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 Chemical Formula 1A or Chemical Formula 1B; and an organic optoelectronic device and a display device including the same. The detailed description of the chemical formula 1A and the chemical formula 1B is 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 photodiode) 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 generate electrical energy by separating excitons formed by light energy into electrons and holes and transferring these excitons to separate electrodes, while light-emitting devices generate light energy from electrical energy by applying voltage or current to electrodes.

[0004] Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting diodes, organic solar cells, and organic photoconductors.

[0005] Among them, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to the increasing demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by the organic material between electrodes. Summary of the Invention

[0006] Technical issues

[0007] One embodiment provides a compound for an organic optoelectronic device, which can realize an organic optoelectronic device with high efficiency and a long lifetime.

[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.

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

[0011] Technical Solution

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

[0013]

[0014] In Chemical Formula 1,

[0015] X 1 It is O or S,

[0016] R 1 to R 13 、R 17 and R 18 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclyl,

[0017] R 14 to R 16 are each independently hydrogen or deuterium,

[0018] Ar 1 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0019] m1 is an integer from 1 to 3,

[0020] m2 is an integer from 1 to 4,

[0021] When m1 is 2 or greater, each R 17 are the same as or different from each other, and

[0022] When m2 is 2 or greater, each R 18 are the same as or different from each other.

[0023] According to another embodiment, provided is a composition for an organic optoelectronic device including a first compound and a second compound.

[0024] The first compound may be the compound for an organic optoelectronic device described above, and the second compound may be represented by Chemical Formula 2; a combination of Chemical Formula 3 and Chemical Formula 4; or Chemical Formula 5.

[0025] [Chemical Formula 2]

[0026]

[0027] In Chemical Formula 2,

[0028] R 19 to R 23 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,

[0029] Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0030] L1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0031] m3, m6 and m7 are each independently an integer from 1 to 4,

[0032] m4 and m5 are each independently an integer from 1 to 3, and

[0033] n is an integer from 0 to 2;

[0034]

[0035]

[0036] Among them, in Chemical Formula 3 and Chemical Formula 4,

[0037] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R a ,

[0038] Among a1* to a4* in Chemical Formula 3, adjacent two are each connected to * in Chemical Formula 4,

[0039] L a 、L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0040] R a 、R 24 and R 25 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,

[0041] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0042] m8 and m9 are each independently an integer from 1 to 4;

[0043] [Chemical Formula 5]

[0044]

[0045] In Chemical Formula 5,

[0046] L 6are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0047] R 26 to R 29 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,

[0048] Ar 6 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0049] m10, m12 and m13 are each independently an integer from 1 to 4,

[0050] m11 is an integer from 1 to 3,

[0051] When m10 is 2 or greater, each R 26 are the same as or different from each other,

[0052] When m11 is 2 or greater, each R 27 are the same as or different from each other,

[0053] When m12 is 2 or greater, each R 28 are the same as or different from each other, and

[0054] When m13 is 2 or greater, each R 29 are the same as or different from each other.

[0055] 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.

[0056] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0057] Beneficial effects

[0058] An organic optoelectronic device with high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0059] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0060] <Description of Reference Numerals>

[0061] 100: Organic Light-Emitting Diode

[0062] 105: Organic layer

[0063] 110: cathode

[0064] 120: Anode

[0065] 130: Luminous layer

[0066] 140: Hole transport zone

[0067] 150: Electron transport region DETAILED DESCRIPTION

[0068] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present disclosure is not limited thereto.

[0069] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or 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.

[0070] In one embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0071] In the present specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0072] In the present specification, "hydrogen substitution (—H)" may include "deuterium substitution (—D)" or "tritium substitution (—T)".

[0073] As used herein, when a definition is not otherwise provided, "hetero" refers to a group containing 1 to 3 heteroatoms selected from N, O, S, P and Si in one functional group and the rest being carbon.

[0074] As used herein, "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 linked by a σ bond and the hydrocarbon aromatic moiety 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.

[0075] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0076] As used herein, "heterocyclyl" is a general concept of heteroaryl and may contain 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 heterocyclyl is a condensed ring, the entire ring or each ring of the heterocyclyl may contain one or more heteroatoms.

[0077] For example, "heteroaryl" may refer to an aryl group containing at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryls may be directly linked by a sigma bond, or when the heteroaryl group contains two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0078] 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 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.

[0079] 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 substituted quinolinyl, substituted or unsubstituted isoquinazolyl, 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, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofuranofluorenyl, substituted or unsubstituted benzothiophenefluorenyl, or a combination thereof, but not limited thereto.

[0080] As used herein, hole characteristics refer to the ability to contribute electrons to form holes when an electric field is applied, and due to the conductive properties 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.

[0081] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductive properties based on 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.

[0082] Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

[0083] A compound for an organic optoelectronic device according to one embodiment is represented by Chemical Formula 1.

[0084]

[0085] In Chemical Formula 1,

[0086] X 1 It is O or S,

[0087] R1 to R 13 、R 17 and R 18 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclyl,

[0088] R 14 to R 16 are each independently hydrogen or deuterium,

[0089] Ar 1 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0090] m1 is an integer from 1 to 3, and

[0091] m2 is one of integers from 1 to 4.

[0092] The compounds represented by Chemical Formula 1A and Chemical Formula 1B have N-carbazole substituted at the ortho position of the phenylene group connected to the triazine, a substituted or unsubstituted phenyl group substituted at the meta position of the phenylene group relative to the triazine, and the triazine substituted with at least one dibenzofuran (or dibenzothiophene).

[0093] The compound represented by Chemical Formula 1A or Chemical Formula 1B has a structure including an ortho-carbazole in a triazine and has particularly excellent energy transfer efficiency as a phosphorescent dopant, and therefore can be used as a favorable material for a phosphorescent host. When used as a phosphorescent host, the triazine-substituted m-biphenyl structure contained in Chemical Formula 1A or Chemical Formula 1B can improve lifetime by accelerating electron mobility and improving stability compared to a single phenyl structure. In addition, the phenyl groups at the ends of the m-biphenyl structure are each substituted at the ortho and para positions relative to the carbazole moiety, which helps expand the resonance structure of the carbazole moiety and helps stabilize the hole transport portion within the molecule. This leads to an optimization of the charge balance between the electron transport and hole transport portions within the molecule, which further helps improve lifetime.

[0094] Furthermore, when carbazole is substituted at the ortho position of triazine, the dihedral angle increases due to steric hindrance between the triazine and carbazole, and the triazine and carbazole moieties twist relative to each other, thereby increasing the dihedral angle. This means that the electron clouds of the HOMO and LUMO levels are essentially separate, without overlap. This, coupled with a low ΔEst, enables rapid energy transfer and exhibits high efficiency, particularly when used as a phosphorescent host. Furthermore, side reaction pathways in the excited state are reduced, further enhancing the lifetime.

[0095] In addition, by substituting at least one dibenzofuran (or dibenzothiophene) for triazine, electron mobility can be accelerated and stability can be increased compared to diphenyltriazine or bisbiphenyltriazine, thereby improving driving performance and lifespan.

[0096] In addition, by designing three substituents differently surrounding the six-membered nitrogen ring, steric hindrance is achieved, resulting in a low deposition temperature and thus significantly improving the lifetime characteristics of the organic light-emitting diode to which it is applied.

[0097] In Formula 1A and Formula 1B, when two or more R 17 When replaced, each R 17 Can be the same as or different from each other.

[0098] In Chemical Formula 1A and Chemical Formula 1B, when two or more R 18 When replaced, each R 18 Can be the same as or different from each other.

[0099] For example, Chemical Formula 1A may be represented by any one of Chemical Formula 1A-1 to Chemical Formula 1A-4.

[0100]

[0101] In Chemical Formula 1A-1 to Chemical Formula 1A-4,

[0102] R 1 to R 18 、Ar 1 The definitions of m1 and m2 are the same as above.

[0103] For example, Chemical Formula 1B may be represented by any one of Chemical Formula 1B-1 to Chemical Formula 1B-4.

[0104]

[0105] In Chemical Formulas 1B-1 to 1B-4,

[0106] R 1 to R 18 、Ar 1 The definitions of m1 and m2 are the same as above.

[0107] As a specific example, the above Chemical Formula 1 may be represented by Chemical Formula 1A-3 or Chemical Formula 1B-3.

[0108] For example, Ar 1 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0109] For example, R 1to R 13 、R 17 and R 18 and may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group.

[0110] As a specific example, R 17 and R 18 and may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0111] In the most specific embodiment, the compound represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1, but is not limited thereto.

[0112] [Group 1]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] (Dn refers to the number of substituted deuterium atoms and represents a structure in which one or more deuterium atoms are substituted)

[0126] An organic optoelectronic device composition according to one embodiment includes a first compound and a second compound, wherein the first compound is a compound for the above-described organic optoelectronic device, and the second compound may be represented by Chemical Formula 2; a combination of Chemical Formula 3 and Chemical Formula 4; or Chemical Formula 5.

[0127] [Chemical Formula 2]

[0128]

[0129] In Chemical Formula 2,

[0130] R 19 to R 23 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,

[0131] Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0132] L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0133] m3, m6 and m7 are each independently an integer from 1 to 4,

[0134] m4 and m5 are each independently an integer from 1 to 3, and

[0135] n is an integer from 0 to 2;

[0136]

[0137] Among them, in Chemical Formula 3 and Chemical Formula 4,

[0138] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R a ,

[0139] Among a1* to a4* in Chemical Formula 3, adjacent two are each connected to * in Chemical Formula 4,

[0140] L a 、L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0141] R a 、R 24 and R 25 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,

[0142] Ar 4 and Ar 5are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0143] m8 and m9 are each independently an integer from 1 to 4;

[0144] [Chemical Formula 5]

[0145]

[0146] Wherein, in Chemical Formula 5,

[0147] L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0148] R 26 to R 29 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,

[0149] Ar 6 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0150] m10, m12 and m13 are each independently an integer from 1 to 4, and

[0151] m11 is one of integers from 1 to 3.

[0152] 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.

[0153] In Chemical Formula 2, when m3 is 2 or greater, each R 19 Can be the same as or different from each other.

[0154] In Chemical Formula 2, when m4 is 2 or greater, each R 20 Can be the same as or different from each other.

[0155] In Chemical Formula 2, when m5 is 2 or greater, each R 21 Can be the same as or different from each other.

[0156] In Chemical Formula 2, when m6 is 2 or greater, each R 22 Can be the same as or different from each other.

[0157] In Chemical Formula 2, when m7 is 2 or greater, each R 23Can be the same as or different from each other.

[0158] In Chemical Formula 3 and Chemical Formula 4, when m8 is 2 or greater, each R 24 Can be the same as or different from each other.

[0159] In Chemical Formula 3 and Chemical Formula 4, when m9 is 2 or greater, each R 25 Can be the same as or different from each other.

[0160] In Chemical Formula 3 and Chemical Formula 4, when R a is 2 or greater, each R a Can be the same as or different from each other.

[0161] In Chemical Formula 5, when m10 is 2 or greater, each R 26 Can be the same as or different from each other.

[0162] In Chemical Formula 5, when m11 is 2 or greater, each R 27 Can be the same as or different from each other.

[0163] In Chemical Formula 5, when m12 is 2 or greater, each R 28 Can be the same as or different from each other.

[0164] In Chemical Formula 5, when m13 is 2 or greater, each R 29 Can be the same as or different from each other.

[0165] For example, in Chemical Formula 2, Ar 2 and Ar 3 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,

[0166] In Chemical Formula 2, L 2 and L 3 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0167] In Chemical Formula 2, R 19 to R 23 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group,

[0168] n can be 0 or 1.

[0169] For example, in Chemical Formula 2, “substituted” means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0170] For example, in Chemical Formula 2, Ar 2 and Ar 3 Each of the groups may independently 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.

[0171] In a specific embodiment of the present invention, Chemical Formula 2 may be represented by one of Chemical Formulas 2-1 to 2-15.

[0172]

[0173]

[0174] In Chemical Formulas 2-1 to 2-15, R 19 to R 23 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and L 2 -Ar 2 and L 3 -Ar 3 Each may independently be one of the substituents listed in Group I.

[0175] [Group I]

[0176]

[0177] In Group I,

[0178] R 30 to R 34 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl, or C6 to C12 aryl,

[0179] m14 is an integer from 1 to 5,

[0180] m15 is an integer from 1 to 4,

[0181] m16 is an integer from 1 to 3,

[0182] m17 is an integer of 1 or 2,

[0183] m18 is an integer from 1 to 7, and

[0184] * is the connection point.

[0185] In Group I, when m14 is 2 or greater, each R 26Can be the same as or different from each other.

[0186] In Group I, when m15 is 2 or greater, each R 27 Can be the same as or different from each other.

[0187] In Group I, when m16 is 2 or greater, each R 28 Can be the same as or different from each other.

[0188] In Group I, when m17 is 2 or greater, each R 29 Can be the same as or different from each other.

[0189] In Group I, when m18 is 2 or greater, each R 30 Can be the same as or different from each other.

[0190] The combination of Chemical Formula 3 and Chemical Formula 4 can be represented by, for example, any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0191]

[0192] In Chemical Formulae 3A to 3E, L 4 、L 5 、Ar 4 、Ar 5 、R 24 and R 25 Same as above,

[0193] L a1 To L a4 Defined as the above L 4 and L 5 ,and

[0194] R a1 to R a4 Defined as the above R 24 and R 25 .

[0195] For example, in Chemical Formulas 3 and 4, Ar 4 and Ar 5 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 dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0196] R a1 to R a4 、R24 and R 25 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.

[0197] In another embodiment of the present invention, in Chemical Formulas 3 and 4, L 4 -Ar 4 and L 5 -Ar 5 Each may independently be one of the substituents listed in Group I.

[0198] In one embodiment, R a1 to R a4 、R 24 and R 25 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.

[0199] For example, R a1 to R a4 、R 24 and R 25 may each independently be hydrogen, deuterium, cyano or substituted or unsubstituted phenyl, and

[0200] In a specific embodiment, R a1 to R a4 、R 24 and R 25 and may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0201] In another embodiment of the present invention, the second compound can be represented by Chemical Formula 2-8, and in Chemical Formula 2-8, Ar 2 and Ar 3 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, 2 and L 3 may each independently be a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 19 to R 22Each 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.

[0202] For example, in Chemical Formula 2-8, R 19 to R 22 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and L 2 -Ar 2 and L 3 -Ar 3 Each may independently be one of the substituents listed in Group I.

[0203] In another embodiment of the present invention, the second compound can be represented by Chemical Formula 3C, and in Chemical Formula 3C, L a3 and L a4 Can be a single bond, L 4 and L 5 may be each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 24 、R 25 、R a3 and R a4 can each be hydrogen, deuterium or phenyl, and Ar 2 and Ar 3 Each of the groups may independently be 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.

[0204] For example, in Formula 3C, L a3 and L a4 Can be a single bond, R 24 、R 25 、R a3 and R a4 may be each independently hydrogen, deuterium or C6 to C12 aryl, and L 4 -Ar 4 and L 5 -Ar 5 Each may independently be one of the substituents listed in Group I.

[0205] Chemical Formula 5 can be represented by, for example, any one of Chemical Formula 5-1 to Chemical Formula 5-4.

[0206]

[0207]

[0208] In Chemical Formula 5-1 to Chemical Formula 5-4, L 6 、Ar 6 and R 26 to R 29 Same as above.

[0209] For example, in Chemical Formula 5, Ar 6 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, and

[0210] R 26 to R 29 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0211] In another embodiment of the present invention, in Chemical Formula 5, L 6 -Ar 6 The substituents listed in Group I may be selected.

[0212] For example, R 26 to R 29 and may each independently be hydrogen, deuterium, cyano, or substituted or unsubstituted phenyl.

[0213] For example, the compound of the second organic optoelectronic device may be one selected from the compounds listed in Group 2, but is not limited thereto.

[0214] [Group 2]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221] In addition, examples of Compound B-1 to Compound B-150 listed in Group 2 in which at least one hydrogen is replaced with deuterium are shown below, but the present invention is not limited thereto.

[0222] [B-151][B-152][B-153][B-154][B-155]

[0223]

[0224]

[0225] (Dn refers to the number of substituted deuterium atoms and represents a structure in which one or more deuterium atoms are substituted)

[0226] The most specific structures of Compound B-151 to Compound B-195 of Group 2 are provided below as examples according to the position and degree of deuterium substitution, which does not limit the scope of the rights to compounds not shown below.

[0227] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds exemplified below, and the position of deuterium substitution and the degree of substitution of deuterium substitution can include all variable ranges within the range of Compound B-1 to Compound B-195.

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235] In addition, examples of Compound C-1 to Compound C-57 listed in Group 2 in which at least one hydrogen is replaced with deuterium are shown below, but the present invention is not limited thereto.

[0236]

[0237] (Dn refers to the number of substituted deuterium atoms and represents a structure in which one or more deuterium atoms are substituted)

[0238] The most specific structures of compounds C-58 to C-72 of Group 2 are provided below as examples according to the position and degree of deuterium substitution, which does not limit the scope of the rights to compounds not shown below.

[0239] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds exemplified below, and the position of deuterium substitution and the degree of substitution of deuterium substitution can include all variable ranges within the range of compound C-1 to compound C-72.

[0240]

[0241]

[0242]

[0243]

[0244] In addition, examples of Compound D-1 to Compound D-60 listed in Group 2 in which at least one hydrogen is replaced with deuterium are shown below, but the present invention is not limited thereto.

[0245]

[0246]

[0247]

[0248] (Dn refers to the number of substituted deuterium atoms and represents a structure in which one or more deuterium atoms are substituted)

[0249] In the most specific embodiment, the first compound may be represented by Chemical Formula 1A-3 or Chemical Formula 1B-3, and the second compound may be represented by Chemical Formula 2-8.

[0250] For example, the first compound and the second compound may be included in a weight ratio of 1:99 to 99:1. Within this range, the electron transport ability of the first compound and the hole transport ability of the second compound can be utilized to adjust the desired weight ratio to achieve bipolar characteristics, thereby improving efficiency and lifespan. Within the above range, for example, they may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, such as about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, they may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0251] In addition to the above-mentioned first compound and second compound, one or more compounds may be further contained.

[0252] The compound for an organic optoelectronic device or the composition for an organic optoelectronic device may be a composition further including a dopant.

[0253] 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.

[0254] A dopant is a material that is mixed in a small amount with a compound or composition used in an organic optoelectronic device to induce light emission, and is generally a material such as a metal complex that emits light by multiple excitations to a triplet state or higher. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0255] 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.

[0256] [Chemical formula Z]

[0257] L 6 MX 2

[0258] In the chemical formula Z, M is a metal, and L 6 and X 2 are the same or different and are ligands that form a complex with M.

[0259] 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 6 and X 2 This may be, for example, a bidentate ligand.

[0260] By L 6 and X 2 Examples of the represented ligands may be selected from the chemical formulae listed in Group A, but are not limited thereto.

[0261] [Group A]

[0262]

[0263] In Group A,

[0264] R 300 to R 302are each independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted by halogen, or C6 to C30 aryl which may be substituted by C1 to C30 alkyl or halogen, and

[0265] 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.

[0266] The dopant according to one embodiment may be an iridium complex, and may be represented, for example, by Chemical Formula 4-1 or Chemical Formula 4-2.

[0267] [Chemical Formula 4-1]

[0268]

[0269] In Chemical Formula 4-1,

[0270] R 101 to R 116 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0271] R 132 to R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0272] R 101 to R 116 At least one of them is a functional group represented by Chemical Formula V-1,

[0273] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of carbon or a heteroatom, and

[0274] 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,

[0275] [Chemical Formula V-1]

[0276]

[0277] Wherein, in Chemical Formula V-1,

[0278] 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

[0279] * refers to the moiety attached to the carbon atom.

[0280] [Chemical Formula 4-2]

[0281]

[0282] Among them, in Chemical Formula 4-2,

[0283] R 101 to R 117 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 ,

[0284] R 133 to R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0285] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of carbon or a heteroatom, and

[0286] n1 and n2 are each independently any one of integers from 0 to 3, and n1+n2 is any one of integers from 1 to 3.

[0287] In another embodiment, the dopant may be a platinum complex, such as the platinum complex represented by Chemical Formula Z-1.

[0288] [Chemical Formula Z-1]

[0289]

[0290] In chemical formula Z-1, rings A, B, C, and D are each independently a five-membered or six-membered carbocyclic or heterocyclic ring;

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

[0292] L B 、L C and L D are each independently a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' or a combination thereof,

[0293] When nA is 1, L E It can be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' or a combination thereof; and when nA is 0, L E does not exist;

[0294] R A 、R B 、R C 、R D R and R' are each independently hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, cyano, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, or a combination 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 platinum complex can be represented by, for example, Chemical Formula 5-1 or Chemical Formula 5-2.

[0296] [Chemical Formula 5-1]

[0297]

[0298] [Chemical Formula 5-2]

[0299]

[0300] In Chemical Formula 5-1 and Chemical Formula 5-2,

[0301] X 100 Selected from O, S and NR 132 ,

[0302] R 118 to R 132 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 133 R 134 R 135 ,

[0303] R 133 to R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0304] R 118 to R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl, and

[0305] R 133 to R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0306] Hereinafter, an organic optoelectronic device including the above-mentioned compound for an organic optoelectronic device or the composition for an organic optoelectronic device is described.

[0307] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy (or vice versa), such as an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photoconductor.

[0308] Herein, an organic light emitting diode is described as an example of an organic optoelectronic device with reference to the accompanying drawings.

[0309] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0310] 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 .

[0311] The anode 120 may be made of a conductor having a high work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or 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) (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0312] The cathode 110 may be made of a conductor having a low work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0313] The organic layer 105 may include the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[0314] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-described compound for an organic optoelectronic device or composition for an organic optoelectronic device.

[0315] The composition for an organic optoelectronic device further including a dopant may be, for example, a green light emitting composition.

[0316] The light emitting layer 130 may include, for example, the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device as a phosphorescent host.

[0317] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0318] The charge transport region may be, for example, a hole transport region 140 .

[0319] 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.

[0320] Specifically, the hole transport region 140 may include a hole transport layer located between the anode 120 and the light-emitting layer 130, and a hole transport auxiliary layer located between the light-emitting layer 130 and the hole transport layer, and at least one of the compounds listed in group B may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0321] [Group B]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327]

[0328] (Dn refers to the number of substituted deuterium atoms and represents a structure in which one or more deuterium atoms are substituted)

[0329] In the hole transport region 140 , in addition to the compounds described above, known compounds disclosed in US Pat. No. 5,061,569 A, JP 1993-009471 A, WO 1995-009147 A1, JP 1995-126615 A, JP 1998-095973 A, etc., and compounds having similar structures can be used.

[0330] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0331] 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.

[0332] 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 C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0333] [Group C]

[0334]

[0335]

[0336]

[0337]

[0338] One embodiment may be an organic light emitting diode including a light emitting layer as an organic layer.

[0339] Another embodiment may be an organic light emitting diode including a light emitting layer and a hole transport region as organic layers.

[0340] Another embodiment may be an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0341] In addition to the light emitting layer 130, the organic light emitting diode according to one embodiment includes a hole transport region 140 and an electron transport region 150 as the organic layer 105, such as Figure 1 shown.

[0342] 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.

[0343] The organic light emitting diode 100 may be produced by forming an anode or cathode on a substrate, then forming an organic layer by dry film formation such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming the cathode or anode thereon.

[0344] The organic light emitting diode may be applied to an organic light emitting diode display device.

[0345] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the present invention is not limited thereto.

[0346] Invention Mode

[0347] Hereinafter, unless otherwise specified, the starting materials and reactants used in the Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry or P&H tech, or were synthesized by known methods.

[0348] (Preparation of Compounds for Organic Optoelectronic Devices)

[0349] Synthesis Example 1: Synthesis of Compound 1

[0350] [Reaction formula 1]

[0351]

[0352] Step 1: Synthesis of intermediate int-01

[0353] 2,4-dichloro-6-phenyl-1,3,5-triazine (20.0 g, 88.5 mmol), 3-dibenzofuranylboronic acid (17.8 g, 84.1 mmol), K2CO3 (24.5 g, 176.9 mmol) and Pd (dppf) Cl2 (3.6 g, 4.4 mmol) were added to a round-bottom flask and dissolved in toluene (250 ml) and distilled water (90 ml), and then stirred at 60 ° C for 6 hours. When the reaction was completed, after separating the aqueous layer using a separatory funnel, the organic layer thus obtained was distilled under reduced pressure. The obtained product was dissolved by heating with monochlorobenzene, and then filtered and recrystallized through silica to obtain 14.4 g (48%) of intermediate int-01.

[0354] Step 2: Synthesis of intermediate int-02

[0355] Intermediate int-01 (14.4 g, 40.2 mmol), 5-chloro-2-fluorophenylboronic acid (6.8 g, 39.0 mmol), K2CO3 (10.8 g, 78.0 mmol) and Pd(PPh3)4 (2.25 g, 1.95 mmol) were added to a round-bottom flask and dissolved in THF (180 ml) and distilled water (40 ml), and then refluxed at 55°C with stirring for 6 hours. When the reaction was complete, after removing the aqueous layer, 13.2 g (75%) of intermediate int-02 was obtained by using column chromatography (hexane:DCM (30%)).

[0356] Step 3: Synthesis of intermediate int-03

[0357] Intermediate int-02 (13.2 g, 29.2 mmol), phenylboronic acid (10.7 g, 86.6 mmol), Cs2CO3 (19.0 g, 58.4 mmol), tri-tert-butylphosphine (2.9 ml, 5.8 mmol) and Pd2(dba)3 (1.3 g, 1.5 mmol) were added to a round-bottom flask and dissolved in 120 ml of 1,4-dioxane, followed by stirring at reflux at 100°C for 8 hours. When the reaction was complete, after cooling to room temperature, the reactant was poured into excess methanol to precipitate a solid, which was filtered and recrystallized from monochlorobenzene to obtain 10.8 g (75%) of intermediate int-03.

[0358] Step 4: Synthesis of Compound 1

[0359] Intermediate int-03 (10.8 g, 21.9 mmol), 2-phenyl-9H-carbazole (6.4 g, 26.3 mmol) and K 3 PO 4 (9.3 g, 43.8 mmol) were added to a round-bottom flask and dissolved in DMF (100 ml), and then refluxed at 150° C. with stirring for 4 hours. When the reaction was complete, the reactants were slowly added dropwise to excess water to precipitate a solid, which was recrystallized from toluene to obtain 12.6 g (80%) of compound 1.

[0360] Synthesis Example 2: Synthesis of Compound 40

[0361] [Reaction formula 2]

[0362]

[0363] Step 1: Synthesis of intermediate int-05

[0364] By using 2,4-dichloro-6-phenyl-1,3,5-triazine (30.0 g, 132.7 mmol), intermediate Int-04 (46.7 g, 126.1 mmol), K2CO3 (36.7 g, 265.4 mmol) and Pd(dppf)Cl2 (5.42 g, 6.64 mmol), 45.6 g (83%) of intermediate int-05 was obtained in the same manner as in step 1 of Synthesis Example 1.

[0365] Step 2: Synthesis of intermediate int-06

[0366] 1-Bromo-3-chloro-2-fluorobenzene (25.0 g, 119.4 mmol), phenylboronic acid (16.0 g, 131.3 mmol), K CO (33.0 g, 238.7 mmol) and Pd (PPh) (6.9 g, 6.0 mmol) were added to a round-bottom flask and dissolved in THF (350 ml) and distilled water (120 ml), and then refluxed at 65° C. with stirring for 6 hours. When the reaction was completed, after removing the aqueous layer, 21.7 g (88%) of intermediate int-06 was obtained by using column chromatography (hexane: DCM (20%)).

[0367] Step 3: Synthesis of intermediate int-07

[0368] Intermediate int-06 (21.7g, 105.0mmol), bis-boronic acid pinacol ester (32.0g, 126.0mmol), tricyclohexylphosphine (5.1g, 21.0mmol), potassium acetate (20.6g, 210.0mmol) and Pd (dppf) Cl 2 (4.29g, 5.25mmol) are added to a round-bottom flask and dissolved in DMF (250ml). The mixture is refluxed at 140°C for 8 hours. When the reaction is complete, after cooling to room temperature and removing salt by filtration, excessive DCM and distilled water are added thereto for extraction. By using column chromatography (hexane: DCM (30% to 50%)) 25.1g (80%) of intermediate int-07 are thus obtained.

[0369] Step 4: Synthesis of intermediate int-08

[0370] Intermediate int-05 (14.5 g, 33.4 mmol), intermediate int-07 (11.0 g, 36.8 mmol), K2CO3 (9.2 g, 66.8 mmol) and Pd(PPh3)4 (1.93 g, 1.67 mmol) were added to a round-bottom flask and dissolved in THF (170 ml) and distilled water (40 ml), and then refluxed at 70°C with stirring for 6 hours. When the reaction was completed, after removing the aqueous layer, 13.3 g (70%) of intermediate int-08 was obtained by using column chromatography (hexane:DCM (30%)).

[0371] Step 5: Synthesis of Compound 40

[0372] Intermediate int-08 (13.3 g, 23.4 mmol), 9H-carbazole (4.7 g, 28.0 mmol) and K 3 PO 4 (9.9 g, 46.7 mmol) were added to a round-bottom flask and dissolved in DMF (100 ml), and then refluxed at 150° C. with stirring for 4 hours. When the reaction was complete, the reactants were slowly added dropwise to excess water to precipitate a solid, which was filtered and recrystallized from monochlorobenzene to obtain 14.1 g (84%) of compound 40.

[0373] Synthesis Example 3: Synthesis of Compound B-136

[0374]

[0375] Compound B-136 was synthesized with reference to the synthesis method of patent EP3034581.

[0376] Comparative Synthesis Example 1: Synthesis of Compound 1

[0377] [Reaction formula 5]

[0378]

[0379] Step 1: Synthesis of intermediate int-09

[0380] 24.4 g (65%) of intermediate int-09 were synthesized in the same manner as in step 1 of Synthesis Example 1, except that 2,4-dichloro-6-phenyl-1,3,5-triazine (25.0 g, 110.6 mmol), 2-dibenzofuranylboronic acid (22.3 g, 105.1 mmol), K2CO3 (30.6 g, 221.2 mmol) and Pd(dppf)Cl2 (4.52 g, 5.53 mmol) were used.

[0381] Step 2: Synthesis of intermediate int-10

[0382] Intermediate int-9 (24.4 g, 68.2 mmol), 2-fluorophenylboronic acid (11.5 g, 81.8 mmol), K CO (18.9 g, 136.4 mmol) and Pd (PPh) (3.94 g, 3.41 mmol) were added to a round-bottom flask and dissolved in THF (270 ml) and distilled water (70 ml), and then stirred at 70° C. for 6 hours under reflux. When the reaction was complete, after removing the aqueous layer, 17.1 g (60%) of intermediate int-10 was obtained by using column chromatography (hexane: DCM (30%)).

[0383] Step 3: Synthesis of Compound 1

[0384] Intermediate int-10 (17.1 g, 41.0 mmol), 9H-carbazole (13.7 g, 81.9 mmol) and K 3 PO 4 (17.4 g, 81.9 mmol) were added to a round-bottom flask and dissolved in 150 ml of DMF, followed by stirring under reflux at 150° C. for 4 hours. When the reaction was complete, the reactants were slowly added dropwise to excess water to precipitate a solid, which was filtered and recrystallized from monochlorobenzene to obtain 18.5 g (80%) of compound 1.

[0385] Comparative Synthesis Example 2: Synthesis of Compound 2

[0386]

[0387] The main compound 2 was synthesized by referring to the synthesis method of patent KR2020-0023984.

[0388] Comparative Synthesis Example 3: Synthesis of Compound 3

[0389]

[0390] The main compound 3 was synthesized by referring to the synthesis method of patent WO2014-146752.

[0391] Example 1

[0392] An 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 using oxygen plasma, and moved to a vacuum depositor. The obtained ITO transparent electrode was used as an anode, and Compound A doped with 3% NDP-9 (available from Novaled) was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form Compound B is deposited on the hole transport layer by vacuum deposition to form a A thick hole transport auxiliary layer was formed, and the compound 1 synthesized in Synthesis Example 1 was used as a host on the hole transport auxiliary layer and doped with 9 wt% of PhGD as a dopant to form The ratios are described for the following examples and comparative examples. Subsequently, compound C is deposited on the luminescent 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.

[0393] The organic light emitting diode has the following structure: ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[Compound 1 (91 wt%):PhGD (9 wt%)] Compound C / Compound D:LiQ / LiQ / Al

[0394] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0395] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0396] 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

[0397] Compound D: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0398] [PhGD]

[0399]

[0400] Example 2 and Comparative Examples 1 to 3

[0401] Each organic light emitting diode was produced in the same manner as in Example 1, except that the composition was changed to the composition described in Table 1.

[0402] Example 3

[0403] An 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 using oxygen plasma, and moved to a vacuum depositor. The obtained ITO transparent electrode was used as an anode, and Compound A doped with 3% NDP-9 (available from Novaled) was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form Compound E is deposited on the hole transport layer to The hole transport auxiliary layer was formed by simultaneously using the compound 1 synthesized in Synthesis Example 1 and the compound B-136 synthesized in Synthesis Example 3 as the host on the hole transport auxiliary layer, and 9 wt% of PhGD was doped as a dopant by vacuum deposition to form a hole transport auxiliary layer. Thick light-emitting layer. Herein, compound 1 and compound B-136 were used in a weight ratio of 3:7. Then, compound F was deposited on the light-emitting layer to form Thick electron transport auxiliary layer, and compound G and Liq were 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.

[0404] The organic light emitting diode has the following structure: ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound E / EML [Host (Compound 1: Compound B-136 = 30 wt%: 70 wt%): Dopant (PhGD) = 91 wt%: 9 wt%] / Compound F / Compound G:LiQ / LiQ / Al

[0405] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0406] Compound F: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0407] Compound G: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0408] Example 4 and Comparative Examples 4 to 6

[0409] Each organic light emitting diode was produced in the same manner as in Example 3, except that the composition was changed to the composition described in Table 2.

[0410] evaluate

[0411] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 4 and Comparative Examples 1 to 6 were evaluated.

[0412] The specific measurement method is as follows, and the results are shown in Tables 1 and 2.

[0413] (1) Measuring the change in current density according to voltage change

[0414] While increasing the voltage from 0 V to 10 V, a current value flowing through a unit diode in the obtained organic light emitting diode was measured using a voltammeter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0415] (2) Measuring the brightness change according to the voltage change

[0416] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured using a photometer (Minolta Cs-1000A).

[0417] (3) Measurement of luminous efficiency

[0418] The same current density (10 mA / cm2) was calculated using the luminance and current density and voltage measured according to (1) and (2) above. 2 ) under luminous efficiency (cd / A).

[0419] The luminous efficiency values ​​of Examples 1 to 2 and Comparative Examples 1 to 3 were calculated based on Comparative Example 1 as relative values ​​and are listed in Table 1.

[0420] The luminous efficiency values ​​of Examples 3 to 4 and Comparative Examples 4 to 6 were calculated based on Comparative Example 4 as relative values ​​and are listed in Table 2.

[0421] (4) Lifespan measurement

[0422] The brightness (cd / m 2 ) maintained at 24000cd / m 2 Meanwhile, the time for each current efficiency (cd / A) to decrease to 97% was measured as the lifespan.

[0423] The life measurement values ​​of Examples 1 to 2 and Comparative Examples 1 to 3 were calculated based on Comparative Example 1 as relative values ​​and are listed in Table 1.

[0424] The life measurement values ​​of Examples 3 to 4 and Comparative Examples 4 to 6 were calculated based on Comparative Example 4 as relative values ​​and are listed in Table 2.

[0425] (5) Measurement of driving voltage

[0426] An ammeter-voltmeter (Keithley 2400) was used at 15 mA / cm 2 The driving voltage of each diode is measured to obtain the results.

[0427] The driving voltages of Examples 1 to 2 and Comparative Examples 1 to 3 were calculated based on Comparative Example 1 as relative values ​​and are listed in Table 1.

[0428] The driving voltages of Examples 3 to 4 and Comparative Examples 4 to 6 were calculated based on Comparative Example 4 as relative values ​​and are listed in Table 2.

[0429] (Table 1)

[0430]

[0431] (Table 2)

[0432]

[0433] Referring to Tables 1 and 2, the organic light emitting diodes according to Examples 1 to 4 exhibited significantly improved driving voltage, luminous efficiency, and lifespan characteristics compared to the organic light emitting diodes according to Comparative Examples 1 to 6.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1A or Chemical Formula 1B: In Chemical Formula 1, X 1 It is O or S, R 1 to R 13 、R 17 and R 18 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclyl, R 14 to R 16 are each independently hydrogen or deuterium, Ar 1 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group, m1 is an integer from 1 to 3, m2 is an integer from 1 to 4, When m1 is 2 or greater, each R 17 are the same as or different from each other, and when m2 is 2 or greater, each R 18 are the same as or different from each other.

2. The compound for an organic optoelectronic device according to claim 1, wherein Chemical Formula 1A is represented by any one of Chemical Formula 1A-1 to Chemical Formula 1A-4: In Chemical Formula 1A-1 to Chemical Formula 1A-4, R 1 to R 18 、Ar 1 , m1 and m2 are as defined in claim 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein Chemical Formula 1B is represented by any one of Chemical Formula 1B-1 to Chemical Formula 1B-4: In Chemical Formulas 1B-1 to 1B-4, R 1 to R 18 、Ar 1 , m1 and m2 are as defined in claim 1.

4. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

5. The compound for an organic optoelectronic device according to claim 1, wherein R 1 to R 13 、R 17 and R 18 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group.

6. 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] (Dn refers to the number of substituted deuterium atoms and represents a structure in which one or more deuterium atoms are substituted).

7. A composition for an organic optoelectronic device, comprising a first compound and a second compound, wherein the first compound is the compound for an organic optoelectronic device according to claim 1, and The second compound is represented by Chemical Formula 2, a combination of Chemical Formula 3 and Chemical Formula 4, or Chemical Formula 5: [Chemical Formula 2] In Chemical Formula 2, R 19 to R 23 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, Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 1 and L 2 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 an integer from 1 to 3, and n is an integer from 0 to 2; In Chemical Formula 3 and Chemical Formula 4, a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R a , Among a1* to a4* in Chemical Formula 3, adjacent two are each connected to * in Chemical Formula 4, L a 、L 4 and L 5 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a 、R 24 and R 25 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, Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m8 and m9 are each independently an integer from 1 to 4; [Chemical Formula 5] In Chemical Formula 5, L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 26 to R 29 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, Ar 6 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m10, m12 and m13 are each independently an integer from 1 to 4, m11 is an integer from 1 to 3, When m10 is 2 or greater, each R 26 are the same as or different from each other, When m11 is 2 or greater, each R 27 are the same as or different from each other, When m12 is 2 or greater, each R 28 are the same as or different from each other, When m13 is 2 or greater, each R 29 are the same as or different from each other.

8. The composition for an organic optoelectronic device according to claim 7, wherein Chemical formula 2 is represented by Chemical formula 2-8: [Chemical Formula 2-8] In Chemical Formula 2-8, R 19 to R 22 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 an integer from 1 to 3, and L 1 -Ar 2 and L 2 -Ar 3 are each independently one of the substituents listed in Group I, [Group I] In Group I, R 30 to R 34 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl, or C6 to C12 aryl, m14 is an integer from 1 to 5, m15 is an integer from 1 to 4, m16 is an integer from 1 to 3, m17 is an integer of 1 or 2, m18 is an integer from 1 to 7, and * is the connection point.

9. The composition for an organic optoelectronic device according to claim 7, wherein The combination of Chemical Formula 3 and Chemical Formula 4 is represented by Chemical Formula 3C: [Chemical formula 3C] In Chemical Formula 3C, L a3 and L a4 is a single bond, R 24 、R 25 、R a3 and R a4 are each independently hydrogen, deuterium or C6 to C12 aryl, m8 and m9 are each independently an integer from 1 to 4, and L 4 -Ar 4 and L 5 -Ar 5 are each independently one of the substituents listed in Group I, [Group I] In Group I, R 30 to R 34 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl, or C6 to C12 aryl, m14 is an integer from 1 to 5, m15 is an integer from 1 to 4, m16 is an integer from 1 to 3, m17 is an integer of 1 or 2, m18 is an integer from 1 to 7, and * is the connection point.

10. An organic optoelectronic device comprising an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises The compound for an organic optoelectronic device according to any one of claims 1 to 6; or The composition for an organic optoelectronic device according to any one of claims 7 to 9. The organic optoelectronic device according to claim 10 , 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. 12 . A display device comprising the organic optoelectronic device according to claim 10 .

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