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

Abstract

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

Description

Technical Field

[0001] Disclosed are a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Background Art

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

[0003] Organic optoelectronic devices can be roughly divided into two categories based on their working principles: one is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes and transferring the electrons and holes to different electrodes, respectively; the other is a light-emitting device that generates light energy from electrical energy by supplying voltage or current to electrodes.

[0004] Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0005] Among them, organic light emitting diodes (OLEDs) have attracted much attention in recent years due to an increase in demand for flat panel display devices. Organic light emitting diodes are devices that convert electrical energy into light, and the performance of organic light emitting diodes is greatly affected by organic materials between electrodes. Summary of the invention

[0006] Technical issues

[0007] One embodiment provides a compound for an organic optoelectronic device capable of realizing an organic optoelectronic device with high efficiency and long lifetime.

[0008] Another embodiment provides a composition for an organic optoelectronic device including the compound for an organic optoelectronic device.

[0009] Another embodiment provides an organic optoelectronic device including the compound for an organic optoelectronic device.

[0010] Another embodiment provides a display device including the organic optoelectronic device.

[0011] Technical Solution

[0012] According to one embodiment, a compound for an organic optoelectronic device represented by Chemical Formula 1 is provided.

[0013] [Chemical formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] X 1 and X2 Each independently is O, S or SiR a R b ,

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

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

[0019] R a , R b , R c and R 1 To R 7 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic,

[0020] R 4 To R 7 Each exists independently, or adjacent groups are linked to form a substituted or unsubstituted aromatic monocyclic ring or a substituted or unsubstituted aromatic polycyclic ring,

[0021] Ar 1 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0022] L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0023] m1, m4, m5 and m6 are each independently one of integers from 1 to 3, and

[0024] m2, m3 and m7 are each independently one of integers from 1 to 4.

[0025] According to another embodiment, a composition for an organic optoelectronic device includes a first compound and a second compound.

[0026] The first compound is the above-described compound for an organic optoelectronic device, and the second compound may be represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4.

[0027] [Chemical formula 2]

[0028]

[0029] In chemical formula 2,

[0030] R9 To R 13 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[0031] 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,

[0032] L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0033] m9, m12 and m13 are each independently one of integers from 1 to 4,

[0034] m10 and m11 are each independently one of integers from 1 to 3, and

[0035] n is an integer from 0 to 2;

[0036]

[0037] In Chemical Formula 3 and Chemical Formula 4,

[0038] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R d ,

[0039] Among a1* to a4* in Chemical Formula 3, two adjacent ones are each connected to * in Chemical Formula 4, L a , L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0040] R d , R 14 and R 15 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[0041] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0042] m14 and m15 are each independently one of integers from 1 to 4.

[0043] According to another embodiment, an organic optoelectronic device includes an anode and a cathode facing each other and at least one organic layer between the anode and the cathode, wherein the organic layer includes the above-mentioned compound for an organic optoelectronic device.

[0044] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0045] Beneficial Effects

[0046] High-efficiency and long-life organic optoelectronic devices can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0047] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0048] <Description of Reference Numerals>

[0049] 100: Organic light-emitting diode

[0050] 105: Organic layer

[0051] 110: cathode

[0052] 120: Anode

[0053] 130: Luminous layer

[0054] 140: Hole transport region

[0055] 150: Electron transport region DETAILED DESCRIPTION

[0056] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, and the present disclosure is not limited thereto.

[0057] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.

[0058] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C20 alkyl, C6 to C30 aryl or cyano. In a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl or cyano. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or compound is replaced by deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl or naphthyl.

[0059] In the present specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0060] In the present specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0061] In the present specification, when a definition is not otherwise provided, "hetero" means containing one to three hetero atoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0062] In the present specification, "aryl" refers to a group including at least one hydrocarbon aromatic portion, and all elements of the hydrocarbon aromatic portion have p orbitals forming conjugation, such as phenyl, naphthyl, etc., two or more hydrocarbon aromatic portions may be connected by a σ bond, and may be, for example, a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic portions are directly or indirectly fused to provide a non-aromatic fused ring, such as a fluorenyl group.

[0063] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings which share adjacent pairs of carbon atoms) functional groups.

[0064] As used herein, "heterocyclic group" is a general concept of heteroaryl, and may include at least one heteroatom selected from N, O, S, P and Si in place of carbon (C) in a cyclic compound such as an aryl, a cycloalkyl, a condensed ring thereof or a combination thereof. When the heterocyclic group is a condensed ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0065] For example, "heteroaryl" may refer to an aryl group including at least one heteroatom selected from N, O, S, P and Si. Two or more heteroaryls are directly connected by a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may include one to three heteroatoms.

[0066] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be 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 tetraphenyl group, a substituted or unsubstituted pyrene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted para-terphenyl group, a substituted or unsubstituted meta-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysene group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted peryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0067] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furanyl, a substituted or unsubstituted thienyl, a substituted or unsubstituted pyrrolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted imidazolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted oxazolyl, a substituted or unsubstituted thiazolyl, a substituted or unsubstituted oxadiazolyl, a substituted or unsubstituted thiadiazolyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzothienyl, a substituted or unsubstituted benzimidazolyl, a substituted or unsubstituted indolyl, a substituted or unsubstituted The invention may include, but is not limited to, a substituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazinyl, a substituted or unsubstituted acridinyl, a substituted or unsubstituted phenazinyl, a substituted or unsubstituted phenothiazinyl, a substituted or unsubstituted phenoxazinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl or a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted benzofuranofluorenyl, a substituted or unsubstituted benzothiophenefluorenyl, or a combination thereof, but is not limited thereto.

[0068] As used herein, hole characteristics refer to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0069] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer due to conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level.

[0070] Hereinafter, a compound for an organic optoelectronic device according to one embodiment is described.

[0071] The compound for an organic optoelectronic device according to one embodiment is represented by Chemical Formula 1.

[0072] [Chemical formula 1]

[0073]

[0074] In Chemical Formula 1,

[0075] X 1 and X 2 Each independently is O, S or SiR a R b ,

[0076] Z 1 To Z 3 Each independently is N or CR c ,

[0077] Z 1 To Z 3 At least one of them is N,

[0078] R a , R b , R c and R 1 To R 7 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic,

[0079] R 4 To R 7 Each exists independently, or adjacent groups are linked to form a substituted or unsubstituted aromatic monocyclic ring or a substituted or unsubstituted aromatic polycyclic ring,

[0080] Ar 1 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0081] L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0082] m1, m4, m5 and m6 are each independently one of integers from 1 to 3, and

[0083] m2 and m3 are each independently one of integers from 1 to 4.

[0084] The compound represented by Chemical Formula 1 has a structure including triphenylene and two consecutive dibenzofuran derivatives (the substituents are selected from dibenzofuran, dibenzothiophene and dibenzosilole) located at the center of a nitrogen-containing 6-membered ring having at least one nitrogen atom.

[0085] By including two consecutive dibenzofuran derivatives, electron delocalization can be achieved, thereby increasing charge mobility. Therefore, hole transport characteristics can be further improved, so that low-driving and high-efficiency performance of an organic optoelectronic device including the compound can be achieved.

[0086] Furthermore, by introducing triphenylene, the LUMO electron cloud of the nitrogen-containing 6-membered ring can be expanded, thereby preventing the degradation caused by anions.

[0087] Furthermore, by designing three substituents differently around the nitrogen-containing six-membered ring center, steric hindrance is achieved, thereby resulting in a low deposition temperature and thus significantly improving the lifetime characteristics of the organic light-emitting diode to which it is applied.

[0088] In Formula 1, when two or more R 1 When replaced, each R 1 Can be the same as or different from each other.

[0089] In Formula 1, when two or more R 2 When replaced, each R 2 Can be the same as or different from each other.

[0090] In Formula 1, when two or more R 3 When replaced, each R 3 Can be the same as or different from each other.

[0091] In Formula 1, when two or more R 4 When replaced, each R 4 Can be the same as or different from each other.

[0092] In Formula 1, when two or more R 5 When replaced, each R 5 Can be the same as or different from each other.

[0093] In Formula 1, when two or more R 6 When replaced, each R 6 Can be the same as or different from each other.

[0094] In the above chemical formula 1, when two or more R 7 When replaced, each R 7 Can be the same as or different from each other.

[0095] In the above chemical formula 1, when two or more R c When replaced, each R c Can be the same as or different from each other.

[0096] For example, Chemical Formula 1 may be represented by any one of Chemical Formula 1-1 to Chemical Formula 1-4.

[0097] [Chemical formula 1-1]

[0098]

[0099] [Chemical formula 1-2]

[0100]

[0101] [Chemical formula 1-3]

[0102]

[0103] [Chemical formula 1-4]

[0104]

[0105] In Chemical Formula 1-1 to Chemical Formula 1-4,

[0106] 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 the same as above.

[0107] For example, Chemical Formula 1 may be represented by Chemical Formula 1-1 or Chemical Formula 1-4.

[0108] Chemical Formula 1-1 may be represented by any one of Chemical Formula 1-1-(i), Chemical Formula 1-1-(ii), Chemical Formula 1-1-(iii), and Chemical Formula 1-1-(iv).

[0109] [Chemical formula 1-1-(i)]

[0110]

[0111] [Chemical formula 1-1-(ii)]

[0112]

[0113] [Chemical formula 1-1-(iii)]

[0114]

[0115] [Chemical formula 1-1-(iv)]

[0116]

[0117] In Chemical Formula 1-1-(i), Chemical Formula 1-1-(ii), Chemical Formula 1-1-(iii) and Chemical Formula 1-1-(iv),

[0118] 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 the same as above.

[0119] Chemical Formula 1-4 may be represented by any one of Chemical Formula 1-4-(i), Chemical Formula 1-4-(ii), Chemical Formula 1-4-(iii), and Chemical Formula 1-4-(iv).

[0120] [Chemical formula 1-4-(i)]

[0121]

[0122] [Chemical formula 1-4-(ii)]

[0123]

[0124] [Chemical formula 1-4-(iii)]

[0125]

[0126] [Chemical formula 1-4-(iv)]

[0127]

[0128] In Chemical Formula 1-4-(i), Chemical Formula 1-4-(ii), Chemical Formula 1-4-(iii) and Chemical Formula 1-4-(iv),

[0129] X 1 , X 2 , Z 1 To Z3 , R 1 To R 7 ,Ar 1 , L 1 To L 3 The definitions of and m1 to m7 are the same as above.

[0130] For example, Chemical Formula 1 may be represented by any one of Chemical Formula 1-1-(i), Chemical Formula 1-1-(ii), Chemical Formula 1-1-(iii), Chemical Formula 1-1-(iv), and Chemical Formula 1-4-(iv).

[0131] Specifically, when the dibenzofuran derivative adjacent to the nitrogen-containing 6-membered ring is connected at the 1st or 2nd position in the direction of the nitrogen-containing 6-membered ring (as in Chemical Formula 1-1-(i) or Chemical Formula 1-1-(ii)), the structural torsion can be maximized due to the further increase in steric hindrance relative to the 9th position, and the structural torsion significantly reduces the energy barrier that can be expected for the non-shared electron pairs of O, S and Si in the dibenzofuran derivative, thereby promoting charge transfer between molecules. In addition, Ar 1 The molecular stability of the dibenzofuran derivatives themselves can be increased, which can help improve the lifetime of the device.

[0132] For example, Ar 1 It may 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 dibenzosilyl group, or a substituted or unsubstituted carbazolyl group.

[0133] As Ar 1 , which can further improve the molecular stability of the dibenzofuran derivative itself, examples of which may include substituents other than substituted or unsubstituted triphenylene and two consecutive dibenzofuran derivatives within the above range.

[0134] For example, in Chemical Formula 1, L 1 It may be a single bond or a substituted or unsubstituted phenylene group.

[0135] For example, in Chemical Formula 1, L 2 and L 3 Each may independently be a single bond or a substituted or unsubstituted C6 to C12 arylene group.

[0136] For example, in Chemical Formula 1, L 2 and L 3 Each independently may be a single bond or a substituted or unsubstituted phenylene group.

[0137] For example, Z 1 To Z3 At least two of can be N.

[0138] For example, Z 1 To Z 3 They can each be N.

[0139] For example, R a and R b Each may independently be a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group.

[0140] For example, R 1 To R 7 Each may independently be hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl or substituted or unsubstituted dibenzosilyl.

[0141] In one embodiment, when R 4 To R 7 When present independently of each other, they may include a form in which two consecutive dibenzofuran derivatives are linked.

[0142] In another embodiment, R 4 To R 7 may be linked to adjacent groups to form a substituted or unsubstituted aromatic monocyclic ring, and

[0143] For example, they may be represented by any one of Chemical Formula 1A to Chemical Formula 1D.

[0144] [Chemical Formula 1A]

[0145]

[0146] [Chemical formula 1B]

[0147]

[0148] [Chemical formula 1C]

[0149]

[0150] [Chemical formula 1D]

[0151]

[0152] In Chemical Formulae 1A to 1D, X 1 , X 2 , Z 1 To Z 3 ,Ar1 , L 1 To L 3 and m1 to m7 are defined the same as above,

[0153] R 1 To R 8 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic, and

[0154] m8 is an integer from 1 to 4.

[0155] In Formulae 1A to 1D, when two or more R 8 When replaced, each R 8 Can be the same as or different from each other.

[0156] As the most specific example, Chemical Formula 1 can be represented by any one of the above-mentioned Chemical Formula 1-1-(i), Chemical Formula 1-1-(ii), Chemical Formula 1-1-(iii), Chemical Formula 1-1-(iv), and Chemical Formula 1-4-(iv).

[0157] In the most specific embodiment, the compound represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1, but is not limited thereto.

[0158] [Group 1]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169] A composition for an organic optoelectronic device according to one embodiment includes a first compound and a second compound, wherein the first compound may be the above-mentioned compound for an organic optoelectronic device, and the second compound may be represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4.

[0170] [Chemical formula 2]

[0171]

[0172] In chemical formula 2,

[0173] R 9 To R 13 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[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] L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0176] m9, m12 and m13 are each independently one of integers from 1 to 4,

[0177] m10 and m11 are each independently one of integers from 1 to 3, and

[0178] n is an integer from 0 to 2;

[0179]

[0180] In Chemical Formula 3 and Chemical Formula 4,

[0181] a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R d ,

[0182] Among a1* to a4* in Chemical Formula 3, two adjacent ones are each connected to * in Chemical Formula 4, L a , L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0183] R d , R 14and R 15 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic,

[0184] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0185] m14 and m15 are each independently one of integers from 1 to 4.

[0186] The second compound may be used together with the first compound in the light emitting layer to improve light emitting efficiency and lifespan characteristics by increasing charge mobility and stability.

[0187] In Formula 2, when two or more R 9 When replaced, each R 9 Can be the same as or different from each other.

[0188] In Formula 2, when two or more R 10 When replaced, each R 10 Can be the same as or different from each other.

[0189] In Formula 2, when two or more R 11 When replaced, each R 11 Can be the same as or different from each other.

[0190] In Formula 2, when two or more R 12 When replaced, each R 12 Can be the same as or different from each other.

[0191] In Formula 2, when two or more R 13 When replaced, each R 13 Can be the same as or different from each other.

[0192] In Formula 3 and Formula 4, when two or more R 14 When replaced, each R 14 Can be the same as or different from each other.

[0193] In Formula 3 and Formula 4, when two or more R 15 When replaced, each R 15 Can be the same as or different from each other.

[0194] In Formula 3 and Formula 4, when two or more R d When replaced, each Rd Can be the same as or different from each other.

[0195] For example, in Formula 2, Ar 2 and Ar 3 may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted fluorenyl group,

[0196] In chemical formula 2, L 5 and L 6 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0197] In chemical formula 2, R 9 To R 13 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and

[0198] n can be 0 or 1.

[0199] As an example, in Chemical Formula 2, “substituted” means that at least one hydrogen is replaced by deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C30 heteroaryl group.

[0200] For example, in Formula 2, Ar 2 and Ar 3 Each of them independently may be 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.

[0201] In a specific embodiment of the present invention, Chemical Formula 2 may be represented by one of Chemical Formulas 2-1 to 2-15.

[0202]

[0203]

[0204] In Chemical Formulae 2-1 to 2-15, R 9 To R 13 are each independently hydrogen, deuterium, or substituted or unsubstituted C6 to C12 aryl, *-L 2 -Ar 5 and *-L 3 -Ar 6 Each may independently be one of the substituents listed in Group I.

[0205] [Group I]

[0206]

[0207] In Group I,

[0208] R 16 To R 20 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl,

[0209] m16 is an integer from 1 to 5,

[0210] m17 is an integer from 1 to 4,

[0211] m18 is an integer from 1 to 3,

[0212] m19 is an integer of 1 or 2.

[0213] m20 is an integer from 1 to 7, and

[0214] * is the connection point.

[0215] In Group I, when two or more R 16 When replaced, each R 16 Can be the same as or different from each other.

[0216] In Group I, when two or more R 17 When replaced, each R 17 Can be the same as or different from each other.

[0217] In Group I, when two or more R 18 When replaced, each R 18 Can be the same as or different from each other.

[0218] In Group I, when two or more R 19 When replaced, each R 19 Can be the same as or different from each other.

[0219] In Group I, when two or more R 20 When replaced, each R 20 Can be the same as or different from each other.

[0220] The second compound may be represented, for example, by any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0221]

[0222] In Chemical Formulae 3A to 3E, L 7 , L 8,Ar 4 ,Ar 5 , R 14 and R 15 Same as above,

[0223] L a1 To L a4 With the above L 7 and L 8 The definition of is the same as

[0224] R d1 To R d4 With the above R 14 and R 15 The definition is the same.

[0225] For example, in Formulas 3 and 4, Ar 4 and Ar 5 may 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 triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group, and

[0226] R d1 To R d4 , R 14 and R 15 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0227] In a specific embodiment of the present invention, in Chemical Formulas 3 and 4, *-L 7 -Ar 4 and *-L 8 -Ar 5 The substituents listed in Group I may be each independently selected.

[0228] In one embodiment, R d1 To R d4 , R 14 and R 15 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0229] For example, R d1 To R d4 , R14 and R 15 may each independently be hydrogen, deuterium, cyano or substituted or unsubstituted phenyl, and

[0230] In a specific embodiment, R d1 To R d4 , R 14 and R 15 and may each independently be hydrogen, deuterium, or substituted or unsubstituted phenyl.

[0231] In a specific embodiment of the present invention, the second compound can be represented by Chemical Formula 2-8, in which Ar 2 and Ar 3 may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group, L 5 and L 6 may each independently be a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 9 To R 12 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl or substituted or unsubstituted dibenzothiophenyl.

[0232] For example, in Chemical Formula 2-8, R 9 To R 12 may each independently be hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, and *-L 5 -Ar 2 and *-L 6 -Ar 3 Each may independently be one of the substituents listed in Group I.

[0233] In another embodiment of the present invention, the second compound can be represented by Chemical Formula 3C, in which L a3 and L a4 Can be a single bond, L 7 and L 8 may be each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 14 , R 15 , R d3 and R d4 are each hydrogen, deuterium or phenyl, and Ar 4 and Ar 5Each of them independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group or a substituted or unsubstituted dibenzothiophenyl group.

[0234] For example, in Formula 3C, L c3 and L c4 Can be a single bond, R 14 , R 15 , R d3 and R d4 may each independently be hydrogen, deuterium or C6 to C12 aryl, and *-L 7 -Ar 4 and *-L 8 -Ar 5 Each may independently be one of the substituents listed in Group I.

[0235] For example, the second compound for an organic optoelectronic device may be one selected from the compounds listed in Group 2, but is not limited thereto.

[0236] [Group 2]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244] In addition, examples in which at least one hydrogen in Compound B-1 to Compound B-150 listed in Group 2 is replaced by deuterium are shown below, but are not limited thereto.

[0245]

[0246]

[0247] (Dn refers to the number of deuterium substitution and represents a structure substituted with one or more deuteriums)

[0248] The most specific structures of Compound B-151 to Compound B-195 of Group 2 are provided below as examples according to the position and substitution rate of deuterium substitution, and are not intended to limit the scope of rights of compounds not listed below.

[0249] The scope of the present disclosure is determined by the claims, and when substituted with deuterium, it is not limited to the compounds exemplified below, but may include all variable ranges within the range of Compound B-1 to Compound B-195 according to the deuterium substitution position, deuterium substitution rate, etc.

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257] In addition, examples in which at least one hydrogen in Compound C-1 to Compound C-57 listed in Group 2 is replaced by deuterium are shown below, but are not limited thereto.

[0258]

[0259]

[0260] (Dn refers to the number of deuterium substitution and represents a structure substituted with one or more deuteriums)

[0261] The most specific structures of Compound C-58 to Compound C-72 of Group 2 are provided below as examples according to the position and substitution rate of deuterium substitution, and are not intended to limit the scope of rights of compounds not listed below.

[0262] The scope of the present disclosure is determined by the claims, and when substituted with deuterium, it is not limited to the compounds exemplified below, but can include all variable ranges within the range of compound C-58 to compound C-72 according to the deuterium substitution position, deuterium substitution rate, etc.

[0263]

[0264]

[0265]

[0266] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. Within the above range, bipolar characteristics may be achieved by matching the appropriate weight ratio using the electron transport capability of the first compound and the hole transport capability of the second compound, thereby improving efficiency and lifespan. Within this range, for example, they may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20 (e.g., 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.

[0267] In addition to the above-mentioned first compound and second compound, one or more additional compounds may be contained.

[0268] The above-mentioned compound for an organic optoelectronic device or the composition for an organic optoelectronic device may be a composition further including a dopant.

[0269] The dopant may be, for example, a phosphorescent dopant, such as a red, green, or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0270] A dopant is a material mixed in a small amount with a compound or composition for an organic optoelectronic device to cause light emission, and may generally be a material such as a metal complex that emits light by multiple excitations to a triplet state or more. The dopant may be, for example, an inorganic, organic, or organic / inorganic compound, and one or more types thereof may be used.

[0271] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organic metal compound including 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 chemical formula Z, but is not limited thereto.

[0272] [Chemical formula Z]

[0273] L 9 MX 3

[0274] In the chemical formula Z, M is a metal and L 9 and X 3 are the same or different and are ligands that form a complex with M.

[0275] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L 9 and X 3This may be, for example, a bidentate ligand.

[0276] By L 9 and X 3 Examples of the ligand represented by may be selected from the chemical formulae listed in Group A, but are not limited thereto.

[0277] [Group A]

[0278]

[0279] In Group A,

[0280] R 300 To R 302 are each independently hydrogen, deuterium, C1 to C30 alkyl which may be substituted by halogen, C6 to C30 aryl which may be substituted by C1 to C30 alkyl, or halogen, and

[0281] R 303 To R 324 Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, 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.

[0282] As an example, it may include a dopant represented by Chemical Formula V.

[0283] [Chemical Formula V]

[0284]

[0285] In chemical formula V,

[0286] R 101 To R 116 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0287] R 132 To R 134 are each independently C1 to C6 alkyl,

[0288] R101 To R 116 At least one of them is a functional group represented by the chemical formula V-1,

[0289] L 100 is a bidentate ligand for a monovalent anion and is coordinated to iridium via a lone electron pair of a carbon or heteroatom, and

[0290] m14 and m15 are each independently any one of integers from 0 to 3 and m14+m15 is any one of integers from 1 to 3,

[0291] [Chemical formula V-1]

[0292]

[0293] In chemical formula V-1,

[0294] R 135 To R 139 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,and

[0295] * indicates a moiety attached to a carbon atom.

[0296] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0297] [Chemical formula Z-1]

[0298]

[0299] In the chemical formula Z-1, rings A, B, C and D independently represent a 5-membered or 6-membered carbon ring or a heterocyclic ring. A , R B , R C and R D independently represents mono-, di-, tri- or tetra-substituted or unsubstituted;

[0300] L B , L C and L D Each is independently selected from a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof;

[0301] When nA is 1, L E is selected from the group consisting of direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' and combinations thereof; when nA is 0, LE does not exist; and

[0302] R A , R B , R C , R D R, R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino and combinations thereof; any adjacent R A , R B , R C , R D , R and R' are optionally linked to each other to provide a ring; X B , X C , X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Each represents oxygen or a direct bond.

[0303] The dopant according to one embodiment may be a platinum complex, and may be represented, for example, by Chemical Formula VI.

[0304] [Chemical Formula VI]

[0305]

[0306] In Chemical Formula VI,

[0307] X 100 Selected from O, S and NR 131 ,

[0308] R 117 To R 131 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0309] R 132 To R 134 are each independently C1 to C6 alkyl,

[0310] R 117 To R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl, and

[0311] R 132 To R 134 Each is independently a C1 to C6 alkyl group.

[0312] Hereinafter, an organic optoelectronic device using the above-mentioned compound for an organic optoelectronic device or the composition for an organic optoelectronic device is described.

[0313] The organic optoelectronic device may be a suitable device that converts electrical energy into light energy, and vice versa, such as an organic photovoltaic device, an organic light emitting diode, an organic solar cell, or an organic photosensitive drum.

[0314] Herein, an organic light emitting diode as one example of an organic optoelectronic device is described with reference to the accompanying drawings.

[0315] Figure 1 is a cross-sectional view showing an organic light emitting diode according to one embodiment.

[0316] Reference Figure 1 , an organic light emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0317] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or the like, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; 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) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0318] The cathode 110 may be made of a conductor having a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may include 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 LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0319] The organic layer 105 may include the above-described compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[0320] The organic layer 105 may include a light emitting layer 130 , and the light emitting layer 130 may include the above-described compound for an organic optoelectronic device or composition for an organic optoelectronic device.

[0321] The composition for an organic optoelectronic device further including a dopant may be, for example, a green light emitting composition.

[0322] The light emitting layer 130 may include, for example, the above-described compound for an organic optoelectronic device as a phosphorescent host.

[0323] In addition to the light-emitting layer, the organic layer may further include a charge transport region.

[0324] The charge transport region may be, for example, a hole transport region 140 .

[0325] The hole transport region 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0326] 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 of group B may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[0327] [Group B]

[0328]

[0329]

[0330]

[0331]

[0332]

[0333]

[0334] (Dn refers to the number of deuterium substitution and represents a structure substituted with one or more deuteriums)

[0335] In the hole transport region 140, in addition to the above-mentioned compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having similar structures can be used.

[0336] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0337] The electron transport region 150 may further increase electron injection and / or electron mobility between the cathode 110 and the light emitting layer 130 and block holes.

[0338] 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 of group C may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[0339] [Group C]

[0340]

[0341]

[0342]

[0343] One embodiment may be an organic light emitting diode including a light emitting layer as an organic layer.

[0344] Another embodiment may be an organic light emitting diode including a light emitting layer and a hole transporting region as organic layers.

[0345] Another embodiment may be an organic light emitting diode including a light emitting layer and an electron transport region as organic layers.

[0346] Another embodiment of the present invention may provide an organic light emitting diode including a hole transport region 140 and an electron transport region 150 as the organic layer 105 in addition to the light emitting layer 130, such as Figure 1 as shown in .

[0347] On the other hand, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as organic layers in addition to the light emitting layer.

[0348] The organic light emitting diode 100 may be manufactured by forming an anode or a cathode on a substrate, then forming an organic layer by a dry film method such as vacuum deposition, sputtering, plasma plating, and ion plating, and forming a cathode or an anode thereon.

[0349] The organic light emitting diode can be applied to an organic light emitting display device.

[0350] Invention Mode

[0351] Hereinafter, the embodiments are described in more detail with reference to examples. However, these examples are exemplary, and the scope of claims is not limited thereto.

[0352] Hereinafter, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo Chemical Industry or P&H Tech, or synthesized by known methods unless otherwise specified.

[0353] (Preparation of Compounds for Organic Optoelectronic Devices)

[0354] Synthesis Example 1: Synthesis of Intermediate I-1

[0355]

[0356] In a nitrogen environment, 2-bromo-1-chloro-3-fluorobenzene (1000 g, 4,775 mmol) purchased from Henan Tianfu Chemical Co., Ltd. (www.tianfuchem.net) was dissolved in 10 L toluene, and 2,6-dimethoxyphenylboric acid (1043 g, 5,730 mmol) and tetrakis (triphenylphosphine) palladium (110 g, 95.5 mmol) purchased from BidePharmatech Ltd. (https: / / jlchem.co.kr / ) were added thereto, and then stirred. Subsequently, a saturated solution of potassium carbonate (1,650 g, 11,938 mmol) in water was added thereto, and then heated to reflux at 130 ° C for 3 days. When the reaction was complete, after adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM) and treated with anhydrous magnesium sulfate to remove moisture, then filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain Intermediate I-1 (535 g, 42%).

[0357] HRMS (70 eV, EI+): m / z theoretical value for C14H12ClFO2: 266.0510, measured value: 266.

[0358] Elemental analysis: C, 63%; H, 5%

[0359] Synthesis Example 2: Synthesis of Intermediate I-2

[0360]

[0361] In a nitrogen environment, intermediate I-1 (500 g, 1,875 mmol) and pyridine hydrochloride (1,483 g, 18,748 mmol) were added and heated to reflux for 12 hours at 180 ° C. When the reaction was completed, after adding water to the reaction solution, the mixture was extracted with ethyl acetate (EA) and treated with anhydrous magnesium sulfate to remove moisture, then filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-2 (361 g, 81%).

[0362] HRMS (70 eV, EI+): m / z theoretical value for C12H8ClFO2: 238.0197, measured value: 238.

[0363] Elemental analysis: C, 60%; H, 3%

[0364] Synthesis Example 3: Synthesis of Intermediate I-3

[0365]

[0366] In a nitrogen environment, intermediate I-2 (350g, 1,467mmol) was dissolved in 0.3L of N-methyl-2-pyrrolidone (NMP), and potassium carbonate (406g, 2,934mmol) was added thereto, and then heated to reflux for 3 hours. When the reaction was complete, after adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM) and treated with anhydrous magnesium sulfate to remove moisture, then filtered and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain intermediate I-3 (103g, 32%).

[0367] HRMS (70 eV, EI+): m / z theoretical value for C12H7ClO2: 218.0135, measured value: 218.

[0368] Elemental analysis: C, 66%; H, 3%

[0369] Synthesis Example 4: Synthesis of Intermediate I-4

[0370]

[0371] In a nitrogen environment, intermediate I-3 (100g, 457mmol) is dissolved in 1.0L dichloromethane (DCM), and then cooled to 0°C. After adding pyridine (43.4g, 549mmol) and stirring the mixture for 30 minutes, trifluoromethanesulfonic anhydride (155g, 549mmol) is slowly added thereto, and then stirred. After 3 hours, the reaction solution is cooled to 0°C, and after slowly adding water thereto within 30 minutes, the mixture is extracted with dichloromethane (DCM), and treated with anhydrous magnesium sulfate to remove moisture, then filtered and concentrated under reduced pressure. The obtained residue is separated and purified by flash column chromatography to obtain intermediate I-4 (157g, 98%).

[0372] HRMS (70 eV, EI+): m / z theoretical value of C13H6ClF3O4S: 349.9627, measured value: 350.

[0373] Elemental analysis: C, 45%; H, 2%

[0374] Synthesis Example 5: Synthesis of Intermediate I-5

[0375]

[0376] Intermediate I-5 (103 g, 65%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-4 (150 g, 428 mmol) and dibenzofuran-1-boric acid (99.8 g, 471 mmol) purchased from Tokyo Chemical Industry Co., Ltd. were used.

[0377] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClO2: 368.0604, measured value: 368.

[0378] Elemental analysis: C, 78%; H, 4%

[0379] Synthesis Example 6: Synthesis of Intermediate I-6

[0380]

[0381] In nitrogen environment, intermediate I-5 (100g, 271mmol) is dissolved in 0.1L dimethylbenzene, then bis (pinacol) diboron (82.6g, 325mmol), tris (dibenzylideneacetone) dipalladium (0) (2.48g, 2.71mmol), tricyclohexylphosphine (3.04g, 10.8mmol) and potassium acetate (79.8g, 813mmol) are added thereto, then heated to reflux for 12 hours. When the reaction is complete, after adding water to the reaction solution, the mixture is extracted with ethyl acetate (EA) and treated with anhydrous magnesium sulfate to remove moisture, then filtered and concentrated under reduced pressure. The obtained residue is separated and purified by flash column chromatography to obtain intermediate I-6 (62.4g, 50%).

[0382] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO4: 460.1846, measured value: 460.

[0383] Elemental analysis: C, 78%; H, 5%

[0384] Synthesis Example 7: Synthesis of Compound 1

[0385]

[0386] Compound 1 (28.0 g, 90%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-6 (20 g, 43.4 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (18.2 g, 43.4 mmol) purchased from P&H Tech (http: / / www.phtech.co.kr / ) were used.

[0387] HRMS (70 eV, EI+): m / z theoretical value of C51H29N3O2: 715.2260, measured value: 715.

[0388] Elemental analysis: C, 86%; H, 4%

[0389] Synthesis Example 8: Synthesis of Intermediate I-7

[0390]

[0391] Intermediate I-7 (42.2 g, 80%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-4 (50 g, 143 mmol) and dibenzofuran-2-boric acid (33.2 g, 157 mmol) purchased from Tokyo Chemical Industry Co., Ltd. were used.

[0392] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClO2: 368.0604, measured value: 368.

[0393] Elemental analysis: C, 78%; H, 4%

[0394] Synthesis Example 9: Synthesis of Intermediate I-8

[0395]

[0396] Intermediate I-8 (37.3 g, 75%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-7 (40 g, 108 mmol) was used.

[0397] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO4: 460.1846, measured value: 460.

[0398] Elemental analysis: C, 78%; H, 5%

[0399] Synthesis Example 10: Synthesis of Compound 2

[0400]

[0401] Compound 1 (28.9 g, 93%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-8 (20 g, 43.4 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (18.2 g, 43.4 mmol) purchased from P&H Tech were used.

[0402] HRMS (70 eV, EI+): m / z theoretical value of C51H29N3O2: 715.2260, measured value: 715.

[0403] Elemental analysis: C, 86%; H, 4%

[0404] Synthesis Example 11: Synthesis of Intermediate I-9

[0405]

[0406] Intermediate I-9 (40.6 g, 77%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-4 (50 g, 143 mmol) and dibenzofuran-3-boric acid (33.2 g, 157 mmol) purchased from Tokyo Chemical Industry Co., Ltd. were used.

[0407] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClO2: 368.0604, measured value: 368.

[0408] Elemental analysis: C, 78%; H, 4%

[0409] Synthesis Example 12: Synthesis of Intermediate I-10

[0410]

[0411] Intermediate I-10 (40.3 g, 81%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-9 (40 g, 108 mmol) was used.

[0412] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO4: 460.1846, measured value: 460.

[0413] Elemental analysis: C, 78%; H, 5%

[0414] Synthesis Example 13: Synthesis of Compound 3

[0415]

[0416] Compound 3 (29.5 g, 95%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-10 (20 g, 43.4 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (18.2 g, 43.4 mmol) purchased from P&H Tech were used.

[0417] HRMS (70 eV, EI+): m / z theoretical value of C51H29N3O2: 715.2260, measured value: 715.

[0418] Elemental analysis: C, 86%; H, 4%

[0419] Synthesis Example 14: Synthesis of Intermediate I-11

[0420]

[0421] Intermediate I-11 (32.7 g, 62%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-4 (50 g, 143 mmol) and dibenzofuran-4-boric acid (33.2 g, 157 mmol) purchased from Tokyo Chemical Industry Co., Ltd. were used.

[0422] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClO2: 368.0604, measured value: 368.

[0423] Elemental analysis: C, 78%; H, 4%

[0424] Synthesis Example 15: Synthesis of Intermediate I-12

[0425]

[0426] Intermediate I-12 (21.4 g, 43%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-11 (40 g, 108 mmol) was used.

[0427] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO4: 460.1846, measured value: 460.

[0428] Elemental analysis: C, 78%; H, 5%

[0429] Synthesis Example 16: Synthesis of Compound 4

[0430]

[0431] Compound 4 (26.4 g, 85%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-12 (20 g, 43.4 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (18.2 g, 43.4 mmol) purchased from P&H Tech were used.

[0432] HRMS (70 eV, EI+): m / z theoretical value of C51H29N3O2: 715.2260, measured value: 715.

[0433] Elemental analysis: C, 86%; H, 4%

[0434] Synthesis Example 17: Synthesis of Intermediate I-13

[0435]

[0436] Intermediate I-13 (102 g, 80%) was obtained in the same manner as in Synthesis Example 1, except that 2-bromo-4-chloro-1-fluorobenzene (100 g, 477 mmol) purchased from Tokyo Chemical Industry Co., Ltd. and 2,6-dimethoxyphenylboronic acid (101 g, 525 mmol) purchased from P&HTech Bide Pharmatech Ltd. were used.

[0437] HRMS (70 eV, EI+): m / z theoretical value for C14H12ClFO2: 266.0510, measured value: 266.

[0438] Elemental analysis: C, 63%; H, 5%

[0439] Synthesis Example 18: Synthesis of Intermediate I-14

[0440]

[0441] Intermediate I-14 (85.0 g, 95%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-13 (100 g, 375 mmol) was used.

[0442] HRMS (70 eV, EI+): m / z theoretical value for C12H8ClFO2: 238.0197, measured value: 238.

[0443] Elemental analysis: C, 60%; H, 3%

[0444] Synthesis Example 19: Synthesis of Intermediate I-15

[0445]

[0446] Intermediate I-15 (67.8 g, 65%) was obtained in the same manner as in Synthesis Example 3, except that Intermediate I-14 (100 g, 477 mmol) was used.

[0447] HRMS (70 eV, EI+): m / z theoretical value for C12H7ClO2: 218.0135, measured value: 218.

[0448] Elemental analysis: C, 66%; H, 3%

[0449] Synthesis Example 20: Synthesis of Intermediate I-16

[0450]

[0451] Intermediate I-16 (63.7 g, 98%) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-15 (65 g, 185 mmol) was used.

[0452] HRMS (70 eV, EI+): m / z theoretical value of C13H6ClF3O4S: 349.9627, measured value: 350.

[0453] Elemental analysis: C, 45%; H, 2%

[0454] Synthesis Example 21: Synthesis of Intermediate I-17

[0455]

[0456] Intermediate I-17 (38.5 g, 61%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-16 (60 g, 171 mmol) and dibenzofuran-1-boric acid (39.9 g, 188 mmol) purchased from Tokyo Chemical Industry Co., Ltd. were used.

[0457] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClO2: 368.0604, measured value: 368.

[0458] Elemental analysis: C, 78%; H, 4%

[0459] Synthesis Example 22: Synthesis of Intermediate I-18

[0460]

[0461] Intermediate I-18 (12.6 g, 78%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-17 (35 g, 94.9 mmol) was used.

[0462] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO4: 460.1846, measured value: 460.

[0463] Elemental analysis: C, 78%; H, 5%

[0464] Synthesis Example 23: Synthesis of Compound 5

[0465]

[0466] Compound 5 (14.3 g, 92%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-18 (10 g, 21.7 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (9.08 g, 21.7 mmol) purchased from P&H Tech were used.

[0467] HRMS (70 eV, EI+): m / z theoretical value of C51H29N3O2: 715.2260, measured value: 715.

[0468] Elemental analysis: C, 86%; H, 4%

[0469] Synthesis Example 24: Synthesis of Intermediate I-19

[0470]

[0471] Intermediate I-19 (122 g, 96%) was obtained in the same manner as in Synthesis Example 1, except that 1-bromo-4-chloro-2-fluorobenzene (100 g, 477 mmol) purchased from Tokyo Chemical Industry Co., Ltd. and 2,6-dimethoxyphenylboronic acid (101 g, 525 mmol) purchased from P&HTech or Bide Pharmatech Ltd. were used.

[0472] HRMS (70 eV, EI+): m / z theoretical value for C14H12ClFO2: 266.0510, measured value: 266.

[0473] Elemental analysis: C, 63%; H, 5%

[0474] Synthesis Example 25: Synthesis of Intermediate I-20

[0475]

[0476] Intermediate I-20 (97.7 g, 91%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-19 (120 g, 450 mmol) was used.

[0477] HRMS (70 eV, EI+): m / z theoretical value for C12H8ClFO2: 238.0197, measured value: 238.

[0478] Elemental analysis: C, 60%; H, 3%

[0479] Synthesis Example 26: Synthesis of Intermediate I-21

[0480]

[0481] Intermediate I-21 (60.9 g, 70%) was obtained in the same manner as in Synthesis Example 3, except that Intermediate I-20 (95 g, 398 mmol) was used.

[0482] HRMS (70 eV, EI+): m / z theoretical value for C12H7ClO2: 218.0135, measured value: 218.

[0483] Elemental analysis: C, 66%; H, 3%

[0484] Synthesis Example 27: Synthesis of Intermediate I-22

[0485]

[0486] Intermediate I-22 (83.8 g, 95%) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-21 (55 g, 252 mmol) was used.

[0487] HRMS (70 eV, EI+): m / z theoretical value of C13H6ClF3O4S: 349.9627, measured value: 350.

[0488] Elemental analysis: C, 45%; H, 2%

[0489] Synthesis Example 28: Synthesis of Intermediate I-23

[0490]

[0491] Intermediate I-23 (63.1 g, 75%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-22 (80 g, 228 mmol) and dibenzofuran-1-boric acid (53.2 g, 251 mmol) purchased from Tokyo Chemical Industry Co., Ltd. were used.

[0492] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClO2: 368.0604, measured value: 368.

[0493] Elemental analysis: C, 78%; H, 4%

[0494] Synthesis Example 29: Synthesis of Intermediate I-24

[0495]

[0496] Intermediate I-24 (54.1 g, 70%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-23 (62 g, 168 mmol) was used.

[0497] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO4: 460.1846, measured value: 460.

[0498] Elemental analysis: C, 78%; H, 5%

[0499] Synthesis Example 30: Synthesis of Compound 6

[0500]

[0501] Compound 5 (31.1 g, 85%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-24 (20 g, 43.4 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (18.2 g, 43.4 mmol) purchased from P&H Tech were used.

[0502] HRMS (70 eV, EI+): m / z theoretical value of C51H29N3O2: 715.2260, measured value: 715.

[0503] Elemental analysis: C, 86%; H, 4%

[0504] Synthesis Example 31: Synthesis of Intermediate I-25

[0505]

[0506] Intermediate I-25 (114 g, 90%) was obtained in the same manner as in Synthesis Example 1, except that 1-bromo-3-chloro-2-fluorobenzene (100 g, 477 mmol) purchased from Tokyo Chemical Industry Co., Ltd. and 2,6-dimethoxyphenylboronic acid (101 g, 525 mmol) purchased from P&HTech Bide Pharmatech Ltd. were used.

[0507] HRMS (70 eV, EI+): m / z theoretical value for C14H12ClFO2: 266.0510, measured value: 266.

[0508] Elemental analysis: C, 63%; H, 5%

[0509] Synthesis Example 32: Synthesis of Intermediate I-26

[0510]

[0511] Intermediate I-26 (100 g, 99%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-25 (113 g, 424 mmol) was used.

[0512] HRMS (70 eV, EI+): m / z theoretical value for C12H8ClFO2: 238.0197, measured value: 238.

[0513] Elemental analysis: C, 60%; H, 3%

[0514] Synthesis Example 33: Synthesis of Intermediate I-27

[0515]

[0516] Intermediate I-27 (46.7 g, 52%) was obtained in the same manner as in Synthesis Example 3, except that Intermediate I-26 (98 g, 411 mmol) was used.

[0517] HRMS (70 eV, EI+): m / z theoretical value for C12H7ClO2: 218.0135, measured value: 218.

[0518] Elemental analysis: C, 66%; H, 3%

[0519] Synthesis Example 34: Synthesis of Intermediate I-28

[0520]

[0521] Intermediate I-28 (70.8 g, 98%) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-27 (45 g, 206 mmol) was used.

[0522] HRMS (70 eV, EI+): m / z theoretical value of C13H6ClF3O4S: 349.9627, measured value: 350.

[0523] Elemental analysis: C, 45%; H, 2%

[0524] Synthesis Example 35: Synthesis of Intermediate I-29

[0525]

[0526] Intermediate I-29 (50.9 g, 70%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-28 (69 g, 197 mmol) and dibenzofuran-1-boric acid (45.8 g, 216 mmol) purchased from Tokyo Chemical Industry Co., Ltd. were used.

[0527] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClO2: 368.0604, measured value: 368.

[0528] Elemental analysis: C, 78%; H, 4%

[0529] Synthesis Example 36: Synthesis of Intermediate I-30

[0530]

[0531] Intermediate I-30 (44.9 g, 72%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-29 (50 g, 136 mmol) was used.

[0532] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO4: 460.1846, measured value: 460.

[0533] Elemental analysis: C, 78%; H, 5%

[0534] Synthesis Example 37: Synthesis of Compound 7

[0535]

[0536] Compound 5 (28.0 g, 90%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-30 (20 g, 43.4 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (18.2 g, 43.4 mmol) purchased from P&H Tech were used.

[0537] HRMS (70 eV, EI+): m / z theoretical value of C51H29N3O2: 715.2260, measured value: 715.

[0538] Elemental analysis: C, 86%; H, 4%

[0539] Synthesis Example 38: Synthesis of Intermediate I-31

[0540]

[0541] Intermediate I-31 (76.8 g, 70%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-4 (100 g, 285 mmol) and dibenzothiophene-1-boronic acid (78.0 g, 342 mmol) were used.

[0542] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClOS: 384.0376, measured value: 384.

[0543] Elemental analysis: C, 75%; H, 3%

[0544] Synthesis Example 39: Synthesis of Intermediate I-32

[0545]

[0546] Intermediate I-32 (40.8 g, 44%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-31 (75 g, 195 mmol) was used.

[0547] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO3S: 476.1617, measured value: 476.

[0548] Elemental analysis: C, 76%; H, 5%

[0549] Synthesis Example 40: Synthesis of Compound 8

[0550]

[0551] Compound 8 (26.7 g, 87%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-32 (20 g, 42.0 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (17.5 g, 42.0 mmol) purchased from P&H Tech were used.

[0552] HRMS (70 eV, EI+): m / z theoretical value for C51H29N3OS: 731.2031, measured value: 731.

[0553] Elemental analysis: C, 84%; H, 4%

[0554] Synthesis Example 41: Synthesis of Intermediate I-33

[0555]

[0556] Intermediate I-33 (71.3 g, 65%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-4 (100 g, 285 mmol) and dibenzothiophene-4-boric acid (78.0 g, 342 mmol) were used.

[0557] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClOS: 384.0376, measured value: 384.

[0558] Elemental analysis: C, 75%; H, 3%

[0559] Synthesis Example 42: Synthesis of Intermediate I-34

[0560]

[0561] Intermediate I-34 (35.5 g, 41%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-33 (70 g, 182 mmol) was used.

[0562] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO3S: 476.1617, measured value: 476.

[0563] Elemental analysis: C, 76%; H, 5%

[0564] Synthesis Example 43: Synthesis of Compound 12

[0565]

[0566] Compound 12 (27.0 g, 88%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-34 (20 g, 42.0 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (17.5 g, 42.0 mmol) purchased from P&H Tech were used.

[0567] HRMS (70 eV, EI+): m / z theoretical value for C51H29N3OS: 731.2031, measured value: 731.

[0568] Elemental analysis: C, 84%; H, 4%

[0569] Synthesis Example 44: Synthesis of Compound 13

[0570]

[0571] Compound 13 (29.2 g, 85%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-6 (20 g, 43.4 mmol) and 2-(biphenyl-3-yl)-4-chloro-6-(triphenyl-2-yl)-1,3,5-triazine (19.1 g, 43.4 mmol) purchased from P&H Tech were used.

[0572] HRMS (70 eV, EI+): Calculated m / z value for C57H33N3O2: 791.2573, measured value: 791.

[0573] Elemental analysis: C, 86%; H, 4%

[0574] Synthesis Example 45: Synthesis of Intermediate I-35

[0575]

[0576] Intermediate I-35 (20.0 g, 35%) was obtained in the same manner as in Synthesis Example 1, except that 4,4,5,5-tetramethyl-2-(3-(triphenyl-2-yl)phenyl)-1,3,2-dioxaborolane (50 g, 116 mmol) and 2,4-dichloro-6-phenyl-1,3,5-triazine (39.4 g, 174 mmol) were used.

[0577] HRMS (70 eV, EI+): m / z theoretical value for C33H20ClN3: 493.1346, measured value: 493.

[0578] Elemental analysis: C, 80%; H, 4%

[0579] Synthesis Example 46: Synthesis of Compound 25

[0580]

[0581] Compound 25 (15.3 g, 89%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-6 (10 g, 21.7 mmol) and Intermediate I-35 (10.7 g, 21.7 mmol) were used.

[0582] HRMS (70 eV, EI+): Calculated m / z value for C57H33N3O2: 791.2573, measured value: 791.

[0583] Elemental analysis: C, 86%; H, 4%

[0584] Synthesis Example 47: Synthesis of Intermediate I-36

[0585]

[0586] Intermediate I-36 (113 g, 92%) was obtained in the same manner as in Synthesis Example 6, except that 4-bromo-1-chloro-2-fluorobenzene (100 g, 477 mmol) was used.

[0587] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO3S: 256.0838, measured value: 256.

[0588] Elemental analysis: C, 56%; H, 6%

[0589] Synthesis Example 48: Synthesis of Intermediate I-37

[0590]

[0591] Intermediate I-37 (124 g, 80%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-36 (110 g, 429 mmol) and 2,2′-dibromobiphenyl (201 g, 643 mmol) were used.

[0592] HRMS (70 eV, EI+): m / z calcd. for C18H11BrClF: 359.9717, measured: 359.

[0593] Elemental analysis: C, 60%; H, 3%

[0594] Synthesis Example 49: Synthesis of Intermediate I-38

[0595]

[0596] In a nitrogen environment, intermediate I-37 (120g, 332mmol) is dissolved in 1.2L dimethylbenzene, and bis (dibenzylideneacetone) palladium (0) (15.2g, 16.6mmol), triphenylphosphine (17.5g, 66.6mmol) and cesium carbonate (130g, 400mmol) are added thereto, then heated to reflux for 24 hours at 140°C. When the reaction is complete, after adding water to the reaction solution, the mixture is extracted with dichloromethane (DCM) and treated with anhydrous magnesium sulfate to remove moisture, then filtered and concentrated under reduced pressure. The obtained residue is separated and purified by flash column chromatography to obtain intermediate I-38 (14.9g, 16%).

[0597] HRMS (70 eV, EI+): m / z theoretical value for C18H10ClF: 280.0455, measured value: 280.

[0598] Elemental analysis: C, 77%; H, 4%

[0599] Synthesis Example 50: Synthesis of Intermediate I-39

[0600]

[0601] Intermediate I-39 (14.9 g, 80%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-38 (14 g, 49.9 mmol) was used.

[0602] HRMS (70 eV, EI+): m / z theoretical value of C24H22BFO2: 372.1697, measured value: 372.

[0603] Elemental analysis: C, 77%; H, 6%

[0604] Synthesis Example 51: Synthesis of Intermediate I-40

[0605]

[0606] Intermediate I-40 (7.4 g, 45%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-39 (14 g, 37.6 mmol) and 2,4-dichloro-6-phenyl-1,3,5-triazine (12.8 g, 56.4 mmol) were used.

[0607] HRMS (70 eV, EI+): m / z theoretical value for C27H15ClFN3: 435.0939, measured value: 435.

[0608] Elemental analysis: C, 74%; H, 3%

[0609] Synthesis Example 52: Synthesis of Intermediate I-41

[0610]

[0611] Intermediate I-41 (15.3 g, 89%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-40 (6.5 g, 14.9 mmol) and Intermediate I-6 (8.24 g, 17.9 mmol) were used.

[0612] HRMS (70 eV, EI+): m / z theoretical value of C51H28FN3O2: 733.2166, measured value: 733.

[0613] Elemental analysis: C, 83%; H, 4%

[0614] Synthesis Example 53: Synthesis of Compound 45

[0615]

[0616] In a nitrogen environment, intermediate I-41 (14g, 19.1mmol) was dissolved in 0.2L of N-methyl-2-pyrrolidone (NMP), and 9H-carbazole (3.51g, 21.0mmol) and cesium carbonate (12.4g, 38.2mmol) were added thereto, and heated to reflux for 24 hours. When the reaction was complete, after distillation and removal of solvent and then adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM), and treated with anhydrous magnesium sulfate to remove moisture, then filtered and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain compound 45 (11.8g, 70%).

[0617] HRMS (70 eV, EI+): Calculated m / z value of C63H36N4O2: 880.2838, measured value: 880.

[0618] Elemental analysis: C, 86%; H, 5%

[0619] Synthesis Example 54: Synthesis of Intermediate I-42

[0620]

[0621] Intermediate I-42 (48.5 g, 91%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-12 (50 g, 109 mmol) and 1-bromo-2-iodobenzene (46.1 g, 163 mmol) were used.

[0622] HRMS (70 eV, EI+): m / z theoretical value for C30H17BrO2: 488.0412, measured value: 488.

[0623] Elemental analysis: C, 74%; H, 4%

[0624] Synthesis Example 55: Synthesis of Intermediate I-43

[0625]

[0626] Intermediate I-43 (39.5 g, 75%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-42 (14 g, 98.1 mmol) was used.

[0627] HRMS (70 eV, EI+): m / z theoretical value of C36H29BO4: 536.2159, measured value: 536.

[0628] Elemental analysis: C, 81%; H, 5%

[0629] Synthesis Example 56: Synthesis of Compound 69

[0630]

[0631] Compound 69 (20.7 g, 70%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-43 (20 g, 37.3 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (15.6 g, 37.3 mmol) were used.

[0632] HRMS (70 eV, EI+): Calculated m / z value for C57H33N3O2: 791.2573, measured value: 791.

[0633] Elemental analysis: C, 86%; H, 4%

[0634] Synthesis Example 57: Synthesis of Intermediate I-44

[0635]

[0636] Intermediate I-44 (121 g, 95%) was obtained in the same manner as in Synthesis Example 1, except that 2-bromo-1-chloro-3-fluorobenzene (100 g, 477 mmol) and 2,3-dimethoxyphenylboronic acid (95.6 g, 525 mmol) were used.

[0637] HRMS (70 eV, EI+): m / z theoretical value for C14H12ClFO2: 266.0510, measured value: 266.

[0638] Elemental analysis: C, 63%; H, 5%

[0639] Synthesis Example 58: Synthesis of Intermediate I-45

[0640]

[0641] Intermediate I-45 (106 g, 99%) was obtained in the same manner as in Synthesis Example 2, except that Intermediate I-44 (120 g, 450 mmol) was used.

[0642] HRMS (70 eV, EI+): m / z theoretical value for C12H8ClFO2: 238.0197, measured value: 238.

[0643] Elemental analysis: C, 60%; H, 3%

[0644] Synthesis Example 59: Synthesis of Intermediate I-46

[0645]

[0646] Intermediate I-46 (67.3 g, 70%) was obtained in the same manner as in Synthesis Example 3, except that Intermediate I-45 (105 g, 440 mmol) was used.

[0647] HRMS (70 eV, EI+): m / z theoretical value for C12H7ClO2: 218.0135, measured value: 218.

[0648] Elemental analysis: C, 66%; H, 3%

[0649] Synthesis Example 60: Synthesis of Intermediate I-47

[0650]

[0651] Intermediate I-47 (103 g, 99%) was obtained in the same manner as in Synthesis Example 4, except that Intermediate I-46 (65 g, 297 mmol) was used.

[0652] HRMS (70 eV, EI+): m / z theoretical value of C13H6ClF3O4S: 349.9627, measured value: 349.

[0653] Elemental analysis: C, 45%; H, 2%

[0654] Synthesis Example 61: Synthesis of Intermediate I-48

[0655]

[0656] Intermediate I-48 (76.7 g, 73%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-47 (100 g, 285 mmol) and dibenzofuran-4-boronic acid (66.5 g, 314 mmol) were used.

[0657] HRMS (70 eV, EI+): m / z theoretical value for C24H13ClO2: 368.0604, measured value: 368.

[0658] Elemental analysis: C, 78%; H, 4%

[0659] Synthesis Example 62: Synthesis of Intermediate I-49

[0660]

[0661] Intermediate I-49 (47.7 g, 51%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-48 (75 g, 203 mmol) was used.

[0662] HRMS (70 eV, EI+): m / z theoretical value of C30H25BO4: 460.1846, measured value: 460.

[0663] Elemental analysis: C, 78%; H, 5%

[0664] Synthesis Example 63: Synthesis of Compound 225

[0665]

[0666] Compound 225 (27.3 g, 88%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-49 (20 g, 43.4 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (18.2 g, 43.4 mmol) purchased from P&H Tech were used.

[0667] HRMS (70 eV, EI+): m / z theoretical value of C51H29N3O2: 715.2260, measured value: 715.

[0668] Elemental analysis: C, 86%; H, 4%

[0669] Synthesis Example 64: Synthesis of Intermediate I-50

[0670]

[0671] Intermediate I-50 (67.5 g, 85%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-4 (100 g, 285 mmol) and phenylboronic acid (41.7 g, 342 mmol) were used.

[0672] HRMS (70 eV, EI+): m / z theoretical value for C18H11ClO: 278.0498, measured value: 278.

[0673] Elemental analysis: C, 78%; H, 4%

[0674] Synthesis Example 65: Synthesis of Intermediate I-51

[0675]

[0676] Intermediate I-51 (46.6 g, 54%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-50 (65 g, 233 mmol) was used.

[0677] HRMS (70 eV, EI+): m / z theoretical value of C24H23BO3: 370.1740, measured value: 370.

[0678] Elemental analysis: C, 78%; H, 6%

[0679] Synthesis Example 66: Synthesis of Intermediate I-52

[0680]

[0681] Intermediate I-52 (64.7 g, 51%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-4 (100 g, 285 mmol) and Intermediate I-51 (116 g, 314 mmol) were used.

[0682] HRMS (70 eV, EI+): m / z theoretical value for C30H17ClO2: 444.0917, measured value: 444.

[0683] Elemental analysis: C, 81%; H, 4%

[0684] Synthesis Example 67: Synthesis of Intermediate I-53

[0685]

[0686] Intermediate I-53 (36.5 g, 48%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-52 (63 g, 142 mmol) was used.

[0687] HRMS (70 eV, EI+): m / z theoretical value of C36H29BO4: 536.2159, measured value: 536.

[0688] Elemental analysis: C, 81%; H, 5%

[0689] Synthesis Example 68: Synthesis of Compound 57

[0690]

[0691] Compound 57 (25.1 g, 85%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-53 (20 g, 37.3 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (15.6 g, 37.3 mmol) purchased from P&H Tech were used.

[0692] HRMS (70 eV, EI+): Calculated m / z value for C57H33N3O2: 791.2573, measured value: 791.

[0693] Elemental analysis: C, 86%; H, 4%

[0694] Synthesis Example 69: Synthesis of Intermediate I-54

[0695]

[0696] Intermediate I-54 (44.1 g, 75%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-4 (50 g, 143 mmol) and 5,5-dimethyl-5H-dibenzothiorol-3-ylboronic acid (39.9 g, 157 mmol) were used.

[0697] HRMS (70 eV, EI+): m / z theoretical value for C26H19ClOSi: 410.0894, measured value: 410.

[0698] Elemental analysis: C, 76%; H, 5%

[0699] Synthesis Example 70: Synthesis of Intermediate I-55

[0700]

[0701] Intermediate I-55 (26.3 g, 50%) was obtained in the same manner as in Synthesis Example 6, except that Intermediate I-54 (43 g, 105 mmol) was used.

[0702] HRMS (70 eV, EI+): m / z theoretical value of C32H31BO3Si: 502.2136, measured value: 502.

[0703] Elemental analysis: C, 76%; H, 6%

[0704] Synthesis Example 71: Synthesis of Compound 119

[0705]

[0706] Compound 119 (2.4 g, 81%) was obtained in the same manner as in Synthesis Example 1, except that intermediate I-55 (20 g, 39.8 mmol) and 2-chloro-4-phenyl-6-(triphenyl-2-yl)-1,3,5-triazine (16.6 g, 39.8 mmol) purchased from P&H Tech were used.

[0707] HRMS (70 eV, EI+): m / z theoretical value of C53H35N3OSi: 757.2549, measured value: 757.

[0708] Elemental analysis: C, 84%; H, 5%

[0709] Synthesis Example 72: Synthesis of Intermediate I-56

[0710]

[0711] Intermediate I-56 (150 g, 78%) was obtained in the same manner as in Synthesis Example 53, except that 9H-carbazole (100 g, 598 mmol) and 1-bromo-2-fluorobenzene (115 g, 658 mmol) were used.

[0712] HRMS (70 eV, EI+): m / z theoretical value for C18H12BrN: 321.0153, measured value: 321.

[0713] Elemental analysis: C, 67%; H, 4%

[0714] Synthesis Example 73: Synthesis of Intermediate I-57

[0715]

[0716] In a nitrogen environment, magnesium (10.5g, 435mmol) and iodine (2.21g, 8.7mmol) are dissolved in 0.1L tetrahydrofuran (THF), and then stirred for 30 minutes. Subsequently, the intermediate I-56 (140g, 435mmol) dissolved in 0.1L THF is slowly added thereto within 30 minutes. Within 30 minutes, the Grignard reagent prepared in this way is slowly added to the solution prepared by dissolving cyanuric chloride (96.3g, 522mmol) purchased from Tokyo Chemical Industry Co., Ltd. in 1L THF, and then stirred for 3 hours. When the reaction is complete, after adding water to the reaction solution, the mixture is extracted with dichloromethane (DCM) and treated with anhydrous magnesium sulfate to remove moisture, then filtered and concentrated under reduced pressure. The obtained residue is separated and purified by flash column chromatography to obtain intermediate I-57 (73.2g, 43%).

[0717] HRMS (7eV, EI+): m / z theoretical value of C21H12Cl2N4: 390.0439, measured value: 390.

[0718] Elemental analysis: C, 64%; H, 3%

[0719] Synthesis Example 74: Synthesis of Intermediate I-58

[0720]

[0721] Intermediate I-58 (30.9 g, 50%) was obtained in the same manner as in Synthesis Example 1, except that 4,4,5,5-tetramethyl-2-(triphenyl-2-yl)-1,3,2-dioxaborolane (37.7 g, 106 mmol) and intermediate I-57 (50 g, 128 mmol) were used.

[0722] HRMS (70 eV, EI+): m / z theoretical value for C39H23ClN4: 582.1611, measured value: 582.

[0723] Elemental analysis: C, 80%; H, 4%

[0724] Synthesis Example 75: Synthesis of Compound 181

[0725]

[0726] Compound 181 (30.6 g, 80%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-6 (20 g, 43.4 mmol) and Intermediate I-58 (25.3 g, 43.4 mmol) were used.

[0727] HRMS (70 eV, EI+): Calculated m / z value of C63H36N4O2: 880.2838, measured value: 880.

[0728] Elemental analysis: C, 86%; H, 4%

[0729] Synthesis Example 76: Synthesis of Intermediate I-59

[0730]

[0731] Intermediate I-59 (31.1 g, 45%) was obtained in the same manner as in Synthesis Example 73, except that 3-bromobenzonitrile (50 g, 275 mmol) was used.

[0732] HRMS (70 eV, EI+): m / z theoretical value for C10H4Cl2N4: 249.9813, measured value: 249.

[0733] Elemental analysis: C, 48%; H, 1%

[0734] Synthesis Example 77: Synthesis of Intermediate I-60

[0735]

[0736] Intermediate I-60 (17.2 g, 39%) was obtained in the same manner as in Synthesis Example 1, except that 4,4,5,5-tetramethyl-2-(triphenyl-2-yl)-1,3,2-dioxaborolane (35.3 g, 99.6 mmol) and intermediate I-59 (30 g, 119 mmol) were used.

[0737] HRMS (70 eV, EI+): m / z theoretical value for C28H15ClN4: 442.0985, measured value: 442.

[0738] Elemental analysis: C, 76%; H, 3%

[0739] Synthesis Example 78: Synthesis of Compound 221

[0740]

[0741] Compound 221 (26.7 g, 83%) was obtained in the same manner as in Synthesis Example 1, except that Intermediate I-6 (20 g, 43.4 mmol) and Intermediate I-60 (19.2 g, 43.4 mmol) were used.

[0742] HRMS (70 eV, EI+): Calculated m / z value of C52H28N4O2: 740.2212, measured value: 740.

[0743] Elemental analysis: C, 84%; H, 4%

[0744] Synthesis Example 79: Synthesis of Compound 1

[0745]

[0746] The main compound 1 was synthesized by the synthesis method of reference patent KR1959821.

[0747] HRMS (70 eV, EI+): m / z theoretical value of C51H29N3O2: 715.2260, measured value: 715.

[0748] Elemental analysis: C, 86%; H, 4%

[0749] Synthesis Example 80: Synthesis of Compound 2

[0750]

[0751] The compound main body 2 was synthesized by the synthesis method of reference patent US20200377489.

[0752] HRMS (70 eV, EI+): m / z theoretical value of C45H26N4O2: 654.2056, measured value: 654.

[0753] Elemental analysis: C, 83%; H, 4%

[0754] Synthesis Example 81: Synthesis of Compound 3

[0755]

[0756] The main compound 3 was synthesized by referring to the synthesis method of patent KR2019135398.

[0757] HRMS (70 eV, EI+): m / z theoretical value for C45H27N3O: 625.2154, measured value: 625.

[0758] Elemental analysis: C, 86%; H, 4%

[0759] Synthesis Example 82: Synthesis of Compound 4

[0760]

[0761] The main compound 4 was synthesized by the synthesis method of reference patent WO2021182893.

[0762] HRMS (70 eV, EI+): m / z theoretical value of C39H23N3O2: 565.1790, measured value: 565.

[0763] Elemental analysis: C, 83%; H, 4%

[0764] Synthesis Example 83: Synthesis of Compound 5

[0765]

[0766] The main compound 5 was synthesized by the synthesis method of reference patent WO2021182893.

[0767] HRMS (70 eV, EI+): Calculated m / z for C43H25N3O2: 615.6775, measured: 615.

[0768] Elemental analysis: C, 84%; H, 4%

[0769] Synthesis Example 84: Synthesis of Compound 6

[0770]

[0771] The main compound 6 was synthesized by the synthesis method of reference patent WO2021182893.

[0772] HRMS (70 eV, EI+): m / z theoretical value of C47H27N3O2: 665.2103, measured value: 665.

[0773] Elemental analysis: C, 85%; H, 4%

[0774] Synthesis Example 85: Synthesis of Compound 7

[0775]

[0776] The main compound 7 was synthesized by the synthesis method of reference patent WO2021182893.

[0777] HRMS (70 eV, EI+): m / z theoretical value of C45H27N3O2: 641.2103, measured value: 641.

[0778] Elemental analysis: C, 84%; H, 4%

[0779] Synthesis Example 86: Synthesis of Compound B-136

[0780]

[0781] Compound B-136 was synthesized by referring to the synthesis method of patent EP3034581.

[0782] HRMS (70 eV, EI+): m / z theoretical value of C42H28N2: 560.2252, measured value: 560.

[0783] Elemental analysis: C, 90%; H, 5%

[0784] Synthesis Example 87: Synthesis of Compound B-99

[0785]

[0786] Compound B-99 was synthesized by referring to the synthesis method of patent KR10-2019-0000597.

[0787] HRMS (70 eV, EI+): m / z theoretical value of C48H32N2: 636.2565, measured value: 636.

[0788] Elemental analysis: C, 91%; H, 5%

[0789] Synthesis Example 88: Synthesis of Compound B-31

[0790]

[0791] Compound B-31 was synthesized by referring to the synthesis method of patent EP2947071.

[0792] HRMS (70 eV, EI+): m / z theoretical value of C48H32N2: 636.2565, measured value: 636.

[0793] Elemental analysis: C, 91%; H, 5%

[0794] Synthesis Example 89: Synthesis of Compound C-4

[0795]

[0796] Compound C-4 was synthesized by referring to the synthesis method of patent KR2031300.

[0797] HRMS (70 eV, EI+): m / z theoretical value of C42H28N2: 560.2252, measured value: 560.

[0798] Elemental analysis: C, 90%; H, 5%

[0799] Synthesis Example 90: Synthesis of Compound C-57

[0800]

[0801] Compound C-57 was synthesized by referring to the synthesis method of patent WO2018-095391.

[0802] HRMS (70 eV, EI+): m / z theoretical value of C48H32N2: 636.2565, measured value: 636.

[0803] Elemental analysis: C, 91%; H, 5%

[0804] Example 1

[0805] A glass substrate coated with an ITO (indium tin oxide) thin film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A (Novaled GmbH) doped with 3% NDP-9 was vacuum deposited on the ITO substrate to form A thick hole injection layer is formed, and compound A is deposited on the hole injection layer to form Compound B is deposited on the hole transport layer to form A hole transport auxiliary layer having a thickness of 100 nm was formed, and on the hole transport auxiliary layer, the compound 1 synthesized in Synthesis Example 7 was used as a host and doped with 7 wt % of PhGD as a dopant to form a The ratios are described for the following examples and comparative examples. Subsequently, compound C is deposited on the light-emitting layer to form The thick electron transport auxiliary layer is formed by vacuum depositing compound D and LiQ at a weight ratio of 1:1 simultaneously. On the electron transport layer, vacuum deposition is performed in sequence. LiQ and Al is used to form a cathode to manufacture an organic light emitting diode.

[0806] The organic light emitting diode manufactured has the following structure: ITO / compound A (3% NDP-9 doping, ) / Compound A( ) / Compound B( ) / EML[Compound 1 (93wt%):PhGD (7wt%)]( ) / Compound C( ) / Compound D:LiQ( ) / LiQ( ) / Al( ).

[0807] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0808] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0809] Compound C: 2,4-diphenyl-6-(4',5',6'-triphenyl[1,1':2',1":3",1"':3"',1""-pentaphenyl]-3""-yl)-1,3,5-triazine

[0810] Compound D: 2-(1,1'-biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0811] [PhGD]

[0812]

[0813] Examples 2 to 18 and Comparative Examples 1 to 7

[0814] Each organic light emitting diode was manufactured in the same manner as in Example 1, except that the composition was changed as described in Table 1.

[0815] Embodiment 19

[0816] A glass substrate coated with an ITO (indium tin oxide) thin film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned by using oxygen plasma for 10 minutes, and moved to a vacuum depositor. The ITO transparent electrode thus prepared was used as an anode, and Compound A (Novaled GmbH) doped with 3% NDP-9 was vacuum deposited on the ITO substrate to form A hole injection layer is formed on the hole injection layer to a thickness of Compound E is deposited on the hole transport layer to a thickness of On the hole transport auxiliary layer, the compound 1 of Synthesis Example 7 and the compound B-136 of Synthesis Example 86 were used as the host at the same time, and 10 wt % of PhGD was doped as a dopant to form a hole transport auxiliary layer by vacuum deposition. Here, compound 1 and compound B-136 are used in a weight ratio of 3:7. Subsequently, compound F is deposited on the light-emitting layer to form A thick electron transport auxiliary layer is formed thereon by simultaneously vacuum depositing compound G and LiQ in a weight ratio of 1:1 On the electron transport layer, vacuum deposition is performed in sequence. LiQ and Al is used to form a cathode to manufacture an organic light emitting diode.

[0817] The organic light emitting diode manufactured has the following structure: ITO / compound A (3% NDP-9 doping, ) / Compound A( ) / Compound E( ) / EML[{host=compound 1:compound B-136:dopant=PhGD}=27:63:10 (wt%)]( ) / Compound F( ) / Compound G:LiQ( ) / LiQ( ) / Al( ).

[0818] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0819] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0820] Compound F: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0821] Compound G: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0822] Examples 20 to 42 and Comparative Examples 8 to 14

[0823] Each organic light emitting diode was manufactured in the same manner as in Example 19, except that the composition was changed to each composition shown in Table 2.

[0824] evaluate

[0825] The organic light emitting diodes of Examples 1 to 42 and Comparative Examples 1 to 14 were evaluated with respect to driving voltage, luminous efficiency, and lifespan characteristics.

[0826] The specific measurement method is as follows, and the results are shown in Tables 1 and 2.

[0827] (1) Measuring the change in current density due to voltage change

[0828] While increasing the voltage from 0 V to 10 V, a current flowing through a unit device in the manufactured organic light emitting diode was measured by using a current-voltage meter (Keithley 2400), and the measured current value was divided by the area to provide a result.

[0829] (2) Measuring the change in brightness due to voltage changes

[0830] While increasing the voltage of the organic light emitting diode from 0 V to 10 V, the luminance was measured using a luminance meter (Minolta Cs-1000A).

[0831] (3) Measurement of luminous efficiency

[0832] The luminance and current density measured in (1) and (2) are used to calculate the current density (10 mA / cm 2 ) under current efficiency (cd / A).

[0833] The luminous efficiency values ​​of Examples 1 to 18 and Comparative Examples 1 to 7 were calculated based on Comparative Example 1 as relative values ​​and are shown in Table 1.

[0834] The luminous efficiency values ​​of Examples 19 to 42 and Comparative Examples 8 to 14 were calculated based on Comparative Example 8 as relative values ​​and are shown in Table 2.

[0835] (4) Measurement life

[0836] In the case of brightness (cd / m 2 ) maintained at 24000cd / m 2 At the same time, the results were obtained by measuring the time when the current efficiency (cd / A) dropped to 97%.

[0837] The life measurement values ​​of Examples 1 to 18 and Comparative Examples 1 to 7 were calculated based on Comparative Example 1 as relative values ​​and are shown in Table 1.

[0838] The life measurement values ​​of Examples 19 to 42 and Comparative Examples 8 to 14 were calculated based on Comparative Example 8 as relative values ​​and are shown in Table 2.

[0839] (5) Measure the driving voltage

[0840] The current was measured by using a current-voltage meter (Keithley 2400) at 15 mA / cm 2 The results were obtained for each device at a driving voltage.

[0841] The driving voltages of Examples 1 to 18 and Comparative Examples 1 to 7 were calculated based on Comparative Example 1 as relative values ​​and are shown in Table 1.

[0842] The driving voltages of Examples 19 to 42 and Comparative Examples 8 to 14 were calculated based on Comparative Example 8 as relative values ​​and are shown in Table 2.

[0843] [Table 1]

[0844]

[0845]

[0846] [Table 2]

[0847]

[0848]

[0849] Referring to Table 1 and Table 2, the organic light emitting diodes according to Examples 1 to 42 showed significantly improved driving voltage, luminous efficiency, and lifespan characteristics compared to the organic light emitting diodes according to Comparative Examples 1 to 14.

[0850] The life span of "0%" indicates that the organic light emitting diode is suddenly turned off, and the current efficiency (cd / A) is rapidly reduced to 97%.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1: [Chemical formula 1] In Chemical Formula 1, X 1 and X 2 Each independently is O, S or SiR a R b , Z 1 To Z 3 Each independently is N or CR c , Z 1 To Z 3 At least one of them is N, R a , R b , R c and R 1 To R 7 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C2 to C20 heterocyclic, R 4 To R 7 Each exists independently, or adjacent groups are linked to form a substituted or unsubstituted aromatic monocyclic ring or a substituted or unsubstituted aromatic polycyclic ring, Ar 1 is a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C20 heterocyclic group, L 1 To L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m1, m4, m5 and m6 are each independently one of integers from 1 to 3, and m2, m3 and m7 are each independently one of integers from 1 to 4.

2. The compound for an organic optoelectronic device according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formula 1-1 to Chemical Formula 1-4: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] [Chemical formula 1-4] In Chemical Formula 1-1 to Chemical Formula 1-4, 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 the same as defined in claim 1.

3. The compound for an organic optoelectronic device according to claim 2, wherein Chemical formula 1-1 is represented by any one of Chemical formula 1-1-(i), Chemical formula 1-1-(ii), Chemical formula 1-1-(iii), and Chemical formula 1-1-(iv): [Chemical formula 1-1-(i)] [Chemical formula 1-1-(ii)] [Chemical formula 1-1-(iii)] [Chemical formula 1-1-(iv)] In Chemical Formula 1-1-(i), Chemical Formula 1-1-(ii), Chemical Formula 1-1-(iii) and Chemical Formula 1-1-(iv), 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 the same as defined in claim 1.

4. The compound for an organic optoelectronic device according to claim 2, wherein Chemical formula 1-4 is represented by any one of Chemical formula 1-4-(i) to Chemical formula 1-4-(iv): [Chemical formula 1-4-(i)] [Chemical formula 1-4-(ii)] [Chemical formula 1-4-(iii)] [Chemical formula 1-4-(iv)] In Chemical Formula 1-4-(i), Chemical Formula 1-4-(ii), Chemical Formula 1-4-(iii) and Chemical Formula 1-4-(iv), 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 the same as defined in claim 1.

5. The compound for an organic optoelectronic device according to claim 1, In Chemical Formula 1, Ar 1 It is 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 dibenzosilyl group or a substituted or unsubstituted carbazolyl group.

6. The compound for an organic optoelectronic device according to claim 1, wherein The compound is selected from the compounds listed in Group 1: [Group 1] 7. A composition for an organic optoelectronic device, comprising: a first compound and a second compound, in, The first compound is the compound for an organic optoelectronic device according to claim 1, and The second compound is represented by Chemical Formula 2 or a combination of Chemical Formula 3 and Chemical Formula 4: [Chemical formula 2] In chemical formula 2, R 9 To R 13 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, 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, L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, m9, m12 and m13 are each independently one of integers from 1 to 4, m10 and m11 are each independently one of integers from 1 to 3, and n is an integer from 0 to 2; In Chemical Formula 3 and Chemical Formula 4, a1* to a4* in Chemical Formula 3 are each independently a connecting carbon (C) or CL a -R d , among a1* to a4* in Chemical Formula 3, two adjacent ones are each connected to * in Chemical Formula 4, L a , L 7 and L 8 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R d , R 14 and R 15 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic, Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and m14 and m15 are each independently one of integers from 1 to 4.

8. The composition for an organic optoelectronic device according to claim 7, wherein: Chemical formula 2 is represented by Chemical formula 2-8: [Chemical formula 2-8] In Chemical Formula 2-8, R 9 To R 12 are each independently hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, m9 and m12 are each independently an integer from 1 to 4, m10 and m11 are each independently one of integers from 1 to 3, and *-L 5 -Ar 2 and *-L 6 -Ar 3 Each is independently one of the substituents listed in Group I, [Group I] In Group I, R 16 To R 20 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl, m16 is an integer from 1 to 5, m17 is an integer from 1 to 4, m18 is an integer from 1 to 3, m19 is an integer of 1 or 2. m20 is an integer from 1 to 7, and * is the connection point.

9. The composition for an organic optoelectronic device according to claim 7, wherein: The combination of Chemical Formula 3 and Chemical Formula 4 is represented by Chemical Formula 3C: [Chemical formula 3C] In chemical formula 3C, L a3 and L a4 is a single key, R 9 , R 10 , R d3 and R d4 are each independently hydrogen, deuterium or C6 to C12 aryl, m14 and m15 are each independently an integer from 1 to 4, *-L 7 -Ar 4 and *-L 8 -Ar 5 are each independently selected from the substituents listed in Group I, [Group I] In Group I, R 13 To R 17 are each independently hydrogen, deuterium, cyano, C1 to C10 alkyl or C6 to C12 aryl, m13 is an integer from 1 to 5, m14 is an integer from 1 to 4, m15 is an integer from 1 to 3, m16 is an integer of 1 or 2. m17 is an integer from 1 to 7, and * is the connection point.

10. An organic optoelectronic device, comprising: an anode and a cathode facing each other, and at least one organic layer between the anode and the cathode, wherein the organic layer comprises the compound for an organic optoelectronic device according to any one of claims 1 to 6; or The composition for an organic optoelectronic device according to any one of claims 7 to 11.

11. The organic optoelectronic device according to claim 10, wherein: The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic optoelectronic device or the composition for an organic optoelectronic device. 12 . A display device comprising the organic optoelectronic device according to claim 10 .

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