COMPOUND OF Formula (I), ORGANIC ELECTRONIC DEVICE COMPRISING COMPOUND OF Formula (I), DISPLAY DEVICE COMPRISING ORGANIC ELECTRONIC DEVICE

Abstract

The present invention relates to an organic electronic device comprising a semiconductor layer comprising a compound of formula (1).

Description

Technical Field

[0001] This invention relates to compounds of formula (I), organic electronic devices comprising compounds of formula (I), and display devices comprising said organic electronic devices. The invention also relates to novel compounds of formula (I) that can be used in organic electronic devices. Background Technology

[0002] Organic electronic devices, such as organic light-emitting diodes (OLEDs), are self-emissive and possess wide viewing angles, excellent contrast ratios, fast response times, high brightness, superior operating voltage characteristics, and excellent color reproduction. A typical OLED comprises an anode, a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode, sequentially stacked on a substrate. In this regard, the HTL, EML, and ETL are thin films formed from organic compounds.

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

[0004] The performance of an organic light-emitting diode can be affected by the characteristics of the organic semiconductor layer, and in particular by the characteristics of the compound of formula (I) also contained in the organic semiconductor layer.

[0005] EP 3 945 125 A1 relates to compounds of formula (I), semiconductor materials comprising at least one compound of formula (I), semiconductor layers comprising at least one compound of formula (I), and electronic devices comprising at least one compound of formula (I).

[0006] WO 2022 / 189431 A1 relates to cerium(IV) complexes. Furthermore, it relates to electron-doped semiconductor materials and electronic components incorporating cerium(IV) complexes. Another objective is the use of cerium(IV) complexes as electron acceptors, particularly as p-type dopants, and as electron transport materials in organic electronic components.

[0007] There is still a need to improve the performance of organic semiconductor materials, semiconductor layers, and their organic electronic devices, particularly by improving the properties of the compounds contained therein to achieve improved stability of the operating voltage over time. Summary of the Invention

[0008] One aspect of the present invention provides a compound of formula (I).

[0009] (I),

[0010] in

[0011] M is a metal ion, where M is selected from alkali metals, alkaline earth metals, group III to V or transition metals;

[0012] n is the valence of M and is selected from 1 to 3;

[0013] L is the ligand of formula (II)

[0014] (II),

[0015] in

[0016] X 1 Selected from CR 1 Or N;

[0017] X 2 Selected from CR 2 Or N;

[0018] X 3 Selected from CR 3 Or N;

[0019] X 4 Selected from CR 4 Or N;

[0020] Where X 1 X 2 X 3 X 4 The 0, 1, or 2 in the N are selected;

[0021] R 1 To R 4 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl, halogen, F, Cl or CN; and any R therein k To R k+1 It can form a ring, preferably a 5- or 6-membered ring; where k is an integer from 1 to 3;

[0022] R 5 Selected from unsubstituted and substituted C1 to C1 12 Alkyl, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl;

[0023] in

[0024] Replacement of C1 to C12 Alkyl, substituted C6 to C 19 Aryl, substituted C2 to C 20 At least one of the substituents of the heteroaryl or substituted 6-membered heteroaryl is independently selected from halogen, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl, partially or perfluorinated C1 to C8 alkoxy;

[0025] in

[0026] R 1 To R 4 and / or R 5 At least one of them contains at least one CF3 portion, and / or R 1 R 2 R 3 R 4 and R 5 One of them is CF3.

[0027] in

[0028] AL is an auxiliary ligand that coordinates with the metal ion M;

[0029] m is an integer selected from 0 to 2.

[0030] The term "R" 1 To R 4 and / or R 5 Includes at least one CF3 part and / or R 1 R 2 R 3 R 4 and R 5 One of them is CF3, which is understood to include C1 to C. 12 The terminal CF3 group in the alkyl group.

[0031] The negative charge in the compound of formula (I) may be partially or completely delocalized over the β-dicarbonyl group, and optionally also over one or more aryl groups.

[0032] It should be noted that throughout the application and claims, unless otherwise stated, any R... k "Equal" always refers to the same part. k is an integer from 1 to 4.

[0033] In this specification, unless otherwise defined, "partially fluorinated" refers to an alkyl or alkoxy group in which only a portion of the hydrogen atoms are replaced by fluorine atoms.

[0034] In this specification, unless otherwise defined, "perfluorinated" refers to an alkyl or alkoxy group in which all hydrogen atoms are replaced by fluorine atoms.

[0035] In this specification, unless otherwise defined, "substituted" means that the group is replaced by deuterium, C1 to C2. 12 Alkyl and C1 to C 12 Alkyl-substituted.

[0036] However, in this specification, "aryl-substituted" means substituted by one or more aryl groups, which themselves may be substituted by one or more aryl and / or heteroaryl groups.

[0037] Accordingly, in this specification, "heteroaryl substituted" means substituted by one or more heteroaryl groups, wherein the heteroaryl group itself may be substituted by one or more aryl and / or heteroaryl groups.

[0038] In this specification, unless otherwise defined, "alkyl group" refers to a saturated aliphatic hydrocarbon group. Alkyl groups can be C1 to C2. 12 Alkyl groups. More specifically, the alkyl groups can be C1 to C2. 10 Alkyl groups or C1 to C6 alkyl groups. For example, C1 to C4 alkyl groups contain 1 to 4 carbons in the alkyl chain and can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.

[0039] Specific examples of alkyl groups include methyl groups, ethyl groups, propyl groups, isopropyl groups, butyl groups, isobutyl groups, tert-butyl groups, pentyl groups, and hexyl groups.

[0040] In the context of this invention, " i C n H (2n+1) "Indicates an isoalkyl group, and " i C n F (2n+1) "" indicates a perfluorinated isoalkyl group.

[0041] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane by formally extracting a hydrogen atom from the ring atoms contained in the corresponding cycloalkane. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, adamantyl, and others.

[0042] The term "heteroatom" is understood to mean that at least one carbon atom in a structure that can be formed by covalently bonded carbon atoms is replaced by another multivalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, and S; more preferably, it is selected from N, P, O, and S.

[0043] In this specification, "aryl group" refers to a hydrocarbon group that can be formed by formally extracting a hydrogen atom from the aromatic ring of the corresponding aromatic hydrocarbon. An aromatic hydrocarbon is a hydrocarbon containing at least one aromatic ring or aromatic ring system. An aromatic ring or aromatic ring system is a planar ring or ring system with covalently bonded carbon atoms, wherein the planar ring or ring system comprises a conjugated system of delocalized electrons satisfying Hückel's rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl; polycyclic groups containing multiple aromatic rings linked by single bonds, such as biphenyl; and polycyclic groups containing fused rings, such as naphthyl or fluorenyl.

[0044] Similarly, heteroaryl is particularly well understood as a group obtained by formally extracting a cyclic hydrogen from such a ring in a compound containing at least one heterocyclic aromatic ring.

[0045] Heterocyclic alkyl groups are particularly well understood as groups obtained by formally extracting a cyclic hydrogen from such a ring in a compound containing at least one saturated cycloalkyl ring.

[0046] The term "fused aryl ring" or "condensed aryl ring" is understood as when two aryl rings share at least two common sp... 2 When carbon atoms are hybridized, they are considered to be either fused or condensed.

[0047] In this specification, a single key refers to a direct key.

[0048] In the context of this invention, "different" means that the compounds do not have the same chemical structure.

[0049] The terms "free from," "does not contain," and "does not include" do not exclude impurities that may be present in the compound before deposition. Impurities have no technical impact on the objectives achieved by this invention.

[0050] The term "contact sandwich" refers to a three-layer arrangement in which the middle layer is in direct contact with the two adjacent layers.

[0051] The terms "light-absorbing layer" and "light-absorbing layer" are used synonymously.

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

[0053] The terms “OLED,” “organic light-emitting diode,” and “organic light-emitting device” are used synonymously.

[0054] The terms anode, anode layer, and anode electrode are used synonymously.

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

[0056] In this specification, hole characteristics refer to the ability to provide an electron to form a hole when an electric field is applied, and due to the conductivity characteristics based on the highest occupied molecular orbital (HOMO) energy level, the hole formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0057] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0058] The term "LUMO level" is understood to refer to the lowest unoccupied molecular orbital and is defined in eV (electron volts).

[0059] The term "LUMO level further away from the vacuum level" is understood to mean that the absolute value of the LUMO level is higher than the absolute value of the LUMO level of the reference compound.

[0060] The term "HOMO level" is understood to refer to the highest occupied molecular orbital and is defined in eV (electron volts).

[0061] 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 "far from the vacuum level than the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirodi[fluorene]-2,2',7,7'-tetramine" is understood to mean that the absolute value of the HOMO level of the matrix compound of the hole injection layer is higher than the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirodi[fluorene]-2,2',7,7'-tetramine.

[0062] The term "absolute value" is understood to refer to a value without a "-" sign. According to one embodiment of the present invention, the HOMO energy level of the matrix compound of the hole injection layer can be calculated using quantum mechanical methods.

[0063] Beneficial effects

[0064] Surprisingly, it was found that the compound according to formula (I) enables the device to have improved voltage stability over time.

[0065] According to one implementation, LHs selected from the following are excluded:

[0066] , , , , , and .

[0067] According to one embodiment, M of the compound of formula (I) may be selected from a metal ion, wherein the corresponding metal has an electronegativity of ≥0.65 and ≤1.9 according to Allen.

[0068] The term “according to Allen’s electronegativity” is of particular reference to Allen, Leland C. (1989). “Electronegativity is the average one-electron energy of the valence-shell electrons in ground-state free atoms”, Journal of the American Chemical Society 111 (25):9003-9014.

[0069] According to one implementation, M can be selected from transition metals or group III or V metals.

[0070] According to the present invention, internal transition metals are excluded from the list of transition metals. Internal transition metals include lanthanides, including La, Ce, Pr, Nd, Pm, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb, and Lu; and actinides, including Ac, Th, Pa, U, Np, Pu, Am, Cm, Bk, Cf, Es, Fm, Md, No, and Lr.

[0071] According to one embodiment, the atomic weight of M is selected in the range of ≥54Da and ≤200Da, preferably in the range of ≥55Da and ≤200Da.

[0072] According to one embodiment, M is a metal ion selected from Li(I), K(I), Rb(I), Cs(I), Ag(I), Cu(II), Zn(II), Pd(II), Ir(III), Al(III), Ga(III), Mn(III), Ru(III), In(III), Fe(II) or Fe(III); more preferably, M is a metal ion selected from Cu(II), Fe(II) and Fe(III), and particularly preferred, M is Cu(II) or Fe(III), wherein the number in parentheses indicates the oxidation state.

[0073] According to one embodiment, the molecular weight of L is selected in the range of ≤600Da and ≥240Da, preferably ≤500Da and ≥280Da.

[0074] According to one embodiment of the present invention, X 1 To X 4 Zero or one of them is N.

[0075] According to one implementation, X 1 To X 4 None of them are N.

[0076] According to one embodiment of the present invention, R 1 To R 4 At least one of them is CF3 or CN.

[0077] According to one embodiment of the present invention, R 1 To R 4 At least two of them are H or F.

[0078] According to one embodiment of the present invention, R 5 Selected from partially or fully fluorinated C1 to C125C4 ... 12 Alkyl groups, preferably perfluorinated C1 to C6 alkyl groups, more preferably CF3 or C2F5.

[0079] According to one embodiment of the present invention, the ligand of formula (II) is selected from one of the following formulas (B1) to (B113):

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086] Preferably, the ligand of formula (II) is selected from formulas (B1) to (B108) and (B113), more preferably from formulas (B1) to (B108).

[0087] According to one embodiment of the invention, M is selected from Cu or Fe, and when M is Cu or Fe, n is selected from 2, or when M is Fe, n is selected from 3, and L is selected from formulas (B1) to (B113), preferably from formulas (B1) to (B108) and (B113).

[0088] According to one embodiment of the present invention, M is selected from Cu, Fe, Zn, In or Mn. When M is Cu, Fe, Zn or Mn, preferably Cu, Fe or Mn, n is selected from 2, or when M is Fe or In, n is selected from 3, and L is selected from formulas (B1) to (B113), preferably from formulas (B1) to (B108) and / or (B113).

[0089] According to one embodiment of the invention, M is selected from Zn, In or Mn. When M is Zn or Mn, preferably Mn, n is selected from 2, or when M is In, n is selected from 3, and L is selected from formulas (B1) to (B113), preferably from formulas (B1) to (B108) and / or (B113).

[0090] According to one embodiment of the present invention, the compound of formula (I) is selected from one of the following formulas (A1) to (A70):

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097] Preferably, the compound of formula (I) is selected from formulas (A1) to (A29), (A38) to (A48) and / or (A60) to (A70).

[0098] According to one embodiment, compounds of formula (I) are excluded, wherein

[0099] -M = Na, Li, K and / or Cs, L = B1, n = 1 and m = 0; and / or

[0100] -M = Li, K and / or Cs, L = B82, n = 1 and m = 0.

[0101] According to one embodiment of this application, AL (auxiliary ligand) is selected from H2O, C2 to C2. 40 Monodentate or multidentate ethers and C2 to C 40 Sulfides, C2 to C 40 Amines, C2 to C 40 Phosphine, C2 to C 20 Alkyl nitrile or C2 to C 40Aryl nitrile, or compounds according to formula (AL-I);

[0102] (AL-I),

[0103] in

[0104] R 6 and R 7 Independently selected from C1 to C 20 Alkyl, C1 to C 20 Heteroalkyl, C6 to C 20 aryl, heteroaryl with 5 to 20 cyclic atoms, halogenated or perhalogenated C1 to C2 groups 20 Alkyl, halogenated or fully halogenated C1 to C 20 Heteroalkyl, halogenated or fully halogenated C6 to C 20 aryl, a halogenated or fully halogenated heteroaryl group having 5 to 20 cyclic atoms, or at least one R 6 and R 7 Bridge and form 5 to 20 element rings, or two Rs 6 and / or two Rs 7 Bridges and forms 5 to 40-membered rings or forms rings containing unsubstituted elements or C1 to C1. 12 Substituted phenanthroline rings of 5 to 40 members.

[0105] semiconductor materials

[0106] According to another aspect, a semiconductor material is provided, the semiconductor material comprising at least one compound of formula (I) according to the invention.

[0107] According to one embodiment, the semiconductor material further comprises at least one covalent matrix compound or at least one substantially covalent matrix compound.

[0108] According to another aspect, the semiconductor material comprises at least one compound of formula (I) according to the invention and at least one other covalent matrix compound or at least one substantially covalent matrix compound.

[0109] Organic semiconductor layer

[0110] According to another aspect, an organic semiconductor layer is provided, the organic semiconductor layer comprising at least one compound of formula (I) according to the invention.

[0111] Organic semiconductor layers can be formed on the anode or cathode layer through vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When forming an organic semiconductor layer using vacuum deposition, the deposition conditions can vary depending on one or more compounds used to form the layer, as well as the desired structure and thermal properties of the layer. However, typically, vacuum deposition conditions can include a deposition temperature of 100°C to 350°C, and 10... -8 Up to 10 -3 The pressure of Torr (1 Torr equals 133.322 Pa) and the deposition rate from 0.1 to 10 nm / sec.

[0112] When forming an organic semiconductor layer using spin coating or printing, the coating conditions can vary depending on one or more compounds used to form the organic semiconductor layer and the desired structure and thermal properties of the layer. For example, coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C. After coating, heat treatment removes the solvent.

[0113] The thickness of the organic semiconductor layer can be in the range of about 1 nm to about 20 nm, for example about 2 nm to about 15 nm, or about 2 nm to about 12 nm.

[0114] When the thickness of the organic semiconductor layer is within this range, the organic semiconductor layer can have excellent hole injection and / or hole generation characteristics without causing substantial damage to the driving voltage.

[0115] According to one embodiment of the present invention, the organic semiconductor layer may comprise:

[0116] - at least about ≥0.5 wt% to about ≤30 wt%, preferably about ≥0.5 wt% to about ≤20 wt%, more preferably about ≥1 wt% to about ≤15 wt% of the compound of formula (I), and

[0117] - At least about ≥70% by weight to about ≤99.5% by weight, preferably about ≥80% by weight to about ≤99.5% by weight, more preferably about ≥85% by weight to about ≤99% by weight; preferably, the weight percentage of the compound of formula (I) is less than the weight percentage of the fundamental covalent matrix compound; wherein the weight percentage of the component is based on the total weight of the organic semiconductor layer.

[0118] According to one embodiment of the present invention, the organic semiconductor layer and / or the compound of formula (1) is non-luminescent.

[0119] In the context of this specification, the terms "substantially non-luminescent" or "non-luminescent" mean that the contribution of a compound or layer to the visible emission spectrum derived from the device is less than 10%, preferably less than 5%, relative to the visible emission spectrum. The visible emission spectrum is an emission spectrum with wavelengths from about ≥380 nm to about ≤780 nm.

[0120] Basic covalent matrix compound / covalent matrix compound

[0121] According to another aspect of the invention, the semiconductor material and / or organic semiconductor layer may also comprise a substantially covalent matrix compound.

[0122] The fundamentally covalent matrix compound, also known as the matrix compound, can be an organic aromatic matrix compound containing covalently bonded carbon atoms. The fundamentally covalent matrix compound can be an organic compound consisting essentially of covalently bonded C, H, O, N, and S, and optionally also contains covalently bonded B, P, or Si. The fundamentally covalent matrix compound can be an organic aromatic covalently bonded compound that does not contain metal atoms, and the majority of its skeleton atoms can be selected from C, O, S, and N, and preferably from C, O, and N, wherein the majority of the atoms are C atoms. Alternatively, the covalent matrix compound does not contain metal atoms, and the majority of its skeleton atoms can be selected from C and N; preferably, the covalent matrix compound does not contain metal atoms, and the majority of its skeleton atoms can be selected from C, with a small portion of its skeleton atoms being N.

[0123] According to one embodiment, the fundamentally covalent matrix compound may have a molecular weight Mw of ≥400 g / mol and ≤2000 g / mol, preferably ≥450 g / mol and ≤1500 g / mol, even more preferably ≥500 g / mol and ≤1000 g / mol, further preferably ≥550 g / mol and ≤900 g / mol, and even more preferably ≥600 g / mol and ≤800 g / mol.

[0124] In one embodiment, when determined under the same conditions, the HOMO level of the essentially covalent matrix compound can be more negative than the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirodi[fluorene]-2,2',7,7'-tetramine (CAS 207739-72-8).

[0125] In one embodiment of the invention, the fundamentally covalent matrix compound may be free of alkoxy groups.

[0126] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, or a diarylamine moiety, or a triarylamine moiety.

[0127] Preferably, the fundamentally covalent matrix compound does not contain TPD or NPB.

[0128] Compounds of formula (IIIa) or compounds of formula (IIIb)

[0129] According to another aspect of the invention, the essentially covalent matrix compound, or covalent matrix compound, also referred to herein as a matrix compound, may comprise at least one arylamine compound, a diarylamine compound, a triarylamine compound, a compound of formula (IIIa), or a compound of formula (IIIb):

[0130]

[0131] in:

[0132] T 1 T 2 T 3 T 4 and T 5 It is independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably single bond or phenylene group;

[0133] T 6 It is a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group;

[0134] Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Independently selected from substituted or unsubstituted C6 to C6. 20 aryl; or substituted or unsubstituted C3 to C4. 20Heteroarylene groups; substituted or unsubstituted biphenylidene; substituted or unsubstituted fluorene; substituted 9-fluorene; substituted 9,9-fluorene; substituted or unsubstituted naphthalene; substituted or unsubstituted anthracene; substituted or unsubstituted phenanthrene; substituted or unsubstituted pyrene; substituted or unsubstituted perylene; substituted or unsubstituted biphenylidene; substituted or unsubstituted tetraphenyl; substituted or unsubstituted benzo[b,f]-anthracene; substituted or unsubstituted dibenzofuran; substituted or unsubstituted dibenzothiophene; substituted or unsubstituted xanthones; substituted or unsubstituted carbazole; substituted 9-phenylcarbazole; substituted or unsubstituted azaheptanyl; substituted or unsubstituted dibenzo[b,f]-azaheptanyl; substituted or unsubstituted 9,9'-spirodi[fluorene]; substituted or unsubstituted spiro[fluorene-9,9'-xanton]; or substituted or unsubstituted aromatic fused ring systems comprising at least three substituted or unsubstituted aromatic rings selected from: substituted or unsubstituted non-heterocyclic rings, substituted or unsubstituted 5-membered heterocyclic rings, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted 7-membered rings, substituted or unsubstituted fluorene; or fused ring systems comprising 2 to 6 substituted or unsubstituted 5 to 7-membered rings, wherein the rings are selected from: (i) unsaturated 5 to 7-membered heterocyclic rings; (ii) 5 to 6-membered aromatic heterocyclic rings; (iii) unsaturated 5 to 7-membered non-heterocyclic rings; (IIIa) 6-membered aromatic non-heterocyclic rings;

[0135] in

[0136] Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from H, D, F, C(-O)R, either the same or different. 2 CN, Si(R) 2 3. P(-O)(R) 2 2. OR 2 S(-O)R 2 S(-O)2R 2 Substituted or unsubstituted straight-chain alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted branched alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms; substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms; substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms; and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms; unsubstituted C6 to C6... 18 Aryl, unsubstituted C3 to C 18 A heteroaryl fused ring system comprising 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: unsaturated 5 to 7-membered heterocycles, 5 to 6-membered aromatic heterocycles, unsaturated 5 to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles.

[0137] Where R 2 The following can be selected from H, D, straight-chain alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 1 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms, alkenyl or ynyl groups having 2 to 6 carbon atoms, C6 to C 18 Aryl or C3 to C 18 Mixed aromatic compounds.

[0138] Preferably, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are selected from H, straight-chain alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 1 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms, alkenyl or ynyl groups having 2 to 6 carbon atoms, and C6 to C6 substituents. 18 Aryl, C3 to C 18 The heteroaryl group comprises a fused ring system containing 2 to 4 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: unsaturated 5 to 7-membered heterocycles, 5 to 6-membered aromatic heterocycles, unsaturated 5 to 7-membered non-heterocycles, and 6-membered aromatic non-heterocycles; more preferably, the substituents are selected from H, straight-chain alkyl groups having 1 to 4 carbon atoms, branched alkyl groups having 1 to 4 carbon atoms, cyclic alkyl groups having 3 to 4 carbon atoms, and / or phenyl groups.

[0139] Therefore, compounds of formula (IIIa) or (IIIb) can have standard starting temperatures suitable for large-scale production.

[0140] According to one embodiment of the semiconductor material and / or organic semiconductor layer, the substantially covalent matrix compound comprises a compound of formula (IIIa) or (IIIb):

[0141]

[0142] in

[0143] T 1 T 2 T 3 T 4 and T 5 It can be independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably single bond or phenylene group;

[0144] T 6 It is a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group;

[0145] Ar 1 Ar 2 Ar 3 Ar 4 and Ar5 It can be independently selected from unsubstituted C6 to C6. 20 aryl; or unsubstituted C3 to C4 20 Heteroarylene; Unsubstituted biphenylidene; Unsubstituted fluorene; Substituted 9-fluorene; Substituted 9,9-fluorene; Unsubstituted naphthalene; Unsubstituted anthracene; Unsubstituted phenanthrene; Unsubstituted pyrene; Unsubstituted perylene; Unsubstituted triphenylidene; Unsubstituted tetraphenyl; Unsubstituted benzo[b,f]-anthracene; Unsubstituted dibenzofuran; Unsubstituted dibenzothiophene; Unsubstituted xanthones; Unsubstituted carbazole; Substituted 9-phenylcarbazole; Unsubstituted azirrocycloheptanyl; Unsubstituted dibenzo[b,f]azirrocycloheptanyl; Unsubstituted 9,9'-spirodi[fluorene]; Unsubstituted spiro[fluorene-9,9'-xanton]; or unsubstituted aromatic fused ring systems comprising at least three unsubstituted aromatic rings selected from: unsubstituted non-heterocyclic rings, unsubstituted 5-membered heterocyclic rings, unsubstituted 6-membered rings and / or unsubstituted 7-membered rings, unsubstituted fluorene; or fused ring systems comprising 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are selected from: (i) unsaturated 5 to 7-membered heterocyclic rings; (ii) 5 to 6-membered aromatic heterocyclic rings; (iii) unsaturated 5 to 7-membered non-heterocyclic rings; (IIIa) 6-membered aromatic non-heterocyclic rings.

[0146] According to one embodiment of the semiconductor material and / or organic semiconductor layer, the substantially covalent matrix compound comprises a compound of formula (IIIa) or (IIIb):

[0147]

[0148] in

[0149] T 1 T 2 T 3 T 4 and T 5 It can be independently selected from single bond, phenylene group, biphenylene group, triphenylene group or naphthylene group, preferably single bond or phenylene group;

[0150] T 6 It is a benzene group, a biphenyl group, a terphenyl group, or a naphthyl group;

[0151] Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be independently selected from unsubstituted C6 to C6. 20 aryl, or unsubstituted C3 to C 20Heteroarylene, unsubstituted biphenylidene, unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, unsubstituted naphthalene, unsubstituted anthracene, unsubstituted phenanthrene, unsubstituted pyrene, unsubstituted perylene, unsubstituted triphenylidene, unsubstituted tetraphenylene, unsubstituted benzo[b,f]-anthracene, unsubstituted dibenzofuran, unsubstituted dibenzothiophene, unsubstituted saxon, unsubstituted carbazole, substituted 9-phenylcarbazole, unsubstituted azaheptanyl, unsubstituted dibenzo[b,f]azaheptanyl, unsubstituted 9,9'-spirodi[fluorene], unsubstituted spiro[fluorene-9,9'-saxon].

[0152] Therefore, compounds of formula (IIIa) or (IIIb) can have standard starting temperatures suitable for large-scale production.

[0153] According to one implementation, where T 1 T 2 T 3 T 4 and T 5 It can be independently selected from single bonds, phenylene groups, biphenylene groups, or triphenylene groups.

[0154] According to one implementation, where T 1 T 2 T 3 T 4 and T 5 It can be independently selected from phenylene, biphenylene, or terphenylene, and T 1 T 2 T 3 T 4 and T 5 One of them is a single bond.

[0155] According to one implementation, where T 1 T 2 T 3 T 4 and T 5 It can be independently selected from phenylene group or biphenylene group, and T 1 T 2 T 3 T 4 and T 5 One of them is a single bond.

[0156] According to one implementation, where T 1 T 2 T 3 T 4 and T 5 It can be independently selected from phenylene group or biphenylene group, and T 1 T 2 T 3 T4 and T 5 The two in it are single bonds.

[0157] According to one implementation, where T 1 T 2 and T 3 It can be independently selected from phenylene groups, and T 1 T 2 and T 3 One of them is a single bond.

[0158] According to one implementation, where T 1 T 2 and T 3 It can be independently selected from phenylene groups, and T 1 T 2 and T 3 The two in it are single bonds.

[0159] According to one implementation, where T 6 It can be phenylene oxide, biphenylene oxide, or terphenylene oxide. According to one embodiment, wherein T... 6 It can be a phenylene group.

[0160] According to one implementation, where T 6 It can be a biphenylene group. According to one embodiment, wherein T... 6 It can be a triphenylene group.

[0161] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 Can be selected independently from B1 to B16:

[0162]

[0163] Among them, the asterisk Indicates the bonding location.

[0164] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 It can be selected independently from B1 to B15; or selected from B1 to B10 and B13 to B15.

[0165] According to one implementation, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5It can be independently selected from B1, B2, B5, B7, B9, B10, B13 to B16.

[0166] When Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 When selected within this range, the standard starting temperature can be within a range particularly suitable for mass production.

[0167] "Matrix compounds of formula (IIIa) or (IIIb)" may also be called "hole transport compounds".

[0168] According to one embodiment, the compound of formula (IIIa) or formula (IIIb) may contain at least 1 to 6 substituted or unsubstituted aromatic fused ring systems comprising heteroaromatic rings.

[0169] According to one embodiment, the compound of formula (IIIa) or formula (IIIb) may comprise at least 1 to 6 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings and at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings.

[0170] According to one embodiment, the compound of formula (IIIa) or (IIIb) may comprise at least 1 to 6 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings and at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles, preferably 2 to 5 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings and at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles, even more preferably 3 or 4 substituted or unsubstituted aromatic fused ring systems containing heteroaromatic rings and optionally at least 1 to 3 substituted or unsubstituted unsaturated 5 to 7-membered heterocycles, and further preferably the aromatic fused ring system containing heteroaromatic rings is unsubstituted; and optionally at least 1 to 3 unsubstituted unsaturated 5 to 7-membered heterocycles.

[0171] According to one embodiment, the compound of formula (IIIa) or (IIIb) may comprise:

[0172] - A substituted or unsubstituted aromatic fused ring system having at least 2 to ≤6, preferably 3 to ≤5 or 4 fused aromatic rings selected from: substituted or unsubstituted non-heteroaromatic rings, substituted or unsubstituted 5-membered heterocycles, substituted or unsubstituted 6-membered rings and / or substituted or unsubstituted unsaturated 5- to 7-membered heterocycles; or

[0173] - An unsubstituted aromatic fused ring system having at least 2 to ≤6, preferably 3 to ≤5 or 4 fused aromatic rings selected from the following: unsubstituted non-heteroaromatic rings, unsubstituted 5-membered heterocycles, unsubstituted 6-membered rings and / or unsubstituted unsaturated 5- to 7-membered heterocycles.

[0174] 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 also be noted that the substituted or unsubstituted unsaturated 5- to 7-membered ring is not necessarily an aromatic ring.

[0175] According to one embodiment, the essentially covalent matrix compound comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group and / or a substituted fluorenyl group, wherein the substituent is independently selected from methyl, phenyl or fluorenyl.

[0176] According to one embodiment of the invention, the compound of formula (IIIa) or (IIIb) is selected from formulas (F1) to (F21):

[0177] (F1) (F2)

[0178] (F3) (F4)

[0179] (F5) (F6)

[0180] (F7) (F8)

[0181] (F9) (F10)

[0182] (F11) (F12)

[0183] (F13) (F14)

[0184] (F15) (F16)

[0185] (F17) (F18)

[0186] (F19) (F20)

[0187] (F21);

[0188] Preferably, the compound of formula (IIIa) or formula (IIIb) is selected from formula (F3) to (F21), more preferably from (F4) to (F21).

[0189] Organic electronic devices

[0190] According to another aspect of the present invention, an organic electronic device is provided, wherein the organic electronic device comprises a semiconductor material, wherein at least one semiconductor material comprises a compound of formula (I).

[0191] According to another aspect of the present invention, an organic electronic device is provided, wherein the organic electronic device comprises an organic semiconductor layer, wherein the organic semiconductor layer comprises a compound of formula (I).

[0192] Surprisingly, it has been shown that this organic electronic device has improved properties for many applications within the present invention, especially improved stability of the operating voltage over time.

[0193] According to one embodiment of the present invention, the organic electronic device is selected from light-emitting devices, thin-film transistors, batteries, display devices or photovoltaic cells, and preferably light-emitting devices, and preferably the electronic device is part of a display device or a lighting device.

[0194] According to one embodiment, an organic electronic device comprising a compound according to formula (I) of the present invention is a light-emitting device, a thin-film transistor, a battery, a display device, or a photovoltaic device, and preferably a light-emitting device, preferably said electronic device being part of a display device or a lighting device.

[0195] According to one embodiment of the present invention, the organic electronic device further includes at least one photoactive layer, wherein the at least one photoactive layer is disposed between the anode layer and the cathode layer.

[0196] According to one embodiment of the present invention, the organic electronic device includes at least one photoactive layer, and the at least one organic semiconductor layer is disposed between the anode and the at least one photoactive layer.

[0197] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, at least one photoactive layer and at least one semiconductor layer, wherein the at least one semiconductor layer is disposed between the anode layer and the at least one photoactive layer; and wherein the at least one organic semiconductor layer comprises a compound of formula (1).

[0198] According to one embodiment, the organic electronic device includes an anode layer, a cathode layer, and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is disposed between the anode layer and the cathode layer, and wherein the at least one organic semiconductor layer is an organic semiconductor layer according to the present invention.

[0199] According to one embodiment of the present invention, the organic semiconductor layer is arranged and / or configured to be adjacent to the anode layer.

[0200] According to one embodiment of the present invention, the organic semiconductor layer of the present invention is a hole injection layer.

[0201] In cases where the semiconductor layer of the present invention is a hole injection layer and / or is arranged and / or configured to be adjacent to the anode layer, it is particularly preferred that the layer is substantially composed of a compound of formula (1).

[0202] In the context of this specification, the term "consistently of" specifically refers to and / or includes a concentration of ≥90% (volume / volume), more preferably ≥95% (volume / volume), and most preferably ≥99% (volume / volume).

[0203] According to another aspect, the thickness of the semiconductor layer is at least about ≥0.5nm to about ≤10nm, preferably about ≥2nm to about ≤8nm, and even more preferably about ≥3nm to about ≤5nm.

[0204] According to one embodiment of the present invention, the semiconductor layer may further comprise a substantially covalent matrix compound. Preferably, at least one semiconductor layer further comprising a substantially covalent matrix compound is arranged and / or configured adjacent to the anode layer.

[0205] According to one embodiment of the present invention, the electronic organic device is an electroluminescent device, preferably an organic light-emitting diode.

[0206] According to one embodiment of the present invention, the electronic organic device is an electroluminescent device, preferably an organic light-emitting diode, and light is emitted through a cathode layer.

[0207] The present invention also relates to a display device comprising organic electronic devices according to the present invention.

[0208] According to one embodiment of the present invention, the electronic organic device is an electroluminescent device, preferably an organic light-emitting diode.

[0209] The present invention also relates to a display device comprising organic electronic devices according to the present invention.

[0210] Other layers

[0211] According to the present invention, in addition to the layers already mentioned above, the organic electronic device may also include other layers. Exemplary embodiments of each layer are described below:

[0212] base

[0213] The substrate can be any substrate commonly used to manufacture electronic devices such as organic light-emitting diodes. If light is to be emitted through the substrate, the substrate should be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be either a transparent or opaque material, such as a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate.

[0214] Anode layer

[0215] The anode layer, also known as the anode electrode, can be formed by deposition or sputtering of the material used to form the anode layer. The material used to form the anode layer can be a high work function material, which facilitates 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 metals (typically silver (Ag) or gold (Au)) or metal alloys.

[0216] An anode layer may contain two or more anode sublayers.

[0217] According to one embodiment, the anode layer includes a first anode sublayer and a second anode sublayer, wherein the first anode sublayer is arranged closer to the substrate and the second anode sublayer is arranged closer to the cathode layer.

[0218] 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.

[0219] According to one embodiment, the anode layer includes a first anode sublayer, a second anode sublayer, and a third anode sublayer, wherein the first anode sublayer is arranged closer to the substrate, the second anode sublayer is arranged closer to the cathode layer, and the third anode sublayer is arranged between the substrate and the first anode sublayer.

[0220] According to one embodiment, the anode layer may include 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 composed of Ag, the second anode sublayer may comprise or composed of ITO or IZO, and the third anode sublayer may comprise or composed of ITO or IZO.

[0221] Preferably, the first anode sublayer may contain or be composed of Ag, the second anode sublayer may contain or be composed of ITO, and the third anode sublayer may contain or be composed of ITO.

[0222] Preferably, the transparent conductive oxides in the second and third anode sublayers can be the same.

[0223] According to one embodiment, the anode layer may include a first anode sublayer containing Ag or Au with a thickness of 100 to 150 nm, a second anode sublayer containing a transparent conductive oxide or composed thereof with a thickness of 3 to 20 nm, and a third anode sublayer containing a transparent conductive oxide or composed thereof with a thickness of 3 to 20 nm.

[0224] It should be understood that the third anode layer is not part of the substrate.

[0225] According to one embodiment of the present invention, a compound comprising formula (I) or an organic semiconductor layer thereof is in direct contact with the anode layer.

[0226] Hole injection layer

[0227] Hole injection layers (HILs) can be formed on anode electrodes via vacuum deposition, spin coating, printing, casting, slot die coating, and Langmuir-Blodgett (LB) deposition. When using vacuum deposition to form HILs, the deposition conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. However, typically, vacuum deposition conditions can include deposition temperatures ranging from 100°C to 500°C, and 10... -8 Up to 10 -3 The pressure of Torr (1 Torr equals 133.322 Pa) and the deposition rate from 0.1 to 10 nm / sec.

[0228] When spin coating or printing is used to form HILs, the coating conditions can vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C. After coating, heat treatment removes the solvent.

[0229] HILs can be formed from any compound commonly used to form HILs. Examples of compounds that can be used to form HILs include phthalocyanine compounds such as copper phthalocyanine (CuPc), 4,4',4''-tris(3-methylphenylphenylamino)triphenylamine (m-MTDATA), TDATA, 2T-NATA, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylidene dioxothiophene) / poly(4-styrene sulfonate) (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), and polyaniline / poly(4-styrene sulfonate) (PANI / PSS).

[0230] HILs may contain or be composed of p-type dopants, and the p-type dopants may be selected from, but are not limited to, tetrafluoro-tetracyanoquinone dimethyl ether (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diethylenedimethyl ether)malononitrile or 2,2',2''-(cyclopropane-1,2,3-triethylenedimethyl ether)tris(2-(p-cyanotetrafluorophenyl)acetonitrile). HILs may be selected from hole transport matrix compounds doped with p-type dopants. Typical examples of known doped hole transport materials are: copper phthalocyanine (CuPc) with a HOMO level of approximately -5.2 eV; tetrafluoro-tetracyanoquinone dimethane (F4TCNQ) doped with a LUMO level of approximately -5.2 eV; zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO = -5.2 eV); α-NPD (N,N'-bis(naphthyl-1-yl)-N,N'-bis(phenyl)-benzidine) doped with F4TCNQ; and α-NPD doped with 2,2'-(perfluoronaphthyl-2,6-diethylenediamine)dimalonitrile. The concentration of the p-type dopant can be selected from 1 wt% to 20 wt%, more preferably from 3 wt% to 10 wt%.

[0231] The thickness of the HIL can range from about 1 nm to about 100 nm, and for example from about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL can have excellent hole injection characteristics without causing substantial damage to the driving voltage.

[0232] Hole transport layer

[0233] According to one embodiment of the present invention, the organic electronic device may further include a hole transport layer, wherein the hole transport layer is disposed between the anode layer and the cathode layer, preferably between the organic semiconductor layer and the cathode layer of the present invention.

[0234] Hole transport layers (HTLs) can be formed on high-intensity interphase (HILs) via vacuum deposition, spin coating, slot die coating, printing, casting, and Langmuir-Blodgett (LB) deposition. When forming HTLs via vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used to form HILs. However, the conditions for vacuum or solution deposition can vary depending on the compound used to form the HTL.

[0235] HTLs can be formed from any compound commonly used to form HTLs. For example, suitable compounds are disclosed in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. (Chemical Reviews) 2007, 107, 953-1010, and the aforementioned literature is incorporated herein by reference. Examples of compounds that can be used to form HTLs are: carbazole derivatives, such as N-phenylcarbazole or polyvinylcarbazole; benzidine derivatives, such as N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthyl-1-yl)-N,N'-diphenylbenzidine (α-NPD); and triphenylamine compounds, such as 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA). In these compounds, TCTA can transport holes and inhibit exciton diffusion into the EML.

[0236] According to a preferred embodiment of the invention, the hole transport layer may comprise a substantially covalent matrix compound.

[0237] According to one embodiment of the present invention, the hole transport layer may contain the same essentially covalent matrix compound as the organic semiconductor layer of the present invention, preferably, the hole transport layer may contain the same compound of formula (IIIa) or (IIIb) as the organic semiconductor layer of the present invention.

[0238] The thickness of the HTL can be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, even more preferably about 20 nm to about 190 nm, even more preferably about 40 nm to about 180 nm, even more preferably about 60 nm to about 170 nm, even more preferably about 80 nm to about 160 nm, even more preferably about 100 nm to about 160 nm, and even more preferably about 120 nm to about 140 nm. The preferred thickness of the HTL is 170 nm to 200 nm.

[0239] When the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without causing substantial damage to the drive voltage.

[0240] Electron blocking layer

[0241] The function of an electron blocking layer (EBL) is to prevent electrons from transferring from the emissive layer to the hole transport layer, thereby confining electrons within the emissive layer. This improves efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer contains a triarylamine compound. The LUMO level of the triarylamine compound can be closer to the vacuum level than the LUMO level of the hole transport layer. Compared to the HOMO level of the hole transport layer, the electron blocking layer can have a HOMO level further away from the vacuum level. The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0242] If the electron blocking layer has a high triplet energy level, it can also be described as a triplet control layer.

[0243] If a phosphorescent green or blue emitting layer is used, the function of the triplet control layer is to reduce triplet quenching. This allows for higher luminous efficiency derived from the phosphorescent emitting layer. The triplet control layer is selected from triarylamine compounds whose triplet energy level is higher than that of the phosphorescent emitter in the adjacent emitting layer. Suitable compounds, particularly triarylamine compounds, for triplet control layers are described in EP 2 722 908 A1.

[0244] Photoactive Alpha Layer (PAL)

[0245] The photoactive layer converts electric current into photons or photons into electric current.

[0246] PALs can be formed on HTLs via vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When using vacuum deposition or spin coating to form PALs, the deposition and coating conditions can be similar to those used to form HILs. However, the deposition and coating conditions can vary depending on the compound used to form the PAL.

[0247] The photoactive layer may not contain the compound of formula (1).

[0248] The photoactive layer can be a light-emitting layer (EML) (also known as a light-emitting layer) or a light-absorbing layer.

[0249] Emissive Layer (EML)

[0250] According to one embodiment, the organic electronic device of the present invention may further include a light-emitting layer (EML), wherein the light-emitting layer is disposed between the anode layer and the cathode layer, preferably, the light-emitting layer is disposed between the organic semiconductor layer and the cathode layer.

[0251] EMLs can be formed on HTLs via vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When forming EMLs using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used for forming HILs. However, the deposition and coating conditions can vary depending on the compound used to form the EML.

[0252] The emissive layer (EML) may comprise an organic light-emitting body and a light-emitting compound dopant. Examples of organic light-emitting bodies are Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-bis(naphthyl-2-yl)anthracene (ADN), 4,4',4''-tris(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-bis-2-naphthylanthracene (TBADN), stilbeneyl arylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0253] The luminescent dopant can be a phosphorescent or fluorescent luminescent material. Phosphorescent luminescent materials and those emitting light via thermally activated delayed fluorescence (TADF) are preferred due to their high efficiency. The luminescent material can be a small molecule or a polymer.

[0254] Examples of red-emitting dopants include PtOEP, Ir(piq)3, and Btp2Ir(acac), but are not limited to these. These compounds are phosphorescent; however, fluorescent red-emitting dopants can also be used.

[0255] Examples of phosphorescent green luminescent dopants are Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2(acac), and Ir(mpyp)3.

[0256] Examples of phosphorescent blue emitting electron dopants are F₂Irpic, (F₂ppy)₂Ir(tmd), and Ir(dfppz)₃, as well as trifluorene. Examples of fluorescent blue emitting electron dopants are 4,4'-bis(4-diphenylaminostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetratert-butylperylene (TBPe).

[0257] The luminescent layer may not contain the compound of formula (1).

[0258] Based on 100 parts by weight of the host, the amount of luminescent dopant can range from about 0.01 to about 50 parts by weight. Alternatively, the luminescent layer can be composed of a luminescent polymer. The EML can have a thickness of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can exhibit excellent luminescence without causing substantial damage to the driving voltage.

[0259] According to a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting compound of formula (IV):

[0260] (IV),

[0261] in

[0262] Z 1 Z 2 and Z 3 They may be the same as or different from each other, and each is independently selected from monocyclic to polycyclic aromatic hydrocarbon rings or monocyclic to polycyclic aromatic heterocycles;

[0263] Ar 31 and Ar 32 They may be chosen, either the same or different from each other, and each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or bonded to an adjacent substituent to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aliphatic ring;

[0264] R 31 R 32 and R 33 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amine groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups, or adjacent substituents are bonded to each other to form substituted or unsubstituted aromatic rings or substituted or unsubstituted aliphatic rings.

[0265] One or more of the substituents are selected from deuterium, alkyl groups having 1 to 6 carbon atoms, alkylsilyl groups having 1 to 30 carbon atoms, arylsilyl groups having 6 to 50 carbon atoms, alkylamine groups having 1 to 30 carbon atoms, alkylarylamine groups having 1 to 50 carbon atoms, arylamine groups having 6 to 50 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heteroaryl groups having 2 to 30 carbon atoms, or substituents connected to two or more substituents selected from said groups, or adjacent substituents bonded to each other to form an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, said aliphatic hydrocarbon ring being unsubstituted or substituted by said substituents;

[0266] r 31 r 32 and r 33 Each is an integer of 0, 1, 2, 3, or 4, and when r 31 to r 33 When the number is 2 or higher, the substituents in parentheses may be the same or different from each other.

[0267] According to one implementation, for equation (III):

[0268] Z 1 Z 2 and Z 3They are selected from the same or different ones, and each is independently selected from monocyclic to bicyclic aromatic hydrocarbon rings, or monocyclic to bicyclic aromatic heterocycles containing O, N or S;

[0269] Ar 31 and Ar 32 They are selected from each other, either the same or different, and each is independently selected from an alkyl group having 1 to 10 carbon atoms that is unsubstituted or substituted with an aryl group, an aryl group having 6 to 30 carbon atoms that is unsubstituted or substituted with an aryl group, or a heteroaryl group having 2 to 30 carbon atoms.

[0270] R 31 R 32 and R 33 They are selected from each other, either the same or different, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups.

[0271] According to one implementation, for equation (III):

[0272] Z 1 Z 2 and Z 3 They are selected from the same or different rings, and each is independently selected from the benzene ring or the thiophene ring;

[0273] Ar 31 and Ar 32 They may be selected from the same or different groups, and each is independently selected from the phenyl group, biphenyl group, naphthyl group, dimethylfluorenyl group, diphenylfluorenyl group, dibenzofuran group or dibenzothiophene group;

[0274] R 31 R 32 and R 33 They are selected from each other, either the same or different, and each independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl groups having 5 to 30 carbon atoms, substituted or unsubstituted silyl groups having 1 to 10 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 2 to 30 carbon atoms.

[0275] According to a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting compound of formula (IV), wherein formula (IV) is selected from formulas (BD1) to (BD9):

[0276] (BD1) (BD2)

[0277] (BD3) (BD4)

[0278] (BD5) (BD6)

[0279] (BD7) (BD8)

[0280] (BD9)

[0281] According to a preferred embodiment of the present invention, the light-emitting layer comprises an organic light-emitting host compound, wherein the organic light-emitting host compound comprises

[0282] - At least one fused aromatic ring system consisting of 3 to 5 rings, and

[0283] -3 to 7 aromatic or heteroaromatic rings, wherein one or more daughter groups of the aromatic and / or heteroaromatic rings may fuse to form a fused aromatic or heteroaromatic ring system;

[0284] The molecular weight (Mw) of the organic light-emitting host compound is in the range of ≥400 g / mol to ≤2000 g / mol.

[0285] According to a preferred embodiment of the present invention, the organic light-emitting host compound has the formula (V).

[0286] (V),

[0287] in

[0288] Ar 41 and Ar 42 Independently selected from substituted or unsubstituted C6 to C6. 24 Aryl, substituted or unsubstituted C3 to C 24 Mixed aromatics;

[0289] L 41 and L 42 Independently selected from direct bonds or substituted or unsubstituted C6 to C1 bonds. 24 Aranediol, substituted or unsubstituted C3 to C4 24 Mixed aromatic subunits;

[0290] R 41 and R 48 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C3 to C 12Mixed aromatics;

[0291] in

[0292] Ar 41 Ar 42 L 41 L 42 R 41 To R 48 The substituents on the surface are independently selected from D, C6 to C6. 10 Aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or perfluorinated C1 to C 16 Alkyl, partially or perfluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, halogen, F or CN.

[0293] According to a preferred embodiment of the present invention, the organic light-emitting body and / or the compound of formula (V) are selected from formulas (BH1) to (BH13):

[0294] (BH1) (BH2) (BH3) (BH4)

[0295] (BH5) (BH6) (BH7)

[0296] (BH8) (BH9)

[0297] (BH10) (BH11)

[0298] (BH12) (BH13).

[0299] According to a preferred embodiment of the present invention, the light-emitting layer comprises a light-emitting dopant of formula (IV) and an organic light-emitting body of formula (V).

[0300] According to a preferred embodiment of the present invention, the organic semiconductor layer comprises a compound of formula (I) and a compound of formula (IIIa) or (IIIb), the hole transport layer comprises a compound of formula (IIIa) or (IIIb), preferably, the organic semiconductor layer and the hole transport layer comprise the same compound of formula (IIIa) or (IIIb), and the light-emitting layer comprises a light-emitting dopant of formula (IV) and an organic light-emitting body of formula (V).

[0301] The organic semiconductor layer is arranged between the anode layer and the hole transport layer, the hole transport layer is arranged between the organic semiconductor layer and the light-emitting layer, and the light-emitting layer is arranged between the hole transport layer and the cathode layer.

[0302] According to a preferred embodiment of the present invention, the organic semiconductor layer comprises a compound of formula (I) and a compound of formula (IIIa) or (IIIb), the hole transport layer comprises a compound of formula (IIIa) or (IIIb), preferably, the organic semiconductor layer and the hole transport layer comprise the same compound of formula (IIIa) or (IIIb), and the light-emitting layer comprises a light-emitting dopant of formula (IV) and an organic light-emitting body of formula (V).

[0303] The organic semiconductor layer is arranged between the anode layer and the hole transport layer, the hole transport layer is arranged between the organic semiconductor layer and the light-emitting layer, and the light-emitting layer is arranged between the hole transport layer and the cathode layer.

[0304] The anode layer may include a first anode sublayer containing Ag or Au with a thickness of 100 to 150 nm, a second anode sublayer containing transparent conductive oxide or composed thereof with a thickness of 3 to 20 nm, and a third anode sublayer containing transparent conductive oxide or composed thereof with a thickness of 3 to 20 nm. Preferably, the transparent conductive oxide is selected from ITO or IZO.

[0305] Hole blocking layer (HBL)

[0306] Hole blocking layers (HBLs) can be formed on EMLs using methods such as vacuum deposition, spin coating, slot die coating, printing, casting, and LB deposition to prevent holes from diffusing into the ETL. When the EML contains phosphorescent dopants, the HBL can also have triplet exciton blocking functionality.

[0307] HBL can also be referred to as auxiliary ETL or a-ETL.

[0308] When forming HBLs using vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used for forming HILs. However, the deposition and coating conditions can vary depending on the compound used to form the HBL. Any compound commonly used to form HBLs can be used. Examples of compounds used to form HBLs include diazole derivatives, triazole derivatives, phenanthroline derivatives, and triazine derivatives.

[0309] HBLs can have a thickness ranging from about 5 nm to about 100 nm, for example, from about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL can have excellent hole blocking properties without causing substantial damage to the driving voltage.

[0310] Electron Transport Layer (ETL)

[0311] The organic electronic device according to the present invention may further include an electron transport layer (ETL), wherein the electron transport layer is disposed between the anode layer and the cathode layer, preferably between the organic semiconductor layer and the cathode layer.

[0312] According to another embodiment of the invention, the electron transport layer may further comprise an azazine compound, preferably a triazine compound.

[0313] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organic complexes, preferably LiQ.

[0314] The thickness of the ETL can range from about 15 nm to about 50 nm, for example, from about 20 nm to about 40 nm. When the thickness of the ETL is within this range, the ETL can have satisfactory electron injection properties without causing substantial damage to the drive voltage.

[0315] According to another embodiment of the present invention, the organic electronic device may further include a hole-blocking layer and an electron transport layer, wherein the hole-blocking layer and the electron transport layer comprise an azazine compound. Preferably, the azazine compound is a triazine compound.

[0316] Electron Injection Layer (EIL)

[0317] Optional electron-transporting layers (EILs) that facilitate electron injection from the cathode can be formed on the electron transport layer (ETL), preferably directly on it. Examples of materials used to form EILs include lithium 8-hydroxyquinoline (LiQ), LiF, NaCl, CsF, Li₂O, BaO, Ca, Ba, Yb, and Mg, which are known in the art. The deposition and coating conditions for forming EILs are similar to those for forming HILs, but the deposition and coating conditions may vary depending on the material used to form the EIL.

[0318] The thickness of the EIL can range from about 0.1 nm to about 10 nm, for example, from about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL can have satisfactory electron injection properties without causing substantial damage to the driving voltage.

[0319] cathode layer

[0320] The cathode layer is formed on an ETL or optionally an EIL. The cathode layer can be formed of a metal, alloy, conductive compound, or a mixture thereof. The cathode layer can have a low work function. For example, the cathode layer can be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode layer can be formed of a transparent conductive oxide such as ITO or IZO.

[0321] The thickness of the cathode layer can range from about 5 nm to about 1000 nm, for example, from about 10 nm to about 100 nm. When the thickness of the cathode layer is in the range of about 5 nm to about 50 nm, it can be transparent or translucent even if the cathode layer is formed of metal or metal alloy.

[0322] It should be understood that the cathode layer is not part of the electron injection layer or the electron transport layer.

[0323] Organic light-emitting diode (OLED)

[0324] The organic electronic device according to the present invention can be an organic light-emitting device.

[0325] According to one aspect of the present invention, an organic light-emitting diode (OLED) is provided, the OLED comprising: a substrate; an anode layer formed on the substrate; an organic semiconductor layer comprising a compound of formula (I); a hole transport layer; a light-emitting layer; an electron transport layer; and a cathode layer.

[0326] According to another aspect of the present invention, an OLED is provided, the OLED comprising: a substrate; an anode layer formed on the substrate; an organic semiconductor layer comprising a compound of formula (I); a hole transport layer; an electron blocking layer; a light-emitting layer; a hole blocking layer; an electron transport layer; and a cathode layer.

[0327] According to another aspect of the present invention, an OLED is provided, the OLED comprising: a substrate; an anode layer formed on the substrate; an organic semiconductor layer comprising a compound of formula (I); a hole transport layer; an electron blocking layer; a light-emitting layer; a hole blocking layer; an electron transport layer; an electron injection layer; and a cathode layer.

[0328] According to various embodiments of the present invention, OLED layers can be provided disposed between the aforementioned layers, on a substrate, or on a top layer.

[0329] Organic electronic devices

[0330] The organic electronic device according to the present invention can be a light-emitting device or a photovoltaic cell, and is preferably a light-emitting device.

[0331] According to another aspect of the present invention, a method for manufacturing an organic electronic device is provided, the method using:

[0332] - At least one sedimentation source, preferably two sedimentation sources, more preferably at least three sedimentation sources.

[0333] Suitable deposition methods include:

[0334] - Deposition via vacuum thermal evaporation;

[0335] - Deposition via solution processing, preferably the processing being selected from spin coating, printing, casting; and / or

[0336] - Slit-type die coating.

[0337] According to various embodiments of the present invention, a method is provided using the following deposition source:

[0338] - A first deposition source for releasing the compound according to formula (I) of the invention, and

[0339] - A second deposition source for releasing fundamentally covalent matrix compounds;

[0340] The method includes the step of forming an organic semiconductor layer; wherein, for organic light-emitting diodes (OLEDs):

[0341] - An organic semiconductor layer is formed by releasing a compound of formula (I) according to the invention from a first deposition source and releasing a substantially covalent matrix compound from a second deposition source.

[0342] According to various embodiments of the present invention, the method may further include forming at least one layer selected from the following on the anode layer: forming a hole transport layer or forming a hole blocking layer; and forming a light-emitting layer between the anode layer and the first electron transport layer.

[0343] According to various embodiments of the present invention, the method may further include a step for forming an organic light-emitting diode (OLED), wherein

[0344] - Form an anode layer on the substrate.

[0345] - An organic semiconductor layer comprising a compound of formula (I) is formed on the anode layer.

[0346] - A hole transport layer is formed on an organic semiconductor layer containing a compound of formula (I).

[0347] - A light-emitting layer is formed on the hole transport layer.

[0348] - An electron transport layer is formed on the light-emitting layer, and optionally a hole blocking layer is formed on the light-emitting layer.

[0349] -And finally, a cathode layer is formed.

[0350] - An optional hole-blocking layer is formed between the first anode layer and the light-emitting layer in the order described.

[0351] - An optional electron injection layer is formed between the electron transport layer and the cathode layer.

[0352] According to various embodiments, the OLED may have the following layer structure, wherein these layers have the following order:

[0353] The anode layer, an organic semiconductor layer comprising a compound according to formula (I) of the present invention, a first hole transport layer, a second hole transport layer, a light-emitting layer, an optional hole blocking layer, an electron transport layer, an optional electron injection layer, and a cathode layer.

[0354] According to another aspect of the invention, an electronic device is provided, the electronic device comprising at least one organic light-emitting device according to any embodiment described throughout this application, preferably, the electronic device comprising an organic light-emitting diode as described in one of the embodiments described throughout this application. More preferably, the electronic device is a display device.

[0355] In the following description, implementation methods will be illustrated with reference to embodiments. However, this disclosure is not limited to the following embodiments. Exemplary aspects will now be referred to in detail. Attached Figure Description

[0356] The aforementioned components in the described embodiments, as well as the claimed components and components to be used according to the invention, have no particular exceptions in terms of their size, shape, material selection, and technical concept, thereby allowing the application of selection criteria known in the relevant field without limitation.

[0357] Further details, features, and advantages of the invention are disclosed in the dependent claims and the following description of the various drawings, which illustrate preferred embodiments of the invention by way of example. However, any embodiment is not necessarily representative of the full scope of the invention, and therefore the scope of the invention is to be understood with reference to the claims and this document. It should be understood that the foregoing general description and the following detailed description are merely exemplary and explanatory, and are intended to provide further explanation of the claimed invention.

[0358] Figures 1 to 6

[0359] Figure 1 This is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention;

[0360] Figure 2 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0361] Figure 3 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0362] Figure 4 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0363] Figure 5 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0364] Figure 6 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention.

[0365] In the following text, reference is made to the embodiments. Figures 1 to 6 A more detailed explanation will follow. However, this disclosure is not limited to the following figures.

[0366] In this document, when a first element is referred to as being formed or disposed "on" or "above" a second element, the first element may be disposed directly on the second element, or one or more other elements may be disposed between them. When a first element is referred to as being "directly" formed or disposed "on" or "above" a second element, no other elements are disposed between them.

[0367] Figure 1 This is a schematic cross-sectional view of an organic electronic device 101 according to an exemplary embodiment of the present invention. The organic electronic device 101 includes a substrate (110), an anode layer (120), an organic semiconductor layer (130) comprising a compound of formula (I), a photoactive layer (PAL) (151), and a cathode layer (190).

[0368] Figure 2 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110), an anode layer (120), an organic semiconductor layer (130) comprising a compound of formula (I), a light-emitting layer (EML) (150), and a cathode layer (190).

[0369] Figure 3 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110), an anode layer (120), an organic semiconductor layer (130) comprising a compound of formula (I), a hole transport layer (HTL) (140), an emissive layer (EML) (150), an electron transport layer (ETL) (160), and a cathode layer (190).

[0370] Figure 4 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110), an anode layer (120), an organic semiconductor layer (130) comprising a compound of formula (I), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), a light-emitting layer (EML) (150), a hole blocking layer (HBL) (155), an electron transport layer (ETL) (160), an optional electron injection layer (EIL) (180), and a cathode layer (190).

[0371] Figure 5 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110), an anode layer (120) including a first anode sublayer (121) and a second anode sublayer (122), an organic semiconductor layer (130) including a compound of formula (I), a hole transport layer (HTL) (140), an electron blocking layer (EBL) (145), a light-emitting layer (EML) (150), a hole blocking layer (EBL) (155), an electron transport layer (ETL) (160), and a cathode layer (190).

[0372] Figure 6 This is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate (110); an anode layer (120) including a first anode sublayer (121), a second anode sublayer (122), and a third anode sublayer (123); an organic semiconductor layer (130) including a compound of formula (I); a hole transport layer (HTL) (140); an electron blocking layer (EBL) (145); a light-emitting layer (EML) (150); a hole blocking layer (EBL) (155); an electron transport layer (ETL) (160); and a cathode layer (190). The layers are arranged in exactly the order described above.

[0373] In the above description, the method of manufacturing the organic electronic device 101 of the present invention begins, for example, with forming an anode layer (120) thereon on a substrate (110), and forming an organic semiconductor layer (130) comprising a compound of formula (I), a photoactive layer (151) and a cathode layer 190 on the anode layer (120), either exactly in the order described or exactly in the reverse order.

[0374] In the above description, the method of manufacturing the OLED 100 of the present invention begins with forming an anode layer (120) thereon on a substrate (110), and forming on the anode layer (120) an organic semiconductor layer (130) comprising a compound of formula (I), an optional hole transport layer (140), an optional electron blocking layer (145), a light-emitting layer (150), an optional hole blocking layer (155), an optional electron transport layer (160), an optional electron injection layer (180), and a cathode layer 190, in exactly the order described or in exactly the reverse order.

[0375] The organic semiconductor layer (130) of the compound containing formula (I) can be a hole injection layer.

[0376] Despite Figures 1 to 6 Not shown, but a capping layer and / or sealing layer may also be formed on the cathode layer (190) to seal the OLED 100. Various other modifications may also be made thereto.

[0377] In the following description, one or more exemplary embodiments of the present invention will be described in detail with reference to the following examples. However, these embodiments are not intended to limit the purpose and scope of the one or more exemplary embodiments of the present invention. Detailed Implementation

[0378] The present invention is further illustrated by the following embodiments, which are merely exemplary and not restrictive.

[0379] The protonated form of the ligand of formula (II), LH, can be prepared by methods known in the art.

[0380] The ligand B1-H can be prepared by the method described in Sloop, Joseph C. et al., Journal of Fluorine Chemistry, 2002, 118(1-2), 135-147.

[0381] Ligand B83-H can be prepared by methods known in the art or as described below.

[0382] Synthesis of 2-(3,5-bis(trifluoromethyl)benzoyl)-3-hydroxy-1H-inden-1-one (B83-H)

[0383]

[0384] 3.78 g (25.86 mmol) of 1,3-indanedion was dissolved in 35 mL of dialkylene and 4.79 g (64.65 mmol) of calcium hydroxide was added. 7.15 g (25.86 mmol) of 3,5-bis(trifluoromethyl)benzoyl chloride was added dropwise and the mixture was stirred at room temperature for 2 days. The reaction mixture was poured onto 300 mL of 10% hydrochloric acid solution. The precipitate was filtered off, washed with 800 mL of water, dried, and crystallized from ethanol to obtain 7.12 g (71%) of the product as a pale yellow powder.

[0385] The compounds of formula (I) can be prepared by methods known in the art and as described below.

[0386] Compounds of formula (I), where M is Cu, Zn, Cd, Pb and n is 2, can be prepared by the method described in Enchev, Venelin et al., J. Mol. Struct. (Journal of Molecular Structure), 2001, 595(1-3), 67-76.

[0387] Compounds of formula (I), where M is Fe and n is 3, can be prepared by the method described in Ahmedova, Anife et al., Inorg.Chim. Acta (Chinese Journal of Inorganic Chemistry), 2006, 359(10), 3123-3128.

[0388] The compound of formula (I), wherein M is Fe and n is 2, can be prepared by the method described in Rusanov, Ventzislav et al., Eur. J. Chem. (European Journal of Chemistry), 2014, 5(1), 176-180.

[0389] Compounds of formula (I), wherein M is Mn and n is 2, can be prepared by methods known in the art or as described below.

[0390] Compounds of formula (I), wherein M is In and n is 3, can be prepared by methods known in the art or as described below.

[0391] Synthesis of bis((2-(3,5-bis(trifluoromethyl)benzoyl)-1-oxo-1H-inden-3-yl)oxy)manganese (A56)

[0392]

[0393] 3.44 g (8.91 mmol) of 2-(3,5-bis(trifluoromethyl)benzoyl)-3-hydroxy-1H-inden-1-one was suspended in 30 mL of ethanol, and a solution of 1.09 g (4.45 mmol) of manganese acetate tetrahydrate in 30 mL of ethanol was added. The mixture was stirred overnight at room temperature. The mixture was cooled using an ice bath, and the precipitate was filtered off, washed with ethanol, and dried under high vacuum at 120 °C to obtain 3.37 g (92%) of orange solid, which was further purified by sublimation.

[0394] Synthesis of 1-oxo-2-(2,2,2-trifluoroacetyl)-1H-inden-3-ol indium(III) (A60)

[0395]

[0396] 4.84 g (20 mmol) of 3-hydroxy-2-(2,2,2-trifluoroacetyl)-1H-inden-1-one was dissolved in 100 mL of THF, and 1.08 g (20 mmol) of sodium methoxide was added. The mixture was stirred for 5 minutes, then 1.46 g (6.66 mmol) of indium trichloride was added, and the reaction was stirred overnight. The solvent was removed under reduced pressure, and the residue slurry was washed with 60 mL of water. The solid was filtered off and dried under high vacuum. 4.66 g (83%) of the product as a yellow powder was obtained, which was further purified by sublimation.

[0397] Compounds of formulas (III), (IV) and (V) can be prepared by methods known in the art.

[0398] Calculated LUMO for compounds of formula (I) and comparative compounds

[0399] The energies of the lowest unoccupied molecular orbitals (LUMOs) of the compounds of formula (I) and the comparative compounds were calculated using the packages ORCAV 5.0.3 (Max Planck Institute for Kohlenforschung, Kaiser Wilhelm Platz 1,45470, Muelheim / Ruhr, Germany) and WEASEL 1.9.2 (FAccTs GmbH, Rolandstrasse 67,50677 Köln, Germany). The HOMO and LUMO energy levels of the molecular structure were determined from the optimized geometry by applying the hybrid functionals B3LYP and Def2-TZVP basis sets and the Stuttgart / Dresden (SDD) effective nuclear potential (ECP) of the metal. The optimized geometry was obtained by applying the functionals BP86 and Def2-SVP basis sets and the Stuttgart / Dresden (SDD) effective nuclear potential (ECP) of the metal. All calculations were performed in the gas phase. If more than one conformation is feasible, the conformation with the lowest total energy is chosen. Different multistates can be applied depending on the metal cation. For the following metal cations, multistates are shown in parentheses: Cu 2+ (Double state), Fe 2+ (pentet state), Fe 3+ (six-fold state), Zn 2+ (singlet state), Mn 2+ (six-fold state), In 3+ (Singlet state).

[0400] Unless otherwise stated, the LUMO values ​​in Tables 1 and 2 are calculated using this method.

[0401] HOMO and LUMO of compounds of formulas (III), (IV) and (V)

[0402] The HOMO and LUMO of compounds of formulas (III), (IV), and (V) were calculated using the package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The results were obtained by applying the hybrid functional B3LYP in the gas phase. The basis set was used to determine the optimized geometry and the HOMO and LUMO levels of the molecular structure. If more than one conformation was feasible, the conformation with the lowest total energy was selected. Under these conditions, the HOMO level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirobis[fluorene]-2,2',7,7'-tetraamine was -4.27 eV.

[0403] Alternatively, the HOMO and LUMO of the compounds of formulas (III), (IV) and (V) can be calculated as described above for the compounds of formula (I).

[0404] Melting point

[0405] Melting point (mp) was determined from the DSC curve obtained from the TGA-DSC measurement described above or from a separate DSC measurement (Mettler Toledo DSC822e, where the sample was heated from room temperature to complete melting at a heating rate of 10 K / min under a pure nitrogen flow. Samples of 4 to 6 mg were placed in a 40 μL covered Mettler Toledo aluminum dish with a hole of <1 mm punched in the cover).

[0406] Glass transition temperature

[0407] As described in DIN EN ISO 11357 published in March 2010, the glass transition temperature (Tg) is measured in nitrogen and at a heating rate of 10 K / min in a Mettler Toledo DSC 822e differential scanning calorimeter.

[0408] Decomposition temperature T dec

[0409] The decomposition temperature T was measured by loading 9 to 11 mg of sample into a Mettler Toledo 100 µL uncovered aluminum dish under nitrogen atmosphere in a Mettler Toledo TGA-DSC 1 instrument. dec Use the following heating program: isothermal at 25°C for 3 min; from 25°C to 600°C, 10 K / min.

[0410] Decomposition temperature is determined based on the decomposition initiation point in the TGA.

[0411] Decomposition temperature indicates the temperature at which a compound decomposes. The higher the decomposition temperature, the higher the thermal stability of the compound.

[0412] Standard starting temperature

[0413] The standard onset temperature (T) was determined by loading 100 mg of the compound into a VTE source. RO As a VTE source, point sources for organic materials, such as those supplied by Kurt J. Lesker (www.lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com), can be used. (The last part, "in less than 10," appears to be an unrelated fragment and is omitted from the translation.) -5The VTE source was heated at a constant rate of 15 K / min under a pressure of millibars, and the internal temperature of the source was measured using thermocouples. The evaporation of the compound was detected using a QCM detector, which detected the deposition of the compound on a quartz crystal of the detector. The deposition rate on the quartz crystal was measured in angstroms per second. To determine the standard onset temperature, the deposition rate was plotted against the VTE source temperature. The standard onset is the temperature at which significant deposition occurs on the QCM detector. To obtain accurate results, the VTE source was heated and cooled three times, and only the results of the second and third runs were used to determine the standard onset temperature.

[0414] To effectively control the evaporation rate of organic compounds, a standard starting temperature can be in the range of 200°C to 300°C. If the standard starting temperature is significantly below 200°C, evaporation may be too rapid and therefore difficult to control. If the standard starting temperature is above 300°C, the evaporation rate may be too low, which could result in a low cycle time, and the compound of formula (I) in the VTE source may decompose due to prolonged exposure to high temperatures.

[0415] The standard onset temperature is an indirect measure of a compound's volatility. The higher the standard onset temperature, the lower the compound's volatility.

[0416] Table 2 shows the standard onset temperature T for compounds of formula (I) and comparative compounds. RO .

[0417] General procedures for manufacturing OLEDs

[0418] For Invention Examples 1-1 to 1-18 and Comparative Examples 1-1 to 1-4 in Table 3, a glass substrate having an anode layer comprising a first anode sublayer of 120 nm Ag, a second anode sublayer of 8 nm ITO, and a third anode sublayer of 10 nm ITO was cut into 50 mm × 50 mm × 0.7 mm dimensions, ultrasonically washed with water for 60 minutes, and then ultrasonically washed with isopropanol for 20 minutes. The liquid film was removed in a nitrogen stream, followed by plasma treatment to prepare the anode layer. The plasma treatment was performed in an atmosphere containing 97.6 vol% nitrogen and 2.4 vol% oxygen.

[0419] Then, the compound of formula (I) and the matrix compound 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 is shown in Table 3. The formula of the compound of formula (I) is as described above or can be found in Tables 1 and 2.

[0420] The matrix compound was then vacuum-deposited onto the HIL to form an HTL with a thickness of 123 nm. The compound of formula (II) in the HTL was selected to be the same as the matrix compound in the HIL. The matrix compounds are shown in Table 3.

[0421] Then, N,N-bis([1,1'-biphenyl]-4-yl)-3'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine was vacuum deposited on HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0422] Then, a light-emitting layer (EML) with a thickness of 20 nm was formed on the EBL by co-depositing 99 vol% EML host compound BH9 and 1 vol% EML dopant BD8.

[0423] Then, a hole-blocking layer with a thickness of 5 nm was formed by depositing 4-([1,1'-biphenyl]-4-yl)-6-(3'-(9,9-dimethyl-9H-fluorene-4-yl)-[1,1'-biphenyl]-4-yl)-2-phenylpyrimidine on the luminescent layer EML.

[0424] Then, an electron transport layer with a thickness of 31 nm was formed on the hole blocking layer by depositing 50 wt% 6,6'-(naphthalene-1,2-dimethylbis(4,1-phenyleneyl))bis(2,4-diphenyl-1,3,5-triazine) and 50 wt% LiQ.

[0425] Then, an electron injection layer is formed on the electron transport layer by depositing a 1.3 nm Yb layer.

[0426] In 10 -7 Ag:Mg (90:10, volume%) was evaporated at a rate of 0.01 to 1 Å / s under millibars to form a cathode layer with a thickness of 13 nm on the electron transport layer.

[0427] Then, N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazole-3-yl)phenyl)-9H-fluorene-2-amine was deposited on the cathode layer to form a capping layer with a thickness of 75 nm.

[0428] The OLED stack is protected from environmental conditions by encapsulating the device with a glass slide. This creates a cavity containing a getter material for further protection.

[0429] To evaluate the performance of the invention relative to the prior art, current efficiency was measured at 20°C. The current-voltage characteristics were determined using a Keithley 2635 source measurement unit by applying a voltage in V and measuring the current flowing through the device under test in mA. The voltage applied to the device varied in 0.1V steps within the range of 0V to 10V. Similarly, individual voltage values ​​were measured in cd / m² using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 The luminance-voltage characteristics and CIE coordinates are determined using unit luminance.

[0430] To determine the voltage stability over time U(100h)-(1h), a voltage of 20mA / cm was applied to the device. 2 The current density was measured. The operating voltage was measured after 1 hour and 100 hours, and the voltage stability over the time period from 1 hour to 100 hours was calculated. A low U(100h)-(1h) value indicates a lower operating voltage increase over time, thus improving voltage stability.

[0431] Technical effects of the present invention

[0432] Table 1 shows the calculated LUMO in electron volts for compounds of formula (I). The following multivariates are applied based on the metal cation: Cu 2+ (Double state), Fe 2+ (pentet state), Fe 3+ (six-fold state), Zn 2+ (singlet state), Mn 2+ (six-fold state), In 3 + (Singlet state).

[0433] Table 1: LUMO values ​​of compounds of formula (I) and comparative compounds

[0434]

[0435]

[0436]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443] In comparative compound 4 (CC-4), the compound contains a Cu(II) cation and a ligand without a CF3 group. The LUMO is -3.73 eV.

[0444] In comparative compound 5 (CC-5), the compound comprises an Fe(II) cation and a ligand without a CF3 group. The LUMO is -2.62 eV.

[0445] In comparative compound 6 (CC-6), the compound comprises an Fe(III) cation and a ligand without a CF3 group. The LUMO is -4.02 eV.

[0446] In comparative compound 7 (CC-7), the compound comprises a Zn(II) cation and a ligand without a CF3 group. The LUMO is -2.64 eV.

[0447] In comparative compound 8 (CC-8), the compound comprises a Mn(II) cation and a ligand without a CF3 group. The LUMO is -2.82 eV.

[0448] In comparative compound 9 (CC-9), the compound contains an In(III) cation and a ligand without a CF3 group. The LUMO is -2.65 eV.

[0449] As can be seen in Table 1, the LUMO energy levels of the compounds of formula (I) are within the range suitable for organic electronic devices.

[0450] Unbound by theory, LUMO levels further away from vacuum levels could be beneficial for improving the performance of organic electronic devices.

[0451] Table 2 shows the LUMO energy and thermal properties of compounds 1 to 3 and the compound of formula (I).

[0452] The LUMO of the comparison compound 1 (CC-1) is -3.76 eV. The standard onset temperature is 187 °C.

[0453] In comparative compound 2 (CC-2), the Cu(II) cation has been replaced by the Fe(III) cation. The LUMO has been improved to -4.14 eV. The standard onset temperature has been improved to 196 °C.

[0454] Comparative compound 3 (CC-3) contains a different ligand than CC-2. LUMO was further improved to -4.76 eV. However, the melting point and standard onset temperature were significantly reduced.

[0455] Compound 1 (A1) contains a different ligand than CC-1. In compound 1, the LUMO is -4.4 eV. Compared to CC-1 and CC-5, the LUMO is further away from the vacuum level. In addition, the thermal properties are significantly improved compared to comparative compounds 1 to 3.

[0456] Compared to compound 1, in compound 2 (A11), the Cu(II) cation has been replaced by the Fe(II) cation. The LUMO is -3.08 eV. Compared to CC-4, the LUMO is further away from the vacuum level. The thermal properties are significantly improved compared to comparative compounds 1 to 3, see Table 2.

[0457] Compared to compound 2, in compound 3 (A27), the Fe(II) cation has been replaced by the Fe(III) cation. Furthermore, compound 3 contains different R... 5 Group. LUMO is -4.55 eV. Compared to CC-6, LUMO is further away from the vacuum energy level. Compared to comparative compounds 1 to 3, the thermal properties are significantly improved, see Table 2.

[0458] Compared to compound 3, in compound 4 (A56), the Fe(III) cation has been replaced by the Mn(II) cation. The LUMO is -3.29 eV. Compared to CC-8, the LUMO is further away from the vacuum level. The thermal properties are significantly improved compared to comparative compounds 1 to 3, see Table 2.

[0459] Compared to compound 2, in compound 5 (A60), the Fe(II) cation has been replaced by the In(III) cation. The LUMO is -3.23 eV. Compared to CC-9, the LUMO is further away from the vacuum level. The thermal properties are significantly improved compared to comparative compounds 1 to 3, see Table 2.

[0460] In summary, the compounds of formula (I) may have LUMO energy levels within the range suitable for organic electronic devices and / or thermal properties that enable the mass production of organic electronic devices.

[0461] Table 3 shows the properties of organic electronic devices comprising semiconductor layers of compounds of formula (I) and comparative compounds CC-1 and CC-2.

[0462] In Comparative Example 1-1, the semiconductor layer contains 7.5 wt% CC-1. As can be seen in Table 3, the operating voltage is 3.45V and U(100h)-(1h) is 0.747V.

[0463] In Comparative Examples 1-2, the semiconductor layer contained 12.5 wt% CC-1. As can be seen in Table 3, the operating voltage was improved to 3.43V, and U(100h)-(1h) was improved to 0.630V.

[0464] In Comparative Examples 1-3, the semiconductor layer contained 7.5% by weight of CC-2. The difference between CC-2 and CC-1 is the presence of metal cations. As can be seen in Table 3, compared with Comparative Example 1-1, the operating voltage was 3.46V, and U(100h)-(1h) increased to 0.951V.

[0465] In Comparative Examples 1-4, the semiconductor layer contained 12.5 wt% CC-2. As can be seen in Table 3, compared with Comparative Examples 1-3, the operating voltage was improved to 3.44V and U(100h)-(1h) was improved to 0.657V.

[0466] In Example 1-1, the semiconductor layer contains 6% by weight of compound A1 of formula (I). A1 differs from CC-1 in the ligand. As can be seen in Table 3, compared with Comparative Examples 1-1 to 1-4, the operating voltage is improved to 3.33V and U(100h)-(1h) is improved to 0.047V.

[0467] In Examples 1-2 to 1-4, the semiconductor layer contained a higher concentration of compound Al of formula (I). As can be seen in Table 3, the operating voltage and U(100h)-(1h) were improved compared to Comparative Examples 1-1 to 1-4.

[0468] In Examples 1-5, the semiconductor layer comprises 8% by weight of compound A11 of formula (I). A11 differs from A1 in that it is a metal cation. As can be seen in Table 3, compared with Comparative Examples 1-1 to 1-4, the operating voltage is improved to 3.33V and U(100h)-(1h) is improved to 0.048V.

[0469] In Examples 1-6 and 1-7, the semiconductor layer contained a higher concentration of compound A11 of formula (I). As can be seen in Table 3, the operating voltage and U(100h)-(1h) were improved compared to Comparative Examples 1-1 to 1-4.

[0470] In Examples 1-8 to 1-10, the semiconductor layer comprises compound A11 of formula (I) and matrix compound F10. As can be seen in Table 3, the operating voltage and U(100h)-(1h) are improved compared to Comparative Examples 1-1 to 1-4.

[0471] In Examples 1-11 and 1-12, the semiconductor layer comprised two different concentrations of compound A1 of formula (I) and matrix compound F20. As can be seen in Table 3, the operating voltage and U(100h)-(1h) were improved compared to Comparative Examples 1-1 to 1-4.

[0472] In Examples 1-13 and 1-16, the semiconductor layer contained different concentrations of compound A60 of formula (I) and matrix compound F18. As can be seen in Table 3, the operating voltage and U(100h)-(1h) were improved compared to Comparative Examples 1-1 to 1-4.

[0473] In Examples 1-17 and 1-18, the semiconductor layer comprised two different concentrations of compound A60 of formula (I) and matrix compound F4. As can be seen in Table 3, the operating voltage and U(100h)-(1h) were improved compared to Comparative Examples 1-1 to 1-4.

[0474] Low operating voltage is important for low power consumption in organic electronic devices, especially mobile devices.

[0475] For the long-term operational stability of organic electronic devices, the voltage rise over time, U(100h)-(1h), is low.

[0476] Table 2: Properties of compounds of formula (I) and comparative compounds 1 to 3

[0477]

[0478]

[0479] 1) “no” = Not observed. 2) “nd” = Undetermined

[0480] Table 3: Performance of organic electroluminescent devices including organic semiconductor layers of compounds containing formula (I) or comparative compounds

[0481]

[0482]

[0483] The specific combinations of elements and features in the detailed embodiments described above are merely exemplary; these teachings are interchanged and substituted with other teachings herein and in the series / applications incorporated by reference. As will be appreciated by those skilled in the art, variations, modifications, and other implementations of the description herein will be apparent to those of ordinary skill in the art without departing from the spirit and scope of the claimed invention. Therefore, the above description is by way of example only and is not intended to be limiting. In the claims, the word “comprising” does not exclude other elements or steps, and the singular forms “a” or “an” do not exclude the plural. The fact that specific measures are enumerated in dissimilar dependent claims does not imply that combinations of these measures cannot be used advantageously. The scope of the invention is defined by the claims and their equivalents. Furthermore, the reference numerals used in the specification and claims do not limit the scope of the claimed invention.

Claims

1. A compound of formula (1): (I)， in: M is a metal ion, where M is selected from alkali metals, alkaline earth metals, group III to V or transition metals; n is the valence of M and is selected from 1 to 3; L is the ligand of formula (II) (II), in X 1 Selected from CR 1 Or N; X 2 Selected from CR 2 Or N; X 3 Selected from CR 3 Or N; X 4 Selected from CR 4 Or N; Where X 1 X 2 X 3 X 4 The 0, 1, or 2 in the N are selected; R 1 To R 4 Independently selected from H, D, substituted or unsubstituted C1 to C2 12 Alkyl, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl, halogen, F, Cl or CN; and any R therein k To R k+1 They can form a ring; where k is an integer from 1 to 3; R 5 Selected from unsubstituted and substituted C1 to C1 12 Alkyl, substituted or unsubstituted C6 to C 19 Aryl, substituted or unsubstituted C2 to C 20 Heteroaryl, substituted or unsubstituted 6-membered heteroaryl; in Replacement of C1 to C 12 Alkyl, substituted C6 to C 19 Aryl, substituted C2 to C 20 At least one of the substituents of the heteroaryl or substituted 6-membered heteroaryl is independently selected from halogen, Cl, F, CN, partially or perfluorinated C1 to C8 alkyl, partially or perfluorinated C1 to C8 alkoxy; in R 1 To R 4 and / or R 5 At least one of them contains at least one CF3 portion, and / or R 1 R 2 R 3 R 4 and R 5 One of them is CF3; in AL is an auxiliary ligand that coordinates with the metal ion M; m is an integer selected from 0 to 2.

2. The compound according to claim 1, wherein M of the compound of formula (I) may be selected from a metal ion, wherein the corresponding metal has an electronegativity of ≥1.5 and ≤2.4 according to Allen.

3. The compound according to claim 1 or 2, wherein M has an atomic weight of ≥54 Da.

4. The compound according to claims 1 to 3, wherein M may be selected from group III to V or a transition metal.

5. The compound according to any one of claims 1 to 4, wherein R 1 To R 4 At least two of them are H or F.

6. The compound according to claims 1 to 5, wherein R 1 To R 4 At least one of them is CF3 or CN.

7. The compound according to any one of claims 1 to 6, wherein R 5 Selected from partially or fully fluorinated C1 to C125C4 ... 12 Alkyl groups, preferably perfluorinated C1 to C6 alkyl groups.

8. An organic semiconductor layer, wherein the organic semiconductor layer comprises a compound of formula (I) according to any one of claims 1 to 7.

9. An organic electronic device comprising an anode layer, a cathode layer and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is disposed between the anode layer and the cathode layer, and wherein the at least one organic semiconductor layer is the organic semiconductor layer according to claim 8.

10. The organic electronic device of claim 9, wherein the anode layer comprises at least a first anode sublayer and a second anode sublayer.

11. The organic electronic device according to claim 9 or 10, wherein the organic electronic device further comprises at least one photoactive layer, wherein the at least one photoactive layer is disposed between the anode layer and the cathode layer; preferably, the photoactive layer is disposed between the organic semiconductor layer and the cathode layer.

12. The organic electronic device according to any one of claims 9 to 11, wherein the photoactive layer is a light-emitting layer.

13. The organic electronic device according to any one of claims 9 to 12, wherein the device comprises at least one light-emitting layer comprising a light-emitting compound of formula (IV). (IV), in Z 1 Z 2 and Z 3 They may be the same as or different from each other, and each is independently selected from monocyclic to polycyclic aromatic hydrocarbon rings or monocyclic to polycyclic aromatic heterocycles; Ar 31 and Ar 32 They may be chosen, either the same or different from each other, and each independently is a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or bonded to an adjacent substituent to form a substituted or unsubstituted aromatic ring or a substituted or unsubstituted aliphatic ring; R 31 R 32 and R 33 They may be the same as or different from each other, and each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl groups, substituted or unsubstituted silyl groups, substituted or unsubstituted amine groups, substituted or unsubstituted aryl groups, or substituted or unsubstituted heteroaryl groups, or adjacent substituents are bonded to each other to form substituted or unsubstituted aromatic rings or substituted or unsubstituted aliphatic rings. One or more of the substituents are selected from deuterium, alkyl groups having 1 to 6 carbon atoms, alkylsilyl groups having 1 to 30 carbon atoms, arylsilyl groups having 6 to 50 carbon atoms, alkylamine groups having 1 to 30 carbon atoms, alkylarylamine groups having 1 to 50 carbon atoms, arylamine groups having 6 to 50 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heteroaryl groups having 2 to 30 carbon atoms, or substituents connected to two or more substituents selected from said groups, or adjacent substituents bonded to each other to form an aliphatic hydrocarbon ring having 3 to 60 carbon atoms, said aliphatic hydrocarbon ring being unsubstituted or substituted by said substituents; r 31 r 32 and r 33 Each is an integer of 0, 1, 2, 3, or 4, and when r 31 to r 33 When the number is 2 or higher, the substituents in parentheses may be the same or different from each other.

14. The organic electronic device according to any one of claims 9 to 13, wherein the organic electronic device is an electroluminescent device, an organic light-emitting diode (OLED), a light-emitting device, a thin-film transistor, a battery, a display device, or an organic photovoltaic cell (OPV).

15. A display device comprising an organic electronic device according to any one of claims 9 to 14.

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