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

Abstract

The present invention relates to a compound for an organic optoelectronic device, the compound represented by Chemical Formula 1; and an organic optoelectronic device and a display device each comprising the compound. Detailed explanation of Chemical Formula 1 is defined in the specification.

Description

Technical Field

[0001] Compounds for use in organic optoelectronic devices, organic optoelectronic devices, and display devices are disclosed. Background Technology

[0002] Organic optoelectronic devices (organic optoelectronic diodes) are devices that can convert electrical energy into light energy and vice versa.

[0003] Based on their working principles, organic optoelectronic devices can be broadly classified into two categories. One category consists of optoelectronic devices that generate electrical energy by separating excitons formed by light energy into electrons and holes, and then transferring the electrons and holes to different electrodes. The other category consists of light-emitting devices that generate light energy from electrical energy by providing voltage or current to the electrodes.

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

[0005] In recent years, organic light-emitting diodes (OLEDs) have attracted much attention due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is significantly affected by the organic materials between the electrodes. Summary of the Invention

[0006] Technical issues

[0007] One embodiment provides a compound for organic optoelectronic devices that enables long cycle life organic optoelectronic devices to operate effectively even at low voltages.

[0008] Another embodiment provides an organic optoelectronic device comprising the compound for the organic optoelectronic device.

[0009] Another embodiment provides a display device including the organic optoelectronic device.

[0010] Technical solution

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

[0012] [Chemical Formula 1]

[0013] In chemical formula 1, X 1 Is it O or S? R 1 and R 2Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R 3 To R 5 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. 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. m1 and m2 are each an independent integer from 1 to 3, and When m1 and m2 are 2 or greater, each R 1 and R 2 They are the same as or different from each other.

[0014] According to another embodiment, the organic optoelectronic device includes 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 contains the compound for the organic optoelectronic device.

[0015] According to another embodiment, a display device including the organic optoelectronic device is provided.

[0016] Beneficial effects

[0017] It can realize long-life organic optoelectronic devices that can operate effectively even at low voltages. Attached Figure Description

[0018] Figure 1 This is a cross-sectional view showing an organic light-emitting diode according to one embodiment.

[0019] <Explanation of Figure Markers>

[0020] 10: Anode 20: Cathode

[0021] 30: Organic layer; 31: Hole transport layer

[0022] 32: Emissive layer; 33: Hole transport auxiliary layer

[0023] 34: Electronic transmission area Detailed Implementation

[0024] Embodiments of the present invention are described in detail below. However, these embodiments are exemplary, and this disclosure is not limited thereto.

[0025] In this specification, unless otherwise defined, “substituted” means that at least one hydrogen atom of a substituent or compound is replaced by a deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amino, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or combinations thereof.

[0026] In one embodiment of the invention, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. In a specific embodiment of the invention, "substituted" means that at least one hydrogen atom of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0027] "Unsubstituted" means that the hydrogen atom has not been replaced by another substituent and the hydrogen atom is retained.

[0028] In this specification, "hydrogen (-H)" may include "deuterium-substituted (-D)" or "tritium-substituted (-T)".

[0029] In this specification, unless otherwise defined, "hetero" means a group that contains one to three heteroatoms selected from N, O, S, P and Si in one functional group and the remainder is carbon.

[0030] In this specification, "aryl" means a group containing at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have conjugated p orbitals, such as phenyl, naphthyl, etc., which can be linked by σ bonds, and the hydrocarbon aromatic moiety can be, for example, biphenyl, terphenyl, tetraphenyl, etc., and the two or more hydrocarbon aromatic moiety are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorene.

[0031] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0032] In this specification, "heterocyclic group" is a superordinate concept of heteroaryl and may contain at least one heteroatom selected from N, O, S, P, and Si to replace carbon (C) in cyclic compounds such as aryl, cycloalkyl, their fused rings, or combinations thereof. When the heterocyclic group is fused, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0033] For example, "heteroaryl" can represent an aryl group comprising at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly linked by σ bonds, or when a heteroaryl group comprises two or more rings, the two or more rings can be fused. When a heteroaryl group is a fused ring, each ring can contain 1 to 3 heteroatoms.

[0034] More specifically, the substituted or unsubstituted C6 to C30 aryl group can be a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthraquinone, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted pyrene, a substituted or unsubstituted biphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted meta-terphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted trefyl, a substituted or unsubstituted benzophenone, a substituted or unsubstituted triphenyl, a substituted or unsubstituted perylene, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted indene, or a combination thereof, but is not limited thereto.

[0035] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group can be a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indoleyl group, a substituted or unsubstituted quinolinyl group, or a substituted or unsubstituted... The following are substituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxolinyl, substituted or unsubstituted naphthinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted xanthanyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzonaphthothiophenyl, substituted or unsubstituted benzofuran fluorenyl, substituted or unsubstituted benzothiophene fluorenyl, or combinations thereof, but not limited thereto.

[0036] In this specification, hole characteristics refer to the ability to contribute electrons to form holes when an electric field is applied, and due to the conductivity characteristics of the highest occupied molecular orbital (HOMO) energy level, holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0037] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductivity of the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0038] The following describes a compound for an organic optoelectronic device according to one embodiment.

[0039] The compound represented by chemical formula 1 is used in an organic optoelectronic device according to one embodiment.

[0040] [Chemical Formula 1]

[0041] In chemical formula 1, X 1 Is it O or S? R 1 and R 2 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R 3 To R 5 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. L 1 and L 2 Each is independently a single bond or a substituted or unsubstituted C6 to C30 arylene group. 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. m1 and m2 are each an independent integer from 1 to 3. When m1 is 2 or greater, each R 1 They are the same as or different from each other.

[0042] When m2 is 2 or greater, each R 2 They are the same as or different from each other.

[0043] In compounds represented by Formula 1 for organic optoelectronic devices, the 6-position of dibenzofuran (or dibenzothiophene) is a highly reactive site that can affect molecular stability during hole injection and electron leakage. Therefore, silane groups with high electronic stability have been introduced at the 6-position to improve the lifetime of organic light-emitting diodes (OLEDs) using them.

[0044] In addition, by introducing silane, the glass transition temperature of the compound was improved and a high T1 energy was achieved, thereby attempting to improve the efficiency of organic light-emitting diodes using it.

[0045] For example, Ar 1 and Ar 2It can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted 1-fluorenyl, a substituted or unsubstituted 2-fluorenyl, a substituted or unsubstituted 3-fluorenyl, a substituted or unsubstituted 4-fluorenyl, a substituted or unsubstituted 9-fluorenyl, or a substituted or unsubstituted dibenzofuran. The following are compounds: 1-yl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted 9,9'-spirofluorenyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted xanthonyl, substituted or unsubstituted spirocyclopentane-1,9'-fluorenyl, substituted or unsubstituted spirocyclohexane-1,9'-fluorenyl, substituted or unsubstituted spirofluorene-9,9'-xanthonyl, or substituted or unsubstituted spirofluorene-9,9'-thiaxanthonyl.

[0046] As a specific example, Ar 1 and Ar 2 Each can be independently selected from the substituents listed in Group I.

[0047] Group I

[0048] In group I, R 16 To R 20 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, or substituted or unsubstituted C6 to C12 aryl. R 21 and R 22 Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl. m5 is an integer from 1 to 5. m6 is an integer from 1 to 4. m7 is an integer from 1 to 3. m8 is an integer from 1 to 8. m9 is an integer from 1 to 10, and It is a connection point.

[0049] When m5 is 2 or greater, each R 16 They can be the same as or different from each other.

[0050] When m6 is 2 or greater, each R 17 They can be the same as or different from each other.

[0051] When m7 is 2 or greater, each R 18They can be the same as or different from each other.

[0052] When m8 is 2 or greater, each R 19 They can be the same as or different from each other.

[0053] When m9 is 2 or greater, each R 20 They can be the same as or different from each other.

[0054] For example, Ar 1 and Ar 2 It can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted 1-fluorenyl, a substituted or unsubstituted 2-fluorenyl, a substituted or unsubstituted 3-fluorenyl, a substituted or unsubstituted 4-fluorenyl, a substituted or unsubstituted 9-fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0055] In one implementation, Ar 1 It can be a substituted or unsubstituted 2-fluorene group, and Ar 2 It can be a substituted or unsubstituted 4-fluorene group.

[0056] For example, L 1 and L 2 Each can be a single bond or a substituted or unsubstituted C6 to C12 aryl group.

[0057] For example, L 1 and L 2 Each can be a single bond or a substituted or unsubstituted phenylene group, and each can be independent of the others.

[0058] For example, R 3 To R 5 They can be substituted or unsubstituted C1 to C10 alkyl groups or substituted or unsubstituted C6 to C12 aryl groups, each independently.

[0059] As a specific example, R 3 To R 5 Each can be independently a substituted or unsubstituted isopropyl, a substituted or unsubstituted tert-butyl, a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

[0060] For example, a compound represented by chemical formula 1 for an organic optoelectronic device may be selected from, but is not limited to, one of the compounds listed in group 1.

[0061] [Group 1]

[0062] [1-1] [1-2] [1-3] [1-4] [1-5]

[0063] [1-6] [1-7] [1-8] [1-9] [1-10]

[0064] [1-11] [1-12] [1-13] [1-14] [1-15]

[0065] [1-16] [1-17] [1-18] [1-19] [1-20]

[0066] [1-21] [1-22] [1-23] [1-24] [1-25]

[0067] [1-26] [1-27] [1-28] [1-29] [1-30]

[0068] [1-31] [1-32] [1-33] [1-34] [1-35]

[0069] [1-36] [1-37] [1-38] [1-39] [1-40]

[0070] [1-41] [1-42] [1-43] [1-44] [1-45]

[0071] [1-46] [1-47] [1-48] [1-49] [1-50]

[0072] [1-51] [1-52] [1-53] [1-54] [1-55]

[0073] [1-56] [1-57] [1-58] [1-59] [1-60]

[0074] [1-61] [1-62] [1-63] [1-64] [1-65]

[0075] [1-66] [1-67] [1-68] [1-69] [1-70]

[0076] [1-71] [1-72] [1-73] [1-74] [1-75]

[0077] [1-76] [1-77] [1-78] [1-79] [1-80]

[0078] [1-81] [1-82] [1-83] [1-84] [1-85]

[0079] [1-86] [1-87] [1-88] [1-89] [1-90]

[0080] [1-91] [1-92] [1-93] [1-94] [1-95]

[0081] [1-96] [1-97] [1-98] [1-99] [1-100]

[0082] [1-101] [1-102] [1-103] [1-104] [1-105]

[0083] [1-106] [1-107] [1-108] [1-109] [1-110]

[0084] [1-111] [1-112] [1-113] [1-114] [1-115]

[0085] [1-116] [1-117] [1-118] [1-119] [1-120]

[0086] [1-121] [1-122] [1-123] [1-124] [1-125]

[0087] [1-126] [1-127] [1-128] [1-129] [1-130]

[0088] [1-131] [1-132] [1-133] [1-134] [1-135]

[0089] [1-136] [1-137] [1-138] [1-139] [1-140]

[0090] [1-141] [1-142] [1-143] [1-144] [1-145]

[0091] [1-146] [1-147] [1-148] [1-149] [1-150]

[0092] [1-151] [1-152] [1-153] [1-154] [1-155]

[0093] [1-156] [1-157] [1-158] [1-159] [1-160]

[0094] [1-161] [1-162] [1-163] [1-164] [1-165]

[0095] [1-166] [1-167] [1-168] [1-169] [1-170]

[0096] [1-171] [1-172] [1-173] [1-174] [1-175]

[0097] [1-176] [1-177] [1-178] [1-179] [1-180]

[0098] [1-181] [1-182] [1-183] [1-184] [1-185]

[0099] [1-186] [1-187] [1-188] [1-189] [1-190]

[0100] [1-191] [1-192] [1-193] [1-194] [1-195]

[0101] [1-196] [1-197] [1-198] [1-199] [1-200]

[0102] [1-201] [1-202] [1-203] [1-204] [1-205]

[0103] [1-206] [1-207] [1-208] [1-209] [1-210]

[0104] [1-211] [1-212] [1-213] [1-214] [1-215]

[0105] [1-216] [1-217] [1-218] [1-219] [1-220]

[0106] [1-221] [1-222] [1-223] [1-224] [1-225]

[0107] [1-226] [1-227] [1-228] [1-229] [1-230]

[0108] [1-231] [1-232] [1-233] [1-234] [1-235]

[0109] [1-236] [1-237] [1-238] [1-239] [1-240]

[0110] [1-241] [1-242] [1-243] [1-244] [1-245]

[0111] [1-246] [1-247] [1-248] [1-249] [1-250]

[0112] [1-251] [1-252] [1-253] [1-254] [1-255]

[0113] [1-256] [1-257] [1-258] [1-259] [1-260]

[0114] [1-261] [1-262] [1-263] [1-264] [1-265]

[0115] [1-266] [1-267] [1-268] [1-269] [1-270]

[0116] [1-271] [1-272] [1-273] [1-274] [1-275]

[0117] [1-276] [1-277] [1-278] [1-279] [1-280]

[0118] [1-281] [1-282] [1-283] [1-284] [1-285]

[0119] [1-286] [1-287] [1-288] [1-289] [1-290]

[0120] [1-291] [1-292] [1-293] [1-294] [1-295]

[0121] [1-296] [1-297] [1-298] [1-299] [1-300]

[0122] [1-301] [1-302] [1-303] [1-304] [1-305]

[0123] [1-306] [1-307] [1-308] [1-309] [1-310]

[0124] Dn represents the number of hydrogen atoms that are replaced by deuterium, where n is an integer of 0 or greater, and the maximum value of n corresponds to the number of hydrogen sites that can be substituted.

[0125] An organic optoelectronic device using the above-described compound for organic optoelectronic devices is described.

[0126] Organic optoelectronic devices can be suitable devices that convert electrical energy into light energy (and vice versa), such as organic photoelectric devices, organic light-emitting diodes, organic solar cells, or organic photoconductor drums.

[0127] In this paper, an organic light-emitting diode (OLED) is described as an example of an organic optoelectronic device, with reference to the accompanying drawings.

[0128] Figure 1 This is a schematic cross-sectional view of an organic light-emitting diode according to one embodiment.

[0129] refer to Figure 1 An organic light-emitting diode 100 according to one embodiment includes an anode 10 and a cathode 20, and an organic layer 30 located between the anode 10 and the cathode 20.

[0130] The anode 10 can be made of a conductor with a high work function to facilitate hole injection, such as metals, metal oxides, and / or conductive polymers. The anode 10 can be made of metals such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO and Al or SnO2 and Sb; and conductive polymers such as, but not limited to, poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxo)thiophene) (PEDOT), polypyrrole, and polyaniline.

[0131] For example, the cathode 20 can be made of a conductor with a low work function to facilitate electron injection, and can be made of metals, metal oxides, and / or conductive polymers. The cathode 20 can be made of the following materials: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or alloys thereof; multilayer structure materials, such as LiF / Al, LiO2 / Al, LiF / Ca, and BaF2 / Ca, but not limited to these.

[0132] 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.

[0133] The organic layer 30 may contain the compounds described above for organic optoelectronic devices.

[0134] For example, the light-emitting layer 32 may contain the compounds described above for organic optoelectronic devices.

[0135] At this time, the light-emitting layer 32 may contain, for example, the compound used in organic optoelectronic devices described above as a host, and the host may be, for example, a phosphorescent host.

[0136] The phosphorescent host should facilitate the injection and transport of holes and electrons within the luminescent layer, ultimately enabling holes and electrons to meet and form excitons, and should be able to effectively transfer the energy of the formed excitons to the dopant.

[0137] The light-emitting layer 32 may also contain dopants, and the composition containing the phosphorescent host and the dopants may be, for example, a red-emitting or green-emitting composition.

[0138] The dopant can be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, such as a red or green phosphorescent dopant.

[0139] A dopant is a material that is mixed in small amounts with the host to induce luminescence, and can typically be a material that emits light by being excited to a triplet or more states multiple times, such as a metal complex. Dopants can be, for example, inorganic, organic, or organic-inorganic compounds, and one or more of these types can be used.

[0140] Examples of dopants can be phosphorescent dopants, and examples of phosphorescent dopants can be organometallic compounds, including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants can be, for example, compounds represented by the chemical formula Z, but are not limited thereto.

[0141] [Chemical Formula Z]

[0142] L 3 MX 2

[0143] In the chemical formula Z, M is a metal, and L 3 and X 2 They may be the same or different, and they are ligands that form complexes with M.

[0144] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 3 and X 2 It could be, for example, a bidentate ligand.

[0145] By L 3 and X 2 The ligands represented may be selected from chemical formulas Z-1 to Z-8, but are not limited thereto.

[0146] [Z-1] [Z-2] [Z-3]

[0147] [Z-4] [Z-5]

[0148] [Chemical Formula Z-6] [Chemical Formula Z-7]

[0149] [Z-8]

[0150] In chemical formulas Z-1 to Z-8 X 14 Selected from carbon and nitrogen, Y 100 Is it O or S? R 101 To R 122Each of these elements is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C6 to C20 aryl, -SiR. 133 R 134 R 135 Or -GeR 133 R 134 R 135 Alternatively, it can be attached to an adjacent substituent to form a substituted or unsubstituted ring, and, for example, together with pyridine, can be a substituted or unsubstituted quinoline, a substituted or unsubstituted benzofuranopyridine, a substituted or unsubstituted benzothiophenopyridine, a substituted or unsubstituted indenepyridine, a substituted or unsubstituted benzofuranoquinoline, a substituted or unsubstituted benzothiophenoquinoline, or a substituted or unsubstituted indenequinoline; m18 is an integer from 1 to 4, and m19 is an integer from 1 to 5.

[0151] By L 3 and X 2 Specific examples of the ligands represented may be selected from (but are not limited to) the chemical formulas listed in group A.

[0152] [Group A]

[0153] In group A, R 300 To R 302 Each is independently hydrogen, deuterium, halogen-substituted or unsubstituted C1 to C30 alkyl, or C6 to C30 aryl substituted or unsubstituted C1 to C30 alkyl or halogen-substituted. R 303 To R 308 Each of the following is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, trialkylsilyl having substituted or unsubstituted C1 to C30 alkyl, dialkylarylsilyl having substituted or unsubstituted C1 to C30 alkyl and C6 to C30 aryl, or triarylsilyl having substituted or unsubstituted C6 to C30 aryl. m25 is an integer from 1 to 5. m26 is an integer from 1 to 4. m27 is an integer from 1 to 3. m28 is an integer of 1 or 2. m29 is an integer from 1 to 6, and When m25 to m29 are 2 or greater, each R 303 To R 307 They are the same as or different from each other.

[0154] In one embodiment, the phosphorescent dopant may be an iridium complex and may be represented by, for example, any of the formulas 9 to 11.

[0155] [Chemical Formula 9]

[0156] In chemical formula 9, Ring A is a monocyclic or polycyclic fused ring. In both monocyclic and polycyclic fused rings, each ring is a five- or six-membered carbon ring or heterocyclic ring. R 100 Represents a monovalent substituent up to a maximum number. When R 100 When it is 2 or greater, each R 100 Are they the same or different from each other? R 101 To R 104 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them, R 114 To R 116 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. X 10 and X 11 Each is independently selected from carbon and nitrogen. L 100 It is a ligand or bidentate ligand of a monovalent anion, which coordinates to iridium via the lone pair electrons of a carbon or heteroatom, and m21 is any integer between 0 and 3.

[0157] [Chemical Formula 10]

[0158] In chemical formula 10, Ring B is a monocyclic or polycyclic fused ring. In both monocyclic and polycyclic fused rings, each ring is a five- or six-membered carbon ring or heterocyclic ring. Y 100 Is it O or S? R 201 Represents a monovalent substituent up to a maximum number. When R 201 When it is 2 or greater, each R 201 Are they the same or different from each other? R 206 To R 213 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them, R 114 To R 116 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. X 12 and X 13 Each is independently selected from carbon and nitrogen. L 100 It is a ligand or bidentate ligand of a monovalent anion, which coordinates to iridium via the lone pair electrons of a carbon or heteroatom, and m21 is any integer between 0 and 3.

[0159] [Chemical Formula 11]

[0160] In chemical formula 11, Y 100 Is it O or S? R 101 To R 111 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 114 R 115 R 116 -GeR 114 R 115 R 116 Or a combination of them, R 114 To R 116 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. L 100 It is a ligand or bidentate ligand of a monovalent anion, which coordinates to iridium via the lone pair electrons of a carbon or heteroatom, and m21 is any integer between 0 and 3.

[0161] As a more specific example, iridium complexes can be represented by one of chemical formulas 9-1 to 9-6.

[0162] [Chemical Formula 9-1]

[0163] In chemical formula 9-1, R 101 To R 116 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 132 R 133 R 134 Or -GeR 132 R 133 R 134 , R 132 To R 134 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. R 101 To R 116 At least one of them is a functional group represented by the chemical formula V-1. L 100 It is a bidentate ligand for monovalent anions, and is a ligand that coordinates to iridium via the lone pair electrons of carbon or heteroatoms. m21 and m22 are each independent integers from 0 to 3, and m21 + m22 is an integer from 1 to 3. [Chemical Formula V-1]

[0164] In chemical formula V-1, R 135 To R 139 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 132 R 133 R 134 ,and It refers to the part that is attached to a carbon atom.

[0165] [Chemical Formula 9-2]

[0166] [Chemical Formula 9-3]

[0167] [Chemical Formula 9-4]

[0168] [Chemical Formula 9-5]

[0169] [Chemical Formula 9-6]

[0170] Among them, in chemical formulas 9-2 to 9-6, X 14 Selected from carbon and nitrogen, Y 100 Is it O or S? R 101 To R 122 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 , R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. L 100 It is a bidentate ligand for monovalent anions, and is a ligand that coordinates to iridium via the lone pair electrons of carbon or heteroatoms. m111 is an integer between 1 and 2, and n1 and n2 are independent integers from 0 to 3, and n1 + n2 is an integer from 1 to 3. In another embodiment, the dopant may be, for example, a platinum complex represented by the chemical formula Z-9.

[0171] [Chemical Formula Z-9]

[0172] In chemical formula Z-9, rings A, B, C, and D are each independently a five- or six-membered carbon ring or a heterocyclic ring; R A R B R C and R D Each can be independently monosubstituted, disubstituted, trisubstituted, or tetrasubstituted, or unsubstituted; nA is an integer that is either 0 or 1; L B L C and LD Each is independently a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof. When nA is 1, L E It can be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', or a combination thereof; and when nA is 0, L E It does not exist; R A R B R C R D R and R' are each independently hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxyl, ester, cyano, isonitrile, thioalkyl, thionyl, sulfonyl, phosphinyl, or combinations thereof; any adjacent R A R B R C R D R and R' are optionally connected to each other to provide a loop; X B X C X D and X E Each is independently selected from carbon and nitrogen; and Q 1 Q 2 Q 3 and Q 4 Each represents oxygen or a direct bond.

[0173] Platinum complexes can be represented, for example, by chemical formula 12-1 or chemical formula 12-2.

[0174] [Chemical Formula 12-1]

[0175] [Chemical Formula 12-2]

[0176] In chemical formulas 12-1 and 12-2, X 100 Selected from O, S and NR 132 , R 118 To R 132 Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR. 133 R 134 R 135 , R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group. R 118 To R 132 At least one of them is -SiR 133 R 134 R 135 Or tert-butyl, and R 133 To R 135 Each is independently a substituted or unsubstituted C1 to C6 alkyl group.

[0177] In addition, the compounds described above for organic optoelectronic devices may be included in the light-emitting layer 32, and at least one of the compounds listed in group B may be included in at least one layer of the hole transport layer 31 and the hole transport auxiliary layer 33.

[0178] [Group B]

[0179] (Dn represents the number of hydrogen atoms replaced by deuterium, where n is an integer of 0 or greater, and the maximum value of n corresponds to the number of hydrogen sites that can be substituted.)

[0180] In addition to the compounds described above, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A and compounds with similar structures may also be used in hole transport layer 31 and hole transport auxiliary layer 33.

[0181] For example, hole transport auxiliary layer 33 may contain the compounds described above for organic optoelectronic devices.

[0182] In this document, examples of phosphorescent hosts contained in the luminescent layer 32 may include organic compounds, including carbazole, indolocarbazole, dibenzofuran, dibenzothiophene, indolodibenzopyran, indolodibenzothiophene, fluorene, indobenzocarbazole, triphenylene, pyrimidine, triazine, or combinations thereof.

[0183] Phosphorescent substrates can be used without restriction, as long as they are known materials, and can be, for example, a single substrate or a mixture of substrates.

[0184] In addition, the dopants contained in the light-emitting layer 32 are as described above.

[0185] Meanwhile, the hole transport layer 31 is a layer that helps holes to be transported from the anode 10 to the light-emitting layer 32, and may be, for example, an amine compound, but is not limited thereto.

[0186] Amine compounds may contain, for example, at least one aryl and / or heteroaryl group. Amine compounds may be represented by, for example, chemical formula a or chemical formula b, but are not limited thereto.

[0187] [Chemical Formula a] [Chemical Formula b]

[0188] In chemical formula a or b Ar a To Ar g Each is independently hydrogen, deuterium, substituted or unsubstituted C1 to C20 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heteroaryl, or a combination thereof. Ar a To Ar c At least one of them and Ar d To Ar g At 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 Ar h It 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.

[0189] For example, hole transport auxiliary layer 33 contains the compounds for organic optoelectronic devices described above, and hole transport layer 31 may contain compounds represented by chemical formula 2.

[0190] [Chemical Formula 2]

[0191] In 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. L 3 and L 4 Each is independently a single bond or a substituted or unsubstituted C6 to C30 arylene group. Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 6 To R 10 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. m3 is an integer from 1 to 3, and When m3 is 2 or greater, each R 6 They are the same as or different from each other.

[0192] Since the amine core is replaced by at least one fluorene group, steric hindrance can be minimized by reducing the deposition temperature, thereby further improving lifetime characteristics.

[0193] For example, based on the substitution position of fluorene, chemical formula 2 can be represented by any of chemical formulas 2-1 to 2-4.

[0194] [Chemical Formula 2-1] [Chemical Formula 2-2]

[0195] [Chemical Formula 2-3] [Chemical Formula 2-4]

[0196] In chemical formulas 2-1 to 2-4 Ar 3 To Ar 6 L 3 L 4 R 6 To R 10 The same applies to m3 as described above.

[0197] For example, compounds contained in the hole transport layer can be represented by chemical formulas 2-4.

[0198] In chemical formula 2, Ar 3 and Ar 4 Each of these can be independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophene.

[0199] For example, Ar 3 and Ar 4 Each can be independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted fluorene group.

[0200] In chemical formula 2, Ar 5 and Ar 6 Each can be independently a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0201] For example, Ar 5 and Ar 6 Each can be independently a substituted or unsubstituted C1 to C5 alkyl, a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

[0202] In chemical formula 2, R6 To R 10 Each can be hydrogen, deuterium, or substituted or unsubstituted C1 to C5 alkyl groups, independently.

[0203] For example, R 6 To R 10 They can be hydrogen, deuterium, or tert-butyl, each independently.

[0204] For example, Ar 3 and Ar 4 At least one of them can be a substituted or unsubstituted fluorene group, for example, it can be represented by chemical formula 2-4-1.

[0205] [Chemical Formula 2-4-1]

[0206] In chemical formula 2-4-1, Ar 4 To Ar 6 L 3 L 4 R 6 To R 10 The same applies to m3 as described above. Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 11 To R 15 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m4 is an integer from 1 to 3.

[0207] In chemical formula 2-4-1, when m4 is 2 or greater, each R 11 They can be the same as or different from each other.

[0208] In chemical formula 2-4-1, Ar 7 and Ar 8 Each can be independently a substituted or unsubstituted C1 to C5 alkyl or a substituted or unsubstituted C6 to C12 aryl.

[0209] For example, Ar 7 and Ar 8 Each can be independently a substituted or unsubstituted C1 to C5 alkyl group, or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted naphthyl group.

[0210] In chemical formula 2-4-1, R6 To R 10 Each can be hydrogen, deuterium, or substituted or unsubstituted C1 to C5 alkyl groups, independently.

[0211] For example, R 6 To R 10 They can be hydrogen, deuterium, or tert-butyl, each independently.

[0212] As a specific example, L in chemical formula 2-4-1 3 and L 4 Each can be a single key.

[0213] As a more specific example, chemical formula 2-4-1 can be selected from chemical formula 2-4-1a, chemical formula 2-4-1b, chemical formula 2-4-1c and chemical formula 2-4-1d.

[0214] [Chemical Formula 2-4-1a] [Chemical Formula 2-4-1b]

[0215] [Chemical Formula 2-4-1c] [Chemical Formula 2-4-1d]

[0216] In chemical formulas 2-4-1a, 2-4-1b, 2-4-1c, and 2-4-1d, Ar 4 To Ar 8 R 6 To R 10 R 11 To R 15 m3 and m4 are the same as above.

[0217] As a most concrete example, the hole transport layer may contain compounds represented by the chemical formula 2-4-1b.

[0218] For example, R in chemical formula 2 7 To R 10 At least two of them can be tert-butyl.

[0219] As a specific example, R in chemical formula 2 8 and R 10 Each can be a tert-butyl.

[0220] Heat resistance can be improved by introducing alkyl groups that can improve the glass transition temperature.

[0221] In addition, by reducing the refractive index of the material, improvements in device efficiency can be expected.

[0222] For example, the compound represented by chemical formula 2 may be selected from one of the compounds listed in group 2, but is not limited thereto.

[0223] [Group 2]

[0224] [F-1] [F-2] [F-3] [F-4]

[0225] [F-5] [F-6] [F-7] [F-8]

[0226] [F-9] [F-10] [F-11] [F-12]

[0227] [F-13] [F-14] [F-15] [F-16]

[0228] [F-17] [F-18] [F-19] [F-20]

[0229] [F-21] [F-22] [F-23] [F-24]

[0230] [F-25] [F-26] [F-27] [F-28]

[0231] [F-29] [F-30] [F-31] [F-32]

[0232] [F-33] [F-34] [F-35] [F-36]

[0233] [F-37] [F-38] [F-39] [F-40]

[0234] [F-41] [F-42] [F-43] [F-44]

[0235] [F-45] [F-46] [F-47] [F-48]

[0236] [F-49] [F-50] [F-51] [F-52]

[0237] [F-53] [F-54] [F-55] [F-56]

[0238] [F-57] [F-58] [F-59] [F-60]

[0239] (Dn represents the number of hydrogen atoms replaced by deuterium, where n is an integer of 0 or greater, and the maximum value of n corresponds to the number of hydrogen sites that can be substituted.)

[0240] In addition, the organic layer 30 may also include an electron transport region 34.

[0241] The electron transport region 34 can further improve electron injection and / or electron mobility, and block holes between the cathode 20 and the light-emitting layer 32.

[0242] Specifically, the electron transport region may include an electron transport layer located between the cathode 20 and the light-emitting layer 32, and an electron transport auxiliary layer located between the light-emitting layer 32 and the electron transport layer, and may contain at least one of the compounds listed in group C in at least one of the electron transport layer and the electron transport auxiliary layer.

[0243] [Group C]

[0244] In addition to the light-emitting layer, an organic light-emitting diode may also include an electron injection layer (not shown), a hole injection layer (not shown), etc., as the aforementioned organic layer.

[0245] The hole injection layer is a layer that helps holes to be injected from the anode 10 into the light-emitting layer 32 and blocks electrons, and can be located between the anode 10 and the hole transport layer 31.

[0246] For example, the hole injection layer may contain at least one of the compounds listed in Group B.

[0247] Similarly, in addition to the hole injection layer, known compounds and compounds with similar structures described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A can also be used.

[0248] Organic light-emitting diodes 100 can be produced by forming an anode or cathode on a substrate, then forming an organic layer by dry film deposition, such as vacuum deposition, sputtering, plasma plating and ion plating, and forming a cathode or anode thereon.

[0249] Organic light-emitting diodes (OLEDs) can be used in OLED display devices.

[0250] Invention Model

[0251] In the following description, embodiments are illustrated in more detail with reference to examples. However, these embodiments are exemplary, and the scope of the invention is not limited thereto.

[0252] Unless otherwise specified, the starting materials and reactants used in the examples and synthesis examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry, or P&H Tech, or synthesized by known methods.

[0253] (Preparation of compounds for organic optoelectronic devices)

[0254] Synthesis Example 1: Synthesis of Compounds 1-25

[0255] [Reaction Formula 1]

[0256] 10.00 g (21.69 mmol) of the intermediate 9-chlorodibenzo[b,d]furan-4-yl)tripropylsilane, 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 tert-butoxide, and 0.99 g (4.88 mmol) of tritert-butylphosphine were dissolved in 220 mL of toluene. Then, 0.99 g (1.09 mmol) of Pd2(dba)3 was added, and the mixture was refluxed and stirred under nitrogen atmosphere for 4 hours. After the reaction was complete, the mixture was extracted with ethyl acetate and distilled water, and the organic layer was dried over anhydrous magnesium sulfate. The filtrate was filtered and concentrated under reduced pressure. The product was purified by silica gel column chromatography using hexane / dichloromethane (3:1 volume ratio) to obtain 13.54 g (78% yield) of compound 1-25 as a white solid.

[0257] Synthesis Example 2: Synthesis of Compounds 1-86

[0258] [Reaction 2]

[0259] Compounds 1-86 were synthesized in the same manner as in Synthesis Example 1, except that 12.00 g of intermediate 9-chlorodibenzo[b,d]furan-4-yl)tripropylsilane and 9.99 g of intermediate N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]thiophene-1-amine (14.87 g, 70% yield) were used in an equivalent ratio of 1:0.98.

[0260] Synthesis Example 3: Synthesis of Compounds 1-89

[0261] [Reaction 3]

[0262] Compounds 1-89 were synthesized in the same manner as in Synthesis Example 1, except that 25.00 g of intermediate 9-chlorodibenzo[b,d]furan-4-yl)tripropylsilane and 21.34 g of intermediate N-(9,9-dimethyl-9H-fluorene-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (35.84 g, yield 82%) were used in an equivalent ratio of 1:0.98.

[0263] Synthesis Example 4: Synthesis of Compounds 1-262

[0264] [Reaction 4]

[0265] Compound 1-262 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)tripropylsilane and 6.83 g of the intermediate di([1,1'-biphenyl]-4-yl)amine (12.62 g, 78% yield) were used in an equivalent ratio of 1:0.98.

[0266] Comparative Synthesis Example 1: Synthesis of Compound R1

[0267] Compound R1 was synthesized in the same manner as in Synthesis Example 1, except that 10.00 g of intermediate 1-chlorodibenzo[b,d]furan and 19.42 g of intermediate N-(9,9-dimethyl-9H-fluorene-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (21.01 g, 75% yield) were used in an equivalent ratio of 1:0.98.

[0268] Comparative Synthesis Example 2: Synthesis of Compound R2

[0269] Compound R2 was synthesized in the same manner as in Synthesis Example 1, except that 12.00 g of intermediate 1-chloro-6-phenyldibenzo[b,d]furan and 19.42 g of intermediate N-(9,9-dimethyl-9H-fluorene-4-yl)-9,9-dimethyl-9H-fluorene-2-amine (22.17 g, 80% yield) were used in an equivalent ratio of 1:0.98.

[0270] Comparative Synthesis Example 3: Synthesis of Compound R3

[0271] Compound R3 was synthesized in the same manner as in Synthesis Example 1, except that 15.00 g of intermediate (6-(4-bromophenyl)dibenzo[b,d]furan-4-yl)tripropylsilane and 4.28 g of intermediate diphenylamine (14.17 g, yield 82%) were used in an equivalent ratio of 1:0.98.

[0272] Comparative Synthesis Example 4: Synthesis of Compound R4

[0273] Compound R4 was synthesized in the same manner as in Synthesis Example 1, except that 10.00 g of intermediate (9-chlorodibenzo[b,d]furan-4-yl)tripropylsilane and 7.07 g of intermediate 9H-3,9'-bicarbazole (11.33 g, yield 69%) were used in an equivalent ratio of 1:0.98.

[0274] Comparative Synthesis Example 5: Synthesis of Compound R5

[0275] Compound R5 was synthesized in the same manner as in Synthesis Example 1, except that 10.00 g of intermediate 9-chlorodibenzo[b,d]furan-2-yl)tripropylsilane and 7.98 g of intermediate N-(9,9-dimethyl-9H-fluoren-2-yl)dibenzo[b,d]furan-1-amine (12.49 g, yield 72%) were used in an equivalent ratio of 1:0.98.

[0276] Evaluation 1: Comparison of simulation properties

[0277] The energy levels of each material were calculated using the Gaussian 09 method on the GAIA supercomputer (IBM power 6), and the results are shown in Table 1.

[0278] (Table 1)

[0279] Referring to Table 1, when a silane group is introduced at the 6-position of dibenzofuran, the T1 energy can be higher compared to when a substituent other than silane is introduced (Comparative Synthesis Example 2) and when silane is substituted at positions other than the 6-position (Comparative Synthesis Example 5), thus improving the efficiency of the organic light-emitting diode using it is expected. Furthermore, when Ar of Formula 1... 1 and Ar 2 When each is 2-fluorenyl and 4-fluorenyl (Synthesis Example 3), it has a shallow HOMO energy level, so low driving characteristics can be expected. Therefore, in the organic light-emitting diode using Synthesis Example 3, low driving characteristics and improved efficiency can be expected due to the above effects.

[0280] (Production of organic light-emitting diodes)

[0281] Example 1

[0282] The glass substrate coated with the ITO / Ag / ITO film was ultrasonically cleaned with distilled water. After cleaning with distilled water, the glass substrate was ultrasonically cleaned with solvents such as acetone and isopropanol and dried. It was then transferred to a plasma cleaner and cleaned with oxygen plasma for 10 minutes before being transferred to a vacuum depositor. The prepared ITO / Ag / ITO (reflective electrode) electrode was used as the anode, and compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO / Ag / ITO substrate to form a 100 Å thick hole injection layer. Compound A was then deposited on the 1350 Å thick hole injection layer to form a hole transport layer. Compounds 1-25 obtained in Synthesis Example 1 were deposited on the hole transport layer to a thickness of 335 Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, 90 wt% of host H1 (40%) and host H2 (60%) were used as the host, and 10 wt% GD was used as the dopant. A light-emitting layer with a thickness of 380 Å was formed by vacuum deposition. Subsequently, compound C was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compounds D and Liq were simultaneously vacuum deposited in a 1:1 weight ratio to form an electron transport layer with a thickness of 310 Å. An organic light-emitting diode was produced by sequentially vacuum depositing Yb and AgMg on the electron transport layer to form a cathode.

[0283] Organic light-emitting diodes are produced with the following structure: ITO / Ag / ITO / compound A (3% NDP-9 doped, 100 Å) / compound A (1350 Å) / hole transport auxiliary layer (compound 1-25, 335 Å) / light-emitting layer [body (body H1:body H2 = 40 wt%: 60 wt%): GD = 90 wt%: 10 wt%] (380 Å) / compound C (50 Å) / compound D: Liq (310 Å) / Yb (15 Å) / AgMg (1200 Å).

[0284] Compound A: N-(6,8-di-tert-butyl-9,9-dimethyl-9H-fluorene-4-yl)-N-(9,9-dimethyl-9H-fluorene-2-yl)-9,9-dimethyl-9H-fluorene-2-amine

[0285] Compound C: 2-(3'-(9,9-dimethyl-9H-fluorene-2-yl)-[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0286] Compound D: 6,6'-(naphthalene-1,2-dimethylbis(4,1-phenylene))bis(2,4-diphenyl-1,3,5-triazine))

[0287] Main component H1: 2-([1,1'-biphenyl]-4-yl)-4-phenyl-6-(3-(triphenyl-2-yl)phenyl)-1,3,5-triazine

[0288] Main component H2: 9,9''-diphenyl-9H,9''H-3,3':9',3''-tricarbazole

[0289] GD:

[0290] Examples 2 to 4 and Comparative Examples 1 to 5

[0291] The diodes of Examples 2 to 4 and Comparative Examples 1 to 5 were produced in the same manner as in Example 1, except that the composition of the hole transport auxiliary layer was changed as described in Table 1.

[0292] evaluate

[0293] (1) Measure the change in current density based on the voltage change

[0294] While increasing the voltage from 0V to 10V, the current flowing through the unit diode in the obtained organic light-emitting diode was measured using a voltmeter (Keithley 2400), and the measured current value was divided by the area to provide the result.

[0295] (2) Measure the change in brightness based on voltage changes

[0296] While increasing the voltage of the organic light-emitting diode from 0V to 10V, the brightness was measured using a photometer (Minolta Cs-1000A).

[0297] (3) Measurement of luminous efficiency

[0298] The brightness and current density measured in (1) and (2) above will be used to calculate the same current density (10 mA / cm²). 2 Luminous efficiency (cd / A) at ).

[0299] (4) Measurement of driving voltage

[0300] Each diode was measured at 15mA / cm using an ammeter-voltmeter (Keithley 2400). 2 The result is obtained by applying the driving voltage.

[0301] (5) Life measurement

[0302] By using brightness (cd / m 2 Maintained at 24000 cd / m 2 The results were obtained by measuring the time it took for the current efficiency (cd / A) to drop to 97%.

[0303] Table 2 shows the relative values ​​of luminous efficiency, lifetime, and driving voltage based on Comparative Example 1.

[0304] (Table 2)

[0305] Referring to Table 2, the efficiency and lifetime of the organic light-emitting diodes using the compounds according to the embodiments are significantly improved compared to the organic light-emitting diodes according to the comparative examples.

[0306] Although this disclosure has been described in conjunction with exemplary embodiments that are now considered practical, it should be understood that the invention is not limited to the disclosed embodiments, but rather is intended to cover a variety of changes and equivalent arrangements contained within the spirit and scope of the appended claims.

Claims

1. A compound for use in organic optoelectronic devices, said compound being represented by chemical formula 1: [Chemical Formula 1] in, In chemical formula 1, X 1 Is it O or S? R 1 and R 2 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. R 3 To R 5 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. L 1 and L 2 Each is independently a single bond or a substituted or unsubstituted C6 to C30 arylene group. 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. m1 and m2 are each an independent integer from 1 to 3, and When m1 and m2 are 2 or greater, each R 1 and R 2 They are the same as or different from each other.

2. The compound for organic optoelectronic devices according to claim 1, wherein... Ar 1 and Ar 2 Each of the following is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted triphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted 1-fluorenyl, a substituted or unsubstituted 2-fluorenyl, a substituted or unsubstituted 3-fluorenyl, a substituted or unsubstituted 4-fluorenyl, a substituted or unsubstituted 9-fluorenyl, or a substituted or unsubstituted dibenzofuran. The substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted 9,9'-spirofluorenyl group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted xanthonyl group, substituted or unsubstituted spirocyclopentane-1,9'-fluorenyl group, substituted or unsubstituted spirocyclohexane-1,9'-fluorenyl group, substituted or unsubstituted spirofluorene-9,9'-xanthonyl group, or substituted or unsubstituted spirofluorene-9,9'-thiaxanthonyl group.

3. The compound for organic optoelectronic devices according to claim 1, wherein... Ar 1 and Ar 2 Each is independently selected from one of the substituents listed in Group I: Group I in, In group I, R 16 To R 20 Each is independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C3 to C10 cycloalkyl, or substituted or unsubstituted C6 to C12 aryl. R 21 and R 22 Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl. m5 is an integer from 1 to 5. m6 is an integer from 1 to 4. m7 is an integer from 1 to 3. m8 is an integer from 1 to 8. m9 is an integer from 1 to 10, and It is a connection point.

4. The compound for organic optoelectronic devices according to claim 1, wherein... R 3 To R 5 Each is independently a substituted or unsubstituted C1 to C10 alkyl or a substituted or unsubstituted C6 to C12 aryl.

5. The compound for organic optoelectronic devices according to claim 1, wherein... R 3 To R 5 Each is independently a substituted or unsubstituted isopropyl, a substituted or unsubstituted tert-butyl, a substituted or unsubstituted phenyl, or a substituted or unsubstituted biphenyl.

6. The compound for organic optoelectronic devices according to claim 1, wherein... The compound represented by chemical formula 1 for use in organic optoelectronic devices is selected from one of the compounds listed in group 1: [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] Where Dn represents the number of hydrogen atoms that are replaced by deuterium, n is an integer of 0 or greater, and the maximum value of n corresponds to the number of hydrogen sites that can be substituted.

7. An organic optoelectronic device, comprising: The anode and cathode facing each other, and At least one organic layer located between the anode and the cathode, The organic layer comprises a compound for an organic optoelectronic device according to any one of claims 1 to 6.

8. The organic optoelectronic device according to claim 7, wherein... The organic layer includes a light-emitting layer, and The light-emitting layer contains compounds for organic optoelectronic devices.

9. The organic optoelectronic device according to claim 7, wherein... The organic layer includes Emissive layer, The hole transport layer located between the anode and the light-emitting layer, and A hole transport auxiliary layer located between the light-emitting layer and the hole transport layer. The hole transport auxiliary layer contains the compound used in the organic optoelectronic device.

10. The organic optoelectronic device according to claim 9, wherein... The hole transport layer comprises a compound represented by chemical formula 2: [Chemical Formula 2] in, In 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. L 3 and L 4 Each is independently a single bond or a substituted or unsubstituted C6 to C30 arylene group. Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 6 To R 10 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic. m3 is an integer from 1 to 3, and When m3 is 2 or greater, each R 6 They are the same as or different from each other.

11. The organic optoelectronic device according to claim 10, wherein... Chemical formula 2 is represented by chemical formula 2-4: [Chemical Formula 2-4] in, In chemical formula 2-4, Ar 3 To Ar 6 L 3 L 4 R 6 To R 10 And m3 as defined in claim 10.

12. The organic optoelectronic device according to claim 10, wherein... The hole transport layer comprises a compound represented by chemical formula 2-4-1: [Chemical Formula 2-4-1] in, In chemical formula 2-4-1, Ar 4 To Ar 6 L 3 L 4 R 6 To R 10 and m3 as defined in claim 10, Ar 7 and Ar 8 Each is independently a substituted or unsubstituted C1 to C30 alkyl or a substituted or unsubstituted C6 to C30 aryl. R 11 To R 15 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, and m4 is an integer from 1 to 3.

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

14. The organic optoelectronic device according to claim 10, wherein... The compounds represented by chemical formula 2 are selected from the compounds listed in group 2: [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 hydrogen atoms that are replaced by deuterium, where n is an integer of 0 or greater, and the maximum value of n corresponds to the number of hydrogen sites that can be substituted).

15. A display device comprising the organic optoelectronic device according to claim 7.

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