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

Abstract

The present invention provides a compound for an organic optoelectronic device, a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device. Specifically, the present invention provides a compound for an organic optoelectronic device represented by Chemical Formula 1, a composition for an organic optoelectronic device containing the compound, an organic optoelectronic device, and a display device. The details of Chemical Formula 1 are as defined in the specification.

Description

[0001] Citations of Related Applications

[0002] This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0126582, filed on September 24, 2021, in the Korean Intellectual Property Office, and Korean Patent Application No. 10-2022-0120144, filed on September 22, 2022, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present invention discloses a compound for an organic photoelectric device, a composition for an organic photoelectric device, an organic photoelectric device and a display device. Background Art

[0004] An organic photovoltaic device (organic photodiode) is a device that converts electrical energy into light energy (or vice versa).

[0005] Organic optoelectronic devices can be classified into the following categories based on their driving principles: a photoelectric device in which excitons generated by light energy are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to generate electrical energy; and a light-emitting device in which light energy is generated from electrical energy by supplying voltage or current to electrodes.

[0006] Examples of the organic optoelectronic device include an organic optoelectronic device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0007] Among them, organic light emitting diodes (OLEDs) have recently attracted attention due to the increasing demand for flat panel displays. OLEDs convert electrical energy into light, and the organic material disposed between electrodes has a significant impact on the performance of OLEDs. Summary of the Invention

[0008] One embodiment provides a compound for an organic photoelectric device, which can realize an organic photoelectric device with low driving, high efficiency, and long lifespan.

[0009] Another embodiment provides a composition for an organic photoelectric device, which can realize an organic photoelectric device with high efficiency and long lifespan.

[0010] Another embodiment provides an organic photoelectric device including the compound.

[0011] Another embodiment provides a display device including the organic optoelectronic device.

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

[0013] [Chemical Formula 1]

[0014]

[0015] In Chemical Formula 1,

[0016] Ar 1 is a substituted or unsubstituted C6 to C30 non-fused aromatic group,

[0017] R 1 are each independently hydrogen, deuterium, or unsubstituted C6 to C12 aryl,

[0018] R 2 to R 5 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

[0019] m1 to m5 are each independently one of integers from 1 to 4.

[0020] According to another embodiment, provided is a composition for an organic optoelectronic device including a first compound and a second compound.

[0021] The first compound may be the same as described above, and the second compound may be the compound for an organic photoelectric device represented by Chemical Formula 2; or a compound for an organic photoelectric device represented by a combination of Chemical Formula 3 and Chemical Formula 4.

[0022] [Chemical Formula 2]

[0023]

[0024] In Chemical Formula 2,

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

[0026] L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0027] R 11 to R 21 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group,

[0028] m6 and m7 are each independently one of integers from 1 to 3,

[0029] m8 is one of integers from 1 to 4, and

[0030] n is an integer from 0 to 2;

[0031]

[0032] Among them, in Chemical Formula 3 and Chemical Formula 4,

[0033] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0034] Each of adjacent two of b1* to b4* in Chemical Formula 3 is a connecting carbon (C) connected to * in Chemical Formula 4,

[0035] And the remaining two of b1* to b4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are each independently CL a -R a ,

[0036] L a 、L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0037] R a and R 22 to R 29 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0038] According to another embodiment, an organic photoelectric device includes an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the compound for an organic photoelectric device or the composition for an organic photoelectric device.

[0039] According to another embodiment, a display device including an organic optoelectronic device is provided.

[0040] Organic photoelectric devices with low drive, high efficiency and long life can be realized. BRIEF DESCRIPTION OF THE DRAWINGS

[0041] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment. DETAILED DESCRIPTION

[0042] Hereinafter, embodiments of the present invention will be described in detail. However, these embodiments are exemplary, and the present invention is not limited thereto, and the present invention is defined by the scope of the claims.

[0043] As used herein, when no definition is otherwise provided, "substituted" means that at least one hydrogen of a substituent or compound is replaced with deuterium, halogen, hydroxyl, amino, substituted or unsubstituted C1 to C30 amine, nitro, substituted or unsubstituted C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, C1 to C20 alkoxy, C1 to C10 trifluoroalkyl, cyano, or a combination thereof.

[0044] In one embodiment of the present invention, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound with deuterium, C1 to C30 alkyl, C1 to C10 alkylsilyl, C6 to C30 arylsilyl, C3 to C30 cycloalkyl, C3 to C30 heterocycloalkyl, C6 to C30 aryl, C2 to C30 heteroaryl, or cyano. Furthermore, in a specific embodiment of the present invention, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound with deuterium, C1 to C20 alkyl, C6 to C30 aryl, or cyano. Furthermore, in a specific embodiment of the present invention, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound with deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano. Furthermore, in a specific embodiment of the present invention, "substituted" refers to the replacement of at least one hydrogen of a substituent or compound with deuterium, cyano, methyl, ethyl, propyl, butyl, phenyl, biphenyl, terphenyl, or naphthyl.

[0045] As used herein, "unsubstituted" means that a hydrogen atom is not replaced by another substituent and the hydrogen atom remains.

[0046] As used herein, "hydrogen substitution (—H)" may include "deuterium substitution (—D)" or "tritium substitution (—T)."

[0047] As used herein, when no definition is otherwise provided, "hetero" means containing one to three heteroatoms selected from N, O, S, P and Si and the remaining carbon in one functional group.

[0048] As used herein, “aryl” refers to a group containing at least one hydrocarbon aromatic moiety, and may include a group in which all elements of the hydrocarbon aromatic moiety have p-orbitals forming a conjugation, such as phenyl, naphthyl, etc., a group in which two or more hydrocarbon aromatic moieties can be linked by a σ bond, such as biphenyl, terphenyl, quaterphenyl, etc., and a group in which two or more hydrocarbon aromatic moieties are directly or indirectly fused to provide a non-aromatic fused ring, such as fluorenyl, etc.

[0049] Aryl groups can include monocyclic, polycyclic, or fused-ring polycyclic (ie, rings that share adjacent pairs of carbon atoms) functional groups.

[0050] As used herein, "heterocyclic group" is a general concept of heteroaryl, and may contain at least one heteroatom selected from N, O, S, P, and Si in place of carbon (C) in cyclic compounds such as aryl, cycloalkyl, fused rings thereof, or combinations thereof. When the heterocyclic group is a fused ring, the entire ring or each ring of the heterocyclic group may contain one or more heteroatoms.

[0051] For example, "heteroaryl" refers to an aryl group containing at least one heteroatom selected from N, O, S, P, and Si. Two or more heteroaryl groups are directly linked by a sigma bond, or when the heteroaryl group contains two or more rings, the two or more rings may be fused. When the heteroaryl group is a fused ring, each ring may contain 1 to 3 heteroatoms.

[0052] More specifically, the substituted or unsubstituted C6 to C30 aryl group may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthyl 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 chrysyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or a combination thereof, but is not limited thereto.

[0053] More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group may be a substituted or unsubstituted furyl group, a substituted or unsubstituted phenylthio 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, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl, or a combination thereof, but not limited thereto.

[0054] As used herein, the term "non-fused aryl" refers to a monocyclic aryl group in which all carbon atoms of the hydrocarbon aromatic portion have p-orbitals and these p-orbitals form a conjugation, or an aryl group in which the above monocyclic aryl groups are connected by sigma bonds.

[0055] More specifically, the substituted or unsubstituted C6 to C30 non-condensed aryl group may 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, or a combination thereof, but is not limited thereto.

[0056] In this specification, hole characteristics refer to the ability to donate electrons to form holes when an electric field is applied, and due to the conductive characteristics according to the highest occupied molecular orbital (HOMO) energy level, the holes formed in the anode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0057] In addition, electronic properties refer to the ability to accept electrons when an electric field is applied, and due to the conductive properties according to the lowest unoccupied molecular orbital (LUMO) energy level, electrons formed in the cathode can be easily injected into the light-emitting layer and transported in the light-emitting layer.

[0058] Hereinafter, a compound for an organic photoelectric device according to one embodiment is described.

[0059] The compound for an organic photoelectric device according to one embodiment is represented by Chemical Formula 1.

[0060] [Chemical Formula 1]

[0061]

[0062] In Chemical Formula 1,

[0063] Ar 1 is a substituted or unsubstituted C6 to C30 non-fused aromatic group,

[0064] R 1 are each independently hydrogen, deuterium, or unsubstituted C6 to C12 aryl,

[0065] R 2 to R 5 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amine, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof, and

[0066] m1 to m5 are each independently one of integers from 1 to 4.

[0067] In the compound represented by Chemical Formula 1, in the N direction centered on triazine, one carbazole group is directly connected to triazine without a linking group, another carbazole group is connected to triazine in the N direction through an o-phenylene group, and the substituted or unsubstituted C6 to C30 non-condensed aryl group may have a substituted structure.

[0068] The carbazole group is directly linked to the triazine in the N direction (ie, the 9th position) without a linking group, so that it has a relatively deep LUMO energy level, which is beneficial for electron injection and movement.

[0069] Furthermore, another carbazole group is attached to the triazine in the N direction (i.e., at the 9th position), thereby breaking the π-bond via the C-N bond, allowing the electron cloud between the HOMO-LUMO to be clearly localized into the hole-transporting and electron-transporting moieties.

[0070] In particular, since the HOMO-LUMO band gap is widened due to the o-phenylene group, the efficiency improvement effect can be maximized, and the steric hindrance of the molecules is increased, so that the deposition temperature can be relatively not high, which is advantageous in the process.

[0071] Furthermore, since the substituted or unsubstituted C6 to C30 non-fused aryl group is substituted, an organic optoelectronic device with low driving force, high efficiency, and long lifetime can be manufactured by controlling the electron transport capability in the electron transport layer to have appropriate mobility and charge balance.

[0072] Ar in Chemical Formula 1 1 may be a substituted or unsubstituted C6 to C30 non-fused aryl group, and

[0073] The substituted or unsubstituted C6 to C30 non-condensed aryl group may be, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quaterphenyl group, or a combination thereof.

[0074] For example, the substituted or unsubstituted C6 to C30 non-condensed aryl group may be selected from the substituents of Group I.

[0075] [Group I]

[0076]

[0077] In group I, * is the connection point, and

[0078] The substituents of Group I may be unsubstituted or substituted with another substituent.

[0079] The additional substituent may be deuterium, cyano, substituted or unsubstituted C1 to C10 alkyl, or substituted or unsubstituted C6 to C12 aryl.

[0080] In one example, the additional substituent can be deuterium, a substituted or unsubstituted C1 to C5 alkyl, a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, or a substituted or unsubstituted naphthyl.

[0081] For example, R 1 It may be hydrogen, deuterium, or unsubstituted phenyl.

[0082] For example, R 2 to R 5 Each may independently be hydrogen, deuterium, cyano, or a substituted or unsubstituted C6 to C12 aryl group.

[0083] In the most specific embodiment, the compound for an organic photoelectric device represented by Chemical Formula 1 may be one selected from Group 1, but is not limited thereto.

[0084] [Group 1]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] A composition for an organic photoelectric device according to another embodiment includes a first compound and a second compound, wherein the first compound is the above-mentioned compound for an organic photoelectric device, and the second compound may be a compound for an organic photoelectric device represented by Chemical Formula 2; or a compound for an organic photoelectric device represented by a combination of Chemical Formula 3 and Chemical Formula 4.

[0093] [Chemical Formula 2]

[0094]

[0095] In Chemical Formula 2,

[0096] Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0097] L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

[0098] R 11 to R 21 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group,

[0099] m6 and m7 are each independently one of integers from 1 to 3,

[0100] m8 is one of integers from 1 to 4, and

[0101] n is an integer from 0 to 2;

[0102]

[0103] Among them, in Chemical Formula 3 and Chemical Formula 4,

[0104] Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

[0105] Each of adjacent two of b1* to b4* in Chemical Formula 3 is a connecting carbon (C) connected to * in Chemical Formula 4,

[0106] And the remaining two of b1* to b4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are each independently CLa -R a As used herein, the term "linking carbon" refers to the shared carbon to which the fused ring is attached.

[0107] L a 、L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, and

[0108] R a and R 22 to R 29 Each is independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted amino, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclic group.

[0109] The second compound may be used together with the first compound in the light emitting layer to improve light emitting efficiency and lifespan characteristics by increasing charge mobility and increasing stability.

[0110] For example, Ar in Chemical Formula 2 2 and Ar 3 may each independently be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0111] Ar 2 and Ar 3 At least one of may be a C6 to C20 aryl group substituted by deuterium or a C2 to C30 heterocyclic group substituted by deuterium.

[0112] For example, R in Formula 2 11 to R 21 may each independently be hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0113] R 11 to R 21 At least one of may be deuterium, a C1 to C30 alkyl group substituted with deuterium, a C6 to C30 aryl group substituted with deuterium, or a C2 to C30 heterocyclic group substituted with deuterium.

[0114] For example, Ar in Chemical Formula 2 2 and Ar 3 At least one of may be a C6 to C20 aryl group substituted by deuterium, or a C2 to C30 heterocyclic group substituted by deuterium, and

[0115] R in Chemical Formula 2 11 to R21 At least one of may be deuterium, a C1 to C30 alkyl group substituted with deuterium, a C6 to C30 aryl group substituted with deuterium, or a C2 to C30 heterocyclic group substituted with deuterium.

[0116] For example, Ar in Formulas 3 and 4 4 and Ar 5 may each independently be a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0117] Ar 4 and Ar 5 At least one of them may be a C6 to C20 aryl group substituted by deuterium, or a C2 to C30 heterocyclic group substituted by deuterium.

[0118] For example, in Chemical Formulas 3 and 4, R a and R 22 to R 29 may each independently be hydrogen, deuterium, a cyano group, a halogen group, a substituted or unsubstituted amino group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

[0119] R a and R 22 to R 29 At least one of may be deuterium, a C1 to C30 alkyl group substituted with deuterium, a C6 to C30 aryl group substituted with deuterium, or a C2 to C30 heterocyclic group substituted with deuterium.

[0120] For example, Ar in Formulas 3 and 4 4 and Ar 5 At least one of may be a C6 to C20 aryl group substituted by deuterium, or a C2 to C30 heterocyclic group substituted by deuterium, and

[0121] R a and R 22 to R 29 At least one of may be deuterium, a C1 to C30 alkyl group substituted with deuterium, a C6 to C30 aryl group substituted with deuterium, or a C2 to C30 heterocyclic group substituted with deuterium.

[0122] In a specific example, Ar in Chemical Formula 2 2 and Ar 3 each independently may 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 dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted fluorenyl group.

[0123] L in Chemical Formula 2 1 and L 2 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group,

[0124] R in Chemical Formula 2 11 to R 21 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0125] n can be 0 or 1.

[0126] For example, Ar in chemical formula 2 2 and Ar 3 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

[0127] Ar 2 and Ar 3 At least one of the groups may be a deuterium-substituted phenyl group, a deuterium-substituted biphenyl group, a deuterium-substituted terphenyl group, a deuterium-substituted naphthyl group, a deuterium-substituted anthracenyl group, a deuterium-substituted triphenylene group, a deuterium-substituted carbazolyl group, a deuterium-substituted dibenzothiophenyl group, a deuterium-substituted dibenzofuranyl group or a deuterium-substituted fluorenyl group.

[0128] For example, R in Formula 2 11 to R 21 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, and

[0129] R 11 to R 21 At least one of may be deuterium, or a C6 to C12 aryl group substituted with deuterium.

[0130] For example, Ar in Chemical Formula 2 2 and Ar 3 At least one of the groups may be a deuterium-substituted phenyl group, a deuterium-substituted biphenyl group, a deuterium-substituted terphenyl group, a deuterium-substituted naphthyl group, a deuterium-substituted anthracenyl group, a deuterium-substituted triphenylene group, a deuterium-substituted carbazolyl group, a deuterium-substituted dibenzothienyl group, a deuterium-substituted dibenzofuranyl group, or a deuterium-substituted fluorenyl group, and

[0131] R in Chemical Formula 2 11 to R 21 At least one of may be deuterium or a C6 to C12 aryl group substituted with deuterium.

[0132] For example, “substituted” in Chemical Formula 2 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.

[0133] In one embodiment of the present invention, Chemical Formula 2 can be represented by Chemical Formula 2-1 to Chemical Formula

[0134] One of the expressions in Equation 2-15.

[0135]

[0136]

[0137] In Chemical Formulas 2-1 to 2-15, R 11 to R 21 may be each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, m6 and m7 may each independently be one of integers from 1 to 3, m8 may be one of integers from 1 to 4, and *-L 1 -Ar 2 and *-L 2 -Ar 3 Each may independently be one of the substituents in Group II.

[0138] [Group II]

[0139]

[0140] In Group II,

[0141] R 6 to R 8 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl, substituted or unsubstituted C6 to C18 aryl, or substituted or unsubstituted C2 to C30 heteroaryl,

[0142] m8 is an integer from 1 to 5,

[0143] m9 is an integer from 1 to 4,

[0144] m10 is one of integers from 1 to 3, and

[0145] * is the connection point.

[0146] In one embodiment, Chemical Formula 2 may be represented by Chemical Formula 2-8.

[0147] In addition, *-L in Chemical Formula 2-8 1 -Ar 2 and *-L 2 -Ar 3Each may be independently selected from Group II, and may be, for example, any one of C-1, C-2, C-3, C-4, C-7, C-8, and C-9.

[0148] For example, the second compound represented by the combination of Chemical Formula 3 and Chemical Formula 4 may be represented by any one of Chemical Formula 3A, Chemical Formula 3B, Chemical Formula 3C, Chemical Formula 3D, and Chemical Formula 3E.

[0149]

[0150] In Chemical Formulae 3A to 3E, Ar 4 、Ar 5 、L 3 、L 4 and R 22 to R 29 Same as above,

[0151] L a1 To L a4 With L 3 and L 4 The definition of is the same as

[0152] R a1 to R a4 With R 22 to R 29 The definition is the same.

[0153] For example, Ar in Formulas 3 and 4 4 and Ar 5 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0154] R a1 to R a4 and R 22 to R 29 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0155] In one embodiment of the present invention, Ar in Chemical Formulas 3 and 4 4 and Ar 5 The substituents may be each independently selected from group II.

[0156] In an exemplary embodiment, R a1 to R a4 and R22 to R 29 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0157] For example, R a1 to R a4 and R 22 to R 29 may each independently be hydrogen, deuterium, cyano or substituted or unsubstituted phenyl, and

[0158] In a specific embodiment, R a1 to R a4 and R 22 to R 29 and may each independently be hydrogen, deuterium or unsubstituted phenyl.

[0159] For example, Ar in Formulas 3 and 4 4 and Ar 5 may each independently be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

[0160] Ar 4 and Ar 5 At least one of the groups may be a deuterium-substituted phenyl group, a deuterium-substituted biphenyl group, a deuterium-substituted pyridyl group, a deuterium-substituted carbazolyl group, a deuterium-substituted dibenzofuranyl group, a deuterium-substituted dibenzofuranyl group, or a deuterium-substituted dibenzothiophenyl group.

[0161] For example, in formulas 3 and 4, R a1 to R a4 and R 22 to R 29 may each 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, and

[0162] R a1 to R a4 and R 22 to R 29 At least one of the groups may be a deuterium-substituted phenyl group, a deuterium-substituted biphenyl group, a deuterium-substituted pyridyl group, a deuterium-substituted carbazolyl group, a deuterium-substituted dibenzofuranyl group, a deuterium-substituted dibenzofuranyl group, or a deuterium-substituted dibenzothiophenyl group.

[0163] For example, Ar in Chemical Formula 3 and Chemical Formula 4 4 and Ar 5 At least one of the following may be a deuterium-substituted phenyl group, a deuterium-substituted biphenyl group, a deuterium-substituted pyridyl group, a deuterium-substituted carbazolyl group, a deuterium-substituted dibenzofuranyl group, a deuterium-substituted dibenzofuranyl group, or a deuterium-substituted dibenzothienyl group, and

[0164] R a1 to R a4 and R 22 to R 29 At least one of the groups may be a deuterium-substituted phenyl group, a deuterium-substituted biphenyl group, a deuterium-substituted pyridyl group, a deuterium-substituted carbazolyl group, a deuterium-substituted dibenzofuranyl group, a deuterium-substituted dibenzofuranyl group, or a deuterium-substituted dibenzothiophenyl group.

[0165] In a specific embodiment of the present invention, the second compound can be represented by Chemical Formula 2-8, and in Chemical Formula 2-8, Ar 2 and Ar 3 L may be each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group. 1 and L 2 may each independently be a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and R 11 to R 20 Each of them may independently be hydrogen, deuterium, cyano, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted dibenzothiophenyl.

[0166] In another embodiment of the present invention, the second compound can be represented by Chemical Formula 3C, wherein in Chemical Formula 3C, L a1 and L a2 Can be a single bond, L 3 and L 4 may be each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 22 to R 29 , R a1 and R a2 can each be hydrogen, deuterium or phenyl, and Ar 4 and Ar 5 Each independently may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

[0167] For example, the second compound may be one of the compounds selected from Group 2, but is not limited thereto.

[0168] [Group 2]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183] For example, the first compound and the second compound can be included in a weight ratio of about 1:99 to about 99:1. Within this range, the electron transport ability of the first compound and the hole transport ability of the second compound can be used to adjust the desired weight ratio to achieve bipolar characteristics and thus improve efficiency and life. Within this range, they can be included, for example, in a weight ratio of about 10:90 to about 90:10, or about 20:80 to about 80:20, such as about 20:80 to about 70:30, about 20:80 to about 60:40, and about 20:80 to about 50:50. As a specific example, they can be included in a weight ratio of about 20:80, about 30:70, or about 40:60.

[0184] In addition to the above-mentioned first and second compounds, one or more compounds may be further included.

[0185] For example, the above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device may further include a dopant.

[0186] 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.

[0187] A dopant is a material mixed in small amounts with a compound used in an organic optoelectronic device to induce light emission, and is typically a material such as a metal complex that emits light by multiple excitations to a triplet state or higher. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and one or more types thereof may be used.

[0188] Examples of the dopant may be a phosphorescent dopant, and examples of the phosphorescent dopant may be an organometallic compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. The phosphorescent dopant may be, for example, a compound represented by the chemical formula Z, but is not limited thereto.

[0189] [Chemical formula Z]

[0190] LMX

[0191] In the chemical formula Z, M is a metal, and L and X are the same as or different from each other and are ligands that form a coordination compound with M.

[0192] M can be, for example, Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, and L and X can be, for example, bidentate ligands.

[0193] Examples of the ligand represented by L and X may be selected from the chemical formulae of Group A, but are not limited thereto.

[0194] [Group A]

[0195]

[0196] In Group A,

[0197] R 300 to R 302 are each independently hydrogen, deuterium, a C1 to C30 alkyl group which may be substituted with a halogen, a C6 to C30 aryl group which may be substituted with a C1 to C30 alkyl group, or a halogen, and

[0198] R 303 to R 324Each is independently hydrogen, deuterium, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C1 to C30 alkoxy, substituted or unsubstituted C3 to C30 cycloalkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted C6 to C30 aryl, substituted or unsubstituted C1 to C30 heteroaryl, substituted or unsubstituted C1 to C30 amino, substituted or unsubstituted C6 to C30 arylamino, SF5, a trialkylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group, a dialkylarylsilyl group having a substituted or unsubstituted C1 to C30 alkyl group and a C6 to C30 aryl group, or a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

[0199] As an example, it may include a dopant represented by Chemical Formula V.

[0200] [Chemical Formula V]

[0201]

[0202] In Chemical Formula V,

[0203] R 101 to R 116 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or SiR 132 R 133 R 134 ,

[0204] R 132 to 134 are each independently C1 to C6 alkyl,

[0205] R 101 to R 116 At least one of them is a functional group represented by Chemical Formula V-1,

[0206] L 100 It is a bidentate ligand of a monovalent anion and is coordinated to iridium through the lone pair of electrons of carbon or heteroatoms.

[0207] n1 and n2 are each independently any one of integers from 0 to 3, and n1+n2 is any one of integers from 1 to 3,

[0208] [Chemical Formula V-1]

[0209]

[0210] Among them, in Chemical Formula V-1,

[0211] R 135 to R 139are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,as well as

[0212] * indicates a moiety attached to a carbon atom.

[0213] As an example, a dopant represented by Chemical Formula Z-1 may be included.

[0214] [Chemical Formula Z-1]

[0215]

[0216] In the chemical formula Z-1, rings A, B, C and D each independently represent a 5-membered or 6-membered carbocyclic or heterocyclic ring;

[0217] R A 、R B 、R C and R D Each independently represents mono-, di-, tri-, or tetra-substituted, or unsubstituted;

[0218] L B 、L C , and L D Each is independently selected from a single bond, BR, NR, PR, O, S, Se, C=O, S=O, SO2, CRR', SiRR', GeRR', and combinations thereof;

[0219] When nA is 1, L E is selected from a single bond, 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; and

[0220] R A 、R B 、R C 、R D , R and R' are each independently selected from hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof; any adjacent R A 、R B 、R C 、R D , R and R' are optionally linked to each other to provide a ring; X B 、X C、X D and X E are each independently selected from carbon and nitrogen; and Q 1 , Q 2 , Q 3 and Q 4 Each represents oxygen or a single bond.

[0221] The dopant according to one embodiment may be a platinum complex, and may be represented, for example, by Chemical Formula VI.

[0222] [Chemical Formula VI]

[0223]

[0224] In Chemical Formula VI,

[0225] X 100 Selected from O, S and NR 131 ,

[0226] R 117 to R 131 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C10 alkyl, substituted or unsubstituted C6 to C20 aryl, or -SiR 132 R 133 R 134 ,

[0227] R 132 to 134 are each independently C1 to C6 alkyl, and

[0228] R 117 to R 131 At least one of them is -SiR 132 R 133 R 134 or tert-butyl.

[0229] Hereinafter, an organic photoelectric device including the above-mentioned compound for an organic photoelectric device or the composition for an organic photoelectric device is described.

[0230] The organic photoelectric device may be any device that converts electrical energy into light energy, and vice versa, without particular limitation, and may be, for example, an organic photoelectric device, an organic light emitting diode, an organic solar cell, and an organic photosensitive drum.

[0231] Herein, an organic light emitting diode as one example of an organic photoelectric device is described with reference to the accompanying drawings.

[0232] Figure 1 is a cross-sectional view showing an organic light emitting diode according to an embodiment.

[0233] Reference Figure 1, an organic light emitting diode 100 according to one embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 disposed between the anode 120 and the cathode 110 .

[0234] The anode 120 may be made of a conductor having a large work function to facilitate hole injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 may be, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; a metal oxide such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), or the like; a combination of a metal and an oxide such as ZnO and Al or SnO2 and Sb; or a conductive polymer such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (PEDOT), polypyrrole, and polyaniline, but is not limited thereto.

[0235] The cathode 110 may be made of a conductor with a small work function to facilitate electron injection, and may be, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 may be, 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, and BaF2 / Ca, but is not limited thereto.

[0236] The organic layer 105 may include the above-described compound for an organic photoelectric device or composition for an organic photoelectric device.

[0237] The organic layer 105 may include a light-emitting layer 130 , and the light-emitting layer 130 may include the above-described compound for an organic photoelectric device or composition for an organic photoelectric device.

[0238] The composition for an organic photoelectric device further including a dopant may be, for example, a composition emitting red light or green light.

[0239] For example, the light emitting layer 130 may include the above-described compound for an organic photoelectric device or composition for an organic photoelectric device as a phosphorescent host.

[0240] The organic layer may further include a charge transport region in addition to the light emitting layer.

[0241] The charge transport region may be, for example, a hole transport region 140 .

[0242] The hole transport region 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.

[0243] Specifically, the hole transport region 140 may include a hole transport layer between the anode 120 and the light-emitting layer 130, and a hole transport auxiliary layer between the light-emitting layer 130 and the hole transport layer, and at least one of the compounds of group B may be contained in at least one of the hole transport layer and the hole transport auxiliary layer.

[0244] [Group B]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250] In the hole transport region 140 , in addition to this compound, known compounds disclosed in US Pat. No. 5,061,569 A, JP 1993-009471 A, WO 1995-009147 A1, JP 1995-126615 A, JP 1998-095973 A, etc., and compounds similar thereto can be used.

[0251] In addition, the charge transport region may be, for example, the electron transport region 150 .

[0252] The electron transport region 150 may further increase electron injection and / or electron mobility and block holes between the cathode 110 and the light emitting layer 130 .

[0253] Specifically, the electron transport region 150 may include an electron transport layer between the cathode 110 and the light emitting layer 130 and an electron transport auxiliary layer between the light emitting layer 130 and the electron transport layer, and at least one of the compounds of group C may be contained in at least one of the electron transport layer and the electron transport auxiliary layer.

[0254] [Group C]

[0255]

[0256]

[0257]

[0258]

[0259] One embodiment may be an organic light emitting diode including a light emitting layer as an organic layer.

[0260] Another embodiment may provide an organic light emitting diode including a light emitting layer and a hole transport region as organic layers.

[0261] Another embodiment may provide an organic light emitting diode including a light emitting layer and an electron transport region as an organic layer.

[0262] like Figure 1 As shown, the organic light emitting diode according to the embodiment of the present invention may include a hole transport region 140 and an electron transport region 150 in addition to the light emitting layer 130 as the organic layer 105 .

[0263] On the other hand, the organic light emitting diode may further include an electron injection layer (not shown), a hole injection layer (not shown), and the like in addition to the light emitting layer of the above-mentioned organic layers.

[0264] The organic light emitting diode 100 may be manufactured by forming an anode or cathode on a substrate, forming an organic layer using a dry film forming method such as vacuum deposition (evaporation), sputtering, plasma plating, and ion plating, and forming the cathode or anode thereon.

[0265] Organic light emitting diodes can be applied to organic light emitting display devices.

[0266] Hereinafter, the embodiments will be described in more detail with reference to Examples. However, these Examples are exemplary, and the present scope is not limited thereto.

[0267] Hereinafter, unless otherwise specified, starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich Co. Ltd., TCI Inc., Tokyo chemical industry or P&H tech, or synthesized by known methods.

[0268] (Preparation of Compounds for Organic Photoelectric Devices)

[0269] The compounds presented as more specific examples of the compounds of the present invention were synthesized by the following steps.

[0270] Synthesis Example 1: Synthesis of Compound A-4

[0271] [Reaction Scheme 1]

[0272]

[0273] Step 1: Synthesis of intermediate Int-01

[0274] 2,4-Dichloro-6-(biphenyl-4-yl)-1,3,5-triazine (39.2 g, 129.78 mmol), carbazole (15.5 g, 92.7 mmol), and sodium tert-butoxide (9.35 g, 97.3 mmol) were placed in a round-bottom flask and stirred with 650 ml of THF at room temperature for 12 hours. The resulting solid was filtered, and then stirred with the aqueous layer for 30 minutes. The resulting mixture was filtered and dried to obtain 28 g (70%) of Intermediate Int-01.

[0275] Step 2: Synthesis of Compound A-4

[0276] 15 g (34.65 mmol) of Intermediate Int-01, 9.95 g (34.65 mmol) of 2-(9H-carbazol-9-yl)phenylboronic acid (CAS No. 1189047-28-6), 2 g (1.73 mmol) of Pd(PPh ) , 9.58 g (69.3 mmol) of K CO , 400 ml of toluene, and 200 ml of distilled water were placed in a flask and stirred under reflux for 12 hours. When the reaction was complete, the resultant was cooled to room temperature, and the solid produced therein was filtered, washed with acetone, and dried. 16.4 g (yield: 74%) of Compound A-4 was obtained.

[0277] Synthesis Example 2: Synthesis of Intermediate Int-04

[0278] [Reaction Scheme 2]

[0279]

[0280] Step 1: Synthesis of intermediate Int-02

[0281] 3-Bromocarbazole (15 g, 60.95 mmol), phenylboronic acid (11.44 g, 73.14 mmol), K CO (21.06 g, 152.38 mmol) and Pd (PPh) (3.52 g, 3.05 mmol) were placed in a round-bottom flask and dissolved in 200 ml of THF and 75 ml of distilled water, followed by stirring at 60° C. under reflux for 12 hours. When the reaction was complete, after removing the aqueous layer therefrom, the residue was treated by column chromatography (hexane: DCM (20%)) to obtain 12.3 g (83%) of Intermediate Int-02.

[0282] Step 2: Synthesis of intermediate Int-03

[0283] Intermediate Int-02 (50 g, 205.51 mmol), 1-bromo-2-fluorobenzene (36 g, 205.51 mmol) and K 3 PO 4 (65.44 g, 308.26 mmol) were placed in a round-bottom flask, and 500 ml of DMF was added thereto, followed by stirring at 130° C. under reflux for 12 hours. When the reaction was complete, the resultant was treated by column chromatography (hexane:DCM (10%)) to obtain 65.3 g (80%) of Intermediate Int-03.

[0284] Step 3: Synthesis of intermediate Int-04

[0285] Intermediate Int-03 (65g, 163.2mmol) is placed in a round-bottom flask, and 500ml of THF is added thereto, then cooled to -78°C. Subsequently, n-BuLi (84.86ml, 212.16mmol) is added thereto, and then stirred for 30 minutes. At -78°C, isopropyl borate (48.66ml, 212.16mmol) is added thereto, then, stirred for 7 hours, and HCl is added thereto to complete the reaction, and after adding water thereto, the aqueous layer is removed therefrom by extraction. The residue is processed by column chromatography (hexane: DCM (30%)) to obtain 41.6g (59%) of intermediate Int-04.

[0286] Synthesis Example 3: Synthesis of Compound A-63

[0287]

[0288] 11.6 g (71%) of Compound A-65 was obtained in the same manner as in the second step of Synthesis Example 1, except that the intermediate (Int-01, Int-04) was changed.

[0289] Synthesis Example 4: Synthesis of Intermediate Int-05

[0290] [Reaction Scheme 4]

[0291]

[0292] 56.4 g (52%) of the intermediate Int-05 was obtained in the same manner as in the first to third steps of Reaction Scheme 2, except that 2,7-bromocarbazole was used instead of 3-bromocarbazole in the first step of Reaction Scheme 2.

[0293] Synthesis Example 5: Synthesis of Compound A-69

[0294] [Reaction Scheme 5]

[0295]

[0296] 8.97 g (74%) of Compound A-69 was obtained in the same manner as in the second step of Synthesis Example 1, except that the intermediate (Int-01, Int-05) was changed.

[0297] Synthesis Example 6: Synthesis of Intermediate Int-06

[0298] [Reaction Scheme 6]

[0299]

[0300] 35.1 g (54%) of the intermediate Int-06 was obtained in the same manner as in the second to third steps of Reaction Scheme 2, except that carbazole was used instead of Int-02 in the second step of Reaction Scheme 2, and 4-bromo-3-fluoro-1,1′-biphenyl was used instead of 1-bromo-2-fluorobenzene in the first step of Reaction Scheme 2.

[0301] Synthesis Example 7: Synthesis of Compound A-98

[0302] [Reaction Scheme 7]

[0303]

[0304] 12.6 g (79%) of Compound A-98 was obtained in the same manner as in the second step of Synthesis Example 1, except that the intermediates (Int-01, Int-06) were changed.

[0305] Synthesis Example 8: Synthesis of Compound B-136

[0306]

[0307] Compound B-136 was synthesized with reference to the synthesis method known from patent registered in US 10476008 B2.

[0308] Comparative Synthesis Example 1: Synthesis of Compound Y1

[0309]

[0310] Compound Y1 was synthesized by referring to the known synthesis method in patent publication KR10-2020-0087020.

[0311] Comparative Synthesis Example 2: Synthesis of Compound Y2

[0312]

[0313] Step 1: Synthesis of intermediate Int-07

[0314] 2,4-dichloro-6-phenyl-1,3,5-triazine (19.5 g, 86.26 mmol), (3-(carbazole-9H)phenyl)pinacol ester (35.04 g, 94.89 mmol), K2CO3 (23.84 g, 172.52 mmol) and Pd(PPh3)4 (2.99 g, 2.59 mmol) were placed in a round-bottom flask and dissolved in 250 ml of THF and 85 ml of distilled water, followed by stirring at 60°C under reflux for 12 hours. When the reaction was complete, after removing the aqueous layer therefrom, the residue was treated by column chromatography (hexane:DCM (30%)) to obtain 24.68 g (66%) of Intermediate Int-07.

[0315] Step 2: Synthesis of Compound Y2

[0316] Compound Y2 (13.6 g, 81%) was obtained in the same manner as in the second step of Synthesis Example 1, except that the intermediate (Int-07, (4-(9H-carbazol-9-yl)phenyl)boronic acid) was changed.

[0317] Comparative Synthesis Example 3: Synthesis of Compound Y3

[0318] [Reaction Scheme 9]

[0319]

[0320]

[0321] Step 1: Synthesis of intermediate Int-08

[0322] 28.6g (170.8mmol) of carbazole and 180ml of THF are placed in a round-bottom flask, then stirred and cooled to 0°C in an ice bath, and 68.3ml (170.8mmol) of n-BuLi (2.5M in hexane) are slowly added dropwise thereto. The obtained mixture is stirred for another 30 minutes at room temperature. Subsequently, 30g (162.7mmol) of 2,4,6-trichloro-1,3,5-triazine and 180ml of THF are added thereto under a nitrogen stream, then stirred, and the pre-prepared Li reagent is slowly added dropwise thereto. Subsequently, the mixture is stirred at room temperature for 1 hour. 300ml of distilled water is added thereto, and the precipitated solid is collected therein by filtration. The solid is dried to obtain 40.1g (78%) of intermediate Int-08.

[0323] Step 2: Synthesis of intermediate Int-09

[0324] Intermediate Int-09 (21.4 g, 68%) was obtained in the same manner as in the first step of Synthesis Example 1, except that Int-08 was used instead of 2,4-dichloro-6-(biphenyl-4-yl)-1,3,5-triazine in the first step of Reaction Scheme 1.

[0325] Step 3: Synthesis of Compound Y3

[0326] Intermediate Y3 (11.7 g, 71%) was obtained in the same manner as in the second step of Synthesis Example 1, except that the intermediate was changed (Int-09, (4′-(9H-carbazol-9-yl)-[1,1′-biphenyl]-4-yl)boronic acid).

[0327] (Manufacturing of organic light-emitting diodes)

[0328] Example 1

[0329] A glass substrate coated with an indium tin oxide (ITO) film was washed with distilled water and ultrasonically. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried, and then moved to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The resulting ITO transparent electrode was used as an anode, and compound A doped with 3% NDP-9 (Novaled) was vacuum deposited on the ITO substrate to form a 100-μm thick hole injection layer, on which compound A was deposited. Hole transport layer formation Thick hole transport layer. On the hole transport layer, Compound B was deposited to form a hole transport auxiliary layer with a thickness of 1000 nm. On the hole transport auxiliary layer, a layer was formed by using Compound A-4 obtained in Synthesis Example 1 and doping 7 wt % of PhGD as a dopant by vacuum deposition. Then, on the light-emitting layer, Compound C was deposited at a thickness of 1:1 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 On the electron transport layer, LiQ and Al are vacuum deposited sequentially to Thick and harmonious thick, thereby manufacturing an organic light emitting diode.

[0330] ITO / Compound A (3% NDP-9 doping, ) / Compound A / Compound B / EML[93 wt% host (Compound A-4):7 wt% PhGD] Compound C / Compound D:LiQ / LiQ / Al

[0331] Compound A: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

[0332] Compound B: N-[4-(4-dibenzofuranyl)phenyl]-N-[4-(9-phenyl-9H-fluoren-9-yl)phenyl][1,1'-diphenyl]-4-amine

[0333] Compound C: 2,4-diphenyl-6-(4',5',6'-triphenyl[1,1':2',1":3",1':3',1''-pentaphenyl]-3''-yl)-1,3,5-triazine

[0334] Compound D: 2-(1,1'-diphenyl-4-yl)-4-(9,9-diphenyl-9H-fluoren-4-yl)-6-phenyl-1,3,5-triazine

[0335] [PhGD]

[0336]

[0337] Example 2

[0338] A glass substrate coated with an ITO (indium tin oxide) thin film was washed with distilled water and ultrasonic waves. After washing with distilled water, the glass substrate was ultrasonically washed with a solvent such as isopropyl alcohol, acetone, methanol, etc. and dried. Then, the glass substrate was moved to a plasma cleaner, cleaned for 10 minutes using oxygen plasma, and moved to a vacuum depositor. The resulting ITO transparent electrode was used as an anode, and compound A doped with 3% NDP-9 (Novaled) was vacuum deposited on the ITO substrate to form Thick hole injection layer, on which compound A is deposited. Hole transport layer is formed On the hole transport layer, Compound E was deposited to form a hole transport auxiliary layer with a thickness of 1000 nm. On the hole transport auxiliary layer, a hole transport auxiliary layer was formed by simultaneously using Compound A-63 obtained in Synthesis Example 3 and Compound B-136 obtained in Synthesis Example 8 as a host and doping 10 wt% of PhGD as a dopant by vacuum deposition. Thick emitting layer. Compound A-63 and compound B-136 were used in a weight ratio of 3:7. Compound F is deposited at a thickness of 1:1 to form an electron transport auxiliary layer, and compound G and LiQ are vacuum deposited at a weight ratio of 1:1 to form On the electron transport layer, LiQ and Al are vacuum deposited sequentially to Thick and harmonious thick, thereby manufacturing an organic light emitting diode.

[0339] ITO / Compound A (3% NDP-9 doping, ) / Compound A / Compound E / EML[host (Compound A-63:Compound B-136=3:7):PhGD=90wt%:10wt%] / Compound F / Compound G:LiQ / LiQ / Al

[0340] Compound E: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluoren)-2-amine

[0341] Compound F: 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-diphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine

[0342] Compound G: 2-[4-[4-(4'-cyano-1,1'-diphenyl-4-yl)-1-naphthyl]phenyl]-4,6-diphenyl-1,3,5-triazine

[0343] Comparative Examples 1 to 3

[0344] Diodes of Comparative Examples 1 to 3 were respectively manufactured in the same manner as in Example 1 except that the main body was changed as shown in Table 1.

[0345] Example 3 and Comparative Example 4

[0346] Diodes of Example 3 and Comparative Example 4 were manufactured in the same manner as in Example 2, except that the main body was changed as shown in Table 2.

[0347] Evaluate

[0348] (1) Measuring current density changes based on voltage changes

[0349] The obtained organic light emitting diode was measured with respect to a current value flowing in a unit device while increasing a voltage from 0 V to 10 V using a current-voltage meter (Keithley 2400), and the measured current value was divided by an area to provide a result.

[0350] (2) Measuring brightness changes based on voltage changes

[0351] While the voltage of the organic light emitting diode was increased from 0V to 10V, the luminance was measured by using a luminance meter (Minolta Cs-1000A).

[0352] (3) Measurement of luminous efficiency

[0353] Using the luminance and current density measured from (1) and (2), calculate the current density (10 mA / cm 2 ) current efficiency (cd / A).

[0354] Table 1 shows relative values ​​of luminous efficiency based on Example 1.

[0355] Table 2 shows relative values ​​of luminous efficiency based on Example 2.

[0356] (4) Lifespan measurement

[0357] The life of the T95 diode is measured at 24000 cd / m 2 As the initial luminance (cd / m 2 ) and measured their brightness reduction over time using the Polanonix lifetime measurement system. Their brightness relative to the initial brightness (cd / m 2 ) is reduced to 95%.

[0358] The relative values ​​of T95 life based on Example 1 are shown in Table 1.

[0359] Table 2 shows the relative values ​​of T95 life based on Example 2.

[0360] (5) Measurement of driving voltage

[0361] A current-voltage meter (Keithley 2400) was used at 15 mA / cm 2 Measure the driving voltage of each diode and obtain the result.

[0362] Table 1 shows relative values ​​of driving voltages based on Example 1.

[0363] (Table 1)

[0364]

[0365] (Table 2)

[0366]

[0367] Referring to Table 1, the organic light-emitting diode manufactured by applying the compound according to the embodiment of the present invention exhibited significantly improved driving, efficiency, and lifespan characteristics compared to the organic light-emitting diode according to the comparative example, and specifically, referring to Table 2, the organic light-emitting diode applying the composition including the compound according to the embodiment of the present invention also exhibited improved efficiency and lifespan characteristics.

[0368] While the present invention has been described in conjunction with what are presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims.

[0369] <Description of Reference Signs>

[0370] 100 organic light-emitting diodes

[0371] 105 organic layer

[0372] 110 cathode

[0373] 120 Anode

[0374] 130 Luminescent Layer

[0375] 140 Hole transport region

[0376] 150 Electron transport region.

Claims

1. A compound for an organic optoelectronic device, which is represented by Chemical Formula 1: [Chemical formula 1] in, In Chemical Formula 1, Ar 1 a substituent selected from Group I, and is unsubstituted or substituted with deuterium, [Group I] Where, in group I, * is the connection point, R 1 are each independently hydrogen, deuterium, or unsubstituted phenyl, R 2 To R 5 are each independently hydrogen, deuterium, unsubstituted C6 to C12 aryl, or C6 to C12 aryl substituted with deuterium, and m1 to m5 are each independently one of integers from 1 to 4.

2. The compound according to claim 1, wherein The compound is selected from the group consisting of: [Group 1] 3. A composition for an organic optoelectronic device, comprising a first compound and a second compound, in, The first compound is the compound for an organic optoelectronic device according to claim 1, and The second compound is a compound for an organic photoelectric device represented by Chemical Formula 2; or a compound for an organic photoelectric device represented by a combination of Chemical Formula 3 and Chemical Formula 4: [Chemical formula 2] Wherein, in Chemical Formula 2, Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, L 1 and L 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R 11 To R 21 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl, m6 and m7 are each independently one of integers from 1 to 3, m8 is one of integers from 1 to 4, and n is an integer from 0 to 2; Among them, in Chemical Formula 3 and Chemical Formula 4, Ar 4 and Ar 5 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, Adjacent two of b1* to b4* of Chemical Formula 3 are each a connecting carbon (C) connected to * of Chemical Formula 4, And the remaining two of b1* to b4* in Chemical Formula 3 that are not connected to * in Chemical Formula 4 are each independently CL a -R a , L a , L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R a and R 22 To R 29 are each independently hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C6 to C30 aryl, or substituted or unsubstituted C2 to C30 heterocyclyl, and Herein, "substituted" means that at least one hydrogen of the substituent is replaced by deuterium, C1 to C5 alkyl, C6 to C18 aryl, or cyano.

4. The composition according to claim 3, wherein Chemical formula 2 is represented by Chemical formula 2-8: [Chemical formula 2-8] in, In Chemical Formula 2-8, R 11 To R 20 are each independently hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group, m6 and m7 are each independently an integer from 1 to 3, and *-L 1 -Ar 2 and *-L 2 -Ar 3 are each independently one of the substituents of Group II, [Group II] Among them, in Group II, R 6 To R 8 are each independently hydrogen, deuterium, substituted or unsubstituted C1 to C4 alkyl, or substituted or unsubstituted C6 to C18 aryl, m8 is an integer from 1 to 5, m9 is an integer from 1 to 4, m10 is one of integers from 1 to 3, and * is the connection point.

5. The composition according to claim 3, wherein The combination of Chemical Formula 3 and Chemical Formula 4 is represented by Chemical Formula 3C: [Chemical formula 3C] in, In chemical formula 3C, L a1 and L a2 is a single key, L 3 and L 4 are each independently a single bond or a substituted or unsubstituted C6 to C12 arylene group, R 22 To R 29 , R a1 and R a2 are each independently hydrogen, deuterium, or C6 to C12 aryl, and Ar 4 and Ar 5 Each is independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group or a substituted or unsubstituted biphenyl group.

6. 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, in, The organic layer comprises the compound for an organic optoelectronic device according to claim 1 or claim 2; or The composition for an organic optoelectronic device according to any one of claims 3 to 5.

7. The organic optoelectronic device according to claim 6, wherein: The organic layer includes a light-emitting layer, and The light-emitting layer includes the compound for an organic photoelectric device or the composition for an organic photoelectric device. A display device comprising the organic optoelectronic device according to claim 6 .

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