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

Abstract

The present invention relates to a compound for an organic optoelectronic diode represented by Chemical Formula 1; and an organic optoelectronic diode and a display device including the same. The details of the chemical formula 1 are the same as the definitions in the specification.

Description

Technical Field

[0001] Disclosed are a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

[0002] Organic optoelectronic devices (organic optoelectronic diodes) are devices that can convert electrical energy and light energy into one another.

[0003] Organic optoelectronic devices can be mainly divided into two types according to the working principle. 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, while 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 photoelectric devices, organic light emitting diodes, organic solar cells, and organic photoconductors.

[0005] Among them, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to the increasing 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

[0006] [Technical issues]

[0007] One embodiment provides a compound for an organic optoelectronic device capable of realizing an organic optoelectronic device with low driving, high efficiency, and long lifetime.

[0008] Another embodiment provides a composition for an organic optoelectronic device capable of realizing an organic optoelectronic device with high efficiency and long lifetime.

[0009] Another embodiment provides an organic optoelectronic device including the compound for an organic optoelectronic device.

[0010] Another embodiment provides a display device including an organic optoelectronic device.

[0011] [Technical solution]

[0012] According to one embodiment, a compound for an organic optoelectronic device represented by Chemical Formula 1 is provided.

[0013]

[0014] In Chemical Formula 1,

[0015] Ar 1 and Ar 2are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0016] Ar 3 is a substituted or unsubstituted C6 to C30 aryl group,

[0017] L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

[0018] Z is hydrogen or unsubstituted phenyl,

[0019] R 1 To R 14 are each independently hydrogen, deuterium, cyano, or a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0020] R 1 To R 14 Each independently existing or adjacent groups are linked to form a substituted or unsubstituted aromatic monocyclic ring or a substituted or unsubstituted aromatic polycyclic ring, and

[0021] R 15 To R 18 Each is independently hydrogen, deuterium, cyano or phenyl which is unsubstituted or substituted with deuterium.

[0022] According to another embodiment, a composition for an organic optoelectronic device includes a first compound and a second compound.

[0023] The first compound is as described above, and the second compound may be a compound for an organic optoelectronic device represented by Chemical Formula 2; or a compound for an organic optoelectronic device represented by a combination of Chemical Formula 3 and Chemical Formula 4.

[0024]

[0025]

[0026] In chemical formula 2,

[0027] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0028] L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0029] R 23 To R27 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,

[0030] m3, m5 and m7 are each independently an integer from 1 to 4,

[0031] m4 and m6 are each independently one of integers from 1 to 3, and

[0032] p is an integer from 0 to 2;

[0033]

[0034] In chemical formulas 3 and 4,

[0035] Ar 6 and Ar 7 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0036] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R a , among a1* to a4* in Chemical Formula 3, two adjacent ones are each connected to * in Chemical Formula 4, L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0037] R a , R 28 and R 29 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, and

[0038] m8 and m9 are each independently one of integers from 1 to 4.

[0039] According to another embodiment, an organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the organic layer includes a light emitting layer and the light emitting layer includes the above compound for an organic optoelectronic device.

[0040] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0041] [Beneficial Effects]

[0042] It is possible to realize organic optoelectronic devices with low driving force, high efficiency and long life. BRIEF DESCRIPTION OF THE DRAWINGS

[0043] Figure 1 is a cross-sectional view showing an organic light emitting diode according to the embodiment.

[0044] <Description of Reference Numerals>

[0045] 100: Organic Light Emitting Diode

[0046] 105: Organic layer

[0047] 110: cathode

[0048] 120: Anode

[0049] 130: Luminous layer

[0050] 140: Hole transport zone

[0051] 150: Electron transport region DETAILED DESCRIPTION

[0052] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present disclosure is not limited thereto.

[0053] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or 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.

[0054] In one embodiment of the invention, "substituted" means 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 embodiment of the invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0055] In the present specification, when a definition is not otherwise provided, "hetero" means including one to three hetero atoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0056] In the present specification, "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, such as 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 are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0057] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0058] As used herein, "heterocyclic group" is a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound such as an aryl group, a cycloalkyl group, a condensed ring thereof or a combination thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0059] 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 1 to 3 heteroatoms.

[0060] More specifically, 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 p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted The invention may include, but is not limited to, 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.

[0061] More specifically, 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 triazine, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothiophenyl, A substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazoline, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazolyl, a substituted or unsubstituted acridinyl, a substituted or unsubstituted phenazinyl, a substituted or unsubstituted phenothiazinyl, a substituted or unsubstituted phenoxazinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl or a combination thereof, but not limited thereto.

[0062] In the present specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0063] In the present specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0064] As used herein, hole characteristics refer to the ability to donate 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, holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0065] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level, the electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0066] Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

[0067] The compound for an organic optoelectronic device according to one embodiment is represented by Chemical Formula 1.

[0068]

[0069] In Chemical Formula 1,

[0070] 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,

[0071] Ar 3 is a substituted or unsubstituted C6 to C30 aryl group,

[0072] L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

[0073] R 1 To R 14 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[0074] R 1 to R14 are each independently present or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic ring or a substituted or unsubstituted aromatic polycyclic ring,

[0075] R 15 To R 18 Each is independently hydrogen, deuterium, cyano or phenyl which is unsubstituted or substituted with deuterium.

[0076] The compound represented by Chemical Formula 1 has a structure including a phenyl or biphenyl group substituted by o-carbazole and triazine, and when o-carbazole is additionally substituted by carbazole, the dihedral angle increases due to the steric hindrance between triazine and carbazole, resulting in distortion of the two parts. For this reason, the HOMO energy level and the LUMO energy level are mostly separated without overlapping, and fast energy transfer with a small ΔEst is possible, so that it exhibits high efficiency / low driving characteristics, especially when applied as a phosphorescent host.

[0077] In particular, the carbazole additionally substituted for o-carbazole is linked at the 4-4′-position, which can reduce the deposition temperature and facilitate the formation of a spherical shape, thereby improving the life of an organic light-emitting diode to which it is applied.

[0078] At the same time, the o-phenyl linker can significantly weaken triplet-triplet annihilation (TTA) by ensuring sufficient intermolecular distance, thereby enabling high-efficiency devices compared to existing materials.

[0079] In addition, due to its high T1 energy level compared to dopants, side reaction pathways in the excited state can be reduced, which can improve lifetime, and due to the presence of ortho isomers, the deposition temperature is reduced by about 10% compared to para or meta, which can minimize degradation.

[0080] Finally, by operating in a hybrid host system, TPQ (triplet-polaron quenching) is suppressed, enabling the realization of devices with superior long lifetimes compared to conventional devices.

[0081] As an example, Chemical Formula 1 may be represented by any one of Chemical Formula 1-1 to Chemical Formula 1-5.

[0082] [Chemical formula 1-1]

[0083]

[0084]

[0085]

[0086] In Chemical Formula 1-1 to Chemical Formula 1-5,

[0087] Ar 1 To Ar 3 , R 1 To R 14 and L 1 To L 3 Same as above,

[0088] Z is deuterium or cyano,

[0089] D is deuterium,

[0090] m1 is an integer from 0 to 3, and

[0091] m2 is one of integers from 0 to 5.

[0092] m1=0 means that the substituents 'Z' other than hydrogen are unsubstituted, ie, all substitution sites are hydrogen.

[0093] m2=0 means that deuterium 'D' is unsubstituted, ie, all substitution sites are hydrogen.

[0094] As a specific example, Chemical Formula 1 may be represented by Chemical Formula 1-3.

[0095] The para-substituted structures included in Chemical Formulae 1-3 may induce electronic stability through a resonance effect, thereby improving the lifetime, especially when applied as a phosphorescent host.

[0096] Furthermore, when triazine and biscarbazole are substituted at the ortho-position of the para-position, the dihedral angle increases due to the steric hindrance between the triazine and biscarbazole, and the triazine moiety and the biscarbazole moiety are twisted with each other.

[0097] This means that the HOMO and LUMO energy levels are mostly separated without any overlap, and fast energy transfer is possible with a small ΔEst, making it exhibit high efficiency characteristics, especially when applied as a phosphorescent host.

[0098] Furthermore, side reaction pathways are reduced in this state, which increases the lifetime, especially when applied as phosphorescent hosts.

[0099] For example, R in Formula 1 1 To R 14 Can exist independently of each other.

[0100] For example, R in Formula 1 1 To R 14 It may be connected to an adjacent group to form a substituted or unsubstituted aromatic monocyclic ring, and may be represented by, for example, any one of Chemical Formula 1A to Chemical Formula 1J.

[0101]

[0102]

[0103]

[0104]

[0105]

[0106] In Chemical Formulae 1A to 1J, Ar 1 To Ar 3 , R 1 To R 18 and L 1 To L 3 Same as above, and

[0107] R 19 To R 22 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic.

[0108] For example, R in Formula 1 1 To R 14Each may exist independently or may be represented by Chemical Formula 1J.

[0109] As an example, R 1 To R 14 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted dibenzosilyl.

[0110] As a specific example, R 1 To R 14 and may each independently be hydrogen, deuterium, or substituted or unsubstituted phenyl.

[0111] For example, Ar 1 and Ar 2 Each of them may independently be 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 triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted dibenzosilyl group.

[0112] As a specific example, Ar 1 and Ar 2 Each of them may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl 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.

[0113] For example, L 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted C6 to C12 arylene group.

[0114] For example, *-L 1 -Ar 1 and *-L 2 -Ar 2 The substituents listed in Group I may be each independently selected.

[0115] [Group I]

[0116]

[0117] In Group I, * is the point of attachment, and each substituent may further include additional substituents.

[0118] Additional substituents may be deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl.

[0119] In one embodiment, the additional substituent may be deuterium, C1 to C5 alkyl, phenyl, biphenyl or naphthyl.

[0120] In a specific embodiment, Ar 1 and Ar 2 Each of them may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilyl group.

[0121] For example, Ar 3 It may be a substituted or unsubstituted C6 to C12 aryl group.

[0122] For example, L3 may be a single bond or a substituted or unsubstituted C6 to C12 arylene group.

[0123] In the most specific embodiment, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1, but is not limited thereto.

[0124] [Group 1]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153] A composition for an organic optoelectronic device according to another embodiment includes a first compound and a second compound, wherein the first compound may be the above-mentioned compound for an organic optoelectronic device, and the second compound may be a compound for an organic optoelectronic device represented by Chemical Formula 2; or a compound for an organic optoelectronic device represented by a combination of Chemical Formula 3 and Chemical Formula 4.

[0154]

[0155] In chemical formula 2,

[0156] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0157] L 4 and L 5are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0158] R 23 to R27 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 group,

[0159] m3, m5 and m7 are each independently an integer from 1 to 4,

[0160] m4 and m6 are each independently one of integers from 1 to 3, and

[0161] p is an integer from 0 to 2;

[0162]

[0163] In chemical formulas 3 and 4,

[0164] Ar 6 and Ar 7 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0165] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R a , among a1* to a4* in Chemical Formula 3, two adjacent ones are each connected to * in Chemical Formula 4, L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0166] R a , R 28 and R 29 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, and

[0167] m8 and m9 are each independently one of integers from 1 to 4.

[0168] The second compound may be used together with the first compound in the light emitting layer to improve light emitting efficiency and lifespan characteristics by increasing charge mobility and stability.

[0169] For example, in Formula 2, Ar4 and Ar 5may be each 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 triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted fluorenyl group,

[0170] In chemical formula 2, L 4 and L 5 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0171] In chemical formula 2, R 23 To R 27 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and

[0172] p can be 0 or 1.

[0173] As an example, in Chemical Formula 2, “substituted” means that at least one hydrogen is replaced by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0174] In a specific embodiment of the present invention, Chemical Formula 2 may be represented by one of Chemical Formulas 2-1 to 2-15.

[0175]

[0176]

[0177] In Chemical Formulae 2-1 to 2-15, R 23 To R 27 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, m3, m5 and m7 may each independently be one of integers from 1 to 4, m4 and m6 may each independently be one of integers from 1 to 3, and *-L 4 -Ar 4 and *-L 5 -Ar 5 may each independently be one of the substituents listed in Group II.

[0178] [Group II]

[0179]

[0180] In Group II, n1 is one of the integers from 1 to 5, n2 is one of the integers from 1 to 4, n3 is one of the integers from 1 to 3, n4 is one of the integers from 1 to 11, n5 is one of the integers from 1 to 7, n6 is one of the integers from 1 to 9, and

[0181] * is the connection point.

[0182] In one embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0183] In addition, *-L in Chemical Formula 2-8 4 -Ar 4 and *-L 5 -Ar 5 Each may be independently selected from Group II, such as C-1, C-2, C-3, C-4, C-7, C-8 and C-9.

[0184] As an example, the second compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 may be represented by any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0185]

[0186] In Chemical Formulae 3A to 3E, Ar 6 ,Ar 7 , L 6 , L 7 , R 28 , R 29 , m8 and m9 are the same as above,

[0187] L a1 To L a4 With the above L 6 and L 7 The definition of is the same as

[0188] R a1 To R a4 With the above R 28 and R 29 The definition is the same.

[0189] For example, in Formulas 3 and 4, Ar 6 and Ar 7 may be each independently 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,

[0190] R a1 To R a4 , R 28 and R 29Each of them may independently be hydrogen, deuterium, cyano, 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.

[0191] In a specific embodiment of the present invention, *-L in Chemical Formulas 3 and 4 6 -Ar 6 and *-L 7 -Ar 7 The substituents listed in Group II may be each independently selected.

[0192] In one embodiment, R a1 To R a4 , R 28 and R 29 Each of them may independently be hydrogen, deuterium, cyano, 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.

[0193] For example, R a1 To R a4 , R 28 and R 29 may each independently be hydrogen, deuterium, cyano or a substituted or unsubstituted C6 to C12 aryl group, and

[0194] In a specific embodiment, R a1 To R a4 , R 28 and R 29 Each may independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group.

[0195] In a specific embodiment of the present invention, the second compound can be represented by Chemical Formula 2-8, wherein in Chemical Formula 2-8, Ar 4 and Ar 5 may be each independently 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, L 4 and L 5 may each independently be a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 23 To R 27 Each of them may independently be hydrogen, deuterium, cyano, 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.

[0196] In another specific embodiment of the present invention, the second compound can be represented by Chemical Formula 3C, in which L a3 and L a4 Can be a single bond, L 6 and L 7 may be each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 28 and R 29 , R a3 and R a4 may each be hydrogen, deuterium or phenyl, and Ar 6 and Ar 7 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0197] For example, the second compound may be one of the compounds selected from Group 2, but is not limited thereto.

[0198] [Group 2]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. Within the above range, bipolar characteristics may be achieved by matching an appropriate weight ratio using the electron transport capability of the first compound and the hole transport capability of the second compound to improve efficiency and lifespan. Within this range, for example, they may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, such as about 20:80 to about 70:30, about 20:80 to about 60:40, and about 20:80 to about 50:50. As a specific embodiment, they may be included in a weight ratio of about 20:80, 30:70, or 40:60.

[0214] In addition to the above-mentioned first compound and second compound, one or more additional compounds may be included.

[0215] For example, the compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above may further include a dopant.

[0216] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0217] A dopant is a material mixed in a small amount with a compound used for an organic optoelectronic device to cause light emission, and generally may be a material that emits light by multiple excitations to a triplet state or more, such as a metal complex. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and one or more types thereof may be used.

[0218] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0219] [Chemical formula Z]

[0220] L 8 MX

[0221] In the chemical formula Z, M is a metal and L 8 and X are the same or different and are ligands for forming a complex with M.

[0222] 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 8 and X may be, for example, a bidentate ligand.

[0223] By L8 Examples of the ligand represented by and X may be selected from the chemical formulae listed in Group A, but are not limited thereto.

[0224] [Group A]

[0225]

[0226] In Group A,

[0227] R 300 To R 302 are each independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted by halogen, C6 to C30 aryl which may be substituted by C1 to C30 alkyl, or halogen, and

[0228] R 303 To R 324 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, 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.

[0229] As an example, it may include a dopant represented by Chemical Formula V.

[0230]

[0231] In chemical formula V,

[0232] R 101 To R 116 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0233] R 132 To R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0234] R 101 To R 116 At least one of them is a functional group represented by Chemical Formula IV-1,

[0235] L100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone carbon pair or a heteroatom, and

[0236] n1 and n2 are each independently any one of integers from 0 to 3, and n1+n2 is any one of integers from 1 to 3,

[0237]

[0238] In chemical formula V-1,

[0239] R 135 To R 139 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,and

[0240] * indicates a moiety attached to a carbon atom.

[0241] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0242]

[0243] In the chemical formula Z-1, rings A, B, C and D independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0244] R A , R B , R C and R D independently represents mono-, di-, tri- or tetra-substituted or unsubstituted;

[0245] L B , L C and L D Each is independently selected from a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof;

[0246] When nA is 1, L E is selected from the group consisting of direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof; when nA is 0, L E does not exist; and

[0247] R A , R B , R C , R DR, R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfhydryl, sulfinyl, sulfonyl, phosphino and combinations thereof; any adjacent R A , R B , R C , R D , R and R' are optionally linked to each other to provide a ring; X B , X C , X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Each represents oxygen or a direct bond.

[0248] The dopant according to the embodiment may be a platinum complex, and may be represented, for example, by Chemical Formula VI.

[0249]

[0250]

[0251] In Chemical Formula VI,

[0252] X 100 Selected from O, S and NR 131 ,

[0253] R 117 To R 131 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0254] R 132 To R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group, and

[0255] R 117 To R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl.

[0256] Hereinafter, an organic optoelectronic device using the above-mentioned compound for an organic optoelectronic device or the composition for an organic optoelectronic device is described.

[0257] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy and vice versa, for example, an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photoconductor.

[0258] Herein, an organic light emitting diode as one embodiment of an organic optoelectronic device is described with reference to the accompanying drawings.

[0259] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0260] Reference Figure 1 , an organic light emitting diode 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0261] The anode 120 may be made of a conductor having a high 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, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; 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) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0262] The cathode 110 may be made of a conductor with a low 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 include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0263] The organic layer 105 may include the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[0264] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-described compound for an organic optoelectronic device or composition for an organic optoelectronic device.

[0265] The composition for an organic optoelectronic device further including a dopant may be, for example, a red or green light emitting composition.

[0266] The light emitting layer 130 may include, for example, the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device as a phosphorescent host.

[0267] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0268] The charge transport region may be, for example, a hole transport region 140 .

[0269] The hole transport region 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 , and block electrons.

[0270] 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 group B compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0271] [Group B]

[0272]

[0273]

[0274]

[0275]

[0276] In the hole transport region, in addition to the above-mentioned compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having similar structures can be used.

[0277] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0278] The electron transport region 150 may further increase electron injection and / or electron mobility and block holes between the cathode 110 and the light emitting layer 130 .

[0279] 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 group C compounds may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0280] [Group C]

[0281]

[0282]

[0283]

[0284] Embodiments of the present invention may provide an organic light emitting diode including a light emitting layer as an organic layer.

[0285] Another embodiment of the present invention may provide an organic light emitting diode including a light emitting layer and a hole transporting region as an organic layer.

[0286] Another embodiment of the present invention may provide an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0287] Another embodiment of the present invention may provide an organic light emitting diode including a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130, such as Figure 1 as shown in .

[0288] On the other hand, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as an organic layer in addition to the light emitting layer.

[0289] The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0290] The organic light emitting diode may be applied to an organic light emitting display device.

[0291] [Embodiments of the present invention]

[0292] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the claims is not limited thereto.

[0293] Hereinafter, unless otherwise specified, 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 were synthesized by known methods.

[0294] (Preparation of Compounds for Organic Optoelectronic Devices)

[0295] As a more specific example of the compound of the present invention, the provided compound was synthesized by the following steps.

[0296] Synthesis Example 1: Synthesis of Intermediate I-1

[0297]

[0298] In a nitrogen environment, 2-chloro-4,6-diphenyl-1,3,5-triazine (50g, 187mmol) was dissolved in 0.4L of tetrahydrofuran (THF), and 4-chloro-2-fluorophenylboric acid (39g, 224mmol) and tetrakis (triphenylphosphine) palladium (6.5g, 5.6mmol) were added thereto, and then stirred. Subsequently, potassium carbonate (64.5g, 467mmol) saturated in water was added thereto, and then refluxed by heating at 80°C for 12 hours. When the reaction was complete, after water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-1 (38.19g, 56%).

[0299] HRMS (70 eV, EI+): m / z calculated for C21H13ClFN3: 361.0782, found: 361.

[0300] Elemental analysis: C, 70%; H, 4%

[0301] Synthesis Example 2: Synthesis of Intermediate I-2

[0302]

[0303] In a nitrogen environment, intermediate I-1 (38.19 g, 105.5 mmol) was dissolved in 0.4 L of dioxane, and phenylboric acid (19.3 g, 158 mmol), tris (diphenylacetone) dipalladium (0) (2.9 g, 3.2 mmol), tri-tert-butylphosphine (3.2 g, 15.8 mmol) and cesium carbonate (86 g, 264 mmol) were added thereto in sequence, and then, refluxed by heating at 110 ° C for 20 hours. When the reaction was completed, after water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-2 (25.17 g, 59%).

[0304] HRMS (70 eV, EI+): m / z calculated for C27H18FN3: 403.1485, found: 403.

[0305] Elemental analysis: C, 80%; H, 5%

[0306] Synthesis Example 3: Synthesis of Intermediate I-3

[0307]

[0308] Intermediate I-3 (53.86 g, 51%) was obtained in the same manner as in Synthesis Example 1, except that 2-hydroxyphenylboronic acid (50 g, 362 mmol) and 1,4-dibromo-2-nitrobenzene (122.2 g, 435 mmol) were used.

[0309] HRMS (70 eV, EI+): m / z calculated for C12H8BrNO3: 292.9688, found: 292.

[0310] Elemental analysis: C, 49%; H, 3%

[0311] Synthesis Example 4: Synthesis of Intermediate I-4

[0312]

[0313] In a nitrogen environment, intermediate I-3 (54.28g, 184.5mmol) is dissolved in 0.4L acetone, and iodomethane (31.4g, 221.5mmol) and potassium carbonate (30.6g, 221.5mmol) are added thereto, then, by heating to reflux at 50°C for 8 hours. When the reaction is complete, after water is added to the reaction solution, the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained is separated and purified by flash column chromatography to obtain intermediate I-4 (55.55g, 99%).

[0314] HRMS (70 eV, EI+): m / z calculated for C13H10BrNO3: 306.9844, found: 306.

[0315] Elemental analysis: C, 51%; H, 3%

[0316] Synthesis Example 5: Synthesis of Intermediate I-5

[0317]

[0318] In a nitrogen environment, intermediate I-4 (55.55g, 181mmol) was dissolved in 0.5L of dichlorobenzene (DCB), and triphenylphosphine (142.7g, 544mmol) was added thereto, and then, heated to reflux for 3 hours at 200°C. When the reaction was complete, after water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-5 (34.8g, 70%).

[0319] HRMS (70 eV, EI+): m / z calculated for C13H10BrNO: 274.9946, found: 274.

[0320] Elemental analysis: C, 57%; H, 4%

[0321] Synthesis Example 6: Synthesis of Intermediate I-6

[0322]

[0323] Intermediate I-6 (23.24 g, 68%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-5 (34.8 g, 126 mmol) and phenylboronic acid (18.4 g, 151 mmol) were used.

[0324] HRMS (70 eV, EI+): m / z calculated for C19H15NO: 273.1154, found: 273

[0325] Elemental analysis: C, 83%; H, 6%

[0326] Synthesis Example 7: Synthesis of Intermediate I-7

[0327]

[0328] In a nitrogen environment, intermediate I-6 (23.24g, 85mmol) is dissolved in 0.2L of xylene, and iodobenzene (20.8g, 102mmol), copper (I) iodide (3.2g, 17mmol), ethylenediamine (5.1g, 85mmol) and tripotassium phosphate (36g, 170mmol) are added thereto in sequence, and then, by heating to reflux for 16 hours at 130°C. When the reaction is complete, after adding water and ammonium chloride to the reaction solution, the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained is separated and purified by flash column chromatography to obtain intermediate I-7 (28.39g, 96%).

[0329] HRMS (70 eV, EI+): m / z calculated for C25H19NO: 349.1467, found: 349.

[0330] Elemental analysis: C, 86%; H, 5%

[0331] Synthesis Example 8: Synthesis of Intermediate I-8

[0332]

[0333] In a nitrogen environment, intermediate I-7 (28.39 g, 81.2 mmol) and pyridine hydrochloride (46.9 g, 406 mmol) were added and refluxed at 180 ° C for 12 hours. When the reaction was complete, after adding water to the reaction solution, the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-8 (26.12 g, 96%).

[0334] HRMS (70 eV, EI+): m / z calculated for C24H17NO: 335.1310, found: 335.

[0335] Elemental analysis: C, 86%; H, 5%

[0336] Synthesis Example 9: Synthesis of Intermediate I-9

[0337]

[0338] In a nitrogen environment, intermediate I-8 (26.12g, 77.9mmol) was dissolved in 0.3L of dichloromethane (DCM), triethylamine (9.5g, 93.5mmol) was added thereto, and then stirred for 30 minutes, then cooled to 0°C, and trifluoromethanesulfonic anhydride (26.4g, 93.5mmol) was slowly added thereto, and then stirred. After 30 minutes, the reaction solution was cooled to 0°C, and after slowly adding water thereto for 30 minutes, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-9 (30.81g, 85%).

[0339] HRMS (70 eV, EI+): m / z calculated for C25H16F3NO3S: 467.0803, found: 467.

[0340] Elemental analysis: C, 64%; H, 3%

[0341] Synthesis Example 10: Synthesis of Intermediate I-10

[0342]

[0343] In a nitrogen environment, intermediate I-9 (30.71 g, 65.7 mmol) was dissolved in 0.3 L of dioxane, and 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole (19.3 g, 65.7 mmol) and tetrakis (triphenylphosphine) palladium (1.52 g, 1.3 mmol) were added thereto, and then stirred. Subsequently, potassium carbonate saturated in water (22.7 g, 164 mmol) was added thereto, and then, refluxed by heating at 100 ° C for 12 hours. When the reaction was completed, after water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-10 (28.07 g, 88%).

[0344] HRMS (70 eV, EI+): m / z calculated for C36H24N2: 484.1939, found: 484.

[0345] Elemental analysis: C, 89%; H, 5%

[0346] Synthesis Example 11: Synthesis of Compound A-13

[0347]

[0348] In a nitrogen environment, intermediate I-10 (8.4g, 17.4mmol) was dissolved in 0.1L of N-methyl-2-pyrrolidone (NMP), and intermediate I-2 (7g, 17.4mmol) and tripotassium phosphate (5.2g, 34.7mmol) were added thereto, and then refluxed for 18 hours. After the reaction was complete, the solvent was distilled out, and after water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain compound A-13 (14.1g, 93%).

[0349] HRMS (70eV, EI+): m / z calculated for C63H41N5: 867.3362, found: 867.

[0350] Elemental analysis: C, 87%; H, 5%

[0351] Synthesis Example 12: Synthesis of Intermediate I-11

[0352]

[0353] In a nitrogen environment, http: / / www.ytgemchem.comDeuterium-substituted 4-bromo-9-phenyl-9H-carbazole (57.28 g, 172 mmol) was dissolved in 0.4 L of dioxane, and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (42 g, 143 mmol) and (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium (II) (11.7 g, 14.3 mmol) were added thereto, and then stirred. Subsequently, potassium carbonate saturated in water (59 g, 430 mmol) was added thereto, and then, refluxed by heating at 100 ° C for 12 hours. When the reaction was completed, after water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-11 (51.5 g, 86%).

[0354] HRMS (70 eV, EI+): m / z calculated for C30H8D12N2: 420.2367, found: 420.

[0355] Elemental analysis: C, 86%; H, 8%

[0356] Synthesis Example 13: Synthesis of Intermediate I-12

[0357]

[0358] Intermediate I-12 (15.34 g, 40%) was obtained in the same manner as in Synthesis Example 1, except that 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine (30 g, 87 mmol) and 4-chloro-2-fluorophenylboric acid (18.3 g, 105 mmol) were used.

[0359] HRMS (70 eV, EI+): m / z calculated for C27H17ClFN3: 437.1095, found: 437.

[0360] Elemental analysis: C, 74%; H, 4%

[0361] Synthesis Example 14: Synthesis of Intermediate I-13

[0362]

[0363] Intermediate I-13 (10.62 g, 64%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-12 (15.34 g, 35 mmol) and phenylboronic acid (6.4 g, 52.5 mmol) were used.

[0364] HRMS (70 eV, EI+): m / z calculated for C33H22FN3: 479.1798, found: 479.

[0365] Elemental analysis: C, 83%; H, 5%

[0366] Synthesis Example 15: Synthesis of Compound A-26

[0367]

[0368] In a nitrogen environment, intermediate I-11 (8.52g, 17.7mmol) is dissolved in 0.1L of N-methyl-2-pyrrolidone (NMP), and intermediate I-2 (7.14g, 17.7mmol) and cesium carbonate (5.8g, 17.7mmol) are added thereto, then, refluxed for 18 hours. After the reaction is complete, the solvent is distilled out, and after water is added to the reaction solution, the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained is separated and purified by flash column chromatography to obtain compound A-26 (13.61g, 86%).

[0369] HRMS (70eV, EI+): m / z calculated for C58H28D11N5: 816.3885, found: 816.

[0370] Elemental analysis: C, 85%; H, 6%

[0371] Synthesis Example 16: Synthesis of Intermediate I-14

[0372]

[0373] Intermediate I-14 (97.35 g, 76%) was obtained in the same manner as in Synthesis Example 7, except that 4-bromo-9H-carbazole (100 g, 406 mmol) and iodobenzene (99.5 g, 487 mmol) were used.

[0374] HRMS (70 eV, EI+): m / z calculated for C18H12BrN: 321.0153, found: 321.

[0375] Elemental analysis: C, 67%; H, 4%

[0376] Synthesis Example 17: Synthesis of Intermediate I-15

[0377]

[0378] Intermediate I-15 (50.02 g, 86%) was obtained in the same manner as in Synthesis Example 12, except that 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (42 g, 143 mmol), Intermediate I-14 (55.38 g, 172 mmol) and Intermediate I-14 (55.38 g, 172 mmol) purchased from Ukseung Chemical Co., Ltd. (http: / / www.ukseung.co.kr / ) were used.

[0379] HRMS (70eV, EI+): m / z calculated for C30H20N2: 408.1626, found: 408.

[0380] Elemental analysis: C, 88%; H, 5%

[0381] Synthesis Example 18: Synthesis of Compound A-52

[0382]

[0383] Compound A-52 (13.23 g, 86%) was obtained in the same manner as in Synthesis Example 15, except that Intermediate I-13 (8.52 g, 17.7 mmol) and Intermediate I-15 (7.26 g, 17.7 mmol) were used.

[0384] HRMS (70eV, EI+): m / z calculated for C63H41N5: 867.3362, found: 867.

[0385] Elemental analysis: C, 87%; H, 5%

[0386] Synthesis Example 19: Synthesis of Intermediate I-16

[0387]

[0388] Intermediate I-16 (58.48 g, 46%) was obtained in the same manner as in Synthesis Example 1, except that 2-chloro-4-(biphenyl-3-yl)-6-phenyl-1,3,5-triazine (100 g, 291 mmol) and 4-chloro-2-fluorophenylboric acid (60.9 g, 349 mmol) were used.

[0389] HRMS (70 eV, EI+): m / z calculated for C27H17ClFN3: 437.1095, found: 437.

[0390] Elemental analysis: C, 74%; H, 4%

[0391] Synthesis Example 20: Synthesis of Intermediate I-17

[0392]

[0393] Intermediate I-17 (21.25 g, 33%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-16 (58.48 g, 133.5 mmol) and phenylboronic acid (24.4 g, 200 mmol) were used.

[0394] HRMS (70 eV, EI+): m / z calculated for C33H22FN3: 479.1798, found: 479.

[0395] Elemental analysis: C, 83%; H, 5%

[0396] Synthesis Example 21: Synthesis of Compound A-55

[0397]

[0398] Compound A-55 (19.7 g, 98%) was obtained in the same manner as in Synthesis Example 11, except that Intermediate I-17 (11 g, 23 mmol) and Intermediate I-15 (9.4 g, 23 mmol) were used.

[0399] HRMS (70eV, EI+): m / z calculated for C64H41N5: 867.3362, found: 867.

[0400] Elemental analysis: C, 87%; H, 5%

[0401] Synthesis Example 22: Synthesis of Intermediate I-18

[0402]

[0403] In a nitrogen environment, 2-(9,9-dimethyl-9H-fluorene-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (100g, 312.3mmol) was dissolved in 0.4L of xylene, and 2,4-dichloro-phenyl-1,3,5-triazine (84.7g, 374.7mmol) and tetrakis(triphenylphosphine)palladium (3.58g, 3.1mmol) were added thereto, and then stirred. Subsequently, potassium carbonate (107.9g, 780.75mmol) and tetrahydrofuran (THF) saturated in water were added thereto, and then, heated to reflux at 80°C for 12 hours. When the reaction was complete, after water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate 1-18 (46.75 g, 39%).

[0404] HRMS (70 eV, EI+): m / z calculated for C24H18ClN3: 383.1189, found: 383.

[0405] Elemental analysis: C, 75%; H, 5%

[0406] Synthesis Example 23: Synthesis of Intermediate I-19

[0407]

[0408] Intermediate I-19 (41.33 g, 71%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-18 (46.75 g, 121.8 mmol) and 4-chloro-2-fluorophenylboronic acid (25.48 g, 146.1 mmol) were used.

[0409] HRMS (70eV, EI+): m / z calculated for C30H21ClFN3: 477.1408, found: 477.

[0410] Elemental analysis: C, 75%; H, 4%

[0411] Synthesis Example 24: Synthesis of Intermediate I-20

[0412]

[0413] Intermediate I-20 (28.77 g, 64%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-19 (41.33 g, 86.5 mmol) and phenylboronic acid (12.6 g, 103.8 mmol) were used.

[0414] HRMS (70 eV, EI+): m / z calculated for C36H26FN3: 519.2111, found: 519.

[0415] Elemental analysis: C, 83%; H, 5%

[0416] Synthesis Example 25: Synthesis of Compound A-169

[0417]

[0418] Compound A-169 (16.32 g, 85%) was obtained in the same manner as in Synthesis Example 15, except that Intermediate I-20 (10 g, 19.2 mmol) and Intermediate I-15 (7.86 g, 19.2 mmol) were used.

[0419] HRMS (70 eV, EI+): m / z calculated for C66H45N5: 907.3675, found: 907.

[0420] Elemental analysis: C, 87%; H, 5%

[0421] Synthesis Example 26: Synthesis of Intermediate I-21

[0422]

[0423] Intermediate I-21 (92.8 g, 74%) was obtained in the same manner as in Synthesis Example 7, except that 11-bromo-7H-benzo[c]carbazole (100 g, 337 mmol) and iodobenzene (82.7 g, 405 mmol) purchased from Ukseung Chemical Co., Ltd. were used.

[0424] HRMS (70 eV, EI+): m / z calculated for C22H14BrN: 371.0310, found: 371.

[0425] Elemental analysis: C, 71%; H, 4%

[0426] Synthesis Example 27: Synthesis of Intermediate I-22

[0427]

[0428] Intermediate I-22 (76.89 g, 81%) was obtained in the same manner as in Synthesis Example 12, except that 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-carbazole (60.9 g, 207 mmol) and intermediate I-21 (92.8 g, 249 mmol) were used.

[0429] HRMS (70eV, EI+): m / z calculated for C34H22N2: 458.1783, found: 458.

[0430] Elemental analysis: C, 89%; H, 5%

[0431] Synthesis Example 28: Synthesis of Compound A-223

[0432]

[0433] Compound A-223 (13.4 g, 64%) was obtained in the same manner as in Synthesis Example 15, except that Intermediate I-2 (10 g, 24.8 mmol) and Intermediate I-22 (11.37 g, 24.8 mmol) were used.

[0434] HRMS (70 eV, EI+): m / z calculated for C61H39N5: 841.3205, found: 841.

[0435] Elemental analysis: C, 87%; H, 5%

[0436] Synthesis Example 29: Synthesis of Intermediate I-23

[0437]

[0438] Intermediate I-23 (53.5 g, 45%) was obtained in the same manner as in Synthesis Example 22, except that 9,9-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-9H-9-silicon dioxide (100 g, 297.3 mmol) and 2,4-dichloro-phenyl-1,3,5-triazine (80.7 g, 356.8 mmol) purchased from Ukseung Chemical Co., Ltd. were used.

[0439] HRMS (70eV, EI+): m / z calculated for C23H18ClN3Si: 399.0959, found: 399.

[0440] Elemental analysis: C, 69%; H, 5%

[0441] Synthesis Example 30: Synthesis of Intermediate I-24

[0442]

[0443] Intermediate I-24 (47.6 g, 72%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-23 (53.5 g, 133.8 mmol) and 4-chloro-2-fluorophenylboronic acid (28 g, 160.5 mmol) were used.

[0444] HRMS (70 eV, EI+): m / z calculated for C29H21ClFN3Si: 493.1177, found: 493.

[0445] Elemental analysis: C, 71%; H, 4%

[0446] Synthesis Example 31: Synthesis of Intermediate I-25

[0447]

[0448] Intermediate I-25 (28.37 g, 55%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-24 (47.6 g, 96.3 mmol) and phenylboronic acid (14.1 g, 115.5 mmol) were used.

[0449] HRMS (70 eV, EI+): m / z calculated for C35H26FN3Si: 535.1880, found: 535.

[0450] Elemental analysis: C, 78%; H, 5%

[0451] Synthesis Example 32: Synthesis of Compound A-250

[0452]

[0453] Compound A-250 (12.6 g, 73%) was obtained in the same manner as in Synthesis Example 15, except that Intermediate I-25 (10 g, 18.7 mmol) and Intermediate I-15 (7.6 g, 18.7 mmol) were used.

[0454] HRMS (70eV, EI+): m / z calculated value for C65H45N5Si: 923.3444, found value: 923.

[0455] Elemental analysis: C, 84%; H, 5%

[0456] Synthesis Example 33: Synthesis of Intermediate I-26

[0457]

[0458] Intermediate I-26 (82.26 g, 70%) was obtained in the same manner as Synthesis Example 10, except that 2-chloro-4-(biphenyl-4-yl)-6-phenyl-1,3,5-triazine (100 g, 291 mmol) and 2-fluorophenylboric acid (49 g, 349 mmol) were used.

[0459] HRMS (70 eV, EI+): m / z calculated for C27H18FN3: 403.1485, found: 403.

[0460] Elemental analysis: C, 80%; H, 5%

[0461] Synthesis Example 34: Synthesis of Compound A-312

[0462]

[0463] Compound A-312 (19.4 g, 97%) was obtained in the same manner as in Synthesis Example 15, except that Intermediate I-26 (10.1 g, 25.25 mmol) and Intermediate I-15 (10.3 g, 25.25 mmol) were used.

[0464] HRMS (70 eV, EI+): m / z calculated for C57H37N5: 791.3049, found: 791.

[0465] Elemental analysis: C, 86%; H, 5%

[0466] Synthesis Example 35: Synthesis of Intermediate I-27

[0467]

[0468] Intermediate I-27 (16.66 g, 72%) was obtained in the same manner as in Synthesis Example 10, except that 2-chloro-4-(3-dibenzofuranyl)-6-phenyl-1,3,5-triazine (20 g, 56 mmol) and 2-fluorophenylboric acid (8.6 g, 61.5 mmol) purchased from Ukseung Chemical Co., Ltd. were used.

[0469] HRMS (70 eV, EI+): m / z calculated for C27H16FN3O: 417.1277, found: 417.

[0470] Elemental analysis: C, 78%; H, 4%

[0471] Synthesis Example 36: Synthesis of Compound A-342

[0472]

[0473] Compound A-342 (31.34 g, 97%) was obtained in the same manner as in Synthesis Example 15, except that Intermediate I-27 (16.66 g, 40 mmol) and Intermediate I-15 (16.3 g, 40 mmol) were used.

[0474] HRMS (70eV, EI+): m / z calculated for C57H35N5O: 805.2842, found: 805.

[0475] Elemental analysis: C, 85%; H, 4%

[0476] Synthesis Example 37: Synthesis of Compound R-1

[0477] Compound R-1 was synthesized by referring to the synthesis method of patent WO2014-092083.

[0478] HRMS (70 eV, EI+): m / z calculated for C51H33N5: 715.2736, found: 715.

[0479] Elemental analysis: C, 86%; H, 5%

[0480] Synthesis Example 38: Synthesis of Compound R-2

[0481] Compound R-2 was synthesized by referring to the synthesis method of patent KR 10-1926771.

[0482] HRMS (70 eV, EI+): m / z calculated for C57H37N5: 791.3049, found: 791.

[0483] Elemental analysis: C, 86%; H, 5%

[0484] Synthesis Example 39: Synthesis of Compound R-3

[0485] Compound R-3 was synthesized by referring to the synthesis method of Patent KR 10-2171124.

[0486] HRMS (70 eV, EI+): m / z calculated for C51H33N5: 715.2736, found: 715.

[0487] Elemental analysis: C, 86%; H, 5%

[0488] Synthesis Example 40: Synthesis of Compound R-4

[0489] Compound R-4 was synthesized by referring to the synthesis method of patent KR 10-2014-0094520.

[0490] HRMS (70 eV, EI+): m / z calculated for C51H33N5: 715.2736, found: 715.

[0491] Elemental analysis: C, 86%; H, 5%

[0492] Synthesis Example 41: Synthesis of Compound R-5

[0493]

[0494] Compound R-5 was synthesized by referring to the synthesis method of patent US2018-0145262.

[0495] HRMS (70 eV, EI+): m / z calculated for C57H37N5: 791.3049, found: 791.

[0496] Elemental analysis: C, 86%; H, 5%

[0497] Synthesis Example 42: Synthesis of Compound R-6

[0498] Compound R-6 was synthesized by referring to the synthesis method of patent US2018-0145262.

[0499] HRMS (70 eV, EI+): m / z calculated for C57H37N5: 791.3049, found: 791.

[0500] Elemental analysis: C, 86%; H, 5%

[0501] Synthesis Example 43: Synthesis of Compound B-136

[0502]

[0503] Compound B-136 was synthesized by referring to the synthesis method of patent EP 3034581.

[0504] HRMS (70eV, EI+): m / z calculated for C42H28N2: 560.2252, found: 560.

[0505] Elemental analysis: C, 90%; H, 5%

[0506] Synthesis Example 44: Synthesis of Compound B-99

[0507]

[0508] Compound B-99 was synthesized by referring to the synthesis method of patent KR10-2019-0000597.

[0509] HRMS (70eV, EI+): m / z calculated for C48H32N2: 636.2565, found: 636.

[0510] Elemental analysis: C, 91%; H, 5%

[0511] Synthesis Example 45: Synthesis of Compound B-31

[0512]

[0513] Compound B-31 was synthesized by referring to the synthesis method of patent EP2947071.

[0514] HRMS (70eV, EI+): m / z calculated for C48H32N2: 636.2565, found: 636.

[0515] Elemental analysis: C, 91%; H, 5%

[0516] Synthesis Example 46: Synthesis of Compound C-4

[0517]

[0518] Compound C-4 was synthesized by referring to the synthesis method of patent KR2031300.

[0519] HRMS (70eV, EI+): m / z calculated for C42H28N2: 560.2252, found: 560.

[0520] Elemental analysis: C, 90%; H, 5%

[0521] Synthesis Example 47: Synthesis of Compound C-57

[0522]

[0523] Compound C-57 was synthesized by referring to the synthesis method of patent WO2018-095391.

[0524] HRMS (70eV, EI+): m / z calculated for C48H32N2: 636.2565, found: 636.

[0525] Elemental analysis: C, 91%; H, 5%

[0526] Manufacturing of organic light-emitting diodes (green)

[0527] Example 1

[0528] A glass substrate coated with an ITO (indium tin oxide) thin film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The prepared ITO transparent electrode was used as an anode, and Compound A (Novaled GmbH) doped with 3% NDP-9 was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form Compound B is deposited on the hole transport layer to form A hole transport auxiliary layer having a thickness of 100 nm was formed, and the compound A-13 synthesized in Synthesis Example 11 was used as a host and PhGD was doped as a dopant at 7 wt % on the hole transport auxiliary layer by vacuum deposition to form a The ratios are described separately in the following examples and comparative examples. Subsequently, compound C is deposited on the light-emitting layer to form A thick electron transport auxiliary layer was formed, and compound D and Liq were simultaneously vacuum deposited in a weight ratio of 1:1 to form A thick electron transport layer (ETL) is formed on the electron transport layer by sequentially vacuum depositing LiQ and Al forms a cathode to manufacture an organic light emitting diode.

[0529] An organic light emitting diode was manufactured to have the following structure: ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[Compound A-13 (93 wt%):PhGD (7 wt%)] / Compound C / Compound D: LiQ / LiQ / Al

[0530] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0531] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0532] 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

[0533] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0534] [PhGD]

[0535]

[0536] Examples 2-9 and Comparative Examples 1-6

[0537] Each organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed as described in Table 1.

[0538] Example 10

[0539] A glass substrate coated with an ITO (indium tin oxide) thin film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A (Novaled GmbH) doped with 3% NDP-9 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 E is deposited on the hole transport layer to a thickness of On the hole transport auxiliary layer, the compound A-13 of Synthesis Example 11 and the compound B-136 of Synthesis Example 43, which were both used as a host and doped with 10 wt % of PhGD as a dopant, were vacuum deposited to form Herein, compound A-13 and compound B-136 are used in a weight ratio of 3:7. Subsequently, compound F is deposited on the light-emitting layer to form A thick electron transport auxiliary layer is formed thereon by vacuum depositing compound G and Liq at a weight ratio of 1:1 at the same time. On the electron transport layer, vacuum deposition is performed in sequence. LiQ and Al forms a cathode to manufacture an organic light emitting diode.

[0540] An organic light emitting diode was manufactured to have the following structure: ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound E / EML[Compound A-13:Compound B-136:PhGD=27:63:10 (wt%)] / Compound F / Compound G: LiQ / LiQ / Al

[0541] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0542] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0543] Compound F: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0544] Compound G: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0545] Examples 11 to 22 and Comparative Examples 7 to 12

[0546] Each organic light emitting diode was manufactured in the same manner as in Example 10, except that the composition was changed to each composition shown in Table 2.

[0547] Embodiment 23

[0548] An organic light emitting diode was manufactured in the same manner as in Example 10, except that the composition was changed to the composition shown in Table 2 and A-52:B-136 was mixed at a weight ratio of 4:6.

[0549] Embodiment 24

[0550] An organic light emitting diode was manufactured in the same manner as in Example 10, except that the composition was changed to the composition shown in Table 2 and A-52:B-136 was mixed at a weight ratio of 2:8.

[0551] evaluate

[0552] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes of Examples 1 to 24 and Comparative Examples 1 to 12 were evaluated.

[0553] The specific measurement method is as follows, and the results are shown in Tables 1 and 2.

[0554] (1) Measuring the change in current density due to voltage change

[0555] While increasing the voltage from 0 V to 10 V, the current flowing through the unit device of the manufactured organic light emitting diode was measured by using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0556] (2) Measuring the change in brightness due to voltage changes

[0557] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured by using a luminance meter (Minolta Cs-1000A).

[0558] (3) Measurement of luminous efficiency

[0559] The luminance, current density, and voltage measured in (1) and (2) were used to calculate the luminance at the same current density (10 mA / cm 2 ) under current efficiency (cd / A).

[0560] The luminous efficiency values ​​of Examples 1 to 9 and Comparative Examples 1 to 6 were calculated as relative values ​​based on Comparative Example 1 and are shown in Table 1.

[0561] The luminous efficiency values ​​of Examples 10 to 24 and Comparative Examples 7 to 12 were calculated as relative values ​​based on Comparative Example 7 and are shown in Table 2.

[0562] (4) Measurement life

[0563] While maintaining brightness (cd / m 2 ) is 24000cd / m 2 The results were obtained by measuring the time it took for the current efficiency (cd / A) to drop to 97%.

[0564] The life measurement values ​​of Examples 1 to 9 and Comparative Examples 1 to 6 were calculated as relative values ​​based on Comparative Example 1 and are shown in Table 1.

[0565] The life measurement values ​​of Examples 10 to 24 and Comparative Examples 7 to 12 were calculated as relative values ​​based on Comparative Example 7 and are shown in Table 2.

[0566] (5) Measure the driving voltage

[0567] The current-voltage meter (Keithley 2400) was used to measure the current of each device at 15 mA / cm 2 The driving voltage is as follows.

[0568] The driving voltages of Examples 1 to 9 and Comparative Examples 1 to 6 were calculated as relative values ​​based on Comparative Example 1 and are shown in Table 1.

[0569] The driving voltages of Examples 10 to 24 and Comparative Examples 7 to 12 were calculated as relative values ​​based on Comparative Example 7 and are shown in Table 2.

[0570] (Table 1)

[0571]

[0572] (Table 2)

[0573]

[0574]

[0575] Referring to Table 1 and Table 2, the organic light emitting diodes according to Examples 1 to 24 exhibited significantly improved light emitting efficiency and lifespan characteristics compared to the organic light emitting diodes according to Comparative Examples 1 to 12.

[0576] While the invention has been described in conjunction with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A compound for an organic optoelectronic device represented by Chemical Formula 1: [Chemical formula 1] In Chemical Formula 1, 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, Ar 3 is a substituted or unsubstituted C6 to C30 aryl group, L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, R 1 To R 14 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, R 1 To R 14 Each independently existing or adjacent groups are linked to form a substituted or unsubstituted aromatic monocyclic ring or a substituted or unsubstituted aromatic polycyclic ring, and R 15 To R 18 Each is independently hydrogen, deuterium, cyano or phenyl which is unsubstituted or substituted with deuterium.

2. The compound for an organic optoelectronic device according to claim 1, wherein The compound is represented by Chemical Formula 1-3: [Chemical formula 1-3] In chemical formula 1-3, Ar 1 To Ar 3 , R 1 To R 14 and L 1 To L 3 As defined in claim 1, Z is deuterium or cyano, D is deuterium, m1 is an integer from 0 to 3, and m2 is one of integers from 0 to 5.

3. The compound for an organic optoelectronic device according to claim 1, wherein R in Formula 1 1 To R 14 The groups each independently exist or are adjacent to each other to form a substituted or unsubstituted aromatic monocyclic ring, and are a compound for an organic optoelectronic device represented by any one of Chemical Formula 1A to Chemical Formula 1J: [Chemical Formula 1A] [Chemical formula 1B] [Chemical formula 1C] [Chemical formula 1D] [Chemical formula 1E] [Chemical formula 1F] [Chemical formula 1G] [Chemical formula 1H] [Chemical Formula 1I] [Chemical formula 1J] In Chemical Formulae 1A to 1J, Ar 1 To Ar 3 , R 1 To R 18 and L 1 To L 3 Same as defined in claim 1, and R 19 To R 22 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic.

4. The compound for an organic optoelectronic device according to claim 1, wherein R 1 To R 14 and each is independently hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted dibenzosilyl.

5. 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 phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazolyl group or a substituted or unsubstituted dibenzosilyl group.

6. The compound for an organic optoelectronic device according to claim 1, wherein *-L 1 -Ar 1 and *-L 2 -Ar 2 Each is independently selected from the substituents listed in Group I: [Group I] In Group I, * is the connection point.

7. The compound for an organic optoelectronic device according to claim 1, wherein the compound is selected from the compounds listed in Group 1: [Group 1] 8. A composition for an organic optoelectronic device, comprising a first compound and a second compound, in, The first compound is the compound for an organic optoelectronic device according to claim 1, and The second compound is a compound for an organic optoelectronic device represented by Chemical Formula 2; or a compound for an organic optoelectronic device represented by a combination of Chemical Formula 3 and Chemical Formula 4: [Chemical formula 2] In chemical formula 2, Ar 4 and Ar 5 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 23 To R 27 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, m3, m5 and m7 are each independently an integer from 1 to 4, m4 and m6 are each independently one of integers from 1 to 3, and p is an integer from 0 to 2; [Chemical formula 3] [Chemical formula 4] In chemical formulas 3 and 4, Ar 6 and Ar 7 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R a , Among a1* to a4* in Chemical Formula 3, two adjacent ones are each connected to * in Chemical Formula 4, L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a , R 28 and R 29 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, and m8 and m9 are each independently one of integers from 1 to 4.

9. The composition for an organic optoelectronic device according to claim 8, wherein: Chemical formula 2 is represented by Chemical formula 2-8: [Chemical formula 2-8] In Chemical Formula 2-8, R 23 , R 24 , R 26 and R 27 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and *-L 4 -Ar 4 and *-L 5 -Ar 5 are each independently one of the substituents listed in Group II, [Group II] In Group II, n1 is an integer from 1 to 5, n2 is an integer from 1 to 4, n3 is an integer from 1 to 3, n4 is an integer from 1 to 11, n5 is an integer from 1 to 7, n6 is an integer from 1 to 9, and * is the connection point.

10. The composition for an organic optoelectronic device according to claim 8, wherein 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 is a single key, L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 28 , R 29 , R a3 and R a4 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, Ar 6 and Ar 7 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl or substituted or unsubstituted biphenyl, and m8 and m9 are each independently one of integers from 1 to 4.

11. 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, in, The 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 10 .

12. The organic optoelectronic device according to claim 11, wherein: The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic optoelectronic device or the composition for an organic optoelectronic device. 13 . A display device comprising the organic optoelectronic device according to claim 11 .

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