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

Abstract

The present invention relates to a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device and a display device. Specifically, the present invention provides a compound for an organic optoelectronic device represented by Chemical Formula 1, a composition for an organic optoelectronic device, an organic optoelectronic device and a display device containing the same. The details of Chemical Formula 1 are as defined in the specification.

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefits of Korean Patent Application No. 10-2021-0117780 filed in the Korean Intellectual Property Office on September 3, 2021, and Korean Patent Application No. 10-2022-0110105 filed in the Korean Intellectual Property Office on August 31, 2022, the entire contents of which are incorporated herein by reference. Technical Field

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

[0004] An organic photoelectric device (organic photodiode) is a device capable of converting electrical energy and light energy into each other.

[0005] Organic optoelectronic devices can be classified as follows according to their driving principles. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively, and the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0006] Examples of the organic optoelectronic device include an organic optoelectronic element, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

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

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

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

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

[0011] Another embodiment provides a display device including an organic optoelectronic device.

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

[0013] [Chemical formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] m1 and m2 are each independently an integer of 0 or 1,

[0017] X 1 and X 2 Each is independently NR g , O, S, CR a R b or SiR c R d ,

[0018] n1 is an integer from 1 to 5,

[0019] Z 1 To Z 6 Each independently is N or CR e ,

[0020] Z 1 To Z 3 At least two of them are N; Z 4 To Z 6 At least two of them are N; or Z 1 To Z 3 At least two of them are N and Z 4 To Z 6 At least two of them are N,

[0021] R a , R b , R c , R d and R g are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0022] R e and R 1 To R 4 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0023] m6 and m8 are each independently an integer from 1 to 4,

[0024] m7 is an integer from 1 to 4,

[0025] m9 is an integer from 1 to 3,

[0026] Ar 1 and Ar 2are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0027] L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0028] According to another embodiment, provided is a composition for an organic optoelectronic device including a first compound and a second compound.

[0029] The first compound is the same as described above, and the second compound may be a compound for an organic photoelectric device represented by Chemical Formula 2; or a compound for an organic photoelectric device represented by a combination of Chemical Formula 3 and Chemical Formula 4.

[0030] [Chemical formula 2]

[0031]

[0032] In chemical formula 2,

[0033] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0034] L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0035] R 6 To R 16 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,

[0036] m3 and m4 are each independently an integer from 1 to 3,

[0037] m5 is an integer from 1 to 4, and

[0038] n2 is an integer from 0 to 2;

[0039]

[0040]

[0041] Among them, in Chemical Formula 3 and Chemical Formula 4,

[0042] Ar 5 and Ar6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0043] Two adjacent ones of b1* to b4* in Chemical Formula 3 are connected to the carbon (C) of * in Chemical Formula 4.

[0044] The other two of b1* to b4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are each independently CL d -R f ,

[0045] L d , L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0046] R f and R 17 To R 24 Each is 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 heterocyclyl.

[0047] According to another embodiment, an organic photoelectric device includes an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the organic layer includes a compound for an organic photoelectric device or a composition for an organic photoelectric device.

[0048] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0049] An organic photoelectric device with high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0050] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment. DETAILED DESCRIPTION

[0051] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0052] In one example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.

[0053] In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or a compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0054] "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and that a hydrogen atom remains.

[0055] As used herein, "hydrogen substitution (-H)" may include deuterium substitution (-D) or "tritium substitution (-T)".

[0056] As used herein, when no definition is otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon atoms in one functional group.

[0057] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and all elements of the hydrocarbon aromatic portion have p orbitals forming conjugation, such as phenyl, naphthyl, etc., two or more hydrocarbon aromatic portions may be connected by a σ bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic portions are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0058] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0059] As used herein, "heterocyclic group" is a general concept of heteroaryl groups, and may contain at least one heteroatom selected from N, O, S, P, and Si to replace carbon (C) in cyclic compounds such as aryl groups, cycloalkyl groups, condensed rings thereof, or combinations thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0060] 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 connected by a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0061] 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 naphthyl group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted para-terphenyl group, a substituted or unsubstituted meta-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0062] 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 benzothiophenyl, A substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazoline, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazinyl, a substituted or unsubstituted acridinyl, a substituted or unsubstituted phenazinyl, a substituted or unsubstituted phenothiazinyl, a substituted or unsubstituted phenoxazinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl, or a combination thereof, but is not limited thereto.

[0063] In this specification, hole characteristics refer to the ability to donate electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) level, holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0064] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and electrons formed in the cathode can be easily injected into the light emitting layer and transported in the light emitting layer due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) level.

[0065] Hereinafter, a compound for an organic photoelectric device according to one embodiment is described.

[0066] The compound for an organic photoelectric device according to one embodiment is represented by Chemical Formula 1.

[0067] [Chemical formula 1]

[0068]

[0069] In Chemical Formula 1,

[0070] m1 and m2 are each independently an integer of 0 or 1,

[0071] X 1 and X 2 Each is independently NR g , O, S, CR a R b or SiR c R d ,

[0072] n1 is an integer from 1 to 5,

[0073] Z 1 To Z 6 Each independently is N or CR e ,

[0074] Z 1 To Z 3 At least two of them are N; Z 4 To Z 6 At least two of them are N; or Z 1 To Z 3 At least two of them are N and Z 4 To Z 6 At least two of them are N,

[0075] R a , R b , R c , R d and R gare each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0076] R e and R 1 To R 4 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0077] m6 and m8 are each independently an integer from 1 to 4,

[0078] m7 is an integer from 1 to 4,

[0079] m9 is an integer from 1 to 3,

[0080] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0081] L 1 and L 2 Each is independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0082] The compound represented by Chemical Formula 1 is a macrocyclic bipolar compound, and has a disordered spatial structure compared to a structure not including a macrocyclic skeleton, so that the molecular freedom is reduced, and thus the molecules are arranged in a specific direction, the intermolecular orientation is increased to increase the intermolecular electron and hole mobility, and exhibits relatively high efficiency. In addition, the macrocyclic skeleton suppresses the molecular freedom, and its molecular structure and energy show a small reorganization with a small difference between the excited state and the ground state, and exhibits a longer life compared to non-macrocyclic.

[0083] For example, Chemical Formula 1 may be represented by any one of Chemical Formula 1A to Chemical Formula 1D.

[0084]

[0085] In Chemical Formulae 1A to 1D,

[0086] Ar 1 ,Ar 2 , L 1 , L 2 , X 1 , X 2 , Z 1 To Z 6 , n1, m6 to m9 and R 1 To R 4 Same as above,

[0087] m7' is an integer from 1 to 3,

[0088] m7" is an integer of 1 or 2, and

[0089] m9' is an integer of 1 or 2.

[0090] For example, Chemical Formula 1 may be represented by any one of Chemical Formula 1-I, Chemical Formula 1-II, and Chemical Formula 1-III.

[0091]

[0092]

[0093] In Chemical Formula 1-I, Chemical Formula 1-II and Chemical Formula 1-III,

[0094] Ar 1 ,Ar 2 , L 1 , L 2 , X 1 , X 2 、m1、m2、m6 to m9、Z 1 To Z 6 , n1 and R 1 To R 4 Same as above.

[0095] For example, n1 may be one of integers of 1 to 3, and for example, Chemical Formula 1 may be represented by any one of Chemical Formula 1-IIa, Chemical Formula 1-IIb, and Chemical Formula 1-IIc.

[0096]

[0097]

[0098] In Chemical Formula 1-IIa, Chemical Formula 1-IIb and Chemical Formula 1-IIc,

[0099] Ar 1 ,Ar 2 , L 1 , L 2 , X 1 , X 2 、m1、m2、m6 to m9、Z 1 To Z 6 and R 1 To R 4 Same as above,

[0100] R 1a , R 1b and R 1c With R as above1 Same definition.

[0101] For example, m1 and m2 may each be 0.

[0102] For example, m1 can be 0 and m2 can be 1. In this case, X 2 It can be NR g , O, S, CR a R b or SiR c R d , and R a , R b , R c , R d and R g Each may independently be a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0103] For example, m2 can be 0 and m1 can be 1. In this case, X 1 YesNR g , O, S, CR a R b or SiR c R d , and R a , R b , R c , R d and R g Each may independently be a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0104] For example, m1 and m2 can each be 1, in which case X 1 and X 2 Can be NR independently g , O, S, CR a R b or SiR c R d , and R a , R b , R c , R d and R g Each of R and R may be independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group. g It may be phenyl.

[0105] For example, X 1 and X 2 can each independently be O or S.

[0106] For example, Z1 To Z 3 can be N, and Z 4 To Z 6 Can be independently CR e . R e Same as above, and may be the same as or different from each other.

[0107] For example, Z 4 To Z 6 Each can be N, and Z 1 To Z 3 Each can be CR independently e . R e Same as above, and may be the same as or different from each other.

[0108] For example, Z 1 To Z 6 Each can be N.

[0109] For example, R e and R 1 To R 4 Each may independently be hydrogen, deuterium, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0110] For example, R e and R 1 To R 4 Each may independently be hydrogen, substituted or unsubstituted C1 to C5 alkyl, or substituted or unsubstituted phenyl.

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

[0112] For example, L 1 and L 2 Each may independently be a single bond, or a substituted or unsubstituted C6 to C18 arylene group.

[0113] In a more specific example, *-L 1 -Ar 1 and *-L 2 -Ar 2 The groups may be independently selected from group I.

[0114] [Group I]

[0115]

[0116] In group I, * is the connection point, and

[0117] The groups of group I may be unsubstituted or substituted with other substituents. The substituents are the same as described above. For example, these substituents may be selected from deuterium, C1 to C10 alkyl groups and C6 to C12 aryl groups.

[0118] The most specific examples of the compound for an organic photoelectric device represented by Chemical Formula 1 may include compounds of Group 1, but are not limited thereto.

[0119] [Group 1]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125] In Group 1, D0 means that hydrogen is not replaced by deuterium.

[0126] D1 means that a hydrogen is replaced by a deuterium.

[0127] D2 means that a hydrogen is replaced by two deuteriums.

[0128] D3 means that hydrogen is replaced by three deuteriums.

[0129] D4 means that hydrogen is replaced by four deuteriums.

[0130] D5 means that hydrogen is replaced by five deuteriums.

[0131] D0 to D2 means that 0 to 2 deuteriums may be substituted.

[0132] D0 to D3 means that 0 to 3 deuteriums may be substituted.

[0133] D0 to D4 means that 0 to 4 deuteriums may be substituted.

[0134] D0 to D5 means that 0 to 5 deuteriums may be substituted.

[0135] A composition for an organic photoelectric device according to another embodiment includes a first compound and a second compound, wherein the first compound is the above-mentioned compound for an organic photoelectric device, and the second compound may be a compound for an organic photoelectric device represented by Chemical Formula 2; or a compound for an organic photoelectric device represented by a combination of Chemical Formula 3 and Chemical Formula 4.

[0136] [Chemical formula 2]

[0137]

[0138] In chemical formula 2,

[0139] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0140] L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0141] R 6 To R 16 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,

[0142] m3 and m4 are each independently an integer from 1 to 3,

[0143] m5 is an integer from 1 to 4, and

[0144] n2 is an integer from 0 to 2;

[0145]

[0146] Among them, in Chemical Formula 3 and Chemical Formula 4,

[0147] Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0148] Two adjacent ones of b1* to b4* in Chemical Formula 3 are connected to the carbon (C) of * in Chemical Formula 4.

[0149] The other two of b1* to b4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are each independently CL d -R f ,

[0150] L d , L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0151] R f and R 17 To R 24 Each is 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 heterocyclyl.

[0152] The second compound may be used in the light emitting layer together with the first compound to increase charge mobility and improve stability, thereby improving light emitting efficiency and lifespan characteristics.

[0153] For example, in Formula 2, Ar 3 and Ar 4 each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group,

[0154] In chemical formula 2, L 3 and L 4 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0155] In chemical formula 2, R 6 To R 16 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0156] n2 can be 0 or 1.

[0157] For example, “substituted” in Chemical Formula 2 means that at least one hydrogen is replaced by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0158] In one embodiment of the present invention, Chemical Formula 2 can be composed of Chemical Formula 2-1 to Chemical Formula

[0159] One of the expressions in formula 2-15.

[0160]

[0161]

[0162] In Chemical Formulae 2-1 to 2-15, R 6 To R 16 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and *-L 3 -Ar 3 and *-L 4 -Ar 4 Each may independently be one of the substituents in Group II.

[0163] [Group II]

[0164]

[0165] In group II, * is a point of attachment, and the group of group II may be unsubstituted or substituted by other substituents. The substituents are the same as described above. For example, the substituents may be selected from deuterium, C1 to C4 alkyl, C6 to C18 aryl, and C2 to C30 heteroaryl.

[0166] In one embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0167] In addition, *-L in Chemical Formula 2-8 3 -Ar 3 and *-L 4 -Ar 4 Each may be independently selected from Group II, and may be, for example, any one of C-1, C-2, C-3, C-4, C-7, C-8 or C-9.

[0168] For example, the second compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 may be represented by any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0169]

[0170] In Chemical Formulae 3A to 3E, Ar 5 ,Ar 6 , L 5 , L 6 and R 17 To R 24 Same as above,

[0171] L d1 To L d4 With the above L 5 and L 6 The definition is the same as

[0172] R f1 To R f4 With the same R 17 To R 24Same definition.

[0173] For example, in Formulas 3 and 4, Ar 5 and Ar 6 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group,

[0174] R f1 To R f4 and R 17 To R 24 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.

[0175] In one embodiment of the present invention, in Chemical Formula 3 and Chemical Formula 4, *-L 5 -Ar 5 and *-L 6 -Ar 6 The substituents may be each independently selected from group II.

[0176] In an example embodiment, R f1 To R f4 and R 17 To R 24 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.

[0177] For example, R f1 To R f4 and R 17 To R 24 may each independently be hydrogen, deuterium, cyano or substituted or unsubstituted phenyl, and

[0178] In a specific example embodiment, R f1 To R f4 and R 17 To R 24 can each independently be hydrogen, deuterium or phenyl.

[0179] In a specific embodiment of the present invention, the second compound can be represented by Chemical Formula 2-8, wherein in Chemical Formula 2-8, Ar 3 and Ar 4may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, L 3 and L 4 Each may independently be a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and R6 to R16 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 dibenzothiophene.

[0180] In another specific embodiment of the present invention, the second compound can be represented by Chemical Formula 3C, wherein in Chemical Formula 3C, L f1 To L f4 can be a single bond, and L 5 and L 6 may be each independently a single bond, or a substituted or unsubstituted C6 to C12 arylene group, R 17 To R 24 and R f1 To R f4 may each be hydrogen, deuterium or phenyl, and Ar 5 and Ar 6 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0181] For example, the second compound may be one of the compounds selected from Group 2, but is not limited thereto.

[0182] [Group 2]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198] For example, the first compound and the second compound may be included in a weight ratio of about 1:99 to about 99:1. Within the above range, the electron transport ability of the first compound and the hole transport ability of the second compound may be used to adjust the appropriate weight ratio to achieve bipolar characteristics and improve efficiency and lifespan. Within the above range, for example, they may be about 10:90 to about 90:10, about 20:80 to about 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 about 40:60, about 50:50, or about 60:40.

[0199] The composition may further comprise one or more compounds in addition to the above-mentioned first and second compounds.

[0200] The above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device may be a composition further including a dopant.

[0201] 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.

[0202] A dopant is a material that emits light by mixing in small amounts with a compound or composition for an organic optoelectronic device. Typically, a dopant can be a material such as a metal complex that emits light by multiple excitations to a triplet state or more. A dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and can include one, two, or more.

[0203] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may include 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 use, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0204] [Chemical formula Z]

[0205] L 7 MX 3

[0206] In the chemical formula Z, M is a metal and L 7 and X 3 They are the same as or different from each other and are ligands that form a complex with M.

[0207] 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 15 and X 5 This may be, for example, a bidentate ligand.

[0208] By L 7 and L 7 Examples of the ligand represented may be selected from the chemical formulae of Group A, but are not limited thereto.

[0209] [Group A]

[0210]

[0211]

[0212] In Group A,

[0213] R 300 To R 302 are each independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted with halogen, C6 to C30 aryl which may be substituted with C1 to C30 alkyl, or halogen, and

[0214] 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.

[0215] As an example, a dopant represented by Chemical Formula I may be included.

[0216] [Chemical Formula I]

[0217]

[0218] In Chemical Formula I,

[0219] 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 ,

[0220] R 132 To R 134 are each independently C1 to C6 alkyl,

[0221] R 101 To R 116 At least one of them is a functional group represented by Chemical Formula I-1,

[0222] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone pair of electrons or a heteroatom, and

[0223] 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,

[0224] [Chemical Formula I-1]

[0225]

[0226] Wherein, in Chemical Formula I-1,

[0227] 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 ,as well as

[0228] * indicates a moiety attached to a carbon atom.

[0229] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0230] [Chemical formula Z-1]

[0231]

[0232] In the chemical formula Z-1, rings A, B, C and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0233] R A , RB , R C and R D each independently mono-, di-, tri-, or tetra-substituted, or unsubstituted;

[0234] L B , L C and L D Each is independently selected from a single bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0235] When nA is 1, L E is selected from a single bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E does not exist; and

[0236] R A , R B , R C , R D R, R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino and combinations thereof; any adjacent R A , R B , R C , R D , R and R' are optionally linked to each other to provide a ring; X B , X C , X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Each represents oxygen or a single bond.

[0237] The dopant according to an embodiment may be a platinum complex, and may be represented, for example, by Chemical Formula II.

[0238] [Chemical Formula II]

[0239]

[0240] In Chemical Formula II,

[0241] X 100 Selected from O, S and NR 131 ,

[0242] 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 ,

[0243] R 132 To R 134 are each independently C1 to C6 alkyl, and

[0244] R 117 To R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl.

[0245] Hereinafter, an organic photoelectric device including the above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device is described.

[0246] The organic photoelectric 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, and an organic photosensitive drum.

[0247] Herein, an organic light emitting diode as one example of an organic photoelectric device is described with reference to the accompanying drawings.

[0248] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0249] Reference Figure 1 , the organic light emitting diode 100 according to the embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0250] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0251] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0252] The organic layer 105 may include the above-described compound for an organic photoelectric device or the composition for an organic photoelectric device.

[0253] The organic layer 105 may include, for example, a light emitting layer 130 , and the light emitting layer 130 may include, for example, the above-described compound for an organic photoelectric device or composition for an organic photoelectric device.

[0254] The composition for an organic optoelectronic device further comprising a dopant may be, for example, a green light-emitting composition.

[0255] For example, the light emitting layer 130 may include the above-described compound for an organic photoelectric device or the composition for an organic photoelectric device as a phosphorescent host.

[0256] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0257] The charge transport region may be, for example, a hole transport region 140 .

[0258] The hole transport region 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130, and block electrons. Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light emitting layer 130, and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer, and at least one of the group B compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0259] [Group B]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265] In the hole transporting zone 140, in addition to these compounds, known compounds disclosed in US 5061569 A, JP 1993-009471 A, WO 1995-009147 A1, JP 1995-126615 A, JP 1998-095973 A, etc., and compounds similar thereto can be used.

[0266] Also, the charge transport region may be, for example, the electron transport region 150 .

[0267] The electron transport region 150 may further increase electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130 , and block holes.

[0268] 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 compound of group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0269] [Group C]

[0270]

[0271]

[0272]

[0273]

[0274] Embodiments may provide an organic light emitting diode including a light emitting layer as an organic layer.

[0275] Another embodiment may provide an organic light emitting diode including a light emitting layer and a hole transport region as an organic layer.

[0276] Another embodiment may provide an organic light emitting diode including a light emitting layer and an electron transport region as an organic layer.

[0277] In addition to the light emitting layer 130 as the organic layer 105, the organic light emitting diode according to the embodiment of the present invention may include a hole transport region 140 and an electron transport region 150, such as Figure 1 shown.

[0278] On the other hand, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), and the like in addition to the light emitting layer of the above-mentioned organic layers.

[0279] The organic light emitting diode 100 may be manufactured 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.

[0280] The organic light emitting diode may be applied to an organic light emitting display device.

[0281] Hereinafter, the embodiments will be described in more detail with reference to examples. However, these examples are exemplary, and the scope of the claims is not limited thereto.

[0282] Hereinafter, unless specifically stated otherwise, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc. or Tokyo chemical industry, or synthesized by known methods.

[0283] (Preparation of compounds for organic optoelectronic devices)

[0284] Synthesis Example 1: Synthesis of Compound 1-1

[0285] [Reaction Scheme 1]

[0286]

[0287] Step 1: Synthesis of intermediate P-2

[0288] 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole (50 g), 2,4-dichloro-6-phenyl-1,3,5-triazine (31 g), Pd(PPh3)4 (7.8 g) and K2CO3 (56 g) were injected into a flask together with THF (500 mL) and distilled water (165 mL) and refluxed at 80°C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM (dichloromethane), washed 3 times with brine, and dried over MgSO4. 35 g of intermediate P-2 was obtained using column chromatography.

[0289] Step 2: Synthesis of intermediate P-1

[0290] Intermediate P-2 (35 g), 2-(3'-chloro[1,1'-diphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (26 g), Pd(PPh3)4 (4.7 g) and K2CO3 (34 g) were added to a flask along with THF (300 mL) and distilled water (100 mL) and refluxed at 80°C. After 12 hours, the reaction was terminated, and the resultant was then diluted with DCM, washed 3 times with brine, and dried over MgSO4. 33 g of intermediate P-1 was obtained by column chromatography.

[0291] Step 3: Synthesis of compound 1-1

[0292] Intermediate P-1 (33 g), Pd(OAc) 2 (1.3 g), P(t-Bu) 3 (2.3 g) and K 2 CO 3 (24 g) were charged into a flask along with xylene (500 mL) and refluxed at 150°C.

[0293] After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried over MgSO 4 17 g of compound 1-1 was obtained by column chromatography.

[0294] Synthesis Example 2: Synthesis of Compound 1-17

[0295] [Reaction Scheme 2]

[0296]

[0297] Step 1: Synthesis of intermediate P-5

[0298] 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-9H-carbazole (50 g), 3-bromo-3'-chloro-1,1'-biphenyl (36 g), Pd(PPh3)4 (7.8 g) and K2CO3 (56 g) were injected into a flask together with THF (500 mL) and distilled water (165 mL) and refluxed at 80°C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried with MgSO4. 29 g of intermediate P-5 was obtained using column chromatography.

[0299] Step 2: Synthesis of intermediate P-4

[0300] The intermediate P-5 29g, bis(pinacolato)diboron 34g, Pd(OAc)2(1.5g), K3PO446g, s-Phos(2.8g) and 1,4-dioxane (300mL) were injected into a flask and refluxed at 100°C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried with MgSO4. 28g of intermediate P-4 was obtained by column chromatography.

[0301] Step 3: Synthesis of intermediate P-3

[0302] Intermediate P-4 (28 g), 2,4-dichloro-6-phenyl-1,3,5-triazine (12 g), Pd(PPh3)4 (3.2 g) and K2CO3 (23 g) were injected into a flask together with THF (300 mL) and distilled water (100 mL) and refluxed at 80°C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried over MgSO4. 19 g of intermediate P-3 was obtained using column chromatography.

[0303] Step 4: Synthesis of Compound 1-17

[0304] Intermediate P-3 (19 g), Pd (OAc) 2 (0.8 g), P (t-Bu) 3 (1.3 g) and K 2 CO 3 (13 g) were injected into a flask together with xylene (200 mL) and refluxed at 150° C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried over MgSO 4. 11 g of compound 1-17 was obtained using column chromatography.

[0305] Synthesis Example 3: Synthesis of Compound 1-33

[0306] [Reaction Scheme 3]

[0307]

[0308] Step 1: Synthesis of intermediate P-9

[0309] 10-Bromo-12H-benzofuran[2,3-a]carbazole (50 g), bis(pinacolato)diboron (75 g), Pd(OAc)2 (3.3 g), K3PO4 (101 g) and s-Phos (6.2 g) were injected into a flask together with 1,4-dioxane (700 mL) and refluxed at 100° C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried over MgSO4. 48 g of intermediate P-9 was obtained using column chromatography.

[0310] Step 2: Synthesis of intermediate P-8

[0311] P-9 (48 g), 3-bromo-3'-chloro-1,1'-biphenyl (34 g), Pd(PPh3)4 (7.3 g) K2CO3 (53 g) were injected into a flask together with THF (500 mL) and distilled water (165 mL) and refluxed at 80°C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried over MgSO4. 39 g of intermediate P-8 was obtained using column chromatography.

[0312] Step 3: Synthesis of intermediate P-7

[0313] Intermediate P-8 (39 g), bis(pinacolato)diboron (45 g), Pd(OAc)2 (2.0 g), K3PO4 (61 g) were injected into a flask together with s-Phos (3.7 g) and 1,4-dioxane (400 mL) and refluxed at 100° C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried over MgSO4. 44 g of intermediate P-7 was obtained using column chromatography.

[0314] Step 4: Synthesis of intermediate P-6

[0315] Intermediate P-7 (44 g), 2,4-dichloro-6-phenyl-1,3,5-triazine (19 g), Pd(PPh3)4 (5.1 g) and K2CO3 (36.3 g) were injected into a flask together with THF (300 mL) and distilled water (100 mL) and refluxed at 80°C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried with MgSO4. 30 g of intermediate P-6 was obtained using column chromatography.

[0316] Step 5: Synthesis of Compound 1-33

[0317] Intermediate P-6 (30 g), Pd (OAc) 2 (1.1 g), P (t-Bu) 3 (1.8 g) and K 2 CO 3 (18 g) were injected into a flask together with xylene (300 mL) and refluxed at 150° C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried over MgSO 4. 22 g of compound 1-33 was obtained using column chromatography.

[0318] Comparative Synthesis Example 1: Synthesis of Compound C1

[0319] [Reaction Scheme 4]

[0320]

[0321] 2-Chloro-4,6-diphenyl-1,3,5-triazine (50 g), [3'-(9H-carbazole-9-yl)[1,1'-diphenyl]-3-yl]-boric acid (68 g), Pd(PPh3)4 (11 g) and K2CO3 (77 g) were injected into a flask together with THF (450 mL) and distilled water (150 mL) and refluxed at 80° C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried with MgSO4. 82 g of compound C1 was obtained using column chromatography.

[0322] Comparative Synthesis Example 2: Synthesis of Compound C2

[0323] [Reaction Scheme 5]

[0324]

[0325] Carbazole (20 g), 2-chloro-4-phenyl-6-[1,1':3',1"-terphenyl]-3-yl-1,3,5-triazine (50 g), Pd(OAc)2(2.7 g), P(t-Bu)3(4.8 g) and K2CO3(50 g) were injected into a flask along with xylene (200 mL) and refluxed at 150°C. After 12 hours, the reaction was terminated, and the resultant was diluted with DCM, washed 3 times with brine, and dried over MgSO4. 52 g of compound C2 was obtained using column chromatography.

[0326] Comparative Synthesis Example 3: Synthesis of Compound C3

[0327] [Reaction Scheme 6]

[0328]

[0329] 12H-Benzofurano[2,3-a]carbazole (20 g), 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine (27 g), Pd(OAc2) (1.5 g), P(t-Bu)3 (2.6 g) and K2CO3 (27 g) were injected into a flask together with xylene (100 mL) and refluxed at 150°C. After 12 hours, the reaction was terminated, and the resultant was then diluted with DCM, washed 3 times with brine, and dried over MgSO4. 39 g of compound C3 was obtained using column chromatography.

[0330] (Manufacturing of organic light-emitting diodes)

[0331] Example 1

[0332] A glass substrate coated with ITO (indium tin oxide) was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form A hole injection layer is formed on the hole injection layer to a thickness of Compound B is deposited on the hole transport layer to a thickness of On the hole transport auxiliary layer, the compound 1-1 of Synthesis Example 1 was used as a host, and 7 wt % of PhGD was used as a dopant to form a hole transport auxiliary layer by vacuum deposition. Subsequently, compound C is deposited to form a light-emitting layer on the light-emitting layer. The thick electron transport auxiliary layer is formed by vacuum depositing compound D and LiQ at a weight ratio of 1:1 simultaneously. On the electron transport layer, LiQ and Al are vacuum deposited sequentially to Thick and harmonious thick, thereby manufacturing an organic light emitting diode.

[0333] The structure is ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[Compound 1-1:PhGD=93:7wt%)] / Compound C / Compound D: LiQ / LiQ / Al

[0334] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0335] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0336] 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

[0337] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0338] [PhGD]

[0339]

[0340] Example 2

[0341] An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 1-17 was used instead of Compound 1-1.

[0342] Example 3

[0343] An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound 1-33 was used instead of Compound 1-1.

[0344] Example 4

[0345] A glass substrate coated with ITO (indium tin oxide) was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form A hole injection layer is formed on the hole injection layer to a thickness of The hole transport layer is formed by depositing Compound E was deposited to form a hole transport auxiliary layer. On the hole transport auxiliary layer, a mixture of Compound 1-1 of Synthesis Example 1 and Compound A-136 in a weight ratio of 3:7 was used as a host and doped with 10 wt % of PhGD as a dopant to form a hole transport auxiliary layer by vacuum deposition. Subsequently, compound F is deposited to form a light-emitting layer on the light-emitting layer. The thick electron transport auxiliary layer is formed by vacuum depositing compound G and LiQ at a weight ratio of 1:1 at the same time. On the electron transport layer, LiQ and Al are vacuum deposited sequentially to Thick and harmonious thick, thereby manufacturing an organic light emitting diode.

[0346] The structure is: ITO / compound A (3% NDP-9 doping, ) / Compound A / Compound E / EML[[{host (Compound 1-1: Compound A-136)}:{dopant (PhGD)}=90:10wt%] / Compound F / Compound G: LiQ / LiQ / Al

[0347] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0348] Compound F: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0349] Compound G: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0350] Example 5

[0351] An organic light emitting diode was manufactured in the same manner as in Example 4, except that Compound 1-17 and Compound A-136 were used in a weight ratio of 3:7 instead of Compound 1-1.

[0352] Example 6

[0353] An organic light emitting diode was manufactured in the same manner as in Example 4, except that Compound 1-33 and Compound A-136 were used in a weight ratio of 3:7 instead of Compound 1-1.

[0354] Comparative Example 1

[0355] An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound C1 was used instead of Compound 1-1.

[0356] Comparative Example 2

[0357] An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound C2 was used instead of Compound 1-1.

[0358] Comparative Example 3

[0359] An organic light emitting diode was manufactured in the same manner as in Example 1, except that Compound C3 was used instead of Compound 1-1.

[0360] Comparative Example 4

[0361] An organic light emitting diode was manufactured in the same manner as in Example 4, except that Compound C1 and Compound A-136 were used in a weight ratio of 3:7 instead of Compound 1-1.

[0362] Comparative Example 5

[0363] An organic light emitting diode was manufactured in the same manner as in Example 4, except that Compound C2 and Compound A-136 were used in a weight ratio of 3:7 instead of Compound 1-1.

[0364] Comparative Example 6

[0365] An organic light emitting diode was manufactured in the same manner as in Example 4, except that Compound C3 and Compound A-136 were used in a weight ratio of 3:7 instead of Compound 1-1.

[0366] evaluate

[0367] The driving voltage and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 6 and Comparative Examples 1 to 6 were evaluated.

[0368] The specific measurement method is as follows, and the results are shown in Table 1.

[0369] (1) Measuring the change in current density based on the change in voltage

[0370] The obtained organic light emitting diode was measured with respect to a current value flowing in a unit device while increasing a voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), and the measured current value was divided by an area to provide a result.

[0371] (2) Measuring brightness changes based on voltage changes

[0372] While the voltage of the organic light emitting diode was increased from 0V to 10V, the luminance was measured by using a luminance meter (Minolta Cs-1000A).

[0373] (3) Measurement of luminous efficiency

[0374] By using the luminance and current density and voltage from items (1) and (2), calculate the same current density (10 mA / cm 2 ) under luminous efficiency (cd / A).

[0375] (4) Lifespan measurement

[0376] Measuring brightness (cd / m 2 ) maintained at 18000cd / m 2 The results were obtained by measuring the time when the current efficiency (cd / A) dropped to 97%.

[0377] (5) Measurement of driving voltage

[0378] The ampere-voltmeter (Keithley 2400) was used to measure the 2 Measure the driving voltage of each diode.

[0379] (Table 1)

[0380]

[0381] (Table 2)

[0382]

[0383] With reference to Table 1 and Table 2, the material of the present invention is a large compound rather than an open structure, which has improved drive, efficiency and lifespan. Due to the extended resonance, this increases the mobility of holes and electrons injected into the EML layer, and stabilizes it by delocalization, thereby increasing lifespan. In addition, as the molecule becomes cyclized, the movement of the molecule is restricted, which inevitably leads to small structural changes in the excited state and the ground state. Thus, the side reaction path of the excited state is restricted, thus having high efficiency and long lifespan.

[0384] While the invention has been described in connection with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary, the invention is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

[0385] <Description of Reference Signs>

[0386] 100 OLED

[0387] 105 organic layer

[0388] 110 cathode

[0389] 120 Anode

[0390] 130 Luminous Layer

[0391] 140 Hole transport region

[0392] 150 Electron transport region.

Claims

1. A compound for an organic optoelectronic device, which is represented by Chemical Formula 1A or Chemical Formula 1B: in, In Chemical Formula 1A and Chemical Formula 1B, X 1 is O or S, n1 is 1, Z 1 To Z 3 are each independently N, and Z 4 To Z 6 Each is independently CR e ; or Z 1 To Z 3 Each is independently CR e , and Z 4 To Z 6 Each independently is N, R e and R 1 To R 4 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, m6, m7 and m8 are each independently an integer from 1 to 4, m7' and m9 are each independently an integer from 1 to 3, m9' is an integer from 1 to 2, Ar 1 and Ar 2 are each independently phenyl, biphenyl, terphenyl, or naphthyl, L 1 and L 2 are each independently a single bond, and Herein, "substituted" means that at least one hydrogen of the substituent is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano.

2. The compound according to claim 1, wherein *-L 1 -Ar 1 and *-L 2 -Ar 2 Each independently selected from the group I: [Group I] in, In Group I, * is the connection point.

3. A compound for an organic optoelectronic device, which is represented by one of the compounds of Group 1: [Group 1] 4. A composition for an organic optoelectronic device, comprising a first compound and a second compound, in, The first compound is the compound for an organic optoelectronic device according to claim 1, and The second compound is a compound for an organic photoelectric device represented by Chemical Formula 2; or a compound for an organic photoelectric device represented by a combination of Chemical Formula 3 and Chemical Formula 4: [Chemical formula 2] Wherein, in Chemical Formula 2, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 6 To R 16 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, m3 and m4 are each independently an integer from 1 to 3, m5 is an integer from 1 to 4, and n2 is an integer from 0 to 2; Among them, in Chemical Formula 3 and Chemical Formula 4, Ar 5 and Ar 6 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, Two adjacent ones of b1* to b4* in Chemical Formula 3 are connected to the carbon (C) of * in Chemical Formula 4. The other two of b1* to b4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are each independently CL d -R f , L d , L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R f and R 17 To R 24 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and Herein, "substituted" means that at least one hydrogen of the substituent is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano.

5. The composition according to claim 4, wherein Chemical formula 2 is represented by Chemical formula 2-8: [Chemical formula 2-8] in, In Chemical Formula 2-8, R 6 To R 15 are each independently hydrogen, deuterium or substituted or unsubstituted C6-C12 aryl, m3 and m4 are each independently an integer from 1 to 3, and *-L 3 -Ar 3 and *-L 4 -Ar 4 are each independently one of the substituents of Group II, [Group II] Where, in Group II, * is the connection point.

6. The composition according to claim 4, wherein The combination of Chemical Formula 3 and Chemical Formula 4 is represented by Chemical Formula 3C: [Chemical formula 3C] in, In chemical formula 3C, L d3 and L d4 is a single key, L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 17 To R 24 , R f3 and R f4 are each independently hydrogen, deuterium or C6 to C12 aryl, and Ar 5 and Ar 6 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group or a substituted or unsubstituted biphenyl group.

7. An organic optoelectronic device comprising an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, in, The organic layer comprises the compound according to any one of claims 1 to 3; or the composition according to any one of claims 4 to 6.

8. The organic optoelectronic device according to claim 7, wherein The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic photoelectric device or the composition for an organic photoelectric device. 9 . A display device comprising the organic optoelectronic device according to claim 7 .

Images