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

Abstract

A compound for an organic optoelectronic device, an organic optoelectronic device, and a display device, the organic optoelectronic device comprising the compound for an organic optoelectronic device, the display device comprising the organic optoelectronic device, the compound for an organic optoelectronic device being represented by a combination of Chemical Formula 1 and Chemical Formula 2. # imgabs0 #

Description

[0001] Citation of Related Applications

[0002] This application claims priority and the benefit of Korean Patent Application No. 10-2024-0002490, filed with the Korean Intellectual Property Office on January 5, 2024, the entire content of which is incorporated herein by reference. Technical Field

[0003] Embodiments relate to a compound for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

[0004] An organic optoelectronic device (e.g., an organic optoelectronic diode) is a device capable of converting electrical energy and light energy into each other.

[0005] According to the working principle, organic optoelectronic devices can be roughly divided into two categories. 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 applying a voltage or current to an electrode.

[0006] Examples of organic optoelectronic devices include organic optoelectronic devices, organic light-emitting diodes, organic solar cells, and organic photo drums.

[0007] Among them, due to the increasing demand for flat panel displays, organic light-emitting diodes (OLEDs) have attracted attention in recent years. An organic light-emitting diode converts electrical energy into light by applying a current to an organic light-emitting material, and the performance of an organic light-emitting diode can be affected by the organic materials disposed between electrodes. Summary of the Invention

[0008] Embodiments can be achieved by providing a compound for an organic optoelectronic device, the compound being represented by a combination of Chemical Formula 1 and Chemical Formula 2:

[0009]

[0010] In Chemical Formula 1 and Chemical Formula 2, two adjacent ones of a1* to a4* in Chemical Formula 2 are connecting carbons connected to * of Chemical Formula 1, and the remaining two of a1* to a4* in Chemical Formula 2 that are not connected to * of Chemical Formula 1 are each independently CR a , X 1 is O or S, R a and R 1 to R 5 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a combination thereof, R 6 and R 7Each independently is a substituted or unsubstituted C1-C20 alkyl group or a substituted or unsubstituted C6-C20 aryl group, L 1 and L 2 Each independently is a single bond, a substituted or unsubstituted C6-C20 arylene group, a substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof, Ar 1 and Ar 2 Each independently is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, m1 is an integer from 1 to 3, provided that: when m1 is 2 or 3, each R 5 is the same as or different from each other, and R 1 to R 4 at least one of which is a substituted or unsubstituted tert-butyl group.

[0011] An embodiment can be achieved by: providing an organic optoelectronic device including an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein at least one organic layer contains a compound for an organic optoelectronic device according to one embodiment.

[0012] An embodiment can be achieved by providing a display device including an organic optoelectronic device according to one embodiment. Description of the Drawings

[0013] By referring to the accompanying drawings and describing the exemplary embodiments in detail, the features will be apparent to those skilled in the art, wherein:

[0014] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to some exemplary embodiments. Detailed Description

[0015] Exemplary embodiments will now be described more fully hereinafter with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments described herein. On the contrary, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the exemplary embodiments to those skilled in the art.

[0016] In the drawings, for clarity of illustration, the dimensions of layers and regions may be exaggerated. It will also be understood that when a layer or element is referred to as being "on" another layer or element, it can be directly on the other layer or element, or an intermediate layer may also be present. Additionally, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or one or more intermediate layers may also be present. The same reference numerals always denote the same elements. As used herein, the term "or" is not necessarily an exclusive term, e.g., "A or B" will include A, B, or A and B.

[0017] As used herein, when no other definition is provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by one of the following: deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1-C30 amino group, nitro, substituted or unsubstituted C1-C40 silyl group, C1-C30 alkyl group, C1-C10 alkylsilyl group, C6-C30 arylsilyl group, C3-C30 cycloalkyl group, C3-C30 heterocycloalkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, C1-C20 alkoxy group, C1-C10 trifluoroalkyl group, cyano group, or a combination thereof.

[0018] In one example, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by one of the following: deuterium, C1-C30 alkyl group, C1-C10 alkylsilyl group, C6-C30 arylsilyl group, C3-C30 cycloalkyl group, C3-C30 heterocycloalkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, or cyano group. In a specific example, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by one of the following: deuterium, C1-C20 alkyl group, C6-C30 aryl group, or cyano group. In a specific example, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by one of the following: deuterium, C1-C5 alkyl group, C6-C18 aryl group, or cyano group. In a specific example, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by one of the following: deuterium, cyano group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, terphenyl group, or naphthyl group.

[0019] "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and retains the hydrogen atom.

[0020] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)". For example, any hydrogen in any compound described herein can be protium, deuterium, or tritium (e.g., based on natural or artificial substitution).

[0021] As used herein, when no other definition is provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P, and Si and the remaining carbon in a functional group.

[0022] As used herein, "aryl" means a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have conjugated p-orbitals, such as phenyl, naphthyl, etc. Two or more hydrocarbon aromatic moieties can be connected by a σ bond and can be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0023] An aryl group may include a monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional group.

[0024] As used herein, "heterocyclic group" is a superordinate concept of heteroaryl group, and may include at least one heteroatom selected from N, O, S, P, and Si in place of carbon (C) in a cyclic compound such as an aryl group, a cycloalkyl group, their fused rings, or a combination thereof. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0025] For example, "heteroaryl group" may refer to an aryl group including at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by a σ bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may include one to three heteroatoms.

[0026] More specifically, the substituted or unsubstituted C6-C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fused 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 chrysenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but not limited thereto.

[0027] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group may be a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzonaphthofuryl group, a substituted or unsubstituted benzonaphthothienyl group, a substituted or unsubstituted benzofurofluorene group, a substituted or unsubstituted benzothienofluorene group, or a combination thereof, but not limited thereto.

[0028] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0029] In addition, electron characteristics refer to the ability to accept electrons when an electric field is applied, and due to the conductive characteristics according to the lowest unoccupied molecular orbital (LUMO) energy level, the electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0030] Hereinafter, compounds for organic optoelectronic devices according to some exemplary embodiments are described.

[0031] The compounds for organic optoelectronic devices according to some exemplary embodiments may be represented by a combination of Chemical Formula 1 and Chemical Formula 2.

[0032]

[0033] In Chemical Formula 1 and Chemical Formula 2, two adjacent ones of a1* to a4* in Chemical Formula 2 are connecting carbons connected to the * of Chemical Formula 1, and the remaining two of a1* to a4* in Chemical Formula 2 that are not connected to the * of Chemical Formula 1 may each independently be CR aAs used herein, the term "connecting carbon" refers to a shared carbon that connects fused rings.

[0034] X 1 may be, for example, O or S.

[0035] R a and R 1 through R 5 may each independently be or include, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl, or a combination thereof.

[0036] R 6 and R 7 may each independently be or include, for example, substituted or unsubstituted C1-C20 alkyl or substituted or unsubstituted C6-C20 aryl.

[0037] L 1 and L 2 may each independently be or include, for example, a single bond, substituted or unsubstituted C6-C20 arylene, substituted or unsubstituted C2-C30 heterocyclic group, or a combination thereof.

[0038] Ar 1 and Ar 2 may each independently be or include, for example, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C2-C30 heterocyclic group.

[0039] m1 may be, for example, an integer from 1 to 3. In one embodiment, m1 may be 2 or 3, and each R 5 may be the same as or different from each other.

[0040] In one embodiment, at least one of R 1 through R 4 may be or may include, for example, substituted or unsubstituted tert-butyl.

[0041] The compound represented by the combination of Chemical Formula 1 and Chemical Formula 2 may have the following structure, wherein in the nucleus, fluorene is fused with benzofuran or benzothiophene, and the amino group may be substituted in or on the fluorene moiety. As the hole mobility becomes faster, charge balance can be increased, and thus the driving voltage of an organic light-emitting diode using or including the compound can be reduced and lifetime can be achieved.

[0042] In one embodiment, tert-butyl may be substituted on the benzofuran (or benzothiophene) side and may improve the efficiency of the organic light-emitting diode as a low refractive index material.

[0043] In one embodiment, the combination of Chemical Formula 1 and Chemical Formula 2 may be represented by, for example, one of Chemical Formula 1A to Chemical Formula 1F.

[0044]

[0045]

[0046] In Chemical Formulas 1A to 1F, X 1 , R 1 to R 7 , L 1 , L 2 , Ar 1 , Ar 2 and m1 can be defined to be the same as those in Chemical Formulas 1 and 2.

[0047] R a1 to R a4 can each independently be defined to be the same as R a in Chemical Formula 2.

[0048] In one embodiment, Chemical Formula 1A can be represented by, for example, one of Chemical Formulas 1A-1 to 1A-4.

[0049]

[0050] In Chemical Formulas 1A-1 to 1A-4, X 1 , R 1 to R 7 , R a1 , R a2 , L 1 , L 2 , Ar 1 , Ar 2 and m1 can be defined to be the same as those above.

[0051] In one embodiment, Chemical Formula 1B can be represented by, for example, one of Chemical Formulas 1B-1 to 1B-4.

[0052] [Chemical Formula 1B-1][Chemical Formula 1B-2]

[0053]

[0054] In Chemical Formulas 1B-1 to 1B-4, X 1 , R 1 to R 7 , R a3 , R a4 , L 1 , L 2 , Ar 1 , Ar 2 and m1 can be defined to be the same as those above.

[0055] In one embodiment, Chemical Formula 1C can be represented by, for example, one of Chemical Formula 1C-1 to Chemical Formula 1C-4.

[0056]

[0057]

[0058] In Chemical Formula 1C-1 to Chemical Formula 1C-4, X 1 , R 1 to R 7 , R a1 , R a2 , L 1 , L 2 , Ar 1 , Ar 2 and m1 can be defined the same as those above.

[0059] In one embodiment, Chemical Formula 1D can be represented by, for example, one of Chemical Formula 1D-1 to Chemical Formula 1D-4.

[0060]

[0061] In Chemical Formula 1D-1 to Chemical Formula 1D-4, X 1 , R 1 to R 7 , R a1 , R a4 , L 1 , L 2 , Ar 1 , Ar 2 and m1 can be defined the same as those above.

[0062] In one embodiment, Chemical Formula 1E can be represented by, for example, one of Chemical Formula 1E-1 to Chemical Formula 1E-4.

[0063] [Chemical Formula 1E-1][Chemical Formula 1E-2]

[0064]

[0065] In Chemical Formula 1E-1 to Chemical Formula 1E-4, X 1 , R 1 to R 7 , R a1 , R a2 , L 1 , L 2 , Ar 1 , Ar 2 and m1 can be defined the same as those above.

[0066] In one embodiment, Chemical Formula 1F can be represented by, for example, one of Chemical Formulas 1F-1 to 1F-4.

[0067]

[0068]

[0069] In Chemical Formulas 1F-1 to 1F-4, X 1 、R 1 to R 7 、R a3 、R a4 、L 1 、L 2 、Ar 1 、Ar 2 and m1 can be defined the same as those described above.

[0070] In one embodiment, the combination of Chemical Formula 1 and Chemical Formula 2 can be represented by, for example, Chemical Formula 1A-2, Chemical Formula 1A-4, Chemical Formula 1B-2, Chemical Formula 1B-4, Chemical Formula 1C-2, Chemical Formula 1C-4, Chemical Formula 1D-2, Chemical Formula 1D-4, Chemical Formula 1E-2, Chemical Formula 1E-4, Chemical Formula 1F-2, or Chemical Formula 1F-4.

[0071] In one embodiment, the combination of Chemical Formula 1 and Chemical Formula 2 can be represented by, for example, Chemical Formula 1A-4, Chemical Formula 1C-4, Chemical Formula 1E-2, Chemical Formula 1E-4, or Chemical Formula 1F-4.

[0072] In one embodiment, Ar 1 and Ar 2 can each independently be, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthracenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted terphenylene, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted dibenzothiophene, or a substituted or unsubstituted dibenzosilole.

[0073] In one embodiment, Ar 1 and Ar 2 can each independently be, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted fluorene, a substituted or unsubstituted dibenzofuran, or a substituted or unsubstituted dibenzothiophene.

[0074] In one embodiment, L 1 and L 2 can each independently be, for example, a single bond or a substituted or unsubstituted phenylene.

[0075] In one embodiment, moieties *-L 1 -Ar 1 and *-L 2- Ar 2 can each independently be, for example, moieties of Group I.

[0076] [Group I]

[0077]

[0078] In Group I, R 9 to R 12 can each independently be, for example, hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C12 aryl.

[0079] R 13 and R 14 can each independently be, for example, substituted or unsubstituted C1-C10 alkyl, or substituted or unsubstituted C6-C12 aryl.

[0080] m5 can be, for example, an integer from 1 to 5.

[0081] m6 can be, for example, an integer from 1 to 4.

[0082] m7 can be, for example, an integer from 1 to 3.

[0083] m8 can be, for example, 1 or 2.

[0084] * is a point of attachment.

[0085] In one embodiment, m5 can be 2 to 5, and each R 9 can be the same as or different from each other.

[0086] In one embodiment, m6 can be 2 to 4, and each R 10 can be the same as or different from each other.

[0087] In one embodiment, m7 can be 2 or 3, and each R 11 can be the same as or different from each other.

[0088] In one embodiment, m8 can be 2, and each R 12 can be the same as or different from each other.

[0089] In one embodiment, R a 、R a1 to R a4 and R 1 to R 4may each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof. In one embodiment, R 1 to R 4 at least one of which may be, for example, a substituted or unsubstituted tert-butyl group.

[0090] In one embodiment, R a , R a1 to R a4 and R 1 to R 4 may each independently be, for example, hydrogen, deuterium, or a substituted or unsubstituted C1 to C10 alkyl group, and at least one of R 1 to R 4 may be a tert-butyl group.

[0091] In one embodiment, R 1 may be a substituted or unsubstituted tert-butyl group.

[0092] In one embodiment, R 2 may be a substituted or unsubstituted tert-butyl group.

[0093] In one embodiment, R 3 may be a substituted or unsubstituted tert-butyl group.

[0094] In one embodiment, R 4 may be a substituted or unsubstituted tert-butyl group.

[0095] In one embodiment, R 1 to R 4 at least two of which may be substituted or unsubstituted tert-butyl groups.

[0096] In one embodiment, R 1 and R 2 may be substituted or unsubstituted tert-butyl groups.

[0097] In one embodiment, R 1 and R 3 may be substituted or unsubstituted tert-butyl groups.

[0098] In one embodiment, R 1 and R 4 may be substituted or unsubstituted tert-butyl groups.

[0099] In one embodiment, R 2 and R 3 may be substituted or unsubstituted tert-butyl groups.

[0100] In one embodiment, R 2 and R4 may be a substituted or unsubstituted tert-butyl group.

[0101] In one embodiment, R 3 and R 4 may be a substituted or unsubstituted tert-butyl group.

[0102] In one embodiment, R 1 , R 2 and R 3 may be a substituted or unsubstituted tert-butyl group.

[0103] In one embodiment, R 1 , R 2 and R 4 may be a substituted or unsubstituted tert-butyl group.

[0104] In one embodiment, R 1 , R 3 and R 4 may be a substituted or unsubstituted tert-butyl group.

[0105] In one embodiment, R 2 , R 3 and R 4 may be a substituted or unsubstituted tert-butyl group.

[0106] In one embodiment, R 1 , R 2 , R 3 and R 4 may each be a substituted or unsubstituted tert-butyl group.

[0107] In one embodiment, R 6 and R 7 may each independently be, for example, a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C12 aryl group.

[0108] In one embodiment, R 6 and R 7 may each independently be, for example, a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

[0109] In one embodiment, the compound for an organic optoelectronic device represented by the combination of Chemical Formula 1 and Chemical Formula 2 may be, for example, a compound of Group 1.

[0110] [Group 1]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] In Group 1, D n refers to the number of hydrogens replaced by deuterium, and the number of n in D n is 0 or greater and at most the number that can be replaced. However, as described above, based on natural or artificial substitution, any hydrogen in any compound can be protium, deuterium, or tritium.

[0127] In addition to the compounds for organic optoelectronic devices described above, one or more compounds may also be included.

[0128] In one embodiment, a dopant may also be included.

[0129] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0130] The dopant is a material that is mixed in a small amount with the compound or composition for an organic optoelectronic device to cause luminescence, and is generally a material such as a metal complex that emits light by being excited to a triplet state or more states multiple times. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0131] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z.

[0132] [Chemical Formula Z]

[0133] L 3 MX 2

[0134] In Chemical Formula Z, M may be a metal, and L 3 and X 2 may each independently be a ligand to form a complex with M.

[0135] M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 3 and X 2 may be, for example, bidentate ligands.

[0136] In one embodiment, the ligands represented by L 3 and X 2 may be ligands of Group A.

[0137] [Group A]

[0138]

[0139] In Group A, R 300 to R 302 may each independently be, for example, hydrogen, deuterium, a C1-C30 alkyl group which is substituted or unsubstituted by halogen, a C6-C30 aryl group which is substituted or unsubstituted by a C1-C30 alkyl group, or halogen.

[0140] R 303 to R 324 may each independently be hydrogen, deuterium, halogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C30 heteroaryl group, a substituted or unsubstituted C1-C30 amino group, a substituted or unsubstituted C6-C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1-C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1-C30 alkyl group and a C6-C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6-C30 aryl group.

[0141] n1 can be, for example, an integer from 1 to 5.

[0142] n2 can be, for example, an integer from 1 to 4.

[0143] n3 can be, for example, an integer from 1 to 3.

[0144] n4 can be, for example, 1 or 2.

[0145] n5 can be, for example, an integer from 1 to 6.

[0146] In one embodiment, n1 can be 2 or greater, and each substituent can be the same as or different from each other.

[0147] In one embodiment, n2 can be 2 or greater, and each substituent can be the same as or different from each other.

[0148] In one embodiment, n3 can be 2 or greater, and each substituent can be the same as or different from each other.

[0149] In one embodiment, n4 can be 2, and each substituent can be the same as or different from each other.

[0150] In one embodiment, n5 can be 2 or greater, and each substituent can be the same as or different from each other.

[0151] The dopant according to some exemplary embodiments can be an iridium complex and can include, for example, a dopant represented by Chemical Formula V-1 or Chemical Formula V-2.

[0152] [Chemical Formula V-1]

[0153]

[0154] In Chemical Formula V-1, R 101 to R 116 can each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 .

[0155] R 132 to R 134 can each independently be, for example, a substituted or unsubstituted C1 to C6 alkyl group.

[0156] In one embodiment, at least one of R 101 to R 116 can be a functional group represented by Chemical Formula V-1-1.

[0157] L 100It can be a bidentate ligand such as a monovalent anion, and is a ligand coordinated with iridium through the lone pair of electrons of a carbon or heteroatom.

[0158] m19 and m20 can each independently be an integer from 0 to 3, for example, and m19 + m20 can be an integer from 1 to 3.

[0159] [Chemical formula V-1-1]

[0160]

[0161] In Chemical formula V-1-1, R 135 to R 139 can each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 .

[0162] * refers to the moiety attached to the carbon atom.

[0163] [Chemical formula V-2]

[0164]

[0165] In Chemical formula V-2, R 101 to R 117 can each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 133 R 134 R 135 .

[0166] R 133 to R 135 can each independently be, for example, a substituted or unsubstituted C1-C6 alkyl group.

[0167] L 100 It can be a bidentate ligand such as a monovalent anion, and is a ligand coordinated with iridium through the lone pair of electrons of a carbon or heteroatom.

[0168] n1 and n2 can each independently be an integer from 0 to 3, for example, and n1 + n2 can be an integer from 1 to 3.

[0169] In one embodiment, the dopant according to some exemplary embodiments can be a platinum complex and can be represented by, for example, Chemical formula Z-1.

[0170] [Chemical formula Z-1]

[0171]

[0172] In Chemical Formula Z-1, rings A, B, C, and D can each independently be, for example, a 5- or 6-membered carbocyclic or heterocyclic ring.

[0173] R A 、R B 、R C and R D can each independently be, for example, mono-substituted, di-substituted, tri-substituted, or tetra-substituted or unsubstituted.

[0174] L B 、L C and L D can each independently be, for example, a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR', SiRR', GeRR', or a combination thereof.

[0175] In one embodiment, nA can be 1, and L E can be a direct bond, BR, NR, PR, O, S, Se, C═O, S═O, SO2, CRR', SiRR', GeRR', or a combination thereof. In one embodiment, nA can be 0, and L E is absent;

[0176] R A 、R B 、R C 、R D 、R and R' can each independently be, for example, hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphino, or a combination thereof; any adjacent R A 、R B 、R C 、R D 、R and R' are optionally connected to each other to provide a ring; X B 、X C 、X D and X E each independently selected from carbon and nitrogen; and Q 1 、Q 2 、Q 3 and Q 4 each represents oxygen or a direct bond.

[0177] The platinum complex can be represented, for example, by Chemical Formula VI-1 or Chemical Formula VI-2.

[0178] [Chemical Formula VI-1]

[0179]

[0180] [Chemical formula VI-2]

[0181]

[0182] In Chemical formula VI-1 and Chemical formula VI-2, X 100 can be O, S or NR 132 .

[0183] R 118 to R 132 can each independently be, for example, hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group or -SiR 133 R 134 R 135 .

[0184] R 133 to R 135 can each independently be, for example, a substituted or unsubstituted C1-C6 alkyl group.

[0185] In one embodiment, at least one of R 118 to R 132 can be -SiR 133 R 134 R 135 or tert-butyl.

[0186] R 133 to R 135 can each independently be, for example, a substituted or unsubstituted C1-C6 alkyl group.

[0187] Hereinafter, an organic optoelectronic device using the above compound for an organic optoelectronic device will be described.

[0188] An organic optoelectronic device can be a suitable device that converts electrical energy into light energy and vice versa. For example, an organic optoelectronic device, an organic light-emitting diode, an organic solar cell or an organic photosensitive drum.

[0189] In this document, an organic light-emitting diode as an example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0190] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to some exemplary embodiments.

[0191] Referring to Figure 1 , an organic light-emitting diode 100 according to some exemplary embodiments can include an anode 120 and a cathode 110 facing each other and an organic layer 105 between the anode 120 and the cathode 110.

[0192] The anode 120 can be made of a conductor with a large work function to assist hole injection, and can be, for example, a metal, a metal oxide, or a conductive polymer. The anode 120 can be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc. or their alloys; 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; or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylenedioxy)thiophene) (PEDOT), polypyrrole, or polyaniline.

[0193] The cathode 110 can be made of a conductor with a small work function to assist electron injection, and can be, for example, a metal, a metal oxide, or a conductive polymer. The cathode 110 can be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc. or their alloys; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, or BaF2 / Ca.

[0194] The organic layer 105 can contain the compounds described above for organic optoelectronic devices.

[0195] The organic layer 105 can include a light-emitting layer 130, and the light-emitting layer 130 can contain the compounds described above for organic optoelectronic devices.

[0196] The composition for an organic optoelectronic device further containing a dopant can be, for example, a green light-emitting composition.

[0197] The light-emitting layer 130 can contain, for example, the compounds described above for organic optoelectronic devices as a phosphorescent host.

[0198] In addition to the light-emitting layer, the organic layer can further include a charge transport region.

[0199] The charge transport region can be, for example, a hole transport region 140.

[0200] The hole transport region 140 can help further increase the hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130, and block electrons.

[0201] In one embodiment, the hole transport region 140 can include a hole transport layer between the anode 120 and the light-emitting layer 130 and a hole transport assisting layer between the light-emitting layer 130 and the hole transport layer, and the hole transport assisting layer can contain the compounds described above for organic optoelectronic devices.

[0202] In one embodiment, the light-emitting layer may include a host and a dopant, and the host may be, for example, a phosphorescent host.

[0203] The phosphorescent host may facilitate the injection and transport of holes and electrons within the light-emitting layer. Eventually, the holes and electrons should meet to form an exciton well, and the energy of the formed exciton should be well transferred to the dopant. Examples of the phosphorescent host may include organic compounds including carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzofuran, indolodibenzothiophene, fluorene, indolocarbazole, terphenyl, pyrimidine, triazine, or combinations thereof.

[0204] The phosphorescent host may be a suitable material and may be, for example, a single host or a mixed host.

[0205] In one embodiment, the above compound for an organic optoelectronic device may be included in the light-emitting layer, and the compound of Group C may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0206] [Group C]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213] (Dn refers to the number of hydrogens replaced by deuterium and represents a structure substituted with one or more deuterium atoms). However, as described above, based on natural or artificial substitution, any hydrogen in any compound may be protium, deuterium, or tritium.

[0214] In the hole transport region, other suitable compounds may also be used in addition to the above compounds.

[0215] In one embodiment, the charge transport region may be, for example, the electron transport region 150.

[0216] The electron transport region 150 may help further increase the electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0217] In one embodiment, 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 assisting layer between the light-emitting layer 130 and the electron transport layer, and the compound of Group D may be included in at least one of the electron transport layer and the electron transport assisting layer.

[0218] [Group D]

[0219]

[0220]

[0221]

[0222]

[0223] Some exemplary embodiments may provide an organic light-emitting diode including a light-emitting layer as an organic layer.

[0224] Some exemplary embodiments may provide an organic light-emitting diode including a light-emitting layer and a hole transport region as organic layers.

[0225] Some exemplary embodiments may provide an organic light-emitting diode including a light-emitting layer and an electron transport region as organic layers.

[0226] Some exemplary embodiments may provide an organic light-emitting diode as Figure 1 shown, which, in addition to the light-emitting layer 130, further includes a hole transport region 140 and an electron transport region 150 as organic layers 105.

[0227] In one embodiment, in addition to the light-emitting layer, the organic light-emitting diode may further include an electron injection layer, a hole injection layer, etc. as organic layers.

[0228] The organic light-emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, then forming organic layers by a dry film method (such as vacuum deposition, sputtering, plasma electroplating, and ion electroplating), and forming a cathode or an anode thereon.

[0229] The above organic light-emitting diode may be applied to an organic light-emitting display device.

[0230] The following examples and comparative examples are provided to highlight the features of one or more embodiments, but it will be understood that the examples and comparative examples should not be construed as limiting the scope of the embodiments, and the comparative examples should not be construed as being outside the scope of the embodiments. Further, it will be understood that the embodiments are not limited to the specific details described in the examples and comparative examples.

[0231] Hereinafter, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry or P&H tech, or synthesized by known methods unless otherwise specified.

[0232] (Preparation of Compounds for Organic Optoelectronic Devices)

[0233] Synthesis Example 1: Synthesis of Compound 1-4

[0234]

[0235] 10.0 g (23.20 mmol) of 2,4-di-tert-butyl-12-chloro-8,8-dimethyl-8H-fluorene [3,4-b] benzofuran, 10.06 g (27.84 mmol) of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine, 4.46 g (46.40 mmol) of sodium tert-butoxide and 0.56 g (1.39 mmol) of tri-tert-butylphosphine were dissolved in 232 ml of toluene, and 0.64 g (0.696 mmol) of Pd2(dba)3 was added thereto, and then stirred and refluxed for 12 hours under a nitrogen atmosphere. After the reaction was completed, the organic layer was extracted with ethyl acetate and distilled water, dried with anhydrous magnesium sulfate and filtered, and the filtrate therefrom was concentrated under reduced pressure. The product therefrom was purified by silica gel column chromatography with n-hexane / dichloromethane (volume ratio of 3:1) to obtain 14.2 g (yield: 81%) of Compound 1-4 as a white solid.

[0236] Calculated values: C, 88.96; H, 7.07; N, 1.85; O, 2.12.

[0237] Analytical values: C, 88.96; H, 7.07; N, 1.85; O, 2.12.

[0238] Synthesis Example 2: Synthesis of Compound 1-89

[0239]

[0240] Compound 1-89 (17.3 g, yield: 81%) was synthesized in the same manner as in Synthesis Example 1, except that 12.0 g of 1,3-di-tert-butyl-11-chloro-7,7-dimethyl-7H-fluoren-[4,3-b]benzofuran and 12.54 g of N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine were used in an equivalent ratio of 1:1.2.

[0241] Calculated values: C, 87.35; H, 6.68; N, 1.82; O, 4.16.

[0242] Analytical values: C, 87.35; H, 6.68; N, 1.82; O, 4.16.

[0243] Synthesis Example 3: Synthesis of Compound 1-91

[0244]

[0245] Compound 1-91 (14.0 g, yield: 84%) was synthesized in the same manner as in Synthesis Example 1, except that 9.0 g of 1,3-di-tert-butyl-11-chloro-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran and 10.06 g of N-(9,9-dimethyl-9H-fluoren-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.

[0246] Calculated values: C, 89.01; H, 7.22; N, 1.76; O, 2.01.

[0247] Analytical values: C, 89.01; H, 7.22; N, 1.76; O, 2.01.

[0248] Synthesis Example 4: Synthesis of Compound 1-114

[0249]

[0250] Compound 1-114 (14.9 g, yield: 82%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of 1,3-di-tert-butyl-11-chloro-7,7-dimethyl-7H-benzo[b]fluoreno[3,4-d]thiophene and 10.78 g of bis(9,9-dimethyl-9H-fluoren-2-yl)amine were used in an equivalent ratio of 1:1.2.

[0251] Calculated values: C, 87.25; H, 7.07; N, 1.72; S, 3.95.

[0252] Analytical values: C, 87.25; H, 7.07; N, 1.72; S, 3.95.

[0253] Synthesis Example 5: Synthesis of Compound 1-126

[0254]

[0255] Compound 1-126 (17.3 g, yield: 82%) was synthesized in the same manner as in Synthesis Example 1, except that 12.0 g of 3-(tert-butyl)-11-chloro-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran and 12.35 g of bis([1,1'-biphenyl]-4-yl)amine were used in an equivalent ratio of 1:1.2.

[0256] Calculated values: C, 89.19; H, 6.26; N, 2.12; O, 2.42.

[0257] Analytical values: C, 89.19; H, 6.26; N, 2.12; O, 2.42.

[0258] Synthesis Example 6: Synthesis of Compound 1-156

[0259]

[0260] Compound 1-156 (13.1 g, yield: 79%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of 1,3-di-tert-butyl-9-chloro-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran and 8.95 g of bis([1,1'-biphenyl]-4-yl)amine were used in an equivalent ratio of 1:1.2.

[0261] Calculated values: C, 88.91; H, 6.90; N, 1.96; O, 2.23.

[0262] Analytical values: C, 88.91; H, 6.90; N, 1.96; O, 2.23.

[0263] Synthesis Example 7: Synthesis of Compound 1-186

[0264]

[0265] Compound 1-186 (17.8 g, yield: 83%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of 2,4-di-tert-butyl-11-chloro-7,7-dimethyl-7H-fluoreno[2,3-b]benzofuran and 14.64 g of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluoren-2-amine were used in an equivalent ratio of 1:1.2.

[0266] Calculated values: C, 90.06; H, 6.68; N, 1.52; O, 1.74.

[0267] Analytical values: C, 90.06; H, 6.68; N, 1.52; O, 1.74.

[0268] Synthesis Example 8: Synthesis of Compound 1-329

[0269]

[0270] Compound 1-329 (11.6 g, yield: 83%) was synthesized in the same manner as in Synthesis Example 1, except that 8.0 g of 2,4-di-tert-butyl-8-chloro-12,12-dimethyl-12H-fluoreno[2,1-b]benzofuran and 8.05 g of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine were used in an equivalent ratio of 1:1.2.

[0271] Calculated values: C, 88.96; H, 7.07; N, 1.85; O, 2.12.

[0272] Analytical values: C, 88.96; H, 7.07; N, 1.85; O, 2.12.

[0273] Synthesis Example 9: Synthesis of Compound 1-336

[0274]

[0275] Compound 1-336 (21.2 g, yield: 83%) was synthesized in the same manner as in Synthesis Example 1, except that 12.0 g of 2,4-di-tert-butyl-8-chloro-12,12-dimethyl-12H-fluoreno[2,1-b]benzofuran and 17.56 g of 9,9-dimethyl-N-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-9H-fluorene-2-amine were used in an equivalent ratio of 1:1.2.

[0276] Calculated values: C, 90.06; H, 6.68; N, 1.52; O, 1.74.

[0277] Analytical values: C, 90.06; H, 6.68; N, 1.52; O, 1.74.

[0278] Comparative Synthesis Example 1: Synthesis of Compound R1

[0279]

[0280] Compound R1 (14.5 g, yield: 75%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of 10-chloro-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran and 12.63 g of N-([1,1'-biphenyl]-4-yl)dibenz[b,d]furan-2-amine were used in an equivalent ratio of 1:1.2.

[0281] Calculated values: C, 87.49; H, 5.06; N, 2.27; O, 5.18.

[0282] Analytical values: C, 87.49; H, 5.06; N, 2.27; O, 5.18.

[0283] Comparative Synthesis Example 2: Synthesis of Compound R2

[0284]

[0285] Compound R2 (15.1 g, yield: 75%) was synthesized in the same manner as in Synthesis Example 1, except that 10.0 g of 9-chloro-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran and 13.61 g of N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-4-amine were used in an equivalent ratio of 1:1.2.

[0286] Calculated values: C, 89.55; H, 5.79; N, 2.18; O, 2.48.

[0287] Analytical values: C, 89.55; H, 5.79; N, 2.18; O, 2.48.

[0288] Comparative Synthesis Example 3: Synthesis of Compound R3

[0289]

[0290] Compound R3 (24.5 g, yield: 79%) was synthesized in the same manner as in Synthesis Example 1, except that 15.0 g of 8-chloro-12,12-dimethyl-12H-fluoreno[2,1-b]benzofuran and 21.2 g of N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-3-amine were used in an equivalent ratio of 1:1.2.

[0291] Calculated values: C, 87.64; H, 5.36; N, 2.13; O, 4.86.

[0292] Analytical values: C, 87.64; H, 5.36; N, 2.13; O, 4.86.

[0293] (Manufacture of Organic Light-Emitting Diodes)

[0294] Example 1

[0295] The glass substrate coated with ITO / Ag / ITO film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically washed with acetone or isopropanol and dried, then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. The prepared ITO / Ag / ITO (reflective electrode) was used as the anode, and compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO / Ag / ITO substrate to form a thick hole injection layer, and compound A was deposited on the hole injection layer to a thickness to form a hole transport layer. Compound 1-4 obtained in Synthesis Example 1 was deposited on the hole transport layer to a thickness to form a hole transport auxiliary layer. On the hole transport auxiliary layer, 85 wt% of host H1 (40 wt%) and host H2 (60 wt%) were used as hosts, and 15 wt% of GD was doped as a dopant to form a thick light-emitting layer by vacuum deposition. Subsequently, compound C was deposited on the light-emitting layer to a thickness to form an electron transport auxiliary layer, and compound D and Liq were simultaneously vacuum deposited at a ratio of 1:1 to form a thick electron transport layer. An organic light-emitting diode was fabricated by sequentially vacuum depositing Yb and AgMg on the electron transport layer to form the cathode.

[0296] ITO / Ag / ITO / compound A (3% NDP-9 doped, ) / compound A / hole transport auxiliary layer / light-emitting layer [host (host H1, host H2):GD = 85 wt%:15 wt%] / compound C / compound D:Liq / Yb / AgMg.

[0297] Compound A: N-([1,1'-biphenyl]-2-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobi[fluorene]-2-amine

[0298] Compound C: 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0299] Compound D: 6,6'-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine)

[0300] Host H1: 2-([1,1'-Biphenyl]-4-yl)-4-phenyl-6-(3-(terphenyl-2-yl)phenyl)-1,3,5-triazine

[0301] Host H2: 9,9”-Diphenyl-9H,9”H-3,3':9',3”-tercarbazole

[0302] GD:

[0303]

[0304] Examples 2 to 9 and Comparative Examples 1 to 3

[0305] The diodes of Examples 2 to 9 and Comparative Examples 1 to 3 were fabricated in the same manner as in Example 1, except that the composition of the hole transport auxiliary layer was changed as shown in Table 1.

[0306] Evaluation

[0307] (1) Measure the change in current density according to the change in voltage

[0308] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit device in the obtained organic light-emitting diode was measured using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0309] (2) Measure the change in luminance according to the change in voltage

[0310] While increasing the voltage of the organic light-emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).

[0311] (3) Measure the luminous efficiency

[0312] The luminous efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated by using the luminance and current density from the above (1) and (2).

[0313] The relative values of the luminous efficiency based on Comparative Example 1 are shown in Table 1 as a reference.

[0314] (4) Measure the lifetime

[0315] The result was obtained by maintaining the luminance (cd / m 2 ) at 24000 cd / m 2 and measuring the time when the current efficiency (cd / A) decreased to 97%.

[0316] The relative values of the lifetime measurements based on Comparative Example 1 are shown in Table 1 as a reference.

[0317] (Table 1)

[0318] Hole transport auxiliary layer Luminous efficiency (%) Lifetime (%) Example 1 1-4 108 145 Example 2 1-89 109 149 Example 3 1-91 108 144 Example 4 1-114 108 141 Example 5 1-126 109 148 Example 6 1-156 107 139 Example 7 1-186 109 145 Example 8 1-329 108 147 Example 9 1-336 107 142 Comparative Example 1 R1 100 100 Comparative Example 2 R2 97 86 Comparative Example 3 R3 95 91

[0319] Referring to Table 1, compared with the organic light-emitting diodes according to the comparative examples, the organic light-emitting diodes applying the compounds according to the embodiments have significantly improved efficiency characteristics and lifetime characteristics.

[0320] One or more embodiments can provide compounds for organic optoelectronic devices, and the compounds can realize organic optoelectronic devices with low driving, high efficiency, and long lifetime.

[0321] Organic optoelectronic devices with high efficiency and long lifetime can be realized.

[0322] Exemplary embodiments have been disclosed herein, and although specific terms are employed, they are used and interpreted only in a generic and descriptive sense and not for purposes of limitation. In some cases, as of the filing date of this application, it will be apparent to those of ordinary skill in the art that the features, characteristics, and / or elements described in connection with a particular embodiment may be used alone, or they may be combined with the features, characteristics, and / or elements described in connection with other embodiments, unless otherwise clearly indicated. Accordingly, those skilled in the art will understand that various changes may be made in form and detail without departing from the spirit and scope of the invention as set forth in the appended claims.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by a combination of Chemical Formula 1 and Chemical Formula 2: In Chemical Formula 1 and Chemical Formula 2, Two adjacent ones of a1* to a4* in Chemical Formula 2 are linking carbons linked to the * of Chemical Formula 1, and the remaining two of a1* to a4* in Chemical Formula 2 that are not linked to the * of Chemical Formula 1 are each independently CR a , X 1 is O or S, R a and R 1 to R 5 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C20 aryl, or a combination thereof, R 6 and R 7 each independently is a substituted or unsubstituted C1-C20 alkyl group or a substituted or unsubstituted C6-C20 aryl group, L 1 and L 2 each independently is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6-C30 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, m1 is an integer from 1 to 3, provided that: when m1 is 2 or 3, each R 5 is the same as or different from one another, and R 1 to R 4 at least one of which is a substituted or unsubstituted tert-butyl group.

2. The compound for an organic optoelectronic device according to Claim 1, wherein: The combination of Chemical Formula 1 and Chemical Formula 2 is represented by one of Chemical Formula 1A to Chemical Formula 1F: In Chemical Formula 1A to Chemical Formula 1F, X 1 、R 1 to R 7 、L 1 、L 2 、Ar 1 、Ar 2 and m1 are defined to be the same as those of Chemical Formula 1 and Chemical Formula 2, and R a1 to R a4 are each independently defined to be the same as R of Chemical Formula 2 a identical.

3. The compound for an organic optoelectronic device according to Claim 1, wherein: The combination of Chemical Formula 1 and Chemical Formula 2 is represented by Chemical Formula 1A-4, Chemical Formula 1C-4, Chemical Formula 1E-2, Chemical Formula 1E-4 or Chemical Formula 1F-4: In Chemical Formula 1A-4, Chemical Formula 1C-4, Chemical Formula 1E-2, Chemical Formula 1E-4 and Chemical Formula 1F-4, X 1 , R 1 to R 7 , L 1 , L 2 , Ar 1 , Ar 2 and m1 are defined to be the same as those of Chemical Formula 1 and Chemical Formula 2, and R a1 to R a4 are each independently defined to be the same as R of Chemical Formula 2 a identical.

4. The compound for an organic optoelectronic device according to claim 1, wherein, R 1 to R 4 at least two of which are substituted or unsubstituted tert-butyl groups.

5. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted terphenylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl or a substituted or unsubstituted dibenzosilolyl.

6. The compound for an organic optoelectronic device according to Claim 1, wherein: Part *-L 1 -Ar 1 and *-L 2 -Ar 2 are each independently a part of Group I: [Group I] In Group I, R 9 to R 12 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl or substituted or unsubstituted C6-C12 aryl, R 13 and R 14 each independently is a substituted or unsubstituted C1-C10 alkyl group or a substituted or unsubstituted C6-C12 aryl group, m5 is an integer from 1 to 5, m6 is an integer from 1 to 4, m7 is an integer from 1 to 3, m8 is 1 or 2, and * is a connection point.

7. A compound for an organic optoelectronic device, the compound being a compound of Group 1: [Group 1] In Group 1, D n refers to the number of hydrogens replaced by deuterium, and the number of n in D n is 0 or greater and at most the number that can be replaced.

8. 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, Wherein the at least one organic layer contains the compound for an organic optoelectronic device according to any one of Claims 1 to 7.

9. The organic optoelectronic device according to Claim 8, wherein: The at least one organic layer includes a light-emitting layer, and The light-emitting layer contains the compound for an organic optoelectronic device.

10. The organic optoelectronic device according to Claim 8, wherein: The at least one organic layer includes: A light-emitting layer, A hole transport layer between the anode and the light-emitting layer, and A hole transport auxiliary layer between the light-emitting layer and the hole transport layer, and The hole transport auxiliary layer contains the compound for an organic optoelectronic device.

11. A display device, comprising the organic optoelectronic device according to any one of Claims 8 to 10.

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