Compound for organic optoelectronic device, organic optoelectronic device, and display device

Abstract

The present invention relates to: a compound for an organic optoelectronic device, the compound being represented by chemical formula 1; and an organic optoelectronic device and a display device, each comprising the compound. The details of chemical formula 1 are as defined in the specification.

Description

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

[0001] This relates to compounds for organic optoelectronic devices, organic optoelectronic devices, and display devices.

[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 compound for an organic optoelectronic device that enables the realization of a long-life organic optoelectronic device that operates effectively even at low voltages.

[0007] Another embodiment provides an organic optoelectronic device comprising a compound 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 compound for an organic optoelectronic device represented by the following chemical formula 1 is provided.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] X 1 is O or S,

[0014] R 1 and R 2 Each is independently hydrogen, deuterium, cyano group, halogen 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

[0015] R 3 to R 5 Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and

[0016] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0017] m1 and m2 are each independently one of integers from 1 to 3, and

[0018] If m1 and m2 are 2 or more, respectively R 1 and R 2 They are identical or different from each other.

[0019] 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 compound for the organic optoelectronic device.

[0020] According to another embodiment, a display device comprising the organic optoelectronic element is provided.

[0021] It is possible to realize long-life organic optoelectronic devices that can be effectively driven even at low voltages.

[0022] FIG. 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0023] <Explanation of Symbols>

[0024] 10: Anode 20: Cathode

[0025] 30: Organic layer 31: Hole transport layer

[0026] 32: Emissive layer 33: Hole transport assist layer

[0027] 34: Electronic Transport Domain

[0028]

[0029] 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.

[0030] 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.

[0031] 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 C6 to C30 aryl 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 C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen of a substituent or compound is substituted with a deuterium, cyano group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, terphenyl group, or naphthyl group.

[0032] In this specification, “non-substituted” means that a hydrogen atom remains a hydrogen atom without being substituted by another substituent.

[0033] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0034] 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.

[0035] 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.

[0036] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0037] 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.

[0038] 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.

[0039] 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.

[0040] 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 benzoxazinyl group, a substituted or unsubstituted benzthiazineyl group, a substituted or unsubstituted acrridinyl group, a substituted or unsubstituted phenazineyl group, a substituted or unsubstituted phenothiazineyl group, a substituted or unsubstituted phenoxazineyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, a substituted or unsubstituted xanthenyl group, a substituted or unsubstituted benzonaphtufuranyl group, a substituted or unsubstituted benzonaphthiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof. However, it is not limited to this.

[0041] 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.

[0042] 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.

[0043] A compound for an organic optoelectronic device according to one embodiment is described below.

[0044] A compound for an organic optoelectronic device according to one embodiment is represented by the following chemical formula 1.

[0045] [Chemical Formula 1]

[0046]

[0047] In the above chemical formula 1,

[0048] X 1 is O or S,

[0049] R 1 and R 2 Each is independently hydrogen, deuterium, cyano group, halogen 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

[0050] R 3 to R 5 Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and

[0051] L 1 and L 2Each is independently a single bonded, substituted, or unsubstituted C6 to C30 arylene group, and

[0052] Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0053] m1 and m2 are each independently one of integers from 1 to 3, and

[0054] If m1 is 2 or greater, each R 1 They are identical or different from each other.

[0055] If m2 is 2 or greater, each R 2 They are identical or different from each other.

[0056] In the compound for organic optoelectronic devices represented by Chemical Formula 1 above, the 6th position of dibenzofuran (or dibenzothiophene) is a highly reactive site and can affect molecular stability during hole injection and electron leakage. Therefore, a silyl group with high electron stability was introduced at the 6th position to improve the lifespan of the organic light-emitting device to which it is applied.

[0057] In addition, the glass transition temperature of the compound was improved through the introduction of silyl groups, and the efficiency of the organic light-emitting diode to which it is applied was improved by having a high T1 energy.

[0058] For example, the above Ar 1 and Ar 2are each 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 triphenylene group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted dibenzosilolyl group, a substituted or unsubstituted xanthenyl group, a substituted or unsubstituted spirocyclopentane-1,9'-fluorenyl group, a substituted or unsubstituted spirocyclohexane-1,9'-fluorenyl group, or a substituted or unsubstituted It may be a spirofluorene-9,9'-xanthen group.

[0059] As a specific example, the aforementioned Ar 1 and Ar 2 Each can be independently selected from the substituents listed in Group I below.

[0060] [Group I]

[0061]

[0062] In the above Group I,

[0063] R 16 to R 20 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[0064] R 21 and R 22 Each is independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, and

[0065] m5 is one of integers from 1 to 5, and

[0066] m6 is one of integers from 1 to 4, and

[0067] m7 is one of integers from 1 to 3, and

[0068] m8 is one of integers from 1 to 8, and

[0069] m9 is one of the integers from 1 to 10, and

[0070] * is a connection point.

[0071] If m5 is 2 or greater, each R 16 They may be the same or different from each other.

[0072] If m6 is 2 or greater, each R 17 They may be identical or different from each other.

[0073] If m7 is 2 or greater, each R 18 They may be the same or different from each other.

[0074] If m8 is 2 or greater, each R 19 They may be the same or different from each other.

[0075] If m9 is 2 or greater, each R 20 They may be the same or different from each other.

[0076] For example, the above Ar 1 and Ar 2 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0077] In one embodiment, the Ar 1 is a substituted or unsubstituted 2-fluorenyl group, and the Ar 2 It may be a substituted or unsubstituted 4-fluorenyl group.

[0078] For example, the above L 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted C6 to C12 arylene group.

[0079] For example, the above L 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted phenylene group.

[0080] For example, the above R 3 to R 5 Each may be an independently substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0081] As a specific example, the above R 3 to R 5 Each may independently be a substituted or unsubstituted iso-propyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0082] For example, a compound for an organic optoelectronic device represented by Chemical Formula 1 may be selected from the compounds listed in Group 1 below, but is not limited thereto.

[0083] [Group 1]

[0084] [1-1] [1-2] [1-3] [1-4] [1-5]

[0085]

[0086] [1-6] [1-7] [1-8] [1-9] [1-10]

[0087]

[0088] [1-11] [1-12] [1-13] [1-14] [1-15]

[0089]

[0090] [1-16] [1-17] [1-18] [1-19] [1-20]

[0091]

[0092] [1-21] [1-22] [1-23] [1-24] [1-25]

[0093]

[0094] [1-26] [1-27] [1-28] [1-29] [1-30]

[0095]

[0096] [1-31] [1-32] [1-33] [1-34] [1-35]

[0097]

[0098] [1-36] [1-37] [1-38] [1-39] [1-40]

[0099]

[0100] [1-41] [1-42] [1-43] [1-44] [1-45]

[0101]

[0102] [1-46] [1-47] [1-48] [1-49] [1-50]

[0103]

[0104] [1-51] [1-52] [1-53] [1-54] [1-55]

[0105]

[0106] [1-56] [1-57] [1-58] [1-59] [1-60]

[0107]

[0108] [1-61] [1-62] [1-63] [1-64] [1-65]

[0109]

[0110] [1-66] [1-67] [1-68] [1-69] [1-70]

[0111]

[0112] [1-71] [1-72] [1-73] [1-74] [1-75]

[0113]

[0114] [1-76] [1-77] [1-78] [1-79] [1-80]

[0115]

[0116] [1-81] [1-82] [1-83] [1-84] [1-85]

[0117]

[0118] [1-86] [1-87] [1-88] [1-89] [1-90]

[0119]

[0120] [1-91] [1-92] [1-93] [1-94] [1-95]

[0121]

[0122] [1-96] [1-97] [1-98] [1-99] [1-100]

[0123]

[0124] [1-101] [1-102] [1-103] [1-104] [1-105]

[0125]

[0126] [1-106] [1-107] [1-108] [1-109] [1-110]

[0127]

[0128] [1-111] [1-112] [1-113] [1-114] [1-115]

[0129]

[0130] [1-116] [1-117] [1-118] [1-119] [1-120]

[0131]

[0132] [1-121] [1-122] [1-123] [1-124] [1-125]

[0133]

[0134] [1-126] [1-127] [1-128] [1-129] [1-130]

[0135]

[0136] [1-131] [1-132] [1-133] [1-134] [1-135]

[0137]

[0138] [1-136] [1-137] [1-138] [1-139] [1-140]

[0139]

[0140] [1-141] [1-142] [1-143] [1-144] [1-145]

[0141]

[0142] [1-146] [1-147] [1-148] [1-149] [1-150]

[0143]

[0144] [1-151] [1-152] [1-153] [1-154] [1-155]

[0145]

[0146] [1-156] [1-157] [1-158] [1-159] [1-160]

[0147]

[0148] [1-161] [1-162] [1-163] [1-164] [1-165]

[0149]

[0150] [1-166] [1-167] [1-168] [1-169] [1-170]

[0151]

[0152] [1-171] [1-172] [1-173] [1-174] [1-175]

[0153]

[0154] [1-176] [1-177] [1-178] [1-179] [1-180]

[0155]

[0156] [1-181] [1-182] [1-183] [1-184] [1-185]

[0157]

[0158] [1-186] [1-187] [1-188] [1-189] [1-190]

[0159]

[0160] [1-191] [1-192] [1-193] [1-194] [1-195]

[0161]

[0162] [1-196] [1-197] [1-198] [1-199] [1-200]

[0163]

[0164] [1-201] [1-202] [1-203] [1-204] [1-205]

[0165]

[0166] [1-206] [1-207] [1-208] [1-209] [1-210]

[0167]

[0168] [1-211] [1-212] [1-213] [1-214] [1-215]

[0169]

[0170] [1-216] [1-217] [1-218] [1-219] [1-220]

[0171]

[0172] [1-221] [1-222] [1-223] [1-224] [1-225]

[0173]

[0174] [1-226] [1-227] [1-228] [1-229] [1-230]

[0175]

[0176] [1-231] [1-232] [1-233] [1-234] [1-235]

[0177]

[0178] [1-236] [1-237] [1-238] [1-239] [1-240]

[0179]

[0180] [1-241] [1-242] [1-243] [1-244] [1-245]

[0181]

[0182] [1-246] [1-247] [1-248] [1-249] [1-250]

[0183]

[0184] [1-251] [1-252] [1-253] [1-254] [1-255]

[0185]

[0186] [1-256] [1-257] [1-258] [1-259] [1-260]

[0187]

[0188] [1-261] [1-262] [1-263] [1-264] [1-265]

[0189]

[0190] [1-266] [1-267] [1-268] [1-269] [1-270]

[0191]

[0192] [1-271] [1-272] [1-273] [1-274] [1-275]

[0193]

[0194] [1-276] [1-277] [1-278] [1-279] [1-280]

[0195]

[0196] [1-281] [1-282] [1-283] [1-284] [1-285]

[0197]

[0198] [1-286] [1-287] [1-288] [1-289] [1-290]

[0199]

[0200] [1-291] [1-292] [1-293] [1-294] [1-295]

[0201]

[0202] [1-296] [1-297] [1-298] [1-299] [1-300]

[0203]

[0204] [1-301] [1-302] [1-303] [1-304] [1-305]

[0205]

[0206] [1-306] [1-307] [1-308] [1-309] [1-310]

[0207]

[0208] Dn represents the number of hydrogens substituted with deuterium, and n is an integer greater than or equal to 0, and the maximum number of n corresponds to the number of hydrogen positions that can be substituted.

[0209] An organic optoelectronic device incorporating the compound for organic optoelectronic devices described above is described below.

[0210] 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.

[0211] Here, an organic light-emitting diode, which is an example of an organic optoelectronic device, is described with reference to the drawing.

[0212] FIG. 1 is a cross-sectional view schematically illustrating an organic light-emitting device according to one embodiment.

[0213] Referring to FIG. 1, an organic light-emitting device according to one embodiment includes an anode (10) and a cathode (20) facing each other, and an organic layer (30) located between the anode (10) and the cathode (20).

[0214] The anode (10) 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 (10) 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.

[0215] The cathode (20) 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 (20) 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 material such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but is not limited thereto.

[0216] The organic layer (30) includes a hole transport layer (31), a light-emitting layer (32), and a hole transport auxiliary layer (33) located between the hole transport layer (31) and the light-emitting layer (32).

[0217] The organic layer (30) may include the aforementioned organic optoelectronic device compound.

[0218] For example, the light-emitting layer (32) may include the aforementioned compound for organic photoelectronic devices.

[0219] At this time, the light-emitting layer (32) may include, for example, the aforementioned compound for organic optoelectronic devices as a host, and the host may be, for example, a phosphorescent host.

[0220] The phosphorescent host must facilitate the injection and transport of holes and electrons within the emissive layer, ultimately enabling holes and electrons to meet and form excitons effectively, and must be able to effectively transfer the formed exciton energy to the dopant.

[0221] The light-emitting layer (32) may further include a dopant, and the composition including the phosphorescent host and the dopant may be, for example, a red or green light-emitting composition.

[0222] The dopant can be, for example, a phosphorescent dopant, for example, a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0223] A dopant is a substance that is mixed in trace amounts into a host to produce luminescence, and generally, substances such as metal complexes that emit light through multiple excitation, which excites the host 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.

[0224] Phosphorescent dopants are an example of a dopant, and examples of phosphorescent dopants include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants may include, for example, compounds represented by the following chemical formula Z, but are not limited thereto.

[0225] [Chemical Formula Z]

[0226] L 3 MX 2

[0227] In the above chemical formula Z, M is a metal, and L 3 and X 2 is a ligand that is the same or different from each other and forms a complex with M.

[0228] The above M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and the above L 3 and X 2 It can be, for example, a bitentate ligand.

[0229] L 3 and X 2 The ligand represented by may be one selected from the following chemical formulas Z-1 to Z-8.

[0230] [Z-1] [Z-2] [Z-3]

[0231]

[0232] [Z-4] [Z-5]

[0233]

[0234] [Chemical Formula Z-6] [Chemical Formula Z-7]

[0235]

[0236] [Z-8]

[0237]

[0238] In the above chemical formulas Z-1 to Z-8,

[0239] X 14 is selected from the group consisting of carbon and nitrogen, and

[0240] Y 100 is O or S,

[0241] 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 R135 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;

[0242] m18 is an integer from 1 to 4, and

[0243] m19 is an integer from 1 to 5.

[0244] L 3 and X 2 Specific examples of ligands represented by may be selected from the chemical formulas listed in Group A below, but are not limited thereto.

[0245] [Group A]

[0246]

[0247]

[0248] In the above group A,

[0249] R 300 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.

[0250] R 303 to R 308Each 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.

[0251] m25 is one of integers from 1 to 5, and

[0252] m26 is one of integers from 1 to 4, and

[0253] m27 is one of integers from 1 to 3, and

[0254] m28 is an integer of 1 or 2, and

[0255] m29 is one of integers from 1 to 6, and

[0256] If m25 to m29 are 2 or more, each R 303 to R 307 They are identical or different from each other.

[0257] A phosphorescent dopant according to one embodiment may be an iridium complex and may be represented, for example, by any one of the following chemical formulas 9 to 11.

[0258] [Chemical Formula 9]

[0259]

[0260] In the above chemical formula 9,

[0261] Ring A is a monocyclic ring or a polycyclic fused ring, and

[0262] Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and

[0263] R 100 ...represents one to a maximum number of monovalent substituents,

[0264] R 100 If there are 2 or more of these, each R 100 They are identical or different from each other,

[0265] 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,

[0266] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0267] X 10 and X 11 Each is independently selected from the group consisting of carbon and nitrogen, and

[0268] 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

[0269] m21 is any one of integers from 0 to 3.

[0270] [Chemical Formula 10]

[0271]

[0272] In the above chemical formula 10,

[0273] Ring B is a monocyclic ring or a polycyclic fused ring, and

[0274] Here, each of the monocyclic ring and the polycyclic fused ring is a pentagonal or hexacyclic carbocyclic or heterocyclic, and

[0275] Y 100 is O or S,

[0276] R 201 ...represents one to a maximum number of monovalent substituents,

[0277] R 201 If there are 2 or more of these, each R 201 They are identical or different from each other,

[0278] 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,

[0279] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0280] X 12 and X 13 Each is independently selected from the group consisting of carbon and nitrogen, and

[0281] 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

[0282] m21 is any one of integers from 0 to 3.

[0283] [Chemical Formula 11]

[0284]

[0285] In the above chemical formula 11,

[0286] Y 100 is O or S,

[0287] R 101 to R 111 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,

[0288] The above R 114 to R 116 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0289] 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

[0290] m21 is any one of integers from 0 to 3.

[0291] As a more specific example, the above iridium complex can be represented by one of the following chemical formulas 9-1 to 9-6.

[0292] [Chemical Formula 9-1]

[0293]

[0294] In the above chemical formula 9-1,

[0295] 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,

[0296] The above R 132to R 134 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0297] R 101 to R 116 At least one of them is a functional group represented by the following chemical formula V-1, and

[0298] 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

[0299] 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

[0300] [Chemical Formula V-1]

[0301]

[0302] In the above chemical formula V-1,

[0303] R 135 to R 139 Each 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,

[0304] * represents the part connected to the carbon atom.

[0305] [Chemical Formula 9-2]

[0306]

[0307] [Chemical Formula 9-3]

[0308]

[0309] [Chemical Formula 9-4]

[0310]

[0311] [Chemical Formula 9-5]

[0312]

[0313] [Chemical Formula 9-6]

[0314]

[0315] In the above chemical formulas 9-2 to 9-6,

[0316] X 14 is selected from the group consisting of carbon and nitrogen, and

[0317] Y 100 is O or S,

[0318] 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,

[0319] The above R 133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0320] 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

[0321] m111 is an integer from 1 to 2, and

[0322] 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.

[0323] A dopant according to another embodiment may be a platinum complex, for example, represented by the chemical formula Z-9.

[0324] [Chemical Formula Z-9]

[0325]

[0326] In the above chemical formula Z-9, rings A, B, C, and D each independently represent a pentagonal or hexagonal carbocyclic or heterocyclic ring;

[0327] R A , R B , R C , and R D Each independently represents a uniform, bisubstitution, trisubstitution, or quadruple substitution, or no substitution;

[0328] nA is an integer of 0 or 1;

[0329] L B , L C , and L D Each is independently selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0330] If nA is 1, L E is selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; and when nA is 0, L E is not present;

[0331] R A , R B , R C , R D , R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; any adjacent R A , R B , R C , R D, R, and R' are arbitrarily connected to form a ring; X B , X C , X D , and X E are each independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 Each represents oxygen or direct bonding.

[0332] The above platinum complex can be represented, for example, by the following chemical formula 12-1 or chemical formula 12-2.

[0333] [Chemical Formula 12-1]

[0334]

[0335] [Chemical Formula 12-2]

[0336]

[0337] In the above chemical formulas 12-1 and 12-2,

[0338] X 100 It contains O, S, and NR 132 Selected from among,

[0339] R 118 to R 132 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 133 R 134 R 135 And,

[0340] The above R 133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group, and

[0341] R 118 to R 132 At least one of them is -SiR 133 R 134 R 135 or is a tert-butyl group, and

[0342] The above R133 to R 135 Each is an independently substituted or unsubstituted C1 to C6 alkyl group.

[0343] Additionally, the aforementioned compound for organic optoelectronic devices is included in the light-emitting layer (32), 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 (31) and the hole transport assist layer (33).

[0344] [Group B]

[0345]

[0346]

[0347]

[0348]

[0349]

[0350]

[0351]

[0352]

[0353]

[0354]

[0355]

[0356]

[0357]

[0358]

[0359]

[0360]

[0361]

[0362]

[0363]

[0364]

[0365]

[0366]

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378] (Dn represents the number of hydrogens substituted with deuterium, n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of replaceable hydrogen positions.)

[0379] In addition to the aforementioned compounds, known compounds listed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds having a similar structure may also be used in the hole transport layer (31) and hole transport assist layer (33).

[0380] For example, the hole transport assist layer (33) may include the aforementioned organic optoelectronic device compound.

[0381] At this time, examples of phosphorescent hosts included in the light-emitting layer (32) may include organic compounds comprising carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzofuran, indolodibenzothiophene, fluorene, indenocarbazole, triphenylene, pyrimidine, triazine, or combinations thereof.

[0382] The above phosphorescent host can be used without restriction as long as it is a known material, and, for example, it may be a single host or a mixed host.

[0383] In addition, the dopant included in the light-emitting layer (32) is as described above.

[0384] Meanwhile, the hole transport layer (31) is a layer for facilitating hole transfer from the anode (10) to the light-emitting layer (32), and may be, for example, an amine compound, but is not limited thereto.

[0385] The above amine compound may include, for example, at least one aryl group and / or heteroaryl group. The above amine compound may be represented, for example, by the following formula a or formula b, but is not limited thereto.

[0386] [Chemical formula a] [Chemical formula b]

[0387]

[0388] In the above chemical formula a or b,

[0389] Ar a or Ar g Each 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 heteroaryl group, or a combination thereof, and

[0390] Ar a or Ar c At least one of and Ar d or Ar gAt least one of them is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, or a combination thereof, and

[0391] Ar h is 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.

[0392] For example, the hole transport assist layer (33) may include the aforementioned compound for organic optoelectronic devices, and the hole transport layer (31) may include a compound represented by the following chemical formula 2.

[0393] [Chemical Formula 2]

[0394]

[0395] In the above chemical formula 2,

[0396] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0397] L 3 and L 4 Each is independently a single bonded, substituted, or unsubstituted C6 to C30 arylene group, and

[0398] Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and

[0399] R 6 to R 10 Each is independently hydrogen, deuterium, cyano group, halogen 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

[0400] m3 is one of integers from 1 to 3, and

[0401] If m3 is 2 or greater, each R 6 They are identical or different from each other.

[0402] Since at least one fluorene group is substituted on the amine core, the degradation decomposition can be minimized by reducing the deposition temperature due to steric hindrance, so the lifespan characteristics can be further improved.

[0403] For example, the above chemical formula 2 can be represented as any one of the following chemical formulas 2-1 to 2-4, depending on the substitution position of fluorene.

[0404] [Chemical Formula 2-1] [Chemical Formula 2-2]

[0405]

[0406] [Chemical Formula 2-3] [Chemical Formula 2-4]

[0407]

[0408] In the above chemical formulas 2-1 to 2-4,

[0409] Ar 3 or Ar 6 , L 3 , L 4 , R 6 to R 10 The definitions of and m3 are as described above.

[0410] For example, a compound included in the hole transport layer can be represented by the above chemical formula 2-4.

[0411] In the above chemical formula 2, Ar 3 and Ar 4Each 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 fluorenyl group, a substituted or unsubstituted spirobifluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0412] For example, the above Ar 3 and Ar 4 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group.

[0413] In the above chemical formula 2, Ar 5 and Ar 6 Each may be an independently substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0414] For example, the above Ar 5 and Ar 6 Each may be an independently substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0415] In the above chemical formula 2, R 6 to R 10 Each can independently be hydrogen, deuterium, or a substituted or unsubstituted C1 to C5 alkyl group.

[0416] For example, the above R 6 to R 10 Each can independently be hydrogen, deuterium, or tert-butyl group.

[0417] For example, the above Ar 3 and Ar 4 At least one of them may be a substituted or unsubstituted fluorenyl group, and may be represented, for example, by the following chemical formula 2-4-1.

[0418] [Chemical Formula 2-4-1]

[0419]

[0420] In the above chemical formula 2-4-1,

[0421] Ar 4 or Ar 6 , L 3 , L 4 , R 6 to R 10 The definitions of and m3 are as previously stated, and

[0422] Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and

[0423] R 11 to R 15 Each is independently hydrogen, deuterium, cyano group, halogen 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

[0424] m4 is one of the integers 1 to 3.

[0425] In the above chemical formula 2-4-1, when m4 is 2 or more, each R 11 They may be the same or different from each other.

[0426] In the above chemical formula 2-4-1, Ar 7 and Ar 8 Each may be an independently substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0427] For example, the above Ar 7 and Ar 8 Each may be an independently substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0428] In the above chemical formula 2-4-1, R 6 to R10 Each may independently be hydrogen, deuterium, or a substituted or unsubstituted C1 to C5 alkyl group.

[0429] For example, the above R 6 to R 10 Each can independently be hydrogen, deuterium, or tert-butyl group.

[0430] As a specific example, L of the above chemical formula 2-4-1 3 and L 4 Each can be a single bond.

[0431] As a more specific example, the above chemical formula 2-4-1 may be selected from the following chemical formulas 2-4-1a, 2-4-1b, 2-4-1c, and 2-4-1d.

[0432] [Chemical Formula 2-4-1a] [Chemical Formula 2-4-1b]

[0433]

[0434] [Chemical Formula 2-4-1c] [Chemical Formula 2-4-1d]

[0435]

[0436] In the above formulas 2-4-1a, 2-4-1b, 2-4-1c, and 2-4-1d,

[0437] Ar 4 or Ar 8 , R 6 to R 10 , R 11 to R 15 The definitions of , m3 and m4 are as described above.

[0438] As a most specific example, the hole transport layer may include a compound represented by the chemical formula 2-4-1b.

[0439] As an example, R of the above chemical formula 2 7 to R 10 At least two of them may be tert-butyl groups.

[0440] As a specific example, R of the above chemical formula 2 8 and R 10 Each can be a tert-butyl group.

[0441] Heat resistance can be improved by introducing an alkyl group that can improve the glass transition temperature.

[0442] In addition, improving the efficiency of the device can also be expected by lowering the refractive index of the material.

[0443] For example, the compound represented by the above chemical formula 2 may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0444] [Group 2]

[0445] [F-1] [F-2] [F-3] [F-4]

[0446]

[0447] [F-5] [F-6] [F-7] [F-8]

[0448]

[0449] [F-9] [F-10] [F-11] [F-12]

[0450]

[0451] [F-13] [F-14] [F-15] [F-16]

[0452]

[0453] [F-17] [F-18] [F-19] [F-20]

[0454]

[0455] [F-21] [F-22] [F-23] [F-24]

[0456]

[0457] [F-25] [F-26] [F-27] [F-28]

[0458]

[0459] [F-29] [F-30] [F-31] [F-32]

[0460]

[0461] [F-33] [F-34] [F-35] [F-36]

[0462]

[0463] [F-37] [F-38] [F-39] [F-40]

[0464]

[0465] [F-41] [F-42] [F-43] [F-44]

[0466]

[0467] [F-45] [F-46] [F-47] [F-48]

[0468]

[0469] [F-49] [F-50] [F-51] [F-52]

[0470]

[0471] [F-53] [F-54] [F-55] [F-56]

[0472]

[0473] [F-57] [F-58] [F-59] [F-60]

[0474]

[0475] (Dn represents the number of hydrogens substituted with deuterium, n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of replaceable hydrogen positions.)

[0476] Additionally, the organic layer (30) may further include an electron transport region (34).

[0477] The above electron transport region (34) can further increase electron injection and / or electron mobility between the cathode (20) and the light-emitting layer (32) and block holes.

[0478] Specifically, the electron transport region may include an electron transport layer between the cathode (20) and the light-emitting layer (32), and an electron transport auxiliary layer between the light-emitting layer (32) 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.

[0479] [Group C]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493] 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.

[0494] The hole injection layer is a layer for facilitating hole injection from the anode (10) to the light-emitting layer (32) and blocking electrons, and can be located between the anode (10) and the hole transport layer (31).

[0495] For example, the hole injection layer may include at least one of the compounds listed in the aforementioned group B.

[0496] Similarly, in addition to this, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc., and compounds with similar structures may also be used in the hole injection layer.

[0497] 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.

[0498] The above-described organic light-emitting element can be applied to an organic light-emitting display device.

[0499] 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.

[0500] 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.

[0501]

[0502] (Preparation of compounds for organic optoelectronic devices)

[0503] Synthesis Example 1: Synthesis of Compound 1-25

[0504] [Reaction Equation 1]

[0505]

[0506] 10.00 g (21.69 mmol) of the intermediate (9-chlorodibenzo[b,d]furan-4-yl)triphenylsilane, 7.98 g (21.26 mmol) of the intermediate N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine, 3.13 g (32.53 mmol) of sodium t-butoxide, and 0.99 g (4.88 mmol) of tri-tert-butylphosphine were dissolved in 220 ml of toluene, and 30.99 g (1.09 mmol) of Pd2(dba) was added and the mixture was refluxed and stirred under a nitrogen atmosphere for 4 hours. After the reaction was complete, the mixture was extracted with ethyl acetate and distilled water, the organic layer was dried with anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with normal hexane / dichloromethane (3:1 volume ratio) to obtain 13.54 g (yield 78%) of compound 1-25 as a white solid.

[0507]

[0508] Synthesis Example 2: Synthesis of Compound 1-86

[0509] [Reaction Equation 2]

[0510]

[0511] Compound 1-86 was synthesized in the same manner as Synthesis Example 1, except that 12.00 g of the intermediate (9-chlorodibenzo[b,d]furan-4-yl)triphenylsilane and 9.99 g of the intermediate N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophen-1-amine were used in an equivalent ratio of 1:0.98 (14.87 g, yield 70%).

[0512]

[0513]

[0514] Synthesis Example 3: Synthesis of Compound 1-89

[0515] [Reaction Equation 3]

[0516]

[0517] Compound 1-89 was synthesized in the same manner as Synthesis Example 1, except that 25.00 g of the intermediate (9-chlorodibenzo[b,d]furan-4-yl)triphenylsilane and 21.34 g of the intermediate N-(9,9-dimethyl-9H-fluoren-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.98 (35.84 g, yield 82%).

[0518]

[0519] Synthesis Example 4: Synthesis of Compound 1-262

[0520] [Reaction Equation 4]

[0521]

[0522] Compound 1-262 was synthesized in the same manner as Synthesis Example 1, except that 10.00 g of the intermediate (9-chlorodibenzo[b,d]furan-4-yl)triphenylsilane and 6.83 g of the intermediate di([1,1'-biphenyl]-4-yl)amine were used in a 1:0.98 equivalent ratio (12.62 g, yield 78%).

[0523]

[0524] Comparative Synthesis Example 1: Synthesis of Compound R1

[0525]

[0526] Compound R1 was synthesized in the same manner as in Synthesis Example 1, except that 10.00 g of the intermediate 1-chlorodibenzo[b,d]furan and 19.42 g of the intermediate N-(9,9-dimethyl-9H-fluoren-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.98 (21.01 g, yield 75%).

[0527]

[0528] Comparative Synthesis Example 2: Synthesis of Compound R2

[0529]

[0530] Compound R2 was synthesized in the same manner as Synthesis Example 1, except that 12.00 g of the intermediate 1-chloro-6-phenyldibenzo[b,d]furan and 19.42 g of the intermediate N-(9,9-dimethyl-9H-fluoren-4-yl)-9,9-dimethyl-9H-fluoren-2-amine were used in an equivalent ratio of 1:0.98 (22.17 g, yield 80%).

[0531]

[0532] Comparative Synthesis Example 3: Synthesis of Compound R3

[0533]

[0534] Compound R3 was synthesized in the same manner as Synthesis Example 1, except that 15.00 g of the intermediate (6-(4-bromophenyl)dibenzo[b,d]furan-4-yl)triphenylsilane) and 4.28 g of the intermediate diphenylamine were used in a 1:0.98 equivalent ratio (14.17 g, yield 82%).

[0535]

[0536] Comparative Synthesis Example 4: Synthesis of Compound R4

[0537]

[0538] Compound R4 was synthesized in the same manner as in Synthesis Example 1, except that 10.00 g of the intermediate (9-chlorodibenzo[b,d]furan-4-yl)triphenylsilane and 7.07 g of the intermediate 9H-3,9'-bicarbazole were used in a 1:0.98 equivalent ratio (11.33 g, yield 69%).

[0539]

[0540] Comparative Synthesis Example 5: Synthesis of Compound R5

[0541]

[0542] Compound R5 was synthesized in the same manner as Synthesis Example 1, except that 10.00 g of the intermediate (9-chlorodibenzo[b,d]furan-2-yl)triphenylsilane and 7.98 g of the intermediate N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine were used in a 1:0.98 equivalent ratio (12.49 g, yield 72%).

[0543]

[0544] Evaluation 1: Comparison of Simulation Characteristics

[0545] The energy levels of each material were calculated using the Gaussian 09 method with the supercomputer GAIA (IBM power 6), and the results are shown in Table 1 below.

[0546] Example Compound No. HOMO(eV) LUMO(eV) T1 Energy Level (eV) Synthesizing Example 11-25 -4.982 -1.203 2.755 Synthesizing Example 21-86 -5.080 -1.093 2.768 Synthesizing Example 31-89 -4.978 -1.016 2.770 Synthesizing Example 41-26 -5.003 -1.108 2.818 Comparative Synthesizing Example 2 R2 -4.923 -1.071 2.691 Comparative Synthesizing Example 4 R4 -5.151 -1.314 3.115 Comparative Synthesizing Example 5 R5 -4.946 -1.101 2.682

[0547] Referring to Table 1, when a silyl group is introduced at the 6th position of dibenzofuran, it results in a higher T1 energy compared to the case where a substituent other than a silyl group is introduced (Comparative Synthesis Example 2) and the case where a silyl group is substituted at a position other than 6 (Comparative Synthesis Example 5); therefore, it can be expected that the efficiency of the organic light-emitting device to which this is applied will be improved. In addition, Ar of Chemical Formula 1 1 and Ar 2 When each is a 2-fluorenyl group and a 4th fluorenyl group (Synthetic Example 3), it is expected that low driving characteristics will appear because they have shallow HOMO energy levels. Accordingly, it can be expected that the organic light-emitting device to which Synthetic Example 3 is applied will exhibit low driving characteristics along with improved efficiency due to the above effects.

[0548]

[0549] (Fabrication of Organic Light Emitting Diodes)

[0550] Example 1

[0551] A glass substrate coated with a thin film of ITO / Ag / ITO was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as acetone or isopropyl alcohol, 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 / Ag / ITO (reflective 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 / Ag / 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 1-25 obtained in Synthesis Example 1 to a thickness of 335 Å on top of the hole transport layer. On the above hole transport assist layer, a 380 Å thick emissive layer was formed by vacuum deposition using 90 wt% of host H1 (40%) and host H2 (60%) as hosts and 10 wt% of GD as a dopant. Subsequently, an electron transport assist layer was formed by depositing compound C to a thickness of 50 Å on the above emissive layer, and an electron transport layer to a thickness of 310 Å was formed by vacuum deposition of compound D and Liq simultaneously in a weight ratio of 1:1. An organic light-emitting diode was fabricated by forming a cathode by sequentially vacuum depositing Yb and AgMg on the above electron transport layer.

[0552] It was fabricated with a structure of ITO / Ag / ITO / compound A (3% NDP-9 doping, 100Å) / compound A (1350Å) / hole transport assist layer (compound 1-25, 335Å) / emissive layer [Host (host H1 : host H2 = 40 wt% : 60 wt%) : GD = 90 wt% : 10 wt%] (380Å) / compound C (50Å) / compound D : Liq (310Å) / Yb (15Å) / AgMg (1200Å).

[0553] Compound A: N-(6,8-di-tert-butyl-9,9-dimethyl-9H-fluoren-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9-dimethyl-9H-fluoren-2-amine

[0554] Compound C: 2-(3'-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine

[0555] Compound D: 6,6'-(naphthalene-1,2-diylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine)

[0556] Host H1: 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(triphenylen-2-yl)phenyl)-1,3,5-triazine

[0557] Host H2: 9,9''-diphenyl-9H,9''H-3,3':9',3''-tercarbazole

[0558] GD:

[0559]

[0560]

[0561] Examples 2 to 4, Comparative Examples 1 to 5

[0562] The devices of Examples 2 to 4 and Comparative Examples 1 to 5 were fabricated in the same manner as Example 1, except that the composition of the hole transport assist layer was changed as described in Table 1 below.

[0563]

[0564] evaluation

[0565] (1) Measurement of change in current density according to voltage change

[0566] 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.

[0567] (2) Measurement of change in brightness according to voltage change

[0568] 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.

[0569] (3) Measurement of luminous efficiency

[0570] 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.

[0571] (4) Driving voltage measurement

[0572] Using a current-voltage meter (Keithley 2400) at 15 mA / cm 2 The driving voltage of each component was measured to obtain the results.

[0573] (5) Life measurement

[0574] 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%.

[0575] The relative values ​​based on the luminous efficiency, lifespan, and driving voltage of Comparative Example 1 are shown in Table 2 below.

[0576] Hole Transport Auxiliary Layer Driving Voltage (%) Efficiency (%) Lifetime (%) Example 11-25 106 106 262 Example 21-86 107 107 257 Example 31-899 6108 297 Example 41-262 108 106 270 Comparative Example 1 R1 100 100 100 Comparative Example 2 R295 104 154 Comparative Example 3 R3 108 105 211 Comparative Example 4 R4 119 102 243 Comparative Example 5 R5 110 104 178

[0577] Referring to Table 2, it can be seen that the organic light-emitting device to which the compound according to the embodiment of the present invention is applied has significantly improved efficiency and lifespan compared to the organic light-emitting device according to the comparative example.

[0578] Although the embodiments 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 compound for organic optoelectronic devices represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X 1 is O or S, R 1 and R 2 Each is independently hydrogen, deuterium, cyano group, halogen 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 R 3 to R 5 Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and L 1 and L 2 Each is independently a single bonded, substituted, or unsubstituted C6 to C30 arylene group, and Ar 1 and Ar 2 Each is independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m1 and m2 are each independently one of integers from 1 to 3, and If m1 and m2 are 2 or more, respectively R 1 and R 2 They are identical or different from each other.

2. In Paragraph 1, The above Ar 1 and Ar 2 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 triphenylene group, a substituted or unsubstituted 1-fluorenyl group, a substituted or unsubstituted 2-fluorenyl group, a substituted or unsubstituted 3-fluorenyl group, a substituted or unsubstituted 4-fluorenyl group, a substituted or unsubstituted 9-fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9'-spirobifluorenyl group, a substituted or unsubstituted dibenzosilolyl group, a substituted or unsubstituted xanthenyl group, a substituted or unsubstituted spirocyclopentane-1,9'-fluorenyl group, a substituted or unsubstituted spirocyclohexane-1,9'-fluorenyl group, or a substituted or unsubstituted A compound for organic optoelectronic devices containing a spirofluorene-9,9'-xanthenyl group.

3. In Paragraph 1, The above Ar 1 and Ar 2 Compounds for organic optoelectronic devices, each independently selected from the substituents listed in Group I below: [Group I] In the above Group I, R 16 to R 20 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, or a substituted or unsubstituted C6 to C12 aryl group, and R 21 and R 22 Each is independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group, and m5 is one of integers from 1 to 5, and m6 is one of integers from 1 to 4, and m7 is one of integers from 1 to 3, and m8 is one of integers from 1 to 8, and m9 is one of the integers 1 to 10, and * is a connection point.

4. In Paragraph 1, The above R 3 to R 5 A compound for an organic optoelectronic device, wherein each is independently a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.

5. In Paragraph 1, The above R 3 to R 5 A compound for an organic optoelectronic device, wherein each is independently a substituted or unsubstituted iso-propyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

6. In Paragraph 1, The compound for an organic optoelectronic device represented by the above chemical formula 1 is an organic optoelectronic device compound selected from the compounds listed in Group 1 below: [Group 1] [1-1] [1-2] [1-3] [1-4] [1-5] [1-6] [1-7] [1-8] [1-9] [1-10] [1-11] [1-12] [1-13] [1-14] [1-15] [1-16] [1-17] [1-18] [1-19] [1-20] [1-21] [1-22] [1-23] [1-24] [1-25] [1-26] [1-27] [1-28] [1-29] [1-30] [1-31] [1-32] [1-33] [1-34] [1-35] [1-36] [1-37] [1-38] [1-39] [1-40] [1-41] [1-42] [1-43] [1-44] [1-45] [1-46] [1-47] [1-48] [1-49] [1-50] [1-51] [1-52] [1-53] [1-54] [1-55] [1-56] [1-57] [1-58] [1-59] [1-60] [1-61] [1-62] [1-63] [1-64] [1-65] [1-66] [1-67] [1-68] [1-69] [1-70] [1-71] [1-72] [1-73] [1-74] [1-75] [1-76] [1-77] [1-78] [1-79] [1-80] [1-81] [1-82] [1-83] [1-84] [1-85] [1-86] [1-87] [1-88] [1-89] [1-90] [1-91] [1-92] [1-93] [1-94] [1-95] [1-96] [1-97] [1-98] [1-99] [1-100] [1-101] [1-102] [1-103] [1-104] [1-105] [1-106] [1-107] [1-108] [1-109] [1-110] [1-111] [1-112] [1-113] [1-114] [1-115] [1-116] [1-117] [1-118] [1-119] [1-120] [1-121] [1-122] [1-123] [1-124] [1-125] [1-126] [1-127] [1-128] [1-129] [1-130] [1-131] [1-132] [1-133] [1-134] [1-135] [1-136] [1-137] [1-138] [1-139] [1-140] [1-141] [1-142] [1-143] [1-144] [1-145] [1-146] [1-147] [1-148] [1-149] [1-150] [1-151] [1-152] [1-153] [1-154] [1-155] [1-156] [1-157] [1-158] [1-159] [1-160] [1-161] [1-162] [1-163] [1-164] [1-165] [1-166] [1-167] [1-168] [1-169] [1-170] [1-171] [1-172] [1-173] [1-174] [1-175] [1-176] [1-177] [1-178] [1-179] [1-180] [1-181] [1-182] [1-183] [1-184] [1-185] [1-186] [1-187] [1-188] [1-189] [1-190] [1-191] [1-192] [1-193] [1-194] [1-195] [1-196] [1-197] [1-198] [1-199] [1-200] [1-201] [1-202] [1-203] [1-204] [1-205] [1-206] [1-207] [1-208] [1-209] [1-210] [1-211] [1-212] [1-213] [1-214] [1-215] [1-216] [1-217] [1-218] [1-219] [1-220] [1-221] [1-222] [1-223] [1-224] [1-225] [1-226] [1-227] [1-228] [1-229] [1-230] [1-231] [1-232] [1-233] [1-234] [1-235] [1-236] [1-237] [1-238] [1-239] [1-240] [1-241] [1-242] [1-243] [1-244] [1-245] [1-246] [1-247] [1-248] [1-249] [1-250] [1-251] [1-252] [1-253] [1-254] [1-255] [1-256] [1-257] [1-258] [1-259] [1-260] [1-261] [1-262] [1-263] [1-264] [1-265] [1-266] [1-267] [1-268] [1-269] [1-270] [1-271] [1-272] [1-273] [1-274] [1-275] [1-276] [1-277] [1-278] [1-279] [1-280] [1-281] [1-282] [1-283] [1-284] [1-285] [1-286] [1-287] [1-288] [1-289] [1-290] [1-291] [1-292] [1-293] [1-294] [1-295] [1-296] [1-297] [1-298] [1-299] [1-300] [1-301] [1-302] [1-303] [1-304] [1-305] [1-306] [1-307] [1-308] [1-309] [1-310] Dn represents the number of hydrogens substituted with deuterium, and n is an integer greater than or equal to 0, and the maximum number of n corresponds to the number of hydrogen positions that can be substituted.

7. 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 compound for an organic optoelectronic device according to any one of claims 1 to 6.

8. In Paragraph 7, The above organic layer includes a light-emitting layer, and The above-mentioned light-emitting layer is an organic optoelectronic device comprising a compound for the organic optoelectronic device.

9. In Paragraph 7, The above organic layer includes a light-emitting layer, and A hole transport layer is included between the anode and the light-emitting layer, It includes a hole transport auxiliary layer between the light-emitting layer and the hole transport layer, The above hole transport assist layer is an organic optoelectronic device comprising a compound for the organic optoelectronic device.

10. In Paragraph 9, An organic optoelectronic device wherein the hole transport layer comprises a compound represented by the following chemical formula 2: [Chemical Formula 2] In the above chemical formula 2, Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and L 3 and L 4 Each is independently a single bonded, substituted, or unsubstituted C6 to C30 arylene group, and Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and R 6 to R 10 Each is independently hydrogen, deuterium, cyano group, halogen 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 m3 is one of integers from 1 to 3, and If m3 is 2 or greater, each R 6 They are identical or different from each other.

11. In Paragraph 10, An organic optoelectronic device wherein the above chemical formula 2 is represented by the following chemical formula 2-4: [Chemical Formula 2-4] In the above chemical formula 2-4, Ar 3 or Ar 6 , L 3 , L 4 , R 6 to R 10 and m3 are as defined in Paragraph 10.

12. In Paragraph 10, An organic optoelectronic device wherein the hole transport layer comprises a compound represented by the following chemical formula 2-4-1: [Chemical Formula 2-4-1] In the above chemical formula 2-4-1, Ar 4 or Ar 6 , L 3 , L 4 , R 6 to R 10 and m3 are as defined in Paragraph 10, and Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group, and R 11 to R 15 Each is independently hydrogen, deuterium, cyano group, halogen 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 m4 is one of the integers 1 to 3.

13. In Paragraph 10, An organic optoelectronic device wherein the hole transport layer comprises a compound represented by the following chemical formula 2-4-1b: [Chemical Formula 2-4-1b] In the above chemical formula 2-4-1b, Ar 4 or Ar 8 , R 6 to R 15 , m3 and m4 are as defined in Paragraph 10.

14. In Paragraph 10, An organic optoelectronic device in which the compound represented by the above chemical formula 2 is one selected from the compounds listed in Group 2 below: [Group 2] [F-1] [F-2] [F-3] [F-4] [F-5] [F-6] [F-7] [F-8] [F-9] [F-10] [F-11] [F-12] [F-13] [F-14] [F-15] [F-16] [F-17] [F-18] [F-19] [F-20] [F-21] [F-22] [F-23] [F-24] [F-25] [F-26] [F-27] [F-28] [F-29] [F-30] [F-31] [F-32] [F-33] [F-34] [F-35] [F-36] [F-37] [F-38] [F-39] [F-40] [F-41] [F-42] [F-43] [F-44] [F-45] [F-46] [F-47] [F-48] [F-49] [F-50] [F-51] [F-52] [F-53] [F-54] [F-55] [F-56] [F-57] [F-58] [F-59] [F-60] (Dn represents the number of hydrogens substituted with deuterium, n is an integer greater than or equal to 0, and the maximum value of n corresponds to the number of replaceable hydrogen positions.) 15. A display device comprising an organic optoelectronic element according to paragraph 7.

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