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

Abstract

The present invention relates to: a compound for an organic optoelectronic device represented by a combination of Chemical Formula 1 and Chemical Formula 2; a composition for an organic optoelectronic device comprising the same; an organic optoelectronic device; and a display device. Details of Chemical Formula 1 and Chemical Formula 2 are the same as those defined 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] An organic optoelectronic device (organic optoelectronic diode) is a device that can convert electrical energy into light energy and vice versa.

[0003] Organic optoelectronic devices can be broadly divided into two categories based on their operating principles: photovoltaic devices that generate electrical energy by separating excitons formed from light energy into electrons and holes and transferring these electrons and holes to different electrodes; and light-emitting devices that generate light energy from electrical energy by applying voltage or current to electrodes.

[0004] Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[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 the organic material between electrodes. Summary of the Invention

[0006] Technical issues

[0007] One embodiment provides a compound for an organic optoelectronic device that realizes a low-driving, high-efficiency, and long-life organic optoelectronic device.

[0008] Another embodiment provides a composition for an organic optoelectronic device including the compound for an organic optoelectronic device.

[0009] Another embodiment provides an organic optoelectronic device including the compound for an organic optoelectronic device or the composition 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 a combination of Chemical Formula 1 and Chemical Formula 2 is provided.

[0013]

[0014] In Chemical Formula 1 and Chemical Formula 2,

[0015] X 1 It is O or S,

[0016] * Each is a connecting carbon (C),

[0017] * in Chemical Formula 1 is connected to * in Chemical Formula 2, respectively,

[0018] R 1 and R 2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0019] R 3 to R 12 are each independently hydrogen, deuterium or substituted or unsubstituted phenyl,

[0020] m1 is an integer from 1 to 4,

[0021] m2 is an integer of 1 or 2, and

[0022] R 1 and R 2 At least one of them is a group represented by chemical formula a,

[0023] [Chemical formula a]

[0024]

[0025] In chemical formula a,

[0026] Z 1 to Z 3 Each independently is N or CL a -R a ,

[0027] Z 1 to Z 3 At least two of them are N,

[0028] L a and 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,

[0029] R a is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0030] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0031] According to another embodiment, provided is a composition for an organic optoelectronic device including a first compound and a second compound.

[0032] The first compound may be the compound for an organic optoelectronic device described above, and the second compound may be represented by Chemical Formula 3 or by a combination of Chemical Formula 4 and Chemical Formula 5.

[0033] [Chemical Formula 3]

[0034]

[0035] In Chemical Formula 3,

[0036] R 13 to R 17 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 heterocyclic group,

[0037] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0038] L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0039] m3, m6 and m7 are each independently an integer from 1 to 4,

[0040] m4 and m5 are each independently one of integers from 1 to 3, and

[0041] n is an integer from 0 to 2;

[0042]

[0043] In Chemical Formula 4 and Chemical Formula 5,

[0044] a1* to a4* in Chemical Formula 4 are each independently a connecting carbon (C) or CL b -R b ,

[0045] Among a1* to a4* in Chemical Formula 4, adjacent two are each connected to * in Chemical Formula 5,

[0046] Among a1* to a4* in Chemical Formula 4, the remaining two not connected to * in Chemical Formula 5 are CL b -R b ,

[0047] L b , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0048] R b 、R 18 and R 19 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 heterocyclic group,

[0049] 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, and

[0050] m8 and m9 are each independently one of integers from 1 to 4.

[0051] 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 compound for an organic optoelectronic device or a composition for an organic optoelectronic device.

[0052] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0053] Beneficial effects

[0054] An organic optoelectronic device with low driving force, high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0055] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0056] <Description of Reference Numerals>

[0057] 100: Organic Light-Emitting Diode

[0058] 105: Organic layer

[0059] 110: cathode

[0060] 120: Anode

[0061] 130: Luminous layer

[0062] 140: Hole transport zone

[0063] 150: Electron transport region DETAILED DESCRIPTION

[0064] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present disclosure is not limited thereto.

[0065] In the present specification, when no definition is otherwise provided, "substituted" means that at least one hydrogen of the 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.

[0066] In one embodiment of the present invention, "substituted" means that at least one hydrogen atom 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 one specific embodiment of the present invention, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In one specific embodiment of the present invention, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In one specific embodiment of the present invention, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0067] In the present specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0068] In the present specification, "hydrogen (—H)" may include "deuterium substitution (—D)" or "tritium substitution (—T)".

[0069] In the present specification, when a definition is not otherwise provided, "hetero" means containing one to three hetero atoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0070] In this specification, "aryl" refers to a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p orbitals forming conjugation, such as phenyl, naphthyl, etc., two or more hydrocarbon aromatic moieties may be connected by a σ bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic moieties may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0071] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.

[0072] As used herein, "heterocyclyl" 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, a cycloalkyl, a fused ring thereof or a combination thereof. When the heterocyclyl is a fused ring, the entire ring or each ring of the heterocyclyl may include one or more heteroatoms.

[0073] For example, "heteroaryl" may refer to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups may be directly linked by a sigma bond, or when the heteroaryl group comprises two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may comprise one to three heteroatoms.

[0074] 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 chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0075] 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 triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted The present invention also includes, but is not limited to, a substituted or unsubstituted quinolinyl, a substituted or unsubstituted isoquinolinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazinyl, 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, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted benzofuranofluorenyl, a substituted or unsubstituted benzothienofluorenyl, or a combination thereof, but is not limited thereto.

[0076] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0077] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0078] Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

[0079] The compound for an organic optoelectronic device according to one embodiment is composed of Chemical Formula 1 and Chemical Formula

[0080] The combination of formula 2 is expressed.

[0081]

[0082] In Chemical Formula 1 and Chemical Formula 2,

[0083] X 1 It is O or S,

[0084] * Each is a connecting carbon (C),

[0085] * in Chemical Formula 1 is connected to * in Chemical Formula 2, respectively,

[0086] R 1 and R 2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0087] R 3 to R 12 are each independently hydrogen, deuterium or substituted or unsubstituted phenyl,

[0088] m1 is an integer from 1 to 4,

[0089] m2 is an integer of 1 or 2, and

[0090] R 1 and R 2 At least one of them is a group represented by chemical formula a,

[0091] [Chemical formula a]

[0092]

[0093] In chemical formula a,

[0094] Z 1 to Z 3 Each independently is N or CL a -R a ,

[0095] Z 1 to Z 3 At least two of them are N,

[0096] L a and 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,

[0097] R a is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0098] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0099] The first compound has a structure in which imidazole is fused to dibenzofuran (dibenzothiophene); and has advantages of high charge mobility, a large current on / off ratio, a very low driving voltage, and excellent efficiency and lifespan characteristics by including the dibenzofuran (dibenzothiophene) portion.

[0100] Furthermore, the imidazole moiety is a five-membered heterocyclic compound including two non-adjacent nitrogen atoms, which is structurally stable and has particularly excellent thermal stability.

[0101] Therefore, the core in which imidazole is fused to dibenzofuran (dibenzothiophene) exhibits excellent electrical properties due to its low dielectric constant and has a low dipole moment value, enabling it to achieve high-definition images in the final device. In particular, the hole mobility of the structure fused to the 1- and 2-positions of dibenzofuran (or dibenzothiophene) is very excellent, which helps improve the low voltage / high efficiency / long life characteristics of the organic light-emitting diode to which it is applied. Therefore, the core in which imidazole is fused to the 1- and 2-positions of dibenzofuran (dibenzothiophene) can be used as a host material with low voltage / high efficiency / long life characteristics.

[0102] In Formula 1 and Formula 2, when there are two or more R 1 When R 1 Each may be the same as or different from each other.

[0103] In Formula 1 and Formula 2, when there are two or more R 2 When R 2 Each may be the same as or different from each other.

[0104] In Formula 1 and Formula 2, when there are two or more R a When R a Each may be the same as or different from each other.

[0105] The combination of Chemical Formula 1 and Chemical Formula 2 may be represented, for example, by Chemical Formula 1A or Chemical Formula 1B, depending on the fusion position and fusion direction.

[0106]

[0107] In Chemical Formula 1A and Chemical Formula 1B,

[0108] X 1 、R 1 to R 12 , m1 and m2 are as defined in Chemical Formula 1.

[0109] A specific example of the combination of Chemical Formula 1 and Chemical Formula 2 may be represented by any one of the following Chemical Formula 1A-I, Chemical Formula 1A-II, Chemical Formula 1B-I, and Chemical Formula 1B-II.

[0110]

[0111]

[0112] In Chemical Formula 1A-I, Chemical Formula 1A-II, Chemical Formula 1B-I, and Chemical Formula 1B-II,

[0113] X 1 , Z 1 to Z 3 、R 3 to R 12 、Ar 1 、Ar 2 , L 1 To L 3 , m1 and m2 are as defined in Chemical Formula 1,

[0114] R 1 and R 2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0115] m1' is one of integers from 1 to 3, and

[0116] m2' is 1.

[0117] A more specific example of the combination of Chemical Formula 1 and Chemical Formula 2 can be represented by Chemical Formula 1A-I-1 to Chemical Formula 1A-I-4, Chemical Formula 1A-II-1, Chemical Formula 1A-II-2, Chemical Formula 1B-I-1 to Chemical Formula

[0118] Any one of Formula 1B-I-4, Chemical Formula 1B-II-1 and Chemical Formula 1B-II-2 is represented.

[0119]

[0120]

[0121]

[0122] In Chemical Formulas 1A-I-1 to 1A-I-4, Chemical Formula 1A-II-1, Chemical Formula 1A-II-2, Chemical Formulas 1B-I-1 to 1B-I-4, Chemical Formula 1B-II-1, and Chemical Formula 1B-II-2,

[0123] X 1 , Z 1 to Z 3 、R 1 to R 12、Ar 1 、Ar 2 , L 1 To L 3 , m1, m1', m2 and m2' are as defined in Formula 1A-I, Formula 1A-II, Formula 1B-I and Formula 1B-II.

[0124] A more specific example of the combination of Chemical Formula 1 and Chemical Formula 2 can be represented by Chemical Formula 1A-I-1 or Chemical Formula 1B-I-1.

[0125] For example, R 1 and R 2 and may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0126] For example, L a and L 1 To L 3 Each independently may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0127] For example, Ar 1 and Ar 2 The substituted or unsubstituted phenyl groups may be substituted or unsubstituted biphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted quaterphenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthracenyl groups, substituted or unsubstituted phenanthrenyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted carbazolyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiorol groups, substituted or unsubstituted 9,9-spirobifluorenyl ... group, 9,9-spirobifluorenyl), substituted or unsubstituted xanthenyl, substituted or unsubstituted thioxanthenyl, substituted or unsubstituted (10-phenyl-9,10-dihydroacridinyl), substituted or unsubstituted spiro[fluorene-9,9'-xanthenyl], substituted or unsubstituted spiro[fluorene-9,9'-thioxanthenyl] or substituted or unsubstituted (10-phenyl-10H-spiro[acridinyl-9,9'-fluorenyl]).

[0128] For example, L 2 -Ar 1 and L 3 -Ar 2 The substituents listed in Group I may be each independently selected.

[0129] [Group I]

[0130]

[0131]

[0132] In Group I,

[0133] R 20 to R 24 、R 30 and R 31 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl,

[0134] Ar 7 to Ar 9 are each independently a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0135] m11 is an integer from 1 to 5,

[0136] m12 is an integer from 1 to 4,

[0137] m13 is an integer from 1 to 3,

[0138] m14 is an integer of 1 or 2,

[0139] m15 is 1, and

[0140] * is the connection point.

[0141] In the most specific embodiment, a specific example of the combination of Chemical Formula 1 and Chemical Formula 2 may be one selected from the compounds listed in Group 1, but is not limited thereto.

[0142] [Group 1]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159] According to another embodiment, a composition for an organic optoelectronic device includes a first compound and a second compound, wherein the first compound is the above-described compound for an organic optoelectronic device, and the second compound may be represented by Chemical Formula 3 or a combination of Chemical Formula 4 and Chemical Formula 5.

[0160] [Chemical Formula 3]

[0161]

[0162] In Chemical Formula 3,

[0163] R 13 to R 17 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 heterocyclic group,

[0164] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0165] L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0166] m3, m6 and m7 are each independently an integer from 1 to 4,

[0167] m4 and m5 are each independently one of integers from 1 to 3, and

[0168] n is an integer from 0 to 2;

[0169]

[0170] In Chemical Formula 4 and Chemical Formula 5,

[0171] a1* to a4* in Chemical Formula 4 are each independently a connecting carbon (C) or CL b -R b ,

[0172] Among a1* to a4* in Chemical Formula 4, adjacent two are each connected to * in Chemical Formula 5,

[0173] Among a1* to a4* in Chemical Formula 4, the remaining two not connected to * in Chemical Formula 5 are CL b -R b ,

[0174] L b , L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0175] R b 、R 18 and R 19 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 heterocyclic group,

[0176] 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, and

[0177] m8 and m9 are each independently one of integers from 1 to 4.

[0178] The second compound may be used together with the above-mentioned first compound in the light-emitting layer to improve light-emitting efficiency and lifespan characteristics by increasing charge mobility and enhancing stability.

[0179] In Chemical Formula 3, when m3 is 2 or greater, R 13 Each may be the same as or different from each other.

[0180] In Chemical Formula 3, when m4 is 2 or greater, R 14 Each may be the same as or different from each other.

[0181] In Chemical Formula 3, when m5 is 2 or greater, R 15 Each may be the same as or different from each other.

[0182] In Chemical Formula 3, when m6 is 2 or greater, R 16 Each may be the same as or different from each other.

[0183] In Chemical Formula 3, when m7 is 2 or greater, R17 Each may be the same as or different from each other.

[0184] In Chemical Formula 4 and Chemical Formula 5, when m8 is 2 or greater, R 18 Each may be the same as or different from each other.

[0185] In Chemical Formula 4 and Chemical Formula 5, when m9 is 2 or greater, R 19 Each may be the same as or different from each other.

[0186] In Chemical Formula 4 and Chemical Formula 5, when R b When it is 2 or greater, R b Each may be the same as or different from each other.

[0187] For example, in Chemical Formula 3, Ar 3 and Ar 4 each independently may 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 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.

[0188] In Chemical Formula 3, 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,

[0189] In Chemical Formula 3, R 13 to R 17 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group,

[0190] n can be 0 or 1.

[0191] For example, in Chemical Formula 3, “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.

[0192] For example, in Chemical Formula 3, Ar 3 and Ar 4 Each independently may be 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.

[0193] In a specific embodiment of the present invention, Chemical Formula 3 can be represented by one of Chemical Formulas 3-1 to 3-15.

[0194]

[0195]

[0196] In Chemical Formulas 3-1 to 3-15, R 13 to R 17 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and L 4 -Ar 3 and L 5 -Ar 4 and each independently may be one of the substituents listed in Group II.

[0197] [Group II]

[0198]

[0199] In Group II,

[0200] R 25 to R 29 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl,

[0201] m16 is an integer from 1 to 5,

[0202] m17 is an integer from 1 to 4,

[0203] m18 is an integer from 1 to 3,

[0204] m19 is an integer of 1 or 2,

[0205] m20 is one of integers from 1 to 7, and

[0206] * is the connection point.

[0207] In Group II, when m16 is 2 or greater, R 25 Each may be the same as or different from each other.

[0208] In Group II, when m17 is 2 or greater, R 26 Each may be the same as or different from each other.

[0209] In Group II, when m18 is 2 or greater, R 27 Each may be the same as or different from each other.

[0210] In Group II, when m19 is 2 or greater, R 28 Each may be the same as or different from each other.

[0211] In Group II, when m20 is 2 or greater, R 29 Each may be the same as or different from each other.

[0212] The second compound may be represented, for example, by any one of Chemical Formula 4A, Chemical Formula 4B, Chemical Formula 4C, Chemical Formula 4D, and Chemical Formula 4E.

[0213]

[0214] In Chemical Formulae 4A to 4E, L 5 , L 6 、Ar 5 、Ar 6 、R 12 and R 13 As described above,

[0215] L b1 To L b4 The L described above 6 and L 7 The definition of is the same as

[0216] R b1 to R b4 As described above, R 18 and R 19 The definition is the same.

[0217] For example, in Chemical Formula 4 and Chemical Formula 5, Ar 5 and Ar 6 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 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, and

[0218] R b1 to R b4 、R 18 and R 19 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.

[0219] In a specific embodiment of the present invention, in Chemical Formula 4 and Chemical Formula 5, L 6 -Ar 5 and L 7 -Ar 6 may be each independently selected from the substituents listed in Group II.

[0220] In one embodiment, R b1 to R b4、R 18 and R 19 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.

[0221] For example, R b1 to R b4 、R 18 and R 19 may each independently be hydrogen, deuterium, cyano or substituted or unsubstituted phenyl, and

[0222] In a specific embodiment, R b1 to R b4 、R 18 and R 19 and may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0223] In a specific embodiment of the present invention, the second compound can be represented by Chemical Formula 3-8, and in Chemical Formula 3-8, Ar 3 and Ar 4 L 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, 4 and L 5 may each independently be a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 13 to R 16 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.

[0224] For example, in Chemical Formula 3-8, R 13 to R 16 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and L 4 -Ar 3 and L 5 -Ar 4 and each independently may be one of the substituents listed in Group II.

[0225] In another specific embodiment of the present invention, the second compound can be represented by Chemical Formula 4C or Chemical Formula 4D, and in Chemical Formula 4C and Chemical Formula 4D, L b1 To L b4Each of them 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 18 、R 19 and R b1 to R b4 can each be hydrogen, deuterium or phenyl, and Ar 5 and Ar 6 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 pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0226] For example, in Chemical Formula 4C and Chemical Formula 4D, L b1 To L b4 Each can be a single bond, R 18 、R 19 and R b1 to R b4 may each independently be hydrogen, deuterium or a C6 to C12 aryl group, and L 6 -Ar 5 and L 7 -Ar 6 and each independently may be one of the substituents listed in Group II.

[0227] For example, the second compound for an organic optoelectronic device may be one selected from the compounds listed in Group 2, but is not limited thereto.

[0228] [Group 2]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235] In addition, examples are given below in which at least one hydrogen in Compounds B-1 to B-152 listed in Group 2 is replaced by deuterium, but the present invention is not limited thereto.

[0236]

[0237]

[0238]

[0239] (Dn represents the number of substituted deuterium and indicates a structure substituted with one or more deuteriums).

[0240] For compounds B-153 to B-198 of Group 2, the most specific structures are presented below as examples based on deuterium substitution positions and substitution rates, and the most specific structures are not intended to limit the scope of rights to compounds not presented below.

[0241] The scope of the present invention is determined by the claims, and if substituted with deuterium, the present invention is not limited to the compounds exemplified below, but can include all variable ranges within the above range of compound B-1 to compound B-198 depending on the deuterium substitution position and deuterium substitution rate, etc.

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249] In addition, examples are given below in which at least one hydrogen atom in Compounds C-1 to C-57 listed in Group 2 is replaced by deuterium, but the present invention is not limited thereto.

[0250]

[0251] (Dn represents the number of substituted deuterium and indicates a structure substituted with one or more deuteriums).

[0252] For compounds C-58 to C-72 of Group 2, only the most specific structures are presented below as examples based on deuterium substitution positions and substitution rates, and this most specific structure is not intended to limit the scope of rights to compounds not presented below.

[0253] The scope of the present invention is determined by the claims, and if substituted with deuterium, the present invention is not limited to the compounds exemplified below, but can include all variable ranges within the above range of compound C-58 to compound C-72 depending on the deuterium substitution position and deuterium substitution rate, etc.

[0254]

[0255]

[0256] In the most specific embodiment, the first compound may be represented by Chemical Formula 1A-I-1 or Chemical Formula 1B-I-1, and the second compound may be represented by any one of Chemical Formula 3-8, Chemical Formula 4C, and Chemical Formula 4D.

[0257] For example, the first compound and the second compound can be included in a weight ratio of 1:99 to 99:1. Within the above range, the electron transport ability of the first compound and the hole transport ability of the second compound can be utilized to achieve bipolar properties by matching the appropriate weight ratio to improve efficiency and lifespan. Within this range, for example, they can be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20 (e.g., about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40). As a specific example, they can be included in a weight ratio of 40:60, 50:50, or 60:40.

[0258] In addition to the above-mentioned first compound and second compound, one or more additional compounds may be contained.

[0259] The compound for an organic optoelectronic device or the composition for an organic optoelectronic device may be a composition further including a dopant.

[0260] 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.

[0261] A dopant is a material mixed in a small amount with a compound or composition used in an organic optoelectronic device to induce luminescence, and is generally a material such as a metal complex that emits light by multiple excitations to a triplet state or more. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and one or more types thereof may be used.

[0262] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organometallic 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.

[0263] [Chemical formula Z]

[0264] L 8 MX 2

[0265] In the chemical formula Z, M is a metal, and L 8 and X 2 are the same or different and are ligands that form a complex with M.

[0266] 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 2 This may be, for example, a bidentate ligand.

[0267] By L 8 and X 2 Examples of the ligand represented by may be selected from the chemical formulae listed in Group A, but are not limited thereto.

[0268] [Group A]

[0269]

[0270] In Group A,

[0271] 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

[0272] 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.

[0273] For example, a dopant represented by Chemical Formula V may be included.

[0274] [Chemical Formula V]

[0275]

[0276] In Chemical Formula V,

[0277] R 101 to R 116are 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 ,

[0278] R 132 to R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0279] R 101 to R 116 At least one of them is a functional group represented by Chemical Formula V-1,

[0280] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone pair of electrons of a carbon or heteroatom, and

[0281] m21 and m22 are each independently any one of integers from 0 to 3, and m21+m22 is any one of integers from 1 to 3,

[0282] [Chemical Formula V-1]

[0283]

[0284] In Chemical Formula V-1,

[0285] 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

[0286] * refers to the moiety attached to the carbon atom.

[0287] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0288] [Chemical Formula Z-1]

[0289]

[0290] In the chemical formula Z-1, rings A, B, C and D independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0291] R A 、R B 、R C and R D independently represents mono-, di-, tri- or tetra-substituted or unsubstituted;

[0292] 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;

[0293] When nA is 1, L E is selected from 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

[0294] R A 、R B 、R C 、R D R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, 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.

[0295] The dopant according to one embodiment may be a platinum complex, and may be represented by, for example, Chemical Formula VI.

[0296] [Chemical Formula VI]

[0297]

[0298] In Chemical Formula VI,

[0299] X 100 Selected from O, S and NR 131 ,

[0300] 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 -SiR132 R 133 R 134 ,

[0301] R 132 to R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0302] R 117 to R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl, and

[0303] R 132 to R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0304] 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.

[0305] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy and vice versa, such as an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0306] Herein, an organic light emitting diode is described as one example of an organic optoelectronic device with reference to the accompanying drawings.

[0307] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0308] refer to Figure 1 , the organic light emitting diode 100 according to one 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 .

[0309] 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 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; or 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.

[0310] 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 include a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0311] The organic layer 105 may include the above-described composition for an organic optoelectronic device.

[0312] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-described composition for an organic optoelectronic device.

[0313] The composition for an organic optoelectronic device further including a dopant may be, for example, a green light emitting composition.

[0314] The light emitting layer 130 may include, for example, the first compound and the second compound described above as phosphorescent hosts.

[0315] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0316] The charge transport region may be, for example, a hole transport region 140 .

[0317] The hole transport region 140 may further improve hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0318] 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 of group B may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0319] [Group B]

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326] (Dn represents the number of substituted deuterium and indicates a structure substituted with one or more deuteriums).

[0327] 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 similar structures can also be used.

[0328] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0329] The electron transport region 150 may further improve electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0330] 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 of group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0331] [Group C]

[0332]

[0333]

[0334]

[0335] One embodiment may be an organic light emitting diode including a light emitting layer as an organic layer.

[0336] Another embodiment may be an organic light emitting diode including a light emitting layer and a hole transport region as organic layers.

[0337] Another embodiment may be an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0338] like Figure 1 As shown, 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 .

[0339] 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 organic layers in addition to the light emitting layer.

[0340] The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, and then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating and forming the cathode or anode thereon.

[0341] Organic light emitting diodes can be applied to organic light emitting display devices.

[0342] Invention Mode

[0343] 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.

[0344] Hereinafter, 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 synthesized by known methods unless otherwise specified.

[0345] (Preparation of Compounds for Organic Optoelectronic Devices)

[0346] Synthesis Example 1: Synthesis of Intermediate I-1

[0347]

[0348] Step 1: Synthesis of intermediate a-1

[0349] 2-Bromo-1,4-difluoro-3-nitrobenzene (120.0 g, 504.22 mmol, Merck & Co., Inc.) and aniline (93.92 g, 1008.45 mmol, Merck & Co., Inc.) were dissolved in 840 ml of ethanol and reacted at 130° C. for 5 hours. The reactant was then poured into a large amount of DIW (deionized water), stirred for 30 minutes, filtered, and washed twice or more with water and ethanol, and the solid was separated and dried to obtain Intermediate a-1 (128 g, yield: 82%).

[0350] Step 2: Synthesis of intermediate a-2

[0351] Intermediate a-1 (128.0 g, 411.43 mmol), (2-chloro-6-hydroxyphenyl) boronic acid (177.12 g, 493.72 mmol), Pd(PPh 3 ) 4 (12.77 g, 20.57 mmol) and K 2 CO 3 (142.16 g, 1028.58 mmol) were added to dioxane (600 ml) and DIW (300 ml) and dissolved therein, and then heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled and, after removing the aqueous layer and removing the solvent with a rotary evaporator, extracted with dichloromethane / DIW. The organic layer thus obtained was passed through a column with hexane: EA (ethyl acetate) = 4: 1 (v / v), thereby obtaining intermediate a-2 (80.0 g, yield: 50%).

[0352] Step 3: Synthesis of intermediate a-3

[0353] Intermediate a-2 (80.0 g, 223.00 mmol) and K 3 PO 4 (95.0 g, 445.99 mmol) were added to DMF (dimethylformamide, 200 ml) and dissolved therein, and then heated under reflux at 120° C. for 3 hours. When the reaction was completed, after removing the solvent with a rotary evaporator, the organic layer thus extracted with dichloromethane / DIW was dried with MgSO 4 , concentrated, and then stirred with a small amount of methanol to obtain a solid, which was recrystallized with 200 mL of toluene to obtain Intermediate a-3 (65.0 g, yield: 86%).

[0354] Step 4: Synthesis of intermediate a-4

[0355] Intermediate a-3 (65.0 g, 191.88 mmol) is dissolved in a mixed solvent of 700 mL of ethanol / THF, and sodium hydrosulfite (157.22 g, 767.53 mmol) and K2CO3 (106.28 g, 767.53 mmol) dissolved in DIW are slowly added dropwise thereto at room temperature, and then stirred at room temperature for 2 hours. When the reaction is complete, after separating the organic layer and evaporating the solvent, the organic layer is extracted with EA / DIW, and dried and concentrated to obtain intermediate a-4 (45.0 g, yield: 76%).

[0356] Step 5: Synthesis of intermediate a-5

[0357] 45g (145.94mmol) of intermediate a-4 and 15.5g (145.94mmol) of benzaldehyde (Merck & Co., Inc.) were dissolved in 45g (729.69mmol) of acetic acid and then reacted at room temperature for 3 hours. The reactant was then poured into a large amount of DIW, stirred for 30 minutes and washed with water twice or more. The solid was thus separated, extracted with dichloromethane and DIW and dried over magnesium sulfate to remove all solvents. Subsequently, the solid was dissolved in dichloromethane equivalent to 10 times the amount of the solid, and 35.17g (154.91mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was slowly added thereto, followed by reaction at room temperature for 2 hours to obtain intermediate a-5 (40g, yield: 77%).

[0358] Step 6: Synthesis of Intermediate I-1

[0359] Intermediate a-5 (40.0 g, 101.30 mmol), bis(pinacolato)diboron (30.87 g, 121.56 mmol), Pd2(dba)3 (5.57 g), P(Cy)3 (6.82 g) and KOAc (29.83 g) were dissolved in 300 mL of xylene, and then stirred and refluxed at 150° C. for 12 hours. When the reaction was complete, the reaction solvent was removed by rotary evaporation, and the organic layer extracted with dichloromethane was column-filtered with hexane:EA=4:1 (v / v) to obtain Intermediate I-1 (40.0 g, yield: 81%).

[0360] Synthesis Example 2: Synthesis of Intermediate I-2

[0361]

[0362] Intermediate I-2 (39.0 g, yield: 79%) was prepared in the same manner as steps 1 to 6 of the synthesis method of intermediate I-1, except that 2-bromo-1,3-difluoro-4-nitrobenzene was used instead of 2-bromo-1,4-difluoro-3-nitrobenzene as the starting material.

[0363] Synthesis Example 3: Synthesis of Intermediate I-3

[0364]

[0365] Step 1: Synthesis of intermediate c-1

[0366] Intermediate b-1 (128.0 g, 411.43 mmol), (2-chloro) boronic acid (77.2 g, 493.72 mmol), Pd (PPh 3 ) 4 (23.77 g, 20.57 mmol) and K 2 CO 3 (142.16 g, 1028.58 mmol) were added to dioxane (600 ml) and DIW (300 ml) and dissolved therein, and then heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled and, after removing the aqueous layer and removing the solvent using a rotary evaporator, extracted with dichloromethane / DIW. The organic layer thus obtained was passed through a column with hexane: EA = 4: 1 (v / v) to obtain intermediate c-1 (85.0 g, yield: 60%).

[0367] Step 2: Synthesis of intermediate c-2

[0368] Intermediate c-1 (85.0 g, 247.99 mmol) and K CO (51.41 g, 371.99 mmol) were dissolved in 800 mL of dimethylformamide, and after the reaction solution temperature was adjusted to 0° C., 1200 g (272.79 mmol) of sodium methyl mercaptan was slowly added thereto. When the addition was complete, the temperature was raised to 100° C., and the reaction solution was heated under reflux for 2 hours. The solid was filtered, extracted with ethyl acetate and DIW, and after evaporating the solvent layer, recrystallized with hexane to obtain intermediate c-2 (57.0 g, yield: 65%).

[0369] Step 3: Synthesis of intermediate c-3

[0370] Intermediate c-2 (57.0 g, 153.7 mmol) and sodium periodate (49.31 g, 230.55 mmol) were dissolved in 1000 mL of a mixed solvent of ethanol / DIW, and then stirred and refluxed at 50° C. for 12 hours. When the reaction was complete, a 1 M aqueous sodium thiosulfate solution was added to the reaction solution, followed by stirring for 1 hour and extraction with excess dichloromethane, and the solvent was evaporated to obtain intermediate c-3 (50.0 g, yield: 84%).

[0371] Step 4: Synthesis of intermediate c-4

[0372] Intermediate c-3 (50.0 g, 129.25 mmol) was dissolved in 500 mL of 1,2-dichloroethane, and after the temperature of the reaction solution was set at 0 ° C, 72.93 g (258.50 mmol) of trifluoromethanesulfonic anhydride was slowly added thereto in a dropwise manner, and after the temperature was raised to room temperature, it was stirred for 1 hour. After the internal temperature was adjusted to 5 ° C, pyridine (30.65 g, 193.87 mmol) was slowly added thereto in a dropwise manner, and then reacted at room temperature for 12 hours. The solid thus obtained was filtered and washed with ethanol, and the solvent was removed thereby to obtain intermediate c-4 (35.0 g, yield: 76%).

[0373] Step 5: Synthesis of intermediate c-5

[0374] Intermediate c-4 (35.0 g, 98.64 mmol) was dissolved in a mixed solvent of 200 mL of ethanol / THF, and sodium dithionite (80.82 g, 394.58 mmol) and K CO (54.53 g, 394.58 mmol) dissolved in DIW were slowly added dropwise thereto at room temperature, and then stirred at room temperature for 2 hours under reflux. When the reaction was complete, the organic layer was separated and the solvent was evaporated, and the organic layer was extracted with EA / DIW, dried and concentrated with MgSO to obtain intermediate c-5 (28.0 g, yield: 87%).

[0375] Step 6: Synthesis of intermediate c-6

[0376] Intermediate c-5 (34.0 g, 103.57 mmol) and benzaldehyde (11 g, 103.57 mmol) (Merck & Co., Inc.) were dissolved in 30 g of acetic acid and then reacted at room temperature for 3 hours. The reactant was then poured into a large amount of DIW, stirred for 30 minutes, filtered, and washed with water twice or more. The solid was thus separated, extracted with dichloromethane and DIW, and dried over magnesium sulfate to remove all solvents. Subsequently, the solid was dissolved in dichloromethane equivalent to 10 times the amount of the solid, and 20.0 g (83.15 mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was slowly added thereto, followed by reaction at room temperature for 2 hours to obtain intermediate c-6 (22 g, yield: 74%).

[0377] Step 7: Synthesis of Intermediate I-3

[0378] Intermediate I-3 (20.0 g, yield: 74%) was obtained in the same manner as in Step 6 of Synthesis Example 1 (Synthesis of Intermediate I-1), except that: intermediate c-6 (22.0 g, 55.72 mmol) and bis(pinacolato)diboron (16.98 g, 66.86 mmol) were used.

[0379] <Intermediate>

[0380]

[0381] Synthesis Example 4: Synthesis of Compound 1

[0382] In a round-bottom flask, Intermediate I-1 (31.6 g, 63.99 mmol), 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (Intermediate A, 20.0 g, 58.17 mmol) purchased from P&H Tech (http: / / www.phtech.co.kr / ), Pd(PPh) (3.36 g, 2.91 mmol), and KCO (20.1 g) were dissolved in 100 mL of THF and 50 mL of distilled water, then heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, the aqueous layer was removed, and the organic layer was dried under reduced pressure. The resulting solid was washed with water and methanol and recrystallized twice from 200 mL of toluene to obtain Compound 1 (32 g, 82% yield). LC / MS calculated for C46H29N5O: exact mass: 667.77, found: 667.95 [M+H].

[0383] Synthesis Example 5: Synthesis of Compound 43

[0384] Compound 43 (32.0 g, yield: 84%) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-1 (30.36 g, 61.49 mmol) and 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (Intermediate B, 20.0 g, 55.9 mmol) purchased from P&H Tech (http: / / www.phtech.co.kr / ) were used. LC / MS calculated for C46H27N5O2: exact mass: 681.76, measured value: 682.35 [M+H].

[0385] Synthesis Example 6: Synthesis of Compound 436

[0386] Compound 436 (28.0 g, yield: 90%) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-2 (30.36 g, 61.49 mmol) and Intermediate A (20.0 g, 58.17 mmol) were used. LC / MS calculated for C46H29N5O: exact mass: 681.76, measured value: 667.77 [M+H].

[0387] Synthesis Example 7: Synthesis of Compound 207

[0388] Compound 207 (30.0 g, yield: 79%) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-2 (30.36 g, 61.49 mmol) and Intermediate B (20.0 g, 55.9 mmol) were used. LC / MS calculated for C46H27N5O2: exact mass: 681.76, measured value: 682.22 [M+H].

[0389] Synthesis Example 8: Synthesis of Compound 224

[0390] Compound 224 (30.0 g, 84% yield) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-2 (30.36 g, 61.49 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (Intermediate C, 20 g, 47.86 mmol) were used. LC / MS calculated for C52H31N5O: exact mass: 741.85, measured value: 742.42 [M+H].

[0391] Synthesis Example 9: Synthesis of Compound 229

[0392] Compound 229 (30.0 g, yield: 86%) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-2 (25.09 g, 50.82 mmol) and 9-(4-([1,1′-biphenyl]-4-yl)-6-chloro-1,3,5-triazin-2-yl)-9H-carbazole (Intermediate D, 20 g, 46.20 mmol) were used. LC / MS calculated for C52H32N6O: exact mass: 756.87, measured value: 757.12 [M+H].

[0393] Synthesis Example 10: Synthesis of Compound 437

[0394] Compound 437 (28.0 g, yield: 89%) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-3 (25.92 g, 50.82 mmol) and Intermediate A (20 g, 46.20 mmol) were used. LC / MS calculated for C46H29N5S: exact mass: 683.83, measured value: 683.43 [M+H].

[0395] Synthesis Example 11: Synthesis of Compound 1

[0396]

[0397] The main compound 1 was synthesized by referring to the synthesis method of patent WO2016-194604.

[0398] HRMS (70 eV, EI+): m / z calculated for C45H29N5: 639.2423, found: 639. Elemental analysis: C, 84%; H, 5%.

[0399] Synthesis Example 12: Synthesis of Compound 2

[0400]

[0401] Intermediate d-1 (42 g, yield: 72%) was obtained in the same manner as in Step 6 of Synthesis Example 1 (Synthesis of Intermediate I-1), except that 2-(4'-chloro-[1,1'-biphenyl]-4-yl)-1,4-diphenyl-1H-benzo[2,3]benzofurano[4,5-d]imidazole (50 g, 91.40 mmol) and bis(pinacolato)diboron (27.85 g, 109.68 mmol) purchased from P&H Tech (http: / / www.phtech.co.kr / ) were used, and

[0402] The subject 2 (32.0 g, yield: 76%) was obtained in the same manner as in Synthesis Example 4, except that: Intermediate d-1 (40.21 g, 62.02 mmol) and Intermediate E (16 g, 26.39 mmol) were used. LC / MS calculated for C52H33N5O: accurate mass: 743.87, measured value: 744.19 [M+H].

[0403] Synthesis Example 13: Synthesis of Compound 3

[0404]

[0405] In the same manner as in Step 6 of Synthesis Example 1 (Synthesis of Intermediate I-1), 5-(3-chlorophenyl)-2-phenylbenzo[2,3]benzofurano[5,4-d]thiazole (50 g, 121.38 mmol) and bis(pinacolato)diboron (36.99 g, 145.67 mmol) purchased from P&H Tech (http: / / www.phtech.co.kr / ) were used to obtain Intermediate e-1 (48 g, yield: 79%), and

[0406] The subject 3 (40.0 g, yield: 80%) was obtained in the same manner as in Synthesis Example 4, except that intermediate e-1 (40.88 g, 79.99 mmol) and intermediate E (25 g, 72.71 mmol) were used. LC / MS calculated for C46H28N4OS: accurate mass: 684.82, measured value: 685.33 [M+H].

[0407] Synthesis Example 14: Synthesis of Compound 4

[0408]

[0409] Step 1: Synthesis of intermediate g-1

[0410] 100g (404.86mmol) of 6-amino-2-bromo-3-fluorophenol (Merck & Co., Inc.) and 43g (485.83mmol) of benzaldehyde (Merck & Co., Inc.) were dissolved in 120g (2024.29mmol) of acetic acid and reacted at room temperature for 3 hours. The reactant was then poured into a large amount of DIW, stirred for 30 minutes and washed with water twice or more. The solid was thus separated, extracted with dichloromethane and DIW, and dried over magnesium sulfate to remove all solvents. Subsequently, the solid was dissolved in dichloromethane equivalent to 10 times the amount of the solid, and then 84.9g (374mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) was slowly added and reacted at room temperature for 2 hours to obtain intermediate g-1 (70g, yield: 70%).

[0411] Step 2: Synthesis of intermediate g-2

[0412] Intermediate g-1 (70.0 g, 239.64 mmol), (5-chloro-2-hydroxyphenyl) boronic acid (45.44 g, 263.60 mmol), Pd (PPh 3 ) 4 (13.85 g, 11.98 mmol) and K 2 CO 3 (99.36 g, 718.91 mmol) were added to dioxane (600 ml) and DIW (3000 ml) and dissolved therein, and then heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled and, after removing the aqueous layer and removing the solvent with a rotary evaporator, extracted with dichloromethane / DIW. The organic layer thus obtained in this manner was passed through a column with hexane: EA=4:1 (v / v), thereby obtaining 40.0 g (yield: 49%) of intermediate g-2.

[0413] Step 3: Synthesis of intermediate g-3

[0414] Intermediate g-2 (40.0 g, 117.73 mmol) and K 3 PO 4 (50.0 g, 235.47 mmol) were added to DMF (200 ml) and dissolved therein, and then heated under reflux at 120° C. for 3 hours. When the reaction was completed, after removing the solvent with a rotary evaporator, the organic layer thus extracted with dichloromethane / DIW was dried with MgSO 4 and concentrated, and then stirred with a small amount of methanol to obtain a solid, which was recrystallized with 200 mL of toluene to obtain 30.0 g (yield: 80%) of intermediate g-3.

[0415] Step 4: Synthesis of intermediate g-4

[0416] 30.0 g (93.83 mmol) of Intermediate g-3, 24.0 g (93.83 mmol) of bis(pinacolato)diboron, 5.16 g (5.63 mmol) of Pd2(dba)3, 6.31 g (22.52 mmol) of P(Cy)3, and 27.63 g (281.48 mmol) of KOAc were dissolved in 300 ml of xylene, followed by stirring and reflux at 150° C. for 12 hours. When the reaction was complete, the reaction solvent was removed using a rotary evaporator, and the organic layer extracted with dichloromethane was column-filtered with hexane:EA=4:1 (v / v), thereby obtaining 30.0 g (yield: 78%) of Intermediate g-4.

[0417] Step 5: Composition of Body 4

[0418] In a round-bottom flask, 30.0 g (69.81 mmol) of intermediate g-4, 24.0 g (69.81 mmol) of intermediate F purchased from P&H Tech (http: / / www.phtech.co.kr / ), 4.03 g (3.49 mmol) of Pd(PPh3)4, and 24.12 g (174.51 mmol) of K2CO3 were dissolved in 150 mL of THF and 70 mL of distilled water, and then heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer obtained was dried under reduced pressure. The solid obtained was washed with water and methanol and recrystallized twice with 200 mL of toluene to obtain 33.0 g (yield: 80%) of subject 4. LC / MS calculated for C40H24N4O2: exact mass: 592.19, measured value: 592.88 [M+H].

[0419] Synthesis Example 15: Synthesis of Compound B-136

[0420]

[0421] Compound B-136 was synthesized by referring to patent EP3034581.

[0422] HRMS (70 eV, EI+): m / z calculated for C42H28N2: 560.2252, found: 560.

[0423] Elemental analysis: C, 90%; H, 5%.

[0424] Synthesis Example 16: Synthesis of Compound B-99

[0425]

[0426] Compound B-99 was synthesized with reference to patent KR10-2019-0000597.

[0427] HRMS (70 eV, EI+): m / z calculated for C48H32N2: 636.2565, found: 636.

[0428] Elemental analysis: C, 91%; H, 5%.

[0429] Synthesis Example 17: Synthesis of Compound B-31

[0430]

[0431] Compound B-31 was synthesized by referring to patent EP2947071.

[0432] HRMS (70 eV, EI+): m / z calculated for C48H32N2: 636.2565, found: 636.

[0433] Elemental analysis: C, 91%; H, 5%.

[0434] Synthesis Example 18: Synthesis of Compound C-4

[0435]

[0436] Compound C-4 was synthesized by referring to patent KR2031300.

[0437] HRMS (70 eV, EI+): m / z calculated for C42H28N2: 560.2252, found: 560.

[0438] Elemental analysis: C, 90%; H, 5%.

[0439] Synthesis Example 19: Synthesis of Compound C-57

[0440]

[0441] Compound C-57 was synthesized with reference to patent WO2018-095391.

[0442] HRMS (70 eV, EI+): m / z calculated for C48H32N2: 636.2565, found: 636.

[0443] Elemental analysis: C, 91%; H, 5%.

[0444] (Manufacturing of Organic Optoelectronic Devices)

[0445] Example 1

[0446] 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, then moved to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to Compound B is deposited on the hole transport layer to a thickness of The hole transport auxiliary layer was formed by vacuum deposition of the compound 1 synthesized in Synthesis Example 4 as a host on the hole transport auxiliary layer and doped with PhGD as a dopant at 7 wt %. The ratios are described for the examples and comparative examples, respectively. Compound C is then deposited on the luminescent layer to The thickness of the electron transport auxiliary layer is formed, and the compound D and Liq are vacuum deposited at a weight ratio of 1:1 to form On the electron transport layer, vacuum deposition is performed in sequence LiQ and Al forms the cathode to make green organic light-emitting diodes.

[0447] A green organic light emitting diode was fabricated with the following structure: ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[Compound 1 (93 wt%):PhGD (7 wt%)] Compound C / Compound D:LiQ / LiQ / Al

[0448] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0449] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0450] 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

[0451] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0452] [PhGD]

[0453]

[0454] Examples 2 to 7 and Comparative Examples 1 to 4

[0455] 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.

[0456] Example 8

[0457] 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, then moved to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to Compound E is deposited on the hole transport layer to a thickness of The hole transport auxiliary layer was formed by vacuum deposition of the compound 43 synthesized in Synthesis Example 5 and the compound B-136 synthesized in Synthesis Example 15 as the host on the hole transport auxiliary layer, and 10 wt% of PhGD was doped as a dopant. Thick emitting layer. Here, compound 43 and compound B-136 were used in a weight ratio of 3:7. Subsequently, compound F was deposited on the emitting layer to The thickness of the electron transport auxiliary layer is formed, and the compound G and Liq are vacuum deposited at a weight ratio of 1:1 to form On the electron transport layer, vacuum deposition is performed in sequence LiQ and Al forms the cathode to make green organic light-emitting diodes.

[0458] 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 43:Compound B-136:PhGD=27:63:10 wt%)] / Compound F / Compound G:LiQ / LiQ / Al

[0459] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0460] Compound F: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0461] Compound G: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0462] Examples 9 to 20 and Comparative Examples 5 to 8

[0463] Each organic light emitting diode was manufactured in the same manner as in Example 8, except that the composition was changed as described in Table 2.

[0464] evaluate

[0465] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 20 and Comparative Examples 1 to 8 were evaluated.

[0466] The specific measurement method is as follows, and the results are shown in Tables 1 and 2.

[0467] (1) Measuring the change in current density according to voltage change

[0468] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit device in the obtained organic light emitting diode was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0469] (2) Measuring brightness changes according to voltage changes

[0470] 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).

[0471] (3) Measure luminous efficiency

[0472] By using the luminance and current density and voltage from (1) and (2) above, calculate the 2 ) under the current efficiency (cd / A).

[0473] The luminous efficiency values ​​of Examples 1 to 7 and Comparative Examples 1 to 4 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1.

[0474] The luminous efficiency values ​​of Examples 8 to 20 and Comparative Examples 5 to 8 were calculated as relative values ​​based on Comparative Example 5 and are listed in Table 2.

[0475] (4) Measurement life

[0476] By converting the luminance (cd / m 2 ) maintained at 24000cd / m 2 The results were obtained by measuring the time it takes for the current efficiency (cd / A) to decrease to 97%.

[0477] The life measurement values ​​of Examples 1 to 7 and Comparative Examples 1 to 4 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1.

[0478] The life measurement values ​​of Examples 8 to 20 and Comparative Examples 5 to 8 were calculated as relative values ​​based on Comparative Example 5 and are listed in Table 2.

[0479] (5) Measure the driving voltage

[0480] The ampere-voltmeter (Keithley 2400) was used to measure the 2 The driving voltage of each device was measured to obtain the results.

[0481] The driving voltages of Examples 1 to 7 and Comparative Examples 1 to 4 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1.

[0482] The driving voltages of Examples 8 to 20 and Comparative Examples 5 to 8 were calculated as relative values ​​based on Comparative Example 5 and are listed in Table 2.

[0483] [Table 1]

[0484] serial number Compound Driving voltage (%) efficiency(%) life(%) Example 1 Compound 1 75 150 110 Example 2 Compound 43 75 152 120 Example 3 Compound 436 78 180 135 Example 4 Compound 207 82 180 125 Example 5 Compound 224 75 160 150 Example 6 Compound 229 92 120 160 Example 7 Compound 437 80 170 100 Comparative Example 1 Body 1 100 100 100 Comparative Example 2 Body 2 150 80 50 Comparative Example 3 Body 3 130 75 40 Comparative Example 4 Body 4 95 110 60

[0485] [Table 2]

[0486] serial number Compound Driving voltage (%) efficiency(%) life(%) Example 8 Compound 43 / B-136 85 160 140 Example 9 Compound 43 / B-99 83 162 139 Example 10 Compound 43 / B-31 87 160 142 Example 11 Compound 43 / C-4 80 155 144 Example 12 Compound 43 / C-57 85 150 145 Example 13 Compound 436 / B-136 89 207 145 Example 14 Compound 436 / B-99 87 209 144 Example 15 Compound 436 / B-31 91 207 147 Example 16 Compound 436 / C-4 84 202 150 Example 17 Compound 436 / C-57 89 197 152 Example 18 Compound 224 / C-4 81 180 170 Example 19 Compound 229 / C-4 95 135 180 Example 20 Compound 437 / C-4 88 185 130 Comparative Example 5 Main body 1 / C-4 100 100 100 Comparative Example 6 Main body 2 / C-4 160 90 80 Comparative Example 7 Main body 3 / C-4 140 85 62 Comparative Example 8 Main body 4 / C-4 110 120 60

[0487] Referring to Table 1 and Table 2, the organic light emitting diodes according to Examples 1 to 20 have significantly improved driving voltage, luminous efficiency, and lifespan characteristics compared to the organic light emitting diodes according to Comparative Examples 1 to 8.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by a combination of Chemical Formula 1 and Chemical Formula 2: In Chemical Formula 1 and Chemical Formula 2, X 1 It is O or S, * Each is a connecting carbon (C), * in Chemical Formula 1 is connected to * in Chemical Formula 2, respectively, R 1 and R 2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, R 3 to R 12 are each independently hydrogen, deuterium or substituted or unsubstituted phenyl, m1 is an integer from 1 to 4, m2 is an integer of 1 or 2, and R 1 and R 2 At least one of them is a group represented by chemical formula a, [Chemical formula a] In chemical formula a, Z 1 to Z 3 Each independently is N or CL a -R a , Z 1 to Z 3 At least two of them are N, L a and 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, R a is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

2. The compound for an organic optoelectronic device according to claim 1, wherein The combination of Chemical Formula 1 and Chemical Formula 2 is represented by Chemical Formula 1A or Chemical Formula 1B: In Chemical Formula 1A and Chemical Formula 1B, X 1 、R 1 to R 12 , m1 and m2 are defined in Chemical Formula 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein The combination of Chemical Formula 1 and Chemical Formula 2 is represented by any one of the following Chemical Formulas 1A-I, 1A-II, 1B-I, and 1B-II: In Formula 1A-I, Formula 1A-II, Formula 1B-I, and Formula 1B-II, X 1 、Z 1 to Z 3 、R 3 to R 12 、Ar 1 、Ar 2 、L 1 To L 3 , m1 and m2 are defined in Chemical Formula 1, R 1 and R 2 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, m1' is one of integers from 1 to 3, and m2' is 1.

4. The compound for an organic optoelectronic device according to claim 3, wherein The combination of Chemical Formula 1 and Chemical Formula 2 is represented by Chemical Formula 1A-I-1 or Chemical Formula 1B-I-1: In Chemical Formula 1A-I-1 and Chemical Formula 1B-I-1, X 1 、Z 1 to Z 3 、R 1 to R 12 、Ar 1 、Ar 2 、L 1 To L 3 , m1, m1′, m2, and m2′ are defined in Formula 1A-I and Formula 1B-I.

5. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilole group, substituted or unsubstituted 9,9-spirobifluorenyl, substituted or unsubstituted xanthenyl, substituted or unsubstituted thioxanthenyl, substituted or unsubstituted (10-phenyl-9,10-dihydroacridinyl), substituted or unsubstituted spiro[fluorene-9,9'-xanthenyl], substituted or unsubstituted spiro[fluorene-9,9'-thioxanthenyl] or substituted or unsubstituted (10-phenyl-10H-spiro[acridinyl-9,9'-fluorenyl]).

6. The compound for an organic optoelectronic device according to claim 1, wherein L 2 -Ar 1 and L 3 -Ar 2 Each is independently selected from the substituents listed in Group I: [Group I] In Group I, R 20 to R 24 、R 30 and R 31 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl, Ar 7 to Ar 9 are each independently a substituted or unsubstituted C6 to C12 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m11 is an integer from 1 to 5, m12 is an integer from 1 to 4, m13 is an integer from 1 to 3, m14 is an integer of 1 or 2, m15 is 1, and * 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 represented by Chemical Formula 3 or a combination of Chemical Formula 4 and Chemical Formula 5: [Chemical Formula 3] In Chemical Formula 3, R 13 to R 17 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 heterocyclic group, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m3, m6 and m7 are each independently an integer from 1 to 4, m4 and m5 are each independently one of integers from 1 to 3, and n is an integer from 0 to 2; In Chemical Formula 4 and Chemical Formula 5, a1* to a4* in Chemical Formula 4 are each independently a connecting carbon (C) or CL b -R b , among a1* to a4* in Chemical Formula 4, two adjacent ones are each connected to * in Chemical Formula 5, Among a1* to a4* in Chemical Formula 4, the remaining two not connected to * in Chemical Formula 5 are CL b -R b , L b 、L 6 and L 7 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R b 、R 18 and R 19 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 heterocyclic group, 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, 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 The second compound is represented by Chemical Formula 3-8: [Chemical Formula 3-8] In Chemical Formula 3-8, R 13 to R 16 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, m3 and m6 are each independently an integer from 1 to 4, m4 and m5 are each independently one of integers from 1 to 3, and L 4 -Ar 3 and L 5 -Ar 4 are each independently one of the substituents listed in Group II, [Group II] In Group II, R 25 to R 29 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl, m16 is an integer from 1 to 5, m17 is an integer from 1 to 4, m18 is an integer from 1 to 3, m19 is an integer of 1 or 2, m20 is one of integers from 1 to 7, and * is the connection point.

10. The composition for an organic optoelectronic device according to claim 8, wherein the second compound is represented by Chemical Formula 4C or Chemical Formula 4D: In Chemical Formula 4C and Chemical Formula 4D, L b1 To L b4 Each is a single bond, R 18 、R 19 and R b1 to R b4 are each independently hydrogen, deuterium or C6 to C12 aryl, m8 and m9 are each independently an integer from 1 to 4, and L 6 -Ar 5 and L 7 -Ar 6 Each is independently one of the substituents listed in Group II, [Group II] In Group II, R 25 to R 29 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl, m16 is an integer from 1 to 5, m17 is an integer from 1 to 4, m18 is an integer from 1 to 3, m19 is an integer of 1 or 2, m20 is one of integers from 1 to 7, and * is the connection point.

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 includes 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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