KR102171076B1 - Composition for organic optoelectric device and organic optoelectric device and display device - Google Patents

Abstract

A compound for an organic optoelectronic device represented by a combination of Chemical Formulas 1 and 2; It relates to a composition for an organic optoelectronic device including the same, an organic optoelectronic device and a display device to which the same is applied.
Details of Chemical Formula 1 and Chemical Formula 2 are as defined in the specification.

Description

A composition for an organic optoelectronic device, an organic optoelectronic device, and a display device TECHNICAL FIELD [COMPOSITION FOR ORGANIC OPTOELECTRIC DEVICE AND ORGANIC OPTOELECTRIC DEVICE AND DISPLAY DEVICE}

It relates to a composition for an organic optoelectronic device, an organic optoelectronic device, and a display device.

An organic optoelectronic diode is a device capable of converting electrical energy and optical energy to each other.

Organic optoelectronic devices can be largely divided into two types according to the principle of operation. One is a photoelectric device that generates electrical energy by separating excitons formed by light energy into electrons and holes, and the electrons and holes are transferred to different electrodes, and the other is electricity by supplying voltage or current to the electrode. It is a light-emitting device that generates light energy from energy.

Examples of the organic optoelectronic device include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photo conductor drum.

Among them, organic light emitting diodes (OLEDs) are attracting great attention in recent years due to the increasing demand for flat panel display devices. The organic light-emitting device is a device that converts electrical energy into light by applying a current to an organic light-emitting material, and has a structure in which an organic layer is inserted between an anode and a cathode. Here, the organic layer may include an emission layer and an auxiliary layer optionally, and the auxiliary layer may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, and an electron injection layer to increase the efficiency and stability of the organic light emitting device. And it may include at least one layer selected from the hole blocking layer.

The performance of the organic light emitting device is greatly influenced by the properties of the organic layer, and among them, the organic material included in the organic layer is greatly influenced.

In particular, in order for the organic light-emitting device to be applied to a large-sized flat panel display, it is necessary to develop an organic material capable of enhancing the mobility of holes and electrons while increasing electrochemical stability.

One embodiment provides a compound for an organic optoelectronic device capable of implementing a high efficiency and long life organic optoelectronic device.

Another embodiment provides a composition for an organic optoelectronic device comprising the composition.

Another embodiment provides an organic optoelectronic device and a display device including the composition for an organic optoelectronic device.

According to one embodiment, there is provided a compound for an organic optoelectronic device represented by a combination of Formula 1 and Formula 2 below.

[Formula 1] [Formula 2]

In Formula 1 and Formula 2,

R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group , At least one of the R ¹ to R ⁸ is a substituted or unsubstituted C2 to C30 heterocyclic group containing two or more nitrogen atoms,

R ⁹ is hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C4 alkyl group or a substituted or unsubstituted C6 to C12 aryl group,

L ¹ to L ⁸ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

X ¹ and X ² are each independently O or S,

Two adjacent * in Formula 1 are connected to * in Formula 2.

According to another embodiment, there is provided a composition for an organic optoelectronic device including the compound for an organic optoelectronic device.

According to another embodiment, 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 comprises an organic optoelectronic device including the composition for an organic optoelectronic device described above. to provide.

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

High-efficiency, long-life organic optoelectronic devices can be implemented.

1 and 2 are cross-sectional views each independently illustrating an organic light emitting device according to an embodiment.

Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, and the present invention is not limited thereby, and the present invention is only defined by the scope of the claims to be described later.

Unless otherwise defined, the term "substituted" in the present specification means that at least one hydrogen in a substituent or compound is 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, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 It means substituted with a heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

In an example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is 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 It means substituted with a heterocycloalkyl group, a C6 to C30 aryl group, and a C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "substituted" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a dibenzofuranyl group, or a dibenzothiophenyl group. Means that. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is deuterium, methyl group, ethyl group, propanyl group, butyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, triphenyl group, flu It means substituted with an orenyl group, a dibenzofuranyl group, or a dibenzothiophenyl group.

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

In the present specification, "alkyl (alkyl) group" means an aliphatic hydrocarbon group unless otherwise defined. The alkyl group may be a "saturated alkyl group" that does not contain any double bonds or triple bonds.

The alkyl group may be a C1 to C30 alkyl group. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group. For example, a C1 to C4 alkyl group means that 1 to 4 carbon atoms are included in the alkyl chain, and methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and t-butyl It indicates that it is selected from the group consisting of.

Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group. It means practical skills, etc.

In the present specification, "aryl group" is a concept encompassing a group having one or more hydrocarbon aromatic moieties,

While all the elements of the hydrocarbon aromatic moiety have p-orbitals, these p-orbitals include a form in which conjugation is formed, such as a phenyl group, a naphthyl group, and the like,

Two or more hydrocarbon aromatic moieties are linked through a sigma bond, including a biphenyl group, a terphenyl group, a quarterphenyl group, and the like,

It may also include non-aromatic fused rings in which two or more hydrocarbon aromatic moieties are directly or indirectly fused. For example, a fluorenyl group etc. are mentioned.

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

In the present specification, "heterocyclic group" is a higher concept including a heteroaryl group, and carbon (C) instead of N, O, in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof It means containing at least one hetero atom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, one or more heteroatoms may be included in the entire heterocyclic group or each ring.

As an example, "heteroaryl group" means containing at least one hetero atom selected from the group consisting of N, O, S, P, and Si in the aryl group. Two or more heteroaryl groups are directly linked through a sigma bond, or when the heteroaryl group includes two or more rings, 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 hetero atoms.

For specific examples, the heterocyclic group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and the like.

More specifically, a substituted or unsubstituted C6 to C30 aryl group and/or a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra Senyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted naphthacenyl group, substituted or unsubstituted pyrenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted p-terphenyl group, substituted or unsubstituted A substituted m-terphenyl group, a substituted or unsubstituted o-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted flu Orenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted thiophenyl group, substituted or unsubstituted pyrrolyl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted already Dazolyl group, substituted or unsubstituted triazolyl group, substituted or unsubstituted oxazolyl group, substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted thiadiazolyl group, Substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzo Thiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinyl group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted quinazolinyl group, substituted Or an unsubstituted quinoxalinyl group, a substituted or unsubstituted benzoquinolinyl group, a substituted or unsubstituted benzoisoquinolinyl group, a substituted or unsubstituted benzoquinazolinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or Unsubstituted benzoxazineyl group, substituted or unsubstituted benzthiazinyl group, substituted or unsubstituted acridinyl group, substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenothiazinyl group, substituted or unsubstituted Phenoxazineyl group, substituted or unsubstituted dibenzofuranyl group, or substituted or unsubstituted dibenzothiophenyl group, or It may be a combination of, but is not limited thereto.

In the present specification, the hole property refers to a property capable of donating electrons to form holes when an electric field is applied, and injection of holes formed at the anode into the emission layer by having conduction characteristics according to the HOMO level, and the emission layer It means a property that facilitates the movement of the holes formed in the anode to the anode and in the light emitting layer.

In addition, electronic characteristics refer to the characteristics of receiving electrons when an electric field is applied, and has conduction characteristics according to the LUMO level, so that electrons formed in the cathode are injected into the emission layer, electrons formed in the emission layer move to the cathode, and in the emission layer. It means a property that facilitates movement.

Hereinafter, a composition for an organic optoelectronic device according to an embodiment will be described.

The compound for an organic optoelectronic device according to an embodiment may be represented by a combination of Formulas 1 and 2 below.

[Formula 1] [Formula 2]

In Formula 1 and Formula 2,

R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group , At least one of the R ¹ to R ⁸ is a substituted or unsubstituted C2 to C30 heterocyclic group containing two or more nitrogen atoms,

R ⁹ is hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C4 alkyl group or a substituted or unsubstituted C6 to C12 aryl group,

L ¹ to L ⁸ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

X ¹ and X ² are each independently O or S,

Two adjacent * in Formula 1 are connected to * in Formula 2.

In one embodiment of the present invention, the compound represented by the combination of Formulas 1 and 2 according to the fusion point of the ring is a benzofuranodibenzofuran derivative, a benzofuranodibenzothiophene derivative, a benzothiodibenzofuran derivative Alternatively, it may be expressed as a benzothiodibenzothiophene derivative, for example, by the following Formula 3 or Formula 4.

[Formula 3] [Formula 4]

In Chemical Formulas 3 and 4,

R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group , At least one of the R ¹ to R ⁸ is a substituted or unsubstituted C2 to C30 heterocyclic group containing two or more nitrogen atoms,

R ⁹ is hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C4 alkyl group or a substituted or unsubstituted C6 to C12 aryl group,

L ¹ to L ⁸ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

X ¹ and X ² are each independently O or S,

Two adjacent * in Formula 1 are connected to * in Formula 2.

The benzofuranodibenzofuran derivative, benzofuranodibenzothiophene derivative, benzothiodibenzofuran derivative, or benzothiodibenzothiophene derivative represented by Formula 3 or Formula 4 is difficult to crystallize molecules, and organic When manufacturing an optoelectronic device, it is possible to reduce the driving voltage and improve the yield and lifetime.

For example, Formula 3 may be represented by Formula 3-1 below, and Formula 4 may be represented by Formula 4-1 below.

[Formula 3-1] [Formula 4-1]

In Chemical Formulas 3 and 4,

R ⁹ is hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C4 alkyl group or a substituted or unsubstituted C6 to C12 aryl group,

X ¹ and X ² are each independently O or S,

L ⁹ and L ¹⁰ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

ET is a substituted or unsubstituted heterocyclic group containing at least two Ns.

The compound represented by Formula 3-1 or 4-1 can be used as a light-emitting material by combining benzofuranodibenzofuran and an ET group to perform electron injection, electron transport, or a light emitting material role in an organic electronic device. In this case, it is possible to manufacture an organic light-emitting device having a long life and high efficiency while reducing the driving voltage.

For example, the formula 3-1 is represented by any one of the following formulas 3-1-1 to 3-1-4, and the formula 4-1 is any one of the following formulas 4-1-1 to 4-1-8 It can be expressed as one.

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

[Chemical Formula 3-1-4] [Chemical Formula 4-1-1] [Chemical Formula 4-1-2]

[Formula 4-1-3] [Formula 4-1-4]

[Formula 4-1-5] [Formula 4-1-6] [Formula 4-1-7] [Formula 4-1-8]

In Formula 3-1-1 to Formula 4-1-8,

X ¹ and X ² are each independently O or S,

L ⁹ and L ¹⁰ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

ET is a substituted or unsubstituted heterocyclic group containing at least two Ns.

For example, the ET may be a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted benzothienopyrimidinyl group.

The ET may be substituted with one or more substituents selected from the following group I.

[Group I]

In the group I, * is the point of connection with L ¹ and L ² , respectively.

For example, the compound for an organic optoelectronic device represented by the combination of Formulas 1 and 2 may be selected from compounds listed in Group 1, but is not limited thereto.

[Group 1]

The above-described compound for an organic optoelectronic device may be applied to an organic optoelectronic device alone or together with another compound for an organic optoelectronic device. When the above-described compound for an organic optoelectronic device is used alone or in combination with another compound for an organic optoelectronic device, it may be applied in the form of a composition.

The present invention provides a composition for an organic optoelectronic device comprising the compound for an organic optoelectronic device (a first compound for an organic optoelectronic device) represented by the combination of Formulas 1 and 2 mentioned above.

In addition, the present invention is for an organic electronic device comprising the first compound for an organic optoelectronic device and a compound represented by the following formula 5 or a compound represented by a combination of the following formulas 6 and 7 (a second organic optoelectronic device compound) Compositions can be provided.

[Formula 5]

In Chemical Formula 5,

Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

Ar ¹ and Ar ² 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 ¹⁰ to R ¹⁵ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ego,

m is one of an integer from 0 to 2;

[Formula 6] [Formula 7]

In Formulas 6 and 7,

Y ³ and Y ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,

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 ¹⁶ to R ¹⁹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ego,

Two adjacent * in Formula 6 are connected to two * in Formula 7 to form a fused ring, and * not forming a fused ring in Formula 6 are each independently CR ^a ,

R ^a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C12 heterocyclic group, or a combination thereof;

The "substituted" means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C18 heteroaryl group.

In one embodiment of the present invention, Y ¹ and Y ² in Formula 5 may each independently be a single bond or a substituted or unsubstituted C6 to C18 arylene group.

In an embodiment of the present invention, Ar ¹ and Ar ² in Formula 5 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, substituted or unsubstituted anthracenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted quinazolyl group, substituted Or an unsubstituted isoquinazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or these It may be a combination of.

In one embodiment of the present invention, R ¹⁰ to R ¹⁵ in Formula 5 may each independently be hydrogen, deuterium, or a substituted or unsubstituted C6 to C12 aryl group.

In an embodiment of the present invention, m in Formula 5 may be 0 or 1.

In a specific embodiment of the present invention, Formula 5 is one of the structures listed in Group II below, and *-Y ¹ -Ar ¹ and *-Y ² -Ar ² may be one of the substituents listed in Group III below. have.

[Group Ⅱ]

[Group Ⅲ]

In groups II and III above, * is a connection point.

Specifically, Formula 5 is represented by C-8 of Group II, and *-Y ¹ -Ar ¹ and *-Y ² -Ar ² are represented by any one of B-1 to B-4 of Group III. Can be.

More specifically, the *-Y ¹ -Ar ¹ and *-Y ² -Ar ² may be selected from B-2 and B-3 of the group III, and combinations thereof.

The second compound for an organic optoelectronic device represented by Formula 5 may be, for example, a compound listed in Group 2 below, but is not limited thereto.

[Group 2]

[D-1] [D-2] [D-3] [D-4] [D-5]

[D-6] [D-7] [D-8] [D-9] [D-10]

[D-11] [D-12] [D-13] [D-14] [D-15]

[D-16] [D-17] [D-18] [D-19] [D-20]

[D-21] [D-22] [D-23] [D-24] [D-25]

[D-26] [D-27] [D-28] [D-29] [D-30]

[D-31] [D-32] [D-33] [D-34] [D-35]

[D-36] [D-37] [D-38] [D-39] [D-40]

[D-41] [D-42] [D-43] [D-44] [D-45]

[D-46] [D-47] [D-48] [D-49] [D-50]

[D-51] [D-52] [D-53] [D-54] [D-55]

[D-56] [D-57] [D-58] [D-59] [D-60]

[D-61] [D-62] [D-63] [D-64] [D-65]

[D-66] [D-67] [D-68] [D-69] [D-70]

[D-71] [D-72] [D-73] [D-74] [D-75]

[D-76] [D-77] [D-78] [D-79] [D-80]

[D-81] [D-82] [D-83] [D-84] [D-85]

[D-86] [D-87] [D-88] [D-89] [D-90]

[D-91] [D-92] [D-93] [D-94] [D-95]

[D-96] [D-97] [D-98] [D-99] [D-100]

[D-101] [D-102] [D-103] [D-104] [D-105]

[D-106] [D-107] [D-108] [D-109] [D-110]

[D-111] [D-112] [D-113] [D-114] [D-115]

[D-116] [D-117] [D-118] [D-119] [D-120]

[D-121] [D-122] [D-123] [D-124] [D-125]

[D-126] [D-127] [D-128] [D-129] [D-130]

[D-131] [D-132] [D-133] [D-134] [D-135]

[D-136] [D-137] [D-138] [D-139]

In an embodiment of the present invention, the second compound for an organic optoelectronic device represented by the combination of Formula 6 and Formula 7 may be represented by at least one of the following Formulas 6-I to 6-V.

[Chemical Formula 6-Ⅰ] [Chemical Formula 6-Ⅱ] [Chemical Formula 6-Ⅲ]

[Chemical Formula 6-Ⅳ] [Chemical Formula 6-Ⅴ]

In Formulas 6-I to 6-V, Y ³ , Y ⁴ , Ar ³ , Ar ⁴ and R ¹⁶ to R ¹⁹ are as described above.

In an embodiment of the present invention, Y ³ and Y ⁴ in Formulas 6-I to 6-V may be a single bond, a phenylene group, a biphenylene group, a pyridylene group, or a pyrimidinylene group.

In an embodiment of the present invention, Ar ³ and Ar ⁴ of Formulas 6-I to 6-V are substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted It may be a pyrimidinyl group, or a substituted or unsubstituted triazinyl group.

In an embodiment of the present invention, R ¹⁶ to R ¹⁹ in Formulas 6-I to 6-V may be hydrogen.

The second compound for an organic optoelectronic device represented by the combination of Formula 6 and Formula 7 may be, for example, a compound listed in Group 3, but is not limited thereto.

[Group 3]

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

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

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

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

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

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

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

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

The second compound for an organic optoelectronic device may be used in a light emitting layer together with the compound for an organic optoelectronic device to improve charge mobility and stability, thereby improving luminous efficiency and lifetime characteristics. In addition, by controlling the ratio of the second organic optoelectronic device compound and the first organic optoelectronic device compound, it is possible to control the mobility of electric charges.

In addition, the first organic optoelectronic device compound and the second organic optoelectronic device compound are, for example, about 1:9 to 9:1, 2:8 to 8:2, 3:7 to 7:3, 4:6 to 6 :4, and may be included in a weight ratio of 5:5, specifically 1:9 to 8:2, 1:9 to 7:3, 1:9 to 6:4, 1:9 to 5:5 weight ratio It may be included, and more specifically, may be included in a weight ratio of 2:8 to 7:3, 2:8 to 6:4, and 2:8 to 5:5. In addition, it may be included in a weight ratio of 3:7 to 6:4, and 3:7 to 5:5, and most specifically, it may be included in a weight ratio of 3:7 4:6 or 5:5.

Various compositions may be prepared by various combinations of the above-described first organic optoelectronic device compound and second organic optoelectronic device compound.

The second compound for an organic optoelectronic device may be used in an emission layer together with the compound for a first organic optoelectronic device to increase the mobility and stability of electric charges, thereby improving driving voltage, luminous efficiency, and lifetime characteristics.

The composition including the first compound for an organic optoelectronic device and the compound for a second organic optoelectronic device may further include a dopant.

The dopant may be a red, green, or blue dopant, for example, a red or green phosphorescent dopant.

The dopant is a material that emits light by mixing in a small amount, and in general, a material such as a metal complex that emits light by multiple excitation excitation in a triplet state or more may be used. The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one or two or more.

Examples of the phosphorescent dopant include an organometallic compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof, For example, a compound represented by the following Formula Z may be used, but is not limited thereto.

[Formula Z]

L ₂ MX

In Formula Z, M is a metal, L and X are the same as or different from each other, and are ligands that form a complex compound with M.

The 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 L and X are, for example, bidentate It can be a ligand.

More specifically, the phosphorescent dopant is an organometallic compound including one of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. In a specific embodiment, the phosphorescent dopant may be an organometallic compound represented by Formula 401 below.

<Formula 401>

In Formula 401, M is selected from Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb and Tm; _X401 to _X404 are each independently nitrogen or carbon; A ₄₀₁ and A ₄₀₂ rings are independently of each other, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spiro-fluorene, substituted or unsubstituted indene , Substituted or unsubstituted pyrrole, substituted or unsubstituted thiophene, substituted or unsubstituted furan, substituted or unsubstituted imidazole, substituted or unsubstituted pyrazole, substituted or unsubstituted thiazole, Substituted or unsubstituted isothiazole, substituted or unsubstituted oxazole, substituted or unsubstituted isoxazole, substituted or unsubstituted pyridine, substituted or unsubstituted pyrazine, substituted or unsubstituted pyrimidine, Substituted or unsubstituted pyridazine, substituted or unsubstituted quinoline, substituted or unsubstituted isoquinoline, substituted or unsubstituted benzoquinoline, substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or unsubstituted Substituted carbazole, substituted or unsubstituted benzoimidazole, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophene, substituted or unsubstituted isobenzothiophene, substituted or unsubstituted benzo Oxazole, substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran, and Selected from substituted or unsubstituted dibenzothiophene; Herein, "substituted" means that at least one hydrogen in a substituent or compound is deuterium, a halogen group, a hydroxyl group, a cyano 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, C1 to C30 alkyl group, C1 to C10 alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 heterocyclic group, C1 to A C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a combination thereof; L ₄₀₁ is an organic ligand; xc1 is 1, 2 or 3; xc2 is 0, 1, 2 or 3.

The L ₄₀₁ may be any monovalent, divalent or trivalent organic ligand. For example, L ₄₀₁ is a halogen ligand (eg Cl, F), a diketone ligand (eg, acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2, 6,6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (e.g. picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon A monooxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorus ligand (eg, phosphine, phosphite) may be selected, but is not limited thereto.

If the formula of A 401 ₄₀₁ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₁ can form a saturated or unsaturated ring.

If the formula of A 401 ₄₀₂ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₂ can form a saturated or unsaturated ring.

는 서로 동일하거나 상이할 수 있다. 상기 화학식 401 중 xc1이 2 이상일 경우, A₄₀₁ 및 A₄₀₂는 각각 이웃하는 다른 리간드의 A₄₀₁ 및 A₄₀₂와 각각 직접(directly) 또는 연결기(예를 들면, C1 내지C5 알킬렌기, -N(R')-(여기서, R'은 C1 내지 C10 알킬기 또는 C6 내지 C20 아릴기임) 또는 -C(=O)-)를 사이에 두고 연결될 수 있다.When xc1 in Formula 401 is 2 or more, a plurality of ligands in Formula 401

May be the same or different from each other. If the formula xc1 401 is 2 or more of, A ₄₀₁ and A ₄₀₂ are each of the other ligands neighboring A and ₄₀₁ respectively direct and A ₄₀₂ (directly) or linking group (e.g., C1 to C5 alkylene group, -N (R ')- (here, R'is a C1 to C10 alkyl group or a C6 to C20 aryl group) or -C(=O)-).

For example, the phosphorescent dopant may be a red or green phosphorescent dopant, and may be selected from the following compounds PD1 to PD75, but is not limited thereto.

In addition, by controlling the ratio of the second organic optoelectronic device compound and the first organic optoelectronic device compound, it is possible to control the mobility of electric charges. When the composition of the present invention is used as a host, the combination ratio thereof may vary depending on the type of dopant used or the propensity of the dopant. For example, it may be included in a weight ratio of 1:10 to 10:1. Specifically, it may be 2:8 to 8:2, 9:1 to 5:5, 8:2 to 5:5, 7:3 to 5:5, and as the most specific example, the first organic optoelectronic device compound and agent 2 The mixing weight ratio of the compound for an organic optoelectronic device may be 5:5.

By being included in the weight ratio range, bipolar characteristics are more effectively implemented, and efficiency and lifespan can be improved at the same time.

The composition may be formed by a dry film formation method such as chemical vapor deposition or a solution process.

Hereinafter, an organic optoelectronic device to which the composition for an organic optoelectronic device is applied will be described.

An organic optoelectronic device according to another embodiment may include an anode and a cathode facing each other, and at least one organic layer disposed between the anode and the cathode, and the organic layer may include the composition for an organic optoelectronic device described above. .

For example, the organic layer may include an emission layer, and the emission layer may include the composition for an organic optoelectronic device of the present invention.

Specifically, the composition for an organic optoelectronic device may be included as a host of the emission layer, such as a green host.

In addition, the organic layer includes a light emitting layer, and at least one auxiliary layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer and a hole blocking layer, and the auxiliary layer is the composition for an organic optoelectronic device It may include.

The organic optoelectronic device is not particularly limited as long as it is a device capable of mutually converting electrical energy and light energy, and examples thereof include an organic photoelectric device, an organic light emitting device, an organic solar cell, and an organic photoreceptor drum.

Here, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

1 and 2 are cross-sectional views illustrating an organic light-emitting device according to an embodiment.

Referring to FIG. 1, an organic light emitting diode 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 110. Include.

The anode 120 may be made of a conductor having a high work function to facilitate hole injection, for example, and may be made of a metal, a metal oxide, and/or a conductive polymer. The anode 120 may be a metal such as nickel, platinum, vanadium, chromium, copper, zinc, or gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metals and oxides such as ZnO and Al or SnO ₂ and Sb; Poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDT), conductive polymers such as polypyrrole and polyaniline, but are limited thereto. It is not.

The cathode 110 may be made of, for example, a conductor having a low work function to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and/or a conductive polymer. The negative electrode 110 may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium, or an alloy thereof; A multilayered material such as LiF/Al, LiO ₂ /Al, LiF/Ca, LiF/Al, and BaF ₂ /Ca may be mentioned, but is not limited thereto.

The organic layer 105 includes the emission layer 130 including the compound for an organic optoelectronic device described above.

2 is a cross-sectional view showing an organic light emitting device according to another embodiment.

Referring to FIG. 2, the organic light-emitting device 200 further includes a hole auxiliary layer 140 in addition to the emission layer 130. The hole auxiliary layer 140 may further increase hole injection and/or hole mobility between the anode 120 and the light emitting layer 130 and block electrons. The hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and/or an electron blocking layer, and may include at least one layer.

The organic layer 105 of FIG. 1 or 2 is not shown, but may further include an electron injection layer, an electron transport layer, an electron transport auxiliary layer, a hole transport layer, a hole transport auxiliary layer, a hole injection layer, or a combination layer thereof. have. The compound for an organic optoelectronic device of the present invention may be included in these organic layers. The organic light emitting devices 100 and 200 may include a dry film forming method such as vacuum evaporation, sputtering, plasma plating and ion plating after forming an anode or a cathode on a substrate; Alternatively, the organic layer may be formed by a wet film forming method such as spin coating, dipping, or flow coating, and then a cathode or anode may be formed thereon.

The organic light emitting device described above can be applied to an organic light emitting display device.

Hereinafter, specific embodiments of the present invention are presented. However, the examples described below are merely for illustrating or explaining the present invention in detail, and the present invention is not limited thereto.

Hereinafter, the starting materials and reactants used in the Examples and Synthesis Examples were purchased from Sigma-Aldrich or TCI, or synthesized through a known method, unless otherwise specified.

(Preparation of compound for organic optoelectronic device)

The compounds presented as more specific examples of the compounds of the present invention were synthesized through the following steps.

(First organic optoelectronic device compound)

<Core synthesis 1>

Synthesis Example 1: Synthesis of Intermediate Int-01

<Reaction Scheme 1>

2-Bromophenylboronic Acid (38.86g, 277.76mmol), Bromohydroquinone (50g, 264.54mmol), K ₂ CO ₃ (91.4g, 661.34mmol) and Pd(PPh ₃ ) ₄ (15.28g, 13.23mmol) were added to a round bottom flask. Dissolve in THF (600ml) and distilled water (300ml) and stir under reflux for 12 hours at 60°C. When the reaction was completed, the water layer was removed, and then 30.79 g (57%) of the intermediate (Int-01) was obtained by column chromatography.

Synthesis Example 2: Synthesis of Compound Int-02

<Reaction Scheme 2>

Intermediate (Int-01) (19.8g, 96.96mmol) and K ₂ CO ₃ (14.74g, 106.66mmol) were put in a round bottom flask, dissolved in NMP (200ml), and stirred under reflux for 12 hours at 180℃. When the reaction is complete, the mixture is poured into an excess of distilled water. After stirring for 1 hour, the water layer was removed, and then 23.51 g (87%) of the intermediate (Int-02) was obtained by column chromatography.

Synthesis Example 3: Synthesis of Compound Int-03

<Reaction Scheme 3>

Intermediate (Int-02) (29g, 157.45mmol) and N-Bromosuccinimide (25.22g, 147.70mmol) were put in a round bottom flask, dissolved in EtOH (150ml), and stirred at room temperature for 4 hours. When the reaction is complete, the mixture is poured into an excess of distilled water. After stirring for 1 hour, the water layer was removed, and then 14.08 g (34%) of the intermediate (Int-03) was obtained by column chromatography.

Synthesis Example 4: Synthesis of Compound Int-04

<Reaction Scheme 4>

Intermediate (Int-03) (11.3g, 42.95mmol), 4-Chloro-2-fluorophenylboronic Acid (8.99g, 51.54mmol), K ₂ CO ₃ (14.84g, 138.21mmol) and Pd(PPh ₃ ) ₄ (2.48) g, 2.15mmol) was placed in a round bottom flask, dissolved in THF (150ml) and distilled water (70ml), and stirred under reflux at 70℃ for 12 hours. When the reaction was completed, the water layer was removed, and then 7.2 g (54%) of an intermediate (Int-04) was obtained by column chromatography.

Synthesis Example 5: Synthesis of Compound Int-05

<Reaction Scheme 5>

Intermediate (Int-04) (7.2g, 23.02mmol) and K ₂ CO ₃ (3.5g, 106.66mmol) were put in a round bottom flask, dissolved in NMP (80ml), and stirred under reflux for 12 hours at 180°C. When the reaction is complete, the mixture is poured into an excess of distilled water. After stirring for 1 hour, the water layer was removed, and then 6.14 g (91%) of the intermediate (Int-05) was obtained by column chromatography.

Synthesis Example 6: Synthesis of Compound Int-06

<Reaction Scheme 6>

Intermediate (Int-5) (20g, 68.32mmol), Bis(pinacolato)diboron (26.03g, 102.49mmol), Pd(dppf)Cl ₂ (2.79g, 3.42mmol), Tricyclohexylphosphine (2.87g, 10.25mmol) and Potassium Put acetate (20.12g, 204.97mmol) in a round bottom flask and dissolve with DMF (200ml). The mixture was stirred under reflux at 130° C. for 12 hours. When the reaction is complete, the mixture is poured into an excess of distilled water and stirred for 1 hour. After filtering the solids, they are dissolved in DCM. After removing moisture with MgSO ₄ , the organic solvent is filtered using a silica gel pad, and then removed under reduced pressure. The solid was recrystallized from Ethyl Acetate and Hexane to obtain 22.5 g (86%) of an intermediate (Int-6).

<Core synthesis 2>

Synthesis Example 7: Synthesis of Compound Int-12

The intermediate (Int-12) was synthesized in the same manner as in Synthesis Examples 1 to 6, except that 2-Bromoresorcinol was used instead of Bromohydroquinone in the core synthesis 1.

Synthesis Example 8: Synthesis of Compounds Int-23 to Int-28

Six intermediate cores were synthesized using the same synthesis method except for changing the intermediate reagents of core 1 and core 2.

<Intermediate (substituent) synthesis 1>

Synthesis Example 9: Synthesis of Compound Int-13

<Reaction Scheme 7>

2,4-Dichloro-6-phenyl-1,3,5-triazine (10g, 44.24mmol), 4-Biphenylboronic acid (7.88g, 39.81mmol), K ₂ CO ₃ (15.28g, 110.59mmol) and Pd( PPh ₃ ) ₄ (2.56g, 2.21mmol) was put in a round bottom flask, dissolved in THF (100ml) and distilled water (40ml), and stirred under reflux for 12 hours at 60℃. When the reaction was completed, the water layer was removed, and then 10.04 g (66%) of the intermediate (Int-13) was obtained by column chromatography.

Synthesis Example 10: Synthesis of Compound Int-14

<Reaction Scheme 8>

Intermediate (Int-13) (12g, 34.9mmol), 3-chlorophenylboronic acid (5.46g, 34.9mmol), K ₂ CO ₃ (12.06g, 87.26mmol) and Pd(PPh ₃ ) ₄ (2.02g, 1.75mmol) Was put in a round bottom flask, dissolved in THF (110ml) and distilled water (40ml), and stirred under reflux for 12 hours at 60℃. When the reaction was completed, the water layer was removed, and then 10.70 g (73%) of the intermediate (Int-14) was obtained by column chromatography.

<Intermediate (substituent) synthesis 2>

The intermediate (Int-16) was synthesized in the same synthesis method as in Synthesis Example 8 in Synthesis Example 7 except that 3-Biphenylboronic acid was used instead of 4-Biphenylboronic acid in Synthesis 1 of the intermediate.

<Intermediate (substituent) synthesis 3>

Synthesis of the intermediate (Int-20) was performed in the same manner as in Synthesis Example 9 and Synthesis Example 10, except that phenylboronic acid was used instead of 4-Biphenylboronic acid in Synthesis 1 of the intermediate. In the case of the intermediate (Int-19), synthesis example 6 and It was synthesized in the same way.

<Intermediate (substituent) synthesis 4>

The intermediate (Int-) was used in the same manner as in Synthesis Example 9, except that Boronic acid, B-[1,1':3',1''-terphenyl]-4-yl- was used instead of 4-Biphenylboronic acid in Synthesis 1 21) Synthesis.

Synthesis Example 11: Synthesis of Compound 016

<Reaction Scheme 9>

Intermediate (Int-06) (11.53g, 30.01mmol), Intermediate (Int-21) (12g, 28.58mmol), K2CO3 (9.87g, 71.45mmol) and Pd(PPh ₃ ) ₄ (1.65g, 1.43mmol) Put in a round bottom flask, dissolve in THF (100ml) and distilled water (40ml), and stir under reflux at 70℃ for 12 hours. After the reaction was completed, the mixture was added to 500 mL of methanol to filter out the crystallized solid, dissolved in monochlorobenzene, filtered through silica gel/celite, removed an appropriate amount of organic solvent, and recrystallized with methanol (Compound 016) 12.0 g (72 %) was obtained.

Synthesis Example 12: Synthesis of Compound 026

<Reaction Scheme 10>

Intermediate (Int-06) (9.9g, 25.76mmol), Intermediate (Int-14) (10.3g, 24.53mmol), K2CO3 (8.48g, 61.32mmol) and Pd(PPh3)4 (1.42g, 1.23mmol) Put in a round bottom flask, dissolve in THF (90ml) and distilled water (35ml), and stir under reflux at 70℃ for 12 hours. Upon completion of the reaction, the mixture was added to 500 mL of methanol to filter the crystallized solid, dissolved in monochlorobenzene and filtered through silica gel/celite, and after removing an appropriate amount of organic solvent, recrystallized with methanol (Compound 026) 10.51 g (74) %) was obtained.

<final synthesis>

Eight kinds of synthetic materials (Compounds 033, 059, 071, 099, 109, 116, 154, 164) were prepared using the same synthesis method as Synthesis Example 11 and Synthesis Example 12 except for the synthesis of the synthesized core and intermediate (substituent) reagent changes. Synthesized.

<033 synthesis>

Compound 033 (14.3 g, 76% yield) was obtained.

<059 synthesis>

Compound 059 (14.7 g, 81% yield) was obtained.

<071 synthesis>

Compound 071 (12.7 g, 73% yield) was obtained.

<099 synthesis>

Compound 099 (13.1 g, 74% yield) was obtained.

<109 synthesis>

Compound 109 (13.6 g, 79% yield) was obtained.

<116 synthesis>

Compound 116 (13.7 g, 78% yield) was obtained.

<154 synthesis>

Compound 154 (13.1 g, 75% yield) was obtained.

<164 synthesis>

Compound 164 (14.2 g, 78% yield) was obtained.

(Synthesis of the second organic optoelectronic device compound)

Synthesis Example 13: Synthesis of Compound D-99

After dissolving the compound Biphenylcarbazolyl bromide (12.33 g, 30.95 mmol) in 200 mL of Toluene in a nitrogen environment, biphenylcarbazolylboronic acid (12.37 g, 34.05 mmol) and tetrakis (triphenylphosphine) palladium (1.07 g, 0.93 mmmol) were added and stirred. Potassuim carbonate (12.83 g, 92.86 mmol) saturated in water was added and heated at 90° C. for 12 hours to reflux. After the reaction was completed, water was added to the reaction solution, extracted with dichloromethane (DCM), and then water was removed with anhydrous MgSO ₄ , filtered and concentrated under reduced pressure. The obtained residue was separated and purified by flash column chromatography to obtain compound D-99 (18.7 g, 92%).

LC/MS calculated for: C ₄₈ H ₃₂ N ₂ Exact Mass: 636.26 found for 636.30 [M+H]

Synthesis Example 14: Synthesis of Compound E-43

In a round bottom flask, intermediate 5,8-dihydro-indolo[2,3-C]carbazole 8g(31.2mmol), 4-iodobiphenyl 20.5g(73.32mmol), CuI 1.19g(6.24mmol), 1,10- Phenanthoroline 1.12g (6.24mmol), K ₂ CO ₃ 12.9g (93.6mmol) was added, DMF 50ml was added, and the mixture was stirred under reflux for 24 hours under a nitrogen atmosphere. After completion of the reaction, it was added with distilled water to precipitate crystals and filtered. The solid was dissolved in 250 ml of xylene, filtered through silica gel, and precipitated as a white solid to obtain 16.2 g (yield 93%) of compound E-43.

LC/MS calculated for: C ₄₂ H ₂₈ N ₂ Exact Mass: 560.23 found for 560.27 [M+H]

<Comparative compound synthesis>

Comparative Synthesis Example 1

Compound F-1 was synthesized by referring to the method described in KR2017-0049714 specification.

F-1

Comparative Synthesis Examples 2 and 3

Compounds F-2 and F-3 were synthesized through an intermediate change in the same manner as in Comparative Synthesis Example 1.

<F-2 synthesis>

Compound F-2 (11.3 g, 74% yield) was obtained.

<F-3 synthesis>

Compound F-3 (15.2 g, 68% yield) was obtained.

(Production of organic light emitting device)

Example 1

두께의 발광층을 형성하였다. 발광층에 호스트를 두가지 물질로 사용할 경우, 호스트로 사용되는 두 가지 물질의 혼합 비율을 하기 표 1에 별도로 기술하였다. 이어서 상기 발광층 상부에 화합물 D와 Liq를 동시에 1:1 비율로 진공 증착하여 300Å 두께의 전자수송층을 형성하고 상기 전자수송층 상부에 Liq 15Å과 Al 1200Å을 순차적으로 진공 증착하여 음극을 형성함으로써 유기발광소자를 제작하였다.The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500Å was washed with distilled water and ultrasonic waves. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma cleaner, and then cleaned for 10 minutes using oxygen plasma, and then transferred to a vacuum evaporator. Using the prepared ITO transparent electrode as an anode, Compound A was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 700 Å, and Compound B was deposited on the injection layer to a thickness of 50 Å, and then Compound C was deposited with a thickness of 1020 Å. It was deposited to a thickness to form a hole transport layer. Compound 016 was used as a host on the hole transport layer, and Ir(ppy) ₃ was doped with 7wt% as a dopant to 400Å by vacuum evaporation.

A light emitting layer of thickness was formed. When the host is used as two materials in the emission layer, the mixing ratio of the two materials used as the host is separately described in Table 1 below. Then, compound D and Liq were simultaneously vacuum-deposited at a 1:1 ratio on the emission layer to form an electron transport layer having a thickness of 300 Å, and Liq 15 Å and Al 1200 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby forming an organic light-emitting device. Was produced.

The organic light-emitting device has a structure having a five-layer organic thin film layer, and is specifically as follows.

ITO/Compound A(700Å)/Compound B(50Å)/Compound C(1020Å)/EML[Compound 016:Ir(ppy) ₃ (7wt%)](400Å)/Compound D:Liq(300Å)/Liq(15Å )/Al (1200Å).

Compound A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl-4,4'-diamine

Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN)

Compound C: N-(biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine

Compound D: 8-(4-(4,6-di(naphthalen-2-yl)-1,3,5-triazin-2-yl)phenyl)quinolone

Examples 2 to 11 and Comparative Examples 1 to 5

As shown in Table 1 below, organic light-emitting devices of Examples 2 to 11 and Comparative Examples 1 to 5 were fabricated in the same manner as in Example 1 using a first host and a second host.

evaluation

The effects of the organic light emitting diodes according to Examples 1 to 11 and Comparative Example 1 were evaluated as follows. The specific measurement method is as follows.

(1) Measurement of driving voltage

The result was obtained by measuring the driving voltage of each device at 15 mA/cm ² using a current-voltmeter (Keithley 2400).

(2) Measurement of change in current density due to voltage change

For the prepared organic light emitting device, while increasing the voltage from 0V to 10V, a current-voltmeter (Keithley 2400) was used to measure the current value flowing through the unit device, and the measured current value was divided by the area to obtain a result.

(3) Measurement of luminance change according to voltage change

For the prepared organic light-emitting device, the luminance was measured at that time using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V, and the result was obtained.

(4) Life measurement

The device using the polar Optronics lifetime measuring system for the manufacture of organic light emitting element of the initial luminance (cd / m ²⁾ the brightness of 97% from the initial brightness by measuring the decrease in the luminance according to the light emission and time in 24000cd / m ² The time point at which was decreased was measured as T97 life.

(5) Measurement of luminous efficiency

The current efficiency (cd/A) of the same current density (10 mA/cm ² ) was calculated using the luminance, current density, and voltage measured from (2) and (3).

First
Host Second
Host 1st, 2nd
Host rate color efficiency
Cd/A life span
(T97) Driving
(Vd) Example 1 Compound 016 - Exclusive green 48 20 4.52 Example 2 Compound 016 D-99 3:7 green 67 30 4.02 Example 3 Compound 026 - Exclusive green 51 25 4.41 Example 4 Compound 026 D-99 3:7 green 70 66 3.90 Example 5 Compound 026 E-43 5:5 green 62 39 3.75 Example 6 Compound 033 - Exclusive green 52 18 4.55 Example 7 Compound 033 D-99 3:7 green 70 48 4.06 Example 8 Compound 071 - Exclusive green 47 17 4.54 Example 9 Compound 071 D-99 3:7 green 65 34 4.01 Example 8 Compound 109 - Exclusive green 55 17 4.42 Example 9 Compound 109 D-99 3:7 green 74 33 3.93 Example 10 Compound 109 E-43 5:5 green 66 26 3.80 Example 10 Compound 116 - Exclusive green 53 16 4.49 Example 11 Compound 116 D-99 3:7 green 71 20 4.04 Comparative Example 1 CBP - Exclusive green 40.2 5 5.24 Comparative Example 2 F-1 - Exclusive green 43.5 7 5.12 Comparative Example 3 F-2 - Exclusive green 42.5 8 4.78 Comparative Example 4 F-2 D-99 3:7 green 45.6 11 4.65 Comparative Example 5 F-3 - Exclusive green 42.4 8 4.88

Referring to Table 1, the first host used alone shows great advantages in terms of efficiency and driving life compared to the compounds (CBP, F-1, F-2, F-3) used as comparative examples. In addition, it can be seen that when the first host and the second host are used in combination, an effect of increasing efficiency and lowering driving can be obtained than when the first host is used alone, and the lifespan is significantly improved by the combination of the hosts. However, in the case of the comparative example, it can be seen that there is no significant change in device performance when the second host is used.

The present invention is not limited to the above embodiments, but may be manufactured in a variety of different forms, and a person of ordinary skill in the art to which the present invention pertains to other specific forms without changing the technical spirit or essential features of the present invention. It will be appreciated that it can be implemented with. Therefore, it should be understood that the embodiments described above are illustrative in all respects and not limiting.

100, 200: organic light emitting device
105: organic layer
110: cathode
120: anode
130: light-emitting layer
140: hole auxiliary layer

Claims (16)

delete delete delete A compound for an organic optoelectronic device represented by any one of the following formulas 3-1-3, 4-1-3, and 4-1-7:
[Formula 3-1-3] [Formula 4-1-3] [Formula 4-1-7]

In Formula 3-1-3, Formula 4-1-3, and Formula 4-1-7,
X ¹ and X ² are each independently O or S,
L ⁹ and L ¹⁰ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
ET is a substituted or unsubstituted heterocyclic group containing at least two Ns. The method of claim 4,
The ET is a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinazolinyl group, or a substituted or unsubstituted benzothienopyrimidinyl group. The method of claim 5,
The ET is a compound for an organic optoelectronic device substituted with one or more substituents selected from the following group I:
[Group I]

In the group I, * is a connection point with L ⁹ and L ¹⁰ , respectively. delete A first compound for an organic optoelectronic device represented by a combination of the following Chemical Formulas 1 and 2; And
A composition for an organic optoelectronic device comprising at least one second compound for an organic optoelectronic device among compounds for an organic optoelectronic device represented by the following Formula 5 and compounds for an organic optoelectronic device represented by a combination of Formulas 6 and 7
[Formula 1] [Formula 2]

In Formula 1 and Formula 2,
R ¹ to R ⁸ are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C20 aryl group, or substituted or unsubstituted C2 to C30 heterocyclic group , At least one of the R ¹ to R ⁸ is a substituted or unsubstituted C2 to C30 heterocyclic group containing two or more nitrogen atoms,
R ⁹ is hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C4 alkyl group or a substituted or unsubstituted C6 to C12 aryl group,
L ¹ to L ⁸ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,
X ¹ and X ² are each independently O or S,
Two adjacent * in Formula 1 are connected to * in Formula 2;
[Formula 5]

In Chemical Formula 5,
Y ¹ and Y ² are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
Ar ¹ and Ar ² 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 ¹⁰ to R ¹⁵ are each Independently, hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof,
m is one of an integer from 0 to 2;
[Formula 6] [Formula 7]

In Formulas 6 and 7,
Y ³ and Y ⁴ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a substituted or unsubstituted C2 to C30 heteroarylene group, or a combination thereof,
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 ¹⁶ to R ¹⁹ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heterocyclic group, or a combination thereof ego,
Two adjacent * in Formula 3 are connected to two * of Formula 4 to form a fused ring, and * not forming a fused ring in Formula 3 are each independently CR ^a ,
R ^a is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C12 aryl group, a substituted or unsubstituted C2 to C12 heterocyclic group, or a combination thereof;
The "substituted" means that at least one hydrogen is substituted with deuterium, a C1 to C4 alkyl group, a C6 to C18 aryl group, or a C2 to C18 heteroaryl group. The method of claim 8,
Ar ¹ and Ar ² in Formula 5 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 anthra Senyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted quinazolyl group, a substituted or unsubstituted isoquinazolyl group, A composition for an organic optoelectronic device which is a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof. The method of claim 8,
Formula 5 is one of the structures listed in the following Group II, wherein *-Y ¹ -Ar ¹ , and *-Y ² -Ar ² is one of the substituents listed in the following Group III composition for an organic optoelectronic device:
[Group Ⅱ]

[Group Ⅲ]

In groups II and III above, * is a connection point. The method of claim 10,
Formula 5 is represented by C-8 of Group II, and *-Y ¹ -Ar ¹ and *-Y ² -Ar ² are each independently represented by any one of B-1 to B-4 of Group III. Composition for organic optoelectronic devices. The method of claim 8,
The compound represented by the combination of Formula 6 and Formula 7 is a composition for an organic optoelectronic device represented by at least one of the following Formulas 6-I to 6-V:
[Chemical Formula 6-Ⅰ] [Chemical Formula 6-Ⅱ] [Chemical Formula 6-Ⅲ]

[Chemical Formula 6-Ⅳ] [Chemical Formula 6-Ⅴ]

In Formulas 6-I to 6-V, Y ³ and Y ⁴ are a single bond, a phenylene group, a biphenylene group, a pyridylene group, or a pyrimidinylene group,
Ar ³ and Ar ⁴ are a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted triazinyl group,
R ¹⁶ to R ¹⁹ are hydrogen. The method of claim 8,
The first organic optoelectronic device compound and the second organic optoelectronic device compound are included in a weight ratio of 3:7 to 6:4. The anode and cathode facing each other, and
Including at least one layer of an organic layer positioned between the anode and the cathode,
The organic layer is an organic optoelectronic device comprising the compound for an organic optoelectronic device according to any one of claims 4 to 6 or the composition for an organic optoelectronic device according to any one of claims 8 to 13. The method of claim 14,
The organic layer includes a light emitting layer,
The composition for an organic optoelectronic device is an organic optoelectronic device included as a host of the emission layer. A display device comprising the organic optoelectronic device according to claim 14.

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