KR102465590B1 - Organic light emitting device and display device having the same - Google Patents

Abstract

The organic light emitting device includes a first electrode, a hole transport region provided on the first electrode, a light emitting layer provided on the hole transport region, an electron transport region provided on the light emitting layer, and a second hole transport region provided on the electron transport region. contains electrodes. The electron transport region includes a compound represented by Formula 1 below.
[Formula 1]

Description

Organic light emitting device and display device including the same {ORGANIC LIGHT EMITTING DEVICE AND DISPLAY DEVICE HAVING THE SAME}

The present invention relates to an organic light emitting device and a display device including the same.

A flat display device can be largely classified into a light emitting type and a light receiving type. Examples of the light emitting type include a flat cathode ray tube, a plasma display panel, and an organic light emitting display (OLED). The organic light emitting display device is a self-emitting display device and has advantages of a wide viewing angle, excellent contrast, and fast response speed.

Accordingly, the organic light emitting display device is a display device for mobile devices such as digital cameras, video cameras, camcorders, portable information terminals, smart phones, ultra-slim laptop computers, tablet personal computers, flexible display devices, and ultra-thin devices. It is in the limelight because it can be applied to large electronic products such as televisions or large electrical products.

An organic light emitting display device can realize color based on the principle that holes and electrons injected into the first electrode and the second electrode recombine in the light emitting layer to emit light. Lights up when falling.

An object of the present invention is to provide an organic light emitting device with high efficiency and long lifespan.

An object of the present invention is to provide a display device including an organic light emitting device with high efficiency and long lifespan.

An organic light emitting device according to an embodiment of the present invention includes a first electrode, a hole transport region provided on the first electrode, a light emitting layer provided on the hole transport region, an electron transport region provided on the light emitting layer, and the electron transport region provided on the light emitting layer. and a second electrode provided on the transport region. The electron transport region includes a compound represented by Formula 1 below.

[Formula 1]

In Formula 1, X ₁ and X ₂ are each independently CR ₅ or N, and R ₁ to R ₅ are each independently hydrogen, heavy hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, and Heteroaryl group having 1 to 40 carbon atoms, aryloxy group having 6 to 40 carbon atoms, alkyloxy group having 1 to 40 carbon atoms, arylamino group having 6 to 40 carbon atoms, diarylamino group having 12 to 40 carbon atoms, arylalkyl group having 7 to 40 carbon atoms , It is selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms and a heterocycloalkyl group having 3 to 40 carbon atoms, or forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group A group, a halogen group, or a combination thereof, L is a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted condensed aryl group having 10 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 1 to 30 carbon atoms It is selected from the group consisting of a heteroaryl group containing 30 N, S, and O and a substituted or unsubstituted condensed heteroarylene group containing N, S, and O having 1 to 30 carbon atoms, and Het is a substituted or unsubstituted A heteroaryl group containing 3 to 20 carbon atoms and N, and A ₁ and A ₂ are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 40 carbon atoms It is Ki.

The electron transport region may include at least one of compounds represented by compound group 1 below.

[Compound group 1]

The light emitting layer may include a compound represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2, AA is a cycloalkyl group having 3 to 60 carbon atoms, a 5- to 6-membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 1 to 60 carbon atoms, or a ring containing X and a ring containing Y It condenses with a ring to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

X is selected from N(Ar ₃ ), O and S, Y is selected from N(Ar ₄ ), O and S, Ar ₃ and Ar ₄ are each independently an alkyl group having 1 to 60 carbon atoms, and an alkyl group having 3 to 60 carbon atoms. A cycloalkyl group, a 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms , An alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 1 to 60 carbon atoms, Z ₁ to Z ₈ are each independently selected from C (Ar ₅ ) and N, and Z Ar ₅ contained in each of ₁ to Z ₈ may be different from each other, adjacent Ar ₅ may be bonded to each other to form a ring, and Ar ₅ contained in each of Z ₁ to Z ₈ may independently have hydrogen, 1 to 10 carbon atoms A 60-membered alkyl group, a halogen group, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, a 5- to 6-membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, and a bicycle having 7 to 60 carbon atoms Roalkyl group, adamantyl group, C2-60 alkenyl group, C2-60 alkynyl group, C6-60 aryl group, C1-60 alkoxy group, C6-60 aryloxy group, C1 to 60 heteroaryl group, 6 to 60 carbon atoms arylthio group, 1 to 60 carbon atoms alkylthio group, 1 to 60 carbon atoms mono or dialkylamino group, 6 to 30 carbon atoms monoarylamino group, 3 to 90 carbon atoms A trialkylsilyl group, a dialkylarylsilyl group having 7 to 60 carbon atoms, a triarylsilyl group having 18 to 90 carbon atoms, a mono or diarylboranyl group having 6 to 60 carbon atoms, a mono or dialkylboranyl group having 1 to 120 carbon atoms, is selected from a nitro group and a hydroxy group, provided that X is N(Ar ₃ ), Y is N(Ar ₄ ), Ar ₃ and Ar ₄ are the same, and Z ₁ to Z ₈ are all C(Ar ₅ ), and Ar ₅ included in each of Z ₁ to Z ₈ are the same as each other.

Ar ₃ to Ar ₅ are each independently an alkyl group, a cycloalkyl group, a heterocycloalkyl group, a bicycloalkyl group, an adamantyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, and an aryl group. Ogi, alkylthio group, alkylamino group, arylamino group, trialkylsilyl group, dialkylarylsilyl group, triarylsilyl group, arylboranyl group or alkylboranyl group is an alkyl group having 1 to 60 carbon atoms, a halogen group, a cyano group, a carbon number 3-60 cycloalkyl group, 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, bicycloalkyl group having 7-60 carbon atoms, adamantyl group, 2-60 carbon atoms An alkenyl group, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, P(=O)RaRb [Ra and Rb are independent of each other an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms], an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 1 to 60 carbon atoms, and an aryl group having 6 to 60 carbon atoms substituted with an aryl group having 1 to 60 carbon atoms. Heteroaryl group, heteroaryl group having 1 to 60 carbon atoms substituted with an alkyl group having 1 to 60 carbon atoms, aralkyl group having 7 to 120 carbon atoms, arylthio group having 6 to 60 carbon atoms, alkylthio group having 1 to 60 carbon atoms, and 1 carbon atom to 30 mono or dialkylamino group, C6 to 60 mono or diarylamino group, C3 to 90 trialkylsilyl group, C7 to 60 dialkyl arylsilyl group, C18 to 90 triarylsilyl group , A mono or diaryl boranyl group having 6 to 60 carbon atoms, a mono or dialkyl boranyl group having 1 to 120 carbon atoms, a nitro group, and a hydroxy group.

The light emitting layer may include at least one of compounds represented by compound group 2 below.

[Compound group 2]

The light emitting layer may include at least one of compounds represented by compound group 3 below.

[Compound group 3]

The light emitting layer may further include an arylamine-based compound.

The arylamine-based compound may include at least one of the compounds represented by compound group 4 below.

[Compound group 4]

The emission layer may emit green light.

A display device according to an exemplary embodiment includes a plurality of pixels. At least one of the pixels includes a first electrode, a hole transport region provided on the first electrode, a light emitting layer provided on the hole transport region, an electron transport region provided on the light emitting layer, and a hole transport region provided on the electron transport region. It includes a second electrode to be. The electron transport region includes a compound represented by Formula 1 below.

[Formula 1]

In Formula 1, X ₁ and X ₂ are each independently CR ₅ or N, and R ₁ to R ₅ are each independently hydrogen, heavy hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, and Heteroaryl group having 1 to 40 carbon atoms, aryloxy group having 6 to 40 carbon atoms, alkyloxy group having 1 to 40 carbon atoms, arylamino group having 6 to 40 carbon atoms, diarylamino group having 12 to 40 carbon atoms, arylalkyl group having 7 to 40 carbon atoms , It is selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms and a heterocycloalkyl group having 3 to 40 carbon atoms, or forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group A group, a halogen group, or a combination thereof, L is a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted condensed aryl group having 10 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 1 to 30 carbon atoms It is selected from the group consisting of a heteroaryl group containing 30 N, S, and O and a substituted or unsubstituted condensed heteroarylene group containing N, S, and O having 1 to 30 carbon atoms. Het is a substituted or unsubstituted heteroaryl group containing 3 to 20 carbon atoms and N, and A ₁ and A ₂ are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted It is a heteroaryl group having 1 to 40 carbon atoms.

The electron transport region may include at least one of compounds represented by compound group 1 below.

[Compound group 1]

The light emitting layer may include a compound represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2, AA is a cycloalkyl group having 3 to 60 carbon atoms, a 5- to 6-membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 1 to 60 carbon atoms, or a ring containing X and a ring containing Y It condenses with a ring to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring. X is selected from N(Ar ₃ ), O and S, Y is selected from N(Ar ₄ ), O and S, Ar ₃ and Ar ₄ are each independently an alkyl group having 1 to 60 carbon atoms, and an alkyl group having 3 to 60 carbon atoms. A cycloalkyl group, a 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms , An alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 1 to 60 carbon atoms, Z ₁ to Z ₈ are each independently selected from C (Ar ₅ ) and N, and Z Ar ₅ contained in each of ₁ to Z ₈ may be different from each other, adjacent Ar ₅ may be bonded to each other to form a ring, and Ar ₅ contained in each of Z ₁ to Z ₈ may independently have hydrogen, 1 to 10 carbon atoms A 60-membered alkyl group, a halogen group, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, a 5- to 6-membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, and a bicycle having 7 to 60 carbon atoms Roalkyl group, adamantyl group, C2-60 alkenyl group, C2-60 alkynyl group, C6-60 aryl group, C1-60 alkoxy group, C6-60 aryloxy group, C1 to 60 heteroaryl group, 6 to 60 carbon atoms arylthio group, 1 to 60 carbon atoms alkylthio group, 1 to 60 carbon atoms mono or dialkylamino group, 6 to 30 carbon atoms monoarylamino group, 3 to 90 carbon atoms A trialkylsilyl group, a dialkylarylsilyl group having 7 to 60 carbon atoms, a triarylsilyl group having 18 to 90 carbon atoms, a mono or diarylboranyl group having 6 to 60 carbon atoms, a mono or dialkylboranyl group having 1 to 120 carbon atoms, is selected from a nitro group and a hydroxy group, provided that X is N(Ar ₃ ), Y is N(Ar ₄ ), Ar ₃ and Ar ₄ are the same, and Z ₁ to Z ₈ are all C(Ar ₅ ), and Ar ₅ included in each of Z ₁ to Z ₈ are the same as each other.

Ar ₃ to Ar ₅ are each independently an alkyl group, a cycloalkyl group, a heterocycloalkyl group, a bicycloalkyl group, an adamantyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, and an aryl group. Ogi, alkylthio group, alkylamino group, arylamino group, trialkylsilyl group, dialkylarylsilyl group, triarylsilyl group, arylboranyl group or alkylboranyl group is an alkyl group having 1 to 60 carbon atoms, a halogen group, a cyano group, a carbon number 3-60 cycloalkyl group, 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, bicycloalkyl group having 7-60 carbon atoms, adamantyl group, 2-60 carbon atoms An alkenyl group, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, P(=O)RaRb [Ra and Rb are independent of each other an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms], an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 1 to 60 carbon atoms, and an aryl group having 6 to 60 carbon atoms substituted with an aryl group having 1 to 60 carbon atoms. Heteroaryl group, heteroaryl group having 1 to 60 carbon atoms substituted with an alkyl group having 1 to 60 carbon atoms, aralkyl group having 7 to 120 carbon atoms, arylthio group having 6 to 60 carbon atoms, alkylthio group having 1 to 60 carbon atoms, and 1 carbon atom to 30 mono or dialkylamino group, C6 to 60 mono or diarylamino group, C3 to 90 trialkylsilyl group, C7 to 60 dialkyl arylsilyl group, C18 to 90 triarylsilyl group , A mono or diaryl boranyl group having 6 to 60 carbon atoms, a mono or dialkyl boranyl group having 1 to 120 carbon atoms, a nitro group, and a hydroxy group.

The light emitting layer may include at least one of compounds represented by compound group 2 below.

[Compound group 2]

The light emitting layer may include at least one of compounds represented by compound group 3 below.

[Compound group 3]

The light emitting layer may further include an arylamine-based compound.

The arylamine-based compound may include at least one of the compounds represented by compound group 4 below.

[Compound group 4]

The emission layer may emit green light.

According to the organic light emitting device according to an embodiment of the present invention, efficiency can be increased and lifespan can be extended.

According to the display device according to an exemplary embodiment of the present invention, efficiency can be increased and lifespan can be extended.

1 is a schematic cross-sectional view of an organic light emitting diode according to an exemplary embodiment of the present invention.
2 is a schematic cross-sectional view of an organic light emitting diode according to an exemplary embodiment of the present invention.
3 is a perspective view schematically illustrating a display device according to an exemplary embodiment of the present invention.
4 is a circuit diagram of one of pixels included in a display device according to an exemplary embodiment of the present invention.
5 is a plan view illustrating one of pixels included in a display device according to an exemplary embodiment of the present invention.
6 is a schematic cross-sectional view corresponding to line II' of FIG. 5 .

The above objects, other objects, features and advantages of the present invention will be easily understood through the following preferred embodiments in conjunction with the accompanying drawings. However, the present invention is not limited to the embodiments described herein and may be embodied in other forms. Rather, the embodiments introduced herein are provided so that the disclosed content will be thorough and complete and the spirit of the present invention will be sufficiently conveyed to those skilled in the art.

Like reference numerals have been used for like elements throughout the description of each figure. In the accompanying drawings, the dimensions of the structures are shown enlarged than actual for clarity of the present invention. Terms such as first and second may be used to describe various components, but the components should not be limited by the terms. These terms are only used for the purpose of distinguishing one component from another. For example, a first element may be termed a second element, and similarly, a second element may be termed a first element, without departing from the scope of the present invention. Singular expressions include plural expressions unless the context clearly dictates otherwise.

In this application, the terms "include" or "have" are intended to designate that there is a feature, number, step, operation, component, part, or combination thereof described in the specification, but one or more other features It should be understood that it does not preclude the possibility of the presence or addition of numbers, steps, operations, components, parts, or combinations thereof. In addition, when a part such as a layer, film, region, plate, etc. is said to be “on” another part, this includes not only the case where it is “directly on” the other part, but also the case where there is another part in the middle. Conversely, when a part such as a layer, film, region, plate, etc. is said to be "under" another part, this includes not only the case where it is "directly below" the other part, but also the case where another part exists in the middle.

Hereinafter, an organic light emitting device according to an exemplary embodiment of the present invention will be described.

1 is a schematic cross-sectional view of an organic light emitting device (OEL) according to an exemplary embodiment of the present invention.

Referring to FIG. 1 , an organic light emitting diode OEL according to an exemplary embodiment of the present invention includes a first electrode EL1, a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode (EL2).

The first electrode EL1 has conductivity. The first electrode EL1 may be a pixel electrode or an anode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium ITZO (ITZO). tin zinc oxide) and the like. When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a mixture of metals. can

An organic layer may be disposed on the first electrode EL1. The organic layer includes the light emitting layer (EML). The organic layer may further include a hole transport region (HTR) and an electron transport region (ETR).

The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer, and an electron blocking layer.

The hole transport region HTR may have a single layer structure 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 HTR has a single layer structure made of a plurality of different materials, or a hole injection layer (HIL)/hole transport layer (HTL) sequentially stacked from the first electrode EL1; Structure of hole injection layer (HIL) / hole transport layer (HTL) / buffer layer, hole injection layer (HIL) / buffer layer, hole transport layer (HTL) / buffer layer or hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer It may have, but is not limited thereto.

The hole transport region (HTR) is formed by various methods such as vacuum deposition method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser induced thermal imaging (LITI), and the like. can be formed using

When the hole transport region (HTR) includes the hole injection layer (HIL), the hole transport region (HTR) may include a phthalocyanine compound such as copper phthalocyanine, DNTPD (N,N'-diphenyl-N, N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4',4"-tris(3-methylphenylphenylamino) triphenylamine ), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2TNATA(4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine) , PEDOT/PSS (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), PANI/DBSA(Polyaniline/Dodecylbenzenesulfonic acid), PANI/CSA(Polyaniline/Camphor sulfonicacid), PANI/PSS((Polyaniline)/ Poly(4-styrenesulfonate)) and the like, but are not limited thereto.

When the hole transport region HTR includes the hole transport layer HTL, the hole transport region HTR may include a carbazole-based derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorine-based derivative, or TPD ( N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(N-carbazolyl )triphenylamine), triphenylamine derivatives such as NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TAPC(4,4'-Cyclohexylidene bis[N,N-bis(4 -methylphenyl)benzenamine]) and the like, but are not limited thereto.

The hole transport region HTR may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. If the hole transport region (HTR) includes both the hole injection layer (HIL) and the hole transport layer (HTL), the thickness of the hole injection layer (HIL) is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, The hole transport layer (HTL) may have a thickness of about 50 Å to about 2000 Å, for example, about 100 Å to about 1500 Å. When the thicknesses of the hole transport region HTR, the hole injection layer HIL, and the hole transport layer HTL satisfy the ranges described above, satisfactory hole transport characteristics may be obtained without a substantial increase in driving voltage.

In addition to the aforementioned materials, the hole transport region HTR 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 (HTR). 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 compound containing a cyano group, but is not limited thereto. For example, non-limiting examples of the p-dopant include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, and the like. It may include, but is not limited thereto.

As mentioned above, the hole transport region HTR may further include at least one of a buffer layer and an electron blocking layer in addition to the hole injection layer HIL and the hole transport layer HTL. The buffer layer may increase light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the light emitting layer EML. A material that can be included in the hole transport region (HTR) may be used as a material included in the buffer layer. The electron blocking layer is a layer that serves to prevent injection of electrons from the electron transport region ETR to the hole transport region HTR.

The light emitting layer EML is provided on the hole transport region HTR. The light emitting layer EML may have a single layer structure 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.

The light emitting layer (EML) is formed using various methods such as a vacuum deposition method, a spin coating method, a cast method, a LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method. It can be.

The light emitting layer EML may emit green light. The light emitting layer EML may be made of a material that emits green light and may include a fluorescent material or a phosphorescent material. In addition, the light emitting layer EML may include a host and a dopant.

The host may include a compound represented by Formula 2 below.

[Formula 2]

In Formula 2, AA is a cycloalkyl group having 3 to 60 carbon atoms, a 5- to 6-membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 1 to 60 carbon atoms, or a ring containing X and a ring containing Y It condenses with a ring to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

X is selected from N(Ar ₃ ), O and S, Y is selected from N(Ar ₄ ), O and S, Ar ₃ and Ar ₄ are each independently an alkyl group having 1 to 60 carbon atoms, and an alkyl group having 3 to 60 carbon atoms. A cycloalkyl group, a 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms , An alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 1 to 60 carbon atoms, Z ₁ to Z ₈ are each independently selected from C (Ar ₅ ) and N, and Z Ar ₅ contained in each of ₁ to Z ₈ may be different from each other, adjacent Ar ₅ may be bonded to each other to form a ring, and Ar ₅ contained in each of Z ₁ to Z ₈ may independently have hydrogen, 1 to 10 carbon atoms A 60-membered alkyl group, a halogen group, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, a 5- to 6-membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, and a bicycle having 7 to 60 carbon atoms Roalkyl group, adamantyl group, C2-60 alkenyl group, C2-60 alkynyl group, C6-60 aryl group, C1-60 alkoxy group, C6-60 aryloxy group, C1 to 60 heteroaryl group, 6 to 60 carbon atoms arylthio group, 1 to 60 carbon atoms alkylthio group, 1 to 60 carbon atoms mono or dialkylamino group, 6 to 30 carbon atoms monoarylamino group, 3 to 90 carbon atoms A trialkylsilyl group, a dialkylarylsilyl group having 7 to 60 carbon atoms, a triarylsilyl group having 18 to 90 carbon atoms, a mono or diarylboranyl group having 6 to 60 carbon atoms, a mono or dialkylboranyl group having 1 to 120 carbon atoms, is selected from a nitro group and a hydroxy group, provided that X is N(Ar ₃ ), Y is N(Ar ₄ ), Ar ₃ and Ar ₄ are the same, and Z ₁ to Z ₈ are all C(Ar ₅ ), and Ar ₅ included in each of Z ₁ to Z ₈ are the same as each other.

Ar ₃ to Ar ₅ are each independently an alkyl group, a cycloalkyl group, a heterocycloalkyl group, a bicycloalkyl group, an adamantyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, and an aryl group. Ogi, alkylthio group, alkylamino group, arylamino group, trialkylsilyl group, dialkylarylsilyl group, triarylsilyl group, arylboranyl group or alkylboranyl group is an alkyl group having 1 to 60 carbon atoms, a halogen group, a cyano group, a carbon number 3-60 cycloalkyl group, 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, bicycloalkyl group having 7-60 carbon atoms, adamantyl group, 2-60 carbon atoms An alkenyl group, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, P(=O)RaRb [Ra and Rb are independent of each other an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms], an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 1 to 60 carbon atoms, and an aryl group having 6 to 60 carbon atoms substituted with an aryl group having 1 to 60 carbon atoms. Heteroaryl group, heteroaryl group having 1 to 60 carbon atoms substituted with an alkyl group having 1 to 60 carbon atoms, aralkyl group having 7 to 120 carbon atoms, arylthio group having 6 to 60 carbon atoms, alkylthio group having 1 to 60 carbon atoms, and 1 carbon atom to 30 mono or dialkylamino group, C6 to 60 mono or diarylamino group, C3 to 90 trialkylsilyl group, C7 to 60 dialkyl arylsilyl group, C18 to 90 triarylsilyl group , A mono or diaryl boranyl group having 6 to 60 carbon atoms, a mono or dialkyl boranyl group having 1 to 120 carbon atoms, a nitro group, and a hydroxy group.

The host may include at least one of the compounds represented by compound group 2 below.

[Compound group 2]

The host may include at least one of the compounds represented by compound group 3 below.

[Compound group 3]

The light emitting layer EML may further include at least one of an arylamine-based compound and a styryl arylamine-based compound.

The arylamine-based compound may include at least one of the compounds represented by compound group 4 below.

[Compound group 4]

The electron transport region ETR is provided on the light emitting layer EML. The electron transport region ETR may include at least one of a hole blocking layer, an electron transport layer ETL, and an electron injection layer EIL, but is not limited thereto.

For example, the electron transport region ETR is composed of an electron transport layer (ETL)/electron injection layer (EIL) or a hole blocking layer/electron transport layer (ETL)/electron injection layer (EIL) sequentially stacked from the light emitting layer (EML). structure, or may have a single-layer structure in which two or more layers are mixed, but is not limited thereto.

The electron transport region (ETR) is formed by various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI). can be formed using

When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR includes a compound represented by Chemical Formula 1 below.

[Formula 1]

In Formula 1, X ₁ and X ₂ are each independently CR ₅ or N, and R ₁ to R ₅ are each independently hydrogen, heavy hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, and Heteroaryl group having 1 to 40 carbon atoms, aryloxy group having 6 to 40 carbon atoms, alkyloxy group having 1 to 40 carbon atoms, arylamino group having 6 to 40 carbon atoms, diarylamino group having 12 to 40 carbon atoms, arylalkyl group having 7 to 40 carbon atoms , It is selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms and a heterocycloalkyl group having 3 to 40 carbon atoms, or forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group A group, a halogen group, or a combination thereof, L is a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted condensed aryl group having 10 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 1 to 30 carbon atoms It is selected from the group consisting of a heteroaryl group containing 30 N, S, and O and a substituted or unsubstituted condensed heteroarylene group containing N, S, and O having 1 to 30 carbon atoms.

L is, for example, an aryl substituted with at least one substituent selected from the substituent group including an alkyl group, a hydroxyl group, a cyano group, an alkoxy group, a halogen group, a carboxy group, an alkoxycarbonyl group, a thionyl group, a thiol group, and a sulfone group. group, a condensed aryl group, a heteroaryl group, or a condensed heteroarylene group.

Het is a substituted or unsubstituted heteroaryl group containing 3 to 20 carbon atoms and N, and A ₁ and A ₂ are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted It is a heteroaryl group having 1 to 40 carbon atoms.

The electron transport region (ETR) may include at least one of compounds represented by compound group 1 below.

[Compound group 1]

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

When the electron transport region (ETR) includes the electron injection layer (EIL), the electron transport region (ETR) is a lanthanum group metal such as LiF, lithium quinolate (LiQ), Li ₂ O, BaO, NaCl, CsF, Yb, Alternatively, a metal halide such as RbCl or RbI may be used, but is not limited thereto. The electron injection layer (EIL) may also be made of a mixture of an electron transport material and an insulating organometal salt. The organometallic salt may be a material having an energy band gap of about 4 eV or more. Specifically, for example, the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate or metal stearate. can The thickness of the electron injection layer (EIL) may be about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the electron injection layer (EIL) satisfies the aforementioned range, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

As mentioned above, the electron transport region ETR may include a hole blocking layer. The hole blocking layer may include, for example, at least one of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and Bphen (4,7-diphenyl-1,10-phenanthroline). However, it is not limited thereto. The hole blocking layer may have a thickness of about 20 Å to about 1000 Å, such as about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the aforementioned range, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode or a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode.

When the second electrode EL2 is a transmissive electrode, the second electrode EL2 is Li, Ca, LiF/Ca, LiF/Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof (eg , a mixture of Ag and Mg).

The second electrode EL2 may include an auxiliary electrode. The auxiliary electrode is a film formed by depositing the material toward the light emitting layer (EML), and a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), or zinc oxide (ZnO) on the film. , indium tin zinc oxide (ITZO), Mo, Ti, and the like.

When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 is Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/ Ca, LiF/Al, Mo, Ti, or a compound or mixture thereof (eg, a mixture of Ag and Mg). Alternatively, a plurality of layer structures including a reflective film or semi-transmissive film formed of the above material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), or the like. can be

In the organic light emitting diode OEL according to an embodiment of the present invention, as voltage is applied to the first electrode EL1 and the second electrode EL2, holes injected from the first electrode EL1 are The hole transport region HTR moves to the light emitting layer EML, and the electrons injected from the second electrode EL2 move to the light emitting layer EML through the electron transport region ETR. Electrons and holes recombine in the light emitting layer (EML) to generate excitons, and as the excitons fall from an excited state to a ground state, they emit light.

An organic light emitting device according to an embodiment of the present invention includes an electron transport region including the compound represented by Formula 1 above. An organic light emitting device according to an embodiment of the present invention includes a light emitting layer including the compound represented by Chemical Formula 2 above. Accordingly, in the organic light emitting device, a band gap between an energy band of the hole transport region and an energy band of the light emitting layer may be reduced, and holes may be easily injected into the light emitting layer. In addition, a band gap between an energy band of the light emitting layer and an energy band of the electron transport region may be reduced, and injection of electrons into the light emitting layer may be facilitated. Accordingly, the organic light emitting device according to an embodiment of the present invention can promote high efficiency and long lifespan.

Hereinafter, a display device according to an exemplary embodiment of the present invention will be described. Hereinafter, differences from the organic light emitting device OEL according to an embodiment of the present invention described above will be described in detail, and parts not described depend on the organic light emitting device OEL according to an embodiment of the present invention described above. .

3 is a perspective view schematically illustrating a display device according to an exemplary embodiment of the present invention.

Referring to FIG. 3 , the display device 10 according to an exemplary embodiment includes a display area DA and a non-display area NDA.

The display area DA displays an image. When viewed in the thickness direction of the display device 10 (for example, DR3), the display area DA may have an approximately rectangular shape, but is not limited thereto.

The display area DA includes a plurality of pixel areas PA. The pixel areas PA may be arranged in a matrix form. The pixel areas PA may be defined by a pixel defining layer (PDL in FIG. 6 ). The pixel areas PA may include each of a plurality of pixels (PX in FIG. 4 ).

The non-display area NDA does not display an image. When viewed in the thickness direction of the display device 10 ( DR3 ), the non-display area NDA may surround the display area DA, for example. The non-display area NDA may be adjacent to the display area DA in a first direction (eg DR1) and a second direction (eg DR2) crossing the first direction (eg DR1).

4 is a circuit diagram of one of pixels included in a display device according to an exemplary embodiment of the present invention.

5 is a plan view illustrating one of pixels included in a display device according to an exemplary embodiment of the present invention.

6 is a schematic cross-sectional view corresponding to line II' of FIG. 5 .

4 to 6 , each of the pixels PX includes a wiring part including a gate line GL, a data line DL, and a driving voltage line DVL, and thin film transistors TFT1 and TFT2 connected to the wiring part. ), an organic light emitting element OEL connected to the thin film transistors TFT1 and TFT2, and a capacitor Cst.

Each of the pixels PX may emit light of a specific color, for example, one of red light, green light, and blue light. The type of color light is not limited to the above, and for example, cyan light, magenta light, and yellow light may be added.

The gate line GL extends in the first direction DR1. The data line DL extends in a second direction DR2 crossing the gate line GL. The driving voltage line DVL extends in substantially the same direction as the data line DL, that is, in the second direction DR2. Gate line GL transfers scan signals to thin film transistors TFT1 and TFT2, data line DL transfers data signals to thin film transistors TFT1 and TFT2, and driving voltage line DVL transfers scan signals to thin film transistors. Provides driving voltage.

The thin film transistors TFT1 and TFT2 may include a driving thin film transistor TFT2 for controlling the organic light emitting element OEL and a switching thin film transistor TFT1 for switching the driving thin film transistor TFT2. In an exemplary embodiment, the present invention describes that each of the pixels PX includes two thin film transistors TFT1 and TFT2, but is not limited thereto, and each of the pixels PX includes one thin film transistor and a capacitor. may be included, and each of the pixels PX may include three or more thin film transistors and two or more capacitors.

The switching thin film transistor TFT1 includes a first gate electrode GE1 , a first source electrode SE1 , and a first drain electrode DE1 . The first gate electrode GE1 is connected to the gate line GL, and the first source electrode SE1 is connected to the data line DL. The first drain electrode DE1 is connected to the first common electrode CE1 through the fifth contact hole CH5. The switching thin film transistor TFT1 transfers the data signal applied to the data line DL to the driving thin film transistor TFT2 according to the scan signal applied to the gate line GL.

The driving thin film transistor TFT2 includes a second gate electrode GE2, a second source electrode SE2, and a second drain electrode DE2. The second gate electrode GE2 is connected to the first common electrode CE1. The second source electrode SE2 is connected to the driving voltage line DVL. The second drain electrode DE2 is connected to the first electrode EL1 through the third contact hole CH3.

The first electrode EL1 is connected to the second drain electrode DE2 of the driving thin film transistor TFT2. A common voltage is applied to the second electrode EL2, and the light emitting layer EML emits blue light according to an output signal of the driving thin film transistor TFT2 to display an image. The first electrode EL1 and the second electrode EL2 will be described later in more detail.

The capacitor Cst is connected between the second gate electrode GE2 and the second source electrode SE2 of the driving thin film transistor TFT2, and data input to the second gate electrode GE2 of the driving thin film transistor TFT2 Charge and maintain signal. The capacitor Cst includes a first common electrode CE1 connected to the first drain electrode DE1 through the sixth contact hole CH6 and a second common electrode CE2 connected to the driving voltage line DVL. can do.

Referring to FIGS. 5 and 6 , the display device 10 according to an exemplary embodiment includes a base substrate BS on which thin film transistors and organic light emitting diodes OEL are stacked. The base substrate BS is not particularly limited as long as it is commonly used, but may be formed of, for example, an insulating material such as glass, plastic, or quartz. Examples of the organic polymer constituting the base substrate BS include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyimide, and polyethersulfone. The base substrate BS may be selected in consideration of mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, waterproofness, and the like.

A substrate buffer layer (not shown) may be provided on the base substrate BS. The substrate buffer layer (not shown) prevents diffusion of impurities into the switching thin film transistor TFT1 and the driving thin film transistor TFT2. The substrate buffer layer (not shown) may be formed of silicon nitride (SiNx), silicon oxide (SiOx), silicon nitride oxide (SiOxNy), or the like, and may be omitted depending on the material of the base substrate BS and process conditions.

A first semiconductor layer SM1 and a second semiconductor layer SM2 are provided on the base substrate BS. The first semiconductor layer SM1 and the second semiconductor layer SM2 are formed of a semiconductor material and operate as active layers of the switching thin film transistor TFT1 and the driving thin film transistor TFT2, respectively. The first semiconductor layer SM1 and the second semiconductor layer SM2 each include a source region SA, a drain region DA, and a channel region CA provided between the source region SA and the drain region DA. do. Each of the first semiconductor layer SM1 and the second semiconductor layer SM2 may be formed by selecting an inorganic semiconductor or an organic semiconductor. The source region SA and the drain region DA may be doped with n-type impurities or p-type impurities.

A gate insulating layer GI is provided on the first semiconductor layer SM1 and the second semiconductor layer SM2. The gate insulating layer GI covers the first semiconductor layer SM1 and the second semiconductor layer SM2. The gate insulating layer GI may be formed of an organic insulating material or an inorganic insulating material.

A first gate electrode GE1 and a second gate electrode GE2 are provided on the gate insulating layer GI. The first gate electrode GE1 and the second gate electrode GE2 are formed to cover regions corresponding to the channel regions CA of the first and second semiconductor layers SM1 and SM2, respectively.

An interlayer insulating layer IL is provided on the first gate electrode GE1 and the second gate electrode GE2 . The interlayer insulating layer IL covers the first gate electrode GE1 and the second gate electrode GE2. The interlayer insulating layer IL may be formed of an organic insulating material or an inorganic insulating material.

A first source electrode SE1, a first drain electrode DE1, a second source electrode SE2, and a second drain electrode DE2 are provided on the interlayer insulating layer IL. The second drain electrode DE2 contacts the drain region DA of the second semiconductor layer SM2 through the first contact hole CH1 formed in the gate insulating layer GI and the interlayer insulating layer IL, and The second source electrode SE2 contacts the source region SA of the second semiconductor layer SM2 through the second contact hole CH2 formed in the gate insulating layer GI and the interlayer insulating layer IL. The first source electrode SE1 contacts a source region (not shown) of the first semiconductor layer SM1 through a fourth contact hole CH4 formed in the gate insulating layer GI and the interlayer insulating layer IL; The first drain electrode DE1 contacts the drain region (not shown) of the first semiconductor layer SM1 through the fifth contact hole CH5 formed in the gate insulating layer GI and the interlayer insulating layer IL.

A passivation layer PL is provided on the first source electrode SE1 and the first drain electrode DE1, and on the second source electrode SE2 and the second drain electrode DE2. The passivation layer PL may serve as a protective film for protecting the switching thin film transistor TFT1 and the driving thin film transistor TFT2, or may serve as a planarization film for planarizing upper surfaces thereof.

A first electrode EL1 is provided on the passivation layer PL. The first electrode EL1 may be, for example, an anode. The first electrode EL1 is connected to the second drain electrode DE2 of the driving thin film transistor TR2 through the third contact hole CH3 formed in the passivation layer PL.

A pixel defining layer PDL partitioning pixel areas (PA of FIG. 3 ) to correspond to each of the pixels PX is provided on the passivation layer PL. The pixel defining layer PDL exposes the upper surface of the first electrode EL1 and protrudes from the base substrate BS along the circumference of each of the pixels PX. The pixel defining layer PDL is not limited thereto, but may include a metal-fluorine ion compound. For example, the pixel defining layer PDL may be formed of any one metal-fluorine ion compound among LiF, BaF ₂ , and CsF. When the metal-fluorine ion compound has a predetermined thickness, it has insulating properties. The thickness of the pixel defining layer (PDL) may be, for example, 10 nm to 100 nm.

An organic light emitting element OEL is provided in each pixel area (PA in FIG. 3 ) surrounded by the pixel defining layer PDL. The organic light emitting element OEL includes a first electrode EL1 , a hole transport region HTR, an emission layer EML, an electron transport region ETR, and a second electrode EL2 .

The first electrode EL1 has conductivity. The first electrode EL1 may be a pixel electrode or an anode. The first electrode EL1 may be a transmissive electrode, a transflective electrode, or a reflective electrode. When the first electrode EL1 is a transmissive electrode, the first electrode EL1 is a transparent metal oxide, for example, indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium ITZO (ITZO). tin zinc oxide) and the like. When the first electrode EL1 is a transflective electrode or a reflective electrode, the first electrode EL1 may include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a mixture of metals. can

An organic layer may be disposed on the first electrode EL1. The organic layer includes the light emitting layer (EML). The organic layer may further include a hole transport region (HTR) and an electron transport region (ETR).

The hole transport region HTR is provided on the first electrode EL1. The hole transport region HTR may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer, and an electron blocking layer.

The hole transport region HTR may have a single layer structure 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 HTR has a single layer structure made of a plurality of different materials, or a hole injection layer (HIL)/hole transport layer (HTL) sequentially stacked from the first electrode EL1; Structure of hole injection layer (HIL) / hole transport layer (HTL) / buffer layer, hole injection layer (HIL) / buffer layer, hole transport layer (HTL) / buffer layer or hole injection layer (HIL) / hole transport layer (HTL) / electron blocking layer It may have, but is not limited thereto.

The hole transport region (HTR) is formed by various methods such as vacuum deposition method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, laser induced thermal imaging (LITI), and the like. can be formed using

When the hole transport region (HTR) includes the hole injection layer (HIL), the hole transport region (HTR) may include a phthalocyanine compound such as copper phthalocyanine, DNTPD (N,N'-diphenyl-N, N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA(4,4',4"-tris(3-methylphenylphenylamino) triphenylamine ), TDATA(4,4'4"-Tris(N,N-diphenylamino)triphenylamine), 2TNATA(4,4',4"-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine) , PEDOT/PSS (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), PANI/DBSA(Polyaniline/Dodecylbenzenesulfonic acid), PANI/CSA(Polyaniline/Camphor sulfonicacid), PANI/PSS((Polyaniline)/ Poly(4-styrenesulfonate)) and the like, but are not limited thereto.

When the hole transport region HTR includes the hole transport layer HTL, the hole transport region HTR may include a carbazole-based derivative such as N-phenylcarbazole or polyvinylcarbazole, a fluorine-based derivative, or TPD ( N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA(4,4',4"-tris(N-carbazolyl )triphenylamine), triphenylamine derivatives such as NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TAPC(4,4'-Cyclohexylidene bis[N,N-bis(4 -methylphenyl)benzenamine]) and the like, but are not limited thereto.

The hole transport region HTR may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. If the hole transport region (HTR) includes both the hole injection layer (HIL) and the hole transport layer (HTL), the thickness of the hole injection layer (HIL) is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, The hole transport layer (HTL) may have a thickness of about 50 Å to about 2000 Å, for example, about 100 Å to about 1500 Å. When the thicknesses of the hole transport region HTR, the hole injection layer HIL, and the hole transport layer HTL satisfy the ranges described above, satisfactory hole transport characteristics may be obtained without a substantial increase in driving voltage.

In addition to the aforementioned materials, the hole transport region HTR 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 (HTR). 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 compound containing a cyano group, but is not limited thereto. For example, non-limiting examples of the p-dopant include quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-tetrafluoro-tetracyanoquinodimethane), metal oxides such as tungsten oxide and molybdenum oxide, and the like. It may include, but is not limited thereto.

As mentioned above, the hole transport region HTR may further include at least one of a buffer layer and an electron blocking layer in addition to the hole injection layer HIL and the hole transport layer HTL. The buffer layer may increase light emission efficiency by compensating for a resonance distance according to a wavelength of light emitted from the light emitting layer EML. A material that can be included in the hole transport region (HTR) may be used as a material included in the buffer layer. The electron blocking layer is a layer that serves to prevent injection of electrons from the electron transport region ETR to the hole transport region HTR.

The light emitting layer EML is provided on the hole transport region HTR. The light emitting layer EML may have a single layer structure 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.

The light emitting layer (EML) is formed using various methods such as a vacuum deposition method, a spin coating method, a cast method, a LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, and a laser induced thermal imaging (LITI) method. It can be.

The light emitting layer EML may emit green light. The light emitting layer EML may be made of a material that emits green light and may include a fluorescent material or a phosphorescent material. In addition, the light emitting layer EML may include a host and a dopant.

The host may include a compound represented by Formula 2 below.

[Formula 2]

In Formula 2, AA is a cycloalkyl group having 3 to 60 carbon atoms, a 5- to 6-membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 1 to 60 carbon atoms, or a ring containing X and a ring containing Y It condenses with a ring to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

X is selected from N(Ar ₃ ), O and S, Y is selected from N(Ar ₄ ), O and S, Ar ₃ and Ar ₄ are each independently an alkyl group having 1 to 60 carbon atoms, and an alkyl group having 3 to 60 carbon atoms. A cycloalkyl group, a 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms , An alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 1 to 60 carbon atoms, Z ₁ to Z ₈ are each independently selected from C (Ar ₅ ) and N, and Z Ar ₅ contained in each of ₁ to Z ₈ may be different from each other, adjacent Ar ₅ may be bonded to each other to form a ring, and Ar ₅ contained in each of Z ₁ to Z ₈ may independently have hydrogen, 1 to 10 carbon atoms A 60-membered alkyl group, a halogen group, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, a 5- to 6-membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, and a bicycle having 7 to 60 carbon atoms Roalkyl group, adamantyl group, C2-60 alkenyl group, C2-60 alkynyl group, C6-60 aryl group, C1-60 alkoxy group, C6-60 aryloxy group, C1 to 60 heteroaryl group, 6 to 60 carbon atoms arylthio group, 1 to 60 carbon atoms alkylthio group, 1 to 60 carbon atoms mono or dialkylamino group, 6 to 30 carbon atoms monoarylamino group, 3 to 90 carbon atoms A trialkylsilyl group, a dialkylarylsilyl group having 7 to 60 carbon atoms, a triarylsilyl group having 18 to 90 carbon atoms, a mono or diarylboranyl group having 6 to 60 carbon atoms, a mono or dialkylboranyl group having 1 to 120 carbon atoms, is selected from a nitro group and a hydroxy group, provided that X is N(Ar ₃ ), Y is N(Ar ₄ ), Ar ₃ and Ar ₄ are the same, and Z ₁ to Z ₈ are all C(Ar ₅ ), and Ar ₅ included in each of Z ₁ to Z ₈ are the same as each other.

Ar ₃ to Ar ₅ are each independently an alkyl group, a cycloalkyl group, a heterocycloalkyl group, a bicycloalkyl group, an adamantyl group, an alkenyl group, an alkynyl group, an aryl group, an alkoxy group, an aryloxy group, a heteroaryl group, and an aryl group. Ogi, alkylthio group, alkylamino group, arylamino group, trialkylsilyl group, dialkylarylsilyl group, triarylsilyl group, arylboranyl group or alkylboranyl group is an alkyl group having 1 to 60 carbon atoms, a halogen group, a cyano group, a carbon number 3-60 cycloalkyl group, 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, bicycloalkyl group having 7-60 carbon atoms, adamantyl group, 2-60 carbon atoms An alkenyl group, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, P(=O)RaRb [Ra and Rb are independent of each other an alkyl group having 1 to 60 carbon atoms or an aryl group having 6 to 60 carbon atoms], an aryl group having 6 to 60 carbon atoms, a heteroaryl group having 1 to 60 carbon atoms, and an aryl group having 6 to 60 carbon atoms substituted with an aryl group having 1 to 60 carbon atoms. Heteroaryl group, heteroaryl group having 1 to 60 carbon atoms substituted with an alkyl group having 1 to 60 carbon atoms, aralkyl group having 7 to 120 carbon atoms, arylthio group having 6 to 60 carbon atoms, alkylthio group having 1 to 60 carbon atoms, and 1 carbon atom to 30 mono or dialkylamino group, C6 to 60 mono or diarylamino group, C3 to 90 trialkylsilyl group, C7 to 60 dialkyl arylsilyl group, C18 to 90 triarylsilyl group , A mono or diaryl boranyl group having 6 to 60 carbon atoms, a mono or dialkyl boranyl group having 1 to 120 carbon atoms, a nitro group, and a hydroxy group.

The host may include at least one of the compounds represented by compound group 2 below.

[Compound group 2]

The host may contain at least one of the compounds represented by compound group 3 below.

[Compound group 3]

The light emitting layer EML may further include at least one of an arylamine-based compound and a styryl arylamine-based compound.

The arylamine-based compound may include at least one of the compounds represented by compound group 4 below.

[Compound group 4]

The electron transport region ETR is provided on the light emitting layer EML. The electron transport region ETR may include at least one of a hole blocking layer, an electron transport layer ETL, and an electron injection layer EIL, but is not limited thereto.

For example, the electron transport region ETR is composed of an electron transport layer (ETL)/electron injection layer (EIL) or a hole blocking layer/electron transport layer (ETL)/electron injection layer (EIL) sequentially stacked from the light emitting layer (EML). structure, or may have a single-layer structure in which two or more layers are mixed, but is not limited thereto.

The electron transport region (ETR) is formed by various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), inkjet printing, laser printing, and laser induced thermal imaging (LITI). can be formed using

When the electron transport region ETR includes the electron transport layer ETL, the electron transport region ETR includes a compound represented by Chemical Formula 1 below.

[Formula 1]

In Formula 1, X ₁ and X ₂ are each independently CR ₅ or N, and R ₁ to R ₅ are each independently hydrogen, heavy hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, and Heteroaryl group having 1 to 40 carbon atoms, aryloxy group having 6 to 40 carbon atoms, alkyloxy group having 1 to 40 carbon atoms, arylamino group having 6 to 40 carbon atoms, diarylamino group having 12 to 40 carbon atoms, arylalkyl group having 7 to 40 carbon atoms , It is selected from the group consisting of a cycloalkyl group having 3 to 40 carbon atoms and a heterocycloalkyl group having 3 to 40 carbon atoms, or forms a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group A group, a halogen group, or a combination thereof, L is a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted condensed aryl group having 10 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 1 to 30 carbon atoms It is selected from the group consisting of a heteroaryl group containing 30 N, S, and O and a substituted or unsubstituted condensed heteroarylene group containing N, S, and O having 1 to 30 carbon atoms.

L is, for example, an aryl substituted with at least one substituent selected from the substituent group including an alkyl group, a hydroxyl group, a cyano group, an alkoxy group, a halogen group, a carboxy group, an alkoxycarbonyl group, a thionyl group, a thiol group, and a sulfone group. group, a condensed aryl group, a heteroaryl group, or a condensed heteroarylene group.

Het is a substituted or unsubstituted heteroaryl group containing 3 to 20 carbon atoms and N, and A ₁ and A ₂ are each independently hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted It is a heteroaryl group having 1 to 40 carbon atoms.

The electron transport region (ETR) may include at least one of compounds represented by compound group 1 below.

[Compound group 1]

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

When the electron transport region (ETR) includes the electron injection layer (EIL), the electron transport region (ETR) is a lanthanum group metal such as LiF, lithium quinolate (LiQ), Li ₂ O, BaO, NaCl, CsF, Yb, Alternatively, a metal halide such as RbCl or RbI may be used, but is not limited thereto. The electron injection layer (EIL) may also be made of a mixture of an electron transport material and an insulating organometal salt. The organometallic salt may be a material having an energy band gap of about 4 eV or more. Specifically, for example, the organometallic salt may include metal acetate, metal benzoate, metal acetoacetate, metal acetylacetonate or metal stearate. can The thickness of the electron injection layer (EIL) may be about 1 Å to about 100 Å or about 3 Å to about 90 Å. When the thickness of the electron injection layer (EIL) satisfies the aforementioned range, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

As mentioned above, the electron transport region ETR may include a hole blocking layer. The hole blocking layer may include, for example, at least one of BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) and Bphen (4,7-diphenyl-1,10-phenanthroline). However, it is not limited thereto. The hole blocking layer may have a thickness of about 20 Å to about 1000 Å, such as about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the aforementioned range, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The second electrode EL2 is provided on the electron transport region ETR. The second electrode EL2 may be a common electrode or a cathode. The second electrode EL2 may be a transmissive electrode, a transflective electrode, or a reflective electrode.

When the second electrode EL2 is a transmissive electrode, the second electrode EL2 is Li, Ca, LiF/Ca, LiF/Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof (eg , a mixture of Ag and Mg).

The second electrode EL2 may include an auxiliary electrode. The auxiliary electrode is a film formed by depositing the material toward the light emitting layer (EML), and a transparent metal oxide such as indium tin oxide (ITO), indium zinc oxide (IZO), or zinc oxide (ZnO) on the film. , indium tin zinc oxide (ITZO), Mo, Ti, and the like.

When the second electrode EL2 is a transflective electrode or a reflective electrode, the second electrode EL2 is Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF/ Ca, LiF/Al, Mo, Ti, or a compound or mixture thereof (eg, a mixture of Ag and Mg). Alternatively, a plurality of layer structures including a reflective film or semi-transmissive film formed of the above material and a transparent conductive film formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), indium tin zinc oxide (ITZO), or the like. can be

An encapsulation layer SL covering the second electrode EL2 is provided on the second electrode EL2. The encapsulation layer SL may include at least one of an organic layer and an inorganic layer. The encapsulation layer SL protects the organic light emitting element OEL.

A display device according to an embodiment of the present invention includes an electron transport region including the compound represented by Formula 1 above. A display device according to an exemplary embodiment of the present invention includes a light emitting layer including the compound represented by Chemical Formula 2 above. Accordingly, in the organic light emitting device, a band gap between an energy band of the hole transport region and an energy band of the light emitting layer may be reduced, and holes may be easily injected into the light emitting layer. In addition, a band gap between an energy band of the light emitting layer and an energy band of the electron transport region may be reduced, and injection of electrons into the light emitting layer may be facilitated. Accordingly, the organic light emitting device according to an embodiment of the present invention can promote high efficiency and long lifespan.

Hereinafter, the present invention will be described in more detail through specific examples. The following examples are merely examples to aid understanding of the present invention, and the scope of the present invention is not limited thereto.

Example

Example 1

An anode with a thickness of 500 Å was formed of indium tin oxide (ITO) on a glass substrate. As an organic film layer on the anode, 2-TNATA was used as a hole injection layer (600 Å), NPB was used as a hole transport layer (300 Å), and the following compound H-1 was used as a host for a light emitting layer (400 Å), and Ir (ppy) 3 was used as a dopant. , the dopant was vacuum deposited with the host at 4% by weight. Compound 1 was deposited on the electron transport layer (300 Å), and LiF was deposited on the electron injection layer ((10 Å). A cathode having a thickness of 2000 Å was formed with Al.

Examples 2 to 10

It was performed in the same manner as in Example 1, except that the host and electron transport layer were formed with the compounds of Table 1 below.

host electron transport layer Example 1 Compound H-1 compound 1 Example 2 compound H-6 compound 3 Example 3 compound H-2 compound 3 Example 4 Compound H-5 compound 7 Example 5 compound H-3 compound 8 Example 6 compound H-5 compound 10 Example 7 compound H-2 compound 11 Example 8 compound H-4 compound 11 Example 9 compound H-6 compound 11 Example 10 Compound H-7 compound 11

Comparative Example 1

The same procedure as in Example 1 was performed except that Bis(2-methyl-8-quinolinato)(p-phenylphenolato) aluminum(III)(BAlq) was used as the host and Alq3 was deposited as the electron transport layer.

Experiment result

Current efficiency and lifetime of Examples 1 to 10 and Comparative Example were measured. As for the current efficiency, the current efficiency of the organic light emitting device was measured when driven under a current density of 10 mA/cm ² .

Efficiency (cd/A) T90 (hours) Example 1 54 71 Example 2 57 70 Example 3 61 68 Example 4 58 77 Example 5 67 73 Example 6 53 69 Example 7 69 76 Example 8 66 81 Example 9 58 68 Example 10 63 73 Comparative Example 1 42 47

Referring to Table 2, it was confirmed that the organic light emitting devices of Examples 1 to 10 had higher efficiency and longer lifespan than the organic light emitting device of Comparative Example 1.

Although the embodiments of the present invention have been described with reference to the accompanying drawings, those skilled in the art can implement the present invention in other specific forms without changing its technical spirit or essential features. You will understand that there is Therefore, it should be understood that the embodiments described above are illustrative in all respects and not restrictive.

OEL: organic light emitting element EL1: first electrode
HTR: hole transport region EML: light emitting layer
ETR: electron transport region EL2: second electrode
10: display device

Claims (18)

a first electrode;
a hole transport region provided on the first electrode;
a light emitting layer provided on the hole transport region;
an electron transport region provided on the light emitting layer; and
A second electrode provided on the electron transport region; includes,
wherein the electron transport region includes a compound represented by Formula 1 below, and the emission layer includes a compound represented by Formula 2 below:
[Formula 1]

[Formula 2]

In Formula 1,
X ₁ and X ₂ are each independently CH or N;
R ₁ to R ₄ are each independently selected from hydrogen, heavy hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 1 to 40 carbon atoms, an aryloxy group having 6 to 40 carbon atoms, and an aryl group having 1 to 40 carbon atoms. In the group consisting of an alkyloxy group, an arylamino group having 6 to 40 carbon atoms, a diarylamino group having 12 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, and a heterocycloalkyl group having 3 to 40 carbon atoms selected, or a group forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group, a halogen group, or a combination thereof;
L is selected from the group consisting of a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted condensed aryl group having 10 to 30 carbon atoms,
Het is a substituted or unsubstituted heteroaryl group containing N having 3 to 20 carbon atoms,
A ₁ is hydrogen or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms;
A ₂ is hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 40 carbon atoms;
In Formula 2,
AA is a cycloalkyl group having 3 to 60 carbon atoms, a 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, and a carbon number It is selected from an alkenyl group of 2 to 60, an alkynyl group of 2 to 60 carbon atoms, an aryl group of 6 to 60 carbon atoms, or a heteroaryl group of 1 to 60 carbon atoms;
Condensation bonds with a ring containing X and a ring containing Y to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring,
X is selected from N(Ar ₃ ), O and S;
Y is selected from N(Ar ₄ ), O and S, and Ar ₃ and Ar ₄ are each independently selected from an alkyl group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, N, O, S, Si and P A 5- to 6-membered heterocycloalkyl group containing one or more, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an aryl having 6 to 60 carbon atoms group and a heteroaryl group having 1 to 60 carbon atoms;
Z ₁ to Z ₈ are each independently selected from C(Ar ₅ ) and N, Z ₁ to Z ₈ Ar ₅ contained in each may be different from each other, adjacent Ar ₅ may be bonded to each other to form a ring, ,
Ar ₅ contained in each of Z ₁ to Z ₈ is independently selected from hydrogen, an alkyl group having 1 to 60 carbon atoms, a halogen group, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, N, O, S, Si, and P A 5- to 6-membered heterocycloalkyl group including the above, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms , C1-60 alkoxy group, C6-60 aryloxy group, C1-60 heteroaryl group, C6-60 arylthio group, C1-60 alkylthio group, C1-60 Mono or dialkylamino group, C6-30 monoarylamino group, C3-90 trialkylsilyl group, C7-60 dialkylarylsilyl group, C18-90 triarylsilyl group, C6-60 It is selected from a mono or diaryl boranyl group, a mono or dialkyl boranyl group having 1 to 120 carbon atoms, a nitro group and a hydroxy group,
However, X is N (Ar ₃ ), Y is N (Ar ₄ ), Ar ₃ and Ar ₄ are the same, Z ₁ to Z ₈ are all C (Ar ₅ ), Z ₁ to Z ₈ Each The case where Ar ₅ included is the same as each other is excluded. According to claim 1,
The electron transport region is
An organic light emitting device comprising at least one of the compounds represented by the following compound group 1:
[Compound group 1]

delete According to claim 1,
Ar ₃ to Ar ₅ are each independently
Alkyl group, cycloalkyl group, heterocycloalkyl group, bicycloalkyl group, adamantyl group, alkenyl group, alkynyl group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylthio group, alkylthio group, alkylamino group, arylamino group , Trialkylsilyl group, dialkylarylsilyl group, triarylsilyl group, arylboranyl group or alkylboranyl group is an alkyl group having 1 to 60 carbon atoms, a halogen group, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, N, O, A 5- to 6-membered heterocycloalkyl group containing at least one selected from S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, and an alkynyl group having 2 to 60 carbon atoms. , An aryl group having 6 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, P(=O)RaRb [Ra and Rb are independently of each other an alkyl group having 1 to 60 carbon atoms or an alkyl group having 6 to 60 carbon atoms 60 aryl group], a C6-60 aryl group, a C1-60 heteroaryl group, a C6-60 aryl group substituted with a C1-60 heteroaryl group, a C1-60 alkyl group. Substituted heteroaryl group having 1 to 60 carbon atoms, aralkyl group having 7 to 120 carbon atoms, arylthio group having 6 to 60 carbon atoms, alkylthio group having 1 to 60 carbon atoms, mono or dialkylamino group having 1 to 30 carbon atoms, and 6 carbon atoms to 60 mono or diarylamino group, C3 to 90 trialkylsilyl group, C7 to 60 dialkyl arylsilyl group, C18 to 90 triarylsilyl group, C6 to 60 mono or diarylbora An organic light emitting device further substituted with one or more substituents selected from the group consisting of a yl group, a mono or dialkyl boranyl group having 1 to 120 carbon atoms, a nitro group, and a hydroxy group. According to claim 4,
The light emitting layer
An organic light emitting device comprising at least one of the compounds represented by the following compound group 2:
[Compound group 2]

In the compound group 2
X, Y, and Z ₁ to Z ₈ respectively correspond to X, Y, and Z ₁ to Z ₈ in Formula 2 above. According to claim 1,
The light emitting layer
An organic light emitting device comprising at least one of the compounds represented by the following compound group 3:
[Compound group 3]

According to claim 1,
The light emitting layer
An organic light emitting device further comprising an arylamine-based compound. According to claim 7,
The arylamine-based compound is an organic light emitting device comprising at least one of the compounds represented by compound group 4:
[Compound group 4]

According to claim 1,
The light emitting layer
An organic light emitting device that emits green light. Including a plurality of pixels,
At least one of the pixels
a hole transport region provided on the first electrode;
a light emitting layer provided on the hole transport region;
an electron transport region provided on the light emitting layer; and
A second electrode provided on the electron transport region; includes,
The electron transport region includes a compound represented by Formula 1 below,
A display device wherein the light emitting layer includes a compound represented by Formula 2 below:
[Formula 1]

[Formula 2]

In Formula 1,
X ₁ and X ₂ are each independently CH or N;
R ₁ to R ₄ are each independently selected from hydrogen, heavy hydrogen, an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 1 to 40 carbon atoms, an aryloxy group having 6 to 40 carbon atoms, and an aryl group having 1 to 40 carbon atoms. In the group consisting of an alkyloxy group, an arylamino group having 6 to 40 carbon atoms, a diarylamino group having 12 to 40 carbon atoms, an arylalkyl group having 7 to 40 carbon atoms, a cycloalkyl group having 3 to 40 carbon atoms, and a heterocycloalkyl group having 3 to 40 carbon atoms selected, or a group forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group, a halogen group, or a combination thereof;
L is selected from the group consisting of a single bond, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted condensed aryl group having 10 to 30 carbon atoms,
Het is a substituted or unsubstituted heteroaryl group containing N having 3 to 20 carbon atoms,
A ₁ is hydrogen or a substituted or unsubstituted aryl group having 6 to 40 carbon atoms;
A ₂ is hydrogen, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, or a substituted or unsubstituted heteroaryl group having 1 to 40 carbon atoms;
In Formula 2,
AA is a cycloalkyl group having 3 to 60 carbon atoms, a 5-6 membered heterocycloalkyl group containing at least one selected from N, O, S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, and a carbon number It is selected from an alkenyl group of 2 to 60, an alkynyl group of 2 to 60 carbon atoms, an aryl group of 6 to 60 carbon atoms, or a heteroaryl group of 1 to 60 carbon atoms;
Condensation bonds with a ring containing X and a ring containing Y to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring,
X is selected from N(Ar ₃ ), O and S;
Y is selected from N(Ar ₄ ), O and S, and Ar ₃ and Ar ₄ are each independently selected from an alkyl group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, N, O, S, Si and P A 5- to 6-membered heterocycloalkyl group containing one or more, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an aryl having 6 to 60 carbon atoms group and a heteroaryl group having 1 to 60 carbon atoms;
Z ₁ to Z ₈ are each independently selected from C(Ar ₅ ) and N, Z ₁ to Z ₈ Ar ₅ contained in each may be different from each other, adjacent Ar ₅ may be bonded to each other to form a ring, ,
Ar ₅ contained in each of Z ₁ to Z ₈ is independently selected from hydrogen, an alkyl group having 1 to 60 carbon atoms, a halogen group, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, N, O, S, Si, and P A 5- to 6-membered heterocycloalkyl group including the above, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms , C1-60 alkoxy group, C6-60 aryloxy group, C1-60 heteroaryl group, C6-60 arylthio group, C1-60 alkylthio group, C1-60 Mono or dialkylamino group, C6-30 monoarylamino group, C3-90 trialkylsilyl group, C7-60 dialkylarylsilyl group, C18-90 triarylsilyl group, C6-60 It is selected from a mono or diaryl boranyl group, a mono or dialkyl boranyl group having 1 to 120 carbon atoms, a nitro group and a hydroxy group,
Provided, that X is N(Ar ₃ ), Y is N(Ar ₄ ), Ar ₃ and Ar ₄ are the same, Z ₁ to Z ₈ are all C(Ar ₅ ), and Z ₁ to Z ₈ respectively The case where Ar ₅ included is the same as each other is excluded. According to claim 10,
The electron transport region is
A display device comprising at least one of the compounds represented by the following compound group 1:
[Compound group 1]

delete According to claim 10,
Ar ₃ to Ar ₅ are each independently
Alkyl group, cycloalkyl group, heterocycloalkyl group, bicycloalkyl group, adamantyl group, alkenyl group, alkynyl group, aryl group, alkoxy group, aryloxy group, heteroaryl group, arylthio group, alkylthio group, alkylamino group, arylamino group , Trialkylsilyl group, dialkylarylsilyl group, triarylsilyl group, arylboranyl group or alkylboranyl group is an alkyl group having 1 to 60 carbon atoms, a halogen group, a cyano group, a cycloalkyl group having 3 to 60 carbon atoms, N, O, A 5- to 6-membered heterocycloalkyl group containing at least one selected from S, Si and P, a bicycloalkyl group having 7 to 60 carbon atoms, an adamantyl group, an alkenyl group having 2 to 60 carbon atoms, and an alkynyl group having 2 to 60 carbon atoms. , An aryl group having 6 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, an aryloxy group having 6 to 60 carbon atoms, P(=O)RaRb [Ra and Rb are independently of each other an alkyl group having 1 to 60 carbon atoms or an alkyl group having 6 to 60 carbon atoms 60 aryl group], a C6-60 aryl group, a C1-60 heteroaryl group, a C6-60 aryl group substituted with a C1-60 heteroaryl group, a C1-60 alkyl group. Substituted heteroaryl group having 1 to 60 carbon atoms, aralkyl group having 7 to 120 carbon atoms, arylthio group having 6 to 60 carbon atoms, alkylthio group having 1 to 60 carbon atoms, mono or dialkylamino group having 1 to 30 carbon atoms, and 6 carbon atoms to 60 mono or diarylamino group, C3 to 90 trialkylsilyl group, C7 to 60 dialkyl arylsilyl group, C18 to 90 triarylsilyl group, C6 to 60 mono or diarylbora A display device further substituted with one or more substituents selected from the group consisting of a yl group, a mono or dialkyl boranyl group having 1 to 120 carbon atoms, a nitro group, and a hydroxy group. According to claim 10,
The light emitting layer
A display device comprising at least one of the compounds represented by the following compound group 2:
[Compound group 2]

In the compound group 2
X, Y, and Z ₁ to Z ₈ respectively correspond to X, Y, and Z ₁ to Z ₈ in Formula 2 above. According to claim 10,
The light emitting layer
A display device comprising at least one of the compounds represented by the following compound group 3:
[Compound group 3]

According to claim 10,
The light emitting layer
A display device further comprising an arylamine-based compound. According to claim 16,
A display device wherein the arylamine-based compound includes at least one of compounds represented by compound group 4 below:
[Compound group 4]

According to claim 10,
The light emitting layer
A display device that emits green light.

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