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

Abstract

Provided are a compound for an organic photoelectric device, a composition for an organic photoelectric device, an organic photoelectric device and a display device, wherein the compound is represented by Chemical Formula 1, and the composition comprises the compound. The details of Chemical Formula 1 are as defined in the specification.

Description

Technical Field

[0001] Disclosed are a compound for an organic optoelectronic device (organic optoelectronic device, organic optoelectronic device, organic optoelectronic device, organic optoelectronic device), a composition for an organic optoelectronic device, an organic optoelectronic device and a display device (display device). Background Art

[0002] Organic photoelectric devices (organic photodiodes) are devices that can convert electrical energy into light energy and vice versa.

[0003] Organic optoelectronic devices can be roughly divided into two categories according to their working principles. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively, while the other is a light-emitting device that generates light energy from electrical energy by applying voltage or current to electrodes.

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

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

[0006] One embodiment provides a compound for an organic photoelectric device, which can realize an organic photoelectric device with high efficiency and long lifespan.

[0007] Another embodiment provides a composition for an organic photoelectric device including the compound.

[0008] Another embodiment provides an organic photoelectric device including the compound.

[0009] Another embodiment provides a display device including an organic photoelectric device.

[0010] According to one embodiment, a compound for an organic photoelectric device represented by Chemical Formula 1 is provided.

[0011] [Chemical formula 1]

[0012]

[0013] In Chemical Formula 1,

[0014] X 1 is O or S,

[0015] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0016] L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,

[0017] R 1 To R 6 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0018] R a and R b Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group.

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

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

[0021] [Chemical formula 2]

[0022]

[0023] In chemical formula 2,

[0024] X 2 O, S, NL a -R c , CR d R e or SiR f R g ,

[0025] L a is a single bond or a substituted or unsubstituted C6 to C12 arylene group,

[0026] R c is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0027] R d , Re , R f and R g are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0028] R 7 and R 8 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0029] A is any one selected from the rings of group II,

[0030] [Group II]

[0031]

[0032] Among them, in Group II,

[0033] * is the connection point,

[0034] X 3 is O or S,

[0035] R 10 To R 20 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0036] R c and R 7 To R 20 At least one of them is a group represented by chemical formula a,

[0037] [Chemical formula a]

[0038]

[0039] Among them, in chemical formula a,

[0040] Z 1 To Z 3 Each independently is N or CR h ,

[0041] Z 1 To Z 3 At least two of them are N,

[0042] R h is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0043] L 3 To L 5are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,

[0044] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and

[0045] * is the connection point.

[0046] According to another embodiment, an organic photoelectric device includes an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the organic layer includes a compound for an organic photoelectric device or a composition for an organic photoelectric device.

[0047] According to another embodiment, a display device including an organic photoelectric device is provided.

[0048] Organic optoelectronic devices with high efficiency and long lifetime can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0049] Figures 1 to 4 are cross-sectional views each showing an organic light emitting diode according to an embodiment.

[0050] <Description of Reference Numerals>

[0051] 100, 200, 300, 400: Organic light-emitting diodes

[0052] 105: Organic layer

[0053] 110: cathode

[0054] 120: Anode

[0055] 130: Luminous layer

[0056] 140: Hole transport region

[0057] 150: Electron transport region DETAILED DESCRIPTION

[0058] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0059] In the present specification, when no definition is otherwise provided, "substituted" means that at least one hydrogen of the substituent or the compound is replaced with deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl (silyl), C1 to C30 alkyl, C1 to C10 alkylsilyl (alkylsilyl), C6 to C30 arylsilyl (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.

[0060] In one example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0061] In the present specification, when a definition is not otherwise provided, "hetero" means including 1 to 3 hetero atoms selected from N, O, S, P and Si in one functional group and the rest are carbon atoms.

[0062] In the present specification, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and all elements of the hydrocarbon aromatic portion have p orbitals forming conjugation, such as phenyl, naphthyl, etc., two or more hydrocarbon aromatic portions may be connected by a σ bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic portions are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0063] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0064] In the present specification, "heterocyclic group" is a general concept of heteroaryl, 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, a condensed ring thereof or a combination thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0065] For example, "heteroaryl" refers to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls are directly connected by a sigma bond, or when the heteroaryl includes two or more rings, the two or more rings may be fused. When the heteroaryl is a fused ring, each ring may include one to three heteroatoms.

[0066] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted The invention may include, but is not limited to, a substituted or unsubstituted triphenylene group (triphenylene group), a substituted or unsubstituted peryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group, or a combination thereof.

[0067] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted benzothiophene, or a substituted or unsubstituted benzothiophene. The invention may include, but is not limited to, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazoline, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazinyl, a substituted or unsubstituted acridinyl, a substituted or unsubstituted phenazinyl, a substituted or unsubstituted phenothiazinyl, a substituted or unsubstituted phenoxazinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.

[0068] In this specification, 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.

[0069] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0070] Hereinafter, a compound for an organic photoelectric device according to one embodiment is described.

[0071] The compound for an organic photoelectric device according to one embodiment is represented by Chemical Formula 1.

[0072] [Chemical formula 1]

[0073]

[0074] In Chemical Formula 1,

[0075] X 1 is O or S,

[0076] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0077] L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,

[0078] R 1 To R 6 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0079] R a and R b Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group.

[0080] The compound for an organic photoelectric device represented by Chemical Formula 1 includes a skeleton in which dibenzosilole and benzofuran (or benzothiophene) are condensed, and an amine group is directly substituted in the direction of the dibenzosilole portion of the condensed skeleton.

[0081] Thus, by including a skeleton in which dibenzosilole and benzofuran (or benzothiophene) are fused, hole injection is faster, which is beneficial for the driving voltage of an organic light-emitting diode including the compound. In particular, since the amine group is directly substituted without a linking group, hole injection can be promoted and the driving voltage can be increased. Due to the direct substitution, the molecular weight of the compound is reduced, so the heat resistance stability can be improved.

[0082] Chemical Formula 1 may be represented by one of Chemical Formula 1-1 to Chemical Formula 1-4 depending on the connection position of the amine group.

[0083]

[0084]

[0085] In Chemical Formula 1-1 to Chemical Formula 1-4,

[0086] X 1 ,Ar 1 ,Ar 2 , L 1 , L 2 , R 1 To R 6 , R a and R b Same as above.

[0087] For example, Ar 1 and Ar 2 Each may independently be a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heterocyclic group.

[0088] As a specific example, Ar 1 and Ar 2 The phenyl radicals may be independently substituted or unsubstituted phenyl radicals, substituted or unsubstituted biphenyl radicals, substituted or unsubstituted terphenyl radicals, substituted or unsubstituted naphthyl radicals, substituted or unsubstituted anthracenyl radicals, substituted or unsubstituted phenanthrenyl radicals, substituted or unsubstituted fluorenyl radicals, substituted or unsubstituted substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzosilolyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, or substituted or unsubstituted benzoxazolyl.

[0089] In one embodiment, Ar 1 and Ar 2may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothioyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group, and Ar 1 and Ar 2 At least one of the groups may be a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

[0090] For example, L 1 and L 2 Each independently may be a single bond, or a substituted or unsubstituted C6 to C12 arylene group.

[0091] As a specific example, L 1 and L 2 Each independently may be a single bond, or a substituted or unsubstituted phenylene group.

[0092] For example, *-L 1 -Ar 1 and *-L 2 -Ar 2 The substituents may be each independently selected from Group I.

[0093] [Group I]

[0094]

[0095] In Group I, R i and R j Each may independently be a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0096] For example, R 1 To R 6 Each may independently be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C20 aryl.

[0097] As a specific example, R 1 To R 6 Each may independently be hydrogen, deuterium, cyano, halogen, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

[0098] For example, R 1 To R 6 Each may be hydrogen.

[0099] For example, R a and R b Each may independently be a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0100] As a specific example, R a and R b Each independently may be an unsubstituted methyl group, an unsubstituted ethyl group, an unsubstituted propyl group, an isopropyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0101] More specific examples of the compound for an organic photoelectric device represented by Chemical Formula 1 may include compounds of Group 1, but are not limited thereto.

[0102] [Group 1]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112] A composition for an organic photoelectric device according to another embodiment includes a first compound and a second compound, wherein the first compound may be the aforementioned compound for an organic photoelectric device, and the second compound may be a compound represented by Chemical Formula 2.

[0113] [Chemical formula 2]

[0114]

[0115] In chemical formula 2,

[0116] X 2 O, S, NL a -R c , CR d R e or SiR f Rg ,

[0117] L a is a single bond, or a substituted or unsubstituted C6 to C12 arylene group,

[0118] R c is a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0119] R d , R e , R f and R g are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

[0120] R 7 and R 8 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0121] A is one of the rings selected from Group II,

[0122] [Group II]

[0123]

[0124] In Group II,

[0125] * is the connection point,

[0126] X 3 is O or S,

[0127] R 9 To R 20 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0128] R c and R 7 To R 20 At least one of them is a group represented by chemical formula a,

[0129] [Chemical formula a]

[0130]

[0131] Among them, in chemical formula a,

[0132] Z 1 To Z 3 Each independently is N or CR h ,

[0133] Z 1 To Z 3 At least two of them are N,

[0134] R h is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl,

[0135] L 3 To L 5 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,

[0136] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and

[0137] * is the connection point.

[0138] Since the second compound effectively expands the LUMO energy band by being substituted with a nitrogen-containing 6-membered ring, when used in a light-emitting layer together with the above-mentioned first compound, the balance of holes and electrons can be increased, thereby improving the luminous efficiency and life characteristics of the device containing it and reducing the driving voltage.

[0139] Meanwhile, A of Chemical Formula 2 may be selected from the rings of Group II, and may be represented, for example, by any one of Chemical Formulae 2A to 2J.

[0140]

[0141]

[0142] In Chemical Formulae 2A to 2J,

[0143] X 2 , X 3 , Z 1 To Z 3 , R 7 To R 16 , R 18 To R 20 , L 3 To L 5 ,Ar 3 and Ar 4 Same as above.

[0144] According to one embodiment, Chemical Formula 2 may be represented by one of Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1, and Chemical Formula 2F-3.

[0145]

[0146] In Formula 2A-3, Formula 2C-1, Formula 2F-1 and Formula 2F-3, X 2 , Z 1 To Z 3 , R 7 To R 13 , L 3 To L 5 ,Ar 3 and Ar 4 Same as above.

[0147] For example, Ar 3 and Ar 4 Each of them may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilyl group.

[0148] As a specific example, Ar 3 and Ar 4 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0149] For example, L 3 To L 5 Each independently may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

[0150] For example, *-L 3 -Ar 3 and *-L 4 -Ar 4 The substituents may be selected from Group I.

[0151] For example, R 7 To R 20 Each may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C18 heterocyclic group.

[0152] As a specific example, R 7 To R 20 may each independently be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or a group represented by chemical formula a, and R 7 To R 20 At least one of them may be a group represented by Chemical Formula a.

[0153] For example, X2 Can be O, S, CR d R e or SiR f R g , where R d , R e , R f and R g Each independently may be a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

[0154] As a specific example, R d , R e , R f and R g Each independently may be an unsubstituted methyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0155] For example, the second compound may be one selected from the compounds of Group 2, but is not limited thereto.

[0156] [Group 2]

[0157]

[0158]

[0159]

[0160]

[0161] The composition for an organic photoelectric device according to a more specific embodiment of the present invention may include a first compound represented by Chemical Formula 1-2 and a second compound represented by any one of Chemical Formula 2A-3a, Chemical Formula 2C-1a, and Chemical Formula 2F-1a.

[0162] Ar in chemical formula 1-2 1 and Ar 2 and L may be each independently a phenyl group substituted or unsubstituted by a C6 to C12 aryl group, a biphenyl group substituted or unsubstituted by a C6 to C12 aryl group, a naphthyl group substituted or unsubstituted by a C6 to C12 aryl group, a carbazolyl group substituted or unsubstituted by a C6 to C12 aryl group, a dibenzofuranyl group substituted or unsubstituted by a C6 to C12 aryl group, a dibenzothiophenyl group substituted or unsubstituted by a C6 to C12 aryl group, a dibenzothiorol group substituted or unsubstituted by a C6 to C12 aryl group, a benzonaphthofuranyl group substituted or unsubstituted by a C6 to C12 aryl group, or a benzonaphthothiophenyl group substituted or unsubstituted by a C6 to C12 aryl group. 1 and L 2 may be independently a single bond, or a substituted or unsubstituted phenylene group, R 1 To R6 may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and R a and R b Each may independently be a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0163] Chemical Formula 2A-3a, Chemical Formula 2C-1a, and Chemical Formula 2F-1a can be expressed as follows.

[0164]

[0165] In Chemical Formula 2A-3a, Chemical Formula 2C-1a and Chemical Formula 2F-1a,

[0166] X 2 O, S, CR d R e or SiR f R g ,

[0167] Z 1 To Z 3 Each is N,

[0168] R d , R e , R f and R g are each independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,

[0169] R 9 is hydrogen, deuterium or phenyl,

[0170] L 3 To L 5 are each independently a single bond, or a substituted or unsubstituted phenylene group, and

[0171] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0172] The composition for an organic photoelectric device according to a more specific embodiment of the present invention may include a first compound selected from Group 1-1 and a second compound selected from Group 2-1.

[0173] [Group 1-1]

[0174]

[0175] [Group 2-1]

[0176]

[0177] For example, the first compound and the second compound may be included in a weight ratio of 1:99 to 99:1. Within this range, the electron transport capability of the first compound and the hole transport capability of the second compound may be utilized to adjust the desired weight ratio to achieve bipolar characteristics, thereby improving efficiency and lifespan. Within this range, for example, they may be included in a weight ratio of about 10:90 to 90:10, about 10:90 to 80:20, such as about 10:90 to about 70:30, about 10:90 to about 60:40, and about 10:90 to about 50:50. As a specific example, they may be included in a weight ratio of 20:80, 30:70, 40:60, or 50:50.

[0178] One or more compounds other than the aforementioned first compound and second compound may be further included.

[0179] The aforementioned compound for an organic photoelectric device or the composition for an organic photoelectric device may further include a dopant.

[0180] For example, the dopant may be a phosphorescent dopant, such as a red, green or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0181] A dopant is a material that is mixed in a small amount with a compound or composition for an organic photoelectric device to promote light emission, and generally may be a material that emits light by multiple excitation to a triplet state or a multiplet state, such as a metal complex. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0182] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0183] [Chemical formula Z]

[0184] L 6 MX 4

[0185] In the chemical formula Z, M is a metal, and L 6 and X 4 The same or different ligands that form a complex with M.

[0186] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 6 and X 4 This may be, for example, a bidentate ligand.

[0187] The aforementioned compound for an organic photoelectric device or the composition for an organic photoelectric device may be formed into a film by a dry film forming method such as chemical vapor deposition (CVD).

[0188] Hereinafter, an organic photoelectric device including the compound for an organic photoelectric device or the composition for an organic photoelectric device is described.

[0189] The organic photoelectric device may be any device that converts electrical energy into light energy and vice versa without particular limitation, and may be, for example, an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photoconductor drum.

[0190] Herein, an organic light emitting diode as one example of an organic photoelectric device is described with reference to the accompanying drawings.

[0191] Figures 1 to 4 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0192] refer to Figure 1 , an organic light emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0193] The anode 120 may be made of a conductor having a large work function to assist hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0194] The cathode 110 may be made of a conductor having a small work function to assist electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or the like, or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0195] The organic layer 105 may include the aforementioned compound for an organic photoelectric device or the composition for an organic photoelectric device.

[0196] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the aforementioned compound for an organic photoelectric device or a composition for an organic photoelectric device.

[0197] The composition for an organic photoelectric device further including a dopant may be, for example, a red-light-emitting composition.

[0198] The light emitting layer 130 may include, for example, the aforementioned first compound and the second compound as phosphorescent hosts, respectively.

[0199] The organic layer may further include a charge transport region in addition to the light emitting layer.

[0200] The charge transport region may be, for example, Figure 2 The hole transport zone 140 is shown in FIG.

[0201] refer to Figure 2 , the organic light emitting diode 200 further includes a hole transport region 140 in addition to the light emitting layer 130. 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 may include a hole transport layer between the anode 120 and the light emitting layer 130 and a hole transport auxiliary layer between the light emitting layer 130 and the hole transport layer, and at least one of the compounds of group E may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0202] [Group E]

[0203]

[0204]

[0205]

[0206]

[0207] In the hole transport region, in addition to the aforementioned compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds similar thereto can be used.

[0208] Furthermore, the charge transport region may be e.g. Figure 3 The electron transport region 150 is shown in FIG.

[0209] refer to Figure 3 In addition to the light emitting layer 130, the organic light emitting diode 300 further includes an electron transport region 150. The electron transport region 150 may further increase electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0210] Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130 and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer, and at least one of the electron transport layer and the electron transport auxiliary layer may include at least one compound of group F.

[0211] [Group F]

[0212]

[0213]

[0214]

[0215] One embodiment of the present invention may be as follows Figure 1 The organic light emitting diode shown includes a light emitting layer 130 as the organic layer 105 .

[0216] Another embodiment of the present invention can be as follows Figure 2 The organic light emitting diode shown includes a hole transport region 140 in addition to the light emitting layer 130 serving as the organic layer 105 .

[0217] Another embodiment of the present invention can be as follows Figure 3 The organic light emitting diode shown includes an electron transport region 150 in addition to the light emitting layer 130 serving as the organic layer 105 .

[0218] Another embodiment of the present invention can be as follows Figure 4 The organic light emitting diode shown includes, in addition to the light emitting layer 130 serving as the organic layer 105 , a hole transport region 140 and an electron transport region 150 .

[0219] Another embodiment of the present invention may be an organic light emitting diode, except that Figures 1 to 4 In each of the organic layers 105 , in addition to the light emitting layer 130 , an electron injection layer (not shown), a hole injection layer (not shown), and the like are further included.

[0220] The organic light emitting diodes 100, 200, 300 and 400 may be manufactured by forming an anode or a cathode on a substrate, forming an organic layer using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating and ion plating, and forming a cathode or an anode thereon.

[0221] The organic light emitting diode may be applied to an organic light emitting display device.

[0222] Hereinafter, the embodiments are described in more detail with reference to Examples. However, these Examples are exemplary, and the scope of the present invention is not limited thereto.

[0223] Hereinafter, unless otherwise noted, raw materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry or P&Htech, or synthesized by known methods.

[0224] (Preparation of compounds for organic optoelectronic devices)

[0225] The compound presented as a more specific example of the compound of the present invention was synthesized by the following steps.

[0226] Synthesis Example 1: Synthesis of Compound B-1

[0227] [Reaction Scheme 1]

[0228]

[0229] Step 1: Synthesize Int-3

[0230] Int-2 (2-bromo-4-chloro-1-iodobenzene: 208.74 g, 657.75 mmol) was dissolved in 2.0 L tetrahydrofuran (THF) and 1.0 L distilled water, and Int-1 (dibenzofuran-1-boric acid: 150.00 g, 657.75 mmol) and tetrakis(triphenylphosphine)palladium (22.8 g, 19.73 mmol) were added thereto, and then stirred. Subsequently, potassium carbonate (227.27 g, 1644.38 mmol) saturated in 1000 ml water was added thereto, and then heated to reflux at 80° C. for 12 hours. When the reaction was complete, water was added to the reaction solution, which was then extracted with ethyl acetate (EA) and treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain 178.78 g (76%) of Int-3.

[0231] Step 2: Synthesize Int-4

[0232] Int-3 (178.00 g, 497.72 mmol) was dissolved in 3000 mL of tetrahydrofuran (THF), and the internal temperature thereof was lowered to -78° C. Subsequently, n-BuLi (238.9 ml, 597.29 mmol) was added thereto in a dropwise manner while maintaining the internal temperature of -78° C., and then stirred at the temperature for 1 hour.

[0233] After slowly adding chlorodimethylsilane (71.31 ml, 622.15 mmol) dropwise at -78°C, the obtained mixture was stirred at room temperature for 12 hours. When the reaction was complete, water was added to the reaction solution, which was then extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain 92.22 g (55%) of Int-4.

[0234] Step 3: Synthesize Int-5

[0235] Int-4 (92.2 g, 273.68 mmol) was dissolved in 1000 mL trifluoromethylbenzene, and di-tert-butyl peroxide (153.14 ml, 821.04 mmol) was slowly added thereto in a dropwise manner. The resulting mixture was heated to reflux for 48 hours at an internal temperature of 120° C. When the reaction was complete, the reaction solution was cooled to room temperature, and 1000 ml of water was added thereto, and then stirred for 1 hour. The resulting product was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain 68.74 g (75%) of Int-5.

[0236] Step 4: Synthesis of Compound B-1

[0237] Int-5 3.38g (10.1mmol), Int-6 3.15g (10.1mmol), sodium tert-butoxide 2.42g (25.26mmol) and 0.41g (1.01mmol) tri-tert-butylphosphine were dissolved in 100ml dimethylbenzene, and 0.46g (0.51mmol) Pd2 (dba) 3 was added thereto, and then stirred and refluxed for 12 hours under a nitrogen atmosphere. When the reaction was complete, after extraction with dimethylbenzene and distilled water, the organic layer thus obtained was dried with anhydrous magnesium sulfate, filtered, and the filtrate thus obtained was concentrated under reduced pressure. The product thus obtained was purified by silica gel column chromatography using n-hexane / dichloromethane (volume ratio 2: 1), and 4.6g (yield: 77%) of compound B-1 were obtained.

[0238] Calculated for C42H31NOSi: C, 84.95; H, 5.26; N, 2.36; O, 2.69; Si, 4.73; Measured: C, 84.95; H, 5.26; N, 2.36; O, 2.69; Si, 4.73.

[0239] Synthesis Example 2: Synthesis of Compound C-1

[0240] [Reaction Scheme 2]

[0241]

[0242] Compound C-1 was synthesized in the same manner as in Synthesis Example 1 except that Int-7 (dibenzothiophene-1-boronic acid) was used instead of Int-1 as shown in Reaction Scheme 2.

[0243] Calculated for C42H31NSSi: C, 82.72; H, 5.12; N, 2.30; S, 5.26; Si, 4.61; Measured: C, 82.71; H, 5.12; N, 2.30; S, 5.26; Si, 4.61.

[0244] Synthesis of Synthesis Examples 3 to 24

[0245] Each compound was synthesized in the same manner as in Synthesis Example 1 or Synthesis Example 2, except that Int A in Table 1 was used instead of Int-5 in Synthesis Example 1, and Int B in Table 1 was used instead of Int-6.

[0246] (Table 1)

[0247]

[0248]

[0249] [Int A]

[0250]

[0251] [Int B]

[0252]

[0253] Synthesis Example 25: Synthesis of Compound A-3 [Reaction Scheme 3]

[0254]

[0255] Step 1: Synthesize Int-29

[0256] In a round-bottom flask, 22.6 g (100 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine was added to 200 mL of tetrahydrofuran and 100 mL of distilled water, to which 0.9 equivalents of Int-28 (dibenzofuran-3-boric acid, CAS No.: 395087-89-5), 0.03 equivalents of tetrakistriphenylphosphine palladium and 2 equivalents of potassium carbonate were added, and then heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and after removing the water layer, the organic layer thus obtained was dried under reduced pressure. The obtained solid was washed with water and hexane, and then recrystallized using 200 mL of toluene to obtain 21.4 g (yield: 60%) of Int-29.

[0257] Step 2: Synthesize Int-30

[0258] In a round-bottom flask, 50.0 g (261.16 mmol) of 1-bromo-4-chlorobenzene, 44.9 g (261.16 mmol) of 2-naphthaleneboric acid, 9.1 g (7.83 mmol) of tetrakistriphenylphosphine palladium and 71.2 g (522.33 mmol) of potassium carbonate were dissolved in 1000 mL of tetrahydrofuran and 500 mL of distilled water, and then heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and after removing the water layer therefrom, the organic layer obtained therefrom was dried under reduced pressure. The solid obtained was washed with water and hexane, and recrystallized with 200 mL of toluene to obtain 55.0 g (yield: 88%) of Int-30.

[0259] Step 3: Synthesize Int-31

[0260] In a round-bottomed flask, 100.0 g (418.92 mmol) of the synthesized Int-30 was added to 1000 mL of DMF, and 17.1 g (20.95 mmol) of dichlorodiphenylphosphinoferrocene palladium, 127.7 g (502.70 mmol) of bispinacol diboron and 123.3 g (1256.76 mmol) of potassium acetate were added thereto, and then heated to reflux for 12 hours under a nitrogen atmosphere. The reaction solution was cooled and added dropwise to 2 L of water to capture the solid. The solid was dissolved in boiling toluene, and then filtered through silica gel to concentrate the filtrate. After the concentrated solid was stirred with a small amount of hexane, the solid was filtered out to obtain 28.5 g (yield: 70%) of Int-31.

[0261] Step 4: Synthesis of Compound A-3

[0262] In a round-bottom flask, 10.0 g (27.95 mmol) of Int-31, 11.1 g (33.54 mmol) of Int-29, 1.0 g (0.84 mmol) of tetrakistriphenylphosphine palladium and 7.7 g (55.90 mmol) of potassium carbonate were dissolved in 150 mL of tetrahydrofuran and 75 mL of distilled water, and then heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, and after removing the water layer, the organic layer thus obtained was dried under reduced pressure. The obtained solid was washed with water and methanol, and recrystallized using 200 mL of toluene to obtain 13.4 g (yield: 91%) of compound A-3.

[0263] Calculated for C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Measured: C, 84.55; H, 4.41; N, 8.00; O, 3.03.

[0264] Synthesis Example 26: Synthesis of Compound A-71

[0265] [Reaction Scheme 4]

[0266]

[0267] Step 1: Synthesize Int-32

[0268] Int-32 was synthesized by the same method as Int-29 of Synthesis Example 25, except that 1.0 equivalent of 2,4-dichloro-6-phenyl-1,3,5-triazine and 1-phenyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-dibenzofuran were used respectively.

[0269] Step 2: Synthesis of Compound A-71

[0270] Compound A-71 was synthesized according to the same method as step 4 of Synthesis Example 25, except that 1.0 equivalent of Int-32 and Int-31 were used respectively.

[0271] Calculated for C43H27N3O: C, 85.83; H, 4.52; N, 6.98; O, 2.66; Measured: C, 85.83; H, 4.52; N, 6.98; O, 2.66.

[0272] Synthesis Example 27: Synthesis of Compound A-61

[0273] [Reaction Scheme 5]

[0274]

[0275] Step 1: Synthesize Int-33

[0276] In a round-bottom flask, 21.95 g (135.53 mmol) of 2-benzofuranboronic acid, 26.77 g (121.98 mmol) of 2-bromo-5-chlorobenzaldehyde, 2.74 g (12.20 mmol) of Pd(OAc) and 25.86 g (243.96 mmol) of NaCO were suspended in 200 ml of acetone / 220 ml of distilled water and then stirred at room temperature for 12 hours. When the reaction was complete, the resultant was concentrated and then extracted with dichloromethane, and the organic layer thus obtained was passed through a silica gel column to obtain 21.4 g (yield: 68%) of Int-33.

[0277] Step 2: Synthesize Int-34

[0278] 20.4g (79.47mmol) Int-33 and 29.97g (87.42mmol) (methoxymethyl) triphenylphosphonium chloride are suspended in 400ml THF, and 10.70g (95.37mmol) potassium tert-butoxide is added thereto, then at room temperature, stirred for 12 hours. When the reaction is complete, 400ml distilled water is added thereto, then extraction, the organic layer thus obtained is concentrated, extracted again with dichloromethane, and in the organic layer, magnesium sulfate is added, then stirred for 30 minutes, filtered, and then concentrated filtrate. In concentrated filtrate, 100ml dichloromethane is added again, 10ml methylsulfonic acid is added thereto, then stirred for 1 hour.

[0279] When the reaction was completed, a solid produced therein was filtered and then washed with distilled water and methanol to obtain 21.4 g (yield: 65%) of Int-34.

[0280] Step 3: Synthesize Int-35

[0281] 12.55 g (49.66 mmol) of Int-34, 2.43 g (2.98 mmol) of Pd(dppf)Cl2, 15.13 g (59.60 mmol) of bis(pinacolato)diboron, 14.62 g (148.99 mmol) of KOAc and 3.34 g (11.92 mmol) of P(Cy)3 were suspended in 200 ml of DMF and then refluxed with stirring for 12 hours. When the reaction was completed, 200 ml of distilled water was added thereto, the solid produced therein was filtered, and then extracted with dichloromethane, and the organic layer was passed through a column using hexane:EA=4:1 (v / v) to obtain 13 g (yield: 76%) of Int-35.

[0282] Step 4: Synthesis of Compound A-61

[0283] Compound A-61 was synthesized by the same method as in Step 4 of Synthesis Example 25, except that 1.0 equivalent of Int-35 and Int-36 were used respectively.

[0284] Calculated for C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Measured: C, 84.55; H, 4.41; N, 7.99; O, 3.04.

[0285] Synthesis Example 28: Synthesis of Compound A-17

[0286] [Reaction Scheme 6]

[0287]

[0288] Compound A-17 was synthesized by the same method as in Step 4 of Synthesis Example 25, except that 1.0 equivalent of Int-37 and Int-38 were used respectively.

[0289] Calculated for C41H25N3O: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Measured: C, 85.53; H, 4.38; N, 7.30; O, 2.77.

[0290] Synthesis Example 29: Synthesis of Compound A-37

[0291] [Reaction Scheme 7]

[0292]

[0293] Compound A-37 was synthesized by the same method as in Step 4 of Synthesis Example 25, except that 1.0 equivalent of Int-37 and Int-36 were used respectively.

[0294] Calculated for C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Measured: C, 84.57; H, 4.40; N, 7.99; O, 3.03.

[0295] Synthesis of Synthesis Examples 30 to 32

[0296] Each compound was synthesized in the same manner as in Step 4 of Synthesis Example 25, except that Int C in Table 2 was used instead of Int-31 and Int D in Table 2 was used instead of Int-29.

[0297] (Table 2)

[0298]

[0299]

[0300] [Int C]

[0301]

[0302] [Int D]

[0303]

[0304] Comparative Synthesis Example 1: Synthesis of Comparative Compound 1

[0305] [Reaction Scheme 8]

[0306]

[0307] Step 1: Synthesize Int-45

[0308] Int-2 (100 g, 315.11 mmol) was dissolved in 1.0 L tetrahydrofuran (THF), and Int-44 (63.28 g, 315.11 mmol) and tetrakis (triphenylphosphine) palladium (10.92 g, 9.45 mmol) were added thereto, and then stirred. Subsequently, potassium carbonate (108.88 g, 787.77 mmol) saturated in 500 ml of water was heated to reflux for 12 hours at 80 ° C. When the reaction was complete, water was added to the reaction solution, which was then extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain 86.24 g (79%) of Int-45.

[0309] Step 2: Synthesize Int-46

[0310] Int-45 (86.24 g, 248.92 mmol) was dissolved in 600 mL of tetrahydrofuran (THF), and the internal temperature was lowered to -78° C. Subsequently, n-BuLi (288.75 ml, 721.88 mmol) was slowly added thereto in a dropwise manner while maintaining the internal temperature at -78° C., and then stirred at the temperature for 1 hour.

[0311] Dichlorodimethylsilane (104.31 ml, 871.24 mmol) was slowly added dropwise thereto while maintaining at -78°C, and the resulting mixture was stirred at room temperature for 12 hours. When the reaction was complete, water was added to the reaction solution, extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain 43.12 g (71%) of Int-46.

[0312] Step 3: Synthesis of comparative compound 1

[0313] Comparative Compound 1 (5.69 g, 72%) was synthesized in the same manner as Synthesis Example 1, except that Int-46 was used instead of Int-5.

[0314] Calculated for C36H29NSi: C, 85.84; H, 5.80; N, 2.78; Si, 5.58; Measured: C, 85.84; H, 5.80; N, 2.78; Si, 5.58.

[0315] Comparative Synthesis Example 2: Synthesis of Comparative Compound 2

[0316] [Reaction Scheme 9]

[0317]

[0318] Comparative Compound 2 (4.86 g, 76%) was synthesized in the same manner as Synthesis Example 1, except that Int-50 was used instead of Int-5.

[0319] Calculated for C40H31NSi: C, 86.76; H, 5.64; N, 2.53; Si, 5.07; Measured: C, 86.77; H, 5.64; N, 2.53; Si, 5.06.

[0320] Comparative Synthesis Example 3: Synthesis of Comparative Compound 3

[0321] [Reaction Scheme 10]

[0322]

[0323] Steps 1 to 3: Synthesis of Int-55

[0324] Int-55 (8.20 g, 56%) was synthesized in the same manner as Int-5 in Synthesis Example 1.

[0325] Step 4: Synthesis of comparative compound 3

[0326] In a round-bottom flask, 8.67g (17.19mmol) of Int-55, 9.28g (17.19mmol) of Int-56, 22.41g (34.39mmol) of cesium carbonate and 0.31g (1.55mmol) of tri-tert-butylphosphine were dissolved in 170ml of 1,4-dioxane, and 0.47g (0.52mmol) of Pd2(dba)3 was added thereto, and heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, and the organic layer was dried under reduced pressure. The solid thus obtained was washed with water and methanol and recrystallized using 70mL of toluene to obtain comparative compound 3 (8.34g, 59%).

[0327] Calculated for C60H41NOSi: C, 87.88; H, 5.04; N, 1.71; O, 1.95; Si, 3.42; Measured: C, 87.89; H, 5.04; N, 1.71; O, 1.94; Si, 3.42.

[0328] (Manufacturing organic light-emitting diodes) - Single body

[0329] Example 1

[0330] The glass substrate coated with ITO (indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. The ITO transparent electrode thus obtained was used as an anode, and compound A doped with 1% NDP-9 (available from Novaled) was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form Compound B is deposited on the hole transport layer to form On the hole transport auxiliary layer, a thick hole transport auxiliary layer was formed by using the compound B-1 of Synthesis Example 1 as a host and doping 10 wt% [Ir(piq)2acac] as a dopant Subsequently, compound C is deposited on the light-emitting layer to form The thick electron transport auxiliary layer is formed by vacuum depositing compound D and LiQ at a weight ratio of 1:1 simultaneously. The thick electron transport layer. LiQ is vacuum deposited on the electron transport layer in sequence. and Al To form a cathode, thereby manufacturing an organic light emitting diode.

[0331] ITO / Compound A (1% NDP-9 doping, ) / Compound A / Compound B / EML[Compound B-1 (98 wt%):[Ir(piq)2acac](2 wt%)] / Compound C / Compound D:

[0332] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0333] Compound B: N,N-di([1,1'-diphenyl]-4-yl)-7,7-dimethyl-7H-fluoren[4,3-b]benzofuran-10-amine

[0334] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0335] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazine-2-yl)phenyl)quinolone

[0336] Examples 2 to 24 and Comparative Examples 1 to 3

[0337] Diodes of Examples 2 to 24 and Comparative Examples 1 to 3 were manufactured in the same manner as in Example 1, except that the main body was changed as shown in Table 3.

[0338] (Manufacturing organic light-emitting diodes) - Dual-body

[0339] Embodiment 25

[0340] The glass substrate coated with ITO (indium tin oxide) was washed with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and moved to a vacuum depositor. The ITO transparent electrode thus obtained was used as an anode, and compound A doped with 1% NDP-9 (available from Novaled) was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form Compound B is deposited on the hole transport layer to form On the hole transport auxiliary layer, by using the compound B-1 of Synthesis Example 1 and the compound A-3 of Synthesis Example 25 as the host and doping 2wt% [Ir(piq)2acac] as a dopant, a Herein, compound B-1 and compound A-3 are used in a weight ratio of 5:5. Subsequently, compound C is deposited on the light-emitting layer to form The thick electron transport auxiliary layer is formed by vacuum depositing compound D and LiQ at a weight ratio of 1:1 simultaneously. The thick electron transport layer. LiQ is vacuum deposited on the electron transport layer in sequence. and Al To form a cathode, thereby manufacturing an organic light emitting diode.

[0341] ITO / Compound A (1% NDP-9 doping, ) / Compound A / Compound B / EML[98wt% host (compound B-1:compound A-3=5:5), 2wt% dopant (Ir(piq)2acac)] / Compound C / Compound D:

[0342] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0343] Compound B: N,N-di([1,1'-diphenyl]-4-yl)-7,7-dimethyl-7H-fluoren[4,3-b]benzofuran-10-amine

[0344] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0345] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazine-2-yl)phenyl)quinolone

[0346] Examples 26 to 43 and Comparative Examples 4 to 6

[0347] Diodes of Examples 26 to 43 and Comparative Examples 4 to 6 were manufactured in the same manner as in Example 25, except that the main body was changed as shown in Table 4.

[0348] evaluate

[0349] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light emitting diodes according to Examples 1 to 43 and Comparative Examples 1 to 6 were evaluated. The specific measurement method is as follows.

[0350] (1) Measuring the change in current density based on the change in voltage

[0351] 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 obtain the result.

[0352] (2) Measuring brightness changes based on voltage changes

[0353] 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-1000 A).

[0354] (3) Measurement of luminous efficiency

[0355] By using the luminance and current density from items (1) and (2), we calculated the 2 ) under luminous efficiency (cd / A).

[0356] (4) Measurement life

[0357] The brightness (cd / m 2 ) maintained at 5,000cd / m 2 , measure the time when the current efficiency (cd / A) drops to 90% and obtain the result.

[0358] (5) Measure the driving voltage

[0359] An ampere-voltmeter (Keithley 2400) was used at 15 mA / cm 2 The driving voltage of each diode is measured and the results are obtained.

[0360] (6) Calculate T90 life ratio (%)

[0361] Using T90(h) of Comparative Example 2 in Table 3 and T90(h) of Comparative Example 5 in Table 4 as respective reference values, relative comparative values ​​of respective T90(h) values ​​were calculated and shown in Tables 3 and 4.

[0362] (7) Calculate the driving voltage ratio (%)

[0363] Using the driving voltages of Comparative Example 2 in Table 3 and the driving voltages of Comparative Example 5 in Table 4 as reference values, relative comparative values ​​of the driving voltages were calculated and shown in Tables 3 and 4.

[0364] (8) Calculate the luminous efficiency ratio (%)

[0365] Using the luminous efficiency (cd / A) of Comparative Example 2 in Table 3 and Comparative Example 5 in Table 4 as respective reference values, relative comparative values ​​of respective luminous efficiency (cd / A) were calculated and shown in Tables 3 and 4.

[0366] (Table 3)

[0367] First Subject Driving voltage(V) Luminous efficiency (cd / A) Lifespan T90(h) Example 1 B-1 95％ 107％ 118％ Example 2 B-2 92％ 107％ 127％ Example 3 B-3 93％ 109％ 128％ Example 4 B-4 93％ 106％ 125％ Example 5 B-5 94％ 110％ 116％ Example 6 B-10 92％ 109％ 128％ Example 7 B-18 94％ 111％ 124％ Example 8 B-25 91％ 109％ 126％ Example 9 B-29 94％ 110％ 121％ Example 10 B-41 94％ 108％ 120％ Embodiment 11 B-42 91％ 106％ 124％ Example 12 B-49 95％ 105％ 113％ Example 13 B-69 93％ 108％ 124％ Embodiment 14 B-73 93％ 107％ 127％ Embodiment 15 B-85 95％ 106％ 111％ Example 16 B-89 95％ 107％ 114％ Embodiment 17 B-93 96％ 110％ 110％ Embodiment 18 B-107 92％ 111％ 117％ Embodiment 19 C-1 95％ 108％ 118％ Embodiment 20 C-4 94％ 106％ 125％ Embodiment 21 C-5 95％ 109％ 115％ Embodiment 22 C-29 93％ 109％ 121％ Embodiment 23 C-69 94％ 108％ 120％ Embodiment 24 C-73 94％ 106％ 125％ Comparative Example 1 Comparative Compound 1 109％ 92％ 92％ Comparative Example 2 Comparative Compound 2 100％ 100％ 100％ Comparative Example 3 Comparative Compound 3 107％ 94％ 93％

[0368] (Table 4)

[0369]

[0370] Referring to Table 3 and Table 4, the compounds according to the present invention significantly exhibit improved driving voltage, efficiency and lifespan compared to the comparative compounds.

[0371] While the invention has been described in connection with what are presently considered to be practical embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary, the invention is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: [Chemical formula 1] in, In Chemical Formula 1, X 1 is O or S, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, R 1 To R 6 are each independently hydrogen or deuterium, R a and R b are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and "Substituted" means that at least one hydrogen of the substituent is replaced with deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano.

2. The compound for an organic optoelectronic device according to claim 1, wherein Chemical formula 1 is represented by one of Chemical formula 1-1 to Chemical formula 1-4: Among them, in Chemical Formula 1-1 to Chemical Formula 1-4, X 1 ,Ar 1 ,Ar 2 , L 1 , L 2 , R 1 To R 6 , R a and R b Same as defined in claim 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, or substituted or unsubstituted benzoxazolyl.

4. The compound for an organic optoelectronic device according to claim 1, wherein *-L 1 -Ar 1 and *-L 2 -Ar 2 Each substituent is independently selected from Group I: [Group I] Among them, in group I, R i and R j are independently substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, and * is the connection point.

5. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted dibenzothioyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl, and Ar 1 and Ar 2 At least one of the following is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzothioyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

6. The compound for an organic optoelectronic device according to claim 1, wherein R a and R b Each is independently an unsubstituted methyl group, an unsubstituted ethyl group, an unsubstituted propyl group, an isopropyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

7. The compound for an organic optoelectronic device according to claim 1, wherein The compound is one of the compounds of Group 1: [Group 1] 8. A composition for an organic optoelectronic device, comprising a first compound and a second compound, in, The first compound is the compound for an organic photoelectric device according to claim 1, The second compound is represented by Chemical Formula 2: [Chemical formula 2] Wherein, in Chemical Formula 2, X 2 O, S, NL a -R c , CR d R e or SiR f R g , L a is a single bond, or a substituted or unsubstituted C6 to C12 arylene group, R c is a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, R d , R e , R f and R g are each independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, R 7 and R 8 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group, and A is one of the rings selected from Group II, [Group II] Among them, in Group II, * is the connection point, X 3 is O or S, R 9 To R 20 are each independently hydrogen, deuterium, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and R c and R 7 To R 20 At least one of them is a group represented by chemical formula a, [Chemical formula a] Among them, in chemical formula a, Z 1 To Z 3 Each independently is N or CR h , Z 1 To Z 3 At least two of them are N, R h is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl, L 3 To L 5 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group, and * is the connection point.

9. The composition for an organic optoelectronic device according to claim 8, wherein The second compound is represented by one of Chemical Formula 2A to Chemical Formula 2J: Among them, in Chemical Formulae 2A to 2J, X 2 , X 3 , Z 1 To Z 3 , R 7 To R 16 , R 18 To R 20 , L 3 To L 5 ,Ar 3 and Ar 4 Same as defined in claim 8.

10. The composition for an organic optoelectronic device according to claim 9, wherein The second compound is represented by one of Chemical Formula 2A, Chemical Formula 2C, and Chemical Formula 2F.

11. The composition for an organic optoelectronic device according to claim 8, wherein The second compound is represented by one of Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1 and Chemical Formula 2F-3: Among them, in Chemical Formula 2A-3, Chemical Formula 2C-1, Chemical Formula 2F-1 and Chemical Formula 2F-3, X 2 , Z 1 To Z 3 , R 7 To R 13 , L 3 To L 5 ,Ar 3 and Ar 4 Same as defined in claim 8.

12. The composition for an organic optoelectronic device according to claim 8, wherein Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilyl group.

13. The composition for an organic optoelectronic device according to claim 8, wherein The second compound is one of the compounds of Group 2: [Group 2] 14. The composition for an organic photoelectric device according to claim 8, wherein the first compound is represented by Chemical Formula 1-2, and The second compound is represented by one of Chemical Formula 2A-3a, Chemical Formula 2C-1a and Chemical Formula 2F-1a: [Chemical formula 1-2] in, In Chemical Formula 1-2, X 1 is O or S, Ar 1 and Ar 2 each independently represents a phenyl group which may be substituted by a C6 to C12 aryl group, a biphenyl group which may be substituted by a C6 to C12 aryl group, a naphthyl group which may be substituted by a C6 to C12 aryl group, a carbazolyl group which may be substituted by a C6 to C12 aryl group, a dibenzofuranyl group which may be substituted by a C6 to C12 aryl group, a dibenzothiophenyl group which may be substituted by a C6 to C12 aryl group, a dibenzothiorol group which may be substituted by a C6 to C12 aryl group, a benzonaphthofuranyl group which may be substituted by a C6 to C12 aryl group, or a benzonaphthothiophenyl group which may be substituted by a C6 to C12 aryl group, L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted phenylene group, R 1 To R 6 are each independently hydrogen or deuterium, and R a and R b Each is independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group; [Chemical formula 2F-1a] Among them, in Chemical Formula 2A-3a, Chemical Formula 2C-1a and Chemical Formula 2F-1a, X 2 O, S, CR d R e or SiR f R g , Z 1 To Z 3 Each is N, R d , R e , R f and R g are each independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, R 9 is hydrogen, deuterium or phenyl, L 3 To L 5 are each independently a single bond, or a substituted or unsubstituted phenylene group, and Ar 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

15. An organic optoelectronic device, comprising: an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, The organic layer comprises the compound for an organic photoelectric device according to any one of claims 1 to 7 or the composition for an organic photoelectric device according to any one of claims 8 to 14.

16. The organic optoelectronic device according to claim 15, wherein The organic layer includes a light-emitting layer, and The light-emitting layer comprises the compound for an organic photoelectric device according to any one of claims 1 to 7 or the composition for an organic photoelectric device according to any one of claims 8 to 14.

17. A display device comprising the organic photoelectric device according to claim 15.

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