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)

Abstract

The present invention is a compound represented by the chemical formula (I), wherein M is a metal; L is a charge-neutral ligand coordinating to the metal M; n is an integer selected from 1 to 4 corresponding to the oxidation number of M; m is an integer selected from 0 to 2; and R1, R2 and R3 are substituents; the invention relates to 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): (I)

Description

Technology 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] Electronic devices that are self-emissive devices, such as organic light-emitting diodes (OLEDs), have a wide viewing angle, excellent contrast, fast response, high brightness, excellent operating voltage characteristics, and color reproduction. A typical OLED comprises an anode layer, a hole injection layer (HIL), a hole transport layer (HTL), an emitting layer (EML), an electron transport layer (ETL), and a cathode layer, which are sequentially stacked on a substrate. In this regard, the HIL, HTL, EML, and ETL are thin films formed of organic compounds.

[0003] When voltage is applied to the anode and cathode, holes injected from the anode move to the EML through the HIL and HTL, and electrons injected from the cathode move to the EML through the ETL. The holes and electrons recombine in the EML to generate excitons. When the excitons fall from the excited state to the ground state, light is emitted. For an OLED having the structure described above to have a low driving voltage, excellent efficiency, and / or long lifespan, the injection and flow of holes and electrons must be balanced.

[0004] The performance of an organic light-emitting diode can be affected by the characteristics of the hole injection layer, and in particular, by the characteristics of the metal complex and hole transport compound contained in the hole injection layer.

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

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

[0007] The performance of an organic light-emitting diode can be affected by the characteristics of the semiconductor layer, and among them, by the characteristics of the metal complex included in the semiconductor layer. The problem to be solved

[0008] There remains a need to improve the performance of semiconductor materials, semiconductor layers, and their electronic devices, and in particular, to achieve improved operating voltage stability over time by improving the properties of the compounds included herein.

[0009] In addition, it is necessary to improve the performance of electronic devices by providing a hole injection layer with improved performance, and in particular, it is necessary to achieve an improved operating voltage through the improvement of the characteristics of the hole injection layer and the electronic device.

[0010] In addition, there remains a need to provide a hole injection layer that enables injection into an adjacent layer containing a compound having a HOMO level further away from the vacuum level.

[0011] In addition, the objective is to provide a hole injection layer comprising a compound that can be deposited via vacuum thermal deposition under conditions suitable for mass production. means of solving the problem

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

[0013] (I)

[0014] Here,

[0015] M is a metal;

[0016] L is a charge-neutral ligand coordinating with metal M;

[0017] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0018] m is an integer selected from 0 to 2;

[0019] R 1 , R 2 and R 3 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0020] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0021] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0022] Here

[0023] At least one R 1 , R 2 and / or R 3 is substituted C2 to C 24 It is selected from heteroaryl groups, wherein at least one substituent is selected from halogen, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyl, and partially or completely fluorinated C1 to C6 alkoxy.

[0024] definition

[0025] Unless otherwise specified, any R throughout the specification and claims 1 , R 2 , R 3 It should be noted that , L and M always refer to the same moiety.

[0026] In this specification, unless otherwise defined, "substituted" refers to halogens, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyls, partially or completely fluorinated C1 to C6 alkyls, substituted or unsubstituted C1 to C6 alkoxys, partially or completely fluorinated C1 to C6 alkoxys, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 It means a substituted one selected from heteroaryls, where the substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3.

[0027] In this specification, “aryl group” and “aromatic ring” refer to a hydrocarbyl group that can be produced by the formal extraction of one hydrogen atom from an aromatic ring in a corresponding aromatic hydrocarbon. An aromatic hydrocarbon refers to a hydrocarbon containing at least one aromatic ring or an aromatic ring system. An aromatic ring or an aromatic ring system refers to a planar ring or ring system of covalently bonded carbon atoms, wherein the planar ring or ring system comprises a conjugated system of delocalized electrons satisfying Huckel’s rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl, polycyclic groups comprising more aromatic rings connected by a single bond such as biphenyl, and polycyclic groups comprising fused rings such as naphthyl or fluorenyl.

[0028] Similarly, under "heteroaryl" and "heteroaromatic," this is appropriately understood as a group derived by the formal extraction of one ring hydrogen from a heterocyclic aromatic ring, particularly in compounds containing at least one of these rings.

[0029] The term "non-heterocycle" is understood to mean a ring or ring system that does not contain a heteroatom as a ring member.

[0030] The term "heterocycle" is understood to mean that the heterocycle comprises at least one ring containing one or more heteroatoms. A heterocycle comprising more than one ring means all rings containing heteroatoms or at least one ring containing heteroatoms and at least one ring containing only C-atoms and not containing heteroatoms. A C2 heteroaryl group means that the heteroaryl ring comprises two C-atoms and the other atom is a heteroatom.

[0031] Under heterocycloalkyl, this is appropriately understood as a group derived by the formal extraction of one ring hydrogen from a saturated cycloalkyl ring in a compound containing at least one such ring.

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

[0033] The term "fused aryl ring" or "condensed aryl ring" refers to two aryl rings comprising at least two common sp 2 - It is understood as a method considered to be fused or condensed when sharing hybridized carbon atoms.

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

[0035] The term "5-, 6- or 7-membered ring" is understood to mean a ring containing 5, 6, or 7 atoms. The atoms may be selected from C and one or more heteroatoms.

[0036] In this specification, a single bond means a direct bond.

[0037] In this specification, unless otherwise defined, "substituted" refers to H, deuterium, C1 to C2 12 Alkyl, unsubstituted C6 to C 18 Aryl, and unsubstituted C2 to C 18 It means that it is substituted with a heteroaryl.

[0038] In this specification, "substituted aryl" refers, for example, C6 to C 24 C6 to C6 substituted with aryl or one or more substituents 18 It means aryl, where the substituent may be unsubstituted or substituted with one or more substituents.

[0039] Accordingly, in this specification, "substituted heteroaryl substituted" means substituted with one or more substituents, and these themselves may be substituted with one or more substituents.

[0040] In this specification, unless otherwise specifically defined, a heteroaryl group substituted with at least a C-ring atom 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 can be substituted with 1, 2, 3, 4, or 5 substituents.

[0042] The substituted heteroaryl group may include at least six ring atoms. The substituted heteroaryl group that may include at least six ring atoms may be substituted with one, two, three, or four substituents when the heteroaryl group includes one heteroatom and five C-atoms, or may be substituted with one, two, or three substituents when the heteroaryl group having at least six ring atoms includes two heteroatoms and four C-atoms, or may be substituted with one or two substituents when the heteroaryl group having at least six ring atoms includes three heteroatoms and three C-atoms, wherein the substituents are bonded only to the C-ring atoms.

[0043] In this specification, unless otherwise specifically defined, "alkyl group" means a saturated aliphatic hydrocarbyl group. The alkyl group is C1 to C 12 It may be an alkyl group. More specifically, the alkyl group is C1 to C 10 It may be an alkyl group or a C1 to C6 alkyl group. For example, a C1 to C4 alkyl group comprises 1 to 4 carbons in an alkyl chain and may be selected from methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, and cyclohexyl.

[0044] Specific examples of alkyl groups may be methyl groups, ethyl groups, propyl groups, isopropyl groups, butyl groups, iso-butyl 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 specifically defined, "substituted alkyl group" may mean a linear, branched, or cyclic substituted saturated aliphatic hydrocarbyl group. The substituted alkyl group is a linear, branched, or cyclic C1 to C 12The substituted alkyl group may be an alkyl group. More specifically, the substituted alkyl group is a linear, branched, or cyclically substituted C1 to C1 10 It may be an alkyl group or a linear, branched, or cyclically substituted C1 to C6 alkyl group. For example, a linear, branched, or cyclically substituted C1 to C4 alkyl group comprises 1 to 4 carbons in the alkyl chain and may be selected from methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, and cyclohexyl. Substituents may be selected from halogens, F, Cl, CN, OCH3, and OCF3.

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

[0047] Where a substituent is not named in this specification, the substituent may be H.

[0048] The term "charge-neutral" means that the L group is electrically neutral as a whole.

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

[0050] The terms "not," "not containing," and "not including" do not exclude impurities that may be present in the compound prior to deposition. Impurities have no technical effect in relation to the purpose achieved by the present invention.

[0051] The term "interposed in contact" refers to an arrangement of three layers in which an intermediate layer is in direct contact with two adjacent layers.

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

[0053] The terms "emissive layer," "light-emitting layer," and "emission layer" are used interchangeably.

[0054] The terms "OLED," "organic light-emitting diode," and "organic light-emitting device" are used interchangeably.

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

[0056] The term "at least two anode sublayers" is understood to mean two or more anode sublayers, for example, two or three anode sublayers.

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

[0058] The term "hole injection layer" is understood to mean a layer that improves charge injection from an anode layer to an additional layer in an electronic device, or from an additional layer in an electronic device to an anode.

[0059] The term "hole transport layer" is understood to mean an additional layer arranged between the hole injection layer and the cathode layer, and a layer that transports holes between the hole injection layer.

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

[0061] In the context of this specification, the terms “essentially non-emissive” or “non-emissive” mean that the contribution of the compound of formula (I) or the hole injection layer comprising the compound of formula (I) to the visible light emission spectrum from an electronic device such as an OLED or display device is less than 10%, preferably less than 5%, to the visible light emission spectrum. The visible light emission spectrum is an emission spectrum having wavelengths of about ≥ 380 nm to about ≤ 780 nm.

[0062] In the context of the present invention, the term "sublimation" may mean a transition from a solid state to a gaseous state or from a liquid state to a gaseous state.

[0063] In this specification, hole characteristics refer to the ability to form holes by donating electrons when an electric field is applied, and holes formed in the anode can be easily injected into the light-emitting layer due to their conductive characteristics according to the highest occupied molecular orbital (HOMO) level and transported in the light-emitting layer.

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

[0065] The term "HOMO level" is understood to mean 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 the absolute value of the HOMO level of the reference compound. For example, the term "further from the vacuum level than the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octakis(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine" is understood to mean that the absolute value of the HOMO level of the matrix compound of the hole injection layer is higher than the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octakis(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine.

[0067] The term "absolute value" is understood to mean a value without a "-" sign. According to one embodiment of the present invention, the HOMO level of the matrix compound of the hole injection layer can be calculated by a quantum mechanical method.

[0068] advantageous effects

[0069] Surprisingly, it has been found that the electronic device according to the present invention solves the fundamental problem of the present invention by enabling an electronic device, such as an organic light-emitting diode, to be superior to electronic devices known in the art in various aspects, particularly with respect to operating voltage.

[0070] In addition, it has been found that the fundamental problem of the present invention can be solved by providing a compound suitable for deposition via vacuum thermal deposition under conditions suitable for mass production. In particular, the rate onset temperature of the compound of formula (I) of the present invention may be within a range suitable for mass production.

[0071] The compound of formula (I) is non-luminous. In the context of this specification, the term “essentially non-luminous” or “non-luminous” means that the contribution of the compound of formula (I) to the visible light emission spectrum from an electronic device, such as an OLED or display device, is less than 10%, preferably less than 5%, to the visible light emission spectrum. The visible light emission spectrum is an emission spectrum having wavelengths of about ≥ 380 nm to about ≤ 780 nm.

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

[0073] The term "M" represents a metal. According to one embodiment, the metal M may be selected from alkali, alkaline earth, transition, rare earth metals, or Group III to V metals, preferably the metal M is selected from transition or Group III to V metals; preferably the metal M may be 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), and Bi(III); more preferably, M is selected from Fe(III) and Cu(II). Elements of groups IV through XI are named transition metals.

[0074] Ligand L of chemical formula (I)

[0075] The term "L" represents a charge-neutral ligand coordinating to a metal M. According to one embodiment, L is H2O, C2 to C 40 Mono- or multi-dentate ethers and C2 to C 40 Thioether, C2 to C 40 Amines, C2 to C 40 Phosphine, C2 to C 20 alkyl nitrile or C2 to C 40 Selected from the group comprising aryl nitriles, or compounds according to chemical formula (II):

[0076] (II)

[0077] Here

[0078] R6 and R 7 is independently C1 to C 20 Alkyl, C1 to C 20 Heteroalkyl, C6 to C 20 Aryl, heteroaryl having 5 to 20 ring-forming atoms, halogenated or perhalogenated C1 to C 20 Alkyl, halogenated, or perhalogenated C1 to C 20 Heteroalkyl, halogenated or perhalogenated C6 to C 20 Selected from aryls, halogenated or perhalogenated heteroaryls having 5 to 20 ring-forming atoms, or at least one R 6 and R 7 It is connected to form a 5 to 20-membered ring, or 2 R 6 and / or 2 R 7 This is connected to form a 5 to 40-membered ring, or is unsubstituted or C1 to C 12 It forms a 5 to 40-membered ring containing substituted phenanthroline.

[0079] According to one embodiment, the ligand L in the compound of formula (I) may be selected from the group comprising:

[0080] - At least 3 carbon atoms, alternatively at least 4 carbon atoms, and / or

[0081] - 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

[0082] - At least one group selected from halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, alternatively two or more groups selected from halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, at least one group selected from halogen, F, CN, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, alternatively two or more groups selected from halogen, F, CN, perfluorinated C1 to C6 alkyl, perfluorinated C1 to C6 alkoxy, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl, and / or substituted or unsubstituted C3 to C 12 One or more groups selected from heteroaryls,

[0083] Here, the substituents are D, C6-aryl, C3-C9 heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially or perfluorinated C1-C 16 Alkyl, partially or perfluorinated C1 to C 16 Alkoxy, partially or perfluorinated C1 to C6 alkyl, partially or perfluorinated C1 to C6 alkoxy, COR 3 , COOR 3 Selected from , halogen, F or CN;

[0084] Here, R 3 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 C16 It can be selected from alkoxy, partially or perfluorinated C1 to C6 alkyl, and partially or perfluorinated C1 to C6 alkoxy.

[0085] Term "n"

[0086] 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 another embodiment, "n" is an integer selected from 2 or 3.

[0087] term "m"

[0088] 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 another embodiment, "m" is an integer selected from 0 or 2.

[0089] Implementation example

[0090] Compounds represented by chemical formula (I) can also be named as metal complexes or metal acetylacetonate complexes.

[0091] According to one embodiment, the metal complex of formula (I) may have a molecular weight Mw of ≥ 287 g / mol and ≤ 2000 g / mol, preferably ≥ 400 g / mol and ≤ 1500 g / mol, more preferably ≥ 580 g / mol and ≤ 1500 g / mol, also preferably ≥ 580 g / mol and ≤ 1400 g / mol, and also preferably ≥ 580 g / mol and ≤ 1100 g / mol.

[0092] According to one embodiment, a compound represented by the chemical formula (I):

[0093] (I)

[0094] Here,

[0095] M is a metal;

[0096] L is a charge-neutral ligand coordinating with metal M;

[0097] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0098] m is an integer selected from 0 to 2;

[0099] R 1 , R 2 and R 3 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0100] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0101] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0102] Here

[0103] At least one R 1 , R 2 and / or R3 is substituted C2 to C 24 It is selected from heteroaryl groups, wherein at least one substituent is CN, partially or completely fluorinated C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkoxy; preferably selected from CN and / or partially or completely fluorinated C1 to C6 alkyl.

[0104] According to one embodiment, at least one R 1 , R 2 and / or R 3 is substituted C 2 to C 24 It is selected from heteroaryl groups, wherein at least one substituent is CN, partially or completely fluorinated C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkoxy; preferably selected from CN and / or partially or completely fluorinated C1 to C6 alkyl, and preferably at least one substituent is selected from CF3 or OCF3.

[0105] (I)

[0106] Here,

[0107] M is a metal;

[0108] L is a charge-neutral ligand coordinating with metal M;

[0109] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0110] m is an integer selected from 0 to 2;

[0111] R 1 , R 2 and R 3 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0112] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0113] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0114] Here

[0115] At least one R 1 , R 2 and / or R 3 is substituted C2 to C 24 Selected from heteroaryl groups, wherein at least one substituent is selected from halogen, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkoxy; and

[0116] Here

[0117] - C2 to C 24 At least one substituent on the heteroaryl group is selected from CF3 and / or CN; and / or

[0118] - R 1 and / or R 3 is selected from CF3 and / or CN, and C2 to C 24 At least one substituent on the heteroaryl group is selected from CF3 and / or CN.

[0119] According to one embodiment, the compound is represented by the chemical formula (I):

[0120] (I)

[0121] Here,

[0122] M is a metal;

[0123] L is a charge-neutral ligand coordinating with metal M;

[0124] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0125] m is an integer selected from 0 to 2;

[0126] R 1 , R 2 and R 3 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0127] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0128] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0129] Here

[0130] At least one R 1 , R 2 or R 3is a substituted heteroaryl group of a 6-membered ring containing one, two, or three heteroatoms, where the heteroatom is N, and

[0131] - At least one or two substituents are selected from the group including CF3 and CN; or

[0132] R 1 and / or R 3 is a substituted heteroaryl group of a 6-membered ring containing one, two, or three heteroatoms, where the heteroatom is N, and at least one or two substituents are selected from the group including CF3 and CN.

[0133] According to one embodiment, the compound is represented by the chemical formula (I):

[0134] (I)

[0135] Here,

[0136] M is a metal;

[0137] L is a charge-neutral ligand coordinating with metal M;

[0138] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0139] m is an integer selected from 0 to 2;

[0140] R 1 and R 3 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0141] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0142] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0143] R 2 is independently substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0144] At least one substituent is selected from halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, C6 to C18 aryls that are substituted or unsubstituted, and C2 to C18 heteroaryls that are substituted or unsubstituted, wherein the substitution may be performed as follows.

[0145] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0146] At least one R 1 , R 2 and / or R 3 is substituted C2 to C 24It is selected from heteroaryl groups, wherein at least one substituent is selected from halogen, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyl, and partially or completely fluorinated C1 to C6 alkoxy.

[0147] According to one embodiment, the compound is represented by the chemical formula (I):

[0148] (I)

[0149] Here,

[0150] M is a metal;

[0151] L is a charge-neutral ligand coordinating with metal M;

[0152] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0153] m is an integer selected from 0 to 2;

[0154] R 1 and R 3 C1 to C, independently substituted or unsubstituted 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 It is selected from heteroaryl groups, wherein at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0155] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0156] R 2 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0157] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls, and the substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0158] R 1 , R 2 and R 3 One of them is a substituted C2 to C 24 It is selected from heteroaryl groups, wherein at least one substituent is selected from halogen, F, Cl, CN, CF3, partially or completely fluorinated C1 to C6 alkyl, and partially or completely fluorinated C1 to C6 alkoxy.

[0159] According to one embodiment, the compound is represented by the chemical formula (I):

[0160] (I)

[0161] Here,

[0162] M is a metal;

[0163] L is a charge-neutral ligand coordinating with metal M;

[0164] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0165] m is an integer selected from 0 to 2;

[0166] R 1 and R 3 C1 to C, independently substituted or unsubstituted 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 It is selected from heteroaryl groups, wherein at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0167] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0168] R 2 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0169] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls, and the substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0170] R 1 , R 2 and R 3 One of them is a substituted C2 to C 24 Selected from heteroaryl groups, wherein at least one substituent is selected from halogen, F, Cl, CN, CF3, partially or completely fluorinated C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkoxy;

[0171] At least one R 1 , R 2 or R 3 It is a substituted heteroaryl group of a 6-membered ring containing 1, 2, or 3 heteroatoms, where the heteroatom is N.

[0172] According to one embodiment, the compound is represented by the chemical formula (I):

[0173] (I)

[0174] Here,

[0175] M is a metal;

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

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

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

[0179] R 1 , R 2 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0180] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0181] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0182] R 1 or R 2 is substituted C2 to C 24 Selected from heteroaryl groups, wherein at least one substituent is selected from halogen, F, Cl, CN, CF3; and

[0183] R 3 H, D, substituted or unsubstituted C1 to C 12 It is alkyl, where the substituent is selected from halogen, F, Cl, CN, and CF3.

[0184] According to one embodiment, the compound is represented by the chemical formula (I):

[0185] (I)

[0186] Here,

[0187] M is a metal;

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

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

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

[0191] R 1 , R 2 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0192] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0193] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0194] R 1 or R 2 is substituted C2 to C 24 A 6-membered heteroaryl ring having one, two, or three N atoms and the remaining atoms are C, wherein at least one, two, three, or four of the remaining C atoms of the heteroaryl ring are substituents having substituents independently selected from halogen, F, Cl, CN, CF3, preferably F, CN, CF3 groups;

[0195] R 3 It is H, D, CH3, CF3, CN, preferably CH3 or CF3.

[0196] According to one embodiment, the compound is represented by the chemical formula (I):

[0197] (I)

[0198] Here,

[0199] M is a metal;

[0200] L is a charge-neutral ligand coordinating with metal M;

[0201] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0202] m is an integer selected from 0 to 2;

[0203] R 1 , R 2 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0204] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0205] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0206] R 1 or R 2is selected from a 6-membered heteroaryl ring having 1, 2, or 3 N atoms and the remaining atoms being C, wherein at least 1, 2, 3, or 4 of the remaining C atoms of the heteroaryl ring are substituents having substituents independently selected from halogen, F, Cl, CN, CF3, preferably F, CN, CF3;

[0207] R 3 It is CH3, CF3, CN, preferably CH3 or CF3.

[0208] According to one embodiment, the compound is represented by the chemical formula (I):

[0209] (I)

[0210] Here,

[0211] M is a metal;

[0212] L is a charge-neutral ligand coordinating with metal M;

[0213] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0214] m is an integer selected from 0 to 2;

[0215] R 1 , R 2 and R 3 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0216] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0217] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0218] At least one R 1 , R 2 and / or R 3 is a substituted heteroaryl group of a 6-membered ring containing one, two, or three heteroatoms, wherein the heteroatom is N, and at least one substituent is selected from halogen, F, Cl, CN, and partially or completely fluorinated C1 to C6 alkyl.

[0219] According to one embodiment, the compound is represented by the chemical formula (I):

[0220] (I)

[0221] Here,

[0222] M is a metal;

[0223] L is a charge-neutral ligand coordinating with metal M;

[0224] n is an integer selected from 1 to 4 corresponding to the oxidation number of M;

[0225] m is an integer selected from 0 to 2;

[0226] R 1 , R 2 and R 3 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 Selected from heteroaryl groups,

[0227] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0228] The substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3;

[0229] Here

[0230] At least one substituent is selected from CN, partially or completely fluorinated C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkoxy, preferably CN and / or partially or completely fluorinated C1 to C6 alkyl, and more preferably CF3, OCF3, or CN;

[0231] The heteroaryl group of the substituted heteroaryl group is a 6-membered ring and contains one, two, or three heteroatoms, preferably the heteroatom is N.

[0232] In one embodiment, R 1 , R 2 and R 3 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24It is selected from heteroaryl groups, wherein at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 It is selected from heteroaryls, and the substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3.

[0233] According to one embodiment, R 1 , R 2 and R 3 is independently H, D, substituted or unsubstituted C1 alkyl, substituted C6 to C 24 aryl, and substituted C2 to C 24 It is selected from heteroaryl groups, wherein at least one substituent is selected from halogen, F, Cl, CN, CF3.

[0234] According to one embodiment, at least one R 1 , R 2 or R 3 is substituted C2 to C 24 Selected from heteroaryl groups, where

[0235] - The substituted heteroaryl group comprises at least one 6-membered ring; and / or

[0236] - The substituted heteroaryl group comprises at least 1 to 3 N atoms, preferably 1 or 2 N atoms, or preferably 1 N atom; and / or

[0237] - The heteroaryl group of the substituted heteroaryl group is a 6-membered ring and contains 1, 2, or 3 heteroatoms, preferably the heteroatom is N.

[0238] According to one embodiment, at least one R 1 , R 2 or R 3 is substituted C2 to C 24 A heteroaryl group, wherein the heteroaryl group is selected from pyridyl, pyrimidinyl, pyrazinyl, or triazinyl.

[0239] According to one embodiment, at least one R 1 , R 2 or R 3 is substituted C2 to C 24 Selected from heteroaryl groups, wherein at least one substituent of the substituted heteroaryl group is selected from the group comprising halogens, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyls, and partially or completely fluorinated C1 to C6 alkoxys; preferably selected from the group comprising halogens, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyls, and partially or completely fluorinated C1 to C6 alkoxys; more preferably selected from the group comprising halogens, F, Cl, CN, partially or completely fluorinated C1 to C4 alkyls, and partially or completely fluorinated C1 to C4 alkoxys; even more preferably selected from the group comprising F, CN, and partially or completely fluorinated C1 to C6 alkyls; Also preferably selected from the group comprising F, CN, partially or completely fluorinated C1 to C6 alkyl, also preferably halogen, F, Cl, CN, partially or completely fluorinated C1 to C4 alkyl; more preferably at least one CN, at least one CF3 group and / or at least two F atoms.

[0240] According to one embodiment, at least one R 1 , R 2 or R 3 is substituted C2 to C 24Selected from heteroaryl groups, wherein at least one substituent is selected from halogens, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyls, partially or completely fluorinated C1 to C6 alkoxys, and R 1 , R 2 or R 3 One of them is substituted or unsubstituted C1 to C 12 Alkyl or substituted or unsubstituted C1 to C 12 Selected from alkoxy, wherein at least one substituent is selected from halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, and partially or completely fluorinated C1 to C6 alkoxy; R 1 , R 2 or R 3 One of them is H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Selected from alkoxy, and at least one substituent is selected from halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, and partially or completely fluorinated C1 to C6 alkoxy;

[0241] Substituents are selected from halogens, F, Cl, CN, C1 to C6 alkyls, CF3, OCH3, and OCF3.

[0242] According to one embodiment, R 1 or R 2 is substituted C2 to C 24 Selected from the heteroaryl group, and the remaining R 1 , R 2 and R 3 H, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12Selected from alkoxy, wherein at least one substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, C1 to C6 alkoxy; R 1 and R 3 is not H.

[0243] According to one embodiment, R 1 , R 2 is unsubstituted C1 to C 12 alkyl, preferably CH3, is selected from a substituted 6-membered heteroaryl ring having one, two, or three N atoms and the remainder being C, wherein at least one substituent is selected from F, CN, CF3; R 1 or R 2 is selected from a 6-membered heteroaryl ring having 1, 2, or 3 N atoms and the remaining atoms being C, wherein at least 1, 2, 3, or 4 of the remaining C atoms of the heteroaryl ring are substituents having substituents individually selected from halogens, F, Cl, CN, CF3, preferably F, CN, CF3; and R 3 It is CH3, CF3, CN, preferably CH3 or CF3.

[0244] According to one embodiment, R 1 , R 2 is unsubstituted C1 to C 12 alkyl, preferably CH3, is selected from a substituted 6-membered heteroaryl ring having one, two, or three N atoms and the remainder being C, wherein at least one substituent is selected from F, CN, CF3; R 1 or R 2is selected from a 6-membered heteroaryl ring having 1, 2, or 3 N atoms and the remaining atoms being C, and at least one of the remaining C atoms of the heteroaryl ring is a substituent having a substituent individually selected from halogens, F, Cl, CN, CF3, preferably F, CN, CF3; R 3 It is CH3, CF3, CN, preferably CH3 or CF3.

[0245] According to one embodiment, R 1 , R 2 is unsubstituted C1 to C 12 alkyl, preferably CH3, is selected from a substituted 6-membered heteroaryl ring having one, two, or three N atoms and the remainder being C, wherein at least one substituent is selected from F, CN, CF3; R 1 or R 2 is selected from a 6-membered heteroaryl ring having 1, 2, or 3 N atoms and the remaining atoms being C, and at least 2 of the remaining C atoms of the heteroaryl ring are substituents having substituents individually selected from halogens, F, Cl, CN, CF3, preferably F, CN, CF3; R 3 It is CH3, CF3, CN, preferably CH3 or CF3.

[0246] According to one embodiment, R 1 , R 2 is unsubstituted C1 to C 12 alkyl, preferably CH3, is selected from a substituted 6-membered heteroaryl ring having one, two, or three N atoms and the remainder being C, wherein at least one substituent is selected from F, CN, CF3; R 1 or R 2is selected from a 6-membered heteroaryl ring having 1, 2, or 3 N atoms and the remaining atoms being C, and at least 3 of the remaining C atoms of the heteroaryl ring are substituents having substituents individually selected from halogens, F, Cl, CN, CF3, preferably F, CN, CF3; R 3 It is CH3, CF3, CN, preferably CH3 or CF3.

[0247] According to one embodiment, R 1 , R 2 is unsubstituted C1 to C 12 alkyl, preferably CH3, is selected from a substituted 6-membered heteroaryl ring having one, two, or three N atoms and the remainder being C, wherein at least one substituent is selected from F, CN, CF3; R 1 or R 2 is selected from a 6-membered heteroaryl ring having one or two N atoms and the remaining atoms being C, and at least four of the remaining C atoms of the heteroaryl ring are substituents having substituents individually selected from halogens, F, Cl, CN, CF3, preferably F, CN, CF3; R 3 It is CH3, CF3, CN, preferably CH3 or CF3.

[0248] According to one embodiment, C2 to C 24At least one substituent on the heteroaryl group is selected from halogen, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkoxy; more preferably selected from halogen, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkoxy, and also preferably selected from halogen, F, Cl, CN, partially or completely fluorinated C1 to C4 alkyl, partially or completely fluorinated C1 to C4 alkoxy.

[0249] According to one embodiment, C2 to C 24 At least one substituent on the heteroaryl group is selected from F, CN, partially or completely fluorinated C1 to C6 alkyls; more preferably selected from F, CN, partially or completely fluorinated C1 to C6 alkyls, and also preferably selected from halogen, F, Cl, CN, partially or completely fluorinated C1 to C4 alkyls.

[0250] According to one embodiment, C2 to C 24 At least one substituent on the heteroaryl group is selected from at least one CN or CF3 group, or at least two F atoms.

[0251] According to one embodiment, at least one R 1 , R 2 or R 3 is substituted C2 to C 24 Selected from heteroaryl groups, wherein the heteroaryl group of the substituted heteroaryl group is a 6-membered ring and comprises one, two, or three heteroatoms, preferably the heteroatom is N; and at least one R 1 , R 2 or R 3 Substituted or unsubstituted C6 to C 24 Chosen by Aril,

[0252] Herein, at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls,

[0253] Substituents are selected from halogens, F, Cl, CN, C1 to C6 alkyls, CF3, OCH3, and OCF3.

[0254] According to one embodiment, R 1 , R 2 , R 3 ...substituted or unsubstituted C6 to C 24 aryl group or substituted or unsubstituted C6 to C 18 It may not be selected from Arilgi.

[0255] According to one embodiment, R 1 , R 2 , R 3 It may not be selected from substituted or unsubstituted aryl groups.

[0256] According to one embodiment, the chemical formula (I) is a substituted or unsubstituted C6 to C 24 aryl group or substituted or unsubstituted C6 to C 18 It may not contain aryl groups.

[0257] According to one embodiment, the chemical formula (I) may not contain a substituted or unsubstituted aryl group.

[0258] According to one embodiment, R 1 , R 2 or R 3 At least one substituted C2 to C of 24 The heteroaryl group is selected from the following chemical formulas D1 to D29:

[0259]

[0260] Here, "*" indicates the joining position.

[0261] According to one embodiment, R 1 , R 2 or R 3 At least one substituted C2 to C of 24 The heteroaryl group is selected from chemical formulas D1 to D12 and D13 to D29, where "*" indicates the bonding position.

[0262] According to one embodiment, the compound represented by chemical formula (I) is selected from the following chemical formulas E1 to E37:

[0263]

[0264]

[0265]

[0266]

[0267] According to one embodiment, the compound represented by chemical formula (I) is selected from chemical formulas E1 to E5 and E7 to E37.

[0268] According to one embodiment, the compound represented by chemical formula (I) is selected from chemical formulas E2 to E5, E7 to E14, and E16 to E37.

[0269] According to one embodiment, the compound represented by chemical formula (I) is selected from chemical formulas E33 to E37.

[0270] According to one embodiment, the compound represented by chemical formula (I) is selected from the following chemical formulas G1 to G66:

[0271]

[0272]

[0273]

[0274]

[0275]

[0276] According to one embodiment, the compound represented by chemical formula (I) is selected from chemical formulas G1 to G66, and G5 and G20 are excluded.

[0277] According to one embodiment, the compound represented by chemical formula (I) is selected from chemical formulas G2 to G4, G6 to G13, G17 to G19, G21 to G28, and G32 to G66.

[0278] According to one embodiment, the compound represented by chemical formula (I) is selected from chemical formulas G57 to G66.

[0279] Substantively covalent matrix compound

[0280] A substantially covalent matrix compound, also referred to as a matrix compound, may be an organic aromatic matrix compound containing organic aromatic covalent carbon atoms. A substantially covalent matrix compound may be an organic compound substantially composed of covalent C, H, O, N, and S, which may optionally also include covalent B, P, or Si. A substantially covalent matrix compound may be an organic aromatic covalent compound without metal atoms, and most of its backbone atoms may be selected from C, O, S, and N, preferably selected from C, O, and N, wherein most of the atoms are C atoms. Alternatively, a covalent matrix compound may be without metal atoms, and most of its backbone atoms may be selected from C and N, preferably, a covalent matrix compound may be without metal atoms, and most of its backbone atoms may be C and a minority of its backbone atoms may be N.

[0281] According to one embodiment, the substantially covalent matrix compound has a molecular weight Mw of ≥ 400 and ≤ 2000 g / mol, preferably ≥ 450 and ≤ 1500 g / mol, more preferably ≥ 500 and ≤ 1000 g / mol, additionally preferably ≥ 550 and ≤ 900 g / mol, and also preferably ≥ 600 and ≤ 800 g / mol.

[0282] In one embodiment, the HOMO level of a substantially covalent matrix compound may be more negative than the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octakis(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetraamine (CAS 207739-72-8) when measured under the same conditions.

[0283] In one embodiment of the present invention, the covalent matrix compound may substantially be free of alkoxy groups.

[0284] Preferably, substantially the covalent matrix compound comprises at least one arylamine moiety, alternatively a diarylamine moiety, and alternatively a triarylamine moiety.

[0285] Preferably, substantially the covalent matrix compound is free of TPD or NPB.

[0286] Preferably, the matrix compound of the hole injection layer has no metal and / or ionic bonds.

[0287] Compound of formula (III) or compound of formula (IV)

[0288] According to another aspect of the present invention, substantially the covalent matrix compound may comprise at least one arylamine compound, diarylamine compound, triarylamine compound, compound of formula (III), or compound of formula (IV):

[0289]

[0290] Here:

[0291] T 1 , T 2 , T 3 , T 4 and T 5 is independently selected from single bond, phenylene, biphenylene, terphenylene, or naphthenylene, preferably from single bond or phenylene;

[0292] T 6 is phenylene, biphenylene, terphenylene, or naphthenylene;

[0293] Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 is independently substituted or unsubstituted C6 to C 20 Aryl, or substituted or unsubstituted C3 to C 20Heteroarylene, substituted or unsubstituted biphenylene, 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 tetracene, substituted or unsubstituted tetraphene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthen, substituted or unsubstituted carbazole, substituted or unsubstituted 9-phenylcarbazole, substituted or unsubstituted azepine, substituted or unsubstituted dibenzo[b,f]azepine, substituted or unsubstituted 9,9'-spirobi[fluorene], substituted or unsubstituted A substituted or unsubstituted aromatic fused ring system comprising spiro[fluorene-9,9'-xanthen] or at least three substituted or unsubstituted aromatic rings, wherein the aromatic rings are selected from the group comprising a substituted or unsubstituted non-hetero, a substituted or unsubstituted hetero 5-membered ring, a substituted or unsubstituted 6-membered ring and / or a substituted or unsubstituted 7-membered ring, a substituted or unsubstituted fluorene, or an aromatic fused ring system comprising two to six substituted or unsubstituted 5- to 7-membered rings, and the rings are selected from the group comprising (i) an unsaturated 5- to 7-membered ring of a heterocycle, (ii) a 5- to 6-membered ring of an aromatic heterocycle, (iii) an unsaturated 5- to 7-membered ring of a non-heterocycle, and (iv) a 6-membered ring of a non-heterocycle;

[0294] Here

[0295] Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 The substituents are H, D, F, C(-O)R 2, CN, Si(R 2 )3, P(-O)(R 2 )2, OR 2 , S(-O)R 2 , S(-O)2R 2 , straight-chain alkyl having 1 to 20 substituted or unsubstituted carbon atoms, branched alkyl having 1 to 20 substituted or unsubstituted carbon atoms, cyclic alkyl having 3 to 20 substituted or unsubstituted carbon atoms, alkenyl or alkynyl group having 2 to 20 substituted or unsubstituted carbon atoms, alkoxy group having 1 to 20 substituted or unsubstituted carbon atoms, aromatic ring system having 6 to 40 substituted or unsubstituted aromatic ring atoms, and heteroaromatic ring system having 5 to 40 substituted or unsubstituted aromatic ring atoms, unsubstituted C6 to C 18 Aryl, unsubstituted C3 to C 18 The ring is selected identically or differently from the group comprising a fused ring system comprising a heteroaryl, 2 to 6 unsubstituted 5- to 7-membered rings, and the ring is selected from the group comprising an unsaturated 5- to 7-membered ring of a heterocycle, a 5- to 6-membered ring of an aromatic heterocycle, an unsaturated 5- to 7-membered ring of a non-heterocycle, and a 6-membered ring of a non-heterocycle.

[0296] Here, R 2 is H, D, a straight-chain alkyl having 1 to 6 carbon atoms, a branched alkyl having 1 to 6 carbon atoms, a cyclic alkyl having 3 to 6 carbon atoms, an alkenyl or alkynyl group having 2 to 6 carbon atoms, C6 to C 18 aryl or C3 to C 18 It can be selected from heteroaryls.

[0297] According to an embodiment of the electronic device, the covalent matrix compound substantially comprises a compound of formula (III) or formula (IV):

[0298]

[0299] Here

[0300] T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from single bond, phenylene, biphenylene, terphenylene, or naphthenylene, and preferably can be a single bond or phenylene;

[0301] T 6 is phenylene, biphenylene, terphenylene, or naphthenylene;

[0302] Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 is independently substituted or unsubstituted C6 to C 20 Aryl, or substituted or unsubstituted C3 to C 20Heteroarylene, substituted or unsubstituted biphenylene, 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 tetracene, substituted or unsubstituted tetraphene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthen, substituted or unsubstituted carbazole, substituted or unsubstituted 9-phenylcarbazole, substituted or unsubstituted azepine, substituted or unsubstituted dibenzo[b,f]azepine, substituted or unsubstituted 9,9'-spirobi[fluorene], substituted or unsubstituted A substituted or unsubstituted aromatic fused ring system comprising spiro[fluorene-9,9'-xanthen] or at least three substituted or unsubstituted aromatic rings, wherein the aromatic rings are selected from the group comprising a substituted or unsubstituted non-hetero, a substituted or unsubstituted hetero 5-membered ring, a substituted or unsubstituted 6-membered ring and / or a substituted or unsubstituted 7-membered ring, a substituted or unsubstituted fluorene, or a fused ring system comprising two to six substituted or unsubstituted 5- to 7-membered rings, and the rings may be selected from the group comprising (i) an unsaturated 5- to 7-membered ring of a heterocycle, (ii) a 5- to 6-membered ring of an aromatic heterocycle, (iii) an unsaturated 5- to 7-membered ring of a non-heterocycle, and (iv) a 6-membered ring of a non-heterocycle. and;

[0303] Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5The substituents are H, a straight-chain alkyl having 1 to 20 carbon atoms, a branched alkyl having 1 to 20 carbon atoms, a cyclic alkyl having 3 to 20 carbon atoms, an alkenyl or alkynyl group having 2 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, C6 to C 18 Aryl, C3 to C 18 The fused ring system comprising a heteroaryl, 2 to 6 unsubstituted 5- to 7-membered rings is selected identically or differently from the group comprising heterocyclic unsaturated 5- to 7-membered rings, the rings are selected from the group comprising aromatic heterocyclic 5- to 6-membered rings, non-heterocyclic unsaturated 5- to 7-membered rings, and non-heterocyclic 6-membered rings.

[0304] Preferably, Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 The substituents are the same or different and include H, a straight-chain alkyl having 1 to 6 carbon atoms, a branched alkyl having 1 to 6 carbon atoms, a cyclic alkyl having 3 to 6 carbon atoms, an alkenyl or alkynyl group having 2 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, and C6 to C 18 Aryl, C3 to C 18The fused ring system comprising a heteroaryl, 2 to 4 unsubstituted 5- to 7-membered ring is selected from the group comprising heterocyclic unsaturated 5- to 7-membered rings, aromatic heterocyclic 5- to 6-membered rings, non-heterocyclic unsaturated 5- to 7-membered rings, and aromatic non-heterocyclic 6-membered rings; more preferably, the substituents are the same or different and are selected from the group consisting of H, straight-chain alkyl having 1 to 4 carbon atoms, branched alkyl having 1 to 4 carbon atoms, cyclic alkyl having 3 to 4 carbon atoms, and / or phenyl.

[0305] Thus, the compound of formula (III) or (IV) can have a rate onset temperature suitable for mass production.

[0306] According to an embodiment of the electronic device, the covalent matrix compound substantially comprises a compound of formula (III) or formula (IV):

[0307]

[0308] Here

[0309] T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from single bond, phenylene, biphenylene, terphenylene, or naphthenylene, and preferably can be a single bond or phenylene;

[0310] T 6 is phenylene, biphenylene, terphenylene, or naphthenylene;

[0311] Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 is independently unsubstituted C6 to C 20 Aryl, or unsubstituted C3 to C20 A system of unsubstituted aromatic fused rings comprising heteroarylene, 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 tetraphene, unsubstituted dibenzofuran, unsubstituted dibenzothiophene, unsubstituted xanthen, unsubstituted carbazole, unsubstituted 9-phenylcarbazole, unsubstituted azepine, unsubstituted dibenzo[b,f]azepine, unsubstituted 9,9'-spirobi[fluorene], unsubstituted spiro[fluorene-9,9'-xanthen], or at least three unsubstituted aromatic rings, wherein the aromatic rings are unsubstituted non-hetero, unsubstituted hetero The ring is selected from an aromatic fused ring system selected from the group comprising a fused ring system comprising a 5-membered ring, an unsubstituted 6-membered ring and / or an unsubstituted 7-membered ring, an unsubstituted fluorene, or two to six unsubstituted 5- to 7-membered rings, wherein the ring is selected from the group comprising (i) an unsaturated 5- to 7-membered ring of a heterocycle, (ii) a 5- to 6-membered ring of an aromatic heterocycle, (iii) an unsaturated 5- to 7-membered ring of a non-heterocycle, and (iv) a 6-membered ring of a non-heterocycle.

[0312] According to an embodiment of the electronic device, the covalent matrix compound substantially comprises a compound of formula (III) or formula (IV):

[0313]

[0314] Here

[0315] T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from single bond, phenylene, biphenylene, terphenylene, or naphthenylene, and preferably can be a single bond or phenylene;

[0316] T 6 is phenylene, biphenylene, terphenylene, or naphthenylene;

[0317] Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 is independently unsubstituted C6 to C 20 Aryl, or unsubstituted C3 to C 20 It may be selected from heteroarylene, 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 tetraphene, unsubstituted dibenzofuran, unsubstituted dibenzothiophene, unsubstituted xanthen, unsubstituted carbazole, unsubstituted 9-phenylcarbazole, unsubstituted azepine, unsubstituted dibenzo[b,f]azepine, unsubstituted 9,9'-spirobi[fluorene], and unsubstituted spiro[fluorene-9,9'-xanthen].

[0318] Thus, the compound of formula (III) or (IV) can have a rate onset temperature suitable for mass production.

[0319] According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from single bonds, phenylene, biphenylene, or terphenylene. According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from phenylene, biphenylene, or terphenylene, and T 1 , T 2 , T 3 , T 4 and T 5One of them is a single bond. According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from phenylene or biphenylene, and T 1 , T 2 , T 3 , T 4 and T 5 One of them is a single bond. According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 can be independently selected from phenylene or biphenylene, and T 1 , T 2 , T 3 , T 4 and T 5 Two of them are single bonds.

[0320] According to one embodiment, T 1 , T 2 and T 3 can be independently selected from phenylene, and T 1 , T 2 and T 3 One of them is a single bond. According to one embodiment, T 1 , T 2 and T 3 can be independently selected from phenylene, and T 1 , T 2 and T 3 Two of them are single bonds.

[0321] According to one embodiment, T 6 can be phenylene, biphenylene, or terphenylene. According to one embodiment, T 6 ... may be phenylene. According to one embodiment, T 6 It may be biphenylene. According to one embodiment, T 6 It can be terphenylene.

[0322] According to one embodiment, Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 can be independently selected from B1 to B16:

[0323]

[0324] Here, the asterisk "*" indicates the joining position.

[0325] According to one embodiment, Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 It can be independently selected from B1 to B15; alternatively, it can be selected from B1 to B10, and B13 to B15.

[0326] According to one embodiment, Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 It can be independently selected from the group consisting of B1, B2, B5, B7, B9, B10, B13 to B16.

[0327] The rate onset temperature is Ar 1 , Ar 2 , Ar 3 , Ar 4 and Ar 5 When selected from this range, it may be in a range particularly suitable for mass production.

[0328] "The matrix compound of formula (III) or formula (IV)" may also be referred to as a "hole transport compound".

[0329] 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 a heteroaromatic ring.

[0330] According to one embodiment, the compound of formula (III) or formula (IV) may comprise a substituted or unsubstituted aromatic fused ring system comprising at least ≥ 1 to ≤ 6 heteroaromatic rings, and a substituted or unsubstituted unsaturated 5- to 7-membered ring of at least ≥ 1 to ≤ 3 heterocycles, preferably a substituted or unsubstituted aromatic fused ring system comprising ≥ 2 to ≤ 5 heteroaromatic rings.

[0331] According to one embodiment, the compound of formula (III) or formula (IV) comprises a substituted or unsubstituted aromatic fused ring system comprising at least ≥ 1 to ≤ 6 heteroaromatic rings, and a substituted or unsubstituted aromatic fused ring system comprising at least ≥ 1 to ≤ 3 heterocyclic substituted or unsubstituted unsaturated 5- to 7-membered rings, preferably ≥ 2 to ≤ 5 heteroaromatic rings, and a substituted or unsubstituted aromatic fused ring system comprising at least ≥ 1 to ≤ 3 heterocyclic substituted or unsubstituted unsaturated 5- to 7-membered rings, more preferably 3 or 4 heteroaromatic rings and optionally at least ≥ 1 to ≤ 3 heterocyclic substituted or unsubstituted unsaturated 5- to 7-membered rings, and additionally preferably an aromatic fused ring system comprising heteroaromatic rings, which are unsubstituted and optionally It is an unsubstituted unsaturated 5- to 7-membered ring of at least ≥ 1 to ≤ 3 heterocycles.

[0332] 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, additionally preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems.

[0333] 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, additionally preferably 3 or 4 substituted or unsubstituted heteroaromatic rings, which comprises substituted or unsubstituted aromatic rings.

[0334] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least ≥ 1 to ≤ 3 or 2 heterocyclic substituted or unsubstituted unsaturated 5-membered to 7-membered rings.

[0335] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least ≥ 1 to ≤ 3 or 2 heterocyclic substituted or unsubstituted unsaturated 7-membered rings.

[0336] According to one embodiment, the substituted or unsubstituted aromatic fused ring system of the compound of formula (III) or formula (IV) may comprise at least ≥ 1 to ≤ 3 or 2 heterocycles of substituted or unsubstituted unsaturated 5- to 7-membered rings.

[0337] According to one embodiment, the substituted or unsubstituted aromatic fused ring system of the matrix compound of formula (III) or formula (IV) may comprise at least ≥ 1 to ≤ 3 or 2 heterocyclic substituted or unsubstituted unsaturated 7-membered rings.

[0338] 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, additionally preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, wherein the aromatic fused ring systems comprise a substituted or unsubstituted unsaturated 5- to 7-membered ring of a heterocycle.

[0339] 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, additionally preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, which comprises substituted or unsubstituted heteroaromatic rings, and the aromatic fused ring systems comprise substituted or unsubstituted unsaturated 5- to 7-membered rings of a heterocycle.

[0340] 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, additionally preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems, and the aromatic fused ring systems comprise at least ≥ 1 to ≤ 3 or 2 heterocyclic substituted or unsubstituted unsaturated 5- to 7-membered rings.

[0341] 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, additionally preferably 3 or 4 substituted or unsubstituted heteroaromatic rings, which comprises substituted or unsubstituted aromatic rings, and the aromatic fused ring system comprises at least ≥ 1 to ≤ 3 or 2 heterocycles of substituted or unsubstituted unsaturated 5- to 7-membered rings.

[0342] According to one embodiment, a compound of formula (III) or formula (IV) may include the following:

[0343] - A substituted or unsubstituted aromatic fused ring system having a fused aromatic ring selected from the group comprising at least ≥ 2 to ≤ 6, preferably ≥ 3 to ≤ 5, or 4 substituted or unsubstituted non-hetero-aromatic rings, a substituted or unsubstituted hetero 5-membered ring, a substituted or unsubstituted 6-membered ring and / or a substituted or unsubstituted unsaturated 5- to 7-membered ring of a heterocycle; or

[0344] - An unsubstituted aromatic fused ring system having a fused aromatic ring selected from the group comprising at least ≥ 2 to ≤ 6, preferably ≥ 3 to ≤ 5, or 4 unsubstituted non-hetero-aromatic rings, an unsubstituted hetero 5-membered ring, an unsubstituted 6-membered ring and / or an unsubstituted unsaturated 5- to 7-membered ring of a heterocycle.

[0345] It should be noted 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 be noted that the substituted or unsubstituted unsaturated 5- to 7-membered ring may not be an aromatic ring.

[0346] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least ≥ 1 to ≤ 6, preferably ≥ 2 to ≤ 5, or more preferably 3 or 4 of the following substituted or unsubstituted aromatic fused ring systems:

[0347] - At least one unsaturated 5-membered ring, and / or

[0348] - At least one unsaturated 6-membered ring, and / or

[0349] - At least one unsaturated 7-membered ring; where preferably at least one unsaturated 5-membered ring and / or at least one unsaturated 7-membered ring comprises at least 1 to 3, preferably 1 heteroatom.

[0350] According to one embodiment, the compound of formula (III) or formula (IV) may comprise at least ≥ 1 to ≤ 6, preferably ≥ 2 to ≤ 5, or more preferably 3 or 4 of the following substituted or unsubstituted aromatic fused ring systems:

[0351] - At least one aromatic 5-membered ring, and / or

[0352] - At least one aromatic 6-membered ring, and / or

[0353] - 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 comprises at least 1 to 3, preferably 1 heteroatom;

[0354] The substituted or unsubstituted aromatic fused ring system comprises at least ≥ 1 to ≤ 3 or 2 heterocycles of substituted or unsubstituted unsaturated 5- to 7-membered rings.

[0355] According to one embodiment, a compound of formula (III) or formula (IV) may include the following:

[0356] - at least ≥ 6 to ≤ 12, preferably ≥ 7 to ≤ 11, more preferably ≥ 8 to ≤ 10 or 9 aromatic rings; and / or

[0357] - At least ≥ 4 to ≤ 11, preferably ≥ 5 to ≤ 10, more preferably ≥ 6 to ≤ 9, or additionally preferably 7 or 8 non-heteroaromatic rings, preferably the non-heteroaromatic rings are aromatic C6 rings; and / or

[0358] - At least ≥ 1 to ≤ 4, preferably 2 or 3 aromatic 5-membered rings, preferably heteroaromatic 5-membered rings; and / or

[0359] - At least one or two heterocyclic unsaturated 5- to 7-membered rings, preferably at least one or two heterocyclic unsaturated 7-membered rings;

[0360] - At least ≥ 6 to ≤ 12, preferably ≥ 7 to ≤ 11, more preferably ≥ 8 to ≤ 10 or 9 aromatic rings,

[0361] Here, at least ≥ 4 to ≤ 11, preferably ≥ 5 to ≤ 10, more preferably ≥ 6 to ≤ 9, or additionally preferably 7 or 8 are non-hetero-aromatic rings, and

[0362] Herein, at least ≥ 1 to ≤ 4, preferably 2 or 3 aromatic rings are heteroaromatic rings, and the total number of non-heteroaromatic rings and heteroaromatic rings does not exceed 12 aromatic rings; and / or

[0363] - At least ≥ 6 to ≤ 12, preferably ≥ 7 to ≤ 11, more preferably ≥ 8 to ≤ 10 or 9 aromatic rings,

[0364] Here, at least ≥ 4 to ≤ 11, preferably ≥ 5 to ≤ 10, more preferably ≥ 6 to ≤ 9, or additionally preferably 7 or 8 are non-hetero-aromatic rings, and

[0365] 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 a total of 12 aromatic rings; and

[0366] 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

[0367] A hole transport compound or a hole transport compound according to formula (I) comprises at least one or two heterocyclic unsaturated 5- to 7-membered rings, preferably at least one or two heterocyclic unsaturated 7-membered rings.

[0368] According to one embodiment, the compound of formula (III) or formula (IV) may include a heteroatom selected from a group including O, S, N, B, or P, and preferably the heteroatom may be selected from a group including O, S, or N.

[0369] According to one embodiment, the matrix compound of formula (III) or formula (IV) may comprise at least ≥ 1 to ≤ 6, preferably ≥ 2 to ≤ 5, or more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems:

[0370] - At least one aromatic 5-membered ring, and / or

[0371] - At least one aromatic 6-membered ring, and / or

[0372] - 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 comprises at least 1 to 3, preferably 1 heteroatom;

[0373] The substituted or unsubstituted aromatic fused ring system optionally comprises at least ≥ 1 to ≤ 3 or 2 heterocycles of substituted or unsubstituted unsaturated 5- to 7-membered rings; the substituted or unsubstituted aromatic fused ring system comprises heteroatoms that may be selected from groups including O, S, N, B, P, or Si, and preferably the heteroatoms may be selected from groups including O, S, or N.

[0374] According to one embodiment, the compound of formula (III) or formula (IV) may not have heteroatoms that are not part of the aromatic ring and / or part of the unsaturated 7-membered ring, and preferably, the hole transport compound or the hole transport compound according to formula (I) may not have N atoms except for N atoms that are part of the aromatic ring or part of the unsaturated 7-membered ring.

[0375] According to one embodiment, a substantially covalent matrix compound comprises at least one naphthyl group, a carbazole group, a dibenzofuran group, a dibenzothiophen group and / or a substituted fluorenyl group, wherein the substituent is independently selected from methyl, phenyl, or fluorenyl.

[0376] According to one embodiment of the electronic device, the matrix compound of formula (III) or formula (IV) is selected from K1 to K15:

[0377]

[0378]

[0379]

[0380] Practically, the covalent matrix compounds may not include HTM014, HTM081, HTM163, HTM222, EL-301, HTM226, HTM355, HTM133, HTM334, HTM604, and EL-22T. Abbreviations represent manufacturer names, e.g., Merck or Lumtec.

[0381] semiconductor materials

[0382] According to another aspect, a semiconductor material comprising at least one compound of formula (I) is provided. The semiconductor material may additionally comprise at least one substantially covalent matrix compound.

[0383] semiconductor layer

[0384] According to another aspect, the semiconductor layer comprises one or more compounds of chemical formula (I).

[0385] According to one embodiment, the semiconductor layer comprises at least one compound of formula (I) which is a hole injection layer.

[0386] According to another embodiment, the semiconductor layer comprises a semiconductor material containing at least one compound of formula (I).

[0387] electronic devices

[0388] According to another embodiment, the electronic device comprises a substrate, an anode layer without a sublayer, or an anode layer that may include two or more sublayers, a cathode layer, and a hole injection layer, wherein the hole injection layer comprises a compound according to formula (I).

[0389] 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, and preferably may be a light-emitting layer.

[0390] According to another embodiment, the electronic device may have the following layer structure, and the layers have the following order:

[0391] Anode layer, a hole injection layer, a hole transport layer, an optional electron blocking layer, at least a first hole emission layer, an optional hole blocking layer, an electron transport layer, an optional electron injection layer, and a cathode layer, comprising substantially a covalent matrix compound and a compound of formula (I).

[0392] According to another aspect, an electronic device is provided 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 a light-emitting device, a thin-film transistor, a battery, a display device, or a photovoltaic cell, preferably a light-emitting device, and preferably the electronic device is part of a display device or a lighting device.

[0393] According to another aspect, an electronic device is provided comprising at least one organic light-emitting device according to any embodiment described throughout this specification, preferably the electronic device comprises an organic light-emitting diode of one of the embodiments described throughout this specification. More preferably, the electronic device is a display device.

[0394] According to one embodiment of the present invention, an electronic device may include a semiconductor layer comprising a compound of formula (I) and a substantially covalent matrix compound, wherein the substantially covalent matrix compound comprises at least one arylamine compound, diarylamine compound, or triarylamine compound, and 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), 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); more preferably, M is selected from Cu(II), Fe(III), Co(III), Mn(III), Ir(III), and Bi(III).

[0395] Anode layer

[0396] The anode layer, also referred to as the anode electrode, can be formed by depositing or sputtering the material used to form the anode layer. The material used to form the anode layer may have a high work function 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. The anode layer can also be formed using a metal, typically silver (Ag), gold (Au), or a metal alloy.

[0397] The anode layer may include two or more anode sublayers.

[0398] According to one embodiment, the anode layer includes a first anode sublayer and a second anode sublayer, wherein the first anode sublayer is positioned closer to the substrate and the second anode sublayer is positioned closer to the cathode layer.

[0399] According to one embodiment, the anode layer may include a first anode sublayer comprising or composed of Ag or Au and a second anode sublayer comprising or composed of a transparent conductive oxide.

[0400] According to one embodiment, the anode layer comprises a first anode sublayer, a second anode sublayer, and a third anode sublayer, wherein the first anode sublayer is positioned closer to the substrate, the second anode sublayer is positioned closer to the cathode layer, and the third anode sublayer is positioned between the substrate and the first anode sublayer.

[0401] According to one embodiment, the anode layer may comprise a first anode sublayer comprising or composed of Ag or Au, a second anode sublayer comprising or composed of a transparent conductive oxide, and optionally a third anode sublayer comprising or composed of a transparent conductive oxide. Preferably, the first anode sublayer may comprise or be composed of Ag, the second anode sublayer may comprise or be composed of ITO or IZO, and the third anode sublayer may comprise or be composed of ITO or IZO.

[0402] Preferably, the first anode sublayer may include or be made of Ag, the second anode sublayer may include or be made of ITO, and the third anode sublayer may include or be made of ITO.

[0403] Preferably, the transparent conductive oxides of the second and third anode sublayers can be selected to be the same.

[0404] According to one embodiment, the anode layer may include a first anode sublayer comprising Ag or Au having a thickness of 100 to 150 nm, a second anode sublayer comprising or made of a transparent conductive oxide having a thickness of 3 to 150 nm, and a third anode sublayer comprising or made of a transparent conductive oxide having a thickness of 3 to 20 nm.

[0405] Hole injection layer

[0406] A hole injection layer (HIL) can be formed on an anode layer by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blazette (LB) deposition, etc. When forming the HIL using vacuum deposition, the deposition conditions may vary depending on the hole transport compound used to form the HIL, as well as the desired structure and thermal properties of the HIL. However, generally, the conditions for vacuum deposition are a deposition temperature of 100 °C to 350 °C and a pressure of 10 -8 to 10 -3 It may include Torr (1 Torr = 133.322 Pa) and a deposition rate of 0.1 to 10 nm / sec.

[0407] When forming an HIL using spin coating or printing, the coating conditions may vary depending on the hole transport compound used to form the HIL, and the desired structure and thermal properties of the HIL. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80 °C to about 200 °C. The heat treatment removes the solvent after coating.

[0408] HIL can be formed from a compound of chemical formula (I).

[0409] The thickness of the HIL may be in the range of about 1 nm to about 15 nm, for example, about 2 nm to about 15 nm, or alternatively about 2 nm to about 12 nm.

[0410] When the thickness of the HIL is within this range, the HIL can have excellent hole injection characteristics without a significant penalty to the driving voltage.

[0411] According to one embodiment of the present invention, the hole injection layer may include the following:

[0412] - A compound of formula (I) in an amount of 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%, and

[0413] - at least about ≥ 70 wt% to about ≤ 99.5 wt%, preferably about ≥ 80 wt% to about ≤ 99.5 wt%, more preferably about ≥ 85 wt% to about ≤ 99 wt% of a substantially covalent matrix compound; preferably, the weight% of the compound of formula (I) is substantially lower than the weight% of the covalent matrix compound; wherein the weight% of the components is based on the total weight of the hole injection layer.

[0414] Preferably, the hole injection layer may not contain ionic liquid, metal phthalocyanine, CuPc, HAT-CN, pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile, F4TCNQ, metal fluoride and / or metal oxide, wherein the metal in the metal oxide is selected from Re and / or Mo. This allows the hole injection layer to be deposited under conditions suitable for mass production.

[0415] According to an embodiment of the electronic device, the hole injection layer is non-luminescent.

[0416] The hole injection layer will be understood as not being part of the anode layer.

[0417] additional floor

[0418] According to the present invention, an electronic device may include additional layers in addition to the layers already mentioned above. Exemplary embodiments of each layer are described below:

[0419] substrate

[0420] The substrate may be any substrate commonly used in the manufacture of electronic devices, such as organic light-emitting diodes. If light is emitted through the substrate, the substrate must be a transparent or translucent material, for example, a glass substrate or a transparent plastic substrate. If light is emitted through the top surface, the substrate may be a material that is not only transparent but also opaque, for example, 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.

[0421] The transport layer of the air force

[0422] According to one embodiment of the electronic device, the electronic device further comprises a hole transport layer, and the hole transport layer is disposed between a hole injection layer and at least one first light-emitting layer.

[0423] The hole transport layer may substantially comprise a 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 of substantially covalently bonded C, H, O, N, and S, which optionally further comprise covalently bonded B, P, As, and / or Se.

[0424] According to one embodiment of an electronic device, the hole transport layer substantially comprises a covalent matrix compound, and the substantially covalent matrix compound of the hole transport layer may be selected from organic compounds composed of substantially covalently bonded C, H, O, N, and S, which optionally further comprise covalently bonded B, P, As and / or Se.

[0425] According to one embodiment, the substantially covalent matrix compound of the hole transport layer may have a molecular weight Mw of ≥ 400 and ≤ 2000 g / mol, preferably ≥ 450 and ≤ 1500 g / mol, more preferably ≥ 500 and ≤ 1000 g / mol, additionally preferably ≥ 550 and ≤ 900 g / mol, and also preferably ≥ 600 and ≤ 800 g / mol.

[0426] 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.

[0427] According to one embodiment of an electronic device, the hole transport layer of the electronic device substantially comprises a covalent matrix compound, and preferably, the covalent matrix compound in the hole injection layer and the hole transport layer is selected substantially the same.

[0428] A hole transport layer (HTL) can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, Langmuir-Blazette (LB) deposition, etc. When the HTL is formed by vacuum deposition or spin coating, the deposition and coating conditions may be similar to the conditions for forming the hole injection layer. However, vacuum or solution deposition conditions may vary depending on the compound used to form the HTL.

[0429] The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, further about 20 nm to about 190 nm, further about 40 nm to about 180 nm, further about 60 nm to about 170 nm, further about 80 nm to about 200 nm, further about 100 nm to about 180 nm, and further about 110 nm to about 140 nm.

[0430] When the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without a significant penalty to the driving voltage.

[0431] Electromagnetic blocking layer

[0432] The function of the electron blocking layer (EBL) is to prevent electrons from being transported from the emissive layer to the hole transport layer, thereby confining electrons to the emissive layer. This can improve efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer contains a triarylamine compound.

[0433] If the electron blocking layer has a high triplet level, it can be described as a triplet control layer.

[0434] The function of the triplet control layer is to reduce triplet quenching when using a phosphorescent green or blue emitting layer. This allows for higher luminescence efficiency to be achieved from the phosphorescent emitting layer. The triplet control layer can be selected from triarylamine compounds having a triplet level higher than the triplet level of the phosphorescent emitter in the adjacent emitting layer.

[0435] The thickness of the electron blocking layer can be selected between 2 and 20 nm.

[0436] Photoactive layer (PAL)

[0437] The photoactive layer converts current into photons, or photons into current. The PAL can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the PAL is formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to the HIL formation conditions. However, the deposition and coating conditions may vary depending on the compound used to form the PAL. It may be provided that the photoactive layer does not contain the compound of formula (I). The photoactive layer may be an emitting layer or a light-absorbing layer.

[0438] Emissive layer (EML)

[0439] At least one first light-emitting layer (EML), also referred to as the first light-emitting layer, can be formed on the HTL or EBL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the EML is formed using vacuum deposition or spin coating, the deposition and coating conditions may be similar to the HIL formation conditions. However, the deposition and coating conditions may vary depending on the compound used to form the EML.

[0440] According to the present invention, the electronic device preferably comprises one light-emitting layer named "first light-emitting layer." However, the electronic device optionally comprises two light-emitting layers, wherein the first layer is named the first light-emitting layer and the second layer is named the second light-emitting layer.

[0441] At least one light-emitting layer, also referred to as the first light-emitting layer, may be provided without the matrix compound of the hole injection layer.

[0442] At least one light-emitting layer may be provided not to contain a compound of formula (I).

[0443] At least one emitting layer (EML) may be composed of a combination of a host and an emitter dopant. Examples of hosts are Alq3, 4,4'-N,N'-dicarbazole-biphenyl (HTC-10), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4''-tris(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarylene (DSA), and bis(2-(2-hydroxyphenyl)benzo-thiazolate)zinc (Zn(BTZ)2).

[0444] The emitter dopant can be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to higher efficiency. The emitter can be a small molecule or a polymer.

[0445] Examples of red emitter dopants include, but are not limited to, PtOEP, Ir(piq)3, and Btp2lr(acac). These compounds are phosphorescent emitters, but fluorescent red emitter dopants may also be used.

[0446] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), and Ir(mpyp)3.

[0447] Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd) and Ir(dfppz)3 and ter-fluorene. 4,4'-bis(4-diphenylamiostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetra-tert-butylperylene (TBPe) are examples of fluorescent blue emitter dopants.

[0448] The content of the emitter dopant may be in the range of about 0.01 to about 50 parts by weight based on 100 parts by weight of the host. Alternatively, at least one light-emitting layer may be made of a light-emitting polymer. The EML may have a thickness of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is in this range, the EML can have excellent light emission without a significant penalty to the driving voltage.

[0449] Hole Blocking Layer (HBL)

[0450] To prevent holes from diffusing into the ETL, a hole blocking layer (HBL) can be formed on the EML using vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. If the EML contains a phosphorescent emitter dopant, the HBL may also have a triplet exciton blocking function.

[0451] HBL can also be referred to as an auxiliary ETL or a-ETL.

[0452] When HBL is formed using vacuum deposition or spin coating methods, the deposition and coating conditions may be similar to those for HIL formation. However, the deposition and coating conditions may vary depending on the compounds used for HBL formation. Any compound commonly used to form HBL may be used. Examples of compounds that form HBL include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and triazine derivatives.

[0453] HBL can have a thickness in the range of about 5 nm to about 100 nm, for example, about 10 nm to about 30 nm. When the thickness of the HBL is in this range, the HBL can have excellent hole-blocking characteristics without a significant penalty to the driving voltage.

[0454] Electron Transport Layer (ETL)

[0455] The electronic device according to the present invention may further include an electron transport layer (ETL).

[0456] According to another embodiment of the present invention, the electron transport layer may further include an azine compound, preferably a triazine compound.

[0457] In one embodiment, the electron transport layer may further include a dopant selected from alkali organic complexes, preferably LiQ.

[0458] The thickness of the ETL can be in the range of about 15 nm to about 50 nm, for example, in the range of about 20 nm to about 40 nm. When the thickness of the ETL is in this range, the ETL can have satisfactory electron-injection characteristics without a significant penalty to the driving voltage.

[0459] 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 include an azine compound. Preferably, the azine compound is a triazine compound.

[0460] Electron injection layer (EIL)

[0461] An optional EIL capable of facilitating electron injection from the cathode can be formed directly on the ETL, preferably on the electron transport layer. Examples of materials for forming the EIL include lithium 8-hydroxyquinolinoleate (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, and Mg, which are known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL, but the deposition and coating conditions may vary depending on the material used to form the EIL.

[0462] The thickness of the EIL may be in the range of about 0.1 nm to about 10 nm, for example, in the range of about 0.5 nm to about 9 nm. When the thickness of the EIL is in this range, the electron injection layer can have satisfactory electron-injection characteristics without a significant penalty to the driving voltage.

[0463] cathode layer

[0464] The cathode layer is formed on an ETL or optional EIL. The cathode layer can be formed from a metal, an alloy, an electrically conductive compound, or a mixture thereof. The cathode layer may have a low work function. For example, the cathode layer can be formed from 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 from a transparent conductive oxide such as ITO or IZO.

[0465] The thickness of the cathode layer may be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode layer is in the range of about 5 nm to about 50 nm, the cathode layer may be transparent or translucent even if it is formed of a metal or a metal alloy.

[0466] The cathode layer will be understood as not being part of the electron injection layer or electron transport layer.

[0467] Manufacturing method

[0468] According to another aspect of the present invention, a method for manufacturing an electronic device using the following is provided:

[0469] - At least one deposition source, preferably two deposition sources, more preferably at least three deposition sources.

[0470] Suitable deposition methods include the following:

[0471] - Deposition via vacuum thermal evaporation;

[0472] - Deposition via solution treatment, preferably the treatment may be selected from spin-coating, printing, and casting; and / or

[0473] - Slot die coating.

[0474] According to various embodiments of the present invention, a method of using the following is provided:

[0475] - A first deposition source for releasing a matrix compound, and

[0476] - A second deposition source for releasing a compound of formula (I), also named a metal complex.

[0477] The method includes the step of forming a hole injection layer; accordingly, for an electronic device:

[0478] - The hole injection layer is formed by releasing a matrix compound according to the present invention from a first deposition source and releasing a compound of formula (I), also named a metal complex, from a second deposition source.

[0479] Hereinafter, embodiments are illustrated in more detail with reference to examples. However, the present invention is not limited to the following examples. Exemplary aspects will now be described in detail.

[0480] In addition to the aforementioned components, no special exceptions apply to the size, shape, material selection, and technical concept of the components used according to the present invention in the claimed components and described embodiments, and standards known in the art may be applied without limitation.

[0481] Further details, features, and benefits regarding the object of the present invention are disclosed in the following description of each drawing illustrating the dependent claims and preferred embodiments according to the present invention in an exemplary manner. However, any embodiment does not necessarily represent the entire scope of the present invention, and therefore, the claims and the specification are referenced to interpret the scope of the present invention. The foregoing general description and the following detailed description are merely illustrative and for illustrative purposes and are to be understood as intended to provide further description of the claimed invention. Brief explanation of the drawing

[0482] FIG. 1 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention; FIG. 2 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention; FIG. 3 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention. FIG. 4 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention. FIG. 5 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention. FIG. 6 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention. FIG. 1 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) comprises 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). FIG. 2 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) comprises 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). FIG. 3 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) comprises a substrate (110), an anode layer (120), a semiconductor layer (130) comprising a compound of formula (I), a hole transport layer (HTL) (140), a light-emitting layer (EML) (150), an electron transport layer (ETL) (160), and a cathode layer (190). FIG. 4 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) comprises 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), an 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). FIG. 5 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) comprises a substrate (110), an anode layer (120) comprising a first anode sublayer (121) and a second anode sublayer (122), 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 (EBL) (155), an electron transport layer (ETL) (160), and a cathode layer (190). FIG. 6 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) comprises 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), an emitting layer (EML) (150), a hole blocking layer (EBL) (155), an electron transport layer (ETL) (160), and a cathode layer (190). The layers are arranged in the order mentioned above. In the above description, the method of manufacturing the organic electronic device (101) of the present invention starts, for example, with a substrate (110) having an anode layer (120) formed thereon, and a semiconductor layer (130) containing a compound of formula (I), a photoactive layer (151), and a cathode electrode (190) are formed on the anode layer (120), and these are formed in exactly that order or exactly the opposite order. In the above description, the OLED manufacturing method of the present invention starts with a substrate (110) having an anode layer (120) formed thereon, and on the anode layer (120), a semiconductor layer (130) containing 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, and these are formed in exactly that order or exactly the opposite order. A semiconductor layer (130) containing a compound of chemical formula (I) may be a hole injection layer. Although not illustrated in FIGS. 1, 2, 3, 4, 5 and 6, a capping layer and / or sealing layer may be further formed to seal the OLED (100) on the cathode electrode (190). Additionally, various variations may be applied. Specific details for implementing the invention

[0483] Hereinafter, one or more exemplary embodiments of the present invention will be described in detail with reference to the following examples. However, these examples are not intended to limit the purpose and scope of one or more exemplary embodiments of the present invention.

[0484] Synthesis method

[0485] The compound of chemical formula (I) can be prepared as described below.

[0486] Synthesis of 3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridine-4-yl)pentane-2,4-dione

[0487]

[0488] 200 mL of dry glime was added to 2.41 g (100.43 mmol) of sodium hydride in a flame-dried Schleck flask via a double-needle cannula. The suspension was cooled by ice-batch, and 10.3 mL (100.43 mmol) of acetylacetone was added dropwise. During addition, the temperature must not rise above 10 °C. 20 g (91.30 mmol) of 2,3,4,5-tetrafluoro-6-(trifluoromethyl)pyridine was added by syringe. The mixture was stirred at room temperature for 5 days, then added to 0.5 L of water, and acidified with concentrated hydrochloric acid to a pH of 1. The product was extracted with ethyl acetate. The combined organic layer was washed with water, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. The crude product was dissolved in hot methanol / water (3:1), cooled, the precipitate was filtered out, and dried under high vacuum. Yield: 10.5 g (38%)

[0489] Synthesis of tris(((Z)-4-oxo-3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridine-4-yl)pent-2-en-2-yl)oxy)iron (G6)

[0490]

[0491] 7.0 g (23.4 mmol) of substituted acetylacetone was dissolved in 70 ml of methanol. 1.90 g (23.4 mmol) of sodium bicarbonate was dissolved in 20 mL of water and added to the solution. The resulting suspension was heated and refluxed, and a solution of 1.27 g (7.8 mmol) of iron(III) chloride in 5 mL of water was added dropwise to the turbid solution. The mixture was stirred under reflux for 30 minutes. After cooling, the residue was filtered out and washed with water. The crude product was dissolved in THF, precipitated from methanol / water, filtered, and dried under high vacuum. Yield: 5.17 g (70%)

[0492] Synthesis of bis(((Z)-4-oxo-3-(2,3,5-trifluoro-6-(trifluoromethyl)pyridine-4-yl)pent-2-en-2-yl)oxy)copper(G21)

[0493]

[0494] 2.99 g (10 mmol) of substituted acetylacetone was dissolved in 50 mL of acetonitrile. 1.0 g (5 mmol) of copper(II) acetate monohydrate was added as a solid. 75 mL of water was added to the dark blue solution, and the resulting purple suspension was stirred at room temperature for 2 hours. The solid was filtered out and dried under vacuum. Yield: 2.95 g (95%)

[0495] Synthesis of 3-(perfluoropyridine-4-yl)pentane-2,4-dione

[0496]

[0497] 4.68 g (195 mmol) of sodium hydride was suspended in 200 mL of anhydrous glyme under a nitrogen atmosphere and cooled on an ice batch. 20 mL (195 mmol) of acetylacetone was added dropwise over 15 minutes. After an additional 15 minutes, 10.15 mL (97.4 mmol) of pentafluoropyridine was added dropwise, and the mixture was stirred at room temperature for 16 hours. The suspension was poured into 500 mL of water and acidified with 32% hydrochloric acid. The product was extracted with chloroform, the organic layer was dried with sodium sulfate, and the solvent was removed under reduced pressure. The unrefined product was recrystallized from methanol / water (8:2) to obtain 11.4 g (45%) of solid.

[0498] Synthesis of tris(3-(perfluoropyride-4-yl)pentane-2,4-dionato)iron(III) (G5)

[0499]

[0500] 3.73 g (15 mmol) of 3-(perfluoropyridine-4-yl)pentane-2,4-dione was dissolved in 30 ml of methanol, and 0.8 g (5 mmol) of iron trichloride dissolved in 5 ml of water was added dropwise. 1.26 g (15 mmol) of sodium bicarbonate was added, and the mixture was stirred overnight at room temperature. The precipitate was filtered out, washed with methanol / water (2:1), and dried under high vacuum. 3.75 g (93%) of the product was obtained as a solid.

[0501] Synthesis of 3-(2,4,6-tris(trifluoromethyl)pyrimidine-5-yl)pentane-2,4-dione

[0502]

[0503] 60 ml of anhydrous glyme was added to 1.59 g (66.2 mmol) of sodium hydride in a flame-dried Schlenk flask, and the suspension was cooled on an ice batch. 6.63 g (66.2 mmol) of acetylacetone was diluted in 10 ml of dry glyme and added dropwise to the mixture stirred for 30 minutes. 10 g (33.1 mmol) of 5-fluoro-2,4,6-tris(trifluoromethyl)-pyrimidine was diluted in 10 ml of anhydrous glyme and added to the suspension. The mixture was stirred overnight at room temperature. 250 ml of water was added to the mixture, and 32% hydrochloric acid was added until the pH reached 1. The product was extracted with ethyl acetate. The combined organic layer was washed with water, dried with sodium sulfate, and the solvent was removed under reduced pressure. The unrefined product was refined by bulb-to-bulb distillation to obtain 8.4 g (66%) of oil.

[0504] Synthesis of tris(((Z)-4-oxo-3-(2,4,6-tris(trifluoromethyl)pyrimidine-5-yl)pent-2-en-2-yl)oxy)iron(G13)

[0505]

[0506] 6.37 g (16.67 mmol) of 3-(2,4,6-tris(trifluoromethyl)pyrimidine-5-yl)pentane-2,4-dione was dissolved in 60 ml of methanol, and 1.40 g (16.67 mmol) of sodium bicarbonate dissolved in 20 ml of water was added. The mixture was heated under reflux. 0.90 g (5.56 mmol) of iron trichloride dissolved in 5 ml of water was added dropwise to the solution. The mixture was stirred overnight at 70 °C. After cooling on an ice batch, the precipitate was filtered out and washed with methanol and water. 1.23 g (18%) of the product was obtained as a solid.

[0507] Synthesis of tris((-1,1,1-trifluoro-4-oxo-4-(2-(trifluoromethyl)pyridine-4-yl)but-2-en-2-yl)oxy)iron(G50)

[0508]

[0509] 8.0 g (28.03 mmol) of 4,4,4-trifluoro-1-(2-(trifluoromethyl)pyridine-4-yl)butane-1,3-dione was dissolved in 160 ml of methanol. 2.35 g (38.03 mmol) of sodium bicarbonate and 10 ml of water were added. 1.51 g (9.34 mmol) of iron trichloride dissolved in 2 ml of water was added dropwise to the mixture. 30 mL of water was added to the solution, and the reaction mixture was stirred overnight at room temperature. The precipitate was filtered out and dried overnight under vacuum. 7.17 g (84%) of the product was obtained as a solid.

[0510] Additional compounds according to the present invention may be prepared as described above or by methods known in the art.

[0511] sublimation temperature

[0512] Under nitrogen in a glove box, 0.5 to 5 g of the compound is loaded into the evaporation source of the sublimation unit. The sublimation unit consists of an inner glass tube comprising a 3 cm diameter bulb placed inside a 3.5 cm diameter glass tube. The sublimation unit is placed inside a tube oven (Creaphys DSU 05 / 2.1). The sublimation unit is emptied via a membrane pump (Pfeiffer Vacuum MVP 055-3C) and a turbopump (Pfeiffer Vacuum THM071 YP). Using a pressure gauge (Pfeiffer Vacuum PKR 251), the pressure between the sublimation unit and the turbopump is measured. When the pressure reaches 10 -5When reduced to mbar, the temperature is increased in increments of 10 to 30 K until the compound begins to be deposited in the harvesting zone of the sublimation device. The temperature is further increased in increments of 10 to 30 K until a sublimation rate is reached in which the compound from the source is visibly depleted over a period of 30 minutes to 1 hour and a significant amount of the compound accumulates in the harvesting zone. T subl The sublimation temperature, also known as the sublimation temperature, is the temperature inside the sublimation device where the compound is deposited in the harvesting zone at a visible rate, and is measured in degrees Celsius.

[0513] Rate start temperature

[0514] Rate start temperature (T RO ) is determined by loading 100 mg of the compound into the VTE source. As a VTE source, point sources for organic materials can be used as provided by Kurt J. Lesker Company (www.lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com). The VTE source is 10 -5 At a pressure of less than mbar, it is heated at a constant rate of 15 K / min, and the internal temperature of the source is measured by a thermocouple. The evaporation of the compound is detected by a QCM detector that detects the deposition of the compound on a quartz crystal of the detector. The deposition rate on the quartz crystal is measured in angstroms per second. To determine the rate onset temperature, the deposition rate is plotted against the VTE source temperature. The rate onset is the temperature at which significant deposition occurs on the QCM detector. For accurate results, the VTE source is heated and cooled three times, and only the results from the second and third runs are used to determine the rate onset temperature.

[0515] To achieve good control over the evaporation rate of organic compounds, the rate onset temperature may be in the range of 200 to 255 °C. If the rate onset temperature is below 200 °C, evaporation may be too fast and, consequently, difficult to control. If the rate onset temperature is above 255 °C, the evaporation rate may be too low, which may result in a low tact time, and decomposition of organic compounds in the VTE source may occur due to prolonged exposure to elevated temperatures.

[0516] The rate onset temperature is an indirect measure of the volatility of a compound. The higher the rate onset temperature, the lower the volatility of the compound.

[0517] General procedure for manufacturing an electronic device including a semiconductor layer containing a metal complex and a matrix compound

[0518] For Examples 1 to 9 and Comparative Examples 1 to 3 of the present invention in Table 2, 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 x 50 mm x 0.7 mm, ultrasonically cleaned with water for 60 minutes, and then ultrasonically cleaned with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, and then the anode layer was prepared by plasma treatment. Plasma treatment was performed at 75 W for 35 seconds in an atmosphere containing 97.6 vol% nitrogen and 2.4 vol% oxygen.

[0519] Subsequently, the matrix compound and the metal complex were co-deposited on the anode layer under vacuum to form a hole injection layer (HIL) with a thickness of 10 nm. The composition of the hole injection layer can be seen in Table 2. In Examples 1 to 15 of the present invention, a compound of formula (I) is used.

[0520] The chemical formula of the matrix compound HTM-1 is as follows:

[0521]

[0522] Next, a matrix compound was vacuum-deposited onto the HLI to form an HTL with a thickness of 123 nm. The matrix compound in the HTL is selected to be the same as the matrix compound in the HIL.

[0523] Next, N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluorene-2-amine) was vacuum deposited on the HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0524] Next, 97 volume% H09 (Sun Fine Chemicals, Korea) as an EML host and 3 volume% BD200 (Sun Fine Chemicals, Korea) as a fluorescent blue emitter dopant were deposited on the EBL to form a 20 nm thick blue-emitting first emissive layer (EML).

[0525] Next, 2-(3'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was deposited on the light-emitting layer EML to form a hole-blocking layer with a thickness of 5 nm.

[0526] Subsequently, 50 wt% 4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene-1-yl)-[1,1'-biphenyl]-4-carbonitrile and 50 wt% LiQ were deposited to form an electron transport layer having a thickness of 31 nm on the hole blocking layer.

[0527] Next, 10 -7 Ag:Mg (90:10 volume%) was evaporated at a rate of 0.01 to 1 Å / s at mbar to form a cathode layer with a thickness of 13 nm on the electron transport layer.

[0528] Next, HTM-1 was deposited on the cathode layer to form a capping layer with a thickness of 75 nm.

[0529] The OLED stack is protected from ambient conditions by encapsulating the device with a glass slide. As a result, a cavity containing a getter material for additional protection is formed.

[0530] To evaluate the performance of an embodiment of the present invention in comparison with prior art, current efficiency is measured at 20°C. Current-voltage characteristics are determined by using a Keithley 2635 source measuring device to obtain the voltage as V and measure the current flowing through the device under test as mA. The voltage applied to the device varies in increments of 0.1 V within the range of 0 V to 10 V. Similarly, luminance-voltage characteristics and CIE coordinates are determined by measuring the luminance in cd / m² for each voltage value using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 10 mA / cm² 2 The cd / A efficiency in is determined by interpolating the luminance-voltage and current-voltage characteristics, respectively.

[0531] The device's lifetime LT is under ambient conditions (20 ℃) ​​and 30 mA / cm² 2 It is measured using a Keithley 2400 source meter and recorded in time units.

[0532] The brightness of the device is measured using a calibrated photodiode. Lifetime LT is defined as the time until the brightness of the device decreases to 97% of its initial value.

[0533] To determine voltage stability over time U (100h)–(1h), 30 mA / cm² 2 A current density was applied to the device. The operating voltage was measured after 1 hour and 100 hours, and then the voltage stability was calculated over a period of 1 hour to 100 hours.

[0534] Technical Effects Table 1

[0535] In Table 1, the physical properties of the compound of chemical formula (I) are shown, and reference is made to compounds 1 to 7 of the present invention and comparative compounds 1 to 6.

[0536] As can be seen from Table 1, the sublimation temperatures of comparative compounds 1 to 6 cannot be measured due to decomposition of the compounds, or the sublimation temperatures are in the range of 95 to 120 ℃.

[0537] The rate onset temperatures of comparative compounds 1 to 6 are in the range of < 100 to 101 ℃ (see Table 1).

[0538] Compound 1 of the present invention is a Cu(II) complex of formula (I). Compound 1 of the present invention differs from Comparative Compound 1 in that the substituted heteroaryl substituent is different. The sublimation temperature is increased from 110–120 °C of Comparative Compound 1 to 186 °C of Comparative Compound 1 of the present invention. The rate onset temperature is also improved to 105 °C.

[0539] Compound 2 of the present invention is a Fe(III) complex of formula (I). The sublimation temperature is 182 °C. The rate onset temperature is further improved to 128 °C.

[0540] Compound 3 of the present invention is a Fe(III) complex of formula (I). It differs from Compound 2 of the present invention in that the substituent on the heteroaryl group is different. The sublimation temperature is further improved to 209 °C, and the rate onset temperature is improved to 146 °C.

[0541] Compound 4 of the present invention is an Fe(III) complex of formula (I). The substituted heteroaryl substituent is different from that of compounds 2 and 3 of the present invention. The sublimation temperature is still high at 182 °C, and the rate onset temperature is high at 122 °C.

[0542] Compounds 5 and 6 of the present invention are Fe(III) complexes of formula (I). The sublimation and rate onset temperatures are improved compared to comparative compounds 1 to 6.

[0543] Compound 7 of the present invention is a Cu(II) complex of formula (I). The sublimation and rate onset temperatures are improved compared to comparative compounds 1 to 6.

[0544] In summary, the thermal stability, sublimation temperature, and / or rate onset temperature of the compound of formula (I) are substantially improved compared to the prior art.

[0545] OLED Performance Data Table 2

[0546] In Table 2, OLED performance data for the increase in operating voltage U (100h)-U (1h) and lifetime LT97 over time for Examples 1 to 15 and Comparative Examples 1 to 3 of the present invention are shown.

[0547] In Comparative Example 1, the semiconductor layer contains 3 volume% of the metal complex La(fod)3. The increase in operating voltage over time is 1.07V. The lifetime is 30 hours.

[0548] In Example 1 of the present invention, the semiconductor layer comprises 3 volume% of G6. The increase in operating voltage over time is 0.2 V. The lifetime is 75 hours.

[0549] In Comparative Example 2, the semiconductor layer contains 5 volume% of the metal complex La(fod)3. The increase in operating voltage over time is 0.85 V. The lifetime is 24 hours.

[0550] In Example 2 of the present invention, the semiconductor layer comprises 5 volume% of G6. The increase in operating voltage over time is 0.3 V. The lifetime is 95 hours.

[0551] In Comparative Example 3, the semiconductor layer contains 10 volume% of the metal complex La(fod)3. The increase in operating voltage over time is 0.89 V. The lifetime is 15 hours.

[0552] In Example 3 of the present invention, the semiconductor layer comprises 10 volume% of G6. The increase in operating voltage over time is 0.09 V. The lifetime is 79 hours.

[0553] In Example 4 of the present invention, the semiconductor layer comprises 19 volume% of G5. The increase in operating voltage over time is 0.8 V. The lifetime is 86 hours.

[0554] In Examples 5 to 7 of the present invention, the semiconductor layer comprises various Fe(III) complexes of formula (I) containing at least one CF3 group. Significant improvements in operating voltage stability over time and / or lifetime were achieved compared to Comparative Examples 1 to 3.

[0555] In Examples 8 and 9 of the present invention, the semiconductor layer comprises various Cu(II) complexes of formula (I) containing at least one CF3 group. Significant improvements in operating voltage stability over time and / or lifetime were achieved compared to Comparative Examples 1 to 3.

[0556] In summary, in a semiconductor layer containing a compound of formula (I), the increase in operating voltage is substantially reduced compared to the prior art, and the lifespan is substantially increased.

[0557] A reduced increase in operating voltage over time indicates that the stability of the electronic device has improved. An increase in lifespan is important for improving the stability of the electronic device.

[0558] Table 1: Characteristics of comparative compounds 1 to 6 and the compound of formula (I)

[0559] [Table 1]

[0560]

[0561] Table 2: Performance of electroluminescent devices containing metal complexes

[0562] [Table 2]

[0563]

[0564] In the detailed embodiments above, specific combinations of elements and features are merely illustrative; and the exchange and substitution of these teachings with other teachings in this specification and in the patents / applications by reference are expressly considered. As will be recognized by those skilled in the art, changes, modifications, and other implementations of what is described in this specification may occur to those skilled in the art without departing from the spirit and scope of the claimed invention. Accordingly, the foregoing description is merely illustrative and is not intended to be limiting. In the claims, the word "comprising" does not exclude other elements or steps, and the singular expressions "a" or "an" do not exclude the plural. The mere fact that specific measures are cited in different dependent claims does not indicate that a combination of such measures cannot be used advantageously. The scope of the invention is defined in the following claims and their corresponding parts. Furthermore, the references used in the description and claims do not limit the scope of the claimed invention.

Claims

Claim 1 As a compound represented by the chemical formula (I): (I) Here, M is a metal; L is a charge-neutral ligand coordinating to the metal M; n is an integer selected from 1 to 4 corresponding to the oxidation number of M; m is an integer selected from 0 to 2; and R 1 , R 2 and R 3 is independently H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 Alkoxy, substituted or unsubstituted C6 to C 24 Aryl, and substituted or unsubstituted C2 to C 24 The group is selected from heteroaryl groups, wherein at least one substituent is a halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy, substituted or unsubstituted C6 to C 18 Aryl, and substituted or unsubstituted C2 to C 18 Selected from heteroaryls, and the substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3; wherein at least one R 1 , R 2 and / or R 3 is substituted C2 to C 24 A compound selected from heteroaryl groups, wherein at least one substituent is selected from halogen, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyl, and partially or completely fluorinated C1 to C6 alkoxy. Claim 2 In claim 1, the metal M is selected from alkali, alkaline earth, transition, rare earth metals or group III to V metals, preferably the metal M is selected from transition or group III to V metals; preferably the 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 the metal M is selected from Cu(II), Fe(III), Co(III), Mn(III), Ir(III), Bi(III); More preferably, M is a compound selected from Fe(III) and Cu(II). Claim 3 In paragraph 1 or 2, L is H2O, C2 to C 40 Mono- or multi-dentate ethers and C2 to C 40 Thioether, C2 to C 40 Amines, C2 to C 40 Phosphine, C2 to C 20 alkyl nitrile or C2 to C 40 Selected from the group comprising aryl nitriles, or compounds according to chemical formula (II); (II) Here R 6 and R 7 is independently C1 to C 20 Alkyl, C1 to C 20 Heteroalkyl, C6 to C 20 Aryl, heteroaryl having 5 to 20 ring-forming atoms, halogenated or perhalogenated C1 to C 20 Alkyl, halogenated, or perhalogenated C1 to C 20 Heteroalkyl, halogenated or perhalogenated C6 to C 20 Selected from aryls, halogenated or perhalogenated heteroaryls having 5 to 20 ring-forming atoms, or at least one R 6 and R 7 It is connected to form a 5 to 20-membered ring, or 2 R 6 and / or 2 R 7 This is connected to form a 5 to 40-membered ring, or is unsubstituted or C1 to C 12 A compound forming a 5 to 40-membered ring comprising substituted phenanthroline. Claim 4 A compound according to any one of claims 1 to 3, wherein n is an integer selected from 1, 2 and 3 corresponding to the oxidation number of M. Claim 5 A compound according to any one of claims 1 to 4, wherein m is an integer selected from 0 or 1, preferably 0. Claim 6 In any one of paragraphs 1 to 5, at least one R 1 , R 2 or R 3 is substituted C2 to C 24 A compound selected from heteroaryl groups, wherein the substituted heteroaryl group comprises at least one 6-membered ring; and / or the substituted heteroaryl group comprises at least one to six N atoms, preferably one to three N atoms, more preferably one N atom; and / or the heteroaryl group of the substituted heteroaryl group is a 6-membered ring and comprises one, two, or three heteroatoms, preferably the heteroatom is N. Claim 7 In any one of paragraphs 1 through 6, at least one R 1 , R 2 or R 3 is substituted C2 to C 24 Heteroaryl group, where C2 to C 24 A compound in which the heteroaryl group is selected from pyridyl, pyrimidinyl, pyrazinyl, or triazinyl. Claim 8 In any one of paragraphs 1 through 7, at least one R 1 , R 2 or R 3 is substituted C2 to C 24 Selected from heteroaryl groups, wherein C2 to C2 are substituted 24 At least one substituent of the heteroaryl group is selected from the group comprising halogen, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyl, and partially or completely fluorinated C1 to C6 alkoxy; preferably selected from the group comprising halogen, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyl, and partially or completely fluorinated C1 to C6 alkoxy; more preferably selected from the group comprising halogen, F, Cl, CN, partially or completely fluorinated C1 to C4 alkyl, and partially or completely fluorinated C1 to C4 alkoxy; even more preferably selected from the group comprising F, CN, and partially or completely fluorinated C1 to C6 alkyl; also preferably F, CN, and partially or completely fluorinated C1 to C6 alkyl, and also preferably halogen, F, Cl, CN, and partially or completely fluorinated C1 to C4 alkyl; More preferably, a compound selected from the group comprising at least one CN, at least one CF3 group and / or at least two F atoms. Claim 9 In any one of paragraphs 1 through 8, R 1 , R 2 or R 3 One of them is a substituted C2 to C 24 Selected from heteroaryl groups, wherein at least one substituent is selected from halogens, F, Cl, CN, partially or completely fluorinated C1 to C6 alkyls, partially or completely fluorinated C1 to C6 alkoxys, and R 1 , R 2 or R 3 One of them is substituted or unsubstituted C1 to C 12 Alkyl or substituted or unsubstituted C1 to C 12 Selected from alkoxy, wherein at least one substituent is selected from halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, and partially or completely fluorinated C1 to C6 alkoxy; R 1 , R 2 or R 3 One of them is H, D, substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C1 to C 12 A compound selected from alkoxy, wherein at least one substituent is selected from halogen, F, Cl, CN, substituted or unsubstituted C1 to C6 alkyl, partially or completely fluorinated C1 to C6 alkyl, substituted or unsubstituted C1 to C6 alkoxy, partially or completely fluorinated C1 to C6 alkoxy; and the substituent is selected from halogen, F, Cl, CN, C1 to C6 alkyl, CF3, OCH3, and OCF3. Claim 10 In any one of paragraphs 1 through 9, R 1 , R 2 or R 3 At least one substituted C2 to C of 24 The heteroaryl group is selected from the following chemical formulas D1 to D29: Here, "*" indicates the bonding position, a compound. Claim 11 In any one of claims 1 to 10, the compound represented by chemical formula (I) is selected from the following chemical formulas E1 to E37: Claim 12 A semiconductor material comprising at least one compound of formula (I) according to any one of claims 1 to 11. Claim 13 In claim 12, the above material is a semiconductor material comprising at least one substantially covalent matrix compound. Claim 14 A semiconductor layer comprising a compound of formula (I) according to any one of claims 1 to 13. Claim 15 An electronic device comprising a semiconductor material according to any one of paragraphs 12 to 14. Claim 16 In paragraph 14, the electronic device is a light-emitting device, a thin-film transistor, a battery, a display device, or a photovoltaic cell, preferably a light-emitting device, and preferably the electronic device is part of a display device or a lighting device.

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