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

Abstract

This invention relates to compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices. The composition comprises the compound, the organic optoelectronic device includes the compound or the composition, and the display device includes the organic optoelectronic device. The compound is represented by a combination of Chemical Formula 1 and Chemical Formula 2. [Chemical Formula 1][Chemical Formula 2]

Description

[0001] Citations of relevant applications

[0002] This application claims priority and benefit to Korean Patent Application No. 10-2025-0047618, filed on April 11, 2025, with the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The embodiments relate to compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices. Background Technology

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

[0005] Based on their working principles, organic optoelectronic devices can be divided into two types. One type generates electrical energy by separating excitons formed by 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 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 photoconductor drums.

[0007] In recent years, organic light-emitting diodes (OLEDs) have attracted much attention due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance can be affected by the organic materials between the electrodes. Summary of the Invention

[0008] The embodiments involve compounds for organic optoelectronic devices represented by a combination of chemical formulas 1 and 2: [Chemical Formula 1] [Chemical Formula 2]

[0009] In chemical formula 1 and chemical formula 2, Q 1 Q 2 and Q 3 Each is CR independently a Or in chemical formula 2 The connecting carbon at the point, condition Q 1 Q 2 and Q 3 One of them is in chemical formula 2 The connecting carbon at the point, R a and R 1 To R 9Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl, Ar 1 It is a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl, n1 and n6 are each independently an integer from 1 to 3, n2, n4, n5, n7 and n8 are each independently an integer from 1 to 4, n3 is an integer from 1 to 5, m1 is 0 or 1, and when n1 to n8 are 2 or greater, each R 1 To R 8 Each is the same as or different from the other.

[0010] The implementation can be achieved by providing a composition for an organic optoelectronic device, the composition comprising a first compound and a second compound, wherein the first compound is a compound for an organic optoelectronic device according to some embodiments, and the second compound is represented by chemical formula 3: [Chemical Formula 3]

[0011] In chemical formula 3, Z 1 To Z 3 Each is independently N or CR b The condition is Z 1 To Z 3 At least two of them are N and L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted divalent C2 to C20 heterocyclic group, Ar 2 and Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C20 heterocyclic, or a substituted or unsubstituted silyl group, R b R 10 and R 11 Each of the following is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen, each R 10 and R 11 They exist separately or are connected to form a ring, and m10 and m11 are each an independent integer from 1 to 4.

[0012] The implementation can be achieved by providing an organic optoelectronic device comprising an anode and a cathode facing each other, and an organic layer located between the anode and the cathode, wherein the organic layer comprises a compound for the organic optoelectronic device according to one embodiment.

[0013] The implementation can be achieved by providing an organic optoelectronic device comprising an anode and a cathode facing each other, and an organic layer located between the anode and the cathode, wherein the organic layer comprises a composition for an organic optoelectronic device according to one embodiment.

[0014] The implementation can be achieved by providing a display device that includes an organic optoelectronic device according to one embodiment. Attached Figure Description

[0015] The features will become clear to those skilled in the art from the detailed description of exemplary embodiments with reference to the accompanying drawings, wherein: Figure 1 This is a cross-sectional view showing an embodiment of an organic light-emitting diode, which is an embodiment of an organic optoelectronic device according to some exemplary embodiments, and Figure 2 This is a cross-sectional view showing another embodiment of an organic light-emitting diode, which is an embodiment of an organic optoelectronic device according to some exemplary embodiments. Detailed Implementation

[0016] Exemplary embodiments will now be described more fully below with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as being limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be sufficient and complete, and will fully convey exemplary implementations to those skilled in the art.

[0017] In the accompanying drawings, the dimensions of layers and regions may be enlarged for clarity. It will also be understood that when a layer or element is referred to as being "on" another layer or substrate, it may be directly on that layer or substrate, or there may be intermediate layers present. Furthermore, it will be understood that when a layer is referred to as being "below" another layer, it may be directly below, or there may be one or more intermediate layers present. Additionally, it will be understood that when a layer is referred to as being "between" two layers, it may be the only layer between the two layers, or there may be one or more intermediate layers present. The same reference numerals always denote the same elements. As used herein, the term "or" is not an exclusive term; for example, "A or B" will include A, B, or A and B.

[0018] As used herein, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by a deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or combinations thereof.

[0019] In one embodiment of the present 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 present invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C20 alkyl, C3 to C20 cycloalkyl, C6 to C30 aryl, or cyano. In a specific embodiment of the present invention, "substituted" means that at least one hydrogen atom of the substituent or compound is replaced by deuterium, C1 to C5 alkyl, C3 to C10 cycloalkyl, C6 to C18 aryl, or cyano. In specific examples of embodiments of the present invention, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, tert-butyl, cyclopropyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0020] As used in this article, "unsubstituted" means that the hydrogen atom has not been replaced by another substituent and the hydrogen atom is retained.

[0021] As used herein, “hydrogen substitution (-H)” can include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0022] As used herein, unless otherwise defined, “heterogeneous” means a group that contains one to three heteroatoms selected from N, O, S, P and Si in a functional group and the remainder is carbon.

[0023] As used herein, "aryl" refers to a group comprising at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have conjugated p orbitals, such as phenyl, naphthyl, etc. Two or more hydrocarbon aromatic moiety may be linked by σ bonds and the hydrocarbon aromatic moiety may be, for example, biphenyl, terphenyl, tetraphenyl, etc., and two or more hydrocarbon aromatic moiety may be directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0024] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0025] As used herein, "heterocyclic group" is a superordinate concept of a heteroaryl group and may contain at least one heteroatom selected from N, O, S, P, and Si to replace 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 contain one or more heteroatoms.

[0026] For example, "heteroaryl" can represent an aryl group containing 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 contains two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring can contain 1 to 3 heteroatoms.

[0027] 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 naphthacenyl, 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 trefoil, a substituted or unsubstituted triphenylene, a substituted or unsubstituted perylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof.

[0028] 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 benzo[] Thiophene, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, 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 dibenzothiopheneyl, or combinations thereof.

[0029] As used herein, hole characteristics refer to the ability of contributing electrons to form holes when an electric field is applied, and due to the conductivity of the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be easily injected into the light-emitting layer and transported within the light-emitting layer.

[0030] In addition, 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 in the light-emitting layer.

[0031] The following describes compounds for organic optoelectronic devices according to some exemplary embodiments.

[0032] Compounds for organic optoelectronic devices according to some exemplary embodiments can be represented, for example, by a combination of chemical formula 1 and chemical formula 2.

[0033] [Chemical Formula 1] [Chemical Formula 2]

[0034] In chemical formula 1 and chemical formula 2, Q 1 Q 2 and Q 3 They can be independent of each other, for example, CR a Or in chemical formula 2 The connecting carbon at the point of connection.

[0035] In one implementation, Q 1 Q 2 and Q 3 One of them is connected to chemical formula 2.

[0036] R a and R 1 To R 9 Each can be, independently or include, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl.

[0037] Ar 1 It can be, for example, a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl.

[0038] n1 and n6 can each be an integer, for example, from 1 to 3, independently.

[0039] n2, n4, n5, n7, and n8 can each be an integer from 1 to 4 independently.

[0040] n3 can be, for example, an integer from 1 to 5.

[0041] m1 can be an integer, for example, 0 or 1.

[0042] In one implementation, n1 can be, for example, 2 or 3, and each R 1 They can be the same as or different from each other.

[0043] In one implementation, n2 can be, for example, 2, 3, or 4, and each R 2 They can be the same as or different from each other.

[0044] In one implementation, n3 can be, for example, 2, 3, 4, or 5, and each R 3 They can be the same as or different from each other.

[0045] In one implementation, n4 can be, for example, 2, 3, or 4, and each R 4 They can be the same as or different from each other.

[0046] In one implementation, n5 can be, for example, 2, 3, or 4, and each R 5 They can be the same as or different from each other.

[0047] In one implementation, n6 can be, for example, 2 or 3, and each R 6 They can be the same as or different from each other.

[0048] In one implementation, n7 can be, for example, 2, 3, or 4, and each R7 They can be the same as or different from each other.

[0049] In one implementation, n8 can be, for example, 2, 3, or 4, and each R 8 They can be the same as or different from each other.

[0050] The compound represented by the combination of chemical formula 1 and chemical formula 2 has a structure that connects three carbazoles, and thus can further enhance hole properties and therefore exhibit low driving properties.

[0051] In particular, the lifetime characteristics can be further improved when 9-carbazole is connected to the 1st, 2nd or 4th position of the carbazole, and another 9-carbazole is connected to the 3rd position relative to the 9-carbazole.

[0052] In one implementation, additional lifetime enhancement can be achieved by introducing a LUMO group (the LUMO moiety in the molecule), wherein the terphenyl group attached to carbazole is connected in an ortho-meta orientation.

[0053] In one implementation, based on the connection position of 9-carbazole, chemical formula 1 can be represented, for example, by one of chemical formulas 1-I to 1-III.

[0054] [Chemical Formula 1-I]

[0055] [Chemical Formula 1-II]

[0056] [Chemical Formula 1-III]

[0057] In chemical formulas 1-I to 1-III, R 1 To R 9 Ar 1 n1 to n8 and m1 can be defined as those described above.

[0058] R a1 and R a2 Each can be associated with the R described above. a Same definition.

[0059] In one implementation, based on Ar 1 The substitution position of chemical formula 1 can be represented by, for example, one of chemical formulas 1-1 to 1-4.

[0060] [Chemical Formula 1-1] [Chemical Formula 1-2]

[0061] [Chemical Formula 1-3] [Chemical Formula 1-4]

[0062] In chemical formulas 1-1 to 1-4, Q 1 Q 2 Q 3 R 1 To R 4 R 9 Ar 1 n1 to n4 and m1 can be defined as described above.

[0063] In one implementation, chemical formula 1 can be represented, for example, by chemical formula 1-1 or chemical formula 1-2.

[0064] In one implementation, chemical formula 1 can be represented, for example, by chemical formula 1-1.

[0065] In some exemplary embodiments, the combination of chemical formula 1 and chemical formula 2 may be represented by, for example, one of chemical formula 1-1A, chemical formula 1-1B and chemical formula 1-1C.

[0066] [Chemical Formula 1-1A]

[0067] [Chemical Formula 1-1B]

[0068] [Chemical Formula 1-1C]

[0069] In chemical formulas 1-1A, 1-1B, and 1-1C, R 1 To R 9 R a1 R a2 Ar 1 n1 to n8 and m1 can be defined as those described above.

[0070] When Ar 1 When linked to 9-carbazole at the ortho position, the structure can become more advantageous in terms of T1 energy, and the efficiency and lifespan of the device can be improved.

[0071] In a specific implementation, the combination of chemical formula 1 and chemical formula 2 can be represented by chemical formula 1-1B.

[0072] In one implementation, R a and R 1 To R 9Each of them can be hydrogen, deuterium, substituted or unsubstituted C1 to C6 alkyl or substituted or unsubstituted phenyl.

[0073] In one implementation, R a and R 1 To R 9 Each can be, independently, for example, hydrogen, deuterium, or substituted or unsubstituted phenyl.

[0074] Furthermore, the compound used in organic optoelectronic devices can be substituted with at least one deuterium atom. The number of substituted deuterium atoms can be from 1 to the maximum number of hydrogen atoms in the chemical formula, for example, from 1 to 40 or from 1 to 30.

[0075] Additional lifespan improvements can be achieved through deuterium substitution.

[0076] In one implementation, the compound for organic optoelectronic devices represented by the combination of chemical formula 1 and chemical formula 2 can be, for example, a compound of group 1.

[0077] [Group 1]

[0078] [H-1] [H-2] [H-3] [H-4]

[0079] [H-5] [H-6] [H-7] [H-8]

[0080] [H-9] [H-10] [H-11] [H-12]

[0081] [H-13] [H-14] [H-15] [H-16]

[0082] [H-17] [H-18] [H-19] [H-20]

[0083] [H-21] [H-22] [H-23] [H-24]

[0084] [H-25] [H-26] [H-27] [H-28]

[0085] [H-29] [H-30] [H-31] [H-32]

[0086] [H-33] [H-34] [H-35] [H-36]

[0087] [H-37] [H-38] [H-39] [H-40]

[0088] [H-41] [H-42] [H-43] [H-44]

[0089] [H-45] [H-46] [H-47] [H-48]

[0090] [H-49] [H-50] [H-51] [H-52]

[0091] [H-53] [H-54]

[0092] Dn represents the number of hydrogen atoms replaced by deuterium, and n is an integer between 1 and the maximum possible number of replacements.

[0093] In one implementation, the compound used for the organic optoelectronic device can be deuterated and can be, for example, a compound from group 1-1.

[0094] [Group 1-1]

[0095] [H-55] [H-56]

[0096] [H-57] [H-58] [H-59] [H-60]

[0097] [H-61] [H-62] [H-63] [H-64]

[0098] [H-65] [H-66] [H-67] [H-68]

[0099] [H-69] [H-70] [H-71] [H-72]

[0100] [H-73] [H-74] [H-75] [H-76]

[0101] [H-77] [H-78] [H-79] [H-80]

[0102] [H-81] [H-82] [H-83] [H-84]

[0103] [H-85] [H-86] [H-87] [H-88]

[0104] [H-89] [H-90] [H-91] [H-92]

[0105] [H-93] [H-94] [H-95] [H-96]

[0106] [H-97] [H-98] [H-99] [H-100]

[0107] [H-101] [H-102] [H-103] [H-104]

[0108] [H-105] [H-106] [H-107] [H-108]

[0109] [H-109] [H-110] [H-111] [H-112]

[0110] [H-113] [H-114] [H-115] [H-116]

[0111] [H-117] [H-118] [H-119] [H-120]

[0112] [H-121] [H-122] [H-123] [H-124]

[0113] [H-125] [H-126] [H-127] [H-128]

[0114] [H-129] [H-130] [H-131] [H-132]

[0115] [H-133] [H-134] [H-135]

[0116] The compounds described above for use in organic optoelectronic devices can be used in combination with other compounds to exhibit synergistic effects in improving the performance of organic optoelectronic devices, such as organic light-emitting diodes.

[0117] A composition for an organic optoelectronic device according to some exemplary embodiments may include, for example, the compound described above (the first compound) and a second compound different from the first compound.

[0118] The second compound may have a structure in which one or more substituted or unsubstituted carbazole groups are bonded, for example, directly or indirectly, to a nitrogen-containing ring, thereby helping to effectively control the HOMO and LUMO energy levels and helping to ensure the migration stability of electrons (negative polarons). Therefore, compositions for organic optoelectronic devices can help improve charge mobility in organic optoelectronic devices and help reduce driving voltage, while exhibiting improved lifetime characteristics.

[0119] In one implementation, the second compound can be represented by chemical formula 3.

[0120] [Chemical Formula 3]

[0121] In chemical formula 3, Z 1 To Z 3 They can be, for example, N or CR, independently. b .

[0122] In one implementation, Z 1 To Z 3 At least two of them are N.

[0123] L1 To L 3 Each can be, independently, for example, a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted divalent C2 to C20 heterocyclic group.

[0124] Ar 2 and Ar 3 Each can be independently, for example, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a substituted or unsubstituted silyl group.

[0125] R b R 10 and R 11 Each of these can be, independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen.

[0126] Each R 10 and R 11 They can exist separately, or two adjacent groups can connect to form a ring.

[0127] m10 and m11 can each be an integer, for example, from 1 to 4, independently.

[0128] In one implementation, Z 1 To Z 3 Two of them can be, for example, N, and the remaining one can be, for example, CR. b .

[0129] In one implementation, Z 1 To Z 3 Each can be, for example, N.

[0130] In one implementation, Ar 2 and Ar 3 At least one of them can be, for example, a substituted or unsubstituted carbazoyl group.

[0131] In one implementation, Ar 2 and Ar 3 At least one of them can be, for example, a substituted or unsubstituted silyl group.

[0132] In one implementation, Ar 2 and Ar 3 Each of them can be a substituted or unsubstituted carbazole group, as represented in chemical formula 3a.

[0133] In one implementation, Ar 2 and Ar3 Each of them can be a substituted or unsubstituted silyl group, as represented in chemical formula 3b.

[0134] [Chemical Formula 3a] [Chemical Formula 3b]

[0135] In chemical formulas 3a and 3b, Z 1 To Z 3 L 1 To L 3 m10, m11, R 10 and R 11 As defined in chemical formula 3.

[0136] R 12 To R 16 Each of these can be, independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic, substituted or unsubstituted amino, substituted or unsubstituted silyl, cyano, or halogen.

[0137] m12 and m13 can each be an integer, for example, from 1 to 4, independently.

[0138] m14 to m16 can each be an integer, for example, 1 to 5, independently.

[0139] Each R 12 To R 16 They can exist separately or two adjacent groups can connect to form a ring.

[0140] In one implementation, L 1 It could be, for example, a single key.

[0141] In one implementation, L 2 It can be, for example, a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted bitriphenylene, a substituted or unsubstituted dibenzofuranylene, a substituted or unsubstituted dibenzothiopheneylene, or a substituted or unsubstituted carbazolylene.

[0142] In one implementation, L 3 It can be, for example, a single bond or a substituted or unsubstituted phenylene oxide.

[0143] In one implementation, Ar 2 and Ar 3Each of these can be independently, for example, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazoyl, or a substituted or unsubstituted triphenylsilyl.

[0144] In one implementation, R 12 To R 16 and R b Each of these can be independently, for example, hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted silyl, or cyano.

[0145] In one implementation, at least one of the first and second compounds may be substituted with one or more deuterium atoms. In this document, the number of deuterium atoms substituted in each compound may be, for example, from 1 to the maximum number of hydrogen atoms in the chemical formula, such as 1 to 40 or 1 to 30.

[0146] In one implementation, the second compound represented by chemical formula 3 may include, for example, compounds from group 2.

[0147] [Group 2]

[0148] Dn represents the number of hydrogen atoms replaced by deuterium, and n is an integer between 1 and the maximum possible number of replacements.

[0149] By jointly including the first and second compounds, excellent interfacial properties can be exhibited, and by finely controlling the mobility of holes and electrons, the balance of electrons and holes in the active layer (e.g., the light-emitting layer, 130) of the organic optoelectronic device can be improved, thereby helping to improve luminous efficiency, while reducing unbound charges caused by the imbalance of electron and hole mobility, thus helping to improve lifetime.

[0150] In one implementation, the first compound and the second compound can be included as the main components, and the organic optoelectronic device 100, including the light-emitting layer 130 to which the first compound and the second compound are applied, can be finely controlled so that holes and electrons injected from the anode 110 and the cathode 120 respectively have appropriate mobility within the light-emitting layer 130, thereby strongly inducing the generation of excitons within the light-emitting layer and helping to improve the luminous efficiency within the light-emitting layer.

[0151] The composition for an organic optoelectronic device may contain a first compound and a second compound in different proportions. In one implementation, the composition for an organic optoelectronic device may contain the first compound and the second compound in a weight ratio of, for example, 10:90 to 90:10, and within the above range, may contain the first compound and the second compound in a weight ratio of, for example, about 20:80 to about 80:20, about 30:70 to about 70:30, about 40:60 to about 60:40, or about 50:50.

[0152] In one implementation, the first compound may be included in an amount greater than or equal to that of the second compound, for example, the first compound may be included in an amount of about 50 wt% to about 90 wt% based on the total weight of the first and second compounds.

[0153] In one implementation, the first compound may be included in an amount less than or equal to that of the second compound, for example, the first compound may be included in an amount of about 10 wt% to about 50 wt% based on the total weight of the first and second compounds.

[0154] In addition to the first and second compounds, the composition for the organic optoelectronic device may also contain a luminescent dopant. The luminescent dopant may be a material that causes luminescence when mixed in small amounts into the composition for the organic optoelectronic device, and typically may be a material that emits light through multiple excitation to a triplet or more states, such as a metal complex. The luminescent dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and may be contained in one or more types.

[0155] The luminescent dopant can be, for example, a phosphorescent dopant, a delayed fluorescence dopant, a fluorescent dopant, or a combination thereof. In one implementation, using a phosphorescent dopant or a delayed fluorescence dopant as a phosphorescent photosensitizer or auxiliary dopant can help efficiently transfer energy received from the host to the fluorescent dopant.

[0156] Phosphorescent dopants can be organometallic compounds and can enhance energy migration to fluorescent dopants, thereby enabling excitons formed in the emissive layer to emit light rapidly within the emissive layer, thus helping to reduce the degradation of light-emitting diodes.

[0157] The phosphorescent dopant can be an organometallic compound, and can be, for example, an organometallic compound including iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), or combinations thereof, and can be an organometallic compound containing an organic ligand comprising a nitrogen-containing ring. The nitrogen-containing ring can be, for example, a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted triazine, a substituted or unsubstituted carbazole, a substituted or unsubstituted imidazole, a substituted or unsubstituted benzimidazole, or combinations thereof.

[0158] The phosphorescent dopant can be, for example, one of compounds P1 to P32 and P41 to P52.

[0159]

[0160] Delayed fluorescence dopants can be metal-atom-free compounds with a ΔEST less than or equal to 0.2 eV, and since the upconversion process via reverse intersystem crossing (RISC) can be advantageous, the efficiency of light-emitting diodes containing them can be improved.

[0161] The delayed fluorescence dopant can be, for example, one of compounds T1 to T12.

[0162]

[0163] Fluorescent dopants can be, for example, polycyclic compounds, and due to their high absorption, they can improve the luminous efficiency and lifetime characteristics of light-emitting diodes by accepting energy transfer within the emissive layer.

[0164] The fluorescent dopant can be a condensed polycyclic compound containing, for example, boron (B), nitrogen (N), or a combination thereof, and can be, for example, one of compounds D1 to D38.

[0165]

[0166] The phosphorescent dopant, delayed fluorescence dopant, or fluorescent dopant may each be included in an amount of, for example, less than or equal to about 20 wt%, and within the aforementioned range, may each be included in an amount of, for example, about 0.1 to about 20 wt%, about 0.1 to about 15 wt%, about 0.1 to about 10 wt%, about 0.1 to about 7 wt%, about 0.1 to about 5 wt%, about 0.1 to about 4 wt%, about 1 to about 20 wt%, about 1 to about 15 wt%, about 1 to about 10 wt%, about 1 to about 7 wt%, about 1 to about 5 wt%, or about 1 to about 4 wt%, based on the total amount of the composition for the organic optoelectronic device.

[0167] Compositions for organic optoelectronic devices may additionally contain additives, and the additives may be, for example, organic materials, inorganic materials, organic / inorganic materials, or combinations thereof.

[0168] In the following text, an organic optoelectronic device using the above-described compound for an organic optoelectronic device or a composition for an organic optoelectronic device will be described.

[0169] There is no specific limitation on organic optoelectronic devices, as long as they are devices that can convert electrical energy and light energy into each other, and examples of such devices can include organic light-emitting diodes, organic photoelectric devices, organic solar cells, or organic photoconductor drums.

[0170] Organic optoelectronic devices may include, for example, an anode and a cathode facing each other, and an organic layer located between the anode and the cathode, and the organic layer may include the aforementioned compounds or compositions. The organic layer may include, for example, an active layer, such as a light-emitting layer or a light-absorbing layer, and the aforementioned compounds or compositions may be included in the active layer. The organic layer may include, for example, an auxiliary layer located between the anode and the active layer or between the cathode and the active layer, and the aforementioned compounds or compositions may be included in the auxiliary layer.

[0171] In this document, an organic light-emitting diode (OLED) is described as an example of an organic optoelectronic device, but it can be equally applied to other organic optoelectronic devices.

[0172] Figure 1 This is a cross-sectional view showing an embodiment of an organic light-emitting diode, which is an embodiment of an organic optoelectronic device according to some exemplary embodiments.

[0173] refer to Figure 1 An organic optoelectronic device 100 according to some exemplary embodiments may include, for example, an anode 110 and a cathode 120 facing each other, and a light-emitting layer 130 located between the anode 110 and the cathode 120.

[0174] The anode 110 can be made of a conductor with a high work function to facilitate hole injection, and can be made, for example, of a metal, a metal oxide, or a conductive polymer. The anode 110 can be made, for example, of the following: metals, such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO and Al or SnO2 and Sb; or conductive polymers, such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxo)thiophene) (PEDOT), polypyrrole, or polyaniline.

[0175] The cathode 120 can be made, for example, of a conductor having a low work function to aid in electron injection, and can be made of, for example, of a metal, metal oxide, or conductive polymer. The cathode 120 can be made of metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; or of multilayer materials such as LiF / Al, LiO2 / Al, LiF / Ca, or BaF2 / Ca.

[0176] The light-emitting layer 130 may contain the compounds or compositions described above for organic optoelectronic devices. The light-emitting layer 130 may also contain another organic compound as a mixed host. The light-emitting layer 130 may also contain the light-emitting dopants described above, and may contain fluorescent dopants, phosphorescent photosensitizers, or combinations thereof as described above.

[0177] In one implementation, by combining the aforementioned compound or composition for organic optoelectronic devices with a light-emitting dopant, the light-emitting layer 130 can emit light in a blue light emission spectrum. The peak wavelength of the blue light emission spectrum can be, for example, between about 410 nm and 480 nm, and within this range, it can be, for example, between about 420 nm and 470 nm or between about 430 nm and 470 nm. In one implementation, at least one of the first compound and the aforementioned second compound in the composition for organic optoelectronic devices can have a higher triplet energy level, thereby facilitating exciton transfer to the blue light-emitting dopant, thus enabling the realization of a high-efficiency, long-lifetime organic optoelectronic device.

[0178] The compounds described above for use in organic optoelectronic devices can improve the stability of the material during device operation and improve lifetime and drive voltage by helping to transfer the LUMO group (the LUMO part in the molecule) to the additionally linked phenyl group.

[0179] In one implementation, the composition for the organic optoelectronic device described above can help improve lifetime by including a first compound and a second compound, thereby helping to further improve the balance of electrons and holes in the light-emitting layer 130 and further improve the luminous efficiency, while reducing unbound charges caused by the imbalance of electron and hole mobility. The first compound can be a bipolar compound with relatively strong hole transport characteristics, and the second compound can be a bipolar compound with relatively strong electron transport characteristics.

[0180] In one implementation, the organic optoelectronic device 100 includes a light-emitting layer 130 in which an organic optoelectronic device composition can be applied as a hybrid host. By helping to finely control the holes and electrons injected from the anode 110 and the cathode 120 respectively to have suitable mobility within the light-emitting layer 130, exciton generation is strongly induced within the light-emitting layer 130, which can help enhance the luminous efficiency in the light-emitting layer 130.

[0181] In one implementation, the difference in mobility of holes and electrons injected from the anode 110 and cathode 120 within the light-emitting layer 130 can help reduce or prevent the generation of excitons at inappropriate locations, such as at the interface between the light-emitting layer 130 and adjacent layers, or reduce or prevent the accumulation of unbound charges at the interface between the light-emitting layer 130 and adjacent layers. Therefore, the roll-off phenomenon in which the luminous efficiency of the organic optoelectronic device 100 rapidly decreases due to non-luminescent excitons or unbound charges can be reduced or prevented, and thus the lifetime of the organic optoelectronic device 100 can ultimately be improved.

[0182] Organic optoelectronic devices 100 can be produced by forming an anode 110 or a cathode 120 on a substrate, forming a light-emitting layer 130 using dry film deposition methods such as vacuum evaporation, sputtering, plasma deposition and ion deposition, and forming a cathode 120 or an anode 110 thereon.

[0183] Figure 2 This is a cross-sectional view showing another embodiment of an organic light-emitting diode, which is an embodiment of an organic optoelectronic device according to some exemplary embodiments.

[0184] refer to Figure 2 Similar to the embodiments described above, the organic optoelectronic device 200 according to embodiments of the present invention may include, for example, an anode 110, a cathode 120, and a light-emitting layer 130. However, unlike the embodiments described above, according to... Figure 2 The organic optoelectronic device 200 of the embodiment shown also includes, for example, a hole transport layer 140, a hole transport auxiliary layer 150, and an electron transport layer 160.

[0185] Hole transport layer 140 may be located, for example, between anode 110 and light-emitting layer 130, and hole transport auxiliary layer 150 may be located, for example, between light-emitting layer 130 and hole transport layer 140. Electron transport layer 160 may be located, for example, between cathode 120 and light-emitting layer 130.

[0186] Hole transport layer 140 can assist in the transport of holes from anode 110 to light-emitting layer 130, and may include, for example, an amine compound. In one implementation, the amine compound may have at least one aryl or heteroaryl group that has hole-carrying properties. In one implementation, the amine compound may be represented by chemical formula 6A or 6B.

[0187] [Chemical Formula 6A] [Chemical Formula 6B]

[0188] In chemical formula 6A or 6B, Ar a To Ar g Each can be, independently, for example, hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof.

[0189] Ar a To Ar c At least one of them and Ar d To Ar g At least one of them may be, for example, a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof.

[0190] Ar h It can be, for example, a single bond, a substituted or unsubstituted C1 to C20 alkylene group, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof.

[0191] By being located between and in contact with the hole transport layer 140 and the light-emitting layer 130, the hole transport auxiliary layer 150 can form an interface with the light-emitting layer 130. The hole transport auxiliary layer 150 can help further reduce or prevent the generation of excitons at inappropriate locations, such as the interface between the light-emitting layer 130 and adjacent layers, or further reduce or prevent the accumulation of unbound charges at the interface between the light-emitting layer 130 and adjacent layers. Therefore, the roll-off phenomenon, where the luminous efficiency of the organic optoelectronic device 100 rapidly decreases due to non-luminescent excitons or unbound charges, can be further reduced or prevented, and thus the lifetime of the organic optoelectronic device 100 can be further improved.

[0192] The electron transport layer 160 can help further improve electron injection or electron migration between the cathode 120 and the light-emitting layer 130 and block holes.

[0193] The electron transport layer 160 may contain one or more compounds, such as those in group 3.

[0194] [Group 3]

[0195] Organic optoelectronic devices, including the aforementioned organic light-emitting diodes, can be applied to display devices.

[0196] The following embodiments and comparative examples are provided to highlight the characteristics of one or more implementations; however, it will be understood that the embodiments and comparative examples should not be construed as limiting the scope of the implementations, nor should the comparative examples be construed as being outside the scope of the implementations. Furthermore, it will be understood that the implementations are not limited to the specific details described in the embodiments and comparative examples.

[0197] Unless otherwise specified, 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.

[0198] Preparation of compounds for organic optoelectronic devices

[0199] As a more specific embodiment of the compound of the present invention, the provided compound is synthesized through the following steps.

[0200] (Synthesis of the first compound)

[0201] Synthesis Example 1: Synthesis of Compound H-2

[0202] [Reaction Formula 1]

[0203] Step 1: Synthesis of compound H-2-1

[0204] 2-Fluoro-1,1':3',1''-terphenyl (15 g, 60.4 mmol), 2-bromo-9H-carbazole (14.9 g, 60.4 mmol), and cesium carbonate (49.2 g, 151.0 mmol) were added to 302 mL of N-methyl-2-pyrrolidone, and the mixture was stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid. The solid was filtered under reduced pressure and purified by column chromatography to obtain 17.5 g (yield: 61.0%) of intermediate H-2-1.

[0205] Step 2: Synthesis of compound H-2

[0206] 17.5 g (36.9 mmol) of intermediate H-2-1, 12.3 g (36.9 mmol) of 9H-3,9'-bicarbazole, 1.7 g (1.8 mmol) of tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3), 4.3 g (44.3 mmol) of sodium tert-butoxide (NaOtBu) and 1.1 g (5.5 mmol) of tris(tert-butyl)phosphine (P(tBu)3) were added to 184 mL of toluene, and the mixture was stirred under reflux for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 21.7 g (29.9 mmol, 81.0%) of compound H-2.

[0207] Synthesis Example 2: Synthesis of Compound H-62

[0208] [Reaction 2]

[0209] Step 1: Synthesis of intermediate H-62-1

[0210] 2-Fluoro-1,1':3',1''-terphenyl-2',2'',3,3'',4,4',4'',5,5',5'',6,6',6''-d13 (12 g, 45.9 mmol), 2-bromo-9H-carbazole-1,3,4,5,6,7,8-d7 (11.6 g, 45.9 mmol), and cesium carbonate (37.4 g, 114.8 mmol) were added to 230 mL of N-methyl-2-pyrrolidone, and then stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid. The solid was filtered under reduced pressure and purified by column chromatography to obtain 15.2 g (yield: 67.0%) of intermediate H-62-1.

[0211] Step 2: Synthesis of compound H-62

[0212] 15.2 g (30.7 mmol) of intermediate H-62-1, 10.7 g (30.7 mmol) of 9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15, tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3) (1.4 g, 1.5 mmol), sodium tert-butoxide (NaOtBu) (3.5 g, 36.9 mmol), and tris(tert-butyl)phosphine (P(tBu)3) (0.9 g, 4.6 mmol) were added to 154 mL of toluene, and the mixture was stirred under reflux for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 18.5 g (24.3 mmol, 79.0%) of compound H-62.

[0213] Synthesis Example 3: Synthesis of Compound H-5

[0214] [Reaction 3]

[0215] Step 1: Synthesis of intermediate H-5-1

[0216] 10 g (30.8 mmol) of 2'-fluoro-1,1':3',1'':3'',1'''-tetraphenyl (2'-fluoro-1,1':3',1'''-tetraphenyl) 7.6 g (30.8 mmol) of 2'-bromo-9H-carbazole 1'- and 25.1 g (77.1 mmol) of cesium carbonate were added to 154 mL of N-methyl-2-pyrrolidone and stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid. The solid was filtered under reduced pressure and purified by column chromatography to obtain 9.8 g (yield: 58.0%) of intermediate H-5-1.

[0217] Step 2: Synthesis of compound H-5

[0218] 9.8 g (17.8 mmol) of intermediate H-5-1, 5.9 g (17.8 mmol) of 9H-3,9'-bicarbazole, 0.8 g (0.9 mmol) of tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3), sodium tert-butoxide (NaOtBu) (2.1 g, 21.4 mmol) and tris(tert-butyl)phosphine (P(tBu)3) (0.5 g, 2.7 mmol) were added to 89 mL of toluene, and the mixture was refluxed and stirred for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 10.3 g (12.8 mmol, 72.0%) of compound H-5.

[0219] Synthesis Example 4: Synthesis of Compound H-71

[0220] [Reaction 4]

[0221] Step 1: Synthesis of intermediate H-71-1

[0222] 2'-Fluoro-1,1':3',1'':3'',1'''-Tetraphenyl-2,2'',2''',3,3''',4,4',4'',4''',5,5',5'',5''',6,6',6'',6'''-d17 (12 g, 35.1 mmol), 2-Bromo-9H-Carbazole-1,3,4,5,6,7,8-d7 (8.9 g, 35.1 mmol), and cesium carbonate (28.6 g, 87.8 mmol) were added to 176 mL of N-methyl-2-pyrrolidone, and then stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid. The solid was filtered under reduced pressure and purified by column chromatography to obtain 12.3 g (yield: 61.0%) of intermediate H-71-1.

[0223] Step 2: Synthesis of compound H-71

[0224] 12.3 g (21.4 mmol) of intermediate H-71-1, 7.4 g (21.4 mmol) of 9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15, tris(dibenzylacetone)dipalladium(0) (Pd2(dba)3) (1.0 g, 1.1 mmol), sodium tert-butoxide (NaOtBu) (2.5 g, 25.7 mmol), and tris(tert-butyl)phosphine (P(tBu)3) (0.6 g, 3.2 mmol) were added to 107 mL of toluene, and the mixture was stirred under reflux for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 13.9 g (16.5 mmol, 77.0%) of compound H-71.

[0225] Synthesis Example 5: Synthesis of Compound A-100 (Dn=28)

[0226] [Reaction 5]

[0227] (2-(9H-carbazole-9-yl-d8)phenyl-3,4,5,6-d4)boronic acid (10 g, 33.4 mmol), 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (15.4 g, 33.4 mmol), Pd(PPh3)4 (1.9 g, 1.7 mmol), and potassium carbonate (K2CO3) (13.9 g, 100.3 mmol) were added to 111 mL THF and 56 mL DIW, and then refluxed and stirred for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 20.7 g (yield: 91.0%) of compound A-100 (Dn=28).

[0228] Synthesis Example 6: Synthesis of Compound A-92 (Dn=35)

[0229] [Reaction Formula 6]

[0230] Step 1: Synthesis of intermediate A-92-1

[0231] (3-Bromophenyl-2,4,5,6-d4)tris(phenyl-d5)silane (15.0 g, 34.5 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bismuth(1,3,2-dihexaoxopentaborane) (B2Pin2) (11.4 g, 44.9 mmol), [1,1'-bis(diphenylphosphine)ferrocene]dichloropalladium(II) (Pd(dppf)Cl2) (1.4 g, 1.7 mmol), and potassium acetate (KOAc) (10.2 g, 103.6 mmol) were added to 173 mL of xylene, and the mixture was refluxed and stirred for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 10.5 g (yield: 63.0%) of intermediate A-92-1.

[0232] Step 2: Synthesis of compound A-92 (Dn=35)

[0233] Intermediate A-92-1 (10.5 g, 21.8 mmol), 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (10.1 g, 21.8 mmol), Pd(PPh3)4 (1.3 g, 1.1 mmol), and potassium carbonate (K2CO3) (9.0 g, 65.4 mmol) were added to 73 mL THF and 36 mL DIW, and then refluxed and stirred for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 15.0 g (yield: 88.0%) of compound A-92 (Dn=35).

[0234] Comparative Synthesis Example 1: Synthesis of Compound R-1

[0235] [Reaction Formula 7]

[0236] Step 1: Synthesis of intermediate R-1-1

[0237] 3-Fluoro-1,1':3',1''-terphenyl (15 g, 60.4 mmol), 2-bromo-9H-carbazole (14.9 g, 60.4 mmol), and cesium carbonate (49.2 g, 151.0 mmol) were added to 302 mL of N-methyl-2-pyrrolidone, and the mixture was stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid. The solid was filtered under reduced pressure and purified by column chromatography to obtain 21.5 g (yield: 75.0%) of intermediate R-1-1.

[0238] Step 2: Synthesis of compound R-1

[0239] 21.5 g (45.3 mmol) of intermediate R-1-1, 15.1 g (45.3 mmol) of 9H-3,9'-bicarbazole, tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3) (2.1 g, 2.3 mmol), sodium tert-butoxide (NaOtBu) (5.2 g, 54.4 mmol), and tris(tert-butyl)phosphine (P(tBu)3) (1.4 g, 6.8 mmol) were added to 227 mL of toluene, and the mixture was refluxed and stirred for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 25.7 g (35.3 mmol, 78.0%) of compound R-1.

[0240] Comparative Synthesis Example 2: Synthesis of Compound R-2

[0241] [Reaction Equation 8]

[0242] Step 1: Synthesis of intermediate R-2-1

[0243] 2-Fluoro-1,1':3',1''-terphenyl (15 g, 60.4 mmol), 3-bromo-9H-carbazole (14.9 g, 60.4 mmol), and 49.2 g (151.0 mmol) of cesium carbonate were added to 302 mL of N-methyl-2-pyrrolidone, and then stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid. The solid was filtered under reduced pressure and purified by column chromatography to obtain 18.3 g (yield: 64.0%) of intermediate R-2-1.

[0244] Step 2: Synthesis of compound R-2

[0245] 18.3 g (38.6 mmol) of intermediate R-2-1, 12.8 g (38.6 mmol) of 9H-3,9'-bicarbazole, and tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3) (1.8 g, 1.9 mmol), sodium tert-butoxide (NaOtBu) (4.4 g, 46.3 mmol), and tris(tert-butyl)phosphine (P(tBu)3) (1.2 g, 5.5 mmol) were added to 193 mL of toluene, and the mixture was stirred under reflux for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 23.5 g (32.4 mmol, 84.0%) of compound R-2.

[0246] Comparative Synthesis Example 3: Synthesis of Compound R-3

[0247] [Reaction Formula 9]

[0248] Step 1: Synthesis of compound R-3

[0249] 2'-fluoro-1,1':3',1'':3'',1'''-tetraphenyl (11 g, 33.9 mmol), 9H-3,9'-bicarbazole (11.3 g, 33.9 mmol), and cesium carbonate (27.6 g, 84.8 mmol) were added to 170 mL of N-methyl-2-pyrrolidone, and the mixture was stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid. The solid was filtered under reduced pressure and purified by column chromatography to obtain 13.4 g (21.0 mmol, 62.0%) of compound R-3.

[0250] Comparative Synthesis Example 4: Synthesis of Compound R-4

[0251] [Reaction Formula 10]

[0252] Step 1: Synthesis of intermediate R-4-1

[0253] 5'-bromo-1,1':3',1''-terphenyl (13.0 g, 42.0 mmol), 1-fluoro-9H-carbazole (7.8 g, 42.0 mmol), tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3) (1.9 g, 2.1 mmol), sodium tert-butoxide (NaOtBu) (4.8 g, 50.5 mmol), and tris(tert-butyl)phosphine (P(tBu)3) (1.3 g, 6.3 mmol) were added to 210 mL of toluene, and the mixture was stirred under reflux for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 12.2 g (yield: 70.0%) of intermediate R-4-1.

[0254] Step 2: Synthesis of compound R-4

[0255] 12.2 g (29.5 mmol) of intermediate R-4-1, 9.8 g (29.5 mmol) of 9H-3,9'-bicarbazole, and 24.0 g (73.8 mmol) of cesium carbonate were added to 148 mL of N-methyl-2-pyrrolidone, and the mixture was stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid. The solid was filtered under reduced pressure and purified by column chromatography to obtain 8.8 g (12.1 mmol, 41.0%) of compound R-4.

[0256] Comparative Synthesis Example 5: Synthesis of Compound R-5

[0257] [Reaction Formula 11]

[0258] Step 1: Synthesis of intermediate R-5-1

[0259] 5'-fluoro-1,1':3',1''-terphenyl (15 g, 60.4 mmol), 2-bromo-9H-carbazole (14.9 g, 60.4 mmol), and 49.2 g (151.0 mmol) of cesium carbonate were added to 302 mL of N-methyl-2-pyrrolidone, and then stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid, which was filtered under reduced pressure and purified by column chromatography to obtain 22.1 g (yield: 77.0%) of intermediate R-5-1.

[0260] Step 2: Synthesis of compound R-5

[0261] 22.1 g (46.6 mmol) of intermediate R-5-1, 15.5 g (46.6 mmol) of 9H-3,9'-bicarbazole, tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3) (2.1 g, 2.3 mmol), sodium tert-butoxide (NaOtBu) (5.4 g, 55.9 mmol), and tris(tert-butyl)phosphine (P(tBu)3) (1.4 g, 7.0 mmol) were added to 233 mL of toluene, and the mixture was stirred under reflux for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 25.7 g (35.4 mmol, 76.0%) of compound R-5.

[0262] Comparative Synthesis Example 6: Synthesis of Compound R-6

[0263] [Reaction 12]

[0264] Step 1: Synthesis of intermediate R-6-1

[0265] 5'-fluoro-1,1':3',1''-terphenyl (15 g, 60.4 mmol), 4-bromo-9H-carbazole (14.9 g, 60.4 mmol), and cesium carbonate (49.2 g, 151.0 mmol) were added to 302 mL of N-methyl-2-pyrrolidone, and the mixture was stirred at 180 °C for 18 hours. After cooling to ambient temperature, water was added to produce a solid. The solid was filtered under reduced pressure and purified by column chromatography to obtain 20.3 g (yield: 71.0%) of intermediate R-6-1.

[0266] Step 2: Synthesis of compound R-6

[0267] 20.3 g (42.8 mmol) of intermediate R-6-1, 14.2 g (42.8 mmol) of 9H-3,9'-bicarbazole, tris(dibenzylacetone)dipalladium(O) (Pd2(dba)3) (2.0 g, 2.1 mmol), sodium tert-butoxide (NaOtBu) (4.9 g, 51.3 mmol), and tris(tert-butyl)phosphine (P(tBu)3) (1.3 g, 6.4 mmol) were added to 214 mL of xylene, and the mixture was refluxed and stirred for 12 hours. When the reaction was complete, the product was purified by column chromatography (dichloromethane:n-hexane) to obtain 18.0 g (24.8 mmol, 58.0%) of compound R-6.

[0268] Production of organic light-emitting diodes (OLEDs)

[0269] Example 1

[0270] The glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with isopropanol, acetone, or methanol and dried. It was then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes before being transferred to a vacuum depositor. Using the prepared ITO transparent electrode as the anode, compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form a 100 Å thick hole injection layer. Compound A was then deposited on the hole injection layer to a thickness of 600 Å to form a hole transport layer. mCP (1,3-bis(carbazole-9-yl)benzene) was deposited on the hole transport layer to a thickness of 100 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compounds H-2 (host) and P31 (dopant) obtained in Example 1 were vacuum deposited to form a 400 Å thick luminescent layer. Subsequently, BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) was deposited on the luminescent layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound B and LiQ were simultaneously vacuum-deposited in a 1:1 weight ratio to form a 300 Å thick electron transport layer. An organic light-emitting diode was then produced by sequentially vacuum-depositing 10 Å of LiQ and 1,200 Å of Al on the electron transport layer to form a cathode.

[0271] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazole-2-amine

[0272] Compound B: 8-{4-[bis(naphthyl-2-yl)-1,3,5-triazin-2-yl]phenyl}quinoline

[0273] Example 2 and Comparative Examples 1 to 6

[0274] Each organic light-emitting diode of Example 2 and Comparative Examples 1-6 was produced in the same manner as in Example 1, except that compound H-2, which serves as the host of the light-emitting layer, was changed to the compound described in Table 1.

[0275] Production of Organic Light Emitting Diode II

[0276] Example 3

[0277] Glass substrates coated with ITO (indium tin oxide) films were ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrates were ultrasonically cleaned with isopropanol, acetone, or methanol and dried. They were then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes before being transferred to a vacuum depositor. Using the prepared ITO transparent electrode as the anode, compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form a 100 Å thick hole injection layer. Compound A was then deposited on the hole injection layer to a thickness of 600 Å to form a hole transport layer. mCP was deposited on the hole transport layer to a thickness of 100 Å to form a hole transport auxiliary layer. On the hole transport assist layer, compound H-2 obtained in Synthesis Example 1 and compound A-100 (Dn=28) obtained in Synthesis Example 5 were used simultaneously as the host, doped with 13 wt% P31 as a phosphorescent photosensitizer and 1.5 wt% D3 as a fluorescent dopant to form a 400 Å thick emitting layer by vacuum deposition. In this study, compound H-2 and compound A-100 (Dn=28) were used in a weight ratio of 60:40. Subsequently, BCP was deposited on the emitting layer to a thickness of 50 Å to form an electron transport assist layer, and compound B and LiQ were simultaneously vacuum deposited in a 1:1 weight ratio to form a 300 Å thick electron transport layer. An organic light-emitting diode was produced by sequentially vacuum depositing 10 Å of LiQ and 1,200 Å of Al on the electron transport layer to form a cathode.

[0278] Organic light-emitting diodes were produced with the following structure: ITO / compound A (3% NDP-9 doped, 100 Å) / compound A (600 Å) / mCP (100 Å) / EML [body (compound H-2: compound A-100 (Dn=28)): P31: D3=85.5wt%: 13wt%: 1.5wt%] (400 Å) / BCP (50 Å) / compound B: LiQ (300 Å) / LiQ (10 Å) / Al (1,200 Å).

[0279] Examples 4 to 10 and Comparative Examples 7 to 12

[0280] Each of the organic light-emitting diodes of Examples 4 to 10 and Comparative Examples 7 to 12 was produced in the same manner as in Example 1, except that the composition according to Example 3 was changed to the composition in Table 2 as the main body of the light-emitting layer.

[0281] evaluate

[0282] The driving voltage and lifetime characteristics of the organic light-emitting diodes according to each embodiment and comparative example were evaluated.

[0283] The specific measurement methods are shown below, and the results are shown in Tables 1 and 2.

[0284] (1) Measure the change in current density based on the voltage change

[0285] While increasing the voltage from 0V to 10V, the current flowing through the unit diode in the obtained organic light-emitting diode was measured using a voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0286] (2) Measure the change in brightness based on voltage changes

[0287] While increasing the voltage of the organic light-emitting diode from 0V to 10V, the brightness was measured using a photometer (Minolta Cs-1000A).

[0288] (3) Measurement of luminous efficiency

[0289] The brightness and current density measured in (1) and (2) above will be used to calculate the same current density (10 mA / cm²). 2 Luminous efficiency (cd / A) at ).

[0290] (4) Measurement of lifespan

[0291] The luminous efficiency (cd / A) of the organic light-emitting diode was measured to be reduced to 95%, while the brightness (cd / m²) was also reduced. 2 Maintain at 2000 cd / m 2 The time.

[0292] Table 1 lists the relative values ​​calculated based on the lifespan measurements from Comparative Example 1.

[0293] Table 2 lists the relative values ​​calculated based on the lifespan measurements from Comparative Example 7.

[0294] (Table 1)

[0295] (Table 2)

[0296] Referring to Tables 1 and 2, the organic light-emitting diodes according to the embodiments show improved luminous efficiency and lifetime characteristics compared to the organic light-emitting diodes according to the comparative examples.

[0297] Some exemplary embodiments may provide compounds for organic optoelectronic devices that can achieve high efficiency and long lifetime characteristics.

[0298] Some exemplary embodiments may provide compositions for organic optoelectronic devices that include compounds for organic optoelectronic devices.

[0299] Some exemplary embodiments may provide organic optoelectronic devices comprising compounds or compositions.

[0300] Some exemplary embodiments may provide a display device including an organic optoelectronic device.

[0301] It can realize organic optoelectronic devices with high efficiency and long lifespan.

[0302] Exemplary embodiments have been disclosed herein, and although specific terminology has been used, it is intended to be used and interpreted in a general and descriptive sense only, and not for limiting purposes. In some instances, it will be apparent to those skilled in the art that, as of the date of filing of this application, features, characteristics, and / or elements described in connection with specific embodiments may be used alone or in combination with features, characteristics, and / or elements described in connection with other embodiments. Therefore, those skilled in the art will understand that various changes in form and detail may be made without departing from the spirit and scope of the invention as set forth in the appended claims.

Claims

1. A compound for use in organic optoelectronic devices, said compound Represented by a combination of chemical formula 1 and chemical formula 2: [Chemical Formula 1] [Chemical Formula 2] In chemical formula 1 and chemical formula 2, Q 1 Q 2 and Q 3 Each is CR independently a Or in chemical formula 2 The connecting carbon at the point, condition Q 1 Q 2 and Q 3 One of them is in chemical formula 2 The connecting carbon at the point of connection, R a and R 1 To R 9 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. Ar 1 It is a substituted or unsubstituted phenyl or a substituted or unsubstituted biphenyl. n1 and n6 are each an independent integer from 1 to 3. n2, n4, n5, n7, and n8 are each an independent integer from 1 to 4. n3 is an integer from 1 to 5. m1 is 0 or 1, and When n1 is 2 or 3, each R 1 Are they the same or different from each other? When n2 is 2, 3, or 4, each R 2 Are they the same or different from each other? When n3 is 2, 3, 4, or 5, each R 3 Are they the same or different from each other? When n4 is 2, 3, or 4, each R 4 Are they the same or different from each other? When n5 is 2, 3, or 4, each R 5 Are they the same or different from each other? When n6 is 2 or 3, each R 6 Are they the same or different from each other? When n7 is 2, 3, or 4, each R 7 They are the same or different from each other, and When n8 is 2, 3, or 4, each R 8 They are the same as or different from each other.

2. The compound for organic optoelectronic devices according to claim 1, wherein: The combination of chemical formula 1 and chemical formula 2 is represented by one of chemical formulas 1-I to 1-III: [Chemical Formula 1-I] [Chemical Formula 1-II] [Chemical Formula 1-III] In chemical formulas 1-I to 1-III R 1 To R 9 Ar 1 n1 to n8 and m1 are the same as those defined in chemical formulas 1 and 2, and R a1 and R a2 Each independently of R in chemical formula 1 a The definitions are the same.

3. The compound for organic optoelectronic devices according to claim 1, wherein: Chemical formula 1 is represented by one of chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In chemical formulas 1-1 to 1-4, Q 1 Q 2 Q 3 R 1 To R 4 R 9 Ar 1 n1 to n4 and m1 are the same as those defined in chemical formula 1.

4. The compound for organic optoelectronic devices according to claim 3, wherein: The combination of chemical formula 1 and chemical formula 2 is represented by one of chemical formula 1-1A, chemical formula 1-1B, or chemical formula 1-1C: [Chemical Formula 1-1A] [Chemical Formula 1-1B] [Chemical Formula 1-1C] In chemical formulas 1-1A, 1-1B, and 1-1C, R 1 To R 4 R 9 Ar 1 n1 to n4 and m1 are the same as those defined in chemical formula 1-1. R 5 To R 8 R a1 and R a2 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl or substituted or unsubstituted C6 to C12 aryl. n5, n7, and n8 are each an independent integer from 1 to 4, and n6 is an integer from 1 to 3.

5. The compound for an organic optoelectronic device according to claim 4, wherein the combination of chemical formula 1 and chemical formula 2 is represented by chemical formula 1-1B.

6. The compound for organic optoelectronic devices according to claim 1, wherein: The compound is a compound of group 1: [Group 1] [H-1] [H-2] [H-3] [H-4] [H-5] [H-6] [H-7] [H-8] [H-9] [H-10] [H-11] [H-12] [H-13] [H-14] [H-15] [H-16] [H-17] [H-18] [H-19] [H-20] [H-21] [H-22] [H-23] [H-24] [H-25] [H-26] [H-27] [H-28] [H-29] [H-30] [H-31] [H-32] [H-33] [H-34] [H-35] [H-36] [H-37] [H-38] [H-39] [H-40] [H-41] [H-42] [H-43] [H-44] [H-45] [H-46] [H-47] [H-48] [H-49] [H-50] [H-51] [H-52] [H-53] [H-54] Dn represents the number of hydrogen atoms replaced by deuterium, and n is an integer between 1 and the maximum possible number of replacements.

7. The compound for an organic optoelectronic device according to claim 6, wherein the compound is deuterium-substituted and is a compound of group 1-1: [Group 1-1] [H-55] [H-56] [H-57] [H-58] [H-59] [H-60] [H-61] [H-62] [H-63] [H-64] [H-65] [H-66] [H-67] [H-68] [H-69] [H-70] [H-71] [H-72] [H-73] [H-74] [H-75] [H-76] [H-77] [H-78] [H-79] [H-80] [H-81] [H-82] [H-83] [H-84] [H-85] [H-86] [H-87] [H-88] [H-89] [H-90] [H-91] [H-92] [H-93] [H-94] [H-95] [H-96] [H-97] [H-98] [H-99] [H-100] [H-101] [H-102] [H-103] [H-104] [H-105] [H-106] [H-107] [H-108] [H-109] [H-110] [H-111] [H-112] [H-113] [H-114] [H-115] [H-116] [H-117] [H-118] [H-119] [H-120] [H-121] [H-122] [H-123] [H-124] [H-125] [H-126] [H-127] [H-128] [H-129] [H-130] [H-131] [H-132] [H-133] [H-134] [H-135] .

8. A composition for use in an organic optoelectronic device, comprising: First compound; and The second compound, in: The first compound is a compound for organic optoelectronic devices according to any one of claims 1 to 7, and The second compound is represented by chemical formula 3: [Chemical Formula 3] In chemical formula 3, Z 1 To Z 3 Each is independently N or CR b The condition is Z 1 To Z 3 At least two of them are N. L 1 To L 3 Each is independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted divalent C2 to C20 heterocyclic group. Ar 2 and Ar 3 Each is independently a substituted or unsubstituted C6 to C30 aryl, a substituted or unsubstituted C2 to C20 heterocyclic, or a substituted or unsubstituted silyl group. R b R 10 and R 11 Each of these elements is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group, or a halogen. m10 and m11 are each an independent integer from 1 to 4, and Each R 10 and R 11 They can exist separately or two adjacent groups can be linked to form a ring.

9. The composition for an organic optoelectronic device according to claim 8, wherein in chemical formula 3, L 1 It is a single key.

10. The composition for an organic optoelectronic device according to claim 8, wherein: The second compound is represented by chemical formula 3a or chemical formula 3b: [Chemical Formula 3a] [Chemical Formula 3b] In chemical formulas 3a and 3b Z 1 To Z 3 L 1 To L 3 m10, m11, R 10 and R 11 The definitions are the same as those for chemical formula 3. R 12 To R 16 Each of these elements is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl group, a cyano group, or a halogen. m12 and m13 are each an independent integer from 1 to 4. m14 to m16 are each an independent integer from 1 to 5, and Each R 12 To R 16 They can exist separately or two adjacent groups can be linked to form a ring.

11. The composition for an organic optoelectronic device according to claim 10, wherein: L 1 It's a single key. L 2 It is a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted bitriphenylene, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted carbazolyl. L 3 It is a single-bonded, substituted, or unsubstituted phenylene, and Ar 3 It is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazoyl, or a substituted or unsubstituted triphenylsilyl.

12. The composition for an organic optoelectronic device according to claim 8, wherein at least one of the first compound and the second compound is substituted with one or more deuterium atoms.

13. An organic optoelectronic device, comprising: The anode and cathode facing each other, and The organic layer located between the anode and the cathode, The organic layer includes The compound for an organic optoelectronic device according to any one of claims 1 to 7; or The composition for an organic optoelectronic device according to any one of claims 8 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 includes the compound for organic optoelectronic devices or the composition for organic optoelectronic devices.

15. The organic optoelectronic device of claim 14, wherein the light-emitting layer further comprises a fluorescent dopant, a phosphorescent photosensitizer, or a combination thereof.

16. A display device comprising an organic optoelectronic device according to any one of claims 13 to 15.

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