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

Abstract

The present application relates to compounds for organic optoelectronic devices, organic optoelectronic devices, and displays. The present application provides compounds for organic optoelectronic devices represented by Chemical Formula I, organic optoelectronic devices containing the same, and displays. The details of Chemical Formula I are as defined in the specification. The present invention can achieve high-efficiency and long-life organic optoelectronic devices.

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0117782, filed on September 3, 2021, in the Korean Intellectual Property Office, and Korean Patent Application No. 10-2022-0110104, filed on August 31, 2022, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

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

[0004] An organic photovoltaic device (organic photodiode) is a device that converts electrical energy into light energy (or vice versa).

[0005] Organic optoelectronic devices can be categorized as follows based on their driving principles: One type is a photoelectric device in which excitons generated by light energy are separated into electrons and holes, which are then transferred to different electrodes to generate electrical energy; the other type is a light-emitting device in which electrical energy is converted to light energy by supplying voltage or current to electrodes.

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

[0007] Among them, organic light emitting diodes (OLEDs) have recently attracted attention due to the increasing demand for flat panel displays. OLEDs convert electrical energy into light, and the organic material disposed between electrodes has a significant impact on the performance of OLEDs. Summary of the Invention

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

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

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

[0011] According to one embodiment, a compound for an organic optoelectronic device represented by Chemical Formula I is provided.

[0012] [Chemical Formula I]

[0013]

[0014] In Chemical Formula I,

[0015] L 1 is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0016] R 1 to R 7 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, substituted or unsubstituted silanyl, substituted or unsubstituted amine, halogen, cyano, or a combination thereof,

[0017] m1 to m5 are each independently one of integers from 1 to 4,

[0018] m6 and m7 are each independently one of integers from 1 to 3, and

[0019] Chemical formula I satisfies at least one of the following conditions:

[0020] (i)L 1 is a C6 to C20 arylene group substituted by at least one deuterium group or a C2 to C20 heterocyclyl group substituted by at least one deuterium group; and

[0021] (ii)R 1 to R 7 At least one of is deuterium, a C6 to C30 aryl group substituted by at least one deuterium, or a C2 to C30 heterocyclic group substituted by at least one deuterium.

[0022] According to another embodiment, an organic photoelectric device includes an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes a compound for an organic photoelectric device.

[0023] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0024] High-efficiency and long-life organic photovoltaic devices can be achieved. BRIEF DESCRIPTION OF THE DRAWINGS

[0025] Figure 1 is a cross-sectional view illustrating an organic light emitting diode according to an embodiment.

[0026] <Description of Reference Numerals>

[0027] 100: Organic Light-Emitting Diode

[0028] 105: Organic layer

[0029] 110: cathode

[0030] 120: Anode

[0031] 130: Luminous layer

[0032] 140: Hole transport zone

[0033] 150: Electron transport region DETAILED DESCRIPTION

[0034] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary and the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0035] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl (silyl, silyl), C1 to C30 alkyl, C1 to C10 alkylsilyl (alkylsilyl, alkylsilyl), C6 to C30 arylsilyl (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.

[0036] In one embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In addition, in a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In addition, in a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In addition, in a specific embodiment of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0037] "Unsubstituted" means that a hydrogen atom is not replaced by another substituent and that a hydrogen atom remains.

[0038] As used herein, a "hydrogen substituent (—H)" may include a "deuterium substituent (—D)" or a "tritium substituent (—T)."

[0039] As used herein, when no definition is otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0040] As used herein, “aryl” refers to a group containing at least one hydrocarbon aromatic moiety, and may include a group in which all elements of the hydrocarbon aromatic moiety have p-orbitals forming a conjugation, such as phenyl, naphthyl, etc., a group in which two or more hydrocarbon aromatic moieties can be linked by a σ bond, such as biphenyl, terphenyl, quaterphenyl, etc., and a group in which two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl, etc.

[0041] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.

[0042] As used herein, "heterocyclic group" is a general concept of heteroaryl groups, and may contain at least one heteroatom selected from N, O, S, P and Si instead of carbon (C) in cyclic compounds such as aryl groups, cycloalkyl groups, condensed rings thereof, or combinations thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0043] For example, "heteroaryl" refers to an aryl group containing 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 may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0044] 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 present invention may include, but is not limited to, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0045] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothienyl group , substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, or a combination thereof, but are not limited thereto.

[0046] In this specification, hole characteristics refer to the ability to donate electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0047] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductive properties 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.

[0048] Hereinafter, a compound for an organic photoelectric device according to one embodiment is described.

[0049] A compound for an organic photoelectric device according to one embodiment is represented by Chemical Formula I.

[0050] [Chemical Formula I]

[0051]

[0052] In Chemical Formula I,

[0053] L 1 is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0054] R 1 to R 7are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group (silyl group), a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,

[0055] m1 to m5 are each independently one of integers from 1 to 4, and

[0056] m6 and m7 are each independently one of integers from 1 to 3,

[0057] Chemical formula I satisfies at least one of the following conditions (i) and (ii).

[0058] (i)L 1 is a C6 to C20 arylene group substituted by at least one deuterium group or a C2 to C20 heterocyclyl group substituted by at least one deuterium group; and

[0059] (ii)R 1 to R 7 At least one of is deuterium, a C6 to C30 aryl group substituted by at least one deuterium, or a C2 to C30 heterocyclic group substituted by at least one deuterium.

[0060] The compound represented by Chemical Formula I has a structure in which triphenylene is substituted with spirofluorene as a basic skeleton, and has a structure in which the basic skeleton is substituted with at least one deuterium.

[0061] This compound can have lower zero-point energy and vibrational energy due to the substitution of at least one deuterium. As a result, the ground state energy is further reduced, and thin films formed from it can become amorphous due to weakened intermolecular interactions. This further improves heat resistance and lifetime. Specifically, its application can realize highly efficient, and particularly long-lived, organic light-emitting diodes.

[0062] For example, L 1 can be a single bond, and R 1 to R 7 At least one of may be deuterium, a C6 to C30 aryl group substituted with at least one deuterium, or a C2 to C30 heterocyclic group substituted with at least one deuterium.

[0063] For example, L 1 It may be a C6 to C20 arylene group substituted by at least one deuterium group or a C2 to C20 heterocyclic group substituted by at least one deuterium group, and R 1 to R 7 At least one of may be deuterium, a C6 to C30 aryl group substituted with at least one deuterium, or a C2 to C30 heterocyclic group substituted with at least one deuterium.

[0064] In one embodiment, L 1 It may be a phenylene group substituted by at least one deuterium group, a biphenylene group substituted by at least one deuterium group, a terphenylene group substituted by at least one deuterium group, a naphthylene group substituted by at least one deuterium group, an anthrylene group substituted by at least one deuterium group, a phenanthrenyl group substituted by at least one deuterium group, a triphenylene group substituted by at least one deuterium group, a fluorenylene group substituted by at least one deuterium group, a carbazolylene group substituted by at least one deuterium group, a dibenzofuranyl group substituted by at least one deuterium group, or a dibenzothiophenylene group substituted by at least one deuterium group.

[0065] For example, L 1 It may be a single bond, a phenylene group substituted by at least one deuterium group, a naphthylene group substituted by at least one deuterium group, a carbazolylene group substituted by at least one deuterium group, a dibenzofuranyl group substituted by at least one deuterium group, or a dibenzothiophenyl group substituted by at least one deuterium group.

[0066] In one embodiment, R 1 to R 7 At least one of the groups may be deuterium, a phenyl group substituted by at least one deuterium group, a biphenyl group substituted by at least one deuterium group, a terphenyl group substituted by at least one deuterium group, a naphthyl group substituted by at least one deuterium group, an anthracenyl group substituted by at least one deuterium group, a phenanthrenyl group substituted by at least one deuterium group, a triphenylene group substituted by at least one deuterium group, a fluorenyl group substituted by at least one deuterium group, a carbazolyl group substituted by at least one deuterium group, a dibenzofuranyl group substituted by at least one deuterium group, or a dibenzothiophenyl group substituted by at least one deuterium group.

[0067] For example, R 1 to R 7 At least one of the groups may be deuterium, a phenyl group substituted by at least one deuterium, a carbazolyl group substituted by at least one deuterium, a dibenzofuranyl group substituted by at least one deuterium, or a dibenzothiophenyl group substituted by at least one deuterium.

[0068] For example, depending on the specific substitution site of triphenylene on spirofluorene, Chemical Formula I may be represented by any one of Chemical Formulas I-1 to I-4.

[0069]

[0070]

[0071] In Chemical Formulas I-1 to II-4, L 1 、R 1 to R 7 , and m1 to m7 are the same as above.

[0072] For example, Chemical Formula I can be represented by Chemical Formula I-4.

[0073] Specifically, L in Chemical Formula I-41 The phenylene group may be a single bond or substituted with at least one deuterium group.

[0074] Specifically, R in Chemical Formula I-4 1 to R 7 can be hydrogen, deuterium, substituted or unsubstituted phenyl, or substituted or unsubstituted carbazolyl, and R 1 to R 7 At least one of the may be deuterium, a phenyl group substituted by at least one deuterium, or a carbazolyl group substituted by at least one deuterium.

[0075] For example, L in chemical formula I-4 1 It may be a m-phenylene group substituted with at least one deuterium group or a p-phenylene group substituted with at least one deuterium group.

[0076] For example, L 1 It may be a phenylene group substituted with deuterium, and may be one of the linking groups of Group I.

[0077] [Group I]

[0078]

[0079] In group I, * is the connection point.

[0080] For example, R 1 to R 7 At least two of may be deuterium.

[0081] For example, the four R 1 It could be deuterium.

[0082] For example, the three R 1 One may be deuterium, and the other may be a phenyl group substituted by at least one deuterium, a biphenyl group substituted by at least one deuterium, or a carbazolyl group substituted by at least one deuterium.

[0083] For example, the four R 2 It could be deuterium.

[0084] For example, the three R 2 may be deuterium, and the remaining one may be a phenyl group substituted by at least one deuterium, a biphenyl group substituted by at least one deuterium, or a carbazolyl group substituted by at least one deuterium.

[0085] For example, the four R 3 It could be deuterium.

[0086] For example, the three R 3 may be deuterium, and the remaining one may be a phenyl group substituted by at least one deuterium, a biphenyl group substituted by at least one deuterium, or a carbazolyl group substituted by at least one deuterium.

[0087] For example, the four R4 It could be deuterium.

[0088] For example, the three R 4 may be deuterium, and the remaining one may be a phenyl group substituted by at least one deuterium, a biphenyl group substituted by at least one deuterium, or a carbazolyl group substituted by at least one deuterium.

[0089] For example, the four R 5 It could be deuterium.

[0090] For example, the three R 5 One may be deuterium, and the other may be a phenyl group substituted by at least one deuterium, a biphenyl group substituted by at least one deuterium, or a carbazolyl group substituted by at least one deuterium.

[0091] For example, the three R 6 It could be deuterium.

[0092] For example, two R 6 may be deuterium, and the other may be a phenyl group substituted by at least one deuterium, a biphenyl group substituted by at least one deuterium, or a carbazolyl group substituted by at least one deuterium.

[0093] For example, the three R 7 It could be deuterium.

[0094] For example, two R 7 may be deuterium, and the other may be a phenyl group substituted by at least one deuterium, a biphenyl group substituted by at least one deuterium, or a carbazolyl group substituted by at least one deuterium.

[0095] For example, R 1 to R 7 Each may be deuterium, m1 to m5 may each be an integer of 4, and m6 and m7 may each be an integer of 3.

[0096] For example, L 1 can be a phenylene group substituted by at least one deuterium group, a naphthylene group substituted by at least one deuterium group, or a carbazolylene group substituted by at least one deuterium group, and R 1 to R 7 At least one of them may be a phenyl group substituted by at least one deuterium or a carbazolyl group substituted by at least one deuterium, and the remaining one may be a deuterium or a phenyl group.

[0097] For example, L 1 can be phenylene groups substituted with all deuterium, naphthylene groups substituted with at least one deuterium, or carbazolylene groups substituted with all deuterium, and R 1 to R 7 Each of them may independently be deuterium, a phenyl group entirely substituted with deuterium, or a carbazolyl group entirely substituted with deuterium.

[0098] For example, the compound for an organic photoelectric device represented by Chemical Formula I may be one selected from Group 1, but is not limited thereto.

[0099] [Group 1]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105] In addition to the above-mentioned compounds for an organic optoelectronic device, one or more compounds may be included.

[0106] For example, the above-mentioned compound for an organic optoelectronic device may be used in the form of a composition further comprising a known host material.

[0107] For example, the above-mentioned compound for an organic photoelectric device may further include a dopant.

[0108] The dopant may be, for example, a phosphorescent dopant, such as a red or green phosphorescent dopant.

[0109] A dopant is a material that is mixed in a small amount with a compound used in an organic optoelectronic device to induce light emission, and is generally a material such as a metal complex that emits light by multiple excitation to a triplet state or more. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0110] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organometallic 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.

[0111] [Chemical formula Z]

[0112] L 2 MX

[0113] In the chemical formula Z, M is a metal, and L 2 and X are the same as or different from each other and are ligands that form a complex with M.

[0114] 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 2 and X may be, for example, a bidentate ligand.

[0115] By L 2 Examples of the ligand represented by and X may be selected from the chemical formulae of Group A, but are not limited thereto.

[0116] [Group A]

[0117]

[0118] In Group A,

[0119] R 300 to R 302 are each independently hydrogen, deuterium, a C1 to C30 alkyl group which may be substituted by a halogen, a C6 to C30 aryl group which may be substituted by a C1 to C30 alkyl group, or a halogen, and

[0120] R 303 to R 324 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0121] As an example, it may include a dopant represented by Chemical Formula II.

[0122] [Chemical Formula II]

[0123]

[0124] In Chemical Formula II,

[0125] R 101 to R 116 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0126] R 132 to R134 are each independently C1 to C6 alkyl,

[0127] R 101 to R 116 At least one of them is a functional group represented by Chemical Formula II-1,

[0128] L 100 It is a bidentate ligand for monovalent anions and is coordinated to iridium through the lone pair of electrons of carbon or heteroatoms.

[0129] n1 and n2 are each independently any one of integers from 0 to 3, and

[0130] n1+n2 is any integer from 1 to 3,

[0131] [Chemical Formula II-1]

[0132]

[0133] Wherein, in Chemical Formula II-1,

[0134] R 135 to R 139 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,and

[0135] * means the moiety attached to the carbon atom.

[0136] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0137] [Chemical Formula Z-1]

[0138]

[0139] In the chemical formula Z-1, rings A, B, C and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0140] R A 、R B 、R C and R D Each independently represents mono-, di-, tri-, or tetra-substituted, or unsubstituted;

[0141] L B 、L C and L DEach independently selected from direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof;

[0142] When nA is 1, L E is selected from the group consisting of direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof; when nA is 0, L E does not exist; and

[0143] R A 、R B 、R C 、R D R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silanyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; any adjacent R A 、R B 、R C 、R D , R and R' are optionally linked to each other to provide a ring; X B 、X C 、X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Each represents oxygen or a direct bond.

[0144] The dopant according to one embodiment may be a platinum complex, and may be represented, for example, by Chemical Formula III.

[0145] [Chemical Formula III]

[0146]

[0147] In Chemical Formula III,

[0148] X 100 Selected from O, S and NR 131 ,

[0149] R 117 to R 131 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0150] R 132 to R 134 are each independently C1 to C6 alkyl, and

[0151] R 117 to R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl.

[0152] Hereinafter, an organic photoelectric device including the above-mentioned compound for an organic photoelectric device is described.

[0153] The organic photoelectric device may be any device that converts electrical energy into light energy, or vice versa, without particular limitation, and may be, for example, an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0154] Herein, an organic light emitting diode as one example of an organic photoelectric device is described with reference to the accompanying drawings.

[0155] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0156] Reference 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 .

[0157] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0158] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0159] The organic layer 105 may include the above-described compound for an organic photoelectric device.

[0160] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-described compound for an organic photoelectric device.

[0161] For example, the composition for an organic photoelectric device further including a dopant may be a composition emitting red light or green light.

[0162] The light emitting layer 130 may include, for example, the compound described above for an organic photoelectric device.

[0163] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0164] The charge transport region may be, for example, a hole transport region 140 .

[0165] The hole transport region 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0166] 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 B may be contained in at least one of the hole transport layer and the hole transport auxiliary layer.

[0167] [Group B]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173] In the hole transport region 140 , in addition to this compound, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds similar thereto can be used.

[0174] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0175] 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.

[0176] 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 compounds of group C may be contained in at least one of the electron transport layer and the electron transport auxiliary layer.

[0177] [Group C]

[0178]

[0179]

[0180]

[0181]

[0182] One embodiment may be an organic light emitting diode including a light emitting layer as an organic layer.

[0183] Another embodiment may provide an organic light emitting diode including a light emitting layer and a hole transport region as organic layers.

[0184] Another embodiment may provide an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0185] like Figure 1 As shown, the organic light emitting diode according to the embodiment of the present invention may further include a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130 .

[0186] On the other hand, as the above-mentioned organic layer, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), and the like in addition to the light emitting layer.

[0187] The organic light emitting diode 100 may be manufactured by forming an anode or 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 the cathode or anode thereon.

[0188] Organic light emitting diodes can be applied to organic light emitting display devices.

[0189] 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.

[0190] Hereinafter, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry, or P&H tech, unless specifically noted, or synthesized by known methods.

[0191] (Preparation of Compounds for Organic Photoelectric Devices)

[0192] The compound shown as a more specific example of the compound of the present invention is synthesized by the following steps.

[0193] Comparative Synthesis Example 1: Synthesis of Compound A1

[0194] [Reaction Scheme 1]

[0195]

[0196] Step 1: Synthesis of intermediate Int1-1-a

[0197] 50.3g (142.1mmol) of 4,4,5,5-tetramethyl-2-(triphenylene-2-yl)-1,3,2-dioxaborolane, 40.2g (142.1mmol) of 1-bromo-3-iodobenzene, 29.5g (213.2mmol) of KCO and 4.9g (4.3mmol) of Pd(PPh) were suspended in 280ml of THF and 110ml of distilled water, then stirred under reflux for 8 hours under a stream of nitrogen. When the reaction was complete, the resultant was extracted with DCM (dichloromethane) and processed by column chromatography (hexane:DCM (20%) to obtain 39.3g (78%) of the intermediate Int1-1-a as a solid.

[0198] Step 2: Synthesis of intermediate Int1-1-b

[0199] 77 g (203.3 mmol) of intermediate Int1-1-a, 59.4 g (233.8 mmol) of bis(pinacolato)diboron, 4.8 g (5.9 mmol) of Pd(dppf)Cl2, and 28.9 g (294.8 mmol) of potassium acetate were placed in a round-bottom flask and dissolved in 400 ml of DMF. The mixture was stirred at 120°C under reflux for 12 hours. When the reaction was complete, the mixture was poured into an excess of distilled water and then stirred for 1 hour. The solid was filtered therefrom and dissolved in DCM. After removing water from it with MgSO4, the organic solvent was filtered therefrom with a silica gel pad and removed under reduced pressure. The solid thus obtained was recrystallized from ethyl acetate and hexane to obtain 41.8 g (70%) of intermediate Int1-1-b.

[0200] Step 3: Synthesis of Compound A1

[0201] 61.2 g (142.1 mmol) of intermediate Int1-1-b, 56.2 g (142.1 mmol) of 4-bromo-9,9'-spirobi[9H-fluorene], 29.5 g (213.2 mmol) of K2CO3, and 4.9 g (4.3 mmol) of Pd(PPh3)4 were suspended in 280 ml of THF and 110 ml of distilled water, and then stirred under reflux for 8 hours in a nitrogen stream. When the reaction was complete, the resultant was extracted with DCM and subjected to column chromatography (hexane:DCM (20%)) to obtain 39.3 g (78%) of compound A1 as a solid.

[0202] Liquid chromatography-mass spectrometry (LC-Mass) (theoretical value: 618.23 g / mol, measured value: M+ = 619.40 g / mol)

[0203] Comparative Synthesis Example 2: Synthesis of Compound A2

[0204] [Reaction Scheme 2]

[0205]

[0206] Step 1: Synthesis of intermediate Int2-1-a

[0207] Under nitrogen flow, 50.3 g (142.1 mmol) of 4,4,5,5-tetramethyl-2-(triphenylene-2-yl)-1,3,2-dioxaborolane, 40.2 g (142.1 mmol) of 1-bromo-4-iodobenzene, 29.5 g (213.2 mmol) of K CO , 4.9 g (4.3 mmol) of Pd (PPh ) were suspended in 280 ml of THF and 110 ml of distilled water, and then stirred under reflux for 8 hours. When the reaction was complete, the resultant was extracted with DCM and processed by column chromatography (hexane: DCM (20%)) to obtain 43.6 g (80%) of intermediate Int2-1-a as a solid.

[0208] Step 2: Synthesis of intermediate Int2-1-b

[0209] 77 g (203.3 mmol) of intermediate Int2-1-a, 59.4 g (233.8 mmol) of bis(pinacolato)diboron, 4.8 g (5.9 mmol) of Pd(dppf)Cl2, and 28.9 g (294.8 mmol) of potassium acetate were placed in a round-bottom flask and dissolved in 400 ml of DMF. The mixture was stirred at 120°2 under reflux for 12 hours. When the reaction was complete, the resulting product was poured into an excess of distilled water and then stirred for 1 hour. The solid was filtered from it and dissolved in DCM. After removing the moisture with MgSO4, the organic solvent was filtered from it using a silica gel pad and removed under reduced pressure. The solid was recrystallized from ethyl acetate and hexane to obtain 65.6 g (75%) of intermediate Int2-1-b.

[0210] Step 3: Synthesis of Compound A2

[0211] Under a nitrogen stream, 61.2 g (142.1 mmol) of intermediate Int2-1-b, 56.2 g (142.1 mmol) of 4-bromo-9,9'-spirobi[9H-fluorene], 29.5 g (213.2 mmol) of KCO, and 4.9 g (4.3 mmol) of Pd(PPh) were suspended in 280 ml of THF and 110 ml of distilled water, and then stirred under reflux for 8 hours. When the reaction was complete, the resultant was extracted with DCM and processed by column chromatography (hexane:DCM (20%)) to obtain 39.3 g (78%) of compound A2 as a solid.

[0212] Liquid chromatography-mass spectrometry (theoretical value: 618.23 g / mol, measured value: M+=619.39 g / mol)

[0213] Synthesis Example 1: Synthesis of Compound 1-3

[0214] [Reaction Scheme 3]

[0215]

[0216] 20g of compound A1 was placed in a round-bottom flask, and 390mL of benzene-D6 was added thereto, followed by stirring. 14ml of trifluoromethanesulfonic acid was added thereto, followed by reflux. After 24 hours, the resultant was cooled to room temperature, D2O was added thereto, and then stirred for 30 minutes. The solid therein was dissolved in excess MC, and then neutralized with a K3PO4 aqueous solution. After removing the water layer therefrom, the organic layer was filtered through silica gel to remove the solvent, and then recrystallized to obtain 13g of compound 1-3 (white solid, liquid mass spectrum Mz648.4, C 49 D 30 ).

[0217] Synthesis Example 2: Synthesis of Compound 1-4

[0218] [Reaction Scheme 4]

[0219]

[0220] 15 g of compound 1-4 (white solid, liquid mass spectrum Mz 648.4, C 49 D 30 ).

[0221] (Manufacturing of organic light-emitting diodes)

[0222] Example 1

[0223] A glass substrate coated with an indium tin oxide (ITO) thin film 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 for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The obtained ITO transparent electrode was used as an anode, and Compound A doped with 3% NDP-9 (available from Novaled) was vacuum deposited on the ITO substrate to form Thick hole injection layer, and compound A is deposited on the hole transport layer to form Thick hole transport layer. On the hole transport layer, Compound B was deposited to form a hole transport auxiliary layer with a thickness of 1000 nm. On the hole transport auxiliary layer, a layer was formed by using Compound 1-3 obtained in Synthesis Example 1 and doping 10 wt% of PhGD as a dopant by vacuum deposition. Then, on the light emitting layer, Compound C was deposited at a thickness of 1:1 to form an electron transport auxiliary layer, and compound D and LiQ were simultaneously vacuum deposited at a weight ratio of 1:1 to form On the electron transport layer, LiQ and Al are vacuum deposited sequentially to Thick and harmonious thick, thereby manufacturing an organic light emitting diode.

[0224] ITO / Compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[90 wt% host (compounds 1-3): 10 wt% PhGD] Compound C / Compound D:LiQ / LiQ / Al

[0225] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0226] Compound B: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0227] Compound C: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0228] Compound D: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0229] [PhGD]

[0230]

[0231] Comparative Example 1

[0232] The diode of Comparative Example 1 was manufactured in the same manner as in Example 1 except that the main body was changed as shown in Table 1.

[0233] Evaluation: Confirmed lifespan extension effect

[0234] Brightness (cd / m 2 ) maintained at 6000cd / m 2 , and measured the time it took for the luminous efficiency (cd / A) to drop to 96%.

[0235] Table 1 shows relative values based on the lifespan of Comparative Example 1.

[0236] (Table 1)

[0237] main body Lifespan T96 (%) Example 1 Compounds 1-3 121 Comparative Example 1 Compound A1 100

[0238] Referring to Table 1, the organic light emitting diode according to the embodiment of the present invention has significantly improved lifespan characteristics compared to the organic light emitting diode according to the comparative example.

[0239] While the present invention has been described in conjunction with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A compound for an organic optoelectronic device, represented by Chemical Formula I: [Chemical Formula I] in, In Chemical Formula I, L 1 is a phenylene group substituted with at least one deuterium, R 1 to R 7 are each independently deuterium or phenyl substituted with at least one deuterium, m1 to m5 are each independently one of integers from 1 to 4, and m6 and m7 are each independently one of integers from 1 to 3.

2. The compound according to claim 1, wherein Chemical Formula I is represented by any one of Chemical Formula I-1 to Chemical Formula I-4: in, In Chemical Formulas I-1 to I-4, L 1 、R 1 to R 7 and m1 to m7 are the same as those defined in claim 1.

3. The compound according to claim 1, wherein The compound is one selected from Group 1: [Group 1] 4. An organic optoelectronic device comprising an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, in, The organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 3.

5. The organic optoelectronic device according to claim 4, wherein The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic photoelectric device. A display device comprising the organic optoelectronic device according to claim 4 .

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