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

Abstract

The invention relates to a compound for an organic optoelectronic device represented by Chemical Formula 1 or Chemical Formula 2, an organic optoelectronic device including the same, and a display device. The contents of the above Chemical Formula 1 and Chemical Formula 2 are as defined in the specification.

Description

Technology Field

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

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

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

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

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

[0006] One embodiment provides a compound for organic optoelectronic devices capable of realizing high-efficiency and long-life organic optoelectronic devices.

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

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

[0009] Another embodiment provides a display device including the above-mentioned organic optoelectronic element. means of solving the problem

[0010] According to one embodiment, a compound for an organic optoelectronic device represented by the following chemical formula 1 or chemical formula 2 is provided.

[0011] [Chemical Formula 1]

[0012]

[0013] [Chemical Formula 2]

[0014]

[0015] In the above Chemical Formulas 1 and 2,

[0016] X 1 and X 2 Each is independently O, S, or SiR a R b And,

[0017] Z 1 To Z 3 Each independently N or CR c And,

[0018] Z 1 To Z 3 At least one of them is N, and

[0019] R a , R b , R c and R 1 to R 9 Each is independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C1 to C10 alkylsilyl group, or substituted or unsubstituted C6 to C12 aryl group, and

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

[0021] L 1 to L 4 Each is independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

[0022] m1, m2, and m4 are each independently one of integers from 1 to 4, and

[0023] m3 is one of the integers 1 to 3.

[0024] According to another embodiment, a composition for an organic optoelectronic device comprising a first compound and a second compound is provided.

[0025] The first compound above is a compound for an organic optoelectronic device as described above, and the second compound can be represented by the following chemical formula 3; or a combination of the following chemical formulas 4 and 5.

[0026] [Chemical Formula 3]

[0027]

[0028] In the above chemical formula 3,

[0029] R 10 to R 14 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0030] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0031] L 5 and L 6Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0032] m10, m13, and m14 are each independently one of integers 1 to 4, and

[0033] m11 and m12 are each independently one of integers 1 to 3, and

[0034] n is one of integers from 0 to 2;

[0035] [Chemical Formula 4] [Chemical Formula 5]

[0036]

[0037] In the above chemical formulas 4 and 5,

[0038] a1* to a4* of Chemical Formula 4 are each independently connected carbon (C) or Cl a -R d And,

[0039] Among a1* to a4* of Chemical Formula 4, two adjacent ones are each connected to * of Chemical Formula 5, and

[0040] L a , L 7 and L 8 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0041] R d , R 15 and R 16 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0042] Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0043] m15 and m16 are each independently one of integers from 1 to 4.

[0044] According to another embodiment, an organic optoelectronic device is provided comprising an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises a compound for the organic optoelectronic device.

[0045] According to another embodiment, a display device comprising the organic optoelectronic element is provided. Effects of the invention

[0046] High-efficiency, long-life organic optoelectronic devices can be realized. Brief explanation of the drawing

[0047] FIG. 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment. Specific details for implementing the invention

[0048] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention, and the present invention is defined only by the scope of the claims set forth below.

[0049] In this specification, "substitution" means that, unless otherwise defined, at least one hydrogen of a substituent or compound is substituted with a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

[0050] In one example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. Furthermore, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. Furthermore, in a specific example of the present invention, "substitution" means that at least one hydrogen in the substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen of a substituent or compound is substituted with a deuterium, cyano group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, terphenyl group, or naphthyl group.

[0051] In this specification, “non-substituted” means that a hydrogen atom remains a hydrogen atom without being substituted by another substituent.

[0052] In this specification, “hydrogen substitution (-H)” may include “deuterium substitution (-D) or “tritium substitution (-T).”

[0053] In this specification, "hetero" means, unless otherwise defined, that one functional group contains 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si, and the remainder is carbon.

[0054] In this specification, "aryl group" is a collective concept for a group having one or more hydrocarbon aromatic moietys, including a form in which all elements of the hydrocarbon aromatic moiety have p-orbitals and these p-orbitals form a conjugation, such as a phenyl group, a naphthyl group, etc., and a form in which two or more hydrocarbon aromatic moietys are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quarterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moietys are directly or indirectly fused, such as a fluorenyl group, etc.

[0055] Aryl groups include monocyclic, polycyclic, or fused-ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0056] In this specification, "heterocyclic group" is a superordinate concept including heteroaryl groups, meaning that a cyclic compound, such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, contains at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C). If the heterocyclic group is a fused ring, it may contain one or more heteroatoms in the entire heterocyclic group or in each ring.

[0057] For example, a "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si within the aryl group. Two or more heteroaryl groups may be directly connected through sigma bonds, or if the heteroaryl group comprises two or more rings, the two or more rings may be fused together. If the heteroaryl group is a fused ring, each ring may contain one to three heteroatoms.

[0058] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted crisenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0059] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic groups are a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazoleyl group, a substituted or unsubstituted triazoleyl group, a substituted or unsubstituted oxazoleyl group, a substituted or unsubstituted thiazoleyl group, a substituted or unsubstituted oxadiazoleyl group, a substituted or unsubstituted thiadiazoleyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazoleyl group, a substituted or unsubstituted indoleyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthiridinyl group, a substituted or unsubstituted benzoxazine dil group, a substituted or unsubstituted benzthiazine dil group, a substituted or unsubstituted acrridinyl group, a substituted or unsubstituted phenazine dil group, a substituted or unsubstituted phenothiazine dil group, a substituted or unsubstituted phenoxazine dil group, a substituted or unsubstituted carbazole dil group, a substituted or unsubstituted dibenzofuran dil group, a substituted or unsubstituted dibenzothiophen dil group, a substituted or unsubstituted benzonaphtufuran dil group, a substituted or unsubstituted benzonaphthiophen dil group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0060] In this specification, the term "hole characteristic" refers to a characteristic that can form holes by donating electrons when an electric field is applied, and means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and movement within the light-emitting layer by having a conduction characteristic along the HOMO level.

[0061] In addition, electronic properties refer to the ability to receive electrons when an electric field is applied, and they refer to properties that facilitate the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed at the light-emitting layer to the cathode, and the movement of electrons within the light-emitting layer by having conduction properties along the LUMO level.

[0062] A compound for an organic optoelectronic device according to one embodiment is described below.

[0063] A compound for an organic optoelectronic device according to one embodiment is represented by the following chemical formula 1 or chemical formula 2.

[0064] [Chemical Formula 1]

[0065]

[0066] [Chemical Formula 2]

[0067]

[0068] In the above Chemical Formulas 1 and 2,

[0069] X 1 and X 2 Each is independently O, S, or SiR a R b And,

[0070] Z 1 To Z 3 Each independently N or CR c And,

[0071] Z 1 To Z 3 At least one of them is N, and

[0072] R a , R b , R c and R 1 to R 9 Each is independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group, and

[0073] Ar 1 and Ar2 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group, and

[0074] L 1 to L 4 Each is independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

[0075] m1, m2, and m4 are each independently one of integers from 1 to 4, and

[0076] m3 is one of the integers 1 to 3.

[0077] The compound represented by Chemical Formula 1 has a structure in which a nitrogen-containing six-membered ring is substituted at the 1st or 2nd position of a dibenzofuran derivative, a 9-carbazole group is substituted at the 2nd or 1st position, and another dibenzofuran derivative is substituted at the 9th position.

[0078] In this specification, the term "dibenzofuran derivative" is defined as comprising dibenzofuran, dibenzothiophene, and dibenzosylol.

[0079] The compound represented by Chemical Formula 1 above includes a nitrogen-containing six-membered ring at the 1st or 2nd position, thereby enabling electron delocalization and increasing charge mobility. Accordingly, hole transport characteristics can be further improved, allowing for low driving and high efficiency performance of organic optoelectronic devices containing the same.

[0080] In addition, by introducing the aforementioned dibenzofuran derivative at position 9, electron delocalization is further expanded and steric hindrance is obtained, resulting in a lower deposition temperature, and accordingly, the lifetime characteristics of the organic light-emitting device to which this is applied can be significantly improved.

[0081] Meanwhile, although the stability of the molecule may be reduced due to the expansion of electron delocalization, the degradation of the triazine caused by electron delocalization can be prevented by simultaneously substituting a 9-carbazole group on the phenyl ring to which the nitrogen-containing 6-membered ring is substituted, thereby improving the degradation of the lifetime characteristics.

[0082] In Chemical Formulas 1 and 2, when m1 is 2 or more, each R 6 They may be the same or different from each other.

[0083] In Chemical Formulas 1 and 2, when m2 is 2 or more, respectively R 7 They may be the same or different from each other.

[0084] In Chemical Formulas 1 and 2, when m3 is 2 or more, respectively R 8 They may be the same or different from each other.

[0085] In Chemical Formulas 1 and 2, when m4 is 2 or more, each R 9 They may be the same or different from each other.

[0086] For example, Chemical Formula 1 can be expressed as any one of the following Chemical Formulas 1-1 to 1-4.

[0087] [Chemical Formula 1-1]

[0088]

[0089] [Chemical Formula 1-2]

[0090]

[0091] [Chemical Formula 1-3]

[0092]

[0093] [Chemical Formula 1-4]

[0094]

[0095] In the above chemical formulas 1-1 to 1-4,

[0096] X 1 , X 2 , Z 1To Z 3 , R 1 to R 9 , Ar 1 or Ar 4 , L 1 to L 4 The definitions of , and m1 to m4 are as described above.

[0097] The above chemical formula 2 can be expressed as any one of the following chemical formulas 2-1 to 2-4.

[0098] [Chemical Formula 2-1]

[0099]

[0100] [Chemical Formula 2-2]

[0101]

[0102] [Chemical Formula 2-3]

[0103]

[0104] [Chemical Formula 2-4]

[0105]

[0106] In the above chemical formulas 2-1 to 2-4,

[0107] X 1 , X 2 , Z 1 To Z 3 , R 1 to R 7 , Ar 1 , L 1 to L 3 The definitions of , and m1 to m7 are as described above.

[0108] A compound for an organic optoelectronic device according to one embodiment of the present invention may be represented by any one of the above formulas 1-1, 1-4, 2-1, and 2-4.

[0109] A compound for an organic optoelectronic device according to a specific embodiment of the present invention may be represented by any one of the above formulas 1-1, 1-4, and 2-1.

[0110] For example, L 1 and L 2 Each may independently be a single bond, or a substituted or unsubstituted phenylene group.

[0111] As a specific example, the above L 1 and L 2 Each can be a single bond.

[0112] For example, the above Ar 1 and Ar 2 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a substituted or unsubstituted carbazoleyl group.

[0113] As a specific example, the aforementioned Ar 1 and Ar 2 Each may independently be a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0114] For example, the above R 1 to R 9 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C5 alkylsilyl group, or substituted or unsubstituted C6 to C12 aryl group.

[0115] As a specific example, the above R 1 to R 9 Each may independently be hydrogen, deuterium, cyano group, trimethylsilyl group, substituted or unsubstituted phenyl group, or substituted or unsubstituted biphenyl group.

[0116] As an example, L of the above chemical formula 1 3 and L 4 Each may independently be a single bond or a substituted or unsubstituted C6 to C12 arylene group.

[0117] For example, L of the above chemical formula 1 3and L 4 Each may independently be a single bond, or a substituted or unsubstituted phenylene group.

[0118] For example, Z 1 To Z 3 At least two of them can be N.

[0119] For example, Z 1 To Z 3 Each can be N.

[0120] For example, R a and R b Each may be an independently substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0121] In the most specific embodiment, the compound represented by Formula 1 or Formula 2 may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[0122] [Group 1]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167] A composition for an organic optoelectronic device according to another embodiment comprises a first compound and a second compound, wherein the first compound is the aforementioned compound for an organic optoelectronic device, and the second compound may be represented by the following formula 3; or a combination of formulas 4 and 5.

[0168] [Chemical Formula 3]

[0169]

[0170] In the above chemical formula 3,

[0171] R 10 to R 14 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0172] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0173] L 5 and L 6 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0174] m10, m13, and m14 are each independently one of integers 1 to 4, and

[0175] m11 and m12 are each independently one of integers 1 to 3, and

[0176] n is one of integers from 0 to 2;

[0177] [Chemical Formula 4] [Chemical Formula 5]

[0178]

[0179] In the above chemical formulas 4 and 5,

[0180] a1* to a4* of Chemical Formula 4 are each independently connected carbon (C) or Cl a -R d And,

[0181] Among a1* to a4* of Chemical Formula 4, two adjacent ones are each connected to * of Chemical Formula 5, and

[0182] L a , L 7 and L 8 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0183] R d , R 15 and R 16 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and

[0184] Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0185] m15 and m16 are each independently one of integers from 1 to 4.

[0186] The second compound mentioned above can be used in the light-emitting layer together with the first compound to increase charge mobility and stability, thereby improving luminous efficiency and lifespan characteristics.

[0187] In the above Chemical Formula 3, when m10 is 2 or more, each R 10 They may be the same or different from each other.

[0188] In the above Chemical Formula 3, when m11 is 2 or more, each R 11 They may be the same or different from each other.

[0189] In the above Chemical Formula 3, when m12 is 2 or more, each R 12 They may be identical or different from each other.

[0190] In the above Chemical Formula 3, when m13 is 2 or more, each R 13 They may be the same or different from each other.

[0191] In the above Chemical Formula 3, when m14 is 2 or more, each R 14 They may be identical or different from each other.

[0192] For example, Ar of the above chemical formula 3 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0193] L of the above chemical formula 3 5 and L 6 Each is independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group, and

[0194] R of the above chemical formula 3 10 to R 14Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0195] n can be 0 or 1.

[0196] For example, the term "substitution" in the above chemical formula 3 means that at least one hydrogen is substituted with a deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0197] For example, Ar of the above chemical formula 3 3 and Ar 4 Each may independently be a substituted or unsubstituted carbazole group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0198] In a specific embodiment of the present invention, the formula 3 may be represented by one of the following formulas 3-1 to 3-15.

[0199] [Chemical Formula 3-1] [Chemical Formula 3-2] [Chemical Formula 3-3]

[0200]

[0201] [Chemical Formula 3-4] [Chemical Formula 3-5] [Chemical Formula 3-6]

[0202]

[0203] [Chemical Formula 3-7] [Chemical Formula 3-8] [Chemical Formula 3-9]

[0204]

[0205] [Chemical Formula 3-10] [Chemical Formula 3-11] [Chemical Formula 3-12]

[0206]

[0207] [Chemical Formula 3-13] [Chemical Formula 3-14] [Chemical Formula 3-15]

[0208]

[0209] In the above chemical formulas 3-1 to 3-15, R 9 to R 13 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 5 -Ar 3 and L 6 -Ar 4 Each can be independently one of the substituents listed in Group II below.

[0210] [Group II]

[0211]

[0212] In the above Group II,

[0213] R 17 to R 21 Each is independently hydrogen, deuterium, a cyano group, a C1 to C10 alkyl group, or a C6 to C12 aryl group, and

[0214] m17 is one of integers from 1 to 5, and

[0215] m18 is one of integers from 1 to 4, and

[0216] m19 is one of integers from 1 to 3, and

[0217] m20 is an integer of 1 or 2, and

[0218] m21 is one of integers from 1 to 7, and

[0219] * is a connection point.

[0220] In the above Group II, if m17 is 2 or more, each R 17 They may be the same or different from each other.

[0221] In the above Group II, if m18 is 2 or more, each R 18 They may be the same or different from each other.

[0222] In the above Group II, if m19 is 2 or more, each R 19 They may be identical or different from each other.

[0223] In the above Group II, when m20 is 2, each R 20 They may be the same or different from each other.

[0224] In the above Group II, if m21 is 2 or more, each R 21 They may be the same or different from each other.

[0225] In the above Chemical Formulas 4 and 5, when m15 is 2 or more, each R 15 They may be identical or different from each other.

[0226] In the above Chemical Formulas 4 and 5, when m16 is 2 or more, each R 16 They may be the same or different from each other.

[0227] The second compound above may be represented by, for example, any one of the following formulas 4A, 4B, 4C, 4D, and 4E.

[0228] [Chemical Formula 4A] [Chemical Formula 4B] [Chemical Formula 4C]

[0229]

[0230] [Chemical Formula 4D] [Chemical Formula 4E]

[0231]

[0232] In the above chemical formulas 4A to 4E, L 7 , L 8 , Ar 5 , Ar 6 , R 15 , and R 16 It is as previously stated, and

[0233] L a1 to L a4 is the aforementioned L 7 and L 8 It is the same as the definition of,

[0234] R d1 to R d4 is the aforementioned R 15 , and R 16 It is the same as the definition of.

[0235] For example, Ar of the above Chemical Formulas 4 and 5 5 and Ar 6 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0236] R d1 to R d4 , R 15 , and R 16 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0237] In a specific embodiment of the present invention, L of Formula 4 and Formula 5 7 -Ar 5 and L 8 -Ar 6 Each can be independently selected from the substituents listed in Group II above.

[0238] In one embodiment, the R d1 to R d4 , R 15 , and R 16 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0239] For example, the above R d1 to R d4 , R 15 , and R16 Each can independently be hydrogen, deuterium, a cyano group, or a substituted or unsubstituted phenyl group, and

[0240] In a specific embodiment, the R d1 to R d4 , R 15 , and R 16 Each can independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0241] In a specific embodiment of the present invention, the second compound may be represented by the formula 3-8, and the Ar of the formula 3-8 3 and Ar 4 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and L 5 and L 6 Each is independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and R 10 to R 13 Each may independently be hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group.

[0242] For example, R of the above chemical formula 3-8 10 to R 13 Each is independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and L 5 -Ar 3 and L 6 -Ar 4 Each may independently be one of the substituents listed in Group II above.

[0243] In another specific embodiment of the present invention, the second compound may be represented by the formula 4C, and L of the formula 4C a3 and L a4 is a single bond, and L 7 and L 8 Each is independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, and R 15 , R 16 , R d3 and R d4 are hydrogen, deuterium, or a phenyl group, respectively, and Ar 5 and Ar 6 Each may independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazoleyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0244] For example, L of the above chemical formula 4C c3 and L c4 is a single bond, and R 15 , R 16 , R d3 and R d4 Each is independently hydrogen, deuterium, or a C6 to C12 aryl group, and L 7 -Ar 5 and L 8 -Ar 6 Each may independently be one of the substituents listed in Group II above.

[0245] For example, the compound for the second organic optoelectronic device may be one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0246] [Group 2]

[0247] [B-1] [B-2] [B-3] [B-4] [B-5]

[0248]

[0249] [B-6] [B-7] [B-8] [B-9] [B-10]

[0250]

[0251] [B-11] [B-12] [B-13] [B-14] [B-15]

[0252]

[0253] [B-16] [B-17] [B-18] [B-19] [B-20]

[0254]

[0255] [B-21] [B-22] [B-23] [B-24] [B-25]

[0256]

[0257] [B-26] [B-27] [B-28] [B-29] [B-30]

[0258]

[0259] [B-31] [B-32] [B-33] [B-34] [B-35]

[0260]

[0261] [B-36] [B-37] [B-38] [B-39] [B-40]

[0262]

[0263] [B-41] [B-42] [B-43] [B-44] [B-45]

[0264]

[0265] [B-46] [B-47] [B-48] [B-49] [B-50]

[0266]

[0267] [B-51] [B-52] [B-53] [B-54] [B-55]

[0268]

[0269] [B-56] [B-57] [B-58] [B-59] [B-60]

[0270]

[0271] [B-61] [B-62] [B-63] [B-64] [B-65]

[0272]

[0273] [B-66] [B-67] [B-68] [B-69] [B-70]

[0274]

[0275] [B-71] [B-72] [B-73] [B-74] [B-75]

[0276]

[0277] [B-76] [B-77] [B-78] [B-79] [B-80]

[0278]

[0279] [B-81] [B-82] [B-83] [B-84] [B-85]

[0280]

[0281] [B-86] [B-87] [B-88] [B-89] [B-90]

[0282]

[0283] [B-91] [B-92] [B-93] [B-94] [B-95]

[0284]

[0285] [B-96] [B-97] [B-98] [B-99] [B-100]

[0286]

[0287] [B-101] [B-102] [B-103] [B-104] [B-105]

[0288]

[0289] [B-106] [B-107] [B-108] [B-109] [B-110]

[0290]

[0291] [B-111] [B-112] [B-113] [B-114] [B-115]

[0292]

[0293] [B-116] [B-117] [B-118] [B-119] [B-120]

[0294]

[0295] [B-121] [B-122] [B-123] [B-124] [B-125]

[0296]

[0297] [B-126] [B-127] [B-128] [B-129] [B-130]

[0298]

[0299] [B-131] [B-132] [B-133] [B-134] [B-135]

[0300]

[0301] [B-136] [B-137] [B-138] [B-139] [B-140]

[0302]

[0303] [B-141] [B-142] [B-143] [B-144] [B-145]

[0304]

[0305] [B-143] [B-144] [B-145] [B-146] [B-147]

[0306]

[0307] [B-148] [B-149] [B-150] [B-151]

[0308]

[0309] [B-152] [B-153] [B-154] [B-155]

[0310]

[0311] [B-156] [B-157] [B-158] [B-159]

[0312]

[0313] [B-160] [B-161] [B-162] [B-163]

[0314]

[0315] [B-164] [B-165] [B-166] [B-167]

[0316]

[0317] [B-168] [B-169] [B-170] [B-171]

[0318]

[0319] [B-172] [B-173] [B-174]

[0320]

[0321] [B-175] [B-176] [B-177] [B-178]

[0322]

[0323] [B-179] [B-180] [B-181] [B-182]

[0324]

[0325] [B-183] [B-184] [B-185] [B-185]

[0326]

[0327] [B-186] [B-187] [B-188] [B-189]

[0328]

[0329] [B-190] [B-191] [B-192] [B-193]

[0330]

[0331] [C-1] [C-2] [C-3] [C-4]

[0332]

[0333] [C-5] [C-6] [C-7] [C-8]

[0334]

[0335] [C-9] [C-10] [C-11] [C-12]

[0336]

[0337] [C-13] [C-14] [C-15] [C-16]

[0338]

[0339] [C-17] [C-18] [C-19] [C-20]

[0340]

[0341] [C-21] [C-22] [C-23] [C-24]

[0342]

[0343] [C-25] [C-26] [C-27] [C-28]

[0344]

[0345] [C-29] [C-30] [C-31] [C-32]

[0346]

[0347] [C-33] [C-34] [C-35] [C-36]

[0348]

[0349] [C-37] [C-38] [C-39] [C-40]

[0350]

[0351] [C-41] [C-42] [C-43] [C-44]

[0352]

[0353] [C-45] [C-46] [C-47] [C-48]

[0354]

[0355] [C-49] [C-50] [C-51] [C-52]

[0356]

[0357] [C-53] [C-54] [C-55] [C-56]

[0358]

[0359] [C-57] [C-58] [C-59]

[0360]

[0361] [C-60] [C-61] [C-62] [C-63]

[0362]

[0363] [C-64] [C-65] [C-66] [C-67]

[0364]

[0365] [C-68] [C-69] [C-70] [C-71]

[0366]

[0367] [C-72] [C-73] [C-74] [C-75]

[0368]

[0369] [C-76] [C-77] [C-78] [C-79]

[0370]

[0371] [C-80] [C-81] [C-82] [C-83]

[0372]

[0373] [C-84] [C-85] [C-86] [C-87]

[0374]

[0375] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By including them within the above range, bipolar characteristics can be realized by adjusting the weight ratio appropriately using the electron transport ability of the first compound and the hole transport ability of the second compound, thereby improving efficiency and lifespan. Within the above range, they may be included in a weight ratio of, for example, about 10:90 to 90:10 or about 20:80 to 80:20, and for example, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, they may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0376] In addition to the aforementioned first and second compounds, one or more additional compounds may be included.

[0377] The aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices may be a composition further comprising a dopant.

[0378] The dopant can be, for example, a phosphorescent dopant, for example, a red, green, or blue phosphorescent dopant, for example, a red or green phosphorescent dopant.

[0379] A dopant is a substance that is mixed in trace amounts into a compound or composition for an organic optoelectronic device to produce light emission, and generally, a substance such as a metal complex that emits light through multiple excitation, which excites it to a triplet state or higher, may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or more types.

[0380] Phosphorescent dopants are an example of a dopant, and examples of phosphorescent dopants include organometallic compounds containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. Phosphorescent dopants may include, for example, compounds represented by the following chemical formula Z, but are not limited thereto.

[0381] [Chemical Formula Z]

[0382] L 9 MX 3

[0383] In the above chemical formula Z, M is a metal, and L 9 and X 3 is a ligand that is the same or different from each other and forms a complex with M.

[0384] 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 9 and X 3 It can be, for example, a bidentate ligand.

[0385] L 9 and X 3 Examples of ligands represented by may be selected from the chemical formulas listed in Group A below, but are not limited thereto.

[0386] [Group A]

[0387]

[0388] In the above group A,

[0389] R 300 to R 302 Each is independently hydrogen, deuterium, a C1 to C30 alkyl group substituted or unsubstituted with a halogen, a C6 to C30 aryl group substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen, and

[0390] R 303 to R 324Each is independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0391] For example, it may include a dopant represented by the following chemical formula V.

[0392] [Chemical Formula V]

[0393]

[0394] In the above chemical formula V,

[0395] R 101 to R 116 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0396] The above R 132 to R 134 Each is independently a C1 to C6 alkyl group, and

[0397] R 101 to R 116 At least one of them is a functional group represented by the following chemical formula V-1, and

[0398] L 100It is a bidentate ligand of a monovalent anion that coordinates to iridium through lone pairs of electrons on carbon or heteroatoms, and

[0399] m14 and m15 are independently any one of integers from 0 to 3, and m14 + m15 is any one of integers from 1 to 3, and

[0400] [Chemical Formula V-1]

[0401]

[0402] In the above chemical formula V-1,

[0403] R 135 to R 139 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0404] * represents the part connected to the carbon atom.

[0405] For example, it may include a dopant represented by the following chemical formula Z-1.

[0406] [Chemical Formula Z-1]

[0407]

[0408] In the above chemical formula Z-1, rings A, B, C, and D each independently represent a pentagonal or hexagonal carbocyclic or heterocyclic ring;

[0409] R A , R B , R C , and R D Each independently represents a uniform, bisubstitution, trisubstitution, or quadruple substitution, or no substitution;

[0410] L B , L C , and L DEach is independently selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0411] If nA is 1, L E is selected from the group consisting of direct bonding, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; and when nA is 0, L E is not present;

[0412] R A , R B , R C , R D , R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; any adjacent R A , R B , R C , R D , R, and R' are arbitrarily connected to form a ring; X B , X C , X D , and X E are each independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 Each represents oxygen or direct bonding.

[0413] The dopant according to one embodiment may be a platinum complex, for example, represented by the following chemical formula VI.

[0414] [Chemical Formula VI]

[0415]

[0416] In the above chemical formula VI,

[0417] X 100 It contains O, S, and NR 131 Selected from among,

[0418] R 117 to R 131 Each is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0419] The above R 132 to R 134 Each is independently a C1 to C6 alkyl group, and

[0420] R 117 to R 131 At least one of them is -SiR 132 R 133 R 134 or is a tert-butyl group, and

[0421] The above R 132 to R 134 Each is independently a C1 to C6 alkyl group.

[0422] An organic optoelectronic device to which the compound for organic optoelectronic devices and the composition for organic optoelectronic devices described above are applied is described below.

[0423] Organic optoelectronic devices are not particularly limited as long as they are devices capable of mutually converting electrical energy and light energy, and examples include organic photovoltaic devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0424] Here, an organic light-emitting diode, which is an example of an organic optoelectronic device, is described with reference to the drawing.

[0425] FIG. 1 is a cross-sectional view showing an organic light-emitting device according to one embodiment.

[0426] Referring to FIG. 1, an organic light-emitting device (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other, and an organic layer (105) located between the anode (120) and the cathode (110).

[0427] The anode (120) may be made of a conductor with a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The anode (120) may be a metal or an alloy thereof, such as nickel, platinum, vanadium, chromium, copper, zinc, gold; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole and polyaniline, but is not limited thereto.

[0428] The cathode (110) may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide and / or a conductive polymer. The cathode (110) may be a metal or an alloy thereof, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, etc.; or a multilayer material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al and BaF2 / Ca, but is not limited thereto.

[0429] The organic layer (105) may include the aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices.

[0430] The above organic layer (105) includes a light-emitting layer (130), and the light-emitting layer (130) may include the aforementioned compound for organic optoelectronic devices or composition for organic optoelectronic devices.

[0431] A composition for an organic optoelectronic device that further comprises a dopant may be, for example, a green light-emitting composition.

[0432] The light-emitting layer (130) may include, for example, the aforementioned compounds for organic optoelectronic devices as phosphorescent hosts.

[0433] The organic layer may include additional charge transport regions in addition to the light-emitting layer.

[0434] The above charge transport region may be, for example, a hole transport region (140).

[0435] The hole transport region (140) can further increase hole injection and / or hole mobility between the anode (120) and the light-emitting layer (130) and block electrons.

[0436] 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.

[0437] [Group B]

[0438]

[0439]

[0440]

[0441]

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451]

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461] In addition to the aforementioned compound, known compounds and compounds with similar structures described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. may also be used in the hole transport region (140).

[0462] In addition, the charge transport region may be, for example, an electron transport region (150).

[0463] 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.

[0464] Specifically, the electron transport region (150) may include an electron transport layer between the cathode (110) and the light-emitting layer (130), and an electron transport auxiliary layer between the light-emitting layer (130) and the electron transport layer, and at least one of the compounds listed in Group C below may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0465] [Group C]

[0466]

[0467]

[0468]

[0469]

[0470]

[0471]

[0472]

[0473]

[0474]

[0475]

[0476]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483] One embodiment may be an organic light-emitting device including a light-emitting layer as an organic layer.

[0484] Another embodiment may be an organic light-emitting device including a light-emitting layer and a hole transport region as the organic layer.

[0485] Another embodiment may be an organic light-emitting device including a light-emitting layer and an electron transport region as organic layers.

[0486] An organic light-emitting device according to one embodiment of the present invention may include a hole transport region (140) and an electron transport region (150) in addition to the light-emitting layer (130) as an organic layer (105) as shown in FIG. 1.

[0487] Meanwhile, the organic light-emitting device may additionally include an electron injection layer (not shown), a hole injection layer (not shown), etc., in addition to the light-emitting layer as the aforementioned organic layer.

[0488] An organic light-emitting device (100) can be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer using a dry film deposition method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and then forming a cathode or an anode thereon.

[0489] The above-described organic light-emitting element can be applied to an organic light-emitting display device.

[0491] The above-described embodiment will be explained in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the claims.

[0492] Unless otherwise noted, the starting materials and reactants used in the following examples and synthesis examples were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry, or P&H Tech, or synthesized using known methods.

[0494] Synthesis Example 1: Synthesis of Intermediate I-1

[0495]

[0496] 2,6-dimethoxyphenylboronic acid (100g, 550mmol) was dissolved in 1L of dioxane under a nitrogen environment, to which 2,3-dibromo-1,4-difluorobenzene (179g, 659mmol) and tetrakis(triphenylphosphine)palladium (12.7g, 11.0mmol) were added and stirred. Then, potassium carbonate (190g, 1,375mmol) saturated with water was added, and the mixture was heated and refluxed for 8 hours. After the reaction was complete, water was added to the reaction mixture and extracted with dichloromethane (DCM). Subsequently, water was removed using magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-1 (163g, 90%).

[0497] HRMS (70eV, EI+): m / z calcd for C14H11BrF2O2: 327.9910, found: 327.

[0498] Elemental Analysis: C, 51%; H, 3%

[0500] Synthesis Example 2: Synthesis of Intermediate I-2

[0501]

[0502] Intermediate I-1 (160 g, 486 mmol) and pyridine hydrochloride (562 g, 4,861 mmol) were added under a nitrogen environment and heated at 180°C for 1 hour under reflux. After the reaction was complete, water was added to the reaction solution and extracted with ethyl acetate (EA). Subsequently, water was removed using magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-2 (139 g, 95%).

[0503] HRMS (70eV, EI+): m / z calcd for C12H7BrF2O2: 299.9597, found: 299.

[0504] Elemental Analysis: C, 48%; H, 2%

[0506] Synthesis Example 3: Synthesis of Intermediate I-3

[0507]

[0508] Intermediate I-2 (135 g, 448 mmol) was dissolved in 1.3 L of N,N-dimethylformamide (DMF) under a nitrogen environment, followed by the addition of Potassium phosphate tribasic (190 g, 897 mmol) and refluxing at 180°C for 3 hours. After the reaction was complete, the solvent was removed by distillation, water was added to the reaction mixture, and it was extracted with dichloromethane (DCM). Subsequently, water was removed using magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-3 (101 g, 80%).

[0509] HRMS (70eV, EI+): m / z calcd for C12H6BrFO2: 279.9535, found: 279.

[0510] Elemental Analysis: C, 51%; H, 2%

[0512] Synthesis Example 4: Synthesis of Intermediate I-4

[0513]

[0514] Intermediate I-3 (100g, 356mmol) was dissolved in 0.1L of dichloromethane (DCM) under a nitrogen environment, and the temperature was lowered to 0°C. Pyridine (120g, 427mmol) was added and stirred for 30 minutes, after which difluoromethanesulfonic anhydride (33.8g, 427mmol) was slowly added and stirred. After 3 hours, the reaction mixture was lowered to 0°C, water was slowly added over 30 minutes, and the mixture was extracted with dichloromethane (DCM). Subsequently, water was removed using magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-4 (144g, 98%).

[0515] HRMS (70eV, EI+): m / z calcd for C13H5BrF4O4S: 411.9028, found: 411.

[0516] Elemental Analysis: C, 38%; H, 1%

[0518] Synthesis Example 5: Synthesis of Intermediate I-5

[0519]

[0520] Intermediate I-5 (187g, 78%) was obtained using intermediate I-4 (140g, 339mmol) and dibenzofuran-1-boronic acid (79.0g, 373mmol) purchased from Tokyo Chemical Industry in the same manner as in Synthesis Example 1.

[0521] HRMS (70eV, EI+): m / z calcd for C24H12BrFO2: 430.0005, found: 430.

[0522] Elemental Analysis: C, 67%; H, 3%

[0524] Synthesis Example 6: Synthesis of Intermediate I-6

[0525]

[0526] Intermediate I-5 (185 g, 429 mmol) was dissolved in 0.2 L of N-methyl-2-pyrrolidone (NMP) under a nitrogen environment, to which 9H-carbazole (78.9 g, 472 mmol) and cesium carbonate (280 g, 858 mmol) were added, and the mixture was heated and refluxed for 5 hours. After the reaction was complete, the solvent was removed by distillation, water was added to the reaction mixture, and it was extracted with dichloromethane (DCM). Subsequently, water was removed using magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-6 (151 g, 61%).

[0527] HRMS (70eV, EI+): m / z calcd for C36H20BrNO2: 577.0677, found: 577.

[0528] Elemental Analysis: C, 75%; H, 3%

[0530] Synthesis Example 7: Synthesis of Intermediate I-7

[0531]

[0532] Intermediate I-6 (150 g, 259 mmol) was dissolved in 300 mL of tetrahydrofuran (THF) under a nitrogen environment and cooled to -78°C. To this, 2.5 M n-BuLi dissolved in hexane (124 mL, 311 mmol) was slowly added dropwise over 10 minutes, followed by the addition of triisopropyl borate (58.5 g, 311 mmol) after 30 minutes. After the reaction was complete, 1N HCl water (311 mL, 311 mmol) was added to neutralize the reaction solution. The mixture was then extracted with ethyl acetate (EA) and dehydrated using magnesium sulfate anhydrous. The resulting residue was washed for impurities with hexane and dichloromethane (DCM) to obtain intermediate I-7 (120 g, 85%).

[0533] HRMS (70eV, EI+): m / z calcd for C36H22BNO4: 543.1642, found: 543.

[0534] Elemental Analysis: C, 80%; H, 4%

[0536] Synthesis Example 8: Synthesis of Compound 4

[0537]

[0538] Compound 4 (22.9g, 85%) was obtained by synthesizing intermediate I-7 (20g, 36.8mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.85g, 36.8mmol) purchased from Tokyo Chemical Industry in the same manner as in Synthesis Example 1.

[0539] HRMS (70eV, EI+): m / z calcd for C51H30N4O2: 730.2369, found: 730.

[0540] Elemental Analysis: C, 84%; H, 4%

[0542] Synthesis Example 9: Synthesis of Intermediate I-8

[0543]

[0544] Intermediate I-4 (50g, 121mmol) and dibenzofuran-4-boronic acid (30.8g, 145mmol) purchased from Tokyo Chemical Industry were synthesized in the same manner as in Synthesis Example 1 to obtain intermediate I-8 (41.7g, 80%).

[0545] HRMS (70eV, EI+): m / z calcd for C24H12BrFO2: 430.0005, found: 430.

[0546] Elemental Analysis: C, 67%; H, 3%

[0548] Synthesis Example 10: Synthesis of Intermediate I-9

[0549]

[0550] Intermediate I-8 (40g, 92.8mmol) and 9H-carbazole (17.1g, 102mmol) were synthesized in the same manner as in Synthesis Example 6 to obtain intermediate I-9 (32.2g, 60%).

[0551] HRMS (70eV, EI+): m / z calcd for C36H20BrNO2: 577.0677, found: 577.

[0552] Elemental Analysis: C, 75%; H, 3%

[0554] Synthesis Example 11: Synthesis of Intermediate I-10

[0555]

[0556] Intermediate I-9 (30g, 51.9mmol) was synthesized in the same manner as in Synthesis Example 7 to obtain intermediate I-10 (25.4g, 90%).

[0557] HRMS (70eV, EI+): m / z calcd for C36H22BNO4: 543.1642, found: 543.

[0558] Elemental Analysis: C, 80%; H, 4%

[0560] Synthesis Example 12: Synthesis of Compound 1

[0561]

[0562] Compound 1 (24.2g, 90%) was obtained by synthesizing intermediate I-10 (20g, 36.8mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.85g, 36.8mmol) in the same manner as in Synthesis Example 1.

[0563] HRMS (70eV, EI+): m / z calcd for C51H30N4O2: 730.2369, found: 730.

[0564] Elemental Analysis: C, 84%; H, 4%

[0566] Synthesis Example 13: Synthesis of Intermediate I-11

[0567]

[0568] Intermediate I-4 (50g, 121mmol) and dibenzofuran-3-boronic acid (30.8g, 145mmol) were synthesized in the same manner as in Synthesis Example 1 to obtain intermediate I-11 (40.7g, 78%).

[0569] HRMS (70eV, EI+): m / z calcd for C24H12BrFO2: 430.0005, found: 430.

[0570] Elemental Analysis: C, 67%; H, 3%

[0572] Synthesis Example 14: Synthesis of Intermediate I-12

[0573]

[0574] Intermediate I-11 (40g, 92.8mmol) and 9H-carbazole (17.1g, 102mmol) were synthesized in the same manner as in Synthesis Example 6 to obtain intermediate I-12 (34.9g, 65%).

[0575] HRMS (70eV, EI+): m / z calcd for C36H20BrNO2: 577.0677, found: 577.

[0576] Elemental Analysis: C, 75%; H, 3%

[0578] Synthesis Example 15: Synthesis of Intermediate I-13

[0579]

[0580] Intermediate I-12 (30g, 51.9mmol) was synthesized in the same manner as in Synthesis Example 7 to obtain intermediate I-13 (22.8g, 81%).

[0581] HRMS (70eV, EI+): m / z calcd for C36H22BNO4: 543.1642, found: 543.

[0582] Elemental Analysis: C, 80%; H, 4%

[0584] Synthesis Example 16: Synthesis of Compound 2

[0585]

[0586] Compound 2 (22.6g, 84%) was obtained by synthesizing intermediate I-13 (20g, 36.8mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.85g, 36.8mmol) in the same manner as in Synthesis Example 1.

[0587] HRMS (70eV, EI+): m / z calcd for C51H30N4O2: 730.2369, found: 730.

[0588] Elemental Analysis: C, 84%; H, 4%

[0590] Synthesis Example 17: Synthesis of Intermediate I-14

[0591]

[0592] Intermediate I-4 (50g, 121mmol) and dibenzofuran-2-boronic acid (30.8g, 145mmol) were synthesized in the same manner as in Synthesis Example 1 to obtain intermediate I-14 (41.7g, 80%).

[0593] HRMS (70eV, EI+): m / z calcd for C24H12BrFO2: 430.0005, found: 430.

[0594] Elemental Analysis: C, 67%; H, 3%

[0596] Synthesis Example 18: Synthesis of Intermediate I-15

[0597]

[0598] Intermediate I-14 (40g, 92.8mmol) and 9H-carbazole (17.1g, 102mmol) were synthesized in the same manner as in Synthesis Example 6 to obtain intermediate I-15 (30.1g, 56%).

[0599] HRMS (70eV, EI+): m / z calcd for C36H20BrNO2: 577.0677, found: 577.

[0600] Elemental Analysis: C, 75%; H, 3%

[0602] Synthesis Example 19: Synthesis of Intermediate I-16

[0603]

[0604] Intermediate I-15 (25g, 43.2mmol) was synthesized in the same manner as in Synthesis Example 7 to obtain intermediate I-16 (20.7g, 88%).

[0605] HRMS (70eV, EI+): m / z calcd for C36H22BNO4: 543.1642, found: 543.

[0606] Elemental Analysis: C, 80%; H, 4%

[0608] Synthesis Example 20: Synthesis of Compound 3

[0609]

[0610] Compound 3 (21.5g, 80%) was obtained by synthesizing intermediate I-16 (20g, 36.8mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.85g, 36.8mmol) in the same manner as in Synthesis Example 1.

[0611] HRMS (70eV, EI+): m / z calcd for C51H30N4O2: 730.2369, found: 730.

[0612] Elemental Analysis: C, 84%; H, 4%

[0614] Synthesis Example 21: Synthesis of Intermediate I-17

[0615]

[0616] Intermediate I-4 (50g, 121mmol) and dibenzothiophene-4-boronic acid (33.1g, 145mmol) purchased from Tokyo Chemical Industry were synthesized in the same manner as in Synthesis Example 1 to obtain intermediate I-17 (49.8g, 92%).

[0617] HRMS (70eV, EI+): m / z calcd for C24H12BrFOS: 445.9776, found: 445.

[0618] Elemental Analysis: C, 64%; H, 3%

[0620] Synthesis Example 22: Synthesis of Intermediate I-18

[0621]

[0622] Intermediate I-17 (48g, 107mmol) and 9H-carbazole (19.7g, 118mmol) were synthesized in the same manner as in Synthesis Example 6 to obtain intermediate I-18 (33.7g, 53%).

[0623] HRMS (70eV, EI+): m / z calcd for C36H20BrNOS: 593.0449, found: 593.

[0624] Elemental Analysis: C, 73%; H, 3%

[0626] Synthesis Example 23: Synthesis of Intermediate I-19

[0627]

[0628] Intermediate I-18 (32g, 53.8mmol) was synthesized in the same manner as in Synthesis Example 7 to obtain intermediate I-19 (26.2g, 87%).

[0629] HRMS (70eV, EI+): m / z calcd for C36H22BNO3S: 559.1413, found: 559.

[0630] Elemental Analysis: C, 77%; H, 4%

[0632] Synthesis Example 24: Synthesis of Compound 5

[0633]

[0634] Compound 5 (23.5g, 88%) was obtained by synthesizing intermediate I-19 (20g, 35.8mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.57g, 35.8mmol) in the same manner as in Synthesis Example 1.

[0635] HRMS (70eV, EI+): m / z calcd for C51H30N4OS: 746.2140, found: 746.

[0636] Elemental Analysis: C, 82%; H, 4%

[0638] Synthesis Example 25: Synthesis of Intermediate I-20

[0639]

[0640] 4-cyanophenylboronic acid (63g, 427mmol) and 2,4-dichloro-6-phenyl-1,3,5-triazine (145g, 641mmol) were synthesized in the same manner as in Synthesis Example 1 to obtain intermediate I-20 (65.0g, 52%).

[0641] HRMS (70eV, EI+): m / z calcd for C16H9ClN4: 292.0516, found: 292.

[0642] Elemental Analysis: C, 66%; H, 3%

[0644] Synthesis Example 26: Synthesis of Compound 54

[0645]

[0646] Compound 54 (25.0g, 90%) was obtained by synthesizing intermediate I-7 (20g, 36.8mmol) and intermediate I-20 (10.8g, 36.8mmol) in the same manner as in Synthesis Example 1.

[0647] HRMS (70eV, EI+): m / z calcd for C52H29N5O2: 755.2321, found: 755.

[0648] Elemental Analysis: C, 83%; H, 4%

[0650] Synthesis Example 27: Synthesis of Compound 94

[0651]

[0652] Compound 94 (23.8g, 80%) was obtained by synthesizing intermediate I-7 (20g, 36.8mmol) and 2-(biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (12.7g, 36.8mmol) purchased from Tokyo Chemical Industry in the same manner as in Synthesis Example 1.

[0653] HRMS (70eV, EI+): m / z calcd for C57H34N4O2: 806.2682, found: 806.

[0654] Elemental Analysis: C, 85%; H, 4%

[0656] Synthesis Example 28: Synthesis of Intermediate I-21

[0657]

[0658] Intermediate I-21 (142g, 91%) was obtained using 2,6-dimethoxyphenylboronic acid (100g, 550mmol) and 2-bromo-4-chloro-1,3-difluorobenzene (125g, 550mmol) in the same manner as in Synthesis Example 1.

[0659] HRMS (70eV, EI+): m / z calcd for C14H11ClF2O2: 284.0416, found: 284.

[0660] Elemental Analysis: C, 59%; H, 4%

[0662] Synthesis Example 29: Synthesis of Intermediate I-22

[0663]

[0664] Intermediate I-22 (101g, 80%) was obtained using intermediate I-21 (140g, 492mmol) in the same manner as in Synthesis Example 2.

[0665] HRMS (70eV, EI+): m / z calcd for C12H7ClF2O2: 256.0103, found: 256.

[0666] Elemental Analysis: C, 55%; H, 3%

[0668] Synthesis Example 30: Synthesis of Intermediate I-23

[0669]

[0670] Intermediate I-23 (32.3g, 35%) was obtained using intermediate I-22 (100g, 390mmol) in the same manner as in Synthesis Example 3.

[0671] HRMS (70eV, EI+): m / z calcd for C12H6ClFO2: 236.0040, found: 236.

[0672] Elemental Analysis: C, 61%; H, 3%

[0674] Synthesis Example 31: Synthesis of Intermediate I-24

[0675]

[0676] Intermediate I-24 (43.5g, 93%) was obtained using intermediate I-23 (30g, 127mmol) in the same manner as in Synthesis Example 4.

[0677] HRMS (70eV, EI+): m / z calcd for C13H5ClF4O4S: 367.9533, found: 367.

[0678] Elemental Analysis: C, 42%; H, 1%

[0680] Synthesis Example 32: Synthesis of Intermediate I-25

[0681]

[0682] Intermediate I-25 (35.3g, 80%) was obtained using intermediate I-24 (42g, 114mmol) and dibenzofuran-1-boronic acid (26.6g, 125mmol) in the same manner as in Synthesis Example 1.

[0683] HRMS (70eV, EI+): m / z calcd for C24H12ClFO2: 386.0510, found: 386.

[0684] Elemental Analysis: C, 75%; H, 3%

[0686] Synthesis Example 33: Synthesis of Intermediate I-26

[0687]

[0688] Intermediate I-25 (34 g, 87.9 mmol) was dissolved in 0.4 L of xylene under a nitrogen environment, to which bis(pinacolato)diboron (26.8 g, 105 mmol), tris(dibenzylideneacetone)dipalladium (0) (2.41 g, 2.64 mmol), tricyclohexylphosphine (2.96 g, 10.5 mmol), and potassium acetate (25.9 g, 264 mmol) were added, and the mixture was heated and refluxed for 8 hours. After the reaction was complete, water was added to the reaction mixture and extracted with dichloromethane (DCM). Subsequently, water was removed using magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-26 (18.9 g, 45%).

[0689] HRMS (70eV, EI+): m / z calcd for C30H24BFO4: 478.1752, found: 478.

[0690] Elemental Analysis: C, 75%; H, 5%

[0692] Synthesis Example 34: Synthesis of Intermediate I-27

[0693]

[0694] Intermediate I-27 (22.6g, 84%) was obtained using intermediate I-26 (15g, 31.4mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (8.40g, 31.4mmol) in the same manner as in Synthesis Example 1.

[0695] HRMS (70eV, EI+): m / z calcd for C15H10ClN3: 267.0563, found: 267.

[0696] Elemental Analysis: C, 67%; H, 4%

[0698] Synthesis Example 35: Synthesis of Compound 102

[0699]

[0700] Compound 102 (12.5g, 50%) was obtained using intermediate I-27 (20g, 34.3mmol) and 9H-carbazole (6.3g, 37.7mmol) in the same manner as in Synthesis Example 6.

[0701] HRMS (70eV, EI+): m / z calcd for C51H30N4O2: 730.2369, found: 730.

[0702] Elemental Analysis: C, 84%; H, 4%

[0704] Synthesis Example 36: Synthesis of Compound 126

[0705]

[0706] Compound 126 (11.9g, 43%) was obtained using intermediate I-27 (20g, 34.3mmol) and 2-phenyl-9H-carbazole (9.17g, 37.7mmol) in the same manner as in Synthesis Example 6.

[0707] HRMS (70eV, EI+): m / z calcd for C57H34N4O2: 806.2682, found: 806.

[0708] Elemental Analysis: C, 84%; H, 4%

[0710] Synthesis Example 37: Synthesis of Intermediate I-28

[0711]

[0712] Intermediate I-28 (23.7g, 86%) was obtained using intermediate I-26 (20g, 41.8mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (15.8g, 46.0mmol) in the same manner as in Synthesis Example 1.

[0713] HRMS (70eV, EI+): m / z calcd for C45H26FN3O2: 659.2009, found: 659.

[0714] Elemental Analysis: C, 82%; H, 4%

[0716] Synthesis Example 38: Synthesis of Compound 150

[0717]

[0718] Compound 150 (15.2g, 62%) was obtained using intermediate I-28 (20g, 30.3mmol) and 9H-carbazole (5.6g, 33.3mmol) in the same manner as in Synthesis Example 6.

[0719] HRMS (70eV, EI+): m / z calcd for C57H34N4O2: 806.2682, found: 806.

[0720] Elemental Analysis: C, 85%; H, 4%

[0722] Synthesis Example 39: Synthesis of Compound Host 1

[0723]

[0724] Compound Host 1 was synthesized by referring to patent US9732069.

[0725] HRMS (70eV, EI+): m / z calcd for C39H24N4O: 564.1950, found: 564.

[0726] Elemental Analysis: C, 83%; H, 4%

[0728] Synthesis Example 40: Synthesis of Compound Host 2

[0729]

[0730] Compound Host 2 was synthesized by referring to patent KR2040226.

[0731] HRMS (70eV, EI+): m / z calcd for C42H25NO2: 575.1885, found: 575.

[0732] Elemental Analysis: C, 88%; H, 4%

[0734] Synthesis Example 41: Synthesis of Compound Host 3

[0735]

[0736] Compound Host 3 was synthesized by referring to patent WO2021-029616.

[0737] HRMS (70eV, EI+): m / z calcd for C51H30N4OS: 746.2140, found: 746.

[0738] Elemental Analysis: C, 82%; H, 4%

[0740] Synthesis Example 42: Synthesis of Compound B-136

[0741]

[0742] Compound B-136 was synthesized by referring to patent EP3034581.

[0743] HRMS (70eV, EI+): m / z calcd for C42H28N2: 560.2252, found: 560.

[0744] Elemental Analysis: C, 90%; H, 5%

[0746] Synthesis Example 43: Synthesis of Compound B-99

[0747]

[0748] Compound B-99 was synthesized by referring to patent KR10-2019-0000597.

[0749] HRMS (70eV, EI+): m / z calcd for C48H32N2: 636.2565, found: 636.

[0750] Elemental Analysis: C, 91%; H, 5%

[0752] Synthesis Example 44: Synthesis of Compound B-31

[0753]

[0754] Compound B-31 was synthesized by referring to patent EP2947071.

[0755] HRMS (70eV, EI+): m / z calcd for C48H32N2: 636.2565, found: 636.

[0756] Elemental Analysis: C, 91%; H, 5%

[0758] Synthesis Example 45: Synthesis of Compound C-4

[0759]

[0760] Compound C-4 was synthesized by referring to patent KR2031300.

[0761] HRMS (70eV, EI+): m / z calcd for C42H28N2: 560.2252, found: 560.

[0762] Elemental Analysis: C, 90%; H, 5%

[0764] Synthesis Example 46: Synthesis of Compound C-57

[0765]

[0766] Compound C-57 was synthesized by referring to patent WO2018-095391.

[0767] HRMS (70eV, EI+): m / z calcd for C48H32N2: 636.2565, found: 636.

[0768] Elemental Analysis: C, 91%; H, 5%

[0770] Example 1

[0771] A glass substrate coated with a thin film of ITO (Indium tin oxide) was cleaned with distilled water ultrasonics. After cleaning with distilled water, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition machine. Using the prepared ITO transparent electrode as the anode, a 100 Å thick hole injection layer was formed by vacuum depositing compound A doped with 3% NDP-9 (commercially available from Novaled) on the ITO substrate, and a hole transport layer was formed by depositing compound A to a thickness of 1350 Å on top of the hole injection layer. A hole transport assist layer was formed by depositing compound B to a thickness of 350 Å on the hole transport layer, and a emitting layer with a thickness of 400 Å was formed by vacuum deposition using compound 1 synthesized in Synthesis Example 12 as a host and doping with PhGD at a dopant of 7 wt% on the hole transport assist layer. Subsequently, an electron transport assist layer was formed by depositing compound C to a thickness of 50 Å on the emitting layer, and an electron transport layer with a thickness of 300 Å was formed by vacuum deposition of compound D and Liq simultaneously in a weight ratio of 1:1. A green organic light-emitting diode was fabricated by forming a cathode by sequentially vacuum depositing LiQ 15 Å and Al 1200 Å on the electron transport layer.

[0772] It was fabricated with the structure of ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / Compound B (350Å) / EML [Compound 1 (93wt%) : PhGD (7wt%)] (400Å) / Compound C (50Å) / Compound D : LiQ (300Å) / LiQ (15Å) / Al (1200Å).

[0773] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0774] Compound B: N-[4-(4-Dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0775] Compound C: 2,4-Diphenyl-6-(4',5',6'-triphenyl[1,1':2',1'':3'',1''':3''',1''''-quinquephenyl]-3''''-yl)-1,3,5-triazine

[0776] Compound D: 2-(1,1'-Biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0777] [PhGD]

[0778]

[0780] Examples 2 to 10 and Comparative Examples 1 to 3

[0781] An organic light-emitting diode was fabricated using the same method as in Example 1, except that the composition was changed to the one listed in Table 1 below.

[0783] Example 11

[0784] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was cleaned with distilled water ultrasonics. After the distilled water cleaning was finished, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and then transferred to a vacuum deposition machine. Using the prepared ITO transparent electrode as the anode, a 100 Å thick hole injection layer was formed by vacuum depositing compound A doped with 3% NDP-9 (commercially available from Novaled) on the ITO substrate, and a hole transport layer was formed by depositing compound A to a thickness of 1350 Å on top of the hole injection layer. A hole transport auxiliary layer was formed by depositing compound E to a thickness of 350 Å on top of the hole transport layer. A 400 Å thick emissive layer was formed by vacuum deposition on the above hole transport assist layer using Compound 1 synthesized in Synthesis Example 12 and Compound B-136 synthesized in Synthesis Example 31 as co-hosts, and doping with PhGD at 10 wt% as a dopant. Here, Compound 1 and Compound B-136 were used in a weight ratio of 3:7. Subsequently, Compound F was deposited to a thickness of 50 Å on the emissive layer to form an electron transport assist layer, and Compound G and Liq were vacuum deposited simultaneously in a weight ratio of 1:1 to form an electron transport layer of 300 Å. A green organic light-emitting diode was fabricated by forming a cathode by sequentially vacuum depositing LiQ 15 Å and Al 1200 Å on the electron transport layer.

[0785] It was fabricated with the structure ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / Compound E (350Å) / EML[Host (Compound 1:Compound B-136 = 27:63) 90wt%, PhGD 10wt%)](400Å) / Compound F(50Å) / Compound G:LiQ(300Å) / LiQ(15Å) / Al(1200Å).

[0786] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0787] Compound F: 2-[3'-(9,9-Dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0788] Compound G: 2-[4-[4-(4'-Cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0790] Example 12

[0791] An organic light-emitting diode was fabricated in the same manner as in Example 11, except that compound 1 and compound B-136 were used in a weight ratio of 4:6.

[0793] Example 13

[0794] An organic light-emitting diode was fabricated in the same manner as in Example 11, except that compound 1 and compound B-136 were used in a weight ratio of 5:5.

[0796] Examples 14 to 26 and Comparative Examples 4 to 6

[0797] An organic light-emitting diode was fabricated using the same method as in Example 11, except that the composition was changed to the one listed in Table 2 below.

[0799] evaluation

[0800] The driving voltage, luminous efficiency, and lifespan characteristics of organic light-emitting diodes according to Examples 1 to 26 and Comparative Examples 1 to 6 were evaluated.

[0801] The specific measurement method is as follows, and the results are shown in Table 1 and Table 2.

[0802] (1) Measurement of change in current density according to voltage change

[0803] For the fabricated organic light-emitting diode, the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0V to 10V, and the result was obtained by dividing the measured current value by the area.

[0804] (2) Measurement of change in brightness according to voltage change

[0805] For the fabricated organic light-emitting diode, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and the results were obtained.

[0806] (3) Measurement of luminous efficiency

[0807] Using the luminance, current density, and voltage measured from (1) and (2) above, the same current density (10 mA / cm²) 2 The current efficiency (cd / A) of ) was calculated.

[0808] The luminous efficiency values ​​of Examples 1 to 10 and Comparative Examples 1 to 3 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0809] The luminous efficiency values ​​of Examples 11 to 26 and Comparative Examples 4 to 6 were calculated as relative values ​​based on Comparative Example 4 and are listed in Table 2 below.

[0810] (4) Life measurement

[0811] Luminance (cd / m²) 2 ) 24,000 cd / m 2 The result was obtained by maintaining it and measuring the time it took for the current efficiency (cd / A) to decrease to 97%.

[0812] The lifespan measurements of Examples 1 to 10 and Comparative Examples 1 to 3 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0813] The lifespan measurements of Examples 11 to 26 and Comparative Examples 4 to 6 were calculated as relative values ​​based on Comparative Example 4 and are listed in Table 2 below.

[0814] (5) Driving voltage measurement

[0815] Using a current-voltage meter (Keithley 2400), 15 mA / cm 2 The driving voltage of each component was measured to obtain the results.

[0816] The driving voltages of Examples 1 to 10 and Comparative Examples 1 to 3 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0817] The driving voltages of Examples 11 to 26 and Comparative Examples 4 to 6 were calculated as relative values ​​based on Comparative Example 4 and are listed in Table 2 below.

[0818] No. Host Driving voltage (%) Efficiency (%) life(%) Example 1 Compound 1 96 196 196 Example 2 Compound 2 94 172 189 Example 3 Compound 3 95 192 150 Example 4 Compound 4 91 232 161 Example 5 Compound 5 92 240 182 Example 6 Compound 54 99 140 250 Example 7 Compound 94 88 240 196 Example 8 Compound 102 95 200 161 Example 9 Compound 126 97 192 214 Example 10 Compound 150 99 208 200 Comparative Example 1 Host 1 100 100 100 Comparative Example 2 Host 2 106 60 18 Comparative Example 3 Host 3 101 120 107

[0819] No. Host Driving voltage (%) Efficiency (%) life(%) Example 11 Compound 1 / Compound B-136 98 150 250 Example 12 Compound 1 / Compound B-136 93 175 200 Example 13 Compound 1 / Compound B-136 89 188 183 Example 14 Compound 1 / Compound B-99 95 158 240 Example 15 Compound 1 / Compound B-31 99 163 260 Example 16 Compound 1 / Compound C-4 88 138 183 Example 17 Compound 1 / Compound C-57 93 155 213 Example 18 Compound 2 / Compound B-136 93 163 233 Example 19 Compound 3 / Compound B-136 91 170 220 Example 20 Compound 4 / Compound B-136 93 170 200 Example 21 Compound 5 / Compound B-136 92 195 257 Example 22 Compound 6 / Compound B-136 98 125 300 Example 23 Compound 7 / Compound B-136 93 163 267 Example 24 Compound 102 / Compound B-136 95 165 200 Example 25 Compound 126 / Compound B-136 96 150 233 Example 26 Compound 150 / Compound B-136 97 170 217 Comparative Example 4 Host 1 / Compound B-136 100 100 100 Comparative Example 5 Host 2 / Compound B-136 110 63 33 Comparative Example 6 Host 3 / Compound B-136 100 118 133

[0820] Referring to Tables 1 and 2, it can be seen that the organic light-emitting diodes according to Examples 1 to 26 have significantly improved driving voltage, luminous efficiency, and lifespan characteristics compared to the organic light-emitting diodes according to Comparative Examples 1 to 6. Explanation of the symbols

[0822] 100: Organic light-emitting diode 105: Organic layer 110: Cathode 120: Anode 130: Emissive layer 140: Precision Transport Area 150: Electronic transport area

Claims

Claim 1 Compound for organic optoelectronic devices represented by the following Chemical Formula 1 or Chemical Formula 2: [Chemical Formula 1] [Chemical Formula 2] In the above Chemical Formulas 1 and 2, X 1 and X 2 are independently O or S, and Z 1 To Z 3 are N and R respectively. 1 to R 9 Each is independently a hydrogen, deuterium, or a substituted or unsubstituted phenyl group, and Ar 1 and Ar 2 is each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and L 1 to L 4 Each is independently a single bond, or a substituted or unsubstituted phenylene group, m1, m2, and m4 are each independently one of an integer from 1 to 4, m3 is one of an integer from 1 to 3, and “substituted” means that at least one hydrogen in the substituent or compound is substituted with a deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. Claim 2 In claim 1, the above chemical formula 1 is a compound for an organic optoelectronic device represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, X 1 , X 2 , Z 1 To Z 3 , R 1 to R 9 , Ar 1 or Ar 4 , L 1 to L 4 , and m1 to m4 are as defined in Paragraph 1. Claim 3 In claim 1, the above chemical formula 2 is a compound for an organic optoelectronic device represented by any one of the following chemical formulas 2-1 to 2-4: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] In the above chemical formulas 2-1 to 2-4, X 1 , X 2 , Z 1 To Z 3 , R 1 to R 7 , Ar 1 , L 1 to L 3 , and m1 to m7 are as defined in Paragraph 1. Claim 4 delete Claim 5 delete Claim 6 delete Claim 7 In claim 1, a compound for an organic optoelectronic device selected from the compounds listed in Group 1 below: [Group 1] . Claim 8 A composition for an organic optoelectronic device comprising a first compound and a second compound, wherein the first compound is a compound for an organic optoelectronic device according to claim 1, and the second compound is represented by the following chemical formula 3; or a combination of the following chemical formulas 4 and 5: [Chemical Formula 3] In the above chemical formula 3, R 10 to R 14 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and L 5 and L 6 Each is independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m10, m13, and m14 are each independently one of an integer from 1 to 4, m11 and m12 are each independently one of an integer from 1 to 3, and n is one of an integer from 0 to 2; [Chemical Formula 4] [Chemical Formula 5] In the above Chemical Formulas 4 and 5, a1* to a4* of Chemical Formula 4 are each independently connected carbon (C) or Cl a -R d And, among a1* to a4* of Chemical Formula 4, two adjacent ones are each connected to * of Chemical Formula 5, and L a , L 7 and L 8 Each is independently a single-bonded, substituted, or unsubstituted C6 to C20 arylene group, and R d , R 15 and R 16 Each is independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group, and Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m15 and m16 are each independently one of integers from 1 to 4, and “substituted” means that at least one hydrogen in the substituent or compound is substituted with a deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. Claim 9 In claim 8, the above chemical formula 3 is a composition for an organic optoelectronic device represented by the following chemical formula 3-8: [Chemical Formula 3-8] In the above chemical formula 3-8, R 10 to R 13 is each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, m10 and m13 are each independently one of integers 1 to 4, m11 and m12 are each independently one of integers 1 to 3, and L 5 -Ar 3 and L 6 -Ar 4 Each is independently one of the substituents listed in Group II below, [Group II] In the above Group II, R 17 to R 21 Each is independently hydrogen, deuterium, cyano group, C1 to C10 alkyl group, or C6 to C12 aryl group, m17 is one of integers from 1 to 5, m18 is one of integers from 1 to 4, m19 is one of integers from 1 to 3, m20 is one or two integers, m21 is one of integers from 1 to 7, and * is a connecting point. Claim 10 In claim 8, the combination of the above chemical formulas 4 and 5 is a composition for an organic optoelectronic device represented by the following chemical formula 4C: [Chemical Formula 4C] In the above chemical formula 4C, L a3 and L a4 is a single bond, and R 15 , R 16 , R d3 and R d4 are each independently hydrogen, deuterium, or a C6 to C12 aryl group, and m15 and m16 are each independently one of integers 1 to 4, and*-L 7 -Ar 5 and *-L 8 -Ar 6 Each is independently one of the substituents listed in Group II below, [Group II] In the above Group II, R 17 to R 21 Each is independently hydrogen, deuterium, cyano group, C1 to C10 alkyl group, or C6 to C12 aryl group, m17 is one of integers from 1 to 5, m18 is one of integers from 1 to 4, m19 is one of integers from 1 to 3, m20 is one or two integers, m21 is one of integers from 1 to 7, and * is a connecting point. Claim 11 An organic optoelectronic device comprising an anode and a cathode facing each other, and at least one organic layer located between the anode and the cathode, wherein the organic layer comprises a compound for an organic optoelectronic device according to any one of claims 1 to 3 and 7; or a composition for an organic optoelectronic device according to any one of claims 8 to 10. Claim 12 In claim 11, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises an organic optoelectronic device comprising a compound for the organic optoelectronic device or a composition for the organic optoelectronic device. Claim 13 A display device comprising an organic optoelectronic element according to paragraph 11.

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