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

Abstract

A compound for use in an organic optoelectronic device, an organic optoelectronic device, and a display device are provided. The compound for use in the organic optoelectronic device is represented by Chemical Formula 1, and the organic optoelectronic device comprises the compound. Details of Chemical Formula 1 are as defined in the specification.

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2022-0059692, filed on May 16, 2022, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] Compounds for use in organic optoelectronic devices, organic optoelectronic devices, and display devices are disclosed. Background Technology

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

[0005] Based on their operating principles, organic optoelectronic devices can be broadly classified into two types. One type generates electrical energy by separating excitons formed from light energy into electrons and holes, and then transferring the electrons and holes to different electrodes. The other type generates light energy from electrical energy by supplying 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 photoconductor drums.

[0007] Among these, 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 compound for organic optoelectronic devices that enables organic optoelectronic devices with low drive, high efficiency and long lifetime.

[0009] Another embodiment provides an organic optoelectronic device comprising the compound.

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

[0011] According to one embodiment, a compound for an organic optoelectronic device is provided, the compound being represented by chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In chemical formula 1,

[0015] X 1 To X 4Each is independently O, S, NR a CR b R c or SiR d R e ,

[0016] m1 to m4 are each an independent integer of 0 or 1.

[0017] m5 to m9 are each an independent integer from 1 to 4.

[0018] n is an integer from 1 to 3.

[0019] A is a substituted or unsubstituted carbazole group.

[0020] L 1 It is a single bond or a substituted or unsubstituted C6 to C20 arylene, and

[0021] R a R b R c R d R e and R 1 To R 5 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0022] 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 a compound for the organic optoelectronic device.

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

[0024] It can realize organic optoelectronic devices with low drive, high efficiency and long life. Attached Figure Description

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

[0026] <Explanation of Figure Markers>

[0027] 100: Organic Light Emitting Diode

[0028] 105: Organic layer

[0029] 110: Cathode

[0030] 120: Anode

[0031] 130: Emissive layer

[0032] 140: Hole transport region

[0033] 150: Electron transport region Detailed Implementation

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

[0035] In this specification, 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.

[0036] 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.

[0037] "Unsubstituted" means that the hydrogen atom has not been replaced by another substituent and retains the hydrogen atom.

[0038] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0039] In this specification, unless otherwise defined, "heterogeneous" means a functional group comprising one to three heteroatoms selected from N, O, S, P and Si, with the remainder being carbon.

[0040] 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.; 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.

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

[0042] In this specification, "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 ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0043] For example, "heteroaryl" refers to an aryl group that includes 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 includes two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring can include one to three heteroatoms.

[0044] 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 phenanthryl, 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 perylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof, but is not limited thereto.

[0045] 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, or a substituted or unsubstituted benzothiopheneyl group. The following are substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, 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, or substituted or unsubstituted dibenzothiophenyl, or combinations thereof, but not limited thereto.

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

[0047] 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 the light-emitting layer and transported within the light-emitting layer.

[0048] The following describes a compound for an organic optoelectronic device according to one embodiment.

[0049] According to one embodiment, a compound for an organic optoelectronic device is represented by chemical formula 1.

[0050] [Chemical Formula 1]

[0051]

[0052] In chemical formula 1,

[0053] X 1 To X 4 Each is independently O, S, NR a CR b R cor SiR d R e ,

[0054] m1 to m4 are each an independent integer of 0 or 1.

[0055] m5 to m9 are each an independent integer from 1 to 4.

[0056] n is an integer from 1 to 3.

[0057] A is a substituted or unsubstituted carbazole group.

[0058] L 1 It is a single bond or a substituted or unsubstituted C6 to C20 arylene, and

[0059] R a R b R c R d R e and R 1 To R 5 Each of them is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0060] Compared to structures containing a fused carbazole skeleton, compounds represented by Formula 1 (which are designed as macrocyclic amine-based compounds) are used to overcome structural limitations.

[0061] The improved optical efficiency is due to the enhanced hole injection and transport characteristics as well as the improved electron injection and transport characteristics in the device. The compound represented by chemical formula 1 can exhibit low driving voltage and high efficiency.

[0062] A is a substituted or unsubstituted carbazoyl group and can be specifically represented by chemical formula 1A or chemical formula 1B.

[0063]

[0064] In chemical formula 1A and chemical formula 1B,

[0065] Ar 1 It can be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0066] L 2 It is a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0067] R 6 To R 8Each of these groups is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic.

[0068] m10 and m12 are each an independent integer from 1 to 4.

[0069] m11 is one of the integers from 1 to 3, and

[0070] * is related to L in chemical formula 1 1 The connection point.

[0071] m1 to m4 can each be an independent integer of 0 or 1, and

[0072] For example, when m1 to m4 are 0, X 1 To X 4 It does not exist, and phenyl groups are connected by σ bonds.

[0073] For example, when m1 to m4 are 1, X 1 To X 4 Each independently refers to phenyl and phenyl through X 1 To X 4 They blend together.

[0074] For example, when m1 to m4 are all 0, it can be represented by chemical formula 1-1.

[0075] [Chemical Formula 1-1]

[0076]

[0077] In chemical formula 1-1, R 1 To R 5 m5 to m9, n, L 1 A is the same as above.

[0078] For example, when at least one of m1 to m4 is 1, it can be represented by any one of chemical formulas 1-2 to 1-16.

[0079]

[0080]

[0081]

[0082] [Chemical Formula 1-16]

[0083]

[0084] In chemical formulas 1-2 to 1-16,

[0085] X 1 To X 4 n, A, L 1 m5 to m9 and R 1 To R 5 Similar to the above, m5', m6', m7', m8' and m9' are each independently an integer from 1 to 3, and m6”, m7” and m8” are each independently an integer of 1 or 2.

[0086] As a specific example, chemical formula 1-1 can be represented by chemical formula 1-1A or chemical formula 1-1B.

[0087]

[0088] In chemical formulas 1-1A and 1-1B,

[0089] n, m5 to m9, L 1 and R 1 To R 5 Same as above,

[0090] Ar 1 It can be a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group.

[0091] L 2 It is a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0092] m10 and m12 are each independently an integer from 1 to 4, and

[0093] m11 is one of the integers from 1 to 3, and

[0094] R 6 To R 8 Each of them is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0095] Depending on the position of the carbazol group, chemical formula 1-1A can be represented by any one of chemical formulas 1-1A-1 to 1-1A-4.

[0096]

[0097]

[0098] In chemical formulas 1-1A-1 to 1-1A-4,

[0099] n, L1 L 2 Ar 1 m5 to m11 and R 1 To R 7 Same as above.

[0100] As a specific example, chemical formula 1-2 can be represented by chemical formula 1-2A or chemical formula 1-2B.

[0101]

[0102] In chemical formulas 1-2A and 1-2B,

[0103] X 1 , n, L 1 L 2 Ar 1 m5', m6', m7 to m12 and R 1 To R 8 Same as above.

[0104] Depending on the position of the carbazole group, chemical formula 1-2A can be represented by any one of chemical formulas 1-2A-1 to 1-2A-4.

[0105]

[0106]

[0107] In chemical formulas 1-2A-1 to 1-2A-4,

[0108] X 1 , n, L 1 L 2 Ar 1 m5', m6', m7 to m11 and R 1 To R 7 Same as above.

[0109] As a specific example, chemical formula 1-3 can be represented by chemical formula 1-3A or chemical formula 1-3B.

[0110]

[0111] In chemical formulas 1-3A and 1-3B,

[0112] X 2 , n, L 1 L 2 Ar 1 m5, m6', m7', m8 to m12 and R 1 To R 8 Same as above.

[0113] Depending on the position of the carbazol group, chemical formula 1-3A can be represented by any one of chemical formulas 1-3A-1 to 1-3A-4.

[0114]

[0115]

[0116] In chemical formulas 1-3A-1 to 1-3A-4

[0117] X 2 , n, L 1 L 2 Ar 1 m5, m6', m7', m8 to m11 and R 1 To R 7 Same as above.

[0118] As a specific example, chemical formula 1-4 can be represented by chemical formula 1-4A or chemical formula 1-4B.

[0119]

[0120] In chemical formulas 1-4A and 1-4B,

[0121] X 3 , n, L 1 L 2 Ar 1 m5, m6, m9 to m12, m7', m8' and R 1 To R 8 Same as above.

[0122] Depending on the position of the carbazol group, chemical formula 1-4A can be represented by any one of chemical formulas 1-4A-1 to 1-4A-4.

[0123]

[0124] In chemical formulas 1-4A-1 to 1-4A-4,

[0125] X 3 , n, L 1 L 2 Ar 1 m5, m6, m9 to m11, m7', m8' and R 1 To R 7 Same as above.

[0126] As a specific example, chemical formula 1-5 can be represented by chemical formula 1-5A or chemical formula 1-5B.

[0127]

[0128] In chemical formulas 1-5A and 1-5B,

[0129] X 4 , n, L 1 L 2 Ar 1 m5, m6, m7, m8', m9', m10 to m12 and R 1 To R 8 Same as above.

[0130] Depending on the position of the carbazole group, chemical formula 1-5A can be represented by any one of chemical formulas 1-5A-1 to 1-5A-4.

[0131]

[0132] In chemical formulas 1-5A-1 to 1-5A-4,

[0133] X 4 , n, L 1 L 2 Ar 1 m5, m6, m7, m8', m9', m10, m11 and R 1 To R 7 Same as above.

[0134] As a specific example, chemical formula 1-6 can be represented by chemical formula 1-6A or chemical formula 1-6B.

[0135]

[0136]

[0137] In chemical formulas 1-6A and 1-6B,

[0138] X 1 X 2 , n, L 1 L 2 Ar 1 m5', m6", m7', m8 to m12 and R 1 To R 8 Same as above.

[0139] Depending on the position of the carbazol group, chemical formula 1-6A can be represented by any one of chemical formulas 1-6A-1 to 1-6A-4.

[0140]

[0141] In chemical formulas 1-6A-1 to 1-6A-4,

[0142] X 1 X 2 , n, L 1 L 2 Ar 1 m5', m6", m7', m8 to m11 and R 1 To R 7 Same as above.

[0143] As a specific example, chemical formula 1-7 can be represented by chemical formula 1-7A or chemical formula 1-7B.

[0144]

[0145] In chemical formulas 1-7A and 1-7B,

[0146] X 1 X 3 , n, L 1 L 2 Ar 1 m5', m6', m7', m8', m9 to m12 and R 1 To R 8 Same as above.

[0147] Depending on the position of the carbazo group, chemical formula 1-7A can be represented by any one of chemical formulas 1-7A-1 to 1-7A-4.

[0148]

[0149] In chemical formulas 1-7A-1 to 1-7A-4,

[0150] X 1 X 3 , n, L 1 L 2 Ar 1 m5', m6', m7', m8', m9 to m11 and R 1 To R 7 Same as above.

[0151] As a specific example, chemical formula 1-8 can be represented by chemical formula 1-8A or chemical formula 1-8B.

[0152]

[0153] In chemical formulas 1-8A and 1-8B,

[0154] X 1 X 4 , n, L 1 L 2 Ar 1 m5', m6', m7, m8', m9', m10 to m12 and R 1 To R 8 Same as above.

[0155] Depending on the position of the carbazole group, chemical formula 1-8A can be represented by any one of chemical formulas 1-8A-1 to 1-8A-4.

[0156]

[0157] In chemical formulas 1-8A-1 to 1-8A-4,

[0158] X 1 X 4 , n, L 1 L 2 Ar 1 m5', m6', m7, m8', m9', m10, m11 and R 1 To R 7 Same as above.

[0159] As a specific example, chemical formulas 1-9 can be represented by chemical formula 1-9A or chemical formula 1-9B.

[0160]

[0161] In chemical formulas 1-9A and 1-9B,

[0162] X 2 X 3 , n, L 1 L 2 Ar 1 m5, m6', m7", m8', m9, m10 to m12 and R 1 To R 8 Same as above.

[0163] Depending on the position of the carbazol group, chemical formula 1-9A can be represented by any one of chemical formulas 1-9A-1 to 1-9A-4.

[0164]

[0165] In chemical formulas 1-9A-1 to 1-9A-4,

[0166] X 2 X 3 , n, L1 L 2 Ar 1 m5, m6', m7", m8', m9, m10, m11 and R 1 To R 7 Same as above.

[0167] As a specific example, chemical formula 1-10 can be represented by chemical formula 1-10A or chemical formula 1-10B.

[0168]

[0169] In chemical formulas 1-10A and 1-10B,

[0170] X 2 X 4 , n, L 1 L 2 Ar 1 m5, m6', m7', m8', m9', m10 to m12 and R 1 To R 8 Same as above.

[0171] Depending on the position of the carbazole group, chemical formula 1-10A can be derived from chemical formula 1-10A-1 to chemical formula 1-10A-1.

[0172] Any one of the expressions in Equation 1-10A-4.

[0173]

[0174]

[0175] In chemical formulas 1-10A-1 to 1-10A-4,

[0176] X 2 X 4 , n, L 1 L 2 Ar 1 m5, m6', m7', m8', m9', m10, m11 and R 1 To R 7 Same as above.

[0177] As a specific example, chemical formula 1-11 can be represented by chemical formula 1-11A or chemical formula 1-11B.

[0178]

[0179] In chemical formulas 1-11A and 1-11B,

[0180] X3 X 4 , n, L 1 L 2 Ar 1 m5, m6, m7', m8", m9', m10 to m12 and R 1 To R 8 Same as above.

[0181] Depending on the position of the carbazole group, chemical formula 1-11A can be derived from chemical formula 1-11A-1 to chemical formula 1-11A-1.

[0182] Any one of the expressions in Equation 1-11A-4.

[0183]

[0184]

[0185] In chemical formulas 1-11A-1 to 1-11A-4,

[0186] X 3 X 4 , n, L 1 L 2 Ar 1 m5, m6, m7', m8", m9', m10, m11 and R 1 To R 7 Same as above.

[0187] As a specific example, chemical formula 1-12 can be represented by chemical formula 1-12A or chemical formula 1-12B.

[0188]

[0189] In chemical formulas 1-12A and 1-12B,

[0190] X 1 X 2 X 3 , n, L 1 L 2 Ar 1 m5', m6", m7", m8', m9, m10 to m12 and R 1 To R 8 Same as above.

[0191] Depending on the position of the carbazole group, chemical formula 1-12A can be derived from chemical formula 1-12A-1 to chemical formula 1-12A-1.

[0192] Any one of the expressions in Equation 1-12A-4.

[0193]

[0194] In chemical formulas 1-12A-1 to 1-12A-4,

[0195] X 1 X 2 X 3 , n, L 1 L 2 Ar 1 m5', m6”, m7”, m8', m9, m10, m11 and R 1 To R 7 Same as above.

[0196] As a specific example, chemical formula 1-13 can be represented by chemical formula 1-13A or chemical formula 1-13B.

[0197]

[0198] In chemical formulas 1-13A and 1-13B,

[0199] X 1 X 2 X 4 , n, L 1 L 2 Ar 1 m5', m6", m7', m8', m9', m10 to m12 and R 1 To R 8 Same as above.

[0200] Depending on the position of the carbazole group, chemical formula 1-13A can be derived from chemical formula 1-13A-1 to chemical formula 1-13A-1.

[0201] Any one of the expressions in Equation 1-13A-4.

[0202]

[0203] In chemical formulas 1-13A-1 to 1-13A-4,

[0204] X 1 X 2 X 4 , n, L 1 L 2 Ar 1 m5', m6", m7', m8', m9', m10, m11 and R 1 To R 7 Same as above.

[0205] As a specific example, chemical formula 1-14 can be represented by chemical formula 1-14A or chemical formula 1-14B.

[0206]

[0207] In chemical formulas 1-14A and 1-14B,

[0208] X 1 X 3 X 4 , n, L 1 L 2 Ar 1 m5', m6', m7', m8", m9', m10 to m12 and R 1 To R 8 Same as above.

[0209] Depending on the position of the carbazole group, chemical formula 1-14A can be derived from chemical formula 1-14A-1 to chemical formula 1-14A-1.

[0210] Any one of the expressions in Equation 1-14A-4.

[0211]

[0212] In chemical formulas 1-14A-1 to 1-14A-4,

[0213] X 1 X 3 X 4 , n, L 1 L 2 Ar 1 m5', m6', m7', m8", m9', m10, m11 and R 1 To R 7 Same as above.

[0214] As a specific example, chemical formula 1-15 can be represented by chemical formula 1-15A or chemical formula 1-15B.

[0215]

[0216] In chemical formulas 1-15A and 1-15B,

[0217] X 2 X 3 X 4 , n, L 1 L 2 Ar 1 m5, m6', m7", m8", m9', m10 to m12 and R 1 To R8 Same as above.

[0218] Depending on the position of the carbazole group, chemical formula 1-15A can be derived from chemical formula 1-15A-1 to chemical formula 1-15A-1.

[0219] Any one of the expressions in Equation 1-15A-4.

[0220]

[0221] In chemical formulas 1-15A-1 to 1-15A-4,

[0222] X 2 X 3 X 4 , n, L 1 L 2 Ar 1 m5, m6', m7", m8", m9', m10, m11 and R 1 To R 7 Same as above.

[0223] As a specific example, chemical formula 1-16 can be represented by chemical formula 1-16A or chemical formula 1-16B.

[0224]

[0225] In chemical formulas 1-16A and 1-16B,

[0226] X 1 X 2 X 3 X 4 , n, L 1 L 2 Ar 1 m5', m6”, m7”, m8”, m9', m10, m11, m12 and R 1 To R 8 Same as above.

[0227] Depending on the position of the carbazole group, chemical formula 1-16A can be derived from chemical formula 1-16A-1 to chemical formula 1-16A-1.

[0228] Any one of the expressions in Equation 1-16A-4.

[0229]

[0230] In chemical formulas 1-16A-1 to 1-16A-4,

[0231] X 1 X 2 X 3X 4 , n, L 1 L 2 Ar 1 m5', m6”, m7”, m8”, m9', m10, m11 and R 1 To R 7 Same as above.

[0232] For example, chemical formula 1 can be represented by chemical formula 1-1 or chemical formula 1-2.

[0233] In a specific exemplary embodiment, chemical formula 1 can be represented by any one of chemical formula 1-1A-4, chemical formula 1-1B, chemical formula 1-2A-2, and chemical formula 1-2B.

[0234] For example, X 1 To X 4 Each can be independently designated as O, S, or NR. a , where R a It can be a substituted or unsubstituted C6 to C20 aryl group.

[0235] For example, L 1 and L 2 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group.

[0236] For example, Ar 1 It can be a substituted or unsubstituted C6 to C12 aryl group.

[0237] For example, R 1 To R 8 Each can be independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0238] In the most specific exemplary embodiment, the compound for an organic optoelectronic device represented by chemical formula 1 may be one of the compounds in group 1, but is not limited thereto.

[0239] [Group 1]

[0240]

[0241] In addition to the aforementioned compounds for organic optoelectronic devices, one or more compounds may be further included.

[0242] The aforementioned compounds for organic optoelectronic devices may further include dopants.

[0243] For example, the dopant can be a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant.

[0244] A dopant is a material that is mixed in small amounts with a compound used in organic optoelectronic devices to induce luminescence, and can typically be a material that emits light through multiple excitation to a triplet or more triplet states, such as a metal complex. For example, the dopant can be an inorganic, organic, or organic-inorganic compound, and one or more of these types can be used.

[0245] 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. For example, a phosphorescent dopant can be a compound represented by the chemical formula Z, but is not limited thereto.

[0246] [Chemical Formula Z]

[0247] L 6 MX 7

[0248] In the chemical formula Z, M is a metal, and L... 6 and X 7 The same or different, and is a ligand that forms a complex with M.

[0249] For example, M can be Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 6 and X 7 It could be, for example, a bidentate ligand.

[0250] By L 6 and X 7 The examples of the ligands represented may be selected from, but are not limited to, the formulas listed in group A.

[0251] [Group A]

[0252]

[0253] In group A,

[0254] R 300 To R 302 Each is independently hydrogen, deuterium, halogen-substituted or unsubstituted C1 to C30 alkyl, C6 to C30 aryl, or halogen, and

[0255] R 303 To R 324Each 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.

[0256] As an example, it can include dopants represented by the chemical formula V.

[0257] [Chemical Formula V]

[0258]

[0259] In chemical formula V,

[0260] 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 ,

[0261] R 132 To R 134 Each is independently a C1 to C6 alkyl group.

[0262] R 101 To R 116 At least one of them is a functional group represented by the chemical formula V-1.

[0263] L 100 It is a bidentate ligand for monovalent anions, and is a ligand coordinated with iridium via the lone pair electrons of carbon or heteroatoms.

[0264] n1 and n2 are each independent integers from 0 to 3, and

[0265] n1+n2 is any integer from 1 to 3.

[0266] [Chemical Formula V-1]

[0267]

[0268] In chemical formula V-1,

[0269] 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

[0270] * refers to the part connected to a carbon atom.

[0271] As an example, it may include dopants represented by the chemical formula Z-1.

[0272] [Chemical Formula Z-1]

[0273]

[0274] In chemical formula Z-1, rings A, B, C, and D each independently represent a 5- or 6-membered carbon ring or a heterocycle;

[0275] R A R B R C and R D Each can be independently represented as monosubstituted, disubstituted, trisubstituted, tetrasubstituted, or unsubstituted;

[0276] L B L C and L D Each is independently selected from direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof;

[0277] When nA is 1, L E Selected from direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and their combinations; when nA is 0, L E It does not exist; and

[0278] R A R B R C R D R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl group, sulfinyl, sulfonyl, phosphinyl, and combinations thereof; any adjacent R A R B R CR D R and R' are optionally connected to each other to provide a ring; 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.

[0279] According to one embodiment, the dopant may be a platinum complex and may be represented, for example, by chemical formula VI.

[0280] [Chemical Formula VI]

[0281]

[0282] In chemical formula VI,

[0283] X 100 Selected from O, S and NR 131 ,

[0284] 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 ,

[0285] R 132 To R 134 Each is independently a C1 to C6 alkyl group, and

[0286] R 117 To R 131 At least one of them is -SiR 132 R 133 R 134 Or tert-butyl.

[0287] The following describes an organic optoelectronic device comprising the aforementioned compound for an organic optoelectronic device.

[0288] Organic optoelectronic devices can be any device that converts electrical energy into light energy and vice versa, without any particular limitation, and can be, for example, organic photoelectric devices, organic light-emitting diodes, organic solar cells, and organic photoconductor drums.

[0289] 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.

[0290] Figure 1This is a cross-sectional view of an organic light-emitting diode according to one embodiment.

[0291] refer to Figure 1 An organic light-emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110.

[0292] 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, 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.

[0293] 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.

[0294] The organic layer 105 may contain the aforementioned compounds used in organic optoelectronic devices.

[0295] The organic layer 105 may include a light-emitting layer 130, and the light-emitting layer 130 may contain the aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices.

[0296] The composition for organic optoelectronic devices that further includes dopants can be, for example, a red or green luminescent composition.

[0297] The light-emitting layer 130 may contain, for example, the aforementioned compounds used in organic optoelectronic devices as phosphorescent hosts.

[0298] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0299] The charge transport region can be, for example, the hole transport region 140.

[0300] 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.

[0301] 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 include at least one of the compounds of group B.

[0302] [Group B]

[0303]

[0304]

[0305]

[0306]

[0307] In the hole transport region 140, in addition to the aforementioned compounds, known compounds or similar compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A may also be used.

[0308] Alternatively, the charge transport region can be, for example, the electron transport region 150.

[0309] 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.

[0310] Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light-emitting layer 130 and an electron transport auxiliary layer between the light-emitting layer 130 and the electron transport layer, and at least one of the electron transport layer and the electron transport auxiliary layer may include at least one compound of group C.

[0311] [Group C]

[0312]

[0313]

[0314]

[0315] One embodiment may provide an organic light-emitting diode that includes a light-emitting layer as an organic layer.

[0316] Another implementation may provide an organic light-emitting diode that includes an emitting layer and a hole transport region as an organic layer.

[0317] Another embodiment may provide an organic light-emitting diode that includes an emitting layer and an electron transport region as organic layers.

[0318] like Figure 1 As shown, in addition to the light-emitting layer 130, the organic light-emitting diode according to the embodiment of the present invention may also include a hole transport region 140 and an electron transport region 150 as an organic layer 105.

[0319] On the other hand, in addition to the light-emitting layer, an organic light-emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc., as the aforementioned organic layer.

[0320] Organic light-emitting diodes 100 can be produced by forming an organic layer on a substrate using dry film forming methods (such as vacuum deposition (evaporation), sputtering, plasma electroplating and ion electroplating), and forming a cathode or anode thereon.

[0321] Organic light-emitting diodes (OLEDs) can be applied to organic light-emitting display devices.

[0322] 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 claims is not limited thereto.

[0323] Unless otherwise noted, the starting materials and reactants used in the examples and synthesis examples below were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods.

[0324] (Preparation of compounds for organic optoelectronic devices)

[0325] The compound, which is a specific example of the present invention, is synthesized through the following steps.

[0326] Synthesis Example 1: Synthesis of Compound A-1

[0327] [Reaction Formula 1]

[0328]

[0329] Step 1: Synthesis of intermediate A-1-A

[0330] 30 g (101 mmol) of 2-(3'-fluoro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxane-pentaborane and 28.27 g (106 mmol) of 3-bromo-3'-chloro-1,1'-biphenyl were dissolved in 335 ml of tetrahydrofuran (THF) and 167 ml of deionized water (DI water). 3.49 g (0.03 equivalents) of Pd(PPh3)4 and 27.81 g (2.0 equivalents) of K2CO3 were added. The mixture was then heated under nitrogen atmosphere at 80 °C with stirring. After 6 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The dried product was purified by column chromatography using a mixed solvent of hexane and dichloromethane in a volume ratio of 70:30 to obtain 28.6 g (yield: 79.2%) of intermediate A-1-A.

[0331] Step 2: Synthesis of intermediate A-1-B

[0332] 28.6 g (79 mmol) of intermediate A-1-A was dissolved in 316 mL of xylene, and 24.09 g (1.2 equivalents) of bis(pinacol)diboron, 2.17 g (0.03 equivalents) of Pd2(dba)3, 23.27 g (3.0 equivalents) of K(OAc) and 5.32 g (0.24 equivalents) of P(Cy)3 were added. The mixture was then heated under nitrogen atmosphere at 145 °C with stirring. After 12 hours, the reaction solution was cooled and concentrated. The extract obtained from it using dichloromethane and deionized water was purified by column chromatography using a mixed solvent of hexane and dichloromethane in a volume ratio of 40:10 to obtain 31.4 g (yield 88.2%) of intermediate A-1-B.

[0333] Step 3: Synthesis of intermediate A-1-C

[0334] 31.4 g (70 mmol) of intermediate A-1-B and 13.19 g (77 mmol) of 3-bromoaniline were dissolved in 232 mL of tetrahydrofuran (THF) and 116 mL of deionized water. 2.42 g (0.03 equivalents) of Pd(PPh3)4 and 19.27 g (2.0 equivalents) of K2CO3 were added, and the mixture was heated under nitrogen atmosphere at 80 °C with stirring. After 12 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The dried product was purified by column chromatography using a mixture of hexane and ethyl acetate in a volume ratio of 40:10 to give 22.7 g (78.4% yield) of intermediate A-1-C.

[0335] Step 4: Synthesis of intermediate A-1-D

[0336] 22.7 g (55 mmol) of intermediate A-1-C was dissolved in 200 mL of N-methyl-2-pyrrolidone (NMP), and 23.19 g (2.0 equivalents) of K3PO4 was added. The mixture was then heated under nitrogen atmosphere at 200 °C under reflux. After 12 hours, the reaction solution was cooled, and deionized water was slowly added dropwise to give a solid. The solid was washed with hexane and recrystallized from toluene to give 16.4 g (yield: 76%) of intermediate A-1-D.

[0337] Step 5: Synthesis of compound A-1

[0338] 22.7 g (50 mmol) of intermediate A-1-D and 19.5 g (61 mmol) of 9-(4-bromophenyl)-9H-carbazole were dissolved in 300 mL of xylene. 7.27 g (1.5 equivalents) of NaO(t-Bu) and 1.39 g (0.03 equivalents) of Pd2(dba)3, along with 2.82 mL (2.32 g, 0.1 equivalents) of a toluene solution containing 50% tri-tert-butylphosphine (50% P(t-Bu)3 in toluene), were added. The mixture was then heated under nitrogen atmosphere at 145 °C with stirring. After 12 hours, the reaction solution was cooled and concentrated. The product was washed with methanol and water to obtain a solid, which was recrystallized from xylene-acetone to give 30.55 g (yield: 83.3%) of compound A-1.

[0339] Synthesis Example 2: Synthesis of Compound A-2

[0340] [Reaction 2]

[0341]

[0342] Step 1: Synthesis of intermediate A-2-A

[0343] 20 g (81 mmol) of 4-bromo-9H-carbazole and 19.89 g (98 mmol) of iodobenzene were dissolved in 300 mL of toluene. Then, 11.72 g (1.5 equivalents) of NaO(t-Bu), 2.23 g (0.03 equivalents) of Pd2(dba)3, and 4.81 mL (3.95 g, 0.1 equivalents) of a toluene solution containing 50% tri-tert-butylphosphine (50% P(t-Bu)3 in toluene) were added. The mixture was then heated under nitrogen atmosphere at 115 °C with stirring. After 10 hours, the reaction solution was cooled and concentrated. The solution was then purified by column chromatography using a mixture of hexane and dichloromethane (75:25 v / v) to obtain a solid. The solid was washed with hexane to give 21.4 g (yield: 81.7%) of intermediate A-2-A.

[0344] Step 2: Synthesis of compound A-2

[0345] 23.1 g (58 mmol) of intermediate A-1-D synthesized via steps 1 to 4 of Synthetic Example 1 and 21.4 g (68 mmol) of intermediate A-2-A were dissolved in 300 mL of xylene. 8.4 g (1.5 equivalents) of NaO(t-Bu), 1.6 g (0.03 equivalents) of Pd2(dba)3, and 2.87 mL (2.36 g, 0.1 equivalents) of a toluene solution comprising 50% tri-tert-butylphosphine (50% P(t-Bu)3 in toluene) were added. The mixture was then heated under nitrogen atmosphere at 145 °C with stirring. After 12 hours, the reaction solution was cooled and concentrated, washed with methanol and water, and recrystallized from xylene to give 27.32 g (73.7% yield) of solid compound A-2.

[0346] Synthesis Example 3: Synthesis of Compound A-3

[0347] [Reaction 3]

[0348]

[0349] Step 1: A-3-Pre(A ) Synthesis

[0350] 30 g (96 mmol) of 5-bromo-3'-chloro-2-nitro-1,1'-biphenyl and 62.94 g (106 mmol) of triphenylphosphine were dissolved in 300 mL of dichlorobenzene (DCB), and then heated under nitrogen atmosphere at 180 °C with stirring. After 24 hours, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography using 100% hexane to give 23.3 g of solid intermediate A-3-Pre(A).

[0351] Step 2: Synthesis of intermediate A-3-A

[0352] 23.3 g (83 mmol) of intermediate A-3-Pre(A) and 20.33 g (100 mmol) of iodobenzene were dissolved in 300 mL of toluene. 11.97 g (1.5 equivalents) of NaO(t-Bu), 2.28 g (0.03 equivalents) of Pd2(dba)3, and 4.92 mL (4.03 g, 0.12 equivalents) of a toluene solution containing 50% tri-tert-butylphosphine (50% P(t-Bu)3 in toluene) were added. The mixture was then heated under nitrogen atmosphere at 115 °C with stirring. After 10 hours, the reaction solution was cooled and concentrated, purified by column chromatography using a 90:10 mixture of hexane and dichloromethane, and washed with hexane to obtain 20.30 g (68.3% yield) of intermediate A-3-A.

[0353] Step 3: Synthesis of intermediate A-3-B

[0354] 16 g (54 mmol) of 2-(3'-fluoro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxane and 20.1 g (56 mmol) of intermediate A-3-A were dissolved in 150 mL of tetrahydrofuran (THF) and 80 mL of deionized water. 1.86 g (0.03 equivalents) of Pd(PPh3)4 and 14.83 g (2.0 equivalents) of K2CO3 were added, and the mixture was heated under nitrogen atmosphere at 80 °C with stirring. After 6 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The product was purified by column chromatography using a 60:40 mixture of hexane and dichloromethane to give 18.86 g (yield: 78.5%) of intermediate A-3-B.

[0355] Step 4: Synthesis of intermediate A-3-C

[0356] 18.86 g (42 mmol) of intermediate A-3-B was dissolved in 180 mL of xylene, and 12.72 g (1.2 equivalents) of bis(pinacol)diboron, 1.15 g (0.03 equivalents) of Pd2(dba)3, 12.29 g (3.0 equivalents) of K(OAc) and 2.81 g (0.24 equivalents) of P(Cy)3 were added. The mixture was then heated under nitrogen atmosphere at 145 °C with stirring. After 12 hours, the reaction solution was cooled and concentrated. The extract obtained from it using dichloromethane and deionized water was purified by column chromatography using a mixed solvent of hexane and dichloromethane in a volume ratio of 40:10 to obtain 17.3 g (76.8% yield) of intermediate A-3-C.

[0357] Step 5: Synthesis of intermediate A-3-D

[0358] 17.0 g (32 mmol) of intermediate A-3-C and 5.96 g (35 mmol) of 3-bromoaniline were dissolved in 105 mL of tetrahydrofuran (THF) and 53 mL of deionized water. 1.09 g (0.03 equivalents) of Pd(PPh3)4 and 8.71 g (2.0 equivalents) of K2CO3 were added, and the mixture was heated under nitrogen atmosphere at 80 °C with stirring. After 12 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The dried product was purified by column chromatography using a mixture of hexane and ethyl acetate in a volume ratio of 45:5 to give 12.8 g (80.5% yield) of intermediate A-3-D.

[0359] Step 6: Synthesis of intermediate A-3-E

[0360] 12.0 g (25 mmol) of intermediate A-3-D was dissolved in 85 mL of N-methyl-2-pyrrolidone (NMP), and 10.77 g (2.0 equivalents) of K3PO4 was added. The mixture was then heated under nitrogen atmosphere at 200 °C with stirring. After 12 hours, the reaction solution was cooled, and deionized water was slowly added dropwise to obtain a solid. The solid was washed with hexane and recrystallized from toluene to give 10.3 g (yield 83.8%) of intermediate A-3-E.

[0361] Step 7: Synthesis of compound A-3

[0362] 10.3 g (21 mmol) of intermediate A-3-E and 8.2 g (25 mmol) of 9-(3-bromophenyl)-9H-carbazole were dissolved in 300 mL of xylene. Then, 3.06 g (1.5 equivalents) of NaO(t-Bu), 0.58 g (0.03 equivalents) of Pd2(dba)3, and 1.05 mL (0.86 g, 0.1 equivalents) of a toluene solution comprising 50% tri-tert-butylphosphine (50% P(t-Bu)3 in toluene) were added. The mixture was then heated under nitrogen atmosphere at 145 °C with stirring. After 12 hours, the reaction solution was cooled and concentrated, then washed with methanol and water to obtain a solid. The solid was recrystallized from xylene-acetone to give 12.6 g (yield 81.9%) of compound A-3.

[0363] Synthesis Example 4: Synthesis of Compound A-4

[0364] [Reaction 4]

[0365]

[0366] Step 1: Synthesis of intermediate A-4-A

[0367] 40 g (134 mmol) of 2-(3'-fluoro-[1,1'-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxacyclopentaborane and 39.66 g (141 mmol) of 2-bromo-8-chlorodibenzofuran were dissolved in 500 mL of tetrahydrofuran (THF) and 250 mL of deionized water. 4.65 g (0.03 equivalents) of Pd(PPh3)4 and 37.08 g (2.0 equivalents) of K2CO3 were added, and the mixture was heated under nitrogen atmosphere at 80 °C with stirring. After 6 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The dried product was purified by column chromatography using a 70:30 mixture of hexane and dichloromethane to give 38.42 g (76.8% yield) of intermediate A-4-A.

[0368] Step 2: Synthesis of intermediate A-4-B

[0369] 38.4 g (102 mmol) of intermediate A-4-A was dissolved in 400 mL of xylene. Then, 31.13 g (1.2 equivalents) of bis(pinacol)diboron, 2.81 g (0.03 equivalents) of Pd2(dba)3, 30.08 g (3.0 equivalents) of K(OAc) and 6.87 g (0.24 equivalents) of P(Cy)3 were added. The mixture was then heated under nitrogen atmosphere at 145 °C with stirring. After 12 hours, the reaction solution was cooled and concentrated. The extract obtained from the extract using dichloromethane and deionized water was purified by column chromatography using a 40:10 mixture of hexane and dichloromethane to obtain 39.68 g (yield 83.7%) of intermediate A-4-B.

[0370] Step 3: Synthesis of intermediate A-4-C

[0371] 39.6 g (85 mmol) of intermediate A-4-B and 16.14 g (94 mmol) of 3-bromoaniline were dissolved in 285 mL of tetrahydrofuran (THF) and 143 mL of deionized water. 2.96 g (0.03 equivalents) of Pd(PPh3)4 and 23.57 g (2.0 equivalents) of K2CO3 were added, and the mixture was heated under nitrogen atmosphere at 80 °C with stirring. After 12 hours, the reaction solution was cooled, and after removing the aqueous layer, the organic layer was dried under reduced pressure. The dried product was purified by column chromatography using a mixture of hexane and ethyl acetate in a volume ratio of 40:10 to give 27.18 g (74.2% yield) of intermediate A-4-C.

[0372] Step 4: Synthesis of intermediate A-4-D

[0373] 27.1 g (63 mmol) of intermediate A-4-C was dissolved in 210 mL of N-methyl-2-pyrrolidone (NMP), and 26.87 g (2.0 equivalents) of K3PO4 was added. The mixture was then heated under nitrogen atmosphere at 200 °C with stirring. After 12 hours, the reaction solution was cooled, and deionized water was slowly added dropwise to obtain a solid. The solid was washed with hexane and recrystallized from toluene to give 19.67 g (75.9% yield) of intermediate A-4-D.

[0374] Step 5: Synthesis of compound A-4

[0375] 19.6 g (48 mmol) of intermediate A-4-D and 18.46 g (57 mmol) of 2-bromo-9-phenylcarbazole were dissolved in 200 mL of xylene. 6.88 g (1.5 equivalents) of NaO(t-Bu), 1.31 g (0.03 equivalents) of Pd2(dba)3, and 2.36 mL (1.93 g, 0.1 equivalents) of a toluene solution comprising 50% tri-tert-butylphosphine (50% P(t-Bu)3 in toluene) were added. The mixture was then heated under nitrogen atmosphere at 145 °C with stirring. After 12 hours, the reaction solution was cooled and concentrated, then washed with methanol and water to obtain a solid. The solid was recrystallized from xylene-acetone to give 22.61 g (72.8% yield) of compound A-4.

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

[0377] [Reaction 5]

[0378]

[0379] Step 1: Synthesis of intermediate R-1-A

[0380] 50 g (155 mmol) of 2-bromo-7-phenyl-9H-carbazole and 158.29 g (86.5 mL, 776 mmol) of iodobenzene were dissolved in 440 mL of dimethylformamide (DMF). Then, 5.91 g (0.2 equivalents) of copper iodide (CuI), 32.17 g (1.5 equivalents) of potassium carbonate (K₂CO₃), and 5.59 g (0.2 equivalents) of 1,10-phenanthroline were added. The mixture was then heated under nitrogen atmosphere at 160 °C with stirring. After 18 hours, the reaction solution was cooled and concentrated, then washed with methanol to obtain a solid. The solid was recrystallized to give 55.33 g (yield 82.7%) of intermediate R-1-A.

[0381] Step 2: Synthesis of compound R-1

[0382] 55.3 g (139 mmol) of intermediate R-1-A and 40.78 g (166 mmol) of N-phenyl-[1,1'-biphenyl]-4-amine were dissolved in 550 mL of xylene. Then, 19.97 g (1.5 equivalents) of NaO(t-Bu), 3.81 g (0.03 equivalents) of Pd2(dba)3, and 6.84 mL (5.61 g, 0.1 equivalents) of a toluene solution containing 50% tri-tert-butylphosphine (50% P(t-Bu)3 in toluene) were added. The mixture was then heated under nitrogen atmosphere at 145 °C with stirring. After 18 hours, the reaction solution was cooled and concentrated, then dissolved in 130 mL of dichloromethane. The resulting solution was slowly added dropwise to 1,000 mL of methanol over 30 minutes with stirring to obtain a solid. The solid was purified by column chromatography using a mixed solvent of hexane and dichloromethane in a volume ratio of 70:30 to obtain 58.32 g (yield 74.8%) of compound R-1.

[0383] (Manufacturing of Organic Light Emitting Diodes)

[0384] Example 1

[0385] The ITO (indium tin oxide) coated glass substrate was washed with distilled water and ultrasonically. After washing with distilled water, the glass substrate was ultrasonically washed 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. The prepared ITO transparent electrode was used as the anode, and compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form... A thick hole injection layer, and compound A is deposited on the hole injection layer. The thickness is increased to form a hole transport layer. Compound B is deposited on the hole transport layer to... The thickness was adjusted to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound A-1 obtained in Synthesis Example 1 was used as the host, and 10 wt% PhGD was doped as a dopant, and the layer was formed by vacuum deposition. A thick luminescent layer. Subsequently, compound C is deposited on the luminescent layer to... The thickness is such that an electron transport auxiliary layer is formed, and compounds D and LiQ are simultaneously vacuum-deposited at a 1:1 weight ratio to form... A thick electron transport layer. Vacuum deposition on the electron transport layer. LiQ and Al was used to form the cathode, thus creating an organic light-emitting diode.

[0386] ITO / Compound A (3% NDP-9 doped) Compound A / Compound B / EML[90wt% host (compound A-1):10wt% PhGD] / Compound C / Compound D:LiQ / LiQ / Al

[0387] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0388] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluorene-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0389] Compound C: 2,4-Diphenyl-6-(4',5',6'-triphenyl[1,1':2',1”:3”,1”':3”',1””-pentaphenyl]-3””-yl)-1,3,5-triazine

[0390] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluorene-4-yl)-6-phenyl-1,3,5-triazine

[0391] [PhGD]

[0392]

[0393] Reality Examples 2 and 3 and Comparative Example 1

[0394] The diodes of Examples 2 and 3 and Comparative Example 1 were manufactured in the same manner as in Example 1, except that the main body was changed, as shown in Table 1.

[0395] evaluate

[0396] (1) Measure the change in current density based on voltage change.

[0397] 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.

[0398] (2) Measure the brightness change based on voltage changes

[0399] 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.

[0400] (3) Measurement of luminous efficiency

[0401] Using the brightness and current density from terms (1) and (2), the calculation was performed at the same current density (10 mA / cm²). 2 Luminous efficiency (cd / A) at ).

[0402] The relative values ​​of luminous efficiency based on Comparative Example 1 are shown in Table 1.

[0403] (4) Measurement of lifespan

[0404] At 24,000 cd / m 2 As the initial brightness (cd / m 2 The organic light-emitting diodes (OLEDs) emitted light, and their T95 lifetime was measured as the decrease in brightness over time using the Polanonix lifetime measurement system, as a percentage of their brightness relative to their initial brightness (cd / m²). 2 The time it takes for the percentage to drop to 95%.

[0405] The relative values ​​of T95 lifetime based on Comparative Example 1 are shown in Table 1.

[0406] (5) Measurement of driving voltage

[0407] Using a current-voltmeter (Keithley 2400) at 15mA / cm 2 The driving voltage of each device was measured and the results were obtained.

[0408] The relative values ​​of the driving voltage based on Comparative Example 1 are shown in Table 1.

[0409] (Table 1)

[0410] main body Drive voltage (%) Luminous efficiency (%) Lifespan T95 (%) Example 1 A-1 83.8％ 113％ 112％ Example 2 A-2 84.5％ 110％ 108％ Example 3 A-3 85.4％ 109％ 105％ Comparative Example 1 R-1 100％ 100％ 100％

[0411] The lower driving voltage value compared to 100% of the driving voltage value of Comparative Example 1 indicates excellent performance of low driving, but the higher luminous efficiency and lifetime compared to 100% of the luminous efficiency and lifetime of Comparative Example 1 indicate excellent performance.

[0412] Referring to Table 1, compared with the organic light-emitting diodes according to the comparative examples, the organic light-emitting diodes manufactured by applying the compounds according to the exemplary embodiments exhibit significantly improved driving, luminous efficiency and lifetime characteristics.

[0413] While the invention has been described in conjunction with what is now considered to be practical embodiments, 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 an organic optoelectronic device, the compound being represented by Chemical Formula 1-1 or Chemical Formula 1-2: in Chemical Formula 1-1 and Chemical Formula 1-2, each of m5 to m9 is independently one of an integer of 1 to 4, X 1 is NR a , each of m5' and m6' is independently one of an integer of 1 to 3, n is 1, A is a substituted or unsubstituted carbazolyl group, "substituted" means that at least one hydrogen of a substituent is replaced with deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. L 1 is a single bond or substituted or unsubstituted C6to C20arylene, R a is substituted or unsubstituted C6to C20aryl, R 1 to R 5 each independently is hydrogen, deuterium, or substituted or unsubstituted C1to C10alkyl, and 2.The compound for use in an organic optoelectronic device according to claim 1, wherein the compound is represented by one of Chemical Formula 1-1A-4, Chemical Formula 1-1B, Chemical Formula 1-2A-2, and Chemical Formula 1-2B: [Chemical Formula 1-1A-4] [Chemical Formula 1-1B] [Chemical Formula 1-2A-2] [Chemical Formula 1-2B] in Chemical Formula 1-1A-4, Chemical Formula 1-1B, Chemical Formula 1-2A-2, and Chemical Formula 1-2B, m11 is one of an integer of 1 to 3, each of m5' and m6' is independently one of an integer of 1 to 3, X 1 , m5 to m9, n, L 1 and R 1 to R 5 are each independently one of an integer from 1 to 4, and m10 and m12 are each independently one of an integer from 1 to 4, 3.The compound for use in an organic optoelectronic device according to claim 1, wherein the compound is one of compounds of Group 1: [Group 1] Ar 1 substituted or unsubstituted C6to C12aryl, L 2 is a single bond or substituted or unsubstituted C6to C20arylene, and R 6 to R 8 each independently is hydrogen, deuterium, cyano, or substituted or unsubstituted C1to C10alkyl. 4.An organic optoelectronic device comprising an anode and a cathode facing each other, at least one organic layer between the anode and the cathode, the organic layer comprising the compound for use in an organic optoelectronic device according to any one of claims 1 to 3. 5.The organic optoelectronic device according to claim 4, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound for use in an organic optoelectronic device. 6.A display device comprising the organic optoelectronic device according to claim 4 or 5. ​ wherein ​ ​ ​ ​ ​

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