Composition for organic optoelectronic device, organic optoelectronic device and display device

Abstract

Provided are a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. The composition for an organic optoelectronic device includes a first host represented by Chemical Formula 1, a second host represented by a combination of Chemical Formula 2 and Chemical Formula 3, and a dopant represented by Chemical Formula 4. The contents of Chemical Formulae 1 to 4 are as defined in the specification.

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0090637, filed on July 9, 2024, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] A composition for use in an organic optoelectronic device, an organic optoelectronic device, and a display device are disclosed. Background Technology

[0004] Organic optoelectronic devices (organic optoelectronic diodes) are devices that can convert electrical energy into light energy and vice versa.

[0005] 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.

[0006] Examples of organic optoelectronic devices include organic photoelectric devices, organic light-emitting diodes, organic solar cells, and organic photosensitive drums.

[0007] Organic light-emitting diodes (OLEDs) have received 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

[0008] One embodiment provides a composition for organic optoelectronic devices that can reduce driving voltage and achieve high efficiency and long lifespan.

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

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

[0011] According to one embodiment, the composition for an organic optoelectronic device comprises a first body represented by chemical formula 1, a second body represented by a combination of chemical formulas 2 and 3, and a dopant represented by chemical formula 4.

[0012] [Chemical Formula 1]

[0013]

[0014] In chemical formula 1,

[0015] R 1 and R 2 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C2 to C20 heterocyclic group.

[0016] R 3 To R 10 Each of these groups is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic.

[0017] R 3 To R 10 They exist independently or their adjacent groups are connected to each other to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic compounds.

[0018] Ar 1 and Ar 2 Independently, it is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

[0019] Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl.

[0020] L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0021] n1 is 0 or 1.

[0022] m1 and m2 are each an independent integer from 1 to 4, and

[0023] When m1 and m2 are both integers greater than or equal to 2, R 1 and R 2 Each is the same as or different from the other;

[0024]

[0025] In chemical formulas 2 and 3,

[0026] In chemical formula 2, a1* to a4*, each of the two adjacent atoms is a linking carbon (C) connected to the * in chemical formula 3.

[0027] In chemical formula 2, a1* to a4*, the other two not connected to the * in chemical formula 3 are each independently CL. a -R a ,

[0028] L a L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0029] R a and R 33 To R 40 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic.

[0030] R a and R 33 To R 40 They exist independently or adjacent groups are linked together to form substituted or unsubstituted aromatic monocyclic or polycyclic compounds, and

[0031] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0032] [Chemical Formula 4]

[0033] Ir(L A ) n2 (L B ) n3 (L C ) 3-n2-n3

[0034] In chemical formula 4,

[0035] L A It is a ligand represented by chemical formula 4-1.

[0036] L B It is a ligand represented by chemical formula 4-2.

[0037] L C It is a bidentate ligand for a single anion, which coordinates with iridium via unshared electron pairs of carbon or heteroatoms, and

[0038] n2 and n3 are each independent integers from 0 to 3, and n2 + n3 is any integer from 1 to 3.

[0039] [Chemical Formula 4-1]

[0040]

[0041] [Chemical Formula 4-2]

[0042]

[0043] In chemical formulas 4-1 and 4-2,

[0044] Ring A and ring B are each independently monocyclic or polycyclic fused rings.

[0045] In both monocyclic and polycyclic fused ring systems, each ring is a 5- or 6-membered carbon ring or a heterocyclic ring.

[0046] R 17 and R 18 Each can independently represent one to a maximum number of monovalent substituents.

[0047] When R 17 and R 18 When there are 2 or more of each, R 17 and R 18 Each is the same as or different from the other.

[0048] R 13 To R 26 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 50 R 51 R 52 -GeR 50 R 51 R 52 Or a combination of them,

[0049] R 50 To R 52 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0050] X 1 X 2 X 3 and X 4 Each is independently selected from carbon and nitrogen.

[0051] Y is either O or S.

[0052] n4 is an integer that is either 0 or 1.

[0053] m5 is an integer of 1 or 2.

[0054] m6 is an integer from 1 to 3, and

[0055] * indicates a connection point.

[0056] 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, wherein the organic layer contains the composition described above for the organic optoelectronic device.

[0057] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0058] It can realize high-efficiency, long-life organic optoelectronic devices while reducing driving voltage. Attached Figure Description

[0059] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0060] <Explanation of Figure Markers>

[0061] 100: Organic Light Emitting Diode

[0062] 105: Organic layer

[0063] 110: Cathode

[0064] 120: Anode

[0065] 130: Emissive layer

[0066] 140: Hole transport region

[0067] 150: Electronic transmission area Detailed Implementation

[0068] Embodiments of the present invention are described in detail below. However, these embodiments are exemplary, and this disclosure is not limited thereto.

[0069] As used herein, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by: 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.

[0070] 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, C1 to C5 alkylsilyl, C3 to C20 cycloalkyl, C6 to C20 aryl, C2 to C20 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 C5 alkyl, C3 to C20 cycloalkyl, C1 to C5 alkylsilyl, C6 to C18 aryl, C2 to C18 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, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, trimethylsilyl, adamantyl, phenyl, biphenyl, terphenyl or naphthyl.

[0071] In this specification, "unsubstituted" means that the hydrogen atom is not replaced by another substituent and retains the hydrogen atom.

[0072] In this specification, "hydrogen (-H) substitution" may include "deuterium (-D) substitution" or "tritium (-T) substitution".

[0073] In this specification, unless otherwise defined, “heterogeneous” means a functional group containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon.

[0074] In this specification, "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., and 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.

[0075] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent carbon atom pairs) functional groups.

[0076] 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 replacing 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.

[0077] 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.

[0078] 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 phenanthyl, 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 benzo[a]phenanthyl, 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.

[0079] 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, or a substituted or unsubstituted... The following are substituted 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 benzonaphthofuranyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofuran-fluorenyl, substituted or unsubstituted benzothiophene-fluorenyl, or combinations thereof, but not limited thereto.

[0080] As used herein, "adjacent substituents linked together to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic rings" means that any two adjacent substituents are linked together to form a ring. For example, in Formula 1, R 3To R 10 Adjacent groups can connect to each other to form substituted or unsubstituted aromatic monocyclic rings. Aromatic monocyclic rings can include, for example, substituted or unsubstituted phenyl groups.

[0081] In addition, R in chemical formula 1 3 To R 10 Adjacent groups can connect to each other to form substituted or unsubstituted heteroaromatic monocyclic rings. Heteroaromatic monocyclic rings can include, for example, substituted or unsubstituted oxazoles.

[0082] In addition, R in chemical formula 1 3 To R 10 Adjacent groups can connect to each other to form substituted or unsubstituted aromatic polycyclic compounds. Aromatic polycyclic compounds can include, for example, substituted or unsubstituted indene.

[0083] In addition, R in chemical formula 1 3 To R 10 Adjacent groups can be linked together to form substituted or unsubstituted heterocyclic aromatics. Heterocyclic aromatics can include, for example, substituted or unsubstituted indole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, and substituted or unsubstituted silanedene.

[0084] As used herein, hole characteristics 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 readily injected into and transported in the light-emitting layer.

[0085] 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.

[0086] The following describes a composition for an organic optoelectronic device according to one embodiment.

[0087] A composition for an organic optoelectronic device according to one embodiment comprises a first body, a second body, and a dopant.

[0088] The first entity can be represented by chemical formula 1.

[0089] [Chemical Formula 1]

[0090]

[0091] In chemical formula 1,

[0092] R 1 and R 2Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C2 to C20 heterocyclic group.

[0093] R 3 To R 10 Each of these groups is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic.

[0094] R 3 To R 10 They exist independently or their adjacent groups are connected to each other to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic compounds.

[0095] Ar 1 and Ar 2 Each of these can be independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophene group.

[0096] Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl.

[0097] L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0098] n1 is 0 or 1.

[0099] m1 and m2 are each an independent integer from 1 to 4, and

[0100] When m1 and m2 are both integers greater than or equal to 2, R 1 and R 2 They are the same as or different from each other.

[0101] In the compound represented by Formula 1, the o-phenylene bonded to the triazine is replaced by carbazole, and the dihedral angle is increased due to the steric hindrance between the triazine and carbazole. Therefore, the triazine and carbazole moieties twist against each other to increase the dihedral angle. This means that the electron clouds of the HOMO and LUMO energy levels are essentially separated without overlap, and due to its small ΔEst, rapid energy transfer is possible, exhibiting high efficiency, especially when used as a phosphorescent host. Furthermore, the reduced side reaction pathways in the excited state further enhance lifetime extension. Moreover, since the ortho-bonded compound has a relatively lower deposition temperature than the meta- and para-bonded compounds, it is expected that by reducing thermal damage, not only will luminescence efficiency be improved, but also process time and lifetime will be shortened.

[0102] In chemical formula 1, when m1 is 2 or greater, R 1 Each can be the same as or different from the other.

[0103] In chemical formula 1, when m2 is 2 or greater, R 2 Each can be the same as or different from the other, and

[0104] For example, chemical formula 1 can be represented by any one of chemical formulas 1-1 to 1-4.

[0105] [Chemical Formula 1-1]

[0106]

[0107] [Chemical Formula 1-2]

[0108]

[0109] [Chemical Formulas 1-3]

[0110]

[0111] [Chemical Formulas 1-4]

[0112]

[0113] In chemical formulas 1-1 to 1-4

[0114] R 1 To R 10 L 1 L 2 Ar 1 Ar 2 The definitions of m1 and m2 are the same as those above.

[0115] In one implementation, R 1 and R 2Each of them can be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, or substituted or unsubstituted carbazoleyl.

[0116] For example, R 1 and R 2 Each can be hydrogen, deuterium, or a substituted or unsubstituted phenyl group, independently.

[0117] As a specific example, in chemical formula 1-1, R 2 It can be hydrogen, deuterium, or a substituted or unsubstituted phenyl group, and chemical formula 1-1 can be, for example, composed of chemical formula 1-1a, chemical formula 1-1b, ...

[0118] It can be represented by one of the following: Formula 1-1c, Formula 1-1d, and Formula 1-1e.

[0119]

[0120]

[0121] [Chemical formula 1-1e]

[0122]

[0123] In chemical formulas 1-1a, 1-1b, 1-1c, 1-1d, and 1-1e,

[0124] R 3 To R 10 L 1 L 2 Ar 1 and Ar 2 The definition is the same as above.

[0125] R 2a R 2b R 2c R 2d and R 30 Each is independently hydrogen, deuterium, or cyano, and

[0126] m12 is one of the integers from 1 to 5.

[0127] In one implementation, 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 triphenylene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted benzonaphthofuranyl, or substituted or unsubstituted benzonaphthothiophene.

[0128] Ar 1 and Ar 2 At least one of them may be a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl.

[0129] For example, Ar 1 It can be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl, and

[0130] Ar 2 It can be a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenylyl.

[0131] In one implementation, L 1 and L 2 Each can be a single bond or a substituted or unsubstituted phenylene group, and each can be independent of the others.

[0132] In one implementation, R 3 To R 10 It can be hydrogen, deuterium, cyano, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazoyl, or substituted or unsubstituted pyridyl.

[0133] In another implementation, R 3 To R 10 Adjacent groups can be linked to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic compounds.

[0134] For example, by connecting R 3 To R 10 The structure formed by adjacent groups can be represented by one of chemical formulas 1A-1 to 1A-3.

[0135] [Chemical Formula 1A-1]

[0136]

[0137] [Chemical Formula 1A-2]

[0138]

[0139] [Chemical Formula 1A-3]

[0140]

[0141] In chemical formulas 1A-1 to 1A-3,

[0142] R 1 To R 10 L 1 L 2 Ar 1 Ar 2 The definitions of m1, m2, and n1 are the same as those above.

[0143] R 31 It is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0144] m13 is one of the integers from 1 to 4, and

[0145] When m13 is 2 or greater, R 31 Each can be the same as or different from the other.

[0146] As another example, via connecting R 3 To R 10 The structure formed by adjacent groups can be represented by one of chemical formulas 1B-1 to 1B-6.

[0147] [Chemical Formula 1B-1]

[0148]

[0149] [Chemical Formula 1B-2]

[0150]

[0151] [Chemical Formula 1B-3]

[0152]

[0153] [Chemical Formula 1B-4]

[0154]

[0155] [Chemical Formula 1B-5]

[0156]

[0157] [Chemical Formula 1B-6]

[0158]

[0159] In chemical formulas 1B-1 to 1B-6

[0160] R 1 To R 10 L 1 L 2 Ar 1 Ar 2 The definitions of m1, m2, and n1 are the same as those above.

[0161] X 5 It is O or S, and

[0162] Ar 5 It is a substituted or unsubstituted C6 to C12 aryl group.

[0163] As another example, via connecting R 3 To R 10 The structure formed by adjacent groups can be represented by one of the chemical formulas 1C-1 to 1C-6.

[0164] [Chemical formula 1C-1]

[0165]

[0166] [Chemical formula 1C-2]

[0167]

[0168] [Chemical formula 1C-3]

[0169]

[0170] [Chemical formula 1C-4]

[0171]

[0172] [Chemical formula 1C-5]

[0173]

[0174] [Chemical formula 1C-6]

[0175]

[0176] In chemical formulas 1C-1 to 1C-6

[0177] R 1 To R10 L 1 L 2 Ar 1 Ar 2 The definitions of m1, m2, and n1 are the same as those above.

[0178] X 6 It is O, S, NR b or SiR c R d ,

[0179] R b It is a substituted or unsubstituted C6 to C12 aryl group.

[0180] R c and R d Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0181] R 32 It is hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0182] m14 is one of the integers from 1 to 4, and

[0183] When m14 is 2 or greater, R 32 Each can be the same as or different from the other.

[0184] For example, R 3 To R 10 Each of them can be hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0185] In one of the most specific embodiments, the first subject may be one of the compounds listed in Group 1, Group 1-1 and Group 1-2, but is not limited thereto.

[0186] [Group 1]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193] Furthermore, the deuterium-substituted structures of the compounds listed in Group 1 may be selected from, but are not limited to, one of the compounds listed in Group 1-1.

[0194] [Group 1-1]

[0195]

[0196]

[0197]

[0198]

[0199] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions).

[0200] More specific examples of the compounds listed in Group 1-1 may be selected from, but are not limited to, the compounds listed in Group 1-2.

[0201] [Group 1-2]

[0202]

[0203]

[0204]

[0205]

[0206] Meanwhile, the second entity can be represented by a combination of chemical formula 2 and chemical formula 3.

[0207]

[0208] In chemical formulas 2 and 3,

[0209] In chemical formula 2, a1* to a4*, each of the two adjacent atoms is a linking carbon (C) connected to the * in chemical formula 3.

[0210] In chemical formula 2, a1* to a4*, the other two not connected to the * in chemical formula 3 are each independently CL. a -R a ,

[0211] L a L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 aryl group.

[0212] R a and R 33 To R40 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic.

[0213] R a and R 33 To R 40 They exist independently or adjacent groups are linked together to form substituted or unsubstituted aromatic monocyclic or polycyclic compounds, and

[0214] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0215] The second body can be used together with the first body in the luminescent layer to improve luminous efficiency and lifetime characteristics by increasing charge mobility and stability.

[0216] For example, in Formula 2 and Formula 3, "substituted" means that at least one hydrogen atom is replaced by a deuterium, cyano, C1 to C5 alkyl, C3 to C10 cycloalkyl, C6 to C18 aryl, or C2 to C30 heteroaryl.

[0217] In one implementation, 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 anthraquinone, substituted or unsubstituted phenanthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzocarbazolyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted naphthobenzothiophene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted benzofluorenyl, or substituted or unsubstituted dibenzothiophene.

[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 triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene.

[0219] In one implementation, L 3 and L 4They can be substituted or unsubstituted C6 to C12 arylene groups, each independently.

[0220] For example, L 3 and L 4 Each can be independently a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, or a substituted or unsubstituted naphthylene.

[0221] In one implementation, R a and R 33 To R 40 Each can be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl, independently.

[0222] For example, R a and R 33 To R 40 Each can be hydrogen, deuterium, cyano, substituted or unsubstituted tert-butyl, or substituted or unsubstituted phenyl, independently.

[0223] The combination of chemical formula 2 and chemical formula 3 can be represented, for example, by any one of chemical formula 2A, chemical formula 2B, chemical formula 2C, chemical formula 2D, chemical formula 2E, chemical formula 2F, chemical formula 2G, chemical formula 2H and chemical formula 2I.

[0224]

[0225]

[0226] In chemical formulas 2A to 2I, L 3 L 4 Ar 3 Ar 4 R 33 To R 40 Same as above,

[0227] L a1 To L a4 With the above L 3 and L 4 The definitions are the same.

[0228] R a1 To R a4 With the above R 33 To R 40 The definitions are the same.

[0229] m3 is one of the integers from 1 to 4, and

[0230] R 46 It is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0231] When m3 is 2 or greater, R 46 Each can be the same as or different from the other.

[0232] In one implementation, -L 3 -Ar 3 and -L 4 -Ar 4 Each can be one of the substituents listed in Group I, independently.

[0233] [Group I]

[0234]

[0235] In group I,

[0236] R 41 To R 45 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0237] m18 is one of the integers from 1 to 5.

[0238] m19 is one of the integers from 1 to 4.

[0239] m20 is one of the integers from 1 to 3.

[0240] m21 is an integer of 1 or 2.

[0241] m22 is one of the integers from 1 to 7.

[0242] * is a connection point, and

[0243] In group I, when m18 is 2 or greater, R 41 Each can be the same as or different from the other.

[0244] In group I, when m19 is 2 or greater, R 42 Each can be the same as or different from the other.

[0245] In group I, when m20 is 2 or greater, R 43 Each can be the same as or different from the other.

[0246] In group I, when m21 is 2, R 44 Each can be the same as or different from the other.

[0247] In group I, when m22 is 2 or greater, R 45 Each can be the same as or different from the other.

[0248] For example, the second entity can be represented by one of chemical formulas 2A, 2C, 2E, 2F, and 2G.

[0249] As a specific example, the second entity can be represented by one of the chemical formulas 2C, 2F, and 2G.

[0250] In one specific embodiment of the present invention, L a1 To L a4 It can be a single key, L 3 and L 4 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group, R 33 To R 40 R 46 and R a1 To R a4 Each can be independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C5 alkyl, or substituted or unsubstituted phenyl, and Ar 3 and Ar 4 Each of them can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, or substituted or unsubstituted dibenzothiophene.

[0251] For example, the second subject may be one of the compounds listed in Group 2, Group 2-1 and Group 2-2, but is not limited thereto.

[0252] [Group 2]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258] Furthermore, the deuterium-substituted structures of the compounds listed in Group 2 may be selected from, but are not limited to, one of the compounds listed in Group 1-1.

[0259] [Group 2-1]

[0260]

[0261]

[0262]

[0263] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions).

[0264] More specific examples of the compounds listed in Group 2-1 may be selected from, but are not limited to, the compounds listed in Group 2-2.

[0265] [Group 2-2]

[0266]

[0267]

[0268]

[0269] When deuterium is substituted, it is not limited to the compounds exemplified above, and the deuterium substitution position, deuterium substitution rate, etc., can include all variable ranges.

[0270] For example, the first and second bodies can be included in a weight ratio of 1:99 to 99:1. Within this range, the appropriate weight ratio can be adjusted by utilizing the electron transport capability of the first body and the hole transport capability of the second body to achieve bipolar characteristics, thereby improving efficiency and lifetime. Within this range, they can be included in weight ratios of, for example, about 10:90 to 90:10, about 20:80 to 80:20, and, for example, in weight ratios of, for example, 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 included in weight ratios of 40:60, 50:50, or 60:40.

[0271] A dopant is a material that causes luminescence when mixed in small amounts into a composition for use in organic optoelectronic devices, and can be represented by chemical formula 4.

[0272] [Chemical Formula 4]

[0273] Ir(L A ) n2 (L B ) n3 (L C ) 3-n2-n3

[0274] In chemical formula 4,

[0275] L A It is a ligand represented by chemical formula 4-1.

[0276] L B It is a ligand represented by chemical formula 4-2.

[0277] L CIt is a bidentate ligand for monoanions, which coordinates with iridium via unshared electron pairs of carbon or heteroatoms, and

[0278] n2 and n3 are each independent integers from 0 to 3, and n2 + n3 is any integer from 1 to 3.

[0279] [Chemical Formula 4-1]

[0280]

[0281] [Chemical Formula 4-2]

[0282]

[0283] In chemical formulas 4-1 and 4-2,

[0284] Ring A and ring B are each independently monocyclic or polycyclic fused rings.

[0285] In both monocyclic and polycyclic fused ring systems, each ring is a 5- or 6-membered carbon ring or a heterocyclic ring.

[0286] R 17 and R 18 Each can independently represent one to a maximum number of monovalent substituents.

[0287] When R 17 and R 18 When there are 2 or more of each, R 17 and R 18 Each is the same as or different from the other.

[0288] R 13 To R 26 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 50 R 51 R 52 -GeR 50 R 51 R 52 Or a combination of them,

[0289] R 50 To R 52 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0290] X 1 X 2 X 3 and X 4 Each is independently selected from carbon and nitrogen.

[0291] Y is either O or S.

[0292] n4 is an integer that is either 0 or 1.

[0293] m5 is an integer of 1 or 2.

[0294] m6 is an integer from 1 to 3, and

[0295] * indicates a connection point.

[0296] The ligands of the dopants according to the invention are characterized by aryl groups such as phenyl linearly substituted or fused to dibenzofuran or dibenzothiophene. When this structure is used, the planarity of the ligands increases, which improves the optical orientation of the dopant, and the full width at half maximum (FWHM) is relatively narrowed, which can improve overall device characteristics, such as increasing luminescence efficiency. In this document, if a host structure represented by a combination of Formulas 2 and 3 and thus having improved planarity is used together, the intermolecular charge hopping characteristics can be improved, thereby reducing the driving voltage. However, these structural arrangement features increase intermolecular interactions, which may hinder energy transfer between the host and the dopant, leading instead to non-radiative decay. If a host comprising a first host represented by Formula 1 (having a distorted structure due to the ortho-phenylene linker) and a second host represented by a combination of Formulas 2 and 3 are used together, the relatively spherical host can reduce intermolecular interactions due to its high T1 energy, thus facilitating energy transfer between the host and the dopant, thereby improving device performance.

[0297] Furthermore, the host represented by chemical formula 1 has a relatively low deposition temperature, which not only improves luminescence efficiency but also shortens process time and reduces thermal damage, thereby contributing to improved lifetime.

[0298] When n4 is 0, it is a structure in which dibenzofuran (or dibenzothiophene) is substituted with an aryl group, and when n4 is 1, it is a structure in which dibenzofuran (or dibenzothiophene) and a benzene ring are fused.

[0299] For example, ligand L B It can be selected from the groups listed in Group II.

[0300] [Group II]

[0301]

[0302]

[0303] In Group II,

[0304] Ring B, X 3 X 4Y, R 18 To R 26 The definitions of m5 and m6 are the same as above. As a specific example, ligand L... B It can be selected from the groups listed in group II-1.

[0305] [Group II-1]

[0306]

[0307]

[0308] In group II-1,

[0309] Ring B, X 3 X 4 Y, R 18 To R 26 The definitions of m5 and m6 are the same as above, and

[0310] R 19a and R 19b With regard to R 19 The definitions are the same.

[0311] Ring A and ring B can be independently selected from benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, azabenzofuran, benzoxazole, azabenzoxazole, benzothiophene, azabenzothiophene, benzothiazole, azabenzothiazole, benzoselenene, azabenzoselenene, indene, azaindene, indole, azaindole, benzimidazole, azabenzimidazole, carbazole, azacarbazole, dibenzofuran, azadibenzofuran, dibenzothiazole, azadibenzothiazole, quinoxaline, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene.

[0312] L C It can be selected from the groups listed in Group III.

[0313] Group III

[0314]

[0315] In Group III,

[0316] R 300 To R 302 Each of these elements is independently hydrogen, deuterium, halogen, a C1 to C30 alkyl group substituted or unsubstituted with one or more of deuterium and halogen, or a C6 to C30 aryl group substituted or unsubstituted with one or more of halogen, deuterium, and C1 to C30 alkyl.

[0317] R 303 To R308 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 C2 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, a trialkylsilyl having at least one of halogen, deuterium and substituted or unsubstituted C1 to C30 alkyl, a dialkylarylsilyl having at least one of halogen, deuterium, substituted or unsubstituted C1 to C30 alkyl and substituted or unsubstituted C6 to C30 aryl, or a triarylsilyl having at least one of halogen, deuterium and substituted or unsubstituted C6 to C30 aryl.

[0318] m13 is one of the integers from 1 to 5.

[0319] m14 is one of the integers from 1 to 4.

[0320] m15 is one of the integers from 1 to 3.

[0321] m16 is an integer of 1 or 2.

[0322] m17 is one of the integers from 1 to 6, and

[0323] When m13 to m15 and m17 are 2 or greater and m16 is 2, R 303 To R 307 They are the same as or different from each other.

[0324] As a prime example, dopants can be selected from the compounds listed in Group 3.

[0325] [Group 3]

[0326]

[0327]

[0328]

[0329]

[0330]

[0331] The following describes an organic optoelectronic device using the above-described composition for an organic optoelectronic device.

[0332] 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, or organic photosensitive drums.

[0333] In this paper, an organic light-emitting diode (OLED) is described as an example of an organic optoelectronic device with reference to the accompanying drawings.

[0334] Figure 1 This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0335] 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.

[0336] 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.

[0337] The cathode 110 may be made of a conductor with a small work function to aid electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; multilayer materials such as LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but are not limited thereto.

[0338] The organic layer 105 may contain the composition described above for organic optoelectronic devices.

[0339] The organic layer 105 includes a light-emitting layer 130, and the light-emitting layer 130 includes a host and a dopant, as described above.

[0340] In addition to the light-emitting layer, the organic layer may also include a charge transport region.

[0341] The charge transport region can be, for example, the hole transport region 140.

[0342] 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.

[0343] 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 hole transport layer and the hole transport auxiliary layer may contain at least one of the compounds listed in Group A.

[0344] [Group A]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351] (Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions).

[0352] In the hole transport region 140, 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.

[0353] Alternatively, the charge transport region can be, for example, the electron transport region 150.

[0354] 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.

[0355] Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light-emitting layer 130 and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer, and at least one of the electron transport layer and the electron transport auxiliary layer may contain at least one of the compounds of group B.

[0356] [Group B]

[0357]

[0358]

[0359]

[0360]

[0361] One implementation may be an organic light-emitting diode that includes a light-emitting layer as an organic layer.

[0362] Another implementation could be an organic light-emitting diode (OLED) that includes an emitting layer and a hole transport region as organic layers.

[0363] Another implementation could be an organic light-emitting diode (OLED) that includes an emitting layer and an electron transport region as organic layers.

[0364] like Figure 1 As shown, another embodiment of the present invention can provide an organic light-emitting diode that includes a hole transport region 140 and an electron transport region 150 as an organic layer 105 in addition to the light-emitting layer 130.

[0365] On the other hand, in addition to the light-emitting layer, an organic light-emitting diode may also include an electron injection layer (not shown), a hole injection layer (not shown), etc., as organic layers.

[0366] An organic light-emitting diode 100 can be manufactured 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.

[0367] Organic light-emitting diodes (OLEDs) can be used in organic light-emitting display devices.

[0368] In the following description, embodiments are illustrated in more detail. However, these embodiments are exemplary, and the scope of the claims is not limited thereto.

[0369] 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., Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods, unless otherwise specified.

[0370] (The synthesis of the first subject)

[0371] Synthesis Example 1: Synthesis of Compound A-2

[0372] [Reaction Formula 1]

[0373]

[0374] 10.0 g (27.9 mmol) of intermediate 1-1, 11.2 g (30.7 mmol) of intermediate 1-2, 1.6 g (1.4 mmol) of Pd(PPh3)4, and 11.6 g (83.8 mmol) of K2CO3 were added to a round-bottom flask, along with 93 mL of tetrahydrofuran and 47 mL of distilled water. The mixture was then stirred and refluxed at 90 °C for 12 hours. When the reaction was complete, the aqueous layer was removed, and the organic layer was concentrated, dissolved in toluene, filtered through silica gel, and recrystallized to obtain 13.3 g (74%) of compound A-2.

[0375] (LC / MS theoretical value: 640.23 g / mol, measured value: M+ = 641.4 g / mol)

[0376] Synthesis Example 2: Synthesis of Compound A-7

[0377] [Reaction 2]

[0378]

[0379] 10.0 g (27.9 mmol) of intermediate 2-1, 14.4 g (30.7 mmol) of intermediate 2-2, 1.6 g (1.4 mmol) of Pd(PPh3)4, and 11.6 g (83.8 mmol) of K2CO3 were added to a round-bottom flask, along with 93 mL of tetrahydrofuran and 47 mL of distilled water. The mixture was then stirred and refluxed at 90 °C for 12 hours. When the reaction was complete, the aqueous layer was removed, and the organic layer was concentrated, dissolved in toluene, filtered through silica gel, and recrystallized to obtain 14.6 g (70%) of compound A-7.

[0380] (LC / MS theoretical value: 746.21 g / mol, measured value: M+ = 747.4 g / mol)

[0381] Synthesis Example 3: Synthesis of Compound A-25

[0382] [Reaction 3]

[0383]

[0384] 10.0 g (23.0 mmol) of intermediate 3-1, 11.1 g (25.4 mmol) of intermediate 3-2, 1.3 g (1.2 mmol) of Pd(PPh3)4, and 9.6 g (69.1 mmol) of K2CO3 were added to a round-bottom flask, along with 77 mL of tetrahydrofuran and 38 mL of distilled water. The mixture was then stirred and refluxed at 90 °C for 12 hours. When the reaction was complete, the aqueous layer was removed, and the organic layer was concentrated, dissolved in toluene, filtered through silica gel, and recrystallized to obtain 13.9 g (76%) of compound A-25.

[0385] (LC / MS theoretical value: 792.29 g / mol, measured value: M+ = 793.5 g / mol)

[0386] Synthesis Example 4: Synthesis of Compound A-53

[0387] [Reaction 4]

[0388]

[0389] 10.0 g (27.9 mmol) of intermediate 4-1, 12.1 g (30.7 mmol) of intermediate 4-2, 1.6 g (1.4 mmol) of Pd(PPh3)4, and 11.6 g (83.8 mmol) of K2CO3 were added to a round-bottom flask, along with 93 mL of tetrahydrofuran and 47 mL of distilled water. The mixture was then stirred and refluxed at 90 °C for 12 hours. When the reaction was complete, the aqueous layer was removed, and the organic layer was concentrated, dissolved in toluene, filtered through silica gel, and recrystallized to obtain 13.7 g (73%) of compound A-53.

[0390] (LC / MS theoretical value: 670.18 g / mol, measured value: M+ = 671.4 g / mol)

[0391] (The synthesis of the second subject)

[0392] Synthesis Example 5: Synthesis of Compound B-3

[0393] [Reaction 5]

[0394]

[0395] 10.0 g (24.5 mmol) of intermediate 5-1, 6.3 g (26.9 mmol) of intermediate 5-2, 1.1 g (1.2 mmol) of Pd2(dba)3, 3.5 g (36.7 mmol) of NaOtBu, and 0.7 g (3.7 mmol) of P(t-Bu)3 were added to a round-bottom flask, and 122 mL of xylene was added. The mixture was then stirred and refluxed at 140 °C for 12 hours. When the reaction was complete, distilled water was added and the mixture was stirred to remove the aqueous layer. The resulting organic layer was filtered through silica gel and recrystallized to obtain 10.3 g (75%) of compound B-3.

[0396] (LC / MS theoretical value: 560.23 g / mol, measured value: M+ = 561.54 g / mol)

[0397] Synthesis Example 6: Synthesis of Compound B-5

[0398] [Reaction Formula 6]

[0399]

[0400] 10.0 g (24.5 mmol) of intermediate 6-1, 6.3 g (26.9 mmol) of intermediate 6-2, 1.1 g (1.2 mmol) of Pd2(dba)3, 3.5 g (36.7 mmol) of NaOtBu, and 0.7 g (3.7 mmol) of P(t-Bu)3 were added to a round-bottom flask, and 122 mL of xylene was added. The mixture was then stirred and refluxed at 140 °C for 12 hours. When the reaction was complete, distilled water was added and the mixture was stirred to remove the aqueous layer. The resulting organic layer was filtered through silica gel and recrystallized to obtain 9.7 g (71%) of compound B-5.

[0401] (LC / MS theoretical value: 560.23 g / mol, measured value: M+ = 561.57 g / mol)

[0402] (Synthesis of dopants)

[0403] Synthesis Example 7: Synthesis of Compound C-155

[0404] [Reaction Formula 7]

[0405]

[0406] 2-Phenyl-5-(trimethylsilyl)pyridine (7.5 g, 33.1 mmol) and iridium chloride (5.2 g, 14.7 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water, and then stirred under reflux for 24 hours and cooled to room temperature. The resulting solid was filtered and separated, thoroughly washed with water / methanol / hexane sequentially, and dried in a vacuum oven to obtain 8.2 g (yield: 82%) of compound 7-1.

[0407] After mixing compound 7-1 (1.6 g, 1.2 mmol) with 45 mL of dichloromethane, a mixture of AgOTf (silver trifluoromethanesulfonate, 0.6 g, 2.3 mmol) and 15 mL of methanol was added. The mixture was then stirred at room temperature for 18 hours while protected from light by aluminum foil. After filtering with diatomaceous earth to remove the solids produced, the resulting filtrate was subjected to reduced pressure to obtain the material (compound 7-2), which was used in subsequent reactions without further purification.

[0408] Compound 7-2 (1.9 g, 2.2 mmol) and compound 7-3 (1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-2-(7-phenanthro[3,2-b]benzofuran-11-yl)-1H-benzo[d]imidazole) (1.3 g, 2.1 mmol) were mixed with 10 mL of 2-ethoxyethanol and 10 mL of N,N-dimethylformamide, and then stirred under reflux for 48 hours and cooled to room temperature. The resulting mixture was subjected to reduced pressure to obtain a solid, which was treated by column chromatography (elution: MC and hexane) to obtain 1.10 g (yield: 39%) of compound C-155.

[0409] (Composite composition of contrasting subjects)

[0410] Synthesis Example 8: Synthesis of Compound R-1

[0411] [Reaction Equation 8]

[0412]

[0413] 10.0 g (27.9 mmol) of intermediate 8-1, 11.2 g (30.7 mmol) of intermediate 8-2, 1.6 g (1.4 mmol) of Pd(PPh3)4, and 11.6 g (83.8 mmol) of K2CO3 were added to a round-bottom flask, along with 93 mL of tetrahydrofuran and 47 mL of distilled water. The mixture was then stirred and refluxed at 90 °C for 12 hours. When the reaction was complete, the aqueous layer was removed, and the organic layer was concentrated, dissolved in toluene, filtered through silica gel, and recrystallized to obtain 12.2 g (68%) of compound R-1.

[0414] (LC / MS theoretical value: 640.23 g / mol, measured value: M+ = 641.4 g / mol)

[0415] Synthesis Example 9: Synthesis of Compound R-2

[0416] [Reaction Formula 9]

[0417]

[0418] 10.0 g (28.0 mmol) of intermediate 9-1, 14.5 g (30.8 mmol) of intermediate 9-2, 1.6 g (1.4 mmol) of Pd(PPh3)4, and 11.6 g (84.0 mmol) of K2CO3 were added to a round-bottom flask, along with 93 mL of tetrahydrofuran and 47 mL of distilled water. The mixture was then stirred and refluxed at 90 °C for 12 hours. When the reaction was complete, the aqueous layer was removed, and the organic layer was concentrated, dissolved in toluene, filtered through silica gel, and recrystallized to obtain 14.0 g (67%) of compound R-2.

[0419] (LC / MS theoretical value: 746.21 g / mol, measured value: M+ = 747.4 g / mol)

[0420] Synthesis Example 10: Synthesis of Compound R-3

[0421] [Reaction Formula 10]

[0422]

[0423] 10.0 g (23.0 mmol) of intermediate 10⁻¹, 11.1 g (25.4 mmol) of intermediate 10⁻², 1.3 g (1.2 mmol) of Pd(PPh₃)₄, and 9.6 g (69.1 mmol) of K₂CO₃ were added to a round-bottom flask, along with 77 mL of tetrahydrofuran and 38 mL of distilled water. The mixture was then stirred and refluxed at 90 °C for 12 hours. When the reaction was complete, the aqueous layer was removed, and the organic layer was concentrated, dissolved in toluene, filtered through silica gel, and recrystallized to obtain 11.8 g (65%) of compound R-3.

[0424] (LC / MS theoretical value: 792.29 g / mol, measured value: M+ = 793.5 g / mol)

[0425] Synthesis Example 11: Synthesis of Compound R-4

[0426] [Reaction Formula 11]

[0427]

[0428] 10.0 g (28.0 mmol) of intermediate 11-1, 12.1 g (30.7 mmol) of intermediate 11-2, 1.6 g (1.4 mmol) of Pd(PPh3)4, and 11.6 g (84.0 mmol) of K2CO3 were added to a round-bottom flask, along with 93 mL of tetrahydrofuran and 47 mL of distilled water. The mixture was then stirred and refluxed at 90 °C for 12 hours. When the reaction was complete, the aqueous layer was removed, and the organic layer was concentrated, dissolved in toluene, filtered through silica gel, and recrystallized to obtain 12.4 g (66%) of compound R-4.

[0429] (LC / MS theoretical value: 670.18 g / mol, measured value: M+ = 671.4 g / mol)

[0430] Synthesis Example 12: Synthesis of Compound R-5

[0431] [Reaction 12]

[0432]

[0433] 10.0 g (31.0 mmol) of intermediate 12-1, 12.4 g (34.1 mmol) of intermediate 12-2, 1.8 g (1.6 mmol) of Pd(PPh3)4, and 12.9 g (93.1 mmol) of K2CO3 were added to a round-bottom flask, along with 103 mL of tetrahydrofuran and 52 mL of distilled water. The mixture was then stirred and refluxed at 90 °C for 12 hours. When the reaction was complete, the aqueous layer was removed, and the organic layer was concentrated, dissolved in toluene, filtered through silica gel, and recrystallized to obtain 12.5 g (72%) of compound R-5.

[0434] (LC / MS theoretical value: 560.23 g / mol, measured value: M+ = 561.4 g / mol)

[0435] Synthesis Example 13: Synthesis of Compound R-6

[0436]

[0437] Compound R-6 was synthesized according to the synthetic method disclosed in US10844085 B2.

[0438] Example 1: Fabrication of a Green Organic Light Emitting Diode (Hybrid Body)

[0439] A glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. 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 before being transferred to a vacuum deposition apparatus. Using this prepared ITO transparent electrode as the anode, compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited onto the ITO substrate to form... A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form A thick hole transport layer. Compound E is deposited on the hole transport layer to form... A thick hole transport auxiliary layer. Compound A-2 synthesized in Synthesis Example 1 and compound B-3 synthesized in Synthesis Example 5 were used simultaneously as the host material in a weight ratio of 6:4 on the hole transport auxiliary layer, with 10 wt% of dopant compound C-155 as the dopant, to form the layer by vacuum deposition. A thick luminescent layer. Subsequently, compound F is deposited on the luminescent layer to form... A thick electron transport auxiliary layer was formed by simultaneously vacuum depositing compounds G and LiQ at a 1:1 weight ratio to create... A thick electron transport layer. On the electron transport layer, sequential vacuum deposition... LiQ and Al forms the cathode, thereby manufacturing an organic light-emitting diode.

[0440] The manufactured organic light-emitting diode has the following structure: ITO / compound A (3% NDP-9 doped). Compound A / Compound E / EML[body(compound A-2:compound B-3 = 6wt%:4wt%):compound C-155 = 90wt%:10wt%] / compound F / Compound G:LiQ / LiQ / Al

[0441] Compound A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazole-3-yl)biphenyl-4,4'-diamine

[0442] Compound E: N,N-bis(9,9-dimethyl-9H-fluorene-4-yl)-9,9-spirodi(fluorene)-2-amine

[0443] Compound F: 2-[3'-(9,9-dimethyl-9H-fluorene-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0444] Compound G: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0445] Examples 2 to 4 and Comparative Examples 1 to 12

[0446] Each organic light-emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed as described in Tables 1 to 4.

[0447] evaluate

[0448] The power efficiency of the organic light-emitting diodes according to Examples 1 to 4 and Comparative Examples 1 to 12 was evaluated.

[0449] The specific measurement methods are as follows, and the results are shown in Tables 1 to 4.

[0450] (1) Measure the change in current density based on voltage change.

[0451] While increasing the voltage from 0V to 10V, the current flowing through the unit device in the manufactured organic light-emitting diode is measured using a current-voltmeter (Keithley 2400), and the measured current value is divided by the area to provide the result.

[0452] (2) Measure the brightness change based on voltage changes

[0453] The brightness was measured using a luminance meter (MinoltaCs-1000A) while the voltage of the organic light-emitting diode was increased from 0V to 10V.

[0454] (3) Measuring current efficiency

[0455] Using the brightness, current density, and voltage measured according to (1) and (2) above, calculate the voltage at the same current density (10 mA / cm²). 2 Current efficiency (cd / A) at )

[0456] (4) Measure the driving voltage

[0457] The current-voltmeter (Keithley 2400) was used to measure at 15 mA / cm. 2 The result is obtained by applying the driving voltage to each diode.

[0458] (5) Power efficiency

[0459] The power efficiency value is calculated according to Equation 1, and its relative value is calculated and shown in Tables 1 to 4.

[0460] [Equation 1]

[0461] Power efficiency (lm / W) = [Current efficiency (cd / A) / Drive voltage (V)] * π

[0462] (Π refers to pi)

[0463] The power efficiency values ​​for Example 1 and Comparative Examples 1 to 3 were calculated as relative values ​​based on Example 1 and are listed in Table 1.

[0464] The power efficiency values ​​for Examples 2 and Comparative Examples 4 to 6 were calculated as relative values ​​based on Example 2 and are listed in Table 2.

[0465] The power efficiency values ​​for Example 3 and Comparative Examples 7 to 9 were calculated as relative values ​​based on Example 3 and are listed in Table 3.

[0466] The power efficiency values ​​for Examples 4 and Comparative Examples 10 to 12 were calculated as relative values ​​based on Example 4 and are listed in Table 4.

[0467] (Table 1)

[0468]

[0469] (Table 2)

[0470]

[0471] (Table 3)

[0472]

[0473] (Table 4)

[0474]

[0475] Referring to Tables 1 to 4, the organic light-emitting diodes according to Examples 1 to 4 exhibit significantly improved power efficiency compared to the organic light-emitting diodes according to Comparative Examples 1 to 12.

[0476] The ligands of the dopants according to the invention are characterized by linear substitution or fusion of aryl groups, such as phenyl groups, into dibenzofuran or dibenzothiophene. This increases the planarity of the ligand, improves the optical orientation of the dopant, and relatively narrows the full width at half maximum (FWHM), thereby improving luminescent efficiency. Furthermore, when using a host in the form of an indolocarbazole, such as a second host, the planarity increases, which can improve intermolecular charge hopping characteristics, thereby reducing the driving voltage. However, these structural features increase intermolecular interactions, which may hinder energy transfer between the host and the dopant, potentially leading to nonradiative decay. Herein, when using a host in the form of a first host with a twisted structure due to the ortho-phenylene linker, the relatively spherical host reduces intermolecular interactions and has a high T1 energy, thus facilitating energy transfer between the host and the dopant, thereby improving device performance. This combination of host and dopant can improve driving voltage and efficiency characteristics, resulting in significantly improved power efficiency.

[0477] Although the invention has been described in conjunction with exemplary embodiments now considered practical, it should be understood that the invention is not limited to the disclosed embodiments. Rather, it is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

Claims

1. A composition for use in an organic optoelectronic device, comprising: The first entity represented by chemical formula 1, The second entity, represented by a combination of chemical formulas 2 and 3, and Dopant represented by chemical formula 4: [Chemical Formula 1] In chemical formula 1, R 1 and R 2 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C6 to C18 aryl or substituted or unsubstituted C2 to C20 heterocyclic group. R 3 To R 10 Each of these groups is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic. R 3 To R 10 They exist independently or their adjacent groups are connected to each other to form substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic compounds. Ar 1 and Ar 2 Each of these can be independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophene group. Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl. L 1 and L 2 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene group. n1 is 0 or 1. m1 and m2 are each an independent integer from 1 to 4, and When m1 and m2 are both integers greater than or equal to 2, R 1 and R 2 Each is the same as or different from the other; In chemical formulas 2 and 3, In chemical formula 2, a1* to a4*, each of the two adjacent carbons is a linking carbon connected to * in chemical formula 3. In chemical formula 2, a1* to a4*, the other two not connected to the * in chemical formula 3 are each independently CL. a -R a , L a L 3 and L 4 Each is an independent single bond or a substituted or unsubstituted C6 to C20 arylene group. R a and R 33 To R 40 Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R a and R 33 To R 40 They exist independently or adjacent groups are linked together to form substituted or unsubstituted aromatic monocyclic or polycyclic compounds, and Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group; [Chemical Formula 4] Go(L A ) n2 (L B ) n3 (L C ) 3-n2-n3 In chemical formula 4, L A It is a ligand represented by chemical formula 4-1. L B It is a ligand represented by chemical formula 4-2. L C It is a bidentate ligand of a monoanion, wherein the bidentate ligand of the monoanion is coordinated with iridium via unshared electron pairs of carbon or heteroatoms, and n2 and n3 are each independent integers from 0 to 3, and n2 + n3 is any integer from 1 to 3. [Chemical Formula 4-1] [Chemical Formula 4-2] In chemical formulas 4-1 and 4-2, Ring A and ring B are each independently monocyclic or polycyclic fused rings. in, Each ring in the monocyclic and polycyclic fused rings is a 5- or 6-membered carbon ring or a heterocyclic ring. R 17 and R 18 Each can independently represent one to a maximum number of monovalent substituents. When R 17 and R 18 When there are 2 or more of each, R 17 and R 18 Each is the same as or different from the other. R 13 To R 26 Each of these elements is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C20 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 50 R 51 R 52 -GeR 50 R 51 R 52 Or a combination of them, R 50 To R 52 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. X 1 X 2 X 3 and X 4 Each is independently selected from carbon and nitrogen. Y is either O or S. n4 is an integer that is either 0 or 1. m5 is an integer of 1 or 2. m6 is an integer from 1 to 3, and * indicates a connection point.

2. The composition for an organic optoelectronic device according to claim 1, wherein... Chemical formula 1 can be represented by any one of chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] In chemical formulas 1-1 to 1-4 R 1 To R 10 L 1 L 2 Ar 1 Ar 2 m1 and m2 are defined in claim 1.

3. The composition for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 Each of these elements is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophene, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophene. Ar 1 and Ar 2 At least one of them is a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, or a substituted or unsubstituted benzonaphthothiophenyl.

4. The composition for an organic optoelectronic device according to claim 1, wherein... Ar 1 It is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl, and Ar 2 It is a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiopheneyl.

5. The composition for an organic optoelectronic device according to claim 1, wherein... The first subject is selected from the compounds listed in Group 1, Group 1-1 and Group 1-2: [Group 1] Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions, [Group 1-2] D stands for deuterium.

6. The composition for an organic optoelectronic device according to claim 1, wherein... The combination of chemical formulas 2 and 3 is represented by one of chemical formulas 2C, 2F, and 2G: [Chemical formula 2C] In chemical formulas 2C, 2F, and 2G L a3 and L a4 Each is a single key. R 33 To R 40 R 46 R a3 and R a4 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C5 alkyl or substituted or unsubstituted C6 to C12 aryl. m3 is one of the integers from 1 to 4, and -L 3 -Ar 3 and -L 4 -Ar 4 Each is independently one of the substituents listed in Group I. [Group I] In group I, R 41 To R 45 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. m18 is one of the integers from 1 to 5. m19 is one of the integers from 1 to 4. m20 is one of the integers from 1 to 3. m21 is an integer of 1 or 2. m22 is one of the integers from 1 to 7. * is a connection point, and When m18 to m20 and m22 are 2 or greater and m21 is 2, R 41 To R 45 They are the same as or different from each other.

7. The composition for an organic optoelectronic device according to claim 1, wherein... The second subject is selected from the compounds listed in Group 2, Group 2-1 and Group 2-2: [Group 2] Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions. [Group 2-2] D stands for deuterium.

8. The composition for an organic optoelectronic device according to claim 1, wherein the ligand L B Selected from the groups listed in Group II: [Group II] In Group II, Ring B, X 3 X 4 Y, R 18 To R 26 m5 and m6 are defined in claim 1.

9. The composition for an organic optoelectronic device according to claim 1, wherein... ligand L B Selected from the groups listed in Group II-1: [Group II-1] In group II-1, Ring B, X 3 X 4 Y, R 18 To R 26 m5 and m6 are defined in claim 1, and R 19a and R 19b Compared with claim 1 for R 19 The limitations are the same.

10. The composition for an organic optoelectronic device according to claim 1, wherein... Ring A and ring B are each independently selected from benzene, pyridine, pyrimidine, pyridazine, pyrazine, triazine, imidazole, pyrazole, pyrrole, oxazole, furan, thiophene, thiazole, naphthalene, quinoline, isoquinoline, quinazoline, benzofuran, azabenzofuran, benzoxazole, azabenzoxazole, benzothiophene, azabenzothiophene, benzothiazole, azabenzothiazole, benzoselenene, azabenzoselenene, indene, azaindene, indole, azaindole, benzimidazole, azabenzimidazole, carbazole, azacarbazole, dibenzofuran, azadibenzofuran, dibenzothiazole, azadibenzothiazole, quinoxaline, phthalazine, phenanthrene, azaphenanthrene, anthracene, azaanthracene, phenanthridine, fluorene, and azafluorene.

11. The composition for an organic optoelectronic device according to claim 1, wherein... L C Selected from the groups listed in Group III: Group III In group III, R 300 To R 302 Each of these elements is independently hydrogen, deuterium, halogen, a C1 to C30 alkyl group substituted or unsubstituted with one or more of deuterium and halogen, or a C6 to C30 aryl group substituted or unsubstituted with one or more of halogen, deuterium, and C1 to C30 alkyl. R 303 To R 308 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 C2 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, a trialkylsilyl having at least one of halogen, deuterium and substituted or unsubstituted C1 to C30 alkyl, a dialkylarylsilyl having at least one of halogen, deuterium, substituted or unsubstituted C1 to C30 alkyl and substituted or unsubstituted C6 to C30 aryl, or a triarylsilyl having at least one of halogen, deuterium and substituted or unsubstituted C6 to C30 aryl. m13 is one of the integers from 1 to 5. m14 is one of the integers from 1 to 4. m15 is one of the integers from 1 to 3. m16 is an integer of 1 or 2. m17 is one of the integers from 1 to 6, and When m13 to m15 and m17 are 2 or greater and m16 is 2, R 303 To R 307 They are the same as or different from each other.

12. The composition for an organic optoelectronic device according to claim 1, wherein... The dopant is selected from the compounds listed in Group 3: [Group 3] D stands for deuterium.

13. An organic optoelectronic device, comprising The anode and cathode facing each other, and At least one organic layer between the anode and the cathode, in, The organic layer comprises the composition for an organic optoelectronic device according to any one of claims 1 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 composition for organic optoelectronic devices.

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

Images