Technical Effects Table 1

[0522] Table 1 shows the physical properties of the compounds of formula (I), see inventive compounds 1 to 7 and comparative compounds 1 to 6.

[0523] As can be seen from Table 1, the sublimation temperatures of compounds 1 to 6 could not be measured due to the decomposition of the compounds, or the sublimation temperatures were in the range of 95 to 120 °C.

[0524] The standard onset temperatures of compounds 1 to 6 are in the range of <100℃ to 101℃, as shown in Table 1.

[0525] Compound 1 of the invention is a Cu(II) complex of formula (I). Compound 1 of the invention differs from comparative compound 1 in the substituted aryl substituents. The sublimation temperature is increased from 110°C–120°C for comparative compound 1 to 245°C for compound 1 of the invention. The standard onset temperature is also improved to 187°C.

[0526] Compound 2 is an Fe(III) complex of formula (I). The sublimation temperature is further improved to 262°C. The standard onset temperature is further improved to 196°C.

[0527] Compound 3 is an Al(III) complex of formula (I). The sublimation temperature is further improved to 277°C. The standard onset temperature is improved to 194°C.

[0528] Compound 4 is a Fe(III) complex of formula (I) containing four CF3 substituents. Its sublimation temperature is 224°C. The standard onset temperature is as high as 197°C.

[0529] Compounds 5 to 7 are Cu(II) complexes of formula (I) containing at least two independent substituents selected from CF3 and / or CN. Compared with comparative compounds 1 to 6, the sublimation temperature and standard onset temperature are improved.

[0530] In summary, the thermal stability, sublimation temperature and / or standard onset temperature of the compounds of formula (I) are significantly improved compared with the prior art.

[0531] OLED Performance Data Table 2

[0532] Table 2 shows OLED performance data for operating voltage increasing over time U(100h)-U(1h) and lifetime LT97 for Invention Examples 1 to 15 and Comparative Examples 1 to 3.

[0533] In Comparative Example 1, the semiconductor layer contained 3 vol% of the metal complex La(fod)3. The operating voltage increased by 1.07 V over time. The lifetime was 30 hours.

[0534] In Invention Example 1, the semiconductor layer contains 3% by volume G12. The operating voltage decreases to 0.3V over time. Lifetime is improved to 85 hours.

[0535] In Invention Example 2, the semiconductor layer contains 3% by volume G10. The operating voltage increases by 0.33V over time. The lifetime is further improved to 119 hours.

[0536] In Invention Example 3, the semiconductor layer contains 3% by volume G11. The operating voltage increases by 0.6V over time. The lifetime is further improved to 178 hours.

[0537] In Comparative Example 2, the semiconductor layer contained 5 vol% of the metal complex La(fod)3. The operating voltage increased by 0.85V over time. The lifetime was 24 hours.

[0538] In Invention Example 4, the semiconductor layer contains 5% by volume G12. The operating voltage increases by 0.42V over time. The lifetime is further improved to 180 hours.

[0539] In Invention Example 5, the semiconductor layer contains 5% by volume G10. The operating voltage increases by 0.23V over time. The lifetime is as long as 96 hours.

[0540] In Invention Example 6, the semiconductor layer contains 5% by volume G11. The operating voltage increases by 0.65V over time. The lifetime remains as long as 95 hours.

[0541] In Comparative Example 3, the semiconductor layer contained 10 vol% of the metal complex La(fod)3. The operating voltage increased by 0.89 V over time. The lifetime was 15 hours.

[0542] In Invention Example 7, the semiconductor layer contains 10% by volume of G12. The operating voltage increases by 0.6V over time. The lifetime is as long as 172 hours.

[0543] In Example 8, the semiconductor layer contains 10% by volume of G10. The operating voltage increases by 0.28V over time. The lifetime is as long as 109 hours.

[0544] In Invention Example 9, the semiconductor layer contains 5% by volume of G11. The operating voltage increases by 0.68V over time. The lifetime is further improved to 250 hours.

[0545] In Invention Examples 10 and 11, the semiconductor layer comprises Fe(III) complexes of formula (I) containing four CF3 substituents in two different percentages. Compared with Comparative Examples 1 to 3, the stability of the operating voltage over time and the lifetime are improved.

[0546] In Examples 12 to 15, the semiconductor layer comprises a Cu(II) complex of formula (I) containing at least two substituents selected from CF3 and / or CN. Compared with Comparative Examples 1 to 3, the stability of the operating voltage over time and the lifetime are improved.

[0547] In summary, compared with the prior art, the increase in operating voltage and the lifetime are significantly reduced in the semiconductor layer containing the compound of formula (I).

[0548] Reducing the operating voltage over time is an indicator of improved stability in electronic devices. Increased lifespan is also crucial for improving the stability of electronic devices.

[0549]

[0550]

[0551] The specific combinations of elements and features in the embodiments detailed above are merely exemplary; it is also expressly intended that these teachings be exchanged and substituted with other teachings herein and with patents / applications incorporated by reference. As those skilled in the art will recognize, variations, modifications, and other implementations described herein are conceived by those of ordinary skill in the art without departing from the spirit and scope of the claimed invention. Therefore, the foregoing 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 indefinite article “a” or “an” does not exclude a plural. The fact that specific measures are enumerated in mutually different dependent claims does not imply that combinations of these measures cannot be used advantageously. The scope of the invention is defined by the appended claims and their equivalents. Furthermore, the reference numerals used in the specification and claims do not limit the scope of the claimed invention.

Claims

1. A compound represented by formula I: (I), where M is selected from Fe(III), Cu(II) and / or Al(III); L is a charge-neutral ligand coordinated with metal M; n is an integer selected from 2 or 3, which corresponds to the oxidation number of M; m is 0; R 1 R 2 and R 3 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl groups and substituted or unsubstituted C2 to C3 groups 24 heteroaryl groups, in which Substituents are selected from F, Cl, CN, substituted or unsubstituted C1 to C1. 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatics, among which The substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 The substituents of the heteroaryl group are selected from F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3; in At least one R 1 R 2 and / or R 3 Selected from the replaced C6 to C 24 aryl group, The substituents are selected from at least two CN substituents, at least one or two CN substituents and one, two or three CF3 substituents, one CN substituent and one, two, three or four CF3 substituents, at least one CN and / or CF3 substituents and at least one F substituent.

2. The compound according to claim 1, wherein regarding R... 1 R 2 and R 3 The substituents in the definition, the substituted or unsubstituted C1 to C1 12 Alkyl groups are selected from partially or fully fluorinated C1 to C1 alkyl groups. 12 Alkyl groups, the substituted or unsubstituted C1 to C2 groups 12 Alkoxy groups are selected from partially or fully fluorinated C1 to C2 groups. 12 Alkyl group.

3. The compound according to claim 1, wherein... - R 1 Or R 2 Selected from the replaced C6 to C 24 An aryl group, wherein the substituent is selected from at least two CN substituents, at least one or two CN substituents and one, two or three CF3 substituents, one CN substituent and one, two, three or four CF3 substituents, at least one CN and / or CF3 substituent and at least one F substituent; R 3 Selected from substituted or unsubstituted C1 to C 12 Alkyl, wherein R 3 The replacement of C1 to C 12 The alkyl substituents are selected from F, Cl, CN, substituted or unsubstituted C1 to C2. 12 Alkoxy, substituted or unsubstituted C6 to C 18 Aryl groups and substituted or unsubstituted C2 to C3 groups 18 Mixed aromatic compounds.

4. The compound according to claim 3, wherein regarding R 3 The replacement of C1 to C 12 Alkyl substituents, the substituted or unsubstituted C1 to C2 groups 12 Alkoxy groups are selected from partially or fully fluorinated C1 to C2 groups. 12 Alkyl group.

5. The compound according to claim 1, wherein R 1 R 2 Or R 3 At least one substituted C6 to C 24 The aryl group is selected from the following formulas D3 to D19: (D3), (D4), (D5), (D6), (D7), (D8), (D9), (D10), (D11), (D12), (D13), (D14), (D15), (D16), (D17), (D18), (D19), in" "Indicates the location of the combination." 6. The compound according to claim 1, wherein the compound represented by formula I is selected from the following formulas E3 to E15 and E18 to E38: (E3)， (E4), (E5), (E6), (E7) (E8) (E9) (E10), (E11), (E12), (E13), (E14) (E15), (E18)， (E19), (E20), (E21), (E22), (E23), (E24), (E25), (E26), (E27) (E28) (E29) (E30) (E31) (E32) (E33), (E34), (E35), (E36), (E37), (E38).

7. The compound according to claim 1, wherein the compound represented by formula I is selected from the following formulas G4 to G75: (G4), (G5), (G6), (G7), (G8), (G9), (G10), (G11), (G12), (G13), (G14), (G15), (G16), (G17), (G18), (G19), (G20), (G21), (G22), (G23), (G24), (G25), (G26), (G27), (G28), (G29), (G30), (G31) (G32) (G33) (G34) (G35) (G36) (G37) (G38) (G39) (G40), (G41), (G42), (G43), (G44), (G45), (G46), (G47), (G48), (G49), (G50), (G51), (G52), (G53), (G54), (G55), (G56), (G57), (G58) (G59) (G60) (G61), (G62), (G63), (G64), (G65), (G66), (G67) (G68) (G69) (G70), (G71), (G72), (G73) (G74) (G75) 8. An organic semiconductor material comprising at least one compound of formula I according to any one of claims 1 to 7.

9. The organic semiconductor material according to claim 8, wherein the material further comprises at least one organic aromatic matrix compound.

10. An organic semiconductor layer comprising a compound of formula I according to any one of claims 1 to 7.

11. An organic electronic device comprising the organic semiconductor material according to claim 8.

12. The organic electronic device according to claim 11, wherein the organic electronic device is a light-emitting device, a thin-film transistor, a battery, a display device, a photovoltaic cell, and is part of a display device or a lighting device.

Images