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

Abstract

This invention relates to a compound represented by chemical formula 1 for use in organic optoelectronic devices; and compositions comprising the compound for use in organic optoelectronic devices, organic optoelectronic devices, and display devices. Chemical formula 1 is described as defined in the specification.

Description

Technical Field

[0001] A compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device are disclosed. Background Technology

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

[0003] Based on their working principles, organic optoelectronic devices can be broadly classified into two categories. One category consists of optoelectronic devices that generate electrical energy by separating excitons formed from light energy into electrons and holes and transferring the electrons and holes to different electrodes. The other category consists of light-emitting devices that generate light energy from electrical energy by providing voltage or current to the electrodes.

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

[0005] Organic light-emitting diodes (OLEDs) have attracted considerable attention in recent years due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is greatly influenced by the organic materials between the electrodes. Summary of the Invention

[0006] Technical issues

[0007] One embodiment provides a compound for organic optoelectronic devices that enables high-efficiency and long-life organic optoelectronic devices.

[0008] Another embodiment provides a composition for an organic optoelectronic device, the composition comprising the compound for the organic optoelectronic device.

[0009] Another embodiment provides an organic optoelectronic device comprising a compound or composition for an organic optoelectronic device.

[0010] Another embodiment provides a display device that includes an organic optoelectronic device.

[0011] Technical solution

[0012] According to one embodiment, a compound for an organic optoelectronic device, represented by chemical formula 1, is provided.

[0013] [Chemical Formula 1]

[0014]

[0015] In chemical formula 1,

[0016] X 1 and X 2 Each can be either O or S independently.

[0017] L 1 To L 3 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene.

[0018] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0019] R 1 To R 4 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0020] m1 is one of the integers from 1 to 4.

[0021] m2 and m3 are each an independent integer of 1 or 2, and

[0022] m4 is one of the integers from 1 to 3.

[0023] According to another embodiment, the composition for an organic optoelectronic device comprises a first compound and a second compound.

[0024] The first compound is as described above, and the second compound may be a compound represented by chemical formula 2 for use in organic optoelectronic devices.

[0025] [Chemical Formula 2]

[0026]

[0027] In chemical formula 2,

[0028] X 3 For O, S, NL a -R a CR b R c or SiR d R e ,

[0029] L a It is a single bond or a substituted or unsubstituted C6 to C12 arylene.

[0030] R a R b R c R d Re and R 5 Each is independently hydrogen, deuterium, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C2 to C30 heterocyclic group.

[0031] m5 is one of the integers from 1 to 4, and

[0032] A is selected from any of the rings listed in Group II.

[0033] [Group II]

[0034]

[0035] In Group II,

[0036] * indicates a connection point.

[0037] X 4 For O or S,

[0038] R 6 To R 13 Each is independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C30 heterocyclic group.

[0039] m6, m8, m11, and m13 are each an independent integer from 1 to 4.

[0040] m7, m9, m10, and m12 are each an independent integer of 1 or 2, and

[0041] R a and R 5 To R 13 At least one of them is a group represented by the chemical formula a.

[0042] [Chemical formula a]

[0043]

[0044] In chemical formula a,

[0045] Z 1 To Z 3 Each is independently N or CR f ,

[0046] Z 1 To Z 3 At least two of them are N.

[0047] R f It is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl.

[0048] L 4 To L6 Each is an independent single bond or a substituted or unsubstituted C6 to C30 arylene.

[0049] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and

[0050] * indicates a connection point.

[0051] According to another embodiment, the organic optoelectronic device includes an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, and the organic layer contains a compound for the organic optoelectronic device or a composition for the organic optoelectronic device.

[0052] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0053] Beneficial effects

[0054] It can realize organic optoelectronic devices with high efficiency and long life. Attached Figure Description

[0055] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0056] <Explanation of Figure Markers>

[0057] 100: Organic Light Emitting Diode

[0058] 105: Organic layer

[0059] 110: Cathode

[0060] 120: Anode

[0061] 130: Emissive layer

[0062] 140: Hole transport region

[0063] 150: Electron transport region Detailed Implementation

[0064] Embodiments of the invention are described in detail below. However, these embodiments are exemplary, and the invention is not limited thereto; rather, the invention is defined by the scope of the claims.

[0065] As used herein, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by a deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amino, 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 combinations thereof.

[0066] In one embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0067] "Unsubstituted" means that the hydrogen atom has not been replaced by another substituent and retains the hydrogen atom.

[0068] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0069] As used herein, unless otherwise defined, “heterogeneous” means a functional group containing one to three heteroatoms selected from N, O, S, P, and Si, with the remainder being carbon.

[0070] As used herein, “aryl” means a group comprising at least one aromatic hydrocarbon moiety, wherein all elements of the aromatic hydrocarbon moiety have conjugated p-orbitals, such as phenyl, naphthyl, etc.; two or more aromatic hydrocarbon moiety may be linked by σ bonds and may be, for example, biphenyl, terphenyl, tetraphenyl, etc.; and two or more aromatic hydrocarbon moiety may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0071] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0072] As used herein, "heterocyclic group" is a superordinate concept of a heteroaryl group and may include at least one heteroatom selected from N, O, S, P, and Si in place of carbon (C) in cyclic compounds such as aryl, cycloalkyl, their fused rings, or combinations thereof. When the heterocyclic group is fused, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0073] For example, "heteroaryl" can refer to an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly connected by σ bonds, or when a heteroaryl group comprises two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring may comprise one to three heteroatoms.

[0074] More specifically, the substituted or unsubstituted C6 to C30 aryl group can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthrene, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted pyrene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted meta-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted trefyl, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof, but is not limited thereto.

[0075] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted pyrrole 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 benzothiophene group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indoleyl group, etc. Substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzofuranpyrimidyl (benzofuranpyrimidyl), substituted or unsubstituted benzothiophenpyrimidyl (benzothiophenpyrimidyl), or combinations thereof, but not limited thereto.

[0076] As used herein, hole properties refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductivity of the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be easily injected into and transported in the light-emitting layer.

[0077] Furthermore, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into and transported in the light-emitting layer.

[0078] Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

[0079] According to one embodiment, a compound for an organic optoelectronic device is represented by chemical formula 1.

[0080] [Chemical Formula 1]

[0081]

[0082] In chemical formula 1,

[0083] X 1 and X 2 Each can be either O or S independently.

[0084] L 1 To L 3 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene.

[0085] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0086] R 1 To R 4 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0087] m1 is one of the integers from 1 to 4.

[0088] m2 and m3 are each an independent integer of 1 or 2, and

[0089] m4 is one of the integers from 1 to 3.

[0090] In the compound represented by Formula 1, dibenzofuran (or dibenzothiophene) is fused with naphthofuran (or naphthothiophene), thereby increasing the planarity of the molecules and improving the lattice stacking, which in turn increases the glass transition temperature and hole mobility. Furthermore, when it is substituted with an amino group, hole injection and hole movement become faster.

[0091] The high glass transition temperature resulting from these structural features ensures stable device characteristics by maintaining a stable film even under Joule heat generated during device operation, enabling devices with excellent lifespans. Furthermore, the high hole mobility and rapid hole injection characteristics improve the device's drive voltage.

[0092] In chemical formula 1, when m1 is 2 or greater, each R 1 They can be the same as or different from each other.

[0093] In chemical formula 1, when m2 is 2, each R 2 They can be the same as or different from each other.

[0094] In chemical formula 1, when m3 is 2, each R 3 They can be the same as or different from each other.

[0095] In chemical formula 1, when m4 is 2 or greater, each R 4 They can be the same as or different from each other.

[0096] As an example, chemical formula 1 can be represented by any one of chemical formula 1A, chemical formula 1B, and chemical formula 1C.

[0097] [Chemical Formula 1A]

[0098]

[0099] [Chemical Formula 1B]

[0100]

[0101] [Chemical Formula 1C]

[0102]

[0103] In chemical formulas 1A, 1B, and 1C

[0104] X 1 X 2 L 1 To L 3 Ar 1 Ar 2 R 1 To R4 The same applies to m1 to m4 as described above.

[0105] As a specific example, depending on the specific substitution position of the amino group, chemical formula 1A can be represented by one of chemical formulas 1A-1, 1A-2, 1A-3, and 1A-4.

[0106] [Chemical Formula 1A-1]

[0107]

[0108] [Chemical Formula 1A-2]

[0109]

[0110] [Chemical Formula 1A-3]

[0111]

[0112] [Chemical Formula 1A-4]

[0113]

[0114] In chemical formulas 1A-1, 1A-2, 1A-3, and 1A-4, X 1 X 2 L 1 To L 3 Ar 1 Ar 2 R 1 To R 4 The same applies to m1 to m4 as described above.

[0115] As a specific example, depending on the specific substitution position of the amino group, chemical formula 1B can be represented by one of chemical formulas 1B-1, 1B-2, 1B-3, and 1B-4.

[0116] [Chemical Formula 1B-1]

[0117]

[0118] [Chemical Formula 1B-2]

[0119]

[0120] [Chemical Formula 1B-3]

[0121]

[0122] [Chemical Formula 1B-4]

[0123]

[0124] In chemical formulas 1B-1, 1B-2, 1B-3, and 1B-4, X 1 X 2 L 1 To L 3 Ar 1 Ar 2 R 1 To R 4 The same applies to m1 to m4 as described above.

[0125] As a specific example, depending on the specific substitution position of the amino group, the chemical formula 1C can be represented by one of the chemical formulas 1C-1, 1C-2, 1C-3, and 1C-4.

[0126] [Chemical formula 1C-1]

[0127]

[0128] [Chemical formula 1C-2]

[0129]

[0130] [Chemical formula 1C-3]

[0131]

[0132] [Chemical formula 1C-4]

[0133]

[0134] In chemical formulas 1C-1 to 1C-4, X 1 X 2 L 1 To L 3 Ar 1 Ar 2 R 1 To R 4 The same applies to m1 to m4 as described above.

[0135] For example, chemical formula 1 can be represented by any one of chemical formulas 1A-1 to 1A-4.

[0136] For example, Ar 1 and Ar 2Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted trefyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophene, or substituted or unsubstituted dibenzothiophene (dibenzosilolyl group).

[0137] As a specific example, Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted dibenzothiopheneyl.

[0138] For example, Ar 1 and Ar 2 Each can be any of the substituents listed in group I, independently.

[0139] [Group I]

[0140]

[0141] The substituents listed in Group I can be replaced by other substituents, and

[0142] Other substituents may be, for example, deuterium, substituted or unsubstituted C1 to C5 alkyl groups, or substituted or unsubstituted C6 to C12 aryl groups.

[0143] For example, L 1 It can be a single key, and

[0144] L 2 and L 3 Each can be a single bond or a substituted or unsubstituted phenylene group.

[0145] For example, R 1 To R 4 Each can be independently hydrogen, deuterium, substituted or unsubstituted C1 to C5 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0146] As a specific example, R 1 To R 4 They can be either hydrogen or deuterium.

[0147] For example, X 1 It can be O or S, and X 2It can be S.

[0148] For example, compounds represented by chemical formula 1 for use in organic optoelectronic devices may include, but are not limited to, the compounds listed in group 1.

[0149] [Group 1]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] According to another embodiment, the composition for an organic optoelectronic device comprises a first compound and a second compound, wherein the first compound may be the compound described above for an organic optoelectronic device, and the second compound may be a compound for an organic optoelectronic device represented by chemical formula 2.

[0170] [Chemical Formula 2]

[0171]

[0172] In chemical formula 2,

[0173] X 3 For O, S, NL a -R a CR b R c or SiR d R e ,

[0174] L a It is a single bond or a substituted or unsubstituted C6 to C12 arylene.

[0175] R a R b R c R d R e and R 5 Each is independently hydrogen, deuterium, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C2 to C30 heterocyclic group.

[0176] m5 is one of the integers from 1 to 4, and

[0177] A is selected from any of the rings listed in Group II.

[0178] [Group II]

[0179]

[0180] In Group II,

[0181] * indicates a connection point.

[0182] X 4 For O or S,

[0183] R 6 To R 13 Each is independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C30 heterocyclic group.

[0184] m6, m8, m11, and m13 are each an independent integer from 1 to 4.

[0185] m7, m9, m10, and m12 are each an independent integer of 1 or 2, and

[0186] R a and R 5 To R 13 At least one of them is a group represented by the chemical formula a.

[0187] [Chemical formula a]

[0188]

[0189] In chemical formula a,

[0190] Z 1 To Z 3 Each is independently N or CR f ,

[0191] Z 1 To Z 3 At least two of them are N.

[0192] R f It is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl.

[0193] L 4 To L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C30 arylene.

[0194] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and

[0195] * indicates a connection point.

[0196] The second compound has a structure in which a nitrogen-containing six-membered ring is substituted.

[0197] The second compound effectively extends the LUMO band by being substituted with a nitrogen-containing six-membered ring. Therefore, when used together with the first compound in the light-emitting layer, the charge mobility and stability are increased, thereby increasing the balance between holes and electrons, improving the luminous efficiency and lifetime characteristics of the device, and reducing the driving voltage.

[0198] In chemical formula 2, when m5 is 2 or greater, each R 5 They can be the same as or different from each other.

[0199] In group II, when m6 is 2 or greater, each R 6 They can be the same as or different from each other.

[0200] In group II, when m7 is 2, each R 7 They can be the same as or different from each other.

[0201] In group II, when m8 is 2 or greater, each R 8 They can be the same as or different from each other.

[0202] In group II, when m9 is 2, each R 9 They can be the same as or different from each other.

[0203] In group II, when m10 is 2, each R 10 They can be the same as or different from each other.

[0204] In group II, when m11 is 2 or greater, each R 11 They can be the same as or different from each other.

[0205] In group II, when m12 is 2, each R 12 They can be the same as or different from each other.

[0206] In group II, when m13 is 2 or greater, each R 13 They can be the same as or different from each other.

[0207] Furthermore, ring A of the second compound can be selected from the rings listed in Group II. For example, the second compound can be represented by any one of chemical formulas 2-I to 2-X.

[0208]

[0209]

[0210] In chemical formulas 2-I to 2-X

[0211] X 3 X 4 Z 1 To Z 3 R 5 To R 13 m5 to m10, m12 to m13, L 4 To L 6 Ar 3 and Ar 4 Same as above, and

[0212] m5', m8', and m11' are each an independent integer from 1 to 3.

[0213] The second compound according to one embodiment can be represented by any one of chemical formula 2-I, chemical formula 2-III, and chemical formula 2-VI.

[0214] According to a specific embodiment, the second compound may be represented by any one of chemical formulas 2-I-3, 2-III-1, 2-VI-1, and 2-VI-3.

[0215]

[0216] In chemical formulas 2-I-3, 2-III-1, 2-VI-1, and 2-VI-3

[0217] X 3 Z 1 To Z 3 R 5 To R 8 m5, m5', m6 to m8, m8', L 4 To L 6 Ar 3 and Ar 4 Same as above.

[0218] For example, Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene.

[0219] As a specific example, Ar 3 and Ar 4 Each can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.

[0220] For example, L 4 To L 6 Each can be a single bond, a substituted or unsubstituted phenylene, or a substituted or unsubstituted biphenylene.

[0221] As a specific example, L 4 and L 5 Each can be an independent single bond or a substituted or unsubstituted phenylene, and L 6 It can be a single key.

[0222] As an example, R 5 To R 13 Each can be independently hydrogen, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C12 aryl, or substituted or unsubstituted C2 to C18 heterocyclic.

[0223] As a specific example, R 5 To R 13 Each can be hydrogen, deuterium, phenyl, or naphthyl, and each can be independent of the other.

[0224] For example, X 3 It can be O, S, CR b Rc or SiR d R e , where R b R c R d and R e Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C20 aryl.

[0225] As a specific example, R b R c R d and R e Each can be independently methyl, substituted or unsubstituted phenyl, or substituted or unsubstituted biphenyl.

[0226] For example, the second compound may be one of the compounds listed in Group 2.

[0227] [Group 2]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] A composition for an organic optoelectronic device according to a more specific embodiment of the present invention comprises a first compound represented by chemical formula 1A-2 or chemical formula 1A-3 and a second compound represented by chemical formula 2-III-1 or chemical formula 2-VI-1.

[0234] The first and second compounds can be contained in a weight ratio of, for example, 1:99 to 99:1. By including them within this range, bipolar characteristics can be achieved by adjusting the appropriate weight ratio using the electron transport capability of the first compound and the hole transport capability of the second compound, thereby improving efficiency and lifetime. Within this range, they can be contained in weight ratios of, for example, about 10:90 to 90:10, about 20:80 to 80:20 (e.g., about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40). As a specific example, they can be contained in weight ratios of 40:60, 50:50, or 60:40.

[0235] In addition to the first and second compounds mentioned above, it may also contain one or more compounds.

[0236] The compounds or compositions used in organic optoelectronic devices described above may also contain dopants.

[0237] The dopant can be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and can be, for example, a red or green phosphorescent dopant.

[0238] A dopant is a material that is mixed in small amounts with a compound or composition used in organic optoelectronic devices to induce luminescence, and is typically a material such as a metal complex that emits light by being excited multiple times to a triplet or more states. Dopants can be, for example, inorganic, organic, or organic-inorganic compounds, and one or more of these types can be used.

[0239] Examples of dopants can be phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds, including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants can be, for example, compounds represented by the chemical formula Z, but are not limited thereto.

[0240] [Chemical Formula Z]

[0241] L 7 MX 5

[0242] In the chemical formula Z, M is a metal, and L 7 and X 5 The same or different ligands that form a complex with M.

[0243] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 7 and X 5 It could be, for example, a bidentate ligand.

[0244] By L 7 and X 5 Examples of ligands may be selected from, but are not limited to, the chemical formulas listed in group A.

[0245] [Group A]

[0246]

[0247] In group A,

[0248] R 300 To R 302Each is independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen.

[0249] R 303 To R 324 Each of the following 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, trialkylsilyl having substituted or unsubstituted C1 to C30 alkyl, dialkylarylsilyl having substituted or unsubstituted C1 to C30 alkyl and C6 to C30 aryl, or triarylsilyl having substituted or unsubstituted C6 to C30 aryl.

[0250] For example, it may include dopants represented by chemical formula III.

[0251] [Chemical Formula III]

[0252]

[0253] In chemical formula III,

[0254] R 101 To R 116 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 ,

[0255] R 132 To R 134 Each is independently a C1 to C6 alkyl group.

[0256] R 101 To R 116 At least one of them is a functional group represented by the chemical formula IV-1.

[0257] L 100 It can be a bidentate ligand of a monovalent anion, and a ligand coordinated to iridium via the lone pair electrons of a carbon or heteroatom.

[0258] n1 and n2 are each independent integers from 0 to 3, and n1+n2 is an integer from 1 to 3.

[0259] [Chemical Formula III-1]

[0260]

[0261] In chemical formula III-1,

[0262] R 135 To R 139 Each is 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

[0263] * refers to the part that is bonded to a carbon atom.

[0264] For example, it may include dopants represented by the chemical formula Z-1.

[0265] [Chemical Formula Z-1]

[0266]

[0267] In chemical formula Z-1, rings A, B, C, and D are each independently a 5- or 6-membered carbon ring or a heterocycle;

[0268] R A R B R C and R D Each can be independently mono-, di-, tri-, or tetra-substituted or unsubstituted;

[0269] L B L C and L D Each can be independently a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof.

[0270] When nA is 1, L E It can be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof; and when nA is 0, L E It does not exist;

[0271] R A R B R C R DR and R' are each independently hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thioalkyl, sulfinyl, sulfonyl, phosphinyl, or combinations thereof; any adjacent R A R B R C R D R and R' are optionally connected to each other to provide a loop; X B X C X D and X E Each is independently selected from carbon and nitrogen; and Q 1 Q 2 Q 3 and Q 4 Each represents oxygen or a direct bond.

[0272] According to one embodiment, the dopant may be a platinum complex and may be represented by the chemical formula IV.

[0273] [Chemical Formula IV]

[0274]

[0275] In chemical formula IV,

[0276] X 100 Selected from O, S and NR 131 ,

[0277] R 117 To R 131 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 ,

[0278] R 132 To R 134 Each is independently a C1 to C6 alkyl group, and

[0279] R 117 To R 131 At least one of them can be -SiR 132 R 133 R 134 Or tert-butyl.

[0280] The compounds or compositions used in organic optoelectronic devices described above can be formed by dry film deposition methods (such as chemical vapor deposition).

[0281] In the following text, an organic optoelectronic device comprising the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device will be described.

[0282] Organic optoelectronic devices can be suitable devices that convert electrical energy into light energy and vice versa, such as organic photoelectric devices, organic light-emitting diodes, organic solar cells, and organic photosensitive drums.

[0283] In this article, an organic light-emitting diode (OLED) is described as an example of an organic optoelectronic device with reference to the accompanying drawings.

[0284] Figure 1 This is a cross-sectional view showing an organic light-emitting diode according to an embodiment.

[0285] 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.

[0286] The anode 120 may be made of a conductor with a high 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, etc., or alloys thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; a combination of metals and oxides such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0287] The cathode 110 may be made of a conductor with 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 alloys thereof; a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0288] The organic layer 105 may contain the compounds or compositions described above for organic optoelectronic devices.

[0289] The organic layer 105 may include a light-emitting layer 130, and the light-emitting layer 130 may contain the compounds or compositions described above for organic optoelectronic devices.

[0290] Compositions for organic optoelectronic devices that also contain dopants can be, for example, green light emitting compositions.

[0291] The light-emitting layer 130 may contain, for example, the compounds or compositions for organic optoelectronic devices described above as phosphorescent hosts.

[0292] In addition to the light-emitting layer, the organic layer may also include charge transport regions.

[0293] The charge transport region can be, for example, the hole transport region 140.

[0294] The hole transport region 140 can further increase hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0295] 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 included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0296] [Group B]

[0297]

[0298]

[0299]

[0300]

[0301] In the hole transport region, in addition to the compounds mentioned above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, and compounds with similar structures may also be used.

[0302] In addition, the charge transport region can be, for example, the electron transport region 150.

[0303] The electron transport region 150 can further increase electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0304] 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.

[0305] [Group C]

[0306]

[0307]

[0308]

[0309]

[0310] One embodiment of the present invention can provide an organic light-emitting diode including an organic layer as the light-emitting layer.

[0311] Another embodiment of the present invention can provide an organic light-emitting diode comprising an emitting layer and a hole transport region as an organic layer.

[0312] Another embodiment of the present invention can provide an organic light-emitting diode comprising an organic layer and an electron transport region as an organic layer.

[0313] like Figure 1 As shown, in addition to the light-emitting layer 130, another embodiment of the present invention can provide an organic light-emitting diode that also includes a hole transport region 140 and an electron transport region 150 as an organic layer 105.

[0314] In another embodiment of the present invention, in addition to the light-emitting layer, the organic light-emitting diode may also include an electron injection layer (not shown), a hole injection layer (not shown), etc., as organic layers.

[0315] Organic light-emitting diodes 100 can be produced by forming an anode or cathode on a substrate, then forming an organic layer by a dry film method (such as vacuum deposition, sputtering, plasma electroplating and ion electroplating), and forming a cathode or anode thereon.

[0316] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0317] In the following description, implementation methods are illustrated in more detail with reference to embodiments. However, these embodiments are exemplary, and the scope of the invention is not limited thereto.

[0318] In the following text, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., or Tokyo Chemical Industry, or synthesized by known methods, unless otherwise specified.

[0319] (Preparation of compounds for organic optoelectronic devices)

[0320] Synthesis Example 1: Synthesis of Compound 1-130

[0321] [Reaction Formula 1]

[0322]

[0323] Step 1: Synthesis of Int-3

[0324] Int-1 (100 g, 336 mmol) was dissolved in 800 mL of dioxane, and Int-2 (58.7 g, 336 mmol) and tetrakis(triphenylphosphine)palladium (11.7 g, 10.1 mmol) were added, followed by stirring. Then, sodium carbonate saturated in water (89.1 g, 841 mmol) was added, and the mixture was heated to reflux at 110 °C for 24 hours. When the reaction was complete, water was added, and the reaction solution was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by rapid column chromatography to give 100.3 g (86%) of Int-3.

[0325] Step 2: Synthesis of Int-4

[0326] In a 1000 mL round-bottom flask, 100.3 g (289 mmol) of Int-3 was added to 550 mL of N,N-dimethylformamide, and the internal temperature was set to 0 °C. Subsequently, 22.4 g (303.8 mmol) of sodium thiomethoxide (CAS No.: 5188-07-8) and 59.9 g (433.98 mmol) of potassium carbonate were slowly added. The internal temperature was maintained at 0 °C. The flask was then heated to 80 °C under a nitrogen atmosphere. After 16 hours, the reaction solution was cooled, and ethyl acetate and water were added. The mixture was then stirred, and the organic layer was subjected to reduced pressure and column chromatography to give 85 g (yield: 78%) of Int-4.

[0327] Step 3: Synthesis of Int-5

[0328] 85 g (227 mmol) of Int-4 was added to 450 mL of acetic acid, and the internal temperature was set to 0 °C. Then, 50 mL of hydrogen peroxide was slowly added. The internal temperature was maintained at 0 °C. After stirring at room temperature for 12 hours, the reaction solution was placed in ice water, extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure to give 84 g (yield: 95%) of Int-5.

[0329] Step 4: Synthesis of Int-6

[0330] 84 g (214.9 mmol) of Int-5 was added to 500 mL of sulfuric acid. The mixture was stirred at room temperature for 20 hours, then the reaction solution was placed in ice water and adjusted to pH 9 with aqueous NaOH solution. Subsequently, the reaction solution was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered under reduced pressure, and concentrated to obtain 59 g (yield: 77%) of Int-6.

[0331] Step 5: Synthesis of Compounds 1-130

[0332] 3.0 g (8.42 mmol) of Int-6, 2.59 g (8.84 mmol) of Int-7, 2.43 g (25.25 mmol) of sodium tert-butoxide, and 0.84 g (0.84 mmol) of tri-tert-butylphosphine were dissolved in 50 mL of xylene, and 0.39 g (0.42 mmol) of Pd2(dba)3 was added. The mixture was then stirred and refluxed under a nitrogen atmosphere for 12 hours. When the reaction was complete, the mixture was extracted with xylene and distilled water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography using n-hexane / dichloromethane (2:1 v / v) to give 3.78 g (73% yield) of compound 1-130.

[0333] Calculated values ​​for C44H27NOS: C, 85.55; H, 4.41; N, 2.27; O, 2.59; S, 5.19; Measured values: C, 85.55; H, 4.41; N, 2.27; O, 2.59; S, 5.19

[0334] Synthesis Example 2: Synthesis of Int-12 to Int-39

[0335] [Reaction 2]

[0336]

[0337] Except that Int-8, Int-13, and Int-18 were used to replace Int-2 in Synthesis Example 1, Int-12, Int-17, and Int-22 were synthesized in the same manner as steps 1 to 5 of the method in Synthesis Example 1.

[0338] In addition, except that Int-23 was used instead of Int-1 in Synthesis Example 1, and Int-8, Int-13, Int-2 and Int-18 were used respectively, Int-27, Int-31, Int-35 and Int-39 were synthesized in the same manner as steps 1 to 5 of the method of Synthesis Example 1.

[0339] Synthesis Example 3: Synthesis of Int-40 to Int-44

[0340] [Reaction 3]

[0341]

[0342] Int-40 to Int-44 were synthesized in the same manner as step 5 of Synthesis Example 1.

[0343] Synthetic Examples 4 to 17

[0344] Each compound was synthesized in the same manner as in Synthesis Example 1, except that in step 5 of Synthesis Example 1, Int A as shown in Table 1 was used instead of Int-6 and Int B as shown in Table 1 was used instead of Int-7.

[0345] [Table 1]

[0346]

[0347]

[0348]

[0349] Synthesis Example 18: Synthesis of Compound A-3

[0350] [Reaction 4]

[0351]

[0352] Step 1: Synthesis of Int-45

[0353] In a round-bottom flask, 22.6 g (100 mmol) of 2,4-dichloro-6-phenyl-1,3,5-triazine was added to 200 mL of tetrahydrofuran and 100 mL of distilled water. Then, 0.9 equivalents of dibenzofuran-3-boronic acid (CAS No.: 395087-89-5), 0.03 equivalents of tetra-triphenylphosphine palladium, and 2 equivalents of potassium carbonate were added, and the mixture was heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The resulting solid was washed with water and hexane and recrystallized from 200 mL of toluene to give 21.4 g (60% yield) of Int-45.

[0354] Step 2: Synthesis of Int-46

[0355] In a round-bottom flask, 50.0 g (261.16 mmol) of 1-bromo-4-chlorobenzene, 44.9 g (261.16 mmol) of 2-naphthenic acid, 9.1 g (7.83 mmol) of tetraphenylphosphine palladium, and 71.2 g (522.33 mmol) of potassium carbonate were dissolved in 1000 mL of tetrahydrofuran and 500 mL of distilled water, and then heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The resulting solid was washed with water and hexane, and then recrystallized from 200 mL of toluene to give 55.0 g (yield: 88%) of Int-46.

[0356] Step 3: Synthesis of Int-47

[0357] In a round-bottom flask, 100.0 g (418.92 mmol) of the synthesized Int-46 was added to 1000 mL of DMF, along with 17.1 g (20.95 mmol) of dichlorodiphenylphosphinoferrocene palladium and 127.7 g of...

[0358] 502.70 mmol of diboronyl diboron and 123.3 g (1256.76 mmol) of potassium acetate were reacted and heated under reflux for 12 hours under a nitrogen atmosphere. The reaction solution was cooled and then added dropwise to 2 L of water to capture the solid. The resulting solid was dissolved in boiling toluene, filtered through silica gel, and the filtrate was concentrated. The concentrated solid was stirred with a small amount of hexane and filtered to give 28.5 g (yield: 70%) of Int-47.

[0359] Step 4: Synthesis of compound A-3

[0360] In a round-bottom flask, 10.0 g (27.95 mmol) of Int-47, 11.1 g (33.54 mmol) of Int-45, 1.0 g (0.84 mmol) of tetraphenylphosphine palladium, and 7.7 g (55.90 mmol) of potassium carbonate were dissolved in 150 mL of tetrahydrofuran and 75 mL of distilled water, and then heated to reflux under a nitrogen atmosphere. After 12 hours, the reaction solution was cooled, the aqueous layer was removed, and the organic layer was dried under reduced pressure. The resulting solid was washed with water and methanol, and then recrystallized from 200 mL of toluene to give 13.4 g (yield: 91%) of compound A-3.

[0361] Calculated values ​​for C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Measured values: C, 84.55; H, 4.41; N, 8.00; O, 3.03

[0362] Synthesis Example 19: Synthesis of Compound A-17

[0363] [Reaction 5]

[0364]

[0365] Compound A-17 was synthesized in the same manner as step 4 of Synthesis Example 18, except that 1.0 equivalents of Int-53 and Int-54 were used respectively.

[0366] Calculated values ​​for C41H25N3O: C, 85.54; H, 4.38; N, 7.30; O, 2.78; Measured values: C, 85.53; H, 4.38; N, 7.30; O, 2.77

[0367] Synthesis Example 20: Synthesis of Compound A-37

[0368] [Reaction Formula 6]

[0369]

[0370] Compound A-37 was synthesized in the same manner as step 4 of Synthesis Example 18, except that 1.0 equivalents of Int-53 and Int-52 were used respectively.

[0371] Calculated values ​​for C37H23N3O: C, 84.55; H, 4.41; N, 7.99; O, 3.04; Measured values: C, 84.57; H, 4.40; N, 7.99; O, 3.03

[0372] Synthetic Examples 21 and 22

[0373] Each compound was synthesized in the same manner as step 4 of Synthetic Example 18, except that Int C from Table 2 was used instead of Int-47 in Synthetic Example 18 and Int D from Table 2 was used instead of Int-45.

[0374] [Table 2]

[0375]

[0376] Comparative Synthesis Example 1: Synthesis of Compound C-1

[0377] [Reaction Formula 7]

[0378]

[0379] Compound C-1 was synthesized in the same manner as step 5 of Synthesis Example 1, except that Int-58 was used instead of Int-6.

[0380] Calculated values ​​for C40H25NOS: C, 84.63; H, 4.44; N, 2.47; O, 2.82; S, 5.65; Measured values: C, 84.63; H, 4.44; N, 2.47; O, 2.82; S, 5.65

[0381] (Manufacturing of Organic Light Emitting Diodes)

[0382] Example 1

[0383] Wash with distilled water to remove the coating with a thickness of [missing information]. An ITO (indium tin oxide) glass substrate was prepared. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes, followed by a vacuum deposition apparatus. The prepared ITO transparent electrode was used as the anode, and compound A, doped with 3% NDP-9 (Novaled GmbH), was vacuum deposited onto the ITO substrate to form... A thick hole injection layer was formed, and compound A was deposited on the hole injection layer. The thickness is increased to form a hole transport layer. Compound B is deposited onto the hole transport layer... The thickness was adjusted to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound 1-130 obtained in Synthesis Example 1 was used as the host, and 2 wt% of [Ir(piq)₂acac] was doped as a dopant, to form the layer by vacuum deposition. A thick luminescent layer. Subsequently, compound C is deposited on the luminescent layer. The thickness is such that an electron transport auxiliary layer is formed, and compounds D and LiQ are simultaneously vacuum-deposited at a weight ratio of 1:1 to form a thickness of [missing information]. The electron transport layer. This is achieved by sequentially vacuum-depositing on the electron transport layer. LiQ and Al is used to form the cathode to manufacture organic light-emitting diodes.

[0384] ITO / Compound A (3% NDP-9 doped) ) / Compound A( ) / Compound B( ) / EML[body(compound 1-130, 98wt%), [Ir(piq)2acac](2wt%)]( ) / Compound C( Compound D:Liq( ) / LiQ( ) / Al( ).

[0385] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0386] Compound B: N,N-bis([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-fluorenzo[4,3-b]benzofuran-10-amine

[0387] Compound C: 2-(3-(3-(9,9-dimethyl-9H-fluorene-2-yl)phenyl)phenyl)-4,6-diphenyl-1,3,5-triazine

[0388] Compound D: 8-(4-(4,6-bis(naphthyl-2-yl)-1,3,5-triazin-2-yl)phenyl)quinoline

[0389] Examples 2 to 15 and Comparative Example 1

[0390] Except for the changes to the main body as shown in Table 3, each organic light-emitting diode is manufactured in the same manner as in Example 1.

[0391] Example 16

[0392] Wash with distilled water to remove the coating with a thickness of [missing information]. An ITO (indium tin oxide) glass substrate was prepared. After washing with distilled water, the glass substrate was ultrasonically cleaned with solvents such as isopropanol, acetone, and methanol, and then dried. It was then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes, followed by a vacuum deposition apparatus. The prepared ITO transparent electrode was used as the anode, and compound A, doped with 3% NDP-9 (Novaled GmbH), was vacuum deposited onto the ITO substrate to form... A thick hole injection layer was formed, and compound A was deposited on the hole injection layer. The thickness is increased to form a hole transport layer. Compound B is deposited onto the hole transport layer... The thickness was adjusted to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compounds 1-130 obtained in Synthesis Example 1 and A-17 obtained in Synthesis Example 19 were used as the host, and 2 wt% of [Ir(piq)2acac] was doped as a dopant to form the layer by vacuum deposition. A thick luminescent layer. Here, compound 1-130 and compound A-17 were used in a 5:5 weight ratio. Subsequently, compound C was deposited onto the luminescent layer. The thickness is such that an electron transport auxiliary layer is formed, and compounds D and LiQ are simultaneously vacuum-deposited at a weight ratio of 1:1 to form a thickness of [missing information]. The electron transport layer. This is achieved by sequentially vacuum-depositing on the electron transport layer. LiQ and Al is used to form the cathode to manufacture organic light-emitting diodes.

[0393] ITO / Compound A (3% NDP-9 doped) ) / Compound A( ) / Compound B( ) / EML[body(compound 1-130:compound A-17 = 5:5):[Ir(piq)2acac] = 98wt%:2wt%]( ) / Compound C( Compound D:Liq( ) / LiQ( ) / Al( ).

[0394] Examples 17 to 31 and Comparative Example 2

[0395] Except for the changes to the main body as shown in Table 4, each organic light-emitting diode is manufactured in the same manner as in Example 16.

[0396] evaluate

[0397] The luminous efficiency and lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 31 and Comparative Examples 1 and 2 were evaluated.

[0398] The specific measurement methods are as follows, and the results are shown in Tables 3 and 4.

[0399] (1) Measure the change in current density based on voltage change.

[0400] While increasing the voltage from 0V to 10V, the current flowing through the unit device in the obtained organic light-emitting diode is measured using an ammeter-voltmeter (Keithley 2400), and the measured current value is divided by the area to provide the result.

[0401] (2) Measure the brightness change based on voltage changes

[0402] The brightness was measured using a luminance meter (Minolta Cs-1000A) while the voltage of the organic light-emitting diode was increased from 0V to 10V.

[0403] (3) Measure luminous efficiency

[0404] Using the brightness and current density from (1) and (2) above, as well as the voltage, the calculation was performed at the same current density (10 mA / cm²). 2 Luminous efficiency (cd / A) at ).

[0405] The relative values ​​of luminous efficiency based on Comparative Example 1 were calculated and are shown in Table 3.

[0406] The relative values ​​of luminous efficiency based on Comparative Example 2 were calculated and are shown in Table 4.

[0407] (4) Measurement of lifespan

[0408] The T95 lifetime of the diodes according to Examples 1 to 31 and Comparative Examples 1 and 2 was measured at 6,000 cd / m. 2 As the initial brightness (cd / m 2 After emitting light and measuring the decrease in brightness over time using the Polanonix lifetime measurement system, their brightness relative to the initial brightness (cd / m²) was... 2 The time when it drops to 95%.

[0409] The relative values ​​of T95 lifetime based on Comparative Example 1 were calculated and are shown in Table 3.

[0410] The relative values ​​of T95 lifetime based on Comparative Example 2 were calculated and are shown in Table 4.

[0411] [Table 3]

[0412] Example 1 1-130 117％ 114％ Example 2 1-7 108％ 109％ Example 3 1-67 115％ 119％ Example 4 1-106 117％ 116％ Example 5 1-107 118％ 115％ Example 6 1-111 118％ 114％ Example 7 1-122 120％ 119％ Example 8 1-125 117％ 116％ Example 9 1-171 110％ 113％ Example 10 1-194 110％ 116％ Example 11 1-259 110％ 112％ Example 12 1-291 114％ 118％ Example 13 1-304 117％ 118％ Example 14 1-322 112％ 115％ Example 15 1-354 110％ 114％ Comparative Example 1 C-1 100％ 100％

[0413] [Table 4]

[0414]

[0415]

[0416] Referring to Table 3, the efficiency and lifetime of the compounds according to the invention in single-component form are improved compared to comparative compounds. In particular, referring to Table 4, the overall efficiency and lifetime are significantly improved when combined with a second component.

[0417] While the invention has been described in conjunction with exemplary embodiments which are now considered to be practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A compound for use in organic optoelectronic devices, said compound being represented by chemical formula 1A: [Chemical Formula 1A] In chemical formula 1A, X 1 and X 2 Each can be either O or S independently. L 1 To L 3 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene. Ar 1 and Ar 2 Each of these can be independently substituted or unsubstituted C6 to C20 aryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophene, or substituted or unsubstituted dibenzothiophene. R 1 To R 4 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m1 is one of the integers from 1 to 4. m2 and m3 are each an independent integer of 1 or 2. m4 is one of the integers from 1 to 3, and in, "Substitution" means that at least one hydrogen atom of a substituent is replaced by a deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano group.

2. The compound for organic optoelectronic devices according to claim 1, wherein... Chemical formula 1A can be represented by any one of chemical formulas 1A-1 to 1A-4: [Chemical Formula 1A-1] [Chemical Formula 1A-2] [Chemical Formula 1A-3] [Chemical Formula 1A-4] In chemical formulas 1A-1 to 1A-4 X 1 X 2 L 1 To L 3 Ar 1 Ar 2 R 1 To R 4 m1 to m4 are the same as those defined in claim 1.

3. The compound for organic optoelectronic devices according to claim 1, wherein... Ar 1 and Ar 2 Each of these compounds is independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted trefyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophene, or substituted or unsubstituted dibenzothiophene.

4. The compound for organic optoelectronic devices according to claim 1, wherein... Ar 1 and Ar 2 Each is independently any of the substituents listed in group I: [Group I] In group I, This is the connection point.

5. The compound for organic optoelectronic devices according to claim 1, wherein... L 1 It is a single bond, and L 2 and L 3 Each is an independent single bond or a substituted or unsubstituted phenylene.

6. The compound for organic optoelectronic devices according to claim 1, wherein... The compound is selected from one of the compounds listed in Group 1: [Group 1] 1-345 1-346 1-347 1-348 。 7. A composition for an organic optoelectronic device, comprising: First compound and second compound, in, The first compound is the compound for organic optoelectronic devices according to any one of claims 1 to 6, and The second compound is represented by chemical formula 2: [Chemical Formula 2] In chemical formula 2, X 3 For O, S, NL a -R a CR b R c or SiR d R e , L a It is a single bond or a substituted or unsubstituted C6 to C12 arylene. R a R b R c R d R e and R 5 Each is independently hydrogen, deuterium, substituted or unsubstituted C6 to C30 aryl or substituted or unsubstituted C2 to C30 heterocyclic group. m5 is one of the integers from 1 to 4, and A is any one of the rings listed in Group II. [Group II] In Group II, For the connection point, X 4 For O or S, R 6 To R 13 Each is independently hydrogen, deuterium, substituted or unsubstituted C6 to C20 aryl or substituted or unsubstituted C2 to C30 heterocyclic group. m6, m8, m11, and m13 are each an independent integer from 1 to 4. m7, m9, m10, and m12 are each an independent integer of 1 or 2, and R a and R 5 To R 13 At least one of them is a group represented by the chemical formula a. [Chemical formula a] In chemical formula a, Z 1 To Z 3 Each is independently N or CR f , Z 1 To Z 3 At least two of them are N. R f It is hydrogen, deuterium, substituted or unsubstituted C1 to C30 alkyl or substituted or unsubstituted C6 to C30 aryl. L 4 To L 6 Each is an independent single bond or a substituted or unsubstituted C6 to C30 arylene. Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heteroaryl group, and This is the connection point.

8. The composition for an organic optoelectronic device according to claim 7, wherein... Chemical formula 2 can be represented by any one of chemical formulas 2-I to 2-X: [Chemical Formula 2-I] [Chemical Formula 2-II] [Chemical Formula 2-III] [Chemical Formula 2-IV] [Chemical Formula 2-V] [Chemical Formula 2-VI] [Chemical Formula 2-VII] [Chemical Formula 2-VIII] [Chemical Formula 2-IX] [Chemical Formula 2-X] In chemical formulas 2-I to 2-X X 3 X 4 Z 1 To Z 3 R 5 To R 13 m5 to m10, m12 to m13, L 4 To L 6 Ar 3 and Ar 4 Same as in claim 7, and m5', m8', and m11' are each an independent integer from 1 to 3.

9. The composition for an organic optoelectronic device according to claim 8, wherein... The second compound is represented by chemical formula 2-III or chemical formula 2-VI.

10. The composition for an organic optoelectronic device according to claim 7, wherein... The second compound is represented by chemical formula 2-III-1 or chemical formula 2-VI-1: [Chemical Formula 2-III-1] [Chemical Formula 2-VI-1] In chemical formulas 2-III-1 and 2-VI-1, X 3 Z 1 To Z 3 R 5 R 7 R 8 m5, m7, m8, L 4 To L 6 Ar 3 and Ar 4 Same as in claim 7, and m5' and m8' are each an independent integer from 1 to 3.

11. The composition for an organic optoelectronic device according to claim 7, wherein... Ar 3 and Ar 4 Each of these compounds is independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene.

12. The composition for an organic optoelectronic device according to claim 7, wherein... The second compound is selected from the compounds listed in group 2: [Group 2] 。 13. An organic optoelectronic device, comprising: The anode and cathode facing each other, At least one organic layer between the anode and the cathode, in, The organic layer includes The compound for an organic optoelectronic device according to any one of claims 1 to 6; or The composition for an organic optoelectronic device according to any one of claims 7 to 12.

14. The organic optoelectronic device according to claim 13, wherein... The organic layer includes a light-emitting layer, and The light-emitting layer comprises the compound for organic optoelectronic devices or the composition for organic optoelectronic devices.

15. A display device comprising the organic optoelectronic device of claim 13 or 14.

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