KR20190137735A - Organic light-emitting diode - Google Patents

Abstract

Disclosed is an organic light emitting element. In the organic light emitting element, a light emitting layer comprises one or more selected among light emitting materials represented by either chemical formula 1 or chemical formula 2, and a hole transfer layer comprises one or more selected among hole transfer materials represented by chemical formula 2(2). The light emitting element may have a low driving voltage, high efficiency and high color purity.

Description

Organic light-emitting diode

It relates to an organic light emitting device.

Organic light-emitting diodes are self-luminous devices that have a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed, and multi-coloring. .

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

The driving principle of the organic light emitting device having the structure as described above 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 emission layer to generate excitons. The excitons change from excited state to ground state and light is generated.

It is to provide an organic light emitting device having high efficiency and long life.

According to one aspect, the first electrode; A second electrode opposed to the first electrode; And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer; The light emitting layer includes at least one selected from light emitting materials represented by one of Chemical Formulas 1 and 2; There is provided an organic light emitting device in which the organic layer interposed between the first electrode and the light emitting layer comprises at least one selected from a hole transport material represented by one of Formulas 2 (1) and 2 (2):

<Formula 1>

<Formula 2>

In Formulas 1 and 2,

A ₁ is CR ₁ or N; A ₂ is CR ₂ or N; A ₃ is CR ₃ or N; A ₄ is CR ₄ or N; A ₅ is CR ₅ or N; A ₆ is CR ₆ or N; A ₇ is CR ₇ or N; A ₈ is CR ₈ or N; A ₉ is CR ₉ or N; A ₁₀ is CR ₁₀ or N; A ₁₁ is CR ₁₁ or N; A ₁₂ is CR ₁₂ or N; A ₁₃ is CR ₁₃ or N; A ₁₄ is CR ₁₄ or N; A ₁₅ is CR ₁₅ or N; A ₁₆ is CR ₁₆ or N;

R ₁ to R ₁₆ are each independently hydrogen, deuterium, a halogen atom, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, and —Si (Q ₁ ) (Q ₂ ) (Q ₃ ), wherein Q ₁ to Q ₃ are independently of each other a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or a C ₂ -C ₆₀ heteroaryl group; And two or more of R ₁ to R ₁₆ may be linked to each other to selectively form a C ₆ -C ₂₀ saturated ring or a C ₆ -C ₂₀ unsaturated ring;

Y is O, S or C (R ₃₁ ) (R ₃₂ );

L ₁ to L ₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ aryl A ylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, and a substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group; Is selected from;

n1 to n3 are each independently an integer of 0 to 3;

Ar ₁ to Ar ₃ are independently of each other, i) a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ —C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, and —Si (Q ₁ ) (Q ₂ ) (Q ₃ ), wherein Q ₁ to Q ₃ are independently of each other a substituted or unsubstituted C _1- A C ₁₀ alkyl group or a substituted or unsubstituted C ₆ -C ₃₀ aryl group; And

ii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come Im, C ₂ -C ₆₀ hetero aryl group and the -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), wherein Q ₁ to Q ₃ are each independently a substituted or unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₆ -C ₃₀ aryl 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 substituted with at least one selected from among C ₂ -C ₆₀ heteroaryl group; Is selected from;

Z ₁ to Z ₄ , R ₃₁ and R ₃₂ are independently of each other, i) hydrogen, deuterium, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ An alkoxy group;

ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;

iii) 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 and C ₂ -C ₆₀ heteroaryl group; And

iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from;

o1 to o4 are each independently an integer of 0 to 3;

<Formula 2 (1)>

<Formula 2 (2)>

In Formulas 2 (1) and 2 (2),

X ₁₁ is CR ₁₁ or N; X ₁₂ is CR ₁₂ or N; X ₁₃ is CR ₁₃ or N; X ₁₄ is CR ₁₄ or N; X ₁₅ is CR ₁₅ or N; X ₁₆ is CR ₁₆ or N; X ₁₇ is CR ₁₇ or N; X ₁₈ is CR ₁₈ or N; X ₁₉ is CR ₁₉ or N; X ₂₀ is CR ₂₀ or N; X ₂₁ is CR ₂₁ or N; X ₂₂ is CR ₂₂ or N; X ₂₃ is CR ₂₃ or N; X ₂₄ is CR ₂₄ or N;

Z ₅ , Z ₆ and R ₁₁ to R ₂₄ independently of one another, i) hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof , Sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl groups, C ₂ -C ₆₀ alkenyl groups, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy groups;

ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;

iii) 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 and C ₂ -C ₆₀ heteroaryl group;

iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; And

v) -N (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) and -B (Q ₁₆ ) (Q ₁₇ ) (where Q ₁₁ and Q ₁₇ are independently of one another) , 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; Is selected from;

Ar ₁₃ and Ar ₁₄ independently of one another, i) 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 and C ₂ -C ₆₀ heteroaryl group; And

ii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from;

Z ₁₁ and Z ₁₂ independently of one another, i) a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;

iii) 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 and C ₂ -C ₆₀ heteroaryl group; And

iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from;

p and q are each independently an integer from 1 to 4.

The organic light emitting diode may have a low driving voltage, high efficiency, and high color purity.

1 is a view schematically showing the structure of an organic light emitting device according to an embodiment of the present invention.
2 and 3 are luminance vs. It is a figure which shows an efficiency graph.

1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The organic light emitting diode 10 includes a substrate 11, a first electrode 13, an organic layer 15, and a second electrode 17. Hereinafter, a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG. 1.

As the substrate 11, a substrate used in a conventional organic light emitting device may be used, but a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance may be used.

The first electrode 13 may be formed by using a deposition method, a sputtering method, or the like for the first electrode material on the substrate. When the first electrode 13 is an anode, the material for the first electrode may be selected from materials having a high work function to facilitate hole injection. The first electrode 13 may be a reflective electrode or a transmissive electrode. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used as the material for the first electrode. Alternatively, when magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. are used, One electrode 13 may be formed as a reflective electrode.

The first electrode 13 may have a single layer or a multilayer structure of two or more. For example, the first electrode 13 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

The organic layer 15 is provided on the first electrode 13.

The organic layer 15 refers to a plurality of layers interposed between the first electrode 13 and the second electrode 17 of the organic light emitting element 10, and the organic layer 15 includes a light emitting layer, and hole injection At least one of a layer, a hole transporting layer, a functional layer having a hole injection function and a hole transporting function, a buffer layer, an electron blocking layer, a hole blocking layer, an electron transporting layer, an electron injection layer and a functional layer having an electron injection and electron transporting function at the same time It may further include.

According to an embodiment, the organic layer 15 may sequentially include a hole injection layer, a hole transport layer, a buffer layer, a light emitting layer, an electron transport layer, and an electron injection layer.

The hole injection layer HIL may be formed on the first electrode 13 by using various methods such as vacuum deposition, spin coating, casting, and LB.

In the case of forming the 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 properties of the hole injection layer, and the like. It may be selected from a range of about 500 ° C., a vacuum degree of about 10 ⁻⁸ to about 10 ⁻³ torr, and a deposition rate of about 0.01 to about 100 μs / sec, but is not limited thereto.

In the case of forming the 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 properties of the desired hole injection layer, but the coating is about 2000 rpm to about 5000 rpm. Rate, heat treatment temperature for solvent removal after coating may be selected from a temperature range of about 80 ℃ to 200 ℃, but is not limited thereto.

A well-known hole injecting material can be used as the hole injecting material, for example, N, N'-diphenyl-N, N'-bis- [4- (phenyl-m- Tolyl-amino) -phenyl] -biphenyl-4,4′-diamine (N, N′-diphenyl-N, N′-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl- 4,4′-diamine: Phthalocyanine compounds such as DNTPD), copper phthalocyanine, 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 / Dodecylbenzenesulfonicacid: polyaniline / dodecyl benzenesulfonic acid), PEDOT / PSS (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrene sulfonate): 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)) may be used, but is not limited thereto.

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

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as vacuum deposition, spin coating, casting, and LB. In the case of forming the hole transport layer by vacuum deposition and spinning, the deposition conditions and coating conditions vary depending on the compound used, and in general, the hole transport layer may be selected from almost the same range of conditions as the formation of the hole injection layer.

The hole transport layer includes at least one selected from a hole transport material represented by any one of the following Chemical Formula 2 (1) or 2 (2).

<Formula 2 (1)>

<Formula 2 (2)>

In Formulas 2 (1) and 2 (2), X ₁₁ is CR ₁₁ or N; X ₁₂ is CR ₁₂ or N; X ₁₃ is CR ₁₃ or N; X ₁₄ is CR ₁₄ or N; X ₁₅ is CR ₁₅ or N; X ₁₆ is CR ₁₆ or N; X ₁₇ is CR ₁₇ or N; X ₁₈ is CR ₁₈ or N; X ₁₉ is CR ₁₉ or N; X ₂₀ is CR ₂₀ or N; X ₂₁ is CR ₂₁ or N; X ₂₂ is CR ₂₂ or N; X ₂₃ is CR ₂₃ or N; X ₂₄ is CR ₂₄ or N.

For example, in Formulas 2 (1) and 2 (2), X ₁₁ is C (R ₁₁ ), X ₁₂ is C (R ₁₂ ), X ₁₃ is C (R ₁₃ ), and X ₁₄ is C (R ₁₄ ), X ₁₅ is C (R ₁₅ ), X ₁₆ is C (R ₁₆ ), X ₁₇ is C (R ₁₇ ), X ₁₈ is C (R ₁₈ ), and X ₁₉ is C (R ₁₉ ), X ₂₀ is C (R ₂₀ ), X ₂₁ is C (R ₂₁ ), X ₂₂ is C (R ₂₂ ), X ₂₃ is C (R ₂₃ ), X ₂₄ is C (R ₂₄ ), but is not limited thereto.

For example, in Formulas 2 (1) and 2 (2), Ar ₁₃ and Ar ₁₄ independently of each other, i) a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group; And

ii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from.

For example, in Formulas 2 (1) and 2 (2), Ar ₁₃ and Ar ₁₄ independently of each other, i) a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group ( naphtyl, azulenyl, azulenyl, heptarenyl, heptanenyl, indasenyl, innacenyl, acenaphtyl, fluorenyl, spiro-fluorenyl, phenalenyl ), Phenanthrenyl group (phenanthrenyl), anthryl group (anthryl), fluoranthenyl group, triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group, naphthacenyl group ( naphthacenyl, picenyl, perenlenyl, perylenyl, pentaphenyl, hexacenyl, hexacenyl, pyrrolyl, imidazolyl, pyrazolyl, Pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, phosphorus Indazolyl, purinyl, quinolinyl, quinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinoxalinyl Quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, phenazinyl, Benzooxazolyl, Benzoimidazolyl, Furanyl, Furanyl, Benzofuranyl, Thiophenyl, Benzothiophenyl, Thiazolylene, Thiazolyl Thiazolyl group (isothiazolyl), benzothiazolyl group, isoxazolyl group (isoxazolyl), oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group ( triazinyl), benzooxazolyl group, dibenzofuranyl group (dibenzofuranyl), dibenzothiophenyl group, and benzocarbazolyl group; And

ii) 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 salt thereof, C ₁ -C ₂₀ alkyl group, A phenyl group, pentarenyl group, indenyl group, naphthyl group, azulenyl group, heptarenyl group, substituted with at least one selected from a C ₁ -C ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heteroaryl group, Indasenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, penalenyl, phenanthrenyl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphtha Senyl group, pisenyl group, peryleneyl group, pentaphenyl group, hexasenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, Indolyl group, indazolyl group, furinyl group, quinolinyl group, benzoquinolinyl group, Thalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolininylene group, carbazolyl group, phenantridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoxazolyl group, benzoimidazole Diary, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolylene group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazole Diary, triazinyl group, benzoxazolyl group, dibenzofuranyl group, dibenzothiophenyl group, and benzocarbazolyl group; It may be selected from, but is not limited thereto.

As another example, in Formulas 2 (1) and 2 (2), Ar ₁₃ and Ar ₁₄ may be each independently i) a phenyl group, a naphtyl group, a fluorenyl group, a spiro- Fluorenyl group, phenanthrenyl group (phenanthrenyl), anthryl group (anthryl), fluoranthenyl group, triphenylenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, chrysenyl group, pyridi Pyridinyl, pyrazinyl, pyrimidinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, quinolinyl, benzoquinolin Benzoquinolinyl, quinoxalinyl, quinazolinyl, quinnolinyl, carnozolyl, carbazolyl, and triazinyl; And

ii) 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 salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, quinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cynolinylene, carbazolyl and Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group substituted with at least one selected from triazinyl group , Pyridinyl, pyrazinyl, pyrimidy Group, a pyridazinyl group, iso-indole group, indole group, a quinolinyl group, a benzo quinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbonyl group when fun, carbazole group and a triazole group possess; It may be selected from, but is not limited thereto.

As another example, Ar ₁₃ and Ar ₁₄ of Formulas 2 (1) and 2 (2) may be independently of each other, and may be represented by any one of Formulas 3-1 to 3-20, but are not limited thereto. :

* In Formulas 3-1 to 3-20 represents a binding site with N in Formulas 2 (1) to 2 (2).

In Formulas 2 (1) and 2 (2), Z ₁₁ and Z ₁₂ are each independently i) a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and C ₁ -C ₆₀ alkoxy group;

ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;

iii) 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 and C ₂ -C ₆₀ heteroaryl group; And

iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from.

For example, in Formulas 2 (1) and 2 (2), Z ₁₁ and Z ₁₂ are independently of each other,

i) a C ₁ -C ₂₀ alkyl group;

ii) Deuterium, halogen atoms, hydroxyl groups, cyano groups, nitro groups, amino groups, amidino groups, hydrazines, hydrazones, carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, phenyl groups, naphthyl groups, fluores Nyl group, spiro-fluorenyl group, phenanthrenyl group, anthryl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl A C ₁ -C ₂₀ alkyl group substituted with at least one selected from a group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cynolinylene group, a carbazolyl group, and a triazinyl group ;

iii) phenyl, naphtyl, fluorenyl, spiro-fluorenyl, phenanthrenyl, phenanthrenyl, anthryl, fluoranthenyl, Triphenylenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridazinyl , Isoindolyl group, indolyl group, indolyl group, quinolinyl group, benzoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, quinazolinyl group, cinnolinyl group Carbazolyl and triazinyl groups; And

iv) 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 salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, quinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cynolinylene, carbazolyl and Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group substituted with at least one selected from triazinyl group , Pyridinyl, pyrazinyl, pyrimidy Group, a pyridazinyl group, iso-indole group, indole group, a quinolinyl group, a benzo quinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbonyl group when fun, carbazole group and a triazole group possess; It may be selected from, but is not limited thereto.

As another example, in Formulas 2 (1) and 2 (2), Z ₁₁ and Z ₁₂ may be each independently selected from a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and the following Formula 3- It may be selected from groups represented by 1 to 3-20, but is not limited thereto:

* In Formulas 3-1 to 3-20 represents carbon of the fluorene ring in Formulas 2 (1) to 2 (2).

In Formulas 2 (1) and 2 (2), Z ₅ , Z _6, and R ₁₁ to R ₂₄ are each independently i) hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, Amidino groups, hydrazines, hydrazones, carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl groups, C ₂ -C ₆₀ alkenyl groups, C ₂ -C ₆₀ alkynyl groups and C _1- C ₆₀ alkoxy group;

ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;

iii) 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 and C ₂ -C ₆₀ heteroaryl group;

iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; And

v) -N (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) and -B (Q ₁₆ ) (Q ₁₇ ) (where Q ₁₁ and Q ₁₇ are independently of one another) , 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; Is selected from.

For example, in Formulas 2 (1) and 2 (2), Z ₅ , Z _6, and R ₁₁ to R ₂₄ may be each independently,

i) hydrogen, deuterium, halogen atoms, hydroxyl groups, cyano groups, nitro groups, amino groups, amidino groups, hydrazines, hydrazones, carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof and C ₁ -C ₂₀ An alkyl group;

ii) Deuterium, halogen atoms, hydroxyl groups, cyano groups, nitro groups, amino groups, amidino groups, hydrazines, hydrazones, carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, phenyl groups, naphthyl groups, fluores Nyl group, spiro-fluorenyl group, phenanthrenyl group, anthryl group, fluoranthhenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl A C ₁ -C ₂₀ alkyl group substituted with at least one selected from a group, an isoindolyl group, an indolyl group, a quinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cynolinylene group, a carbazolyl group, and a triazinyl group ;

iii) phenyl, naphtyl, fluorenyl, spiro-fluorenyl, phenanthrenyl, phenanthrenyl, anthryl, fluoranthenyl, Triphenylenyl, pyrenyl, chrysenyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyridazinyl , Isoindolyl group, indolyl group, indolyl group, quinolinyl group, benzoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, quinazolinyl group, cinnolinyl group Carbazolyl and triazinyl groups; And

iv) 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 salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, Pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, quinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cynolinylene, carbazolyl and Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group substituted with at least one selected from triazinyl group , Pyridinyl, pyrazinyl, pyrimidy Group, a pyridazinyl group, iso-indole group, indole group, a quinolinyl group, a benzo quinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbonyl group when fun, carbazole group and a triazole group possess; It may be selected from, but is not limited thereto.

As another example, in Formulas 2 (1) and 2 (2), Z ₅ , Z ₆ and R ₁₁ to R ₂₄ may be each independently of each other, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, It may be selected from amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof and C ₁ -C ₂₀ alkyl group, but is not limited thereto.

As another example, in Formulas 2 (1) and 2 (2), Z ₅ , Z _6, and R ₁₁ to R ₂₄ may be each independently hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, or a nitro group. , Amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group and the following formula 3- It may be selected from groups represented by any one of 1 to 3-20, but is not limited thereto:

In said Formula (2) and (2), p represents the number of Z <_5> , p is an integer of 1-4. When p is 2 or more, p Z ₅ may be the same or different from each other. q represents the number of Z ₆ and is an integer from 1 to 4. When q is 2 or more, q Z ₆ may be the same or different from each other.

According to one embodiment, the hole transport material may be represented by any one of Formulas 2a to 2b, but is not limited thereto.

<Formula 2a>

<Formula 2b>

In Formula 2a or 2b,

Ar ₁₃ and Ar ₁₄ are each independently represented by one of the following Chemical Formulas 3-1 to 3-20;

Z ₁₁ and Z ₁₂ are each independently represented by a C ₁ -C ₂₀ alkyl group and any one of Formulas 3-1 to 3-20;

Z ₅ , Z ₆ and R ₁₁ to R ₂₄ 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 A group or a salt thereof, phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a group represented by any one of the following Formulas 3-1 to 3-20;

p and q are each independently an integer from 1 to 4.

In another embodiment, the hole transport material may be selected from any one of the following Compounds 6-1 to 6-144, but is not limited thereto:

The hole transport layer may further comprise a known hole transport material. As a known hole transport material, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1 , 1-biphenyl] -4,4'-diamine (TPD), TCTA (4,4 ', 4 "-tris (N-carbazolyl) triphenylamine (4,4', 4" -tris (N- carbazolyl) triphenylamine)), NPB (N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine (N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine)) And the like, but is not limited thereto.

The hole transport layer may have a thickness of about 50 kPa to about 2000 kPa, for example, about 100 kPa to about 1500 kPa. When the thickness of the hole transport layer satisfies the above range, a satisfactory hole transport characteristic may be obtained without a substantial increase in driving voltage.

The H-functionality (functional layer having a hole transporting function at the same time) may include at least one of the hole injection layer material and the hole transporting material as described above, the thickness of the H-functional layer is about 100Å to about 10000Å, For example, about 100 kPa to about 1000 kPa. When the thickness of the H-functional layer satisfies the above-described range, satisfactory hole injection and aqueous characteristics can be obtained without a substantial increase in driving voltage.

Meanwhile, at least one of the hole injection layer, the hole transport layer, and the H-functional layer may include one or more of a compound represented by the following Formula 300 and a compound represented by the following Formula 301:

<Formula 300>

<Formula 301>

In Formula 300, Ar ₁₀₁ and Ar ₁₀₂ may be each independently a substituted or unsubstituted C ₆ -C ₆₀ arylene group. For example, Ar ₁₀₁ and Ar ₁₀₂ are each independently a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalylene group, a substituted or unsubstituted acenaphthylene group, fluore Nylene group, phenenylene group, phenanthrenylene group, anthylene group, fluoranthhenylene group, triphenylenylene group, pyrenylene group, chrysenenylene group, naphthacenylene group, pisenylene group, perenylene group and pentanyl group Ren group; And 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl group, at least one of the substituted phenyl group , Pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptalylene group, substituted or unsubstituted acenaphthylene group, fluorenylene group, phenenalenylene group, phenanthrenylene group, anthylene group, Fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenenylene group, naphthacenylene group, pisenylene group, peryleneylene And penta-hexenyl group; It may be one of the.

In Formula 300, xa and xb may be each independently an integer of 0 to 5, or 0, 1 or 2. For example, xa may be 1 and xb may be 0, but is not limited thereto.

In Formulas 300 and 301, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R _119, and R ₁₂₁ to R ₁₂₄ are each independently of each other hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amino group, and an amidino Group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted A substituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₆₀ aryl group, substituted Or an unsubstituted C ₅ -C ₆₀ aryloxy group, or a substituted or unsubstituted C ₅ -C ₆₀ arylthio group. For example, R ₅₁ to R ₅₈ , R ₆₁ to R ₆₉ and R ₇₁ and R ₇₂ are each independently hydrogen; heavy hydrogen; Halogen atom; Hydroxyl group; Cyano group; Nitro group; Amino group; Amidino groups; Hydrazine; Hydrazone; Carboxyl groups or salts thereof; Sulfonic acid groups or salts thereof; Phosphoric acid or salts thereof; C ₁ -C ₁₀ alkyl groups (eg, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.); C ₁ -C ₁₀ alkoxy groups (for example, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, etc.); C ₁ -C substituted with one or more of deuterium, halogen atoms, hydroxyl groups, cyano groups, nitro groups, amino groups, amidino groups, hydrazines, hydrazones, carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, and phosphoric acid or salts thereof _{A 10} alkyl group and a C ₁ -C ₁₀ alkoxy group; Phenyl group; Naphthyl group; Anthryl group; Fluorenyl group; Pyrenyl group; 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 salt thereof, C ₁ -C ₁₀ alkyl group and C ₁ Phenyl, naphthyl, anthryl, fluorenyl and pyrenyl groups substituted with one or more of —C ₁₀ alkoxy groups; It may be one of, but is not limited thereto.

In Formula 300, R ₁₀₉ is a phenyl group; Naphthyl group; Anthryl group; Biphenyl group; Pyridyl groups; And 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 salt thereof, substituted or unsubstituted C _1- Phenyl group, naphthyl group, anthryl group, biphenyl group and pyridyl group substituted with at least one of C ₂₀ alkyl group and substituted or unsubstituted C ₁ -C ₂₀ alkoxy group; It may be one of the.

According to one embodiment, the compound represented by Formula 300 may be represented by the following Formula 300A, but is not limited thereto.

<Formula 300A>

In Formula 300A, a detailed description of R ₁₀₁ , R ₁₁₁ , R _112, and R ₁₀₉ may be referred to above.

For example, at least one of the hole injection layer, the hole transport layer, and the H-functional layer may include one or more of the following compounds 301 to 320, but is not limited thereto:

At least one of the hole injection layer, the hole transport layer, and the H-functional layer may have a conductivity of the film, in addition to a known hole injection material, a known hole transport material, and / or a material having a hole injection function and a hole transport function at the same time. It may further include a charge-generating material to improve the back and the like.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethe. Quinone derivatives such as phosphorus (F4-TCNQ) and the like; Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as Compound 200, and the like, but are not limited thereto.

<Compound 200> <F4-TCNQ>

When the hole injection layer, the hole transport layer or the H-functional layer further includes the charge-generating material, the charge-generating material is homogeneous in the hole injection layer, the hole transport layer or the H-functional layer. A variety of modifications are possible, such as dispersed or evenly distributed.

A buffer layer may be interposed between at least one of the hole injection layer, the hole transport layer, and the H-functional layer and the light emitting layer. The buffer layer may serve to increase efficiency by compensating an optical resonance distance according to a wavelength of light emitted from the emission layer. The buffer layer may comprise a known hole injection material, a hole transport material. Alternatively, the buffer layer may include the same material as one of the materials included in the hole injection layer, the hole transport layer, and the H-functional layer formed under the buffer layer.

Subsequently, the emission layer EML may be formed on the hole transport layer, the H-functional layer, or the buffer layer by using a method such as vacuum deposition, spin coating, cast, LB, or the like. When the light emitting layer is formed by a vacuum deposition method or a spin coating method, the deposition conditions vary depending on the compound used, and in general, may be selected from a range of conditions substantially the same as that of forming the hole injection layer.

The light emitting layer includes at least one selected from light emitting materials represented by one of Formulas 1 and 2:

<Formula 1>

<Formula 2>

In Formulas 1 and 2, A ₁ is CR ₁ or N; A ₂ is CR ₂ or N; A ₃ is CR ₃ or N; A ₄ is CR ₄ or N; A ₅ is CR ₅ or N; A ₆ is CR ₆ or N; A ₇ is CR ₇ or N; A ₈ is CR ₈ or N; A ₉ is CR ₉ or N; A ₁₀ is CR ₁₀ or N; A ₁₁ is CR ₁₁ or N; A ₁₂ is CR ₁₂ or N; A ₁₃ is CR ₁₃ or N; A ₁₄ is CR ₁₄ or N; A ₁₅ is CR ₁₅ or N; A ₁₆ is CR ₁₆ or N.

In Formulas 1 and 2, Y is O, S or C (R ₃₁ ) (R ₃₂ ).

In Formulas 1 and 2, L ₁ to L ₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted group. C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, and a substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group; Is selected from.

For example, in Formulas 1 and 2, L ₁ to L ₃ may be each independently i) a C ₃ -C ₁₀ cycloalkylene group, a C ₃ -C ₁₀ cycloalkenylene group, a C ₆ -C ₆₀ arylene group, C ₂ -C ₁₀ heterocycloalkylene group, C ₂ -C ₁₀ heterocycloalkenylene group and C ₂ -C ₆₀ heteroarylene group;

ii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of , C ₃ -C ₁₀ cycloalkylene group, C ₃ -C ₁₀ cycloalkenylene group, C ₆ -C ₆₀ arylene group, C ₂ -C ₁₀ heterocycloalkylene group, C ₂ -C ₁₀ heterocycloalkenylene group and C ₂ -C ₆₀ heteroarylene group; And

iii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of A C ₃ -C ₁₀ cycloalkylene group, a C ₃ -C ₁₀ cycloalkenylene group, a C ₆ -C ₆₀ arylene group, substituted with at least one selected from a C ₆ -C ₆₀ aryl group and a C ₂ -C ₆₀ heteroaryl group , A C ₂ -C ₁₀ heterocycloalkylene group, a C ₂ -C ₁₀ heterocycloalkenylene group, and a C ₂ -C ₆₀ heteroarylene group; It may be selected from, but is not limited thereto.

As another example, in Formulas 1 and 2, L ₁ to L ₃ may be each independently i) a C ₆ -C ₆₀ arylene group and a C ₂ -C ₆₀ heteroarylene group;

ii) a C ₆ -C ₆₀ arylene group and a C ₂ -C ₆₀ heteroarylene group substituted with at least one selected from a C ₆ -C ₆₀ aryl group and a C ₂ -C ₆₀ heteroaryl group; And

iii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl groups substituted with at least one, selected from C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group selected from the group consisting of at least C ₆ -C ₆₀ arylene group and C ₂ -C ₆₀ heteroarylene group substituted with one; It may be selected from, but is not limited thereto.

As another example, in Formulas 1 and 2, L ₁ to L ₃ may be each independently i) a phenylene group, a fluorenylene group, a pyridylene group, a pyrimidylene group, a triazinylene group, and a quinazolinylene group;

ii) a phenylene group, a fluorenylene group, a pyridylene group, a pyrimidylene group, a triazinylene group and a quinazolinylene group substituted with at least one selected from a phenyl group, a naphthyl group and a pyridyl group;

iii) phenylene group, fluorenylene group, pyridylene group, pyrimidyl substituted with at least one selected from deuterium, methyl group, ethyl group, n-octyl group, methoxy group, ethoxy group, phenyl group, naphthyl group, pyridyl group and carbazole group A ethylene group, a triazinylene group and a quinazolinylene group; It may be selected from, but is not limited thereto.

In Formulas 1 and 2, n1 represents the number of L ₁ , and n1 is an integer of 0 to 3. When n1 is 2 or more, n1 L ₁ may be the same as or different from each other. n2 represents the number of L _2, n2 is an integer from 0 to 3. When n2 is 2 or more, n2 L ₂ may be the same or different from each other. n3 represents the number of L _3, n3 is an integer from 0 to 3. When n3 is 2 or more, n3 L ₃ may be the same or different from each other.

In Formulas 1 and 2, Ar ₁ to Ar ₃ are each independently i) a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ Heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), wherein Q ₁ to Q ₃ are independently of each other substituted Or an unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₆ -C ₃₀ aryl group; And

ii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come Im, C ₂ -C ₆₀ hetero aryl group and the -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), wherein Q ₁ to Q ₃ are each independently a substituted or unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₆ -C ₃₀ aryl 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 substituted with at least one selected from among C ₂ -C ₆₀ heteroaryl group; Is selected from.

For example, in Formulas 1 and 2, Ar ₁ to Ar ₃ may be each independently i) a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, and —Si (Q ₁ ) (Q ₂ ) (Q ₃ ), wherein Q ₁ to Q ₃ are, independently from each other, a C ₁ -C ₁₀ alkyl group or a C ₆ -C ₃₀ aryl group; And

ii) deuterium, a halogen atom, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), where Q ₁ To Q ₃ are each independently a C ₆ -C ₆₀ aryl group and a C ₂ -C ₆₀ heteroaryl group substituted with at least one selected from C ₁ -C ₁₀ alkyl group or C ₆ -C ₃₀ aryl group; It may be selected from, but is not limited thereto.

As another example, in Formulas 1 and 2, Ar ₁ to Ar ₃ may be each independently i) a phenyl group, a pyridyl group, a pyrimidyl group, a triazinyl group, and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ) Wherein Q ₁ to Q ₃ are each independently a methyl group, an ethyl group, an n-propyl group, an i-propyl group or a phenyl group; And

ii) deuterium, a halogen atom, a phenyl group, a pyridyl group and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ) wherein Q ₁ to Q ₃ are independently of each other methyl, ethyl, n-propyl, i- Propyl group or phenyl group; A phenyl group, a pyridyl group, a pyrimidyl group and a triazinyl group substituted with at least one selected from among; It may be selected from, but is not limited thereto.

As another example, Ar ₁ to Ar ₃ of Formulas 1 and 2 may be each independently represented by one selected from Formulas H1 to H5, but are not limited thereto.

In Formulas H1 to H5, * is any one of L ₁ to L ₃ in Formulas 1 and 2; Or a binding site with N.

In Chemical Formulas 1 and 2, Z ₁ , Z ₂ , R _31, and R ₃₂ may be each independently i) hydrogen, deuterium, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkoxy A silyl group and a C ₁ -C ₆₀ alkoxy group;

ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;

iii) 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 and C ₂ -C ₆₀ heteroaryl group; And

iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from.

For example, in Formulas 1 and 2, Z ₁ , Z ₂ , R _31, and R ₃₂ may be each independently i) a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group;

ii) a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group substituted with at least one of deuterium, a halogen atom, a C ₆ -C ₆₀ aryl group and a C ₂ -C ₆₀ heteroaryl group;

iii) a C ₆ -C ₆₀ aryl group and a C ₂ -C ₆₀ heteroaryl group; And

iv) heavy hydrogen, halogen atoms, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ substituted with at least one selected from a heteroaryl group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ Heteroaryl group; It may be selected from, but is not limited thereto.

As another example, in Formulas 1 to 3, Z ₁ , Z ₂ , R _31, and R ₃₂ may be each independently i) a methyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso- Butyl group, sec-butyl group and tert-butyl group;

ii) phenyl group, naphthyl group and pyridyl group;

iv) phenyl, naphthyl and pyridyl groups substituted with at least one selected from methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl and tert-butyl groups; It may be selected from, but is not limited thereto.

In Formulas 1 to 3, R ₁ to R ₁₆ are each independently hydrogen, deuterium, a halogen atom, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ) wherein Q ₁ to Q ₃ are independently of each other a C ₁ -C ₆₀ alkyl group, C ₆ -C ₆₀ aryl group, or C ₂ -C ₆₀ heteroaryl group; And two or more of R ₁ to R ₁₆ may be linked to each other to selectively form a C ₆ -C ₂₀ saturated ring or a C ₆ -C ₂₀ unsaturated ring.

For example, in Formulas 1 and 2, R ₁ to R ₁₆ may be hydrogen, or two or more of R ₁ to R ₁₆ may be linked to each other to selectively form a C ₆ -C ₂₀ saturated ring or a C ₆ -C ₂₀ unsaturated ring It may be formed, but is not limited thereto.

In Formulas 1 and 2, o1 represents the number of Z ₁ , and o1 is an integer of 0 to 3. When o1 is 2 or more, o1 Z ₁ may be the same as or different from each other.

In Formulas 1 and 2, o2 represents the number of Z ₂ , and o2 is an integer of 0 to 3. When o2 is 2 or more, o2 Z ₂ may be identical to or different from each other.

In Formulas 1 and 2, o 3 represents the number of Z ₃ , and o 3 is an integer of 0 to 3. When o3 is 2 or more, o3 Z ₃ may be the same as or different from each other.

In Formulas 1 and 2, o4 represents the number of Z ₄ , and o4 is an integer of 0 to 3. When o4 is 2 or more, o4 Z ₄ may be the same or different from each other.

In one embodiment, any one of Formulas 1 and 2 may be represented by any one selected from Formulas 1-1 to 1-24, but is not limited thereto.

In Formulas 1-1 to 1-24,

Y is O, S or C (R ₃₁ ) (R ₃₂ );

L ₁ to L ₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ aryl A ylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, and a substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group; Is selected from;

n1 to n3 are each independently an integer of 0 to 3;

Ar ₁ to Ar ₃ are independently of each other, i) a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group and C ₂ -C ₆₀ heteroaryl group; And

ii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from;

R ₃₁ and R ₃₂ are each independently of one another: i) hydrogen, deuterium, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;

iii) 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 and C ₂ -C ₆₀ heteroaryl group; And

iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from.

In another embodiment, the light emitting material may be selected from any one of Compounds 1 to 108, but is not limited thereto.

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may emit white light by stacking two or more of the red light emitting layer, the green light emitting layer, and the blue light emitting layer.

The light emitting layer may further include a known light emitting material. For example, the light emitting layer may further include a known host and / or dopant.

Examples of known hosts include Alq ₃ (tris (8-quinolinolato) aluminum), CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole) )), ADN (9,10-di (naphthalen-2-yl) anthracene), TCTA (4,4 ', 4''-tris (carbazol-9-yl) triphenylamine), TPBI (1,3 , 5-tris (N-phenylbenzimidazol-2-yl) benzene (1,3,5-tris (N-phenylbenzimidazole-2-yl) benzene)), TBADN (3-tert-butyl-9,10- Di (naphth-2-yl) anthracene), mCP (9,9 '-(1,3-phenylene) bis-9H-carbazole), E3, OXD-7 (1,3-bis [2- ( 4-tert-butylphenyl) -1,3,4-oxadiazo-5-yl]), DSA (distyrylarylene), dmCBP (see formula below), the following compounds 501 to 509, etc. can be used, It is not limited to this.

Alternatively, as the host, an anthracene-based compound represented by Formula 400 may be used:

* <Formula 400>

In Formula 400, Ar ₁₁₁ and Ar ₁₁₂ are each independently a substituted or unsubstituted C ₅ -C ₆₀ arylene group; Ar ₁₁₃ to Ar ₁₁₆ are each independently a substituted or unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₅ -C ₆₀ aryl group; g, h, i and j may be an integer of 0 to 4 independently of each other.

For example, in Formula 60, Ar ₁₁₁ and Ar ₁₁₂ may be selected from a phenylene group, a naphthylene group, a phenanthrenylene group, or a pyrenylene group; Or a phenylene group, naphthylene group, phenanthrenylene group, fluorenyl group, or pyrenylene group substituted with at least one of phenyl group, naphthyl group and anthryl group, but is not limited thereto.

In Formula 60, g, h, i, and j may be each independently 0, 1, or 2.

중 하나일 수 있으나, 이에 한정되는 것은 아니다.In Formula 400, Ar ₁₁₃ to Ar ₁₁₆ may be each independently selected from a C ₁ -C ₁₀ alkyl group substituted with one or more of a phenyl group, a naphthyl group, and an anthryl group; Phenyl group; Naphthyl group; Anthryl group; Pyrenyl group; Phenanthrenyl group; Fluorenyl group; 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ A phenyl group substituted with at least one of -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthryl group, pyrenyl group, phenanthrenyl group, and fluorenyl group, Naphthyl group, anthryl group, pyrenyl group, phenanthrenyl group, and fluorenyl group; And

It may be one of, but is not limited thereto.

For example, the anthracene-based compound represented by Formula 400 may be one of the following compounds, but is not limited thereto:

Alternatively, as the host, an anthracene-based compound represented by Formula 401 may be used:

* <Formula 401>

For a detailed description of Ar ₁₂₂ to Ar ₁₂₅ in Formula 401, refer to the description of Ar ₁₁₃ of Formula 400.

Ar ₁₂₆ and Ar ₁₂₇ in Formula 401 may be each independently a C ₁ -C ₁₀ alkyl group (eg, a methyl group, an ethyl group, or a propyl group).

In Formula 401 k and l may be an integer of 0 to 4 independently of each other. For example, k and l may be 0, 1 or 2.

For example, the anthracene-based compound represented by Formula 401 may be one of the following compounds, but is not limited thereto:

The dopant may be at least one of a fluorescent dopant and a phosphorescent dopant. The phosphorescent dopant may be an organometallic complex including Ir, Pt, Os, Re, Ti, Zr, Hf, or a combination of two or more thereof, but is not limited thereto.

Examples of known blue dopants include F ₂ Irpic, (F ₂ ppy) ₂ Ir (tmd), Ir (dfppz) ₃ , ter-fluorene, DPAVBi (4,4′-bis (4-diphenyl) Aminostyryl) biphenyl), TBPe (2,5,8,11-tetra- tert -butyl perylene), DPVBi (4,4'-bis (2,2, -diphenylvinyl) -1,1 ' -Biphenyl) and the like, but is not limited thereto.

               DPAVBi TBPe

For example, the following compounds may be used as the red dopant, but are not limited thereto. Alternatively, DCM or DCJTB described later may be used as the red dopant.

For example, the following compounds may be used as the green dopant, but are not limited thereto. Alternatively, as the green dopant, the following C545T can be used.

The light emitting layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 200 kPa to about 600 kPa. When the thickness of the light emitting layer satisfies the aforementioned range, the light emitting layer may exhibit excellent light emission characteristics without a substantial increase in driving voltage.

Next, an electron transporting layer (ETL) is formed on the light emitting layer by various methods such as vacuum deposition, spin coating, and casting. In the case of forming the electron transporting layer by vacuum deposition and spin coating, the conditions vary depending on the compound used, and in general, the electron transporting layer may be selected from a range of conditions substantially the same as the formation of the hole injection layer. As the electron transport layer material, a known electron transport material may be used as a function of stably transporting electrons injected from an electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, especially tris (8-quinolinorate) aluminum (Alq ₃ ), TAZ, Balq, beryllium bis (benzoquinolin-10-noate) -olate: Materials such as Bebq ₂ ), ADN, Compound 201, Compound 202, etc. may be used, but are not limited thereto.

<Compound 201> <Compound 202>

           BCP

The electron transport layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 150 kPa to about 500 kPa. When the thickness of the electron transporting layer satisfies the aforementioned range, a satisfactory electron transporting characteristic can be obtained without a substantial increase in driving voltage.

Alternatively, the electron transport layer may further include a metal-containing material, in addition to a known electron transport organic compound.

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

Compound 203 <LiQ>

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, which does not particularly limit the material.

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, which does not particularly limit the material.

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, or the like may be used. Although the deposition conditions of the electron injection layer vary depending on the compound used, they may be generally selected from the same range of conditions as the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 kPa to about 100 kPa and about 3 kPa to about 90 kPa. When the thickness of the electron injection layer satisfies the aforementioned range, a satisfactory electron injection characteristic may be obtained without a substantial increase in driving voltage.

The second electrode 17 is provided above the organic layer 15. The second electrode may be a cathode, which is an electron injection electrode, and as the metal for forming the second electrode, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. It can be formed into a thin film to obtain a transmissive electrode. On the other hand, various modifications are possible, such as to form a transmissive electrode using ITO and IZO to obtain a front light emitting device.

The organic light emitting device has been described above with reference to FIG. 1, but is not limited thereto.

In addition, when the phosphorescent dopant is used in the light emitting layer, in order to prevent the triplet exciton or hole from diffusing into the electron transporting layer, the vacuum deposition method, the spin coating method, between the hole transporting layer and the light emitting layer or between the H-functional layer and the light emitting layer, The hole blocking layer HBL can be formed by a method such as a cast method, an LB method, or the like. In the case of forming the hole blocking layer by vacuum deposition or spin coating, the conditions vary depending on the compound used, but can be generally within the same condition range as the formation of the hole injection layer. Known hole blocking materials can also be used, and examples thereof include oxadiazole derivatives, triazole derivatives, and phenanthroline derivatives. For example, the following BCP can be used as the hole blocking layer material.

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

The light emitting material represented by any one of Formulas 1 and 2 has a wide energy gap, and triplet energy is suitable for phosphorescence emission. In addition, the organic light emitting device including the light emitting material exhibits high efficiency.

In the hole transport material represented by any one of Formulas 2 (1) and 2 (2), a second benzene is bonded to a meta position based on a first carbon bonded to a carbazole ring among the first benzenes bonded to a carbazole ring. It has a structure that is lower than the compound having a structure in which the second benzene is bonded to the para position based on the first carbon bonded to the carbazole ring among the first benzene bound to the carbazole ring. Reference) and slow hole mobility. Therefore, since the hole mobility is generally faster than the electron mobility, in the light emitting layer of the organic light emitting device employing the compound represented by any one of Formulas (1) and (2) in the hole transport region between the anode and the light emitting layer Hole transfer and electron transfer can be balanced. In addition, the electron injected from the second electrode (cathode) may serve to block leakage from the light emitting layer to the hole transport layer. Therefore, when the compound represented by any one of Chemical Formulas 2 (1) and 2 (2) is employed in the hole transport region, the organic light emitting device may have high efficiency and long life (following Formulas 2 (1) '> and 2 ( 2) '> reference).

<Formula 2 (1) '>

<Formula 2 (2) '>

An organic light emitting device including a light emitting material represented by any one of the above Chemical Formulas 1 and 2 and a hole transport material represented by any one of the above Chemical Formulas 2 (1) and 2 (2) uses a material suitable for phosphorescent emission as a host in the light emitting layer. As a result, excitons are well formed in the light emitting layer to exhibit high efficiency characteristics, and since the electrons leaking from the light emitting layer to the hole transport layer can be minimized, most of the excitons formed in the light emitting layer can contribute to light emission. Therefore, even if the driving voltage of the organic light-emitting device rises, the efficiency decreases relatively little (because roll-off does not occur), so that luminance vs. An efficiency graph is shown.

Therefore, the organic light emitting device including the light emitting material represented by any one of Formulas 1 and 2 and the hole transport material represented by any one of Formulas 2 (1) and 2 (2) has a low driving voltage, high efficiency and high color purity. Indicates.

Particularly, the light emitting layer including the light emitting material represented by any one of Formulas 1 and 2 and the hole transporting layer including the hole transporting material represented by any one of Formulas 2 (1) and 2 (2) may be in contact with each other. It is not limited.

Hereinafter, the organic light emitting device according to one embodiment of the present invention, for example, synthesis examples and examples will be described in more detail, but the present invention is not limited to the following synthesis examples and examples.

In the present specification, specific examples of the unsubstituted C ₁ -C ₆₀ alkyl group (or C ₁ -C ₆₀ alkyl group) include 1 carbon atom such as methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, and the like. And a linear or branched alkyl group from 60 to 60, wherein the substituted C ₁ -C ₆₀ alkyl group has at least one hydrogen atom of the unsubstituted C ₁ -C ₆₀ alkyl group deuterium, halogen atom, hydroxyl group, cyano group, nitro Groups, amino groups, amidino groups, hydrazines, hydrazones, carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl groups, C ₁ -C ₆₀ fluoroalkyl groups, C ₂ -C ₆₀ alkenyl groups , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ heterocyclo alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come Im, C ₂ -C ₆₀ heteroaryl _{group, -N (Q 11) (Q} 12) And and -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ), wherein Q ₁₁ to Q ₁₅ are independently of each other hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ Alkynyl group, C ₆ -C ₆₀ aryl group, and C ₂ -C ₆₀ heteroaryl group.

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

In this specification, an unsubstituted C ₂ -C ₆₀ alkenyl group (or a C ₂ -C ₆₀ alkenyl group) includes one or more carbon double bonds in the middle or the end of the unsubstituted C ₂ -C ₆₀ alkyl group. it means. Examples are ethenyl, propenyl, butenyl and the like. At least one hydrogen atom of these unsubstituted C ₂ -C ₆₀ alkenyl groups may be substituted with the same substituent as in the case of the substituted C ₁ -C ₆₀ alkyl group described above.

An unsubstituted C ₂ -C ₆₀ alkynyl group (or C ₂ -C ₆₀ alkynyl group) herein includes one or more carbon triple bonds in the middle or at the end of the C ₂ -C ₆₀ alkyl group as defined above. Means that. Examples include ethynyl, propynyl, and the like. At least one hydrogen atom of these alkynyl groups may 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 having 6 to 60 carbon atoms containing at least one aromatic ring, and unsubstituted C _5- C ₆₀ arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms containing at least one aromatic ring. When the aryl group and the arylene group include two or more rings, the two or more rings may be fused to each other. At least one hydrogen atom 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 a phenyl group, a C ₁ -C ₁₀ alkylphenyl group (eg, ethylphenyl group), a C ₁ -C ₁₀ alkylbiphenyl group (eg, ethylbiphenyl group ), Halophenyl groups (e.g., o-, m- and p-fluorophenyl groups, dichlorophenyl groups), dicyanophenyl groups, trifluoromethoxyphenyl groups, o-, m-, and p-tolyl groups, o-, m- and p-cumenyl groups, mesityl groups, phenoxyphenyl groups, (α, α-dimethylbenzene) phenyl groups, (N, N'-dimethyl) aminophenyl groups, (N, N'-diphenyl) aminophenyl groups, penteres Neyl group, indenyl group, naphthyl group, halonaphthyl group (e.g. fluoronaphthyl group), C ₁ -C ₁₀ alkylnaphthyl group (e.g. methylnaphthyl group), C ₁ -C ₁₀ alkoxynaphthyl group (e.g. For example, methoxy naphthyl group), anthracenyl group, azurenyl group, heptarenyl group, acenaphthylenyl group, phenenalenyl group, fluorenyl group, anthraquinolyl group, methyl anthryl group, phenanthryl group, triphenyle Nilyl, pyrenyl , Cryenyl, ethyl-crisenyl, pisenyl, peryleneyl, chloroperylenyl, pentaphenyl, pentasenyl, tetraphenylenyl, hexaphenyl, hexasenyl, rubisenyl, coroneyl , Trinaphthylenyl group, heptaphenyl group, heptasenyl group, pyrantrenyl group, obarenyl group, spiro-fluorenyl group, and the like, and examples of the substituted C ₆ -C ₆₀ aryl group include It can be easily recognized with reference to the example of a substituted C ₆ -C ₆₀ aryl group and the substituent of the substituted C ₁ -C ₆₀ alkyl group. Examples of the substituted or unsubstituted C ₆ -C ₆₀ arylene group may be easily recognized with reference to the examples of the substituted or unsubstituted C ₆ -C ₆₀ aryl group.

Unsubstituted C ₂ -C ₆₀ heteroaryl group used herein has a monovalent group having a system consisting of one or more aromatic rings containing one or more heteroatoms selected from N, O, P, S and Si and the remaining ring atoms being C And an unsubstituted C ₂ -C ₆₀ heteroarylene group having a system comprising at least one heteroatom selected from N, O, P or S and consisting of at least one aromatic ring having the remaining ring atom C Means. Here, when the heteroaryl group and heteroarylene group includes two or more rings, two or more rings may be fused to each other. At least one hydrogen atom 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, pyrazolyl group, imidazolyl group, oxazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyridinyl group, pyri Dazinyl, pyrimidinyl, triazinyl, carbazolyl, indolyl, quinolinyl, isoquinolinyl, benzoimidazolyl, imidazopyridinyl, imidazopyrimidinyl, furanyl and thiophenyl groups , Benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group and the like. Examples of the unsubstituted C ₂ -C ₆₀ hetero arylene groups may be easily recognized with reference 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 , wherein A ₂ is the substituted or unsubstituted C ₆ -C ₆₀ aryl group, and the substituted or unsubstituted C ₆ -C ₆₀ arylthio refers to -SA ₃ , wherein A ₃ is the substituted or unsubstituted C ₆ -C ₆₀ aryl group.

EXAMPLE

Example 1

As substrate and anode, ITO (7nm) / Ag (100nm) / ITO (7nm) glass substrates were cut into 50mm x 50mm x 0.7mm size and ultrasonically cleaned for 30 minutes with isopropyl alcohol and ultrapure water for 10 minutes. Ultraviolet rays were irradiated, exposed to ozone and washed, and the glass substrate was installed in a vacuum deposition apparatus.

Compound B was deposited on the anode ITO layer to form a hole injection layer having a thickness of 1200 Å, and then a compound 6-12 was deposited to a thickness of 350 Å on the hole injection layer to form a hole transport layer.

Compound 49 (host) and the following compound D (1) (dopant) were co-deposited on the hole transport layer at a weight ratio of 10: 1 to form a light emitting layer having a thickness of 400 kHz.

Subsequently, a compound of 201 and LiQ is co-deposited on the light emitting layer in a weight ratio of 1: 1 to form an electron transport layer having a thickness of 300 kV. Then, LiQ is deposited on the electron transport layer to form an electron injection layer having a thickness of 5 kV. Mg-Ag was deposited on the electron injection layer in a weight ratio of 10: 1 to form a second electrode (cathode) having a thickness of 130 kHz, thereby manufacturing an organic light emitting device.

<Compound D (1)>

<Compound B>

Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6-132 was used instead of Compound 6-12 to form the hole transport layer and Compound 61 was used instead of Compound 49 to form the emission layer. .

Example 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6-84 was used instead of Compound 6-12 to form the hole transport layer, and Compound 80 was used instead of Compound 49 to form the emission layer. .

Example 4

An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound 6-36 instead of the compound 6-122 in forming the hole transport layer and using the 99 instead of the compound 49 in forming the emission layer.

Example 5

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6-4, instead of Compound 6-12, and 104 instead of Compound 49 were used to form the hole transport layer.

Example 6

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 6-10 was used instead of Compound 6-12 to form the hole transport layer, and Compound 50 was used instead of Compound 49 to form the emission layer. .

Example 7

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 34, instead of Compound 49, and Compound D (2) were used instead of Compound D (1) to form the EML. .

<Compound D (2)>

Example 8

An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 6-132 was used instead of Compound 6-12 to form the hole transport layer and Compound 32 was used instead of Compound 34 to form the emission layer. .

Example 9

An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 6-84 was used instead of Compound 6-12 to form the hole transport layer and Compound 81 was used instead of Compound 34 to form the emission layer. .

Example 10

An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 6-36 was used instead of Compound 6-12 to form the hole transport layer and Compound 82 was used instead of Compound 34 to form the emission layer. .

Example 11

An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 6-4 was used instead of Compound 6-12 to form the hole transport layer and Compound 83 was used instead of Compound 34 to form the emission layer. .

Example 12

An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound 6-10 was used instead of Compound 6-12 to form the hole transport layer and Compound 84 was used instead of Compound 34 to form the emission layer. .

Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 6-12 to form the hole transport layer and Compound 61 was used instead of Compound 49 to form the emission layer.

<Compound A>

Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound B was used instead of Compound 6-12 to form the hole transport layer, and Compound 61 was used instead of Compound 49 to form the emission layer.

<Compound B>

Comparative Example 3

An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound A was used instead of Compound 6-12 to form the hole transport layer and Compound 83 was used instead of Compound 34 to form the emission layer.

Comparative Example 4

An organic light-emitting device was manufactured in the same manner as in Example 7, except that Compound B was used instead of Compound 6-12 to form the hole transport layer and Compound 83 was used instead of Compound 34 to form the emission layer.

Evaluation example

The driving voltage, current density, efficiency, and color purity of the organic light emitting diodes of Examples 1 to 12 and Comparative Examples 1 to 4 were supplied from a current voltmeter (Kethley SMU 236), and the luminance meter PR650 Spectroscan Source Measurement Unit. Product). Examples 1-6, Comparative Examples 1 and 2 were evaluated at 9000 cd / m ² , and Examples 7-12, Comparative Examples 3 and 4 were evaluated at 3000 cd / m ² in the evaluation. The results are shown in Table 1 below:

Driving voltage
(V) Current density
(mA / cm ² ) Current efficiency
(cd / A) Power efficiency
(lm / W) Color coordinates CIE_x CIE_y Example 1 4.8 8.6 104.4 69.0 0.227 0.732 Example 2 4.4 8.7 103.1 73.2 0.212 0.742 Example 3 4.5 8.7 103.8 73.2 0.308 0.672 Example 4 4.9 8.9 101.6 65.0 0.229 0.734 Example 5 4.6 8.9 101.5 69.1 0.287 0.690 Example 6 4.5 8.9 101.3 71.4 0.220 0.737 Example 7 4.5 7.3 41.0 28.7 0.657 0.341 Example 8 4.7 7.1 42.4 28.2 0.651 0.347 Example 9 4.6 7.6 39.4 26.8 0.661 0.337 Example 10 5.0 7.4 40.7 25.7 0.669 0.329 Example 11 4.8 7.3 41.1 26.9 0.659 0.339 Example 12 4.9 7.3 41.1 26.5 0.652 0.348 Comparative Example 1 4.6 12.4 72.4 49.5 0.293 0.685 Comparative Example 2 4.6 12.3 73.5 49.7 0.279 0.695 Comparative Example 3 4.7 9.8 30.6 20.3 0.671 0.327 Comparative Example 4 4.6 9.5 31.4 21.7 0.658 0.340

From Table 1, it can be seen that Examples 1 to 12 have a lower driving voltage and higher efficiency than the Comparative Examples 1 to 4, and have excellent color purity characteristics.

Claims (2)

A first electrode;
A second electrode opposed to the first electrode; And
An organic layer interposed between the first electrode and the second electrode and including an emission layer and a hole transport layer;
The hole transport layer is interposed between the first electrode and the light emitting layer, the light emitting layer and the hole transport layer is in contact with each other,
The light emitting layer includes at least one selected from light emitting materials represented by one of Chemical Formulas 1 and 2;
An organic light emitting device in which the hole transport layer includes at least one selected from a hole transport material represented by Chemical Formula 2 (2):
<Formula 1>

<Formula 2>

In Formulas 1 and 2,
A ₁ is CR ₁ or N; A ₂ is CR ₂ or N; A ₃ is CR ₃ or N; A ₄ is CR ₄ or N; A ₅ is CR ₅ or N; A ₆ is CR ₆ or N; A ₇ is CR ₇ or N; A ₈ is CR ₈ or N; A ₉ is CR ₉ or N; A ₁₀ is CR ₁₀ or N; A ₁₁ is CR ₁₁ or N; A ₁₂ is CR ₁₂ or N; A ₁₃ is CR ₁₃ or N; A ₁₄ is CR ₁₄ or N; A ₁₅ is CR ₁₅ or N; A ₁₆ is CR ₁₆ or N;
R ₁ to R ₁₆ are each independently hydrogen, deuterium, a halogen atom, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, a C ₂ -C ₆₀ heteroaryl group, and —Si (Q ₁ ) (Q ₂ ) (Q ₃ ), wherein Q ₁ to Q ₃ are independently of each other a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or a C ₂ -C ₆₀ heteroaryl group; Or two or more of R ₁ to R ₁₆ may be linked to each other to selectively form a C ₆ -C ₂₀ saturated ring or a C ₆ -C ₂₀ unsaturated ring;
Y is O, S or C (R ₃₁ ) (R ₃₂ );
L ₁ to L ₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ aryl A ylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, and a substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group; Is selected from;
n1 to n3 are each independently an integer of 0 to 3;
Ar ₁ to Ar ₃ are independently of each other, i) a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ —C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, and —Si (Q ₁ ) (Q ₂ ) (Q ₃ ), wherein Q ₁ to Q ₃ are independently of each other a substituted or unsubstituted C _1- A C ₁₀ alkyl group or a substituted or unsubstituted C ₆ -C ₃₀ aryl group; And
ii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come Im, C ₂ -C ₆₀ hetero aryl group and the -Si (Q ₁ ) (Q ₂ ) (Q ₃ ), wherein Q ₁ to Q ₃ are each independently a substituted or unsubstituted C ₁ -C ₁₀ alkyl group or a substituted or unsubstituted C ₆ -C ₃₀ aryl 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 substituted with at least one selected from among C ₂ -C ₆₀ heteroaryl group; Is selected from;
Z ₁ to Z ₄ , R ₃₁ and R ₃₂ are independently of each other, i) hydrogen, deuterium, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ An alkoxy group;
ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;
iii) 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 and C ₂ -C ₆₀ heteroaryl group; And
iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from;
o1 to o4 are each independently an integer of 0 to 3;
<Formula 2 (2)>

In Chemical Formula 2 (2),
X ₁₁ is CR ₁₁ or N; X ₁₂ is CR ₁₂ or N; X ₁₃ is CR ₁₃ or N; X ₁₄ is CR ₁₄ or N; X ₁₅ is CR ₁₅ or N; X ₁₆ is CR ₁₆ or N; X ₁₇ is CR ₁₇ or N; X ₁₈ is CR ₁₈ or N; X ₁₉ is CR ₁₉ or N; X ₂₀ is CR ₂₀ or N; X ₂₁ is CR ₂₁ or N; X ₂₂ is CR ₂₂ or N; X ₂₃ is CR ₂₃ or N; X ₂₄ is CR ₂₄ or N;
Z ₅ , Z ₆ and R ₁₁ to R ₂₄ independently of one another, i) hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salts thereof , Sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, C ₁ -C ₆₀ alkyl groups, C ₂ -C ₆₀ alkenyl groups, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy groups;
ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;
iii) 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 and C ₂ -C ₆₀ heteroaryl group;
iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; And
v) -N (Q ₁₁ ) (Q ₁₂ ), -Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) and -B (Q ₁₆ ) (Q ₁₇ ) (where Q ₁₁ and Q ₁₇ are independently of one another) , 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; Is selected from;
Ar ₁₃ and Ar ₁₄ independently of one another, i) 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 and C ₂ -C ₆₀ heteroaryl group; And
ii) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from;
Z ₁₁ and Z ₁₂ independently of one another, i) a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
ii) 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 and phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group , C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ Im coming aryl and C ₂ -C ₆₀ heteroaryl group, at least one substituted C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ -C ₆₀ alkoxy group of;
iii) 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 and C ₂ -C ₆₀ heteroaryl group; And
iv) 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 salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl Im import and C ₂ -C ₆₀ heteroaryl groups substituted with at least one selected from the group consisting of 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 and C ₂ -C ₆₀ hetero Aryl group; Is selected from;
p and q are each independently an integer from 1 to 4. The method of claim 1,
The organic layer further includes a hole injection layer,
The hole injection layer is interposed between the first electrode and the hole transport layer,
The hole transport layer comprises an organic light emitting device comprising at least one of a compound represented by the formula (300) and a compound represented by the formula (301):
<Formula 300>

<Formula 301>

In Formulas 300 and 301,
Ar ₁₀₁ and Ar ₁₀₂ are each independently selected from a substituted or unsubstituted C ₆ -C ₆₀ arylene group,
Xa and xb are each independently an integer of 0 to 5,
R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R ₁₁₉ and R ₁₂₁ to R ₁₂₄ are each independently hydrogen, deuterium, halogen atom, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine, hydrazone, Carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl groups, substituted or unsubstituted C ₂ -C ₆₀ alkenyl groups, substituted or unsubstituted C ₂ -C ₆₀ Alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₆₀ cycloalkyl group, substituted or unsubstituted C ₅ -C ₆₀ aryl group, substituted or unsubstituted C _5- A C ₆₀ aryloxy group, and a substituted or unsubstituted C ₅ -C ₆₀ arylthio group;
R ₁₀₉ is a phenyl group; Naphthyl group; Anthryl group; Biphenyl group; Pyridyl groups; And 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 salt thereof, substituted or unsubstituted C _1- Phenyl group, naphthyl group, anthryl group, biphenyl group and pyridyl group substituted with at least one of C ₂₀ alkyl group and substituted or unsubstituted C ₁ -C ₂₀ alkoxy group; Is selected from.

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