KR102595358B1 - Organic light emitting diode - Google Patents

Abstract

An organic light emitting device is provided.

Description

Organic light emitting diode

It relates to organic light emitting devices.

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

A typical organic light-emitting device may have a structure in which an anode is formed on top of a substrate, and a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode are sequentially formed on top of the anode. Here, the hole transport layer, light emitting layer, and electron transport layer are organic thin films made of organic compounds.

The driving principle of the organic light-emitting device having the above-described structure is as follows.

When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light-emitting layer via the hole transport layer, and electrons injected from the cathode move to the light-emitting layer via the electron transport layer. 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.

An organic light emitting device with a novel structure is provided.

According to one aspect,

first electrode;

a second electrode opposite the first electrode;

a light emitting layer interposed between the first electrode and the second electrode and including a host and a dopant;

a first hole transport layer interposed between the first electrode and the light emitting layer; and

a second hole transport layer interposed between the first hole transport layer and the light emitting layer;

Including,

The first hole transport layer includes a first carbazole-based compound and a p-dopant,

The second hole transport layer includes a second carbazole-based compound and does not include the p-dopant,

The host in the light-emitting layer includes a third carbazole-based compound,

The first carbazole-based compound is represented by the following formula (1), the second carbazole-based compound is represented by the following formula (2), and the third carbazole-based compound is represented by the following formula (3),

The first carbazole-based compound, the second carbazole-based compound, and the third carbazole-based compound are all different from each other,

The HOMO energy of the first carbazole-based compound is higher than the HOMO energy of the second carbazole-based compound,

The first hole transport layer and the second hole transport layer are in direct contact, and the second hole transport layer and the light emitting layer are in direct contact,

An organic light emitting device in which the first hole transport layer and the first electrode are in direct contact is provided:

<Formula 1>

<Formula 2>

<Formula 3>

(T ₁ ) _q1 -(Ar ₂₁ ) _p -(T ₂ ) _q2

Of formulas 1 to 3,

X ₁ is selected from N, B and P;

Ar ₁ to Ar ₃ , Ar ₁₁ and Ar ₂₁ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C 2 -C 10 heterocycloalkylene group, or a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group. C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group and substituted or unsubstituted C ₂ -C ₆₀ hetero selected from arylene groups;

a1 to a3 and p are independently integers from 0 to 5;

c1 is an integer from 1 to 5;

*p is an integer from 0 to 5;

R ₁ , R ₂ , R ₄ to R ₈ , R ₁₃ and R ₁₄ are each independently selected from hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, Carboxyl group or its salt, sulfonic acid group or its salt, phosphoric acid or its salt, 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 ₂ -C ₆₀ heteroaryl group, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein Q ₁ to Q ₅ are independently selected from C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, and C ₂ -C ₆₀ heteroaryl group) being selected;

R ₃ , R ₁₁ and R ₁₂ are independently of each other hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof , phosphoric acid or a salt thereof, 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 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, A substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein Q ₃ to Q ₅ are independently of one another, selected from C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group), wherein R ₁₁ and R ₁₂ are substituted or Does not contain an unsubstituted carbazolyl group;

b1, b4, c2 and c3 are independently integers from 1 to 4;

b2 and b3 are independently integers from 1 to 3;

T ₁ is selected from a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, and a substituted or unsubstituted fused carbazolyl group;

T ₂ is an N-containing cyclic group;

q1 and q2 are independently integers from 1 to 5.

The organic light emitting device has improved interfacial stability between organic layers of the organic light emitting device, improved lifespan through control of the light emitting area, and has low driving voltage, high brightness, and high efficiency. By employing the organic light emitting device, a high-quality display device can be implemented.

Figure 1 is a diagram schematically showing the structure of an organic light-emitting device according to an embodiment.
Figure 2 is an energy diagram of a first carbazole-based compound, a second carbazole-based compound, a third carbazole-based compound, and a phosphorescent metal complex.

The organic light-emitting device of FIG. 1 has a structure in which a first electrode, a first hole transport layer, a second hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a second electrode are sequentially stacked.

In Figure 1, the first electrode is an anode that injects holes, and the second electrode is a cathode that injects electrons.

*Although not shown in FIG. 1, an additional substrate may be provided below the first electrode or above the second electrode. When a substrate is provided on the second electrode, the organic light emitting device of FIG. 1 may be an inverted type organic light emitting device.

As the substrate, a substrate used in a typical organic light emitting device can be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofing can be used.

When a substrate is provided below the first electrode, the first electrode may be formed by providing a material for the first electrode on the upper part of the substrate using a deposition method or sputtering method. As the first electrode material, a material with a high work function may be selected to facilitate hole injection.

The first electrode may be a reflective electrode, a transflective electrode, or a transmissive electrode. When a substrate is provided below the first electrode and the first electrode is a reflective electrode, the organic light-emitting device of FIG. 1 may be a top-emission organic light-emitting device, and a substrate is provided below the first electrode. In the case where the first electrode is a transflective electrode or a transmissive electrode, the organic light emitting device of FIG. 1 may be a bottom emitting type or a double side emitting type organic light emitting device.

Materials for the first electrode include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), and zinc oxide (ZnO), which are transparent and have excellent conductivity. Alternatively, as the first electrode material, magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag) ), etc., may be used, but are not limited thereto.

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

Meanwhile, a second electrode is formed opposite the first electrode. As the material for the second electrode, metals, alloys, electrically conductive compounds, and combinations thereof having a low work function can be used. For example, the materials for the second electrode include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), Magnesium-silver (Mg-Ag) may be used, but is not limited thereto. Meanwhile, various modifications are possible, such as forming a transmission-type second electrode by using ITO and IZO to obtain a top-emission organic light-emitting device.

A light-emitting layer is provided between the first electrode and the second electrode, a first hole transport layer is provided between the first electrode and the light-emitting layer, and a second hole transport layer is provided between the first hole transport layer and the light-emitting layer. It is done.

Meanwhile, an electron transport layer and an electron injection layer are provided one after another between the light emitting layer and the second electrode.

In the organic light-emitting device of FIG. 1, holes are injected through the first electrode and move to the light-emitting layer via the first hole transport layer and the second hole transport layer, and electrons are injected through the second electrode to form the electron injection layer and the electron transport layer. It moves to the light-emitting layer. Holes and electrons that reach the light-emitting layer recombine in the light-emitting layer to generate excitons, and as the excitons change from the excited state to the ground state, light is generated.

In the organic light emitting device of FIG. 1, the first hole transport layer and the second hole transport layer are in direct contact, and the second hole transport layer and the light emitting layer are in direct contact.

Although not shown in FIG. 1, a hole injection layer may be additionally provided between the first electrode and the first hole transport layer.

The hole injection layer may be formed on the first electrode using various methods such as vacuum deposition, spin coating, casting, and LB method.

When forming a hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the target hole injection layer, etc., but for example, the deposition temperature is about 100 to 100 degrees Celsius. It may be selected from a range of about 500°C, a vacuum level of about 10 ^-8 to about 10 ^-3 torr, and a deposition rate of about 0.01 to about 100 Å/sec, but is not limited thereto.

When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal characteristics of the desired hole injection layer, but coating at about 2000 rpm to about 5000 rpm Speed and heat treatment temperature for solvent removal after coating may be selected in the temperature range of about 80°C to 200°C, but are not limited thereto.

As the hole injection layer material, for example, N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'- Phthalocyanine compounds such as diamine (N,N′-diphenyl-N,N′-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4′-diamine: DNTPD), copper phthalocyanine, etc. , m-MTDATA [4,4',4''-tris (3-methylphenylphenylamino) triphenylamine], NPB(N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine(N,N '-di(1-naphthyl)-N,N'-diphenylbenzidine)), TDATA, 2-TNATA, 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/camphorsulfonic acid) or PANI/ PSS (Polyaniline)/Poly(4-styrenesulfonate):Polyaniline)/Poly(4-styrenesulfonate)) can be used, but are not limited to these:

The thickness of the hole injection layer may be about 100Å to about 10000Å, for example, about 100Å to about 1000Å. When the thickness of the hole injection layer satisfies the range described above, satisfactory hole injection characteristics can be obtained without a substantial increase in driving voltage.

Next, a first hole transport layer, a second hole transport layer, and a light emitting layer are formed on the top of the first electrode (if forming a hole injection layer, on top of the hole injection layer) using various methods such as vacuum deposition, spin coating, casting, and LB method. are formed respectively in turn. When forming the first hole transport layer, the second hole transport layer, and the light-emitting layer by vacuum deposition and spin coating, the deposition and coating conditions vary depending on the compound used, but are generally approximately the same condition range as the formation of the hole injection layer. can be selected from among.

The first hole transport layer includes a first carbazole-based compound and a p-dopant.

The second hole transport layer includes a second carbazole-based compound, but does not include the p-dopant included in the first hole transport layer.

The light-emitting layer includes a host and a dopant, where the host in the light-emitting layer includes a third carbazole-based compound, and the dopant in the light-emitting layer includes a phosphorescent metal complex.

As used herein, “carbazole-based compound” refers to a compound containing at least one of carbazole and carbazole derivatives as a terminal group and/or linking group. The carbazole derivatives include, for example, carbazole in which at least one of the carbons constituting the ring is substituted with nitrogen (e.g., azacarbazole, etc.) and fused derivatives in which any ring is fused. It may include carbazole (e.g., benzocarbazole, naphthocarbazole, dibenzocarbazole, indolocarbazole, etc.).

The carbazole and carbazole derivatives include substituents as described below (e.g., R ₁ , R ₂ , R ₅ and R ₆ of the formula 1, R ₁₃ and R ₁₄ of the formula 2, and T ₁ of the formula 3) (see) may be optionally replaced.

The first carbazole-based compound included in the first hole transport layer, the second carbazole-based compound included in the second hole transport layer, and the third carbazole-based compound included as a host in the light-emitting layer are all carbazole and Since it contains at least one of the carbazole derivatives, when driving an organic light-emitting device, deterioration at the interface between the first hole transport layer and the second hole transport layer and deterioration at the interface between the second hole transport layer and the light-emitting layer are minimized. You can. Accordingly, the stability and lifespan characteristics of the organic light emitting device can be improved.

The first carbazole-based compound, the second carbazole-based compound, and the third carbazole-based compound all necessarily include at least one of carbazole and carbazole derivatives as described above, but the first carbazole-based compound, the The second carbazole-based compound and the third carbazole-based compound are different from each other.

The weight ratio of the p-dopant and the first carbazole-based compound in the first hole transport layer may be selected in the range of 0.1:99.9 to 20:80, for example, 0.5:99.5 to 15:85. When the weight ratio of the p-dopant and the first carbazole-based compound in the first hole transport layer satisfies the above range, excessive injection of holes from the first electrode into the light-emitting layer can be prevented, thereby improving the lifespan of the organic light-emitting device.

The p-dopant included in the first hole transport layer may be selected from any material that promotes hole transport.

For example, the p-dopant may include at least one material selected from quinone derivatives, metal oxides, and cyano group-containing compounds, but is not limited thereto. Non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4- quinone derivatives such as TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and cyano group-containing compounds such as Compound 200 below, but are not limited thereto.

<Compound 200> <F4-TCNQ>

The second hole transport layer includes the second carbazole-based compound, but does not include the p-dopant included in the first hole transport layer. As a result, hole injection from the first electrode to the second hole transport layer is promoted, but an increase in driving voltage can be prevented.

For example, the second hole transport layer may be made of the second carbazole-based compound.

The hole mobility of the first carbazole-based compound included in the first hole transport layer may be greater than the hole mobility of the second carbazole-based compound included in the second hole transport layer. Here, the hole mobility of the first carbazole-based compound and the hole mobility of the second carbazole-based compound were measured using the same method under the same conditions (for example, the same electric field conditions). As a result, hole injection from the first electrode through the first hole transport layer to the second hole transport layer is promoted, thereby achieving a balance in hole and electron transport between the first and second electrodes of the organic light-emitting device, and achieving a balance in the light-emitting area. It can be effectively fixed within this light-emitting layer. Additionally, excessive holes can be prevented from reaching the light-emitting layer, reaching the interface between the light-emitting layer and the electron transport layer, or being transferred to the electron transport layer. As a result, the light-emitting region can be effectively fixed within the light-emitting layer without forming a separate hole blocking layer between the light-emitting layer and the electron transport layer. Therefore, the light-emitting layer of the organic light-emitting device may directly contact the electron transport layer.

In the organic light emitting device of FIG. 1, the difference between the HOMO level of the first hole transport layer and the HOMO level of the second hole transport layer may be less than 0.3 eV, for example, less than 0.2, specifically less than 0.1. As a result, the movement of holes from the first hole transport layer to the second hole transport layer becomes smooth, so the driving voltage of the organic light emitting device can be reduced.

The dopant in the light-emitting layer includes a phosphorescent metal complex, and the triplet energy of the second carbazole-based compound in the second hole transport layer may be greater than the triplet energy of the phosphorescent metal complex in the light-emitting layer. As a result, triplet excitons of the phosphorescent metal complex included in the light-emitting layer can be efficiently confined within the light-emitting layer, and thus the stability of the organic light-emitting device can be improved.

Figure 2 shows an energy diagram of the first carbazole-based compound, the second carbazole-based compound, the third carbazole-based compound, and the phosphorescent metal complex.

In Figure 2, the difference (D) between the HOMO level of the first carbazole-based compound and the HOMO level of the second carbazole-based compound is less than 0.3 eV.

Meanwhile, in FIG. 2, the triplet energy level of the second carbazole-based compound in the second hole transport layer is greater than the triplet energy level of the phosphorescent metal complex in the light-emitting layer.

If the triplet energy level of the phosphorescent metal complex in the light-emitting layer of FIG. 2 is greater than the triplet energy (A) of the second carbazole-based compound in the second hole transport layer, the triplet energy (B) of the phosphorescent metal complex in the light-emitting layer is greater than the triplet energy (A) of the second carbazole-based compound in the light-emitting layer of FIG. As it transfers to the second hole transport layer, the luminous efficiency of the organic light-emitting device of FIG. 1 may decrease.

However, in the organic light emitting device of FIG. 1, as shown in FIG. 2, the triplet energy level of the second carbazole-based compound in the second hole transport layer is greater than the triplet energy level of the phosphorescent metal complex in the light emitting layer. As designed, the triplet energy level of the phosphorescent metal complex in the light-emitting layer is not transferred to the second hole transport layer and excitons in the light-emitting layer can be effectively generated, thereby maximizing light emission efficiency.

According to one embodiment, in the organic light emitting device of FIG. 1, as shown in FIG. 2, the HOMO energy of the second carbazole-based compound may be higher than the HOMO energy of the third carbazole-based compound.

According to one embodiment, the organic light emitting device of FIG. 1 may satisfy at least one of the following <Condition 1-1> to <Condition 1-3>, as shown in FIG. 2:

<Condition 1-1>

The LUMO energy of the second carbazole-based compound is higher than the LUMO energy of the first carbazole-based compound.

<Condition 1-2>

The LUMO energy of the first carbazole-based compound is higher than the LUMO energy of the third carbazole-based compound

<Condition 1-3>

The LUMO energy of the third carbazole-based compound is higher than the LUMO energy of the phosphorescent metal complex.

According to another embodiment, the organic light emitting device of FIG. 1 may satisfy at least one of the following <Condition 2-1> to <Condition 2-6>, as shown in FIG. 2:

<Condition 2-1>

The triplet energy (T1) of the second carbazole-based compound is higher than the triplet energy (T1) of the first carbazole-based compound.

<Condition 2-2>

The triplet energy (T1) of the second carbazole-based compound is higher than the triplet energy (T1) of the phosphorescent metal complex.

<Condition 2-3>

The triplet energy (T1) of the second carbazole-based compound is higher than the triplet energy (T1) of the third carbazole-based compound.

<Condition 2-4>

The triplet energy (T1) of the first carbazole-based compound is higher than the triplet energy (T1) of the phosphorescent metal complex.

<Condition 2-5>

The triplet energy (T1) of the first carbazole-based compound is higher than the triplet energy (T1) of the third carbazole-based compound.

<Condition 2-6>

The triplet energy (T1) of the third carbazole-based compound is higher than the triplet energy (T1) of the phosphorescent metal complex.

The weight average molecular weight of the third carbazole-based compound in the light-emitting layer may be 400 g/mol or more, for example, in the range of 400 g/mol to 1200 g/mol. When the weight average molecular weight of the third carbazole-based compound in the light-emitting layer satisfies the above range, a stable deposition rate and deposition temperature can be secured when depositing the third carbazole-based compound to form the light-emitting layer.

The phosphorescent metal complex included in the dopant in the light-emitting layer has a maximum phosphorescent emission peak wavelength in the range of 480 nm to 650 nm. Accordingly, the phosphorescent metal complex may emit red light, green light, or blue light.

When the maximum phosphorescent emission peak range of the phosphorescent metal complex satisfies the above range, the triplet energy of the phosphorescent metal complex becomes smaller than the triplet energy of the second hole transport layer, and quenching by the second hole transport layer can be prevented. As such, the luminous efficiency of the organic light emitting device can be improved. In addition, since the maximum phosphorescence emission peak wavelength does not include a longer wavelength range than necessary, a decrease in efficiency and a decrease in lifespan due to emission of unnecessary color light can be prevented. The optimal emission peak wavelength of red light in the currently required color coordinate system is known to be about 620 nm, but is not limited thereto.

The phosphorescent metal complex may be selected from any complex that satisfies the triplet energy level and maximum phosphorescent emission peak wavelength range as described above.

The dopant in the light emitting layer may be a known dopant.

For example, the following compounds can be used as the blue phosphorescent metal complex, but are not limited thereto.

As the red phosphorescent metal complex, the following compounds can be used, but are not limited thereto.

As the green phosphorescent metal complex, the following compounds can be used, but are not limited thereto.

Alternatively, specific examples of the phosphorescent metal complex included in the dopant in the light-emitting layer are as follows, but are not limited thereto:

Alternatively, the phosphorescent metal complex included in the dopant in the light-emitting layer may be an Os-complex as described later, but is not limited thereto:

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

According to one embodiment, the first carbazole-based compound included in the first hole transport layer is represented by the following Chemical Formula 1, and the second carbazole-based compound included in the second hole transport layer is expressed by the following Chemical Formula 2, The third carbazole-based compound included in the host of the light-emitting layer may be represented by the following formula (3):

<Formula 1>

<Formula 2>

<Formula 3>

(T ₁ ) _q1 -(Ar ₂₁ ) _p -(T ₂ ) _q2

In Formula 1, X ₁ is selected from N, B and P. For example, in Formula 1, X ₁ may be N.

In chemistry 1 to 3, Ar ₁ to Ar ₃ , Ar ₁₁ and Ar ₂₁ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, or a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl. lene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group and substituted or unsubstituted It may be selected from C ₂ -C ₆₀ heteroarylene groups.

For example, in Formulas 1 to 3, Ar ₁ to Ar ₃ , Ar ₁₁ and Ar ₂₁ are independently of each other,

Phenylene, pentalenylene, indenylene, naphtylene, azulenylene, heptalenylene, indacenylene, Acenaphtylene group, fluorenylene group, spiro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthrylene group, fluoranthenylene group (fluoranthenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene. picenylene, perylenylene, pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene , pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene ( indazolylene, purinylene, quinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene , quinazolinylene, cinnolinylene, carbazolilene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinyl. phenazinylene, benzoxazolylene, benzoimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene ), thiazolylene, isothiazolylene, benzothiazolylene, isoxazolylene, oxazolylene, triazonylene, tetrazolylene, oxadia oxadiazolylene, triazinylene, benzoxazolylene, dibenzopuranylene, dibenzothiophenylene, and benzocarbazolylene; and

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; C ₁ -C ₂₀ substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof Alkyl group and C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, 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, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, C ₆ -C ₂₀ aryl group and C ₂ -C substituted with at least one of phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, and isoquinolyl group ₂₀ heteroaryl group; -N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (wherein Q ₁₁ to Q ₁₅ are independently of each other, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group, or C ₂ -C ₂₀ heteroaryl group); Substituted with at least one substituent selected from among, phenylene, pentalenylene, indenylene, naphtylene, azulenylene, heptarenylene ( heptalenylene, indacenylene, acenaphtylene, fluorenylene, spiro-fluorenylene, phenalenylene, phenanthrenylene, Anthrylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene. picenylene, perylenylene, pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene , pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene ( indazolylene, purinylene, quinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene , quinazolinylene, cinnolinylene, carbazolilene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinyl. phenazinylene, benzoxazolylene, benzoimidazolylene, furanylene, benzofuranylene, thiophenylene, benzothiophenylene ), thiazolylene, isothiazolylene, benzothiazolylene, isoxazolylene, oxazolylene, triazonylene, tetrazolylene, oxadia oxadiazolylene, triazinylene, benzoxazolylene, dibenzopuranylene, dibenzothiophenylene, and benzocarbazolylene;

can be selected from among.

For example, Ar ₁ to Ar ₃ , Ar ₁₁ and Ar ₂₁ in Formulas 1 to 3 may be independently represented by one of the following Formulas 10-1 to 10-24, but are not limited thereto:

In formulas 10-1 to 10-24,

Y ₁ is O, S, C(R ₂₁ )(R ₂₂ ) or N(R ₂₃ );

Z ₁ , Z ₂ and R ₂₁ to R ₂₃ are independently of each other,

Hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy group;

C ₁ -C substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group;

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, 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, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, C ₆ -C ₂₀ aryl group substituted with at least one of phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, and C ₂ -C ₂₀ heteroaryl group; and

**-N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (wherein Q ₁₁ to Q ₁₅ are each independently selected from C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group or C ₂ -C ₂₀ heteroaryl group); is selected from;

d1 is an integer from 1 to 4;

d2 is an integer from 1 to 3;

d3 is an integer from 1 to 6;

d4 is an integer from 1 to 8;

d5 can be 1 or 2. * and *' are binding sites with neighboring atoms.

For example, Z ₁ , Z ₂ and R ₂₁ to R ₂₃ are independently of each other,

Hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy group;

C ₁ -C ₂₀ substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof Alkyl group and C ₁ -C ₂₀ alkoxy group;

phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, substituted with at least one of phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;

-N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (wherein Q ₁₁ to Q ₁₅ are independently of each other, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridinyl group dazinyl group, triazinyl group, quinolinyl group, or isoquinolinyl group); It may be selected from among, but is not limited to.

In Formulas 10-1 to 19-24, d1 is an integer of 1 to 4; d2 is an integer from 1 to 3; d3 is an integer from 1 to 6; d4 is an integer from 1 to 8; d5 can be 1 or 2.

According to one embodiment, Ar ₁ to Ar ₃ , Ar ₁₁ and Ar ₂₁ in Formulas 1 to 3 may be independently represented by one of the following Formulas 11-1 to 11-11, but are not limited thereto:

In Formula 1, a1 represents the number of Ar ₁ , a2 represents the number of Ar ₂ , and a3 represents the number of Ar ₃ . a1 to a3 may independently be an integer of 0 to 5, for example, an integer of 0 to 3. When a1 and/or a2 are 0, “carbazole” and/or “fluorene” in Formula 1 may be directly connected to “N”. When a1 is 2 or more, two or more Ar _1s may be the same or different from each other. When a2 is 2 or more, 2 or more Ar ₂ may be the same or different from each other. When a3 is 2 or more, two or more Ar ₃ may be the same or different from each other. * and *' are binding sites with neighboring atoms.

According to one embodiment, in Formula 1, i) a1 = 0 & a2 = 0; ii) a1 = 1 & a2 = 0; iii) a1 = 2 & a2 = 0; iv) a1 = 0 & a2 = 1; v) a1 = 0 & a2 = 2; vi) a1 = 1 & a2 = 1.

In Formula 2, c1 represents the number of Ar ₁₁ . c1 is an integer from 1 to 5, for example 1, 2 or 3. When c1 is 2 or more, 2 or more Ar ₁₁ may be the same or different from each other.

In Formula 3, p represents the number of Ar ₂₁ and is selected from an integer of 0 to 5. For example, p can be 0, 1, 2, or 3. When p is 0, T ₁ and T ₂ in Formula 1 are directly bonded. When p is 2 or more, 2 or more Ar ₂₁ may be the same or different from each other.

Of formulas 1 and 2,

R ₁ , R ₂ , R ₄ to R ₈ , R ₁₃ and R ₁₄ are each independently selected from hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, Carboxyl group or its salt, sulfonic acid group or its salt, phosphoric acid or its salt, 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 ₂ -C ₆₀ heteroaryl group, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein Q ₁ to Q ₅ are independently selected from C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, and C ₂ -C ₆₀ heteroaryl group) being selected;

R ₃ , R ₁₁ and R ₁₂ are independently of each other hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof , phosphoric acid or a salt thereof, 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 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, A substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein Q ₁ to Q ₅ are Independently of one another, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group).

In Formulas 1 and 2, R ₁ to R ₈ and R ₁₁ to R ₁₄ are independently of each other,

Phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphthyl ), fluorenyl, spiro-fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl ( triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl , pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, Isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, benzoquinolinyl, phthalazinyl, naphthy naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenan phenanthrolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothio Phenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group , oxadiazolyl, triazinyl, benzooxazolyl, dibenzopuranyl, dibenzothiophenyl, and benzocarbazolyl; and

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; C ₁ -C ₂₀ substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof Alkyl group and C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, 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, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, C ₆ -C ₂₀ aryl group and C ₂ -C substituted with at least one of phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, and isoquinolyl group ₂₀ heteroaryl group; -N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (wherein Q ₁₁ to Q ₁₅ are independently of each other, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group, or C ₂ -C ₂₀ heteroaryl group); Substituted with at least one substituent selected from phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, phenalenyl, phenanthrenyl, anthryl, fluorante Fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl. (pentaphenyl), hexacenyl, pyrrolyl, imidazolyl, pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl ), pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, benzoquinolinyl , phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl ), acridinyl, phenanthrolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl, benzofuranyl ), thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl ( oxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzooxazolyl, dibenzofuranyl, dibenzothiophenyl, and benzocarbazolyl group;

can be selected from among.

For example, in Formulas 1 and 2, R ₃ to R ₈ and R ₁₁ to R ₁₄ may be independently represented by one of the following Formulas 12-1 to 12-22:

In formulas 12-20 to 12-22,

Y ₂ is O, S, C(R ₂₅ )(R ₂₆ ) or N(R ₂₇ );

Z ₁₁ to Z ₁₄ and R ₂₅ to R ₂₇ are independently of each other,

Hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy group;

C ₁ -C substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group;

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, 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, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, C ₆ -C ₂₀ aryl group substituted with at least one of phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, and C ₂ -C ₂₀ heteroaryl group; and

**-N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (wherein Q ₁₁ to Q ₁₅ are independently of each other, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group or C ₂ -C ₂₀ heteroaryl group); is selected from;

e1 is an integer from 1 to 5;

e2 is an integer from 1 to 7;

e3 is an integer from 1 to 3;

e4 is an integer from 1 to 4;

e5 can be 1 or 2. * is a bonding site with a neighboring atom.

According to another embodiment, R ₃ to R ₈ and R ₁₁ to R ₁₄ in Formulas 1 and 2 may be independently represented by one of the following Formulas 13-1 to 13-19, but are not limited thereto:

For descriptions of Z _11a and Z _11c in Formulas 13-1 to 13-19, refer to the description of Z ₁₁ above, respectively. In Formulas 13-1 to 13-19, * is a bonding site with a neighboring atom.

For example, in Formulas 13-1 to 13-19, Z _11a , to Z _11c , R ₂₅ and R ₂₆ are independently of each other,

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

C ₁ -C substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; and

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, substituted with at least one of phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;

can be selected from among.

According to another embodiment, in Formula 1, R ₁ and R ₂ are independently of each other,

C ₁ -C ₂₀ alkyl group;

C ₁ -C substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof ₂₀ alkyl group;

phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; and

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, substituted with at least one of phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;

can be selected from among.

In Formula 1, b1 represents the number of R5, b2 represents the number of R6, b3 represents the number of R7, b4 represents the number of R8, and in Formula 2, c2 represents the number of R13, and c3 represents the number of R14. Indicates the number of . b1, b4, c2, and c3 may independently be integers from 1 to 4, and b2 and b3 may independently be integers from 1 to 3.

The first carbazole-based compound in the first hole transport layer may be represented by the following formula 1A(1) or 1B(1), but is not limited thereto:

<Formula 1A(1)>

<Formula 1B(1)>

The descriptions of R ₁ to R ₄ , Ar ₁ to Ar ₃ , X ₁ , a1, a2 and a3 in Formulas 1A(1) and 1B(1) are the same as described herein.

In Formula 3, T ₁ is selected from a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, and a substituted or unsubstituted condensed carbazolyl group; T ₂ is an N-containing cyclic group; q1 and q2 are independently integers from 1 to 5.

According to one embodiment, T ₁ in Formula 3 is,

Carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; and

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, 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 ₂ -C ₆₀ hetero Aryl group, -N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (where Q ₁₁ to Q ₁₅ are independently of each other, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group) substituted with at least one selected from among) carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazole diary and indolocarbazole diary; is selected from,

In Formula 3, T ₂ is,

Imidazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, oxatriazolyl group, cyatriazolyl group, benzoimidazolyl group, benzotriazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group, Pyrazinyl group, pyridazinyl group, furanyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, imidazopyridinyl group, carbazolyl group , azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; and

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, 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 ₂ -C ₆₀ hetero Aryl group, -N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (where Q ₁₁ to Q ₁₅ are independently of each other, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group) substituted with at least one selected from among) imidazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, oxa Triazolyl group, cyatriazolyl group, benzoimidazolyl group, benzotriazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group, pyrazinyl group, pyridazinyl group, furanyl group, quinolinyl group, isoquinol group Nolinyl group, quinoxalinyl group, quinazolinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, imidazopyridinyl group, carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolinyl group and indole Rocarbazole Diary; can be selected from among.

According to another embodiment, T ₁ in Formula 3 is,

Carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; and

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group substituted with at least one of pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group. ; It may be selected from among, but is not limited to.

According to another embodiment, T ₂ in Formula 3 is,

Imidazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, oxatriazolyl group, cyatriazolyl group, benzoimidazolyl group, benzotriazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group, Pyrazinyl group, pyridazinyl group, furanyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, imidazopyridinyl group, carbazolyl group , azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; and

Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, imidazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, oxatriazolyl group, cyatria. Zolyl group, benzoimidazolyl group, benzotriazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group, pyrazinyl group, pyridazinyl group, furanyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, imidazopyridinyl group, carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; It may be selected from among, but is not limited to.

In Formula 3, q1 represents the number of T ₁ and q2 represents the number of T ₂ . q1 and q2 are independently integers of 1 to 5. For example, q1 and q2 may be independently 1 or 2, but are not limited thereto.

According to one embodiment, the first carbazole-based compound included in the first hole transport layer is N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N-(4- (9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine(N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-N -(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine), N-([1,1'-biphenyl]-4-yl)-9,9 -Diphenyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine(N-([1,1'-biphenyl]-4-yl )-9,9-diphenyl-N-(4-(9-phenyl-9H-carbazol-3-yl)phenyl)-9H-fluoren-2-amine), and N,9,9,-triphenyl-N -(4-9-phenyl-9H-carbazol-3-yl)-9H-fluoren-2-amine(N,9,9-triphenyl-N-(4-(9-phenyl-9H-carbazol-3 -yl)phenyl)-9H-fluoren-2-amine), but is not limited thereto.

According to another embodiment, the second carbazole-based compound included in the second hole transport layer is 4-(9H-carbazol-9-yl)-N,N-diphenylaniline (4-(9H-carbazol-9 -yl)-N,N-diphenylaniline), 3,5-di(9H-carbazol-9-yl)-N,N-diphenylaniline (3,5-di(9H-carbazol-9-yl)- N,N-diphenylaniline), 6-(9H-carbazol-9-yl)-N,N-diphenylnaphthalen-2-amine (6-(9H-carbazol-9-yl)-N,N-diphenylnaphthalen- 2-amine), 4'-(9H-carbazol-9-yl)-N,N-diphenyl-[1,1'-biphenyl]-4-amine (4'-(9H-carbazol-9- yl)-N,N-diphenyl-[1,1'-biphenyl]-4-amine), N-(4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]- 4-yl)-N-phenylnaphthalen-1-amine (N-(4'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1- amine) and N,N-di([1,1'-diphenyl]-4-yl)-7-(9H-carbazol-9-yl)-9,9-dimethyl-9H-fluorene-2- Amine (N,N-di([1,1'-biphenyl]-4-yl)-7-(9H-carbazol-9-yl)-9,9-dimethyl-9H-fluoren-2-amine) It may include at least one compound, but is not limited thereto.

According to another embodiment, the third carbazole-based compound included in the light-emitting layer is 4,4'-N,N'-dicarbazole-biphenyl, N,N'-dicarbazolyl-3,5-benzene, 2,6-bis(3-(9H-carbazolyl-9-yl)phenyl)pyridine (2,6-bis(3-(9H-carbazol-9-yl)phenyl)pyridine), 2,6-bis(3-(9H-carbazol-9-yl)phenyl)pyrazine (2,6-bis (3-(9H-carbazol-9-yl)phenyl)pyrazine), 9-(4,6-diphenylpyrimidin-2-yl)-3,6-diphenyl-9H-carbazole (9-(4 ,6-diphenylpyrimidin-2-yl)-3,6-diphenyl-9H-carbazole), 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole ( 9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9H-carbazole), 9-phenyl-9'-(pyridin-2-yl)-9H,9'H-3, 3'-bicarbazole (9-phenyl-9'-(pyridin-2-yl)-9H,9'H-3,3'-bicarbazole), 9-phenyl-9'-(quinolin-2-yl) -9H,9'H-3,3'-bicarbazole (9-phenyl-9'-(quinolin-2-yl)-9H,9'H-3,3'-bicarbazole), 9-([1 ,1'-biphenyl]-3-yl)-9'-(pyridin-2-yl)-9H,9'H-3,3'-bicapazole (9-([1,1'-biphenyl] -3-yl)-9'-(pyridin-2-yl)-9H,9'H-3,3'-bicarbazole), 9-(4,6-diphenyl-1,3,5-triazine- 2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole (9-(4,6-diphenyl-1,3,5-triazin-2-yl)-9'- phenyl-9H,9'H-3,3'-bicarbazole), 9-(4,6-diphenylpyrimidin-2-yl)-9'-phenyl-9H,9'H-3,3'-bi Carbazole (9-(4,6-diphenylpyrimidin-2-yl)-9'-phenyl-9H,9'H-3,3'-bicarbazole), and 5-phenyl-11-(pyridin-2-yl) -5,11-dihydroindolo[3,2-b]carbazole (5-phenyl-11-(pyridin-2-yl)-5,11-dihydroindolo[3,2-b]carbazole) It includes, but is not limited to, one compound.

The substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₂ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₂ -C ₁₀ heterocycloalkenyl lene group, the substituted C ₆ -C ₆₀ arylene group, the substituted C ₂ -C ₆₀ heteroarylene group, the substituted C ₃ -C ₁₀ cycloalkyl group, the substituted C ₂ -C ₁₀ heterocycloalkyl group, the substitution C ₃ -C ₁₀ cycloalkenyl group, the substituted C ₂ -C ₁₀ heterocycloalkenyl group, the substituted C ₆ -C ₆₀ aryl group, the substituted C ₂ -C ₆₀ heteroaryl group, the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₂ -C ₆₀ alkynyl group, the substituted C ₁ -C ₆₀ alkoxy group, the substituted C ₆ -C ₆₀ aryloxy group And at least one substituent of the substituted C ₆ -C ₆₀ arylthio group is deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or a salt thereof, Sulfonic acid group 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 and C ₁ -C ₆₀ alkoxy group; C ₁ -C ₆₀ substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof 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 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 aryl Oxy group, C ₆ -C ₆₀ arylthio group and C ₂ -C ₆₀ heteroaryl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, 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, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, C ₃ -C ₁₀ cycloalkyl group substituted with at least one of phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl 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 aryl cy radical and C ₂ -C ₆₀ heteroaryl group; and -N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (where Q ₁₁ to Q ₁₅ are independently of each other, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, and C ₂ -C ₆₀ heteroaryl group); It may be selected from among, but is not limited to.

In the present specification, specific examples of unsubstituted C ₁ -C ₆₀ alkyl groups (or C ₁ -C ₆₀ alkyl groups) include those having 1 carbon atom such as methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc. to 60 linear or branched alkyl groups, and at least one substituent of the substituted C ₁ -C ₆₀ alkyl group is deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine. , hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, 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; C ₁ -C ₆₀ substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof 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 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 aryl Oxy group, C ₆ -C ₆₀ arylthio group and C ₂ -C ₆₀ heteroaryl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, 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, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, C ₃ -C ₁₀ cycloalkyl group substituted with at least one of phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl 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 aryl cy radical and C ₂ -C ₆₀ heteroaryl group; and -N(Q ₁₁ )(Q ₁₂ ); and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) (wherein Q ₁₁ and Q ₁₂ are each independently a C ₆ -C ₆₀ aryl group, or a C ₂ -C ₆₀ heteroaryl group, and Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ aryl group, or a C ₂ -C ₆₀ heteroaryl group); It may be selected from among, but is not limited to.

In the present specification, the unsubstituted C ₁ -C ₆₀ alkoxy group (or C ₁ -C ₆₀ alkoxy group) has the chemical formula -OA (where A is an unsubstituted C ₁ -C ₆₀ alkyl group as described above). , Specific examples thereof include methoxy, ethoxy, isopropyloxy, etc., and at least one hydrogen atom of these alkoxy groups can be substituted with the same substituent as in the case of the substituted C ₁ -C ₆₀ alkyl group described above. .

As used herein, an unsubstituted C ₂ -C ₆₀ alkenyl group (or C ₂ -C ₆₀ alkenyl group) refers to one that contains one or more carbon double bonds in the middle or end of the unsubstituted C ₂ -C ₆₀ alkyl group. it means. Examples include ethenyl, propenyl, butenyl, etc. At least one hydrogen atom of these unsubstituted C ₂ -C ₆₀ alkenyl groups can be substituted with the same substituent as in the case of the substituted C ₁ -C ₆₀ alkyl group described above.

As used herein, an unsubstituted C ₂ -C ₆₀ alkynyl group (or C ₂ -C ₆₀ alkynyl group) contains one or more carbon triple bonds in the middle or end of the C ₂ -C ₆₀ alkyl group as defined above. means that Examples include ethynyl, propynyl, etc. At least one hydrogen atom of these alkynyl groups can be substituted with the same substituent as in the case of the substituted C ₁ -C ₆₀ alkyl group described above.

As used herein, an unsubstituted C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms containing at least one aromatic ring, and an unsubstituted C ₆ - The C ₆₀ arylene group refers to a divalent group having a carbocyclic aromatic system with 6 to 60 carbon atoms including one or more aromatic rings. When the aryl group and the arylene group include two or more rings, the two or more rings may be fused to each other. One or more hydrogen atoms of the aryl group and the arylene group may be substituted with the same substituent as in the case of the substituted C ₁ -C ₆₀ alkyl group described above.

Examples of the substituted or unsubstituted C ₆ -C ₆₀ aryl group include phenyl group, C ₁ -C ₁₀ alkylphenyl group (for example, ethylphenyl group), C ₁ -C ₁₀ alkylbiphenyl group (for example, ethylbiphenyl group) ), halopenyl groups (e.g., o-, m-, and p-fluorophenyl groups, dichlorophenyl groups), dicyanophenyl groups, trifluoromethoxyphenyl groups, o-, m-, and p-toryl groups, o-, m- and p-cumenyl group, mesityl group, phenoxyphenyl group, (α,α-dimethylbenzene)phenyl group, (N,N'-dimethyl)aminophenyl group, (N,N'-diphenyl)aminophenyl group, pentare Nyl group, indenyl group, naphthyl group, halonaphthyl group (for example, fluoronaphthyl group), C ₁ -C ₁₀ alkylnaphthyl group (for example, methylnaphthyl group), C ₁ -C ₁₀ alkoxynaphthyl group (for example, For example, methoxynaphthyl group), anthracenyl group, azurenyl group, heptharenyl group, acenaphthylenyl group, phenarenyl group, fluorenyl group, anthraquinolinyl group, methylanthryl group, phenanthryl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, ethyl-chrysenyl group, picenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexacenyl group, rubisenyl group group, coroneryl group, trinaphthylenyl group, heptaphenyl group, heptasenyl group, pyranthrenyl group, obarenyl group, etc. Examples of substituted C ₆ -C ₆₀ aryl groups include unsubstituted groups as described above. It can be easily recognized by referring to examples of C ₆ -C ₆₀ aryl groups and substituents of the substituted C ₁ -C ₆₀ alkyl groups. Examples of the substituted or unsubstituted C ₆ -C ₆₀ arylene group can be easily recognized by referring to the examples of the substituted or unsubstituted C ₆ -C ₆₀ aryl group.

As used herein, an unsubstituted C ₂ -C ₆₀ heteroaryl group refers to a monovalent group having a system consisting of one or more aromatic rings containing one or more heteroatoms selected from N, O, P, or S and the remaining ring atoms being C. And the unsubstituted C ₂ -C ₆₀ heteroarylene group refers to a divalent group having a system consisting of one or more aromatic rings containing one or more heteroatoms selected from N, O, P or S and the remaining ring atom being C. do. Here, when the heteroaryl group and the heteroarylene group include two or more rings, the two or more rings may be fused to each other. One or more hydrogen atoms of the heteroaryl group and the heteroarylene group may be substituted with the same substituent as in the case of the C ₁ -C ₆₀ alkyl group described above.

Examples of the unsubstituted C ₂ -C ₆₀ heteroaryl group include pyrazolyl group, imidazolyl group, oxazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyridinyl group, pyridinyl group. Daazinyl group, pyrimidinyl group, triazinyl group, carbazolyl group, indolyl group, quinolinyl group, isoquinolinyl group, benzoimidazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, etc. Examples of the unsubstituted C ₂ -C ₆₀ heteroarylene group can be easily recognized by referring to the examples of the substituted or unsubstituted C ₂ -C ₆₀ arylene group.

The substituted or unsubstituted C ₆ -C ₆₀ aryloxy group refers to -OA ₂ (where A ₂ is the substituted or unsubstituted C ₆ -C 60 aryl group), and the substituted or unsubstituted C 6 -C ₆₀ aryloxy group refers to -OA 2 (where A 2 is the substituted or unsubstituted C 6 -C ₆₀ aryl group). ₆₀ Arylthio group refers to -SA ₃ (where A ₃ is the substituted or unsubstituted C ₆ -C ₆₀ aryl group).

The total thickness of the first hole transport layer and the second hole transport layer may be about 50Å to about 2500Å, for example, about 100Å to about 2000Å. The thickness ratio of the first hole transport layer and the second hole transport layer may be 1:9 to 9:1, for example, 3:7 to 7:3, but is not limited thereto. The thickness of the second hole transport layer may be 5 nm to 300 nm. When the total thickness of the first hole transport layer and the second hole transport layer and the ratio between the first hole transport layer and the second hole transport layer satisfy the above-mentioned range, a satisfactory level of hole transport characteristics can be obtained without a substantial increase in driving voltage. You can.

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.

Each of the first hole transport layer, the second hole transport layer, and the light emitting layer is formed using various methods such as vacuum deposition, spin coating, or casting. When forming the first hole transport layer, the second hole transport layer, and the light emitting layer by vacuum deposition and spin coating, the conditions vary depending on the compound used, but can generally be selected from the range of conditions that are almost the same as those for forming the hole injection layer. there is.

Next, an electron transport layer is formed on top of the light emitting layer using various methods such as vacuum deposition, spin coating, or casting. When forming an electron transport layer by vacuum deposition or spin coating, the conditions vary depending on the compound used, but can generally be selected from a range of conditions that are almost the same as those for forming the hole injection layer.

As the material for the electron transport layer, a known electron transport material that functions to stably transport electrons injected from the second electrode can be used. Examples of known electron transport substances include quinoline derivatives, especially tris(8-quinolinolate)aluminum(Alq ₃ ), TAZ, Balq, beryllium bis(benzoquinolin-10) -olate: Bebq ₂ ), Compound 201, Compound 202, PBD (2-(4-biphenyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole) spiro-PBD(spiro-2-biphenyl Materials such as -4-yl-5-(4-t-butylphenyl)-1,3,4-oxadiazole), SAlq, etc. may be used, but are not limited thereto.

<Compound 201> <Compound 202>

BCP

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 electron transport organic material described above.

The metal-containing material may include a Li complex. Non-limiting examples of the Li complex include lithium quinolate (LiQ) or the following compound 203:

<Compound 203>

Additionally, an electron injection layer, which is a material that has the function of facilitating injection of electrons from the second electrode, may be laminated on the electron transport layer.

As the electron injection layer forming material, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li ₂ O, BaO, etc. can be used. The deposition conditions for the electron injection layer vary depending on the compound used, but can generally be selected from a range of conditions that are substantially the same as those for forming the hole injection layer.

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.

OLEDs 1 to 6 were manufactured to evaluate the efficiency, driving voltage, and lifespan characteristics of the organic light emitting device. OLED 6 was manufactured according to the following method:

The ITO glass substrate was cut into 50mm ITO electrode HT1 and 2wt% F4-TCNQ were vacuum deposited to form a first hole transport layer with a thickness of 600Å, and HT2 was vacuum deposited on the first hole transport layer at a deposition rate of 1Å/sec to form a second hole transport layer with a thickness of 600Å. formed. Subsequently, PH1 (host) and PRD1 (dopant) were co-deposited on the second hole transport layer at a deposition rate of 1 Å/sec and 0.1 Å/sec, respectively, to form a light emitting layer with a thickness of 400 Å. Alq ₃ was vacuum deposited to a thickness of 300Å on the light emitting layer to form an electron transport layer, and LiF 10Å (electron injection layer) and Al 2000Å (second electrode) were sequentially vacuum deposited on the electron transport layer to produce OLED 6. did.

OLEDs 1 to 5 were manufactured using the same method as the manufacturing method of OLED 6, except that the materials and thicknesses of the first hole transport layer, second hole transport layer, and light emitting layer were changed as shown in Table 1 below. In the case of OLED 1, a light emitting layer was formed directly on the first hole transport layer without forming a second hole transport layer.

First hole transport layer Second hole transport layer luminescent layer OLED 1 HT1:F4-TCNQ (2wt%)
(600Å) - PH1:PRD1 (5wt%)
(400Å) OLED 2 HT1:F4-TCNQ (2wt%)
(600Å) α-NPB
(600Å) PH1:PRD1 (5wt%)
(400Å) OLED 3 HT1:F4-TCNQ (2wt%)
(600Å) HT2
(600Å) PH2:PRD1 (5wt%)
(400Å) OLED 4 α-NPB:F4-TCNQ (2wt%)
(600Å) HT2
(600Å) PH1:PRD1 (5wt%)
(400Å) OLED 5 α-NPB:F4-TCNQ (2wt%)
(600Å) HT2'
(600Å) PH2:PRD1 (5wt%)
(400Å) OLED 6 HT1:F4-TCNQ (2wt%)
(600Å) HT2
(600Å) PH1:PRD1 (5wt%)
(400Å)

α-NPB

Table 2 below shows the efficiency, driving voltage, and T ₈₀ lifespan data of OLEDs 1 to 6. Efficiency, driving voltage, and half lifespan are expressed as relative values compared to the efficiency, driving voltage, and lifespan of OLED 1 (100%). T ₈₀ lifespan is a measurement of the time (hr) it takes for the luminance to reach 80% of the initial luminance under 150 nit conditions. Efficiency, driving voltage, and luminance were measured using a luminance meter PR650 with power supplied from a current-voltage meter (Kethley SMU 236).

efficiency
(cd/A) driving voltage
(V) T ₈₀ life
(hr) OLED 1 100% 100% 100% OLED 2 105% 97% 91% OLED 3 115% 93% 111% OLED 4 121% 85% 145% OLED 5 107% 105% 70% OLED 6 148% 81% 192%

According to Table 2, it can be confirmed that OLED 6 has the highest efficiency and lifespan, and the lowest driving voltage. Although the organic light-emitting device has been described above based on FIGS. 1 and 2, the organic light-emitting device It is not limited to this, and of course various modifications are possible.

Claims (18)

first electrode;
a second electrode opposite the first electrode;
a light emitting layer interposed between the first electrode and the second electrode and including a host and a dopant;
a first hole transport layer interposed between the first electrode and the light emitting layer; and
a second hole transport layer interposed between the first hole transport layer and the light emitting layer;
Including,
The first hole transport layer includes a first carbazole-based compound and a p-dopant,
The second hole transport layer includes a second carbazole-based compound and does not include the p-dopant,
The host in the light-emitting layer includes a third carbazole-based compound,
The first carbazole-based compound is represented by the following formula (1), the second carbazole-based compound is represented by the following formula (2), and the third carbazole-based compound is represented by the following formula (3),
The first carbazole-based compound, the second carbazole-based compound, and the third carbazole-based compound are all different from each other,
The HOMO energy of the first carbazole-based compound is higher than the HOMO energy of the second carbazole-based compound,
The first hole transport layer and the second hole transport layer are in direct contact, and the second hole transport layer and the light emitting layer are in direct contact,
An organic light-emitting device in which the first hole transport layer and the first electrode are in direct contact:
<Formula 1>

<Formula 2>

<Formula 3>
(T ₁ ) _q1 -(Ar ₂₁ ) _p -(T ₂ ) _q2
In formulas 1 to 3,
X ₁ is selected from N, B and P;
Ar ₁ to Ar ₃ , Ar ₁₁ and Ar ₂₁ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C _{2 -C 10 heterocycloalkylene group, or a substituted or unsubstituted C 2} -C ₁₀ heterocycloalkylene group. C ₃ -C ₁₀ cycloalkenylene group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group and substituted or unsubstituted C ₂ -C ₆₀ hetero selected from arylene groups;
The C ₂ -C ₁₀ heterocycloalkylene group, C ₂ -C ₁₀ heterocycloalkenylene group and C ₂ -C ₆₀ heteroarylene group each independently contain one or more heteroatoms selected from N, O, P or S. Contains;
a1 to a3 are independently integers from 0 to 5;
c1 is an integer from 1 to 5;
p is an integer from 0 to 5;
R ₁ , R ₂ , R ₄ to R ₈ , R ₁₃ and R ₁₄ are each independently selected from hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, Carboxyl group or its salt, sulfonic acid group or its salt, phosphoric acid or its salt, 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 ₂ -C ₆₀ heteroaryl group, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein Q ₁ to Q ₅ are independently selected from C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, and C ₂ -C ₆₀ heteroaryl group) being selected;
R ₃ , R ₁₁ and R ₁₂ are independently of each other hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof , phosphoric acid or a salt thereof, 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 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, A substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein Q ₃ to Q ₅ are independently of one another, selected from C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group), wherein R ₁₁ and R ₁₂ are substituted or Does not contain an unsubstituted carbazolyl group;
The C ₂ -C ₁₀ heterocycloalkyl group, C ₂ -C ₁₀ heterocycloalkenyl group, and C ₂ -C ₆₀ heteroaryl group independently contain one or more heteroatoms selected from N, O, P, or S;
b1, b4, c2 and c3 are independently integers from 1 to 4;
b2 and b3 are independently integers from 1 to 3;
T ₁ is selected from a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted azacarbazolyl group, and a substituted or unsubstituted fused carbazolyl group;
T ₂ is an N-containing cyclic group;
q1 and q2 are independently integers from 1 to 5. According to paragraph 1,
An organic light-emitting device wherein the HOMO energy of the second carbazole-based compound is higher than the HOMO energy of the third carbazole-based compound. According to paragraph 1,
The dopant in the light-emitting layer includes a phosphorescent metal complex,
The organic light emitting device satisfies at least one of the following <Condition 1-1> to <Condition 1-3>:
<Condition 1-1>
The LUMO energy of the second carbazole-based compound is higher than the LUMO energy of the first carbazole-based compound.
<Condition 1-2>
The LUMO energy of the first carbazole-based compound is higher than the LUMO energy of the third carbazole-based compound
<Condition 1-3>
The LUMO energy of the third carbazole-based compound is higher than the LUMO energy of the phosphorescent metal complex. According to paragraph 1,
The dopant in the light-emitting layer includes a phosphorescent metal complex,
The organic light emitting device satisfies at least one of the following <Condition 2-1> to <Condition 2-6>:
<Condition 2-1>
The triplet energy (T1) of the second carbazole-based compound is higher than the triplet energy (T1) of the first carbazole-based compound.
<Condition 2-2>
The triplet energy (T1) of the second carbazole-based compound is higher than the triplet energy (T1) of the phosphorescent metal complex.
<Condition 2-3>
The triplet energy (T1) of the second carbazole-based compound is higher than the triplet energy (T1) of the third carbazole-based compound.
<Condition 2-4>
The triplet energy (T1) of the first carbazole-based compound is higher than the triplet energy (T1) of the phosphorescent metal complex.
<Condition 2-5>
The triplet energy (T1) of the first carbazole-based compound is higher than the triplet energy (T1) of the third carbazole-based compound.
<Condition 2-6>
The triplet energy (T1) of the third carbazole-based compound is higher than the triplet energy (T1) of the phosphorescent metal complex. According to any one of claims 2 to 4,
The weight ratio of the p-dopant and the first carbazole-based compound is selected from the range of 0.1:99.9 to 20:80. According to any one of claims 2 to 4,
An organic light emitting device wherein the hole mobility of the first carbazole-based compound is greater than the hole mobility of the second carbazole-based compound. According to any one of claims 2 to 4,
An organic light emitting device wherein the difference between the HOMO level of the first hole transport layer and the HOMO level of the second hole transport layer is less than 0.3 eV. According to any one of claims 2 to 4,
An organic light-emitting device wherein the weight average molecular weight of the third carbazole-based compound in the light-emitting layer is 400 g/mol or more. According to any one of claims 2 to 4,
In Formulas 1 to 3, Ar ₁ to Ar ₃ , Ar ₁₁ and Ar ₂₁ are each independently represented by one of the following Formulas 10-1 to 10-24:



In formulas 10-1 to 10-24,
Y ₁ is O, S, C(R ₂₁ )(R ₂₂ ) or N(R ₂₃ );
Z ₁ , Z ₂ and R ₂₁ to R ₂₃ are independently of each other,
Hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, and C ₁ -C ₂₀ alkoxy group;
C ₁ -C substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group;
Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, 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, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, C ₆ -C ₂₀ aryl group substituted with at least one of phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, and C ₂ -C ₂₀ heteroaryl group; and
-N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (wherein Q ₁₁ to Q ₁₅ are independently of each other, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₂₀ aryl group, or C ₂ -C ₂₀ heteroaryl group); is selected from;
The C ₂ -C ₂₀ heteroaryl group contains one or more heteroatoms selected from N, O, P or S;
d1 is an integer from 1 to 4;
d2 is an integer from 1 to 3;
d3 is an integer from 1 to 6;
d4 is an integer from 1 to 8;
d5 is 1 or 2,
* and *' are binding sites with neighboring atoms. According to any one of claims 2 to 4,
In Formulas 1 to 3, Ar ₁ to Ar ₃ , Ar ₁₁ and Ar ₂₁ are each independently represented by one of the following Formulas 11-1 to 11-11:

In formulas 11-1 to 11-11,
* and *' are binding sites with neighboring atoms. According to any one of claims 2 to 4,
In Formula 1, i) a1 = 0 & a2 = 0; ii) a1 = 1 & a2 = 0; iii) a1 = 2 & a2 = 0; iv) a1 = 0 & a2 = 1; v) a1 = 0 & a2 = 2; vi) a1 = 1 & a2 = 1;
In Formula 2, c1 is 1, 2, or 3;
In Formula 3, p is 0, 1, 2 or 3, an organic light emitting device. According to any one of claims 2 to 4,
In Formulas 1 and 2, R ₃ to R ₈ and R ₁₁ to R ₁₄ are each independently represented by one of the following Formulas 12-1 to 12-22:



In formulas 12-1 to 12-22,
In R ₃ to R ₈ , R ₁₃ and R ₁₄ Y ₂ is O, S, C(R ₂₅ )(R ₂₆ ) or N(R ₂₇ ), and in R ₁₁ and R ₁₂ Y ₂ is O, S or C (R ₂₅ )(R ₂₆ );
Z ₁₁ to Z ₁₄ and R ₂₅ to R ₂₇ are each independently selected from hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid. group or its salt, phosphoric acid or its salt, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group; C ₁ -C ₂₀ substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof Alkyl group and C ₁ -C ₂₀ alkoxy group; C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group; Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, 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, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, A C ₆ -C ₂₀ aryl group substituted with at least one of phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, and C ₂ -C ₂₀ heteroaryl group; -N(Q ₁₁ )(Q ₁₂ ); and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (wherein Q ₁₁ to Q ₁₅ are each independently selected from a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, and a C ₆ -C ₂₀ aryl group. group or C ₂ -C ₂₀ heteroaryl group); is selected from;
The C ₂ -C ₂₀ heteroaryl group contains one or more heteroatoms selected from N, O, P or S;
e1 is an integer from 1 to 5;
e2 is an integer from 1 to 7;
e3 is an integer from 1 to 3;
e4 is an integer from 1 to 4;
e5 is 1 or 2,
* is a bonding site with a neighboring atom. According to any one of claims 2 to 4,
In Formulas 1 and 2, R ₃ to R ₈ , R ₁₃ and R ₁₄ are independently represented by one of Formulas 13-1 to 13-19 below, and R ₁₁ and R ₁₂ are independently represented by Formulas 13-1 to 13-19 below. Organic light-emitting device represented by one of 13-9 and 13-11 to 13-19:


In Formulas 13-1 to 13-19, Z _11a to Z _11d , R ₂₅ and R ₂₆ are independently of each other,
Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
C ₁ -C substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;
phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; and
Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, substituted with at least one of phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;
is selected from,
* is a bonding site with a neighboring atom. According to any one of claims 2 to 4,
In Formula 1, R ₁ and R ₂ are independently of each other,
C ₁ -C ₂₀ alkyl group;
C ₁ -C substituted with at least one of deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, and phosphoric acid or salts thereof ₂₀ alkyl group;
phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; and
Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, substituted with at least one of phenyl group, naphthyl group, anthryl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;
An organic light emitting device selected from among. According to any one of claims 2 to 4,
An organic light-emitting device in which the first carbazole-based compound is represented by the following formula 1A(1) or 1B(1):
<Formula 1A(1)>

<Formula 1B(1)>

The descriptions of R ₁ to R ₄ , Ar ₁ to Ar _{3 ,} According to any one of claims 2 to 4,
In Formula 3, T ₁ is,
Carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; and
Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, 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 ₂ -C ₆₀ hetero Aryl group, -N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ) (where Q ₁₁ to Q ₁₅ are independently of each other, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group) substituted with at least one selected from among) carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazole diary and indolocarbazole diary; is selected from,
The C ₂ -C ₁₀ heterocycloalkyl group, C ₂ -C ₁₀ heterocycloalkenyl group and C ₂ -C ₆₀ heteroaryl group each independently contain one or more heteroatoms selected from N, O, P or S,
In Formula 3, T ₂ is,
Imidazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, oxatriazolyl group, cyatriazolyl group, benzoimidazolyl group, benzotriazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group, Pyrazinyl group, pyridazinyl group, furanyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, imidazopyridinyl group, carbazolyl group , azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; and
Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, 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 ₂ -C ₆₀ hetero Aryl group, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein Q ₁ to Q ₅ are independently of each other, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group) substituted with at least one selected from among) imidazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, oxa Triazolyl group, cyatriazolyl group, benzoimidazolyl group, benzotriazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group, pyrazinyl group, pyridazinyl group, furanyl group, quinolinyl group, isoquinol group Nolinyl group, quinoxalinyl group, quinazolinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, imidazopyridinyl group, carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolinyl group and indole Rocarbazole diary; is selected from,
The C ₂ -C ₁₀ heterocycloalkyl group, C ₂ -C ₁₀ heterocycloalkenyl group and C ₂ -C ₆₀ heteroaryl group are each independently an organic group containing at least one heteroatom selected from N, O, P or S. Light-emitting device. According to any one of claims 2 to 4,
In Formula 3, T ₁ is,
Carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; and
Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ Alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group substituted with at least one of pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group. ; An organic light emitting device selected from among. According to any one of claims 2 to 4,
In Formula 3, T ₂ is,
Imidazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, oxatriazolyl group, cyatriazolyl group, benzoimidazolyl group, benzotriazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group, Pyrazinyl group, pyridazinyl group, furanyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, imidazopyridinyl group, carbazolyl group , azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; and
Deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof, sulfonic acid group or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthryl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group , pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group, imidazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, oxatriazolyl group, cyatria. Zolyl group, benzoimidazolyl group, benzotriazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group, pyrazinyl group, pyridazinyl group, furanyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, imidazopyridinyl group, carbazolyl group, azacarbazolyl group, benzocarbazolyl group, naphthocarbazolyl group and indolocarbazolyl group; An organic light emitting device selected from among.