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

Abstract

The present invention relates to: a composition for an organic optoelectronic diode; and an organic optoelectronic diode and a display device, comprising same, the composition comprising a first compound represented by chemical formula 1 and a second compound represented by a combination of chemical formula 2 and chemical formula 3. The details of chemical formula 1 to chemical formula 3 are the same as defined in the specification.

Description

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

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

[0002] Organic optoelectronic diodes are devices that can convert electrical energy and light energy to each other.

[0003] Organic optoelectronic devices can be broadly divided into two types based on their operating principles. One type is a photoelectric device, in which excitons formed by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy. The other type is a light-emitting device, in which light energy is generated from electrical energy by supplying voltage or current to an electrode.

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

[0005] Among these, organic light-emitting diodes (OLEDs) have recently attracted significant 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 influenced by the organic materials located between the electrodes.

[0006] One embodiment provides a composition for an organic optoelectronic device capable of lowering the driving voltage and implementing a high-efficiency and long-life organic optoelectronic device.

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

[0008] Another embodiment provides a display device including the organic optoelectronic device.

[0009] According to one embodiment, a composition for an organic optoelectronic device is provided, comprising a first compound represented by the following chemical formula 1, and a second compound represented by a combination of the following chemical formulas 2 and 3.

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] R 1 Inland R 7 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C18 aryl group,

[0014] L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

[0015] Ar 1 is a substituted or unsubstituted C6 to C30 aryl group,

[0016] m1 to m7 are each independently one of the integers 1 to 4,

[0017] When m1 to m7 are each integers greater than or equal to 2, each R 1 Inland R 7 are identical or different from each other;

[0018] [Chemical Formula 2] [Chemical Formula 3]

[0019]

[0020] In the above chemical formulas 2 and 3,

[0021] Among a1* to a4* in chemical formula 2, two adjacent ones are each a connecting carbon (C) connected to * in chemical formula 3,

[0022] Among a1* to a4* in chemical formula 2, the remaining two that are not connected to chemical formula 4 are CL a -R a And,

[0023] L a , L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0024] R a , R 8 and R 9 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0025] Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0026] m8 and m9 are each independently one of the integers 1 to 4,

[0027] If m8 and m9 are each 2 or greater, each R 8 Inland R 9 are identical or different from each other.

[0028] 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 positioned between the anode and the cathode, wherein the organic layer comprises the composition for an organic optoelectronic device.

[0029] According to another embodiment, a display device including the organic optoelectronic device is provided.

[0030] High-efficiency, long-life organic optoelectronic devices can be realized while lowering the operating voltage.

[0031] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0032] <Explanation of symbols>

[0033] 100: Organic light-emitting diode

[0034] 105: Organic layer

[0035] 110: Cathode

[0036] 120: Bipolar

[0037] 130: Emissive layer

[0038] 140: Hole transport region

[0039] 150: Electron transport region

[0040]

[0041] 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, which is defined solely by the scope of the claims set forth below.

[0042] As used herein, “substituted” means that at least one hydrogen in a substituent or compound is substituted with 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, unless otherwise defined.

[0043] In one embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a 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. In addition, in one specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C20 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C20 aryl group, a C2 to C20 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is replaced with deuterium, a C1 to C5 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C18 aryl group, a C2 to C18 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is replaced with deuterium, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a trimethylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0044] As used herein, “unsubstituted” means that a hydrogen atom is not replaced by another substituent and remains a hydrogen atom.

[0045] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0046] In this specification, unless otherwise defined, “hetero” means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon.

[0047] In this specification, "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group, a naphthyl group, etc., a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc.

[0048] Aryl groups include monocyclic, polycyclic, or fused ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0049] In this specification, "heterocyclic group" is a superordinate concept including a heteroaryl group, and means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the heterocyclic group as a whole or each ring may contain one or more heteroatoms.

[0050] For example, a "heteroaryl group" means an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly connected via a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 of the heteroatoms.

[0051] 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 chrysenyl 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.

[0052] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is 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 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 benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl 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 naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthfuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0053] In this specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has a conductive characteristic along the HOMO level, which 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 the movement in the light-emitting layer.

[0054] In addition, electronic properties refer to the property of being able to receive electrons when an electric field is applied, and have conductive properties along the LUMO level, which means the property of facilitating the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the cathode, and the movement in the light-emitting layer.

[0055] Hereinafter, a composition for an organic optoelectronic device according to an embodiment is described.

[0056] A composition for an organic optoelectronic device according to one embodiment comprises a first compound and a second compound.

[0057] The above first compound can be expressed by the following chemical formula 1.

[0058] [Chemical Formula 1]

[0059]

[0060] In the above chemical formula 1,

[0061] R 1 Inland R 7 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C18 aryl group,

[0062] L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

[0063] Ar 1 is a substituted or unsubstituted C6 to C30 aryl group,

[0064] m1 to m7 are each independently one of the integers 1 to 4,

[0065] When m1 to m7 are each integers greater than or equal to 2, each R 1 Inland R 7 are identical or different from each other.

[0066] The compound represented by the above chemical formula 1 has a structure containing ortho-carbazole in triazine, and has particularly excellent energy transfer efficiency to a phosphorescent dopant, so it can be used as an advantageous material as a phosphorescent host. The biphenyl structure substituted in the triazine included in the above chemical formula 1 can accelerate electron mobility and increase stability compared to mono-phenyl, thereby improving the lifespan when applied as a phosphorescent host.

[0067] In addition, when carbazole is substituted on the ortho-phenylene connected to the triazine, the dihedral angle increases due to the steric hindrance between the triazine and carbazole, and the triazine moiety and the carbazole moiety twist with each other, thereby increasing the dihedral angle. This means that the electron clouds of the HOMO level and the LUMO level are mostly separated without overlapping, and since it has a small ΔEst, rapid energy transfer is possible, and therefore, it exhibits high efficiency characteristics, especially when applied as a phosphorescent host. In addition, since the side reaction path in the excited state is reduced, the lifespan increase effect can be further obtained.

[0068] In addition, by substituting at least one biphenyl group in the triazine, electron mobility can be increased and stability can be increased, thereby improving the driving effect and lifespan.

[0069] In the above chemical formula 1, when m1 is 2 or more, each R 1 may be identical or different from each other,

[0070] In the above chemical formula 1, when m2 is 2 or more, each R 2 may be identical or different from each other,

[0071] In the above chemical formula 1, when m3 is 2 or more, each R 3 may be identical or different from each other,

[0072] In the above chemical formula 1, when m4 is 2 or more, each R 4may be identical or different from each other,

[0073] In the above chemical formula 1, when m5 is 2 or more, each R 5 may be identical or different from each other,

[0074] In the above chemical formula 1, when m6 is 2 or more, each R 6 may be identical or different from each other,

[0075] In the above chemical formula 1, when m7 is 2 or more, each R 7 may be identical or different.

[0076] For example, the above chemical formula 1 can be expressed by any one of the following chemical formulas 1-1 to 1-3.

[0077] [Chemical Formula 1-1]

[0078]

[0079] [Chemical Formula 1-2]

[0080]

[0081] [Chemical Formula 1-3]

[0082]

[0083] In the above chemical formulas 1-1 to 1-3,

[0084] R 1 Inland R 7 , L 1 and L 2 , Ar 1 , and m1 to m7 are as described above.

[0085] In one embodiment, the Ar 1 may be a substituted or unsubstituted C6 to C20 aryl group.

[0086] In a specific embodiment, the Ar 1 may be a substituted or unsubstituted C6 to C18 aryl group.

[0087] For example, the above Ar 1It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0088] In one embodiment, the L 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted C6 to C20 arylene group.

[0089] In a specific embodiment, the L 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted C6 to C12 arylene group.

[0090] For example, the above L 1 and L 2 Each may independently be a single bond or a substituted or unsubstituted phenylene group.

[0091] In a more specific embodiment, the L 1 and L 2 Each can be a single bond.

[0092] In one embodiment, the R 1 Inland R 7 Each of may independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted C3 to C12 cycloalkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0093] In a specific embodiment, the R 1 Inland R 7 may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0094] In a most specific embodiment, the first compound may be, but is not limited to, one selected from the compounds listed in Group 1 below.

[0095] [Group 1]

[0096] [A-1][A-2][A-3][A-4][A-5]

[0097]

[0098] [A-6][A-7][A-8][A-9][A-10]

[0099]

[0100] [A-11][A-12][A-13][A-14][A-15]

[0101]

[0102] [A-16][A-17][A-18][A-19][A-20]

[0103]

[0104] [A-21][A-22][A-23][A-24][A-25]

[0105]

[0106] [A-26][A-27][A-28][A-29][A-30]

[0107]

[0108] [A-31][A-32][A-33][A-34][A-35]

[0109]

[0110] [A-36][A-37][A-38][A-39][A-40]

[0111]

[0112] [A-41][A-42][A-43][A-44][A-45]

[0113]

[0114] [A-46][A-47][A-48][A-49][A-50]

[0115]

[0116] [A-51][A-52][A-53][A-54][A-55]

[0117]

[0118] [A-56][A-57][A-58][A-59][A-60]

[0119]

[0120] [A-61][A-62][A-63][A-64][A-65]

[0121]

[0122] [A-66][A-67][A-68][A-69][A-70]

[0123]

[0124] [A-71][A-72][A-73][A-74][A-75]

[0125]

[0126] [A-76][A-77][A-78][A-79][A-80]

[0127]

[0128] [A-81][A-82][A-83][A-84][A-85]

[0129]

[0130] [A-86][A-87][A-88][A-89][A-90]

[0131]

[0132] [A-91][A-92][A-93][A-94][A-95]

[0133]

[0134] [A-96][A-97][A-98][A-99][A-100]

[0135]

[0136] [A-101][A-102][A-103][A-104][A-105]

[0137]

[0138] [A-106][A-107][A-108][A-109][A-110]

[0139]

[0140] [A-111][A-112][A-113][A-114][A-115]

[0141]

[0142] [A-116][A-117][A-118][A-119][A-120]

[0143]

[0144] [A-121][A-122][A-123][A-124][A-125]

[0145]

[0146] [A-126][A-127][A-128][A-129][A-130]

[0147]

[0148] [A-131][A-132][A-133][A-134][A-135]

[0149]

[0150] [A-136][A-137][A-138][A-139][A-140]

[0151]

[0152] [A-141][A-142][A-143][A-144][A-145]

[0153]

[0154] [A-146][A-147][A-148][A-149][A-150]

[0155]

[0156] [A-151][A-152][A-153][A-154][A-155]

[0157]

[0158] [A-156][A-157][A-158][A-159][A-160]

[0159]

[0160] [A-161][A-162][A-163][A-164][A-165]

[0161]

[0162] [A-166][A-167][A-168][A-169][A-170]

[0163]

[0164] [A-171][A-172][A-173][A-174][A-175]

[0165]

[0166] Meanwhile, the second compound can be expressed by a combination of the following chemical formulas 2 and 3.

[0167] [Chemical Formula 2] [Chemical Formula 3]

[0168]

[0169] In the above chemical formulas 2 and 3,

[0170] Among a1* to a4* in chemical formula 2, two adjacent ones are each a connecting carbon (C) connected to * in chemical formula 3,

[0171] Among a1* to a4* in chemical formula 2, the remaining two that are not connected to chemical formula 4 are CL a -R a And,

[0172] L a , L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0173] R a , R 8 and R 9are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0174] Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0175] m8 and m9 are each independently one of the integers 1 to 4,

[0176] If m8 and m9 are each 2 or greater, each R 8 Inland R 9 are identical or different from each other.

[0177] The above second compound can be used in a light-emitting layer together with the above first compound to improve light-emitting efficiency and lifespan characteristics by increasing charge mobility and increasing stability.

[0178] In the above chemical formula 2, when m8 is 2 or more, each R 8 may be identical or different from each other,

[0179] In the above chemical formula 3, when m9 is 2 or more, each R 9 may be identical or different.

[0180] For example, “substitution” in the above chemical formulas 2 and 3 means that at least one hydrogen is substituted with deuterium, a cyano group, a C1 to C5 alkyl group, a C3 to C10 cycloalkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0181] The combination of the above chemical formulas 2 and 3 can be expressed, for example, by any one of the following chemical formulas 2A, 2B, 2C, 2D, and 2E.

[0182] [Formula 2A] [Formula 2B] [Formula 2C]

[0183]

[0184] [Chemical Formula 2D] [Chemical Formula 2E]

[0185]

[0186] In the above chemical formulas 2A to 2E, L 3 , L 4 , Ar 2 , Ar 3 , R 8 , R 9 , m8 and m9 are as described above,

[0187] L a1 Inland L a4 is the aforementioned L 3 and L 4 is the same as the definition of

[0188] R a1 Inland R a4 is the aforementioned R 8 and R 9 It is the same as the definition of .

[0189] In one embodiment, the L 3 -Ar 2 and L 4 -Ar 3 Each may independently be one of the substituents listed in Group Ⅰ below.

[0190] [Group Ⅰ]

[0191]

[0192] In the above group Ⅰ,

[0193] R 10 Inland R 14 are each independently hydrogen, deuterium, cyano group, C1 to C10 alkyl group or C6 to C12 aryl group,

[0194] m10 is an integer between 1 and 5,

[0195] m11 is one of the integers 1 to 4,

[0196] m12 is an integer between 1 and 3,

[0197] m13 is an integer of 1 or 2,

[0198] m14 is an integer between 1 and 7,

[0199] * is a connection point.

[0200] In the above group Ⅰ, if m10 is 2 or more, each R 10 may be identical or different.

[0201] In the above group Ⅰ, if m11 is 2 or more, each R 11 may be identical or different.

[0202] In the above group Ⅰ, if m12 is 2 or more, each R 12 may be the same or different.

[0203] In the above group Ⅰ, when m13 is 2, each R 13 may be the same or different.

[0204] In the above group Ⅰ, if m14 is 2 or more, each R 14 may be the same or different.

[0205] For example, the second compound can be represented by one of the chemical formulas 2A, 2C, and 2E.

[0206] As a specific example, the second compound can be expressed by the chemical formula 2C.

[0207] For example, Ar of the above chemical formula 2 and chemical formula 3 2 and Ar 3may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0208] For example, Ar of the above chemical formula 2 and chemical formula 3 2 and Ar 3 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0209] For example, the above R a1 Inland R a4 , R 8 and R 9 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0210] For example, the above R a1 Inland R a4 , R 8 and R 9 may each independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group.

[0211] In a specific embodiment, the R a1 Inland R a4 , R 8 and R 9 may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0212] In a specific embodiment of the present invention, the second compound may be represented by the chemical formula 2C, and L of the chemical formula 2C a3 and L a4 is a single bond, and L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and R 8 R 9 , R a3 and R a4 are hydrogen, deuterium, cyano or phenyl groups, respectively, and Ar 2 and Ar 3 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0213] For example, L of the above chemical formula 2C a3 and L a4 is a single bond, and R 8 , R 9 , R a3 and R a4 are each independently hydrogen, deuterium or a C6 to C12 aryl group, and L 3 -Ar 2 and L 4 -Ar 3 Each of may independently be one of the substituents listed in Group I above.

[0214] For example, the second compound may be, but is not limited to, one selected from the compounds listed in Group 2 below.

[0215] [Group 2]

[0216] [C-1] [C-2] [C-3] [C-4]

[0217]

[0218] [C-5] [C-6] [C-7] [C-8]

[0219]

[0220] [C-9] [C-10] [C-11] [C-12]

[0221]

[0222] [C-13] [C-14] [C-15] [C-16]

[0223]

[0224] [C-17] [C-18] [C-19] [C-20]

[0225]

[0226] [C-21] [C-22] [C-23] [C-24]

[0227]

[0228] [C-25] [C-26] [C-27] [C-28]

[0229]

[0230] [C-29] [C-30] [C-31] [C-32]

[0231]

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

[0233]

[0234] [C-37] [C-38] [C-39] [C-40]

[0235]

[0236] [C-41] [C-42] [C-43] [C-44]

[0237]

[0238] [C-45] [C-46] [C-47] [C-48]

[0239]

[0240] [C-49] [C-50] [C-51] [C-52]

[0241]

[0242] [C-53] [C-54] [C-55] [C-56]

[0243]

[0244] [C-57]

[0245]

[0246] Additionally, examples of compounds C-1 to C-57 listed in Group 2 above in which at least one hydrogen is replaced with deuterium are provided below, but are not limited thereto.

[0247] [C-58] [C-59] [C-60] [C-61] [C-62]

[0248]

[0249] [C-63] [C-64] [C-65] [C-66] [C-67]

[0250]

[0251] [C-68] [C-69] [C-70] [C-71] [C-72]

[0252]

[0253] (Dn refers to the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms are substituted)

[0254] The most specific structures according to the deuterium substitution position and substitution rate for compounds C-58 to C-72 of the above group 2 are presented as examples only, and there is no intention to limit the scope of rights to compounds not presented below.

[0255] The scope of the present invention is determined by the claims, and when deuterium is substituted, it is not limited to the compounds exemplified below, and the deuterium substitution position and deuterium substitution rate, etc. may include all ranges that can be changed within the range of Compound C-1 to Compound C-72.

[0256] [C-73] [C-74]

[0257]

[0258] [C-75] [C-76] [C-77] [C-78]

[0259]

[0260] [C-79] [C-80] [C-81] [C-82]

[0261]

[0262] [C-83] [C-84] [C-85] [C-86]

[0263]

[0264] [C-87] [C-88] [C-89] [C-90]

[0265]

[0266] [C-91] [C-92] [C-93] [C-94]

[0267]

[0268] [C-95] [C-96] [C-97] [C-98]

[0269]

[0270] [C-99] [C-100] [C-101] [C-102]

[0271]

[0272] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By being included in the above range, the electron transport ability of the first compound and the hole transport ability of the second compound can be used to achieve an appropriate weight ratio to implement bipolar characteristics, thereby improving efficiency and lifespan. Within the above range, the weight ratio may be included in a weight ratio of, for example, about 10:90 to 90:10, about 20:80 to 80:20, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, the weight ratio may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0273] An organic optoelectronic device using the composition for an organic optoelectronic device described above is described below.

[0274] Organic optoelectronic devices are not particularly limited as long as they can convert electrical energy and light energy to each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0275] Here, an organic light-emitting device, which is an example of an organic optoelectronic device, is described with reference to drawings.

[0276] Fig. 1 is a cross-sectional view showing an organic light-emitting device according to one embodiment.

[0277] Referring to FIG. 1, an organic light-emitting device (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other, and an organic layer (105) positioned between the anode (120) and the cathode (110).

[0278] The anode (120) can be made of a conductor having a high work function, for example, to facilitate hole injection, and can be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode (120) may be, but is not limited to, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; 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.

[0279] The cathode (110) may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide, and / or a conductive polymer. The cathode (110) may be made of, but is not limited to, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; a multilayer structure material such as LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca.

[0280] The organic layer (105) may include the composition for the organic optoelectronic device described above.

[0281] The organic layer (105) includes a light-emitting layer (130), and the light-emitting layer (130) includes a host and a dopant, and the host may include the composition for an organic optoelectronic device described above, and the dopant may be, for example, a phosphorescent dopant, and may be, for example, a red, green, or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0282] A dopant is a substance that causes light emission when mixed in a trace amount in a composition for an organic optoelectronic device. Generally, a substance such as a metal complex that emits light by multiple excitation that excites to a triplet state or higher can be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may be included in one or more types.

[0283] An example of a dopant is a phosphorescent dopant, and examples of a phosphorescent dopant include an organometallic compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0284] [Chemical formula Z]

[0285] L 6 MX 1

[0286] In the above chemical formula Z, M is a metal, and L 6 and X 1 are ligands that are the same or different and form complexes with M.

[0287] 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 6 and X 1 may be, for example, a bidentate ligand.

[0288] [Chemical Formula Z-1]

[0289]

[0290] [Chemical Formula Z-2]

[0291]

[0292] In the above chemical formulas Z-1 and Z-2,

[0293] Ring A and ring B are each independently a monocyclic ring or a polycyclic fused ring,

[0294] wherein each ring among the monocyclic ring and polycyclic fused ring is a 5-membered or 6-membered carbocyclic or heterocyclic ring,

[0295] R 200 and R 201 Each independently represents one to a maximum number of monovalent substituents,

[0296] R 200 and R 201 If there are two or more, each R 200 and R 201 are identical or different from each other,

[0297] R 202 Inland R 213 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, -SiR 214 R 215 R 216 , -GeR 214 R 215 R 216 or a combination of these,

[0298] The above R 214 Inland R 216 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0299] X 10 , X 11 , X 12 and X 13 are each independently selected from the group consisting of carbon and nitrogen,

[0300] Y 100 is O or S,

[0301] m100 is an integer from 1 to 3,

[0302] m101 is an integer from 1 to 2,

[0303] n100 is 0 or 1,

[0304] * is a connection point.

[0305] When n100 is 0, it is formed with a monovalent substituent,

[0306] If n100 is 1, a fusion ring can be formed.

[0307] L 6 and X 1 Examples of ligands represented by may be selected from, but are not limited to, the chemical formulas listed in Group A below.

[0308] [Group A]

[0309]

[0310] In the above group A,

[0311] R 300 Inland R 302 are each independently a C1 to C30 alkyl group substituted or unsubstituted with hydrogen, deuterium, halogen, a C6 to C30 aryl group substituted or unsubstituted with C1 to C30 alkyl, or halogen,

[0312] R 303 Inland R 308 are each 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,

[0313] m25 is an integer between 1 and 5,

[0314] m26 is one of the integers 1 to 4,

[0315] m27 is one of the integers 1 to 3,

[0316] m28 is an integer of 1 or 2,

[0317] m29 is an integer between 1 and 6,

[0318] If m25 to m29 are 2 or more, each R 303 Inland R 307 are identical or different from each other.

[0319] In one embodiment, the dopant may be an iridium complex, and may be represented by one of the following chemical formulae 6-1 to 6-5.

[0320] [Chemical Formula 6-1]

[0321]

[0322] In the above chemical formula 6-1,

[0323] R 101 Inland R 116 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, -SiR 132 R 133 R 134 or -GeR 132 R 133 R 134 And,

[0324] The above R 132 Inland R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0325] R 101 Inland R 116 At least one of them is a functional group represented by the following chemical formula V-1,

[0326] L 100is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0327] m21 and m22 are independently any integer from 0 to 3, and m21 + m22 is any integer from 1 to 3,

[0328] [Chemical Formula V-1]

[0329]

[0330] In the above chemical formula V-1,

[0331] R 135 Inland R 139 are each 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,

[0332] * indicates a part connected to a carbon atom.

[0333] [Chemical Formula 6-2]

[0334]

[0335] [Chemical Formula 6-3]

[0336]

[0337] [Chemical Formula 6-4]

[0338]

[0339] [Chemical Formula 6-5]

[0340]

[0341] In the above chemical formulas 6-2 to 6-5,

[0342] X 14 is selected from the group consisting of carbon and nitrogen,

[0343] Y 100 is O or S,

[0344] R 101 Inland R 122 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, -SiR 133 R 134 R 135 or -GeR 133 R 134 R 135 And,

[0345] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0346] L 100 is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0347] m111 is an integer from 1 to 2,

[0348] n1 and n2 are independently any integer from 0 to 3, and n1 + n2 is any integer from 1 to 3.

[0349] In another embodiment, the dopant may be a platinum complex, for example represented by the chemical formula Z-1.

[0350] [Chemical Formula Z-1]

[0351]

[0352] In the above chemical formula Z-1, rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0353] R A , R B , R C , and R D each independently represents monosubstitution, disubstitution, trisubstitution, tetrasubstitution, or no substitution;

[0354] L B, L C , and L D are independently selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0355] If nA is 1, L E is selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E does not exist;

[0356] 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 randomly connected to form a ring; X B , X C , X D , and X E are independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 represent oxygen or direct bonds, respectively.

[0357] The above platinum complex can be represented, for example, by the following chemical formula 7-1 or chemical formula 7-2.

[0358] [Chemical Formula 7-1]

[0359]

[0360] [Chemical Formula 7-2]

[0361]

[0362] In the above chemical formulas 7-1 and 7-2,

[0363] X 100 Silver O, S and NR 132 Selected from among,

[0364] R 118 Inland R 132 are each 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,

[0365] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0366] R 118 Inland R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl group,

[0367] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group.

[0368] The organic layer may further include a charge transport region in addition to the light-emitting layer.

[0369] The above charge transport region may be, for example, a hole transport region (140).

[0370] The above hole transport region (140) can further increase hole injection and / or hole mobility between the anode (120) and the light-emitting layer (130) and block electrons.

[0371] Specifically, the hole transport region (140) may include a hole transport layer between the anode (120) and the light-emitting layer (130), and a hole transport auxiliary layer between the light-emitting layer (130) and the hole transport layer, and at least one of the compounds listed in Group B below may be included in at least one layer of the hole transport layer and the hole transport auxiliary layer.

[0372] [Group B]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397]

[0398]

[0399]

[0400]

[0401]

[0402]

[0403]

[0404]

[0405]

[0406] (Dn refers to the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms are substituted)

[0407] In addition to the above-described compound, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having a similar structure thereto may also be used in the above-described hole transport region (140).

[0408] Additionally, the charge transport region may be, for example, an electron transport region (150).

[0409] The above electron transport region (150) can further increase electron injection and / or electron mobility between the cathode (110) and the light-emitting layer (130) and block holes.

[0410] Specifically, the electron transport region (150) may include an electron transport layer between the cathode (110) and the light-emitting layer (130), and an electron transport auxiliary layer between the light-emitting layer (130) and the electron transport layer, and at least one of the compounds listed in Group C below may be included in at least one layer of the electron transport layer and the electron transport auxiliary layer.

[0411] [Group C]

[0412]

[0413]

[0414]

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429] One embodiment may be an organic light-emitting device including a light-emitting layer as an organic layer.

[0430] Another embodiment may be an organic light-emitting device including an emission layer and a hole transport region as the organic layer.

[0431] Another embodiment may be an organic light-emitting device including an emission layer and an electron transport region as the organic layer.

[0432] An organic light-emitting device according to one embodiment of the present invention may include a hole transport region (140) and an electron transport region (150) in addition to a light-emitting layer (130) as an organic layer (105), as shown in FIG. 1.

[0433] Meanwhile, the organic light-emitting device may further 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.

[0434] An organic light-emitting device (100) can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film forming method such as evaporation, sputtering, plasma plating, and ion plating, and then forming a cathode or anode thereon.

[0435] The above-described organic light-emitting device can be applied to an organic light-emitting display device.

[0436] The implementation examples described above are described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0437] The starting materials and reactants used in the examples and synthesis examples below were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry or P&H Tech, or synthesized using known methods, unless otherwise specified.

[0438]

[0439] (Synthesis of the first compound)

[0440] Synthesis Example 1: Synthesis of Intermediate Int-01

[0441] [Reaction Formula 1]

[0442]

[0443] 1-bromo-4-chlorobenzene (60 g, 313.4 mmol), 2-fluorophenyl boronic acid (46.04 g, 139.92 mmol), K2CO3 (108.29 g, 783.49 mmol), and Pd(PPh3)4 (18.11 g, 15.67 mmol) were placed in a round-bottomed flask and dissolved in THF (700 ml) and distilled water (300 ml), and then stirred under reflux at 60°C for 12 hours. After the reaction was completed, the aqueous layer was removed and column chromatography (Hexane:DCM (20%)) was used to obtain 55.05 g (85%) of an intermediate (Int-01).

[0444]

[0445] Synthesis Example 2: Synthesis of Intermediate Int-02

[0446] [Reaction Formula 2]

[0447]

[0448] Intermediate (Int-01) (30 g, 145.18 mmol), Bis(pinacolato)diboron (55.30 g, 217.77 mmol), Pd2(dba)3 (6.65 g, 7.26 mmol), and potassium acetate (28.50 g, 290.36 mmol) were placed in a round-bottomed flask and dissolved in toluene (350 ml). The mixture was refluxed and stirred at 120°C for 10 hours. When the reaction was complete, the mixture was poured into an excess of distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized with ethyl acetate and hexane to obtain 27.65 g (64%) of intermediate (Int-02).

[0449]

[0450] Synthesis Example 3: Synthesis of Intermediate Int-03

[0451] [Reaction Formula 3]

[0452]

[0453] 2, 4- Dichloro- 6-phenyl - 1, 3, 5- triazine (15 g, 66.35 mmol), intermediate Int-02 (23.64 g, 53.08 mmol), K2CO3 (22.93 g, 165.89 mmol), and Pd(dppf)Cl2 (2.71 g, 3.32 mmol) were placed in a round-bottomed flask and dissolved in toluene (500 ml) and distilled water (200 ml), and then refluxed and stirred at 60°C for 12 hours. After the reaction was completed, the aqueous layer was removed and a solid was obtained through a filter, which was then dissolved in monochlorobenzene and filtered through silica gel / Celite, and an appropriate amount of organic solvent was removed and recrystallized with methanol to obtain 18.5 g (77%) of intermediate (Int-03).

[0454]

[0455] Synthesis Example 4: Synthesis of Intermediate Int-04

[0456] [Reaction Formula 4]

[0457]

[0458] Intermediate Int-03 (10 g, 27.64 mmol), 2-fluorophenyl boronic acid (4.64 g, 33.17 mmol), K2CO3 (9.55 g, 69.10 mmol), and Pd(PPh3)4 (1.60 g, 1.38 mmol) were placed in a round-bottomed flask and dissolved in THF (120 ml) and distilled water (50 ml), and then refluxed and stirred at 60°C for 12 hours. After the reaction was completed, the aqueous layer was removed, and a solid was obtained. This was dissolved in monochlorobenzene, filtered through silica gel / Celite, and an appropriate amount of organic solvent was removed, and then recrystallized with methanol to obtain 9.545 g (82%) of the intermediate (Int-04).

[0459]

[0460] Synthesis Example 5: Synthesis of Compound A-1

[0461] [Reaction Formula 5]

[0462]

[0463] Intermediate Int-04 (15g, 35.59mmol), carbazole (17.85g, 106.77mmol), K3PO4 (22.66g, 106.77mmol) were placed in a round bottom flask, dissolved in NMP (200ml), and stirred under reflux at 170°C for 12 hours. When the reaction was complete, water was added to form a solid, stirred, and filtered to obtain the solid. Dissolved in monochlorobenzene, filtered through silica gel / Celite, and after removing an appropriate amount of organic solvent, recrystallized with methanol to obtain compound A-1 (17.83g, 70% yield).

[0464]

[0465] Synthesis Example 6: Synthesis of Intermediate Int-05

[0466] [Reaction Formula 6]

[0467]

[0468] 4-Bromocarbazole (15g, 60.95mmol), phenylboronic acid (11.44g, 73.14mmol), K2CO3 (21.06g, 152.38mmol), and Pd(PPh3)4 (3.52g, 3.05mmol) were placed in a round-bottomed flask, dissolved in THF (200ml) and distilled water (75ml), and stirred under reflux at 60°C for 12 hours. After the reaction was completed, the aqueous layer was removed and column chromatography (Hexane:DCM (20%)) was used to obtain 12.3g (83%) of the intermediate (Int-05).

[0469]

[0470] Synthesis Example 7: Synthesis of Intermediate Int-06

[0471] [Reaction Formula 7]

[0472]

[0473] Intermediate Int-05 (15g, 61.65mmol), 2-fluorobromobenzene (11.33g, 64.73mmol), K2PO4 (28.79g, 135.64mmol) were placed in a round bottom flask and refluxed with DMF (200ml) at 150°C for 12 hours. After the reaction was completed, water was added and the mixture was stirred for 30 minutes. After removing the aqueous layer and organic solvent, column chromatography (Hexane:DCM (20%)) was used to obtain 18.2g (74%) of intermediate (Int-06).

[0474]

[0475] Synthesis Example 8: Synthesis of Intermediate Int-07

[0476] [Reaction Formula 8]

[0477]

[0478] Intermediate (Int-06) (15 g, 37.85 mmol), Bis(pinacolato)diboron (12.5 g, 49.21 mmol), Pd(dppf)Cl2 (1.73 g, 1.9 mmol), and potassium acetate (7.43 g, 75.7 mmol) were placed in a round-bottomed flask and dissolved in toluene (100 ml). The mixture was refluxed and stirred at 120°C for 10 hours. When the reaction was complete, the mixture was poured into an excess of distilled water and stirred for 1 hour. The solid was filtered and dissolved in DCM. After removing moisture with MgSO4, the organic solvent was filtered using a silica gel pad and removed under reduced pressure. The solid was recrystallized with acetone and hexane to obtain 14.6 g (87%) of intermediate (Int-07).

[0479]

[0480] Synthesis Example 9: Synthesis of Intermediate Int-08

[0481] [Reaction Formula 9]

[0482]

[0483] In a nitrogen environment, 2-phenyl-4,6-dichloro-1,3,5-triazine (15 g, 66.35 mmol) and intermediate Int-07 (29.55 g, 66.35 mmol), K2CO3 (22.95 g, 165.8 mmol) and Pd(PPh3)4 (3.83 g, 3.32 mmol) were placed in a round-bottom flask and dissolved in THF (150 ml) and distilled water (80 ml), and then refluxed and stirred at 70°C for 12 hours. After the reaction was completed, the mixture was added to 500 ml of methanol, the crystallized solid was filtered, dissolved in monochlorobenzene, filtered through silica gel / Celite, and an appropriate amount of organic solvent was removed. Recrystallized with methanol to obtain 25.61 g (76%) of intermediate Int-08.

[0484]

[0485] Synthesis Example 10: Synthesis of Intermediate Int-09

[0486] [Reaction Formula 10]

[0487]

[0488] Intermediate Int-09 (18.75 g, 75% yield) was obtained through the same synthetic method as Synthesis Example 4, except that intermediate Int-08 was used instead of intermediate Int-03 and intermediate Int-02 was used instead of 2-fluorophenyl boronic acid.

[0489]

[0490] Synthesis Example 11: Synthesis of Compound A-15

[0491] [Reaction Formula 11]

[0492]

[0493] Compound A-15 (15.61 g, 78% yield) was obtained through the same synthetic method as Synthetic Example 5, except that intermediate Int-09 was used instead of intermediate Int-04.

[0494]

[0495] Synthesis Example 12: Synthesis of Intermediate Int-10

[0496] [Reaction Formula 12]

[0497]

[0498] 1-bromo-3-chloro-2-fluorobenzene (50 g, 238.73 mmol), phenyl boronic acid (30.56 g, 250.67 mmol), K2CO3 (82.49 g, 596.83 mmol), and Pd(PPh3)4 (13.79 g, 11.94 mmol) were placed in a round-bottomed flask, dissolved in THF (600 ml) and distilled water (300 ml), and stirred under reflux at 80°C for 12 hours. After the reaction was completed, the aqueous layer was removed and column chromatography (Hexane: DCM (20%)) was used to obtain 40.57 g (82%) of the intermediate (Int-10).

[0499]

[0500] Synthesis Example 13: Synthesis of Intermediate Int-11

[0501] [Reaction Formula 13]

[0502]

[0503] Intermediate Int-11 (21.5 g, 75% yield) was obtained through the same synthetic method as in Synthesis Example 2, except that intermediate Int-10 was used instead of intermediate Int-01.

[0504]

[0505] Synthesis Example 14: Synthesis of Intermediate Int-12

[0506] [Reaction Formula 14]

[0507]

[0508] Intermediate Int-12 (17.87 g, 71% yield) was obtained through the same synthetic method as in Synthesis Example 4, except that 2-fluorophenyl boronic acid was replaced with intermediate Int-11.

[0509]

[0510] Synthesis Example 15: Synthesis of Compound A-8

[0511] [Reaction Formula 15]

[0512]

[0513] Compound A-8 (11.48 g, 69% yield) was obtained through the same synthetic method as in Synthesis Example 5, except that intermediate Int-12 was used instead of intermediate Int-04.

[0514]

[0515] (Synthesis of the second compound)

[0516] Synthesis Example 16: Synthesis of Compound C-4

[0517] [Reaction Formula 16]

[0518]

[0519] 10.0 g (24.5 mmol) of intermediate 9-1, 6.3 g (26.9 mmol) of intermediate 9-2, 31.1 g (1.2 mmol) of Pd2(dba), 3.5 g (36.7 mmol) of NaOtBu, and 30.7 g (3.7 mmol) of P(t-Bu) were placed in a round-bottomed flask, 122 ml of xylene was added, and the mixture was refluxed and stirred at 140°C for 12 hours. When the reaction was complete, distilled water was added, stirred, the aqueous layer was removed, the organic layer was filtered through silica gel, and recrystallized to obtain 10.3 g (75%) of compound C-4.

[0520] (LC / MS theoretical: 560.23 g / mol, measured: M+= 561.54 g / mol)

[0521]

[0522] Synthesis Example 17: Synthesis of Compound C-5

[0523] [Reaction Formula 17]

[0524]

[0525] 10.0 g (24.5 mmol) of intermediate 10-1, 6.3 g (26.9 mmol) of intermediate 10-2, 31.1 g (1.2 mmol) of Pd2(dba), 3.5 g (36.7 mmol) of NaOtBu, and 30.7 g (3.7 mmol) of P(t-Bu) were placed in a round-bottomed flask, 122 ml of xylene was added, and the mixture was refluxed and stirred at 140°C for 12 hours. When the reaction was complete, distilled water was added, stirred, the aqueous layer was removed, and the organic layer was filtered through silica gel and recrystallized to obtain 9.7 g (71%) of compound C-5.

[0526] (LC / MS theoretical: 560.23 g / mol, measured: M+= 561.57 g / mol)

[0527]

[0528] Synthesis Example 18: Synthesis of Compound H-1

[0529] [Reaction Formula 18]

[0530]

[0531] Compound H-1 (11.24 g, 68% yield) was obtained through the same synthetic method as Synthesis Example 4, except that 3-bromo-9-phenyl-9H-carbazole was used instead of intermediate Int-03 and 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole was used instead of 2-fluorophenyl boronic acid.

[0532]

[0533] Example 1: Fabrication of a green organic light-emitting device (mixed host)

[0534] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was ultrasonically washed in distilled water. After washing with distilled water, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 10 minutes using oxygen plasma and then transferred to a vacuum deposition machine. Using the ITO transparent electrode prepared in this way as an anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO substrate to form a 100Å thick hole injection layer, and Compound A was deposited on the hole injection layer to a thickness of 1350Å to form a hole transport layer. Compound E was deposited on the hole transport layer to a thickness of 320Å to form a hole transport auxiliary layer. On the hole transport auxiliary layer, compound A-1 synthesized in Synthesis Example 5 and compound C-4 synthesized in Synthesis Example 16 were simultaneously used as hosts in a weight ratio of 7:3 and PtGD was doped as a dopant in an amount of 15 wt%, thereby forming a light-emitting layer having a thickness of 380 Å by vacuum deposition. Subsequently, compound F was deposited on the light-emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound G and Liq were simultaneously vacuum-deposited at a weight ratio of 1:1 to form an electron transport layer having a thickness of 300 Å. LiQ at 15 Å and Al at 1200 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0535] It was fabricated with the structure of ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / Compound E (320Å) / EML[Host(Compound A-1: ​​Compound C-4 = 7:3 wt% / wt%): PtGD = 85 wt%: 15 wt%](380Å) / Compound F(50Å) / Compound G:LiQ(300Å) / LiQ(15Å) / Al(1200Å).

[0536] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0537] Compound F: 2-[3'-(9,9-Dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0538] Compound G: 2-[4-[4-(4'-Cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0539] [PtGD]

[0540]

[0541]

[0542] Examples 2, 3 and Comparative Examples 1 to 3

[0543] An organic light-emitting device was manufactured in the same manner as Example 1, except that the composition was changed to that described in Table 1 below.

[0544]

[0545] evaluation

[0546] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light-emitting devices according to Examples 1 to 3 and Comparative Examples 1 to 3 were evaluated.

[0547] The specific measurement method is as follows, and the results are as shown in Tables 1 to 3.

[0548] (1) Measurement of changes in current density according to voltage changes

[0549] For the manufactured organic light-emitting device, the current flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

[0550] (2) Measurement of luminance change according to voltage change

[0551] For the manufactured organic light-emitting device, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the results were obtained.

[0552] (3) Measurement of luminous efficiency

[0553] Using the luminance, current density, and voltage measured from the above (1) and (2), the same current density (10 mA / cm 2 ) was calculated for luminous efficacy (cd / A).

[0554] The luminous efficiency values ​​of Example 1 and Comparative Example 1 were calculated as relative values ​​based on Example 1 and are listed in Table 1 below.

[0555] The luminous efficiency values ​​of Example 2 and Comparative Example 2 were calculated as relative values ​​based on Example 2 and are listed in Table 2 below.

[0556] The luminous efficiency values ​​of Example 3 and Comparative Example 3 were calculated as relative values ​​based on Example 3 and are listed in Table 3 below.

[0557] (4) Life span measurement

[0558] Luminance (cd / m 2 ) to 24000cd / m 2 The results were obtained by maintaining the current at 97% and measuring the time until the current efficiency (cd / A) decreased to 97%.

[0559] The life measurement values ​​of Example 1 and Comparative Example 1 were calculated as relative values ​​based on Example 1 and are listed in Table 1 below.

[0560] The life measurement values ​​of Example 2 and Comparative Example 2 were calculated as relative values ​​based on Example 2 and are listed in Table 2 below.

[0561] The life measurement values ​​of Example 3 and Comparative Example 3 were calculated as relative values ​​based on Example 3 and are listed in Table 3 below.

[0562] (5) Driving voltage measurement

[0563] 15mA / cm using a current-voltage meter (Keithley 2400) 2 The results were obtained by measuring the driving voltage of each element.

[0564] The driving voltages of Example 1 and Comparative Example 1 were calculated as relative values ​​based on Example 1 and are listed in Table 1 below.

[0565] The driving voltages of Example 2 and Comparative Example 2 were calculated as relative values ​​based on Example 2 and are listed in Table 2 below.

[0566] The driving voltages of Example 3 and Comparative Example 3 were calculated as relative values ​​based on Example 3 and are listed in Table 3 below.

[0567] No. 1st host 2nd host Driving voltage (%) Efficiency (%) Lifespan (%) Example 1A-1C-4 100 100 100 Comparative example 1A-1H-11 109765

[0568] No. 1 Host 2 Host Driving Voltage (%) Efficiency (%) Lifespan (%) Example 2A-15C-4100100100 Comparative Example 2A-15H-1979845

[0569] No. 1 Host 2 Host Driving Voltage (%) Efficiency (%) Lifespan (%) Example 3A-08C-5100100100 Comparative Example 3A-08H-11089560

[0570] Referring to Tables 1 to 3, it can be confirmed that the organic light-emitting devices according to Examples 1 to 3 have significantly improved driving voltage luminous efficiency and lifespan characteristics compared to the organic light-emitting devices according to Comparative Examples 1 to 3.

[0571]

[0572] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention.

Claims

1. A first compound represented by the following chemical formula 1, and A second compound represented by a combination of the following chemical formulas 2 and 3 Composition for organic optoelectronic devices comprising: [Chemical Formula 1] In the above chemical formula 1, R 1 Inland R 7 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, or a substituted or unsubstituted C6 to C18 aryl group, L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group, Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, m1 to m7 are each independently one of the integers 1 to 4, When m1 to m7 are each integers greater than or equal to 2, each R 1 Inland R 7 are identical or different from each other; [Chemical Formula 2] [Chemical Formula 3] In the above chemical formulas 2 and 3, Among a1* to a4* in chemical formula 2, two adjacent ones are each a connecting carbon (C) connected to * in chemical formula 3, Among a1* to a4* in chemical formula 2, the remaining two that are not connected to chemical formula 4 are CL a -R a And, L a , L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a , R 8 and R 9 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, m8 and m9 are each independently an integer from 1 to 4, If m8 and m9 are each 2 or greater, each R 8 Inland R 9 are identical or different from each other.

2. In paragraph 1, The above chemical formula 1 is a composition for an organic optoelectronic device, which is represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] In the above chemical formulas 1-1 to 1-3, R 1 Inland R 7 , L 1 and L 2 , Ar 1 , and m1 to m7 are as defined in paragraph 1.

3. In paragraph 1, The above Ar 1 A composition for an organic optoelectronic device, wherein the composition comprises a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

4. In paragraph 1, Above L 1 and L 2 A composition for an organic optoelectronic device, wherein each independently represents a single bond or a substituted or unsubstituted phenylene group.

5. In paragraph 1, The above R 1 Inland R 7 A composition for an organic optoelectronic device, wherein each independently represents hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C5 alkyl group, a substituted or unsubstituted C3 to C12 cycloalkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

6. In paragraph 1, The above first compound is a composition for an organic optoelectronic device selected from the compounds listed in Group 1 below: [Group 1] [A-1][A-2][A-3][A-4][A-5] [A-6][A-7][A-8][A-9][A-10] [A-11][A-12][A-13][A-14][A-15] [A-16][A-17][A-18][A-19][A-20] [A-21][A-22][A-23][A-24][A-25] [A-26][A-27][A-28][A-29][A-30] [A-31][A-32][A-33][A-34][A-35] [A-36][A-37][A-38][A-39][A-40] [A-41][A-42][A-43][A-44][A-45] [A-46][A-47][A-48][A-49][A-50] [A-51][A-52][A-53][A-54][A-55] [A-56][A-57][A-58][A-59][A-60] [A-61][A-62][A-63][A-64][A-65] [A-66][A-67][A-68][A-69][A-70] [A-71][A-72][A-73][A-74][A-75] [A-76][A-77][A-78][A-79][A-80] [A-81][A-82][A-83][A-84][A-85] [A-86][A-87][A-88][A-89][A-90] [A-91][A-92][A-93][A-94][A-95] [A-96][A-97][A-98][A-99][A-100] [A-101][A-102][A-103][A-104][A-105] [A-106][A-107][A-108][A-109][A-110] [A-111][A-112][A-113][A-114][A-115] [A-116][A-117][A-118][A-119][A-120] [A-121][A-122][A-123][A-124][A-125] [A-126][A-127][A-128][A-129][A-130] [A-131][A-132][A-133][A-134][A-135] [A-136][A-137][A-138][A-139][A-140] [A-141][A-142][A-143][A-144][A-145] [A-146][A-147][A-148][A-149][A-150] [A-151][A-152][A-153][A-154][A-155] [A-156][A-157][A-158][A-159][A-160] [A-161][A-162][A-163][A-164][A-165] [A-166][A-167][A-168][A-169][A-170] [A-171][A-172][A-173][A-174][A-175] .

7. In paragraph 1, The combination of the above chemical formulas 2 and 3 is a composition for an organic optoelectronic device represented by any one of the following chemical formulas 2A, 2C, and 2E: [Chemical Formula 2A] [Chemical Formula 2C] [Chemical Formula 2E] In the above chemical formulas 2A, 2C and 2E, L a3 and L a4 is a single bond, R 8 , R 9 , and R a1 Inland R a4 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, m8 and m9 are each independently one of the integers 1 to 4, L 3 -Ar 2 and L 4 -Ar 3 are each independently one of the substituents listed in Group Ⅰ below, [Group Ⅰ] In the above group Ⅰ, R 10 Inland R 14 are each independently hydrogen, deuterium, cyano group, C1 to C10 alkyl group or C6 to C12 aryl group, m10 is an integer between 1 and 5, m11 is one of the integers 1 to 4, m12 is an integer between 1 and 3, m13 is an integer of 1 or 2, m14 is an integer between 1 and 7, * is a connection point.

8. In paragraph 1, The second compound is a composition for an organic optoelectronic device selected from the compounds listed in Group 2 below: [Group 2] [C-1] [C-2] [C-3] [C-4] [C-5] [C-6] [C-7] [C-8] [C-9] [C-10] [C-11] [C-12] [C-13] [C-14] [C-15] [C-16] [C-17] [C-18] [C-19] [C-20] [C-21] [C-22] [C-23] [C-24] [C-25] [C-26] [C-27] [C-28] [C-29] [C-30] [C-31] [C-32] [C-33] [C-34] [C-35] [C-36] [C-37] [C-38] [C-39] [C-40] [C-41] [C-42] [C-43] [C-44] [C-45] [C-46] [C-47] [C-48] [C-49] [C-50] [C-51] [C-52] [C-53] [C-54] [C-55] [C-56] [C-57] [C-58] [C-59] [C-60] [C-61] [C-62] [C-63] [C-64] [C-65] [C-66] [C-67] [C-68] [C-69] [C-70] [C-71] [C-72] [C-73] [C-74] [C-75] [C-76] [C-77] [C-78] [C-79] [C-80] [C-81] [C-82] [C-83] [C-84] [C-85] [C-86] [C-87] [C-88] [C-89] [C-90] [C-91] [C-92] [C-93] [C-94] [C-95] [C-96] [C-97] [C-98] [C-99] [C-100] [C-101] [C-102] .

9. Positive and negative poles facing each other, comprising at least one organic layer positioned between the anode and the cathode, An organic optoelectronic device comprising a composition for an organic optoelectronic device according to any one of claims 1 to 8, wherein the organic layer comprises:

10. In paragraph 9, The above organic layer includes a light-emitting layer, An organic optoelectronic device, wherein the light-emitting layer comprises the composition for an organic optoelectronic device.

11. A display device comprising an organic optoelectronic device according to Article 9.

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