WO2023153905A1 - Composition for organic optoelectronic diode, organic optoelectronic diode, and display device - Google Patents

Abstract

The present invention relates to: a composition for an organic optoelectronic diode, comprising a first compound represented by chemical formula 1 and a second compound represented by chemical formula 2; and an organic optoelectronic diode and a display device, comprising same. The details of chemical formulas 1 and 2 are as defined in the specification.

Description

Compositions for organic optoelectronic devices, organic optoelectronic devices and display devices

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 between electrical energy and light energy.

Organic optoelectronic devices can be largely divided into two types according to their operating principles. One is a photoelectric device that generates electrical energy as excitons formed by light energy are separated into electrons and holes and the electrons and holes are transferred to different electrodes, respectively. It is a light emitting device that generates light energy from

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) have recently been attracting great attention due to an increase in demand for flat panel display devices. An organic light emitting device is a device that converts electrical energy into light, and the performance of the organic light emitting device is greatly affected by organic materials positioned between electrodes.

One embodiment provides a composition for an organic optoelectronic device capable of implementing a low-driving, high-efficiency, and long-life organic optoelectronic device.

Another embodiment provides an organic optoelectronic device including the compound.

Another embodiment provides a display device including the organic optoelectronic device.

According to one embodiment, a composition for an organic optoelectronic device including a first compound represented by Formula 1 below and a second compound represented by Formula 2 below is provided.

[Formula 1]

In Formula 1,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group;

L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group,

R ¹ to R ⁴ are each independently hydrogen, heavy hydrogen, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or An unsubstituted C2 to C30 heterocyclic group,

n1 is an integer from 1 to 3;

n2 and n3 are each independently an integer of 1 or 2;

n4 is an integer from 1 to 4;

[Formula 2]

In Formula 2,

Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group;

L ⁴ to L ⁶ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group;

R ⁵ to R ⁹ are each independently hydrogen, heavy hydrogen, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or An unsubstituted C2 to C30 heterocyclic group,

m1 to m3 are each independently an integer of 0 or 1,

0 ≤ m1+m2+m3 ≤ 1, and

n5 to n9 are each independently an integer of 1 to 4;

According to another embodiment, an organic optoelectronic device including 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 composition for an organic optoelectronic device.

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

A low driving, high efficiency and long lifespan organic optoelectronic device can be implemented.

1 is a cross-sectional view illustrating an organic light emitting device according to an exemplary embodiment.

<Description of codes>

100: organic light emitting element

105 organic layer

110: cathode

120: anode

130: light emitting layer

140: hole transport region

150: electron transport area

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.

In this specification, unless otherwise defined, "substitution" 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 A heteroaryl group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, a cyano group, or a combination thereof.

In one 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, a C2 to C30 heteroaryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C20 alkyl group, a C6 to C30 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen in a substituent or compound is substituted with deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, or a cyano group. In addition, in a specific example of the present invention, "substitution" means that at least one hydrogen of a substituent or compound is substituted with deuterium, cyano group, methyl group, ethyl group, propyl group, butyl group, phenyl group, biphenyl group, terphenyl group or naphthyl group. means it has been

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

In the present specification, "aryl group" is a general concept of a group having one or more hydrocarbon aromatic moieties, and all elements of the hydrocarbon aromatic moiety have p-orbitals, and these p-orbitals are conjugated Forming a form, for example, including a phenyl group, a naphthyl group, etc., including a form in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, for example, a biphenyl group, a terphenyl group, a quaterphenyl group, etc., and two or more hydrocarbon aromatic moieties may include a non-aromatic fused ring in which they are directly or indirectly fused, such as a fluorenyl group and the like.

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

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

For example, "heteroaryl group" means containing at least one heteroatom selected from the group consisting of N, O, S, P, and Si in the aryl group. Two or more heteroaryl groups may be directly connected through a sigma bond, or if the heteroaryl group includes two or more rings, the two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may include 1 to 3 hetero atoms.

More specifically, the substituted or unsubstituted C6 to C30 aryl group is 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, or a substituted or unsubstituted phenanthrenyl group. An unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted o- A terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted indenyl group, or any of these It may be a combination, but is not limited thereto.

More specifically, the substituted or unsubstituted C2 to C30 heterocyclic group is a substituted or unsubstituted furanyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, or a substituted or unsubstituted pyrazolyl group. Or an 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, 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 an unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted Quinazolinyl group, substituted or unsubstituted quinoxalinyl group, substituted or unsubstituted naphthyridinyl group, substituted or unsubstituted benzoxazinyl group, substituted or unsubstituted benzothiazinyl group, substituted or unsubstituted acridinyl group , A substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted Or an unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.

In this specification, “unsubstituted” means that a hydrogen atom remains as a hydrogen atom without being substituted with another substituent.

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

In the present specification, the hole characteristic refers to a characteristic that can form holes by donating electrons when an electric field is applied, and has conduction characteristics along the HOMO level, so that holes formed at the anode are injected into the light emitting layer, the light emitting layer It means a property that facilitates the movement of holes formed in the anode to the anode and in the light emitting layer.

In addition, electronic properties refer to the characteristics of receiving electrons when an electric field is applied, and has conductivity along the LUMO level, so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer move to the cathode, and in the light emitting layer A property that facilitates movement.

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

A composition for an organic optoelectronic device according to an embodiment includes a first compound and a second compound.

The first compound is represented by Formula 1 below.

[Formula 1]

In Formula 1,

Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group;

L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group,

R ¹ to R ⁴ are each independently hydrogen, heavy hydrogen, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or An unsubstituted C2 to C30 heterocyclic group,

n1 is an integer from 1 to 3;

n2 and n3 are each independently an integer of 1 or 2,

n4 is an integer from 1 to 4;

The first compound represented by Formula 1 is a structure in which amine is substituted for chrysene, and the long fused chrysene ring helps to stabilize the amine for holes and energy, which is advantageous for realizing a long-life device, and is particularly robust fused arylene Phosphorus Krysen is also very thermally stable.

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

[Formula 1-1] [Formula 1-2]

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

In Formula 1-1 to Formula 1-4,

Ar ¹ , Ar ² , L ¹ to L ³ , R ¹ to R ⁴ , and n1 to n4 are defined as described above.

As a specific example, Chemical Formula 1 may be represented by Chemical Formula 1-2.

Ar ¹ and Ar ² in Formula 1 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, or a substituted or unsubstituted anthrayl group. Cenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted benzonaphtho It may be a furanyl group or a substituted or unsubstituted benzonaphthothiophenyl group.

For example, Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzofuranyl group. It may be a benzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

For example, L ¹ to L ³ may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

For example, L ¹ in Formula 1 is a single bond,

*-L ² -Ar ¹ and *-L ³ -Ar ² may each independently be selected from substituents listed in Group I below.

[Group I]

In Group I, the substituent may be unsubstituted or substituted with an additional substituent, and * is a linking point.

The additional substituent may be deuterium, a C1 to C5 alkyl group, or a C6 to C18 aryl group.

In a most specific embodiment, the first compound represented by Formula 1 may be one selected from compounds listed in Group 1 below, but is not limited thereto.

[Group 1]

[A-1] [A-2] [A-3] [A-4]

[A-5] [A-6] [A-7] [A-8]

[A-9] [A-10] [A-11] [A-12]

[A-13] [A-14] [A-15] [A-16]

[A-17] [A-18] [A-19] [A-20]

[A-21] [A-22] [A-23] [A-24]

[A-25] [A-26] [A-27] [A-28]

[A-29] [A-30] [A-31] [A-32]

[A-33] [A-34] [A-35] [A-36]

[A-37] [A-38] [A-39] [A-40]

[A-41] [A-42] [A-43] [A-44]

[A-45] [A-46] [A-47] [A-48]

[A-49] [A-50] [A-51] [A-52]

[A-53] [A-54] [A-55] [A-56]

[A-57] [A-58] [A-59] [A-60]

[A-61] [A-62] [A-63] [A-64]

[A-65] [A-66] [A-67] [A-68]

[A-69] [A-70] [A-71] [A-72]

[A-73] [A-74] [A-75] [A-76]

[A-77] [A-78] [A-79] [A-80]

[A-81] [A-82] [A-83] [A-84]

[A-85] [A-86] [A-87] [A-88]

[A-89] [A-90] [A-91] [A-92]

[A-93] [A-94] [A-95] [A-96]

[A-97] [A-98] [A-99] [A-100]

[A-101] [A-102] [A-103] [A-104]

[A-105] [A-106] [A-107] [A-108]

[A-109] [A-110] [A-111] [A-112]

[A-113] [A-114] [A-115] [A-116]

[A-117] [A-118] [A-119] [A-120]

[A-121] [A-122] [A-123] [A-124]

[A-125] [A-126] [A-127] [A-128]

[A-129] [A-130] [A-131] [A-132]

[A-133] [A-134] [A-135] [A-136]

[A-137] [A-138] [A-139] [A-140]

[A-141] [A-142] [A-143] [A-144]

[A-145] [A-146] [A-147] [A-148]

[A-149] [A-150] [A-151] [A-152]

[A-153] [A-154] [A-155] [A-156]

[A-157] [A-158] [A-159] [A-160]

[A-161] [A-162] [A-163] [A-164]

[A-165] [A-166] [A-167] [A-168]

The second compound is represented by Formula 2 below.

[Formula 2]

In Formula 2,

Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group;

L ⁴ to L ⁶ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group;

R ⁵ to R ⁹ are each independently hydrogen, heavy hydrogen, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or An unsubstituted C2 to C30 heterocyclic group,

m1 to m3 are each independently an integer of 0 or 1,

0 ≤ m1+m2+m3 ≤ 1, and

n5 to n9 are each independently an integer of 1 to 4;

The second compound may be used together with the first compound in the light emitting layer to increase charge mobility and stability, thereby improving light emitting efficiency and lifetime characteristics.

For example, Chemical Formula 2 may be represented by any one of Chemical Formulas 2A to 2D.

[Formula 2A] [Formula 2B]

[Formula 2C] [Formula 2D]

In Formulas 2A to 2D,

Ar ³ , Ar ⁴ , L ⁴ to L ⁶ , R ⁶ to R ⁹ , and n6 to n9 are defined as described above,

R ^5a and R ^5b are each independently selected from hydrogen, heavy hydrogen, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group. Or a substituted or unsubstituted C2 to C30 heterocyclic group.

For example, Ar ³ and Ar ⁴ in Formula 2 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 biphenyl group, or a substituted or unsubstituted naphthyl group. substituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted It may be a substituted or unsubstituted benzonaphthofuranyl group or a substituted or unsubstituted benzonaphthothiophenyl group.

As a specific example, Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted biphenyl group. may be a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group.

For example, L ⁴ to L ⁶ in Formula 2 may each independently be a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

For example, L ⁴ in Formula 2 is a single bond;

*-L ⁵ -Ar ³ and *-L ⁶ -Ar ⁴ may each independently be selected from substituents listed in Group II below.

[Group II]

In Group II, the substituent may be unsubstituted or substituted with an additional substituent, and * is a linking point.

The additional substituent may be deuterium, a C1 to C5 alkyl group, or a C6 to C18 aryl group.

For example, the second compound may be one selected from compounds listed in Group 2 below, but is not limited thereto.

[Group 2]

[B-1] [B-2] [B-3] [B-4]

[B-5] [B-6] [B-7] [B-8]

[B-9] [B-10] [B-11] [B-12]

[B-13] [B-14] [B-15] [B-16]

[B-17] [B-18] [B-19] [B-20]

[B-21] [B-22] [B-23] [B-24]

[B-25] [B-26] [B-27] [B-28]

[B-29] [B-30] [B-31] [B-32]

[B-33] [B-34] [B-35] [B-36]

[B-37] [B-38] [B-39] [B-40]

[B-41] [B-42] [B-43] [B-44]

[B-45] [B-46] [B-47] [B-48]

[B-49] [B-50] [B-51] [B-52]

[B-53] [B-54] [B-55] [B-56]

[B-57] [B-58] [B-59] [B-60]

[B-61] [B-62] [B-63] [B-64]

[B-65] [B-66] [B-67] [B-68]

[B-69] [B-70] [B-71] [B-72]

[B-73] [B-74] [B-75] [B-76]

[B-77] [B-78] [B-79] [B-80]

[B-81] [B-82] [B-83] [B-84]

[B-85] [B-86] [B-87] [B-88]

[B-89] [B-90] [B-91] [B-92]

[B-93] [B-94] [B-95] [B-96]

[B-97] [B-98] [B-99] [B-100]

[B-101] [B-102] [B-103] [B-104]

[B-105] [B-106] [B-107] [B-108]

[B-109] [B-110] [B-111] [B-112]

[B-113] [B-114] [B-115] [B-116]

[B-117] [B-118] [B-119] [B-120]

[B-121] [B-122] [B-123] [B-124]

[B-125] [B-126] [B-127] [B-128]

[B-129] [B-130] [B-131] [B-132]

[B-133] [B-134] [B-135] [B-136]

[B-137] [B-138] [B-139] [B-140]

[B-141] [B-142] [B-143] [B-144]

[B-145] [B-146] [B-147] [B-148]

[B-149] [B-150] [B-151] [B-152]

[B-153] [B-154] [B-155] [B-156]

[B-157] [B-158] [B-159] [B-160]

[B-161] [B-162] [B-163] [B-164]

[B-165] [B-166] [B-167] [B-168]

[B-169] [B-170] [B-171] [B-172]

[B-173] [B-174] [B-175] [B-176]

[B-177] [B-178] [B-179] [B-180]

[B-181] [B-182] [B-183] [B-184]

[B-185] [B-186] [B-187] [B-188]

[B-189] [B-190] [B-191] [B-192]

[B-193] [B-194] [B-195] [B-196]

[B-197] [B-198] [B-199] [B-200]

[B-201] [B-202] [B-203] [B-204]

[B-205] [B-206] [B-207] [B-208]

In a specific embodiment, the first compound is represented by Formula 1-2,

The second compound may be represented by any one of Chemical Formulas 2B to 2C.

The first compound and the second compound may be included in a weight ratio of, for example, 1:99 to 99:1. By being included within the above range, efficiency and lifespan can be improved by implementing bipolar characteristics by setting an appropriate weight ratio using the hole transport capability of the first compound and the electron transport capability of the second compound. Within the above range, for example, it may be included in a weight ratio of about 10:90 to 90:10, about 20:80 to 80:20, for example, about 20:80 to about 70:30, about 20:80 to about 60:40, And it may be included in a weight ratio of about 20:80 to about 50:50. As a specific example, it may be included in a weight ratio of 20:80, 30:70, or 40:60.

In addition to the first compound and the second compound described above, one or more compounds may be further included.

For example, the above-described composition for an organic optoelectronic device may further include a dopant.

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

A dopant is a material that causes light emission by being mixed in a small amount in a composition for an organic optoelectronic device, and a material such as a metal complex that emits light by multiple excitation that is excited in a triplet state or higher may be used. . The dopant may be, for example, an inorganic, organic, or organic-inorganic compound, and may include one type or two or more types.

An example of the dopant may include a phosphorescent dopant, and examples of the phosphorescent dopant include Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh, Pd, or a combination thereof. Organometallic compounds containing As the phosphorescent dopant, for example, a compound represented by Chemical Formula Z may be used, but is not limited thereto.

[Formula Z]

L ⁷ MX

In Formula Z, M is a metal, L ⁷ and X are the same as or different from each other and are ligands that form a complex with M.

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 ⁷ and X may be, for example, biden It may be a tate ligand.

Examples of the ligand represented by L ⁷ and X may be selected from the formulas listed in Group A below, but are not limited thereto.

[Group A]

In the group A,

R ³⁰⁰ to R ³⁰² are each independently hydrogen, deuterium, a C1 to C30 alkyl group with or without halogen substitution, a C6 to C30 aryl group with or without C1 to C30 alkyl substitution, or halogen;

R ³⁰³ to R ³²⁴ are each independently hydrogen, deuterium, halogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, or a substituted Or an unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 heteroaryl group, a substituted or unsubstituted C1 to C30 amino group, a substituted or unsubstituted C6 to C30 arylamino group, SF ₅ , 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 It is a triarylsilyl group having a substituted or unsubstituted C6 to C30 aryl group.

For example, a dopant represented by Chemical Formula V below may be included.

[Formula V]

In Formula V,

R ¹⁰¹ to R ¹¹⁶ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or -SiR ¹³² R ¹³³ R ¹³⁴ ;

Wherein R ¹³² to R ¹³⁴ are each independently a C1 to C6 alkyl group;

At least one of R ¹⁰¹ to R ¹¹⁶ is a functional group represented by Formula V-1 below;

L ¹⁰⁰ is a bidentate ligand of a monovalent anion, and is a ligand that coordinates with iridium through an unshared electron pair of a carbon or heteroatom,

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

[Formula V-1]

In Formula V-1,

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

* means a part connected to a carbon atom.

For example, a dopant represented by Chemical Formula Z-1 may be included.

[Formula Z-1]

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

R ^A , R ^B , R ^C , and R ^D each independently represent mono-, di-, tri-, or tetra-substituted, or unsubstituted;

L ^B , L ^C , and L ^D are each a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO ₂ , CRR', SiRR', GeRR', and combinations thereof independently selected from the group consisting of;

When nA is 1, L ^E is a group consisting of a direct bond, BR, NR, PR, O, S, Se, C=O, S=O, SO ₂ , CRR', SiRR', GeRR', and combinations thereof is selected from; When nA is 0, L ^E is not present;

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

A dopant according to an embodiment may be a platinum complex, and may be represented by Chemical Formula VI below.

[Formula VI]

In Formula VI,

X ¹⁰⁰ is selected from O, S and NR ¹³¹ ;

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

Wherein R ¹³² to R ¹³⁴ are each independently a C1 to C6 alkyl group;

At least one of R ¹¹⁷ to R ¹³¹ is -SiR ¹³² R ¹³³ R ¹³⁴ or a tert-butyl group.

Hereinafter, organic optoelectronic devices to which the above-described composition for organic optoelectronic devices is applied will be described.

The organic optoelectronic device is not particularly limited as long as it is a device capable of 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 drawings.

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

Referring to FIG. 1 , an organic light emitting device 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, for example, a conductor having a high work function so as to smoothly inject holes, and may be made of, for example, metal, metal oxide, and/or conductive polymer. The anode 120 may be formed of, for example, 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); combinations of metals and oxides such as ZnO and Al or SnO ₂ and Sb; conductive polymers such as poly(3-methylthiophene), poly(3,4-(ethylene-1,2-dioxy)thiophene) (polyehtylenedioxythiophene: PEDOT), polypyrrole, and polyaniline; It is not.

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

The organic layer 105 may include the above-described composition for an organic optoelectronic device.

The organic layer 105 includes the light emitting layer 130, and the light emitting layer 130 may include the above-described composition for an organic optoelectronic device.

The composition for an organic optoelectronic device further comprising a dopant may be, for example, a red or green light emitting composition.

The light emitting layer 130 may include, for example, the aforementioned composition for an organic optoelectronic device as a phosphorescent host.

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

The charge transport region may be, for example, the hole transport region 140 .

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.

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. At least one of the listed compounds may be included in at least one of the hole transport layer and the hole transport auxiliary layer.

[Group B]

In addition to the above compounds, known compounds described in US5061569A, JP1993-009471A, WO1995-009147A1, JP1995-126615A, JP1998-095973A and similar structures may be used for the hole transport region 140.

Also, the charge transport region may be, for example, the electron transport region 150 .

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

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. At least one of the listed compounds may be included in at least one of the electron transport layer and the electron transport auxiliary layer.

[Group C]

One embodiment may be an organic light emitting device including a light emitting layer as an organic layer.

Another embodiment may be an organic light emitting device including a light emitting layer and a hole transport region as an organic layer.

Another embodiment may be an organic light emitting device including an emission layer and an electron transport region as an organic layer.

As shown in FIG. 1 , an organic light emitting device according to an exemplary embodiment of the present invention may include a hole transport region 140 and an electron transport region 150 in addition to the emission layer 130 as the organic layer 105 .

Meanwhile, the organic light emitting device 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 as the organic layer described above.

In the organic light emitting device 100, after forming an anode or a cathode on a substrate, an organic layer is formed by a dry film method such as evaporation, sputtering, plasma plating, or ion plating, and then a cathode or cathode thereon. It can be manufactured by forming an anode.

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

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

Hereinafter, the starting materials and reactants used in Examples and Synthesis Examples were purchased from Sigma-Aldrich, TCI, Tokyo chemical industry or P&H tech, or synthesized through known methods, unless otherwise specified.

(Preparation of compounds for organic optoelectronic devices)

A compound presented as a more specific example of the compound of the present invention was synthesized through the following steps.

Synthesis of First Compound

Synthesis Example 1: Synthesis of Compound A-69

[Scheme 1]

a) synthesis of intermediate int-1

2-bromo-4-chlorobenzaldehyde (40.0 g, 182.2 mmol), 2-naphthaleneboronic acid (34.4 g, 200.4 mmol), tetrakis(triphenylphosphine)palladium(0) (10.6 g, 9.2 mmol) and potassium carbonate (75.6 g, 546.8 mmol) in tetrahydrofuran: distilled water = 2: 1 volume ratio of the mixed solution in 900 mL, and stirred under reflux for 12 hours at 80 ℃. Upon completion of the reaction, 37.2 g of int-1 (yield: 76.7%) was obtained by purification using column chromatography (dichloromethane: n-hexane).

b) synthesis of intermediate int-2

Dissolve int-1 (35.2 g, 132 mmol) and (methoxymethyl)triphenylphosphonium chloride (49.8 g, 146 mmol) in 260 mL of tetrahydrofuran, slowly add potassium tert-butoxide (17.8 g, 158 mmol) at 0 ° C and stir. When the reaction is complete, all solvents are removed using a rotary evaporator. Extract twice with dichloromethane and distilled water and dry the organic layer. Without additional purification, dissolve in dichlromethane 260 mL, slowly add methanesulfonic acid (25.4 g, 264 mmol) at 0 ° C and stir. When the reaction was completed, methyl alcohol was added to the reaction solution to precipitate a solid, which was first filtered, and the solid was dissolved in toluene and filtered/purified on silica gel to obtain 22.7 g of int-2 (yield: 65.5%).

c) Synthesis of Compound A-69

int-2 (5.0 g, 19 mmol), 4-(naphthalen-2-yl)-N-phenylaniline (5.6 g, 19 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.9 g, 1 mmol), sodium tert -butoxide (2.7 g, 29 mmol) and tri-tert-butylphosphine (0.6 g, 3 mmol) were added to 95 mL of xylene and stirred under reflux at 150 °C for 12 hours. When the reaction is complete, the solution is poured into an excess of distilled water to form a precipitate. The precipitate is filtered, boiled and dissolved in toluene, and filtered through silica gel. The filtered solution was recrystallized by mixing with acetone to obtain 7.7 g of A-69 (yield: 77.4%).

Synthesis Example 2: Synthesis of Compound A-71

[Scheme 2]

Synthesis in the same manner as in the synthesis of compound A-69 in Synthesis Example 1 using int-2 and N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-2-amine as starting materials and recrystallized from a mixed solution of toluene: acetone to obtain compound A-71. (Yield: 82.4%)

Synthesis Example 3: Synthesis of Compound A-79

[Scheme 3]

a) Synthesis of Intermediate A-79-1

Compound A-69 was synthesized in the same manner as in Synthesis Example 1 using 4-(naphthalen-2-yl)aniline and 1-bromodibenzofuran as starting materials, and purified by column chromatography to obtain intermediate A-79-1. (Yield: 65.4%)

b) Synthesis of Compound A-79

A-79-1 and int-2 were synthesized in the same manner as in Synthesis Example 1 for the synthesis of compound A-69 using int-2 as starting materials, and recrystallized with toluene to obtain compound A-79. (Yield: 59.8%)

Synthesis Example 4: Synthesis of Compound A-158

[Scheme 4]

a) Synthesis of Intermediate A-158-1

1-bromo-4-chloro-2-fluorobenzene (50.0 g, 239 mmol), 1-naphthol (37.9 g, 267 mmol) and potassium carbonate (99.0 g, 716 mmol) were added to 1200 mL of N-methyl-2-pyrrolidinone. The mixture was stirred under reflux at 180 °C for 12 hours. When the reaction is complete, the solution is poured into an excess of distilled water to form a precipitate. The precipitate is filtered, dissolved in dichloromethane, and filtered through silica gel. The filtered solution was recrystallized by mixing with n-hexane to obtain 53.5 g of intermediate A-158-1 (yield: 67.2%).

b) Synthesis of Intermediate A-158-2

Intermediate A-158-1 (53.5 g, 160 mmol), palladium(II) acetate (1.8 g, 8 mmol), tricyclohexylphosphine tetrafluoroborate (9.3 g, 24 mmol) and potassium carbonate (44.3 g, 321 mmol) were mixed with dimethylacetamide 800 mL. and stirred under reflux at 180 °C for 12 hours. When the reaction is complete, the solution is poured into an excess of distilled water to form a precipitate. The precipitate is filtered, dissolved in dichloromethane, and filtered through silica gel. The filtered solution was recrystallized by mixing with n-hexane to obtain 53.5 g of intermediate A-158-2 (yield: 67.2%).

c) Synthesis of Intermediate A-158-3

Intermediate A-158-2 and 2-aminobiphenyl were synthesized in the same manner as in Synthesis Example 1 of Compound A-69 synthesis using 2-aminobiphenyl as starting materials, and purified by column chromatography to obtain Intermediate A-158-3. (Yield: 71.0%)

d) Synthesis of Compound A-158

Intermediate A-158-3 and int-2 were synthesized in the same manner as in the synthesis of compound A-69 in Synthesis Example 1 using int-2 as starting materials, and recrystallized from toluene to obtain compound A-158. (Yield: 66.5%)

Synthesis Example 5: Synthesis of Compound A-166

[Scheme 5]

a) Synthesis of Intermediate A-166-1

Intermediate A-158-2 (20.0 g, 79 mmol), lithium bis(trimethylsilyl)amide solution (95 mmol), tris(dibenzylideneacetone)dipalladium(0) (2.2 g, 2 mmol) and tri-tert-butylphosphine (1.4 g , 7 mmol) was added to 400 mL of toluene and stirred under reflux at 110 °C for 12 hours. When the reaction is complete, dilute aqueous hydrochloric acid solution is added at room temperature and stirred for about 30 minutes. Filter the precipitated solid, add sodium hydroxide solution to neutralize the solution, and stir for about 30 minutes. Dichloromethane: Extract twice with distilled water, and filter the organic layer through silica gel. The filtered solution was recrystallized by mixing with n-hexane to obtain 13.2 g of intermediate A-166-1 (yield: 71.4%).

b) synthesis of intermediate A-166-2

A-166-1 and 1-bromodibenzofuran were synthesized in the same manner as in the synthesis of compound A-69 in Synthesis Example 1 using 1-bromodibenzofuran as starting materials, and purified by column chromatography to obtain intermediate A-166-2. (Yield: 65.1%)

c) Synthesis of Compound A-166

Intermediate A-166-2 and int-2 were synthesized in the same manner as in the synthesis of compound A-69 in Synthesis Example 1 using int-2 as starting materials, and recrystallized from toluene to obtain compound A-166. (Yield: 59.9%)

Comparative Synthesis Example 1: Synthesis of Compound H1

[Scheme 6]

a) Synthesis of Intermediate H1-1

(2-phenylbenzo[d]oxazol-7-yl)boronic acid and 2-bromo-4-chlorobenzaldeh yde as starting materials were synthesized in the same manner as in the synthesis of intermediate int-1 in Synthesis Example 1, and purified by column chromatography. Intermediate H1-1 was obtained. (Yield: 72.0%)

b) synthesis of intermediate H1-2

Intermediate H1-1 was synthesized in the same manner as the synthesis method of intermediate int-2 in Synthesis Example 1 using intermediate H1-1 as a starting material, and recrystallized from toluene to obtain intermediate H1-2. (Yield: 39.5%)

c) synthesis of compound H1

Intermediate H1-2 and N-([1,1'-biphenyl]-2-yl)dibenzo[b,d]thiophen-2-amine were used as starting materials to synthesize compound A-69 in Synthesis Example 1 by the same method. It was synthesized and recrystallized from toluene to obtain compound H1. (Yield: 67.2%)

Comparative Synthesis Example 2: Synthesis of Compound H2

[Scheme 7]

a) Synthesis of Intermediate H2-1

(2-phenylbenzo[d]oxazol-7-yl)boronic acid and 2-bromo-5-chlorobenzaldeh yde were synthesized in the same manner as in the synthesis of intermediate int-1 in Synthesis Example 1 using boronic acid and 2-bromo-5-chlorobenzaldeh yde as starting materials and purified by column chromatography. Intermediate H2-1 was obtained. (Yield: 77.4%)

b) synthesis of intermediate H2-2

Intermediate H2-1 was synthesized in the same manner as the synthesis of intermediate int-2 in Synthesis Example 1 using intermediate H2-1 as a starting material, and recrystallized from monochlorobenzene to obtain intermediate H2-2. (Yield: 42.1%)

c) synthesis of compound H2

Intermediate H2-2 and di([1,1'-biphenyl]-4-yl)amine were synthesized in the same manner as in Synthesis Example 1 of Compound A-69 synthesis using di([1,1'-biphenyl]-4-yl)amine as starting materials, and recrystallized from monochlorobenzene to obtain compound H2. . (Yield: 55.3%)

Synthesis of Second Compound

Synthesis of Synthesis Examples 6 to 9

Compounds (int-3 to int-6) of Synthesis Examples 6 to 9 were obtained by synthesizing in the same manner as the synthesis method of int-1 and int-2 of Synthesis Example 1 using Intermediate A and Intermediate B of Table 1 as starting materials. synthesized.

synthesis example	Intermediate A	Intermediate B	production intermediates	yield (transference number)
Synthesis Example 6			int-3	13.5 g (55.7%)
Synthesis Example 7			int-4	8.8g (49.8%)
Synthesis Example 8			int-5	11.4g (55.2%)
Synthesis Example 9			int-6	16.5g (52.4%)

Synthesis Example 10: Synthesis of Compound B-4

[Scheme 8]

a) Synthesis of Intermediate B-4-1

int-3 (30.0 g, 114 mmol), bis(pinacolato)diboron (37.7 g, 148 mmol), [1,1'bis(diphenylphosphino)ferrocene]palladium(II) dichloride (4.7 g, 5.7 mmol), potassium acetate (33.6 g, 343 mmol) and tricyclohexylphosphine (6.4 g, 23 mmol) were added to 600 mL of N , N -dimethylformamide and stirred under reflux at 140 °C for 12 hours. When the reaction is complete, the solid is completely precipitated by pouring into an excess of distilled water. Filter the precipitated solid, boil and dissolve the solid in toluene, and filter again through silica gel. The filtered solution was recrystallized to obtain 30.4 g (yield: 75.2%) of intermediate B-4-1.

b) synthesis of compound B-4

Intermediate B-4-1 and 2-([1,1'-biphenyl]-3-yl)-4-chloro-6-phenyl-1,3,5-triazine as starting materials Intermediate of Synthesis Example 1 int Compound B-4 was obtained by recrystallization from monochlorobenzene after synthesis in the same manner as -1 synthesis method. (Yield: 88.3%)

Synthesis Example 11: Synthesis of Compound B-11

[Scheme 9]

Intermediate int- It was synthesized in the same manner as in Synthesis Method 1 and recrystallized from monochlorobenzene to obtain compound B-11. (Yield: 80.5%)

Synthesis Example 12: Synthesis of Compound B-111

[Scheme 10]

a) Synthesis of Intermediate B-111-1

Intermediate B-4-1 was synthesized using int-2 as a starting material and recrystallized from a dichloromethane: n -hexane mixed solution to obtain intermediate B-111-1. (Yield: 57.4%)

b) synthesis of compound B-111

Int- It was synthesized in the same manner as in Synthesis Method 1 and recrystallized from monochlorobenzene to obtain compound B-111. (Yield: 75.9%)

Synthesis Example 13: Synthesis of Compound B-170

[Scheme 11]

a) Synthesis of Compound B-170-1

Intermediate B-4-1 was synthesized in the same manner as in Synthesis Example 10 using int-4 as a starting material and recrystallized from a mixed solution of dichloromethane: n -hexane to obtain intermediate B-170-1. (Yield: 65.2%)

b) synthesis of compound B-170

Intermediate int- It was synthesized in the same manner as in Synthesis Method 1 and recrystallized from toluene to obtain compound B-170. (Yield: 69.5%)

Synthesis Example 14: Synthesis of Compound B-187

[Scheme 12]

a) Synthesis of Intermediate B-187-1

Intermediate B-4-1 was synthesized in the same manner as in Synthesis Example 10 using int-5 as a starting material and recrystallized from a mixed solution of dichloromethane: n -hexane to obtain intermediate B-187-1. (Yield: 70.0 %)

b) synthesis of compound B-187

Int- It was synthesized in the same manner as in Synthesis Method 1 and recrystallized from monochlorobenzene to obtain compound B-187. (Yield: 55.9%)

Synthesis Example 15: Synthesis of Compound B-188

[Scheme 13]

a) Synthesis of Intermediate B-188-1

Intermediate B-4-1 was synthesized in the same manner as in Synthesis Example 10 using int-6 as a starting material and recrystallized from a mixed solution of dichloromethane: n -hexane to obtain intermediate B-188-1. (Yield: 70.0 %)

b) synthesis of compound B-188

Int- It was synthesized in the same manner as in Synthesis Method 1 and recrystallized from toluene to obtain compound B-188. (Yield: 79.6%)

Synthesis Example 16: Synthesis of Compound B-203

[Scheme 14]

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-1,3,2-dioxaborolane and 2-chloro-4-(4-(naphthalen-2-yl)phenyl)-6-phenyl Compound B-203 was obtained by recrystallizing from dichlorobenzene after synthesizing -1,3,5-triazine as a starting material in the same manner as in the synthesis of intermediate int-1 in Synthesis Example 1. (Yield: 77.2%)

Comparative Synthesis Example 3: Synthesis of Compound H3

[Scheme 15]

2,9-dichloro-4,7-diphenyl-1,10-phenanthroline and 9-(3-(4,4,5,5-tetrame thyl-1,3,2-dioxaborolan-2-yl)phenyl)- Compound H3 was obtained by recrystallizing from monochlorobenzene by synthesizing in the same manner as in the synthesis method of intermediate int-1 of Synthesis Example 1 using 2 equivalents of 9H-carbazole as a starting material. (Yield: 53.1%)

(Manufacture of organic light emitting device)

Example 1

A glass substrate coated with ITO (Indium tin oxide) was washed with ultrasonic waves in distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, transferred to a plasma cleaner, 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 doped with 3% NDP-9 (commercially available from Novaled) was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 100 Å, and the hole injection layer Compound A was deposited to a thickness of 1350 Å on top to form a hole transport layer. Compound B was deposited on top of the hole transport layer to a thickness of 350 Å to form a hole transport auxiliary layer, and Compound A-69 obtained in Synthesis Example 1 and Compound B-4 obtained in Synthesis Example 10 were used as hosts on the hole transport auxiliary layer. and 10wt% PhGD was doped as a dopant to form a light emitting layer having a thickness of 400 Å by vacuum deposition, where Compound A-69 and Compound B-4 were used in a weight ratio of 5:5. Subsequently, compound C was deposited on the light emitting layer to a thickness of 50 Å to form an electron transport auxiliary layer, and compound D and Liq were simultaneously vacuum deposited in a weight ratio of 1: 1 to form an electron transport layer with a thickness of 300 Å. An organic light emitting device was fabricated by forming a cathode by sequentially vacuum depositing 15 Å of LiQ and 1200 Å of Al on the electron transport layer.

ITO / Compound A (3% NDP-9 doping, 100Å) / Compound A (1350 Å) / Compound B (350Å) / EML [Compound A-69 and Compound B-4 (90wt%): PhGD (10wt%)] (400Å) / Compound C (50Å) / Compound D: LiQ (300Å) / LiQ (15Å) / Al (1200Å).

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

Compound B: N,N-bis(9,9-dimethyl-9H-fluoren-4-yl)-9,9-spirobi(fluorene)-2-amine

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

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

[PhGD]

Examples 2 to 19 and Comparative Examples 1 to 4

Devices of Examples 2 to 19 and Comparative Examples 1 to 4 were fabricated in the same manner as in Example 2, except that the host was changed as shown in Table 2 below.

evaluation

(1) Measurement of change in current density according to voltage change

With respect to the manufactured organic light emitting device, while increasing the voltage from 0V to 10V, a current value flowing through the unit device was measured using a current-voltmeter (Keithley 2400), and the result was obtained by dividing the measured current value by the area.

(2) Measurement of luminance change according to voltage change

The result was obtained by measuring the luminance of the manufactured organic light emitting device using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0V to 10V.

(3) Measurement of luminous efficiency

Luminous efficiency (cd/A) of the same current density (10 mA/cm ² ) was calculated using the luminance and current density measured from (1) and (2) above.

Relative values based on the luminous efficiency of Comparative Example 1 are shown in Table 2 below.

(4) life measurement

For the manufactured organic light emitting device, the initial luminance (cd/m ² ) was emitted at 24,000 cd/m ² using the Polaronics lifetime measurement system, and the decrease in luminance over time was measured, and the luminance was 95% compared to the initial luminance. The reduced time point was measured as the T95 lifetime.

Relative values based on the T95 lifetime of Comparative Example 1 are shown in Table 2 below.

(5) Driving voltage measurement

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

Relative values based on the driving voltage of Comparative Example 1 are shown in Table 2 below.

	1st host	2nd host	drive voltage (%)	Luminous Efficiency (%)	Lifetime T95 (%)
Example 1	A-69	B-4	96	102	333
Example 2	A-69	B-11	94	107	267
Example 3	A-69	B-111	94	110	267
Example 4	A-69	B-170	94	109	250
Example 5	A-69	B-187	93	107	283
Example 6	A-69	B-188	94	109	250
Example 7	A-69	B-203	91	101	300
Example 8	A-71	B-4	97	102	350
Example 9	A-71	B-11	94	107	283
Example 10	A-71	B-111	94	110	283
Example 11	A-79	B-4	97	103	333
Example 12	A-79	B-170	95	110	267
Example 13	A-79	B-187	94	108	300
Example 14	A-79	B-188	95	109	250
Example 15	A-158	B-4	96	101	367
Example 16	A-158	B-188	95	106	300
Example 17	A-166	B-4	97	101	350
Example 18	A-166	B-11	96	104	300
Example 19	A-166	B-203	91	100	300
Comparative Example 1	H1	B-4	100	100	100
Comparative Example 2	H2	B-4	97	101	67
Comparative Example 3	H2	H3	115	87	3
Comparative Example 4	A-69	H3	113	89	3

Referring to Table 2, it can be seen that the organic light emitting device to which the compound according to the embodiment of the present invention is applied has improved drive, efficiency, and lifespan characteristics compared to the organic light emitting device according to the comparative example, and in particular, lifespan characteristics are remarkably improved.

Although the embodiments have been described in detail, the scope of the present invention is not limited thereto, and various modifications and improvements of those skilled in the art using the basic concepts of the present invention defined in the following claims also fall within the scope of the present invention. will be.

Claims (13)

1. A first compound represented by Formula 1 below, and

   A composition for an organic optoelectronic device comprising a second compound represented by Formula 2 below:

   [Formula 1]

   

   In Formula 1,

   Ar ¹ and Ar ² are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group;

   L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group or a substituted or unsubstituted C2 to C30 heteroarylene group,

   R ¹ to R ⁴ are each independently hydrogen, heavy hydrogen, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or An unsubstituted C2 to C30 heterocyclic group,

   n1 is an integer from 1 to 3;

   n2 and n3 are each independently an integer of 1 or 2;

   n4 is an integer from 1 to 4;

   [Formula 2]

   

   In Formula 2,

   Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group;

   L ⁴ to L ⁶ are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group;

   R ⁵ to R ⁹ are each independently hydrogen, heavy hydrogen, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or An unsubstituted C2 to C30 heterocyclic group,

   m1 to m3 are each independently an integer of 0 or 1,

   0 ≤ m1+m2+m3 ≤ 1, and

   n5 to n9 are each independently an integer of 1 to 4;
2. According to claim 1,

   Formula 1 is a composition for an organic optoelectronic device represented by any one of the following Formulas 1-1 to 1-4:

   [Formula 1-1] [Formula 1-2]

   

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

   

   In Formula 1-1 to Formula 1-4,

   Ar ¹ , Ar ² , L ¹ to L ³ , R ¹ to R ⁴ , and n1 to n4 are as defined in claim 1.
3. According to claim 1,

   Ar ¹ and Ar ² in Formula 1 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, or a substituted or unsubstituted anthrayl group. Cenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted benzonaphtho A composition for an organic optoelectronic device comprising a furanyl group or a substituted or unsubstituted benzonaphthothiophenyl group.
4. According to claim 1,

   L ¹ of Formula 1 is a single bond,

   *-L ² -Ar ¹ and *-L ³ -Ar ² are each independently one selected from the substituents listed in Group I below, a composition for an organic optoelectronic device:

   [Group I]

   

   In Group I above, * is a connection point.
5. According to claim 1,

   The first compound is a composition for an organic optoelectronic device, wherein the first compound is one selected from compounds listed in Group 1:

   [Group 1]

   [A-1] [A-2] [A-3] [A-4]

   

   [A-5] [A-6] [A-7] [A-8]

   

   [A-9] [A-10] [A-11] [A-12]

   

   [A-13] [A-14] [A-15] [A-16]

   

   [A-17] [A-18] [A-19] [A-20]

   

   [A-21] [A-22] [A-23] [A-24]

   

   [A-25] [A-26] [A-27] [A-28]

   

   [A-29] [A-30] [A-31] [A-32]

   

   [A-33] [A-34] [A-35] [A-36]

   

   [A-37] [A-38] [A-39] [A-40]

   

   [A-41] [A-42] [A-43] [A-44]

   

   [A-45] [A-46] [A-47] [A-48]

   

   [A-49] [A-50] [A-51] [A-52]

   

   [A-53] [A-54] [A-55] [A-56]

   

   [A-57] [A-58] [A-59] [A-60]

   

   [A-61] [A-62] [A-63] [A-64]

   

   [A-65] [A-66] [A-67] [A-68]

   

   [A-69] [A-70] [A-71] [A-72]

   

   [A-73] [A-74] [A-75] [A-76]

   

   [A-77] [A-78] [A-79] [A-80]

   

   [A-81] [A-82] [A-83] [A-84]

   

   [A-85] [A-86] [A-87] [A-88]

   

   [A-89] [A-90] [A-91] [A-92]

   

   [A-93] [A-94] [A-95] [A-96]

   

   [A-97] [A-98] [A-99] [A-100]

   

   [A-101] [A-102] [A-103] [A-104]

   

   [A-105] [A-106] [A-107] [A-108]

   

   [A-109] [A-110] [A-111] [A-112]

   

   [A-113] [A-114] [A-115] [A-116]

   

   [A-117] [A-118] [A-119] [A-120]

   

   [A-121] [A-122] [A-123] [A-124]

   

   [A-125] [A-126] [A-127] [A-128]

   

   [A-129] [A-130] [A-131] [A-132]

   

   [A-133] [A-134] [A-135] [A-136]

   

   [A-137] [A-138] [A-139] [A-140]

   

   [A-141] [A-142] [A-143] [A-144]

   

   [A-145] [A-146] [A-147] [A-148]

   

   [A-149] [A-150] [A-151] [A-152]

   

   [A-153] [A-154] [A-155] [A-156]

   

   [A-157] [A-158] [A-159] [A-160]

   

   [A-161] [A-162] [A-163] [A-164]

   

   [A-165] [A-166] [A-167] [A-168]

   

   .
6. According to claim 1,

   Formula 2 is a composition for an organic optoelectronic device represented by any one of Formulas 2A to 2D:

   [Formula 2A] [Formula 2B]

   

   [Formula 2C] [Formula 2D]

   

   In Formulas 2A to 2D,

   Ar ³ , Ar ⁴ , L ⁴ to L ⁶ , R ⁶ to R ⁹ , and n6 to n9 are as defined in claim 1,

   R ^5a and R ^5b are each independently selected from hydrogen, heavy hydrogen, a cyano group, a halogen group, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group. Or a substituted or unsubstituted C2 to C30 heterocyclic group.
7. According to claim 1,

   Ar ³ and Ar ⁴ in Formula 2 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, or a substituted or unsubstituted anthrayl group. Cenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, substituted or unsubstituted substituted or unsubstituted dibenzofuranyl group, A composition for an organic optoelectronic device, which is a substituted benzonaphthofuranyl group or a substituted or unsubstituted benzonaphthothiophenyl group.
8. According to claim 1,

   L ⁴ of Formula 2 is a single bond;

   *-L ⁵ -Ar ³ and *-L ⁶ -Ar ⁴ are each independently one selected from the substituents listed in Group II below, composition for an organic optoelectronic device:

   [Group II]

   

   In Group II above, * is a connection point.
9. According to claim 1,

   The second compound is a composition for an organic optoelectronic device in which one selected from the compounds listed in Group 2 below:

   [Group 2]

   [B-1] [B-2] [B-3] [B-4]

   

   [B-5] [B-6] [B-7] [B-8]

   

   [B-9] [B-10] [B-11] [B-12]

   

   [B-13] [B-14] [B-15] [B-16]

   

   [B-17] [B-18] [B-19] [B-20]

   

   [B-21] [B-22] [B-23] [B-24]

   

   [B-25] [B-26] [B-27] [B-28]

   

   [B-29] [B-30] [B-31] [B-32]

   

   [B-33] [B-34] [B-35] [B-36]

   

   [B-37] [B-38] [B-39] [B-40]

   

   [B-41] [B-42] [B-43] [B-44]

   

   [B-45] [B-46] [B-47] [B-48]

   

   [B-49] [B-50] [B-51] [B-52]

   

   [B-53] [B-54] [B-55] [B-56]

   

   [B-57] [B-58] [B-59] [B-60]

   

   [B-61] [B-62] [B-63] [B-64]

   

   [B-65] [B-66] [B-67] [B-68]

   

   [B-69] [B-70] [B-71] [B-72]

   

   [B-73] [B-74] [B-75] [B-76]

   

   [B-77] [B-78] [B-79] [B-80]

   

   [B-81] [B-82] [B-83] [B-84]

   

   [B-85] [B-86] [B-87] [B-88]

   

   [B-89] [B-90] [B-91] [B-92]

   

   [B-93] [B-94] [B-95] [B-96]

   

   [B-97] [B-98] [B-99] [B-100]

   

   [B-101] [B-102] [B-103] [B-104]

   

   [B-105] [B-106] [B-107] [B-108]

   

   [B-109] [B-110] [B-111] [B-112]

   

   [B-113] [B-114] [B-115] [B-116]

   

   [B-117] [B-118] [B-119] [B-120]

   

   [B-121] [B-122] [B-123] [B-124]

   

   [B-125] [B-126] [B-127] [B-128]

   

   [B-129] [B-130] [B-131] [B-132]

   

   [B-133] [B-134] [B-135] [B-136]

   

   [B-137] [B-138] [B-139] [B-140]

   

   [B-141] [B-142] [B-143] [B-144]

   

   [B-145] [B-146] [B-147] [B-148]

   

   [B-149] [B-150] [B-151] [B-152]

   

   [B-153] [B-154] [B-155] [B-156]

   

   [B-157] [B-158] [B-159] [B-160]

   

   [B-161] [B-162] [B-163] [B-164]

   

   [B-165] [B-166] [B-167] [B-168]

   

   [B-169] [B-170] [B-171] [B-172]

   

   [B-173] [B-174] [B-175] [B-176]

   

   [B-177] [B-178] [B-179] [B-180]

   

   [B-181] [B-182] [B-183] [B-184]

   

   [B-185] [B-186] [B-187] [B-188]

   

   [B-189] [B-190] [B-191] [B-192]

   

   [B-193] [B-194] [B-195] [B-196]

   

   [B-197] [B-198] [B-199] [B-200]

   

   [B-201] [B-202] [B-203] [B-204]

   

   [B-205] [B-206] [B-207] [B-208]

   
10. According to claim 1,

    The first compound is represented by Formula 1-2 below,

    The second compound is a composition for an organic optoelectronic device represented by any one of Formulas 2B to 2D:

    [Formula 1-2]

    

    In Formula 1-2,

    Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothione group. An opayl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group,

    L ¹ is a single bond;

    L ² and L ³ are each independently a single bond, a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group,

    R ¹ to R ⁴ are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group or a substituted or unsubstituted C6 to C12 aryl group,

    n1 to n4 are integers of 0 or 1;

    [Formula 2B]

    

    [Formula 2C] [Formula 2D]

    

    In Formulas 2B to 2D,

    Ar ³ and Ar ⁴ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothio group. An opayl group, a substituted or unsubstituted benzonaphthofuranyl group, or a substituted or unsubstituted benzonaphthothiophenyl group,

    L ⁴ is a single bond;

    L ⁵ and L ⁶ are each independently a single bond, a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group,

    R ⁶ to R ⁹ and R ^5a and R ^5b are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C12 aryl group;

    n6 to n9 are each independently an integer of 0 or 1;
11. anode and cathode facing each other,

    At least one organic layer positioned between the anode and the cathode,

    The organic layer is an organic optoelectronic device comprising the composition for an organic optoelectronic device according to any one of claims 1 to 10.
12. According to claim 11,

    The organic layer includes a light emitting layer,

    The light emitting layer is an organic optoelectronic device comprising the composition for the organic optoelectronic device.
13. A display device comprising the organic optoelectronic device according to claim 11 .

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