Organic electronic device comprising compound, display device comprising the organic electronic device, and compound for organic electronic device

Abstract

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

Description

Technical Field

[0001] The present invention relates to an organic electronic device comprising a compound of formula (1) and a display device comprising the organic electronic device. The present invention also relates to a novel compound of formula (1) that can be used in an organic electronic device. Background Art

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

[0003] When voltage is applied to the anode and cathode, holes injected from the anode move through the HTL to the EML, while electrons injected from the cathode move through the ETL to the EML. Holes and electrons recombine in the EML to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted. The injection and flow of holes and electrons must be balanced to ensure that OLEDs with this structure have excellent efficiency and / or a long lifetime.

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

[0005] There is still a need to improve the performance of organic semiconductor materials, semiconductor layers and organic electronic devices thereof, in particular to achieve improved stability of the operating voltage over time by improving the properties of the compounds contained therein.

[0006] Additionally, there is a need to provide compounds with improved thermal properties. Summary of the Invention

[0007] One aspect of the present invention provides an organic electronic device comprising an anode, a cathode, at least one photoactive layer, and at least one semiconductor layer, wherein the at least one semiconductor layer is arranged between the anode and the at least one photoactive layer; and wherein the at least one semiconductor layer comprises a compound of formula (1),

[0008]

[0009] in

[0010] B 1 selected from substituted or unsubstituted C3 to C 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C12 heteroaryl,

[0011] B 2 selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl,

[0012] Among them B 1 and B 2 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN;

[0013] where R 1 C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy;

[0014] Among them B 1 and / or B 2 At least one substituent is selected from C3 to C9 heteroaryl, C1 to C6 alkoxy, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN.

[0015] The negative charge in the compounds of formula (1) may be partially or completely delocalized on the N(SO2)2 group and optionally also on B 1 and B 2 Delocalized on the group.

[0016] It should be noted that throughout the application and claims, any B n 、Rn Etc. always refers to the same part unless otherwise noted.

[0017] In this specification, when no definition is provided otherwise, "substituted" refers to deuterium, C1 to C 12 Alkyl and C1 to C 12 Alkoxy substituted.

[0018] However, in this specification, "aryl-substituted" means substituted by one or more aryl groups, which may themselves be substituted by one or more aryl and / or heteroaryl groups.

[0019] Accordingly, in this specification, "heteroaryl-substituted" means substituted by one or more aryl groups, which heteroaryl group may itself be substituted by one or more aryl and / or heteroaryl groups.

[0020] In this specification, when no definition is provided otherwise, "alkyl group" refers to a saturated aliphatic hydrocarbon group. The alkyl group can be C1 to C 12 More specifically, the alkyl group may be C1 to C 10 An alkyl group or a C1 to C6 alkyl group. For example, a C1 to C4 alkyl group contains 1 to 4 carbons in the alkyl chain and can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.

[0021] Specific examples of the alkyl group may include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0022] The term "cycloalkyl" refers to a saturated hydrocarbon group derived from a cycloalkane by formally separating a hydrogen atom from a ring atom contained in the corresponding cycloalkane. Examples of the cyclic alkyl group may be a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, an adamantyl group, and the like.

[0023] The term "hetero" is understood to mean that in a structure that can be formed by covalently bonded carbon atoms, at least one carbon atom is replaced by another polyvalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, S; more preferably, from N, P, O, S.

[0024] In this specification, "aryl group" refers to a hydrocarbon group that can be produced by formally separating a hydrogen atom from the aromatic ring of the corresponding aromatic hydrocarbon. Aromatic hydrocarbon refers to a hydrocarbon containing at least one aromatic ring or aromatic ring system. An aromatic ring or aromatic ring system refers to a planar ring or ring system of covalently bound carbon atoms, wherein the planar ring or ring system includes a conjugated system of delocalized electrons that satisfies Hückel's rule. Examples of aryl groups include monocyclic groups such as phenyl or tolyl, polycyclic groups comprising multiple aromatic rings connected by single bonds, such as biphenyl, and polycyclic groups comprising fused rings, such as naphthyl or fluorenyl.

[0025] Similarly, heteroaryl is understood in particular to be a radical which is derived by formally separating a ring hydrogen from a heteroaromatic ring in compounds which contain at least one heteroaromatic ring.

[0026] Heterocycloalkyl is particularly suitably understood to be a radical which is derived by formally separating a ring hydrogen from a saturated cyclic alkyl ring in compounds which contain at least one saturated cycloalkyl ring.

[0027] The term "fused aryl ring" or "condensed aryl ring" is understood to mean when two aryl rings share at least two common sp 2 When carbon atoms are hybridized, they are said to be fused or condensed.

[0028] In this specification, a single bond refers to a direct bond.

[0029] In the context of the present invention, "different" means that the compounds do not have the same chemical structure.

[0030] The terms “without”, “not containing” or “not comprising” do not exclude impurities that may be present in the compound before deposition. Impurities have no technical effect on the purpose to be achieved by the present invention.

[0031] The term "sandwiched in contact" refers to a three-layer arrangement in which the middle layer is in direct contact with two adjacent layers.

[0032] The terms "light absorbing layer" and "light-absorbing layer" are used synonymously.

[0033] The terms "light-emitting layer," "light-emitting layer," and "emissive layer" are used synonymously.

[0034] The terms "OLED," "organic light emitting diode," and "organic light emitting device" are used synonymously.

[0035] The terms anode and anode electrode are used synonymously.

[0036] The terms cathode and cathode electrode are used synonymously.

[0037] In this specification, hole characteristics refer to the ability to form holes by donating electrons when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0038] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0039] Beneficial effects

[0040] It has surprisingly been found that the organic electronic device of the present invention solves the underlying problem of the present invention by enabling the device to outperform organic electroluminescent devices known in the art in various aspects, in particular in terms of operating voltage during lifetime.

[0041] According to one embodiment of the present invention, B 1 and B 2 The substituents on are independently selected from: halogen, particularly preferably F, C1 to C3 perhalogenated, especially perfluorinated alkyl or alkoxy, or -(O) l -C m H 2m -C n Hal n2n+1 , where l=0 or 1, especially 0, m=1 or 2, especially 1, n=1 to 3, especially 1 or 2, and Hal=halogen, especially F.

[0042] According to one embodiment of the present invention, B 1 and B 2 is a substituted alkyl group and the substituent of the alkyl group is fluorine, and the number (of fluorine substituents) n F and the number (of hydrogen) n H Follow the following equation: F >n H +2.

[0043] According to one embodiment of the present invention, B 1 and B 2 At least one of the groups is selected from perfluorinated alkyl or aryl groups.

[0044] According to one embodiment of the present invention, B 1 and B 2 At least one of the groups is a substituted C3 to C6 linear or cyclic alkyl group.

[0045] According to one embodiment of the present invention, B 1 and B 2 are the same.

[0046] According to one embodiment of the present invention, the compound of formula (1) does not contain alkoxy, COR 1 and / or COOR 1 group.

[0047] According to one embodiment of the present invention, B 1 and B 2 At least one of the is an aryl or heteroaryl group, wherein the substituents of the aryl and / or heteroaryl moiety are selected from hydrogen, halogen, F, CN or trifluoromethyl.

[0048] According to one embodiment of the present invention, B 1 and B 2 At least one of the groups is a phenyl group or a six-membered heteroaryl group, and the group is substituted by at least one trifluoromethyl group at the ortho position or the meta position of the substituted sulfoxide moiety.

[0049] According to one embodiment of the present invention, B 1 and B 2 At least one of the groups is a phenyl group or a six-membered heteroaryl group, and the groups are substituted twice with a trifluoromethyl group at the meta position of the substituted sulfoxide moiety.

[0050] According to one embodiment, the anion in the compound of formula (1) is selected from anions A-1 to A-54:

[0051]

[0052]

[0053]

[0054] According to one embodiment of the present invention, the at least one semiconductor layer comprises a compound of formula (1a),

[0055]

[0056] in

[0057] B 3 and B 4 independently selected from substituted or unsubstituted C3 alkyl,

[0058] Among them B 3 and B 4 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN;

[0059] where R 1 C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy;

[0060] Among them B 3 and / or B 4 At least one substituent is selected from C3 to C9 heteroaryl, C1 to C6 alkoxy, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN.

[0061] The negative charge in the compounds of formula (1a) may be partially or completely delocalized on the N(SO2)2 group and optionally also on B 3 and B 4 Delocalized on the group.

[0062] According to one embodiment of the present invention, the at least one semiconductor layer comprises a compound of formula (1b),

[0063]

[0064] in

[0065] B 5 selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl,

[0066] R 2 to R 6 independently selected from H, F, CN, halogen, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C12 heteroaryl,

[0067] Among them B 5 and / or R 2 to R 6 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 7 、COOR 7 , halogen, F or CN;

[0068] where R 7 C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy.

[0069] The negative charge in the compound of formula (1b) may be partially or completely delocalized on the N(SO2)2 group and optionally also on B 5 and delocalized on the phenyl group.

[0070] According to one embodiment, the anion in the compound of formula (1b) is selected from B-1 to B-24:

[0071]

[0072]

[0073] According to one embodiment of the present invention, the compound of formula (1) is selected from compounds A1 to A8:

[0074]

[0075] According to one embodiment of the present invention, the semiconductor layer and / or the compound of formula (1) is non-luminescent.

[0076] In the context of this specification, the term "substantially non-emissive" or "non-emissive" means that the compound or layer contributes less than 10%, preferably less than 5%, to the visible light emission spectrum from the device relative to the visible light emission spectrum. The visible light emission spectrum is the emission spectrum with a wavelength of about ≥380 nm to about ≤780 nm.

[0077] According to one embodiment of the invention, at least one semiconductor layer is arranged and / or provided adjacent to the anode.

[0078] According to one embodiment of the present invention, at least one semiconductor layer is in direct contact with the anode.

[0079] According to one embodiment of the present invention, at least one of the semiconductor layers according to the present invention is a hole injection layer.

[0080] If the at least one semiconductor layer according to the invention is a hole-injection layer and / or is arranged and / or provided adjacent to an anode, it is particularly preferred that this layer consists essentially of the compound of the formula (1).

[0081] In the context of the present specification, the term "essentially consisting of" especially means and / or includes a concentration ≥ 90% (vol / vol), more preferably ≥ 95% (vol / vol), most preferably ≥ 99% (vol / vol).

[0082] According to another aspect, the at least one semiconductor layer can have a layer thickness of at least approximately ≥0.5 nm to approximately ≤10 nm, preferably approximately ≥2 nm to approximately ≤8 nm, further preferably approximately ≥3 nm to approximately ≤5 nm.

[0083] According to one embodiment of the present invention, at least one of the inventive semiconductor layers further comprises a substantially covalent matrix compound.Preferably, the at least one semiconductor layer further comprising a substantially covalent matrix compound is arranged and / or provided adjacent to the anode.

[0084] Preferred examples of covalent matrix compounds are organic compounds consisting essentially of covalently bound C, H, O, N, S, which may optionally also contain covalently bound B, P, As, Se. Organometallic compounds containing covalently bound carbon-metals, metal complexes containing organic ligands, and metal salts of organic acids are other examples of organic compounds that can serve as substantially covalent organic matrix compounds.

[0085] In one embodiment, the substantially covalent host compound has no metal atoms and a majority of its backbone atoms are selected from C, O, S, N. Alternatively, the substantially covalent host compound has no metal atoms and a majority of its backbone atoms are selected from C and N.

[0086] In one embodiment, the HOMO energy level of the substantially covalent host compound may be more negative than the HOMO energy level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetramine (CAS 207739-72-8) when measured under the same conditions.

[0087] In one embodiment, the calculated HOMO energy level of the substantially covalent host compound may be more negative than -4.27 eV, preferably more negative than -4.3 eV, or more negative than -4.5 eV, or more negative than -4.6 eV, or more negative than -4.65 eV.

[0088] According to another aspect of the invention, the semiconductor layer further comprises a substantially covalent matrix compound having an oxidation potential, when measured by cyclic voltammetry in dichloromethane relative to Fc / Fc+, more positive than -0.2 V and more negative than 1.22 V, preferably more positive than -0.18 V and more negative than 1.12 V. Under these conditions, the oxidation potential of spiro-MeO-TAD (CAS 207739-72-8) is -0.07 V.

[0089] In one embodiment, the HOMO energy level of the substantially covalent host compound may be more negative than the HOMO energy level of N2,N2,N2',N2',N7,N7,N7',N7'-octa(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2',7,7'-tetramine (CAS 207739-72-8) and more positive than the HOMO energy level of N4,N4"'-di(naphthalen-1-yl)-N4,N4"'-diphenyl-[1,1':4',1":4",1"'-quaterphenyl]-4,4"'-diamine when measured under the same conditions.

[0090] In one embodiment of the present invention, the substantially covalent matrix compound may be free of alkoxy groups.

[0091] In one embodiment, the calculated HOMO energy level of the substantially covalent host compound may be selected to be within the range of <-4.27 eV and >-4.84 eV, or within the range of <-4.3 eV and >-4.84 eV, or within the range of <-4.5 eV and >-4.84 eV, or within the range of <-4.5 eV and >-4.84 eV, or within the range of <-4.6 eV and >-4.84 eV.

[0092] In one embodiment, the calculated HOMO energy level of the substantially covalent host compound may be selected to be in the range of <-4.27 eV and >-4.8 eV, or in the range of <-4.3 eV and >-4.8 eV, or in the range of <-4.5 eV and >-4.8 eV, or in the range of <-4.5 eV and >-4.8 eV, or in the range of <-4.6 eV and >-4.8 eV, or in the range of <-4.65 eV and >-4.8 eV.

[0093] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, or a diarylamine moiety, or a triarylamine moiety.

[0094] According to another aspect of the present invention, the at least one semiconductor layer further comprises a compound of formula (2):

[0095]

[0096] in:

[0097] L 1 To L 3 independently selected from a single bond, a phenylene group and a naphthalene group, preferably a phenylene group;

[0098] Ar 1 and Ar 2 independently selected from substituted or unsubstituted C6 to C 20 Aryl or substituted or unsubstituted C3 to C 20 heteroaromatic subunits;

[0099] C 1 selected from H, having 1 to 20 carbon atoms and optionally substituted by one or more R 2 Alkyl groups substituted with groups, or Ar 1 ;

[0100] in

[0101] R 2 is the same or different at each occurrence and is selected from: H, D, F, C(-O)R 2 ,CN,Si(R 3 )3,P(-O)(R 3 )2, OR 3 , S(-O)R 3 , S(-O)2R 3, straight-chain alkyl or alkoxy groups having 1 to 20 carbon atoms, branched or cyclic alkyl or alkoxy groups having 3 to 20 carbon atoms, alkenyl or alkynyl groups having 2 to 20 carbon atoms, aromatic ring systems having 6 to 40 aromatic ring atoms, and heteroaromatic ring systems having 5 to 40 aromatic ring atoms; wherein two or more R 1 The radicals are optionally linked to one another and may form a ring; wherein the alkyl, alkoxy, alkenyl and alkynyl radicals mentioned and the aromatic and heteroaromatic ring systems mentioned may each be substituted by one or more R 3 and wherein one or more CH2 groups in the alkyl, alkoxy, alkenyl and alkynyl groups mentioned are optionally replaced by -R 3 C-CR 3 -、-C=C-、Si(R 3 )2. CO, C-NR 3 、-C(-O)O-、-C(-O)NR 3 -、P(-O)(R 3 ), -O-, -S-, SO or SO2;

[0102] -Ar 1 and Ar 2 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN; and

[0103] -R 3 The substituents are independently selected from C1 to C6 alkyl, C6 to C 20 Aryl and C5 to C 20 heteroaryl, halogen, F or CN.

[0104] According to another aspect of the present invention, the at least one semiconductor layer further comprises a compound of formula (2a):

[0105]

[0106] in:

[0107] Ar 7 and Ar 8 independently selected from substituted or unsubstituted C6 to C 20Arylene, or substituted or unsubstituted C3 to C 20 heteroaromatic subunits;

[0108] Ar 3 and Ar 4 independently selected from substituted or unsubstituted C6 to C 20 Aryl, or substituted or unsubstituted C3 to C 20 heteroaromatic subunits;

[0109] Ar 5 and Ar 6 independently selected from substituted or unsubstituted C6 to C 20 Aryl, or C5 to C 40 heteroaryl;

[0110] R 4 is a single bond, unsubstituted or substituted C1 to C6 alkyl or phenylene;

[0111] q = 0, 1, or 2;

[0112] r = 0 or 1;

[0113] in

[0114] -Ar 3 to Ar 8 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN; and

[0115] -R 4 The substituents are independently selected from C1 to C6 alkyl, C6 to C 20 Aryl and C5 to C 20 heteroaryl, halogen, F or CN.

[0116] According to a preferred aspect, the at least semiconducting layer further comprises a compound of formula (2b):

[0117]

[0118] in:

[0119] Ar 9 and Ar 10 independently selected from substituted or unsubstituted C6 to C20 aryl;

[0120] Ar 11 and Ar 12 independently selected from substituted or unsubstituted C6 to C 20 aromatic subunits;

[0121] Ar 13 and Ar 14 independently selected from substituted or unsubstituted C6 to C 20 Aryl, or C5 to C 40 heteroaryl;

[0122] R 5 is a single chemical bond, unsubstituted or substituted C1 to C6 alkyl, and unsubstituted or substituted C1 to C5 heteroalkyl;

[0123] q = 0, 1, or 2;

[0124] r = 0 or 1;

[0125] in

[0126] -Ar 9 to Ar 14 The substituents are independently selected from C1 to C 20 Alkyl, C1 to C 20 heteroalkyl, or halide; and

[0127] -R 5 The substituents are independently selected from C1 to C6 alkyl, C1 to C5 heteroalkyl, C6 to C 20 Aryl and C5 to C 20 Heteroaryl.

[0128] According to another preferred aspect, the semiconductor layer of the present invention may further comprise a compound of formula (2a), wherein Ar 11 and Ar 12 It is Ph; Ar 9 、Ar 10 、Ar 13 and Ar 14 is selected from phenyl, tolyl, xylyl, mesityl, biphenyl, 1-naphthyl, 2-naphthyl, 2-(9,9-dialkyl-fluorenyl), 2-(9-alkyl-9'-aryl-fluorenyl) and 2-(9,9-diaryl-fluorenyl); R 5 = single bond; r=1 and q=1.

[0129] According to another preferred aspect, the semiconductor layer of the present invention may further comprise a compound of formula (2a), wherein Ar 11 and Ar 12 are independently selected from phenyl and biphenyl; Ar 9 、Ar10 、Ar 13 and Ar 14 is selected from phenyl, tolyl, xylyl, mesityl, biphenyl, 1-naphthyl, 2-naphthyl, 2-(9,9-dialkyl-fluorenyl), 2-(9-alkyl-9'-aryl-fluorenyl) and 2-(9,9-diaryl-fluorenyl); R 5 = single bond; r=1 and q=1.

[0130] According to another preferred aspect, the semiconductor layer of the present invention may further comprise a compound of formula (2a), wherein Ar 11 and Ar 12 is phenyl; Ar 9 、Ar 10 、Ar 13 and Ar 14 is selected from phenyl, tolyl, xylyl, mesityl, biphenyl, 1-naphthyl, 2-naphthyl, 2-(9,9-dialkyl-fluorenyl), 2-(9-alkyl-9'-aryl-fluorenyl) and 2-(9,9-diaryl-fluorenyl); R 5 =9,9'-fluorenyl; r=1 and q=1.

[0131] According to another preferred aspect, the semiconductor layer of the present invention may further comprise a compound of formula (2a), wherein Ar 11 is phenyl; Ar 9 、Ar 10 、Ar 13 and Ar 14 is selected from phenyl, tolyl, xylyl, mesityl, biphenyl, 1-naphthyl, 2-naphthyl, 2-(9,9-dialkyl-fluorenyl), 2-(9-alkyl-9'-aryl-fluorenyl) and 2-(9,9-diaryl-fluorenyl); R 5 = single bond; r = 0 and q = 1. Ar 11 The substituents on the group are selected from phenyl, biphenyl, 2-(9,9-dialkyl-fluorenyl), 2-(9-alkyl-9'-aryl-fluorenyl) and 2-(9,9-diaryl-fluorenyl).

[0132] According to another preferred aspect, the semiconductor layer of the present invention may further comprise a compound of formula (2a), wherein N, Ar 9 and Ar 11 Forming a carbazole ring; Ar 12 is phenyl or biphenyl; Ar 10 、Ar 13 and Ar 14is selected from phenyl, tolyl, xylyl, mesityl, biphenyl, 1-naphthyl, 2-naphthyl, 2-(9,9-dialkyl-fluorenyl), 2-(9-alkyl-9'-aryl-fluorenyl) and 2-(9,9-diaryl-fluorenyl); R 5 = single bond; r=1 and q=1.

[0133] Preferably, in formula (2a), q can be selected from 1 or 2.

[0134] The compound of formula (2), (2a) or (2b) may have a molecular weight suitable for thermal vacuum deposition. The molecular weight of the compound of formula (2), (2a) or (2b) that can be preferably used as a substantially covalent matrix compound can be about ≥243 g / mol and about ≤2000 g / mol, more preferably about ≥412 g / mol and about ≤1800 g / mol, and even more preferably about ≥488 g / mol and about ≤1500 g / mol.

[0135] According to a more preferred embodiment, Ar of formula (2) 1 and Ar 2 The phenylene group may be independently selected from a phenylene group, a biphenylene group, a naphthalene group, an anthracene group, a carbazole group or a fluorene group, and is preferably selected from a phenylene group or a biphenylene group.

[0136] According to a more preferred embodiment, Ar of formula (2a) or (2b) x The group may be independently selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl, 9,9'-spirobi[fluorenyl]-yl, naphthyl, anthracenyl, phenanthrenyl, thienyl, fluorenyl, or carbazolyl.

[0137] More preferably, Ar of formula (2a) or (2b) x The group may be independently selected from phenyl, biphenyl, fluorenyl, naphthyl, thienyl, fluorenyl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl, 9,9'-spirobi[fluorenyl]-yl, or carbazolyl.

[0138] At least two Ar in formula (2a) or (2b) x Can form a ring structure, such as Ar 3 and Ar 4 ; or Ar 3 and Ar 7 ; or Ar 9 and Ar 10 ; or Ar 9 and Ar 11 Whenever possible, the cyclic structure may be carbazole, phenazoline or phenazone. Oxazine ring.

[0139] According to another preferred embodiment, the compound has formula (2a), wherein:

[0140] Ar 7 and Ar 8 independently selected from phenylene, biphenylene, naphthalene, anthracene, carbazole and fluorene groups, preferably selected from phenylene and biphenylene groups;

[0141] Ar 3 to Ar 6 Independently selected from phenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl, 9,9'-spirobi[fluorenyl]-yl, naphthyl, anthracenyl, phenanthrenyl, thienyl, 9-carbazolyl; preferably

[0142] Ar 3 to Ar 6 Independently selected from phenyl, biphenyl, fluorenyl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl, 9,9'-spirobi[fluorenyl]-yl, naphthyl, thienyl, carbazolyl.

[0143] More preferably, Ar of formula (2a) 3 to Ar 8 At least one of them may be unsubstituted, more preferably Ar of formula (2a) 3 to Ar 8 At least two of may be unsubstituted.

[0144] According to another preferred embodiment, the compound having formula (2a):

[0145] -Ar 3 and Ar 4 and / or Ar 5 and Ar 6 Connect to form carbazole, phenazoline or phen Oxazine ring.

[0146] Not all Ar 1 to Ar 8 Compounds of the formula (2), (2a) or (2b) which are all substituted are particularly suitable for vacuum thermal deposition.

[0147] Preferably, the at least one semiconductor layer further comprises a compound of formula (2a), wherein Ar 3 to Ar 6 The substituents on 12 Alkyl, C1 to C 12 The alkoxy group or halide group is preferably selected from C1 to C8 alkyl groups or C1 to C8 heteroalkyl groups, and more preferably selected from C1 to C5 alkyl groups or C1 to C5 heteroalkyl groups.

[0148] Preferably, the at least one semiconductor layer further comprises a compound of formula (2a), wherein Ar 3 to Ar 6 The substituents on 12 The alkyl group or the halide is preferably selected from C1 to C8 alkyl groups or fluorides, and more preferably selected from C1 to C5 alkyl groups or fluorides.

[0149] According to a more preferred embodiment, the substantially covalent matrix compound has formulae (T-1) to (T-6) as shown in Table 1.

[0150] Table 1

[0151]

[0152]

[0153] According to another aspect, the at least one semiconductor layer further comprises a substantially covalent matrix compound and may comprise:

[0154] - at least about ≥0.1 wt% to about ≤50 wt%, preferably about ≥1 wt% to about ≤25 wt%, more preferably about ≥2 wt% to about ≤15 wt% of a compound of formula (1), and

[0155] - at least about ≥50 wt. % to about ≤99 wt. %, preferably about ≥75 wt. % to about ≤99 wt. %, more preferably about ≥85 wt. % to about ≤98 wt. % of a compound of formula (2), (2a) or (2b); preferably, the wt. % of the compound of formula (2), (2a) or (2b) is higher than the wt. % of the compound of formula (1); wherein the wt. % of the component is based on the total weight of the semiconductor layer.

[0156] According to one embodiment of the present invention, the at least one semiconductor layer also contains a substantially covalent matrix compound and may contain ≥1 and ≤30 mol% of the compound of formula (1) and ≤99 and ≥70 mol% of the substantially covalent matrix compound; or ≥5 and ≤20 mol% of the compound of formula (1) and ≤95 and ≥80 mol% of the substantially covalent matrix compound.

[0157] According to one embodiment of the present invention, the electronic organic device is an electroluminescent device, preferably an organic light emitting diode.

[0158] The present invention also relates to a display device comprising the organic electronic device of the present invention.

[0159] The present invention also relates to a compound of formula (1a),

[0160]

[0161] in

[0162] B 3 and B 4 independently selected from substituted or unsubstituted C3 alkyl,

[0163] Among them B 3 and B 4 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN;

[0164] where R 1 C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy;

[0165] Among them B 3 and / or B 4 At least one substituent is selected from C3 to C9 heteroaryl, C1 to C6 alkoxy, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN.

[0166] The negative charge in the compounds of formula (1a) may be partially or completely delocalized on the N(SO2)2 group and optionally also on B 3 and B 4 Delocalized on the group.

[0167] Any explanations of formula (1) as described above apply mutatis mutandis in the context of organic electronic devices.

[0168] The present invention also relates to a compound of formula (1b),

[0169]

[0170] in

[0171] B 5 selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl,

[0172] R 2 to R 6 independently selected from H, F, CN, halogen, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl,

[0173] Among them B 5 and / or R 2 to R 6 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 7 、COOR 7 , halogen, F or CN;

[0174] where R 7 C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy.

[0175] The negative charge in the compound of formula (1b) may be partially or completely delocalized on the N(SO2)2 group and optionally also on B 5 and delocalized on the phenyl group.

[0176] Any explanations of formula (1) as described above apply mutatis mutandis in the context of organic electronic devices.

[0177] Other layers

[0178] According to the present invention, the organic electronic device may further include other layers in addition to the layers mentioned above. Exemplary embodiments of the various layers are described below:

[0179] base

[0180] The substrate can be any substrate commonly used in the manufacture of electronic devices, such as organic light-emitting diodes. If light is to be emitted through the substrate, the substrate should be a transparent or translucent material, such as a glass substrate or a transparent plastic substrate. If light is to be emitted through the top surface, the substrate can be a transparent or opaque material, such as a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate.

[0181] Anode electrode

[0182] The anode electrode can be formed by depositing or sputtering the material for forming the anode electrode. The material for forming the anode electrode can be a high work function material to promote hole injection. The anode material can also be selected from a low work function material (i.e., aluminum). The anode electrode can be a transparent or reflective electrode. Transparent conductive oxides, such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO) and zinc oxide (ZnO), can be used to form the anode electrode. Metals, typically silver (Ag), gold (Au) or metal alloys can also be used to form the anode electrode.

[0183] hole injection layer

[0184] A hole injection layer (HIL) can be formed on the anode electrode by vacuum deposition, spin coating, printing, casting, slot die coating, Langmuir-Blodgett (LB) deposition, etc. When vacuum deposition is used to form the HIL, the deposition conditions may vary depending on the compound used to form the HIL and the desired HIL structure and thermal properties. However, in general, the vacuum deposition conditions may include a deposition temperature of 100° C. to 500° C., a pressure of 10° C. to 500° C., and a pressure of 10° C. to 500° C. -8 to 10 -3 Torr (1 Torr equals 133.322 Pa) and a deposition rate of 0.1 to 10 nm / second.

[0185] When the HIL is formed by spin coating or printing, the coating conditions may vary depending on the compound used to form the HIL and the desired structure and thermal properties of the HIL. For example, the coating conditions may include a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80°C to about 200°C. After coating, the heat treatment is performed to remove the solvent.

[0186] The HIL can be formed of any compound that is commonly used to form a HIL. Examples of the compound that can be used to form the HIL 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-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), and polyaniline / poly(4-styrenesulfonate) (PANI / PSS).

[0187] The HIL may include or consist of a p-type dopant, and the p-type dopant may be selected from tetrafluoro-tetracyanoquinodimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene)dimalononitrile, or 2,2',2"-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile), but is not limited thereto. The HIL may be selected from a hole-transporting host compound doped with a p-type dopant. Typical examples of known doped hole-transporting materials include copper phthalocyanine (CuPc) having a HOMO energy level of approximately -5.2 eV, Tetrafluoro-tetracyanoquinodimethane (F4TCNQ) doped with a LUMO energy level of approximately -5.2 eV; zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO = -5.2 eV); α-NPD (N,N'-bis(naphthalene-1-yl)-N,N'-bis(phenyl)-benzidine) doped with F4TCNQ; and α-NPD doped with 2,2'-(perfluoronaphthalene-2,6-diylidene) dimalononitrile. The p-type dopant concentration can be selected from 1% to 20% by weight, more preferably from 3% to 10% by weight.

[0188] The thickness of the HIL may be within a range of about 1 nm to about 100 nm, for example, about 1 nm to about 25 nm. When the thickness of the HIL is within this range, the HIL may have excellent hole injection characteristics without substantially degrading driving voltage.

[0189] hole transport layer

[0190] A hole transport layer (HIL) can be formed on the HIL by vacuum deposition, spin coating, slot die coating, printing, casting, Langmuir-Blodgett (LB) deposition, or the like. When the HTL is formed by vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for forming the HIL. However, the vacuum or solution deposition conditions may vary depending on the compound used to form the HTL.

[0191] In one embodiment of the present invention, the organic electronic device further comprises a hole transport layer, wherein the hole transport layer is arranged between the semiconductor layer and the at least one photoactive layer.

[0192] In one embodiment, the hole transport layer comprises a substantially covalent host compound.

[0193] In one embodiment of the present invention, the at least one semiconductor layer and the hole transport layer comprise an essentially covalent matrix compound, wherein the choice of the essentially covalent matrix compound is identical in both layers.

[0194] In one embodiment, the hole transport layer comprises a compound of formula (2), (2a), or (2b).

[0195] In one embodiment of the present invention, the at least one semiconductor layer and the hole transport layer comprise a compound of formula (2), (2a) or (2b).

[0196] In one embodiment of the present invention, the at least one semiconductor layer comprises a compound of formula (1) and a compound of formula (2), (2a) or (2b) and the hole transport layer comprises a compound of formula (2), (2a) or (2b), wherein the selection of the compound of formula (2), (2a) or (2b) is the same.

[0197] The thickness of the HTL may be in the range of about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, further preferably about 20 nm to about 190 nm, further preferably about 40 nm to about 180 nm, further preferably about 60 nm to about 170 nm, further preferably about 80 nm to about 160 nm, further preferably about 100 nm to about 160 nm, further preferably about 120 nm to about 140 nm.

[0198] When the thickness of the HTL is within this range, the HTL may have excellent hole transport characteristics without substantial deterioration in driving voltage.

[0199] electron blocking layer

[0200] The function of the electron blocking layer (EBL) is to prevent electrons from being transferred from the light-emitting layer to the hole transport layer, thereby confining the electrons to the light-emitting layer. This can improve efficiency, operating voltage, and / or lifetime. Typically, the electron blocking layer comprises a triarylamine compound. The LUMO energy level of the triarylamine compound can be closer to the vacuum level than the LUMO energy level of the hole transport layer. Compared to the HOMO energy level of the hole transport layer, the electron blocking layer can have a HOMO energy level that is further away from the vacuum level. The thickness of the electron blocking layer can be selected between 2 and 20 nm.

[0201] If the triplet energy level of the electron blocking layer is high, it may also be referred to as a triplet control layer.

[0202] If a phosphorescent green or blue emitting layer is used, the function of the triplet control layer is to reduce triplet quenching. This allows for a higher luminous efficiency of the phosphorescent emitting layer. The triplet control layer is selected from triarylamine compounds having a triplet energy level higher than that of the phosphorescent emitter in the adjacent emitting layer. Suitable compounds for triplet control layers, in particular triarylamine compounds, are described in EP 2 722 908 A1.

[0203] Photoactive layer (PAL)

[0204] The photoactive layer converts electrical current into photons or converts photons into electrical current.

[0205] The PAL can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, or the like. When the PAL is formed by vacuum deposition or spin coating, the deposition and coating conditions can be similar to those used to form the HIL. However, the deposition and coating conditions may vary depending on the compound used to form the PAL.

[0206] It may be provided that the photoactive layer does not contain the compound of the formula (1).

[0207] The photoactive layer can be a light emitting layer or a light absorbing layer.

[0208] Emitting Layer (EML)

[0209] The EML can be formed on the HTL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, or the like. When the EML is formed by vacuum deposition or spin coating, the deposition and coating conditions can be similar to those for forming the HIL. However, the deposition and coating conditions may vary depending on the compound used to form the EML.

[0210] It may be provided that the light-emitting layer does not contain the compound of the formula (1).

[0211] The light-emitting layer (EML) can be formed from a combination of a host and an emitter dopant. Examples of hosts include Alq3,4,4'-N,N'-dicarbazole biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4"-tris(carbazol-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazol-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distyrylarene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazole)zinc (Zn(BTZ)2).

[0212] The emitter dopant may be a phosphorescent or fluorescent emitter. Phosphorescent emitters and emitters that emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The emitter may be a small molecule or a polymer.

[0213] Examples of red emitter dopants are PtOEP, Ir(piq)3 and Btp2lr(acac), but are not limited thereto. These compounds are phosphorescent emitters, however, fluorescent red emitter dopants may also be used.

[0214] Examples of phosphorescent green emitter dopants are Ir(ppy)3 (ppy=phenylpyridine), Ir(ppy)2(acac), Ir(mpyp)3.

[0215] Examples of phosphorescent blue emitter dopants are F2Irpic, (F2ppy)2Ir(tmd), Ir(dfppz)3 and terfluorene. Examples of fluorescent blue emitter dopants are 4,4′-bis(4-diphenylaminophenyl)biphenyl (DPAVBi), 2,5,8,11-tetra-tert-butylperylene (TBPe).

[0216] The amount of the luminophore dopant can be in a range of about 0.01 to about 50 parts by weight based on 100 parts by weight of the host. Alternatively, the luminescent layer can be composed of a luminescent polymer. The thickness of the EML can be in a range 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 have excellent luminescence without substantially compromising the driving voltage.

[0217] Hole blocking layer (HBL)

[0218] A hole blocking layer (HBL) can be formed on the EML to prevent holes from diffusing into the ETL by vacuum deposition, spin coating, slot die coating, printing, casting, LB deposition, etc. When the EML contains a phosphorescent dopant, the HBL can also have a triplet exciton blocking function.

[0219] HBL may also be called auxiliary ETL or a-ETL.

[0220] When the HBL is formed by vacuum deposition or spin coating, the deposition and coating conditions may be similar to those for forming the HIL. However, the deposition and coating conditions may vary depending on the compound used to form the HBL. Any compound commonly used to form the HBL may be used. Examples of the compound used to form the HBL include Oxadiazole derivatives, triazole derivatives, phenanthroline derivatives and triazine derivatives.

[0221] The thickness of the HBL may be within a range of about 5 nm to about 100 nm, for example, about 10 nm to about 30 nm. When the thickness of the HBL is within this range, the HBL may have excellent hole-blocking properties without substantially compromising driving voltage.

[0222] Electron Transport Layer (ETL)

[0223] The organic electronic device of the present invention may further include an electron transport layer (ETL).

[0224] According to another embodiment of the present invention, the electron transport layer may further comprise an azine compound, preferably a triazine compound.

[0225] In one embodiment, the electron transport layer may further comprise a dopant selected from alkali metal organic complexes, preferably LiQ.

[0226] The thickness of the ETL may be within a range of about 15 nm to about 50 nm, for example, within a range of about 20 nm to about 40 nm. When the thickness of the ETL is within this range, the ETL may have satisfactory electron injection properties without substantially degrading driving voltage.

[0227] 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 azine compound. Preferably, the azine compound is a triazine compound.

[0228] Electron injection layer (EIL)

[0229] An optional EIL, which can facilitate electron injection from the cathode, can be formed on the ETL, preferably directly on the electron transport layer. Examples of materials for forming the EIL include 8-hydroxyquinoline lithium (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, and Mg, which are known in the art. The deposition and coating conditions for forming the EIL are similar to those for forming the HIL. However, the deposition and coating conditions may vary depending on the material used to form the EIL.

[0230] The thickness of the EIL may be within a range of about 0.1 nm to about 10 nm, for example, about 0.5 nm to about 9 nm. When the thickness of the EIL is within this range, the EIL may have satisfactory electron injection properties without substantially degrading driving voltage.

[0231] cathode electrode

[0232] A cathode electrode is formed on the ETL or optional EIL. The cathode electrode may be formed of a metal, an alloy, a conductive compound, or a mixture thereof. The cathode electrode may have a low work function. For example, the cathode electrode may be formed of lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode may be formed of a transparent conductive oxide such as ITO or IZO.

[0233] The thickness of the cathode electrode may be in the range of about 5 nm to about 1000 nm, for example, in the range of about 10 nm to about 100 nm. When the thickness of the cathode electrode is in the range of about 5 nm to about 50 nm, the cathode electrode may be transparent or translucent even if formed of a metal or a metal alloy.

[0234] It is understood that the cathode electrode is not part of the electron injection layer or the electron transport layer.

[0235] Organic light-emitting diodes (OLEDs)

[0236] The organic electronic device of the present invention may be an organic light-emitting device.

[0237] According to one aspect of the present invention, an organic light emitting diode (OLED) is provided, comprising: a substrate; an anode electrode formed on the substrate; a semiconductor layer comprising a compound of formula (1), a hole transport layer, a light emitting layer, an electron transport layer, and a cathode electrode.

[0238] According to another aspect of the present invention, an OLED is provided, comprising: a substrate; an anode electrode formed on the substrate; a semiconductor layer comprising a compound of formula (1), a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and a cathode electrode.

[0239] According to another aspect of the present invention, an OLED is provided, comprising: a substrate; an anode electrode formed on the substrate; a semiconductor layer comprising a compound of formula (1), 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 electrode.

[0240] According to various embodiments of the present invention, OLED layers may be provided arranged between the above-mentioned layers, on the substrate, or on the top electrode.

[0241] According to one aspect, the OLED may include the following layer structure: a substrate is arranged adjacent to an anode electrode, the anode electrode is arranged adjacent to a first hole injection layer, the first hole injection layer is arranged adjacent to a first hole transport layer, the first hole transport layer is arranged adjacent to a first electron blocking layer, the first electron blocking layer is arranged adjacent to a first light-emitting layer, the first light-emitting layer is arranged adjacent to a first electron transport layer, the first electron transport layer is arranged adjacent to an n-type charge generation layer, the n-type charge generation layer is arranged adjacent to a hole generation layer, the hole generation layer is arranged adjacent to a second hole transport layer, the second hole transport layer is arranged adjacent to a second electron blocking layer, the second electron blocking layer is arranged adjacent to a second light-emitting layer, and an optional electron transport layer and / or an optional injection layer are arranged between the second light-emitting layer and the cathode electrode.

[0242] The semiconductor layer of the present invention may be a first hole injection layer and a p-type charge generation layer.

[0243] For example, Figure 2 The OLED can be formed by the following method, wherein an anode (120), a hole injection layer (130), a hole transport layer (140), an electron blocking layer (145), a light emitting layer (150), a hole blocking layer (155), an electron transport layer (160), an electron injection layer (180) and a cathode electrode (190) are successively formed on a substrate (110).

[0244] Organic electronic devices

[0245] The organic electronic device of the present invention may be a light-emitting device or a photovoltaic cell, and is preferably a light-emitting device.

[0246] According to another aspect of the present invention, there is provided a method for manufacturing an organic electronic device, the method using:

[0247] - at least one deposition source, preferably two deposition sources, more preferably at least three deposition sources.

[0248] Suitable deposition methods include:

[0249] -Deposition by vacuum thermal evaporation;

[0250] - deposition by solution processing, preferably selected from spin coating, printing, casting; and / or

[0251] -Slot die coating.

[0252] According to various embodiments of the present invention, there is provided a method using:

[0253] - a first deposition source to release the compound of formula (1) of the present invention, and

[0254] - a second deposition source to release said substantially covalent matrix compound;

[0255] The method comprises the steps of forming the semiconductor layer; wherein for an organic light emitting diode (OLED):

[0256] - forming the semiconductor layer by releasing the compound of formula (1) according to the invention from a first deposition source and releasing the substantially covalent matrix compound from a second deposition source.

[0257] According to various embodiments of the present invention, the method may further include forming at least one layer selected from the group consisting of forming a hole transport layer or a hole blocking layer on the anode electrode, and forming a light emitting layer between the anode electrode and the first electron transport layer.

[0258] According to various embodiments of the present invention, the method may further include the step of forming an organic light emitting diode (OLED), wherein

[0259] - forming an anode electrode on the substrate,

[0260] - forming a semiconductor layer comprising a compound of formula (1) on the anode electrode,

[0261] - forming a hole transport layer on the semiconductor layer comprising the compound of formula (1),

[0262] - forming a light-emitting layer on the hole transport layer,

[0263] - forming an electron transport layer on the light-emitting layer, and optionally forming a hole blocking layer on the light-emitting layer,

[0264] - and finally forming a cathode electrode,

[0265] - Optionally, a hole blocking layer is sequentially formed between the first anode electrode and the light-emitting layer,

[0266] - Optionally, an electron injection layer is formed between the electron transport layer and the cathode electrode.

[0267] According to various embodiments, the OLED may have the following layer structure, wherein the layers have the following order:

[0268] an anode, a semiconductor layer comprising a compound of formula (1), 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.

[0269] According to another aspect of the present invention, an electronic device is provided, comprising at least one organic light-emitting device according to any embodiment described throughout this application. Preferably, the electronic device comprises an organic light-emitting diode according to one of the embodiments described throughout this application. More preferably, the electronic device is a display device.

[0270] Hereinafter, the embodiments will be described in more detail with reference to examples. However, the present disclosure is not limited to the following examples. Reference will now be made in detail to exemplary aspects. BRIEF DESCRIPTION OF THE DRAWINGS

[0271] The aforementioned components in the described embodiments, as well as the components claimed for protection and the components used in the present invention, do not have any special exceptions in terms of their size, shape, material selection and technical concept, so the selection criteria known in the relevant field can be applied without restriction.

[0272] Further details, features, and advantages of the objects of the present invention are disclosed in the dependent claims and in the following description of the various drawings, which show, by way of example, preferred embodiments of the present invention. However, no embodiment necessarily represents the full scope of the invention, and reference should be made to the claims and this document for interpretation of the scope of the invention. It should be understood that both the foregoing general description and the following detailed description are merely exemplary and explanatory and are intended to provide further explanation of the invention as claimed.

[0273] Figure 1 is a schematic cross-sectional view of an organic light emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0274] Figure 2 is a schematic cross-sectional view of an organic light emitting diode (OLED) according to an exemplary embodiment of the present invention;

[0275] Figure 3 is a schematic cross-sectional view of an organic light emitting diode (OLED) according to an exemplary embodiment of the present invention.

[0276] Figure 1 1 is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. OLED 100 includes a substrate 110. An anode 120 is provided on substrate 110. A semiconductor layer including a compound of formula (1) is provided on anode 120, and a hole transport layer 140 is provided thereon. A light-emitting layer 150 and a cathode electrode 190 are provided on hole transport layer 140, in this order.

[0277] Figure 21 is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. OLED 100 includes a substrate 110, a first electrode 120, a semiconductor layer 130 including a compound of formula (1), a hole transport layer (HTL) 140, an emission layer (EML) 150, and an electron transport layer (ETL) 161. Electron transport layer (ETL) 161 is formed directly on EML 150. A cathode electrode 190 is provided on electron transport layer (ETL) 161.

[0278] Optionally, a stack of electron transport layers (ETL) may be used instead of the single electron transport layer 161 .

[0279] Figure 3 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. Figure 3 and Figure 2 The difference is that Figure 3 The OLED 100 includes a hole blocking layer (HBL) 155 and an electron injection layer (EIL) 180 .

[0280] Reference Figure 3 The OLED 100 includes a substrate 110, an anode electrode 120, a semiconductor layer 130 containing a compound of formula (1), a hole transport layer (HTL) 140, an emission layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 161, an electron injection layer (EIL) 180, and a cathode electrode 190. The layers are arranged exactly in the order described above.

[0281] In the above description, the method of manufacturing the OLED of the present invention starts with forming an anode electrode 120 on a substrate 110, and forming a hole injection layer 130, a hole transport layer 140, a light-emitting layer 150, an optional hole blocking layer 155, an optional at least one electron transport layer 161, an optional at least one electron injection layer 180, and a cathode electrode 190 on the anode electrode 120, exactly in this order or exactly in the reverse order.

[0282] Although Figure 1 、 Figure 2 and Figure 3 Although not shown in FIG. 1 , a sealing layer may be further formed on the cathode electrode 190 to seal the OLED 100. In addition, various other modifications may be applied thereto.

[0283] Hereinafter, one or more exemplary embodiments of the present invention will be described in detail with reference to the following examples. However, these examples are not intended to limit the purpose and scope of the one or more exemplary embodiments of the present invention. DETAILED DESCRIPTION

[0284] The present invention is further illustrated by the following examples, which are intended to be illustrative only and not limiting.

[0285] The preparation of several compounds of the present invention is shown below, using the following general procedures:

[0286] The sulfonamide ligands were synthesized by methods known in the literature.

[0287] The sulfonamide ligand is dissolved in MeOH (about 5ml / g) and 0.55eq AgCO is added. The reaction mixture is stirred at room temperature overnight. Excess silver carbonate is filtered out and washed with a small amount of methanol. The combined liquid phase is removed under reduced pressure and the solvent is removed. The remaining solid is dried in a high vacuum. The crude material is purified by decompression sublimation.

[0288] As comparative examples, the following compounds were used:

[0289]

[0290] Sublimation temperature

[0291] In a glove box under nitrogen, 0.5 to 5 g of compound was loaded into the evaporation source of a sublimator. The sublimator consisted of an inner glass tube consisting of a 3 cm diameter bulb placed in a 3.5 cm diameter glass tube. The sublimator was placed in a tubular oven (Creaphys DSU 05 / 2.1). The sublimator was evacuated by a diaphragm pump (Pfeiffer Vacuum MVP 055-3C) and a turbo pump (Pfeiffer Vacuum THM071 YP). A pressure gauge (Pfeiffer Vacuum PKR 251) was used to measure the pressure between the sublimator and the turbo pump. When the pressure dropped to 10 -5 The temperature is raised in increments of 10 to 30 K at 100 mbar until compound begins to deposit in the harvest zone of the sublimator. The temperature is further raised in increments of 10 to 30 K until a sublimation rate is reached at which the compound in the source is visibly depleted over a period of 30 minutes to 1 hour and a significant amount of compound accumulates in the harvest zone.

[0292] Sublimation temperature, also known as T subl , is the temperature inside the sublimator at which the compound is deposited in the harvest zone at an appreciable rate and is measured in degrees Celsius.

[0293] In the context of the present invention, the term "sublimation" may refer to the transfer from the solid to the gas phase or from the liquid to the gas phase.

[0294] Decomposition temperature

[0295] Decomposition temperature, also known as T dec , determined in degrees Celsius.

[0296] Decomposition temperature was measured by loading 9 to 11 mg of sample into a Mettler Toledo 100 μL uncovered aluminum pan under nitrogen in a Mettler Toledo TGA-DSC 1 machine. The following heating program was used: 25°C isothermal for 3 minutes; 25°C to 600°C at 10 K / min.

[0297] The decomposition temperature was determined based on the onset of decomposition in TGA.

[0298] Standard starting temperature

[0299] Standard starting temperature (T RO ) is determined by loading 100 mg of compound into a VTE source. As a VTE source, a point source of organic material such as supplied by Kurt J. Lesker Company (www.lesker.com) or CreaPhys GmbH (http: / / www.creaphys.com) can be used. -5 The VTE source was heated at a constant rate of 15 K / min under a pressure of 100 mbar, and the temperature inside the source was measured with a thermocouple. Compound evaporation was monitored using a QCM detector, which measures compound deposition on the detector's quartz crystal. The deposition rate on the quartz crystal was measured in angstroms / second. To determine the standard onset temperature, the deposition rate was plotted against the VTE source temperature. The standard onset was the temperature at which significant deposition occurred on the QCM detector. To ensure accurate results, the VTE source was heated and cooled three times, and only the results from the second and third runs were used to determine the standard onset temperature.

[0300] To achieve good control over the evaporation rate of organic compounds, the standard starting temperature may be in the range of 200 to 255°C. If the standard starting temperature is below 200°C, evaporation may be too rapid, making it difficult to control. If the standard starting temperature is above 255°C, the evaporation rate may be too slow, which may result in a low cycle time, and decomposition of organic compounds in the VTE source may occur due to prolonged exposure to high temperatures.

[0301] The standard onset temperature is an indirect measure of the volatility of a compound. The higher the standard onset temperature, the lower the volatility of the compound.

[0302] Reduction potential

[0303] The reduction potential was determined by cyclic voltammetry at room temperature using a potentiostat apparatus Metrohm PGSTAT30 and software Metrohm Autolab GPES. The redox potential given for a specific compound was measured as follows: in a dry 0.1M THF solution of the experimental substance degassed with argon, under an argon atmosphere, with a 0.1M tetrabutylammonium hexafluorophosphate supporting electrolyte between platinum working electrodes, and with an Ag / AgCl pseudo-standard electrode (Metrohm silver rod electrode) consisting of a silver wire covered with silver chloride and directly immersed in the solution being tested, at a scan rate of 100 mV / s. The first run was performed within the widest potential range set for the working electrode, and the range was then appropriately adjusted in subsequent runs. The last three runs were performed with the addition of ferrocene (at a concentration of 0.1M) as a standard. The average potential corresponding to the cathode and anode peaks of the compound under study was calculated after subtracting the potential for the standard Fc + The values ​​reported above were obtained by averaging the cathodic and anodic potentials observed for the α / Fc redox couple. All investigated compounds, as well as the reported comparative compounds, showed clear reversible electrochemical behavior.

[0304] Calculated HOMO and LUMO

[0305] HOMO and LUMO calculations were performed using the TURBOMOLE V6.5 program package (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometry of the molecular structure, as well as the HOMO and LUMO energy levels, were determined in the gas phase using the hybrid functional B3LYP with the 6-31G* basis set. If more than one conformation was feasible, the one with the lowest total energy was selected. HOMO and LUMO energy levels are reported in electron volts (eV).

[0306] General procedure for manufacturing OLEDs

[0307] For OLED, see Examples 7 to 11, Examples 14 to 15 and Comparative Examples 4 and 5 in Table 3. 2 A glass substrate (available from Corning Co.) was cut into a size of 50 mm×50 mm×0.7 mm, ultrasonically cleaned with isopropyl alcohol for 5 minutes, then ultrasonically cleaned with pure water for 5 minutes, and further cleaned with UV ozone for 30 minutes to prepare an anode.

[0308] Then, 92 mol% of biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine (CAS 1242056-42-3) and 8 mol% of the compound of formula (1) were vacuum deposited on the anode to form a HIL having a thickness of 10 nm. In Comparative Examples 4 and 5, the compounds shown in Table 3 were used instead of the compound of formula (1).

[0309] Then, biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine was vacuum-deposited on the HIL to form a first HTL with a thickness of 128 nm.

[0310] Then, N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1′:4′,1″-terphenyl]-4-amine (CAS 1198399-61-9) was vacuum deposited on the HTL to form an electron blocking layer (EBL) with a thickness of 5 nm.

[0311] Then, 97 vol% H09 (Sun Fine Chemicals, Korea) as an EML host and 3 vol% BD200 (Sun Fine Chemicals, Korea) as a fluorescent blue dopant were deposited on the EBL to form a first blue emission layer (EML) with a thickness of 20 nm.

[0312] Then, a hole blocking layer having a thickness of 5 nm was formed by depositing 2-(3′-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine on the light emitting layer.

[0313] Then, an electron transport layer having a thickness of 31 nm was formed on the hole blocking layer by depositing 4′-(4-(4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl)naphthalen-1-yl)-[1,1′-biphenyl]-4-carbonitrile and LiQ at a ratio of 50:50 volume %.

[0314] In 10 -7 0.01 to mbar Al was evaporated at a rate of 100 nm to form a cathode with a thickness of 100 nm.

[0315] A covering layer of biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-amine was formed on the cathode to a thickness of 75 nm.

[0316] The OLED stack is protected from environmental conditions by encapsulating the device with a glass slide, thereby forming a cavity that contains a getter material for further protection.

[0317] In order to evaluate the performance of the embodiments of the present invention compared to the prior art, the current efficiency was measured at 20°C. The current-voltage characteristics were determined by supplying a voltage in V and measuring the current in mA flowing through the device under test using a Keithley 2635 source measurement unit. The voltage applied to the device was varied in steps of 0.1 V over a range of 0 V to 10 V. Similarly, the current efficiency in cd / m² was measured at each voltage value using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)). 2 The luminance-voltage characteristics and CIE coordinates are determined by interpolating the luminance-voltage and current-voltage characteristics. 10 mA / cm 2 cd / A efficiency under .

[0318] The device life LT is under ambient conditions (20℃) and 30mA / cm 2 The measurements were made using a Keithley 2400 source meter and recorded in hours.

[0319] The luminance of the device is measured using a calibrated photodiode. The lifetime LT is defined as the time until the luminance of the device decreases to 97% of its initial value.

[0320] To determine the voltage stability over time, U(100h)-(1h) and U(100h-50h), a 30 mA / cm 2 The operating voltage was measured after 1 hour, 50 hours, and 100 hours, and the voltage stability for the 1 to 100 hour period and the 50 to 100 hour period was calculated.

[0321] Technical effects of the invention

[0322] To investigate the usefulness of the compounds of the present invention, preferred materials were tested for their thermal properties.

[0323] Since organic electronic materials are usually purified by sublimation, the large gap between the decomposition temperature and the sublimation temperature T dec -T subl This is very ideal. Thus, a high sublimation rate can be achieved.

[0324] Table 2: Properties of the compound of formula (1) and comparative examples 1 to 3

[0325]

[0326] Table 2 shows the temperatures at which thermal decomposition is observed (T dec ), the difference between decomposition and sublimation temperatures T dec -T subl As well as the yield after purification by sublimation. Obviously, the compounds of the present invention show a higher decomposition temperature and / or a much larger gap between the decomposition and sublimation temperatures.

[0327] Furthermore, for several devices comprising comparative compounds and compounds of the present invention, the change in operating voltage over time was determined for a period between 1 hour and 100 hours and a period between 50 and 100 hours.

[0328] A low or even decreasing operating voltage over time is highly desirable because power consumption does not increase over time. Low power consumption is important for long battery life, especially in mobile devices.

[0329] Table 3 shows the properties of organic electronic devices comprising the compound of formula (1) and Comparative Examples 4 and 5.

[0330] Table 3: Properties of organic electronic devices comprising the compound of Formula 1 and Comparative Examples 4 and 5

[0331]

[0332] Clearly, the device of the present invention shows much better performance than the comparative device.

[0333] The particular combination of elements and features in the above detailed embodiments is merely exemplary; it is expressly contemplated that these teachings may be exchanged and replaced with other teachings in this and the patents / applications incorporated by reference. As will be appreciated by those skilled in the art, variations, modifications and other implementations of the description herein are within the scope of the invention as claimed and can be envisaged by those skilled in the art without departing from the spirit and scope of the invention as claimed. Therefore, the foregoing description is intended to be illustrative only and not limiting. In the claims, the word "comprising" does not exclude other elements or steps, and the singular form "a" or "an" does not exclude plural referents. The fact that particular measures are listed in mutually different dependent claims does not indicate that a combination of these measures cannot be used to advantage. The scope of the invention is defined by the claims and their equivalents. In addition, the reference symbols used in the specification and claims do not limit the scope of the invention as claimed.

Claims

1. An organic electronic device comprising an anode, a cathode, at least one photoactive layer, and at least one semiconductor layer, wherein the at least one semiconductor layer is arranged between the anode and the at least one photoactive layer; and wherein the at least one semiconductor layer comprises a compound of formula (1): in B 1 selected from substituted or unsubstituted C3 to C 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, B 2 selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, Among them B 1 and B 2 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN; where R 1 C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy; Among them B 1 and / or B 2 At least one substituent is selected from C3 to C9 heteroaryl, C1 to C6 alkoxy, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN.

2. The organic electronic device according to claim 1, wherein B 1 and B 2 The substituents on the alkyl group are independently selected from: halogen, C1 to C3 perhalogenated alkyl or alkoxy, or -(O) l -C m H 2m -C n Hal 2n+1 , wherein l=0 or 1, m=1 or 2, and n=1 to 3, and Hal=halogen.

3. The organic electronic device according to claim 1, wherein B 1 and B 2 The substituents on the alkyl group are independently selected from: F, C1 to C3 perfluorinated alkyl or alkoxy, or -(O) l -C m H 2m -C n Hal 2n+1 , where l is 0, m is 1, and n is 1 or 2, and Hal is F.

4. The organic electronic device according to any one of claims 1 to 3, wherein B 1 and B 2 is a substituted alkyl group and the substituent of the alkyl group is fluorine, and the number (of fluorine substituents) n F and the number (of hydrogen) n H Follow the following equation: F >n H +2.

5. The organic electronic device according to any one of claims 1 to 3, wherein B 1 and B 2 At least one of the groups is selected from perfluorinated alkyl or aryl groups.

6. The organic electronic device according to any one of claims 1 to 3, wherein B 1 and B 2 At least one of the groups is a substituted C3 to C6 linear or cyclic alkyl group.

7. The organic electronic device according to any one of claims 1 to 3, wherein B 1 and B 2 At least one of the is an aryl or heteroaryl group, wherein the substituents of the aryl and / or heteroaryl moiety are selected from hydrogen, halogen, F, CN or trifluoromethyl.

8. The organic electronic device according to any one of claims 1 to 3, wherein B 1 and B 2 At least one of the is a phenyl group or a six-membered heteroaryl group, and the phenyl group or the six-membered heteroaryl group is substituted with at least one trifluoromethyl group at the ortho position or the meta position of the substituted sulfoxide moiety.

9. The organic electronic device according to any one of claims 1 to 3, wherein B 1 and B 2 At least one of the is a phenyl group or a six-membered heteroaryl group, and the phenyl group or the six-membered heteroaryl group is substituted twice with a trifluoromethyl group at the meta position of the substituted sulfoxide moiety.

10. The organic electronic device according to any one of claims 1 to 3, wherein the at least one semiconductor layer is non-luminescent. 11 . The organic electronic device according to claim 1 , wherein at least one of the semiconductor layers is a hole injection layer, and the hole injection layer is composed of the compound of formula (1). 12 . The organic electronic device according to claim 1 , wherein at least one of the at least one semiconductor layer further comprises a covalent matrix compound.

13. The organic electronic device according to any one of claims 1 to 3, wherein the organic electronic device is an electroluminescent device.

14. The organic electronic device according to any one of claims 1 to 3, wherein the organic electronic device is an organic light emitting diode. 15 . A display device comprising the organic electronic device according to claim 1 .

16. A compound of formula (1a): in B 3 and B 4 independently selected from substituted or unsubstituted C3 alkyl, Among them B 3 and B 4 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN; where R 1 C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy; Among them B 3 and / or B 4 At least one substituent is selected from C3 to C9 heteroaryl, C1 to C6 alkoxy, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkoxy, COR 1 、COOR 1 , halogen, F or CN.

17. A compound of formula (1b): in B 5 selected from substituted or unsubstituted C1 to C 12 Alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, R 2 to R 6 independently selected from H, F, CN, halogen, substituted or unsubstituted C1 to C6 alkyl, substituted or unsubstituted C6 to C 12 Aryl, substituted or unsubstituted C3 to C 12 heteroaryl, Among them B 5 and / or R 2 to R 6 The substituents are independently selected from D, C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy, COR 7 、COOR 7 , halogen, F or CN; where R 7 C6 aryl, C3 to C9 heteroaryl, C1 to C6 alkyl, C1 to C6 alkoxy, C3 to C6 branched alkyl, C3 to C6 cyclic alkyl, C3 to C6 branched alkoxy, C3 to C6 cyclic alkoxy, partially or fully fluorinated C1 to C 16 Alkyl, partially or fully fluorinated C1 to C 16 Alkoxy, partially or fully deuterated C1 to C6 alkyl, partially or fully deuterated C1 to C6 alkoxy.

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