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, the compound being represented by Chemical Formula 1 or Chemical Formula 2; an organic optoelectronic device and a display device including the same. Chemical formula 1 and chemical formula 2 are as defined in the specification.

Description

Technical Field

[0001] Compounds for organic optoelectronic devices, compositions for organic optoelectronic devices, organic optoelectronic devices, and display devices are disclosed. Background Art

[0002] An organic optoelectronic device (organic optoelectronic diode) is a device capable of converting electrical energy and light energy into each other.

[0003] According to the working principle, organic optoelectronic devices can be roughly divided into two categories. 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, and the other is a light-emitting device that generates light energy from electrical energy by applying a voltage or current to the electrodes.

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

[0005] Among them, due to the increasing demand for flat panel display devices, organic light-emitting diodes (OLEDs) have attracted much attention in recent years. An organic light-emitting diode is a device that converts electrical energy into light, and the performance of an organic light-emitting diode is greatly affected by the organic materials between the electrodes. Summary of the Invention

[0006] Technical Problem

[0007] One embodiment provides a compound for an organic optoelectronic device that achieves high efficiency and long life for an organic optoelectronic device.

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

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

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

[0011] Technical Solution

[0012] According to one embodiment, a compound for an organic optoelectronic device represented by Chemical Formula 1 or Chemical Formula 2 is provided.

[0013] [Chemical Formula 1]

[0014]

[0015] [Chemical Formula 2]

[0016]

[0017] In Chemical Formula 1 and Chemical Formula 2,

[0018] X 1 and X 2 are each independently O, S or SiR a R b ,

[0019] Z 1 to Z 3 are each independently N or CR c ,

[0020] Z 1 to Z 3 at least one of which is N,

[0021] R a 、R b 、R c and R 1 to R 9 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkylsilyl or substituted or unsubstituted C6-C12 aryl,

[0022] Ar 1 and Ar 2 are each independently substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heterocyclic group,

[0023] L 1 to L 4 are each independently a single bond or substituted or unsubstituted C6-C20 arylene,

[0024] m1, m2 and m4 are each independently one of the integers from 1 to 4, and

[0025] m3 is one of the integers from 1 to 3.

[0026] According to another embodiment, there is provided a composition for an organic optoelectronic device comprising a first compound and a second compound.

[0027] The first compound may be the compound for an organic optoelectronic device as described above, and the second compound may be represented by Chemical Formula 3 or a combination of Chemical Formula 4 and Chemical Formula 5.

[0028] [Chemical Formula 3]

[0029]

[0030] In Chemical Formula 3,

[0031] R 10 to R14 Each independently is hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C2-C30 heterocyclic group,

[0032] Ar 3 and Ar 4 Each independently is substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C30 heterocyclic group,

[0033] L 5 and L 6 Each independently is a single bond or substituted or unsubstituted C6-C20 arylene,

[0034] m10, m13 and m14 are each independently one of the integers from 1 to 4,

[0035] m11 and m12 are each independently one of the integers from 1 to 3, and

[0036] n is one of the integers from 0 to 2;

[0037]

[0038] In Chemical Formula 4 and Chemical Formula 5,

[0039] a1* to a4* in Chemical Formula 4 each independently is a bond to carbon (C) or C-L a -R d ,

[0040] In a1* to a4* of Chemical Formula 4, two adjacent ones are each bonded to * in Chemical Formula 5, L a 、L 7 and L 8 Each independently is a single bond or substituted or unsubstituted C6-C20 arylene,

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

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

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

[0044] 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 contains the compound for an organic optoelectronic device described above.

[0045] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0046] Advantageous Effects

[0047] An organic optoelectronic device with high efficiency and long lifetime can be achieved. Description of the Drawings

[0048] Figure 1 is a cross-sectional view showing an organic light-emitting diode according to one embodiment.

[0049] <Description of the Reference Numerals>

[0050] 100: Organic light-emitting diode

[0051] 105: Organic layer

[0052] 110: Cathode

[0053] 120: Anode

[0054] 130: Light-emitting layer

[0055] 140: Hole transport region

[0056] 150: Electron transport region Detailed Description of the Embodiments

[0057] Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary and the present disclosure is not limited thereto.

[0058] In the present specification, when no definition is provided otherwise, "substituted" means that at least one hydrogen of a substituent or a compound is replaced with the following: deuterium, halogen, hydroxyl group, amino group, substituted or unsubstituted C1-C30 amino group, nitro group, substituted or unsubstituted C1-C40 silyl group, C1-C30 alkyl group, C1-C10 alkylsilyl group, C6-C30 arylsilyl group, C3-C30 cycloalkyl group, C3-C30 heterocycloalkyl group, C6-C30 aryl group, C2-C30 heteroaryl group, C1-C20 alkoxy group, C1-C10 trifluoroalkyl group, cyano group, or a combination thereof.

[0059] In one example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, C1-C30 alkyl, C1-C10 alkylsilyl, C6-C30 arylsilyl, C3-C30 cycloalkyl, C3-C30 heterocycloalkyl, C6-C30 aryl, C2-C30 heteroaryl, or cyano. In one specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, C1-C20 alkyl, C6-C30 aryl, or cyano. In one specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, C1-C5 alkyl, C6-C18 aryl, or cyano. In one specific example of the present invention, "substituted" means that at least one hydrogen of a substituent or a compound is replaced by the following: deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0060] In this specification, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom is retained.

[0061] In this specification, "hydrogen substitution (-H)" may include "deuterium substitution (-D)" or "tritium substitution (-T)".

[0062] In this specification, when no other definition is provided, "hetero" means including one to three heteroatoms selected from N, O, S, P, and Si and the remaining carbon in a functional group.

[0063] In this specification, "aryl" means a group including at least one hydrocarbon aromatic moiety, and all elements of the hydrocarbon aromatic moiety have p orbitals forming conjugation, such as phenyl, naphthyl, etc. Two or more hydrocarbon aromatic moieties may be connected by a σ bond and may be, for example, biphenyl, terphenyl, quaterphenyl, etc., and two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl.

[0064] Aryl may include monocyclic, polycyclic, or fused polycyclic (i.e., rings sharing adjacent carbon atom pairs) functional groups.

[0065] As used herein, "heterocyclic group" is a superordinate concept of heteroaryl and may include at least one heteroatom selected from N, O, S, P, and Si in a cyclic compound instead of carbon (C), such as aryl, cycloalkyl, their fused rings, or their combinations. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may include one or more heteroatoms.

[0066] 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 heteroaryl groups are directly connected by a σ bond, or when a 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.

[0067] More specifically, the substituted or unsubstituted C6-C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzophenanthryl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but not limited thereto.

[0068] More specifically, the substituted or unsubstituted C2-C30 heterocyclic group may be a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted benzonaphthofuryl group, a substituted or unsubstituted benzonaphthothienyl group, a substituted or unsubstituted benzofurofluorene group, a substituted or unsubstituted benzothienofluorene group, or a combination thereof, but not limited thereto.

[0069] In this specification, the hole property refers to the ability to provide electrons to form holes when an electric field is applied, and due to the conductive property 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.

[0070] In addition, the electron property refers to the ability to accept electrons when an electric field is applied, and due to the conductive property according to the lowest unoccupied molecular orbital (LUMO) energy level, the electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0071] Hereinafter, a compound for an organic optoelectronic device according to an embodiment is described.

[0072] The compound for an organic optoelectronic device according to an embodiment is represented by Chemical Formula 1 or Chemical Formula 2.

[0073] [Chemical Formula 1]

[0074]

[0075] [Chemical Formula 2]

[0076]

[0077] In Chemical Formula 1 and Chemical Formula 2,

[0078] X 1 and X 2 are each independently O, S, or SiR a R b , Z 1 to Z 3 are each independently N or CR c ,

[0079] Z 1 to Z 3 at least one of them is N,

[0080] R a , R b , R c and R 1 to R 9 are each independently hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkylsilyl, or substituted or unsubstituted C6-C12 aryl,

[0081] Ar 1 and Ar 2 are each independently substituted or unsubstituted C6-C20 aryl or substituted or unsubstituted C2-C20 heterocyclic group,

[0082] L 1 to L 4 are each independently a single bond or substituted or unsubstituted C6-C20 arylene,

[0083] m1, m2, and m4 are each independently one of the integers from 1 to 4, and

[0084] m3 is one of the integers from 1 to 3.

[0085] The compound represented by Chemical Formula 1 has a structure in which a nitrogen-containing 6-membered ring is substituted at the 1-position or 2-position of the dibenzofuran derivative, a 9-carbazolyl group is substituted at the 2-position or 1-position, and another dibenzofuran derivative is substituted at the 9-position.

[0086] In the present specification, the term "dibenzofuran derivative" is defined to include dibenzofuran, dibenzothiophene, and dibenzosilole.

[0087] The compound represented by Chemical Formula 1 can achieve electron delocalization by including a nitrogen-containing 6-membered ring at the 1-position or 2-position, thereby improving the charge mobility. Therefore, the hole transport characteristics can be further improved, and thus the low driving and high efficiency performance of the organic optoelectronic device including the compound can be achieved.

[0088] In addition, by introducing another dibenzofuran derivative at the 9-position, the electron delocalization is further extended and steric hindrance is provided, resulting in a low deposition temperature, and thus the lifetime characteristics of the organic light-emitting diode including the same can be significantly improved.

[0089] Meanwhile, due to the extension of the electron delocalization, the stability of the molecule can be reduced, but by simultaneously substituting the benzene ring substituted with the nitrogen-containing 6-membered ring with a 9-carbazolyl group, the deterioration of the triazine caused by the electron delocalization can be prevented, thereby improving the deterioration of the lifetime characteristics.

[0090] In Chemical Formula 1 and Chemical Formula 2, when m1 is 2 or greater, R 6 may be the same as or different from each other.

[0091] In Chemical Formula 1 and Chemical Formula 2, when m2 is 2 or greater, R 7 may be the same as or different from each other.

[0092] In Chemical Formula 1 and Chemical Formula 2, when m3 is 2 or greater, R 8 may be the same as or different from each other.

[0093] In Chemical Formula 1 and Chemical Formula 2, when m4 is 2 or greater, R 9 may be the same as or different from each other.

[0094] For example, Chemical Formula 1 may be represented by any one of Chemical Formulas 1-1 to 1-4.

[0095] [Chemical Formula 1-1]

[0096]

[0097] [Chemical formula 1-2]

[0098]

[0099] [Chemical formula 1-3]

[0100]

[0101] [Chemical formula 1-4]

[0102]

[0103] In Chemical formulas 1-1 to 1-4,

[0104] X 1 、X 2 、Z 1 to Z 3 、R 1 to R 9 、Ar 1 to Ar 4 、L 1 to L 4 and m1 to m4 are the same as above.

[0105] Chemical formula 2 can be represented by any one of Chemical formulas 2-1 to 2-4.

[0106] [Chemical formula 2-1]

[0107]

[0108] [Chemical formula 2-2]

[0109]

[0110] [Chemical formula 2-3]

[0111]

[0112] [Chemical formula 2-4]

[0113]

[0114] In Chemical formulas 2-1 to 2-4,

[0115] 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 above.

[0116] The compound for an organic optoelectronic device according to an embodiment of the present invention may be represented by any one of Chemical Formula 1-1, Chemical Formula 1-4, Chemical Formula 2-1, and Chemical Formula 2-4.

[0117] The compound for an organic optoelectronic device according to a specific embodiment of the present invention may be represented by any one of Chemical Formula 1-1, Chemical Formula 1-4, and Chemical Formula 2-1.

[0118] For example, L 1 and L 2 may each independently be a single bond or a substituted or unsubstituted phenylene group.

[0119] As a specific example, L 1 and L 2 may each be a single bond.

[0120] For example, Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a substituted or unsubstituted carbazolyl group.

[0121] As a specific example, Ar 1 and Ar 2 may each independently be a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.

[0122] For example, R 1 to R 9 may each independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1-C5 alkylsilyl group, or a substituted or unsubstituted C6-C12 aryl group.

[0123] As a specific example, R 1 to R 9 may each independently be hydrogen, deuterium, a cyano group, trimethylsilyl, a substituted or unsubstituted phenyl group, or a substituted or unsubstituted biphenyl group.

[0124] For example, L 3 and L 4 in Chemical Formula 1 may each independently be a single bond or a substituted or unsubstituted C6-C12 arylene group.

[0125] For example, L 3 and L 4 in Chemical Formula 1 may each independently be a single bond or a substituted or unsubstituted phenylene group.

[0126] For example, Z1 from Z 3 at least two of which may be N.

[0127] For example, Z 1 to Z 3 may each be N.

[0128] For example, R a and R b may each independently be a substituted or unsubstituted C1 - C10 alkyl group or a substituted or unsubstituted C6 - C12 aryl group.

[0129] In a specific embodiment, the compound represented by Chemical Formula 1 or Chemical Formula 2 may be one of the compounds listed in Group 1, but is not limited thereto.

[0130] [Group 1]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140] The composition for an organic optoelectronic device according to another embodiment includes a first compound and a second compound, wherein the first compound may be the compound for an organic optoelectronic device as described above, and the second compound may be represented by Chemical Formula 3 or by a combination of Chemical Formula 4 and Chemical Formula 5.

[0141] [Chemical Formula 3]

[0142]

[0143] In Chemical Formula 3,

[0144] R 10 to R 14Each is independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group,

[0145] Ar 3 and Ar 4 Each is independently a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group,

[0146] L 5 and L 6 Each is independently a single bond or a substituted or unsubstituted C6-C20 arylene group,

[0147] m10, m13, and m14 are each independently one of the integers from 1 to 4,

[0148] m11 and m12 are each independently one of the integers from 1 to 3, and

[0149] n is one of the integers from 0 to 2;

[0150]

[0151] In Chemical Formulas 4 and 5,

[0152] a1* to a4* in Chemical Formula 4 are each independently a bond to carbon (C) or C-L a -R d ,

[0153] In a1* to a4* of Chemical Formula 4, two adjacent ones are each bonded to * in Chemical Formula 5, L a 、L 7 and L 8 Each is independently a single bond or a substituted or unsubstituted C6-C20 arylene group,

[0154] R d 、R 15 and R 16 Each is independently hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group,

[0155] Ar 5 and Ar 6 Each is independently a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, and

[0156] m15 and m16 are each independently one of the integers from 1 to 4.

[0157] The second compound can be used together with the first compound in a light-emitting layer to improve the light-emitting efficiency and lifetime characteristics by enhancing the charge mobility and stability.

[0158] In Chemical Formula 3, m10 is 2 or greater, and R 10 may each be the same as or different from one another.

[0159] In Chemical Formula 3, m11 is 2 or greater, and R 11 may each be the same as or different from one another.

[0160] In Chemical Formula 3, m12 is 2 or greater, and R 12 may each be the same as or different from one another.

[0161] In Chemical Formula 3, m13 is 2 or greater, and R 13 may each be the same as or different from one another.

[0162] In Chemical Formula 3, m14 is 2 or greater, and R 14 may each be the same as or different from one another.

[0163] As an example, in Chemical Formula 3, Ar 3 and Ar 4 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 terphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0164] In Chemical Formula 3, 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.

[0165] In Chemical Formula 3, R 10 to R 14 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0166] n may be 0 or 1.

[0167] As an example, in Chemical Formula 3, "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.

[0168] For example, in Chemical Formula 3, Ar 3 and Ar 4Each may independently 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.

[0169] In a specific embodiment of the present invention, Formula 3 may be represented by any one of Formula 3-1 to Formula 3-15.

[0170]

[0171]

[0172] In Formulas 3-1 to 3-15, R 9 to R 13 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6-C12 aryl group, and L 5 -Ar 3 and L 6 -Ar 4 may each independently be one of the substituents listed in Group II.

[0173] [Group II]

[0174]

[0175] In Group II,

[0176] R 17 to R 21 are each independently hydrogen, deuterium, cyano, a C1-C10 alkyl group, or a C6-C12 aryl group,

[0177] m17 is one of the integers from 1 to 5,

[0178] m18 is one of the integers from 1 to 4,

[0179] m19 is one of the integers from 1 to 3,

[0180] m20 is an integer of 1 or 2,

[0181] m21 is one of the integers from 1 to 7, and

[0182] * is a connection point.

[0183] In Group II, when m17 is 2 or greater, R 17 may each be the same as or different from each other.

[0184] In Group II, when m18 is 2 or greater, R 18 may each be the same as or different from each other.

[0185] In Group II, when m19 is 2 or greater, R 19Each may be the same as or different from each other.

[0186] In Group II, when m20 is 2, R 20 Each may be the same as or different from each other.

[0187] In Group II, when m21 is 2 or greater, R 21 Each may be the same as or different from each other.

[0188] In Chemical Formula 4 and Chemical Formula 5, when m15 is 2 or more, R 15 Each may be the same as or different from each other.

[0189] In Chemical Formula 4 and Chemical Formula 5, when m16 is 2 or more, R 16 Each may be the same as or different from each other.

[0190] The second compound may be represented, for example, by one of Chemical Formula 4A, Chemical Formula 4B, Chemical Formula 4C, Chemical Formula 4D, and Chemical Formula 4E.

[0191]

[0192] In Chemical Formulae 4A to 4E, L 7 , L 8 ,Ar 5 ,Ar 6 , R 15 and R 16 Same as above,

[0193] L a1 To L a4 With L 7 and L 8 The definition of is the same as

[0194] R d1 To R d4 With R 15 and R 16 The definition is the same.

[0195] For example, in Chemical Formula 4 and Chemical Formula 5, Ar 5 and Ar 6 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

[0196] R d1 To R d4 , R 15 and R16 may each independently be hydrogen, deuterium, cyano, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

[0197] In a specific embodiment of the present invention, in Chemical Formulas 4 and 5, L 7 -Ar 5 and L 8 -Ar 6 may each independently be selected from the substituents listed in Group II.

[0198] In one embodiment, R d1 to R d4 , R 15 and R 16 may each independently be hydrogen, deuterium, cyano, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

[0199] For example, R d1 to R d4 , R 15 and R 16 may each independently be hydrogen, deuterium, cyano, or a substituted or unsubstituted phenyl, and

[0200] In one embodiment, R d1 to R d4 , R 15 and R 16 may each independently be hydrogen, deuterium, or a substituted or unsubstituted phenyl.

[0201] In a specific embodiment of the present invention, the second compound may be represented by Chemical Formula 3-8, and in Chemical Formula 3-8, Ar 3 and Ar 4 may each independently be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl, L 5 and L 6 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and R 10 to R 13Each 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.

[0202] For example, in Chemical Formula 3-8, R 10 to R 13 may each independently be hydrogen, deuterium, or substituted or unsubstituted C6-C12 aryl, and L 5 -Ar 3 and L 6 -Ar 4 may each independently be one of the substituents listed in Group II.

[0203] In a specific embodiment of the present invention, the second compound may be represented by Chemical Formula 4C, and in Chemical Formula 4C, L a3 and L a4 may be a single bond, L 7 and L 8 may each independently be a single bond or substituted or unsubstituted C6-C12 arylene, R 15 , R 16 , R d3 and R d4 may each be hydrogen, deuterium, or phenyl, and Ar 5 and Ar 6 may each independently be 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.

[0204] For example, in Chemical Formula 4C, L c3 and L c4 may be a single bond, R 15 , R 16 , R d3 and R d4 may each independently be hydrogen, deuterium, or C6-C12 aryl, and L 7 -Ar 5 and L 8 -Ar 6 may each independently be one of the substituents listed in Group II.

[0205] For example, the second organic optoelectronic device compound may be one of the compounds listed in Group 2, but is not limited thereto.

[0206] [Group 2]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214] In addition, examples are given below of at least one hydrogen in compounds B-1 to B-155 listed in Group 2 being replaced by deuterium, but are not limited thereto.

[0215]

[0216]

[0217] (Dn refers to the number of deuterium substitutions and represents a structure substituted by one or more deuteriums).

[0218] According to the position and substitution rate of deuterium substitution, the most specific structures of compounds B-153 to B-197 in Group 2 are presented below as examples, and the structures are not intended to limit the scope of the claims to compounds not listed below.

[0219] The scope of the present invention is determined by the claims, and when substituted with deuterium, it is not limited to the compounds illustrated below, and the deuterium substitution position, deuterium substitution rate, etc. may include all variable ranges within the scope of compounds B-1 to B-197.

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226] In addition, examples are given below of at least one hydrogen in compounds C-1 to C-57 listed in Group 2 being replaced by deuterium, but are not limited thereto.

[0227]

[0228]

[0229] (Dn refers to the number of deuterium substitutions and represents a structure substituted with one or more deuteriums).

[0230] According to the position and substitution rate of deuterium substitution, the most specific structures of Compounds C-58 to C-72 of Group 2 are presented below as examples, and these structures are not intended to limit the scope of the claims to compounds not listed below.

[0231] The scope of the present invention is determined by the claims, and when substituted with deuterium, it is not limited to the compounds illustrated below, and the deuterium substitution position, deuterium substitution rate, etc. may include all variable ranges within the range of Compounds C-58 to C-72.

[0232]

[0233]

[0234]

[0235] For example, the first compound and the second compound may be included in a weight ratio of 1:99 to 99:1. Within the above range, by utilizing the electron transport ability of the first compound and the hole transport ability of the second compound, bipolar characteristics can be achieved by adjusting an appropriate weight ratio, thereby improving efficiency and lifetime. Within the above range, they may be included, for example, 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.

[0236] In addition to the first compound and the second compound, one or more additional compounds may also be included.

[0237] The compound for an organic optoelectronic device or the composition for an organic optoelectronic device may be a composition further comprising a dopant.

[0238] 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.

[0239] The dopant is a material that is mixed in a small amount with the compound or composition for an organic optoelectronic device to cause luminescence, and is generally a material such as a metal complex that emits light by being excited to a triplet state or more states multiple times. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0240] Examples of the dopant may be phosphorescent dopants, and examples of the phosphorescent dopants may be organometallic compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof. The phosphorescent dopant may be, for example, a compound represented by Chemical Formula Z, but is not limited thereto.

[0241] [Chemical Formula Z]

[0242] L 9 MX 3

[0243] In 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.

[0244] M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or combinations thereof, and L 9 and X 3 may be, for example, bidentate ligands.

[0245] Examples of the ligands represented by L 9 and X 3 may be selected from the chemical formulas listed in Group A, but are not limited thereto.

[0246] [Group A]

[0247]

[0248] In Group A,

[0249] R 300 to R 302 are each independently hydrogen, deuterium, a C1 to C30 alkyl group that is substituted or unsubstituted with a halogen, a C6 to C30 aryl group that is substituted or unsubstituted with a C1 to C30 alkyl group, or a halogen, and

[0250] R 303 to R 324Each independently is hydrogen, deuterium, a halogen, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C2-C30 alkenyl group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C1-C30 heteroaryl group, a substituted or unsubstituted C1-C30 amino group, a substituted or unsubstituted C6-C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1-C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1-C30 alkyl group and a C6-C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6-C30 aryl group.

[0251] In one embodiment, the dopant may be an iridium complex and may be represented by Chemical Formula 5-1 or Chemical Formula 5-2.

[0252] [Chemical Formula 5-1]

[0253]

[0254] In Chemical Formula 5-1,

[0255] R 101 to R 116 Each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 ,

[0256] R 132 to R 134 Each independently is a substituted or unsubstituted C1-C6 alkyl group,

[0257] R 101 to R 116 At least one of them is a functional group represented by Chemical Formula V-1,

[0258] L 100 is a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium through a lone pair of electrons of a carbon or heteroatom, and

[0259] m21 and m22 each independently is any one of integers from 0 to 3, and m21 + m22 is any one of integers from 1 to 3,

[0260] [Chemical Formula V-1]

[0261]

[0262] In Chemical Formula V-1,

[0263] R135 to R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 132 R 133 R 134 , and

[0264] * represents a moiety attached to a carbon atom.

[0265] [Chemical Formula 5-2]

[0266]

[0267] In Chemical Formula 5-2,

[0268] R 101 to R 117 are each independently hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group, or -SiR 133 R 134 R 135 ,

[0269] R 133 to R 135 are each independently a substituted or unsubstituted C1-C6 alkyl group,

[0270] L 100 is a bidentate ligand of a monovalent anion and is a ligand coordinated to iridium through a lone pair of electrons of a carbon or heteroatom, and

[0271] n1 and n2 are each independently any one of the integers from 0 to 3, and n1 + n2 is any one of the integers from 1 to 3.

[0272] In another embodiment, the dopant can be a platinum complex, for example, a platinum complex represented by Chemical Formula Z-1.

[0273] [Chemical Formula Z-1]

[0274]

[0275] In Chemical Formula Z-1, rings A, B, C, and D are each independently a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0276] R A , R B , R C and R D are each independently monosubstituted, disubstituted, trisubstituted, or tetrasubstituted or unsubstituted;

[0277] L B , L C and LD each independently a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' or a combination thereof,

[0278] When nA is 1, L E can be a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR' or a combination thereof; and when nA is 0, L E does not exist;

[0279] R A , R B , R C , R D R, R and R' are each independently hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino or a combination 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.

[0280] The platinum complex may be represented, for example, by Chemical Formula 6-1 or Chemical Formula 6-2.

[0281] [Chemical formula 6-1]

[0282]

[0283] [Chemical formula 6-2]

[0284]

[0285] In Chemical Formula 6-1 and Chemical Formula 6-2,

[0286] X 100 Selected from O, S and NR 132 ,

[0287] R 118 To R 132Each independently is hydrogen, deuterium, a substituted or unsubstituted C1-C10 alkyl group, a substituted or unsubstituted C6-C20 aryl group or -SiR 133 R 134 R 135 ,

[0288] R 133 to R 135 Each independently is a substituted or unsubstituted C1-C6 alkyl group,

[0289] R 118 to R 132 At least one of is -SiR 133 R 134 R 135 or tert-butyl, and

[0290] R 133 to R 135 Each independently is a substituted or unsubstituted C1-C6 alkyl group.

[0291] Hereinafter, an organic optoelectronic device including the above compound for an organic optoelectronic device or a composition for an organic optoelectronic device will be described.

[0292] The organic optoelectronic device can be a suitable device that converts electrical energy into light energy and vice versa, for example, an organic optoelectronic device, an organic light emitting diode, an organic solar cell or an organic photoreceptor drum.

[0293] Herein, with reference to the drawings, an organic light emitting diode as an example of an organic optoelectronic device is described.

[0294] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0295] With reference to Figure 1 , the organic light emitting diode 100 according to an 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.

[0296] The anode 120 can be made of a conductor having a large work function to assist hole injection, and can be, for example, a metal, a metal oxide and / or a conductive polymer. The anode 120 can be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, etc. or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.; 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-(ethylenedioxy)thiophene) (PEDOT), polypyrrole and polyaniline, but is not limited thereto.

[0297] The cathode 110 can be made of a conductor with a small work function to assist electron injection, and can be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 can 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 multi-layer structural material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but not limited thereto.

[0298] The organic layer 105 can contain the above compounds for organic optoelectronic devices or compositions for organic optoelectronic devices.

[0299] The organic layer 105 can include a light-emitting layer 130, and the light-emitting layer 130 can contain the above compounds for organic optoelectronic devices or compositions for organic optoelectronic devices.

[0300] The composition for organic optoelectronic devices further containing a dopant can be, for example, a green light-emitting composition.

[0301] The light-emitting layer 130 can contain, for example, each of the above compounds for organic optoelectronic devices as a phosphorescent host.

[0302] In addition to the light-emitting layer, the organic layer can further include a charge transport region.

[0303] The charge transport region can be, for example, a hole transport region 140.

[0304] The hole transport region 140 can further increase the hole injection and / or hole mobility between the anode 120 and the light-emitting layer 130 and block electrons.

[0305] Specifically, the hole transport region 140 can include a hole transport layer between the anode 120 and the light-emitting layer 130 and a hole transport assisting layer between the light-emitting layer 130 and the hole transport layer, and at least one of the hole transport layer and the hole transport assisting layer can include at least one of the compounds in Group B.

[0306] [Group B]

[0307]

[0308]

[0309]

[0310]

[0311]

[0312]

[0313] (Dn represents the number of deuterium substitutions and indicates a structure substituted with one or more deuteriums).

[0314] In the hole transport region 140, in addition to the above compounds, known compounds disclosed in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having a similar structure can also be used.

[0315] In addition, the charge transport region may be, for example, the electron transport region 150.

[0316] The electron transport region 150 can further increase the electron injection and / or electron mobility between the cathode 110 and the light-emitting layer 130 and block holes.

[0317] 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 electron transport layer and the electron transport auxiliary layer may include at least one of the compounds in Group C.

[0318] [Group C]

[0319]

[0320]

[0321]

[0322] One embodiment may be an organic light-emitting diode including a light-emitting layer as an organic layer.

[0323] Another embodiment may be an organic light-emitting diode including a light-emitting layer and a hole transport region as organic layers.

[0324] Another embodiment may be an organic light-emitting diode including a light-emitting layer and an electron transport region as organic layers.

[0325] As Figure 1 shown, 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 organic layers 105 in addition to the light-emitting layer 130.

[0326] On the other hand, in addition to the light-emitting layer, the organic light-emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. as organic layers.

[0327] An organic light-emitting diode 100 can be fabricated as follows: An anode or a cathode is formed on a substrate, and then an organic layer is formed by a dry film method (such as vacuum deposition, sputtering, plasma electroplating, and ion electroplating), and a cathode or an anode is formed thereon.

[0328] The above organic light-emitting diode can be applied to an organic light-emitting display device.

[0329] Hereinafter, the embodiments will be described in more detail with reference to the examples. However, these examples are illustrative, and the scope of the claims is not limited thereto.

[0330] Mode of the Invention

[0331] Hereinafter, starting materials and reactants used in the examples and synthesis examples are purchased from Sigma-Aldrich Co., Ltd., TCI Inc., Tokyo chemical industry, or P&H tech or synthesized by known methods unless otherwise specified.

[0332] Synthesis Example 1: Synthesis of Intermediate I-1

[0333]

[0334] In a nitrogen atmosphere, 2,6-dimethoxyphenylboronic acid (100 g, 550 mmol) was dissolved in 1 L of dioxane, and 2,3-dibromo-1,4-difluorobenzene (179 g, 659 mmol) and tetrakis(triphenylphosphine)palladium (12.7 g, 11.0 mmol) were added thereto, followed by stirring. Subsequently, a saturated aqueous solution of potassium carbonate (190 g, 1,375 mmol) was added thereto, and then the mixture was heated under reflux for 8 hours. When the reaction was completed, after adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain Intermediate I-1 (163 g, 90%).

[0335] HRMS (70 eV, EI+): Calculated m / z for C14H11BrF2O2: 327.9910, measured value: 327.

[0336] Elemental analysis: C, 51%; H, 3%.

[0337] Synthesis Example 2: Synthesis of Intermediate I-2

[0338]

[0339] In a nitrogen atmosphere, intermediate I-1 (160 g, 486 mmol) and pyridine hydrochloride (562 g, 4,861 mmol) were added thereto, and then the mixture was heated under reflux at 180 °C for 1 hour. When the reaction was completed, after adding water to the reaction solution, the mixture was extracted with ethyl acetate (EA), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-2 (139 g, 95%).

[0340] HRMS (70 eV, EI+): Calculated m / z for C12H7BrF2O2: 299.9597, Measured: 299.

[0341] Elemental analysis: C, 48%; H, 2%.

[0342] Synthesis Example 3: Synthesis of Intermediate I-3

[0343]

[0344] In a nitrogen atmosphere, intermediate I-2 (135 g, 448 mmol) was dissolved in 1.3 L of N,N-dimethylformamide (DMF), and tripotassium phosphate (190 g, 897 mmol) was added thereto, and then the mixture was heated under reflux at 180 °C for 3 hours. When the reaction was completed, after removing the solvent by distillation and adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-3 (101 g, 80%).

[0345] HRMS (70 eV, EI+): Calculated m / z for C12H6BrFO2: 279.9535, Measured: 279.

[0346] Elemental analysis: C, 51%; H, 2%.

[0347] Synthesis Example 4: Synthesis of Intermediate I-4

[0348]

[0349] In a nitrogen atmosphere, intermediate I-3 (100 g, 356 mmol) was dissolved in 0.1 L of dichloromethane (DCM), and then cooled to 180 °C. Subsequently, pyridine (120 g, 427 mmol) was added thereto, and then stirred for 30 minutes. Then, trifluoromethanesulfonic anhydride (33.8 g, 427 mmol) was slowly added thereto, and then stirred. After 3 hours, the reaction solution was cooled to 0 °C, and water was slowly added thereto within 30 minutes. Then, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-4 (144 g, 98%).

[0350] HRMS (70 eV, EI+): Calculated m / z for C13H5BrF4O4S: 411.9028, measured: 411.

[0351] Elemental analysis: C, 38%; H, 1%.

[0352] Synthesis Example 5: Synthesis of Intermediate I-5

[0353]

[0354] Intermediate I-5 (187 g, 78%) was obtained in the same manner as in Synthesis Example 1 by using intermediate I-4 (140 g, 339 mmol) and dibenzofuran-1-boronic acid (79.0 g, 373 mmol) purchased from Tokyo Chemical Industry Co., Ltd.

[0355] HRMS (70 eV, EI+): Calculated m / z for C24H12BrFO2: 430.0005, measured: 430.

[0356] Elemental analysis: C, 67%; H, 3%.

[0357] Synthesis Example 6: Synthesis of Intermediate I-6

[0358]

[0359] In a nitrogen atmosphere, intermediate I-5 (185 g, 429 mmol) was dissolved in 0.2 L of N-methyl-2-pyrrolidone (NMP), and 9H-carbazole (78.9 g, 472 mmol) and cesium carbonate (280 g, 858 mmol) were added thereto. Then, the mixture was heated under reflux for 5 hours. When the reaction was completed, after removing the solvent by distillation and adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove water, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-6 (151 g, 61%).

[0360] HRMS (70 eV, EI+): Calculated m / z for C36H20BrNO2: 577.0677, measured: 577.

[0361] Elemental analysis: C, 75%; H, 3%.

[0362] Synthesis Example 7: Synthesis of Intermediate I-7

[0363]

[0364] In a nitrogen atmosphere, intermediate I-6 (150 g, 259 mmol) was dissolved in 300 mL of tetrahydrofuran (THF), and then cooled to -78 °C. Subsequently, 2.5 M n-BuLi in hexane (124 mL, 311 mmol) was slowly added dropwise thereto within 10 minutes, and after 30 minutes, triisopropyl borate (58.5 g, 311 mmol) was added thereto. When the reaction was completed, 1 N HCl (311 mL, 311 mmol) was added thereto to neutralize the reaction solution. After extracting the neutralized reaction solution with ethyl acetate (EA) and removing water therefrom with anhydrous magnesium sulfate, impurities were washed off from the resulting residue with hexane and dichloromethane (DCM) to obtain intermediate I-7 (120 g, 85%).

[0365] HRMS (70 eV, EI+): Calculated m / z for C36H22BNO4: 543.1642, measured: 543.

[0366] Elemental analysis: C, 80%; H, 4%.

[0367] Synthesis Example 8: Synthesis of Compound 4

[0368]

[0369] Compound 4 (22.9 g, 85%) was obtained in the same manner as in Synthesis Example 1 by synthesizing intermediate I-7 (20 g, 36.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.85 g, 36.8 mmol) purchased from Tokyo Chemical Industry Co., Ltd.

[0370] HRMS (70 eV, EI+): Calculated m / z for C51H30N4O2: 730.2369, measured: 730.

[0371] Elemental analysis: C, 84%; H, 4%.

[0372] Synthesis Example 9: Synthesis of Intermediate I-8

[0373]

[0374] Intermediate I-8 (41.7 g, 80%) was obtained in the same manner as in Synthesis Example 1 by synthesizing intermediate I-4 (50 g, 121 mmol) and dibenzofuran-4-boronic acid (30.8 g, 145 mmol) purchased from Tokyo Chemical Industry Co., Ltd.

[0375] HRMS (70 eV, EI+): Calculated m / z for C24H12BrFO2: 430.0005, measured: 430.

[0376] Elemental analysis: C, 67%; H, 3%.

[0377] Synthesis Example 10: Synthesis of Intermediate I-9

[0378]

[0379] Intermediate I-9 (32.2 g, 60%) was obtained in the same manner as in Synthesis Example 6 by synthesizing intermediate I-8 (40 g, 92.8 mmol) and 9H-carbazole (17.1 g, 102 mmol).

[0380] HRMS (70 eV, EI+): Calculated m / z for C36H20BrNO2: 577.0677, measured: 577.

[0381] Elemental analysis: C, 75%; H, 3%.

[0382] Synthesis Example 11: Synthesis of Intermediate I-10

[0383]

[0384] Intermediate I-10 (25.4 g, 90%) was obtained in the same manner as in Synthesis Example 7 by synthesizing intermediate I-9 (30 g, 51.9 mmol).

[0385] HRMS (70 eV, EI+): Calculated m / z for C36H22BNO4: 543.1642, measured: 543.

[0386] Elemental analysis: C, 80%; H, 4%.

[0387] Synthesis Example 12: Synthesis of Compound 1

[0388]

[0389] Compound 1 (24.2 g, 90%) was obtained in the same manner as in Synthesis Example 1 by synthesizing intermediate I-10 (20 g, 36.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.85 g, 36.8 mmol).

[0390] HRMS (70 eV, EI+): Calculated m / z for C51H30N4O2: 730.2369, measured: 730.

[0391] Elemental analysis: C, 84%; H, 4%.

[0392] Synthesis Example 13: Synthesis of Intermediate I-11

[0393]

[0394] Intermediate I-11 (40.7 g, 78%) was obtained in the same manner as in Synthesis Example 1 by synthesizing intermediate I-4 (50 g, 121 mmol) and dibenzofuran-3-boronic acid (30.8 g, 145 mmol).

[0395] HRMS (70 eV, EI+): Calculated m / z for C24H12BrFO2: 430.0005, measured: 430.

[0396] Elemental analysis: C, 67%; H, 3%.

[0397] Synthesis Example 14: Synthesis of Intermediate I-12

[0398]

[0399] Intermediate I-12 (34.9 g, 65%) was obtained in the same manner as in Synthesis Example 6 by synthesizing intermediate I-11 (40 g, 92.8 mmol) and 9H-carbazole (17.1 g, 102 mmol).

[0400] HRMS (70eV, EI+): Calculated m / z for C36H20BrNO2: 577.0677, Measured: 577.

[0401] Elemental analysis: C, 75%; H, 3%.

[0402] Synthesis Example 15: Synthesis of Intermediate I-13

[0403]

[0404] Intermediate I-13 (22.8 g, 81%) was obtained in the same manner as in Synthesis Example 7 by synthesizing Intermediate I-12 (30 g, 51.9 mmol).

[0405] HRMS (70eV, EI+): Calculated m / z for C36H22BNO4: 543.1642, Measured: 543.

[0406] Elemental analysis: C, 80%; H, 4%.

[0407] Synthesis Example 16: Synthesis of Compound 2

[0408]

[0409] Compound 2 (22.6 g, 84%) was obtained in the same manner as in Synthesis Example 1 by synthesizing Intermediate I-13 (20 g, 36.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.85 g, 36.8 mmol).

[0410] HRMS (70eV, EI+): Calculated m / z for C51H30N4O2: 730.2369, Measured: 730.

[0411] Elemental analysis: C, 84%; H, 4%.

[0412] Synthesis Example 17: Synthesis of Intermediate I-14

[0413]

[0414] Intermediate I-14 (41.7 g, 80%) was obtained in the same manner as in Synthesis Example 1 by synthesizing Intermediate I-4 (50 g, 121 mmol) and dibenzofuran-2-boronic acid (30.8 g, 145 mmol).

[0415] HRMS (70eV, EI+): Calculated m / z for C24H12BrFO2: 430.0005, Measured: 430.

[0416] Elemental analysis: C, 67%; H, 3%.

[0417] Synthesis Example 18: Synthesis of Intermediate I-15

[0418]

[0419] Intermediate I-15 (30.1 g, 56%) was obtained in the same manner as in Synthesis Example 6 by synthesizing intermediate I-14 (40 g, 92.8 mmol) and 9H-carbazole (17.1 g, 102 mmol).

[0420] HRMS (70 eV, EI+): Calculated m / z for C36H20BrNO2: 577.0677, measured: 577.

[0421] Elemental analysis: C, 75%; H, 3%.

[0422] Synthesis Example 19: Synthesis of Intermediate I-16

[0423]

[0424] Intermediate I-16 (20.7 g, 88%) was obtained in the same manner as in Synthesis Example 7 by synthesizing intermediate I-15 (25 g, 43.2 mmol).

[0425] HRMS (70 eV, EI+): Calculated m / z for C36H22BNO4: 543.1642, measured: 543.

[0426] Elemental analysis: C, 80%; H, 4%.

[0427] Synthesis Example 20: Synthesis of Compound 3

[0428]

[0429] Compound 3 (21.5 g, 80%) was obtained in the same manner as in Synthesis Example 1 by synthesizing intermediate I-16 (20 g, 36.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.85 g, 36.8 mmol).

[0430] HRMS (70 eV, EI+): Calculated m / z for C51H30N4O2: 730.2369, measured: 730.

[0431] Elemental analysis: C, 84%; H, 4%.

[0432] Synthesis Example 21: Synthesis of Intermediate I-17

[0433]

[0434] Intermediate I-17 (49.8 g, 92%) was obtained in the same manner as in Synthesis Example 1 by synthesizing Intermediate I-4 (50 g, 121 mmol) and dibenzothiophene-4-boronic acid (33.1 g, 145 mmol) purchased from Tokyo Chemical Industry Co., Ltd.

[0435] HRMS (70 eV, EI+): Calculated m / z for C24H12BrFOS: 445.9776, Measured: 445.

[0436] Elemental analysis: C, 64%; H, 3%.

[0437] Synthesis Example 22: Synthesis of Intermediate I-18

[0438]

[0439] Intermediate I-18 (33.7 g, 53%) was obtained in the same manner as in Synthesis Example 6 by synthesizing Intermediate I-17 (48 g, 107 mmol) and 9H-carbazole (19.7 g, 118 mmol).

[0440] HRMS (70 eV, EI+): Calculated m / z for C36H20BrNOS: 593.0449, Measured: 593.

[0441] Elemental analysis: C, 73%; H, 3%.

[0442] Synthesis Example 23: Synthesis of Intermediate I-19

[0443]

[0444] Intermediate I-19 (26.2 g, 87%) was obtained in the same manner as in Synthesis Example 7 by synthesizing Intermediate I-18 (32 g, 53.8 mmol).

[0445] HRMS (70 eV, EI+): Calculated m / z for C36H22BNO3S: 559.1413, Measured: 559.

[0446] Elemental analysis: C, 77%; H, 4%.

[0447] Synthesis Example 24: Synthesis of Compound 5

[0448]

[0449] Compound 5 (23.5 g, 88%) was obtained in the same manner as in Synthesis Example 1 by synthesizing intermediate I-19 (20 g, 35.8 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.57 g, 35.8 mmol).

[0450] HRMS (70 eV, EI+): Calculated m / z for C51H30N4OS: 746.2140, Measured: 746.

[0451] Elemental analysis: C, 82%; H, 4%.

[0452] Synthesis Example 25: Synthesis of Intermediate I-20

[0453]

[0454] Intermediate I-20 (65.0 g, 52%) was obtained in the same manner as in Synthesis Example 1 by synthesizing 4-cyanophenylboronic acid (63 g, 427 mmol) and 2,4-dichloro-6-phenyl-1,3,5-triazine (145 g, 641 mmol).

[0455] HRMS (70 eV, EI+): Calculated m / z for C16H9ClN4: 292.0516, Measured: 292.

[0456] Elemental analysis: C, 66%; H, 3%.

[0457] Synthesis Example 26: Synthesis of Compound 54

[0458]

[0459] Compound 54 (25.0 g, 90%) was obtained in the same manner as in Synthesis Example 1 by synthesizing intermediate I-7 (20 g, 36.8 mmol) and intermediate I-20 (10.8 g, 36.8 mmol).

[0460] HRMS (70 eV, EI+): Calculated m / z for C52H29N5O2: 755.2321, Measured: 755.

[0461] Elemental analysis: C, 83%; H, 4%.

[0462] Synthesis Example 27: Synthesis of Compound 94

[0463]

[0464] Compound 94 (23.8 g, 80%) was obtained in the same manner as in Synthesis Example 1 by combining synthetic intermediate I-7 (20 g, 36.8 mmol) and 2-(biphenyl-4-yl)-4-chloro-6-phenyl-1,3,5-triazine (12.7 g, 36.8 mmol) purchased from Tokyo Chemical Industry Co., Ltd.

[0465] HRMS (70 eV, EI+): calculated m / z for C57H34N4O2: 806.2682, measured: 806.

[0466] Elemental analysis: C, 85%; H, 4%.

[0467] Synthesis Example 28: Synthesis of Intermediate I-21

[0468]

[0469] Intermediate I-21 (142 g, 91%) was obtained in the same manner as in Synthesis Example 1 by using 2,6-dimethoxyphenylboronic acid (100 g, 550 mmol) and 2-bromo-4-chloro-1,3-difluorobenzene (125 g, 550 mmol).

[0470] HRMS (70 eV, EI+): calculated m / z for C14H11ClF2O2: 284.0416, measured: 284.

[0471] Elemental analysis: C, 59%; H, 4%.

[0472] Synthesis Example 29: Synthesis of Intermediate I-22

[0473]

[0474] Intermediate I-22 (101 g, 80%) was obtained in the same manner as in Synthesis Example 2 by using intermediate I-21 (140 g, 492 mmol).

[0475] HRMS (70 eV, EI+): calculated m / z for C12H7ClF2O2: 256.0103, measured: 256.

[0476] Elemental analysis: C, 55%; H, 3%.

[0477] Synthesis Example 30: Synthesis of Intermediate I-23

[0478]

[0479] Intermediate I-23 (32.3 g, 35%) was obtained in the same manner as in Synthesis Example 3 by using Intermediate I-22 (100 g, 390 mmol).

[0480] HRMS (70 eV, EI+): Calculated m / z for C12H6ClFO2: 236.0040, measured: 236.

[0481] Elemental analysis: C, 61%; H, 3%.

[0482] Synthesis Example 31: Synthesis of Intermediate I-24

[0483]

[0484] Intermediate I-24 (43.5 g, 93%) was obtained in the same manner as in Synthesis Example 4 by using Intermediate I-23 (30 g, 127 mmol).

[0485] HRMS (70 eV, EI+): Calculated m / z for C13H5ClF4O4S: 367.9533, measured: 367.

[0486] Elemental analysis: C, 42%; H, 1%.

[0487] Synthesis Example 32: Synthesis of Intermediate I-25

[0488]

[0489] Intermediate I-25 (35.3 g, 80%) was obtained in the same manner as in Synthesis Example 1 by using Intermediate I-24 (42 g, 114 mmol) and dibenzofuran-1-boronic acid (26.6 g, 125 mmol).

[0490] HRMS (70 eV, EI+): Calculated m / z for C24H12ClFO2: 386.0510, measured: 386.

[0491] Elemental analysis: C, 75%; H, 3%.

[0492] Synthesis Example 33: Synthesis of Intermediate I-26

[0493]

[0494] In a nitrogen atmosphere, intermediate I-25 (34 g, 87.9 mmol) was dissolved in 0.4 L of xylene, and bis(pinacolato)diboron (26.8 g, 105 mmol), tris(dibenzylideneacetone)dipalladium(0) (2.41 g, 2.64 mmol), tricyclohexylphosphine (2.96 g, 10.5 mmol), and potassium acetate (25.9 g, 264 mmol) were added thereto. Then, the mixture was heated under reflux for 8 hours. When the reaction was completed, after adding water to the reaction solution, the mixture was extracted with dichloromethane (DCM), treated with anhydrous magnesium sulfate to remove moisture, filtered, and concentrated under reduced pressure. The resulting residue was separated and purified by flash column chromatography to obtain intermediate I-26 (18.9 g, 45%).

[0495] HRMS (70 eV, EI+): Calculated m / z for C30H24BFO4: 478.1752, Measured: 478.

[0496] Elemental analysis: C, 75%; H, 5%.

[0497] Synthesis Example 34: Synthesis of Intermediate I-27

[0498]

[0499] Intermediate I-27 (22.6 g, 84%) was obtained in the same manner as in Synthesis Example 1 by using intermediate I-26 (15 g, 31.4 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (8.40 g, 31.4 mmol).

[0500] HRMS (70 eV, EI+): Calculated m / z for C15H10ClN3: 267.0563, Measured: 267.

[0501] Elemental analysis: C, 67%; H, 4%.

[0502] Synthesis Example 35: Synthesis of Compound 102

[0503]

[0504] Compound 102 (12.5 g, 50%) was obtained in the same manner as in Synthesis Example 6 by using intermediate I-27 (20 g, 34.3 mmol) and 9H-carbazole (6.3 g, 37.7 mmol).

[0505] HRMS (70 eV, EI+): Calculated m / z for C51H30N4O2: 730.2369, Measured: 730.

[0506] Elemental analysis: C, 84%; H, 4%.

[0507] Synthesis Example 36: Synthesis of Compound 126

[0508]

[0509] Compound 126 (11.9 g, 43%) was obtained in the same manner as in Synthesis Example 6 by using intermediate I-27 (20 g, 34.3 mmol) and 2-phenyl-9H-carbazole (9.17 g, 37.7 mmol).

[0510] HRMS (70 eV, EI+): calculated m / z for C57H34N4O2: 806.2682, measured: 806.

[0511] Elemental analysis: C, 84%; H, 4%.

[0512] Synthesis Example 37: Synthesis of Intermediate I-28

[0513]

[0514] Intermediate I-28 (23.7 g, 86%) was obtained in the same manner as in Synthesis Example 1 by using intermediate I-26 (20 g, 41.8 mmol) and 2-(3-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (15.8 g, 46.0 mmol).

[0515] HRMS (70 eV, EI+): calculated m / z for C45H26FN3O2: 659.2009, measured: 659.

[0516] Elemental analysis: C, 82%; H, 4%.

[0517] Synthesis Example 38: Synthesis of Compound 150

[0518]

[0519] Compound 150 (15.2 g, 62%) was obtained in the same manner as in Synthesis Example 6 by using intermediate I-28 (20 g, 30.3 mmol) and 9H-carbazole (5.6 g, 33.3 mmol).

[0520] HRMS (70 eV, EI+): calculated m / z for C57H34N4O2: 806.2682, measured: 806.

[0521] Elemental analysis: C, 85%; H, 4%.

[0522] Synthesis Example 39: Synthesis of Compound Main Body 1

[0523]

[0524] Compound main body 1 was synthesized with reference to Patent US9732069.

[0525] HRMS(70eV, EI+): Calculated m / z for C39H24N4O: 564.1950, Measured: 564.

[0526] Elemental analysis: C, 83%; H, 4%.

[0527] Synthesis Example 40: Synthesis of Compound Main Body 2

[0528]

[0529] Compound main body 2 was synthesized with reference to Patent KR2040226.

[0530] HRMS(70eV, EI+): Calculated m / z for C42H25NO2: 575.1885, Measured: 575.

[0531] Elemental analysis: C, 88%; H, 4%.

[0532] Synthesis Example 41: Synthesis of Compound Main Body 3

[0533]

[0534] Compound main body 3 was synthesized with reference to Patent WO2021-029616.

[0535] HRMS(70eV, EI+): Calculated m / z for C51H30N4OS: 746.2140, Measured: 746.

[0536] Elemental analysis: C, 82%; H, 4%.

[0537] Synthesis Example 42: Synthesis of Compound B-136

[0538]

[0539] Compound B-136 was synthesized with reference to Patent EP3034581.

[0540] HRMS(70eV, EI+): Calculated m / z for C42H28N2: 560.2252, Measured: 560.

[0541] Elemental analysis: C, 90%; H, 5%.

[0542] Synthesis Example 43: Synthesis of Compound B-99

[0543]

[0544] Refer to patent KR10-2019-0000597 to synthesize compound B-99.

[0545] HRMS(70eV, EI+): Calculated m / z for C48H32N2: 636.2565, Measured: 636.

[0546] Elemental analysis: C, 91%; H, 5%.

[0547] Synthesis Example 44: Synthesis of Compound B-31

[0548]

[0549] Refer to patent EP2947071 to synthesize compound B-31.

[0550] HRMS(70eV, EI+): Calculated m / z for C48H32N2: 636.2565, Measured: 636.

[0551] Elemental analysis: C, 91%; H, 5%.

[0552] Synthesis Example 45: Synthesis of Compound C-4

[0553]

[0554] Refer to patent KR2031300 to synthesize compound C-4.

[0555] HRMS(70eV, EI+): Calculated m / z for C42H28N2: 560.2252, Measured: 560.

[0556] Elemental analysis: C, 90%; H, 5%.

[0557] Synthesis Example 46: Synthesis of Compound C-57

[0558]

[0559] Refer to patent WO2018-095391 to synthesize compound C-57.

[0560] HRMS(70eV, EI+): Calculated m / z for C48H32N2: 636.2565, Measured: 636.

[0561] Elemental analysis: C, 91%; H, 5%.

[0562] Example 1

[0563] The 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 washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and transferred to a vacuum depositor. The prepared ITO transparent electrode was used as the anode, and Compound A doped with 3% NDP-9 (commercially available from Novaled GmbH) was vacuum deposited on the ITO substrate to form a thick hole injection layer, and a thick hole transport layer was formed thereon by depositing Compound A. Compound B was deposited on the hole transport layer to a thickness of to form a hole transport auxiliary layer, and on the hole transport auxiliary layer, Compound 1 synthesized in Synthesis Example 12 was used as the host and PhGD was doped as a dopant at 7 wt% to form a thick light-emitting layer by vacuum deposition. Subsequently, Compound C was deposited on the light-emitting layer to a thickness of to form an electron transport auxiliary layer, and Compound D and Liq were co-vacuum deposited at a weight ratio of 1:1 to form a thick electron transport layer. An organic light-emitting diode was fabricated by sequentially vacuum depositing of LiQ and of Al on the electron transport layer to form a cathode.

[0564] The organic light-emitting diode was fabricated with the following structure: ITO / Compound A (doped with 3% NDP-9, ) / Compound A / Compound B / EML [Compound 1 (93 wt%): PhGD (7 wt%)] / Compound C / Compound D:LiQ / LiQ / Al

[0565] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluorene-2-amine

[0566] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0567] Compound C: 2,4-diphenyl-6-(4',5',6'-triphenyl[1,1':2',1”:3”,1”':3”',1””-quaterphenyl]-3””-yl)-1,3,5-triazine

[0568] Compound D: 2-(1,1'-Biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0569] [PhGD]

[0570]

[0571] Examples 2 to 10 and Comparative Examples 1 to 3

[0572] Each organic light-emitting diode was fabricated in the same manner as in Example 1, except that the composition was changed as described in Table 1.

[0573] Example 11

[0574] A glass substrate coated with an ITO (indium tin oxide) film was ultrasonically cleaned with distilled water. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, then transferred to a plasma cleaner, cleaned with oxygen plasma for 10 minutes, and transferred to a vacuum depositor. This prepared ITO transparent electrode was used as the anode, and Compound A doped with 3% NDP-9 (Novaled GmbH) was vacuum deposited on the ITO substrate to form a thick hole injection layer, and Compound A was deposited on the hole injection layer to form a thick hole transport layer. Compound E was deposited on the hole transport layer to a thickness of to form a hole transport auxiliary layer. On the hole transport auxiliary layer, Compound 1 synthesized in Synthesis Example 12 and Compound B-136 synthesized in Synthesis Example 31 were used as hosts simultaneously, and PhGD was doped at 10 wt% as a dopant to form a thick light-emitting layer by vacuum deposition. Here, Compound 1 and Compound B-136 were used in a weight ratio of 3:7. Subsequently, Compound F was deposited on the light-emitting layer to form a thick electron transport auxiliary layer, and Compound G and Liq were co-vacuum deposited in a weight ratio of 1:1 to form a thick electron transport layer. On the electron transport layer, a cathode was formed by sequentially vacuum depositing LiQ of and Al of

[0575] An organic light-emitting diode was fabricated to have the following structure: ITO / Compound A (doped with 3% NDP-9, ) / Compound A / Compound E / EML [Matrix (Compound 1: Compound B-136 = 27:63) 90 wt%, PhGD 10 wt%)] / Compound F / Compound G:LiQ / LiQ / Al

[0576] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0577] Compound F: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0578] Compound G: 2-[4-[4-(4'-cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0579] Example 12

[0580] An organic light-emitting diode was fabricated in the same manner as in Example 11, except that Compound 1 and Compound B-136 were used at a weight ratio of 4:6.

[0581] Example 13

[0582] An organic light-emitting diode was fabricated in the same manner as in Example 11, except that Compound 1 and Compound B-136 were used at a weight ratio of 5:5.

[0583] Examples 14 to 26 and Comparative Examples 4 to 6

[0584] Each organic light-emitting diode was fabricated in the same manner as in Example 11, except that the composition was changed as described in Table 2.

[0585] Evaluation

[0586] The driving voltage, luminous efficiency, and lifetime characteristics of the organic light-emitting diodes according to Examples 1 to 26 and Comparative Examples 1 to 6 were evaluated.

[0587] The specific measurement methods are as follows, and the results are shown in Tables 1 and 2.

[0588] (1) Measuring the change in current density according to the change in voltage

[0589] While increasing the voltage from 0 V to 10 V, the current value flowing through the unit device in the organic light-emitting diode is measured using a current-voltage meter (Keithley 2400), and the measured current value is divided by the area to provide the result.

[0590] (2) Measure the change in luminance according to the change in voltage

[0591] While increasing the voltage of the organic light-emitting diode from 0 V to 10 V, the luminance is measured by using a luminance meter (Minolta Cs-1000A).

[0592] (3) Measure the luminous efficiency

[0593] By using the luminance, current density, and voltage from (1) and (2) above, calculate the current efficiency (cd / A) at the same current density (10 mA / cm 2 ).

[0594] The luminous efficiency values of Examples 1 to 10 and Comparative Examples 1 to 3 are calculated as relative values based on Comparative Example 1 and listed in Table 1.

[0595] The luminous efficiency values of Examples 11 to 26 and Comparative Examples 4 to 6 are calculated as relative values based on Comparative Example 4 and listed in Table 2.

[0596] (4) Measure the lifetime

[0597] By maintaining the luminance (cd / m 2 ) at 24000 cd / m 2 and measuring the time when the current efficiency (cd / A) decreases to 97%, the result is obtained.

[0598] The lifetime measurement values of Examples 1 to 10 and Comparative Examples 1 to 3 are calculated as relative values based on Comparative Example 1 and listed in Table 1.

[0599] The lifetime measurement values of Examples 11 to 26 and Comparative Examples 4 to 6 are calculated as relative values based on Comparative Example 4 and listed in Table 2.

[0600] (5) Measure the driving voltage

[0601] Use a current-voltage meter (Keithley 2400) to measure the driving voltage of each device at 15 mA / cm 2 to obtain the result.

[0602] The driving voltages of Examples 1 to 10 and Comparative Examples 1 to 3 are calculated as relative values based on Comparative Example 1 and listed in Table 1.

[0603] The driving voltages of Examples 11 to 26 and Comparative Examples 4 to 6 are calculated as relative values based on Comparative Example 4 and listed in Table 2.

[0604] [Table 1]

[0605] Number Main Body Drive Voltage (%) Efficiency (%) Lifetime (%) Example 1 Compound 1 96 196 196 Example 2 Compound 2 94 172 189 Example 3 Compound 3 95 192 150 Example 4 Compound 4 91 232 161 Example 5 Compound 5 92 240 182 Example 6 Compound 54 99 140 250 Example 7 Compound 94 88 240 196 Example 8 Compound 102 95 200 161 Example 9 Compound 126 97 192 214 Example 10 Compound 150 99 208 200 Comparative Example 1 Main Body 1 100 100 100 Comparative Example 2 Main Body 2 106 60 18 Comparative Example 3 Main Body 3 101 120 107

[0606] [Table 2]

[0607]

[0608]

[0609] Referring to Table 1 and Table 2, compared with the organic light-emitting diodes according to Comparative Examples 1 to 6, the organic light-emitting diodes according to Examples 1 to 26 have significantly improved driving voltage, luminous efficiency, and lifetime characteristics.

Claims

1. A compound for an organic optoelectronic device, the compound being represented by Chemical Formula 1 or Chemical Formula 2: [Chemical Formula 1] [Chemical Formula 2] In Chemical Formula 1 and Chemical Formula 2, X 1 and X 2 each independently is O, S or SiR a R b , Z 1 from Z 3 each independently is N or CR c , Z 1 from Z 3 to Z, at least one of them is N R a 、 R b 、 R c and R 1 to R 9 each independently is hydrogen, deuterium, cyano, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C1-C10 alkylsilyl, or substituted or unsubstituted C6-C12 aryl, Ar 1 and Ar 2 each independently is a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C20 heterocyclic group, L 1 to L 4 each independently is a single bond or a substituted or unsubstituted C6 to C20 arylene group, m1, m2 and m4 are each independently one of the integers from 1 to 4, and m3 is one of the integers from 1 to 3.

2. The compound for an organic optoelectronic device according to claim 1, wherein Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In Chemical Formulas 1-1 to 1-4, X 1 、 X 2 、 Z 1 to Z 3 、 R 1 to R 9 、 Ar 1 to Ar 4 、 L 1 to L 4 and m1 to m4 are defined in claim 1.

3. The compound for an organic optoelectronic device according to claim 1, wherein Chemical Formula 2 is represented by any one of Chemical Formulas 2-1 to 2-4: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] In Chemical Formulas 2-1 to 2-4, X 1 , X 2 , Z 1 to Z 3 , R 1 to R 7 , Ar 1 , L 1 to L 3 and m1 to m7 are defined in claim 1.

4. The compound for an organic optoelectronic device according to claim 1, wherein L 1 and L 2 are each independently a single bond or a substituted or unsubstituted phenylene group.

5. The compound for an organic optoelectronic device according to claim 1, wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a substituted or unsubstituted carbazolyl group.

6. The compound for an organic optoelectronic device according to claim 1, wherein R 1 to R 9 are each independently hydrogen, deuterium, cyano, a substituted or unsubstituted C1-C5 alkylsilyl, or a substituted or unsubstituted C6-C12 aryl.

7. 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] 8. A composition for an organic optoelectronic device, comprising a first compound and a second compound, Among them, the first compound being the compound for an organic optoelectronic device according to claim 1, and the second compound being represented by Chemical Formula 3 or by a combination of Chemical Formulas 4 and 5: [Chemical Formula 3] In Chemical Formula 3, R 10 to R 14 each independently is hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, Ar 3 and Ar 4 each independently is a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, L 5 and L 6 each independently is a single bond or a substituted or unsubstituted C6-C20 arylene group, m10, m13 and m14 are each independently one of the integers from 1 to 4, m11 and m12 are each independently one of the integers from 1 to 3, and n is one of the integers from 0 to 2; In Chemical Formulas 4 and 5, In Chemical Formula 4, each of a1* to a4* is independently a linking carbon (C) or C-L a -R d ; in a1* to a4* of Chemical Formula 4, two adjacent ones of them are each linked to * in Chemical Formula 5 L a , L 7 and L 8 each independently is a single bond or a substituted or unsubstituted C6 to C20 arylene group, R d 、R 15 and R 16 each independently is hydrogen, deuterium, cyano, halogen, a substituted or unsubstituted amino group, a substituted or unsubstituted C1-C30 alkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C2-C30 heterocyclic group, Ar 5 and Ar 6 each independently is a substituted or unsubstituted C6-C20 aryl group or a substituted or unsubstituted C2-C30 heterocyclic group, and m15 and m16 are each independently one of the integers from 1 to 4.

9. The composition for an organic optoelectronic device according to claim 8, wherein Chemical Formula 3 is represented by Chemical Formula 3-8: [Chemical Formula 3-8] In Chemical Formula 3-8, R 10 to R 13 each independently is hydrogen, deuterium or a substituted or unsubstituted C6 to C12 aryl group, m10 and m13 are each independently one of the integers from 1 to 4, m11 and m12 are each independently one of the integers from 1 to 3, and L 5 -Ar 3 and L 6 -Ar 4 each independently is one of the substituents listed in Group II [Group II] In Group II, R 17 to R 21 each independently is hydrogen, deuterium, cyano, C1-C10 alkyl or C6-C12 aryl, m17 is one of the integers from 1 to 5, m18 is one of the integers from 1 to 4, m19 is one of the integers from 1 to 3, m20 is an integer of 1 or 2, m21 is one of the integers from 1 to 7, and * is a connection point.

10. The composition for an organic optoelectronic device according to claim 8, wherein the combination of Chemical Formulas 4 and 5 is represented by Chemical Formula 4C: [Chemical Formula 4C] In Chemical Formula 4C, L a3 and L a4 is a single bond, R 15 、R 16 、R d3 and R d4 each independently is hydrogen, deuterium or a C6 to C12 aryl group, m15 and m16 are each independently one of the integers from 1 to 4, and *-L 7 -Ar 5 and *-L 8 -Ar 6 each independently is one of the substituents listed in Group II, [Group II] In Group II, R 17 to R 21 each independently is hydrogen, deuterium, cyano, C1-C10 alkyl or C6-C12 aryl, m17 is one of the integers from 1 to 5, m18 is one of the integers from 1 to 4, m19 is one of the integers from 1 to 3, m20 is an integer of 1 or 2, m21 is one of the integers from 1 to 7, and * is a connection point.

11. 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, Among them, the organic layer comprising the compound for an organic optoelectronic device according to any one of claims 1 to 7; or The composition for an organic optoelectronic device according to any one of claims 8 to 10.

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

13. A display device comprising the organic optoelectronic device according to claim 11.

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