Compounds, compositions, organic optoelectronic devices, and display devices for organic optoelectronic devices

Abstract

The present application relates to 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. Specific details of Chemical Formula 1 are defined in the specification. The present application can achieve an organic optoelectronic device with high efficiency and long lifespan.

Description

TECHNICAL FIELD

[0001] Disclosed are a compound for an organic optoelectric device, a composition for an organic optoelectric device, an organic optoelectric device, and a display device. BACKGROUND

[0002] An organic optoelectric device (organic photodiode) is a device capable of converting electric energy and optical energy into each other.

[0003] According to the principle of operation, an organic optoelectric device can be broadly classified into two types. One is a photovoltaic device that generates electric energy by separating excitons formed by optical 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 optical energy from electric energy by supplying a voltage or a current to an electrode.

[0004] Embodiments of the organic optoelectric device include an organic optoelectric device, an organic light emitting diode (OLED), an organic solar cell, and an organic photoconductor drum.

[0005] Among them, an organic light emitting diode (OLED) has recently attracted much attention due to increasing demand for flat panel display devices. The organic light emitting diode is a device that converts electric energy into light, and an organic material between electrodes greatly affects the performance of the organic light emitting diode. SUMMARY

[0006] TECHNICAL PROBLEM

[0007] One embodiment provides a compound for an organic optoelectric device capable of implementing an organic optoelectric device having high efficiency and long lifespan.

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

[0009] Another embodiment provides an organic optoelectric device including the compound.

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

[0011] MEANS FOR SOLVING PROBLEM

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

[0013] [Chemical Formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] L1 to L 3 each independently is a substituted or unsubstituted C6 to C30 arylene,

[0017] Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0018] R 1 to R 10 each independently is hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

[0019] According to another embodiment, a composition for an organic optoelectric device includes a first compound and a second compound.

[0020] The first compound can be the aforementioned compound for an organic optoelectric device, and the second compound can be represented by Chemical Formula 2.

[0021] [Chemical Formula 2]

[0022]

[0023] In Chemical Formula 2,

[0024] X 1 is O, S, NR a , CR b R c , or SiR d R e ,

[0025] R a , R b , R c , R d , R e , and R 11 to R 14 each independently is hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0026] A is any one selected from rings of Group II and Group III,

[0027] [Group II]

[0028]

[0029] [Group III]

[0030]

[0031] In Groups II and III

[0032] * indicates a linking point.

[0033] X 2 It is O, S, NR f CR g R h or SiR i R j ,

[0034] R f R g R h R i R j and R 15 To R 21 Each of these groups is independently hydrogen, deuterium, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0035] R 11 To R 14 and R 15 To R 21 At least one of them is a group represented by the chemical formula a.

[0036] [Chemical formula a]

[0037]

[0038] In chemical formula a,

[0039] L 4 To L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C30 arylene.

[0040] Ar 3 and Ar 4 Each group is independently a substituted or unsubstituted amino group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0041] * indicates a connection node.

[0042] According to another embodiment, an organic optoelectronic device includes: an anode and a cathode facing each other; and at least one organic layer located between the anode and the cathode, wherein the organic layer contains the compound for the organic optoelectronic device or the composition for the organic optoelectronic device.

[0043] According to another embodiment, a display device including the organic optoelectric device is provided.

[0044] Effects of Invention

[0045] An organic optoelectric device having high efficiency and long lifespan can be achieved. BRIEF DESCRIPTION OF DRAWINGS

[0046] Figures 1 to 4 are each a cross-sectional view of an organic light emitting diode according to an embodiment.

[0047] Explanation of Symbols

[0048] 100, 200, 300, 400: Organic light emitting diode

[0049] 105: Organic layer

[0050] 110: Cathode

[0051] 120: Anode

[0052] 130: Light emitting layer

[0053] 140: Hole transporting zone

[0054] 150: Electron transporting zone DETAILED DESCRIPTION

[0055] Hereinafter, embodiments of the present application will be described in detail. However, these embodiments are exemplary, the present application is not limited thereto and the present application is defined by the scope of the claims.

[0056] In the present specification, when a definition is not otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, halogen, hydroxyl, amine, 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.

[0057] In an embodiment of the application, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, C1to C30alkyl, C1to C10alkylsilyl, C6to C30arylsilyl, C3to C30cycloalkyl, C3to C30heterocycloalkyl, C6to C30aryl, C2to C30heteroaryl, or cyano. In a specific embodiment of the application, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, C1to C20alkyl, C6to C30aryl, or cyano. In a specific embodiment of the application, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, C1to C5alkyl, C6to C18aryl, or cyano. In a specific embodiment of the application, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0058] In the present specification, when a definition is not otherwise provided, "hetero" means including one to three heteroatoms selected from N, O, S, P, and Si in one functional group, and the rest is carbon.

[0059] In the present specification, "aryl" means a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p-orbitals that form a conjugated system (e.g., phenyl, naphthyl, and the like), two or more hydrocarbon aromatic moieties can be linked by a sigma bond and can be, for example, biphenyl, terphenyl, quaterphenyl, and the like, and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide non-aromatic fused rings, for example, fluorenyl.

[0060] The aryl group can include a monocyclic, polycyclic, or fused polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional group.

[0061] In the present specification, "heterocyclyl" is a general concept of heteroaryl, and can include at least one heteroatom selected from N, O, S, P, and Si instead of carbon (C) in a cyclic compound such as aryl, cycloalkyl, a fused ring thereof, or a combination thereof. When the heterocyclyl is a fused ring, the entire ring or each ring of the heterocyclyl can include one or more heteroatoms.

[0062] For example, "heteroaryl" can mean an aryl group including at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly linked by a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings can be fused. When the heteroaryl group is a fused ring, each ring can include one to three heteroatoms.

[0063] More specifically, the substituted or unsubstituted C6 to C30 aryl groups can be substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted o-terphenyl, substituted or unsubstituted The group may contain, but is not limited to, triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted indole, substituted or unsubstituted furanyl, or combinations thereof.

[0064] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted thiophene group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted pyrazol 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 benzofuranyl group, a substituted or unsubstituted benzothiophene group, or a substituted or unsubstituted pyrazinyl group. The substituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or combinations thereof, but not limited thereto.

[0065] In this specification, hole characteristics refer to the ability to donate electrons to form holes when an electric field is applied, and based on the highest occupied molecular orbital (HOMO) level, holes formed in the anode can be easily injected into and transported in the light-emitting layer due to their conductivity.

[0066] Further, the electronic property refers to the ability to accept electrons when an electric field is applied, and according to the lowest unoccupied molecular orbital (LUMO) level, electrons formed in the cathode can be easily injected into and transported in the light-emitting layer due to the presence of the conductive property.

[0067] Hereinafter, a compound for an organic optoelectric device according to one embodiment is described.

[0068] A compound for an organic optoelectric device according to one embodiment is represented by Chemical Formula 1.

[0069] [Chemical Formula 1]

[0070]

[0071] In Chemical Formula 1,

[0072] L 1 to L 3 each independently is a single bond or a substituted or unsubstituted C6 to C30 arylene,

[0073] Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0074] R 1 to R 10 each independently is hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl, or a substituted or unsubstituted C6 to C20 aryl.

[0075] The compound represented by Chemical Formula 1 has a structure in which is substituted with triazine at the end.

[0076] Since Since substituted with triazine at the end, the molecule becomes stable due to the longer conjugation length compared to the case linked to the center, and thus the molecule can have a long lifetime effect. Further, by enhancing the stability of the ring through the fusion to the aromatic ring, the lifetime can be further maximized.

[0077] Depending on the specific substitution point of triazine, Chemical Formula 1 can be represented by any one of Chemical Formulae 1-1 to 1-4.

[0078] [Chemical Formula 1-1]

[0079]

[0080] [Chemical Formula 1-2]

[0081]

[0082] [Chemical Formula 1-3]

[0083]

[0084] [Chemical Formula 1-4]

[0085]

[0086] In Chemical Formulae 1-1 to 1-4,

[0087] L 1 to L 3 , Ar 1 , and Ar 2 , and R 1 to R 10 are the same as described above.

[0088] The compound for an organic photoelectric device according to one embodiment can be represented by any one of Chemical Formula 1-1, Chemical Formula 1-2, and Chemical Formula 1-4.

[0089] In an embodiment of the present application, at least one of Ar 1 and Ar 2 may be a substituted or unsubstituted C10 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0090] In a more specific embodiment of the present application, at least one of Ar 1 and Ar 2 may be a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0091] In an exemplary embodiment of the present application, L 1 to L 3 may each independently be a single bond or a substituted or unsubstituted phenylene group.

[0092] For example, L 1 may be a single bond, Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and Ar 1 and Ar 2At least one of,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,

[0093] For example, L 1 may be a substituted or unsubstituted phenylene group, and Ar 1 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. 2 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0094] As a more specific example, each of *-L 2 -Ar 1 and *-L 3 -Ar 2 may be independently selected from the substituents of Group I.

[0095] [Group I]

[0096]

[0097] In Group I, * is a linking point.

[0098] For example, the compound for an organic optoelectric device represented by Chemical Formula 1 can be a compound selected from Group 1, but is not limited thereto.

[0099] [Group 1]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] A composition for an organic optoelectric device according to another embodiment includes a first compound and a second compound, wherein the first compound can be the aforementioned compound for an organic optoelectric device, and the second compound can be represented by Chemical Formula 2.

[0106] [Chemical Formula 2]

[0107]

[0108] In Chemical Formula 2,

[0109] X1is O, S, NR a , CR b R c or SiR d R e ,

[0110] R a , R b , R c , R d , R e and R 11 to R 14 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0111] A is any one of a ring selected from Group II and Group III,

[0112] [Group II]

[0113]

[0114] [Group III]

[0115]

[0116] wherein, in Group II and Group III,

[0117] * is a linking point,

[0118] X 2 is O, S, NR f , CR g R h or SiR i R j ,

[0119] R f , R g , R h , R i , R j and R 15 to R 21 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0120] R 11 to R 14 and R 15 to R 21 at least one of which is a group represented by Chemical Formula a,

[0121] [Chemical Formula a]

[0122]

[0123] wherein, in Chemical Formula a,

[0124] L 4 to L 6 each independently is a single bond or a substituted or unsubstituted C6 to C30 arylene,

[0125] Ar 3 and Ar 4 each independently is a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0126] * is a linking point.

[0127] The second compound can have a structure in which a carbazole / fused carbazole / fused dibenzofuran / fused dibenzothiophene / fused dibenzosilole is substituted with an amine, and depending on the type and the position of fusion of the additional benzene ring, can be represented by, for example, any one of Chemical Formulae 2-I to 2-IX.

[0128]

[0129]

[0130] In Chemical Formulae 2-I to 2-IX, X 1 , X 2 , and R 11 to R 21 are the same as described above.

[0131] In addition, depending on the substitution direction of the amine group, the second compound can be represented by one of Chemical Formulae 2-IA to 2-IXA, Chemical Formulae 2-IB to 2-IXB, and Chemical Formulae 2-IC to 2-IIIC.

[0132]

[0133]

[0134]

[0135] In Chemical Formulae 2-IA to 2-IXA, Chemical Formulae 2-IB to 2-IXB, and Chemical Formulae 2-IC to 2-IIIC, X 1 , X 2 , L 2 to L4 , Ar 3 , and Ar 4 are the same as described above, and

[0136] R 11 to R 21 each independently are hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl.

[0137] The second compound according to the embodiment can be represented by one of Chemical Formula 2-VIIIA, Chemical Formula 2-IVB, and Chemical Formula 2-VIIIB.

[0138] For example, in Chemical Formula 2-VIIIA, X 1 may be O or S, and X 2 may be CR g R h , or SiR i R j .

[0139] For example, in Chemical Formula 2-VIIIB, X 1 may be O or S, and X 2 may be CR g R h , or SiR i R j .

[0140] For example, in Chemical Formula 2-VIIIA, X 1 may be CR g R h , or SiR i R j , and X 2 may be O or S.

[0141] For example, in Chemical Formula 2-VIIIB, X 1 may be CR g R h , or SiR i R j , and X 2 may be O or S.

[0142] Here, R g , R h , R i , and R j may each independently represent substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C20 aryl.

[0143] The second compound according to certain embodiments can be represented by any one of Chemical Formula 2-VIIIA-2, Chemical Formula 2-IVB-2, and Chemical Formula 2-VIIIB-2.

[0144]

[0145]

[0146] In Chemical Formula 2-VIIIA-2, Chemical Formula 2-IVB-2, and Chemical Formula 2-VIIIB-2,

[0147] L 4 to L 6 each independently is a single bond or a substituted or unsubstituted phenylene,

[0148] Ar 3 and Ar 4 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl,

[0149] X 1 is NR a , O, S, CR b R c or SiR d R e ,

[0150] X 2 is O, S, CR g R h or SiR i R j ,

[0151] R a , R b , R c , R d , R e , R g , R h , R i and R j each independently is a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl, and

[0152] R 11 to R 15 and R 19 to R 21 each independently is hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl, a substituted or unsubstituted C6 to C30 aryl, or a substituted or unsubstituted C2 to C30 heterocyclyl.

[0153] For example, L5 and L 6 may each independently be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0154] For example, Ar 3 and Ar 4 may each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted terphenanthryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzofuranofluorenyl, or a substituted or unsubstituted benzothiophenofluorenyl.

[0155] For example, the second compound can be a compound selected from Group 2, but is not limited thereto.

[0156] [Group 2]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171] The first compound and the second compound can be included, for example, in a weight ratio of 1:99 to 99:1. Within the range, the electron-transporting ability of the first compound and the hole-transporting ability of the second compound can be used to adjust the desired weight ratio to achieve ambipolar characteristics and thus improve efficiency and lifetime. Within the range, it can be included, for example, in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, or about 30:70 to about 60:40. For example, it can be included in a weight ratio of 40:60, 50:50, or 60:40.

[0172] In addition to the aforementioned first compound and the second compound, one or more compounds can be further included.

[0173] The aforementioned compound for an organic optoelectric device or the composition for an organic optoelectric device can be a composition further including a dopant.

[0174] The dopant can be, for example, a phosphorescent dopant (for example, a red, green, or blue phosphorescent dopant), for example, a red or green phosphorescent dopant.

[0175] The dopant is a material mixed in a trace amount with a compound or a composition for an organic optoelectric device to cause light emission, and can be generally a material (for example, a metal complex) that emits light by multiple excitations into a triplet state or more. The dopant can be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof can be used.

[0176] An embodiment of the dopant can be a phosphorescent dopant, and an embodiment of the phosphorescent dopant can be an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant can be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.

[0177] [Chemical Formula Z]

[0178] L 5 MX

[0179] In Chemical Formula Z, M is a metal, and L 5 is the same as or different from X, and is a ligand forming a complex compound with M.

[0180] 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 5 and X can be, for example, a bidentate ligand.

[0181] Hereinafter, an organic optoelectric device including the aforementioned compound for an organic optoelectric device or the composition for an organic optoelectric device is described.

[0182] The organic optoelectric device can be any device that converts electrical energy into optical energy and vice versa without particular limitation, and can be, for example, an organic optoelectric device, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum.

[0183] Herein, an organic light emitting diode as one embodiment of an organic optoelectric device is described with reference to the accompanying drawings.

[0184] Figures 1 to 4 is a cross-sectional view illustrating an organic light emitting diode according to an embodiment.

[0185] Referring to Figure 1 , an organic light emitting diode 100 according to an 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.

[0186] The anode 120 can be made of a conductor having a large work function to help hole injection, and can be, for example, a metal, a metal oxide, and / or a conductive polymer, but is not limited thereto. The anode 120 can be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, and the like or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and 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.

[0187] The cathode 110 can be made of a conductor having a small work function to help electron injection, and can be, for example, a metal, a metal oxide, and / or a conductive polymer, but is not limited thereto. 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, and the like or an alloy thereof; a multi-layered structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but is not limited thereto.

[0188] The organic layer 105 can include the aforementioned compound for an organic optoelectric device or the composition for an organic optoelectric device.

[0189] The organic layer 105 can include the light-emitting layer 130, and the light-emitting layer 130 can contain the aforementioned compound for an organic optoelectric device or the composition for an organic optoelectric device.

[0190] The composition for an organic optoelectric device further containing a dopant can be, for example, a red light-emitting composition.

[0191] The light-emitting layer 130 can contain, for example, the aforementioned first compound for an organic optoelectric device and the second compound for an organic optoelectric device as a phosphorescent host, respectively.

[0192] In addition to the light-emitting layer, the organic layer can further include a charge transport region.

[0193] The auxiliary layer can be, for example, a hole auxiliary layer (hole transport region) 140.

[0194] Referring to Figure 2 In addition to the light-emitting layer 130, the organic light-emitting diode 200 further includes a hole transport region 140. The hole transport region 140 can further increase the 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 can include a hole transport layer positioned between the anode 120 and the light-emitting layer 130, and a hole transport auxiliary layer positioned between the light-emitting layer 130 and the hole transport layer, and at least one of the compounds of Group E can be contained in at least one of the hole transport layer and the hole transport auxiliary layer.

[0195] [Group E]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] In the hole transport region, in addition to the aforementioned compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and the like, and compounds having similar structures can also be used.

[0202] Further, the charge transport region can be, for example, an electron transport region 150.

[0203] Referring to Figure 3The organic light emitting diode 300 further includes an electron transport zone 150 in addition to the light emitting layer 130. The electron transport zone 150 can further increase electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130, and block holes.

[0204] Specifically, the electron transport zone 150 can include an electron transport layer positioned between the cathode 110 and the light emitting layer 130, and an electron transport auxiliary layer positioned between the light emitting layer 130 and the electron transport layer, and at least one of the compounds of Group F can be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0205] [Group F]

[0206]

[0207]

[0208]

[0209] As shown in Figure 1 , one embodiment of the present application can provide an organic light emitting diode including the light emitting layer 130 as the organic layer 105.

[0210] As shown in Figure 2 , another embodiment of the present application can provide an organic light emitting diode including the hole transport zone 140 as the organic layer 105 in addition to the light emitting layer 130.

[0211] As shown in Figure 3 , another embodiment of the present application can provide an organic light emitting diode including the electron transport zone 150 as the organic layer 105 in addition to the light emitting layer 130.

[0212] As shown in Figure 4 , another embodiment of the present application can provide an organic light emitting diode including the hole transport zone 140 and the electron transport zone 150 as the organic layer 105 in addition to the light emitting layer 130.

[0213] In another embodiment of the present application, an organic light emitting diode can include an electron injection layer (not shown), a hole injection layer (not shown), etc. as the organic layer 105 in each of Figures 1 to 4 .

[0214] The organic light emitting diodes 100, 200, 300, and 400 can be manufactured by forming an anode or a cathode on a substrate, and then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma coating, and ion coating, etc., and forming a cathode or an anode thereon.

[0215] The organic light emitting diode can be applied to an organic light emitting display device.

[0216] Hereinafter, the embodiments are shown in more detail with reference to examples. However, the examples are exemplary, and the scope of the claims is not limited thereto.

[0217] Hereinafter, the starting materials and reactants used in the examples and synthesis examples are purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry, or P&H tech, or synthesized by a known method, unless there is a particular note.

[0218] (Preparation of compounds for organic optoelectronic devices)

[0219] The compounds presented as more specific examples of the compounds of the present application were synthesized by the following steps.

[0220] Synthesis Example 1: Synthesis of int 1

[0221] [Reaction Scheme 1]

[0222]

[0223] a) Synthesis of int 1-1

[0224] Dissolved 2-bromo-5-chlorobenzaldehyde (20.0 g, 91.1 mmol), 2-naphthaleneboronic acid (17.2 g, 100.2 mmol), Pd(PPh3)4(5.3 g, 4.6 mmol), and K2CO3(37.8 g, 273.4 mmol) in a 450 mL mixed solution of tetrahydrofuran:distilled water = 2:1, and then, stirred for 12 hours at 80°C under reflux. When the reaction was completed, the resulting product was purified by column chromatography (dichloromethane:n-hexane) to obtain 17.6 g (72.6%) of int 1-1.

[0225] b) Synthesis of int 1-2

[0226] Int 1-1 (17.6 g, 66 mmol) and (methoxymethyl)triphenylphosphonium chloride (24.9 g, 73 mmol) were dissolved in 130 mL of tetrahydrofuran, and to this, potassium tert-butoxide (8.9 g, 79 mmol) was slowly added and stirred at 0°C. When the reaction was completed, all the solvent was removed using a rotary evaporator. Subsequently, the organic layer obtained therefrom by extraction twice with dichloromethane and distilled water was dried. Without performing a separate additional purification, the dried organic layer was dissolved in 130 mL of dichloromethane, and to this, methanesulfonic acid (12.7 g, 132 mmol) was slowly added and then, stirred at 0°C. When the reaction was completed, the solid precipitated by adding methanol to the reaction solution was primarily filtered and then, dissolved in toluene and filtered / purified with silica gel to obtain 8.9 g (51.4%) of int 1-2.

[0227] c) Synthesis of int 1

[0228] Int 1-2 (8.9 g, 34 mmol), bis(pinacolato)diboron (11.2 g, 44 mmol), potassium acetate (10.0 g, 102 mmol), tricyclohexylphosphine (1.9 g, 7 mmol), and [1,1'-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1.4 g, 2 mmol) were added to 170 mL of N,N-dimethylformamide and then, stirred at 150°C under reflux for 12 hours. When the reaction was completed, the reaction solution was added to an excess of DIW to form a precipitate. The precipitate was filtered and then, boiled and dissolved in toluene and filtered with silica gel. The filtered solution was recrystallized as it was to obtain 7.1 g (63.1%) of int 1.

[0229] Synthesis Example 2: Synthesis of int 2

[0230] [Reaction Scheme 2]

[0231]

[0232] a) Synthesis of int 2

[0233] Int 2 was synthesized according to the same method as the third step of the synthesis method of int 1 according to Synthesis Example 1, except that 2-bromo-6-chlorobenzaldehyde was used instead of 2-bromo-5-chlorobenzaldehyde.

[0234] Synthesis Example 3: Synthesis of int 3

[0235] [Reaction Scheme 3]

[0236]

[0237] a) Synthesis of int 3

[0238] Int 3 was synthesized according to the same method as the third step of the synthetic method of int 1 according to Synthesis Example 1 except that 2-bromo-3-chlorobenzaldehyde was used instead of 2-bromo-5-chlorobenzaldehyde.

[0239] Synthesis Synthesis Example 4 to Synthesis Example 10

[0240] Each of the compounds according to Synthesis Example 4 to Synthesis Example 10 was synthesized using the intermediates A and B synthesized by the same Suzuki reaction as the synthetic method of int 1-1 shown in Table 1.

[0241] (Table 1)

[0242]

[0243] Comparative Synthesis Example 1: Synthesis of Compound B-1

[0244] [Reaction Scheme 4]

[0245]

[0246] a) Synthesis of Intermediate B-1-1

[0247] Int 1-1 was synthesized according to the same method as the synthetic method of int 1 according to Synthesis Example 1 except that 6,12-dibromo Int 1-1 was synthesized according to the same method as the synthetic method of int 1 according to Synthesis Example 1 except that 6,12-dibromo

[0248] b) Synthesis of Intermediate B-1-2

[0249] Int 1-2 was synthesized according to the same method as the synthetic method of int 1 according to Synthesis Example 1 except that Intermediate B-1-1 was used as a starting material 1 and then recrystallized with toluene.

[0250] c) Synthesis of Compound B-1

[0251] Compound B-1 was synthesized according to the same method as the synthetic method of int 1-1 according to Synthesis Example 1 except that Intermediate B-1-2 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used as starting materials 1 and then recrystallized with monochlorobenzene.

[0252] Comparative Synthesis Example 2: Synthesis of Compound B-2

[0253] [Reaction Scheme 5]

[0254]

[0255] a) Synthesis of intermediate B-2-1

[0256] Intermediate B-2-1 was synthesized according to the same method as the synthesis method of int 1-1 according to Synthesis Example 1, except that 3-methoxy-2-bromonaphthalene and 2-formylphenylboronic acid were used as starting material 1 and then recrystallized using toluene.

[0257] b) Synthesis of intermediate B-2-2

[0258] Intermediate B-2-2 was synthesized according to the same method as the synthesis method of int 1-2 according to Synthesis Example 1, except that intermediate B-2-1 was used as starting material 1 and then recrystallized using monochlorobenzene.

[0259] c) Synthesis of intermediate B-2-3

[0260] Intermediate B-2-3 was synthesized according to the same method as the bromination of 2-methoxynaphthalene set forth in Tetrahedron Letters, 47(27), 4581-4584; 2006, except that intermediate B-2-2 was used as starting material 1 and toluene was used for recrystallization.

[0261] d) Synthesis of intermediate B-2-4

[0262] Intermediate B-2-4 was synthesized according to the same method as the synthesis method of int 1-1 according to Synthesis Example 1, except that intermediate B-2-3 and 1-naphthalenboronic acid were used as starting material 1 and then recrystallized using monochlorobenzene.

[0263] e) Synthesis of intermediate B-2-5

[0264] Intermediate B-2-4 (22.0 g, 57 mmol) and pyridine hydrochloride (66 g, 572 mmol) were mixed and then stirred at 200°C under reflux for 12 hours. When the reaction was completed, the resultant was cooled to a predetermined temperature and then completely cooled to room temperature by adding distilled water thereto. The resultant was extracted twice with ethyl acetate and distilled water and then filtered with silica gel to obtain 16.9 g (79.7%) of intermediate B-2-5.

[0265] f) Synthesis of intermediate B-2-6

[0266] Intermediate B-2-5 (16 g, 43 mmol) and triethylamine (6.6 g, 65 mmol) were dissolved in 85 mL of dichloromethane, and to this, triflic anhydride (14.0 g, 50 mmol) was slowly added at 0°C. When the addition was completed, the mixture was heated to room temperature and then, stirred for 12 hours. When the reaction was completed, ice water was added thereto and then, extracted twice with dichloromethane, and the organic layer obtained therefrom was filtered with silica gel. Methanol was added thereto to precipitate, and the precipitate was filtered to obtain 20.1 g (92.6%) of intermediate B-2-6.

[0267] g) Synthesis of intermediate B-2-7

[0268] Intermediate B-2-7 was synthesized in the same manner as the synthesis of int 1 of Synthesis Example 1, except that intermediate B-2-6 was used as a starting material and the solvent was changed to dioxane alone and then recrystallized with toluene.

[0269] h) Synthesis of compound B-2

[0270] Compound B-2 was synthesized in the same manner as the synthesis of int 1-1 of Synthesis Example 1, except that intermediate B-2-7 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used as starting materials and then recrystallized with chlorobenzene.

[0271] Comparative Synthesis Example 3: Synthesis of compound B-3

[0272] [Reaction Scheme 6]

[0273]

[0274] a) Synthesis of intermediate B-3-1

[0275] Intermediate B-3-1 was synthesized / purified in the same manner as the synthesis of intermediate B-2-5 of Comparative Synthesis Example 2, except that intermediate B-2-2 was used as a starting material.

[0276] b) Synthesis of intermediate B-3-2

[0277] Intermediate B-3-2 was synthesized / purified in the same manner as the synthesis of intermediate B-2-6 of Comparative Synthesis Example 2, except that intermediate B-3-1 was used as a starting material.

[0278] c) Synthesis of compound B-3

[0279] The compound B-3 was synthesized / purified according to the same method as the synthetic method of int 1-1 of Synthesis Example 1, except that intermediate B-3-2 and 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine were used as starting materials and then recrystallization was performed with chlorobenzene.

[0280] Synthesis of a second compound

[0281] Synthesis Example 11: Synthesis of compound A-84

[0282] [Reaction Scheme 7]

[0283]

[0284] a) Synthesis of intermediate 2-1a

[0285] Phenylhydrazine hydrochloride (70.0 g, 484.1 mmol) and 7-bromo-3,4-dihydro-2H-naphthalen-1-one (108.9 g, 484.1 mmol) were put into a round bottom flask and then dissolved in ethanol (1200 mL). To this, 60 mL of hydrochloric acid was slowly added dropwise at room temperature and then stirred at 90°C for 12 hours. When the reaction was completed, after removing the solvent under reduced pressure, extraction was performed using an excess of ethyl acrylate (EA). After removing the organic solvent under reduced pressure, the residue was stirred in a small amount of methanol and then filtered to obtain 95.2 g (66%) of intermediate 2-1a.

[0286] b) Synthesis of intermediate 2-1b

[0287] Intermediate 2-1a (95.2 g, 319.3 mmol) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (108.7 g, 478.9 mmol) were put into a round bottom flask and then dissolved in 600 mL of toluene. The solution was stirred at 80°C for 12 hours. When the reaction was completed, after removing the reaction solvent, the residue was treated by column chromatography to obtain 41.3 g (44%) of intermediate 2-1b.

[0288] c) Synthesis of intermediate 2-1c

[0289] Intermediate 2-1b (41.3 g, 139.0 mmol), iodobenzene (199.2 g, 976.0 mmol), CuI (5.31 g, 28.0 mmol), K2CO3(28.9 g, 209.0 mmol), and 1,10-phenanthroline (5.03 g, 28.0 mmol) were put into a round bottom flask and dissolved in 500 mL of dimethyl formamide (DMF). The solution was stirred at 180°C for 12 hours. When the reaction was completed, after removing the reaction solvent under reduced pressure, the residue was dissolved in dichloromethane and then, silica gel filtration was performed. After concentrating the dichloromethane, the resulting product was recrystallized with hexane to obtain 39.0 g (75%) of intermediate 2-1c.

[0290] d) Synthesis of Compound A-84

[0291] Intermediate 2-1b (41.3 g, 139.0 mmol), iodobenzene (199.2 g, 976.0 mmol), CuI (5.31 g, 28.0 mmol), K2CO3(28.9 g, 209.0 mmol), and 1,10-phenanthroline (5.03 g, 28.0 mmol) were put into a round bottom flask and dissolved in 500 mL of dimethyl formamide (DMF). The solution was stirred at 180°C for 12 hours. When the reaction was completed, after removing the reaction solvent under reduced pressure, the residue was dissolved in dichloromethane and then, silica gel filtration was performed. After concentrating the dichloromethane, the resulting product was recrystallized with hexane to obtain 39.0 g (75%) of intermediate 2-1c.

[0292] Synthesis Example 12: Synthesis of Compound 2-92

[0293] [Reaction Scheme 8]

[0294]

[0295] a) Synthesis of Intermediate 2-92a

[0296] It was synthesized with reference to KR 10-1423173 B1.

[0297] b) Synthesis of Compound 2-92

[0298] Dissolved 5.0 g (16.93 mmol) of intermediate 2-92a, 5.4 g (16.93 mmol) of amine intermediate 2-92b, 2.44 g (25.39 mmol) of sodium tert-butoxide, and 0.68 g (1.69 mmol) of tri-tert-butylphosphine in 100 mL of toluene, and added 0.47 g (0.51 mmol) of Pd(dba)2thereto, and then, stirred for 12 hours under reflux under a nitrogen atmosphere. When the reaction was completed, the organic layer extracted with toluene and distilled water was dried with anhydrous magnesium sulfate and filtered, and the filtrate obtained therefrom was concentrated under reduced pressure. The product obtained therefrom was purified by column chromatography on silica gel with n-hexane / dichloromethane (volume ratio 2:1), obtaining 8.2 g (yield: 84.0%) of compound 2-92.

[0299] (Manufacturing an organic light emitting diode)

[0300] Example 1

[0301] A glass substrate coated with indium tin oxide (ITO) was cleaned with distilled water and ultrasonic waves. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, and the like, and dried, and then, moved to a plasma cleaner, cleaned for 10 minutes using an oxygen plasma, and moved to a vacuum depositor. The ITO transparent electrode thus obtained was used as an anode, compound A doped with 1% NDP-9 (available from Novaled GmbH) was vacuum deposited on the ITO substrate to form a 1400 angstrom-thick hole transport layer, and compound B was deposited on the hole transport layer to form a 350 angstrom-thick hole transport auxiliary layer. On the hole transport auxiliary layer, a 400 angstrom-thick light emitting layer was formed by using the compound 1 of Synthesis Example 4 and by vacuum depositing 2% by weight (wt%) of [Ir(piq)2acac] as a dopant. Subsequently, compound C was deposited on the light emitting layer to form a 50 angstrom-thick electron transport auxiliary layer, and compound D and Liq were simultaneously vacuum deposited at a weight ratio of 1:1 to form a 300 angstrom-thick electron transport layer. LiQ (15 angstroms) and Al (1200 angstroms) were sequentially vacuum deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light emitting diode. An organic light emitting diode has a five-layered organic thin layer, and particularly, the following structure.

[0302]

[0303] ​ITO / Compound A (1% NDP-9 doping, 1400 angstroms) / Compound B (350 angstroms) / EML [Compound 1: [Ir(piq)2acac] (2 wt%)] (400 angstroms) / Compound C (50 angstroms) / Compound D: Liq (300 angstroms) / LiQ (15 angstroms) / Al (1200 angstroms).

[0304] Compound A: N-(diphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0305] Compound B: N,N-di([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoren-10-amine

[0306] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0307] Compound D: 8-(4-(4,6-bis(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0308] Example 2 and Comparative Example 1 and Comparative Example 2

[0309] The diodes of Example 2, Comparative Example 1 and Comparative Example 2 were manufactured in the same manner as in Example 1 except that the host was changed as shown in Table 2.

[0310] Examples 3 to 12 and Comparative Examples 3 to 5

[0311] The diodes of Examples 3 to 12 and Comparative Examples 3 to 5 were manufactured in the same manner as in Example 1 except that the host was changed as shown in Table 3 and the first host and the second host were mixed in a weight ratio of 5:5.

[0312] Evaluation

[0313] The luminous efficiency and the lifetime characteristics of the organic light emitting diodes according to Examples 1 to 12, Comparative Examples 1 to 5 were evaluated. The specific measurement method was as follows, and the results are shown in Tables 2 and 3.

[0314] (1) Measurement of current density change according to voltage change

[0315] The organic light emitting diodes obtained were measured for the current value flowing in the unit device while the voltage was increased from 0 volt to 10 volt using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0316] (2) Measuring luminance change according to voltage change

[0317] The luminance was measured by using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light emitting diode was increased from 0 volt to 10 volt.

[0318] (3) Measuring luminous efficiency

[0319] The luminous efficiency (cd / A) at the same current density (10 milliampere / square centimeter (mA / cm 2 ) was calculated by using the luminance, current density and voltage from items (1) and (2).

[0320] The relative value evaluated with respect to the luminous efficiency of Comparative Example 1 and Comparative Example 3 is shown in Table 2 and Table 3.

[0321] (4) Measuring lifetime

[0322] The T95 lifetime of the organic light emitting diodes according to Example 1 to Example 12 and Comparative Example 1 to Comparative Example 5 was measured as the time when the luminance was reduced to 95% with respect to the initial luminance (candela / square meter) after measuring the luminance reduction according to time using a Polanonix lifetime measuring system, which emitted light with 6,000 candela / square meter (cd / m 2 ) as the initial luminance (candela / square meter).

[0323] The relative value evaluated with respect to the T95 lifetime of Comparative Example 1 and Comparative Example 3 is shown in Table 2 and Table 3.

[0324] (Table 2)

[0325] Single body T95 lifetime (%) Efficiency (%) Example 1 Compound 1 160 115 Example 2 Compound 88 220 110 Comparative Example 1 B-1 100 100 Comparative Example 2 B-3 55 102

[0326] (Table 3)

[0327]

[0328] Referring to Table 2 and Table 3, the compound according to the present application as a single host showed improved efficiency and lifetime compared to the comparative compound, and in particular, showed overall greatly improved driving voltage, efficiency and lifetime when mixed with a second host.

[0329] While the application has been described in connection with what is presently considered to be the actual embodiments, it is to be understood that the application is not limited to the disclosed embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A composition for an organic optoelectric device, comprising: a first compound and a second compound, wherein the first compound is a compound for an organic optoelectric device represented by any one of Chemical Formula 1-1, Chemical Formula 1-2, Chemical Formula 1-3, and Chemical Formula 1-4, and wherein the second compound is a compound for an organic optoelectric device represented by Chemical Formula 2-IVB-2 or Chemical Formula 2-VIIIB-2: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In Chemical Formula 1-1, Chemical Formula 1-2, Chemical Formula 1-3, and Chemical Formula 1-4, [Chemical Formula 2-IVB-2] [Chemical Formula 2-VIIIB-2] wherein, in Chemical Formula 2-IVB-2 and Chemical Formula 2-VIIIB-2, wherein "substituted" means that at least one hydrogen of a substituent or a compound is replaced with deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. L 1 to L 3 each independently is a single bond or a substituted or unsubstituted phenylene, Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl, and R 1 R 2 and R 5 To R 8 Each can be independently hydrogen, deuterium, or an unsubstituted phenyl group. R 3 , R 4 , R 9 , and R 10 are each independently hydrogen or deuterium, 2.The composition of claim 1, wherein 3.The composition of claim 1, wherein X 1 is O, S or NR a , X 2 is CR g R h or SiR i R j , L 4 to L 6 each independently is a single bond or a substituted or unsubstituted phenylene, Ar 3 and Ar 4 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl, R a , R g , R h , R i , and R j are each independently a substituted or unsubstituted C1to C30alkyl or a substituted or unsubstituted C6to C30aryl, R 11 to R 15 and R 19 each independently is hydrogen, deuterium, substituted or unsubstituted C6to C30aryl, or substituted or unsubstituted C2to C30heterocyclyl, and [Group I] 5.The composition of claim 1, the first compound is one of compounds of Group 1: L 1 is a single bond, Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl, and Ar 1 and at least one of Ar 2 is substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl. [Group 1] L 1 is substituted or unsubstituted phenylene, and Ar 1 and Ar 2 each independently is a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

4. The composition of claim 1, wherein and each independently is selected from the group I substituents: 6.An organic optoelectric device comprising wherein In Group I, is a junction point. an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, [121] [122] [123] [124] 。 wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the composition for an organic optoelectric device according to any one of claims 1 to 5. 7.The organic optoelectric device of claim 6, wherein the compound for the organic optoelectric device or the composition for the organic optoelectric device is included in the light-emitting layer as a host. 8.A display device comprising the organic optoelectric device of claim 6. ​ ​ ​

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