Organic optoelectronic device compound, organic optoelectronic device composition, organic optoelectronic device, and display device

Abstract

The present invention relates to an organic optoelectronic device compound represented by chemical formula 1, an organic optoelectronic device composition comprising same, an organic optoelectronic device, and a display device. The details of chemical formula 1 are the same as those defined in the specification.

Description

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

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

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

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

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

[0005] Among these, organic light-emitting diodes (OLEDs) have recently attracted significant attention due to the increasing demand for flat panel display devices. OLEDs are devices that convert electrical energy into light, and their performance is significantly influenced by the organic materials located between the electrodes.

[0006] One embodiment provides a compound for an organic optoelectronic device that can lower the driving voltage and realize a high-efficiency and long-life organic optoelectronic device.

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

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

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

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

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] X 1 Silver O, S, CR a R b , or SiR c R d And,

[0015] L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,

[0016] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0017] R a , R b , R c and R d are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0018] R 1 Inland R 19are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0019] According to another embodiment, a composition for an organic optoelectronic device is provided, comprising a first compound and a second compound.

[0020] The above first compound is a compound for the above-mentioned organic optoelectronic device, and the above second compound can be represented by the following chemical formula 2.

[0021] [Chemical Formula 2]

[0022]

[0023] In the above chemical formula 2,

[0024] Z 1 Inland Z 6 are each independently N or CL a -R e And,

[0025] Z 1 Inland Z 6 At least two of them are N,

[0026] L a are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0027] R e are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof,

[0028] R eare each independently present or adjacent groups are linked to form a substituted or substituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring.

[0029] According to another embodiment, an organic optoelectronic device is provided, comprising an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises the compound for an organic optoelectronic device or the composition for an organic optoelectronic device.

[0030] According to another embodiment, a display device including the organic optoelectronic device is provided.

[0031] High-efficiency, long-life organic optoelectronic devices can be realized while lowering the operating voltage.

[0032] Figure 1 is a cross-sectional view illustrating an organic light-emitting device according to one embodiment.

[0033] <Explanation of symbols>

[0034] Hereinafter, embodiments of the present invention will be described in detail. However, these are presented as examples and are not intended to limit the present invention. The present invention is defined solely by the scope of the claims set forth below.

[0035] As used herein, “substituted” means that at least one hydrogen in a substituent or compound is substituted with deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof, unless otherwise defined.

[0036] In one embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C6 to C30 arylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, or a cyano group. In addition, in one specific embodiment of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is substituted with deuterium, a C1 to C20 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C20 aryl group, a C2 to C20 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is replaced with deuterium, a C1 to C5 alkyl group, a C1 to C5 alkylsilyl group, a C6 to C18 aryl group, a C2 to C18 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or a compound is replaced with deuterium, a cyano group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a trimethylsilyl group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.

[0037] As used herein, “unsubstituted” means that a hydrogen atom remains a hydrogen atom without being replaced by another substituent.

[0038] In this specification, “hydrogen (-H)” may include “deuterium substitution (-D)” or “tritium substitution (-T)”.

[0039] In this specification, unless otherwise defined, “hetero” means containing 1 to 3 heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon.

[0040] In this specification, "aryl group" is a concept that encompasses a group having one or more hydrocarbon aromatic moieties, and includes a form in which all elements of the hydrocarbon aromatic moieties have p-orbitals and these p-orbitals form conjugation, such as a phenyl group, a naphthyl group, etc., a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, such as a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are directly or indirectly fused, such as a fluorenyl group, etc.

[0041] Aryl groups include monocyclic, polycyclic, or fused ring polycyclic (i.e., rings that share adjacent pairs of carbon atoms) functional groups.

[0042] In this specification, "heterocyclic group" is a superordinate concept including a heteroaryl group, and means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof. When the heterocyclic group is a fused ring, the heterocyclic group as a whole or each ring may contain one or more heteroatoms.

[0043] For example, a "heteroaryl group" means an aryl group containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si. Two or more heteroaryl groups may be directly connected via a sigma bond, or when the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 of the heteroatoms.

[0044] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be, but is not limited to, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof.

[0045] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted It may be an isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthfuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenfluorenyl group, or a combination thereof, but is not limited thereto.

[0046] In this specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has a conductive characteristic along the HOMO level, which means a characteristic that facilitates the injection of holes formed at the anode into the light-emitting layer, the movement of holes formed in the light-emitting layer to the anode, and the movement in the light-emitting layer.

[0047] In addition, electronic properties refer to the property of being able to receive electrons when an electric field is applied, and have conductive properties along the LUMO level, which means the property of facilitating the injection of electrons formed at the cathode into the light-emitting layer, the movement of electrons formed in the light-emitting layer to the cathode, and the movement in the light-emitting layer.

[0048] Hereinafter, a compound for an organic optoelectronic device according to an embodiment is described.

[0049] A compound for an organic optoelectronic device according to one embodiment is represented by the following chemical formula 1.

[0050] [Chemical Formula 1]

[0051]

[0052] In the above chemical formula 1,

[0053] X 1 Silver O, S, CR a R b , or SiR c R d And,

[0054] L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,

[0055] Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0056] R a , R b , R c and R d are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0057] R 1 Inland R 19 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

[0058] The compound represented by chemical formula 1 is a structure in which two carbazoles are connected in the direction of the phenyl ring of the carbazole, and 1-dibenzofuran (1-dibenzothiophene, 4-fluorene, 4-dibenzosilole) is substituted at the 4th position of the opposite phenyl ring.

[0059] By connecting 1-dibenzofuran (1-dibenzothiophene, 4-fluorene, 4-dibenzosilole) to the 4th position of the phenyl ring opposite to the 3rd position of the phenyl ring of carbazole, hole mobility increases, which enables obtaining a fast operating voltage, and the HOMO pore is expanded, which can drastically reduce hole trapping by the dopant. As a result, devices applying the compound can realize the effects of low driving / high efficiency / long life.

[0060] In particular, the 4th position in the phenyl ring of carbazole is a position where steric hindrance is strong, so it has a lower △Est value based on a higher T1 and lower S1 than materials connected to other positions, and thus the exciplex is amplified, resulting in high efficiency.

[0061] For example, the above L 1 and L 2 may each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted dibenzofuranylene group, a substituted or unsubstituted dibenzothiophenylene group, or a substituted or unsubstituted dibenzosiloylene group.

[0062] For example, the above Ar 1 and Ar 2may 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 fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

[0063] In one embodiment, the Ar 1 and Ar 2 Each of the substituents may be independently selected from the substituents listed in Group I below.

[0064] [Group Ⅰ]

[0065]

[0066] In the above group Ⅰ,

[0067] R 20 Inland R 22 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group,

[0068] m2 is an integer between 1 and 5,

[0069] m3 is one of the integers 1 to 4,

[0070] m4 is one of the integers 1 to 3,

[0071] * is a connection point.

[0072] If m2 is 2 or more, each R 20 may be identical or different.

[0073] If m3 is 2 or more, each R 21 may be identical or different.

[0074] If m4 is 2 or more, each R 22 may be identical or different.

[0075] For example, the above R 1 Inland R 19 may each independently be hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a combination thereof.

[0076] In one embodiment, the R 1 Inland R 19 may be independently selected from hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted iso-propyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted iso-butyl group, a substituted or unsubstituted sec-butyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted trimethylsilyl group, or a substituent listed in Group II below.

[0077] [Group II]

[0078]

[0079] In the above group II,

[0080] R 20 Inland R 22 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group,

[0081] m2 is an integer between 1 and 5,

[0082] m3 is one of the integers 1 to 4,

[0083] m4 is one of the integers 1 to 3,

[0084] * is a connection point.

[0085] In a specific embodiment, the compound for an organic optoelectronic device represented by Chemical Formula 1 may be one selected from the compounds listed in Group 1 below, but is not limited thereto.

[0086] [Group 1]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] According to another embodiment, a composition for an organic optoelectronic device includes a first compound and a second compound, wherein the first compound is the compound for an organic optoelectronic device described above, and the second compound can be represented by the following chemical formula 2.

[0128] [Chemical Formula 2]

[0129]

[0130] In the above chemical formula 2,

[0131] Z 1 Inland Z 6 are each independently N or CL a -R e And,

[0132] Z 1 Inland Z 6 At least two of them are N,

[0133] L a are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0134] R e are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof,

[0135] R e are each independently present or adjacent groups are linked to form a substituted or substituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring.

[0136] The second compound effectively expands the LUMO energy band by including a nitrogen-containing hexagonal moiety, and thus, when included together with the first compound described above, it can increase the balance between holes and electrons, thereby significantly improving the lifespan characteristics of a device to which it is applied.

[0137] For example, Z 1 Inland Z 6 Two of them are nitrogen (N) and the rest are CL a -R e It could be.

[0138] For example Z 1 and Z 3 is nitrogen and Z 2 is N or CLa -R e And Z 4 is N or CL a -R e And Z 5 is N or CL a -R e And Z 6 is N or CL a -R e It could be.

[0139] For example, Z 1 Inland Z 6 Three of them are nitrogen (N) and the rest are CL a -R e It could be.

[0140] For example Z 1 , Z 3 and Z 5 is nitrogen and Z 2 is N or CL a -R e And Z 4 is N or CL a -R e And Z 6 is N or CL a -R e It could be.

[0141] As a specific example, the above R e Depending on the specific substituent, the second compound may be represented by, for example, any one of the following chemical formulas 2A to 2C.

[0142] [Chemical Formula 2A] [Chemical Formula 2B]

[0143]

[0144] [Chemical Formula 2C]

[0145]

[0146] In the above chemical formulas 2A to 2C,

[0147] Z 1 , Z 3 and Z 5 are each independently N or CLa -R e And,

[0148] Z 1 , Z 3 and Z 5 At least two of them are N,

[0149] X 2 is O, S or NR f And,

[0150] L a , and L 3 Inland L 5 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

[0151] R e , R f and R 23 Inland R 44 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof,

[0152] R 23 Inland R 30 are each independently present or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring,

[0153] R 31 Inland R 35 are each independently present or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring,

[0154] Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

[0155] Ra , Ar 3 and Ar 4 exist independently of each other, or

[0156] R a , Ar 3 and Ar 4 Adjacent groups are connected to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring,

[0157] m5 and m6 are each independently an integer from 1 to 3.

[0158] In the above chemical formula 2B, when m5 is 2 or more, each R 31 may be the same or different.

[0159] In the above chemical formula 2C, when m6 is 2 or more, each R 36 may be the same or different.

[0160] In this specification, "adjacent groups are linked to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring" means that any two adjacent substituents are linked to each other to form a ring. For example, in Chemical Formula 2A, R 23 Inland R 30 Adjacent groups can be linked to each other to form a substituted or unsubstituted aromatic monocyclic ring. The aromatic monocyclic ring formed at this time may include, for example, a substituted or unsubstituted phenyl group.

[0161] As a more specific example, the chemical formula 2A may be represented by any one of the following chemical formulas 2A-Ⅰ to 2A-ⅩⅡ.

[0162] [Chemical Formula 2A-Ⅰ] [Chemical Formula 2A-Ⅱ]

[0163]

[0164] [Chemical Formula 2A-Ⅲ] [Chemical Formula 2A-Ⅳ]

[0165]

[0166] [Chemical Formula 2A-Ⅴ] [Chemical Formula 2A-Ⅵ]

[0167]

[0168] [Chemical Formula 2A-Ⅶ] [Chemical Formula 2A-Ⅷ]

[0169]

[0170] [Chemical Formula 2A-Ⅸ] [Chemical Formula 2A-Ⅹ]

[0171]

[0172] [Chemical Formula 2A-ⅩⅠ] [Chemical Formula 2A-ⅩⅡ]

[0173]

[0174] [Chemical Formula 2A-ⅩⅢ] [Chemical Formula 2A-ⅩⅣ]

[0175]

[0176] [Chemical Formula 2A-ⅩⅤ] [Chemical Formula 2A-ⅩⅥ]

[0177]

[0178] [Chemical Formula 2A-Ⅶ] [Chemical Formula 2A-Ⅷ]

[0179]

[0180] In the above chemical formulas 2A-Ⅰ to 2A-Ⅷ,

[0181] L 2 Inland L 4 , Ar 3 and Ar 4 , R 23 Inland R 30 is as described above,

[0182] X 3 is O or S,

[0183] Ar 6 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0184] L 6is a single bond, a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heterocyclic group,

[0185] R 45 Inland R 64 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted C1 to C10 alkylsilyl group, a substituted or unsubstituted amine group, halogen, cyano group, or a combination thereof.

[0186] For example, the above L 3 Inland L 6 may each independently be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

[0187] For example, the above Ar 3 , Ar 4 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 quaterphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0188] For example, the above R 23 Inland R 30 and R 45 Inland R 64may each independently be hydrogen, a deuterium cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

[0189] For example, the above chemical formula 2B can be represented by any one of the following chemical formulas 2B-Ⅰ to 2B-Ⅳ.

[0190] [Chemical Formula 2B-Ⅰ] [Chemical Formula 2B-Ⅱ]

[0191]

[0192] [Chemical Formula 2B-Ⅲ] [Chemical Formula 2B-Ⅳ]

[0193]

[0194] In the above chemical formulas 2B-Ⅰ to 2B-Ⅳ, X 2 , L 3 Inland L 5 , Ar 3 and Ar 4 , R 31 Inland R 35 and m5 are as described above.

[0195] For example, the above chemical formula 2C can be represented by the following chemical formula 2C-Ⅰ or chemical formula 2C-Ⅱ.

[0196] [Chemical Formula 2C-Ⅰ] [Chemical Formula 2C-Ⅱ]

[0197]

[0198] In the above chemical formulas 2C-Ⅰ and 2C-Ⅱ, L 3 Inland L 5 , Ar 3 and Ar 4 , R 36 Inland R 44 and m6 are as described above.

[0199] In a specific embodiment, the chemical formula 2 may be represented by the chemical formula 2A-ⅩⅣ or the chemical formula 2C-Ⅰ.

[0200] For example, in the above chemical formula 2A-ⅩⅣ, L 3 Inland L 6 are each independently a single bond or a substituted or unsubstituted C6 to C12 aryl group, and Ar 3 , Ar 4 and Ar 6 are 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 triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, and R 23 Inland R 28 , R 61 Inland R 64 Each of may independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0201] For example, in the above chemical formula 2C-Ⅰ, L 3 Inland L 5 are each independently a single bond or a substituted or unsubstituted C6 to C12 aryl group, and Ar 3 and Ar 4 are 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 triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, and R 36 Inland R 44 Each of may independently be hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group.

[0202] The second compound may be, for example, one selected from the compounds listed in Group 2 below, but is not limited thereto.

[0203] [Group 2]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236]

[0237]

[0238]

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276]

[0277]

[0278]

[0279]

[0280]

[0281]

[0282]

[0283]

[0284]

[0285]

[0286]

[0287]

[0288]

[0289]

[0290]

[0291]

[0292]

[0293] [E-1] [E-2] [E-3] [E-4] [E-5]

[0294]

[0295] [E-6] [E-7] [E-8] [E-9] [E-10]

[0296]

[0297] [E-11] [E-12] [E-13] [E-14] [E-15]

[0298]

[0299] [E-16] [E-17] [E-18] [E-19] [E-20]

[0300]

[0301] [E-21] [E-22] [E-23] [E-24] [E-25]

[0302]

[0303] [E-26] [E-27] [E-28] [E-29] [E-30]

[0304]

[0305] [E-31] [E-32] [E-33] [E-34] [E-35]

[0306]

[0307] [E-36] [E-37] [E-38] [E-39] [E-40]

[0308]

[0309] [E-41] [E-42] [E-43] [E-44] [E-45]

[0310]

[0311] [E-46] [E-47] [E-48] [E-49] [E-50]

[0312]

[0313] [E-51] [E-52] [E-53] [E-54] [E-55]

[0314]

[0315] [E-56] [E-57] [E-58] [E-59] [E-60]

[0316]

[0317] [E-61] [E-62] [E-63] [E-64] [E-65]

[0318]

[0319] [E-66] [E-67] [E-68] [E-69] [E-70]

[0320]

[0321] [E-71] [E-72] [E-73] [E-74] [E-75]

[0322]

[0323] [E-76] [E-77] [E-78] [E-79] [E-80]

[0324]

[0325] [E-81] [E-82] [E-83] [E-84] [E-85]

[0326]

[0327] [E-86] [E-87] [E-88] [E-89] [E-90]

[0328]

[0329] [E-91] [E-92] [E-93] [E-94] [E-95]

[0330]

[0331] [E-96] [E-97] [E-98] [E-99] [E-100]

[0332]

[0333] [E-101] [E-102] [E-103] [E-104] [E-105]

[0334]

[0335] [E-106] [E-107] [E-108] [E-109] [E-110]

[0336]

[0337] [E-111] [E-112] [E-113] [E-114] [E-115]

[0338]

[0339] [E-116] [E-117] [E-118] [E-119] [E-120]

[0340]

[0341] [E-121] [E-122] [E-123] [E-124] [E-125]

[0342]

[0343] [E-126] [E-127] [E-128] [E-129] [E-130]

[0344]

[0345] [E-131] [E-132] [E-133] [E-134] [E-135]

[0346]

[0347] [E-136] [E-137] [E-138] [E-139] [E-140]

[0348]

[0349] [E-141] [E-142] [E-143] [E-144] [E-145]

[0350]

[0351] [E-146] [E-147] [E-148] [E-149] [E-150]

[0352]

[0353] [E-151] [E-152] [E-153] [E-154] [E-155]

[0354]

[0355] [E-156] [E-157] [E-158] [E-159] [E-160]

[0356]

[0357] [E-161] [E-162] [E-163] [E-164] [E-165]

[0358]

[0359] [E-166] [E-167] [E-168] [E-169] [E-170]

[0360]

[0361] [E-171] [E-172] [E-173] [E-174] [E-175]

[0362]

[0363] [E-176] [E-177] [E-178] [E-179] [E-180]

[0364]

[0365] [E-181] [E-182] [E-183] [E-184] [E-185]

[0366]

[0367] [E-186] [E-187] [E-188] [E-189] [E-190]

[0368]

[0369] [E-191] [E-192] [E-193] [E-194] [E-195]

[0370]

[0371] [E-196] [E-197] [E-198] [E-199] [E-200]

[0372]

[0373] [E-201] [E-202] [E-203] [E-204] [E-205]

[0374]

[0375] [E-206] [E-207] [E-208] [E-209] [E-210]

[0376]

[0377] [E-211] [E-212] [E-213] [E-214] [E-215]

[0378]

[0379] [E-216] [E-217] [E-218] [E-219] [E-220]

[0380]

[0381] [E-221] [E-222] [E-223] [E-224] [E-225]

[0382]

[0383] [E-226] [E-227] [E-228] [E-229] [E-230]

[0384]

[0385] [E-231] [E-232] [E-233] [E-234] [E-235]

[0386]

[0387] [E-236] [E-237] [E-238] [E-239]

[0388]

[0389] [E-240] [E-241] [E-242] [E-243]

[0390]

[0391] [E-244] [E-245] [E-246] [E-247]

[0392]

[0393] [E-248] [E-249] [E-250] [E-251]

[0394]

[0395] [E-252] [E-253] [E-254] [E-255]

[0396]

[0397] [E-256] [E-257] [E-258] [E-259]

[0398]

[0399] [E-260] [E-261] [E-262] [E-263]

[0400]

[0401] [E-264] [E-265] [E-266] [E-267]

[0402]

[0403] [E-268] [E-269] [E-270] [E-271]

[0404]

[0405] [E-272] [E-273] [E-274] [E-275]

[0406]

[0407] [E-276] [E-277] [E-278] [E-279]

[0408]

[0409] [E-280] [E-281] [E-282] [E-283]

[0410] The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By being included in the above range, the hole transport ability of the first compound and the electron transport ability of the second compound can be used to achieve an appropriate weight ratio to implement bipolar characteristics, thereby improving efficiency and lifespan. Within the above range, the weight ratio may be included in a weight ratio of, for example, about 10:90 to 90:10, about 20:80 to 80:20, about 20:80 to about 70:30, about 20:80 to about 60:40, and about 30:70 to about 60:40. As a specific example, the weight ratio may be included in a weight ratio of 40:60, 50:50, or 60:40.

[0411] Hereinafter, an organic optoelectronic device using the compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above will be described.

[0412] Organic optoelectronic devices are not particularly limited as long as they can convert electrical energy and light energy to each other, and examples thereof include organic photoelectric devices, organic light-emitting devices, organic solar cells, and organic photosensitive drums.

[0413] Here, an organic light-emitting device, which is an example of an organic optoelectronic device, is described with reference to drawings.

[0414] Fig. 1 is a cross-sectional view showing an organic light-emitting device according to one embodiment.

[0415] Referring to FIG. 1, an organic light-emitting device (100) according to one embodiment includes an anode (120) and a cathode (110) facing each other, and an organic layer (105) positioned between the anode (120) and the cathode (110).

[0416] The anode (120) can be made of a conductor having a high work function, for example, to facilitate hole injection, and can be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode (120) may be, but is not limited to, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), or indium zinc oxide (IZO); a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyethylenedioxythiophene: PEDOT), polypyrrole, and polyaniline.

[0417] The cathode (110) may be made of a conductor with a low work function to facilitate electron injection, for example, and may be made of a metal, a metal oxide, and / or a conductive polymer. The cathode (110) may be made of, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; or a multilayer structure material such as LiF / Al, LiO2 / Al, LiF / Ca, LiF / Al, and BaF2 / Ca, but is not limited thereto.

[0418] The organic layer (105) may include the compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above.

[0419] The organic layer (105) includes a light-emitting layer (130), and the light-emitting layer (130) includes a host and a dopant, and the host may include the compound for an organic optoelectronic device or the composition for an organic optoelectronic device described above, and the dopant may be, for example, a phosphorescent dopant, and may be, for example, a red, green, or blue phosphorescent dopant, and may be, for example, a red or green phosphorescent dopant.

[0420] A dopant is a substance that causes light emission when mixed in trace amounts into a compound or composition for an organic optoelectronic device. Generally, a substance such as a metal complex that emits light by multiple excitation that excites to a triplet state or higher can be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may be included in one or more types.

[0421] An example of a dopant is a phosphorescent dopant, and examples of a phosphorescent dopant include an organometallic compound containing Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the following chemical formula Z, but is not limited thereto.

[0422] [Chemical formula Z]

[0423] L 7 MX 4

[0424] In the above chemical formula Z, M is a metal, and L 7 and X 4 are ligands that are the same or different and form complexes with M.

[0425] The above M may be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd or a combination thereof, and the above L 7 and X 4 may be, for example, a bidentate ligand.

[0426] L 7 and X 4 Examples of ligands represented by may be selected from, but are not limited to, the chemical formulas listed in Group A below.

[0427] [Group A]

[0428]

[0429] In the above group A,

[0430] R 300 Inland R 302 are each independently a C1 to C30 alkyl group substituted or unsubstituted with hydrogen, deuterium, halogen, a C6 to C30 aryl group substituted or unsubstituted with C1 to C30 alkyl, or halogen,

[0431] R 303 Inland R 324 are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0432] The dopant according to one embodiment may be an iridium complex, for example, represented by the following chemical formula 4-1 or chemical formula 4-2.

[0433] [Chemical Formula 4-1]

[0434]

[0435] In the above chemical formula 4-1,

[0436] R 101 Inland R 116 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R134 And,

[0437] The above R 132 Inland R 134 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0438] R 101 Inland R 116 At least one of them is a functional group represented by the following chemical formula V-1,

[0439] L 100 is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0440] m21 and m22 are independently any integer from 0 to 3, and m21 + m22 is any integer from 1 to 3,

[0441] [Chemical Formula V-1]

[0442]

[0443] In the above chemical formula V-1,

[0444] R 135 Inland R 139 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR 132 R 133 R 134 And,

[0445] * indicates a part connected to a carbon atom.

[0446] [Chemical Formula 4-2]

[0447]

[0448] In the above chemical formula 4-2,

[0449] R 101 Inland R 117are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -Si R 133 R 134 R 135 And,

[0450] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0451] L 100 is a bidentate ligand of a single anion, and is a ligand that coordinates to iridium through the unshared electron pair of carbon or a heteroatom.

[0452] n1 and n2 are independently any integer from 0 to 3, and n1 + n2 is any integer from 1 to 3.

[0453] In another embodiment, the dopant may be a platinum complex, for example represented by the chemical formula Z-1.

[0454] [Chemical Formula Z-1]

[0455]

[0456] In the above chemical formula Z-1, rings A, B, C, and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0457] R A , R B , R C , and R D each independently represents monosubstitution, disubstitution, trisubstitution, tetrasubstitution, or no substitution;

[0458] L B , L C , and L D are independently selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0459] If nA is 1, L E is selected from the group consisting of direct bonds, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof; when nA is 0, L E does not exist;

[0460] R A , R B , R C , R D , R, and R' are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, heteroalkyl group, arylalkyl group, alkoxy group, aryloxy group, amino group, silyl group, alkenyl group, cycloalkenyl group, heteroalkenyl group, alkynyl group, aryl group, heteroaryl group, acyl group, carbonyl group, carboxylic acid group, ester group, nitrile group, isonitrile group, sulfanyl group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof; any adjacent R A , R B , R C , R D , R, and R' are randomly connected to form a ring; X B , X C , X D , and X E are independently selected from the group consisting of carbon and nitrogen; Q 1 , Q 2 , Q 3 , and Q 4 represent oxygen or direct bonds, respectively.

[0461] The above platinum complex can be represented, for example, by the following chemical formula 5-1 or chemical formula 5-2.

[0462] [Chemical Formula 5-1]

[0463]

[0464] [Chemical Formula 5-2]

[0465]

[0466] In the above chemical formulas 5-1 and 5-2,

[0467] X 100 Silver O, S and NR 132 Selected from among,

[0468] R 118 Inland R 132 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or - SiR 133 R 134 R 135 And,

[0469] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group,

[0470] R 118 Inland R 132 At least one of them is -SiR 133 R 134 R 135 or tert-butyl group,

[0471] The above R 133 Inland R 135 are each independently a substituted or unsubstituted C1 to C6 alkyl group.

[0472] The organic layer may further include a charge transport region in addition to the light-emitting layer.

[0473] The above charge transport region may be, for example, a hole transport region (140).

[0474] The above hole transport region (140) can further increase hole injection and / or hole mobility between the anode (120) and the light-emitting layer (130) and block electrons.

[0475] Specifically, the hole transport region (140) may include a hole transport layer between the anode (120) and the light-emitting layer (130), and a hole transport auxiliary layer between the light-emitting layer (130) and the hole transport layer, and at least one of the compounds listed in Group B below may be included in at least one layer of the hole transport layer and the hole transport auxiliary layer.

[0476] [Group B]

[0477]

[0478]

[0479]

[0480]

[0481]

[0482]

[0483]

[0484]

[0485]

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492]

[0493]

[0494]

[0495]

[0496]

[0497]

[0498]

[0499]

[0500]

[0501]

[0502]

[0503]

[0504]

[0505]

[0506]

[0507]

[0508]

[0509]

[0510] (Dn refers to the number of deuterium atoms substituted, and indicates a structure in which one or more deuterium atoms are substituted)

[0511] In addition to the above-described compound, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A, etc. and compounds having a similar structure thereto may also be used in the above-described hole transport region (140).

[0512] Additionally, the charge transport region may be, for example, an electron transport region (150).

[0513] The above electron transport region (150) can further increase electron injection and / or electron mobility between the cathode (110) and the light-emitting layer (130) and block holes.

[0514] Specifically, the electron transport region (150) may include an electron transport layer between the cathode (110) and the light-emitting layer (130), and an electron transport auxiliary layer between the light-emitting layer (130) and the electron transport layer, and at least one of the compounds listed in Group C below may be included in at least one layer of the electron transport layer and the electron transport auxiliary layer.

[0515] [Group C]

[0516]

[0517]

[0518]

[0519]

[0520]

[0521]

[0522]

[0523]

[0524]

[0525]

[0526]

[0527]

[0528]

[0529]

[0530]

[0531]

[0532]

[0533] One embodiment may be an organic light-emitting device including a light-emitting layer as an organic layer.

[0534] Another embodiment may be an organic light-emitting device including an emission layer and a hole transport region as the organic layer.

[0535] Another embodiment may be an organic light-emitting device including an emission layer and an electron transport region as the organic layer.

[0536] An organic light-emitting device according to one embodiment of the present invention may include a hole transport region (140) and an electron transport region (150) in addition to a light-emitting layer (130) as an organic layer (105), as shown in FIG. 1.

[0537] Meanwhile, the organic light-emitting device may further include an electron injection layer (not shown), a hole injection layer (not shown), etc. in addition to the light-emitting layer as the aforementioned organic layer.

[0538] An organic light-emitting device (100) can be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film forming method such as evaporation, sputtering, plasma plating, and ion plating, and then forming a cathode or anode thereon.

[0539] The above-described organic light-emitting device can be applied to an organic light-emitting display device.

[0540] The implementation examples described above are described in more detail through the following examples. However, the following examples are for illustrative purposes only and do not limit the scope of the rights.

[0541] The starting materials and reactants used in the examples and synthesis examples below were purchased from Sigma-Aldrich, TCI, Tokyo Chemical Industry or P&H Tech, or synthesized using known methods, unless otherwise specified.

[0542]

[0543] (Synthesis of compounds for organic optoelectronic devices)

[0544] Synthesis Example 1: Synthesis of Intermediate I-1

[0545] [Reaction Formula 1]

[0546]

[0547] In a nitrogen environment, 3-bromo-5-chloro-9H-carbazole (100 g, 356 mmol) purchased from P&H tech (http: / www.phtech.co.kr / ) was dissolved in 1 L of xylene, and then iodobenzene (87 g, 428 mmol), copper(I) iodide (13.58 g, 71 mmol), ethylenediamine (EDA) (21.42 g, 356 mmol), and potassium phosphate tribasic (151 g, 713 mmol) purchased from tokyo chemical industry (http: / www.tcichemicals.com / ) were added, and the mixture was heated and refluxed for 17 hours. After completion of the reaction, water was added to the reaction solution, extracted with dichloromethane (DCM), and then water was removed with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The residue thus obtained was separated and purified by flash column chromatography to obtain intermediate I-1 (120.6 g, 95%).

[0548] HRMS (70eV, EI+): m / z calcd for C18H11BrClN: 354.9763, found: 354.

[0549] Elemental Analysis: C, 61%; H, 3%

[0550]

[0551] Synthesis Example 2: Synthesis of Intermediate I-2

[0552] [Reaction Formula 2]

[0553]

[0554] In a nitrogen environment, intermediate I-1 (40 g, 112 mmol) was dissolved in 0.4 L of dioxane, and 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (50 g, 135 mmol) and tetrakis(triphenylphosphine)palladium (2.60 g, 2.24 mmol) purchased from Mascot (Asia) Company Limited were added and stirred. Then, potassium carbonate (39 g, 280 mmol) saturated in water was added and heated at 120°C for 1 hour under reflux. After completion of the reaction, water was added to the reaction solution, and the mixture was filtered. The obtained residue was purified by flash column chromatography to obtain intermediate I-2 (48 g, 83%).

[0555] HRMS (70eV, EI+): m / z calcd for C36H23ClN2: 518.1550, found: 518.

[0556] Elemental Analysis: C, 83%; H, 4%

[0557]

[0558] Synthesis Example 3: Synthesis of Intermediate I-3

[0559] [Reaction Formula 3]

[0560]

[0561] In a nitrogen environment, intermediate I-2 (48 g, 92.5 mmol) was dissolved in 0.4 L of xylene, and bis(pinacolato)diboron (35.2 g, 139 mmol), Tris(dibenzylideneacetone)dipalladium(0) (2.5 g, 2.8 mmol), Tricyclohexylphosphine (6.2 g, 22 mmol), and potassium acetate (27.2 g, 277 mmol) were added thereto, and the mixture was heated and refluxed for 15 hours. After completion of the reaction, water was added to the reaction solution, extracted with dichloromethane (DCM), and then dried with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography to obtain intermediate I-3 (35.54 g, 63%).

[0562] HRMS (70eV, EI+): m / z calcd for C42H35BN2O2: 610.2792, found: 610.

[0563] Elemental Analysis: C, 83%; H, 6%

[0564]

[0565] Synthesis Example 4: Synthesis of Compound 1

[0566] [Reaction Formula 4]

[0567]

[0568] Compound 1 (10.14 g, 63%) was obtained using intermediate I-3 (15 g, 24.6 mmol) and 1-bromo-dibenzo[b,d]furan (6.1 g, 24.6 mmol) purchased from Ukseung Chemical (http: / www.ukseung.co.kr / ) in the same manner as in Synthesis Example 2.

[0569] HRMS (70eV, EI+): m / z calcd for C48H30N2O: 650.2358, found: 650.

[0570] Elemental Analysis: C, 89%; H, 5%

[0571]

[0572] Synthesis Example 5: Synthesis of Intermediate I-4

[0573] [Reaction Formula 5]

[0574]

[0575] Intermediate I-4 (18.35 g, 82%) was obtained using the same method as in Synthesis Example 2, using intermediate I-3 (20 g, 32.8 mmol) and 9-chlorodibenzo[b,d]furan-1-yl trifluoromethanesulfonate (11.5 g, 32.8 mmol) purchased from gemchem (http: / www.ytgemchem.com).

[0576] HRMS (70eV, EI+): m / z calcd for C48H29ClN2O: 684.1968, found: 684.

[0577] Elemental Analysis: C, 84%; H, 4%

[0578]

[0579] Synthesis Example 6: Synthesis of Intermediate I-5

[0580] [Reaction Formula 6]

[0581]

[0582] Intermediate I-5 (12.18 g, 62%) was obtained using intermediate I-4 (14.72 g, 21.5 mmol) in the same manner as in Synthesis Example 3.

[0583] HRMS (70eV, EI+): m / z calcd for C54H41BN2O3: 776.3210, found: 776.

[0584] Elemental Analysis: C, 84%; H, 5%

[0585]

[0586] Synthesis Example 7: Synthesis of Compound 24

[0587] [Reaction Formula 7]

[0588]

[0589] Compound 24 (9.57 g, 85%) was obtained using the same method as in Synthesis Example 2, using intermediate I-5 (12 g, 15.4 mmol) and bromobenzene (2.9 g, 18.5 mmol) purchased from Tokyo Chemical Industry (http: / www.tcichemicals.com / ).

[0590] HRMS (70eV, EI+): m / z calcd for C54H34N2O: 726.2671, found: 726.

[0591] Elemental Analysis: C, 89%; H, 5%

[0592]

[0593] Synthesis Example 8: Synthesis of Intermediate I-6

[0594] [Reaction Formula 8]

[0595]

[0596] Intermediate I-6 (40.5 g, 81%) was obtained using the same method as in Synthesis Example 2, using intermediate I-1 (30 g, 84.1 mmol) and 9-([1,1'-biphenyl]-2-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (44.9 g, 100.1 mmol) purchased from Ukseung Chemical (http: / www.ukseung.co.kr / ).

[0597] HRMS (70eV, EI+): m / z calcd for C42H27ClN2: 594.1863, found: 594.

[0598] Elemental Analysis: C, 85%; H, 5%

[0599]

[0600] Synthesis Example 9: Synthesis of Intermediate I-7

[0601] [Reaction Formula 9]

[0602]

[0603] Compound I-7 (25.4 g, 55%) was obtained using intermediate I-6 (40 g, 67 mmol) in the same manner as in Synthesis Example 3.

[0604] HRMS (70eV, EI+): m / z calcd for C48H39BN2O2: 686.3105, found: 686.

[0605] Elemental Analysis: C, 84%; H, 6%

[0606]

[0607] Synthesis Example 10: Synthesis of Intermediate I-8

[0608] [Reaction Formula 10]

[0609]

[0610] Intermediate I-8 (17.5 g, 79%) was obtained using the same method as in Synthesis Example 2, using intermediate I-7 (20 g, 29.1 mmol) and 9-chlorodibenzo[b,d]furan-1-yl trifluoromethanesulfonate (10.2 g, 29.1 mmol) purchased from gemchem (http: / www.ytgemchem.com).

[0611] HRMS (70eV, EI+): m / z calcd for C54H33ClN2O: 760.2281, found: 760.

[0612] Elemental Analysis: C, 85%; H, 4%

[0613]

[0614] Synthesis Example 11: Synthesis of Intermediate I-9

[0615] [Reaction Formula 11]

[0616]

[0617] Intermediate I-9 (12.76 g, 65%) was obtained using intermediate I-8 (17.5 g, 23.0 mmol) in the same manner as in Synthesis Example 3.

[0618] HRMS (70eV, EI+): m / z calcd for C59H44BN2O3: 839.3445, found: 839.

[0619] Elemental Analysis: C, 84%; H, 5%

[0620]

[0621] Synthesis Example 12: Synthesis of Compound 103

[0622] [Reaction Formula 12]

[0623]

[0624] Compound 103 (12.1 g, 83%) was obtained using the intermediate I-9 (12.7 g, 15.2 mmol) and bromobenzene (2.9 g, 18.2 mmol) purchased from Tokyo Chemical Industry (http: / www.tcichemicals.com / ) in the same manner as in Synthesis Example 2.

[0625] HRMS (70eV, EI+): m / z calcd for C60H38BN2O: 802.2984, found: 802.

[0626] Elemental Analysis: C, 90%; H, 5%

[0627]

[0628] Synthesis Example 13: Synthesis of Intermediate I-10

[0629] [Reaction Formula 13]

[0630]

[0631] Intermediate I-10 (60.16 g, 78%) was obtained using the same method as in Synthesis Example 1, 3-bromo-5-chloro-9H-carbazole (50 g, 178 mmol) purchased from P&H tech (http: / www.phtech.co.kr / ) and 2-iodobiphenyl (60 g, 214 mmol) purchased from tokyo chemical industry (http: / www.tcichemicals.com / ).

[0632] HRMS (70eV, EI+): m / z calcd for C24H15BrClN: 431.0076, found: 431.

[0633] Elemental Analysis: C, 67%; H, 3%

[0634]

[0635] Synthesis Example 14: Synthesis of Intermediate I-11

[0636] [Reaction Formula 14]

[0637]

[0638] Intermediate I-11 (66 g, 80%) was obtained using the same method as in Synthesis Example 2, using intermediate I-10 (60 g, 139 mmol) and 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (61.4 g, 166 mmol) purchased from Mascot (Asia) Company Limited.

[0639] HRMS (70eV, EI+): m / z calcd for C42H27ClN2: 594.1863, found: 594.

[0640] Elemental Analysis: C, 85%; H, 5%

[0641]

[0642] Synthesis Example 15: Synthesis of Intermediate I-12

[0643] [Reaction Formula 15]

[0644]

[0645] Intermediate I-12 (44 g, 58%) was obtained using intermediate I-11 (66 g, 110 mmol) in the same manner as in Synthesis Example 3.

[0646] HRMS (70eV, EI+): m / z calcd for C48H39BN2O2: 686.3105, found: 686.

[0647] Elemental Analysis: C, 84%; H, 6%

[0648]

[0649] Synthesis Example 16: Synthesis of Intermediate I-13

[0650] [Reaction Formula 16]

[0651]

[0652] Intermediate I-13 (17.5 g, 79%) was obtained using the same method as in Synthesis Example 2, using intermediate I-12 (20 g, 29.1 mmol) and 9-chlorodibenzo[b,d]furan-1-yl trifluoromethanesulfonate (10.2 g, 29.1 mmol) purchased from gemchem (http: / www.ytgemchem.com).

[0653] HRMS (70eV, EI+): m / z calcd for C54H33ClN2O: 760.2281, found: 760.

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

[0655]

[0656] Synthesis Example 17: Synthesis of Intermediate I-14

[0657] [Reaction Formula 17]

[0658]

[0659] Intermediate I-14 (12.76 g, 65%) was obtained using intermediate I-13 (17.5 g, 23.0 mmol) in the same manner as in Synthesis Example 3.

[0660] HRMS (70eV, EI+): m / z calcd for C59H44BN2O3: 839.3445, found: 839.

[0661] Elemental Analysis: C, 84%; H, 5%

[0662]

[0663] Synthesis Example 18: Synthesis of Compound 106

[0664] [Reaction Formula 18]

[0665]

[0666] Compound 106 (12.1 g, 83%) was obtained using the intermediate I-14 (12.7 g, 15.2 mmol) and bromobenzene (2.9 g, 18.2 mmol) purchased from Tokyo Chemical Industry (http: / www.tcichemicals.com / ) in the same manner as in Synthesis Example 2.

[0667] HRMS (70eV, EI+): m / z calcd for C60H38BN2O: 802.2984, found: 802.

[0668] Elemental Analysis: C, 90%; H, 5%

[0669]

[0670] Synthesis Example 19: Synthesis of Intermediate I-15

[0671] [Reaction Formula 19]

[0672]

[0673] Intermediate I-1 (50 g, 140.2 mmol) and 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (41.1 g, 140.2 mmol) purchased from Ukseung Chemical (http: / www.ukseung.co.kr / ) were used in the same manner as in Synthesis Example 2 to obtain intermediate I-15 (49.7 g, 80%).

[0674] HRMS (70eV, EI+): m / z calcd for C30H19ClN2: 442.1237, found: 442.

[0675] Elemental Analysis: C, 81%; H, 4%

[0676]

[0677] Synthesis Example 20: Synthesis of Intermediate I-16

[0678] [Reaction Formula 20]

[0679]

[0680] Intermediate I-16 (37.7 g, 63%) was obtained using intermediate I-15 (49.7 g, 112.2 mmol) in the same manner as in Synthesis Example 3.

[0681] HRMS (70eV, EI+): m / z calcd for C36H31BN2O2: 534.2479, found: 534.

[0682] Elemental Analysis: C, 81%; H, 6%

[0683]

[0684] Synthesis Example 21: Synthesis of Intermediate I-17

[0685] [Reaction Formula 21]

[0686]

[0687] Intermediate I-16 (30 g, 56.1 mmol) and 4-bromo-9-phenyl-9H-carbazole (19.7 g, 56.1 mmol) purchased from Ukseung Chemical (http: / www.ukseung.co.kr / ) were used in the same manner as in Synthesis Example 4 to obtain intermediate I-17 (27.4 g, 80%).

[0688] HRMS (70eV, EI+): m / z calcd for C42H25ClN2O: 608.1655, found: 608.

[0689] Elemental Analysis: C, 83%; H, 4%

[0690]

[0691] Synthesis Example 22: Synthesis of Intermediate I-18

[0692] [Reaction Formula 22]

[0693]

[0694] Intermediate I-18 (20.5 g, 65%) was obtained using intermediate I-17 (27 g, 44.9 mmol) in the same manner as in Synthesis Example 3.

[0695] HRMS (70eV, EI+): m / z calcd for C48H37BN2O3: 700.2897, found: 700.

[0696] Elemental Analysis: C, 82%; H, 5%

[0697]

[0698] Synthesis Example 23: Synthesis of Intermediate I-19

[0699] [Reaction Formula 23]

[0700]

[0701] Intermediate I-19 (15.2 g, 82%) was obtained using the same method as in Synthesis Example 2, using intermediate I-18 (20 g, 28.5 mmol) and bromobenzene (4.4 g, 28.5 mmol) purchased from Tokyo Chemical Industry (http: / www.tcichemicals.com / ).

[0702] HRMS (70eV, EI+): m / z calcd for C48H30N2O: 650.2358, found: 650.

[0703] Elemental Analysis: C, 89%; H, 5%

[0704]

[0705] Synthesis Example 24: Synthesis of Compound 112

[0706] [Reaction Formula 24]

[0707]

[0708] In a nitrogen environment, intermediate I-19 (10 g, 15.4 mmol) and 1-fluorotriphenylene (4.6 g, 18.4 mmol) purchased from gemchem (http: / www.ytgemchem.com) were dissolved in 0.2 L of dimethylforamide (DMF), and then potassium phosphate tribasic (3.9 g, 18.5 mmol) was added and heated and refluxed for 18 hours. After completion of the reaction, the solvent was distilled off, water was added to the reaction solution, extracted with dichloromethane (DCM), and then dried with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography to obtain compound 112 (10.1 g, 63%).

[0709] HRMS (70eV, EI+): m / z calcd for C66H40N2O: 876.3141, found: 876.

[0710] Elemental Analysis: C, 90%; H, 5%

[0711]

[0712] Synthesis Example 25: Synthesis of Intermediate I-20

[0713]

[0714] Intermediate I-20 (125 g, 91%) was obtained using 2,6-dimethoxyphenylboronic acid (100 g, 550 mmol) and 2-bromo-1,3-difluorobenzene (106 g, 550 mmol) in the same manner as in Synthesis Example 1.

[0715] HRMS (70eV, EI+): m / z calcd for C14H12F2O2: 250.0805, found: 250.

[0716] Elemental Analysis: C, 67%; H, 5%

[0717]

[0718] Synthesis Example 26: Synthesis of Intermediate I-21

[0719]

[0720] Intermediate I-20 (121 g, 486 mmol) and pyridine hydrochloride (562 g, 4,861 mmol) were added in a nitrogen atmosphere and heated at 180°C for 1 hour under reflux. After completion of the reaction, water was added to the reaction solution, extracted with ethyl acetate (EA), and then dried with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography to obtain intermediate I-21 (102 g, 95%).

[0721] HRMS (70eV, EI+): m / z calcd for C12H8F2O2: 222.0492, found: 222.

[0722] Elemental Analysis: C, 65%; H, 4%

[0723]

[0724] Synthesis Example 27: Synthesis of Intermediate I-22

[0725]

[0726] Intermediate I-22 (72.5 g, 80%) was obtained using intermediate I-21 (99.5 g, 448 mmol) in the same manner as in Synthesis Example 24.

[0727] HRMS (70eV, EI+): m / z calcd for C12H7FO2: 202.0430, found: 202.

[0728] Elemental Analysis: C, 71%; H, 3%

[0729]

[0730] Synthesis Example 28: Synthesis of Intermediate I-23

[0731]

[0732] In a nitrogen environment, intermediate I-22 (72 g, 356 mmol) was dissolved in 0.1 L of dichloromethane (DCM), and the temperature was lowered to 0℃. Pyridine (120 g, 427 mmol) was added and stirred for 30 minutes, and then tifluoromethanesulfonic anhydride (33.8 g, 427 mmol) was slowly added and stirred. After 3 hours, the temperature of the reaction solution was lowered to 0℃, water was slowly added for 30 minutes, extracted with dichloromethane (DCM), and then moisture was removed with magnesium sulfate anhydrous, filtered, and concentrated under reduced pressure. The obtained residue was purified by flash column chromatography to obtain intermediate I-23 (116 g, 98%).

[0733] HRMS (70eV, EI+): m / z calcd for C13H6F4O4S: 333.9923, found: 333.

[0734] Elemental Analysis: C, 47%; H, 2%

[0735]

[0736] Synthesis Example 29: Synthesis of Intermediate I-24

[0737]

[0738] Intermediate I-24 (69.4 g, 78%) was obtained using the same method as in Synthesis Example 1, using intermediate I-23 (113 g, 339 mmol) and phenylboronic acid (45.5 g, 373 mmol) purchased from Tokyo Chemical Industry.

[0739] HRMS (70eV, EI+): m / z calcd for C18H11FO: 262.0794, found: 262.

[0740] Elemental Analysis: C, 82%; H, 4%

[0741]

[0742] Synthesis Example 30: Synthesis of Compound 145

[0743]

[0744] Compound 145 (10.3 g, 75%) was obtained using intermediate I-19 (10 g, 15.3 mmol) and intermediate I-24 (4.8 g, 18.4 mmol) in the same manner as in Synthesis Example 24.

[0745] HRMS (70eV, EI+): m / z calcd for C66H40N2O2: 892.3090, found: 892.

[0746] Elemental Analysis: C, 89%; H, 5%

[0747]

[0748] Synthesis Example 31: Synthesis of Compound 157

[0749] [Reaction Formula 31]

[0750]

[0751] Compound 157 (7.10 g, 65%) was obtained using the intermediate I-3 (10 g, 16.3 mmol) and 1-bromodibenzo[b,d]thiophene (4.3 g, 16.3 mmol) purchased from tokyo chemical industry (http: / www.tcichemicals.com / ) in the same manner as in Synthesis Example 2.

[0752] HRMS (70eV, EI+): m / z calcd for C48H30N2S: 666.2130, found: 666.

[0753] Elemental Analysis: C, 86%; H, 5%

[0754]

[0755] Synthesis Example 32: Synthesis of Compound 159

[0756] [Reaction Formula 32]

[0757]

[0758] Compound 159 (7.72 g, 70%) was obtained using intermediate I-3 (10 g, 16.3 mmol) and 4-bromo-9,9-dimethyl-9H-fluorene (4.5 g, 16.3 mmol) purchased from sigma aldrich (http: / www.sigmaaldrich.com / ) in the same manner as in Synthesis Example 2.

[0759] HRMS (70eV, EI+): m / z calcd for C51H36N2: 676.2878, found: 676.

[0760] Elemental Analysis: C, 91%; H, 5%

[0761]

[0762] Synthesis Example 33: Synthesis of Compound R-1

[0763] [Reaction Formula 33]

[0764]

[0765] Compound R-1 was synthesized with reference to the synthetic method of patent WO2016 / 153283.

[0766] HRMS (70eV, EI+): m / z calcd for C60H36N2O2: 816.2777, found: 816.

[0767] Elemental Analysis: C, 88%; H, 4%

[0768]

[0769] Synthesis Example 34: Synthesis of Compound R-2

[0770] [Reaction Formula 34]

[0771]

[0772] Compound R-2 was synthesized with reference to the synthetic method of patent WO2016 / 153283.

[0773] HRMS (70eV, EI+): m / z calcd for C60H36N2O2: 816.2777, found: 816.

[0774] Elemental Analysis: C, 88%; H, 4%

[0775]

[0776] Synthesis Example 35: Synthesis of Compound R-3

[0777] [Reaction Formula 35]

[0778]

[0779] Compound R-3 was synthesized with reference to the synthetic method of patent WO2016 / 153283.

[0780] HRMS (70eV, EI+): m / z calcd for C60H36N2O2: 816.2777, found: 816.

[0781] Elemental Analysis: C, 88%; H, 4%

[0782]

[0783] Synthesis Example 36: Synthesis of Compound R-4

[0784] [Reaction Formula 36]

[0785]

[0786] Compound R-4 was synthesized by referring to the synthetic method of patent KR2015-0043669.

[0787] HRMS (70eV, EI+): m / z calcd for C48H30N2S: 666.2130, found: 666.

[0788] Elemental Analysis: C, 86%; H, 5%

[0789]

[0790] Synthesis Example 37: Synthesis of Compound R-5

[0791] [Reaction Formula 37]

[0792]

[0793] Compound R-5 was synthesized by referring to the synthetic method of patent KR2013-0134426.

[0794] HRMS (70eV, EI+): m / z calcd for C42H25NO2: 575.1885, found: 575.

[0795] Elemental Analysis: C, 88%; H, 4%

[0796]

[0797] Synthesis Example 38: Synthesis of Compound E-86

[0798]

[0799] Compound E-86 was synthesized with reference to the synthetic method described in Publication No. KR 10-2022-0095942 A.

[0800]

[0801] Synthesis Example 39: Synthesis of Compound D-33

[0802]

[0803] Compound E-86 was synthesized with reference to the synthetic method described in Registration Publication KR 10-1618683 B1.

[0804]

[0805] Example 1: Fabrication of a green organic light-emitting device (sole host)

[0806] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was ultrasonically washed in distilled water. After washing with distilled water, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 10 minutes using oxygen plasma and then transferred to a vacuum deposition machine. Using the ITO transparent electrode prepared in this way as an anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO substrate to form a 100Å thick hole injection layer, and Compound A was deposited on the hole injection layer to a thickness of 1350Å to form a hole transport layer. Compound B was deposited on the hole transport layer to a thickness of 350Å to form a hole transport auxiliary layer. Compound 1 synthesized in Synthesis Example 4 was used as a host on the hole transport auxiliary layer, and PhGD was doped at 10 wt% as a dopant to form a 400 Å thick light-emitting layer by vacuum deposition. Next, Compound C was deposited at a thickness of 50 Å on the light-emitting layer to form an electron transport auxiliary layer, and Compound D and Liq were simultaneously vacuum-deposited at a weight ratio of 1:1 to form an electron transport layer at a thickness of 300 Å. LiQ at 15 Å and Al at 1200 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0807] It was fabricated with the structure of ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / Compound B (350Å) / EML[Host (Compound 1) : PhGD = 90 wt% : 10 wt%](400Å) / Compound C (50Å) / Compound D:LiQ (300Å) / LiQ (15Å) / Al (1200Å).

[0808] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0809] Compound B: N-[4-(4-Dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-biphenyl]-4-amine

[0810] Compound C: 2,4-Diphenyl-6-(4',5',6'-triphenyl[1,1':2',1'':3'',1''':3''',1''''-quinquephenyl]-3''''-yl)-1,3,5-triazine

[0811] Compound D: 2-(1,1'-Biphenyl-4-yl)-4-(9,9-diphenylfluoren-4-yl)-6-phenyl-1,3,5-triazine

[0812] [PhGD]

[0813]

[0814]

[0815] Examples 2 to 8 and Comparative Examples 1 to 5

[0816] An organic light-emitting device was manufactured in the same manner as Example 1, except that the composition was changed to that described in Table 1 below.

[0817]

[0818] Example 9: Fabrication of a green organic light-emitting device (mixed host)

[0819] A glass substrate coated with a thin film of ITO (Indium Tin Oxide) was ultrasonically washed in distilled water. After washing with distilled water, it was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 10 minutes using oxygen plasma and then transferred to a vacuum deposition machine. Using the ITO transparent electrode prepared in this way as an anode, Compound A doped with 3% NDP-9 (commercially available from Novaled) was vacuum-deposited on the ITO substrate to form a 100Å thick hole injection layer, and Compound A was deposited on the hole injection layer to a thickness of 1350Å to form a hole transport layer. Compound E was deposited on the hole transport layer to a thickness of 320Å to form a hole transport auxiliary layer. Compound 1 synthesized in Synthesis Example 4 and Compound E-86 synthesized in Synthesis Example 38 were simultaneously used as hosts in a weight ratio of 7:3 on the hole transport auxiliary layer, and PtGD was doped as a dopant in an amount of 15 wt% to form a 380 Å thick light-emitting layer by vacuum deposition. Subsequently, Compound F was deposited in a thickness of 50 Å on the light-emitting layer to form an electron transport auxiliary layer, and Compound G and Liq were simultaneously vacuum-deposited in a weight ratio of 1:1 to form an electron transport layer in an amount of 300 Å thick. LiQ at 15 Å and Al at 1200 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light-emitting device.

[0820] It was fabricated with the structure of ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350Å) / Compound E (320Å) / EML[Host(Compound 1: Compound E-86 = 7:3 wt% / wt%): PtGD = 85 wt%: 15 wt%](380Å) / Compound F(50Å) / Compound G:LiQ(300Å) / LiQ(15Å) / Al(1200Å).

[0821] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

[0822] Compound F: 2-[3'-(9,9-Dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0823] Compound G: 2-[4-[4-(4'-Cyano-1,1'-biphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0824] [PtGD]

[0825]

[0826]

[0827] Examples 10 and 12

[0828] An organic light-emitting device was manufactured by changing the mixing ratio of the host to a weight ratio of 6:4.

[0829]

[0830] Example 11, Examples 13 to 18 and Comparative Examples 6 to 10

[0831] An organic light-emitting device was manufactured in the same manner as Example 9, except that the composition was changed to that described in Table 2 below.

[0832]

[0833] evaluation

[0834] The driving voltage, luminous efficiency, and lifespan characteristics of the organic light-emitting devices according to Examples 1 to 18 and Comparative Examples 1 to 10 were evaluated.

[0835] The specific measurement method is as follows, and the results are as shown in Tables 1 and 2.

[0836] (1) Measurement of changes in current density according to voltage changes

[0837] For the manufactured organic light-emitting device, the current flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while increasing the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

[0838] (2) Measurement of luminance change according to voltage change

[0839] For the manufactured organic light-emitting device, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the results were obtained.

[0840] (3) Measurement of luminous efficiency

[0841] Using the luminance, current density, and voltage measured from the above (1) and (2), the same current density (10 mA / cm 2 ) was calculated for the current efficiency (cd / A).

[0842] The luminous efficiency values ​​of Examples 1 to 8 and Comparative Examples 1 to 5 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0843] The luminous efficiency values ​​of Examples 9 to 18 and Comparative Examples 6 to 10 were calculated as relative values ​​based on Comparative Example 6 and are listed in Table 2 below.

[0844] (4) Life span measurement

[0845] Luminance (cd / m 2 ) to 24000cd / m 2 The results were obtained by maintaining the current at 97% and measuring the time until the current efficiency (cd / A) decreased to 97%.

[0846] The life measurement values ​​of Examples 1 to 8 and Comparative Examples 1 to 5 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0847] The life measurement values ​​of Examples 9 to 18 and Comparative Examples 6 to 10 were calculated as relative values ​​based on Comparative Example 6 and are listed in Table 2 below.

[0848] (5) Driving voltage measurement

[0849] 15mA / cm using a current-voltage meter (Keithley 2400) 2 The results were obtained by measuring the driving voltage of each element.

[0850] The driving voltages of Examples 1 to 8 and Comparative Examples 1 to 5 were calculated as relative values ​​based on Comparative Example 1 and are listed in Table 1 below.

[0851] The driving voltages of Examples 9 to 18 and Comparative Examples 6 to 10 were calculated as relative values ​​based on Comparative Example 6 and are listed in Table 2 below.

[0852] No. Compound Driving voltage (%) Luminous efficiency (%) Lifespan (%) Example 1 18 1200 200 Example 2 247 8189 310 Example 3 10 38 320 7190 Example 4 10 68 720 2210 Example 5 11 28 5 19 3260 Example 6 145 8320 2270 Example 7 15 78 1200 170 Example 8 15 9 831 89 125 Comparative Example 1R-1 10 0 10 0 10 0 Comparative Example 2R-2 9 4 12 225 Comparative Example 3R-3 9 0 11 150 Comparative Example 4R-4 8 8 13 3 125 Comparative Example 5R-5 11 5 7 8 115

[0853] No. Compound Driving voltage (%) Luminous efficiency (%) Lifespan (%) First compound Second compound Example 91E-8683164241 Example 101E-8678176352 Example 111D-3384180333 Example 121D-3379184222 Example 1324E-8680160389 Example 14103E-8686170200 Example 15106E-8688168222 Example 16112E-8686162333 Example 17145E-8686166444 Example 18157E-8684164189 Comparative example 6R-1E-86100100100Comparative Example 7R-2E-869612422Comparative Example 8R-3E-869211444Comparative Example 9R-4E-8691136167Comparative Example 10R-5E-8610680156

[0854] Referring to Table 1 and Table 2, it can be confirmed that the organic light-emitting devices according to Examples 1 to 18 have significantly improved driving voltage, luminous efficiency, and lifespan characteristics compared to the organic light-emitting devices according to Comparative Examples 1 to 10.

[0855] Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements made by those skilled in the art using the basic concept of the present invention defined in the following claims also fall within the scope of the present invention.

Claims

1. A compound for an organic optoelectronic device represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, X 1 Silver O, S, CR a R b , or SiR c R d And, Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group, R a , R b , R c and R d are each independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, R 1 Inland R 19 are each independently hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkylsilyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

2. In paragraph 1, Above Ar 1 and Ar 2 A compound for an organic optoelectronic device, wherein each independently represents 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 fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted dibenzosilolyl group.

3. In paragraph 1, Above Ar 1 and Ar 2 A compound for an organic optoelectronic device, wherein each of the substituents is independently selected from the substituents listed in Group I below: [Group I] In the above group I, R 20 Inland R 22 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group, m2 is an integer between 1 and 5, m3 is one of the integers 1 to 4, m4 is one of the integers 1 to 3, * is a connection point.

4. In paragraph 1, Above R 1 Inland R 19 A compound for an organic optoelectronic device, wherein each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted trimethylsilyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzosilolyl group, or a combination thereof.

5. In paragraph 1, Above R 1 Inland R 19 is a compound for an organic optoelectronic device, wherein each independently represents hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted n-propyl group, a substituted or unsubstituted iso-propyl group, a substituted or unsubstituted n-butyl group, a substituted or unsubstituted iso-butyl group, a substituted or unsubstituted sec-butyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted trimethylsilyl group, or one of the substituents listed in Group II below: [Group II] In the above group II, R 20 Inland R 22 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group, m2 is an integer between 1 and 5, m3 is one of the integers 1 to 4, m4 is one of the integers 1 to 3, * is a connection point.

6. In paragraph 1, A compound for organic optoelectronic devices, selected from the compounds listed in Group 1 below: [Group 1] In the above group 1, Dn means the number of deuterium atoms substituted.

7. Containing a first compound and a second compound, The above first compound is a compound for an organic optoelectronic device according to claim 1, The second compound is a composition for an organic optoelectronic device represented by the following chemical formula 2: [Chemical formula 2] In the above chemical formula 2, Z 1 Inland Z 6 are each independently N or CL a -R e And, Z 1 Inland Z 6 At least two of them are N, L a are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, R e are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group or a combination thereof, R e are each independently present or adjacent groups are linked to form a substituted or unsubstituted aliphatic, aromatic or heteroaromatic monocyclic or polycyclic ring.

8. In paragraph 7, The above chemical formula 2 is a composition for an organic optoelectronic device represented by any one of the following chemical formulas 2A to 2C: [Chemical Formula 2A] [Chemical Formula 2B] [Chemical Formula 2C] In the above chemical formulas 2A to 2C, Z 1 , Z 3 and Z 5 are each independently N or CL a -R e And, Z 1 , Z 3 and Z 5 At least two of them are N, X 2 is O, S or NR f And, L a , and L 3 Inside L 5 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof, R e , R f and R 23 Inland R 44 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, halogen, cyano group or a combination thereof, R 23 Inland R 30 are each independently present or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, R 31 Inland R 35 are each independently present or adjacent groups are connected to form a substituted or unsubstituted aromatic monocyclic or polycyclic ring, Ar 3 and Ar 4 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, R e , Ar 3 and Ar 4 exist independently of each other, or R e , Ar 3 and Ar 4 Adjacent groups are connected to form a substituted or unsubstituted aromatic or heteroaromatic monocyclic or polycyclic ring, m5 and m6 are each independently an integer from 1 to 3.

9. In paragraph 7, The above chemical formula 2 is a composition for an organic optoelectronic device represented by the following chemical formula 2A-ⅩⅣ or chemical formula 2C-Ⅰ: [Chemical Formula 2A-Ⅳ] [Chemical Formula 2C-Ⅰ] In the above chemical formulas 2A-ⅩⅣ and 2C-Ⅰ, L a , and L 3 Inside L 6 are each independently a single bond or a substituted or unsubstituted C6 to C12 aryl group, Ar 3 , Ar 4 and Ar 6 are 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 triphenylene group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group, R 23 Inland R 28 , R 61 Inland R 64 are each independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C12 aryl group.

10. Positive and negative poles facing each other, Comprising at least one organic layer positioned between the anode and the cathode, The organic layer is a compound for an organic optoelectronic device according to any one of claims 1 to 6; or An organic optoelectronic device comprising a composition for an organic optoelectronic device according to any one of claims 7 to 9.

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

12. A display device comprising an organic optoelectronic device according to Article 10.

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