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

Abstract

The present invention relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device and a display device. Specifically, the present invention discloses a compound for an organic optoelectronic device represented by Chemical Formula 1, a composition for an organic optoelectronic device including the compound, an organic optoelectronic device and a display device. The detailed description of Chemical Formula 1 is as described in the specification.

Description

[0001] Citations of Related Applications

[0002] This application claims the priority benefit of Korean Patent Application No. 10-2020-0114710 filed in the Korean Intellectual Property Office on September 8, 2020, the entire contents of which are incorporated herein by reference. Technical Field

[0003] 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

[0004] An organic photoelectric device (organic photodiode) is a device that can convert electrical energy into light energy and vice versa.

[0005] Organic photoelectric devices can be basically 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, and 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 include an organic optoelectronic 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 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

[0008] One embodiment provides a compound for an organic photoelectric device having high efficiency and long lifespan.

[0009] Another embodiment provides a composition for an organic photoelectric device including the compound.

[0010] Another embodiment provides an organic photoelectric device including the compound.

[0011] Another embodiment provides a display device including the organic photoelectric device.

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

[0013]

[0014] In Chemical Formula 1,

[0015] X 1 and X2 N or CR a ,

[0016] X 1 and X 2 At least one of them is N,

[0017] Ar 1 To Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0018] L 1 To L 3 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, and

[0019] R a and R 1 To R 8 and are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl.

[0020] According to another embodiment, a composition for an organic photoelectric device includes a first compound for an organic photoelectric device and a second compound for an organic photoelectric device.

[0021] The first compound for an organic photoelectric device may be the above-mentioned compound for an organic photoelectric device, and the second compound for an organic photoelectric device may be represented by Chemical Formula 2; or a combination of Chemical Formula 3 and Chemical Formula 4.

[0022]

[0023]

[0024] In chemical formula 2,

[0025] Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0026] L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0027] Rb and R 9 To R 18are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl, and

[0028] m is an integer from 0 to 2;

[0029]

[0030] In chemical formulas 3 and 4,

[0031] Y 3 and Y 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0032] Two adjacent ones of a1* to a4* in Chemical Formula 3 are connected to the connecting carbons of * in Chemical Formula 4, respectively.

[0033] The remaining two of a1* to a4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are independently CL a -R c ,

[0034] L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0035] R c and R 19 To R 26 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl.

[0036] According to another embodiment, an organic photoelectric 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 the compound for an organic photoelectric device or the composition for an organic photoelectric device.

[0037] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0038] An organic photoelectric device with high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figures 1 to 4 are cross-sectional views respectively showing organic light emitting diodes according to embodiments.

[0040] <Description of symbols>

[0041] 100, 200, 300, 400: Organic light emitting diodes

[0042] 105: Organic layer

[0043] 110: cathode

[0044] 120: Anode

[0045] 130: Luminous layer

[0046] 140: Hole transport zone

[0047] 150: Electron transport region DETAILED DESCRIPTION

[0048] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto and is defined by the scope of claims.

[0049] In the present specification, when no definition is otherwise provided, "substituted" means that at least one hydrogen of the substituent or the compound is replaced with 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.

[0050] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or a 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 of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0051] In the present specification, when a definition is not otherwise provided, "hetero" means a group including 1 to 3 hetero atoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0052] In the present specification, "aryl" refers to a group including at least one hydrocarbon aromatic part, and all elements of the hydrocarbon aromatic part have p-orbitals forming a conjugation, for example, phenyl, naphthyl, etc., two or more hydrocarbon aromatic parts can be connected by a σ bond and the hydrocarbon aromatic part can be (for example) biphenyl, terphenyl, tetraphenyl, etc., and two or more hydrocarbon aromatic parts are directly or indirectly fused to provide a non-aromatic fused ring, for example, fluorenyl.

[0053] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0054] In the present specification, "heterocyclic group" is a general concept of heteroaryl group, and may include at least one heteroatom selected from N, O, S, P and Si to replace 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 include one or more heteroatoms.

[0055] 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 may be directly connected by a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.

[0056] 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 naphthacenyl group, a substituted or unsubstituted pyrene 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 chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, or a combination thereof, but is not limited thereto.

[0057] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted phenylthio group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted unsubstituted benzimidazolyl, substituted or 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 or substituted or unsubstituted dibenzothiophenyl or a combination thereof, but are not limited thereto.

[0058] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and according to the highest occupied molecular orbital (HOMO) level, holes formed in the anode can be easily injected into the light-emitting layer due to the conductive characteristics and transported in the light-emitting layer.

[0059] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and according to the lowest unoccupied molecular orbital (LUMO) level, electrons formed in the cathode can be easily injected into the light-emitting layer due to the conductive property and transported in the light-emitting layer.

[0060] Hereinafter, a compound for an organic photoelectric device according to one embodiment is described.

[0061] The compound for an organic photoelectric device according to an embodiment is shown in Chemical Formula 1.

[0062]

[0063] In Chemical Formula 1,

[0064] X 1 and X 2 N or CR a ,

[0065] X 1 and X 2 At least one of them is N,

[0066] Ar 1 To Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0067] L 1 To L 3 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,

[0068] R a and R 1 To R 8 and are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl.

[0069] The compound represented by Chemical Formula 1 includes an indolo[2,3-a]carbazole skeleton and nitrogen (N) at the 1st and / or 10th positions in the indolo[2,3-a]carbazole skeleton, and has a structure in which indolo[2,3-a]carbazole is directly substituted with triazine in its N direction.

[0070] In the N direction of the indolo[2,3-a]carbazole, nitrogen (N) is included at the 1st and / or 10th position in the indolo[2,3-a]carbazole skeleton, and thus includes steric hindrance between the triazine and indolo[2,3-a]carbazole moieties that substitute the indolo[2,3-a]carbazole in its N direction.

[0071] When CH other than nitrogen (N) is included at the 1st or 10th position in the main chain of indolo[2,3-a]carbazole, the CH of indolo[2,3-a]carbazole and the hydrogen of triazine substituted in the N direction thereof are hindered in the degree of deviation from the plane due to steric hindrance, but by replacing the 1st or 10th position with nitrogen (N) to remove the hydrogen of CH as an interfering element, the plane deviation angle between the N-direction substituent of indolo[2,3-a]carbazole and the indolo[2,3-a]carbazole part can be larger, which reduces the interaction caused by the π-bond of the indolo[2,3-a]carbazole part and the triazine, thereby resulting in a higher LUMO energy level.

[0072] Therefore, it is possible to achieve high efficiency and long life characteristics of the organic light emitting diode to which it is applied.

[0073] Chemical Formula 1 may be represented by any one of Chemical Formulas 1A to 1C based on the substitution position of nitrogen (N) in the indolizine skeleton.

[0074]

[0075]

[0076] In Chemical Formulae 1A to 1C,

[0077] X 1 , X 2 ,Ar 1 To Ar 3 , L 1 To L 3 and R 1 To R 8 The definition of is the same as above.

[0078] In one embodiment, Ar 1 To Ar 3 and the like. Each of the above groups 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 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, or a substituted or unsubstituted dibenzosilyl group.

[0079] In a specific embodiment, Ar 1 To Ar 3 They may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group or a substituted or unsubstituted dibenzosilacyclyl group.

[0080] For example, Ar 1 To Ar 3 The groups may be independently selected from group I.

[0081] [Group I]

[0082]

[0083] In Group I, * is the connection point.

[0084] In a more specific embodiment, Ar 1 may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted terphenyl, and

[0085] Ar 2 and Ar 3They may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group.

[0086] When Ar 2 To Ar 3 When substituted, the substituent may be a C6 to C12 aryl group. More specifically, the substituent may be a phenyl group.

[0087] For example, Ar 1 and Ar 2 At least one of may be a substituted or unsubstituted C12 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0088] In a specific example, Ar 1 and Ar 2 At least one of the may be 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 or a substituted or unsubstituted dibenzosilolyl group.

[0089] In one embodiment, L 1 To L 3 They may each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzophenylenethio group.

[0090] In a specific embodiment, L 1 To L 3 Each independently may be a single bond or a substituted or unsubstituted phenylene group.

[0091] In one embodiment, R 1 To R 8 They may each independently be hydrogen or a substituted or unsubstituted phenyl group.

[0092] In a specific embodiment, R 1 To R 8 Each of may be hydrogen.

[0093] In another specific embodiment, R 1 To R 3 At least one of them may be a phenyl group, and R 4 To R 8 They may be hydrogen respectively.

[0094] More specific examples of the compound for an organic photoelectric device represented by Chemical Formula 1 include, but are not limited to, compounds of Group 1.

[0095] [Group 1]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] According to another embodiment, the composition for an organic optoelectronic device includes a first compound for an organic optoelectronic device and a second compound for an organic optoelectronic device. The first compound for an organic optoelectronic device may be the above-mentioned compound for an organic optoelectronic device, and the second compound for an organic optoelectronic device may be represented by Chemical Formula 2; or a combination of Chemical Formula 3 and Chemical Formula 4.

[0104]

[0105] In chemical formula 2,

[0106] Y 1 and Y 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0107] L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0108] R b and R 9 To R 18 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl, and

[0109] m is an integer from 0 to 2;

[0110]

[0111]

[0112] Wherein, in Chemical Formulas 3 and 4,

[0113] Y 3 and Y 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0114] Two adjacent ones of a1* to a4* in Chemical Formula 3 are connected to the connecting carbons of * in Chemical Formula 4, respectively.

[0115] The remaining two of a1* to a4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are independently CL a -R c .

[0116] As used herein, the term "attaching carbon" refers to the common carbon at which a fused ring is attached.

[0117] L a , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0118] R c and R 19 To R 26 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl.

[0119] The second compound for an organic photoelectric device may be used together with the first compound for an organic photoelectric device in the light emitting layer to improve charge mobility and improve stability, thereby improving light emitting efficiency and lifespan characteristics.

[0120] For example, Y in formula 2 1 and Y 2 may be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted fluorenyl,

[0121] L in chemical formula 2 4 and L 5may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0122] R in chemical formula 2 9 To R 18 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and

[0123] m can be 0 or 1.

[0124] For example, “substituted” in Chemical Formula 2 means that at least one hydrogen is replaced with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0125] In a specific embodiment of the present invention, Chemical Formula 2 may be represented by one of Chemical Formula 2-1 to Chemical Formula 2-15.

[0126]

[0127]

[0128] In Chemical Formulae 2-1 to 2-15, R 9 To R 18 may be independently hydrogen or a substituted or unsubstituted C6 to C12 aryl group, and *-L 4 -Y 1 and *-L 5 -Y 2 Each may independently be one of the substituents in Group II.

[0129] [Group II]

[0130]

[0131] In Group II, * is the connection point.

[0132] In one embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0133] In addition, *-L in Chemical Formula 2-8 4 -Y 1 and *-L 5 -Y 2 They may be independently selected from Group II, for example, any one of C-1, C-2, C-3 and C-4.

[0134] For example, the second compound for an organic photoelectric device represented by a 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.

[0135]

[0136]

[0137] In Chemical Formulae 3A to 3E, Y 3 , Y 4 , L 6 , L 7 and R 19 To R 26 Same as above,

[0138] L a1 To L a4 The definition of L is the same as above 6 and L 7 Same, and

[0139] R c1 To R c4 With R as mentioned above 19 To R 26 Same definition.

[0140] For example, Y in formula 3 and 4 3 and Y 4 may be independently 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, and

[0141] R c1 To R c4 and R 19 To R 26 They may each 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.

[0142] In a specific embodiment of the present invention, Y in Chemical Formulas 3 and 4 3 and Y 4 The substituents may be independently selected from group II.

[0143] In one embodiment, R c1 To R c4 and R 19 To R 26 They may each 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.

[0144] For example, R c1 To R c4 and R 19 To R 26 may be independently hydrogen, deuterium, cyano or substituted or unsubstituted phenyl,

[0145] In a specific embodiment, R c1 To R c4 can be hydrogen, and R 19 To R 26 They may each independently be hydrogen or phenyl.

[0146] In a specific embodiment of the present invention, the second compound for an organic optoelectronic device may be represented by Chemical Formula 2-8, and in Chemical Formula 2-8, Y 1 and Y 2 may be independently 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, L 4 and L 5 may each independently be a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 9 To R 18 They may each 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.

[0147] In another embodiment of the present invention, the second compound for an organic optoelectronic device may be represented by Chemical Formula 3C or Chemical Formula 3D, and in Chemical Formula 3C and Chemical Formula 3D, L a1 To L a4 Can be a single bond, L 6 and L 7 may be independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 19 To R 26 , R c1 To R c4 can be each independently hydrogen, and Y 3 and Y 4 The groups may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0148] For example, the second compound for an organic photoelectric device may be one of the compounds selected from Group 2, but is not limited thereto.

[0149] [Group 2]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158] The first compound for an organic optoelectronic device and the second compound for an organic optoelectronic device may be included in a weight ratio of about 1:99 to 99:1. Within this range, the desired weight ratio can be adjusted using the electron transport capability of the first compound for an organic optoelectronic device and the hole transport capability of the second compound for an organic optoelectronic device to achieve bipolar characteristics, and thus improve efficiency and lifespan. Within this range, they may be included, for example, in a weight ratio of about 10:90 to about 90:10, about 20:80 to 80:20, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, or about 30:70 to about 60:40. For example, they may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0159] In addition to the above-mentioned first compound for an organic photoelectric device and the second compound for an organic photoelectric device, one or more compounds may be further included.

[0160] The compound for an organic photoelectric device or the composition for an organic photoelectric device may be a composition further including a dopant.

[0161] 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.

[0162] The dopant is a material mixed in a trace amount with a compound or composition for an organic photoelectric device to cause light emission, and generally can be a material such as a metal complex that emits light by multiple excitations to a triplet state or more. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof can be used.

[0163] 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.

[0164] [Chemical formula Z]

[0165] L 8 MX 3

[0166] In the chemical formula Z, M is a metal and L 8 and X 3 are the same or different and are ligands that form a complex with M.

[0167] 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 3 It may be, for example, a bidentate ligand.

[0168] Hereinafter, an organic photoelectric device including the above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device is described.

[0169] The organic photoelectric device may be any device that converts electrical energy into light energy (or vice versa) without particular limitation, and it may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0170] Herein, an organic light emitting diode is described as an example of an organic photoelectric device with reference to the accompanying drawings.

[0171] Figures 1 to 4 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0172] refer to Figure 1 , the organic light emitting diode 100 according to the 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 .

[0173] 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, 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) (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0174] 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 an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0175] The organic layer 105 may include the above-described compound for an organic photoelectric device or the composition for an organic photoelectric device.

[0176] 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 photoelectric device or a composition for an organic photoelectric device.

[0177] The composition for an organic optoelectronic device further including a dopant may be, for example, a red light emitting composition.

[0178] The light emitting layer 130 may include, for example, the above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device as a phosphorescent host.

[0179] The organic layer may include a charge transport region in addition to the light emitting layer.

[0180] The auxiliary layer may be, for example, a hole auxiliary layer 140 .

[0181] refer to Figure 2 In addition to the light-emitting layer 130, the organic light-emitting diode 200 further includes a hole transport region 140. The hole transport region 140 can further increase the hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons. Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light-emitting layer 130 and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and at least one of the compounds in group A may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0182] [Group A]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188] In the hole transport region, in addition to the compounds described above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having a similar structure can be used.

[0189] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0190] refer to Figure 3 In addition to the light emitting layer 130, the organic light emitting diode 300 further includes an electron transport region 150. The electron transport region 150 may also improve electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0191] Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130 and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer, and at least one of the compounds in group B may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0192] [Group B]

[0193]

[0194]

[0195]

[0196] Embodiments of the present invention may provide an organic light emitting diode including a light emitting layer 130 as an organic layer 105, such as Figure 1 shown.

[0197] Another embodiment of the present invention may provide an organic light emitting diode including a hole transport region 140 in addition to the light emitting layer 130 as the organic layer 105, such as Figure 2 shown.

[0198] Another embodiment of the present invention may provide an organic light emitting diode including an electron transport region 150 in addition to the light emitting layer 130 as the organic layer 105, such as Figure 3 shown.

[0199] 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 in addition to the light emitting layer 130 as the organic layer 105, such as Figure 4 shown.

[0200] In another embodiment of the present invention, in addition to Figures 1 to 4 In each of the drawings, in addition to the light-emitting layer 130 as the organic layer 105 , the organic light-emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), and the like.

[0201] The organic light emitting diodes 100 , 200 , 300 and 400 may be produced by forming an anode or a cathode on a substrate, and then forming an organic layer by dry film formation such as vacuum deposition, sputtering, plasma plating and ion plating and forming a cathode or an anode thereon.

[0202] The organic light emitting diode may be applied to an organic light emitting diode display device.

[0203] 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.

[0204] Hereinafter, unless specifically noted, starting materials and reactants used in 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.

[0205] (Preparation of compounds for organic optoelectronic devices)

[0206] Synthesis Example 1: Synthesis of Intermediate I-1

[0207]

[0208] 1,3-Dibromo-2-nitrobenzene (100 g, 356 mmol) purchased from BLD PharmaTech Ltd. (https: / / www.bldpharm.com / ) was dissolved in 0.4 L of tetrahydrofuran (THF) under a nitrogen atmosphere, and phenylboric acid (39.1 g, 320 mmol) and tetrakis(triphenylphosphine)palladium (7.40 g, 6.40 mmol) purchased from Tokyo Chemical Industry (http: / / www.tcichemicals.com / ) were added thereto, followed by stirring.

[0209] Subsequently, a saturated solution of potassium carbonate (111 g, 800 mmol) in water was added thereto, and then heated under reflux at 80 ° C for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-1 (71.2 g, 80%).

[0210] HRMS (70eV, EI+): theoretical value of m / z for C12H8BrNO2: 276.9738, experimental value: 276.

[0211] Elemental analysis: C, 52%; H, 3%

[0212] Synthesis Example 2: Synthesis of Intermediate I-2

[0213]

[0214] Intermediate I-1 (70 g, 252 mmol) was dissolved in 0.3 L toluene in a nitrogen atmosphere, and a solution of 1 M bis(trimethylsilyl) lithium amide (purchased from Sigma Aldrich Co., Ltd. (http: / / www.sigmaaldrich.com / )) in THF (378 mL, 378 mmol), tris(dibenzylideneacetone)dipalladium (0) (4.62 g, 5.04 mmol) and tributylphosphine (5.10 g, 25.2 mmol) were added thereto, and heated under reflux at 60 ° C for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-2 (51.3 g, 95%).

[0215] HRMS (70eV, EI+): theoretical value of m / z for C12H10N2O2: 214.0742, experimental value: 214.

[0216] Elemental analysis: C, 67%; H, 5%

[0217] Synthesis Example 3: Synthesis of Intermediate I-3

[0218]

[0219] Intermediate I-2 (50g, 233mmol) is dissolved in 0.2L xylene in a nitrogen environment, and 2,3-dichloropyridine (34.5g, 233mmol), palladium acetate (II) (1.31g, 5.83mmol), triphenylphosphine (4.58g, 17.5mmol) and sodium tert-butoxide (33.6g, 350mmol) purchased from Tokyo Chemical Industry are added thereto, and then heated under reflux at 100°C for 8 hours. When the reaction is complete, water is added to the reaction solution, and the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The obtained residue is separated and purified by flash column chromatography to obtain intermediate I-3 (59.2g, 78%).

[0220] HRMS (70eV, EI+): theoretical value of m / z for C17H12ClN3O2: 325.0618, experimental value: 325.

[0221] Elemental analysis: C, 63%; H, 4%

[0222] Synthesis Example 4: Synthesis of Intermediate I-4

[0223]

[0224] Intermediate I-3 (55 g, 169 mmol) was dissolved in 0.2 L dimethylformamide (DMF) in a nitrogen environment, and sodium hydride (6.08 g, 253 mmol) was added thereto, and then stirred at 0 ° C. After 1 hour, 2-(biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (87.0 g, 253 mmol) purchased from Tokyo Chemical Industry was added thereto, and then stirred for 1 hour. When the reaction was completed, water was added to the reaction solution at 0 ° C, and then extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water therefrom, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-4 (107 g, 90%).

[0225] HRMS (70eV, EI+): Calculated m / z value of C38H25ClN6O2: 632.1728, experimental value: 632.

[0226] Elemental analysis: C, 72%; H, 4%

[0227] Synthesis Example 5: Synthesis of Intermediate I-5

[0228]

[0229] Intermediate I-4 (100 g, 158 mmol) was dissolved in 0.1 L dichlorobenzene (DCB) in a nitrogen atmosphere, and triphenylphosphine (82.9 g, 316 mmol) was added thereto, and then heated under reflux at 200 ° C for 10 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain intermediate I-5 (71.2 g, 75%).

[0230] HRMS (70eV, EI+): m / z theoretical value of C38H25ClN6: 600.1829, experimental value: 600.

[0231] Elemental analysis: C, 76%; H, 4%

[0232] Synthesis Example 6: Synthesis of Intermediate I-6

[0233]

[0234] Intermediate I-5 (70g, 116mmol) is dissolved in 0.7L dimethylbenzene in a nitrogen environment, iodobenzene (28.4g, 139mmol), tri(dibenzylideneacetone)dipalladium (0) (1.06g, 1.16mmol), tri-tert-butylphosphine (2.35g, 11.6mmol) and sodium tert-butoxide (13.4g, 139mmol) purchased from Tokyo Chemical Industry are added sequentially thereto, and then refluxed at 140°C for 15 hours. When the reaction is complete, water is added to the reaction solution, and the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The obtained residue is separated and purified by flash column chromatography to obtain intermediate I-6 (65.2g, 83%).

[0235] HRMS (70eV, EI+): Calculated m / z value of C44H29ClN6: 676.2142, experimental value: 676.

[0236] Elemental analysis: C, 78%; H, 4%

[0237] Synthesis Example 7: Synthesis of Compound 1

[0238]

[0239] Intermediate I-6 (10g, 14.8mmol) was dissolved in 0.1L dimethylformamide (DMF) in a nitrogen environment, and palladium acetate (II) (0.083g, 0.37mmol), triphenylphosphine (0.29g, 1.11mmol) and 1,8-diazabicyclo [5.4.0] undec-7-ene (4.51g, 29.6mmol) were sequentially added thereto, and then refluxed at 130°C for 8 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain compound 1 (8.25g, 87%).

[0240] HRMS (70eV, EI+): Calculated m / z value of C44H28N6: 640.2375, experimental value: 640.

[0241] Elemental analysis: C, 82%; H, 4%

[0242] Synthesis Example 8: Synthesis of Intermediate I-7

[0243]

[0244] Intermediate I-7 (49.0 g, 84%) was obtained according to the same method as Synthesis Example 4, except that intermediate I-3 (30 g, 92.1 mmol) and 2-(biphenyl-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (38.0 g, 111 mmol) purchased from Tokyo Chemical Industry were used.

[0245] HRMS (70eV, EI+): Calculated m / z value of C38H25ClN6O2: 632.1728, experimental value: 632.

[0246] Elemental analysis: C, 72%; H, 4%

[0247] Synthesis Example 9: Synthesis of Intermediate I-8

[0248]

[0249] Intermediate I-8 (29.9 g, 70%) was obtained according to the same method as Synthesis Example 5 except that Intermediate I-7 (45 g, 71.1 mmol) was used.

[0250] HRMS (70eV, EI+): m / z theoretical value of C38H25ClN6: 600.1829, experimental value: 600.

[0251] Elemental analysis: C, 76%; H, 4%

[0252] Synthesis Example 10: Synthesis of Intermediate I-9

[0253]

[0254] Intermediate I-9 (22.8 g, 81%) was obtained according to the same method as Synthesis Example 6 except that Intermediate I-8 (25 g, 41.6 mmol) was used.

[0255] HRMS (70eV, EI+): Calculated m / z value of C44H29ClN6: 676.2142, experimental value: 676.

[0256] Elemental analysis: C, 78%; H, 4%

[0257] Synthesis Example 11: Synthesis of Compound 2

[0258]

[0259] Compound 2 (8.34 g, 88%) was obtained according to the same method as Synthesis Example 7, except that Intermediate I-9 (10 g, 14.8 mmol) was used.

[0260] HRMS (70eV, EI+): Calculated m / z value of C44H28N6: 640.2375, experimental value: 640.

[0261] Elemental analysis: C, 82%; H, 4%

[0262] Synthesis Example 12: Synthesis of Intermediate I-10

[0263]

[0264] Intermediate I-10 (47.7 g, 80%) was obtained according to the same method as Synthesis Example 4, except that intermediate I-3 (30 g, 92.1 mmol) and 2-chloro-4-(dibenzofuran-3-yl)-6-phenyl-1,3,5-triazine (39.5 g, 111 mmol) purchased from P&H Tech Co., Ltd. (http: / / www.phtech.co.kr / ) were used.

[0265] HRMS (70eV, EI+): Calculated m / z value of C38H23ClN6O3: 646.1520, experimental value: 646.

[0266] Elemental analysis: C, 71%; H, 4%

[0267] Synthesis Example 13: Synthesis of Intermediate I-11

[0268]

[0269] Intermediate I-11 (28.2 g, 66%) was obtained according to the same method as Synthesis Example 5, except that Intermediate I-10 (45 g, 69.5 mmol) was used.

[0270] HRMS (70eV, EI+): Calculated m / z value of C38H23ClN6O: 614.1622, experimental value: 614.

[0271] Elemental analysis: C, 74%; H, 4%

[0272] Synthesis Example 14: Synthesis of Intermediate I-12

[0273]

[0274] Intermediate I-12 (22.2 g, 79%) was obtained according to the same method as Synthesis Example 6 except that Intermediate I-11 (25 g, 40.6 mmol) was used.

[0275] HRMS (70eV, EI+): Calculated m / z value of C44H27ClN6O: 690.1935, experimental value: 690.

[0276] Elemental analysis: C, 76%; H, 4%

[0277] Synthesis Example 15: Synthesis of Compound 15

[0278]

[0279] Compound 15 (8.07 g, 85%) was obtained according to the same method as Synthesis Example 7, except that Intermediate I-12 (10 g, 14.5 mmol) was used.

[0280] HRMS (70eV, EI+): Calculated m / z value of C44H26N6O: 654.2168, experimental value: 654.

[0281] Elemental analysis: C, 81%; H, 4%

[0282] Synthesis Example 16: Synthesis of Intermediate I-13

[0283]

[0284] 2-Bromo-1-chloro-3-fluorobenzene (1000 g, 4,775 mmol) purchased from Henan Tianfu Chemical Co., Ltd. (www.tianfuchem.net) was dissolved in 10 L toluene in a nitrogen environment, and 2,6-dimethoxyphenylboric acid (1043 g, 5,730 mmol) and tetrakis (triphenylphosphine) palladium (110 g, 95.5 mmol) purchased from JL Chem Co. Ltd. (Bide Pharmatech, https: / / jlchem.co.kr / ) were added thereto, and then stirred. Subsequently, a saturated solution of potassium carbonate (1,650 g, 11,938 mmol) in water was added thereto, and then refluxed at 100 ° C for 3 days. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-13 (535 g, 42%).

[0285] HRMS (70 eV, EI+): theoretical value of m / z for C14H12ClFO2: 266.0510, experimental value: 266.

[0286] Elemental analysis: C, 63%; H, 5%

[0287] Synthesis Example 17: Synthesis of Intermediate I-14

[0288]

[0289] Intermediate I-13 (500 g, 1,875 mmol) and pyridine hydrochloride (1,483 g, 18,748 mmol) were placed under nitrogen and then heated under reflux at 180 ° C for 12 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-14 (361 g, 81%).

[0290] HRMS (70 eV, EI+): theoretical value of m / z for C12H8ClFO2: 238.0197, experimental value: 238.

[0291] Elemental analysis: C, 60%; H, 3%

[0292] Synthesis Example 18: Synthesis of Intermediate I-15

[0293]

[0294] Intermediate I-14 (350 g, 1,467 mmol) was dissolved in 3.5 L N-methyl-2-pyrrolidone (NMP) under nitrogen atmosphere, and potassium carbonate (406 g, 2,934 mmol) was added thereto, and then refluxed for 3 hours. When the reaction was complete, after removing the solvent by distillation, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-15 (103 g, 32%).

[0295] HRMS (70eV, EI+): theoretical value of m / z for C12H7ClO2: 218.0135, experimental value: 218.

[0296] Elemental analysis: C, 66%; H, 3%

[0297] Synthesis Example 19: Synthesis of Intermediate I-16

[0298]

[0299] Intermediate I-15 (100 g, 457 mmol) was dissolved in 1.0 L dichloromethane (DCM) in a nitrogen environment, and pyridine (43.4 g, 549 mmol) was added thereto, and then cooled to 0 ° C. Subsequently, trifluoromethanesulfonic anhydride (155 g, 549 mmol) was slowly added thereto, and then stirred. After 3 hours, the reaction solution was cooled to 0 ° C, water was slowly added thereto within 30 minutes, and the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-16 (157 / g, 98%).

[0300] HRMS (70eV, EI+): theoretical value of m / z for C13H6ClF3O4S: 349.9627, experimental value: 349.

[0301] Elemental analysis: C, 45%; H, 2%

[0302] Synthesis Example 20: Synthesis of Intermediate I-17

[0303]

[0304] Intermediate I-17 (113 g, 95%) was obtained according to the same method as Synthesis Example 1, except that the solvent was changed from THF to toluene and Intermediate I-16 (150 g, 428 mmol) and phenylboronic acid (62.6 g, 513 mmol) purchased from Tokyo Chemical Industry were used.

[0305] HRMS (70 eV, EI+): m / z theoretical value of C18H11ClO: 278.0498, experimental value: 278.

[0306] Elemental analysis: C, 78%; H, 4%

[0307] Synthesis Example 21: Synthesis of Intermediate I-18

[0308]

[0309] Intermediate I-17 (113 g, 405 mmol) was dissolved in 0.1 L of xylene in a nitrogen atmosphere, and bis-boronic acid pinacol ester (124 g, 486 mmol), tris(dibenzylideneacetone)dipalladium (0) (3.71 g, 4.05 mmol), tricyclohexylphosphine (4.54 g, 16.2 mmol) and potassium acetate (119 g, 1215 mmol) were added thereto, and then refluxed for 8 hours. When the reaction was complete, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-18 (55.5 g, 37%).

[0310] HRMS (70 eV, EI+): theoretical value of m / z for C24H23BO3: 370.1740, experimental value: 370.

[0311] Elemental analysis: C, 78%; H, 6%

[0312] Synthesis Example 22: Synthesis of Intermediate I-19

[0313]

[0314] Intermediate I-19 (10.5 g, 18%) was obtained according to the same method as Synthesis Example 1, except that intermediate I-18 (50 g, 135 mmol) and 2,4-dichloro-6-phenyl-1,3,5-triazine (30.5 g, 135 mmol) purchased from Tokyo Chemical Industry were used and the solvent was changed from THF to toluene.

[0315] HRMS (70 eV, EI+): m / z theoretical value of C27H16ClN3O: 433.0982, experimental value: 433.

[0316] Elemental analysis: C, 75%; H, 4%

[0317] Synthesis Example 23: Synthesis of Intermediate I-20

[0318]

[0319] Intermediate I-20 (18.0 g, 81%) was obtained according to the same method as Synthesis Example 4 except that Intermediate I-3 (10 g, 30.7 mmol) and Intermediate I-19 (16.0 g, 36.8 mmol) were used.

[0320] HRMS (70eV, EI+): Calculated m / z value of C44H27ClN6O3: 722.1833, experimental value: 722.

[0321] Elemental analysis: C, 73%; H, 4%

[0322] Synthesis Example 24: Synthesis of Intermediate I-21

[0323]

[0324] Intermediate I-21 (8.6 g, 60%) was obtained according to the same method as Synthesis Example 5 except that Intermediate I-20 (15 g, 20.7 mmol) was used.

[0325] HRMS (70eV, EI+): Calculated m / z value of C44H27ClN6O: 690.1935, experimental value: 690.

[0326] Elemental analysis: C, 76%; H, 4%

[0327] Synthesis Example 25: Synthesis of Intermediate I-22

[0328]

[0329] Intermediate I-22 (7.37 g, 83%) was obtained according to the same method as Synthesis Example 6 except that Intermediate I-21 (8 g, 11.6 mmol) was used.

[0330] HRMS (70eV, EI+): Calculated m / z value of C50H31ClN6O: 766.2248, experimental value: 766.

[0331] Elemental analysis: C, 78%; H, 4%

[0332] Synthesis Example 26: Synthesis of Compound 17

[0333]

[0334] Compound 17 (3.85 g, 81%) was obtained according to the same method as Synthesis Example 7 except that Intermediate I-22 (5 g, 6.52 mmol) was used.

[0335] HRMS (70eV, EI+): theoretical value of m / z for C50H30N6O: 730.2481, experimental value: 730.

[0336] Elemental analysis: C, 82%; H, 4%

[0337] Synthesis Example 27: Synthesis of Intermediate I-23

[0338]

[0339] Intermediate I-23 (51.9 g, 85%) was obtained according to the same method as Synthesis Example 4, except that intermediate I-3 (30 g, 92.1 mmol) and 2-chloro-4-(dibenzothiophene-3-yl)-6-phenyl-1,3,5-triazine (41.5 g, 111 mmol) purchased from P&H Tech Co., Ltd. (http: / / www.phtech.co.kr / ) were used.

[0340] HRMS (70eV, EI+): Calculated m / z value of C38H23ClN6O2S: 662.1292, experimental value: 662.

[0341] Elemental analysis: C, 69%; H, 4%

[0342] Synthesis Example 28: Synthesis of Intermediate I-24

[0343]

[0344] Intermediate I-24 (38.1 g, 80%) was obtained according to the same method as Synthesis Example 5 except that Intermediate I-23 (50 g, 75.4 mmol) was used.

[0345] HRMS (70eV, EI+): Calculated m / z value of C38H23ClN6S: 630.1393, experimental value: 630.

[0346] Elemental analysis: C, 72%; H, 4%

[0347] Synthesis Example 29: Synthesis of Intermediate I-25

[0348]

[0349] Intermediate I-25 (32.9 g, 84%) was obtained according to the same method as Synthesis Example 6 except that Intermediate I-24 (35 g, 55.5 mmol) was used.

[0350] HRMS (70eV, EI+): m / z theoretical value of C44H27ClN6S: 706.1706, experimental value: 706.

[0351] Elemental analysis: C, 75%; H, 4%

[0352] Synthesis Example 30: Synthesis of Compound 23

[0353]

[0354] Compound 23 (7.57 g, 80%) was obtained according to the same method as Synthesis Example 7 except that Intermediate I-25 (10 g, 14.1 mmol) was used.

[0355] HRMS (70eV, EI+): Calculated m / z value of C44H26N6S: 670.7824, experimental value: 670.

[0356] Elemental analysis: C, 79%; H, 4%

[0357] Synthesis Example 31: Synthesis of Intermediate I-26

[0358]

[0359] Intermediate I-26 (29.3 g, 78%) was obtained according to the same method as Synthesis Example 6 except that Intermediate I-5 (30 g, 49.9 mmol) and 3-bromobiphenyl (12.8 g, 54.9 mmol) purchased from Tokyo Chemical Industry were used.

[0360] HRMS (70eV, EI+): Calculated m / z value of C50H33ClN6: 752.2455, experimental value: 752.

[0361] Elemental analysis: C, 80%; H, 4%

[0362] Synthesis Example 32: Synthesis of Compound 37

[0363]

[0364] Compound 37 (7.14 g, 75%) was obtained according to the same method as Synthesis Example 7 except that Intermediate I-26 (10 g, 13.3 mmol) was used.

[0365] HRMS (70eV, EI+): Calculated m / z value of C50H32N6: 716.8293, experimental value: 716.

[0366] Elemental analysis: C, 84%; H, 5%

[0367] Synthesis Example 33: Synthesis of Intermediate I-27

[0368]

[0369] 1,3-dibromo-2-nitrobenzene (100 g, 356 mmol) purchased from BLD PharmaTech Ltd. was dissolved in 1.0 L dimethylformamide (DMF) in a nitrogen environment, and 3-pyridylboronic acid (36.5 g, 297 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (4.85 g, 5.94 mmol) purchased from Tokyo Chemical Industry were added thereto, and then heated under reflux at 100°C for 1 hour. When the reaction was complete, water was added to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-27 (66.3 g, 80%).

[0370] HRMS (70eV, EI+): Calculated m / z value of C11H7BrN2O2: 277.9691, experimental value: 277.

[0371] Elemental analysis: C, 47%; H, 3%

[0372] Synthesis Example 34: Synthesis of Intermediate I-28

[0373]

[0374] Intermediate I-28 (46.1 g, 92%) was obtained according to the same method as Synthesis Example 2 except that Intermediate I-27 (65 g, 233 mmol) was used.

[0375] HRMS (70eV, EI+): Calculated m / z value of C11H9N3O2: 215.0695, experimental value: 215.

[0376] Elemental analysis: C, 61%; H, 4%

[0377] Synthesis Example 35: Synthesis of Intermediate I-29

[0378]

[0379] Intermediate I-29 (54.7 g, 80%) was obtained according to the same method as Synthesis Example 3 except that Intermediate I-28 (45 g, 209 mmol) was used.

[0380] HRMS (70eV, EI+): theoretical value of m / z for C16H11ClN4O2: 326.0571, experimental value: 326.

[0381] Elemental analysis: C, 59%; H, 3%

[0382] Synthesis Example 36: Synthesis of Intermediate I-30

[0383]

[0384] Intermediate I-30 (59.2 g, 61%) was obtained according to the same method as Synthesis Example 4 except that Intermediate I-29 (50 g, 153 mmol) was used.

[0385] HRMS (70eV, EI+): Calculated m / z value of C37H24ClN7O2: 633.1680, experimental value: 633.

[0386] Elemental analysis: C, 70%; H, 4%

[0387] Synthesis Example 37: Synthesis of Intermediate I-31

[0388]

[0389] Intermediate I-31 (27.7 g, 53%) was obtained according to the same method as Synthesis Example 5 except that Intermediate I-30 (55 g, 86.7 mmol) was used.

[0390] HRMS (70eV, EI+): Calculated m / z value of C37H24ClN7: 601.1782, experimental value: 601.

[0391] Elemental analysis: C, 74%; H, 4%

[0392] Synthesis Example 38: Synthesis of Intermediate I-32

[0393]

[0394] Intermediate I-32 (15.0 g, 48%) was obtained according to the same method as Synthesis Example 31 except that Intermediate I-31 (25 g, 41.5 mmol) was used.

[0395] HRMS (70eV, EI+): Calculated m / z value of C49H32ClN7: 753.2408, experimental value: 753.

[0396] Elemental analysis: C, 78%; H, 4%

[0397] Synthesis Example 39: Synthesis of Compound 117

[0398]

[0399] Compound 117 (4.76 g, 50%) was obtained according to the same method as Synthesis Example 7 except that Intermediate I-32 (10 g, 13.3 mmol) was used.

[0400] HRMS (70eV, EI+): Calculated m / z value of C49H31N7: 717.2641, experimental value: 717.

[0401] Elemental analysis: C, 82%; H, 4%

[0402] Synthesis Example 40: Synthesis of Intermediate I-33

[0403]

[0404] Intermediate I-33 (56.7 g, 75%) was obtained according to the same method as Synthesis Example 31, except that intermediate I-28 (50 g, 232 mmol) and 2-bromo-1-chlorobenzene (53.4 g, 279 mmol) purchased from Tokyo Chemical Industry were used and the heating temperature was changed from 140°C to 80°C.

[0405] HRMS (70eV, EI+): theoretical value of m / z for C17H12ClN3O2: 325.0618, experimental value: 325.

[0406] Elemental analysis: C, 63%; H, 4%

[0407] Synthesis Example 41: Synthesis of Intermediate I-34

[0408]

[0409] Intermediate I-34 (57.3 g, 59%) was obtained according to the same method as Synthesis Example 4, except that Intermediate I-34 (57.3 g, 59%) was used.

[0410] HRMS (70eV, EI+): Calculated m / z value of C38H25ClN6O2: 632.1728, experimental value: 632.

[0411] Elemental analysis: C, 67%; H, 4%

[0412] Synthesis Example 42: Synthesis of Intermediate I-35

[0413]

[0414] Intermediate I-35 (20.4 g, 43%) was obtained according to the same method as Synthesis Example 5 except that Intermediate I-34 (50 g, 79.0 mmol) was used.

[0415] HRMS (70eV, EI+): m / z theoretical value of C38H25ClN6: 600.1829, experimental value: 600.

[0416] Elemental analysis: C, 76%; H, 4%

[0417] Synthesis Example 43: Synthesis of Intermediate I-36

[0418]

[0419] Intermediate I-36 (10 g, 40%) was obtained according to the same method as Synthesis Example 31, except that Intermediate I-35 (20 g, 33.3 mmol) was used.

[0420] HRMS (70eV, EI+): Calculated m / z value of C50H33ClN6: 752.2455, experimental value: 752.

[0421] Elemental analysis: C, 80%; H, 4%

[0422] Synthesis Example 44: Synthesis of Compound 77

[0423]

[0424] Intermediate I-36 (8g, 10.6mmol) is dissolved in 0.1L dimethylbenzene in a nitrogen environment, and palladium acetate (II) (0.24g, 1.06mmol), tricyclohexylphosphine tetrafluoroborate (0.78g, 2.12mmol) and cesium carbonate (6.91g, 21.2mmol) are sequentially added thereto, then heated at reflux for 24 hours at 130°C. When the reaction is complete, water is added to the reaction solution, and the mixture is extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The obtained residue is separated and purified by flash column chromatography to obtain compound 77 (2.66g, 35%).

[0425] HRMS (70eV, EI+): Calculated m / z value of C50H32N6: 716.2688, experimental value: 716.

[0426] Elemental analysis: C, 84%; H, 5%

[0427] Synthesis Example 45: Synthesis of Compound Main Body 1

[0428]

[0429] The main compound 1 was synthesized by referring to the synthesis method of patent KR2010-0105099.

[0430] HRMS (70eV, EI+): Calculated m / z value of C50H32N6: 716.2688, experimental value: 716.

[0431] Elemental analysis: C, 84%; H, 5%

[0432] Synthesis Example 46: Synthesis of Compound Host 2

[0433]

[0434] The main compound 2 was synthesized by referring to the synthesis method of patent CN110294760.

[0435] HRMS (70eV, EI+): Calculated m / z value of C50H32N6: 716.2688, experimental value: 716.

[0436] Elemental analysis: C, 84%; H, 4%

[0437] Synthesis Example 47: Synthesis of Compound Host 3

[0438]

[0439] The main compound 3 was synthesized by referring to the synthesis method of patent WO2019-179497.

[0440] HRMS (70eV, EI+): theoretical value of m / z for C37H23N7: 565.2015, experimental value: 565.

[0441] Elemental analysis: C, 79%; H, 4%

[0442] Synthesis Example 48: Synthesis of Compound Host 4

[0443]

[0444] The main compound 4 was synthesized by referring to the synthesis method of patent JP6319097.

[0445] HRMS (70eV, EI+): Calculated m / z value of C39H25N5: 563.2110, experimental value: 563.

[0446] Elemental analysis: C, 83%; H, 4%

[0447] Synthesis Example 49: Synthesis of Compound Host 5

[0448]

[0449] The main compound 5 was synthesized by referring to the synthesis method of patent CN110372715.

[0450] HRMS (70 eV, EI+): Calculated m / z value of C41H25N5: 587.2110, experimental value: 587.

[0451] Elemental analysis: C, 84%; H, 4%

[0452] Synthesis Example 50: Synthesis of Intermediate I-37

[0453]

[0454] Intermediate I-37 (100 g, 91%) was obtained according to the same method as Synthesis Example 3 except that aniline (50 g, 537 mmol) purchased from Tokyo Chemical Industry was used.

[0455] HRMS (70eV, EI+): theoretical value of m / z for C11H9ClN2: 204.0454, experimental value: 204.

[0456] Elemental analysis: C, 65%; H, 4%

[0457] Synthesis Example 51: Synthesis of Intermediate I-38

[0458]

[0459] Intermediate I-38 (191 g, 85%) was obtained according to the same method as Synthesis Example 4 except that Intermediate I-37 (90 g, 440 mmol) was used.

[0460] HRMS (70eV, EI+): Calculated m / z value of C32H22ClN5: 511.1564, experimental value: 511.

[0461] Elemental analysis: C, 75%; H, 4%

[0462] Synthesis Example 52: Synthesis of Compound Host 6

[0463]

[0464] The host 6 (191 g, 85%) was obtained according to the same method as Synthesis Example 7 except that the intermediate I-38 (10 g, 19.5 mmol) was used.

[0465] HRMS (70eV, EI+): Calculated m / z value of C32H21N5: 475.1797, experimental value: 475.

[0466] Elemental analysis: C, 81%; H, 4%

[0467] Synthesis Example 53: Synthesis of Compound A-136

[0468]

[0469] Compound A-136 was synthesized by referring to the synthesis method of patent EP3034581.

[0470] HRMS (70eV, EI+): Calculated m / z value of C42H28N2: 560.2252, experimental value: 560.

[0471] Elemental analysis: C, 90%; H, 5%

[0472] Synthesis Example 54: Synthesis of Compound A-99

[0473]

[0474] Compound A-99 was synthesized by referring to the synthesis method of patent KR10-2019-0000597.

[0475] HRMS (70eV, EI+): Calculated m / z value of C48H32N2: 636.2565, experimental value: 636.

[0476] Elemental analysis: C, 91%; H, 5%

[0477] Synthesis Example 55: Synthesis of Compound A-31

[0478]

[0479] Compound A-31 was synthesized by referring to the synthesis method of patent EP2947071.

[0480] HRMS (70eV, EI+): Calculated m / z value of C48H32N2: 636.2565, experimental value: 636.

[0481] Elemental analysis: C, 91%; H, 5%

[0482] Synthesis Example 56: Synthesis of Compound B-4

[0483]

[0484] Compound B-4 was synthesized by referring to the synthesis method of patent KR2031300.

[0485] HRMS (70eV, EI+): Calculated m / z value of C42H28N2: 560.2252, experimental value: 560.

[0486] Elemental analysis: C, 90%; H, 5%

[0487] Synthesis Example 57: Synthesis of Compound B-57

[0488]

[0489] Compound B-57 was synthesized by referring to the synthesis method of patent WO2018-095391.

[0490] HRMS (70eV, EI+): Calculated m / z value of C48H32N2: 636.2565, experimental value: 636.

[0491] Elemental analysis: C, 91%; H, 5%

[0492] (Calculation results of energy levels and bond angles using Gaussian tools)

[0493] The energy level and bond angle of each material were calculated in the B3LYP / 6-31G** method by using the Gaussian 09 program, through the supercomputer GAIA (IBM power 6), and the results are shown in Tables 1 and Figure 1 as shown in .

[0494] (Table 1)

[0495]

[0496] Referring to the calculation results, a structure in which at least one of the 1st and 10th positions of indolizine is substituted with nitrogen (N) shows a relatively low LUMO energy level compared to a structure in which nitrogen (N) is substituted at positions other than the 1st and 10th positions.

[0497] When substituted with nitrogen (N) at position 1, since hydrogen (H) of CH which carbon usually has is not included therein, triazine-carbazole can be arranged to have a larger angle. This increase in bond angle weakens the π-π bond between indolizine and triazine, and the electron cloud boundary between the LUMO region and the HOMO region is clearly localized. Since the LUMO region and the HOMO region are clearly localized, both the LUMO energy level and the HOMO energy level become stronger.

[0498] In contrast, when N is substituted below the position substituted by triazine in indolizine, the HOMO energy level becomes relatively weak. The portion having a triazine-indolizine bond is sterically hindered by its adjacent portion having a biphenyl-indolizine bond, resulting in a structure in which its angle may not be able to rotate greatly. This structure significantly leads to a deep LUMO, resulting in low efficiency in OLED devices. Figure 1 A more detailed description is shown in .

[0499]

[0500] (Structure in which the first position is substituted with nitrogen (N))

[0501]

[0502] (Structure substituted with nitrogen (N) at position 7)

[0503] [ Figure 1 ] The bond angles of triazine-carbazole and phenyl-carbazole

[0504]

[0505] (Production of organic light-emitting diodes)

[0506] Example 1

[0507] The ITO (indium tin oxide) coated glass substrate was cleaned with distilled water and ultrasonic waves. After cleaning 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 for 10 minutes by using oxygen plasma, and moved to a vacuum depositor. The resulting ITO transparent electrode was used as an anode, and Compound A doped with 1% NDP-9 (obtained from Novaled GmbH) was vacuum deposited on the ITO substrate to form -thick hole transport layer, and depositing compound B on the hole transport layer to form -thick hole transport auxiliary layer. On the hole transport auxiliary layer, a 10 wt% PhGD was formed by using Compound 1 of Synthesis Example 7 and Compound A-136 of Synthesis Example 53 as a host and doping with 10 wt% of PhGD as a dopant. -thick light-emitting layer. Herein, compound 1 and compound A-136 were used in a weight ratio of 3:7. Subsequently, compound C was deposited on the light-emitting layer to form -thick electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a weight ratio of 1:1 to form -Thick electron transport layer. and Al A cathode is formed by sequential vacuum deposition on the electron transport layer, thereby producing an organic light emitting diode.

[0508] ITO / Compound A (1% NDP-9 doped, ) / Compound B / EML[Compound 1:Compound A-136:PhGD=3:7:10wt%)] / Compound C / Compound D: LiQ / LiQ / Al

[0509] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0510] Compound B: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0511] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0512] Compound D: 8-(4-(4,6-di(naphthalene-2-yl)-1,3,5-triazine-2-yl)phenyl)quinolone

[0513] Example 2

[0514] An organic light emitting diode was produced according to the same method as Example 1, except that Compound 2 was used instead of Compound 1.

[0515] Example 3

[0516] An organic light emitting diode was produced according to the same method as Example 1, except that Compound 15 was used instead of Compound 1.

[0517] Example 4

[0518] An organic light emitting diode was produced according to the same method as Example 1, except that Compound 17 was used instead of Compound 1.

[0519] Example 5

[0520] An organic light emitting diode was produced according to the same method as Example 1, except that Compound 23 was used instead of Compound 1.

[0521] Example 6

[0522] An organic light emitting diode was produced according to the same method as Example 1, except that Compound 37 was used instead of Compound 1.

[0523] Example 7

[0524] An organic light emitting diode was produced according to the same method as Example 1, except that Compound 77 was used instead of Compound 1.

[0525] Example 8

[0526] An organic light emitting diode was produced according to the same method as in Example 1, except that Compound 117 was used instead of Compound 1.

[0527] Example 9

[0528] An organic light emitting diode was produced according to the same method as Example 6, except that Compound A-99 was used instead of Compound A-136.

[0529] Example 10

[0530] An organic light emitting diode was produced according to the same method as Example 6, except that Compound A-31 was used instead of Compound A-136.

[0531] Embodiment 11

[0532] An organic light emitting diode was produced according to the same method as in Example 6, except that Compound B-4 was used instead of Compound A-136.

[0533] Example 12

[0534] An organic light emitting diode was produced according to the same method as Example 6, except that Compound B-57 was used instead of Compound A-136.

[0535] Embodiment 13

[0536] An organic light emitting diode was produced according to the same method as Example 6, except that the weight ratio of Compound 37 to Compound A-136 was changed from 3:7 to 4:6.

[0537] Embodiment 14

[0538] An organic light emitting diode was produced according to the same method as Example 6, except that the weight ratio of Compound 37 to Compound A-136 was changed from 3:7 to 2:8.

[0539] Comparative Example 1

[0540] An organic light emitting diode was produced according to the same method as Example 1, except that Compound Host 1 was used instead of Compound 1.

[0541] Comparative Example 2

[0542] An organic light emitting diode was produced according to the same method as in Example 1, except that Compound Host 2 was used instead of Compound 1.

[0543] Comparative Example 3

[0544] An organic light emitting diode was produced according to the same method as in Example 1, except that Compound Host 3 was used instead of Compound 1.

[0545] Comparative Example 4

[0546] An organic light emitting diode was produced according to the same method as in Example 1, except that Compound Host 4 was used instead of Compound 1.

[0547] Comparative Example 5

[0548] An organic light emitting diode was produced according to the same method as Example 1, except that Compound Host 5 was used instead of Compound 1.

[0549] Comparative Example 6

[0550] An organic light emitting diode was produced according to the same method as in Example 1, except that Compound Host 6 was used instead of Compound 1.

[0551] evaluate

[0552] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 14 and Comparative Examples 1 to 6 were evaluated.

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

[0554] (1) Measuring the change in current density based on the change in voltage

[0555] The resulting organic light emitting diode was measured for a current value flowing into the unit device while increasing the voltage from 0 V to 10 V using a voltammeter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0556] (2) Measuring brightness changes based on voltage changes

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

[0558] (3) Measurement of luminous efficiency

[0559] Using the luminance, current density, and voltage from items (1) and (2), calculate the same current density (10 mA / cm 2 ) under luminous efficiency (cd / A).

[0560] The relative values ​​of the current efficiency based on Comparative Example 1 are shown in Table 1.

[0561] (4) Lifespan measurement

[0562] When the current efficiency (cd / A) is reduced to 97%, the brightness (cd / m 2 ) maintained at 24000cd / m 2 The result was obtained by measuring the time.

[0563] The relative values ​​of the lifespan based on Comparative Example 1 are shown in Table 1.

[0564] (5) Measurement of driving voltage

[0565] A voltammeter (Keithley 2400) was used at 15 mA / cm 2 Measure the driving voltage of each diode.

[0566] The relative values ​​of the driving voltage based on Comparative Example 1 are shown in Table 1.

[0567] (Table 2)

[0568]

[0569]

[0570] Referring to Table 2, the driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 14 are significantly improved compared to those of the organic light emitting diodes according to Comparative Examples 1 to 6.

[0571] While the invention has been described in connection 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 on the contrary, the invention 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, In Chemical Formula 1, X 1 and X 2 N or CR a , X 1 and X 2 At least one of them is N, Ar 1 and Ar 3 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, Ar 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothienyl group, L 1 To L 3 Each is independently a single bond R a and R 1 To R 8 are independently hydrogen, deuterium, or substituted or unsubstituted phenyl, and Herein, "substituted" means that at least one hydrogen of the substituent is replaced by deuterium, C1 to C5 alkyl, cyano, phenyl or biphenyl.

2. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formula 1A to Chemical Formula 1C: [Chemical formula 1C] in, In Chemical Formulae 1A to 1C, X 1 , X 2 ,Ar 1 To Ar 3 , L 1 To L 3 and R 1 To R 8 The definition is the same as that in claim 1.

3. The compound according to claim 1, wherein Ar 1 To Ar 3 Each independently selected from the group I: [Group I] in, In Group I, * is the connection point.

4. The compound according to claim 1, which is one of the compounds shown in Group 1: [Group 1] 5. A composition for an organic optoelectronic device, comprising a first compound for an organic photoelectric device and a second compound for an organic photoelectric device, wherein the first compound for an organic optoelectronic device is the compound for an organic optoelectronic device according to claim 1, and The second compound for an organic optoelectronic device is represented by Chemical Formula 2; or a combination of Chemical Formula 3 and Chemical Formula 4: [Chemical formula 2] in, In chemical formula 2, Y 1 and Y 2 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 b and R 9 To R 18 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl, and m is an integer from 0 to 2; Wherein, in chemical formulas 3 and 4, Y 3 and Y 4 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 connected to the connecting carbons of * in Chemical Formula 4, respectively. The remaining two of a1* to a4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are independently CL a -R c , 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 c and R 19 To R 26 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl.

6. The composition according to claim 5, wherein Chemical Formula 2 is represented by Chemical Formula 2-8: [Chemical formula 2-8] in, In Chemical Formula 2-8, R 9 To R 18 are each independently hydrogen or a substituted or unsubstituted C6 to C12 aryl group, and *-L 4 -Y 1 and *-L 5 -Y 2 are each independently one of the substituents in Group II: [Group II] Where, in Group II, * is the connection point.

7. The composition according to claim 5, wherein the combination of Chemical Formula 3 and Chemical Formula 4 is represented by Chemical Formula 3C or Chemical Formula 3D: in, In Chemical Formula 3C and Chemical Formula 3D, 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 19 To R 26 , R c3 and R c4 are hydrogen, and Y 3 and Y 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group.

8. An organic optoelectronic device comprising an anode and a cathode opposite each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 4; or The composition for an organic optoelectronic device according to any one of claims 5 to 7.

9. The organic optoelectronic device according to claim 8, wherein The organic layer comprises a light-emitting layer, and The light-emitting layer includes the compound for an organic photoelectric device according to any one of claims 1 to 4 or the composition for an organic photoelectric device according to any one of claims 5 to 7 . 10 . A display device comprising the organic optoelectronic device according to claim 8 .

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