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

Abstract

A compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device, the composition comprising the compound, the organic optoelectronic device comprising the compound or the composition for an organic optoelectronic device, the display device comprising the organic optoelectronic device, the compound is represented by Chemical Formula 1. [Chemical Formula 1] # imgabs0 #

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0152970 filed in the Korean Intellectual Property Office on November 7, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Embodiments relate to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

[0004] An organic optoelectronic device (eg, an organic optoelectronic diode) is a device capable of converting electrical energy and light energy into each other.

[0005] Organic optoelectronic devices can be divided into two categories according to their working principles: one is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively; the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0006] Examples of the organic optoelectronic device may include an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0007] Among them, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to an increase in demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by organic materials between electrodes. Summary of the invention

[0008] The embodiment may be implemented by providing a compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1:

[0009] [Chemical formula 1]

[0010]

[0011] In Chemical Formula 1, L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, L 3 is a single bond or a substituted or unsubstituted C6 to C30 arylene group, Z 1 To Z 3 Each independently is N or CR a , Z 1 To Z 3 At least one of them is N, R aand R 1 To R 6 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 3 is a substituted or unsubstituted C6 to C30 aryl group.

[0012] The embodiment may be implemented by providing a composition for an organic optoelectronic device, the composition including a first compound and a second compound, wherein the first compound is the compound for an organic optoelectronic device according to one embodiment, and the second compound is represented by Chemical Formula 2, by a combination of Chemical Formula 3 and Chemical Formula 4, or by Chemical Formula 5,

[0013] [Chemical formula 2]

[0014]

[0015] In chemical formula 2, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 12 To R 22 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl, m6 and m7 are each independently an integer from 1 to 3, m8 is an integer from 1 to 4, and n is an integer from 0 to 2;

[0016]

[0017] In Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group. 1 * to a 4 The two adjacent carbon atoms in * are connected to the carbon atoms (C) in * of chemical formula 4. 1 * to a 4The other two *'s not connected to the chemical formula 4 are each independently CL a -R b , L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R b and R 23 To R 30 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl;

[0018] [Chemical formula 5]

[0019]

[0020] In Chemical Formula 5, L 8 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 31 To R 43 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 7 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m9 is an integer of 1 to 3.

[0021] The embodiment may be implemented by providing an organic optoelectronic device including an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes the compound for an organic optoelectronic device according to one embodiment.

[0022] The embodiments may be implemented by providing an organic optoelectronic device including an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the at least one organic layer includes the composition for an organic optoelectronic device according to one embodiment.

[0023] The embodiments may be implemented by providing a display device including the organic optoelectronic device according to one embodiment. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Features will become apparent to those skilled in the art by describing in detail exemplary embodiments with reference to the accompanying drawings, in which:

[0025] Figure 1is a cross-sectional view showing an organic light emitting diode according to some embodiments. DETAILED DESCRIPTION

[0026] Exemplary embodiments will now be described more fully below with reference to the accompanying drawings; however, they may be embodied in different forms and should not be considered limited to the embodiments shown herein. However, these embodiments are provided so that this disclosure will be thorough and complete for those skilled in the art and will fully convey exemplary implementations.

[0027] In the accompanying drawings, the sizes of layers and regions may be exaggerated for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or element, it may be directly on the other layer or element, or there may also be intervening layers. In addition, it will be understood that when a layer is referred to as being "between" two layers, it may be the only layer between the two layers, or there may also be one or more intervening layers. Throughout the invention, similar reference numerals refer to similar elements. As used herein, the term "or" is not necessarily an exclusive term, for example, "A or B" will include A, B, or A and B.

[0028] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.

[0029] In one example, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl or cyano. In a specific example, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C1 to C10 alkylsilyl, C6 to C30 aryl or cyano. In a specific example, "substituted" refers to that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C1 to C5 alkylsilyl, C6 to C18 aryl or cyano. In one embodiment, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, trimethylsilyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0030] "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and that a hydrogen atom remains.

[0031] In the present specification, "hydrogen (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)". For example, any hydrogen in any compound described herein may be protium, deuterium or tritium (e.g., based on natural or artificial substitution).

[0032] As used herein, when a definition is not otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbons in one functional group.

[0033] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and all elements of the hydrocarbon aromatic portion have p-orbitals forming conjugation, for example, phenyl, naphthyl, etc.; two or more hydrocarbon aromatic portions may be connected by a σ bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc.; and two or more hydrocarbon aromatic portions may be directly or indirectly fused to provide a non-aromatic fused ring, for example, fluorenyl.

[0034] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0035] As used in this article, "heterocyclic group" is a general concept of heteroaryl, and can include at least one heteroatom selected from N, O, S, P and Si in a cyclic compound to replace carbon (C), such as aryl, cycloalkyl, their condensed rings or their combinations. In one embodiment, the heterocyclic group can be a condensed ring, and the entire ring or each ring of the heterocyclic group can include one or more heteroatoms.

[0036] For example, "heteroaryl" may refer to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls are directly connected by a sigma bond, or when the heteroaryl includes two or more rings, the two or more rings may be fused. When the heteroaryl is a fused ring, each ring may include one to three heteroatoms.

[0037] For example, the substituted or unsubstituted C6 to C30 aryl group may be 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 tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted para-terphenyl group, a substituted or unsubstituted meta-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0038] For example, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzofuranopyrimidinyl, substituted or unsubstituted benzothienopyrimidinyl, or a combination thereof, but are not limited thereto.

[0039] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0040] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level.

[0041] Hereinafter, a compound for an organic optoelectronic device according to some embodiments is described.

[0042] The compound for an organic optoelectronic device according to some embodiments may be represented by Chemical Formula 1.

[0043] [Chemical formula 1]

[0044]

[0045] In Chemical Formula 1, L 1 and L 2 Each independently may be or include, for example, a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0046] L 3 It may be or may include, for example, a single bond or a substituted or unsubstituted C6 to C30 arylene group.

[0047] Z 1 To Z 3 can be independently N or CR a In one embodiment, Z 1 To Z 3 At least one of them is N.

[0048] R a and R 1 To R 6 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0049] Ar 1 and Ar 2 Each independently may be or include, for example, a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0050] Ar 3 It may be or may include, for example, a substituted or unsubstituted C6 to C30 aryl group.

[0051] By including α-carboline, the compound represented by Chemical Formula 1 may have high T1 energy and shallow LUMO characteristics, realizing a high-efficiency device.

[0052] In one embodiment, the β position (Ar) of the α-carboline having relatively high chemical reactivity can be substituted with an aromatic group. 3 ) to achieve a long life device.

[0053] In one embodiment, Ar 3It may be, for example, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl or substituted or unsubstituted triphenylene.

[0054] In one embodiment, Ar 3 It may be, for example, a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0055] In one embodiment, Ar 1 and Ar 2 Each of them may independently be, for example, 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 phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilyl group.

[0056] In one embodiment, Ar 1 and Ar 2 Each independently may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0057] In one embodiment, moieties -L 1 -Ar 1 and -L 2 -Ar 2 Can each independently be part of Group I.

[0058] [Group I]

[0059]

[0060] In Group I, R 7 To R 9 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, or substituted or unsubstituted C6 to C12 aryl.

[0061] Ar 8 It may be, for example, a substituted or unsubstituted C6 to C12 aryl group.

[0062] m1 may be an integer from 1 to 5, for example.

[0063] m2 may be an integer from 1 to 4, for example.

[0064] m3 may be an integer from 1 to 3, for example.

[0065] * is the connection point.

[0066] In one embodiment, R 1 To R 6 Each may independently be, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0067] In one embodiment, R 1 To R 6 Each may independently be, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C5 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0068] In one embodiment, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be, for example, a compound of Group 1.

[0069] [Group 1]

[0070]

[0071]

[0072] (Dn represents the number of deuterium substituted, and represents a structure substituted with one or more deuteriums).

[0073] According to some embodiments, the composition for an organic optoelectronic device may include a first compound and a second compound. In one embodiment, the first compound may be the above-mentioned compound for an organic optoelectronic device. In one embodiment, the second compound may be represented by, for example, Chemical Formula 2, a combination of Chemical Formula 3 and Chemical Formula 4, or Chemical Formula 5.

[0074] [Chemical formula 2]

[0075]

[0076] In chemical formula 2, Ar 3 and Ar 4 Each independently may be or include, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0077] L 4 and L 5 Each independently may be or include, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0078] R 12 To R22 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0079] m6 and m7 may each independently be an integer of 1 to 3, for example.

[0080] m8 may be an integer from 1 to 4, for example.

[0081] n may be an integer from 0 to 2, for example.

[0082]

[0083] In Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 Each independently may be or include, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0084] a in chemical formula 3 1 * to a 4 The two adjacent carbon atoms in * are connected to the carbon atoms (C) in * of Chemical Formula 4. 1 * to a 4 The other two *'s not connected to the chemical formula 4 are each independently, for example, CL a -R b As used herein, the term "connecting carbon" refers to a shared carbon connecting a fused ring.

[0085] L a , L 6 and L 7 Each independently may be or include, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0086] R b and R 23 To R 30 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0087] [Chemical formula 5]

[0088]

[0089] In Chemical Formula 5, L 8 It may be or may include, for example, a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0090] R 31 To R 43 Each independently may be or include, for example, hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0091] Ar 7 It may be or may include, for example, a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0092] m9 may be an integer from 1 to 3, for example.

[0093] In one embodiment, one or two or more types of first compounds may be used or included.

[0094] The second compound may be used together with the first compound or included in the light emitting layer to improve light emitting efficiency and lifespan characteristics by increasing charge mobility and stability.

[0095] In one embodiment, m6 may be, for example, 2 or 3, and each R 16 May be the same as or different from each other.

[0096] In one embodiment, m7 may be, for example, 2 or 3, and each R 17 May be the same as or different from each other.

[0097] In one embodiment, m8 may be, for example, 2, 3, or 4, and each R 22 May be the same as or different from each other.

[0098] In one embodiment, Ar of Formula 2 3 and Ar 4 Each of them may independently be, for example, 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 triphenylene group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0099] In one embodiment, L in Chemical Formula 2 4 and L 5 Each independently may be, for example, a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0100] In one embodiment, R in Chemical Formula 2 12 To R 22may each independently be, for example, hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0101] In one embodiment, n can be, for example, 0 or 1.

[0102] As an example, “substituted” in Chemical Formula 2 means that at least one hydrogen is replaced by deuterium, a C1 to C4 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0103] In one embodiment, Chemical Formula 2 may be represented by, for example, one of Chemical Formula 2-1 to Chemical Formula 2-15.

[0104]

[0105]

[0106] In Chemical Formulae 2-1 to 2-15, R 12 To R 22 Each independently may be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0107] m6 and m7 may each independently be an integer of 1 to 3, for example.

[0108] m8 may be an integer from 1 to 4, for example.

[0109] Part-L 4 -Ar 3 and -L 5 -Ar 4 can each independently be part of Group II.

[0110] [Group II]

[0111]

[0112] In Group II, R 44 To R 47 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0113] m10 may be an integer from 1 to 5, for example.

[0114] m11 may be an integer of 1 to 4, for example.

[0115] m12 may be an integer from 1 to 3, for example.

[0116] m13 can be 1 or 2, for example.

[0117] * is the connection point.

[0118] In one embodiment, m10 may be, for example, 2, 3, 4 or 5, and each R 44 May be the same as or different from each other.

[0119] In one embodiment, m11 may be, for example, 2, 3 or 4, and each R 45 May be the same as or different from each other.

[0120] In one embodiment, m12 may be, for example, 2 or 3, and each R 46 May be the same as or different from each other.

[0121] In one embodiment, m13 may be 2, and each R 47 May be the same as or different from each other.

[0122] In one embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0123] In one embodiment, the part -L of Chemical Formula 2-8 4 -Ar 3 and -L 5 -Ar 4 Each may independently be part of Group II, for example, may be E-1, E-2, E-3, E-4, E-7, E-8 or E-9.

[0124] In one embodiment, the second compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 may be represented by, for example, Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, or Chemical Formula 3E.

[0125]

[0126]

[0127] In Chemical Formulae 3A to 3E, Ar 5 ,Ar 6 , L 6 , L 7 and R 23 To R 30 Can be defined as the same as those above.

[0128] L a1 To L a4 It can be defined as 6 and L 7 same.

[0129] R b1 To R b4 can be defined as 23 To R30 same.

[0130] In one embodiment, Ar of Chemical Formula 3 and Chemical Formula 4 5 and Ar 6 Each independently may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0131] In one embodiment, R b1 To R b4 and R 23 To R 30 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0132] In one embodiment, the moiety -L of Chemical Formula 3 and Chemical Formula 4 6 -Ar 5 and -L 7 -Ar 6 can each independently be part of Group II.

[0133] In one embodiment, R b1 To R b4 and R 23 To R 30 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0134] In one embodiment, R b1 To R b4 and R 23 To R 30 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C5 alkyl, or substituted or unsubstituted phenyl.

[0135] In one embodiment, R b1 To R b4 and R 23 To R 30 Each independently may be, for example, hydrogen, deuterium or substituted or unsubstituted phenyl.

[0136] In one embodiment, m9 can be 2 or 3, and each R35 May be the same as or different from each other.

[0137] In one embodiment, Chemical Formula 5 may be represented by, for example, one of Chemical Formula 5-1 to Chemical Formula 5-4.

[0138]

[0139] In Chemical Formula 5-1 to Chemical Formula 5-4, L 8 , R 31 To R 43 ,Ar 7 and m9 can be defined as the same as those above.

[0140] In one embodiment, Ar of Chemical Formula 5 7 It may be, for example, 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 triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0141] In one embodiment, R 31 To R 43 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0142] In one embodiment, the moiety -L of Formula 5 8 -Ar 7 Can be part of Group II.

[0143] In one embodiment, R 31 To R 43 Each independently may be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted phenyl.

[0144] In one embodiment, the second compound may be, for example, a compound of Group 2.

[0145] [Group 2]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153] The following are examples of compounds B-1 to B-150 from Group 2 in which at least one hydrogen is replaced by deuterium.

[0154]

[0155]

[0156] (Dn refers to the number of deuterium substitutions and denotes structures having one or more deuterium substitutions).

[0157] For Compound B-151 to Compound B-195 of Group 2, the most specific structures according to deuterium substitution positions and substitution ratios are exemplarily shown below.

[0158] In one embodiment, deuterium may be substituted, and the deuterium substitution position and the deuterium substitution ratio may include all variable ranges within the range of Compound B-1 to Compound B-195.

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166] Examples in which at least one hydrogen in Compound C-1 to Compound C-57 listed in Group 2 is replaced by deuterium are shown below.

[0167]

[0168]

[0169] (Dn represents the number of deuterium substituted, and represents a structure substituted with one or more deuteriums).

[0170] For Compound C-58 to Compound C-72 of Group 2, the most specific structures according to deuterium substitution positions and substitution ratios are exemplarily shown below.

[0171] In one embodiment, the deuterium substitution position and the deuterium substitution ratio may include all variable ranges within the range of Compound C-1 to Compound C-72.

[0172]

[0173]

[0174]

[0175]

[0176] Examples in which at least one hydrogen in Compound D-1 to Compound D-60 listed in Group 2 is replaced by deuterium are shown below.

[0177]

[0178]

[0179]

[0180] (Dn represents the number of deuterium substituted, and represents a structure substituted with one or more deuteriums).

[0181] In one embodiment, one or two or more types of the second compound may be used.

[0182] The first compound and the second compound may be included (e.g., mixed) in a weight ratio of, for example, about 1:99 to about 99:1. Within this range, bipolar properties may be achieved by matching the appropriate weight ratio using the electron transport capability of the first compound and the hole transport capability of the second compound to help improve efficiency and lifespan. In one embodiment, they may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20 (e.g., about 20:80 to about 70:30, about 20:80 to about 60:40, or about 30:70 to about 60:40). In one embodiment, they may be included in a weight ratio of about 40:60, about 50:50, or about 60:40.

[0183] Hereinafter, an organic optoelectronic device including the above-mentioned compound for an organic optoelectronic device or the composition for an organic optoelectronic device is described.

[0184] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy, or vice versa, and may be, for example, an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0185] Herein, an organic light emitting diode as one example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0186] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments.

[0187] refer to Figure 1 , the organic light emitting diode 100 according to some embodiments may include, for example, an anode 120 and a cathode 110 facing each other, and an organic layer 105 between the anode 120 and the cathode 110 .

[0188] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc., or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of a metal and an oxide such as ZnO and Al or SnO 2 and Sb; conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0189] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or alloys thereof; a multilayer structure material such as LiF / Al, LiO 2 / Al, LiF / Ca or BaF 2 / Ca.

[0190] The organic layer 105 may include the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[0191] The organic layer 105 may include a light-emitting layer 130, and the light-emitting layer 130 may include a host and a dopant, and the host may include the above-mentioned compound for an organic optoelectronic device or a composition for an organic optoelectronic device. The dopant may be, for example, a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0192] The dopant may be a substance that emits light when mixed in a small amount in a compound or composition for an organic optoelectronic device, and may generally be a material such as a metal complex that emits light by multiple excitations of a triplet state or more. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and may be included in one or two or more types.

[0193] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may include an organic metal compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may include, for example, a compound represented by the chemical formula Z.

[0194] [Chemical formula Z]

[0195] L 9 MX

[0196] In the chemical formula Z, M may be a metal, and L 9 and X may each independently be a ligand that forms a complex with M.

[0197] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 9 and X may be, for example, a bidentate ligand.

[0198] In one embodiment, L 9 The ligand represented by and X may be a ligand of Group A.

[0199] [Group A]

[0200]

[0201] In group A, R 300 To R 302 Each independently may be, for example, hydrogen, deuterium, a C1 to C30 alkyl group which may be substituted by a halogen or not, a C6 to C30 aryl group which may be substituted by a C1 to C30 alkyl group or a halogen.

[0202] R 303 To R 324 The substituted or unsubstituted C1 to C30 alkyl groups, substituted or unsubstituted C1 to C30 alkoxy groups, substituted or unsubstituted C3 to C30 cycloalkyl groups, substituted or unsubstituted C2 to C30 alkenyl groups, substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C1 to C30 heteroaryl groups, substituted or unsubstituted C1 to C30 amino groups, substituted or unsubstituted C6 to C30 arylamino groups, SF 5, 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.

[0203] n1 may be an integer from 1 to 5, for example.

[0204] n2 may be an integer from 1 to 4, for example.

[0205] n3 may be an integer from 1 to 3, for example.

[0206] n4 may be an integer such as 1 or 2.

[0207] n5 may be an integer of 1 to 6, for example.

[0208] The dopant according to some embodiments may be an iridium complex, and may be represented by, for example, Chemical Formula 4-1 or Chemical Formula 4-2.

[0209] [Chemical formula 4-1]

[0210]

[0211] In chemical formula 4-1, R 101 To R 116 can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 .

[0212] R 132 To R 134 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0213] R 101 To R 116 At least one of may be a functional group represented by Chemical Formula V-1.

[0214] L 100 The bidentate ligand may be a monovalent anion and may be a ligand coordinated to iridium via a lone electron pair of carbon or a heteroatom.

[0215] m21 and m22 may each independently be an integer of, for example, 0 to 3, and m21+m22 may be an integer of 1 to 3.

[0216] [Chemical formula V-1]

[0217]

[0218] In chemical formula V-1, R 135 To R 139 can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 .

[0219] *Indicates the moiety attached to the carbon atom.

[0220] [Chemical formula 4-2]

[0221]

[0222] In chemical formula 4-2, R 101 To R 117 can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 .

[0223] R 133 To R 135 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0224] L 100 The bidentate ligand may be a monovalent anion and may be a ligand coordinated to iridium via a lone electron pair of carbon or a heteroatom.

[0225] n1 and n2 may each independently be an integer of, for example, 0 to 3, and n1+n2 may be an integer of 1 to 3.

[0226] The dopant according to some embodiments may be a platinum complex, and may be represented, for example, by Chemical Formula Z-1.

[0227] [Chemical formula Z-1]

[0228]

[0229] In the chemical formula Z-1, the rings A, B, C and D may each independently be, for example, a 5-membered or 6-membered carbocyclic ring or a heterocyclic ring.

[0230] R A , R B , R C and R D Each may independently be, for example, mono-, di-, tri-, or tetra-substituted or unsubstituted.

[0231] L B , L C and LD Each of them can be, for example, a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO 2 , CRR', SiRR', GeRR' or a combination thereof.

[0232] In one embodiment, nA may be 1, and L E Can be direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO 2 , CRR', SiRR', GeRR' or a combination thereof. In one embodiment, nA may be 0, and L E Does not exist.

[0233] R A , R B , R C , R D R, R and R' can each independently be, for example, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino or a combination thereof. In one embodiment, any adjacent R A , R B , R C , R D , R and R' may be independent or may be linked to each other to provide a ring; X B , X C , X D and X E can each independently be, for example, carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 can each independently be, for example, oxygen or a direct bond.

[0234] The platinum complex may be represented, for example, by Chemical Formula 6-1 or Chemical Formula 6-2.

[0235] [Chemical formula 6-1]

[0236]

[0237] [Chemical formula 6-2]

[0238]

[0239] In Chemical Formula 6-1 and Chemical Formula 6-2, X 100 Can be O, S or NR 132 .

[0240] R 118 To R 132 can each independently be, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 .

[0241] R 133 To R 135 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0242] In one embodiment, R 118 To R 132 At least one of them may be -SiR 133 R 134 R 135 or tert-butyl.

[0243] R 133 To R 135 Each independently may be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0244] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0245] The charge transport region may be, for example, a hole transport region 140 .

[0246] The hole transport region 140 may further increase hole injection or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0247] In one embodiment, 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 a compound of group B may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0248] [Group B]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255] (Dn represents the number of deuterium substituted, and represents a structure substituted with one or more deuteriums).

[0256] In the hole transporting zone 140 , other suitable compounds besides the compounds may be used.

[0257] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0258] The electron transport region 150 may help to further increase electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0259] In one embodiment, 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 a compound of group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0260] [Group C]

[0261]

[0262]

[0263]

[0264]

[0265] Some embodiments may provide an organic light emitting diode including a light emitting layer as an organic layer.

[0266] Some embodiments may provide an organic light emitting diode including a light emitting layer and a hole transport region as an organic layer.

[0267] Some embodiments may provide an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0268] like Figure 1 As shown, the organic light emitting diode according to some embodiments may further include a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130 .

[0269] In one embodiment, in addition to the light-emitting layer, the organic light-emitting diode may further include an electron injection layer, a hole injection layer, etc. as the organic layer.

[0270] The organic light emitting diode 100 may be produced by forming an anode or a cathode on a substrate, forming an organic layer using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating, or ion plating, and forming a cathode or an anode thereon.

[0271] The organic light emitting diode may be applied to an organic light emitting display device.

[0272] The following examples and comparative examples are provided to highlight the characteristics of one or more embodiments, but it will be understood that the examples and comparative examples should not be considered as limiting the scope of the embodiments, and the comparative examples should not be considered as being outside the scope of the embodiments. In addition, it will be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0273] Hereinafter, the starting materials and reactants used in the Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry or P&H tech, or synthesized by appropriate methods unless otherwise specified.

[0274] (Synthesis of compounds for organic optoelectronic devices)

[0275] Synthesis Example 1: Synthesis of Compound A-4

[0276] [Reaction 1]

[0277]

[0278] Step 1: Synthesis of intermediate P-1

[0279] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (100 g / 1.0 equivalent), (4-fluorophenyl)boric acid (1.1 equivalent), Pd(PPh 3 ) 4 (0.05 equivalent) and K 2 CO 3 (3.0 equiv) was injected into the flask along with THF (750 mL) and distilled water (250 mL) and refluxed at 80° C. After 12 h, the reaction was complete and diluted with dichloromethane (DCM), washed three times with brine, and washed with MgSO 4 After drying, 90 g of intermediate P-1 was obtained by column chromatography.

[0280] Step 2: Synthesis of Compound A-4

[0281] Intermediate P-1 (30 g / 1.0 equivalent), 2-phenyl-9H-pyrido[2,3-b]indole (1.5 equivalent) and K 3 PO 4(3.0 equiv) was added to the flask along with DMF (500 mL) and refluxed to 150° C. After 12 h, the reaction was complete and diluted with DCM, washed three times with brine, and washed with MgSO 4 The mixture was dried and column chromatography was used to obtain 15 g of compound A-4.

[0282] Synthesis Example 2: Synthesis of Compound A-5

[0283] [Reaction 2]

[0284]

[0285] Step 1: Synthesis of intermediate P-2

[0286] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (100 g / 1.0 equivalent), (3-fluorophenyl)boric acid (1.1 equivalent), Pd(PPh 3 ) 4 (0.05 equivalent) and K 2 CO 3 (3.0 equiv) was injected into the flask along with THF (750 mL) and distilled water (250 mL) and refluxed at 80 °C. After 12 h, the reaction was complete and diluted with DCM, washed three times with brine, and washed with MgSO 4 After drying, 92 g of intermediate P-2 was obtained by column chromatography.

[0287] Step 2: Synthesis of Compound A-5

[0288] Intermediate P-2 (30 g / 1.0 equivalent), 2-phenyl-9H-pyrido[2,3-b]indole (1.5 equivalent) and K 3 PO 4 (3.0 equiv) was added to the flask along with DMF (500 mL) and refluxed to 150° C. After 12 h, the reaction was complete and diluted with DCM, washed three times with brine, and washed with MgSO 4 The mixture was dried and column chromatography was used to obtain 14 g of compound A-5.

[0289] Synthesis Example 3: Synthesis of Compound A-6

[0290] [Reaction 3]

[0291]

[0292] Step 1: Synthesis of intermediate P-3

[0293] 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (100 g / 1.0 equivalent), (2-fluorophenyl)boronic acid (1.1 equivalent), Pd(PPh 3 ) 4 (0.05 equivalent) and K 2 CO 3 (3.0 equiv) was injected into the flask along with THF (750 mL) and distilled water (250 mL) and refluxed to 80 °C. After 12 h, the reaction was complete and diluted with DCM, washed three times with brine, and washed with MgSO 4 After drying, 82 g of intermediate P-3 was obtained by column chromatography.

[0294] Step 2: Synthesis of Compound A-6

[0295] Intermediate P-3 (30 g / 1.0 equivalent), 2-phenyl-9H-pyrido[2,3-b]indole (1.5 equivalent) and K 3 PO 4 (3.0 equiv) was added to the flask along with DMF (500 mL) and refluxed to 150° C. After 12 h, the reaction was complete and diluted with DCM, washed three times with brine, and washed with MgSO 4 After drying, 18 g of compound A-6 was obtained by column chromatography.

[0296] Synthesis Example 4: Synthesis of Compound B-136

[0297]

[0298] Compound B-136 was synthesized by referring to the synthesis method described in European Patent No. EP3034581.

[0299] HRMS (70 eV, EI+): m / z calculated for C42H28N2: 560.2252, measured: 560.

[0300] Elemental analysis: C, 90%; H, 5%

[0301] Comparative Synthesis Example 1: Synthesis of Compound R-1

[0302]

[0303] Compound R-1 was synthesized by referring to the synthesis method described in Chinese Patent No. CN111689960.

[0304] Comparative Synthesis Example 2: Synthesis of Compound R-2

[0305]

[0306] Compound R-2 was synthesized by referring to the synthesis method described in Korean Patent No. KR2023-0052860.

[0307] Example 1: Fabrication of a green organic light emitting diode (single body)

[0308] A glass substrate coated with ITO (indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone or methanol, and dried, then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. This prepared ITO transparent electrode was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form A hole injection layer is formed on the hole injection layer to a thickness of Compound B is deposited on the hole transport layer to a thickness of On the hole transport auxiliary layer, compound A-4 was used as a host, and 7 wt % of PhGD was doped as a dopant by vacuum deposition to form a hole transport auxiliary layer. Subsequently, compound C is deposited to form a light-emitting layer on the light-emitting layer. A thick electron transport auxiliary layer is formed, and compound D and Liq are simultaneously vacuum deposited at a weight ratio of 1:1 to form On the electron transport layer, Liq and Al are vacuum deposited sequentially to Thick and harmonious thick, thereby manufacturing an organic light emitting diode.

[0309] The structure is ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[host (compound A-4):PhGD=93wt%:7wt%] / Compound C / Compound D: Liq / Liq / Al

[0310] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0311] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0312] Compound C: 2,4-diphenyl-6-(4',5',6'-triphenyl[1,1':2',1":3",1"':3"',1""-pentaphenyl]-3""-yl)-1,3,5-triazine

[0313] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0314] [PhGD]

[0315]

[0316] Examples 2 to 3 and Comparative Examples 1 to 2

[0317] An organic light emitting diode was manufactured in the same manner as in Example 1, except that the compositions were changed to those shown in Table 1.

[0318] Example 4: Fabrication of a green organic light-emitting diode (hybrid host)

[0319] A glass substrate coated with ITO (indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate was ultrasonically washed with isopropyl alcohol, acetone or methanol, and dried, then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. This prepared ITO transparent electrode was used as an anode, and Compound E doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form The hole injection layer is formed into a layer having a thickness of 1000 nm and a thickness of 1000 nm, and compound E is deposited on the hole injection layer to a thickness of Compound F is deposited on the hole transport layer to a thickness of On the hole transport auxiliary layer, compound A-4 and compound B-136 were used as hosts at a weight ratio of 3:7, and 15 wt % of PtGD was used as a dopant to form a hole transport auxiliary layer by vacuum deposition. Subsequently, compound G is deposited to form a light-emitting layer on the light-emitting layer. A thick electron transport auxiliary layer is formed, and compound H and Liq are simultaneously vacuum deposited at a weight ratio of 1:1 to form On the electron transport layer, Liq and Al are vacuum deposited sequentially to Thick and harmonious thick, thereby manufacturing an organic light emitting diode.

[0320] The structure is ITO / compound E (3% NDP-9 doping, ) / Compound E / Compound F / EML[host (Compound A-4:Compound B-136=3:7wt% / wt%):PtGD=85wt%:15wt%] / Compound G / Compound H:Liq / Liq / Al

[0321] Compound E: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0322] Compound F: 9,9-dimethyl-N-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-4-(4-phenylphenyl)-9H-fluoren-2-amine

[0323] Compound G: 4-{4-[4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0324] Compound H: 2-(4-{1-[4-(diphenyl-1,3,5-triazine-2-yl)phenyl]naphthalen-2-yl}-4,6-diphenyl-1,3,5-triazine

[0325] [PtGD]

[0326]

[0327] Examples 5 to 6 and Comparative Examples 3 to 4

[0328] An organic light emitting diode was manufactured in the same manner as in Example 4, except that the compositions were changed to those shown in Table 2.

[0329] evaluate

[0330] The luminous efficiency and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 6 and Comparative Examples 1 to 4 were evaluated.

[0331] The specific measurement method is as follows, and the results are shown in Tables 1 and 2.

[0332] (1) Measuring the change in current density due to voltage change

[0333] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit device in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0334] (2) Measuring the change in brightness due to voltage changes

[0335] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).

[0336] (3) Measurement of luminous efficiency

[0337] Using the luminance and current density and voltage measured according to (1) and (2) above, calculate the same current density (10 mA / cm 2 ) under current efficiency (cd / A).

[0338] Based on Comparative Example 1, the luminous efficiency values ​​of Examples 1 to 3 and Comparative Example 2 were calculated as relative values ​​and are listed in Table 1.

[0339] Based on Comparative Example 3, the luminous efficiency values ​​of Examples 4 to 6 and Comparative Example 4 were calculated as relative values ​​and are listed in Table 2.

[0340] (4) Measurement life

[0341] By converting the brightness (cd / m 2 ) maintained at 24,000cd / m 2 And the time when the current efficiency (cd / A) dropped to 97% was measured to obtain the result.

[0342] Based on Comparative Example 1, the life measurement values ​​of Examples 1 to 3 and Comparative Example 2 were calculated as relative values ​​and are listed in Table 1.

[0343] Based on Comparative Example 3, the life measurement values ​​of Examples 4 to 6 and Comparative Example 4 were calculated as relative values ​​and are listed in Table 2.

[0344] (Table 1)

[0345]

[0346] (Table 2)

[0347]

[0348] Referring to Tables 1 and 2, the luminous efficiency and life characteristics of the organic light emitting diodes according to Examples 1 to 6 are significantly improved compared to the organic light emitting diodes according to Comparative Examples 1 and 3. Compared to the organic light emitting diodes according to Comparative Examples 2 and 4, the luminous efficiency is improved and the life characteristics are improved by more than 200%.

[0349] One or more embodiments may provide a compound for an organic optoelectronic device, which may help reduce a driving voltage and realize a high-efficiency and long-life organic optoelectronic device.

[0350] An organic optoelectronic device with high efficiency and long lifetime can be realized while reducing the driving voltage.

[0351] Exemplary embodiments have been disclosed herein, and although specific terms are used, they are used and understood only in a general and descriptive sense and not for limiting purposes. In some cases, as will be apparent to those of ordinary skill in the art upon filing this application, unless otherwise specifically indicated, the features, characteristics, and / or elements described in conjunction with a specific embodiment may be used alone or in combination with the features, characteristics, and / or elements described in conjunction with other embodiments. Therefore, those skilled in the art will appreciate that changes in various forms and details may be made without departing from the spirit and scope of the invention as set forth in the appended claims.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: [Chemical formula 1] In Chemical Formula 1, L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group, L 3 is a single bond or a substituted or unsubstituted C6 to C30 arylene group, Z 1 To Z 3 Each independently is N or CR a , Z 1 To Z 3 At least one of them is N, R a and R 1 To R 6 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 3 is a substituted or unsubstituted C6 to C30 aryl group.

2. The compound for an organic optoelectronic device according to claim 1, wherein Ar 3 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl or substituted or unsubstituted triphenylene.

3. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 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 phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilyl group.

4. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.

5. The compound for an organic optoelectronic device according to claim 1, wherein: Part-L 1 -Ar 1 and -L 2 -Ar 2 Each independently is part of Group I: [Group I] In Group I, R 7 To R 9 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C1 to C10 alkylsilyl, or substituted or unsubstituted C6 to C12 aryl, Ar 8 is a substituted or unsubstituted C6 to C12 aryl group, m1 is an integer from 1 to 5, m2 is an integer from 1 to 4, m3 is an integer from 1 to 3, and * is the connection point.

6. The compound for an organic optoelectronic device according to claim 1, wherein R 1 To R 6 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

7. The compound for an organic optoelectronic device according to claim 1, wherein The compound is a compound of Group 1: [Group 1] 8. A composition for an organic optoelectronic device, comprising: a first compound; and The second compound, in: The first compound is the compound for an organic optoelectronic device according to any one of claims 1 to 7, and The second compound is represented by: Chemical formula 2; A combination of Chemical Formula 3 and Chemical Formula 4; or Chemical formula 5, [Chemical formula 2] In chemical formula 2, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 12 To R 22 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, m6 and m7 are each independently an integer from 1 to 3, m8 is an integer from 1 to 4, and n is an integer from 0 to 2; In Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, Two adjacent ones of a1* to a4* in Chemical Formula 3 are carbon atoms connected to * in Chemical Formula 4, and the remaining two of a1* to a4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are each independently CL a -R b , L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R b and R 23 To R 30 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl; [Chemical formula 5] In Chemical Formula 5, L 8 is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 31 To R 43 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 7 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m9 is an integer from 1 to 3.

9. The composition for an organic optoelectronic device according to claim 8, wherein: The second compound is represented by Chemical Formula 2, Chemical formula 2 is represented by Chemical formula 2-8, [Chemical formula 2-8] In Chemical Formula 2-8, R 12 To R 21 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, m6 and m7 are each independently an integer from 1 to 3, and Part-L 4 -Ar 3 and -L 5 -Ar 4 each independently being part of Group II, [Group II] In Group II, R 44 To R 47 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m10 is an integer from 1 to 5, m11 is an integer from 1 to 4, m12 is an integer from 1 to 3, m13 is 1 or 2, and * is the connection point.

10. The composition for an organic optoelectronic device according to claim 8, wherein: The second compound is represented by a combination of Chemical Formula 3 and Chemical Formula 4, The combination of Chemical Formula 3 and Chemical Formula 4 is represented by Chemical Formula 3C: [Chemical formula 3C] In chemical formula 3C, L a3 and L a4 Each is a single bond, R 23 To R 30 , R b3 and R b4 are each independently hydrogen or substituted or unsubstituted C6 to C12 aryl, and Part of Chemical Formula 3 and Chemical Formula 4 -L 6 -Ar 5 and -L 7 -Ar 6 each independently being part of Group II, [Group II] In Group II, R 44 To R 47 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m10 is an integer from 1 to 5, m11 is an integer from 1 to 4, m12 is an integer from 1 to 3, m13 is 1 or 2, and * is the connection point.

11. The composition for an organic optoelectronic device according to claim 8, wherein: The second compound is represented by Chemical Formula 5, Chemical formula 5 is represented by one of Chemical formula 5-2 or Chemical formula 5-3, In Chemical Formula 5-2 and Chemical Formula 5-3, L 8 , R 31 To R 43 ,Ar 7 and m9 are defined to be the same as those of Chemical Formula 5.

12. An organic optoelectronic device, comprising: an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, The at least one organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 7 or the composition for an organic optoelectronic device according to any one of claims 8 to 11.

13. The organic optoelectronic device according to claim 12, wherein: The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound or the composition. 14 . A display device comprising the organic optoelectronic device according to claim 12 or 13 .

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