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

Abstract

The present invention relates to a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device, wherein the composition comprises a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2. The details of chemical formula 1 and chemical formula 2 are as defined in the specification.

Description

Composition for organic optoelectronic devices, organic optoelectronic devices, and display devices

[0001] This relates to a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device.

[0002] An organic optoelectronic diode is a device capable of converting electrical energy and light energy.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles. One is a photovoltaic device that generates electrical energy as excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

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

[0005] Among these, organic light-emitting diodes (OLEDs) have recently been receiving significant attention due to the increasing demand for flat panel display devices. As an organic light-emitting diode is a device that converts electrical energy into light, its performance is greatly influenced by the organic material located between the electrodes.

[0006] One embodiment provides a composition for an organic optoelectronic device that can lower the driving voltage and realize a high-efficiency and long-life organic optoelectronic device.

[0007] Another embodiment provides an organic optoelectronic device comprising the above composition for the organic optoelectronic device.

[0008] Another embodiment provides a display device including the above-mentioned organic optoelectronic element.

[0009] According to one embodiment, a composition for an organic optoelectronic device is provided, comprising a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] R 1 to R 9 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group or substituted or unsubstituted C6 to C20 aryl group, and

[0014] m1 to m9 are each independently one of integers 1 to 4, and

[0015] When m1 to m9 are integers greater than or equal to 2, each R 1 to R 9 They are identical or different from each other;

[0016] [Chemical Formula 2]

[0017]

[0018] In the above chemical formula 2,

[0019] L 1 and L 2 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0020] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0021] R 11 and R 14Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and

[0022] m11 and m12 are each independently one of integers 1 to 4, and

[0023] If m11 and m12 are 2 or more, respectively R 11 and R 12 They are identical or different from each other.

[0024] According to another embodiment, an organic optoelectronic device is provided comprising an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises a composition for the organic optoelectronic device.

[0025] According to another embodiment, a display device comprising the organic optoelectronic element is provided.

[0026] It is possible to realize high-efficiency, long-life organic optoelectronic devices while lowering the driving voltage.

[0027] FIG. 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0028] <Explanation of Symbols>

[0029] 100: Organic light-emitting diode

[0030] 105: Organic layer

[0031] 110: Cathode

[0032] 120: Anode

[0033] 130: Emissive layer

[0034] 140: Precision Transport Area

[0035] 150: Electronic transport area

[0036]

[0037] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention, and the present invention is defined only by the scope of the claims set forth below.

[0038] In this specification, "substitution" means that, unless otherwise defined, at least one hydrogen of a substituent or compound is substituted with a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0039] In one example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. Furthermore, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C20 aryl group, a C2 to C20 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C18 aryl group, a C2 to C18 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a trimethylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0040] In this specification, “non-substituted” means that a hydrogen atom remains a hydrogen atom without being substituted by another substituent.

[0041] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0042] In this specification, "hetero" means, unless otherwise defined, that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder is carbon.

[0043] In this specification, "aryl group" is a collective concept for a group having one or more hydrocarbon aromatic moietys, including a form in which all elements of the hydrocarbon aromatic moiety have p-orbitals and these p-orbitals form a conjugation, such as a phenyl group, a naphthyl group, etc., and a form in which two or more hydrocarbon aromatic moietys are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moietys are directly or indirectly fused, such as a fluorenyl group, etc.

[0044] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0045] In this specification, "heterocyclic group" is a superordinate concept including heteroaryl groups, meaning that a cyclic compound, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C). If the heterocyclic group is a fused ring, it may contain one or more heteroatoms in the entire heterocyclic group or in each ring.

[0046] For example, a "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si within the aryl group. Two or more heteroaryl groups may be directly connected through sigma bonds, or if the heteroaryl group comprises two or more rings, the two or more rings may be fused together. If the heteroaryl group is a fused ring, each ring may contain one to three heteroatoms.

[0047] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0048] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic groups are a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazoleyl group, a substituted or unsubstituted triazoleyl group, a substituted or unsubstituted oxazoleyl group, a substituted or unsubstituted thiazoleyl group, a substituted or unsubstituted oxadiazoleyl group, a substituted or unsubstituted thiadiazoleyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazoleyl group, a substituted or unsubstituted indoleyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthiridinyl group, a substituted or unsubstituted benzoxazine dil group, a substituted or unsubstituted benzthiazine dil group, a substituted or unsubstituted acrridinyl group, a substituted or unsubstituted phenazine dil group, a substituted or unsubstituted phenothiazine dil group, a substituted or unsubstituted phenoxazine dil group, a substituted or unsubstituted carbazole dil group, a substituted or unsubstituted dibenzofuran dil group, a substituted or unsubstituted dibenzothiophen dil group, a substituted or unsubstituted benzonaphtufuran dil group, a substituted or unsubstituted benzonaphthiophen dil group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0049] In this specification, the term "hole characteristic" refers to a characteristic that can form holes by donating electrons when an electric field is applied, and means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and movement within the light-emitting layer by having a conduction characteristic along the HOMO level.

[0050] In addition, electronic properties refer to the ability to receive electrons when an electric field is applied, and they refer to properties that facilitate the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed at the light-emitting layer to the cathode, and the movement of electrons within the light-emitting layer by having conduction properties along the LUMO level.

[0051] A composition for an organic optoelectronic device according to one embodiment is described below.

[0052] A composition for an organic optoelectronic device according to one embodiment comprises a first compound represented by the following chemical formula 1 and a second compound represented by the following chemical formula 2.

[0053] [Chemical Formula 1]

[0054]

[0055] In the above chemical formula 1,

[0056] R 1 to R 9 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group or substituted or unsubstituted C6 to C20 aryl group, and

[0057] m1 to m9 are each independently one of integers 1 to 4, and

[0058] When m1 to m9 are integers greater than or equal to 2, each R 1 to R 9 They are identical or different from each other;

[0059] [Chemical Formula 2]

[0060]

[0061] In the above chemical formula 2,

[0062] L 1 and L 2 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and

[0063] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0064] R 11 and R 14 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and

[0065] m11 and m12 are each independently one of integers 1 to 4, and

[0066] If m11 and m12 are 2 or more, respectively R 11 and R 12 They are identical or different from each other.

[0067] The first compound represented by the above chemical formula 1 is a carbazole in which all three substituents connected to the triazine are substituted on ortho-phenylene. By substituting the carbazole at the ortho-position to have steric hindrance, a low LUMO energy region and a small ΔEst are induced, and the relaxation route of excitons due to steric hindrance is prevented, thereby enabling high efficiency and a long lifespan.

[0068] In addition, by combining it with an indolocarbazole compound represented by Chemical Formula 2, the driving voltage can be lowered while further improving the lifespan characteristics.

[0069] As an example, R of the above chemical formula 1 1 to R 3 Each may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C1 to C6 alkylsilyl group, a substituted or unsubstituted C6 to C12 arylsilyl group, or a substituted or unsubstituted C6 to C18 aryl group.

[0070] As a specific example, the above R 1 to R 3 Each may independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0071] As an example, R of the above chemical formula 1 4 to R 9 Each may independently be hydrogen, deuterium, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C1 to C6 alkylsilyl group, a substituted or unsubstituted C6 to C12 arylsilyl group, or a substituted or unsubstituted C6 to C18 aryl group.

[0072] As a specific example, the above R 4 to R 9 Each may independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

[0073] In one embodiment, the R 1 to R 3 Each can independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0074] In one embodiment, the R 4 to R 9 Each may independently be hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted triphenylene group.

[0075] In a specific embodiment, the above chemical formula 1 may be represented by one of the following chemical formulas 1A to 1I.

[0076] [Chemical Formula 1A]

[0077]

[0078] [Chemical Formula 1B]

[0079]

[0080] [Chemical Formula 1C]

[0081]

[0082] [Chemical Formula 1D]

[0083]

[0084] [Chemical Formula 1E]

[0085]

[0086] [Chemical Formula 1F]

[0087]

[0088] [Chemical Formula 1G]

[0089]

[0090] [Chemical Formula 1H]

[0091]

[0092] [Chemical Formula 1I]

[0093]

[0094] In Chemical Formulas 1A to 1I, m1 to m9 are as described above, and

[0095] R 1 to R 9 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C18 aryl group, and

[0096] Ar 3 It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted triphenylene group.

[0097] In the most specific embodiment, the first compound may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[0098] [Group 1]

[0099] [A-1] [A-2] [A-3] [A-4]

[0100]

[0101] [A-5] [A-6] [A-7] [A-8]

[0102]

[0103] [A-9] [A-10] [A-11] [A-12]

[0104]

[0105] [A-13] [A-14] [A-15] [A-16]

[0106]

[0107] [A-17] [A-18] [A-19] [A-20]

[0108]

[0109] [A-21] [A-22] [A-23] [A-24]

[0110]

[0111] [A-25] [A-26] [A-27] [A-28]

[0112]

[0113] [A-29] [A-30] [A-31] [A-32]

[0114]

[0115] [A-33] [A-34] [A-35] [A-36]

[0116]

[0117] [A-37] [A-38] [A-39] [A-40]

[0118]

[0119] [A-41] [A-42] [A-43] [A-44]

[0120]

[0121] [A-45] [A-46] [A-47] [A-48]

[0122]

[0123] [A-49] [A-50] [A-51] [A-52]

[0124]

[0125] [A-52] [A-53] [A-54] [A-55]

[0126]

[0127] [A-56] [A-57] [A-59] [A-60]

[0128]

[0129] [A-61] [A-62] [A-63] [A-64]

[0130]

[0131] [A-65] [A-66] [A-67] [A-68]

[0132]

[0133] [A-69] [A-70] [A-71] [A-72]

[0134]

[0135] [A-73] [A-74] [A-75] [A-76]

[0136]

[0137] [A-77] [A-78] [A-79] [A-80]

[0138]

[0139] [A-81] [A-82] [A-83] [A-84]

[0140]

[0141] [A-85] [A-86] [A-87] [A-88]

[0142]

[0143] [A-89] [A-90] [A-91] [A-92]

[0144]

[0145] [A-93] [A-94] [A-95] [A-96]

[0146]

[0147] [A-97] [A-98] [A-99] [A-100]

[0148]

[0149] [A-101] [A-102] [A-103] [A-104]

[0150]

[0151] [A-105] [A-106] [A-107] [A-108]

[0152]

[0153] [A-109] [A-110] [A-111] [A-112]

[0154]

[0155] [A-113] [A-114] [A-115] [A-116]

[0156]

[0157] [A-117] [A-118] [A-119] [A-120]

[0158]

[0159] [A-121] [A-122] [A-123] [A-124]

[0160]

[0161] [A-125] [A-126] [A-127] [A-128]

[0162]

[0163] [A-129] [A-130] [A-131] [A-132]

[0164]

[0165] [A-133] [A-134] [A-135] [A-136]

[0166]

[0167] [A-137] [A-138] [A-139] [A-140]

[0168]

[0169] [A-141] [A-142] [A-143] [A-144]

[0170]

[0171] [A-145] [A-146] [A-147] [A-148]

[0172]

[0173] [A-149] [A-150] [A-151] [A-152]

[0174]

[0175] [A-152] [A-153] [A-154] [A-155]

[0176]

[0177] [A-156] [A-157] [A-158]

[0178]

[0179] Dn means the number of deuterium substitutions, where n means a number greater than or equal to 1 and less than or equal to the maximum number of substitutions possible.

[0180] As an example, L of the above chemical formula 2 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted phenylene group.

[0181] As an example, Ar of the above chemical formula 2 1 and Ar 2 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0182] As a specific example, Ar of the above chemical formula 2 1 and Ar 2 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted triphenylene group.

[0183] As an example, R of the above chemical formula 2 11 to R 14 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0184] As a specific example, R of the above chemical formula 2 11 to R 14 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, or substituted or unsubstituted carbazole group.

[0185] For example, the above L1 -Ar 1 and L 2 -Ar 2 Each can be independently one of the substituents listed in Group I below.

[0186] [Group I]

[0187]

[0188] In the above Group I,

[0189] R 15 to R 20 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[0190] m13 is one of integers from 1 to 5, and

[0191] m14 is one of integers from 1 to 4, and

[0192] m15 is one of integers from 1 to 3, and

[0193] m16 is an integer of 1 or 2, and

[0194] m17 is one of integers from 1 to 7, and

[0195] * is a connection point.

[0196] The second compound mentioned above can be used in the light-emitting layer together with the first compound to increase charge mobility and stability, thereby improving luminous efficiency and lifespan characteristics.

[0197] In the most specific embodiment, the second compound may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0198] [Group 2]

[0199] [C-1] [C-2] [C-3] [C-4]

[0200]

[0201] [C-5] [C-6] [C-7] [C-8]

[0202]

[0203] [C-9] [C-10] [C-11] [C-12]

[0204]

[0205] [C-13] [C-14] [C-15] [C-16]

[0206]

[0207] [C-17] [C-18] [C-19] [C-20]

[0208]

[0209] [C-21] [C-22] [C-23] [C-24]

[0210]

[0211] [C-25] [C-26] [C-27] [C-28]

[0212]

[0213] [C-29] [C-30] [C-31] [C-32]

[0214]

[0215] [C-33] [C-34] [C-35] [C-36]

[0216]

[0217] [C-37] [C-38] [C-39] [C-40]

[0218]

[0219] [C-41] [C-42] [C-43] [C-44]

[0220]

[0221] [C-45] [C-46] [C-47] [C-48]

[0222]

[0223] [C-49] [C-50] [C-51] [C-52]

[0224]

[0225] [C-53] [C-54] [C-55] [C-56]

[0226]

[0227] Additionally, an example of a form in which at least one hydrogen in compounds C-1 to C-56 listed in Group 2 above is substituted with deuterium is presented below, but is not limited thereto.

[0228] [C-57] [C-58] [C-59] [C-60] [C-61]

[0229]

[0230] [C-62] [C-63] [C-64] [C-65] [C-66]

[0231]

[0232] [C-67] ​​[C-68] [C-69] [C-70] [C-71]

[0233]

[0234] (Dn refers to the number of deuterium substitutions, where n represents a number greater than or equal to 1 and less than or equal to the maximum possible substitution number.)

[0235] The most specific structures of compounds C-57 to C-71 of Group 2 above are presented below as examples based on the deuterium substitution positions and substitution rates, and there is no intention to limit the scope of rights for compounds not presented below.

[0236] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds exemplified below, and the deuterium substitution position and deuterium substitution rate, etc., may include all ranges that can be changed within the range of compounds C-1 to C-71.

[0237] [C-72] [C-73]

[0238]

[0239] [C-74] [C-75] [C-76] [C-77]

[0240]

[0241] [C-78] [C-79] [C-80] [C-81]

[0242]

[0243] [C-82] [C-83] [C-84] [C-85]

[0244]

[0245] [C-86] [C-87] [C-88] [C-89]

[0246]

[0247] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By including them within the above range, bipolar characteristics can be realized by adjusting the weight ratio appropriately using the electron transport ability of the first compound and the hole transport ability of the second compound, thereby improving efficiency and lifespan. Within the above range, they may be included in a weight ratio of, for example, about 10:90 to 90:10 or about 20:80 to 80:20, and for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, they may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0248] An organic optoelectronic device to which the composition for an organic optoelectronic device described above is applied is described below.

[0249] Organic optoelectronic devices are not particularly limited as long as they are devices capable of mutually converting electrical energy and light energy, and examples include organic photovoltaic devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0250] Here, an organic light-emitting diode, which is an example of an organic optoelectronic device, is described with reference to the drawing.

[0251] FIG. 1 is a cross-sectional view showing an organic light-emitting device according to one embodiment.

[0252] Referring to FIG. 1, an organic light-emitting device (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other, and an organic layer (105) located between the anode (120) and the cathode (110).

[0253] The anode (120) may be made of a conductor with a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The anode (120) may be a metal or an alloy thereof, such as nickel, platinum, vanadium, chromium, copper, zinc, gold; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole and polyaniline, but is not limited thereto.

[0254] The cathode (110) may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The cathode (110) may be a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc.; or a multilayer structure material such as LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca, but is not limited thereto.

[0255] The organic layer (105) may include the aforementioned composition for organic optoelectronic devices.

[0256] The above organic layer (105) includes a light-emitting layer (130), and the light-emitting layer (130) includes a host and a dopant, the host may include the above-described composition for organic optoelectronic devices, and the dopant may be a green phosphorescent dopant.

[0257] A dopant is a substance that is mixed in trace amounts into a composition for an organic optoelectronic device to produce light emission, and generally, a substance such as a metal complex that emits light through multiple excitation, which excites the material to a triplet state or higher, may be used. The dopant may be, for example, inorganic, organic, or organic-inorganic compounds, and may include one or more types.

[0258] The above dopant may be an iridium complex represented, for example, by one of the following chemical formulas 7 to 9.

[0259] [Chemical Formula 7]

[0260]

[0261] In the above chemical formula 7,

[0262] Ring A is a monocyclic ring or a polycyclic fused ring, and

[0263] Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and

[0264] R 100 ...represents one to a maximum number of monovalent substituents,

[0265] R 100 If there are 2 or more of these, each R 100 They are identical or different from each other,

[0266] R 101 to R 104 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these,

[0267] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0268] X 10 and X 11 Each is independently selected from the group consisting of carbon and nitrogen, and

[0269] L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and

[0270] m21 is any one of integers from 0 to 3;

[0271] [Chemical Formula 8]

[0272]

[0273] In the above chemical formula 8,

[0274] Ring B is a monocyclic ring or a polycyclic fused ring, and

[0275] Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and

[0276] Y 100 is O or S,

[0277] R 201 ...represents one to a maximum number of monovalent substituents,

[0278] R 201 If there are 2 or more of these, each R 201 They are identical or different from each other,

[0279] R 206 to R 213 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these,

[0280] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0281] X 12 and X 13 Each is independently selected from the group consisting of carbon and nitrogen, and

[0282] L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and

[0283] m21 is any one of integers from 0 to 3;

[0284] [Chemical Formula 9]

[0285]

[0286] In the above chemical formula 9,

[0287] Y100 is O or S,

[0288] R 101 to R 112 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these,

[0289] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0290] L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and

[0291] m21 is any one of integers from 0 to 3.

[0292] For example, the above L 100 It may be one selected from the following chemical formulas Z-1 to Z-8.

[0293] [Z-1] [Z-2] [Z-3]

[0294]

[0295] [Z-4] [Z-5]

[0296]

[0297] [Chemical Formula Z-6] [Chemical Formula Z-7]

[0298]

[0299] [Z-8]

[0300]

[0301] In the above chemical formulas Z-1 to Z-8,

[0302] X 14 is selected from the group consisting of carbon and nitrogen, and

[0303] Y 100 is O or S,

[0304] R 101 to R 122 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C3 to C30 cycloalkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 Or; or may be connected to adjacent substituents to form a substituted or unsubstituted ring, for example, together with pyridine, may form a substituted or unsubstituted quinoline, substituted or unsubstituted benzopropyridine, substituted or unsubstituted benzothienopyridine, substituted or unsubstituted indenopyridine, substituted or unsubstituted benzopropynoline, substituted or unsubstituted benzothienoquinoline, or substituted or unsubstituted indenopyridine;

[0305] m18 is an integer from 1 to 4, and

[0306] m19 is an integer from 1 to 5.

[0307] The above L 100 More specific examples may be selected from the chemical formulas listed in Group A below, but are not limited thereto.

[0308] [Group A]

[0309]

[0310]

[0311] In the above group A,

[0312] R300 to R 302 Each is independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen.

[0313] R 303 to R 308 Each is independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0314] m25 is one of the integers 1 to 5, and

[0315] m26 is one of integers from 1 to 4, and

[0316] m27 is one of integers from 1 to 3, and

[0317] m28 is an integer of 1 or 2, and

[0318] m29 is one of integers from 1 to 6, and

[0319] If m25 to m29 are 2 or more, each R 303 to R 307 They are identical or different from each other.

[0320] As a more specific example, the above iridium complex can be represented by one of the following chemical formulas 7-1 to 7-6.

[0321] [Chemical Formula 7-1]

[0322]

[0323] In the above chemical formula 7-1,

[0324] R 101 to R 116 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 132 R 133 R 134 or -GeR 132 R 133 R 134 And,

[0325] The above R 132 to R 134 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0326] R 101 to R 116 At least one of them is a functional group represented by the following chemical formula V-1, and

[0327] L 100 It is a bidentate ligand of a monovalent anion that coordinates to iridium through lone pairs of electrons on carbon or heteroatoms, and

[0328] m21 and m22 are independently any one of integers from 0 to 3, and m21 + m22 is any one of integers from 1 to 3, and

[0329] [Chemical Formula V-1]

[0330]

[0331] In the above chemical formula V-1,

[0332] R 135 to R 139Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0333] * represents the part connected to the carbon atom.

[0334] [Chemical Formula 7-2]

[0335]

[0336] [Chemical Formula 7-3]

[0337]

[0338] [Chemical Formula 7-4]

[0339]

[0340] [Chemical Formula 7-5]

[0341]

[0342] [Chemical Formula 7-6]

[0343]

[0344] In the above chemical formulas 7-2 to 7-6,

[0345] X 14 is selected from the group consisting of carbon and nitrogen, and

[0346] Y 100 is O or S,

[0347] R 101 to R 122 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 And,

[0348] The above R 133 to R135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0349] L 100 It is a bidentate ligand of a monovalent anion that coordinates to iridium through lone pairs of electrons on carbon or heteroatoms, and

[0350] m111 is an integer from 1 to 2, and

[0351] n1 and n2 are independently any one of integers from 0 to 3, and n1 + n2 is any one of integers from 1 to 3.

[0352] The organic layer may include additional charge transport regions in addition to the light-emitting layer.

[0353] The above charge transport region may be, for example, a hole transport region (140).

[0354] 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.

[0355] Specifically, the hole transport region (140) may include a hole transport layer between the anode (120) and the light-emitting layer (130), and a hole transport auxiliary layer between the light-emitting layer (130) and the hole transport layer, and at least one of the compounds listed in Group B below may be included in at least one layer of the hole transport layer and the hole transport auxiliary layer.

[0356] [Group B]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390] (Dn refers to the number of deuterium substitutions, where n represents a number greater than or equal to 1 and less than or equal to the maximum possible substitution number.)

[0391] In addition to the aforementioned compound, known compounds and compounds with similar structures described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. may also be used in the hole transport region (140).

[0392] In addition, the charge transport region may be, for example, an electron transport region (150).

[0393] The above 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.

[0394] Specifically, the electron transport region (150) may include an electron transport layer between the cathode (110) and the light-emitting layer (130), and an electron transport auxiliary layer between the light-emitting layer (130) and the electron transport layer, and at least one of the compounds listed in Group C below may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0395] [Group C]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406]

[0407]

[0408]

[0409]

[0410]

[0411]

[0412]

[0413] One embodiment may be an organic light-emitting device including a light-emitting layer as an organic layer.

[0414] Another embodiment may be an organic light-emitting device including a light-emitting layer and a hole transport region as the organic layer.

[0415] Another embodiment may be an organic light-emitting device including a light-emitting layer and an electron transport region as organic layers.

[0416] An organic light-emitting device according to one embodiment of the present invention may include a hole transport region (140) and an electron transport region (150) in addition to the light-emitting layer (130) as an organic layer (105) as shown in FIG. 1.

[0417] Meanwhile, the organic light-emitting device may additionally include an electron injection layer (not shown), a hole injection layer (not shown), etc., in addition to the light-emitting layer as the aforementioned organic layer.

[0418] An organic light-emitting device (100) can be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer using a dry film deposition method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and then forming a cathode or an anode thereon.

[0419] The above-described organic light-emitting element can be applied to an organic light-emitting display device.

[0420] The above-described embodiment will be explained in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the claims.

[0421] Unless otherwise noted, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or synthesized using known methods.

[0422] (Synthesis of compounds for organic optoelectronic devices)

[0423] Synthesis Example 1: Synthesis of Compound A-1

[0424] [Reaction Equation 1]

[0425]

[0426] Step 1: Synthesis of Intermediate Int-1

[0427] 30 g (163 mmol) of cyanuric chloride, 82 g (586 mmol) of 2-fluorophenylboronic acid, 67.5 g (488 mmol) of K2CO3, and 411.3 g (10 mmol) of Pd(PPh3) were suspended in 540 ml of toluene under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was completed, extraction was performed, and 50 g (85%) of intermediate Int-1 was obtained by recrystallization of toluene.

[0428] Step 2: Synthesis of Compound A-1

[0429] 20 g (55 mmol) of Int-1, 33.1 g (198 mmol) of 9H-carbazole, and 35.1 g (165 mmol) of K3PO4 were suspended in 183 ml of DMF under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized with ethyl acetate and hexane to obtain 38 g (86%) of compound A-1.

[0430] LC-Mass (Theoretical value: 804.30 g / mol, Measured value: M+ = 804.68 g / mol)

[0431]

[0432] Synthesis Example 2: Synthesis of Compound A-5

[0433] [Reaction Equation 2]

[0434]

[0435] Step 1: Synthesis of the intermediate Int-2

[0436] 20 g (55 mmol) of Int-1, 17.5 g (105 mmol) of 9H-carbazole, and 35.1 g (165 mmol) of K3PO4 were suspended in 183 ml of DMF under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing water with MgSO4, the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized with ethyl acetate and hexane to obtain 25 g (69%) of the intermediate Int-2.

[0437] Step 2: Synthesis of Compound A-5

[0438] 25 g (30 mmol) of Int-2, 8.1 g (33 mmol) of 4-phneyl-9H-carbazole, and 19.4 g (91 mmol) of K3PO4 were suspended in 101 ml of DMF under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized with ethyl acetate and hexane to obtain 22 g (82%) of compound A-5.

[0439] LC-Mass (Theoretical value: 880.33 g / mol, Measured value: M+ = 880.74 g / mol)

[0440]

[0441] Synthesis Example 3: Synthesis of Compound A-18

[0442] [Reaction Equation 3]

[0443]

[0444] Step 1: Synthesis of the intermediate Int-3

[0445] 30 g (163 mmol) of cyanuric chloride, 43.3 g (309 mmol) of 2-fluorophenylboronic acid, 67.5 g (488 mmol) of K2CO3, and 411.3 g (10 mmol) of Pd(PPh3) were suspended in 540 ml of toluene under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was completed, extraction was performed, and 40 g (81%) of the intermediate Int-3 was obtained by recrystallization of toluene.

[0446] Step 2: Synthesis of the intermediate Int-4

[0447] 30 g (99 mmol) of Int-3, 40.5 g (188 mmol) of (2-fluoro-[1,1'-biphenyl]-3-yl)boronic acid, 41.0 g (296 mmol) of K2CO3, and 46.9 g (6 mmol) of Pd(PPh3) were suspended in 329 ml of THF and 148 ml of distilled water under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was completed, extraction was performed, and 38 g (88%) of the intermediate Int-4 was obtained by toluene recrystallization.

[0448] Step 2: Synthesis of Compound A-18

[0449] 20 g (46 mmol) of Int-4, 27.4 g (164 mmol) of 9H-carbazole, and 29.0 g (137 mmol) of K3PO4 were suspended in 152 ml of DMF under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized with ethyl acetate and hexane to obtain 31 g (77%) of compound A-18.

[0450] LC-Mass (Theoretical value: 880.33 g / mol, Measured value: M+ = 880.57 g / mol)

[0451]

[0452] Synthesis Example 4: Synthesis of Compound A-65

[0453] [Reaction Equation 4]

[0454]

[0455] 10 g (15 mmol) of Int-2, 6.6 g (17 mmol) of 4-(triphenylen-2-yl)-9H-carbazole, and 49.7 g (46 mmol) of K3PO were suspended in 51 ml of DMF under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized with ethyl acetate and hexane to obtain 13 g (83%) of compound A-65.

[0456] LC-Mass (Theoretical value: 1030.38 g / mol, Measured value: M+ = 1030.74 g / mol)

[0457]

[0458] Synthesis Example 5: Synthesis of Compound A-110

[0459] [Reaction Equation 5]

[0460]

[0461] 10 g (15 mmol) of Int-2, 6.6 g (17 mmol) of 1-([1,1':3',1''-terphenyl]-5'-yl)-9H-carbazole, and 49.7 g (46 mmol) of K3PO were suspended in 51 ml of DMF under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized with ethyl acetate and hexane to obtain 11 g (70%) of compound A-110.

[0462] LC-Mass (Theoretical value: 1032.39 g / mol, Measured value: M+ = 1032.81 g / mol)

[0463]

[0464] Synthesis Example 6: Synthesis of Compound A-151

[0465] [Reaction Equation 6]

[0466]

[0467] Step 1: Synthesis of the intermediate Int-5

[0468] 30 g (163 mmol) of cyanuric chloride, 84.3 g (586 mmol) of (2-fluorophenyl-3,4,5,6-d4)boronic acid, 67.5 g (488 mmol) of K2CO3, and 411.3 g (10 mmol) of Pd(PPh3) were suspended in 542 ml of toluene under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was completed, extraction was performed, and 53 g (87%) of intermediate Int-5 was obtained by recrystallization of toluene.

[0469] Step 2: Synthesis of Compound A-151

[0470] 20 g (53 mmol) of Int-5, 10.3 g (59 mmol) of 9H-carbazole-1,2,3,4,5,6,7,8-d8, and 34.0 g (160 mmol) of K3PO4 were suspended in 178 ml of DMF under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was complete, the mixture was poured into excess distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing water with MgSO4, the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized with ethyl acetate and hexane to obtain 39 g (87%) of compound A-151 (Dn=20).

[0471] LC-Mass (Theoretical value: 840.53 g / mol, Measured value: M+ = 840.91 g / mol)

[0472]

[0473] Synthesis Example 7: Synthesis of Compound C-4

[0474] [Reaction Equation 7]

[0475]

[0476] 10.0 g (24.5 mmol) of intermediate 9-1, 6.3 g (26.9 mmol) of intermediate 9-2, 31.1 g (1.2 mmol) of Pd2(dba), 3.5 g (36.7 mmol) of NaOtBu, and 30.7 g (3.7 mmol) of P(t-Bu) were placed in a round-bottom flask, 122 ml of Xylene was added, and the mixture was refluxed and stirred at 140 °C for 12 hours. After the reaction was finished, distilled water was added and stirred, the aqueous layer was removed, the organic layer was filtered through silica gel, and recrystallized to obtain 10.3 g (75%) of compound C-4.

[0477] (LC / MS Theoretical value: 560.23 g / mol, Measured value: M+= 561.54 g / mol)

[0478]

[0479] Synthesis Example 8: Synthesis of Compound R-1 (Comparative Example)

[0480] [Reaction Equation 8]

[0481]

[0482] Step 1: Synthesis of Compound R-1

[0483] 20 g (48 mmol) of 2,4-di([1,1'-biphenyl]-4-yl)-6-chloro-1,3,5-triazine, 15 g (52 mmol) of (2-(9H-carbazol-9-yl)phenyl)boronic acid, 19.8 g (143 mmol) of K2CO3, and 43.3 g (3 mmol) of Pd(PPh3) were suspended in 329 ml of THF and 148 ml of distilled water under a nitrogen stream and stirred under reflux for 12 hours. After the reaction was completed, extraction was performed, and 25 g (84%) of compound R-1 was obtained by toluene recrystallization.

[0484] LC-Mass (Theoretical value: 626.25 g / mol, Measured value: M+ = 626.76 g / mol)

[0485]

[0486] Example 1: Fabrication of a green organic light-emitting diode

[0487] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition machine. Using the prepared ITO transparent electrode as the anode, a 100 Å thick hole injection layer was formed by vacuum depositing compound A doped with 3% NDP-9 (commercially available from Novaled) on the ITO substrate, and a hole transport layer was formed by depositing compound A to a thickness of 1350 Å on top of the hole injection layer. A hole transport auxiliary layer was formed by depositing compound B to a thickness of 320 Å on top of the hole transport layer. On the above hole transport assist layer, compounds A-1 and C-4 were simultaneously used as hosts in a weight ratio of 4:6 and doped with PhGD at 10 wt% as a dopant to form an emissive layer with a thickness of 380 Å by vacuum deposition. Subsequently, compound C was deposited to a thickness of 50 Å on the emissive layer to form an electron transport assist layer, and compounds D and Liq were simultaneously vacuum deposited in a weight ratio of 1:1 to form an electron transport layer with a thickness of 300 Å. An organic light-emitting diode was fabricated by sequentially vacuum depositing LiQ 15 Å and Al 1200 Å on the electron transport layer to form a cathode.

[0488] It was fabricated with the structure ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / Compound B (320Å) / EML[Host(Compound A-1 : Compound C-4 = 4 : 6 wt% / wt%) : PhGD = 90wt% : 10wt%](380Å) / Compound C(50Å) / Compound D:LiQ(300Å) / LiQ(15Å) / Al(1200Å).

[0489] Compound A: N-(9,9-diphenyl-9H-fluoren-2-yl)-N,9-diphenyl-9H-carbazol-2-amine

[0490] Compound B: 9,9-dimethyl-N-[3-(9-phenyl-9H-fluoren-9-yl)phenyl]-4-(4-phenylphenyl)-9H-fluoren-2-amine

[0491] Compound C: 4-{4-[4-(9,9-dimethyl-9H-fluoren-4-yl)phenyl]phenyl}-2-phenyl-6-(4-phenylphenyl)pyrimidine

[0492] Compound D: 2-(4-{1-[4-(diphenyl-1,3,5-triazin-2-yl)phenyl]naphthalene-2-yl}-4,6-diphenyl-1,3,5-triazine

[0493] [PhGD]

[0494]

[0495]

[0496] Examples 2 to 6, and Comparative Examples 1 and 2

[0497] An organic light-emitting diode was fabricated using the same method as in Example 1, except that the composition was changed to the one listed in Table 1 below.

[0498]

[0499] evaluation

[0500] The luminous efficiency and lifespan characteristics of organic light-emitting diodes according to Examples 1 to 6 and Comparative Examples 1 and 2 were evaluated.

[0501] The specific measurement method is as follows, and the results are shown in Table 1.

[0502] (1) Measurement of change in current density according to voltage change

[0503] For the fabricated organic light-emitting diode, the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0V to 10V, and the result was obtained by dividing the measured current value by the area.

[0504] (2) Measurement of change in brightness according to voltage change

[0505] For the fabricated organic light-emitting diode, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and the results were obtained.

[0506] (3) Measurement of luminous efficiency

[0507] Using the luminance, current density, and voltage measured from (1) and (2) above, the same current density (10 mA / cm²) 2 The luminous efficiency (cd / A) of ) was calculated.

[0508] The luminous efficiency values ​​of Examples 1 to 6 and Comparative Examples 1 and 2 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0509] (4) Life measurement

[0510] Luminance (cd / m²) 2 ) 24,000 cd / m 2 The result was obtained by maintaining it and measuring the time it took for the current efficiency (cd / A) to decrease to 97%.

[0511] The life measurement values ​​of Examples 1 to 6 and Comparative Examples 1 and 2 were calculated as relative values ​​based on Comparative Example 1 and listed in Table 1 below.

[0512] No. Host Luminous Efficiency (%) Lifetime (%) Example 1A-1C-4105120 Example 2A-5C-4103125 Example 3A-18C-4106110 Example 4A-65C-4103125 Example 5A-110C-4105115 Example 6A-15C-4105140 Comparative Example 1R-1C-4100100 Comparative Example 2A-1--8743

[0513] Referring to Table 1, it can be seen that the organic light-emitting diodes according to Examples 1 to 6 have significantly improved luminous efficiency and lifespan characteristics compared to the organic light-emitting diodes according to Comparative Examples 1 to 2. Although the examples have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements by those skilled in the art using the basic concept of the present invention as defined in the following claims also fall within the scope of the present invention.

Claims

1. A first compound represented by the following chemical formula 1; and A second compound represented by the following chemical formula 2 Composition for organic optoelectronic devices comprising: [Chemical Formula 1] In the above chemical formula 1, R 1 to R 9 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, substituted or unsubstituted C6 to C30 arylsilyl group or substituted or unsubstituted C6 to C20 aryl group, and m1 to m9 are each independently one of integers 1 to 4, and When m1 to m9 are integers greater than or equal to 2, each R 1 to R 9 They are identical or different from each other; [Chemical Formula 2] In the above chemical formula 2, L 1 and L 2 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and R 11 and R 14 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine 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, and m11 and m12 are each independently one of integers 1 to 4, and If m11 and m12 are 2 or more, respectively R 11 and R 12 They are identical or different from each other.

2. In Paragraph 1, The above R 1 to R 3 A composition for an organic optoelectronic device, wherein each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C1 to C6 alkylsilyl group, a substituted or unsubstituted C6 to C12 arylsilyl group, or a substituted or unsubstituted C6 to C18 aryl group.

3. In Paragraph 1, The above R 1 to R 3 A composition for an organic optoelectronic device, wherein each is independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

4. In Paragraph 1, The above R 4 to R 9 A composition for an organic optoelectronic device, wherein each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C1 to C6 alkylsilyl group, a substituted or unsubstituted C6 to C12 arylsilyl group, or a substituted or unsubstituted C6 to C18 aryl group.

5. In Paragraph 1, The above R 4 to R 9 A composition for an organic optoelectronic device, wherein each is independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

6. In Paragraph 1, The above first compound is a composition for an organic optoelectronic device selected from the compounds listed in Group 1 below: [Group 1] [A-1] [A-2] [A-3] [A-4] [A-5] [A-6] [A-7] [A-8] [A-9] [A-10] [A-11] [A-12] [A-13] [A-14] [A-15] [A-16] [A-17] [A-18] [A-19] [A-20] [A-21] [A-22] [A-23] [A-24] [A-25] [A-26] [A-27] [A-28] [A-29] [A-30] [A-31] [A-32] [A-33] [A-34] [A-35] [A-36] [A-37] [A-38] [A-39] [A-40] [A-41] [A-42] [A-43] [A-44] [A-45] [A-46] [A-47] [A-48] [A-49] [A-50] [A-51] [A-52] [A-52] [A-53] [A-54] [A-55] [A-56] [A-57] [A-59] [A-60] [A-61] [A-62] [A-63] [A-64] [A-65] [A-66] [A-67] [A-68] [A-69] [A-70] [A-71] [A-72] [A-73] [A-74] [A-75] [A-76] [A-77] [A-78] [A-79] [A-80] [A-81] [A-82] [A-83] [A-84] [A-85] [A-86] [A-87] [A-88] [A-89] [A-90] [A-91] [A-92] [A-93] [A-94] [A-95] [A-96] [A-97] [A-98] [A-99] [A-100] [A-101] [A-102] [A-103] [A-104] [A-105] [A-106] [A-107] [A-108] [A-109] [A-110] [A-111] [A-112] [A-113] [A-114] [A-115] [A-116] [A-117] [A-118] [A-119] [A-120] [A-121] [A-122] [A-123] [A-124] [A-125] [A-126] [A-127] [A-128] [A-129] [A-130] [A-131] [A-132] [A-133] [A-134] [A-135] [A-136] [A-137] [A-138] [A-139] [A-140] [A-141] [A-142] [A-143] [A-144] [A-145] [A-146] [A-147] [A-148] [A-149] [A-150] [A-151] [A-152] [A-152] [A-153] [A-154] [A-155] [A-156] [A-157] [A-158] Dn means the number of deuterium substitutions, where n means a number greater than or equal to 1 and less than or equal to the maximum number of substitutions possible.

7. In Paragraph 1, The above L 1 and L 2 A composition for an organic optoelectronic device, each independently comprising a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylenylene group.

8. In Paragraph 1, The above Ar 1 and Ar 2 A composition for an organic optoelectronic device, wherein each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

9. In Paragraph 1, The above R 11 to R 14 A composition for an organic optoelectronic device, each independently comprising hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

10. In Paragraph 1, The above L 1 -Ar 1 and L 2 -Ar 2 Each is independently one of the substituents listed in Group I below, and [Group I] In the above Group I, R 15 to R 20 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and m13 is one of integers from 1 to 5, and m14 is one of integers from 1 to 4, and m15 is one of integers from 1 to 3, and m16 is an integer of 1 or 2, and m17 is one of integers from 1 to 7, and * is a connection point.

11. In Paragraph 1, The above second compound is a composition for an organic optoelectronic device selected from the compounds listed in Group 2 below: [Group 2] [C-1] [C-2] [C-3] [C-4] [C-5] [C-6] [C-7] [C-8] [C-9] [C-10] [C-11] [C-12] [C-13] [C-14] [C-15] [C-16] [C-17] [C-18] [C-19] [C-20] [C-21] [C-22] [C-23] [C-24] [C-25] [C-26] [C-27] [C-28] [C-29] [C-30] [C-31] [C-32] [C-33] [C-34] [C-35] [C-36] [C-37] [C-38] [C-39] [C-40] [C-41] [C-42] [C-43] [C-44] [C-45] [C-46] [C-47] [C-48] [C-49] [C-50] [C-51] [C-52] [C-53] [C-54] [C-55] [C-56] [C-57] [C-58] [C-59] [C-60] [C-61] [C-62] [C-63] [C-64] [C-65] [C-66] [C-67] ​​[C-68] [C-69] [C-70] [C-71] [C-72] [C-73] [C-74] [C-75] [C-76] [C-77] [C-78] [C-79] [C-80] [C-81] [C-82] [C-83] [C-84] [C-85] [C-86] [C-87] [C-88] [C-89] Dn refers to the number of deuterium substitutions and indicates a structure with one or more deuterium substitutions.

12. Positive and negative poles facing each other, It includes at least one organic layer located between the anode and the cathode, and The above organic layer is an organic optoelectronic device comprising a composition for an organic optoelectronic device according to any one of claims 1 to 11.

13. In Paragraph 12, The above organic layer includes a light-emitting layer, and The above-mentioned light-emitting layer is an organic optoelectronic device comprising the above-mentioned composition for the organic optoelectronic device.

14. In Paragraph 13, The above-mentioned light-emitting layer further comprises a dopant, and An organic optoelectronic device in which the above dopant is an iridium complex represented by one of the following chemical formulas 7 to 9: [Chemical Formula 7] In the above chemical formula 7, Ring A is a monocyclic ring or a polycyclic fused ring, and Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and R 100 ...represents one to a maximum number of monovalent substituents, R 100 If there are 2 or more of these, each R 100 They are identical or different from each other, R 101 to R 104 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these, The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and X 10 and X 11 Each is independently selected from the group consisting of carbon and nitrogen, and L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and m21 is any one of integers from 0 to 3; [Chemical Formula 8] In the above chemical formula 8, Ring B is a monocyclic ring or a polycyclic fused ring, and Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and Y 100 is O or S, R 201 ...represents one to a maximum number of monovalent substituents, R 201 If there are 2 or more of these, each R 201 They are identical or different from each other, R 206 to R 213 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these, The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and X 12 and X 13 Each is independently selected from the group consisting of carbon and nitrogen, and L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and m21 is any one of integers from 0 to 3; [Chemical Formula 9] In the above chemical formula 9, Y 100 is O or S, R 101 to R 112 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, -SiR 114 R 115 R 116 , -GeR 114 R 115 R 116 or a combination of these, The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and L 100 It is a monovalent anion ligand or bitentate ligand that coordinates to iridium through non-covalent electron pairs of carbon or heteroatoms, and m21 is any one of integers from 0 to 3.

15. A display device comprising an organic optoelectronic element according to paragraph 12.

Images