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

Abstract

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

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefits of Korean Patent Application No. 10-2021-0060893 filed in the Korean Intellectual Property Office on May 11, 2021, and Korean Patent Application No. 10-2022-0052335 filed in the Korean Intellectual Property Office on April 27, 2022, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Disclosed are a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

[0004] An organic photoelectric device (organic photodiode) is a device that can convert electrical energy into light energy and vice versa.

[0005] Organic photoelectric devices can be classified according to their driving principles as follows: 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 supplying voltage or current to electrodes.

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

[0007] Among them, organic light emitting diodes (OLEDs) have recently attracted attention due to an increase in demand for flat panel displays. 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

[0008] One embodiment provides a compound for an organic photoelectric device capable of realizing an organic photoelectric device having high efficiency and a long lifespan.

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

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

[0011] Another embodiment provides a display device including the organic photoelectric device.

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

[0013] [Chemical formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] X 1 is O or S,

[0017] L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0018] 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,

[0019] R 1 To R 9 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl, and

[0020] A is any one of the linking groups selected from Group I,

[0021] [Group I]

[0022]

[0023] Among them, in group I,

[0024] R a , R b , R c and R d are each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group,

[0025] n1 is an integer of 0 or 1,

[0026] m1, m2 and m4 are each independently an integer from 1 to 4,

[0027] m3 is an integer of 1 or 2,

[0028] m5 and m6 are each independently an integer from 1 to 3, and

[0029] * is the connection point.

[0030] According to another embodiment, provided is a composition for an organic photoelectric device including a first compound and a second compound.

[0031] The first compound may be the same as described above, and the second compound may be the compound for an organic photoelectric device represented by Chemical Formula 2.

[0032] [Chemical formula 2]

[0033]

[0034] In chemical formula 2,

[0035] X 2 O, S, NL a -R e , CR f R g or SiR h R i ,

[0036] L a is a single bond or a substituted or unsubstituted C6 to C12 arylene group,

[0037] R e , R f , R g , R h , R i and R 10 are each independently hydrogen, deuterium, 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,

[0038] n2 is an integer from 1 to 4, and

[0039] B is any one selected from the rings of Group III.

[0040] [Group III]

[0041]

[0042] In Group III,

[0043] * is the connection point,

[0044] X 3 O, S, CR j R k or SiR l R m ,

[0045] R j , R k , R l , R m and R 11 To R 18are each independently hydrogen, deuterium, 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,

[0046] n3, n5, n8 and n10 are each independently an integer from 1 to 4,

[0047] n4, n6, n7 and n9 are each independently an integer of 1 or 2, and

[0048] R e and R 10 To R 18 At least one of them is a group represented by chemical formula a,

[0049] [Chemical formula a]

[0050]

[0051] Among them, in chemical formula a,

[0052] L 3 To L 5 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,

[0053] Ar 3 and Ar 4 are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0054] * is the connection point.

[0055] 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.

[0056] According to another embodiment, a display device including the organic photoelectric device is provided.

[0057] An organic photoelectric device with high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0058] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0059] <Description of Reference Numerals>

[0060] 100: Organic Light Emitting Diode

[0061] 105: Organic layer

[0062] 110: cathode

[0063] 120: Anode

[0064] 130: Luminous layer

[0065] 140: Hole transport zone

[0066] 150: Electron transport region DETAILED DESCRIPTION

[0067] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto and is defined by the scope of claims.

[0068] In one example disclosed in the present invention, "substituted" means that at least one hydrogen of the substituent or compound is replaced by deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano or a combination thereof.

[0069] In the specific examples disclosed in the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl or cyano. In the specific examples disclosed in the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl or cyano. In the specific examples disclosed in the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl or cyano. In the specific examples disclosed in the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0070] As used herein, "unsubstituted" means that hydrogen remains, which has not been replaced with any other substituent.

[0071] As used herein, "hydrogen substitution (—H)" may include "deuterium substitution (—D)" or "tritium substitution (—T)".

[0072] As used herein, when a definition is not otherwise provided, "hetero" refers to a group including 1 to 3 heteroatoms selected from N, O, S, P and Si in one functional group and the rest are carbon.

[0073] As used herein, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and all elements of the hydrocarbon aromatic portion have p-orbitals forming conjugation, for example, phenyl, naphthyl, etc., two or more hydrocarbon aromatic portions may be connected by a σ bond and the hydrocarbon aromatic portion may be (for example) biphenyl, terphenyl, tetraphenyl, etc., and two or more hydrocarbon aromatic portions may be directly or indirectly fused to provide a non-aromatic fused ring, for example, fluorenyl.

[0074] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0075] As used herein, "heterocyclic group" is a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P and Si to replace 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.

[0076] For example, "heteroaryl" may refer to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls may be directly connected by a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.

[0077] 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 naphthacenyl 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 chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted 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, but is not limited thereto.

[0078] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted phenylthio 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 benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinoline group, or a substituted or unsubstituted benzothiophene group. The invention may be a substituted or unsubstituted isoquinazolyl, a substituted or unsubstituted quinazolinyl, 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, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted benzofuranofluorenyl, a substituted or unsubstituted benzothiophenefluorenyl, or a combination thereof, but is not limited thereto.

[0079] In this specification, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and according to the highest occupied molecular orbital (HOMO) level, holes formed in the anode can be easily injected into the light-emitting layer due to the conductive characteristics and transported in the light-emitting layer.

[0080] In addition, the electronic property refers to the ability to accept electrons when an electric field is applied, and according to the lowest unoccupied molecular orbital (LUMO) level, electrons formed in the cathode can be easily injected into the light-emitting layer due to the conductive property and transported in the light-emitting layer.

[0081] Hereinafter, a compound for an organic photoelectric device according to one embodiment is described.

[0082] The compound for an organic photoelectric device according to an embodiment is shown in Chemical Formula 1.

[0083] [Chemical formula 1]

[0084]

[0085] In Chemical Formula 1,

[0086] X 1 is O or S,

[0087] L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0088] 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,

[0089] R 1 To R 9 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C20 alkyl, or substituted or unsubstituted C6 to C20 aryl, and

[0090] A is any one of the linking groups selected from Group I,

[0091] [Group I]

[0092]

[0093] In Group I,

[0094] R a , R b , R c and R d are each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group,

[0095] n1 is an integer of 0 or 1,

[0096] m1, m2 and m4 are each independently an integer from 1 to 4,

[0097] m3 is an integer of 1 or 2,

[0098] m5 and m6 are each independently an integer from 1 to 3, and

[0099] * is the connection point.

[0100] The compound represented by Chemical Formula 1 has a structure in which a benzo[b]naphtho[1,2-d]furan (or benzo[b]naphtho[1,2-d]thiophene) skeleton is substituted with an ET unit at position 11. As the torsion angle between the benzo[b]naphtho[1,2-d]furan (or benzo[b]naphtho[1,2-d]thiophene) skeleton and the ET unit increases, HOMO-LUMO separation increases and electron mobility increases, and due to limited molecular migration, Tg can be increased relative to Tev.

[0101] Therefore, the organic light emitting diode including the compound represented by Chemical Formula 1 can ensure stable driving voltage and excellent efficiency characteristics. The high glass transition temperature maintains a stable film even for Joule heat generated during device driving, thereby ensuring stable device characteristics and allowing the device to have an excellent lifespan.

[0102] In Chemical Formula 1, the linking group A may be linked to the para position, and, for example, it may be represented by any one of Chemical Formula 1-I to Chemical Formula 1-VI.

[0103] [Chemical Formula 1-I]

[0104]

[0105] [Chemical Formula 1-II]

[0106]

[0107] [Chemical Formula 1-III]

[0108]

[0109]

[0110] [Chemical Formula 1-VI]

[0111]

[0112] In Chemical Formula 1-I to Chemical Formula 1-VI,

[0113] X 1 , L 1 , L 2 ,Ar 1 ,Ar 2 , R 1 To R 9 , R a , R b , R c , R d And m1 to m6 are the same as above.

[0114] For example, Ar 1 and Ar 2and the like. The substituted or unsubstituted phenyl group and the substituted or unsubstituted biphenyl group may be independently substituted or unsubstituted naphthyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted chrysene group or substituted or unsubstituted triphenylene group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group or substituted or unsubstituted dibenzosilyl group (dibenzosilolyl group).

[0115] In a specific example, Ar 1 and Ar 2 They may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted dibenzosilolyl.

[0116] For example, L 1 and L 2 Each independently may be a single bond or a substituted or unsubstituted phenylene group.

[0117] For example, *-L 1 -Ar 1 and *-L 2 -Ar 2 Each of the substituents may be independently any one selected from Group II.

[0118] [Group II]

[0119]

[0120] In Group II,

[0121] D can be deuterium,

[0122] m11 is an integer from 1 to 5,

[0123] m12 is an integer from 1 to 4,

[0124] m13 is an integer from 1 to 3,

[0125] m14 is an integer from 1 to 7, and

[0126] * is the connection point.

[0127] For example, R 1 To R 9 They 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.

[0128] In a specific example, R 1 To R 9 and may each independently be hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted naphthyl.

[0129] For example, R 1 To R 9 and may each independently be hydrogen or deuterium.

[0130] For example, the compound for an organic photoelectric device represented by Chemical Formula 1 may include compounds of Group 1, but is not limited thereto.

[0131] [Group 1]

[0132]

[0133]

[0134]

[0135]

[0136] A composition for an organic photoelectric device according to another embodiment includes a first compound and a second compound, wherein the first compound is the above-mentioned compound for an organic photoelectric device and the second compound is the compound for an organic photoelectric device represented by Chemical Formula 2.

[0137] [Chemical formula 2]

[0138]

[0139] In chemical formula 2,

[0140] X 2 O, S, NL a -R e , CR f R g or SiR h R i ,

[0141] L a is a single bond or a substituted or unsubstituted C6 to C12 arylene group,

[0142] R e , R f , R g , R h , R i and R 10are each independently hydrogen, deuterium, 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,

[0143] n2 is an integer from 1 to 4, and

[0144] B is any one selected from the rings of Group III.

[0145] [Group III]

[0146]

[0147] In Group III,

[0148] * is the connection point,

[0149] X 3 O, S, CR j R k or SiR l R m ,

[0150] R j , R k , R l , R m and R 11 To R 18 are each independently hydrogen, deuterium, 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,

[0151] n3, n5, n8 and n10 are each independently an integer from 1 to 4,

[0152] n4, n6, n7 and n9 are each independently an integer of 1 or 2, and

[0153] R e and R 10 To R 18 At least one of them is a group represented by chemical formula a,

[0154] [Chemical formula a]

[0155]

[0156] Among them, in chemical formula a,

[0157] L 3 To L 5 are each independently a single bond, or a substituted or unsubstituted C6 to C30 arylene group,

[0158] Ar3 and Ar 4 are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0159] * is the connection point.

[0160] The second compound may be used together with the first compound in the light emitting layer to increase charge mobility and improve stability, thereby improving light emitting efficiency and lifespan characteristics.

[0161] The second compound may have a structure in which carbazole / fused carbazole / fused dibenzofuran / fused dithiophene / fused dibenzosilole is substituted with amine, and may be represented by any one of Chemical Formula 2-I to Chemical Formula 2-X based on the type of other benzene rings and the fusion position.

[0162]

[0163]

[0164] In Chemical Formulae 2-I to 2-X,

[0165] X 2 , X 3 , R 10 To R 13 , R 17 , R 18 , n2 to n5, n9 and n10 are the same as above.

[0166] In addition, the second compound may be represented by any one of Chemical Formula 2-IA to Chemical Formula 2-XA, Chemical Formula 2-IIB to Chemical Formula 2-IVB, and Chemical Formula 2-IIC to Chemical Formula 2-XC based on the substitution direction of the amine group.

[0167]

[0168]

[0169] In Chemical Formulae 2-IA to 2-XA,

[0170] X 2 , X 3 , L 3 To L 5 ,Ar 3 , R 10 To R 13 , R 17 , R 18 ,Ar 4 , n3 to n5, n9 and n10 are as described above, and

[0171] n2 is an integer from 1 to 3.

[0172]

[0173]

[0174] [Chemical formula 2-IVB]

[0175]

[0176] In Chemical Formula 2-IIB to Chemical Formula 2-IVB,

[0177] X 2 , L 3 To L 5 , R 10 , R 12 , R 13 ,Ar 3 ,Ar 4 And n2 to n4 are the same as above, and n5 is an integer of 1 to 3.

[0178]

[0179] [Chemical formula 2-IVC]

[0180]

[0181] In Chemical Formulae 2-IIC to 2-IVC,

[0182] X 2 , L 3 To L 5 ,Ar 3 ,Ar 4 , R 10 , R 12 , R 13 , n2 and n5 are the same as above, and n4 is an integer of 1.

[0183] [Chemical formula 2-VC]

[0184]

[0185]

[0186] [Chemical formula 2-XC]

[0187]

[0188] In the chemical formulae 2-VC to 2-XC,

[0189] X2 , X 3 , L 3 To L 5 ,Ar 3 ,Ar 4 , R 10 , R 17 , R 18 , n2 and n10 are the same as above, and

[0190] n9 is an integer of 1.

[0191] For example, R 10 To R 13 , R 17 and R 18 and may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group.

[0192] For example, Ar 3 and Ar 4 The substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted chrysene group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted benzofuranofluorenyl group or substituted or unsubstituted benzothiophenefluorenyl group.

[0193] In a specific example, Ar 3 and Ar 4 They may each independently be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl or substituted or unsubstituted naphthyl.

[0194] For example, L 3 To L 5 Each of them independently may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0195] In a specific example, L 3 may be a single bond or a substituted or unsubstituted phenylene group, and L 4 and L 5 Each of them independently may be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0196] For example, L 3 can be a single bond, and L 4 and L 5Each independently may be a single bond or a substituted or unsubstituted phenylene group.

[0197] For example, X 2 Can be O, S, NL a -R e , CR f R g or SiR h R i .

[0198] In a specific example, X 2 It can be NL a -R e , CR f R g or SiR h R i .

[0199] For example, X 3 Can be O, S, CR j R k or SiR l R m .

[0200] As a specific example, X 3 Can be O or S.

[0201] For example, R e The phenyl group may be substituted or unsubstituted.

[0202] For example, R f , R g , R h , R i , R j , R k , R l and R m They may each independently be a substituted or unsubstituted C1 to C5 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.

[0203] In a specific example, R f , R g , R h , R i , R j , R j , R k , R l and R m They may each independently be a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

[0204] For example, R 10 To R 13 , R 17 and R18 They may each independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0205] In a specific example, R 10 To R 13 , R 17 and R 18 and may each independently be hydrogen or deuterium.

[0206] The second compound according to the embodiment may be represented by any one of Chemical Formula 2-IA, Chemical Formula 2-IVB, and Chemical Formula 2-XA.

[0207] For example, in Formula 2-IVB, X 2 Can be O, S or NL a -R e , L a Can be a single bond and R e The phenyl group may be substituted or unsubstituted.

[0208] For example, in the chemical formula 2-XA, X 2 It can be NL a -R e , CR f R g or SiR h R i , L a Can be a single bond, R e It can be substituted or unsubstituted phenyl, R f , R g , R h and R i can be independently substituted or unsubstituted methyl or substituted or unsubstituted phenyl, X 3 Can be O or S.

[0209] The second compound according to a specific embodiment may be represented by any one of Chemical Formula 2-IA-3, Chemical Formula 2-IVB-2, and Chemical Formula 2-XA-2.

[0210] [Chemical formula 2-IA-3]

[0211]

[0212]

[0213]

[0214] In Chemical Formula 2-IA-3, Chemical Formula 2-IVB-2 and Chemical Formula 2-XA-2,

[0215] L 3 is a single bond, L 4 and L 5 are each independently a single bond or a substituted or unsubstituted phenylene group,

[0216] Ar 3 and Ar 4 are each independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl or a substituted or unsubstituted naphthyl,

[0217] X 2 It is NL a -R e , CR f R g or SiR h R i ,

[0218] X 3 is O or S,

[0219] L a is a single key,

[0220] R e , R f , R g , R h and R i are independently substituted or unsubstituted C1 to C5 alkyl or substituted or unsubstituted C6 to C12 aryl, and

[0221] R 10 To R 13 , R 17 and R 18 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0222] n2 to n5, n9 and n10 are the same as described above.

[0223] For example, the second compound may be one of the compounds selected from Group 2, but is not limited thereto.

[0224] [Group 2]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240] For example, the first compound and the second compound may be included in a weight ratio of about 1:99 to about 99:1. Within the above range, the electron transport ability of the first compound and the hole transport ability of the second compound may be utilized to achieve bipolar characteristics by adjusting an appropriate weight ratio, thereby improving efficiency and life. Within the above range, for example, the first compound and the second compound may be included in a weight ratio of about 10:90 to about 90:10, about 20:80 to about 80:20, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, or about 30:70 to about 60:40. For example, they may be included in a weight ratio of about 40:60, about 50:50, or about 60:40.

[0241] The composition for an organic photoelectric device according to an embodiment may include a compound represented by Chemical Formula 1-I or Chemical Formula 1-V as a first compound and include a compound represented by Chemical Formula 2-IVB or Chemical Formula 2-XA as a second compound.

[0242] The composition for an organic photoelectric device according to a specific embodiment may include a compound represented by Chemical Formula 2-IVB-2 or Chemical Formula 2-XA-2 as the second compound.

[0243] In addition to the above-mentioned first compound and second compound, one or more compounds may be further included.

[0244] The compound for an organic photoelectric device or the composition for an organic photoelectric device may be a composition further including a dopant.

[0245] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0246] A dopant is a material that emits light by mixing in a small amount with a compound or composition for an organic optoelectronic device. Generally, a dopant may be a material that emits light by multiple excitations to a triplet state or more, such as a metal complex. A dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or two or more.

[0247] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may include an organic metal compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0248] [Chemical formula Z]

[0249] L 7 MX 5

[0250] In the chemical formula Z, M is a metal and L 7 and X 5 are the same as or different from each other, and are ligands that form a complex with M.

[0251] 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 7 and X 5 It may be, for example, a bidentate ligand.

[0252] In an embodiment, L 7 and X 5 The ligands represented can be, for example, the ligands shown in Group A.

[0253] [Group A]

[0254]

[0255] In Group A,

[0256] R 300 To R 302 may be, for example, independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted or not substituted by halogen, C6 to C30 aryl which may be substituted or not substituted by C1 to C30 alkyl, or halogen, and

[0257] R 303 To R 324The radicals may be, for example, 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.

[0258] In an embodiment, the dopant may be represented by Chemical Formula V.

[0259] [Chemical Formula V]

[0260]

[0261] In chemical formula V,

[0262] R 101 To R 116 can be, for example, independently hydrogen, deuterium, C1 to C10 alkyl, substituted or unsubstituted C6 to C30 aryl, or SiR 132 R 133 R 134 ,

[0263] R 132 To R 134 may be, for example, independently substituted or unsubstituted C1 to C6 alkyl, R 101 To R 116 At least one of them may be a functional group represented by chemical formula V-1,

[0264] L 100 The bidentate ligand may be, for example, a monovalent anion and is a ligand coordinated to iridium via a lone pair of electrons on carbon or a heteroatom.

[0265] m15 and m16 may be, for example, independently any integer from 0 to 3, and m15+m16 may be, for example, any integer from 1 to 3.

[0266] [Chemical formula V-1]

[0267]

[0268] In chemical formula V-1,

[0269] R 135 To R139 can be, for example, independently hydrogen, deuterium, C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or SiR 132 R 133 R 134 ,

[0270] R 132 To R 134 may be, for example, independently substituted or unsubstituted C1 to C6 alkyl, and

[0271] * indicates the point of attachment to the carbon atom.

[0272] In an embodiment, the dopant may be represented by Chemical Formula Z-1.

[0273] [Chemical formula Z-1]

[0274]

[0275] In formula Z-1, rings A, B, C and D may, for example, independently be 5- or 6-membered carbocyclic or heterocyclic rings;

[0276] R A , R B , R C and R D may independently represent mono-, di-, tri- or tetra-substituted, or unsubstituted;

[0277] L B , L C and L D can be, for example, independently selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0278] When nA is 1, L E It can be, for example, selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; and when nA is 0, L E does not exist;

[0279] R A , R B , R C , R D , R and R' can be, for example, independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, cyano, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; RA , R B , R C , R D Any adjacent groups of R, R and R' are arbitrarily connected to each other to form a ring; X B , X C , X D and X E are independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Independently selected from oxygen or a direct bond.

[0280] The composition for an organic photoelectric device according to an embodiment may include a dopant represented by Chemical Formula VI.

[0281] [Chemical Formula VI]

[0282]

[0283] In Chemical Formula VI,

[0284] X 100 It may be, for example, selected from O, S and NR 131 ,

[0285] R 101 To R 131 may be, for example, independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0286] R 132 To R 134 may, for example, independently be C1 to C6 alkyl, and

[0287] R 117 To R 131 At least one of them may be (for example) -SiR 132 R 133 R 134 or tert-butyl.

[0288] Hereinafter, an organic photoelectric device including the above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device is described.

[0289] The organic photoelectric device may be any device that converts electrical energy into light energy (or vice versa) without particular limitation, and it may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0290] Herein, an organic light emitting diode is described as an example of an organic photoelectric device with reference to the accompanying drawings.

[0291] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0292] refer to Figure 1 , the organic light emitting diode 100 according to the embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0293] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDT), polypyrrole, and polyaniline, but is not limited thereto.

[0294] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc., or an alloy thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0295] The organic layer 105 may include the above-described compound for an organic photoelectric device or the composition for an organic photoelectric device.

[0296] The organic layer 105 may include, for example, a light emitting layer 130 , and the light emitting layer 130 may include, for example, the above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device.

[0297] The composition for an organic optoelectronic device further including a dopant may be, for example, a green light-emitting composition.

[0298] The light emitting layer 130 may include, for example, the above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device as a phosphorescent host.

[0299] The organic layer may include a charge transport region in addition to the light emitting layer.

[0300] The charge migration region may be, for example, a hole transport region 140 .

[0301] The hole transport region 140 may further improve hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0302] 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 in group B may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0303] [Group B]

[0304]

[0305]

[0306]

[0307]

[0308]

[0309] In the hole transporting region 140, in addition to the compounds described above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds similar thereto can be used.

[0310] In addition, the charge migration region may be, for example, the electron transport region 150 .

[0311] The electron transport region 150 may also improve electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0312] 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 in group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0313] [Group C]

[0314]

[0315]

[0316]

[0317]

[0318] One embodiment may provide an organic light emitting diode including a light emitting layer as the organic layer.

[0319] Another embodiment may provide an organic light emitting diode including a light emitting layer and a hole transporting region as the organic layer.

[0320] Another embodiment may provide an organic light emitting diode including a light emitting layer and an electron transport region as the organic layer.

[0321] As the organic layer 105, the organic light emitting diode according to the embodiment of the present invention may include a hole transport region 140 and an electron transport region 150 in addition to the light emitting layer 130, such as Figure 1 shown.

[0322] 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), etc. in addition to the light emitting layer.

[0323] The organic light emitting diode 100 may be produced 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.

[0324] The organic light emitting diode may be applied to an organic light emitting diode display device.

[0325] 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.

[0326] Hereinafter, unless specifically noted, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc. or Tokyo chemical industry, or were synthesized by known methods.

[0327] (Preparation of compounds for organic optoelectronic devices)

[0328] Synthesis Example 1: Synthesis of Compound 1-3

[0329] [Reaction Scheme 1]

[0330]

[0331] Step 1: Synthesis of SM-2

[0332] SM-1 (48 g, 239 mmol) was dissolved in 0.7 L tetrahydrofuran (THF), and 2-bromo-1-chloro-3-fluorobenzene (50 g, 239 mmol) and tetrakis (triphenylphosphine) palladium (13.7 g, 11.9 mmol) were added thereto, and then stirred. Then, a solution of saturated potassium carbonate (66 g, 478 mmol) in 250 ml of water was added, and then heated to reflux at 80 ° C for 12 hours. After the reaction was completed, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), then 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 41 g (60%) of SM-2.

[0333] Step 2: Synthesis of SM-3

[0334] SM-2 (41.4 g, 144.6 mmol) was dissolved in 720 ml of dichloromethane (MC), and BBr 3 (1 M) (217 ml, 217 mmol) was slowly added dropwise thereto at an internal temperature of 0° C., followed by stirring at room temperature for 5 hours.

[0335] After slowly adding a saturated aqueous solution of potassium carbonate thereto in a dropwise manner at 0°C until the pH of the reaction solution reached 7, water was added to the reaction solution, and the mixture was extracted with dichloromethane (MC), 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 20 g (51%) of SM-3.

[0336] Step 3: Synthesis of SM-4

[0337] SM-3 (40 g, 146.7 mmol) was dissolved in 430 mL N-methyl-2-pyrrolidone (NMP), and potassium carbonate (40.6 g, 293.4 mmol) was added thereto, and then heated to reflux at 130 ° C for 12 hours. After the reaction was completed, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The residue was separated and purified by flash column chromatography to obtain 36 g (97%) of SM-4.

[0338] Step 4: Synthesis of SM-5

[0339] SM-4 (37 g, 147 mmol) was dissolved in 300 mL of N, N-dimethylformamide (DMF), and bis-boronic acid pinacol ester (45 g, 177 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (10.8 g, 14.8 mmol), potassium acetate (29 g, 295 mmol) and tricyclohexylphosphine (12.4 g, 44.3 mmol) were added thereto, and then heated under reflux at 150° C. for 12 hours. After the reaction was completed, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain 28 g (75%) of SM-5.

[0340] Step 5: Synthesis of Compound 1-3

[0341] SM-5 (10.6 g, 30.8 mmol) and SM-6 (13 g, 30.8 mmol) were dissolved in 140 mL tetrahydrofuran (THF), and tetrakis (triphenylphosphine) palladium (2.1 g, 1.8 mmol) was added thereto, and then stirred. Subsequently, a saturated solution of potassium carbonate (8.5 g, 62 mmol) in 30 ml of water was added, and then heated to reflux at 80 ° C for 12 hours. After the reaction was completed, water was added to the reaction solution, and the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure. The resulting residue was dissolved in heated xylene, and then silica-filtered. The filtered solution was concentrated under reduced pressure and recrystallized by using a xylene solvent to obtain 15 g (81%) of compound 1-3.

[0342] C 43 H 27 Theoretical values ​​of N3O: C, 85.83; H, 4.52; N, 6.98; O, 2.66. Expected values: C, 85.83; H, 4.52; N, 6.98; O, 2.66

[0343] Synthesis Example 2: Synthesis of Compound 1-4

[0344] [Reaction Scheme 2]

[0345]

[0346] Step 1: Synthesis of SM-7

[0347] Compound SM-7 (72%) was synthesized in the same manner as in Step 1 of Synthesis Example 1, except that naphthalene-1-ylboronic acid was used instead of SM-1.

[0348] Step 2: Synthesis of SM-8

[0349] In a 1000mL round-bottom flask, SM-7 (98.3g, 273mmol) was added to 550mL N, N-dimethylformamide (DMF), and its internal temperature was set to 0°C. Subsequently, sodium thiomethoxide (21.1g, 286.6mmol) and potassium carbonate (56.5g, 409.4mmol) were slowly added thereto. In this article, the internal temperature was maintained at 0°C. The resulting mixture was heated at 80°C under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, ethyl acetate and water were added thereto, then stirred, and the organic layer was separated therefrom, concentrated under reduced pressure and processed by column chromatography to obtain 66.8g (86%) of SM-8.

[0350] Step 3: Synthesis of SM-9

[0351] SM-8 (66.3 g, 233 mmol) was added to 500 mL of acetic acid, and then the internal temperature was set to 0° C. Subsequently, 50 ml of hydrogen peroxide was slowly added thereto. Herein, the internal temperature was maintained at 0° C. The reaction solution was stirred at room temperature for 12 hours, placed in ice water and extracted with dichloromethane (MC), treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure to obtain 66.5 g (95%) of SM-9.

[0352] Step 4: Synthesis of SM-10

[0353] After SM-9 (66 g, 219 mmol) was added to 500 mL of sulfuric acid and the mixture was stirred at room temperature for 20 hours, the reaction solution was placed in ice water and then adjusted to pH 9 with an aqueous NaOH solution. The resultant was extracted with dichloromethane (MC), treated with anhydrous magnesium sulfate to remove moisture, filtered and concentrated under reduced pressure to obtain 41 g (70%) of SM-10.

[0354] Step 5: Synthesis of SM-11

[0355] SM-11 (63%) was synthesized according to Reaction Scheme 2 in the same manner as in Synthesis Example 1, except that SM-10 was used instead of SM-4 in Step 4 of Synthesis Example 1.

[0356] Step 6: Synthesis of Compound 1-4

[0357] Compound 1-4 (85%) was synthesized according to Reaction Scheme 2 in the same manner as in Synthesis Example 1, except that SM-11 was used instead of SM-5 in Step 5 of Synthesis Example 1.

[0358] C 43 H 27Theoretical values ​​of N3S: C, 83.60; H, 4.41; N, 6.80; S, 5.19, Exp. values: C, 83.60; H, 4.41; N, 6.80; S, 5.19

[0359] Synthesis Examples 3 to 8

[0360] Each compound was synthesized in the same manner as in Synthesis Example 1 or 2, except that SM-5 or SM-11 of Synthesis Example 1 or Synthesis Example 2 was used as Int A as shown in Table 1, and Int B of Table 1 was used instead of SM-6.

[0361] (Table 1)

[0362]

[0363]

[0364] <Int B>

[0365]

[0366] Synthesis Example 9: Synthesis of Compound A-28

[0367] [Reaction Scheme 3]

[0368]

[0369] Step 1: Synthesis of Int-17

[0370] 20g (79.46mmol) of 2-chloro-11H-benzo[a]carbazole, 19.45g (95.35mmol) of iodobenzene, 19.09g (198.64mmol) of sodium tert-butyl alcohol and 3.22g (15.89mmol) of tri-tert-butylphosphine were dissolved in 260ml of toluene, and 3.64g (3.97mmol) of Pd(dba)2 was added thereto, and then refluxed and stirred for 12 hours under a nitrogen atmosphere. When the reaction was completed, after extraction with toluene and distilled water, the organic layer obtained therefrom was dried with anhydrous magnesium sulfate and filtered, and the filtrate thus obtained was concentrated under reduced pressure. The product was purified therefrom with n-hexane / dichloromethane (volume ratio 2: 1) by silica gel column chromatography to obtain 23.7g (91%) of the target compound Int-17 as a white solid.

[0371] Step 2: Synthesis of Compound A-28

[0372] 20 g (61.01 mmol) of Int-17, 18.92 g (64.06 mmol) of 4-(2-naphthyl)-N-phenylaniline, 14.66 g (152.53 mmol) of sodium tert-butoxide and 2.47 g (12.20 mmol) of tri-tert-butylphosphine were dissolved in 200 ml of toluene, and 2.79 g (3.05 mmol) of Pd(dba)2 was added thereto, and then refluxed and stirred for 12 hours under a nitrogen atmosphere. When the reaction was completed, after extraction with toluene and distilled water, the organic layer obtained therefrom was dried with anhydrous magnesium sulfate and filtered, and the filtrate thus obtained was concentrated under reduced pressure. The product was purified therefrom with n-hexane / dichloromethane (volume ratio 2: 1) by silica gel column chromatography to obtain 31.5 g (88%) of the target compound A-28 as a white solid.

[0373] Synthesis Example 10: Synthesis of Compound 2-92

[0374] [Reaction Scheme 4]

[0375]

[0376] 20 g (62.74 mmol) of 10-chloro-8,8-dimethyl-8H-benzo[b]fluoren[4,3-d]furan, 19.46 g (65.87 mmol) of 4-(2-naphthyl)-N-phenylaniline, 15.07 g (156.84 mmol) of sodium tert-butoxide and 2.54 g (12.55 mmol) of tri-tert-butylphosphine were dissolved in 300 ml of toluene, 2.87 g (3.14 mmol) of Pd(dba)2 was added thereto, and then refluxed and stirred for 12 hours under a nitrogen atmosphere. When the reaction was completed, after extraction with toluene and distilled water, the organic layer obtained therefrom was dried with anhydrous magnesium sulfate and filtered, and the filtrate thus obtained was concentrated under reduced pressure. The product was purified by silica gel column chromatography using n-hexane / dichloromethane (volume ratio 2:1) to obtain 31.5 g (87%) of the target compound 2-92 as a white solid.

[0377] Comparative Synthesis Example 1: Synthesis of Compound Main Body 1

[0378]

[0379] The compound Host 1 (80%) according to Comparative Synthesis Example 1 was synthesized in the same manner as Synthesis Example 1, except that SM-12 was used instead of SM-6.

[0380] Theoretical values ​​for C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04, Exp. values: C, 84.55; H, 4.41; N, 7.99; O, 3.04

[0381] Comparative Synthesis Example 2: Synthesis of Compound Main Body 2

[0382]

[0383] Referring to the method known from KR 10-1814875, the compound main body 2 (89%) was synthesized.

[0384] Theoretical values ​​for C37H23N3S: C, 82.04; H, 4.28; N, 7.76; S, 5.92, Exp. values: C, 82.04; H, 4.28; N, 7.76; S, 5.92

[0385] (Production of organic light-emitting diodes)

[0386] Example 1

[0387] Thickness cleaning with distilled water and ultrasonic cleaning A glass substrate coated with ITO (indium tin oxide) was prepared. After washing with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The obtained ITO transparent electrode was used as an anode, and compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum deposited on the ITO substrate to form -thick hole injection layer, and then deposit compound A onto -thick to form a hole transport layer. Compound B is deposited on the hole transport layer as -Thick hole transport auxiliary layer. A thick hole transport auxiliary layer was formed by vacuum deposition on the hole transport auxiliary layer using the compound 1-3 obtained in Synthesis Example 1 as a host and 2 wt % of [Ir(piq)2acac] as a dopant. -thick light-emitting layer. Subsequently, on the light-emitting layer, a film was formed by simultaneously vacuum-depositing compound D and LiQ in a weight ratio of 1:1. -thick electron transport layer. On the electron transport layer, LiQ and Al are sequentially vacuum deposited to -Houhe -thick, thereby manufacturing an organic light emitting diode.

[0388] ITO / Compound A (doped with 3% NDP-9, ) / Compound A / Compound B / EML [Compound 1-3 (98wt%), [Ir(piq)2acac] (2wt%)] / Compound D: Liq / LiQ / Al Structure

[0389] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0390] Compound B: N,N-di([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoren[4,3-b]benzofuran-10-amine

[0391] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0392] Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazine-2-yl)phenyl)quinoline

[0393] Examples 2 to 10 and Comparative Examples 1 and 2

[0394] Diodes of Examples 2 to 10 and Comparative Examples 1 and 2 were produced in the same manner as in Example 1, except that the body was changed as shown in Table 2.

[0395] Embodiment 11

[0396] Thickness cleaning with distilled water and ultrasonic cleaning A glass substrate coated with ITO (indium tin oxide) was prepared. After washing with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned for 10 minutes by 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 (commercially available from Novaled) was vacuum deposited on the ITO substrate to form -thick hole injection layer, and then deposit compound A onto -thick to form a hole transport layer. Compound B is deposited on the hole transport layer as -Thick hole transport auxiliary layer. By using the compound 1-3 obtained in Synthesis Example 1 and the compound 2-92 obtained in Synthesis Example 10 as the host and 2 wt % of [Ir(piq)2acac] as the dopant, a thick hole transport auxiliary layer was formed by vacuum deposition on the hole transport auxiliary layer. -thick light-emitting layer. Herein, compound 1-3 and compound 2-92 were used in a weight ratio of 5:5. Subsequently, on the light-emitting layer, a layer was formed by simultaneously vacuum-depositing compound D and LiQ in a weight ratio of 1:1. -thick electron transport layer. On the electron transport layer, LiQ and Al are sequentially vacuum deposited to -Houhe -thick, thereby manufacturing an organic light emitting diode.

[0397] ITO / Compound A (doped with 3% NDP-9, ) / Compound A / Compound B / EML[98wt% host (Compound 1-3:Compound 2-92=5:5w / w), 2wt% [Ir(piq)2acac]] / Compound D: Liq / LiQ / Al structure.

[0398] Examples 12 to 18 and Comparative Examples 3 to 6

[0399] Diodes of Examples 12 to 18 and Comparative Examples 3 to 6 were produced in the same manner as in Example 11, except that the body was changed as shown in Table 3.

[0400] evaluate

[0401] The luminous efficiency and lifespan characteristics of the organic light emitting diodes of Examples 1 to 18 and Comparative Examples 1 to 6 were evaluated.

[0402] The specific measurement method is as follows, and the results are shown in Tables 2 and 3.

[0403] (1) Measuring the change in current density based on the change in voltage

[0404] The resulting organic light emitting diode was measured for a current value flowing into the unit device while increasing the voltage from 0 V to 10 V using a voltammeter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0405] (2) Measuring brightness changes based on voltage changes

[0406] While the voltage of the organic light emitting diode was increased from 0 V to 10 V, the luminance was measured using a photometer (Minolta Cs-1000A).

[0407] (3) Measurement of luminous efficiency

[0408] Using the luminance and current density and voltage from items (1) and (2), calculate the same current density (10 mA / cm 2 ) under luminous efficiency (cd / A).

[0409] The relative value of the luminous efficiency based on Comparative Example 2 was calculated and shown in Table 2.

[0410] The relative value of the luminous efficiency based on Comparative Example 6 was calculated and shown in Table 3.

[0411] (4) Lifespan measurement

[0412] The organic light emitting diodes of Examples 1 to 18 and Comparative Examples 1 to 6 were measured with respect to T95 lifespan in the following manner: 2 Initial brightness (cd / m 2 ) and measure the decrease in brightness over time, so that the T95 lifespan is obtained when the brightness decreases to 95% of the initial brightness.

[0413] The relative value of T95 life based on Comparative Example 2 was calculated and shown in Table 2.

[0414] The relative value of T95 life based on Comparative Example 6 was calculated and shown in Table 3.

[0415] (Table 2)

[0416] main body T95 life (%) efficiency(%) Example 1 1-3 152 107 Example 2 1-4 155 108 Example 3 1-7 145 102 Example 4 1-11 158 109 Example 5 1-12 159 106 Example 6 1-17 142 106 Example 7 1-30 120 112 Example 8 1-34 140 105 Example 9 1-35 144 104 Example 10 1-39 135 104 Comparative Example 1 Body 1 39 97 Comparative Example 2 Body 2 100 100

[0417] (Table 3)

[0418]

[0419] Referring to Table 2, the compounds according to the present invention show improved efficiency and lifetime as a single host compared to comparative compounds, and specifically, referring to Table 3, greatly improve the overall efficiency and lifetime when combined with a second host.

[0420] While the invention has been described in connection with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but on the contrary, the invention is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A compound for an organic optoelectronic device represented by Chemical Formula 1: [Chemical formula 1] in, In Chemical Formula 1, X 1 is O or S, L 1 and L 2 are each independently a single bond or a substituted or unsubstituted phenylene group, Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group or a substituted or unsubstituted dibenzosilyl group, R 1 To R 9 are independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl, and A is any one of the linking groups selected from Group I, [Group I] Among them, in group I, R a , R b , R c and R d are each independently hydrogen, deuterium or a substituted or unsubstituted C1 to C10 alkyl group, n1 is 0, m1, m2 and m4 are each independently an integer from 1 to 4, m3 is an integer of 1 or 2, m5 and m6 are each independently an integer from 1 to 3, and * is the connection point, Herein, "substituted" means that at least one hydrogen of the substituent is replaced by deuterium, C1 to C5 alkyl or cyano.

2. The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formula 1-I to Chemical Formula 1-VI: [Chemical Formula 1-I] in, In Chemical Formula 1-I to Chemical Formula 1-VI, X 1 , L 1 , L 2 ,Ar 1 ,Ar 2 , R 1 To R 9 , R a , R c , R d and m1, m3 to m6 are the same as defined in claim 1.

3. The compound according to claim 1, wherein *-L 1 -Ar 1 and *-L 2 -Ar 2 are each independently any one of the substituents selected from Group II: [Group II] in, In Group II, D is deuterium, m11 is an integer from 1 to 5, m12 is an integer from 1 to 4, m13 is an integer from 1 to 3, m14 is an integer from 1 to 7, and * is the connection point.

4. The compound according to claim 1, wherein the compound is one of the compounds of Group 1: [Group 1] 5. A composition for an organic optoelectronic device, comprising a first compound and a second compound, wherein the first compound is the compound for an organic optoelectronic device according to claim 1, and The second compound is a compound for an organic photoelectric device represented by Chemical Formula 2: [Chemical formula 2] in, In chemical formula 2, X 2 O, S, NL a -R e , CR f R g or SiR h R i , L a is a single bond or a substituted or unsubstituted C6 to C12 arylene group, R e , R f , R g , R h , R i , R 10 and R 11 are each independently hydrogen, deuterium, 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, n2 is an integer from 1 to 4, and B is any one selected from the rings of Group III, [Group III] Among them, in Group III, * is the connection point, X 3 O, S, CR j R k or SiR l R m , R j , R k , R l , R m and R 11 To R 18 are each independently hydrogen, deuterium, 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, n3, n5, n8 and n10 are each independently an integer from 1 to 4, n4, n6, n7 and n9 are each independently an integer of 1 or 2, and R e and R 10 To R 18 At least one of them is a group represented by chemical formula a, [Chemical formula a] Among them, in chemical formula a, 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 amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and * is the connection point.

6. The composition according to claim 5, wherein Chemical Formula 2 is represented by any one of Chemical Formula 2-I to Chemical Formula 2-X: in, In Chemical Formulae 2-I to 2-X, X 2 , X 3 , R 10 To R 13 , R 17 , R 18 , n2 to n5, n9 and n10 are the same as defined in claim 5.

7. The composition according to claim 5, wherein The second compound is represented by any one of Formula 2-IA to Formula 2-XA, Formula 2-IIB to Formula 2-IVB, and Formula 2-IIC to Formula 2-XC: In Chemical Formulae 2-IA to 2-XA, X 2 , X 3 , L 3 To L 5 ,Ar 3 , R 10 To R 13 , R 17 , R 18 ,Ar 4 , n3 to n5, n9 and n10 are the same as defined in claim 5, and n2 is an integer from 1 to 3; In Chemical Formula 2-IIB to Chemical Formula 2-IVB, X 2 , L 3 To L 5 , R 10 , R 12 , R 13 ,Ar 3 ,Ar 4 , n2 to n4 are the same as defined in claim 5, and n5 is an integer from 1 to 3; In Chemical Formulae 2-IIC to 2-IVC, X 2 , L 3 To L 5 ,Ar 3 ,Ar 4 , R 10 , R 12 , R 13 , n2 and n5 are the same as defined in claim 5, and n4 is an integer of 1; and In the chemical formulae 2-VC to 2-XC, X 2 , X 3 , L 3 To L 5 ,Ar 3 ,Ar 4 , R 10 , R 17 , R 18 , n2 and n10 are the same as defined in claim 5, and n9 is an integer of 1.

8. The composition according to claim 7, wherein R 10 To R 13 , R 17 and R 18 and are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl, or substituted or unsubstituted C6 to C30 aryl.

9. The composition according to claim 7, wherein The second compound is represented by any one of Chemical Formula 2-IA-3, Chemical Formula 2-IVB-2 and Chemical Formula 2-XA-2: in, In Formula 2-IA-3, Formula 2-IVB-2 and Formula 2-XA-2, X 2 , X 3 , R 10 , R 11 To R 13 , R 17 , R 18 , L 3 To L 5 ,Ar 3 ,Ar 4 , n2 to n5, n9 and n10 are the same as defined in claim 7.

10. The composition according to claim 5, wherein Ar 3 and Ar 4 and are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted chrysene, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzofuranofluorenyl, or substituted or unsubstituted benzothiophenefluorenyl.

11. The composition according to claim 5, wherein The second compound is one of the compounds of Group 2: [Group 2] 12. An organic optoelectronic device comprising an anode and a cathode opposite each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 4; or The composition for an organic optoelectronic device according to any one of claims 5 to 11.

13. The organic optoelectronic device according to claim 12, wherein The organic layer comprises a light-emitting layer, and The light-emitting layer includes the compound for an organic photoelectric device or the composition for an organic photoelectric device. 14 . A display device comprising the organic optoelectronic device according to claim 12 .

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