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

Abstract

The invention relates to a compound for an organic optoelectronic device, an organic optoelectronic device, and a display device. Specifically, the present invention provides a compound for an organic optoelectronic device represented by Chemical Formula 1 or Chemical Formula 2, an organic optoelectronic device comprising the same, and a display device.

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2023-0074708 filed in the Korean Intellectual Property Office on June 12, 2023, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The invention discloses a compound for an organic optoelectronic device, an organic optoelectronic device and a display device. Background Art

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

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

[0006] Examples of organic optoelectronic devices include organic photoelectric devices, organic light emitting diodes, organic solar cells, and organic photoconductors.

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

[0008] Some embodiments provide a compound for an organic optoelectronic device that can reduce driving voltage and achieve high efficiency and long lifespan.

[0009] Some embodiments provide an organic optoelectronic device including the compound for an organic optoelectronic device.

[0010] Some embodiments provide a display device including an organic optoelectronic device.

[0011] According to some embodiments, a compound for an organic optoelectronic device represented by Chemical Formula 1 or Chemical Formula 2 is provided.

[0012] [Chemical formula 1]

[0013]

[0014] [Chemical formula 2]

[0015]

[0016] In Chemical Formula 1 and Chemical Formula 2,

[0017] X 1 is O or S,

[0018] Among a1* to a4*, the adjacent two are connecting carbon atoms connected to *.

[0019] Among a1* to a4*, the other two not connected to * are each independently CL a -R a ,

[0020] L a and L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0021] R a and R 1 To R 5 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[0022] Ar 1 To Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0023] m1 is an integer from 1 to 3, and

[0024] D n represents the number of hydrogen substituted with deuterium, and n is an integer of 1 or more.

[0025] According to some embodiments, 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.

[0026] According to some embodiments, a display device including an organic optoelectronic device is provided.

[0027] It is possible to realize an organic optoelectronic device with high efficiency and long life while reducing the driving voltage. BRIEF DESCRIPTION OF THE DRAWINGS

[0028] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments.

[0029] <Description of symbols>

[0030] 100: Organic light-emitting diode

[0031] 105: Organic layer

[0032] 110: cathode

[0033] 120: Anode

[0034] 130: Luminous layer

[0035] 140: Hole transport zone

[0036] 150: Electron transport region DETAILED DESCRIPTION

[0037] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto and is defined by the scope of claims.

[0038] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, a halogen, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0039] In one example of the present invention, "substituted" means that at least one hydrogen of the 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 addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl or cyano. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl or cyano. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0040] As used herein, "unsubstituted" means that a hydrogen atom is not replaced with another substituent and that a hydrogen atom remains.

[0041] As used herein, "deuterium substitution (-D)" may include "tritium substitution (-T)".

[0042] As used herein, when a definition is not otherwise provided, "hetero" refers to a group including 1 to 3 heteroatoms selected from N, O, S, P and Si in one functional group and the rest are carbon.

[0043] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and may include a group in which all elements of the hydrocarbon aromatic portion have p-orbitals forming a conjugation, for example, phenyl, naphthyl, etc., a group in which two or more hydrocarbon aromatic portions may be linked by a σ bond, for example, biphenyl, terphenyl, quaterphenyl, etc., and a group in which two or more hydrocarbon aromatic portions are directly or indirectly fused to provide a non-aromatic fused ring, for example, fluorenyl, etc.

[0044] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0045] As used herein, "heterocyclic group" has the general concept of heteroaryl group, and may include at least one heteroatom selected from N, O, S, P and Si to replace carbon (C) in a cyclic compound such as an aryl group, a cycloalkyl group, a condensed ring thereof or a combination thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0046] For example, "heteroaryl" refers to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls are directly connected by a sigma bond, or when the heteroaryl includes two or more rings, the two or more rings may be fused. When the heteroaryl is a fused ring, each ring may include 1 to 3 heteroatoms.

[0047] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted The invention may include, but is not limited to, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0048] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furanyl, 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 unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazoline, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofuranofluorenyl, substituted or unsubstituted benzothiophenefluorenyl, or a combination thereof, but are not limited thereto.

[0049] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) level.

[0050] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and according to the lowest unoccupied molecular orbital (LUMO) level, electrons formed in the cathode can be easily injected into the light-emitting layer due to the conductive property and transported in the light-emitting layer.

[0051] Hereinafter, a compound for an organic optoelectronic device according to some embodiments will be described.

[0052] Chemical Formula 1 or Chemical Formula 2 represents a compound for an organic optoelectronic device according to some embodiments.

[0053] [Chemical formula 1]

[0054]

[0055] [Chemical formula 2]

[0056]

[0057] In Chemical Formula 1 and Chemical Formula 2,

[0058] X 1 is O or S,

[0059] Among a1* to a4*, the adjacent two are connecting carbon atoms connected to *.

[0060] Among a1* to a4*, the other two not connected to * are each independently CL a -R a ,

[0061] L a and L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0062] R a and R 1 To R 5 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[0063] Ar 1 To Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0064] m1 is an integer from 1 to 3, and

[0065] D n represents the number of hydrogen substituted with deuterium, and n is an integer of 1 or more.

[0066] The compound represented by Chemical Formula 1 or Chemical Formula 2 includes an indole dibenzopyran (or indole dibenzothiophene) skeleton, and has a structure in which a triazine is substituted at 1 or 4 positions of dibenzofuran (or dithiophene) in the indole dibenzopyran (or indole dibenzothiophene) skeleton. The compound with this structure has bipolar characteristics, which means that when an electric field is applied, they can accept both holes and electrons. Specifically, the electron cloud is widely diffused, so that it has a fast and stable electron migration characteristic. In addition, due to steric hindrance, the molecular structure has a large reorganization energy. Reorganization energy refers to the energy loss caused by the change in molecular structure arrangement when moving charges, and the smaller the reorganization energy, the faster the charge mobility. Therefore, holes and electrons can move quickly, thereby improving driving voltage, efficiency and life characteristics. In addition, it has a high glass transition temperature and can be deposited at a relatively low temperature, so that it has excellent thermal stability.

[0067] In addition, the lifespan improvement effect can be maximized by a structure in which at least one deuterium is substituted. When deuterium is substituted, due to lower zero-point energy and lower vibration energy compared to hydrogen-bonded compounds, the ground state energy can be reduced, the intermolecular interaction can be reduced, and the film can be prepared in an amorphous state, thereby using it to more effectively improve the heat resistance and lifespan of the organic light-emitting diode. Therefore, the lifespan can be significantly improved by deuterium substitution.

[0068] In Dn, "D" refers to deuterium, and "n" refers to the substitution number.

[0069] More specifically, Dn refers to the number of hydrogens included in the compound represented by Chemical Formula 1 or Chemical Formula 2 that are replaced by deuterium. For example, "D18" means that 18 of the hydrogens included in the compound represented by Chemical Formula 1 or Chemical Formula 2 are replaced by 18 deuteriums, "D19" means that 19 of the hydrogens included in the compound represented by Chemical Formula 1 or Chemical Formula 2 are replaced by 19 deuteriums, "D20" means that 20 of the hydrogens included in the compound represented by Chemical Formula 1 or Chemical Formula 2 are replaced by 20 deuteriums, and "D24" means that 24 of the hydrogens included in the compound represented by Chemical Formula 1 or Chemical Formula 2 are replaced by 24 deuteriums.

[0070] Some of hydrogen included in the compound represented by Chemical Formula 1 or Chemical Formula 2 may be substituted with deuterium, and all of hydrogen included in the compound represented by Chemical Formula 1 or Chemical Formula 2 may be substituted with deuterium.

[0071] The hydrogen included in the compound represented by Chemical Formula 1 or Chemical Formula 2 represents the "Ar 1 To Ar 3 " "L 1 To L 3 ”, “R1 To R 5 " "L a ” and “R a All the hydrogen present in .

[0072] When m1 is 2 or more, each R 1 Can be the same as or different from each other.

[0073] In some embodiments, the compound for an organic optoelectronic device may be represented by Chemical Formula 1A to Chemical Formula 1F and Chemical Formula 2A to Chemical Formula 2F.

[0074]

[0075]

[0076] In Chemical Formulae 1A to 1F and Chemical Formulae 2A to 2F,

[0077] X 1 , L 1 To L 3 ,Ar 1 To Ar 3 , R 1 To R 5 and m1 as defined in claim 1,

[0078] L a1 To L a4 Each independently of the above described L a The definition is the same as

[0079] R a1 To R a4 Each independently of the above described R a The definition is the same.

[0080] For example, the compound for an organic optoelectronic device may be represented by any one of Chemical Formula 1B, Chemical Formula 2B, and Chemical Formula 2E.

[0081] As a specific example, the compound for an organic optoelectronic device may be represented by Chemical Formula 1B.

[0082] For example, L 1 It may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0083] For example, Ar 1It 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 phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0084] For example, L 1 -Ar 1 The substituents listed in Group I may be selected.

[0085] [Group I]

[0086]

[0087] In Group I,

[0088] R 23 To R 25 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl,

[0089] m23 is an integer from 1 to 5,

[0090] m24 is an integer from 1 to 4,

[0091] m25 is an integer from 1 to 3, and

[0092] * is the connection point.

[0093] When m23 is 2 or more, each R 23 Can be the same as or different from each other.

[0094] When m24 is 2 or more, each R 24 Can be the same as or different from each other.

[0095] When m25 is 2 or more, each R 25 Can be the same as or different from each other.

[0096] For example, L a1 To L a4 , L 2 and L 3 Each may independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0097] For example, Ar 2 and Ar 3Each of the above groups may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0098] For example, L 2 -Ar 2 and L 3 -Ar 3 The substituents may be independently selected from the substituents listed in Group II.

[0099] [Group II]

[0100]

[0101] In Group II,

[0102] R 26 To R 28 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl,

[0103] m26 is an integer from 1 to 5,

[0104] m27 is an integer from 1 to 4,

[0105] m28 is an integer from 1 to 3, and

[0106] * is the connection point.

[0107] For example, R a1 To R a4 and R 1 To R 5 Each may independently be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, substituted or unsubstituted C2 to C18 heterocyclic group or a combination thereof.

[0108] For example, R a1 To R a4 and R 1 To R 5 Each of them may independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted carbazolyl group.

[0109] In some embodiments of the present invention, the deuterium substitution rate may be greater than or equal to 50%.

[0110] More specifically, the deuterium substitution rate may be greater than or equal to 60%, greater than or equal to 70%, greater than or equal to 80%, or greater than or equal to 90%.

[0111] In this specification, the deuterium substitution rate refers to the proportion of deuterium replacing hydrogen when the total number of positions in a compound where hydrogen can be replaced by deuterium is 100%. H The deuterium substitution rate is calculated by the integral value of the NMR peak or the molecular weight confirmation by LC / MS, etc. For example, the compound for an organic optoelectronic device represented by Chemical Formula 1 or Chemical Formula 2 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] (Dn refers to the number of hydrogens replaced by deuterium, and indicates a structure with one or more deuterium replacements)

[0120] The compound for an organic optoelectronic device may be a composition further including a dopant.

[0121] The dopant may be, for example, a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0122] The dopant is a material mixed in a small amount with a compound used for an organic optoelectronic device to cause light emission, 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.

[0123] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0124] [Chemical formula Z]

[0125] L 4 MX 2

[0126] In the chemical formula Z, M is a metal, L is 4 and X 2 are the same or different and are ligands that form a complex with M.

[0127] 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 4 and X 2 It may be, for example, a bidentate ligand.

[0128] By L 4 and X 2 Examples of the represented ligands may be selected from the chemical formulae listed in Group A, but are not limited thereto.

[0129] [Group A]

[0130]

[0131] In Group A,

[0132] R 300 To R 302 are each independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted by halogen or not, C6 to C30 aryl which may be substituted by C1 to C30 alkyl or not, or halogen, and

[0133] 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.

[0134] For example, it may include a dopant represented by Chemical Formula V.

[0135] [Chemical Formula V]

[0136]

[0137] In chemical formula V,

[0138] 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 ,

[0139] R 132 To R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0140] R 101 To R 116 At least one of them is a functional group represented by chemical formula V-1,

[0141] 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

[0142] 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,

[0143] [Chemical Formula V-1]

[0144]

[0145] In chemical formula V-1,

[0146] 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

[0147] * indicates a moiety attached to a carbon atom.

[0148] For example, a dopant represented by Chemical Formula Z-1 may be included.

[0149] [Chemical formula Z-1]

[0150]

[0151] In the chemical formula Z-1, rings A, B, C and D are independently 5-membered or 6-membered carbocyclic or heterocyclic rings;

[0152] R A , RB , R C and R D are independently mono-, di-, tri- or tetra-substituted or unsubstituted;

[0153] 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;

[0154] nA is 0 or 1;

[0155] When nA is 1, L E is selected from direct bonds, 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

[0156] R A , R B , R C , R D R, 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, carboxyl, ester, cyano, 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 represent oxygen or a direct bond, respectively.

[0157] The dopant according to some embodiments may be a platinum complex, and may be, for example, represented by Formula VI.

[0158] [Chemical Formula VI]

[0159]

[0160] In Chemical Formula VI,

[0161] X 100 Selected from O, S and NR131 ,

[0162] R 117 To R 131 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0163] R 132 To R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0164] R 117 To R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl, and

[0165] R 132 To R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0166] Hereinafter, an organic optoelectronic device using the above-mentioned compound for an organic optoelectronic device or the composition for an organic optoelectronic device will be described.

[0167] The organic optoelectronic device may be any device that converts electrical energy into light energy (or vice versa) without particular limitation, and may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, an organic photosensitive drum, and the like.

[0168] Herein, an organic light emitting diode is described as an example of an organic optoelectronic device with reference to the accompanying drawings.

[0169] Figure 1 is a cross-sectional view showing an organic light emitting diode according to some embodiments.

[0170] refer to Figure 1 , the organic light emitting diode 100 according to some embodiments 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 .

[0171] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc., or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0172] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0173] The organic layer 105 may include the above-described compound for an organic optoelectronic device.

[0174] The organic layer 105 includes a light emitting layer 130, and the light emitting layer 130 may include the above-mentioned compound for an organic optoelectronic device. For example, the compound for an organic optoelectronic device may be a phosphorescent host.

[0175] The composition further including a dopant can be, for example, a green light emitting composition.

[0176] The organic layer may include a charge transport region in addition to the light emitting layer.

[0177] The charge migration region may be, for example, a hole transport region 140 .

[0178] 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.

[0179] Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light emitting layer 130 and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer, and at least one of the compounds in group B may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0180] [Group B]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] (Dn refers to the number of hydrogens replaced by deuterium, and indicates a structure with one or more deuterium replacements)

[0187] In the hole transporting region 140, in addition to the compounds described above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds similar thereto can be used.

[0188] In addition, the charge migration region may be, for example, the electron transport region 150 .

[0189] 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.

[0190] 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 located 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.

[0191] [Group C]

[0192]

[0193]

[0194]

[0195]

[0196] Some embodiments may provide an organic light emitting diode including a light emitting layer as an organic layer.

[0197] Some embodiments may provide an organic light emitting diode including a light emitting layer and a hole transport region as an organic layer.

[0198] Some embodiments may provide an organic light emitting diode including a light emitting layer and an electron transport region as an organic layer.

[0199] As the organic layer 105, the organic light emitting diode according to some embodiments may include a hole transport region 140 and an electron transport region 150 in addition to the light emitting layer 130, such as Figure 1 shown.

[0200] 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 the above-mentioned organic layer in addition to the light emitting layer.

[0201] The organic light emitting diode 100 may be produced by forming an anode or a cathode on a substrate, forming an organic layer using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

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

[0203] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the present invention is not limited thereto.

[0204] 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.

[0205] (Preparation of Compounds for Organic Optoelectronic Devices)

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

[0207] [Reaction 1]

[0208]

[0209] Under nitrogen environment, 20g (77.73mmol) 12H-benzofuran [2,3-a] carbazole, 30.5g (194.33mmol) bromobenzene, 11.21g (116.6mmol) sodium tert-butoxide and 3.56g (3.89mmol) tri (dibenzylideneacetone) dipalladium were added to 130ml toluene, and then suspended therein, and 4.72ml (11.66mmol) tri-tert-butylphosphine was added thereto, and then refluxed and stirred for 12 hours. Subsequently, distilled water was added to the reaction solution, and the solid produced therein was filtered under reduced pressure and separated. The solid was recrystallized with toluene to obtain intermediate I-1 (29.8g, 80%).

[0210] HRMS (70 eV, EI+): theoretical value of m / z for C23H15NO: 333.1154, experimental value: 333.

[0211] Elemental analysis: C, 86%; H, 5%

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

[0213] [Reaction 2]

[0214]

[0215] Under nitrogen environment, 29.8g (89.39mmol) of intermediate I-1 was dissolved by adding 224ml tetrahydrofuran thereto, then cooled to -78°C and stirred. Subsequently, 42.9ml (107.26mmol) of 2.5M n-BuLi (in n-hexane) solution was slowly added thereto, and stirred at room temperature for 6 hours under nitrogen atmosphere. The obtained reaction solution was cooled to -78°C, and 25.22g (134.08mmol) of triisopropyl borate was slowly added thereto, and then stirred at room temperature for 6 hours under nitrogen atmosphere. After adding 223.5ml 2.0M hydrochloric acid aqueous solution thereto, the mixture was then stirred for 1 hour, and the solid produced therein was filtered under reduced pressure and separated. The obtained solid was dissolved in dimethyl chloride, and then recrystallized to obtain intermediate I-2 (50g, 55%).

[0216] HRMS (70 eV, EI+): theoretical value of m / z for C24H16BNO3: 377.1223, experimental value: 377.

[0217] Elemental analysis: C, 76%; H, 4%

[0218] Synthesis Example 3: Synthesis of Intermediate I-3

[0219] [Reaction 3]

[0220]

[0221] In a nitrogen environment, 12 g (31.9 mmol) of intermediate M-2 and 10 g (29.1 mmol) of 2-([1,1'-biphenyl]-4-yl)-4-chloro-6-phenyl-1,3,5-triazine were dissolved by adding 193 ml of tetrahydrofuran thereto, and 97 ml of an aqueous solution in which 10.1 g (72.7 mmol) of potassium carbonate was dissolved was added thereto, and then stirred. Subsequently, 1.68 g (1.45 mmol) of tetrakis (triphenylphosphine) palladium was added thereto, and then refluxed and stirred for 12 hours. After the reaction was completed, the solid produced therein was separated by reduced pressure filtration and recrystallized by dissolving in toluene to obtain intermediate I-3 (14 g, 75%).

[0222] HRMS (70 eV, EI+): theoretical value of m / z for C45H28N4O: 640.2263, experimental value: 640.

[0223] Elemental analysis: C, 84%; H, 4%

[0224] Synthesis Example 4: Synthesis of Compound A-3

[0225] [Reaction 4]

[0226]

[0227] In a nitrogen atmosphere, 14 g (21.9 mmol) of intermediate I-3, 9.6 ml (109.3 mmol) of trifluoromethanesulfonic acid and 200 ml (2185 mmol) of D6-benzene were added, followed by stirring at 80° C. for 24 hours under reflux. When the reaction was completed, an organic layer was obtained by adding pure water thereto, neutralized with a saturated potassium phosphate solution, concentrated and column purified to obtain compound A-3 (10 g, 71%).

[0228] Synthesis Example 5: Synthesis of Intermediate I-4

[0229] [Reaction 5]

[0230]

[0231] In the same manner as in Synthesis Example 3, Intermediate I-4 (20 g, yield: 79%) was obtained by using 10 g (23.81 mmol) of 2-([1,1′-biphenyl]-3-yl)-4-([1,1′-biphenyl]-4-yl)-6-chloro-1,3,5-triazine.

[0232] HRMS (70 eV, EI+): theoretical value of m / z for C51H32N4O: 716.2576, experimental value: 716.

[0233] Elemental analysis: C, 85%; H, 5%

[0234] Synthesis Example 6: Synthesis of Compound A-2

[0235] [Reaction 6]

[0236]

[0237] In the same manner as in Synthesis Example 4, Compound A-2 (18 g, 90%) was obtained by using 20 g (27.9 mmol) of Intermediate I-4.

[0238] Synthesis Example 7: Synthesis of Intermediate I-5

[0239] [Reaction 7]

[0240]

[0241] In a nitrogen environment, 50g (177.6mmol) of the intermediate of 7-bromo-1-chlorodibenzo [b, d] furan, 54.1g (213.1mmol) of 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bismuth (1,3,2-dioxaborane), 4.9g (5.3mmol) of tris (dibenzylideneacetone) dipalladium, 12.0g (42.6mmol) of tricyclohexylphosphine and 26.2g (266.4mmol) of potassium acetate were dissolved in 800ml of toluene and then refluxed at 120°C for 12 hours. After the reaction was completed, the organic layer was extracted by adding water to the reaction solution, treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-5 (40g, 69%).

[0242] HRMS (70 eV, EI+): theoretical value of m / z for C18H18BClO3: 328.1038, experimental value: 328.

[0243] Elemental analysis: C, 66%; H, 5%

[0244] Synthesis Example 8: Synthesis of Intermediate I-6

[0245] [Reaction formula 8]

[0246]

[0247] In the same manner as in Synthesis Example 3, Intermediate I-6 (30 g, 76%) was obtained by using 40 g (121.7 mmol) of Intermediate I-5 and 29.5 g (146.1 mmol) of 1-bromo-2-nitrobenzene.

[0248] HRMS (70 eV, EI+): theoretical value of m / z for C18H10ClO3: 323.0349, experimental value: 323.

[0249] Elemental analysis: C, 67%; H, 3%

[0250] Synthesis Example 9: Synthesis of Intermediate I-7

[0251] [Reaction formula 9]

[0252]

[0253] In a nitrogen environment, 30g (123.6mmol) of intermediate I-6 and 97.2g (370.7mmol) of triphenylphosphine were dissolved in 1000ml of 1,2-dichlorobenzene, then heated at 200°C for 12 hours and refluxed with stirring. When the reaction was complete, after adding water to the reaction solution, the mixture was extracted with dichloromethane, treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-7 (20g, 55%).

[0254] HRMS (70 eV, EI+): theoretical value of m / z for C18H10ClNO: 291.0451, experimental value: 291.

[0255] Elemental analysis: C, 74%; H, 3%

[0256] Synthesis Example 10: Synthesis of Intermediate I-8

[0257] [Reaction formula 10]

[0258]

[0259] In the same manner as in Synthesis Example 1, Intermediate I-8 (22 g, 87%) was obtained by using 20 g (68.6 mmol) of Intermediate I-7.

[0260] HRMS (70 eV, EI+): theoretical value of m / z for C24H14ClNO: 367.0764, experimental value: 367.

[0261] Elemental analysis: C, 78%; H, 4%

[0262] Synthesis Example 11: Synthesis of Intermediate I-9

[0263] [Reaction formula 11]

[0264]

[0265] In the same manner as in Synthesis Example 7, Intermediate I-9 (17 g, 62%) was obtained by using 22 g (59.8 mmol) of Intermediate I-8.

[0266] HRMS (70 eV, EI+): theoretical value of m / z for C30H26BNO3: 459.2006, experimental value: 459.

[0267] Elemental analysis: C, 78%; H, 6%

[0268] Synthesis Example 12: Synthesis of Intermediate I-10

[0269] [Reaction 12]

[0270]

[0271] In the same manner as in Synthesis Example 3, Intermediate I-10 (20 g, 84%) was obtained by using 17 g (37.0 mmol) of Intermediate I-9.

[0272] HRMS (70 eV, EI+): theoretical value of m / z for C45H28N4O: 640.2263, experimental value: 640.

[0273] Elemental analysis: C, 84%; H, 4%

[0274] Synthesis Example 13: Synthesis of Compound A-55

[0275] [Reaction 13]

[0276]

[0277] In the same manner as in Synthesis Example 4, compound A-55 (15 g, 75%) was obtained by using 20 g of intermediate I-10.

[0278] Synthesis Example 14: Synthesis of Intermediate I-11

[0279] [Reaction 14]

[0280]

[0281] In the same manner as in Synthesis Example 3, Intermediate I-11 (40 g, 76%) was obtained by using 30 g (174.0 mmol) of (2-chloro-6-hydroxyphenyl)boric acid and 52.4 g (174.0 mmol) of 1-bromo-3-fluoro-2-iodobenzene.

[0282] HRMS (70 eV, EI+): theoretical value of m / z for C12H7BrClFO: 299.9353, experimental value: 299.

[0283] Elemental analysis: C, 48%; H, 2%

[0284] Synthesis Example 15: Synthesis of Intermediate I-12

[0285] [Reaction 15]

[0286]

[0287] In a nitrogen environment, 40g (132.7mmol) of intermediate I-11 and 22g (159.2mmol) of potassium carbonate were dissolved in 1000ml of N-methyl-2-pyrrolidone, then heated at 200°C for 12 hours and refluxed with stirring. When the reaction was complete, after adding water to the reaction solution, the mixture was extracted with dichloromethane, treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-12 (25g, 67%).

[0288] HRMS (70 eV, EI+): theoretical value of m / z for C12H6BrClO: 279.9291, experimental value: 279.

[0289] Elemental analysis: C, 51%; H, 2%

[0290] Synthesis Example 16: Synthesis of Intermediate I-13

[0291] [Reaction 16]

[0292]

[0293] In the same manner as in Synthesis Example 1, Intermediate I-13 (21 g, 72%) was obtained by using 25 g (88.8 mmol) of Intermediate I-12 and 11.3 g (88.8 mmol) of 2-chloroaniline.

[0294] HRMS (70 eV, EI+): theoretical value of m / z for C18H11Cl2NO: 327.0218, experimental value: 327.

[0295] Elemental analysis: C, 66%; H, 3%

[0296] Synthesis Example 17: Synthesis of Intermediate I-14

[0297] [Reaction 17]

[0298]

[0299] In a nitrogen environment, 21g (64.0mmol) of intermediate I-13 was dissolved in 900ml N, N-dimethylacetamide (DMAc), and 0.7g (3.2mmol) of palladium acetate, 17.7g (128.0mmol) of potassium carbonate and 2.4g (6.4mmol) of tricyclohexylphosphine tetrafluoroborate were added thereto, and then heated at 200°C for 12 hours and refluxed with stirring. When the reaction was complete, an organic layer was extracted from the reaction solution by adding water thereto, treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-14 (10g, 54%).

[0300] HRMS (70 eV, EI+): theoretical value of m / z for C18H10ClNO: 291.0451, experimental value: 291.

[0301] Elemental analysis: C, 74%; H, 3%

[0302] Synthesis Example 18: Synthesis of Intermediate I-15

[0303] [Reaction 18]

[0304]

[0305] In a nitrogen environment, 10g (54.7mmol) of intermediate I-14, 21.0g (102.8mmol) of iodobenzene, 1.3g (6.9mmol) of cuprous iodide, 7.1g (51.4mmol) of potassium carbonate and 12.9g (51.4mmol) of 3,5-di-tert-butyl salicylic acid were dissolved in 350ml of dodecylbenzene, then heated at 180°C for 12 hours and refluxed with stirring. When the reaction was complete, an organic layer was extracted from the reaction solution by adding water thereto, treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-15 (10g, 79%).

[0306] HRMS (70 eV, EI+): theoretical value of m / z for C24H14ClNO: 367.0764, experimental value: 367.

[0307] Elemental analysis: C, 78%; H, 4%

[0308] Synthesis Example 19: Synthesis of Intermediate I-16

[0309] [Reaction 19]

[0310]

[0311] In the same manner as in Synthesis Example 7, Intermediate I-16 (8 g, 64%) was obtained by using 10 g (27.2 mmol) of Intermediate I-15.

[0312] HRMS (70 eV, EI+): theoretical value of m / z for C30H26BNO3: 459.2006, experimental value: 459.

[0313] Elemental analysis: C, 78%; H, 6%

[0314] Synthesis Example 20: Synthesis of Intermediate I-17

[0315] [Reaction 20]

[0316]

[0317] In the same manner as in Synthesis Example 3, Intermediate I-17 (9 g, 81%) was obtained by using 8 g (17.4 mmol) of Intermediate I-16.

[0318] HRMS (70 eV, EI+): theoretical value of m / z for C45H28N4O: 640.2263, experimental value: 640.

[0319] Elemental analysis: C, 84%; H, 4%

[0320] Synthesis Example 21: Synthesis of Compound A-131

[0321] [Reaction 21]

[0322]

[0323] In the same manner as in Synthesis Example 4, compound A-131 (8 g, 89%) was obtained by using 9 g of intermediate I-17.

[0324] Comparative Synthesis Example 1: Synthesis of Intermediate I-18

[0325] [Reaction 22]

[0326]

[0327] In the same manner as in Synthesis Example 1, Intermediate I-18 (25 g, 86%) was obtained by using 25 g (88.8 mmol) of 6-bromo-2-chlorodibenzo[b,d]furan and 11.3 g (88.8 mmol) of 2-chloroaniline.

[0328] HRMS (70 eV, EI+): theoretical value of m / z for C18H11Cl2NO: 327.0218, experimental value: 327.

[0329] Elemental analysis: C, 66%; H, 3%

[0330] Comparative Synthesis Example 2: Synthesis of Intermediate I-19

[0331] [Reaction 23]

[0332]

[0333] In the same manner as in Synthesis Example 17, Intermediate I-19 (18 g, 81%) was obtained by using 25 g (76.2 mmol) of Intermediate I-18.

[0334] HRMS (70 eV, EI+): theoretical value of m / z for C18H10ClNO: 291.0451, experimental value: 291.

[0335] Elemental analysis: C, 74%; H, 3%

[0336] Comparative Synthesis Example 3: Synthesis of Intermediate I-20

[0337] [Reaction 24]

[0338]

[0339] In the same manner as in Synthesis Example 1, Intermediate I-20 (20 g, 88%) was obtained by using 18 g (61.7 mmol) of Intermediate I-19 and 14.5 g (92.6 mmol) of bromobenzene.

[0340] HRMS (70 eV, EI+): theoretical value of m / z for C24H14ClNO: 367.0764, experimental value: 367.

[0341] Elemental analysis: C, 78%; H, 4%

[0342] Comparative Synthesis Example 4: Synthesis of Intermediate I-21

[0343] [Reaction 25]

[0344]

[0345] In the same manner as in Synthesis Example 7, Intermediate I-21 (19 g, 76%) was obtained by using 20 g (54.4 mmol) of Intermediate I-20.

[0346] HRMS (70 eV, EI+): theoretical value of m / z for C30H26BNO3: 459.2006, experimental value: 459.

[0347] Elemental analysis: C, 78%; H, 6%

[0348] Comparative Synthesis Example 5: Synthesis of Intermediate I-22

[0349] [Reaction 26]

[0350]

[0351] In the same manner as in Synthesis Example 4, Intermediate I-22 (17 g, 82%) was obtained by using 20 g (74.7 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine.

[0352] HRMS (70 eV, EI+): theoretical value of m / z for C15D10ClN3: 277.1191, experimental value: 277.

[0353] Elemental analysis: C, 65%; H, 7%

[0354] Comparative Synthesis Example 6: Synthesis of Compound R-1

[0355] [Reaction 27]

[0356]

[0357] In the same manner as in Synthesis Example 3, Compound R-1 (20 g, 84%) was obtained by using 19 g (41.4 mmol) of Intermediate I-21 and 17 g (62.0 mmol) of Intermediate I-22.

[0358] HRMS (70 eV, EI+): theoretical value of m / z for C39H14D10N4O: 574.2578, experimental value: 574.

[0359] Elemental analysis: C, 82%; H, 6%

[0360] Comparative Synthesis Example 7: Synthesis of Intermediate I-23

[0361] [Reaction 28]

[0362]

[0363] In the same manner as in Synthesis Example 4, Intermediate I-23 (14 g, 70%) was obtained by using 20 g (73.2 mmol) of 12H-benzo[4,5]thieno[2,3-a]carbazole.

[0364] HRMS (70 eV, EI+): theoretical value of m / z for C18HD10NS: 283.1240, experimental value: 283.

[0365] Elemental analysis: C, 76%; H, 7%

[0366] Comparative Synthesis Example 8: Synthesis of Compound R-2

[0367] [Reaction 29]

[0368]

[0369] In a nitrogen environment, 14g (49.4mmol) of intermediate I-23 was dissolved in 500ml of N,N-dimethylformamide. 1.8g (74.1mmol) of sodium hydride was added thereto, and then stirred for 30 minutes. 19.8g (74.1mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine was added thereto, and then stirred at room temperature for 12 hours. After the reaction was completed, a solid was produced by adding pure water thereto, and then filtered under reduced pressure and separated. The solid was dissolved in 19.8g (74.1mmol) of toluene for recrystallization to obtain compound R-2 (18g, 71%).

[0370] HRMS (70 eV, EI+): theoretical value of m / z for C33H10D10N4S: 514.2036, experimental value: 514.

[0371] Elemental analysis: C, 77%; H, 6%

[0372] Comparative Synthesis Example 9: Synthesis of Intermediate I-24

[0373] [Reaction formula 30]

[0374]

[0375] In the same manner as in Synthesis Example 1, intermediate I-24 (25 g, 95%) was obtained using 20 g (77.73 mmol) of 12H-benzofurano[2,3-a]carbazole, 30.5 g (194.33 mmol) of bromobenzene and 15.1 g (93.3 mmol) of 1-bromobenzene-2,3,4,5,6-d5.

[0376] HRMS (70 eV, EI+): theoretical value of m / z for C24H10D5NO: 338.1467, experimental value: 338.

[0377] Elemental analysis: C, 85%; H, 6%

[0378] Comparative Synthesis Example 10: Synthesis of Intermediate I-25

[0379] [Reaction 31]

[0380]

[0381] In the same manner as in Synthesis Example 2, Intermediate I-25 (20 g, 71%) was obtained using 25 g (73.9 mmol) of Intermediate I-24.

[0382] HRMS (70 eV, EI+): theoretical value of m / z for C24H10D5NO: 338.1467, experimental value: 338.

[0383] Elemental analysis: C, 85%; H, 6%

[0384] Comparative Synthesis Example 11: Synthesis of Compound R-3

[0385] [Reaction 32]

[0386]

[0387] In the same manner as in Synthesis Example 25, Compound R-3 (30 g, 89%) was obtained using 20 g (52.3 mmol) of Intermediate I-25.

[0388] HRMS (70 eV, EI+): theoretical value of m / z for C45H23D5N4O: 645.2577, experimental value: 645.

[0389] Elemental analysis: C, 84%; H, 5%

[0390] Production of organic light-emitting diodes

[0391] Example 1

[0392] The ITO (indium tin oxide) coated glass substrate was ultrasonically cleaned with distilled water. 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 by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. This prepared ITO transparent electrode was used as an anode, and compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form - a thick hole injection layer, and depositing compound A on the hole injection layer to The hole transport layer is formed by vacuum deposition of compound B. The hole transport auxiliary layer is formed by using the compound A-3 synthesized in Synthesis Example 4 as a host on the hole transport auxiliary layer and doped with 7 wt % of PhGD as a dopant to form -thick light-emitting layer. In the following examples and comparative examples, this ratio is described separately. Subsequently, compound C is deposited to form a -thick electron transport auxiliary layer, and compound D and LiQ are simultaneously vacuum deposited at a weight ratio of 1:1 to form -thick electron transport layer. On the electron transport layer, Liq and Al are vacuum deposited sequentially to -Houhe -thick, thus producing an organic light-emitting diode.

[0393] The structure is ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[Compound A-3 (93 wt%):PhGD (7 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-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0398] [PhGD]

[0399]

[0400] Example 2 and Comparative Examples 1 to 3

[0401] An organic light emitting diode was produced in the same manner as in Example 1, except that the compositions were changed to those shown in Tables 1 and 2.

[0402] evaluate

[0403] The luminous efficiency and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 2 and Comparative Examples 1 to 3 were evaluated.

[0404] The specific measurement method is described below, and the results are shown in Table 2.

[0405] (1) Measuring the change in current density due to voltage change

[0406] The resulting organic light emitting diode was measured for a current value flowing into a unit diode while increasing a voltage from 0 V to 10 V using a voltammeter (Keithley 2400), and the measured current value was divided by an area to provide a result.

[0407] (2) Measuring the change in brightness due to voltage changes

[0408] While the voltage of the organic light emitting diode was increased from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).

[0409] (3) Measurement of luminous efficiency

[0410] Using the luminance, current density and voltage measured according to (1) and (2) above, at the same current density (10 mA / cm 2 )Calculate the current efficiency (cd / A).

[0411] The luminous efficiency values ​​of Example 1 and Comparative Examples 1 to 2 were calculated based on Comparative Example 1 as relative values ​​and are listed in Table 1.

[0412] (4) Lifespan measurement

[0413] By converting the brightness (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 drop to 95%.

[0414] The life measurements of Examples 1 to 2 and Comparative Examples 1 and 3 were calculated based on Comparative Example 1 as relative values ​​and are listed in Table 2.

[0415] (Table 1)

[0416] serial number main body efficiency(%) Example 1 A-3 106％ Comparative Example 1 R-1 100％ Comparative Example 2 R-2 100％

[0417] (Table 2)

[0418] serial number main body Lifespan T95(%) Example 1 A-3 111％ Example 2 A-2 113％ Comparative Example 1 R-1 100％ Comparative Example 3 R-3 104％

[0419] Referring to Table 1, the luminous efficiency of the organic light-emitting diode according to Example 1 is significantly improved compared to the organic light-emitting diodes according to Comparative Examples 1 and 2. The compound disclosed in Example 1 is different from the compounds disclosed in Comparative Examples 1 and 2 in terms of triazine binding sites. The molecular structure has a higher reorganization energy value than the structure of the present invention. Reorganization energy refers to the energy loss caused by changes in the arrangement of the molecular structure when moving charges, and the smaller the reorganization energy, the faster the charge mobility. Due to these characteristics, Example 1 shows high-efficiency characteristics. In addition, referring to Table 2, when deuterium substitution exceeds a specific ratio compared to the organic light-emitting diodes according to Comparative Examples 1 and 3, the lifespan of the organic light-emitting diodes according to Examples 1 and 2 is significantly improved.

[0420] While the invention has been described in conjunction with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A compound for an organic optoelectronic device, represented by Chemical Formula 1 or Chemical Formula 2: [Chemical formula 1] [Chemical formula 2] In Chemical Formula 1 and Chemical Formula 2, X 1 is O or S, Among a1* to a4*, the adjacent two are connecting carbon atoms connected to *. Among a1* to a4*, the other two not connected to * are each independently CL a -R a , L a and L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a and R 1 To R 5 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 1 To Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m1 is an integer from 1 to 3, and D n represents the number of hydrogen substituted with deuterium, and n is an integer of 1 or more.

2. The compound for an organic optoelectronic device according to claim 1, wherein The compound is represented by any one of Chemical Formula 1A to Chemical Formula 1F and Chemical Formula 2A to Chemical Formula 2F: In Chemical Formulae 1A to 1F and Chemical Formulae 2A to 2F, X 1 , L 1 To L 3 ,Ar 1 To Ar 3 , R 1 To R 5and m1 as defined in claim 1, L a1 To L a4 Each independently of L defined in claim 1 a The definition of is the same, and R a1 To R a4 Each independently of R defined in claim 1 a The definition is the same.

3. The compound for an organic optoelectronic device according to claim 2, wherein The compound is represented by any one of Chemical Formula 1B, Chemical Formula 2B, and Chemical Formula 2E.

4. The compound for an organic optoelectronic device according to claim 2, wherein The compound is represented by Chemical Formula 1B.

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

6. The compound for an organic optoelectronic device according to claim 1, wherein L 1 -Ar 1 is one of the substituents selected from Group I, [Group I] In Group I, R 23 To R 25 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl, m23 is an integer from 1 to 5, m24 is an integer from 1 to 4, m25 is an integer from 1 to 3, and * is the connection point.

7. The compound for an organic optoelectronic device according to claim 1, wherein Ar 2 and Ar 3Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

8. The compound for an organic optoelectronic device according to claim 1, wherein L 2 -Ar 2 and L 3 -Ar 3 Each is independently selected from the substituents listed in Group II: [Group II] In Group II, R 26 To R 28 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl, m26 is an integer from 1 to 5, m27 is an integer from 1 to 4, m28 is an integer from 1 to 3, and * is the connection point.

9. The compound for an organic optoelectronic device according to claim 1, wherein The deuterium substitution rate is greater than or equal to 50%.

10. The compound for an organic optoelectronic device according to claim 1, wherein The compound is one selected from the compounds listed in Group 1: [Group 1] 11. An organic optoelectronic device comprising an anode and a cathode opposite each other, and at least one organic layer located between the anode and the cathode, The organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 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. 13 . A display device comprising the organic optoelectronic device according to claim 11 .

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