Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display device

Abstract

The present invention relates to a compound for organic optoelectronic devices represented by Chemical Formula 1, a composition for organic optoelectronic devices containing the same, an organic optoelectronic device, and a display device. The details regarding the above chemical formula 1 are as defined in the specification.

Description

Technology Field

[0001] This relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Technology

[0002] An organic optoelectronic diode is a device capable of converting electrical energy and light energy.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles. One is a photovoltaic device that generates electrical energy as excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0004] Examples of organic optoelectronic devices include organic photovoltaic devices, organic light-emitting diodes, organic solar cells, and organic photoconductor drums.

[0005] Among these, organic light-emitting diodes (OLEDs) have recently been receiving significant attention due to the increasing demand for flat panel display devices. As an organic light-emitting diode is a device that converts electrical energy into light, its performance is greatly influenced by the organic material located between the electrodes. The problem to be solved

[0006] One embodiment provides a compound for organic optoelectronic devices capable of realizing high-efficiency and long-life organic optoelectronic devices.

[0007] Another embodiment provides a composition for an organic optoelectronic device comprising the above-mentioned compound for the organic optoelectronic device.

[0008] Another embodiment provides an organic optoelectronic device comprising the above-mentioned compound for the organic optoelectronic device or composition for the organic optoelectronic device.

[0009] Another embodiment provides a display device including the organic optoelectronic element. means of solving the problem

[0010] According to one embodiment, a compound represented by the following chemical formula 1 is provided.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] Z 1 To Z 3 Each independently N or CR a And,

[0015] Z 1 To Z 3 At least two of them are N, and

[0016] Ar 1 or Ar 4 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, and

[0017] Ar 1 or Ar 4 One of them is a group represented by the following chemical formula A, and

[0018] [Chemical Formula A]

[0019]

[0020] L 1 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0021] R a and R 1 to R 3Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0022] m1 to m3 are each independently one of integers 1 to 4, and

[0023] * is a connection point,

[0024] Chemical formula 1 satisfies at least one of the following conditions (i) to (iii).

[0025] (i) Ar 1 or Ar 4 Among the remaining substituents not substituted with the above chemical formula A, at least one is a substituted or unsubstituted C10 to C30 aryl group;

[0026] (ii) R 2 and R 3 At least one of the following is a substituted or unsubstituted C10 to C30 aryl group;

[0027] (iii) R 1 It is a substituted or unsubstituted C6 to C30 aryl group

[0028] According to another embodiment, a composition for an organic optoelectronic device comprising a first compound and a second compound is provided.

[0029] The first compound above is a compound for an organic optoelectronic device as described above, and the second compound can be represented by the following chemical formula 2; or a combination of the following chemical formulas 3 and 4.

[0030] [Chemical Formula 2]

[0031]

[0032] In the above chemical formula 2,

[0033] R 4 to R 8Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0034] Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0035] L 2 and L 3 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0036] m4, m7, and m8 are each independently one of integers from 1 to 4, and

[0037] m5 and m6 are each independently one of integers from 1 to 3, and

[0038] n is one of integers from 0 to 2;

[0039] [Chemical Formula 3] [Chemical Formula 4]

[0040]

[0041] In the above chemical formulas 3 and 4,

[0042] a1* to a4* of Chemical Formula 3 are each independently connected carbon (C) or Cl a -R a And,

[0043] Among a1* to a4* of Chemical Formula 3, two adjacent ones are each connected to * of Chemical Formula 4, and

[0044] L a , L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0045] R a , R9 and R 10 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0046] Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0047] m9 and m10 are each independently one of integers from 1 to 4.

[0048] According to another embodiment, an organic optoelectronic device is provided comprising an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises a compound for the organic optoelectronic device or a composition for the organic optoelectronic device.

[0049] According to another embodiment, a display device comprising the organic optoelectronic element is provided. Effects of the invention

[0050] High-efficiency, long-life organic optoelectronic devices can be realized. Brief explanation of the drawing

[0051] FIG. 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment. Specific details for implementing the invention

[0052] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention, and the present invention is defined only by the scope of the claims set forth below.

[0053] In this specification, "substitution" means that, unless otherwise defined, at least one hydrogen of a substituent or compound is substituted with a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0054] In one example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. Furthermore, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. Furthermore, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen of a substituent or compound is substituted with a deuterium, cyano group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, terphenyl group, or naphthyl group.

[0055] In this specification, “non-substituted” means that a hydrogen atom remains a hydrogen atom without being substituted by another substituent.

[0056] In this specification, “hydrogen substitution (-H)” may include “deuterium substitution (-D) or “tritium substitution (-T).”

[0057] In this specification, "hetero" means, unless otherwise defined, that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder is carbon.

[0058] In this specification, "aryl group" is a collective concept for a group having one or more hydrocarbon aromatic moietys, including a form in which all elements of the hydrocarbon aromatic moiety have p-orbitals and these p-orbitals form a conjugation, such as a phenyl group, a naphthyl group, etc., and a form in which two or more hydrocarbon aromatic moietys are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moietys are directly or indirectly fused, such as a fluorenyl group, etc.

[0059] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0060] In this specification, "heterocyclic group" is a superordinate concept including heteroaryl groups, meaning that a cyclic compound, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C). If the heterocyclic group is a fused ring, it may contain one or more heteroatoms in the entire heterocyclic group or in each ring.

[0061] For example, a "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si within the aryl group. Two or more heteroaryl groups may be directly connected through sigma bonds, or if the heteroaryl group comprises two or more rings, the two or more rings may be fused together. If the heteroaryl group is a fused ring, each ring may contain one to three heteroatoms.

[0062] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0063] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic groups are a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazoleyl group, a substituted or unsubstituted triazoleyl group, a substituted or unsubstituted oxazoleyl group, a substituted or unsubstituted thiazoleyl group, a substituted or unsubstituted oxadiazoleyl group, a substituted or unsubstituted thiadiazoleyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazoleyl group, a substituted or unsubstituted indoleyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthiridinyl group, a substituted or unsubstituted benzoxazine dil group, a substituted or unsubstituted benzthiazine dil group, a substituted or unsubstituted acrridinyl group, a substituted or unsubstituted phenazine dil group, a substituted or unsubstituted phenothiazine dil group, a substituted or unsubstituted phenoxazine dil group, a substituted or unsubstituted carbazole dil group, a substituted or unsubstituted dibenzofuran dil group, a substituted or unsubstituted dibenzothiophen dil group, a substituted or unsubstituted benzonaphtufuran dil group, a substituted or unsubstituted benzonaphthiophen dil group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0064] In this specification, the term "hole characteristic" refers to a characteristic that can form holes by donating electrons when an electric field is applied, and means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and movement within the light-emitting layer by having a conduction characteristic along the HOMO level.

[0065] In addition, electronic properties refer to the ability to receive electrons when an electric field is applied, and they refer to properties that facilitate the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed at the light-emitting layer to the cathode, and the movement of electrons within the light-emitting layer by having conduction properties along the LUMO level.

[0066] A compound for an organic optoelectronic device according to one embodiment is described below.

[0067] A compound for an organic optoelectronic device according to one embodiment is represented by the following chemical formula 1.

[0068] [Chemical Formula 1]

[0069]

[0070] In the above chemical formula 1,

[0071] Z 1 To Z 3 Each independently N or CR a And,

[0072] Z 1 To Z 3 At least two of them are N, and

[0073] Ar 1 or Ar 4 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C6 to C30 aryl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, and

[0074] Ar 1 or Ar 4 One of them is a group represented by the following chemical formula A, and

[0075] [Chemical Formula A]

[0076]

[0077] L 1 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0078] Ra and R 1 to R 3 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0079] m1 to m3 are each independently one of integers 1 to 4, and

[0080] * is a connection point,

[0081] Chemical formula 1 satisfies at least one of the following conditions (i) to (iii).

[0082] (i) Ar 1 or Ar 4 Among the remaining substituents not substituted with the above chemical formula A, at least one is a substituted or unsubstituted C10 to C30 aryl group;

[0083] (ii) R 2 and R 3 At least one of the following is a substituted or unsubstituted C10 to C30 aryl group;

[0084] (iii) R 1 It is a substituted or unsubstituted C6 to C30 aryl group

[0085] In the above Chemical Formula 1, when m1 is 2 or more, each R 1 They may be the same or different from each other.

[0086] In the above Chemical Formula 1, when m2 is 2 or more, each R 2 They may be the same or different from each other.

[0087] In the above Chemical Formula 1, when m3 is 2 or more, each R 3 They may be the same or different from each other.

[0088] The compound represented by Chemical Formula 1 is characterized in that another triazine or pyrimidine is linked to the triazine by an ortho-phenylene group, and the triazine and / or pyrimidine essentially comprises a carbazoleyl group, and in particular, the triazine, pyrimidine (or triazine), linker (ortho-phenylene), and carbazoleyl group further comprise an aryl group of C10 or more.

[0089] By linking another triazine or pyrimidine to the triazine via an ortho-phenylene group, the lifetime can be improved compared to other substitution positions, and excellent lifetime characteristics can be achieved, particularly by including a carbazole group as a requirement. By additionally including C10 or higher aryl groups, the electron cloud of the LUMO is expanded, thereby improving electron transport capability, which in turn improves the driving voltage and enables high efficiency by appropriately controlling the emission zone.

[0090] For example, depending on the substitution position of the carbazole group, the above chemical formula 1 can be represented as the following chemical formula 1A or chemical formula 1B.

[0091] [Chemical Formula 1A]

[0092]

[0093] In the above chemical formula 1A, Z 1 To Z 3 , Ar 1 or Ar 4 , L 1 , R 1 to R 3 and the definitions of m1 to m3 are as defined in Chemical Formula 1, and

[0094] Chemical formula 1A satisfies at least one of the following conditions (iii) to (v).

[0095] (iii) Ar 2 or Ar 4 At least one of the following is a substituted or unsubstituted C10 to C30 aryl group;

[0096] (iv) R 2 and R3 At least one of the following is a substituted or unsubstituted C10 to C30 aryl group;

[0097] (v) R 1 It is a substituted or unsubstituted C6 to C30 aryl group

[0098] [Chemical Formula 1B]

[0099]

[0100] In the above chemical formula 1B, Z 1 To Z 3 , Ar 1 or Ar 4 , L 1 , R 1 to R 3 and the definitions of m1 to m3 are as defined in Chemical Formula 1, and

[0101] Chemical formula 1B satisfies at least one of the following conditions (vi) to (viii).

[0102] (vi) Ar 1 or Ar 3 At least one of the following is a substituted or unsubstituted C10 to C30 aryl group;

[0103] (vii) R 2 and R 3 At least one of the following is a substituted or unsubstituted C10 to C30 aryl group;

[0104] (viii) R 1 It is a substituted or unsubstituted C6 to C30 aryl group

[0105] As a specific example, the above chemical formula 1A can be expressed as any one of the following chemical formulas 1A-I, 1A-II, and 1A-III.

[0106] [Chemical Formula 1A-I]

[0107]

[0108] [Chemical Formula 1A-II]

[0109]

[0110] [Chemical Formula 1A-III]

[0111]

[0112] In the above chemical formulas 1A-I, 1A-II, and 1A-III, Ar 2 or Ar 4 , L 1 , R 1 to R 3 and m1 to m3 are as defined in Chemical Formula 1A.

[0113] As a specific example, the above chemical formula 1B can be expressed as either the following chemical formula 1B-II or chemical formula 1B-III.

[0114] [Chemical Formula 1B-II]

[0115]

[0116] [Chemical Formula 1B-III]

[0117]

[0118] In the above Chemical Formulas 1B-II and 1B-III, Ar 1 or Ar 3 , L 1 , R 1 to R 3 and m1 to m3 are as defined in Chemical Formula 1B.

[0119] For example, Ar of the above chemical formula 1 1 or Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazoleyl group, and

[0120] The above Ar 1 or Ar 4 At least one of them is a group represented by the above chemical formula A, and

[0121] Chemical formula 1 satisfies at least one of the following conditions (ix) to (xi).

[0122] (ix) Ar 1 or Ar 4 At least one of the remaining substituents not substituted with the above formula A is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted triphenylene group;

[0123] (x) R 2 and R 3 At least one of the following is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted triphenylene group;

[0124] (xi) R 1 It is a substituted or unsubstituted C6 to C12 aryl group

[0125] For example, R of the above chemical formula 1 1 to R 3 Each may independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0126] A compound for an organic optoelectronic device according to one embodiment may be represented by any one of the above formulas 1A-I, 1A-II, and 1B-II.

[0127] For example, a compound for an organic optoelectronic device represented by Chemical Formula 1 may be selected from the compounds listed in Group 1 below, but is not limited thereto.

[0128] [Group 1]

[0129] [A-1] [A-2] [A-3] [A-4]

[0130]

[0131] [A-5] [A-6] [A-7] [A-8]

[0132]

[0133] [A-9] [A-10] [A-11] [A-12]

[0134]

[0135] [A-13] [A-14] [A-15] [A-16]

[0136]

[0137] [A-17] [A-18] [A-19] [A-20]

[0138]

[0139] [A-21] [A-22] [A-23] [A-24]

[0140]

[0141] [A-25] [A-26] [A-27] [A-28]

[0142]

[0143] [A-29] [A-30] [A-31] [A-32]

[0144]

[0145] [A-33] [A-34] [A-35] [A-36]

[0146]

[0147] [A-37] [A-38] [A-39] [A-40]

[0148]

[0149] [A-41] [A-42] [A-43] [A-44]

[0150]

[0151] [A-45] [A-46] [A-47] [A-48]

[0152]

[0153] [A-49] [A-50] [A-51] [A-52]

[0154]

[0155] [A-53] [A-54] [A-55] [A-56]

[0156]

[0157] [A-57] [A-58] [A-59] [A-60]

[0158]

[0159] [A-61] [A-62] [A-63] [A-64]

[0160]

[0161] [A-65] [A-66] [A-67] [A-68]

[0162]

[0163] [A-69] [A-70] [A-71] [A-72]

[0164]

[0165] [A-73] [A-74] [A-75] [A-76]

[0166]

[0167] [A-77] [A-78] [A-79] [A-80]

[0168]

[0169] [A-81] [A-82] [A-83] [A-84]

[0170]

[0171] [A-85] [A-86] [A-87] [A-88]

[0172]

[0173] [A-89]

[0174]

[0175] A composition for an organic optoelectronic device according to another embodiment comprises a first compound and a second compound, wherein the first compound is the aforementioned compound for an organic optoelectronic device, and the second compound may be represented by the following formula 2; or a combination of formulas 3 and 4.

[0176] [Chemical Formula 2]

[0177]

[0178] In the above chemical formula 2,

[0179] R 4 to R 8 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0180] Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0181] L 2 and L 3 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0182] m4, m7, and m8 are each independently one of integers from 1 to 4, and

[0183] m5 and m6 are each independently one of integers from 1 to 3, and

[0184] n is one of integers from 0 to 2;

[0185] [Chemical Formula 3] [Chemical Formula 4]

[0186]

[0187] In the above chemical formulas 3 and 4,

[0188] a1* to a4* of Chemical Formula 3 are each independently connected carbon (C) or Cl a -R a And,

[0189] Among a1* to a4* of Chemical Formula 3, two adjacent ones are each connected to * of Chemical Formula 4, and

[0190] L a , L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0191] R a , R 9 and R 10 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0192] Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0193] m9 and m10 are each independently one of integers from 1 to 4.

[0194] The second compound mentioned above can be used in the light-emitting layer together with the first compound to increase charge mobility and stability, thereby improving luminous efficiency and lifespan characteristics.

[0195] In the above Chemical Formula 2, when m4 is 2 or more, each R 4 They may be the same or different from each other.

[0196] In the above Chemical Formula 2, when m5 is 2 or more, each R 5 They may be the same or different from each other.

[0197] In the above Chemical Formula 2, when m6 is 2 or more, each R 6 They may be the same or different from each other.

[0198] In the above Chemical Formula 2, when m7 is 2 or more, each R 7 They may be the same or different from each other.

[0199] In the above chemical formula 2, when m8 is 2 or more, each R 8 They may be the same or different from each other.

[0200] As an example, Ar of the above chemical formula 2 5 and Ar 6 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0201] L of the above chemical formula 2 2 and L 3 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and

[0202] R of the above chemical formula 2 4 to R 7 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0203] n can be 0 or 1.

[0204] For example, the term "substitution" in the above chemical formula 2 means that at least one hydrogen is substituted with a deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0205] In a specific embodiment of the present invention, the formula 2 may be represented by one of the following formulas 2-1 to 2-15.

[0206] [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3]

[0207]

[0208] [Chemical Formula 2-4] [Chemical Formula 2-5] [Chemical Formula 2-6]

[0209]

[0210] [Chemical Formula 2-7] [Chemical Formula 2-8] [Chemical Formula 2-9]

[0211]

[0212] [Chemical Formula 2-10] [Chemical Formula 2-11] [Chemical Formula 2-12]

[0213]

[0214] [Chemical Formula 2-13] [Chemical Formula 2-14] [Chemical Formula 2-15]

[0215]

[0216] In the above chemical formulas 2-1 to 2-15, R 4 to R 8 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and *-L 2 -Ar 5 and *-L 3 -Ar 6 Each can be independently one of the substituents listed in Group I below.

[0217] [Group I]

[0218]

[0219] In the above Group I,

[0220] R 11 to R 13Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and

[0221] m11 is one of integers from 1 to 5, and

[0222] m12 is one of integers from 1 to 4, and

[0223] m13 is one of integers from 1 to 3, and

[0224] * is a connection point.

[0225] In the above Group I, when m11 is 2 or more, each R 11 They may be the same or different from each other.

[0226] In the above Group I, when m12 is 2 or more, each R 12 They may be the same or different from each other.

[0227] In the above Group I, when m13 is 2 or more, each R 13 They may be the same or different from each other.

[0228] In one embodiment, the above chemical formula 2 can be represented by the above chemical formula 2-8.

[0229] In addition, *-L of the above chemical formula 2-8 2 -Ar 5 and *-L 3 -Ar 6 Each can be independently selected from the above Group I.

[0230] In the above Chemical Formulas 3 and 4, when m9 is 2 or more, each R 9 They may be the same or different from each other.

[0231] In the above Chemical Formulas 3 and 4, when m10 is 2 or more, each R 10 They may be the same or different from each other.

[0232] For example, the second compound represented by a combination of the above chemical formulas 3 and 4 may be represented by any one of the following chemical formulas 3A, 3B, 3C, 3D, and 3E.

[0233] [Chemical Formula 3A] [Chemical Formula 3B] [Chemical Formula 3C]

[0234]

[0235] [Chemical Formula 3D] [Chemical Formula 3E]

[0236]

[0237] In the above chemical formulas 3A to 3E, L 4 , L 5 , R 9 and R 10 It is as previously stated, and

[0238] L a1 to L a4 is the aforementioned L 4 and L 5 It is the same as the definition of,

[0239] R a1 to R a4 is the aforementioned R 9 and R 10 It is the same as the definition of.

[0240] For example, Ar of the above chemical formulas 3 and 4 7 and Ar 8 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0241] R a1 to R a4 , R 9 , and R 10Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0242] In a specific embodiment of the present invention, *-L of formulas 3 and 4 4 -Ar 7 and *-L 5 -Ar 8 Each can be independently selected from the substituents listed in Group I above.

[0243] In one embodiment, the R a1 to R a4 , R 9 and R 10 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0244] For example, the above R a1 to R a4 , R 9 and R 10 Each can independently be a hydrogen, deuterium, cyano group, or a substituted or unsubstituted phenyl group, and

[0245] In a specific embodiment, the R a1 to R a4 , R 9 , and R 10 Each can independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0246] In a specific embodiment of the present invention, the second compound may be represented by the formula 2-8, and the Ar of the formula 2-8 5 and Ar 6Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and L 2 and L 3 Each is independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and R 4 to R 7 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0247] In another specific embodiment of the present invention, the second compound may be represented by the formula 3C, and L of the formula 3C a3 and L a4 is a single bond, and L 4 and L 5 Each is independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and R 9 , R 10 , R a3 and R a4 Each is independently hydrogen, deuterium, or a phenyl group, and Ar 7 and Ar 8 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0248] For example, the compound for the second organic optoelectronic device may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0249] [Group 2]

[0250] [B-1] [B-2] [B-3] [B-4] [B-5]

[0251]

[0252] [B-6] [B-7] [B-8] [B-9] [B-10]

[0253]

[0254] [B-11] [B-12] [B-13] [B-14] [B-15]

[0255]

[0256] [B-16] [B-17] [B-18] [B-19] [B-20]

[0257]

[0258] [B-21] [B-22] [B-23] [B-24] [B-25]

[0259]

[0260] [B-26] [B-27] [B-28] [B-29] [B-30]

[0261]

[0262] [B-31] [B-32] [B-33] [B-34] [B-35]

[0263]

[0264] [B-36] [B-37] [B-38] [B-39] [B-40]

[0265]

[0266] [B-41] [B-42] [B-43] [B-44] [B-45]

[0267]

[0268] [B-46] [B-47] [B-48] [B-49] [B-50]

[0269]

[0270] [B-51] [B-52] [B-53] [B-54] [B-55]

[0271]

[0272] [B-56] [B-57] [B-58] [B-59] [B-60]

[0273]

[0274] [B-61] [B-62] [B-63] [B-64] [B-65]

[0275]

[0276] [B-66] [B-67] [B-68] [B-69] [B-70]

[0277]

[0278] [B-71] [B-72] [B-73] [B-74] [B-75]

[0279]

[0280] [B-76] [B-77] [B-78] [B-79] [B-80]

[0281]

[0282] [B-81] [B-82] [B-83] [B-84] [B-85]

[0283]

[0284] [B-86] [B-87] [B-88] [B-89] [B-90]

[0285]

[0286] [B-91] [B-92] [B-93] [B-94] [B-95]

[0287]

[0288] [B-96] [B-97] [B-98] [B-99] [B-100]

[0289]

[0290] [B-101] [B-102] [B-103] [B-104] [B-105]

[0291]

[0292] [B-106] [B-107] [B-108] [B-109] [B-110]

[0293]

[0294] [B-111] [B-112] [B-113] [B-114] [B-115]

[0295]

[0296] [B-116] [B-117] [B-118] [B-119] [B-120]

[0297]

[0298] [B-121] [B-122] [B-123] [B-124] [B-125]

[0299]

[0300] [B-126] [B-127] [B-128] [B-129] [B-130]

[0301]

[0302] [B-131] [B-132] [B-133] [B-134] [B-135]

[0303]

[0304] [B-136] [B-137] [B-138] [B-139] [B-140]

[0305]

[0306] [B-141] [B-142] [B-143] [B-144] [B-145]

[0307]

[0308] [B-146] [B-147] [B-148] [B-149] [B-150]

[0309]

[0310] [B-151] [B-152] [B-153] [B-154] [B-155]

[0311]

[0312] [B-156] [B-157] [B-158] [B-159] [B-160]

[0313]

[0314] [B-161] [B-162] [B-163] [B-164]

[0315]

[0316] [B-165] [B-166] [B-167] [B-168]

[0317]

[0318] [B-169] [B-170] [B-171] [B-172]

[0319]

[0320] [B-173] [B-174] [B-175] [B-176] [B-177]

[0321]

[0322] [B-178] [B-177] [B-180] [B-181]

[0323]

[0324] [B-182] [B-183] [B-184] [B-185]

[0325]

[0326] [B-186] [B-187] [B-188] [B-189]

[0327]

[0328] [B-190] [B-191] [B-192] [B-193] [B-194]

[0329]

[0330] [C-1] [C-2] [C-3] [C-4]

[0331]

[0332] [C-5] [C-6] [C-7] [C-8]

[0333]

[0334] [C-9] [C-10] [C-11] [C-12]

[0335]

[0336] [C-13] [C-14] [C-15] [C-16]

[0337]

[0338] [C-17] [C-18] [C-19] [C-20]

[0339]

[0340] [C-21] [C-22] [C-23] [C-24]

[0341]

[0342] [C-25] [C-26] [C-27] [C-28]

[0343]

[0344] [C-29] [C-30] [C-31] [C-32]

[0345]

[0346] [C-33] [C-34] [C-35] [C-36]

[0347]

[0348] [C-37] [C-38] [C-39] [C-40]

[0349]

[0350] [C-41] [C-42] [C-43] [C-44]

[0351]

[0352] [C-45] [C-46] [C-47] [C-48]

[0353]

[0354] [C-49] [C-50] [C-51] [C-52]

[0355]

[0356] [C-53] [C-54] [C-55] [C-56]

[0357]

[0358] [C-57] [C-58] [C-59]

[0359]

[0360] [C-60] [C-61] [C-62] [C-63]

[0361]

[0362] [C-64] [C-65] [C-66] [C-67]

[0363]

[0364] [C-68] [C-69] [C-70] [C-71]

[0365]

[0366] [C-72] [C-73] [C-74] [C-75]

[0367]

[0368] [C-76] [C-77] [C-78] [C-79]

[0369]

[0370] [C-80] [C-81] [C-82] [C-83]

[0371]

[0372] [C-84] [C-85] [C-86] [C-87]

[0373]

[0374] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By including them within the above range, bipolar characteristics can be realized by adjusting the weight ratio appropriately using the electron transport ability of the first compound and the hole transport ability of the second compound, thereby improving efficiency and lifespan. Within the above range, they may be included in a weight ratio of, for example, about 10:90 to 90:10 or about 20:80 to 80:20, and for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, they may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0375] In addition to the aforementioned first and second compounds, one or more additional compounds may be included.

[0376] The aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices may be a composition further comprising a dopant.

[0377] The dopant can be, for example, a phosphorescent dopant, for example, a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0378] A dopant is a substance that is mixed in trace amounts into a compound or composition for an organic optoelectronic device to produce light emission, and generally, a substance such as a metal complex that emits light through multiple excitation, which excites it to a triplet state or higher, may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or more types.

[0379] Phosphorescent dopants are an example of a dopant, and examples of phosphorescent dopants include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants may include, for example, compounds represented by the following chemical formula Z, but are not limited thereto.

[0380] [Chemical Formula Z]

[0381] L 6 MX

[0382] In the above chemical formula Z, M is a metal, and L 6 and X are ligands that are the same or different from each other and form a complex with M.

[0383] The above M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and the above L 6 and X can be, for example, a bitentate ligand.

[0384] L 6 Examples of ligands represented by and X may be selected from the chemical formulas listed in Group A below, but are not limited thereto.

[0385] [Group A]

[0386]

[0387] In the above group A,

[0388] R 300 to R 302 Each is independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen, and

[0389] R 303 to R 324Each is independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0390] For example, it may include a dopant represented by the following chemical formula V.

[0391] [Chemical Formula V]

[0392]

[0393] In the above chemical formula V,

[0394] R 101 to R 116 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0395] The above R 132 to R 134 Each is independently a C1 to C6 alkyl group, and

[0396] R 101 to R 116 At least one of them is a functional group represented by the following chemical formula V-1, and

[0397] L 100It is a bidentate ligand of a monovalent anion that coordinates to iridium through lone pairs of electrons on carbon or heteroatoms, and

[0398] m19 and m20 are independently any one of integers from 0 to 3, and m19 + m20 is any one of integers from 1 to 3, and

[0399] [Chemical Formula V-1]

[0400]

[0401] In the above chemical formula V-1,

[0402] R 135 to R 139 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0403] * represents the part connected to the carbon atom.

[0404] For example, it may include a dopant represented by the following chemical formula Z-1.

[0405] [Chemical Formula Z-1]

[0406]

[0407] In the above chemical formula Z-1, rings A, B, C, and D each independently represent a pentagonal or hexagonal carbocyclic or heterocyclic ring;

[0408] R A , R B , R C , and R D Each independently represents a uniform, bisubstitution, trisubstitution, or quadruple substitution, or no substitution;

[0409] L B , L C , and L DEach is independently selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0410] If nA is 1, L E is selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; and when nA is 0, L E is not present;

[0411] R A , R B , R C , R D , R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; any adjacent R A , R B , R C , R D , R, and R' are arbitrarily connected to form a ring; X B , X C , X D , and X E are each independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 Each represents oxygen or direct bonding.

[0412] The dopant according to one embodiment may be a platinum complex, for example, represented by the following chemical formula VI.

[0413] [Chemical Formula VI]

[0414]

[0415] In the above chemical formula VI,

[0416] X 100 It contains O, S, and NR 131 Selected from among,

[0417] R 117 to R 131 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0418] The above R 132 to R 134 Each is independently a C1 to C6 alkyl group, and

[0419] R 117 to R 131 At least one of them is -SiR 132 R 133 R 134 or is a tert-butyl group, and

[0420] The above R 132 to R 134 Each is independently a C1 to C6 alkyl group.

[0421] An organic optoelectronic device to which the compound for organic optoelectronic devices or the composition for organic optoelectronic devices described above is applied is described below.

[0422] Organic optoelectronic devices are not particularly limited as long as they are devices capable of mutually converting electrical energy and light energy, and examples include organic photovoltaic devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0423] Here, an organic light-emitting diode, which is an example of an organic optoelectronic device, is described with reference to the drawing.

[0424] FIG. 1 is a cross-sectional view showing an organic light-emitting device according to one embodiment.

[0425] Referring to FIG. 1, an organic light-emitting device (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other, and an organic layer (105) located between the anode (120) and the cathode (110).

[0426] The anode (120) may be made of a conductor with a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The anode (120) may be a metal or an alloy thereof, such as nickel, platinum, vanadium, chromium, copper, zinc, gold; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole and polyaniline, but is not limited thereto.

[0427] The cathode (110) may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The cathode (110) may be a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc.; or a multilayer material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca, but is not limited thereto.

[0428] The organic layer (105) may include the aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices.

[0429] The above organic layer (105) includes a light-emitting layer (130), and the light-emitting layer (130) may include the aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices.

[0430] The above composition for an organic optoelectronic device further comprising a dopant may be, for example, a green light-emitting composition.

[0431] The light-emitting layer (130) may include, for example, the aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices as a phosphorescent host.

[0432] The organic layer may include additional charge transport regions in addition to the light-emitting layer.

[0433] The above charge transport region may be, for example, a hole transport region (140).

[0434] The hole transport region (140) can further increase hole injection and / or hole mobility between the anode (120) and the light-emitting layer (130) and block electrons.

[0435] Specifically, the hole transport region (140) may include a hole transport layer between the anode (120) and the light-emitting layer (130), and a hole transport auxiliary layer between the light-emitting layer (130) and the hole transport layer, and at least one of the compounds listed in Group B below may be included in at least one layer of the hole transport layer and the hole transport auxiliary layer.

[0436] [Group B]

[0437]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459] In addition to the aforementioned compound, known compounds and compounds with similar structures described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. may also be used in the hole transport region (140).

[0460] In addition, the charge transport region may be, for example, an electron transport region (150).

[0461] The above electron transport region (150) can further increase electron injection and / or electron mobility between the cathode (110) and the light-emitting layer (130) and block holes.

[0462] Specifically, the electron transport region (150) may include an electron transport layer between the cathode (110) and the light-emitting layer (130), and an electron transport auxiliary layer between the light-emitting layer (130) and the electron transport layer, and at least one of the compounds listed in Group C below may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0463] [Group C]

[0464]

[0465]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480] One embodiment may be an organic light-emitting device including a light-emitting layer as an organic layer.

[0481] Another embodiment may be an organic light-emitting device including a light-emitting layer and a hole transport region as the organic layer.

[0482] Another embodiment may be an organic light-emitting device including a light-emitting layer and an electron transport region as organic layers.

[0483] An organic light-emitting device according to one embodiment of the present invention may include a hole transport region (140) and an electron transport region (150) in addition to the light-emitting layer (130) as an organic layer (105) as shown in FIG. 1.

[0484] Meanwhile, the organic light-emitting device may additionally include an electron injection layer (not shown), a hole injection layer (not shown), etc., in addition to the light-emitting layer as the aforementioned organic layer.

[0485] An organic light-emitting device (100) can be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer using a dry film deposition method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and then forming a cathode or an anode thereon.

[0486] The above-described organic light-emitting element can be applied to an organic light-emitting display device.

[0488] The above-described embodiment will be explained in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the claims.

[0489] Unless otherwise noted, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or synthesized using known methods.

[0491] (Preparation of compounds for organic optoelectronic devices)

[0492] Synthesis Example 1: Synthesis of Compound A-12

[0493] [Reaction Equation 1]

[0494]

[0495] Step 1: Synthesis of Intermediate A-12-1

[0496] 9-(4-chloro-6-phenyl-1,3,5-triazin-2-yl)-9H-carbazole (50.0 g, 140.1 mmol), 2-chlorophenylboronic acid (23.0 g, 147.1 mmol), tetrakis(triphenylph osphine)palladium(0) (8.1 g, 7.0 mmol), and potassium carbonate (58.1 g, 420.4 mmol) were dissolved in 750 mL of a mixed solution of tetrahydrofuran and distilled water in a volume ratio of 2:1 and stirred under reflux at 80 °C for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane: n-hexane) to obtain 51.4 g (yield: 84.7%) of intermediate A-12-1.

[0497] Step 2: Synthesis of Intermediate A-12-2

[0498] Intermediate A-12-1 (51.4 g, 118.7 mmol), bis(pinacolato)diboron (39.2 g, 154.4 mmol), [1,1'bis(diphenylphosphino)ferrocene]palladium(II) dichloride (4.8 g, 5.9 mmol), potassium acetate (35.0 g, 356.2 mmol) and tricyclohexylphosphine (6.7 g, 23.8 mmol) N , N Add to 600 mL of dimethylformamide and reflux at 140 °C for 12 hours. Once the reaction is complete, pour into excess distilled water to completely precipitate the solid. Filter the precipitated solid, boil it in toluene to dissolve it, and filter it again through silica gel. Recrystallize the filtered solution to obtain 27.1 g (yield: 43.6%) of intermediate A-12-2.

[0499] Step 3: Synthesis of Compound A-12

[0500] Intermediate A-12-2 and 4-([1,1'-biphenyl]-4-yl)-2-chloro-6-phenylpyrimidine were used as starting materials and synthesized in the same manner as intermediate A-12-1 of Synthesis Example 1. Compound A-12 was obtained by recrystallization purification with toluene, yielding 4.7 g (yield: 69.2%).

[0502] Synthesis Examples 2 to 9

[0503] The compounds in Table 1 below were synthesized using reactant 1 and reactant 2 as starting materials through the three-step reaction (Suzuki rxn) of Synthesis Example 1.

[0504] Synthetic example Reactant 1 Reactant 2 product transference number Synthesis Example 2 Compound A-20 81.3% Synthesis Example 3 Compound A-89 66.4% Synthesis Example 4 Compound A-24 59.2% Synthesis Example 5 Compound A-51 69.9% Synthesis Example 6 Compound A-57 72.3% Synthesis Example 7 Compound A-74 49.5% Synthesis Example 8 Compound A-76 62.3% Synthesis Example 9 Compound A-84 77.0%

[0505] Comparative Synthesis Examples 1 to 6

[0506] The compounds in Table 2 below were synthesized using reactant 1 and reactant 2 as starting materials through the three-step reaction (Suzuki rxn) of Synthesis Example 1.

[0507] Synthetic example Reactant 1 Reactant 2 product transference number Comparative Synthesis Example 1 Compound C1 68.3% Comparative Synthesis Example 2 Compound C2 77.2% Comparative Synthesis Example 3 Compound C3 35.2% Comparative Synthesis Example 4 Compound C4 62.2% Comparative Synthesis Example 5 Compound C5 75.9% Comparative Synthesis Example 6 Compound C6 74.3%

[0508] (Preparation of the second compound)

[0509] Synthesis Example 10: Synthesis of Compound B-194

[0510] [Reaction Equation 2]

[0511]

[0512] Step 1: Synthesis of Compound Int 5

[0513] Compound Int 5 was synthesized by referring to the method disclosed in Korean Publication No. 2016-0049842.

[0514] Step 2: Synthesis of Compound B-194

[0515] 30 g (0.0535 mol) of Compound Int 5, 40 g (0.267 mol) of Trifluoromethanesulfonic acid, and 282 g (3.35 mol) of D6-benzene were added, and the mixture was stirred at 10°C for 24 hours. Purified water was added, and the mixture was neutralized with a saturated K3PO4 solution. The organic layer was concentrated and column-purified to obtain 18 g of Compound B-194 (white solid, LC-Mass Mz 578.79, C 42 H 10 D 18 Obtain N2).

[0517] (Fabrication of Organic Light Emitting Diodes)

[0518] Example 1

[0519] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition machine. Using the prepared ITO transparent electrode as the anode, a 100 Å thick hole injection layer was formed by vacuum depositing Compound A doped with 3% NDP-9 (commercially available from Novaled) on the ITO substrate, and a hole transport layer was formed by depositing Compound A to a thickness of 1350 Å on top of the hole injection layer. A hole transport auxiliary layer was formed by depositing Compound B to a thickness of 350 Å on top of the hole transport layer. On top of the hole transport assist layer, compound A-74 obtained in Synthesis Example 7 was used as a host and doped with 7 wt% PhGD as a dopant to form a 400 Å thick emissive layer by vacuum deposition. Subsequently, compound C was deposited to a thickness of 50 Å on top of the emissive layer to form an electron transport assist layer, and compound D and LiQ were vacuum deposited simultaneously in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. An organic light-emitting diode was fabricated by forming a cathode by sequentially vacuum depositing LiQ 15 Å and Al 1200 Å on top of the electron transport layer.

[0520] It was fabricated with the structure ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / Compound B (350Å) / EML[93 wt% host (Compound A-74) : 7 wt% PhGD](400Å) / Compound C(50Å) / Compound D:LiQ(300Å) / LiQ(15Å) / Al(1200Å).

[0521] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0522] Compound B: N-[4-(4-Dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0523] Compound C: 2,4-Diphenyl-6-(4',5',6'-triphenyl[1,1':2',1'':3'',1''':3''',1''''-quinquephenyl]-3''''-yl)-1,3,5-triazine

[0524] Compound D: 2-(1,1'-Biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0525] [PhGD]

[0526]

[0528] Examples 2 to 9 and Comparative Examples 1 to 6

[0529] The devices of Examples 2 to 9 and Comparative Examples 1 to 6 were fabricated in the same manner as Example 1, except that the host was changed as described in Tables 3 and 4 below.

[0531] Example 10

[0532] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was cleaned using distilled water ultrasonics. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents such as isopropyl alcohol, acetone, and methanol, dried, transferred to a plasma cleaner, cleaned using oxygen plasma for 10 minutes, and then transferred to a vacuum deposition machine. Using the prepared ITO transparent electrode as the anode, a 100 Å thick hole injection layer was formed by vacuum depositing compound A doped with 3% NDP-9 (commercially available from Novaled) on the ITO substrate, and a hole transport layer was formed by depositing compound A to a thickness of 1350 Å on top of the hole injection layer. A hole transport auxiliary layer was formed by depositing compound E to a thickness of 350 Å on top of the hole transport layer. On top of the hole transport assist layer, compound A-12 obtained in Synthesis Example 1 and compound B-194 obtained in Synthesis Example 10 were simultaneously used as hosts, and PhGD was doped at 10 wt% as a dopant to form a 330 Å thick emissive layer by vacuum deposition. Subsequently, compound F was deposited to a thickness of 50 Å on top of the emissive layer to form an electron transport assist layer, and compound G and LiQ were vacuum deposited simultaneously in a weight ratio of 1:1 to form an electron transport layer of 300 Å. An organic light-emitting diode was fabricated by forming a cathode by sequentially vacuum depositing LiQ 15 Å and Al 1200 Å on top of the electron transport layer.

[0533] It was fabricated with the structure ITO / compound A (3% NDP-9 doping, 100Å) / compound A (1350Å) / compound E (350Å) / EML [90 wt% host (compound A-12:compound B-194 = 4:6 w / w): 10 wt% PhGD] (330Å) / compound F (50Å) / compound G:LiQ (300Å) / LiQ (15Å) / Al (1200Å).

[0534] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0535] Compound F: 2-[3'-(9,9-Dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0536] Compound G: 2-[4-[4-(4'-Cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0538] Examples 11 to 18 and Comparative Examples 7 to 12

[0539] The devices of Examples 11 to 18 and Comparative Examples 7 to 12 were fabricated in the same manner as Example 2, except that the host and composition were changed as described in Tables 5 and 6 below.

[0541] evaluation

[0542] (1) Measurement of change in current density according to voltage change

[0543] For the fabricated organic light-emitting diode, the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0V to 10V, and the result was obtained by dividing the measured current value by the area.

[0544] (2) Measurement of change in brightness according to voltage change

[0545] For the fabricated organic light-emitting diode, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and the results were obtained.

[0546] (3) Measurement of luminous efficiency

[0547] Using the luminance and current density measured from (1) and (2) above, the same current density (10 mA / cm²) 2The luminous efficiency (cd / A) of ) was calculated.

[0548] Relative values ​​based on the luminous efficiency of Comparative Example 1 are shown in Table 3 below.

[0549] The relative values ​​based on the luminous efficiency of Comparative Example 4 are shown in Table 4 below.

[0550] The relative values ​​based on the luminous efficiency of Comparative Example 7 are shown in Table 5 below.

[0551] Relative values ​​based on the luminous efficiency of Comparative Example 10 are shown in Table 6 below.

[0552] (4) Life measurement

[0553] Initial luminance (cd / m²) using a polaronics lifetime measurement system for the fabricated organic light-emitting diodes 2 ) 24,000 cd / m 2 The T95 lifespan was determined by emitting light and measuring the decrease in brightness over time, at which the brightness decreased to 95% of the initial brightness.

[0554] Relative values ​​based on the T95 life of Comparative Example 1 are shown in Table 3 below.

[0555] Relative values ​​based on the T95 life of Comparative Example 4 are shown in Table 4 below.

[0556] The relative values ​​based on the T95 life of Comparative Example 7 are shown in Table 5 below.

[0557] Relative values ​​based on the T95 life of Comparative Example 10 are shown in Table 6 below.

[0558] (5) Driving voltage measurement

[0559] Using a current-voltage meter (Keithley 2400) at 15 mA / cm 2 The driving voltage of each component was measured to obtain the results.

[0560] The relative values ​​based on the driving voltage of Comparative Example 1 are shown in Table 3 below.

[0561] The relative values ​​based on the driving voltage of Comparative Example 4 are shown in Table 4 below.

[0562] The relative values ​​based on the driving voltage of Comparative Example 7 are shown in Table 5 below.

[0563] The relative values ​​based on the driving voltage of Comparative Example 10 are shown in Table 6 below.

[0564] Host Driving voltage (%) Luminous efficiency (%) Lifespan T95(%) Example 1 Compound A-74 88 112 190 Example 2 Compound A-76 85 116 230 Example 3 Compound A-84 93 108 250 Comparative Example 1 Compound C1 100 100 100 Comparative Example 2 Compound C2 96 104 140 Comparative Example 3 Compound C3 109 85 10

[0565] Host Driving voltage (%) Luminous efficiency (%) Lifespan T95(%) Example 4 Compound A-12 92 110 165 Example 5 Compound A-20 85 113 155 Example 6 Compound A-89 80 115 130 Example 7 Compound A-24 84 113 150 Example 8 Compound A-51 91 111 135 Example 9 Compound A-57 85 113 135 Comparative Example 4 Compound C4 100 100 100 Comparative Example 5 Compound C5 92 110 125 Comparative Example 6 Compound C6 92 110 60

[0566] Host No. 1 2nd host Driving voltage (%) Luminous efficiency (%) Example 10 Compound A-12 B-194 95 120 Example 11 Compound A-20 B-194 90 122 Example 12 Compound A-89 B-194 85 123 Example 13 Compound A-24 B-194 89 122 Example 14 Compound A-51 B-194 94 120 Example 15 Compound A-57 B-194 96 124 Comparative Example 7 Compound C1 B-194 100 100 Comparative Example 8 Compound C2 B-194 97 110 Comparative Example 9 Compound C3 B-194 110 80

[0567] Host No. 1 2nd host Driving voltage (%) Lifespan T95(%) Example 16 Compound A-74 B-194 96 170 Example 17 Compound A-76 B-194 94 190 Example 18 Compound A-84 B-194 95 210 Comparative Example 10 Compound C4 B-194 100 100 Comparative Example 11 Compound C5 B-194 99 110 Comparative Example 12 Compound C6 B-194 99 40

[0568] Referring to Tables 3 and 4, it can be confirmed that the organic light-emitting device to which the compound according to the embodiment of the present invention is applied has significantly improved driving voltage, efficiency, and lifespan characteristics compared to the organic light-emitting device according to the comparative example, and

[0569] In particular, referring to Tables 5 and 6, it can be seen that the driving voltage, efficiency, or lifespan characteristics of an organic light-emitting diode to which a composition containing a compound according to an embodiment of the present invention is applied are also improved.

[0570] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention as defined in the following claims are also included within the scope of the present invention. Explanation of the symbols

[0571] 100: Organic light-emitting diode 105: Organic layer 110: Cathode 120: Anode 130: Emissive layer 140: Precision Transport Area 150: Electronic transport area

Claims

Claim 1 Compound for organic optoelectronic devices represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, Z 1 To Z 3 Each independently N or CR a Igo, Z 1 To Z 3 At least two of them are N, and Ar 1 or Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, and Ar 1 or Ar 4 One of them is a group represented by the following chemical formula A, [Chemical Formula A] L 1 is a single bond or a substituted or unsubstituted phenylene group, and R 1 is hydrogen, deuterium, a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and R a , R 2 and R 3 Each is independently hydrogen or deuterium, m1 to m3 are each independently one of integers 1 to 4, * is a linking point, and Chemical Formula 1 satisfies at least one of the following conditions (i) and (iii), (i) Ar 1 or Ar 4 At least one of the remaining substituents not substituted with the above formula A is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted triphenylene group; (iii) R 1 ...is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; the term "substituted" means that at least one hydrogen in the substituent or compound is substituted with a deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. Claim 2 In claim 1, a compound for an organic optoelectronic device represented by the following chemical formula 1A or chemical formula 1B: [Chemical formula 1A] In the above chemical formula 1A, Z 1 To Z 3 , Ar 1 or Ar 4 , L 1 , R 1 to R 3 The definitions of and m1 to m3 are as defined in Chemical Formula 1, and Chemical Formula 1A satisfies at least one of the following conditions (iii) and (v), and (iii) Ar 2 or Ar 4 At least one of which is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted triphenylene group; (v) R 1 Silver is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; [Chemical Formula 1B] In the above chemical formula 1B, Z 1 To Z 3 , Ar 1 or Ar 4 , L 1 , R 1 to R 3 The definitions of m1 to m3 are as defined in Chemical Formula 1, and Chemical Formula 1B satisfies at least one of the following conditions (vi) and (viii). (vi) Ar 1 or Ar 3 At least one of which is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group or a substituted or unsubstituted triphenylene group; (viii) R 1 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group Claim 3 In claim 2, the above chemical formula 1A is a compound for an organic optoelectronic device represented by any one of the following chemical formulas 1A-I, 1A-II, and 1A-III: [Chemical formula 1A-I] [Chemical Formula 1A-II] [Chemical Formula 1A-III] In the above chemical formulas 1A-I, 1A-II, and 1A-III, Ar 2 or Ar 4 , L 1 , R 1 to R 3 The definitions of m1 to m3 are as defined in Chemical Formula 1A. Claim 4 In claim 2, the above chemical formula 1B is a compound for an organic optoelectronic device represented by either the following chemical formula 1B-II or chemical formula 1B-III: [Chemical formula 1B-II] [Chemical Formula 1B-III] In the above Chemical Formulas 1B-II and 1B-III, Ar 1 or Ar 3 , L 1 , R 1 to R 3 The definitions of m1 to m3 are as defined in Chemical Formula 1B. Claim 5 delete Claim 6 delete Claim 7 In claim 1, a compound for an organic optoelectronic device selected from the compounds listed in Group 1 below: [Group 1][A-1] [A-2] [A-3] [A-4] [A-5] [A-6] [A-7] [A-8] [A-9] [A-10] [A-11] [A-12] [A-14] [A-15] [A-16] [A-17] [A-18] [A-19] [A-20] [A-21] [A-22] [A-23] [A-24] [A-25] [A-26] [A-27] [A-28] [A-29] [A-30] [A-31] [A-32] [A-33] [A-34] [A-35] [A-36] [A-37] [A-38] [A-39] [A-40] [A-41] [A-42] [A-43] [A-44] [A-45] [A-46] [A-47] [A-48] [A-49] [A-50] [A-51] [A-52] [A-53] [A-54] [A-55] [A-56] [A-57] [A-58] [A-59] [A-60] [A-61] [A-62] [A-63] [A-64] [A-65] [A-66] [A-67] [A-68] [A-69] [A-70] [A-71] [A-72] [A-73] [A-74] [A-75] [A-76] [A-78] [A-79] [A-80] [A-81] [A-82] [A-83] [A-84] [A-85] [A-86] [A-87] [A-88] [A-89] . Claim 8 A composition for an organic optoelectronic device comprising a first compound and a second compound, wherein the first compound is a compound for an organic optoelectronic device according to claim 1, and the second compound is represented by the following chemical formula 2; or a combination of the following chemical formulas 3 and 4: [Chemical Formula 2] In the above chemical formula 2, R 4 to R 8 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and L 2 and L 3 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m4, m7, and m8 are each independently one of an integer from 1 to 4, m5 and m6 are each independently one of an integer from 1 to 3, and n is one of an integer from 0 to 2; [Chemical Formula 3] [Chemical Formula 4] In the above Chemical Formulas 3 and 4, a1* to a4* of Chemical Formula 3 are each independently connected carbon (C) or Cl a -R a And, among a1* to a4* of Chemical Formula 3, two adjacent ones are each connected to * of Chemical Formula 4, and L a , L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and R a , R 9 and R 10 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m9 and m10 are each independently one of integers 1 to 4. Claim 9 In claim 8, the above chemical formula 2 is a composition for an organic optoelectronic device represented by the following chemical formula 2-8: [Chemical Formula 2-8] In the above chemical formula 2-8, R 4 to R 7 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, m4 and m7 are each independently one of integers 1 to 4, m5 and m6 are each independently one of integers 1 to 3, and *-L 2 -Ar 5 and *-L 3 -Ar 6 Each is independently one of the substituents listed in Group I below, [Group I] In the above Group I, R 11 to R 13 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C4 alkyl group, a substituted or unsubstituted C6 to C18 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, m11 is one of integers from 1 to 5, m12 is one of integers from 1 to 4, m13 is one of integers from 1 to 3, and * is a connecting point. Claim 10 In claim 8, the combination of Chemical Formula 3 and Chemical Formula 4 is a composition for an organic optoelectronic device represented by the following Chemical Formula 3C: [Chemical Formula 3C] In the above chemical formula 3C, L a3 and L a4 is a single bond, and L 4 and L 5 Each is independently a single-bonded, substituted, or unsubstituted C6 to C12 arylene group, and R 9 and R 10 Each is independently hydrogen, deuterium, or a C6 to C12 aryl group, and Ar 7 and Ar 8 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group, and m9 and m10 are each independently one of integers from 1 to 4. Claim 11 An organic optoelectronic device comprising an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises a compound for an organic optoelectronic device according to any one of claims 1 to 4 and 7; or a composition for an organic optoelectronic device according to any one of claims 8 to 10. Claim 12 In claim 11, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises an organic optoelectronic device comprising a compound for the organic optoelectronic device or a composition for the organic optoelectronic device. Claim 13 A display device comprising an organic optoelectronic element according to paragraph 11.

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