KR102625052B1 - Compound and Organic light emitting device comprising same - Google Patents

Abstract

상기 화학식 1에 대해서는 상세한 설명을 참조한다.Compound represented by Formula 1:
<Formula 1>

For the above Chemical Formula 1, please refer to the detailed description.

Description

Compound and organic light emitting device comprising same}

It relates to compounds and organic light-emitting devices containing them.

Organic light emitting devices (organic light emitting devices) are self-emitting devices that not only have a wide viewing angle and excellent contrast, but also have the advantages of fast response time, excellent brightness, driving voltage, and response speed characteristics, and the ability to be multicolored.

The organic light-emitting device has a first electrode disposed on an upper part of a substrate, and a hole transport region, a light-emitting layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. It can have a structure. Holes injected from the first electrode move to the light-emitting layer via the hole transport region, and electrons injected from the second electrode move to the light-emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the light emitting layer region to generate excitons. Light is generated as this exciton changes from the excited state to the ground state.

The goal is to develop compounds that exhibit high glass transition temperature, electrical stability, hole transport ability, and luminous efficiency, and introduce them into the hole transport layer and emitting layer of organic light-emitting devices.

According to one aspect, a compound represented by the following formula (1) is provided:

<Formula 1>

In Formula 1,

R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, amino group, nitro group, nitrile group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group , substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and selected from substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups;

L ₁ and L ₂ are each independently a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic groups;

Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, selected from a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

a, b, c and d are each independently selected from integers from 0 to 3;

A is hydrogen; or a substituted or unsubstituted C ₆ -C ₆₀ aryl group is fused;

The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic heterocondensed polycyclic group, At least one substituent among a substituted C ₆ -C ₆₀ arylene group, a substituted C ₁ -C ₆₀ heteroarylene group, a substituted divalent non-aromatic condensed polycyclic group, and a substituted divalent non-aromatic condensed heteropolycyclic group ,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, - C ₁ -C ₆₀ alkyl group, C ₂ substituted with at least one of N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ) -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), substituted with at least one of C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalke Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non- aromatic heterocondensed polycyclic group; and

Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ); is selected from;

Q ₁₁ to Q ₁₇ and Q ₂₁ to Q ₂₇ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₆₀ alkyl group, C 2 -C ₆₀ alkenyl group, C _{2 -C 60} alkynyl group, C ₁ -C ₆₀ Alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ - C ₆₀ is selected from heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group.

According to another aspect, a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer. An organic light-emitting device is provided, wherein the organic layer includes the compound.

According to another aspect, a flat panel display device is provided, including the organic light emitting device, wherein a first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.

In one embodiment of the present invention, the organic light emitting device exhibits high efficiency, low voltage, high brightness, and long lifespan.

1 is a diagram schematically showing the structure of an organic light-emitting device according to an embodiment.

A compound according to one aspect of the present invention is represented by the following formula (1):

<Formula 1>

In Formula 1,

R ₁ to R ₄ are each independently hydrogen, deuterium, halogen, amino group, nitro group, nitrile group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group , substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and selected from substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups;

L ₁ and L ₂ are each independently a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic groups;

Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, selected from a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

a, b, c and d are each independently selected from integers from 0 to 3;

A is hydrogen; or a substituted or unsubstituted C ₆ -C ₆₀ aryl group is fused;

The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic heterocondensed polycyclic group, At least one substituent among a substituted C ₆ -C ₆₀ arylene group, a substituted C ₁ -C ₆₀ heteroarylene group, a substituted divalent non-aromatic condensed polycyclic group, and a substituted divalent non-aromatic condensed heteropolycyclic group ,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, - C ₁ -C ₆₀ alkyl group, C ₂ substituted with at least one of N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ) -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), substituted with at least one of C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalke Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non- aromatic heterocondensed polycyclic group; and

Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ); is selected from;

Q ₁₁ to Q ₁₇ and Q ₂₁ to Q ₂₇ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₆₀ alkyl group, C 2 -C ₆₀ alkenyl group, C _{2 -C 60} alkynyl group, C ₁ -C ₆₀ Alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ - C ₆₀ is selected from heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group.

The fact that A is hydrogen means that nothing is fused to the benzochromene moiety.

The compounds of Formula 1 according to the present invention function as hole injection materials, hole transport materials, and/or light-emitting materials. In addition, compounds of Formula 1 have a high glass transition temperature (Tg) or melting point due to the introduction of a heterocycle. Therefore, heat resistance to Joule heat generated during light emission, among the organic layers, or between the organic layer and the metal electrode, and resistance in a high temperature environment are increased. Organic light-emitting devices manufactured using these compounds have high durability during storage and operation.

According to one embodiment of the present invention, in Formula 1, A may be a fusion of benzene or naphthalene.

According to one embodiment of the present invention, in Formula 1, R ₃ and R ₄ may each independently be hydrogen or deuterium.

According to one embodiment of the present invention, in Formula 1, L ₁ and L ₂ are each independently a substituted or unsubstituted C ₆ -C ₆₀ arylene group, or a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group. It could be Rengi.

According to one embodiment of the present invention, in Formula 1, Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group or a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group. , a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to one embodiment of the present invention, in Formula 1, R ₁ and R ₂ are each independently hydrogen, deuterium, or one of the following Formulas 2a to 2d,

In the above formulas 2a to 2d, Z ₁ is each independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or Unsubstituted aryl group having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 20 carbon atoms, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic hetero a condensed polycyclic group, and Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ );

p represents an integer from 1 to 5;

* indicates binding site; or

R ₁ and R ₂ may be connected to each other to form a cyclohexyl group or a cycloheptyl group.

According to one embodiment of the present invention, in Formula 1, L ₁ or L ₂ may be of Formula 3a below:

In Formula 3a, * represents a binding site.

According to one embodiment of the present invention, in Formula 1, Ar ₁ to Ar ₄ may each independently represent the following Formulas 4a to 4e:

In Formulas 4a to 4e, H ₁ represents O, S, CR ₁₁ R ₁₂ , or NR ₁₃ ,

R ₁₁ to R ₁₃ , and Z ₁ are each independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or Unsubstituted aryl group having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 20 carbon atoms, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic hetero a condensed polycyclic group, and Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ );

p represents an integer from 1 to 9;

* indicates a binding site.

According to one embodiment of the present invention, Formula 1 may be Formula 2, 3, or 4 below:

<Formula 2>

<Formula 3>

<Formula 4>

In Formula 2, 3, or 4, the definitions of substituents and symbols are as described above.

According to one embodiment of the present invention, Formula 1 may be Formula 5 below:

<Formula 5>

In Formula 5, the definitions of substituents and symbols are as described above.

According to one embodiment of the present invention, the compound of Formula 1 may be any one of the following compounds:

In this specification, “organic layer” is a term referring to all single and/or multiple layers interposed between the first electrode and the second electrode of the organic light emitting device. Materials included in the “organic layer” layer are not limited to organic materials.

Figure 1 schematically shows a cross-sectional view of an organic light-emitting device 10 according to an embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

Hereinafter, the structure and manufacturing method of an organic light-emitting device according to an embodiment of the present invention will be described with reference to FIG. 1.

A substrate may be additionally disposed below the first electrode 110 or above the second electrode 190 in FIG. 1 . The substrate may be a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness.

The first electrode 110 may be formed, for example, by providing a first electrode material on the upper part of the substrate using a deposition method or sputtering method. When the first electrode 110 is an anode, the material for the first electrode may be selected from materials with a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. Materials for the first electrode include transparent and highly conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), and zinc oxide (ZnO). Alternatively, to form the first electrode 110, which is a transflective electrode or a reflective electrode, materials for the first electrode include magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), and calcium (Ca). ), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

The first electrode 110 may have a single layer or a multi-layer structure having multiple layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO, but is not limited to this.

An organic layer 150 is disposed on the first electrode 110. The organic layer 150 includes a light emitting layer.

The organic layer 150 may further include a hole transport region interposed between the first electrode and the light-emitting layer and an electron transport region interposed between the light-emitting layer and the second electrode. You can.

The hole transport region may include at least one of a hole transport layer (HTL), a hole injection layer (HIL), a buffer layer, and an electron blocking layer, and the electron transport region may include a hole blocking layer (HBL) and an electron transport layer (ETL). ) and at least one of an electron injection layer (EIL); but is not limited thereto.

The hole transport region may have a single layer made of a single material, a single layer made of a plurality of different materials, or a multilayer structure having a plurality of layers made of a plurality of different materials.

For example, the hole transport region may have a single layer structure made of a plurality of different materials, or a hole injection layer/hole transport layer, a hole injection layer/hole transport layer/buffer layer sequentially stacked from the first electrode 110. , it may have a structure of a hole injection layer/buffer layer, a hole transport layer/buffer layer, or a hole injection layer/hole transport layer/electron blocking layer, but is not limited thereto.

When the hole transport region includes a hole injection layer, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI) methods are used. The hole injection layer can be formed on the first electrode 110 using various methods such as the like.

When forming a hole injection layer by vacuum deposition, the deposition conditions include, for example, a deposition temperature of about 100 to about 500°C, a vacuum degree of about 10 ^-8 to about ^{10 -3 torr} , and about 0.01 to about 100 Å/sec. Within the deposition rate range, it can be selected in consideration of the hole injection layer compound to be deposited and the hole injection layer structure to be formed.

When forming a hole injection layer by spin coating, the coating conditions are a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature of about 80 ℃ to 200 ℃, the compound for the hole injection layer to be deposited and the hole to be formed It may be selected considering the injection layer structure.

When the hole transport region includes a hole transport layer, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, laser induced thermal imaging (LITI), etc. The hole transport layer can be formed on the first electrode 110 or on the hole injection layer using various methods. When forming a hole transport layer by vacuum deposition or spin coating, the deposition and coating conditions of the hole transport layer refer to the deposition and coating conditions of the hole injection layer.

The hole transport region is m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, alpha-NPB, TAPC, HMTPD, TCTA (4,4',4"- Tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N-carbazolyl)triphenylamine), Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid), PEDOT/PSS( Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate):Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), Pani/CSA (Polyaniline/Camphor sulfonicacid:Polyaniline/Camphor sulfonic acid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), a compound represented by the following formula 201, a compound represented by the following formula 202, or a compound of the present invention According to one embodiment, it may include a compound of Formula 1:

<Formula 201>

<Formula 202>

In formulas 201 and 202,

Descriptions of L ₂₀₁ to L ₂₀₅ include, independently of each other, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic selected from condensed polycyclic groups, and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic groups;

xa1 to xa4 are independently selected from 0, 1, 2, and 3;

xa5 is selected from 1, 2, 3, 4 and 5;

R ₂₀₁ to R ₂₀₄ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group. , substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. is selected.

For example, in formulas 201 and 202,

L ₂₀₁ to L ₂₀₅ are independently of each other,

Phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorene group, dibenzofluorene group, phenanthrenylene group, anthracenylene group, pyrenylene group, chrysenylene group, pyridinyl lene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinenylene group, quinoxalinylene group, quinazolinylene group, carbazonylene group and triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group , phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group. , a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, substituted with at least one of a quinazolinyl group, a carbazolyl group, and a triazinyl group. , phenanthrenylene group, anthracenylene group, pyrenylene group, chrycenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinyl. Len group, quinazolinylene group, carbazonylene group and triazinylene group; is selected from;

xa1 to xa4 are independently 0, 1, or 2;

xa5 is 1, 2, or 3;

R ₂₀₁ to R ₂₀₄ are independently of each other,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, azulenyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, di Benzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group , quinazolinyl group, carbazolyl group and triazinyl group, substituted with at least one of phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group. , phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group. , carbazolyl group and triazinyl group; It may be selected from among, but is not limited to.

The compound represented by Formula 201 may be represented by the following Formula 201A:

<Formula 201A>

For example, the compound represented by Formula 201 may be represented by the following Formula 201A-1, but is not limited thereto:

<Formula 201A-1>

The compound represented by Formula 202 may be represented by the following Formula 202A, but is not limited thereto:

<Formula 202A>

In the above formulas 201A, 201A-1 and 202A, the description of L ₂₀₁ to L ₂₀₃ , xa1 to xa3, xa5 and R ₂₀₂ to R ₂₀₄ refers to the description in this specification, and for R ₂₁₁ , refer to the description of R ₂₀₃ , R ₂₁₃ to R ₂₁₆ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, car Boxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ - C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl group, oxy group, It may be selected from a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

For example, among the formulas 201A, 201A-1 and 202A,

L ₂₀₁ to L ₂₀₃ are independently of each other,

Phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, pyrenylene group, chrysenylene group, Pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group, carbazonylene group and triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group , phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group. , substituted with at least one selected from carbazolyl group and triazinyl group, phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthre. Nylene group, anthracenylene group, pyrenylene group, chrycenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quina Zolinylene group, carbazonylene group and triazinylene group; is selected from;

xa1 to xa3 are independently 0 or 1;

R ₂₀₃ , R ₂₁₁ and R ₂₁₂ are independently of each other,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid Carboxylic acid or salt thereof, sulfonic acid or salt thereof , phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzo. Fluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, substituted with at least one selected from quinazolinyl group, carbazolyl group and triazinyl group. , phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, Quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

R ₂₁₃ and R ₂₁₄ are independently of each other,

C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl Substituted with at least one selected from group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group , phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group. , substituted with at least one selected from carbazolyl group and triazinyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthre. Nyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole diary and triazinyl groups; is selected from;

R ₂₁₅ and R ₂₁₆ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl Substituted with at least one selected from group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group , phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group. , substituted with at least one selected from carbazolyl group and triazinyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthre. Nyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole diary and triazinyl groups; is selected from;

xa5 is 1 or 2.

In Formulas 201A and 201A-1, R ₂₁₃ and R ₂₁₄ may be combined with each other to form a saturated or unsaturated ring.

The compound represented by Formula 201 and the compound represented by Formula 202 may include, but are not limited to, the following compounds HT1 to HT20.

The thickness of the hole transport region may be about 100Å to about 10000Å, for example, about 100Å to about 1000Å. If the hole transport region includes both a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is about 50 Å to about 10000 Å. It may be 2000 Å, for example about 100 Å to about 1500 Å. When the thickness of the hole transport region, hole injection layer, and hole transport layer satisfies the above-mentioned ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

In addition to the materials described above, the hole transport region may further include a charge-generating material to improve conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane. quinone derivatives such as phosphorus (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and the following compound HT-D1, etc., but are not limited thereto.

<Compound HT-D1> <F4-TCNQ>

The hole transport region may further include a buffer layer in addition to the electron blocking layer, hole injection layer, and hole transport layer as described above. The buffer layer may serve to increase light emission efficiency by compensating for an optical resonance distance depending on the wavelength of light emitted from the light emitting layer. The material included in the buffer layer may be a material that can be included in the hole transport region. The electron blocking layer is a layer that serves to prevent electron injection from the electron transport region.

Vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, or laser induced thermal imaging (LITI) method is applied to the top of the first electrode 110 or the hole transport area. ), etc., are used to form the light-emitting layer. When forming the light-emitting layer by vacuum deposition and spin coating, the deposition and coating conditions of the light-emitting layer refer to the deposition and coating conditions of the hole injection layer.

When the organic light emitting device 10 is a full color organic light emitting device, the light emitting layer and each subpixel may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light-emitting layer may have a structure in which a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer are stacked, or a structure in which a red light-emitting material, a green light-emitting material, and a blue light-emitting material are mixed without layer distinction, and may emit white light.

The light emitting layer may include a host and a dopant.

The host may include, for example, at least one of the following: TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, and TCP:

Alternatively, the host may include a compound represented by Chemical Formula 301 below.

<Formula 301>

Ar ₃₀₁ -[(L ₃₀₁ ) _xb1 -R ₃₀₁ ] _xb2

In the above formula 301,

Ar ₃₀₁ is

Naphthalene, hepthalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluorine fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indeno. anthracene (indenoanthracene);

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl group oxy group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, and -Si(Q ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ ) (Q ₃₀₁ to Q ₃₀₃ are independently of each other, substituted with at least one selected from hydrogen, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group), naphthalene, hepthalene, fluorene , spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and inde. noanthracene; is selected from;

L ₃₀₁ is phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorene group, dibenzofluorene group, phenanthrenylene group, anthracenylene group, pyrenylene group, chrysenylene group , pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group, carbazonylene group and triazinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carboxylinyl group Substituted with at least one of a zolyl group and a triazinyl group, phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, Anthracenylene group, pyrenylene group, chrysenylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, quinolinylene group, isoquinolinylene group, quinoxalinylene group, quinazolinylene group , carbazoylene group and triazinylene group; is selected from;

R ₃₀₁ is

C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, A C ₁ -C ₂₀ alkyl group substituted with at least one selected from pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group. and C ₁ -C ₂₀ alkoxy group;

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Cenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and tria Substituted with at least one selected from the group consisting of phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group. group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

xb1 is selected from 0, 1, 2 and 3;

xb2 is selected from 1, 2, 3 and 4.

For example, in Formula 301,

L ₃₀₁ is phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, pyrenylene group and cry Senylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Substituted with at least one selected from cenyl group, pyrenyl group and chrysenyl group, phenylene group, naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, pyrenylene group and chrysenylene group; is selected from;

R ₃₀₁ is

C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Substituted with at least one selected from salts thereof, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group and chrysenyl group. C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group and chrysenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthra Substituted with at least one selected from cenyl group, pyrenyl group and chrysenyl group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group group, pyrenyl group and chrysenyl group; It may be selected from among, but is not limited to.

For example, the host may include a compound represented by the following formula 301A:

<Formula 301A>

For descriptions of substituents in Formula 301A, refer to what is described herein.

The compound represented by Formula 301 may include at least one of the following compounds H1 to H42, but is not limited thereto:

Alternatively, the host may include at least one of the following compounds H43 to H49, but is not limited thereto:

The dopant may include a known fluorescent dopant, a phosphorescent dopant, or the compound of Formula 1 according to an embodiment of the present invention.

The phosphorescent dopant may include an organometallic complex represented by the following chemical formula 401:

<Formula 401>

In the above formula 401,

M is selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb) and tholium (TM);

X ₄₀₁ to X ₄₀₄ are independently nitrogen or carbon;

A ₄₀₁ and A ₄₀₂ rings are each independently selected from substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spiro-fluorene, or 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 isobenzooxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran, and selected from substituted or unsubstituted dibenzothiophene;

The substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrole, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, substituted substituted thiazole, substituted isothiazole, substituted oxazole, substituted isoxazole, substituted pyridine, substituted pyrazine, substituted pyrimidine, substituted pyridazine, substituted quinoline, substituted isoquinoline, substituted benzo Quinoline, substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzoimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzoxazole, substituted iso At least one substituent of benzooxazole, substituted triazole, substituted oxadiazole, substituted triazine, substituted dibenzofuran and substituted dibenzothiophene is:

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, non-monovalent -Aromatic heterocondensed polycyclic group, -N (Q ₄₀₁ ) (Q ₄₀₂ ), -Si (Q ₄₀₃ ) (Q ₄₀₄ ) (Q ₄₀₅ ) and -B (Q ₄₀₆ ) (Q ₄₀₇ ), substituted with at least one of ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl oxy groups, C ₆ -C ₆₀ arylthio groups, C ₁ -C ₆₀ heteroaryl groups and non-aromatic condensed polycyclic groups;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl group oxy group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N(Q ₄₁₁ )(Q ₄₁₂ ), -Si(Q ₄₁₃ )(Q ₄₁₄ )(Q ₄₁₅ ) and -B(Q ₄₁₆ )(Q ₄₁₇ ), substituted with at least one of C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalke Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non- aromatic heterocondensed polycyclic group; and

-N(Q ₄₂₁ )(Q ₄₂₂ ), -Si(Q ₄₂₃ )(Q ₄₂₄ )(Q ₄₂₅ ) and -B(Q ₄₂₆ )(Q ₄₂₇ ); is selected from;

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 (e.g. Cl, F), a diketone ligand (e.g. acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2, 6,6-Tetramethyl-3,5-heptandionate, hexafluoroacetonate), carboxylic acid ligands (e.g. picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon It may be selected from a monooxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorus ligand (e.g., phosphine, phosphite), but is not limited thereto.

In Formula 401, when A ₄₀₁ has two or more substituents, two or more substituents of A ₄₀₁ may be combined to form a saturated or unsaturated ring.

In Formula 401, when A ₄₀₂ has two or more substituents, the two or more substituents of A ₄₀₂ may be combined to form a saturated or unsaturated ring.

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. In Formula 401, when xc1 is 2 or more, A ₄₀₁ and A ₄₀₂ are directly connected to A ₄₀₁ and A ₄₀₂ of other neighboring ligands, respectively, or are connected to a linking group (for example, C ₁ -C ₅ alkylene group, -N (R')-(where R' is a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₂₀ aryl group) or -C(=O)-).

The phosphorescent dopant may include at least one of the following compounds PD1 to PD74, but is not limited thereto:

Alternatively, the phosphorescent dopant may include PtOEP:

The fluorescent dopant may include at least one of the following DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.

Alternatively, the fluorescent dopant may include a compound represented by the following formula 501:

<Formula 501>

In formula 501,

Ar ₅₀₁ silver

Naphthalene, hepthalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluorine fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and indeno. anthracene (indenoanthracene);

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, and -Si(Q ₅₀₁ )(Q ₅₀₂ )(Q ₅₀₃ ) (Q ₅₀₁ to Q ₅₀₃ are independently of each other, substituted with at least one selected from hydrogen, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group), naphthalene, hepthalene, fluorene , spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and inde. noanthracene; is selected from;

For descriptions of L ₅₀₁ to L ₅₀₃ , refer to the description of L ₂₀₃ in this specification, respectively;

R ₅₀₁ and R ₅₀₂ are independently of each other,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazole group, triazinyl group, dibenzofuranyl group and dibenzothiogiphenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group , phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group. , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzoflu, substituted with at least one selected from carbazolyl group, triazinyl group, dibenzofuranyl group and dibenzothiogophenyl group. Orenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group , quinoxalinyl group, quinazolinyl group, carbazolyl group, triazinyl group and dibenzofuranyl group and dibenzothiogiphenyl group; is selected from;

xd1 to xd3 are independently selected from 0, 1, 2, and 3;

xb4 is selected from 1, 2, 3 and 4.

The fluorescent dopant may include at least one of the following compounds FD1 to FD8:

The content of the dopant in the light-emitting layer can typically be selected in the range of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

The thickness of the light emitting layer may be about 100Å to about 1000Å, for example, about 200Å to about 600Å. When the thickness of the light-emitting layer satisfies the range described above, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

Next, an electron transport region may be placed on top of the light emitting layer.

The electron transport region may include at least one of a hole blocking layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

When the electron transport region includes a hole blocking layer, vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser induced thermal imaging (LITI) methods are used. The hole blocking layer can be formed on top of the light emitting layer using various methods such as the like. When forming a hole blocking layer by vacuum deposition or spin coating, the deposition and coating conditions of the hole blocking layer refer to the deposition and coating conditions of the hole injection layer.

The hole blocking layer may include, for example, at least one of the following BCP and Bphen, but is not limited thereto.

The thickness of the hole blocking layer may be about 20Å to about 1000Å, for example, about 30Å to about 300Å. When the thickness of the hole blocking layer satisfies the range described above, excellent hole blocking characteristics can be obtained without a substantial increase in driving voltage.

The electron transport region may have a structure of an electron transport layer/electron injection layer or a hole blocking layer/electron transport layer/electron injection layer sequentially stacked from the light emitting layer, but is not limited thereto.

According to one embodiment, the organic layer 150 of the organic light emitting device includes an electron transport region interposed between the light emitting layer and the second electrode 190, and the electron transport region includes an electron transport layer. The electron transport layer may be comprised of multiple layers. For example, the electron transport region may include a first electron transport layer and a second electron transport layer.

The electron transport layer may include the BCP, Bphen, and at least one of the following Alq ₃ , Balq, TAZ, and NTAZ.

Alternatively, the electron transport layer may include at least one compound selected from a compound represented by the following Chemical Formula 601 and a compound represented by the following Chemical Formula 602:

<Formula 601>

Ar ₆₀₁ -[(L ₆₀₁ ) _xe1 -E ₆₀₁ ] _xe2

In the above formula 601,

Ar ₆₀₁ is

Naphthalene, hepthalene, fluorene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, pycene, perylene, pentaphene and indenoanthracene;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, and -Si(Q ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ ) (Q ₃₀₁ to Q ₃₀₃ are independently of each other, substituted with at least one selected from hydrogen, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group), naphthalene, hepthalene, fluorene , spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene and inde. noanthracene; is selected from;

For a description of L ₆₀₁ , refer to the description of L ₂₀₃ in this specification;

E ₆₀₁ is

Pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group , isoindoleyl group, indoleyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, Carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group , triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group. , azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group. , fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, Ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, Cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, iso Benzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imida Substituted with at least one of zopyridinyl group and imidazopyrimidinyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyrrolyl group Dinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthy Ridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, iso Benzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzo Carbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group; is selected from;

xe1 is selected from 0, 1, 2, and 3;

xe2 is selected from 1, 2, 3 and 4.

<Formula 602>

In the above formula 602,

X ₆₁₁ is N or C-(L ₆₁₁ ) _xe611 -R ₆₁₁ , _{X 612 is} N or C- _{(L 612 ) xe612 -R 612} , _and , at least one of X ₆₁₁ to X ₆₁₃ is N;

For a description of each of L ₆₁₁ to L ₆₁₆ , refer to the description of L ₂₀₃ in this specification;

R ₆₁₁ to R ₆₁₆ are independently of each other,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group , pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group , phenanthrenyl group, anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group. , substituted with at least one of a carbazolyl group and a triazinyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group. , anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group and triazinyl group; is selected from;

xe611 to xe616 are independently selected from 0, 1, 2, and 3.

The compound represented by Formula 601 and 602 may be selected from the following compounds ET1 to ET15:

The thickness of the electron transport layer may be about 100Å to about 1000Å, for example, about 150Å to about 500Å. When the thickness of the electron transport layer satisfies the range described above, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

The electron transport layer may further include a metal-containing material in addition to the materials described above.

The metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate, LiQ) or ET-D2.

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190.

The electron injection layer is formed using various methods such as vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, and laser thermal imaging (LITI). , may be formed on the electron transport layer. When forming an electron injection layer by vacuum deposition or spin coating, the deposition and coating conditions of the electron injection layer refer to the deposition and coating conditions of the hole injection layer.

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li ₂ O, BaO, and LiQ.

The thickness of the electron injection layer may be about 1Å to about 100Å, or about 3Å to about 90Å. When the thickness of the electron injection layer satisfies the range described above, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode, which is an electron injection electrode. In this case, materials for the second electrode 190 include metals, alloys, electrically conductive compounds, and mixtures thereof having a low work function. can be used. Specific examples of materials for the second electrode 190 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), and magnesium-indium (Mg-In). , magnesium-silver (Mg-Ag), etc. may be included. Alternatively, ITO or IZO may be used as a material for the second electrode 190. The second electrode 190 may be a reflective electrode, a transflective electrode, or a transmissive electrode.

Meanwhile, the organic layer of the organic light-emitting device according to an embodiment of the present invention may be formed by a deposition method using a compound according to an embodiment of the present invention, or a compound according to an embodiment of the present invention prepared as a solution. It can also be formed by a wet coating method.

The organic light emitting device according to an embodiment of the present invention may be provided in various types of flat panel displays, for example, a passive matrix organic light emitting display device and an active matrix organic light emitting display device. In particular, when provided in an active matrix organic light emitting display device, the first electrode provided on the substrate side serves as a pixel electrode and may be electrically connected to the source electrode or drain electrode of the thin film transistor. Additionally, the organic light emitting device can be installed in a flat panel display capable of displaying a screen on both sides.

Above, the organic light emitting device has been described with reference to FIG. 1, but it is not limited thereto.

Hereinafter, the definitions of representative substituents among the substituents used in this specification are as follows (the number of carbon atoms defining the substituent is non-limiting and does not limit the characteristics of the substituent, and substituents not defined in this specification are subject to the general definition. follows).

As used herein, C ₁ -C ₆₀ alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include methyl group, ethyl group, propyl group, isobutyl group, and sec-butyl group. group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, etc. As used herein, the C ₁ -C ₆₀ alkylene group refers to a divalent group having the same structure as the C ₁ -C ₆₀ alkyl group.

As used herein, C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the formula -OA ₁₀₁ (where A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include methoxy group and ethoxy group. , isopropyloxy group, etc.

As used herein, the C ₂ -C ₆₀ alkenyl group refers to a hydrocarbon group containing at least one carbon double bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethenyl group, propenyl group, and butenyl group. etc. are included. As used herein, the C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

As used herein, the C ₂ -C ₆₀ alkynyl group refers to a hydrocarbon group containing at least one carbon triple bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl group and propynyl group. (propynyl), etc. are included. As used herein, the C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

As used herein, C ₃ -C ₁₀ cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cyclo Includes heptyl group, etc. As used herein, the C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

As used herein, C ₁ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms containing at least one hetero atom selected from N, O, P and S as a ring-forming atom, and its Specific examples include tetrahydrofuranyl, tetrahydrothiophenyl, etc. As used herein, the C ₂ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₂ -C ₁₀ heterocycloalkyl group.

As used herein, C ₃ -C ₁₀ cycloalkenyl group refers to a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one double bond in the ring but does not have aromaticity, and its specific details Examples include cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, etc. As used herein, the C ₃ -C ₁₀ cycloalkenylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

As used herein, the C ₂ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 2 to 10 carbon atoms containing at least one hetero atom selected from N, O, P and S as a ring-forming atom, and has at least one in the ring. It has one double bond. Specific examples of the C ₂ -C ₁₀ heterocycloalkenyl group include 2,3-hydrofuranyl group, 2,3-hydrothiophenyl group, and the like. As used herein, the C ₂ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₂ -C ₁₀ heterocycloalkenyl group.

As used herein, the C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group refers to a carbocyclic aromatic system having 6 to 60 carbon atoms. It refers to a divalent group with a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group, etc. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group include two or more rings, the two or more rings may be fused to each other.

As used herein, C ₁ -C ₆₀ heteroaryl group refers to a monovalent group containing at least one hetero atom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms. And, the C ₁ -C ₆₀ heteroarylene group refers to a divalent group containing at least one hetero atom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms. do. Specific examples of the C ₁ -C ₆₀ heteroaryl group include pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, etc. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be fused to each other.

As used herein, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (where A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C 60 arylthio group refers to -SA ₁₀₃ (where A 102 is the C 6 -C ₆₀ aryl group). , A ₁₀₃ refers to the C ₆ -C ₆₀ aryl group).

As used herein, a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring forming atom, and the entire molecule is non-aromatic. It means a monovalent group having (for example, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. As used herein, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

As used herein, a monovalent non-aromatic condensed heteropolycyclic group has two or more rings condensed with each other, and contains a hetero atom selected from N, O, P and S in addition to carbon as a ring forming atom. , means a monovalent group (for example, having 2 to 60 carbon atoms) in which the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group and the like. As used herein, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

In the present specification, the substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₂ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₂ -C ₁₀ heterocycloal Kenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group , a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and at least one substituent among a substituted monovalent non-aromatic condensed heteropolycyclic group. Is,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, - C ₁ -C ₆₀ alkyl group, C ₂ substituted with at least one of N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ) -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), substituted with at least one of C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalke Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non- aromatic heterocondensed polycyclic group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group. , amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group. , C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ It may be selected from an aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

For example, the above substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₂ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₂ -C ₁₀ heterocyclo Alkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloc group, at least one of a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed heteropolycyclic group. The substituent is,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaph Tyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, Chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazole Diary group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group , purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridi Nyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadia Zolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -N (Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ), C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkene Nyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, flu Orenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group , naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrrolyl group. Azolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group , quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanyl Trolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, Cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, di Benzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, Hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, Isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, pro Thalasinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, Benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Zolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B (Q ₂₆ ) (Q ₂₇ ), substituted with at least one of a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group , azulenyl group, hepthalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group. , fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, Ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, Cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, iso Benzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imida Zopyridinyl group and imidazopyrimidinyl group; and

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ) and -B(Q ₃₆ )(Q ₃₇ ); is selected from;

Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group. , amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group. , C ₁ -C ₆₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, Indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group Nyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group , furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, Indoleyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenene Tridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, Tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group can be selected from among.

In this specification, “Ph” means a phenyl group, “Me” means a methyl group, “Et” means an ethyl group, and “ter-Bu” or “Bu ^t ” means a tert-butyl group.

Below, an organic light emitting device according to an embodiment of the present invention will be described in more detail through examples.

Synthesis example

[ Synthesis example One: compound of synthesis]

Synthesis example : Synthesis of Compound 3

Synthesis of Intermediate A-1

Starting materials methyl 5-bromo-2-iodobenzoate (5.0 g, 14.67 mmol), (4-chloro-2-methoxyphenyl)boronic acid (3.3 g, 17.6 mmol), Pd(PPh3)4 (847.6 mg, 0.733 mmol) and K2CO3 (4.0 g, 29.34 mmol) was added to 150 mL of THF/H2O (9:1 volume ratio) mixture, stirred at 100°C for 12 hours, cooled to room temperature, and the organic layer was extracted three times with water and diethyl ether. The extracted organic layer was dried over magnesium sulfate, the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain Intermediate A-1 (3.3 g, 9.39 mmol, 64% yield). The produced compound was confirmed through MS/FAB. C15H12BrClO3 cal. 355.61, found 353.97.

Synthesis of Intermediate A-2

After dissolving Intermediate A-1 (3.3 g, 9.39 mmol) in 100 mL of toluene, phenylmagnesium bromide (50 mmol) was slowly added dropwise, and stirred under reflux conditions. When the reaction was completed, it was cooled to room temperature and the organic layer was extracted three times with water and diethyl ether. The extracted organic layer was dried over magnesium sulfate, the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain Intermediate A-2 (2.9 g, 6.01 mmol, 64% yield). The produced compound was confirmed through MS/FAB. C26H20BrClO2 cal. 479.80, found 478.03.

Synthesis of Intermediate A-3

After dissolving Intermediate A-2 (2.9 g, 6.01 mmol) in 50 mL of MeCN, boron tribromide (0.68 mL, 6.01 mmol) was slowly added dropwise and stirred. When the reaction was completed, 50 mL of saturated sodium thiosulfate was added, stirred, and the organic layer was extracted three times with iethyl ether. The extracted organic layer was dried over magnesium sulfate, the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain Intermediate A-2 (2.1 g, 4.81 mmol, 80% yield). The produced compound was confirmed through MS/FAB. C25H16BrClO cal. 447.76, found 446.01.

Synthesis of Compound 3

Intermediate A-2 (2.1 g, 4.81 mmol), diphenylamine (1.79 g, 10.6 mmol), tris(dibenzylideneacetone)dipalladium(0) (220 mg, 0.24 mmol), tri(tert-butyl)phosphine (145.7 mg, 0.72 mmol) ), sodium tert-butoxide (1.99 g, 14.4 mmol) was added to 40mL of toluene and stirred at 80°C for 2 hours. After cooling the reaction solution to room temperature, it is extracted twice with water and diethyl ether. The organic layer obtained from this was dried over magnesium sulfate, the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain Compound 3 (2.57 g, 3.85 mmol, yield 80%). The produced compound was confirmed through MS/FAB. C49H36N2O cal. 668.84, found 668.28.

Synthesis of compound 46

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 46, A-3 (1.0 g, 2.23 mmol) was used as a starting material, and instead of diphenylamine (5'-fluoro-N-phenyl-[1,1':3',1''-terphenyl]-4 Compound 46 (1.19 g, 1.18 mmol, yield 53%) was obtained using '-amine. The produced compound was confirmed through MS/FAB. C73H50F2N2O cal. 1009.21, found 1008.39.

Synthesis of compound 62

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 62, A-3 (1.0 g, 2.23 mmol) was used as a starting material, and 6-(tert-butyl)-N-(5-(tert-butyl)-[1,1'-biphenyl] was used instead of diphenylamine. Compound 62 (1.67 g, 1.36 mmol, yield 61%) was obtained using -2-yl)dibenzo[b,d]furan-4-amine. The produced compound was confirmed through MS/FAB. C89H80N2O3 cal. 1225.63, found 1224.62.

Synthesis example : Synthesis of compound 94

Synthesis of compound 94

A-3 (1.0 g, 2.23 mmol) and (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid (2.95 g, 6.69 mmol), Pd(PPh3)4 (128.8 mg, 0.11 mmol) and K2CO3 (924.6 mg, 6.69 mmol) were added to 20 mL of the THF/H2O (9/1 volume ratio) mixture, stirred at 80°C for 12 hours, cooled to room temperature, and mixed with water and diethyl. Extract with ether 3 times. The organic layer obtained from this was dried with magnesium sulfate, the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain compound 94 (1.86 g, 1.65 mmol, yield 74%). The produced compound was confirmed through MS/FAB. C85H60N2O cal. 1125.43, found 1124.47.

Synthesis of compound 95

The synthesis was carried out in the same manner as for compound 94. For the synthesis of compound 95, A-3 (1.0 g, 2.23 mmol) was used as a starting material, and instead of (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid, (4- Compound 95 (1.50 g, 1.52 mmol, yield 68%) was obtained using (dimesitylamino)phenyl)boronic acid. The produced compound was confirmed through MS/FAB. C73H68N2O cal. 989.36, found 988.53.

Synthesis example : Synthesis of Compound 103

Synthesis of Intermediate B-1

The synthesis was carried out in the same manner as for compound 94. For the synthesis of compound 103, A-3 (1.0 g, 2.23 mmol) was used as a starting material, and instead of (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid, (4- Intermediate B-1 (1.14 g, 1.78 mmol, yield 80%) was obtained using (di-p-tolylamino)phenyl)boronic acid (1.1 equiv). The produced compound was confirmed through MS/FAB. C45H34ClNO cal. 640.22, found 639.23.

Synthesis of compound 103

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 103, B-1 (1.14 g, 1.78 mmol) was used as a starting material, and instead of diphenylamine (di-p-tolylamine (1.1 equiv)) was used to obtain compound 103 (1.17 g, 1.46 mmol, yield 82%). Obtained. The produced compound was confirmed through MS/FAB. C59H48N2O cal. 801.05, found 800.38.

Synthesis example : Synthesis of Compound 2

Synthesis of Intermediate C-1

Compound A-2 was synthesized in the same manner as the synthesis method. For the synthesis of intermediate C-1, A-1 (3.0 g, 8.44 mmol) was used as a starting material, and methylmagnesium bromide was used instead of phenylmagnesium bromide to obtain intermediate C-1 (2.46 g, 6.92 mmol, yield 82%). The produced compound was confirmed through MS/FAB. C16H16BrClO2 cal. 355.66, found 354.00.

Synthesis of Intermediate C-2

Compound A-3 was synthesized in the same manner as the synthesis method. For the synthesis of Intermediate C-2, C-1 (2.46 g, 6.92 mmol) was used as a starting material to obtain Intermediate C-2 (1.72 g, 5.32 mmol, yield 77%). The produced compound was confirmed through MS/FAB. C15H12BrClO cal. 323.61, found 321.98.

Synthesis of Compound 2

The synthesis was carried out in the same manner as for compound 3. In the synthesis of Compound 2, Intermediate C-2 (1.72 g, 5.32 mmol) was used as a starting material to obtain Compound 2 (2.52 g, 4.63 mmol, yield 87%). The produced compound was confirmed through MS/FAB. C39H32N2O cal. 544.70, found 544.25.

Synthesis example : Synthesis of Compound 13

Synthesis of Intermediate D-1

It was carried out in the same manner as the synthesis of Intermediate A-1. For the synthesis of intermediate D-1, methyl 4-bromo-2-iodobenzoate (5.11 g, 15.0 mmol) and (5-bromo-2-methoxyphenyl)boronic acid (4.16g, 18 mmol) were used as starting materials to produce intermediate D-1. 1 (4.80 g, 12.0 mmol, yield 80%) was obtained. The produced compound was confirmed through MS/FAB. C15H12Br2O3 cal. 400.07, found 397.92.

Synthesis of Intermediate D-2

It was carried out in the same manner as the synthesis of Intermediate A-2. For the synthesis of intermediate D-2, D-1 (4.80 g, 12.0 mmol) was used as a starting material to obtain intermediate D-2 (4.08 g, 7.8 mmol, yield 65%). The produced compound was confirmed through MS/FAB. C26H20Br2O2 cal. 524.25, found 521.98.

Synthesis of intermediate D-3

It was carried out in the same manner as the synthesis of Intermediate A-3. For the synthesis of intermediate D-3, D-2 (3.27 g, 6.2 mmol) was used as a starting material to obtain intermediate D-3 (1.58 g, 3.2 mmol, yield 52%). The produced compound was confirmed through MS/FAB. C25H16Br2O cal. 492.21, found 489.96.

Synthesis of compound 13

The synthesis method of compound 3 was carried out in the same manner. For the synthesis of compound 13, D-3 (1.58 g, 3.2 mmol) was used as a starting material to obtain compound 13 (1.35 g, 2.0 mmol, yield 63%). The produced compound was confirmed through MS/FAB. C49H36N2O cal. 668.84, found 668.28

Synthesis of compound 46

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 46, D-3 (2.0 g, 2.9 mmol) was used as a starting material, and instead of diphenylamine, 5'-fluoro-N-phenyl-[1,1':3',1''-terphenyl]-4' Compound 46 (1.26 g, 1.25 mmol, yield 43%) was obtained using -amine. The produced compound was confirmed through MS/FAB. C73H50F2N2O cal. 1009.21, found 1008.39.

Synthesis example : Synthesis of Compound 108

Synthesis of Intermediate C-1

After dissolving 2,6-dibromo-4H-cyclopenta[def]phenanthrene (2 g, 5.75 mmol) in 200 mL of toluene, activated MnO2 (8.4 g, 97.75 mmol) was added and stirred for 12 hours under reflux conditions. After cooling the reaction solution to room temperature, the solvent was evaporated, and the residue obtained was purified by silica gel column chromatography to obtain Intermediate C-1 (1.66 g, 4.6 mmol, yield 80%). The produced compound was confirmed through MS/FAB. C15H6Br2O cal. 362.02, found 359.88.

Synthesis of Intermediate C-2

A mixture of Intermediate C-1 (1.66 g, 4.6 mmol) and CF3CO2H (10 mL) was maintained at 0°C, and then Na2CO4 (1.57 g, 10 mmol) was added five times for 40 minutes. After stirring the reaction solution at room temperature for 48 hours, cold water was added to terminate the reaction, and the organic layer was extracted three times with water and CH2Cl2. The extracted dormant layer was washed with 10% NaHCO3, dried with magnesium sulfate, and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain intermediate C-2 (1.29 g, 3.4 mmol, yield 74%). The produced compound was confirmed through MS/FAB. C15H6Br2O2 cal. 378.02, found 375.87.

Intermediate C-3 synthesis

Intermediate C-2 (1.29 g, 3.4 mmol) was dissolved in 30 mL of toluene, then phenylmagnesium bromide (15 mmol) was slowly added and reacted under reflux conditions for 12 h. After the reaction is completed and cooled to 0°C, NH4Cl is added to terminate the reaction. The organic layer of the resulting mixture was extracted three times with water and CH2Cl2, then the organic layer was dried over magnesium sulfate and the solvent was evaporated. The obtained residue was separated and purified by silica gel column chromatography to obtain intermediate C-3 (1.6 g, 3.0 mmol, 88% yield). The produced compound was confirmed through MS/FAB. : C27H18Br2O2 cal. 534.25, found 531.97.

Intermediate C-4 synthesis

After adding 5 mL of DMF to intermediate C-3 (1.6 g, 3.0 mmol) and K2CO3 (1.66 g, 12.0 mmol), CH3I (468 mg, 3.3 mmol) was slowly added dropwise. The resulting mixture was stirred at 90° C. for 24 hours, and then the resulting solid was filtered. The remaining organic layer was extracted three times using NH4Cl and CH2Cl2. The extracted organic layer was dried over magnesium sulfate, the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain intermediate C-4 (1.22 g, 2.22 mmol, 74% yield). The produced compound was confirmed through MS/FAB. C28H20Br2O2 cal. 548.27, found 545.98.

Intermediate C-5 synthesis

Compound A-3 was synthesized in the same manner as the synthesis method. For the synthesis of Intermediate C-5, C-4 (1.22 g, 2.22 mmol) was used as a starting material to obtain Intermediate C-5 (458 mg, 0.89 mmol, yield 40%). The produced compound was confirmed through MS/FAB. C27H16Br2O cal. 516.23, found 513.96.

Synthesis of compound 108

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 108, C-5 (458 mg, 0.89 mmol) was used as a starting material to obtain compound 108 (443 mg, 0.64 mmol, yield 72%). The produced compound was confirmed through MS/FAB. C51H36N2O cal. 692.86, found 692.28.

Synthesis of compound 146

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 146, C-5 (1.0 g, 1.94 mmol) was used as a starting material, and (di-p- N-([1,1'-biphenyl]-2-yl)pyridin-2-amine was used instead of diphenylamine. Compound 146 (1.05 g, 1.24 mmol, yield 63%) was obtained. The produced compound was confirmed through MS/FAB. C61H42N4O cal. 847.03, found 846.34.

Synthesis of compound 147

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 147, C-5 (1.0 g, 1.94 mmol) was used as a starting material, and 5-methoxy-N-phenyl-[1,1'-biphenyl]-2-amine was used instead of diphenylamine to produce compound 147 (1.28 g, 1.42 mmol, yield 73%) was obtained. The produced compound was confirmed through MS/FAB. C65H48N2O3 cal. 905.11, found 904.37.

Synthesis of compound 153

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 153, C-5 (1.0 g, 1.94 mmol) was used as a starting material, and N-([1,1'-biphenyl]-2-yl)dibenzo[b,d]furan-4-amine was used instead of diphenylamine. Compound 153 (1.27 g, 1.24 mmol, yield 64%) was obtained using . The produced compound was confirmed through MS/FAB. C75H48N2O3 cal. 1025.22, found 1024.37.

Synthesis of compound 155

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 155, C-5 (1.0 g, 1.94 mmol) was used as a starting material, and N-([1,1'-biphenyl]-2-yl)dibenzo[b,d]thiophen-4-amine was used instead of diphenylamine. Compound 155 (1.39 g, 1.32 mmol, yield 68%) was obtained using . The produced compound was confirmed through MS/FAB. C75H48N2OS2 cal. 1057.34, found 1056.32.

Synthesis of compound 160

The synthesis was carried out in the same manner as for compound 3. In the synthesis of compound 160, C-5 (1.0 g, 1.94 mmol) was used as a starting material, and N-(4-(tert-butyl)phenyl)dibenzo[b,d]furan-4-amine was used instead of diphenylamine to produce the compound. 160 (1.37 g, 1.40 mmol, yield 72%) was obtained. The produced compound was confirmed through MS/FAB. C71H56N2O3 cal. 985.24, found 984.43.

Synthesis of compound 184

The synthesis was carried out in the same manner as for compound 3. For the synthesis of compound 184, C-5 (1.0 g, 1.94 mmol) was used as a starting material, and diphenylamine N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-2-amine was used as a starting material. Compound 153 (1.65 g, 1.61 mmol, yield 83%) was obtained. The produced compound was confirmed through MS/FAB. C75H48N2O3 cal. 1025.22, found 1024.37.

Synthesis example : Synthesis of Compound 196

The synthesis was carried out in the same manner as for compound 94. For the synthesis of compound 196, C-5 (1.0 g, 1.94 mmol) was used as a starting material, and instead of (4-(di([1,1'-biphenyl]-4-yl)amino)phenyl)boronic acid, (4- Compound 196 (1.26 g, 1.49 mmol, yield 77%) was obtained using (diphenylamino)phenyl)boronic acid. The produced compound was confirmed through MS/FAB. C63H44N2O cal. 845.06, found 844.35.

Synthesis of Compound 199

The synthesis was carried out in the same manner as for compound 94. For the synthesis of Compound 199, C-5 (1.0 g, 1.94 mmol) was used as a starting material to obtain Compound 199 (1.76 g, 1.53 mmol, yield 79%). The produced compound was confirmed through MS/FAB. C87H60N2O cal. 1149.45, found 1148.47.

Refer to Table 1 below for NMR and MS data of the compounds synthesized in the above synthesis examples:

compound ^1H NMR (CDCl ₃ , 400MHz) MS/FAB calc. found 2 δ= 7.66-7.59(m, 2H), 7.1-7.02(m, 9H), 6.73(d, 1H), 6.7-6.63(m, 4H), 6.53(s, 1H), 6.36-6.29(m, 5H) ),6.23-6.16(m, 4H), 1.72(s, 3H), 1.68(s, 3H) 544.70 544.25
3 δ= 7.5-7.46(m, 4H), 7.43(d, 1H), 7.37(dd, 1H), 7.34-7.25(m, 6H), 7.09-7.01(m, 9H), 6.7-6.62(m, 4H) ), 6.56(dd, 1H), 6.35-6.28(m, 5H), 6.22-6.16(m, 5H) 668.84 668.24 13 7.51-7.46(m, 4H), 7.31-7.26(m, 6H),7.21(d, 1H), 7.09-7.04(m, 8H), 6.89(d, 1H), 6.85(d, 1H), 6.78( s, 1H), 6.77(s, 1H), 6.7-6.64(m, 4H),6.45(dd, 1H), 6.28-6.23(m, 8H) 668.84 668.24 46 δ= 7.73-7.68(m, 4H), 7.65-7.59(m, 6H), 7.56-7.46(m, 14H), 7.45-7.41(m, 2H), 7.33-7.26(m, 7H), 7.2(d) , 1H), 7.13(d, 1H), 7.13(d, 1H), 7.11-7.06(m, 5H), 6.67-6.62(m, 2H), 6.34(dd, 1H), 6.29-6.25(m, 3H) ), 6.18-6.13(m, 2H), 5.99(d, 1H) 1009.21 1008.39 62 δ= 7.47-7.65(m, 4H), 7.7-7.65(m, 2H), 7.65-7.6(m, 2H), 7.6-7.56(m, 4H), 7.53-7.46(m, 10H),7.43(d , 1H), 7.36(s, 1H), 7.36(s, 1H), 7.33(d, 1H), 7.33-7.26(m, 8H), 7.11(d, 1H), 7.11(d, 1H), 7.07( d, 1H), 6.96(dd, 1H), 6.91(dd, 1H), 6.78(d, 1H), 6.62(d, 1H), 6.37(dd, 1H), 6.25(dd, 1H), 6.04-5.99 (m, 1H), 1.56(s, 9H), 1.56(s, 9H), 1.54(s, 9H), 1.54(s, 9H) 1225.63 1224.62 94 δ= 7.87(dd, 1H), 7.82(dd, 1H), 7.75(d, 1H), 7.65-7.6(m, 9H), 7.57-7.51(m, 13H), 7.48-7.39(m, 14H), 7.36-7.26(m, 8H),7.17(d, 1H), 6.96-6.84(m, 10H), 6.61-6.58(m, 2H) 1125.43 1124.47 95 δ= 7.87(dd, 1H), 7.82(dd, 1H), 7.75(d, 1H), 7.64(d, 1H), 7.57-7.51(m, 5H), 7.4-7.36(m, 2H), 7.32- 7.27(m, 8H), 7.18(d, 1H), 6.79-6.73(m, 10H), 6.2-6.15(m, 2H), 2.45(s, 12H), 2.34(s, 24H) 989.36 988.53 103 δ=7.87(d, 1H), 7.75(d, 1H), 7.63(d, 1H), 7.56-7.51(m, 4H), 7.37-7.34(m, 2H), 7.32-7.27(m, 6H), 7.09(d, 1H), 7.03-6.93(m, 10H), 6.59-6.54(m, 8H), 6.42(d, 1H), 6.28(s, 1H), 2.46(s, 12H) 801.05 800.38 108 δ=7.61-7.49(m, 6H), 7.41(d, 1H), 7.36-7.26(m, 6H), 7.12-7.02(m, 9H), 6.82(d, 1H), 6.7-6.65(m, 4H) ), 6.33-6.28(m, 4H), 6.21-6.16(m, 4H), 6.1(d, 1H) 692.86 692.28 146 δ=8.52(dd, 1H), 8.16(dd, 1H), 7.98(d, 1H), 7.61-7.41(m, 18H), 7.36-7.23(m, 11H), 7.21-7.1(m, 4H), 7.02(d, 1H), 6.92(d, 1H), 6.9(t, 1H), 6.82-6.77(m, 1H), 6.06(d, 1H), 5.91(d, 1H) 847.03 846.34 147 δ=7.74-7.69(m, 4H), 7.61-7.46(m, 11H), 7.39(d, 1H), 7.36-7.26(m, 6H), 7.14-7.04(m, 7H), 6.91(d, 1H) ), 6.88-6.77(m, 3H), 6.73(d, 1H), 6.72(d, 1H), 6.68-6.63(m, 2H), 6.27-6.23(m, 2H), 6.16-6.11(m, 2H) ), 5.92(d, 1H), 3.97(s, 3H), 3.95(s, 3H) 905.11 904.37 153 δ=7.85-7.82(m, 2H), 7.74-7.02(m, 2H), 7.64-7.51(m, 15H), 7.49-7.41(m, 6H), 7.36-7.26(m, 7H), 7.21-6.92 (m, 14H), 6.73(d, 1H), 5.85(d, 1H) 1025.22 1024.37 155 δ=8.06-8.02(m, 2H), 7.97-7.93(m, 2H),7.81-7.78(m, 2H), 7.64-7.51(m, 15H), 7.49-7.44(m, 2H), 7.41-7.26 (m, 8H), 7.26-7.18(m, 5H), 7.12(d, 1H), 7.04-6.94(m, 6H), 6.94-6.87(m, 3H), 6.81(d, 1H), 5.67(d) , 1H) 1057.34 1056.32 160 δ=7.85-7.82(m, 2H), 7.75-7.7(m, 2H), 7.61-7.51(m, 8H), 7.49-7.41(m, 4H), 7.36-7.26(m, 10H), 7.15-6.97 (m, 6H), 6.91(d, 1H), 6.51-6.46(m, 4H), 6.18(d, 1H), 1.63(s, 18H) 985.24 984.43 184 δ=7.85-7.7(m, 5H), 7.66-7.61(m, 4H), 7.59-7.39(m, 24H), 7.36-7.26(m, 6H), 7.07-6.94(m, 4H), 6.8-6.77 (m, 2H), 6.63-6.57(m, 2H), 6.18(d, 1H) 1025.22 1024.37 196 δ=8.17(s, 1H), 7.92(s, 1H), 7.9(s, 1H), 7.72(s, 1H), 7.59-7.51(m, 5H), 7.49-7.36(m, 4H), 7.36- 7.31(m, 4H), 7.31-7.26(m, 2H), 7.17(s, 1H), 7.1-7.07(m, 8H), 6.97-6.82(m, 4H), 6.7-6.63(m, 4H), 6.21-6.14(m, 8H) 845.06 844.35 199 δ=8.17(s, 1H), 7.92(s, 1H), 7.9(s, 1H), 7.72(d, 1H), 7.66-7.61(m, 8H), 7.59-7.55(m, 4H), 7.55- 7.49(m, 9H), 7.49-7.44(m, 10H), 7.44-7.36(m, 6H), 7.36-7.34(m, 4H), 7.33-7.26(m, 2H), 7.17(q, 1H), 6.97-6.92(m, 2H), 6.9-6.85(m, 8H), 6.66-6.61(m, 2H) 1145.45 1144.47

Example One

Anode is corning 15Ω/cm ² (1200Å) ITO glass substrate was cut into 50mm This glass substrate was installed.

First, as a hole injection layer, the known compound 2-TNATA was vacuum deposited on the upper part of the substrate to form a hole injection layer to a thickness of 600 Å, and then Compound 3, a compound of the present invention, as a hole transport compound was vacuum deposited to a thickness of 300 Å to form a hole transport layer. did.

A known blue fluorescent host is placed on top of the hole transport layer.9,10-di-naphthalene-2-yl-anthracene (hereinafter referred to as ADN) and N,N,N',N'-tetraphenyl-pyrene-1,6-diamine (TPD), a compound known as a blue fluorescent dopant. A light emitting layer was formed with a thickness of 300 Å by simultaneous deposition at a weight ratio of 98:2.

Then, an electron transport layer was placed on top of the light emitting layer.After depositing Alq3 to a thickness of 300Å, LiF, an alkali metal halide, was deposited to a thickness of 10Å as an electron injection layer on top of this electron transport layer, and Al was vacuum deposited to a thickness of 3000Å (cathode electrode) to create a LiF/Al electrode. An organic light-emitting device was manufactured by forming an organic light-emitting device.

Example 2

An organic EL device was manufactured in the same manner as Example 1, except that Compound 94 was used instead of Compound 3 when forming the hole transport layer.

Example 3

An organic EL device was manufactured in the same manner as Example 1, except that Compound 96 was used instead of Compound 3 when forming the hole transport layer.

Example 4

An organic EL device was manufactured in the same manner as Example 1, except that Compound 103 was used instead of Compound 3 when forming the hole transport layer.

Example 5

An organic EL device was manufactured in the same manner as Example 1, except that Compound 184 was used instead of Compound 3 when forming the hole transport layer.

Example 6

An organic EL device was manufactured in the same manner as Example 1, except that Compound 196 was used instead of Compound 3 when forming the hole transport layer.

Example 7

An organic EL device was manufactured in the same manner as Example 1, except that Compound 199 was used instead of Compound 3 when forming the hole transport layer.

Comparative example One

Organic material was prepared in the same manner as in Example 1, except that the known compound 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (hereinafter referred to as NPB) was used when forming the hole transport layer. An EL device was manufactured.

The device results of the examples and comparative examples are shown in Table 2 below.

hole transport layer driving voltage
(V) current density
(㎃/㎠) Luminance
(cd/㎡) efficiency
(cd/A) Luminous color Half life 　　　　(hr @100㎃/㎠) Example 1 Compound 3 5.42 50 3456 6.43 blue 318 Example 2 Compound 94 6.01 50 3296 6.63 blue 361 Example 3 Compound 95 5.67 50 3125 6.66 blue 306 Example 4 Compound 103 5.55 50 3699 6.23 blue 322 Example 5 Compound 184 5.84 50 3483 6.15 blue 299 Example 6 Compound 196 6.00 50 3010 6.39 blue 318 Example 7 Compound 199 5.63 50 3391 6.45 blue 283 Comparative Example 1 NPB 6.99 50 2745 5.22 blue 256

Example 8

An organic EL device was manufactured in the same manner as in Example 1, except that NPB, a known compound, was used instead of Compound 3 for the hole transport layer, and Compound 2 of the present invention was used instead of TPD, a known dopant compound, when forming the light emitting layer. did.

Example 9

An organic EL device was manufactured in the same manner as Example 8, except that Compound 13 was used instead of Compound 2 when forming the light-emitting layer.

Example 10

An organic EL device was manufactured in the same manner as Example 8, except that Compound 46 was used instead of Compound 2 when forming the light-emitting layer.

Example 11

An organic EL device was manufactured in the same manner as Example 8, except that Compound 62 was used instead of Compound 2 when forming the light-emitting layer.

Example 12

An organic EL device was manufactured in the same manner as Example 8, except that Compound 108 was used instead of Compound 2 when forming the light-emitting layer.

Example 13

An organic EL device was manufactured in the same manner as Example 8, except that Compound 146 was used instead of Compound 2 when forming the light-emitting layer.

Example 14

An organic EL device was manufactured in the same manner as Example 8, except that Compound 147 was used instead of Compound 2 when forming the light-emitting layer.

Example 15

An organic EL device was manufactured in the same manner as Example 8, except that Compound 153 was used instead of Compound 2 when forming the light-emitting layer.

Example 16

An organic EL device was manufactured in the same manner as Example 8, except that Compound 155 was used instead of Compound 2 when forming the light-emitting layer.

Example 17

An organic EL device was manufactured in the same manner as Example 8, except that Compound 160 was used instead of Compound 2 when forming the light-emitting layer.

Comparative example 2

An organic EL device was manufactured in the same manner as Example 8, except that the known compound A was used instead of the compound 2 when forming the light-emitting layer.

The results of the comparative examples and examples are summarized in Table 3.

luminescent layer driving voltage
(V) current density
(㎃/㎠) Luminance
(cd/㎡) efficiency
(cd/A) Luminous color Half life 　　　　(hr @100㎃/㎠) Example 8 compound 2 5.89 50 2962 7.26 blue 351 Example 9 Compound 13 5.22 50 3337 7.41 blue 258 Example 10 Compound 46 5.35 50 3255 7.27 blue 345 Example 11 Compound 62 5.25 50 3456 7.31 blue 331 Example 12 Compound 108 5.70 50 3463 6.98 blue 299 Example 13 Compound 146 5.39 50 3597 7.62 blue 364 Example 14 Compound 147 5.19 50 3328 6.94 blue 347 Example 15 Compound 153 5.66 50 3045 7.01 blue 326 Example 16 Compound 155 5.63 50 3204 7.11 blue 254 Example 17 Compound 160 5.36 50 3654 7.25 blue 368 Comparative Example 2 A 6.33 50 3560 6.15 blue 335

When the structure of Chemical Formula 1 according to an embodiment of the present invention is used as a hole transport layer material and a light emitting layer material, the effect of lowering the driving voltage and increasing efficiency can be obtained compared to known compounds. In particular, the effect of increasing the half-life of the device can be obtained.

Although the present invention has been described with reference to the above embodiments, this is merely illustrative, and those skilled in the art will understand that various modifications and other equivalent embodiments are possible therefrom. . Therefore, the true technical protection scope of the present invention should be determined by the technical spirit of the attached patent claims.

10: Organic light emitting device
110: first electrode
150: Organic layer
190: second electrode

Claims (20)

Compound represented by the following formula (3):
<Formula 3>

Of the above formula 3,
R ₁ to R ₂ are each independently hydrogen, deuterium, halogen, amino group, nitro group, nitrile group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or Unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group , substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and selected from substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups;
Optionally, R ₁ and R ₂ are connected to each other to form a cyclohexyl group or a cycloheptyl group;
L ₁ and L ₂ are each independently a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic groups;
Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, selected from a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;
c and d are each independently selected from integers from 0 to 3;
The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₂ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₂ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, substituted monovalent non-aromatic heterocondensed polycyclic group, At least one substituent among a substituted C ₆ -C ₆₀ arylene group, a substituted C ₁ -C ₆₀ heteroarylene group, a substituted divalent non-aromatic condensed polycyclic group, and a substituted divalent non-aromatic condensed heteropolycyclic group ,
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, - C ₁ -C ₆₀ alkyl group, C ₂ substituted with at least one of N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) and -B(Q ₁₆ )(Q ₁₇ ) -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ) and -B(Q ₂₆ )(Q ₂₇ ), substituted with at least one of C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalke Nyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non- aromatic heterocondensed polycyclic group; and
Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ); is selected from;
Q ₁₁ to Q ₁₇ and Q ₂₁ to Q ₂₇ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C ₁ -C ₆₀ alkyl group, C 2 -C ₆₀ alkenyl group, C _{2 -C 60} alkynyl group, C ₁ -C ₆₀ Alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ - C ₆₀ is selected from heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group. delete delete According to paragraph 1,
In Formula 3, the compound wherein L ₁ and L ₂ are each independently a substituted or unsubstituted C ₆ -C ₆₀ arylene group, or a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group. According to paragraph 1,
In Formula 3, Ar ₁ to Ar ₄ are each independently a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, or a substituted or unsubstituted monovalent non-substituted group. - A compound that is an aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group. According to paragraph 1,
In Formula 3, R ₁ and R ₂ are each independently hydrogen, deuterium, or any one of the following Formulas 2a to 2d,

In the above formulas 2a to 2d, Z ₁ is each independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or Unsubstituted aryl group having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 20 carbon atoms, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic hetero a condensed polycyclic group, and Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ );
p represents an integer from 1 to 5;
* indicates binding site; or
A compound in which R ₁ and R ₂ are connected to each other to form a cyclohexyl group or a cycloheptyl group. According to paragraph 1,
In Formula 3, L ₁ or L ₂ is a compound of Formula 3a:

In Formula 3a, * represents a binding site. According to paragraph 1,
In Formula 3, Ar ₁ to Ar ₄ are each independently one of the following Formulas 4a to 4e:

In Formulas 4a to 4e, H ₁ represents O, S, CR ₁₁ R ₁₂ , or NR ₁₃ ,
R ₁₁ to R ₁₃ , and Z ₁ are each independently hydrogen, deuterium, cyano group, halogen group, substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or Unsubstituted aryl group having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 20 carbon atoms, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic hetero a condensed polycyclic group, and Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ );
p represents an integer from 1 to 9;
* indicates a binding site. delete delete According to paragraph 1,
The compound of formula 3 is any one of the following compounds:

first electrode;
a second electrode opposite the first electrode; and
An organic layer interposed between the first electrode and the second electrode and including a light-emitting layer,
An organic light-emitting device wherein the organic layer includes the compound of claim 1. According to clause 12,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer,
i) a hole transport layer interposed between the first electrode and the light emitting layer; and at least one of a hole injection layer and an electron blocking layer; and a hole transport region including
ii) an organic light emitting device interposed between the light emitting layer and the second electrode and including an electron transport region including at least one of an electron transport layer, a hole blocking layer, and an electron injection layer. According to clause 12,
An organic light-emitting device wherein the light-emitting layer includes the compound of claim 1. According to clause 13,
An organic light-emitting device wherein the hole transport region includes the compound of claim 1. According to clause 13,
An organic light-emitting device wherein the hole transport layer includes the compound of claim 1. According to clause 13,
An organic light emitting device wherein the hole transport region includes a charge-generating material. According to clause 13,
An organic light-emitting device wherein the electron transport region includes a metal complex. According to clause 13,
Organic light-emitting device wherein the electron transport region includes ET-D1 or ET-D2:
A display device comprising the organic light emitting device of claim 12, wherein a first electrode of the organic light emitting device is electrically connected to a source electrode or a drain electrode of a thin film transistor.

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