Organic compound of formula (I) for use in organic electronic devices, organic electronic device containing compound of formula (I), and display device containing organic electronic device.

Abstract

The present invention relates to compounds of formula (I) and organic electronic devices comprising a semiconducting layer comprising a compound of formula (I).

Description

Detailed description of the invention

[0001] [Technical Field] The present invention relates to an organic compound of formula (I) for use in organic electronic devices, an organic electronic device containing the compound of formula (I), and a display device containing the organic electronic device.

[0002] [Background technology] Self-emissive organic electronic devices (e.g., organic light-emitting diodes, or OLEDs) 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 stacked sequentially on a substrate. Here, 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 through the HTL to the EML, and electrons injected from the cathode move through the ETL to the EML. The holes and electrons recombine in the EML to produce excitons. When the exciton falls from the excited state to the ground state, light is emitted. The injection and outflow of holes and electrons must be in equilibrium, and as a result, OLEDs with the above structure have excellent efficiency and / or a long lifetime.

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

[0005] WO2019168368A1 provides an organic light-emitting diode comprising a cathode, an anode, and a light-emitting layer provided between the cathode and the anode, wherein the anode and the light-emitting layer contain a compound represented by chemical formula 1, and one of the compounds represented by chemical formula 2 and chemical formula 3.

[0006] EP1988587A1 discloses an organic mesomeric compound as an organic doping agent for doping an organic semiconductor matrix material, as a blocker layer, as a charge injection layer, or as the organic semiconductor itself. The organic mesomeric compound is an oxocarbon, a pseudo-oxocarbon, or a radialene compound.

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

[0008] 〔Disclosure〕 One aspect of the present invention provides an organic compound for use in an organic electronic device of formula (I):

[0009]

Chemical formula

[0010] Wherein, A 1 is selected from formula (II),

[0011]

Chemical formula

[0012] X 1 is CR 1 or N; X 2 is CR 2 or N; X 3 is CR 3 or N; X 4 is CR 4 or N; X 5 is CR 5 or N; (when present) R 1 、R 2 、R3 , R 4 and R 5 R is independently selected from CN, partially fluorinated or fully fluorinated C1-C8 alkyl, halogen, Cl, F, D, or H, thereby R 1 , R 2 , R 3 , R 4 and R 5 If any of the following exist, the corresponding X 1 , X 2 , X 3 , X 4 and X 5 It is not N; however, R 1 ~R 5 At least one of is selected from D or H, and, R 1 and / or R 5 Either of these is independently selected from CN, partially fluorinated or fully fluorinated C1-C8 alkyl groups, or R n and R n+1 At least one of (n=1~4) is independently selected from CN, partially fluorinated, or fully fluorinated C1-C8 alkyl groups; A 2 and A 3 These are independently selected from equation (III),

[0013] [ka]

[0014] In the formula, Ar is independently either substituted or unsubstituted C6~C 18 Aryl and substituted or unsubstituted C2-C 18 Selected from heteroaryls, the substituent on Ar is independently selected from CN, partially or totally fluorinated C1-C6 alkyls, halogens, Cl, F, and D; and, R' is Ar, substituted or unsubstituted C6-C 18 Aryl, or substituted or unsubstituted C3-C 18Selected from heteroaryls, partially fluorinated or fully fluorinated C1-C8 alkyls, halogens, F, or CN; In the formula, the asterisk "*" indicates the bond position.

[0015] Unless otherwise specified, throughout this application and claims, A n B n , R n Please note that these terms always refer to the same part.

[0016] In this specification, unless otherwise defined, "partially fluorinated" refers to a C1-C8 alkyl group in which only some of the hydrogen atoms are replaced by fluorine atoms.

[0017] In this specification, unless otherwise specified, "total fluorination" refers to a C1-C8 group in which all hydrogen atoms are replaced by fluorine atoms.

[0018] In this specification, unless otherwise defined, “substituted” means deuterium, C1-C 12 Alkyl and C1-C 12 This refers to substances that have been substituted with alkoxy compounds.

[0019] However, in this specification, “aryl substitution” refers to substitution by one or more aryl groups. The aryl group itself may be substituted by one or more aryl groups and / or heteroaryl groups.

[0020] Similarly, in this specification, “heteroaryl substitution” refers to substitution by one or more heteroaryl groups. A heteroaryl group itself may be substituted by one or more aryl and / or heteroaryl groups.

[0021] In this specification, unless otherwise defined, "alkyl group" refers to a saturated aliphatic hydrocarbyl group. Alkyl groups are C1-C 12 It may be an alkyl group. More specifically, the alkyl group is C1-C10 It can be an alkyl group or a C1-C6 alkyl group. For example, a C1-C4 alkyl group contains 1 to 4 carbon atoms in the alkyl chain and can be selected from methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, and tert-butyl.

[0022] Specific examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl groups.

[0023] The term "cycloalkyl" refers to a saturated hydrocarbyl group derived from a cycloalkane by formally abstracting one hydrogen atom from the ring atom contained in the corresponding cycloalkane. Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and adamantyl groups.

[0024] The term "hetero" is understood to mean a state in which at least one carbon atom in a structure that can be formed by covalently bonded carbon atoms is substituted by another polyvalent atom. Preferably, the heteroatom is selected from B, Si, N, P, O, and S; more preferably, the heteroatom is selected from N, P, O, and S.

[0025] In this specification, “aryl group” refers to a hydrocarbyl group that can be produced by formally abstracting one hydrogen atom from an aromatic ring in the corresponding aromatic hydrocarbon. An aromatic hydrocarbon refers to a hydrocarbon comprising 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 bonded carbon atoms, which comprises a conjugated system of delocalized electrons satisfying Hückel's rule. Examples of aryl groups include monocyclic groups (e.g., phenyl or tolyl), polycyclic groups comprising multiple aromatic rings linked by single bonds (e.g., biphenyl), and polycyclic groups comprising fused rings (e.g., naphthyl or fluoren-2-yl).

[0026] Similarly, under the "heteroaryl" designation, groups derived by formally abstracting one ring hydrogen from a heterocyclic aromatic ring in a compound containing at least one such ring are understood to be particularly preferred.

[0027] Under heterocycloalkyl groups, groups derived by formally abstracting one ring hydrogen from a saturated cycloalkyl ring in a compound containing at least one such ring are considered particularly preferred.

[0028] The term "fused aryl rings" or "condensed aryl rings" refers to two aryl rings that share at least two common sp² (sp²). 2 When hybrid carbon atoms share a common carbon atom, it is understood that they are in a fused or condensed state.

[0029] In this specification, a single bond refers to a direct bond.

[0030] The terms "free of," "does not contain," and "does not comprise" do not exclude impurities that may be present in the compound before vapor deposition. These impurities do not have any technical impact on the objectives achieved by this invention.

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

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

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

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

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

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

[0037] In this specification, hole properties refer to the ability to donate electrons and form holes when an electric field is applied, and mean that holes formed on the anode can be easily injected into the light-emitting layer and transported through the light-emitting layer due to the conductive properties corresponding to the highest occupied molecular orbital (HOMO) level.

[0038] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied, and the conductive properties corresponding to the lowest empty molecular orbital (LUMO) level mean that electrons formed on the cathode can be easily injected into the light-emitting layer and transported within the light-emitting layer.

[0039] [Advantageous effects] Surprisingly, the organic compounds of the present invention have been found to solve the underlying problems of the present invention by enabling various embodiments of devices that are superior to organic electroluminescent devices known in the art, particularly in terms of operating potential over service life.

[0040] According to one embodiment of the present invention, the compound is selected from formula (IV),

[0041] [ka]

[0042] In the formula, B 1 is selected from equation (V),

[0043] [ka]

[0044] B 3 and B 5 is Ar, and B 2 B 4 and B 6 is R 3 The asterisk "*" indicates the binding position.

[0045] According to one embodiment of the present invention, R 1 and / or R 5 These are independently selected from CN, totally fluorinated C1-C8 alkyl, or R n and R n+1 At least one of (n=1~4) is independently selected from CN, and all-fluorinated C1~C8 alkyl groups.

[0046] According to one embodiment of the present invention, R 1 and / or R 5 It is independently selected from CN or CF3, or R n and Rn+1 At least one of (n=1~4) is independently selected from CN or CF3.

[0047] According to one embodiment of the present invention, A 1 and A 3 They are not the same.

[0048] Alternatively, according to one embodiment of the present invention, A 2 and A 3 At least one from A 1 It is identical to [the other one].

[0049] According to one embodiment of the present invention, A 1 and A 2 They are identical, A 1 and A 3 They are not the same.

[0050] According to one embodiment of the present invention, A 1 , A 2 and A 3 They are identical.

[0051] According to one embodiment of the present invention, X 3 CR 3 And R 3 The element is selected from partially fluorinated or fully fluorinated C1-C8 alkyl groups, halogens, Cl, F, D, or H.

[0052] According to one embodiment of the present invention, X 1 and / or X 5 One of them is C-CN.

[0053] According to one embodiment of the present invention, X 1 and / or X 2 This is C-CN.

[0054] According to one embodiment of the present invention, X 1 and X 3 This is C-CN.

[0055] According to one embodiment of the present invention, R1 ~R 5 At least three of them are independently selected from CN, partially fluorinated or fully fluorinated C1-C8 alkyl, halogen, Cl, and F.

[0056] According to one embodiment of the present invention, R 1 ~R 5 Three of them are independently selected from CN, partially fluorinated or fully fluorinated C1-C8 alkyl, halogen, Cl, and F.

[0057] According to one embodiment of the present invention, R 1 and R 3 are independently selected from CN, partially fluorinated or fully fluorinated C1-C8 alkyl, halogen, Cl, and F.

[0058] According to one embodiment of the present invention, R 1 and R 3 are independently selected from CN, partially fluorinated or fully fluorinated C1-C8 alkyl, halogen, Cl, and F, and X 2 , X 4 and X 5 is either CH or N.

[0059] According to one embodiment of the present invention, one of X 1 ~X 5 is N, and one of R 1 ~R 5 is independently selected from CN, partially fluorinated or fully fluorinated C1-C8 alkyl, halogen, Cl, and F.

[0060] According to one embodiment of the present invention, one of X 1 and X 5 is N, and one of R 1 ~R 5 is independently selected from CN, partially fluorinated or fully fluorinated C1-C8 alkyl, halogen, Cl, and F.

[0061] According to one embodiment of the present invention, X 1 and X5 Two of them are N, and R 1 ~R 5 Two of these are independently selected from CN, partially fluorinated or fully fluorinated C1-C8 alkyl groups.

[0062] According to one embodiment of the present invention, R' is selected as CN.

[0063] According to one embodiment of the present invention, formula (II) is selected from the group including the following parts:

[0064] [ka] JPEG0007842040000007.jpg217169JPEG0007842040000008.jpg224169JPEG0007842040000009.jpg31169

[0065] According to one embodiment of the present invention, formula (III) is selected from the group including the following parts:

[0066] [ka] JPEG0007842040000011.jpg217169JPEG0007842040000012.jpg223169JPEG0007842040000013.jpg208169JPEG0007842040000014.jpg73169

[0067] According to one embodiment of the present invention, the compound of formula (I) contains fewer than nine CN groups, preferably fewer than eight CN groups.

[0068] According to one embodiment of the present invention, the compound of formula (I) contains 3 to 8 CN groups, preferably 3 to 7 CN groups.

[0069] When the number of CN groups in the compound of formula (I) is selected within this range, improved processing characteristics can be obtained, particularly in vacuum thermal deposition.

[0070] According to one embodiment of the present invention, using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany), 6 to 31 G in the gas phase is used. * When calculated by applying the hybrid functional B3LYP having the basis set, the LUMO levels of the compounds of formula (I) are selected in the range of ≤-4.7eV and ≥-5.4eV, preferably in the range of ≤-4.75eV and ≥-5.36eV, and most preferably in the range of ≤-4.8eV and ≥-5.3eV.

[0071] According to one embodiment of the present invention, the compound of formula (I) contains 3 to 8 CN groups, preferably 3 to 7 CN groups, and is subjected to 6 to 31 G in the gas phase using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). * When calculated by applying the hybrid functional B3LYP having the basis set, the LUMO levels of the compounds of formula (I) are selected in the range of ≤-4.7eV and ≥-5.4eV, preferably in the range of ≤-4.75eV and ≥-5.36eV, and most preferably in the range of ≤-4.8eV and ≥-5.3eV.

[0072] According to one embodiment of the present invention, the LUMO level of the compound of formula (I), when determined under the same conditions, is further away from the vacuum level than 4,4',4'-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenatetris(cyanomethanylidene))tribenzonitrile, preferably further away from the vacuum level than 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenatetris(cyanomethanylidene))tris(3-(fluorobenzonitrile); more preferably further away from the vacuum level than 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenatetris(cyanomethanylidene))tris(3-(trifluoromethyl)benzonitrile).

[0073] According to one embodiment of the present invention, the compound of formula (I) contains 3 to 8 CN groups, preferably 3 to 7 CN groups, and the LUMO level of the compound of formula (I), when determined under the same conditions, is further from the vacuum level than that of 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenateris(cyanomethanylidene))tribenzonitrile, preferably 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenateris(cyanomethanylidene))tribenzonitrile. It is further away from the vacuum level than tanylidene))tris(3-(fluorobenzonitrile); more preferably further away from the vacuum level than 4,4',4''-((1E,1'E,1''E)-cyclopropane-1,2,3-triylidenetris(cyanomethanylidene))tris(3-(trifluoromethyl)benzonitrile). According to one embodiment of the present invention, in the formula R', R' is CN, and the compound of formula (I) contains 3 to 8 CN groups, preferably 3 to 7 CN groups; the following formulas are excluded:

[0074] [ka]

[0075] According to one embodiment, the compound of formula (I) is selected from compounds A1 to A31:

[0076] [ka] JPEG0007842040000017.jpg218169JPEG0007842040000018.jpg231169JPEG0007842040000019.jpg218169

[0077] Furthermore, the present invention relates to 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 the at least one organic semiconductor layer comprises a compound of formula (I).

[0078] According to one embodiment, the organic semiconductor layer comprises a composition containing a compound of formula (IV) and at least one compound of formulas (IVa) to (IVd).

[0079] [ka]

[0080] When an organic semiconductor layer includes such a composition, throughout this specification, the term “compound of formula (I)” is intended to also include the above-mentioned composition.

[0081] According to one embodiment of the present invention, the organic semiconductor layer and / or the compound of formula (I) are non-luminescent.

[0082] In the context of this specification, the terms “essentially non-luminescent” or “non-luminescent” mean that the contribution of the compound or layer to the visible emission spectrum from the device is less than 10%, preferably less than 5%, of the visible emission spectrum. The visible emission spectrum is an emission spectrum having wavelengths from about ≥380 nm to about ≤780 nm.

[0083] According to one embodiment of the present invention, at least one organic semiconductor layer further comprises a substantially covalent matrix compound.

[0084] [Substantially covalent matrix compounds] The organic semiconductor layer may further comprise a substantially covalent matrix compound. According to one embodiment, the substantially covalent matrix compound may be selected from at least one organic compound. The substantially covalent matrix may consist substantially of covalently bonded C, H, O, N, S, and the matrix may optionally further comprise covalently bonded B, P, As, and / or Se.

[0085] According to one embodiment of an organic electronic device, the organic semiconductor layer further comprises a substantially covalent matrix compound, the substantially covalent matrix compound may be selected from organic compounds substantially composed of covalently bonded C, H, O, N, S, and the substantially covalent matrix compound optionally further comprises covalently bonded B, P, As, and / or Se.

[0086] Organometallic compounds containing carbon-metal covalent bonds, metal complexes containing organic ligands, and metal salts of organic acids are further examples of organic compounds that can function as substantially covalent matrix compounds in hole implantation layers.

[0087] In one embodiment, the substantially covalent matrix compound lacks metal atoms, and the majority of its skeletal atoms can be selected from C, O, S, and N. Alternatively, the substantially covalent matrix compound lacks metal atoms, and the majority of its skeletal atoms can be selected from C and N.

[0088] According to one embodiment, the substantially covalent matrix compound may have a molecular weight Mw of ≥400 g / mol and ≤2000 g / mol, preferably ≥450 g / mol and ≤1500 g / mol, more preferably ≥500 g / mol and ≤1000 g / mol, even more preferably ≥550 g / mol and ≤900 g / mol, and also preferably ≥600 g / mol and ≤800 g / mol.

[0089] Preferably, the substantially covalent matrix compound comprises at least one arylamine moiety, or diarylamine moiety, or triarylamine moiety.

[0090] Preferably, the substantially covalent matrix compound does not contain metallic and / or ionic bonds.

[0091] [Compounds of formula (VI) or compounds of formula (VII)] According to another aspect of the present invention, the at least one matrix compound, also called a “substantially covalent matrix compound,” may include at least one arylamine compound, diarylamine compound, triarylamine compound, compound of formula (VI), or compound of formula (VII):

[0092] [ka]

[0093] During the ceremony: T 1 , T 2 , T 3 , T 4 and T 5 This is independently selected from a single bond, phenylene, biphenylene, terphenylene, or naphthenylene, preferably selected from a single bond or phenylene; T 6 These are phenylene, biphenylene, terphenylene, or naphthenylene; Ar1 Ar 2 Ar 3 Ar 4 and Ar 5 These are independently substituted or non-substituted C6~C 20 Aryl, or substituted or unsubstituted C3-C 20 Heteroarylene, substituted or unsubstituted biphenylene, substituted or unsubstituted fluorene, substituted 9-fluorene, substituted 9,9-fluorene, substituted or unsubstituted naphthalene, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrene, substituted or unsubstituted pyrene, substituted or unsubstituted perylene, substituted or unsubstituted triphenylene, substituted or unsubstituted tetracene, substituted or unsubstituted tetrafen, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthene, substituted or unsubstituted carbazole, substituted 9-phenylcarbazole, substituted or unsubstituted azepine, substituted or unsubstituted dibenzo[b,f]azepine, substituted Alternatively, a fused ring system comprising at least three substituted or unsubstituted aromatic rings, substituted or unsubstituted fluorenes, or 2 to 6 substituted or unsubstituted 5 to 7-membered rings selected from the group comprising: (i) unsaturated 5 to 7-membered heterorings, (ii) 5 to 6-membered aromatic heterorings, (iii) unsaturated 5 to 7-membered nonheterorings, or (iv) 6-membered aromatic nonheterorings; Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 The substituents are H, D, F, C(-O)R 2 , CN, Si(R 2 )3, P(-O)(R 2 )2, OR 2S(-O)R 2 S(-O)2R 2 , substituted or unsubstituted linear alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl groups having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl or alkynyl groups having 2 to 20 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aromatic ring systems having 6 to 40 aromatic ring atoms, and substituted or unsubstituted heteroaromatic ring systems having 5 to 40 aromatic ring atoms, unsubstituted C6-C 18 Aryl and unsubstituted C3-C 18 A heteroaryl fused ring system comprising 2 to 6 unsubstituted 5 to 7-membered rings, wherein the rings are selected from the same or different groups from the group comprising unsaturated 5 to 7-membered heterorings, 5 to 6-membered heteroaromatic rings, unsaturated 5 to 7-membered nonheterorings, and 6-membered aromatic nonheterorings. R 2 This includes H, D, linear alkyl groups having 1 to 6 carbon atoms, branched alkyl groups having 1 to 6 carbon atoms, cyclic alkyl groups having 3 to 6 carbon atoms, alkenyl or alkynyl groups having 2 to 6 carbon atoms, and C6-C 18 Aryl, or C3~C 18 It can be selected from heteroaryls.

[0094] According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 T can be independently selected from a single bond, phenylene, biphenylene, or terphenylene. According to one embodiment, 1 , T 2 , T 3 , T 4 and T 5 T can be independently selected from phenylene, biphenylene, or terphenylene. 1 , T 2 , T 3 , T 4 and T5 One of these is a single bond. According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 T can be independently selected from phenylene or biphenylene. 1 , T 2 , T 3 , T 4 and T 5 One of these is a single bond. According to one embodiment, T 1 , T 2 , T 3 , T 4 and T 5 T can be independently selected from phenylene or biphenylene. 1 , T 2 , T 3 , T 4 and T 5 Two of them are single bonds.

[0095] According to one embodiment, T 1 , T 2 and T 3 It can be independently selected from phenylene, T 1 , T 2 and T 3 One of these is a single bond. According to one embodiment, T 1 , T 2 and T 3 It can be independently selected from phenylene, T 1 , T 2 and T 3 Two of them are single bonds.

[0096] According to one embodiment, T 6 This can be phenylene, biphenylene, or terphenylene. According to one embodiment, T 6 It can be phenylene. According to one embodiment, T 6 This may be biphenylene. According to one embodiment, T 6 It could be terphenylene.

[0097] According to one embodiment, Ar1 Ar 2 Ar 3 Ar 4 and Ar 5 These can be independently selected from D1 to D16:

[0098] [ka]

[0099] In the formula, the asterisk "*" indicates the bond position.

[0100] According to one embodiment, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 These can be independently selected from D1 to D15, or selected from D1 to D10 and D13 to D15.

[0101] According to one embodiment, Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 These can be independently selected from the group consisting of D1, D2, D5, D7, D9, D10, and D13-D16.

[0102] Ar 1 Ar 2 Ar 3 Ar 4 and Ar 5 When selected within this range, the rate start temperature may be particularly suitable for mass production.

[0103] "Matrix compounds of formula (VI) or formula (VII)" may also be referred to as "hole transport compounds."

[0104] According to one embodiment, the substantially covalent matrix compound comprises at least one naphthyl group, carbazole group, dibenzofuran group, dibenzothiophene group and / or substituted fluorenyl group, wherein the substituent is independently selected from methyl, phenyl, or fluorenyl.

[0105] According to one embodiment of the electronic device, the matrix compound of formula (VI) or formula (VII) is selected from F1 to F19:

[0106] [ka] JPEG0007842040000024.jpg186169JPEG0007842040000025.jpg165169

[0107] [Organic semiconductor layer] Organic semiconductor layers can be formed on the anode or cathode layer by methods such as vacuum deposition, spin coating, printing, casting, slot-die coating, and Langmuir-Blodgett (LB) deposition. When organic semiconductor layers are formed using vacuum deposition, the deposition conditions can vary depending on the compound used to form the layer, as well as the desired structure and thermal properties of the layer. However, typically, the conditions for vacuum deposition include a deposition temperature of 100°C to 350°C, and 10 -8 ~10 -3 This may include a Torre pressure (1 Torre is equal to 133.322 Pa) and an evaporation rate of 0.1 nm / sec to 10 nm / sec.

[0108] When an organic semiconductor layer is formed using spin coating or printing, the coating conditions may vary depending on the compound used to form the layer, as well as the desired structure and thermal properties of the organic semiconductor 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, the solvent is removed by heat treatment.

[0109] The thickness of the organic semiconductor layer can range from approximately 1 nm to approximately 20 nm, for example, from approximately 2 nm to approximately 15 nm, or from approximately 2 nm to approximately 12 nm.

[0110] If 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 any substantial penalty to the driving voltage.

[0111] According to one embodiment of the present invention, the organic semiconductor layer may include the following: - A compound of formula (I) in an amount of at least about ≥0.5% by weight to about ≤30% by weight, preferably about ≥0.5% by weight to about ≤20% by weight, and more preferably about ≥1% by weight to about ≤15% by weight, - A substantially covalent matrix compound in an amount of 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 % of the compound of formula (I) is lower than the weight % of the substantially covalent matrix compound; where the weight % of the composition is based on the total weight of the organic semiconductor layer.

[0112] According to one embodiment of the present invention, the organic electronic device includes at least one photoactive layer, and at least one of the at least one organic semiconductor layer is disposed between the anode and the at least one photoactive layer.

[0113] According to one embodiment of the present invention, the organic electronic device includes at least two photoactive layers, and at least one of the at least one organic semiconductor layer is disposed between the first photoactive layer and the second photoactive layer.

[0114] According to one embodiment of the present invention, the organic electronic device includes at least one photoactive layer, the photoactive layer being located between an anode layer and a cathode layer.

[0115] According to one embodiment of the present invention, the organic electronic device includes at least one photoactive layer, and at least one organic semiconductor layer is disposed between the anode and the at least one photoactive layer.

[0116] According to one embodiment of the present invention, the organic electronic device includes at least two photoactive layers, and at least one of the at least one organic semiconductor layer is disposed between the first photoactive layer and the second photoactive layer.

[0117] According to one embodiment of the present invention, the organic electronic device includes at least two photoactive layers, one of the at least one organic semiconductor layers is disposed between a first photoactive layer and a second photoactive layer, and one of the at least one organic semiconductor layer is disposed between an anode layer and the first photoactive layer.

[0118] According to one embodiment of the present invention, the electronic organic device is an electroluminescent device, and preferably an organic light-emitting diode.

[0119] According to one embodiment of the present invention, an electronic organic device is not an organic light-emitting diode, but rather an organic light-emitting device comprising a substrate, an anode, a cathode, a first light-emitting layer, an electron injection layer, and a second electron transport layer stack, wherein the second electron transport layer stack is disposed between the first light-emitting layer and the electron injection layer; Here, - At least one of the first electron transport layer stack and the second electron transport layer stack independently comprises a first electron transport layer and a second electron transport layer; - The first electron transport layer contains the compound of formula (X), (Ar 1 -A c ) a -X b (X); -a and b are independently 1 or 2; -c is independently either 0 or 1; -Ar 1 These are independent, C6~C 60 Aryl or C2~C 42 Selected from heteroaryls, - Here, each Ar 1 Independently, C6~C 12 Aryl, C3~C 11 Heteroaryl, C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially or fully fluorinated C1-C6 alkyl, partially or fully fluorinated C1-C6 alkoxy, partially or fully deuterated C1-C6 alkyl, partially or fully deuterated C1-C6 alkoxy, halogen, CN or PY(R) 10 ) may be substituted with one or two substituents selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 Independently, C6~C 12 Aryl, C3~C 12 Selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially or fully fluorinated C1-C6 alkyl, partially or fully fluorinated C1-C6 alkoxy, partially or fully deuterated C1-C6 alkyl, or partially or fully deuterated C1-C6 alkoxy; -Here, Ar 1 Each of the above C6~C 12 Aryl substituents, and Ar 1 Each of the above C3~C 11 Heteroaryl substituents may be substituted with C1-C4 alkyl or halogens. -A is independent of C6~C 30 Selected from the alphabet, - Here, each A is independent of C6~C 12 Aryl and C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially or fully fluorinated C1-C6 alkyl, partially or fully fluorinated C1-C6 alkoxy, partially or fully deuterated C1-C6 alkyl, partially or fully deuterated C1-C6 alkoxy, halogen, CN or PY(R) 10) may be substituted with one or two substituents selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O and R 10 Independently, C6~C 12 Aryl, C3~C 12 Selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially or fully fluorinated C1-C6 alkyl, partially or fully fluorinated C1-C6 alkoxy, partially or fully deuterated C1-C6 alkyl, or partially or fully deuterated C1-C6 alkoxy; - Here, regarding A, C6~C 12 Each aryl substituent may be substituted with a C1-C4 alkyl group or a halogen; -X is independent of C2~C 42 Heteroaryl and C6-C 60 Selected from the group consisting of aryls, - Here, each X is independently C6~C 12 Aryl, C3~C 11 Heteroaryls, and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially or fully fluorinated C1-C6 alkyls, partially or fully fluorinated C1-C6 alkoxys, partially or fully deuterated C1-C6 alkyls, partially or fully deuterated C1-C6 alkoxys, halogens, CN or PY(R) 10 ) may be substituted with one or two substituents selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O, and R 10 Independently, C6~C 12 Aryl, C3~C 12 Selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially or fully fluorinated C1-C6 alkyl, partially or fully fluorinated C1-C6 alkoxy, partially or fully deuterated C1-C6 alkyl, or partially or fully deuterated C1-C6 alkoxy; -Here, for X, each C6~C 12 For the aryl substituent and X, each C3-C 11Heteroaryl substituents may be substituted with C1-C4 alkyl or halogen atoms; - The molecular dipole moments of the compound of formula (X) are ≥0D and ≤4D; - The second electron transport layer contains the compound of formula (XI), (Ar 2 ) m -(Z k -G) n (XI); -m and n are independently 1 or 2; -k is independently 0, 1, or 2; -Ar 2 These are, independently, C2~C 42 Heteroaryl and C6-C 60 Selected from the group consisting of aryls, - Here, each Ar 2 Independently, C6~C 12 Aryl, C3~C 11 Heteroaryls, and C1-C6 alkyls, D, C1-C6 alkoxys, C3-C6 branched alkyls, C3-C6 cyclic alkyls, C3-C6 branched alkoxys, C3-C6 cyclic alkoxys, partially or fully fluorinated C1-C6 alkyls, partially or fully fluorinated C1-C6 alkoxys, partially or fully deuterated C1-C6 alkyls, partially or fully deuterated C1-C6 alkoxys, halogens, CN or PY(R) 10 ) may be substituted with one or two substituents selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O, and R 10 Independently, C6~C 12 Aryl, C3~C 12 Selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially or fully fluorinated C1-C6 alkyl, partially or fully fluorinated C1-C6 alkoxy, partially or fully deuterated C1-C6 alkyl, or partially or fully deuterated C1-C6 alkoxy; -Here, Ar 2 Regarding each of C6~C 12 Aryl substituents, and Ar 2 Regarding each of C3~C 11Heteroaryl substituents may be substituted with C1-C4 alkyl or halogen atoms; -Z is independent of C6~C 30 Selected from the alphabet, - Here, each Z is independently C6~C 12 Aryl and C1-C6 alkyl, D, C1-C6 alkoxy, C3-C6 branched alkyl, C3-C6 cyclic alkyl, C3-C6 branched alkoxy, C3-C6 cyclic alkoxy, partially or fully fluorinated C1-C6 alkyl, partially or fully fluorinated C1-C6 alkoxy, partially or fully deuterated C1-C6 alkyl, partially or fully deuterated C1-C6 alkoxy, halogen, CN or PY(R) 10 ) may be substituted with one or two substituents selected from the group consisting of 2, where Y is selected from O, S or Se, preferably O, and R 10 Independently, C6~C 12 Aryl, C3~C 12 Selected from heteroaryl, C1-C6 alkyl, C1-C6 alkoxy, partially or fully fluorinated C1-C6 alkyl, partially or fully fluorinated C1-C6 alkoxy, partially or fully deuterated C1-C6 alkyl, or partially or fully deuterated C1-C6 alkoxy; -Here, regarding Z, each C6~C 12 The aryl substituent may be substituted with a C1-C4 alkyl group or a halogen; -G was selected such that the dipole moment of compound G-phenyl is ≥1D and ≤7D; and, - The first electron transport layer and the second electron transport layer do not contain electrolytic dopants; It has the following characteristics: -The organic light-emitting diode further comprises a p-type layer; - The p-type layer is positioned between the anode and the first light-emitting layer; and the p-type layer contains a radialene compound.

[0120] Furthermore, the present invention relates to an organic electronic device comprising an anode layer, a cathode layer, at least one photoactive layer, and at least one organic semiconductor layer, wherein the at least one organic semiconductor layer is disposed between the at least one photoactive layer and the cathode, and the at least one organic semiconductor layer contains the compound of the present invention.

[0121] Furthermore, the present invention relates to a display device including an organic electronic device according to the present invention.

[0122] [Further layers] According to the present invention, the organic electronic device may include further layers in addition to the layers described above. Exemplary embodiments of each layer are described below: substrate The substrate can be any substrate commonly used in the manufacture of electronic devices (e.g., organic light-emitting diodes). If light rays are emitted through the substrate, the substrate must be made of a transparent or translucent material (e.g., a glass substrate or a transparent plastic substrate). If light rays are emitted through the top surface, the substrate can be made of both transparent and opaque materials (e.g., a glass substrate, a plastic substrate, a metal substrate, or a silicon substrate).

[0123] anode layer The anode layer can be formed by vapor deposition or sputtering of the material used to form the anode layer. The material used to form the anode layer may be a high work function material, which can facilitate hole injection. The anode material may also be selected from low work function materials (i.e., aluminum). The anode electrode may be a transparent electrode or a reflective electrode. The anode electrode can be formed using transparent conductive oxides (e.g., indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), aluminum zinc oxide (AlZO), and zinc oxide (ZnO)). The anode layer may also be formed using metals, typically silver (Ag), gold (Au), or metallic alloys.

[0124] Hole injection layer Hole injection layers (HILs) can be formed on the anode layer by methods such as vacuum deposition, spin coating, printing, casting, slot-die coating, and Langmuir-Blodgett (LB) deposition. When HILs are formed using vacuum deposition, the deposition conditions can vary depending on the compound used to form the HIL, as well as the desired structure and thermal properties of the HIL. However, typically, the conditions for vacuum deposition are a deposition temperature of 100°C to 500°C, and 10 -8 ~10 -3 This may include a Torre pressure (1 Torre is equal to 133.322 Pa) and an evaporation rate of 0.1 nm / sec to 10 nm / sec.

[0125] When HILs are formed using spin coating or printing, the coating conditions may vary depending on the compound used to form the HIL, as well as 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, the solvent is removed by heat treatment.

[0126] 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 (e.g., copper phthalocyanine (CuPc)), 4,4',4''-tris(3-methylphenylamino)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).

[0127] HIL may contain or consist of a p-type dopant, the p-type dopant may be selected from, but is not limited to, tetrafluoro-tetracyanoquinone dimethane (F4TCNQ), 2,2'-(perfluoronaphthalene-2,6-diylidene) dimalononitrile, or 2,2',2''-(cyclopropane-1,2,3-triylidene)tris(2-(p-cyanotetrafluorophenyl)acetonitrile). HIL may be selected from hole transport matrix compounds doped with a p-type dopant. Typical examples of known doped hole transport materials include copper phthalocyanine (CuPc) doped with tetrafluoro-tetracyanoquinone dimethane (F4TCNQ) with a LUMO level of approximately -5.2 eV, zinc phthalocyanine (ZnPc) doped with F4TCNQ (HOMO=-5.2eV), 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 with a HOMO level of approximately -5.2 eV. The p-type dopant concentration can be selected from 1% to 20% by weight, more preferably from 3% to 10% by weight.

[0128] The thickness of the HIL can range from approximately 1 nm to approximately 100 nm, for example, from approximately 1 nm to approximately 25 nm. Within this thickness range, the HIL can exhibit excellent hole injection characteristics without substantial penalty to the drive voltage.

[0129] Hole transport layer Hole transport layers (HTLs) can be formed on HTLs by methods such as vacuum deposition, spin coating, slot-die coating, printing, casting, and Langmuir-Blodgett (LB) deposition. When HTLs are formed by vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for HIL formation. However, the conditions for vacuum or solution deposition may vary depending on the compound used to form the HTL.

[0130] HTLs can be formed from any compound commonly used to form HTLs. Compounds that can be preferably used are disclosed, for example, in Yasuhiko Shirota and Hiroshi Kageyama, Chem. Rev. 2007, 107, 953-1010, which are incorporated herein by reference. Examples of compounds that can be used to form HTLs include carbazole derivatives (e.g., N-phenylcarbazole or polyvinylcarbazole); benzidine derivatives (e.g., N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di(naphthalene-1-yl)-N,N'-diphenylbenzidine (α-NPD)); and triphenylamine compounds (e.g., 4,4',4''-tris(N-carbazolyl)triphenylamine (TCTA)). Among these compounds, TCTA can transport holes and suppress the diffusion of excitons into EML.

[0131] According to one embodiment of the present invention, the hole transport layer may contain the same substantially covalent matrix compound as the organic semiconductor layer.

[0132] The thickness of the HTL may range from about 5 nm to about 250 nm, preferably about 10 nm to about 200 nm, more preferably about 20 nm to about 190 nm, more preferably about 40 nm to about 180 nm, more preferably about 60 nm to about 170 nm, more preferably about 80 nm to about 160 nm, more preferably about 100 nm to about 160 nm, and more preferably about 120 nm to about 140 nm. A preferred thickness of the HTL may be 170 nm to 200 nm.

[0133] If the thickness of the HTL is within this range, the HTL can have excellent hole transport characteristics without any substantial penalty to the drive voltage.

[0134] electron blocking layer The function of an electron blocking layer (EBL) is to prevent electrons from moving from the light-emitting layer to the hole transport layer, thereby confining electrons to the light-emitting layer. This improves efficiency, operating voltage, and / or lifetime. Typically, electron blocking layers contain triarylamine compounds. Triarylamine compounds may have a LUMO level closer to the vacuum level than the LUMO level of the hole transport layer. The electron blocking layer may have a HOMO level further away from the vacuum level compared to the HOMO level of the hole transport layer. The thickness of the electron blocking layer can be selected between 2 nm and 20 nm.

[0135] If the electron stopping layer has a high triplet level, it may also be described as a triplet control layer.

[0136] The function of the triplet control layer is to reduce triplet quenching when a phosphorescent green or phosphorescent blue emitting layer is used. This can increase the luminescence efficiency from the phosphorescent layer. The triplet control layer can be selected from triarylamine compounds having a triplet level higher than the triplet level of the phosphorescent material in the adjacent emitting layer. Compounds suitable for the triplet control layer, particularly triarylamine compounds, are described in EP2722908A1.

[0137] Photoactive layer (PAL) The photoactive layer converts electric current into photons, or photons into electric current.

[0138] PALs can be formed on HTLs by methods such as vacuum deposition, spin coating, slot-die coating, printing, casting, and LB deposition. When PALs are formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for HIL formation. However, the conditions for deposition and coating may vary depending on the compound used to form the PAL.

[0139] According to one embodiment of the present invention, the photoactive layer does not contain the compound of formula (I).

[0140] The photoactive layer may be a light-emitting layer or a light-absorbing layer.

[0141] Emitting layer (EML) EMLs can be formed on HTLs by methods such as vacuum deposition, spin coating, slot-die coating, printing, casting, and LB deposition. When EMLs are formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for HIL formation. However, the conditions for deposition and coating may vary depending on the compound used to form the EML.

[0142] According to one embodiment of the present invention, the light-emitting layer does not contain the compound of formula (I).

[0143] The luminescent layer (EML) can be formed by a combination of a host and a luminescent dopant. Examples of hosts include Alq3, 4,4'-N,N'-dicarbazole-biphenyl (CBP), poly(n-vinylcarbazole) (PVK), 9,10-di(naphthalene-2-yl)anthracene (ADN), 4,4',4''-tris(carbazole-9-yl)-triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di-2-naphthylanthracene (TBADN), distylyl arylene (DSA), and bis(2-(2-hydroxyphenyl)benzothiazolate)zinc (Zn(BTZ)2).

[0144] The luminescent dopant may be a phosphorescent or fluorescent luminescent material. Phosphorescent luminescent materials and luminescent materials that emit light via a thermally activated delayed fluorescence (TADF) mechanism may be preferred due to their higher efficiency. The luminescent material may be a small molecule or a polymer.

[0145] Examples of red-emitting dopants include, but are not limited to, PtOEP, Ir(piq)3, and Btp2lr(acac). These compounds are phosphorescent, but fluorescent red-emitting dopants can also be used.

[0146] Examples of phosphorescent green dopants include Ir(ppy)3 (ppy = phenylpyridine), Ir(ppy)2 (acac), and Ir(mpyp)3.

[0147] Examples of phosphorescent blue-emitting dopants include F2Irpic, (F2ppy)2Ir(tmd), Ir(dfppz)3, and terfluorene. 4,4'-Bis(4-diphenylamiostyryl)biphenyl (DPAVBi) and 2,5,8,11-tetra-tert-butylperylene (TBPe) are examples of fluorescent blue-emitting dopants.

[0148] The amount of the luminescent dopant may range from about 0.01 to about 50 parts by weight per 100 parts by weight of the host. Alternatively, the luminescent layer may consist of a luminescent polymer. The EML may have a thickness of about 10 nm to about 100 nm, for example, about 20 nm to about 60 nm. When the thickness of the EML is within this range, the EML can exhibit excellent luminescence without substantial penalty in terms of driving voltage.

[0149] Hole Blocking Layer (HBL) To prevent hole diffusion into the ETL, a hole blocking layer (HBL) can be formed on the EML using methods such as vacuum deposition, spin coating, slot-die coating, printing, casting, and LB deposition. If the EML contains a phosphorescent dopant, the HBL may also have triplet exciton blocking properties.

[0150] HBL can also be referred to as auxiliary ETL or a-ETL.

[0151] When HBLs are formed using vacuum deposition or spin coating, the conditions for deposition and coating may be similar to those for HIL formation. However, the conditions for deposition and coating may vary depending on the compound used to form the HBL. Any compound commonly used to form HBLs can be used. Examples of compounds for forming HBLs include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and azine derivatives, preferably triazine or pyrimidine derivatives.

[0152] HBLs can have thicknesses ranging from approximately 5 nm to 100 nm, for example, from approximately 10 nm to 30 nm. Within this thickness range, HBLs can exhibit excellent hole blocking characteristics without substantial penalty to the drive voltage.

[0153] Electron transport layer (ETL) The organic electronic device of the present invention may further include an electron transport layer (ETL).

[0154] According to another embodiment of the present invention, the electron transport layer may further comprise an azine compound, preferably a triazine compound.

[0155] In one embodiment, the electron transport layer may further comprise a dopant selected from an alkali organic complex, preferably LiQ.

[0156] The thickness of the ETL can range from approximately 15 nm to approximately 50 nm, for example, from approximately 20 nm to approximately 40 nm. When the ETL thickness is within this range, the ETL can have satisfactory electron injection characteristics without substantial penalty in terms of drive voltage.

[0157] According to another embodiment of the present invention, the organic electronic device may further include a hole blocking layer and an electron transport layer, the hole blocking layer and the electron transport layer comprising an azine compound. Preferably, the azine compound is a triazine compound.

[0158] Electron injection layer (EIL) Any electron-injection layer (EIL) that facilitates electron injection from the cathode can be formed directly on the electron transport layer (ETL), preferably on the electron transport layer. Examples of materials for forming EILs include lithium 8-hydroxyquinolinoleate (LiQ), LiF, NaCl, CsF, Li2O, BaO, Ca, Ba, Yb, and Mg, which are known in the art. The deposition and coating conditions for forming EILs are similar to those for forming HILs, although the deposition and coating conditions may vary depending on the material used to form the EIL.

[0159] The thickness of the EIL can range from approximately 0.1 nm to approximately 10 nm, for example, from approximately 0.5 nm to approximately 9 nm. When the EIL thickness is within this range, the EIL can have satisfactory electron injection characteristics without a substantial penalty to the drive voltage.

[0160] Cathode layer The cathode layer is formed on the ETL or any EIL. The cathode layer may be formed from a metal, alloy, conductive compound, or mixture thereof. The cathode electrode may have a low work function. For example, the cathode layer may be formed from lithium (Li), magnesium (Mg), aluminum (Al), aluminum (Al)-lithium (Li), calcium (Ca), barium (Ba), ytterbium (Yb), magnesium (Mg)-indium (In), magnesium (Mg)-silver (Ag), etc. Alternatively, the cathode electrode may be formed from a transparent conductive oxide (e.g., ITO or IZO).

[0161] The thickness of the cathode layer can range from approximately 5 nm to approximately 1000 nm, for example, from approximately 10 nm to approximately 100 nm. When the thickness of the cathode layer is in the range of approximately 5 nm to approximately 50 nm, the cathode layer can be transparent or translucent, even if it is formed from a metal or metal alloy.

[0162] It should be understood that the cathode layer is not part of the electron injection layer or electron transport layer.

[0163] Organic light-emitting diode (OLED) The organic electronic device according to the present invention can be an organic light emitting device.

[0164] According to one aspect of the present invention, there is provided an organic light emitting diode (OLED) including a substrate, an anode electrode formed on the substrate, an organic semiconductor layer including a compound of formula (I), a hole transport layer, a light emitting layer, an electron transport layer, and a cathode electrode.

[0165] According to another aspect of the present invention, there is provided an OLED including a substrate, an anode electrode formed on the substrate, an organic semiconductor layer including 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 electrode.

[0166] According to another aspect of the present invention, there is provided an OLED including a substrate, an anode electrode formed on the substrate, an organic semiconductor layer including 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 electrode.

[0167] According to various embodiments of the present invention, an OLED layer disposed between the above-described layers, on the substrate, or on the upper electrode can be provided.

[0168] According to one aspect, the OLED is disposed adjacent to the anode electrode, the anode electrode is disposed adjacent to the first hole injection layer, the first hole injection layer is disposed adjacent to the first hole transport layer, the first hole transport layer is disposed adjacent to the first electron blocking layer, the first electron blocking layer is disposed adjacent to the first light emitting layer, the first light emitting layer is disposed adjacent to the first electron transport layer, the first electron transport layer is disposed adjacent to the n-type charge generation layer, the n-type charge generation layer is disposed adjacent to the hole generation layer, the hole generation layer is disposed adjacent to the second hole transport layer, the second hole transport layer is disposed adjacent to the second electron blocking layer, the second electron blocking layer is disposed adjacent to the second light emitting layer, and an optional electron transport layer and / or an optional injection layer are disposed between the second light emitting layer and the cathode electrode, and it can have a layered structure of the substrate.

[0169] The organic semiconductor layer according to the present invention may be a first hole injection layer and / or a p-type charge generation layer.

[0170] For example, the OLED shown in Figure 2 can be formed by continuously forming an anode layer (120), a hole injection layer (130), a hole transport layer (140), an electron blocking layer (145), an emissive layer (150), a hole blocking layer (155), an electron transport layer (160), an electron injection layer (180), and a cathode layer (190) on a substrate (110) in this order.

[0171] [Organic Electronic Devices] The organic electronic device according to the present invention may be a light-emitting device or a photocell, preferably a light-emitting device.

[0172] According to another aspect of the present invention, a method for manufacturing an organic electronic device is provided. This method uses the following: - At least one deposition source, preferably two deposition sources, more preferably at least three deposition sources.

[0173] Suitable deposition methods include: - Vacuum thermal evaporation for deposition; -Deposition by solution treatment, preferably the treatment is selected from spin coating, printing, and casting; and / or, - Slot die coating.

[0174] According to a certain embodiment of the present invention, a method is provided that uses the following: -A first vapor deposition source for releasing a compound of formula (I) according to the present invention, and - A second deposition source for releasing substantially covalent matrix compounds; A method comprising the step of forming an organic semiconductor layer, for use with organic light-emitting diodes (OLEDs): - The organic semiconductor layer is formed by releasing a compound of formula (I) according to the present invention from a first deposition source and releasing a substantially covalent matrix compound from a second deposition source.

[0175] According to various embodiments of the present invention, the method may further include the steps of forming at least one layer on the anode electrode, selected from the group consisting of forming a hole transport layer or a hole blocking layer, and forming a light-emitting layer between the anode electrode and the first electron transport layer.

[0176] According to various embodiments of the present invention, the method may further include a step for forming an organic light-emitting diode (OLED). Here, -An anode electrode is formed on the substrate, - An organic semiconductor layer containing the compound of formula (I) is formed on the anode electrode. -A hole transport layer is formed on an organic semiconductor layer containing a compound of formula (I), - An luminescent layer is formed on the hole transport layer, - An electron transport layer is formed on the light-emitting layer, and optionally a hole-blocking layer is formed on the light-emitting layer. -Finally, the cathode electrode is formed. -Optionally, a hole blocking layer is formed between the first anode electrode and the light-emitting layer in this order. -Optionally, an electron injection layer is formed between the electron transport layer and the cathode electrode.

[0177] According to various embodiments, an OLED may have the following layered structure, and the layers shall be in the following order: an anode, an organic semiconductor layer containing a compound of formula (I) according to the present invention, a first hole transport layer, a second hole transport layer, an emissive layer, an optional hole blocking layer, an electron transport layer, an optional electron injection layer, and a cathode.

[0178] According to another aspect of the present invention, an electronic device is provided which includes at least one organic light-emitting device according to any embodiment described throughout this specification, preferably the electronic device includes an organic light-emitting diode in one of the embodiments described throughout this specification. More preferably the electronic device is a display device.

[0179] Hereinafter, embodiments will be described in more detail with reference to examples. However, the present invention is not limited to the following examples. Here, exemplary aspects will be referred to in detail.

[0180] [Description of Drawings] The above-described components, as well as the claimed components and the components used in accordance with the present invention in the described embodiments, are not subject to any special exclusion with respect to their size, shape, material selection and technical concept. As a result, the selection criteria known in the relevant art can be applied without limitation.

[0181] Further details, features and advantages of the subject matter are disclosed in the dependent claims and in the following description of the respective drawings. The drawings show, in an exemplary manner, preferred embodiments according to the present invention. However, none of the embodiments necessarily represent all of the scope of the present invention. Therefore, for the purpose of interpreting the scope of the present invention, reference is made to the claims and this specification. It should be understood that both the above summary and the following detailed description are merely exemplary and explanatory and are intended to provide a further description of the claimed invention.

[0182] FIG. 1 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention.

[0183] FIG. 2 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention.

[0184] FIG. 3 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention.

[0185] FIG. 4 is a schematic cross-sectional view of a tandem OLED including a charge generation layer according to an exemplary embodiment of the present invention.

[0186] FIG. 5 is a schematic cross-sectional view of a tandem OLED including a charge generation layer according to an exemplary embodiment of the present invention.

[0187] The drawings will be described in more detail below with reference to examples. However, this disclosure is not limited to the following drawings.

[0188] In this specification, when a first element is referred to as being formed or positioned "on" or "onto" a second element, the first element may be positioned directly on the second element, or one or more other elements may be positioned between them. When a first element is referred to as being formed or positioned "directly on" or "directly onto" a second element, no other elements are positioned between them.

[0189] Figure 1 is a schematic cross-sectional view of an organic electronic device 100 according to an exemplary embodiment of the present invention. The organic electronic device 100 includes a substrate 110, an anode layer 120, and a hole injection layer (HIL) (130) which may contain a compound of formula (I). The HIL 130 is disposed on the anode layer 120. A photoactive layer (PAL) 170 and a cathode layer 190 are disposed on the HIL 130.

[0190] Figure 2 is a schematic cross-sectional view of an organic light-emitting diode (OLED) 100 according to an exemplary embodiment of the present invention. The OLED 100 includes a substrate 110, an anode layer 120, and a hole injection layer (HIL) 130 which may contain a compound of formula (I). The HIL 130 is disposed on the anode layer 120. A hole transport layer (HTL) 140, an emissive layer (EML) 150, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190 are disposed on the HIL 130. Optionally, an electron transport layer stack (ETL) can be used instead of a single electron transport layer 160.

[0191] Figure 3 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. Figure 3 differs from Figure 2 in that the OLED 100 in Figure 3 includes an electron blocking layer (EBL) 145 and a hole blocking layer (HBL) 155.

[0192] Referring to Figure 3, the OLED 100 includes a substrate 110, an anode layer 120, a hole injection layer (HIL) 130 which may contain a compound of formula (I), a hole transport layer (HTL) 140, an electron blocking layer (EBL) 145, an emissive layer (EML) 150, a hole blocking layer (HBL) 155, an electron transport layer (ETL) 160, an electron injection layer (EIL) 180, and a cathode layer 190.

[0193] Figure 4 is a schematic cross-sectional view of an OLED 100 according to another exemplary embodiment of the present invention. Figure 4 differs from Figures 2 and 3 in that the OLED 200 of Figure 4 comprises a charge generation layer (CGL) and an additional electron transport layer (ETL) 161 that replaces the hole injection layer (HIL) 130 of the OLED 100 of Figure 3.

[0194] Referring to Figure 4, the OLED200 includes a substrate 110, an anode 120, a first electron transport layer (ETL1) 161, an n-type charge generation layer (n-type CGL) 185, a p-type charge generation layer (p-type GCL) 135 which may contain a compound of formula (I), a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first light-emitting layer (EML) 150, a first hole blocking layer (HBL) 155, a second electron transport layer (ETL2) 160, and a cathode 190.

[0195] In the above description, the method for manufacturing the OLED 100 of the present invention begins with a substrate 110 on which an anode 120 is formed, and on the anode electrode 120, a first electron transport layer 161, an n-type CGL 185, a p-type CGL 135, a first hole transport layer 140, an optional first electron blocking layer 145, a first light-emitting layer 150, an optional first hole blocking layer 155, an optional second electron transport layer 160, and a cathode 190 are formed in this order or in the reverse order.

[0196] Figure 5 is a schematic cross-sectional view of a series OLED 100 according to another exemplary embodiment of the present invention. Figure 5 differs from Figure 4 in that the OLED 100 of Figure 5 further includes a second light-emitting layer.

[0197] Referring to Figure 5, the OLED200 comprises a substrate 110, an anode 120, a hole injection layer (HIL) 130 which may contain a compound of formula (I), a first hole transport layer (HTL) 140, a first electron blocking layer (EBL) 145, a first light-emitting layer (EML) 150, a first hole blocking layer (HBL) 155, a first electron transport layer (ETL) 160, and an n-type charge generation layer ( The device includes an n-type CGL (185), a p-type charge generation layer (p-type GCL) (135) which may contain a compound of formula (I), a second hole transport layer (HTL) (141), a second electron blocking layer (EBL) (146), a second light-emitting layer (EML) (151), a second hole blocking layer (EBL) (156), a second electron transport layer (ETL) (161), an electron injection layer (EIL) (180), and a cathode (190).

[0198] In the above description, the method for manufacturing the OLED 100 of the present invention begins with a substrate 110 on which an anode 120 is formed, and on the anode electrode 120, a hole injection layer 130, a first hole transport layer 140, an optional first electron blocking layer 145, a first light-emitting layer 150, an optional first hole blocking layer 155, an optional at least one first electron transport layer 160, an n-type CGL 185, a p-type CGL 135, a second hole transport layer 141, an optional second electron blocking layer 146, a second light-emitting layer 151, an optional second hole blocking layer 156, an optional at least one second electron transport layer 161, an optional electron injection layer (EIL) 180, and a cathode 190 are formed in this order or in the reverse order.

[0199] Although not shown in Figures 1 to 5, a capping layer and / or sealing layer may be further formed on the cathode layer 190 to seal the organic electronic device 100. Various other modifications may also be applied.

[0200] One or more exemplary embodiments of the present invention will be described in detail below with reference to examples. However, these examples are not intended to limit the object and scope of one or more exemplary embodiments of the present invention.

[0201] [Detailed explanation] The present invention is merely illustrative and will be further illustrated by the following non-binding examples.

[0202] The compound of formula (I) may be prepared as described in EP2180029A1 or WO2016097017A1.

[0203] [Calculation of HOMO and LUMO] The HOMO and LUMO are calculated using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany). The optimized geometric arrangement of the molecular structure, as well as the energy levels of the HOMO and LUMO, are calculated in the gas phase from 6 to 31 G. * This is measured by applying the hybrid functional B3LYP, which has a basis set of . If more than one conformation is feasible, the conformation with the lowest total energy is selected.

[0204] [Thermogravimetric analysis] The term "TGA 5%" refers to the temperature at which a 5% weight loss occurs during thermogravimetric analysis, and is measured in °C.

[0205] The 5% TGA value can be determined by heating a 9-11 mg sample in an open 100 μL aluminum pan in a thermogravimetric analyzer at a heating rate of 10 K / min, under a nitrogen flow, at a flow rate of 20 mL / min in the balance region and 30 mL / min in the drying oven region.

[0206] The TGA 5% value can provide an indirect measure of a compound's volatility and / or decomposition temperature. In a first approximation, a higher TGA 5% value indicates lower volatility and / or a higher decomposition temperature of the compound.

[0207] According to one embodiment, the 5% TGA value of the compound of formula (I) is selected within the range of ≥280°C and ≤390°C, preferably ≥290°C and ≤380°C, and more preferably ≥295°C and ≤370°C.

[0208] [General procedures for OLED manufacturing] For bottom emission devices, as shown in Tables 3 and 5, there is a 15 Ω / cm² device with 90 nm ITO (available from Corning). 2 The glass substrate was cut to a size of 50 mm x 50 mm x 0.7 mm, ultrasonically cleaned with isopropyl alcohol for 5 minutes, washed with pure water for 5 minutes, and then cleaned again with ultraviolet ozone for 30 minutes to create the anodic layer.

[0209] Next, the compound of formula F3 and the compound of formula (I) according to Tables 3 and 5 were co-deposited onto the anode layer in a vacuum to form a 10 nm thick HIL. In Comparative Examples 1 and 2, comparative compound 1 and comparative compound 2 were used instead of the compound of formula (I). The compositions of the HILs are shown in Tables 3 and 5.

[0210] Next, the compound of formula F3 was vacuum-deposited onto the HIL to form a first HTL with a thickness of 128 nm.

[0211] Next, 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 onto the HTL to form a 5 nm thick electron blocking layer (EBL).

[0212] Next, 97 volume% of H09 (Sun Fine Chemicals, South Korea) as an EML host and 3 volume% of BD200 (Sun Fine Chemicals, South Korea) as a fluorescent blue dopant were co-deposited onto the EBL to form a first blue-emitting EML with a thickness of 20 nm.

[0213] Next, a hole blocking layer (HBL) with a thickness of 5 nm is formed by depositing 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine onto the light-emitting layer.

[0214] Next, a 25 nm thick electron transport layer (ETL) is formed on the hole blocking layer by co-depositing 50 wt% of 4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene-1-yl)-[1,1'-biphenyl]-4-carbonitrile and 50 wt% of LiQ.

[0215] Next, 10 -7 A cathode with a thickness of 100 nm is formed by depositing Al at a rate of 0.01 to 1 angstrom / s in mbar.

[0216] The OLED stack is protected from ambient conditions by encapsulating the device using a glass slide. This creates a cavity containing getter material for further protection.

[0217] [Organic electronic devices including a charge generation layer (CGL)] For devices including CGL, as shown in Table 4, there is 15 Ω / cm with 90 nm ITO (available from Corning). 2 The glass substrate was cut to a size of 50mm x 50mm x 0.7mm and ultrasonically cleaned with isopropyl alcohol for 5 minutes. Then it was washed with pure water for 5 minutes, and then again with ultraviolet ozone for 30 minutes to create the anodic layer.

[0218] Next, a 30 nm thick first electron transport layer (ETL1) is formed on the anode layer by co-depositing 50 wt% of 4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene-1-yl)-[1,1'-biphenyl]-4-carbonitrile and 50 wt% of LiQ.

[0219] Next, a 15 nm thick n-type CGL is formed on ETL1 by co-depositing 99 volume% of 2,2'-(1,3-phenylene)bis[9-phenyl-1,10-phenanthroline] and 1 volume% of Li.

[0220] Next, a p-type CGL with a thickness of 10 nm is formed on an n-type CGL by co-depositing a substantially covalent matrix compound and a compound of formula (I). The composition of the p-type CGL is shown in Table 4.

[0221] Next, a hole transport layer (HTL) with a thickness of 86 nm is formed on the p-type CGL by depositing a substantially covalent matrix compound. The composition of the HTL is shown in Table 4.

[0222] Next, an electron blocking layer (EBL) with a thickness of 5 nm is formed on the HTL by depositing N-([1,1'-biphenyl]-4-yl)-9,9-diphenyl-N-(4-(triphenylsilyl)phenyl)-9H-fluoren-2-amine.

[0223] Next, a 20 nm thick luminescent layer (EML) is formed on the EBL by co-depositing 97 volume% H09 (Sun Fine Chemicals, South Korea) as an EML host and 3 volume% BD200 (Sun Fine Chemicals, South Korea) as a fluorescent blue dopant.

[0224] Next, a 5 nm thick hole-blocking layer (HBL) is formed on the light-emitting layer by depositing 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine.

[0225] Next, a 25 nm thick second electron transport layer (ETL2) is formed on the hole blocking layer by co-depositing 50 wt% of 4'-(4-(4-(4,6-diphenyl-1,3,5-triazine-2-yl)phenyl)naphthalene-1-yl)-[1,1'-biphenyl]-4-carbonitrile and 50 wt% of LiQ.

[0226] Next, 10 -7 A 100 nm thick cathode layer is formed on the ETL2 by depositing Al at a rate of 0.01 to 1 angstrom / s in mbar.

[0227] The OLED stack is protected from ambient conditions by encapsulating the device in a glass slide. This creates a cavity containing getter material for further protection.

[0228] To evaluate the performance of the embodiments of the present invention compared to the prior art, current efficiency is measured at 20°C. The current-voltage characteristics are determined by supplying a voltage U in V and measuring the current flowing through the device under test in mA using a Keithley 2635 source measurement unit. The voltage applied to the device is varied in 0.1V steps in the range of 0V to 10V. Similarly, the luminance-voltage characteristics and CIE coordinates are measured for each voltage value using an Instrument Systems CAS-140CT array spectrometer (calibrated by Deutsche Akkreditierungsstelle (DAkkS)) in cd / m². 2 It is determined by measuring the brightness. The cd / A efficiency at 10 mA / cm2 is determined by interpolating the brightness-voltage and current-voltage characteristics, respectively.

[0229] In bottom-emission devices, luminescence is primarily Lambertian and quantified by % external quantum efficiency (EQE). To determine the EQE efficiency in %, the optical output of the device is measured using a photodiode calibrated at 10 mA / cm².

[0230] In top-emission devices, light emission is directed forward, non-Lambertian, and highly dependent on the microcavity. Therefore, the efficiency EQE is higher compared to bottom-emission devices. To determine the efficiency EQE in percentage, the device's optical output is 10 mA / cm². 2 Measurements are taken using a photodiode calibrated with [specific technology / method].

[0231] The device lifetime LT is calculated under ambient conditions (20°C) and 30 mA / cm². 2 The measurement is then taken using a Keithley 2400 source meter and recorded over time.

[0232] The device brightness is measured using a calibrated photodiode. The lifetime LT is defined as the time it takes for the device brightness to decrease to 97% of its initial value.

[0233] [Technical effects of the invention] Table 1 shows the LUMO levels and TGA 5%-temperature (where available) for Examples A1-A31 and Comparative Examples 1 and 2 (=C1 and C2). Table 2 shows the structures of comparative tests C1 and C2.

[0234] LUMO levels were set using the program package TURBOMOLE V6.5 (TURBOMOLE GmbH, Litzenhardtstrasse 19, 76135 Karlsruhe, Germany) to simulate 6-31G in the gas phase. * This was calculated by applying the hybrid functional B3LYP, which has a basis set of .

[0235] Comparative compound 1 has a LUMO level of -4.58 eV and a TGA 5% value at 265°C.

[0236] Comparative compound 2 has a LUMO level of -4.79 eV and a TGA 5% value at 268°C. Comparative compound 2 differs from comparative compound 1 in the number of CF3 groups. In comparative compound 2, two fluorine atoms are substituted by CF3 groups. As shown in Table 1, the LUMO level of the compound of formula (I) is more negative compared to comparative compound 1. A more negative LUMO level is beneficial because it allows for matrix compounds with a more negative HOMO level. However, the volatility is very similar.

[0237] In compound A1 of the present invention, the LUMO level is -4.82 eV. This is more negative than the LUMO level of comparative compound 2. Furthermore, the volatility is substantially improved at 297°C. Compound A1 of the present invention is A 1 ~A 3 It differs from comparative compound 2 in at least one of these aspects.

[0238] In compounds A2 to A31 of the present invention, the LUMO level and / or TGA 5% value are improved compared to comparative compounds 1 and 2.

[0239] [Table 1]

[0240] [Table 2]

[0241] Table 3 shows performance data for organic electroluminescent devices including a hole injection layer (HIL) containing comparative compounds and the compound of the present invention:

[0242] [Table 3]

[0243] As can be seen from Table 3, the operating voltage U of all devices is lower than that of the comparative compounds. The external quantum efficiency EQE is improved compared to Comparative Examples 1 and 2.

[0244] Lower operating voltage and improved efficiency can be beneficial in reducing power consumption and improving battery life, especially in mobile devices.

[0245] Furthermore, the lifespan (LT) has increased to that of Comparative Examples 1 and 2.

[0246] Improved long-term stability (LT) is beneficial for improving the long-term stability of organic electronic devices.

[0247] Table 4 shows performance data for an organic electroluminescent device including a p-type charge injection layer (p-type CGL) containing the compound of the present invention.

[0248] [Table 4]

[0249] High EQE can be beneficial, particularly in mobile devices, for reducing power consumption and improving battery life.

[0250] The improved LT97 may be beneficial for extending the lifespan of organic electronic devices.

[0251] Table 5 shows performance data for organic electroluminescent devices including a hole injection layer (HIL) containing comparative compounds and the compound of the present invention:

[0252] [Table 5]

[0253] As can be seen from Table 5, the performance of the OLEDs is comparable to that of Examples 1-4 in Table 3. Referring to Table 3, the performance of Examples 7-23 is improved compared to Comparative Examples 1 and 2.

[0254] The specific combinations of elements and features in the detailed embodiments described above are illustrative only, and it is expressly intended that these teachings may be replaced with other teachings in the patent / application incorporated by such teachings and references. As those skilled in the art will recognize, variations, modifications, and other embodiments of those described herein can be conceived by those skilled in the art without departing from the spirit and scope of the claimed invention. Accordingly, the above description is merely illustrative and not intended to limit. In the claims, the term “comprising” does not exclude other elements or steps, and the indefinite article “a” or “an” does not exclude plural states. The mere fact that certain means are described in different dependent claims does not imply that combinations of these means cannot be used advantageously. The scope of the invention is defined in the following claims and their equivalents. Furthermore, the reference numerals used in the description and claims do not limit the scope of the claimed invention. [Brief explanation of the drawing]

[0255] [Figure 1] Figure 1 is a schematic cross-sectional view of an organic electronic device according to an exemplary embodiment of the present invention. [Figure 2] Figure 2 is a schematic cross-sectional view of an organic light-emitting diode (OLED) according to an exemplary embodiment of the present invention. [Figure 3] Figure 3 is a schematic cross-sectional view of an OLED according to an exemplary embodiment of the present invention. [Figure 4] Figure 4 is a schematic cross-sectional view of a series OLED including a charge generation layer according to an exemplary embodiment of the present invention. [Figure 5] Figure 5 is a schematic cross-sectional view of a series OLED including a charge generation layer according to an exemplary embodiment of the present invention.

Claims

1. A compound of formula (I): 【Chemistry 1】 In the formula, A １ This is selected from equation (II), 【Chemistry 2】 X １ CR １ or selected from N; X ２ CR ２ or selected from N; X ３ CR ３ or selected from N; X ４ is selected from CR ４ or N; X ５ CR ５ or selected from N; (If present) R １ , R ２ , R ３ , R ４ and R ５ These are independently CN, partially fluorinated or fully fluorinated C １ ~C ８ Selected from alkyl, F, D, or H, thereby R １ , R ２ , R ３ , R ４ and R ５ If any of the above exists, the corresponding X １ , X ２ , X ３ , X ４ and X ５ It is not N; however, R １ ~R ５ At least one of is selected from D or H, and, R １ and / or R ５ Either of these independently comprises CN, partially fluorinated or fully fluorinated C １ ~C ８ Selected from alkyl groups, or R ｎ and R ｎ＋１ At least one of (n=1-4) is independently CN, partially fluorinated or fully fluorinated C １ ~C ８ Selected from alkyl groups; R １ and R ３ These are independently CN, partially fluorinated or fully fluorinated C １ ~C ８ Selected from alkyl groups, A ２ and A ３ It is independently selected from equation (III), 【Transformation 3】 In the formula, Ar is independently a substituted or unsubstituted C. ６ ~C １８ Aryl and substituted or unsubstituted C ２ ~C １８ Selected from heteroaryls, the substituents on Ar are independently CN, partially or fully fluorinated C １ ~C ６ Selected from alkyl, F, and D, R' is selected from CN; In the formula, the asterisk "*" indicates the bonding position. A １ and A ３ These are not identical compounds.

2. A compound selected from formula (IV), 【Chemistry 4】 In the formula, B １ is selected from equation (V), 【Transformation 5】 B ３ and B ５ is Ar, and B ２ , B ４ and B ６ The compound according to claim 1, wherein R' is present.

3. X １ and / or X ５ The compound according to claim 1 or 2, wherein either of the members is C-CN.

4. X １ and / or X ２ The compound according to any one of claims 1 to 3, wherein is C-CN.

5. X １ and X ３ The compound according to any one of claims 1 to 4, wherein is C-CN.

6. R １ ~R ５ At least three of these are, independently, CN, partially fluorinated or fully fluorinated C １ ~C ８ A compound according to any one of claims 1 to 5, selected from alkyl and F.

7. 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 the at least one organic semiconductor layer comprises a compound according to any one of claims 1 to 6.

8. The organic semiconductor layer comprises a composition containing a compound of formula (IV) and at least one compound of formulas (IVa) to (IVd), 【Transformation 6】 【change】 In the formula, B １ is selected from equation (V), 【Transformation 7】 B ３ and B ５ is Ar, and B ２ , B ４ and B ６ The organic electronic device according to claim 7, wherein R' is R'.

9. The organic electronic device according to claim 7 or 8, wherein the organic electronic device includes at least one photoactive layer, the at least one photoactive layer is disposed between the anode layer and the cathode layer, and at least one of the at least one organic semiconductor layer is disposed between the anode layer and the at least one photoactive layer.

10. The organic electronic device according to any one of claims 7 to 9, wherein the organic electronic device comprises at least two photoactive layers, the at least two photoactive layers comprising a first photoactive layer and a second photoactive layer, and at least one of the at least one organic semiconductor layer is disposed between the first photoactive layer and the second photoactive layer.

11. The organic electronic device according to any one of claims 7 to 10, wherein the aforementioned electronic organic device is an electroluminescent device.

12. A display device comprising an organic electronic device according to any one of claims 7 to 11.

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