KR101879832B1 - An organic light emitting diode - Google Patents

Abstract

Color organic light emitting device having a high efficiency and a high color purity while having a simple manufacturing process and a low manufacturing cost.

Description

An organic light emitting diode (OLED)

There is provided a full-color organic light emitting device having a high efficiency and a high color purity and a simple manufacturing process.

The organic light emitting diode is a self light emitting type device having a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and multi-coloring.

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

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

When a voltage is applied between the anode and the cathode, holes injected from the anode move to the light emitting layer via the hole transporting layer, and electrons injected from the cathode move to the light emitting layer via the electron transporting layer. The carriers such as holes and electrons recombine in the light emitting layer region to generate an exiton. This exciton changes from the excited state to the ground state and light is generated.

An organic light emitting device having a high efficiency and a high color purity and a simple manufacturing process.

According to an embodiment, there is provided a liquid crystal display comprising: a substrate including a first sub-pixel, a second sub-pixel, and a third sub-pixel; A plurality of first electrodes formed for each of the first sub-pixel, the second sub-pixel and the third sub-pixel of the substrate; A second electrode facing the first electrode; A first light emitting layer formed between the first electrode and the second electrode of the first sub-pixel and emitting a first color light; A second light emitting layer formed between the first electrode and the second electrode of the second sub-pixel and emitting a second color light; And a hole transporting third light emitting layer which is a common layer formed over the first sub-pixel, the second sub-pixel and the third sub-pixel, i) the plurality of first electrodes is a reflective electrode, The second electrode is a translucent electrode, or ii) the plurality of first electrodes are translucent electrodes and the second electrode is a reflective electrode.

The hole transporting-third light emitting layer may include at least one of a compound represented by the following Formula 1 and a compound represented by the following Formula 2:

&Lt; Formula 1 > < EMI ID =

Among the above general formulas (1) and (2)

R ₁ to R ₈ and R ₂₀ to R ₃₅ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, A substituted or unsubstituted C ₂ -C ₅₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₅₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₅₀ aryl group, a substituted or unsubstituted C ₅ -C ₅₀ aryloxy group, a substituted or unsubstituted C ₅ -C ₅₀ aryl Im come, a substituted or unsubstituted C ₂ -C ₅₀ A heteroaryl group, - (X ₂ ) _a -N (R ₄₀ ) (R ₄₁ ) and - (X ₃ ) _b -Si (R ₄₂ ) (R ₄₃ ) (R ₄₄ );

X ₁ to X ₃ are each independently of one another a substituted or unsubstituted C ₅ -C ₅₀ aryl group and a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group;

Ar ₁ and Ar ₂ are independently of each other a substituted or unsubstituted C ₅ -C ₅₀ aryl group and a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group;

R ₄₀ to R ₄₄ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₂ -C ₅₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₅₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₅₀ aryl group, a substituted or unsubstituted C ₅ -C ₅₀ aryloxy group, a substituted or unsubstituted C ₅ -C ₅₀ aryl Im import and substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, and one of the ;

a and b are independently of each other an integer of 0 to 5;

The hole transporting-third light emitting layer may further include at least one of a phosphorescent dopant and a fluorescent dopant, in addition to the compound represented by the general formula (1) and / or the compound represented by the general formula (2).

The first color light may be red light, the second color light may be green light, and the third color light may be blue light.

The hole transporting-third light emitting layer includes a first region located in the first sub-pixel, a second region located in the second sub-pixel, and a third region located in the third sub-pixel, The first region transports holes from the first electrode to the first light emitting layer, the second region transports holes from the first electrode to the second light emitting layer, and the third region emits the third color light.

The organic light emitting device may satisfy the following equations (1), (2) and (3):

(1) &quot; (2) &quot;

&Quot; (3) &quot;

Among the above-mentioned expressions 1 to 3,

L ₁ is the distance between the first electrode and the second electrode of the first sub-pixel;

L ₂ is a distance between the first electrode and the second electrode of the second sub-pixel;

L ₃ is a distance between the first electrode and the second electrode of the third sub-pixel;

The wavelengths of the first color light, the second color light, and the third color light are respectively lambda ₁ , lambda ₂ and lambda ₃ ;

N ₁ is the refractive index of the layers located between the first electrode and the second electrode of the first sub-pixel;

And n ₂ is a refractive index of a layer positioned between the first electrode and the second electrode of the second sub-pixel;

And n ₃ is the refractive index of the layers positioned between the first electrode and the second electrode of the third sub-pixel;

M ₁ , m ₂ and m ₃ are independently a natural number.

In the above formulas (1), (2) and (3), m ₁ , m ₂ and m ₃ may be 1. At this time, the distance between the first electrode of the first sub-pixel and the first light emitting layer may be D ₁ , D ₁ may be 400 ANGSTROM to 1000 ANGSTROM; And / or a distance between the first electrode of the second sub-pixel and the second light-emitting layer is D ₂ , and D ₂ may be 300 ANGSTROM to 900 ANGSTROM; And / or a sum of a distance between the first electrode of the third sub-pixel and the hole transporting-third light emitting layer, and a thickness of the hole transporting-third light emitting layer is D ₃ , and D ₃ is 200 Å to 800 Å.

Alternatively, m ₁ , m ₂ and m ₃ in the above formulas (1), (2) and (3) At this time, the distance between the first electrode of the first sub-pixel and the first light emitting layer may be D ₁ , D ₁ may be 1600 A to 2300 A; And / or a distance between the first electrode of the second sub-pixel and the second light-emitting layer is D ₂ , D ₂ may be between 1300 Å and 2000 Å; And / or the sum of the distance between the first electrode of the third sub-pixel and the hole transporting-third emission layer, and the thickness of the hole transporting-third emission layer may be D ₃ , and D ₃ may be 900A to 1800A.

Wherein a distance between a first electrode of the first sub-pixel and the first light emitting layer is D ₁ , a distance between the first electrode of the second sub-pixel and the second light emitting layer is D ₂ , When the sum of the distance between the first electrode of the third sub-pixel and the hole transporting-third emitting layer and the thickness of the hole transporting-emitting layer is D ₃ , D ₁ > D ₂ = D ₃ or D ₁ > D ₂ > D &lt; ₃ &gt;.

Among the organic light emitting devices, a first auxiliary layer may be interposed between the hole transporting-third light emitting layer and the first light emitting layer.

A hole injecting layer or a functional layer simultaneously having a hole injecting function and a hole transporting function is interposed between the hole transporting-emitting layer and the first electrode, and the hole injecting layer or the functional layer And may contact the hole transporting-third light emitting layer.

The organic light emitting device not only has high efficiency and high color purity but also a simple manufacturing process.

1 is a cross-sectional view schematically showing an organic light emitting device according to one embodiment.
2 is a cross-sectional view schematically showing an organic light emitting device according to another embodiment.

1 is a schematic view showing a cross section of an embodiment of the organic light emitting device. 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.

The substrate 101 of the organic light emitting device 100 of FIG. 1 includes a first sub-pixel, a second sub-pixel, and a third sub-pixel. The plurality of first electrodes 103 are patterned for each of the first sub-pixel, the second sub-pixel and the third sub-pixel. A hole injecting layer 107 and a hole transporting-emitting layer 110 are sequentially formed on the first electrode 103. The hole injecting layer 107 and the hole transporting-emitting layer 110 are formed on the first electrode 103, Pixel, the second sub-pixel, and the third sub-pixel. The hole transporting property of the first sub-pixel-The first auxiliary layer 114 and the first light emitting layer 113-1 for emitting the first color light are sequentially disposed on the third light emitting layer 110. The hole transporting property of the second sub- A second light emitting layer 113-2 for emitting a second color light is provided on the third light emitting layer 110. [ An electron transport layer 115, an electron injection layer 117, and a second electrode 119 are sequentially formed on the first, second, and third sub-pixels as a common layer on the first, second, and third sub-pixels.

In the present specification, the " common layer " refers to a layer that is not patterned for red, green, and blue sub-pixels but formed over the entire red, green, and blue sub-pixels.

The first color light, the second color light and the third color light are red light, green light and blue light, respectively. Accordingly, the organic light emitting diode 100 can emit full color light. The first color light, the second color light and the third color light are not limited to red light, green light and blue light, respectively, provided that the combined light can be a white light.

As the substrate 101, a substrate used in a typical organic light emitting device can be used. A glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance can be used.

On the substrate 101, a plurality of first electrodes 103 patterned for the first sub-pixel, the second sub-pixel and the third sub-pixel are formed. The first electrode 103 is a reflective electrode. Accordingly, the first color light, the second color light, and the third color light pass through the second electrode 119 and are extracted in a direction opposite to the substrate 101. [

The first electrode 103 may be formed by providing a first electrode material on the substrate 101 using a deposition method, a sputtering method, or the like. When the first electrode 103 is an anode, the first electrode 103-1, the second light-emitting layer 113-2, and the hole-transporting-light-emitting layer 110 are formed on the first electrode 103 to facilitate injection of holes into the first light- The material for use can be selected from materials having a high work function.

The first electrode 103 may be formed of at least one selected from the group consisting of Mg, Al, Al-Li, Ca, Mg-In, Magnesium-silver (Mg-Ag), and the like. The first electrode 103 may be formed of indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), and the like, which are transparent and excellent in conductivity in addition to the above- And various modifications are possible.

A pixel insulating film 105 is formed on the edge portions of the plurality of first electrodes 103. The pixel insulating layer 105 defines a pixel region and may include various well-known organic insulating materials (for example, a silicon based material), an inorganic insulating material, or an organic / inorganic composite insulating material.

On the plurality of first electrodes 103, a hole injection layer 107 is formed as a common layer. The hole injection layer 107 may be formed in contact with the plurality of first electrodes 103.

The hole injection layer 107 may be formed on the first electrodes 103 by various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, laser thermal transfer, .

When the hole injection layer 107 is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer 107, the structure and the thermal characteristics of the desired hole injection layer 107, For example, the deposition temperature may be selected from the range of about 100 to about 500 ° C, the degree of vacuum of about 10 ^-8 to about 10 ^-3 torr, and the deposition rate of about 0.01 to about 100 Å / sec.

When the hole injection layer 107 is formed by the spin coating method, the coating conditions are different depending on the compound used as the material of the hole injection layer 107, the structure and the thermal properties of the desired hole injection layer 107 However, a coating rate of from about 2000 rpm to about 5000 rpm, and a heat treatment temperature for solvent removal after coating may be selected within a temperature range of about 80 DEG C to 200 DEG C, but are not limited thereto.

As the material of the hole injection layer 107, a well-known hole injection material can be used. For example, the hole injection layer 107 may be formed of a material selected from the group consisting of N, N'-diphenyl-N, N'-bis- [4- (phenyl- (N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4,4'- diamine: DNTPD), copper phthalocyanine 2-TNATA, Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid), PEDOT / Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrene sulfonate) / Pani / CSA / Camphorsulfonic acid) or PANI / PSS (polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate).

The thickness of the hole injection layer 107 may be about 100 Å to about 10,000 Å, for example, about 100 Å to about 1500 Å. When the thickness of the hole injection layer 107 satisfies the above-described range, it is possible to realize an organic light emitting device without substantially increasing the driving voltage.

The hole injection layer 107 may further include a charge-generating material for improving the conductivity and the like of the hole injection layer 107, in addition to the hole injection material as described above.

The charge-producing material may be, for example, a p-dopant. Non-limiting examples of the p-dopant include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracano-1,4-benzoquinone dimethine (F4TCNQ) Quinone derivatives; Metal oxides such as tungsten oxide and molybdenum oxide; And a cyano group-containing compound such as the following compound 100, but are not limited thereto.

<Compound 100>

When the hole injection layer 107 further includes the charge-generating material, the charge-generating material may be homogeneously dispersed in the hole injection layer 107 or may be uniformly distributed Modification is possible.

On the hole injection layer 107, a hole transporting-third light emitting layer 110 is provided as a common layer. The hole injecting layer 107 and the hole transporting-emitting layer 110 are in contact with each other.

The hole transporting-third light emitting layer 110 is formed on the hole injection layer 107 by a method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, an inkjet printing method, a laser printing method, . In the case where the hole transporting-third light emitting layer 110 is formed by a vacuum deposition method or a spin coating method, the deposition conditions vary depending on the compound used, but generally, in the same condition range as the formation of the hole injection layer 107 Can be selected.

The hole transporting-emitting layer 110 includes a first region located in the first sub-pixel, a second region located in the second sub-pixel, and a third region located in the third sub-pixel, And a second region of the first electrode 103 serves to transport holes from the first electrode 103 to the first emitting layer 113-1 and the second region serves to transport holes from the first electrode 103 to the second emitting layer 113-2. And the third region may serve to emit the third color light. That is, in the first sub-pixel, the emission of the third color light by the hole transporting-third emission layer 110 does not substantially occur, and in the second sub-pixel, the hole transporting- The light emission of the color light does not substantially take place.

The hole transporting-third light emitting layer 110 may include a compound having both a hole transporting function and a third color light emitting function. For example, when the third color light is blue light, the hole transporting-third light emitting layer 110 may include a compound having both a hole transporting function and a blue light emitting function.

For example, the hole transporting-third light emitting layer 110 may include at least one compound represented by the following formula (1) and a compound represented by the following formula (2)

&Lt; Formula 1 > < EMI ID =

Among the above general formulas (1) and (2)

R ₁ to R ₈ and R ₂₀ to R ₃₅ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, A substituted or unsubstituted C ₂ -C ₅₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₅₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₅₀ aryl group, a substituted or unsubstituted C ₅ -C ₅₀ aryloxy group, a substituted or unsubstituted C ₅ -C ₅₀ aryl Im come, a substituted or unsubstituted C ₂ -C ₅₀ A heteroaryl group, - (X ₂ ) _a -N (R ₄₀ ) (R ₄₁ ) and - (X ₃ ) _b -Si (R ₄₂ ) (R ₄₃ ) (R ₄₄ );

X ₁ to X ₃ are each independently of one another a substituted or unsubstituted C ₅ -C ₅₀ aryl group and a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group;

Ar ₁ and Ar ₂ are independently of each other a substituted or unsubstituted C ₅ -C ₅₀ aryl group and a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group;

R ₄₀ to R ₄₄ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₂ -C ₅₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₅₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₅₀ aryl group, a substituted or unsubstituted C ₅ -C ₅₀ aryloxy group, a substituted or unsubstituted C ₅ -C ₅₀ aryl Im import and substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, and one of the ;

a and b are each independently an integer of 0 to 5;

For example, in the general formulas (1) and (2), R ₁ to R ₈ and R ₂₀ to R ₃₅ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C ₁ - C ₁₀ alkyl group, a substituted or unsubstituted C ₂ -C ₁₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₁₀ alkoxy group, a C ₆ substituted or unsubstituted -C ₁₄ aryl group, a substituted or unsubstituted C ₃ -C ₁₄ heteroaryl group, or _{- (X 2) a -N (} R 40) may be a (R _41), but is not limited to such. Wherein R ₄₀ and R ₄₁ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted C ₁ -C ₁₀ alkyl group, a substituted or unsubstituted C ₂ -C ₁₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₁₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₁₄ aryl group, or a substituted or unsubstituted C ₃ unsubstituted -C ₁₄ heteroaryl date can, but is not limited to this.

Specifically, R ₁ to R ₈ and R ₂₀ to R ₃₅ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a methyl group, an ethyl group, a propyl group, a butyl group, A substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, Substituted or unsubstituted indenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted azulenyl, substituted or unsubstituted heptenyl, substituted or unsubstituted indenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted azulenyl, substituted or unsubstituted heptenyl, Substituted or unsubstituted phenanthrenyl groups such as indacenyl, substituted or unsubstituted acenaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenalenyl, substituted or unsubstituted phenanthrenyl groups phenanthrenyl), a substituted or unsubstituted anthracenyl group (an thienyl, thracenyl, substituted or unsubstituted fluoranthenyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted pyrenylenyl, substituted or unsubstituted chlorenylenyl group substituted or unsubstituted naphthacenyl, substituted or unsubstituted picenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted pentacenyl (pentaphenyl), substituted or unsubstituted naphthacenyl, Substituted or unsubstituted hexacenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, Imidazopyridinyl, substituted or unsubstituted imidazopyrimidinyl, substituted or unsubstituted pyridinyl (substituted or unsubstituted pyridinyl) groups, or substituted or unsubstituted imidazolinyl groups. ), &Lt; / RTI &gt; Substituted or unsubstituted pyrazinyl, pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted indolyl, substituted or unsubstituted purinyl, substituted or unsubstituted quinolinyl group substituted or unsubstituted quinolinyl, substituted or unsubstituted phthalazinyl, substituted or unsubstituted indolizinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted quinazolinyl substituted or unsubstituted quinazolinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted indazolyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenazinyl, A substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted pyranyl group, a substituted or unsubstituted chromenyl group, a substituted or unsubstituted benzofuranyl group, , Substituted or unsubstituted thiophenyl a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted benzoimidazolyl group, a substituted or unsubstituted isoxazolyl group, isoxazolyl, or - (X ₂ ) _a -N (R ₄₀ ) (R ₄₁ ), but is not limited thereto. Wherein R ₄₀ and R ₄₁ independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentalenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group naphthyl, substituted or unsubstituted azulenyl, substituted or unsubstituted heptalenyl, substituted or unsubstituted indacenyl, substituted or unsubstituted acenaphthyl, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, A substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, an unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenylenyl group, a substituted or unsubstituted chrysenyl group, Or unsubstituted naphthacenyl Naphthacenyl, a substituted or unsubstituted picenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentaphenyl group, a substituted or unsubstituted hexacenyl group ( hexacenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted imidazolinyl, , A substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted imidazopyrimidinyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinylene group ( pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted indolyl, substituted or unsubstituted purinyl, substituted or unsubstituted quinolinyl, substituted Or an unsubstituted phthalazinyl group (phthal a substituted or unsubstituted indolizinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted cinnolinyl group, A substituted or unsubstituted indazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenanthridinyl group, , A substituted or unsubstituted pyranyl group, a substituted or unsubstituted chromenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted benzoimidazolyl group, or a substituted or unsubstituted isoxazolyl group. However, It is not limited.

Specifically, R ₁ to R ₈ and R ₂₀ to R ₃₅ independently of each other represent hydrogen; heavy hydrogen; A halogen atom; A hydroxyl group; Cyano; Methyl group; An ethyl group; Propyl group; Butyl group; Pentyl group; An ethynyl group; A propenyl group; Butenyl group; Pentenyl; An acetyl group; Methoxy group; Ethoxy group; Propionine; Butoxy group; Pentoxy group; A phenyl group; Carbazolyl group; A fluorenyl group; Naphthyl group; Anthryl group; A pyridinyl group; A quinolinyl group; A benzimidazolyl group; Imidazopyridinyl group; An imidazopyrimidinyl group; A phenyl group substituted by at least one of deuterium, a halogen atom, a hydroxyl group cyano group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a C ₆ -C ₁₄ aryl group and a C ₂ -C ₁₄ heteroaryl group, A carbazolyl group, a fluorenyl group, a naphthyl group, an anthryl group, a pyridinyl group, a quinolinyl group, a benzoimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group; And - (X ₂ ) _a -N (R ₄₀ ) (R ₄₁ ). Examples of the C ₁ -C ₁₀ alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group. Examples of the C ₁ -C ₁₀ alkoxy group include a methoxy group, an ethoxy group, , Butoxy group and pentoxy group. Examples of the C ₆ -C ₁₄ aryl group include a phenyl group, a naphthyl group and an anthryl group. Examples of the C ₂ -C ₁₄ heteroaryl group include A pyridinyl group, a pyrimidinyl group, and a carbazolyl group, but the present invention is not limited thereto. R ₄₀ and R ₄₁ independently represent a phenyl group; Carbazolyl group; A fluorenyl group; Naphthyl group; Anthryl group; A pyridinyl group; A quinolinyl group; A benzimidazolyl group; Imidazopyridinyl group; An imidazopyrimidinyl group; A phenyl group substituted with at least one of deuterium, a halogen atom, a hydroxyl group cyano group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a C ₆ -C ₁₄ aryl group and a C ₃ -C ₁₄ heteroaryl group, A carbazolyl group, a fluorenyl group, a naphthyl group, an anthryl group, a pyridinyl group, a quinolinyl group, a benzoimidazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; But is not limited thereto. Examples of the above-mentioned C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, C ₆ -C ₁₄ aryl group and C ₃ -C ₁₄ heteroaryl group are described above.

Wherein R ₁ to R ₈ and R ₂₀ to R ₃₅ are independently, hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, the following formulas 4A to 4G, and each _{- (X 2) a -N (} R 40) (R ₄₁ ), but is not limited thereto:

Of the above formula, Z _1, Z _2, Z ₁₁ and Z ₁₂ are, independently, hydrogen, deuterium, a halogen atom, hydroxyl group, carboxyl group, nitro group, C ₁ -C ₁₀ alkyl groups to each other, C ₁ - C ₁₀ alkoxy group, C ₆ -C ₁₄ aryl group or C ₃ -C ₁₄ heteroaryl group may be date, p and q are, independently, an integer from 1 to 8 to each other.

For example, Z ₁ , Z ₂ , Z ₁₁ and Z ₁₂ are each independently selected from the group consisting of hydrogen, deuterium, halogenated atoms, methyl, ethyl, propyl, butyl, methoxy, ethoxy, An naphthyl group, an anthryl group, a pyridinyl group, a pyrimidinyl group or a carbazolyl group.

R ₄₀ and R ₄₁ in the - (X ₂ ) _a -N (R ₄₀ ) (R ₄₁ ) may independently be any one of the formulas (4A) to (4G), and X ₂ and a are described later.

In the general formulas (1) and (2), X ₁ to X ₃ may be, independently of each other, a substituted or unsubstituted C ₅ -C ₁₄ arylene group or a substituted or unsubstituted C ₃ -C ₁₄ heteroarylene group, But is not limited thereto.

For example, X ₁ to X ₃ independently represent a phenyl group, a C ₁ -C ₁₀ alkylphenylene group, a di (C ₁ -C ₁₀ alkyl) phenylene group, a (C ₆ -C ₁₄ aryl) , A di (C ₆ -C ₁₄ aryl) phenylene group, a carbazolylene group, a C ₁ -C ₁₀ alkylcarbazolylene group, a di (C ₁ -C ₁₀ alkyl) carbazolylene group, a C ₆ -C ₁₄ arylcarbon (C ₆ -C ₁₄ aryl) carbazolylene group, fluorenylene group, C ₁ -C ₁₀ alkylfluorenylenylene group, di (C ₁ -C ₁₀ alkyl) fluorenylene group, ( C ₆ -C ₁₄ aryl) fluorenyl group, a di (C ₆ -C ₁₄ aryl) fluorenyl group, a naphthyl group (naphthylene) group, C ₁ -C ₁₀ alkyl naphthyl group, a di (C ₁ -C ₁₀ alkyl) naphthyl group, a (C ₆ -C ₁₄ aryl) naphthyl group, a di (C ₆ -C ₁₄ aryl) naphthyl group, an anthryl group, a C ₁ -C ₁₀ alkyl anthryl group, a di (C ₁ -C ₁₀ alkyl) anthryl group, a (C ₆ -C ₁₄ aryl) anthryl group, a di (C ₆ -C ₁₄ aryl) anthryl group, a pyridinyl group (pyridinylene), C ₁ -C ₁₀ alkyl blood (C ₆ -C ₁₄ aryl) pyridinylene, di (C ₆ -C ₁₄ aryl) pyridinylene, quinolinylene, di (C ₁ -C ₁₀ alkyl) pyridinylene, C ₁ -C ₁₀ alkyl quinolinyl group, a di (C ₁ -C ₁₀ alkyl) quinolinyl group, a (C ₆ -C ₁₄ aryl) quinolinyl group, a di (C ₆ -C ₁₄ aryl) quinolinyl group, benzo imidazolyl group (benzoimidazolylene), C ₁ -C ₁₀ alkyl, benzo-imidazolyl group, a di (C ₁ -C ₁₀ alkyl), benzo-imidazolyl group, (C ₆ -C ₁₄ aryl) benzo imidazolyl C ₁ -C ₁₀ alkylimidazopyridinylene group, di (C ₁ -C ₁₀ alkyl) imidazopyridylene group, di (C ₆ -C ₁₄ aryl) benzimidazolylene group, imidazopyridinylene group, (C ₆ -C ₁₄ aryl) imidazopyridinylene group, di (C ₆ -C ₁₄ aryl) imidazopyridinylene group, imidazopyrimidinylene group, C ₁ -C ₁₀ alkyl imidazo-pyrimidinyl group, a di (C ₁ -C ₁₀ alkyl) imidazo-pyrimidinyl group, a (C ₆ -C ₁₄ aryl) already Division-pyrimidinyl group, or a di (C ₆ -C ₁₄ aryl) imidazo pyrimidinyl alkenylene date can, but it is not limited to this.

For example, X ₁ is a fluorenylene group, a C ₁ -C ₁₀ alkylfluorenylene group, a di (C ₁ -C ₁₀ alkyl) fluorenylene group, a (C ₆ -C ₁₄ aryl) (C ₆ -C ₁₄ aryl) fluoreneylene group, and X ₂ and X ₃ are, independently of each other, a phenylene group, a C ₁ -C ₁₀ alkylphenylene group, a di (C ₁ -C ₁₀ alkyl ) Phenylene group, (C ₆ -C ₁₄ aryl) phenylene group or di (C ₆ -C ₁₄ aryl) phenylene group, but is not limited thereto. Examples of the C ₁ -C ₁₀ alkyl group include a methyl group, an ethyl group, a propyl group and a butyl group. Examples of the C ₆ -C ₁₄ group include a phenyl group, a naphthyl group and an anthryl group.

In the above formula (1), Ar ₁ and Ar ₂ may be independently of each other a substituted or unsubstituted C ₅ -C ₁₄ aryl group or a substituted or unsubstituted C ₃ -C ₁₄ heteroaryl group, but are not limited thereto.

Specifically, Ar ₁ and Ar ₂ independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted pentarenenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, Substituted or unsubstituted indanediyl, substituted or unsubstituted acenaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenarenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted phenanthryl, A substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted A substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted phenenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted pentacenyl group, a substituted or unsubstituted hexacenyl group , A substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted imidazopyridinyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted pyridinyl group, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinazolinyl group, A substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted indazolyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthridinyl group, a substituted or unsubstituted phenanthridinyl group, A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted isothiazolyl group, a substituted or unsubstituted thiophenyl group, a substituted or unsubstituted thiophenyl group, A substituted or unsubstituted benzoimidazolyl group, or a substituted or unsubstituted isoxazolyl group, but is not limited thereto.

Specifically, each of Ar ₁ and Ar ₂ independently represents a phenyl group, a halogenated phenyl group, a C ₁ -C ₁₀ alkylphenyl group, a di (C ₁ -C ₁₀ alkyl) phenyl group, a (C ₆ -C ₁₄ aryl) ₆ -C ₁₄ aryl) phenyl group, a phenyl group substituted with a diaryl amino group, a carbazole group (carbazolyl), halogenated carbazole group, a C ₁ -C ₁₀ alkyl carbazole group, a di (C ₁ -C ₁₀ alkyl) carbazole group , C ₆ -C ₁₄ aryl carbazole group, a di (C ₆ -C ₁₄ aryl) carbazole group, a phenyl group substituted with a diaryl amino group, a fluorenyl group (fluorenyl), halogenated fluorenyl group, C ₁ -C ₁₀ alkyl fluorenyl group, di (C ₁ -C ₁₀ alkyl) fluorenyl group, a (C ₆ -C ₁₄ aryl) fluorenyl group, a di (C ₆ -C ₁₄ aryl) fluorenyl group, a fluorenyl substituted with diarylamino groups group, a naphthyl group (naphthyl) group, a halogenated naphthyl group, a C ₁ -C ₁₀ alkyl naphthyl group, a di (C ₁ -C ₁₀ alkyl) naphthyl group _{(naphthylene), (C 6 -C} 14 aryl) naphthyl group, a di ( C ₆ -C ₁₄ aryl) naphthyl group, a diarylamino group A substituted naphthyl group, an anthryl group, a halogenated anthryl group, C ₁ -C ₁₀ alkyl anthryl group, a di (C ₁ -C ₁₀ alkyl) anthryl group, a (C ₆ -C ₁₄ aryl) anthryl group, a di (C ₆ -C ₁₄ aryl) anthryl group, an anthryl group substituted with a diarylamino group, a pyridinyl group (pyridinyl), halogenated pyridinyl group, C ₁ -C ₁₀ alkyl pyridinyl group, a di (C ₁ -C ₁₀ alkyl) pyridinyl group, (C ₆ -C ₁₄ aryl) pyridinyl group, a di (C ₆ -C ₁₄ aryl) pyridinyl group, Doni substituted with diarylamino groups pyridinyl group, quinolinyl group (quinolinyl), halogenated quinolinyl group, a C ₁ -C ₁₀ alkyl quinolinyl group, a di (C ₁ -C ₁₀ alkyl) quinolinyl group, a (C ₆ -C ₁₄ aryl) quinolinyl group, a di (C ₆ -C ₁₄ aryl) quinolinyl group, a quinolinyl group, a benzoimidazol group (pyridinyl), halogenated benzoimidazol group, a C ₁ -C ₁₀ alkyl-benzoimidazol group, a di (C ₁ -C ₁₀ alkyl) benzoimidazole group substituted with diarylamino groups , (C ₆ -C ₁₄ aryl) benzoyl imidazole, di (C ₆ -C ₁₄ aryl) benzo imidazole Imidazole substituted with a benzo group, a diaryl amino group, imidazole jopi piperidinyl group, a halogenated imidazole jopi piperidinyl group, a C ₁ -C ₁₀ alkyl imidazole jopi piperidinyl group, a di (C ₁ -C ₁₀ alkyl) imidazole jopi (C ₆ -C ₁₄ aryl) imidazopyridinyl group, a di (C ₆ -C ₁₄ aryl) imidazopyridinyl group, an imidazopyridinyl group substituted with a diarylamino group, an imidazopyrimidinyl group ( imidazopyrimidinyl, halogenated imidazopyrimidinyl, C ₁ -C ₁₀ alkylimidazopyrimidinyl, di (C ₁ -C ₁₀ alkyl) imidazopyrimidinyl, (C ₆ -C ₁₄ aryl) imidazopyrimidyl (C ₆ -C ₁₄ aryl) imidazopyrimidinyl group, an imidazopyrimidinyl group substituted with a diarylamino group, and the like. Examples of the C ₁ -C ₁₀ alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group. Examples of the C ₆ -C ₁₄ aryl group include a phenyl group, a naphthyl group, , And the "aryl group" in the "diarylamino group" may be a phenyl group, a naphthyl group or an anthryl group, but is not limited thereto.

In Formulas 1 and 2, a and b are each independently an integer of 0 to 5. For example, a and b may be, independently of each other, 0, 1 or 2, but are not limited thereto. When a is 2 or more, 2 or more X ₂ may be the same as or different from each other, and when b is 2 or more, 2 or more X ₃ may be the same as or different from each other.

The formula 1 may be represented by, for example, the following formula (1a), but is not limited thereto:

&Lt; Formula 1a > < EMI ID =

In the above formulas (1a) and (1b), R ₁ , Z ₁₁ , Z ₁₂ and Ar ₂ are described above. In the above formulas (1a) and (1b), the description of Z ₂₁ and Z ₂₂ refers to the description of Z ₁₁ above.

For example, R ₁ in the general formulas (1a) and (1b) is a phenyl group; Carbazolyl group; A fluorenyl group; Naphthyl group; Anthryl group; A pyridinyl group; A quinolinyl group; A benzimidazolyl group; Imidazopyridinyl group; An imidazopyrimidinyl group; A phenyl group substituted with at least one of deuterium, a halogen atom, a hydroxyl group cyano group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a C ₆ -C ₁₄ aryl group and a C ₃ -C ₁₄ heteroaryl group, A carbazolyl group, a fluorenyl group, a naphthyl group, an anthryl group, a pyridinyl group, a quinolinyl group, a benzoimidazolyl group, and an imidazopyridinyl group, an imidazopyrimidinyl group; (The above description of the C ₁ -C ₁₀ alkyl group, the C ₁ -C ₁₀ alkoxy group, the C ₆ -C ₁₄ aryl group and the C ₃ -C ₁₄ heteroaryl group is the same as described above); Z ₁₁ , Z ₁₂ , Z ₂₁ and Z ₂₂ are each independently selected from the group consisting of hydrogen, deuterium, halogenated atoms, methyl, ethyl, propyl, butyl, methoxy, ethoxy, propoxy, A pyridinyl group, a pyrimidinyl group or a carbazolyl group; Wherein Ar ₂ is a phenyl group, halogenated phenyl group, C ₁ -C ₁₀ alkyl group, a di (C ₁ -C ₁₀ alkyl) group, a (C ₆ -C ₁₄ aryl) phenyl group, a di (C ₆ -C ₁₄ aryl) phenyl group, Dia a phenyl group substituted with reel group, a carbazole group (carbazolyl), halogenated carbazole group, a C ₁ -C ₁₀ alkyl carbazole group, a di (C ₁ -C ₁₀ alkyl) carbazole group, a C ₆ -C ₁₄ aryl carbazole Di (C ₆ -C ₁₄ aryl) carbazolyl group, a phenyl group substituted with a diarylamino group, a fluorenyl group, a halogenated fluorenyl group, a C ₁ -C ₁₀ alkylfluorenyl group, a di (C ₁ - C ₁₀ alkyl) fluorenyl group, a (C ₆ -C ₁₄ aryl) fluorenyl group, a di (C ₆ -C ₁₄ aryl) fluorenyl group, a fluorenyl group, Boutique, naphthyl, (naphthyl), an amino group substituted with the reel, halogenated naphthyl group, a C ₁ -C ₁₀ alkyl naphthyl group, a di (C ₁ -C ₁₀ alkyl) naphthyl group _{(naphthylene), (C 6 -C} 14 aryl) naphthyl group, a di (C ₆ -C ₁₄ aryl) naphthyl group , A naphthyl group substituted with a diarylamino group, an anthryl group, Gen hwaan Trill group, C ₁ -C ₁₀ alkyl group not Trill, di (C ₁ -C ₁₀ alkyl) anthryl group, a (C ₆ -C ₁₄ aryl) anthryl group, is not di (C ₆ -C ₁₄ aryl) Or an aryl group substituted with a diarylamino group, and the aryl group of the above-mentioned arylamino group may be a phenyl group, a naphthyl group or an anthryl group.

The compound represented by Formula 1 may be, but is not limited to, the following compounds 1 to 18:

&Lt; Compound 1 > < Compound 2 >

&Lt; Compound 3 > < Compound 4 >

&Lt; Compound 5 > < Compound 6 >

&Lt; Compound 7 > < Compound 8 >

&Lt; Compound 9 > < Compound 10 &

&Lt; Compound 11 > < Compound 12 >

&Lt; Compound 13 > < Compound 14 >

&Lt; Compound 15 > < Compound 16 >

&Lt; Compound 17 > < Compound 18 >

Meanwhile, the compound represented by Formula 2 may be represented by Formula 2a:

&Lt; EMI ID =

For details of R ₄₀ , R ₄₁ , X ₂ and a in the above formula (2), see the above description.

For example, R &lt; ₄₀ & gt _; and R &lt; ₄₁ &gt; Carbazolyl group; A fluorenyl group; Naphthyl group; Anthryl group; A pyridinyl group; A quinolinyl group; A benzimidazolyl group; Imidazopyridinyl group; An imidazopyrimidinyl group; A phenyl group substituted with at least one of deuterium, a halogen atom, a hydroxyl group cyano group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a C ₆ -C ₁₄ aryl group and a C ₃ -C ₁₄ heteroaryl group, A carbazolyl group, a fluorenyl group, a naphthyl group, an anthryl group, a pyridinyl group, a quinolinyl group, a benzoimidazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; The description of the C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, C ₆ -C ₁₄ aryl group and C ₃ -C ₁₄ heteroaryl group is the same as described above (for example, Lt; / RTI &gt; X ₂ represents a phenyl group, a C ₁ -C ₁₀ alkylphenylene group, a di (C ₁ -C ₁₀ alkyl) phenylene group, a (C ₆ -C ₁₄ aryl) phenylene group or a di (C ₆ -C ₁₄ aryl) Can be; a may be 1 or 2, but is not limited thereto.

The compound represented by Formula 2 may be the following compounds 19 to 28, but is not limited thereto.

&Lt; Compound 19 > < Compound 20 >

&Lt; Compound 21 > < Compound 22 >

&Lt; Compound 23 > < Compound 24 >

&Lt; Compound 25 > < Compound 26 >

&Lt; Compound 27 > < Compound 28 >

Specific examples of the unsubstituted C ₁ -C ₅₀ alkyl group (or C ₁ -C ₅₀ alkyl group) in the present specification include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, and, a substituted C ₁ -C ₅₀ alkyl group is unsubstituted the beach C ₁ -C ₅₀ alkyl group one or more hydrogen atom is a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, hydrazine, hydrazone, a carboxyl group or A salt thereof, a phosphoric acid or a salt thereof, or a C ₁ -C ₃₀ alkyl group, a C ₂ -C ₃₀ alkenyl group, a C ₂ -C ₃₀ alkynyl group, a C ₆ -C ₃₀ aryl group, a C ₂ -C ₂₀ (Q ₁ ) (Q ₂ ), and -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) wherein Q ₁ to Q ₅ are independently of each other hydrogen, C ₁ -C ₃₀ alkyl , A C ₂ -C ₃₀ alkenyl group, a C ₂ -C ₃₀ alkynyl group, a C ₆ -C ₃₀ aryl group, and a C ₂ -C ₂₀ heteroaryl group. On the other hand, the substituted or unsubstituted C ₁ -C ₅₀ alkylene group has the same structure as the substituted or unsubstituted C ₁ -C ₅₀ alkyl group as described above, but is a different group only in that it is a divalent linking group.

In the present specification, an unsubstituted C ₁ -C ₅₀ alkoxy group (or a C ₁ -C ₅₀ alkoxy group) is a group represented by -OA ₁ (wherein A ₁ is an unsubstituted C ₁ -C ₅₀ alkyl group as described above) And specific examples thereof include methoxy, ethoxy, isopropyloxy, and the like. At least one of the hydrogen atoms of these alkoxy groups is substituted with the same substituent as the above-mentioned substituted C ₁ -C ₅₀ alkyl group It is possible.

In the present specification, the unsubstituted C ₂ -C ₅₀ alkenyl group (or C ₂ -C ₅₀ alkenyl group) includes one or more carbon double bonds at the middle or end of the unsubstituted C ₂ -C ₅₀ alkyl group it means. Examples include ethenyl, propenyl, butenyl, and the like. At least one hydrogen atom in these unsubstituted C ₂ -C ₅₀ alkenyl groups may be substituted with substituents similar to those of the substituted C ₁ -C ₅₀ alkyl group described above. On the other hand, it is a substituted or unsubstituted C ₂ -C ₅₀ alkenylene group substituted or unsubstituted C ₂ -C ₅₀ alkenylene group except that different groups of the same structure branches are divalent linking group as described above.

In the present specification, an unsubstituted C ₂ -C ₅₀ alkynyl group (or C ₂ -C ₅₀ alkynyl group) contains at least one carbon triple bond at the middle or end of a C ₂ -C ₅₀ alkyl group as defined above . 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 ₅₀ alkyl group described above.

In the specification unsubstituted C ₅ -C ₅₀ aryl group refers to a monovalent (monovalent) group with the aromatic system between carbon atoms containing at least one aromatic ring of 5 to 30, and carbonyl, an unsubstituted C ₅ - C ₅₀ arylene group means a divalent group having from 5 to 30 carbon atoms carbocyclic aromatic systems 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 the substituted C ₁ -C ₅₀ alkyl group described above.

Examples of the substituted or unsubstituted C ₅ -C ₅₀ aryl group include a phenyl group, a C ₁ -C ₁₀ alkylphenyl group (for example, ethylphenyl group), a C ₁ -C ₁₀ alkyl biphenyl group (for example, ethyl biphenyl group O-, m- and p-tolyl groups, o-, m- and p-fluorophenyl groups, dichlorophenyl groups), dicyanophenyl groups, trifluoromethoxyphenyl groups, (N, N'-dimethyl) aminophenyl group, (N, N'-diphenyl) aminophenyl group, pentaerythrityl group, p-cumene group, mesityl group, phenoxyphenyl group, group, an indenyl group, a naphthyl group, a halonaphthyl group (e.g., naphthyl fluoro), C ₁ -C ₁₀ alkyl naphthyl group (e.g., a methyl naphthyl group), C ₁ -C ₁₀ alkoxy-naphthyl group (e.g. For example, a methoxynaphthyl group), an anthracenyl group, an azenyl group, an heptalenyl group, an acenaphthylenyl group, a phenarenyl group, a fluorenyl group, an anthraquinolyl group, Nyl, pyrenyl , A chrysenyl group, an ethyl-chrysenyl group, a picenyl group, a perylenyl group, a chloroperylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenylenyl group, a hexaphenyl group, a hexacenyl group, , A trinaphthylanyl group, a heptaphenyl group, a heptacenyl group, a pyranthrenyl group, an obarenyl group and the like. Examples of the substituted C ₅ -C ₅₀ aryl group include unsubstituted C ₅ -C ₅₀ Can be easily recognized by referring to examples of aryl groups and substituents of the substituted C ₁ -C ₅₀ alkyl group. Examples of the substituted or unsubstituted C ₅ -C ₅₀ arylene group may be easily recognized with reference to the examples of the substituted or unsubstituted C ₅ -C ₅₀ aryl group.

In the present specification, an unsubstituted C ₂ -C ₅₀ heteroaryl group means a monovalent group having a system consisting of at least one aromatic ring having at least one heteroatom selected from N, O, P or S and the remaining ring atoms C And the unsubstituted C ₃ -C ₃₀ heteroarylene group means a divalent group having a system consisting of at least one aromatic ring containing at least one heteroatom selected from N, O, P or S and the remaining ring atoms C do. Herein, when the heteroaryl group and the heteroarylene group include two or more rings, two or more rings may be fused with 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 above-mentioned C ₁ -C ₅₀ alkyl group.

Examples of the unsubstituted C ₂ -C ₅₀ heteroaryl group include a pyrazolyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a pyridinyl group, An imidazopyrimidinyl group, an imidazopyrimidinyl group, and the like can be given as examples of the pyrimidinyl group, the pyrimidinyl group, the pyrimidinyl group, the triazinyl group, the carbazolyl group, the indolyl group, the quinolinyl group, the isoquinolinyl group, Examples of the unsubstituted C ₂ -C ₅₀ hetero arylene groups may be easily recognized with reference to the examples of the substituted or unsubstituted C ₂ -C ₅₀ arylene group.

The unsubstituted C ₅ -C ₅₀ aryloxy group -OA ₂ having the formula (where, A ₂ is an unsubstituted C ₅ -C ₅₀ aryl group as described above), the unsubstituted C ₅ -C ₅₀ The arylthio group has the formula -S ₃ wherein A ₃ is an unsubstituted C ₅ -C ₅₀ aryl group as described above. At least one hydrogen atom of the aryloxy group and the arylthio group may be substituted with the same substituent as in the case of the above-mentioned C ₁ -C ₃₀ alkyl group.

The hole transporting-third light emitting layer 110 may further include a fluorescent dopant or a phosphorescent dopant which emits a third color light, in addition to the compound represented by the general formula (1) or the compound represented by the general formula (2). Since the third color light is a blue light, the hole transporting-third light emitting layer 110 may further include a blue dopant.

Examples of blue dopants include F ₂ Irpic, (F ₂ ppy) ₂ Ir (tmd), Ir (dfppz) ₃ , ter-fluorene, 4,4'-bis (4-diphenylaminostyryl) Biphenyl (DPAVBi), 2,5,8,11-tetra- tert -butyl perylene (TBPe), DPVBi, and the like.

               DPAVBi TBPe

The thickness of the hole transporting-third light emitting layer 110 may be 100 ANGSTROM to 500 ANGSTROM, for example, 150 ANGSTROM to 300 ANGSTROM. When the thickness of the third light emitting layer 110 satisfies the above-described range, it is possible to realize an organic light emitting device having substantially no drive voltage rise.

Next, a first auxiliary layer 114 is formed on the hole transporting-third light emitting layer 110 of the first sub-pixel to promote the resonance of the first color light. A first auxiliary layer 114 is formed on the first auxiliary layer 114, Thereby forming the light emitting layer 113-1. On the other hand, the hole transporting property of the second sub-pixel - the second light emitting layer 113 - 2 is formed on the third light emitting layer 110. When the first color light is red light, the first light emitting layer 113-1 may be a red light emitting layer, and when the second color light is green light, the second light emitting layer 113-2 may be a green light emitting layer.

The first auxiliary layer 114 is a layer interposed between the hole transporting-blue light emitting layer 110 and the first light emitting layer 113-1 to control L ₁ and D ₁ as described later, An injecting material, a hole transporting material, or a material having both a hole injecting function and a hole transporting function.

The first auxiliary layer 114 may be a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a carbazole derivative such as N, N'-bis (3-methylphenyl) -N, N'- 1,1-biphenyl] -4,4'-diamine (TPD), 4,4 ', 4 "-tris (N-carbazolyl) triphenylamine -carbazolyl) triphenylamine), NPB (N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine, ), But the present invention is not limited thereto.

The thickness of the first auxiliary layer 114 can be selected within a range that satisfies D ₁ and L ₁ as described later.

The first light emitting layer 113-1 and the second light emitting layer 113-2 may include a known light emitting material. For example, the first light emitting layer 113-1 and the second light emitting layer 113-2 may include a known host and a dopant.

Examples of known hosts include Alq ₃ , CBP (4,4'-N, N'-dicarbazole-biphenyl), PVK (poly (n-vinylcarbazole) (N, N-phenylbenzimidazole-2-yl) benzene), anthracene (ADN), TCTA, TPBI (1,3,5-tris ), TBADN (3-tert-butyl-9,10-di (naphth-2-yl) anthracene), E3 and DSA (distyrylarylene).

ADN

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

When the first color light is red, known red dopants such as PtOEP, Ir (piq) ₃ , BtpIr, and the like can be used, but the present invention is not limited thereto.

Ir (ppy) ₃ (ppy = phenylpyridine), Ir (ppy) ₂ (acac), Ir (mpyp) ₃ and the like can be used as the known green dopant when the second color light is green. no.

When the first light emitting layer 113-1 and / or the second light emitting layer 113-2 include a host and a dopant, the content of the dopant is usually about 0.01 to about 15 parts by weight , But is not limited thereto.

The thicknesses of the first light emitting layer 113-1 and the second light emitting layer 113-2 may be about 100 Å to 1000 Å, for example, 200 Å to 600 Å. When the thickness of the first light emitting layer 113-1 and the second light emitting layer 113-2 is in the range described above, an organic light emitting device exhibiting excellent light emitting characteristics without substantial increase in driving voltage can be manufactured.

When the first light emitting layer 113-1 and the second light emitting layer 113-2 include a phosphorescent dopant, when the first light emitting layer 113-1 and the second light emitting layer 113-2 are used together, A hole blocking layer (HBL) is formed by a method such as a vacuum evaporation method, a spin coating method, a casting method, an LB method, or the like before the formation of the electron transporting layer 115 in order to prevent diffusion of holes into the electron transporting layer 115. [ (Not shown in Fig. 1). In the case of forming the hole blocking layer by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but they can be generally in the same range of conditions as the formation of the hole injection layer 107. Known hole blocking materials can also be used, examples of which include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, Balq, and the like.

The thickness of the hole blocking layer may be about 10 A to 1000 A, for example, 30 A to 300 A. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics can be obtained without increasing the driving voltage substantially.

Next, an electron transporting layer (ETL) 115 is formed over the first, second and third sub-pixels by various methods such as vacuum evaporation, spin coating, and casting. When the electron transporting layer 115 is formed by the vacuum deposition method and the spin coating method, the conditions vary depending on the compound used, but generally, the conditions can be selected from substantially the same range as the formation of the hole injection layer 107. As the material of the electron transport layer 115, a well-known electron transport material can be used as the material that functions to stably transport electrons injected from the second electrode 119. Examples thereof include quinoline derivatives, especially tris (8-quinolinolate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10-olate: Bebq ₂ ) And the like may be used, but the present invention is not limited thereto.

The thickness of the electron transport layer 115 may be about 100 Å to 1000 Å, for example, 150 Å to 500 Å. When the thickness of the electron transporting layer 115 satisfies the above-described range, satisfactory electron transporting characteristics can be obtained without substantially increasing the driving voltage.

Alternatively, the electron transporting layer 115 may include an electron transporting organic compound and a metal-containing material. Non-limiting examples of the electron transporting organic compound include: AND (9,10-di (naphthalen-2-yl) anthracene); And anthracene compounds such as the following compounds 101 and 102, but are not limited thereto.

&Lt; Compound 101 > < Compound 102 >

The metal-containing material may comprise a Li complex. Non-limiting examples of the Li complex include lithium quinolate (LiQ), the following compound 103, and the like:

<Compound 103>

In addition, an electron injection layer (EIL) 117, which is a material having a function of facilitating the injection of electrons, can be deposited on the electron transport layer 115 from the second electrode 119, which is not particularly limited.

As the material for forming the electron injection layer 117, any material known as an electron injection layer forming material such as LiF, NaCl, CsF, Li ₂ O, BaO, or the like can be used. The deposition conditions of the electron injection layer 117 may vary depending on the compound used, but may be selected generally within the same range of conditions as the formation of the hole injection layer 107.

The thickness of the electron injection layer 117 may be about 1 A to about 100 A, for example, about 3 A to about 90 A. When the thickness of the electron injection layer 117 satisfies the above-described range, satisfactory electron injection characteristics can be obtained without substantially increasing the driving voltage.

A second electrode 119 is formed as a common layer on the electron injection layer 117. The second electrode 119 is a translucent electrode. The second electrode 119 may be a cathode, which is an electron injection electrode. At this time, the metal for forming the second electrode 119 may be a metal, an alloy, an electrically conductive compound having a low work function, Mixtures may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- (For example, a thickness of 10 to 500 ANGSTROM) to obtain a semi-transparent electrode. On the other hand, the second electrode 119 can be formed using a transparent electrode using ITO or IZO in order to obtain a front light emitting element.

The organic light emitting diode 100 has a structure in which the first color light, the second color light, and the third color light can resonate between the first electrode 103, which is a reflective electrode, and the second electrode 119, .

For example, the organic light emitting element of Fig. 1 satisfies the following equations (1), (2) and (3)

(1) &quot; (2) &quot;

&Quot; (3) &quot;

Among the above-mentioned expressions 1 to 3,

L ₁ is the distance between the first electrode and the second electrode of the first sub-pixel;

L ₂ is a distance between the first electrode and the second electrode of the second sub-pixel;

L ₃ is a distance between the first electrode and the second electrode of the third sub-pixel;

The wavelengths of the first emergent light, the second color light, and the third color light are respectively lambda ₁ , lambda ₂ and lambda ₃ ;

N ₁ is the refractive index of the layers located between the first electrode and the second electrode of the first sub-pixel;

And n ₂ is a refractive index of a layer positioned between the first electrode and the second electrode of the second sub-pixel;

And n ₃ is the refractive index of the layers positioned between the first electrode and the second electrode of the third sub-pixel;

M ₁ , m ₂ and m ₃ are independently a natural number.

When the organic light emitting diode 100 satisfies the above Equations 1, 2, and 3, the first color light, the second color light, and the third color light are resonated between the first electrode 103 and the second electrode 119 while being resonated The efficiency of the organic light emitting device 100 can be improved because the organic light emitting device 100 can be taken out of the organic light emitting device 100 through the second electrode 119 due to the principle of interference.

In the above formulas (1), (2) and (3), m ₁ , m ₂ and m ₃ may be 1.

Pixels, m ₁ , m _2, and m ₃ are 1 and the first color light is red light, a distance D between the first electrode of the first sub-pixel and the first light-emitting layer is D ₁ ) (i.e., the sum of the thickness of the hole injection layer 107, the hole transporting property, the thickness of the third light emitting layer 110, and the thickness of the first auxiliary layer in FIG. 1) may be 400 ANGSTROM to 1000 ANGSTROM, have.

In the above equations (1), (2) and (3), when m ₁ , m ₂ and m ₃ are 1 and the second color light is green light, a distance D between the first electrode of the second sub- ₂ ) (that is, the sum of the thickness of the hole injection layer 107 and the thickness of the hole transporting layer-the third light emitting layer 110 in FIG. 1) may be 300 ANGSTROM to 900 ANGSTROM, for example, 400 ANGSTROM to 800 ANGSTROM.

When m ₁ , m ₂ and m ₃ are 1 and the third color light is blue light in the equations (1), (2) and (3), a difference between the first electrode and the hole transporting- And the sum of the hole transporting property and the third light emitting layer thickness (D ₃ ) may be 200 Å to 800 Å, for example, 300 Å to 700 Å.

Alternatively, m ₁ , m ₂ and m ₃ in the above-mentioned formulas (1), (2) and (3)

Of the equation (1), 2 and 3, m _1, the distance between the m ₂ and m ₃ is 2, and when the first color light is the red light, the first sub-pixel of the first electrode and the first light-emitting layer (D ₁ ) (i.e., the sum of the thicknesses of the hole injection layer 107, the hole transporting layer-the third light emitting layer 110, and the thickness of the first auxiliary layer 114 in FIG. 1) is in the range of 1600 A to 2300 A, Lt; / RTI &gt;

A distance D between the first electrode of the second sub-pixel and the second light-emitting layer, when m ₁ , m ₂ and m ₃ are 2 and the second color light is green light, ₂ ) (that is, the sum of the thickness of the hole injection layer 107 and the thickness of the hole transporting layer-the third light emitting layer 110 in FIG. 1) may be in the range of 1300 Å to 2000 Å, for example, 1400 Å to 1900 Å.

When m ₁ , m _2, and m ₃ are 2 in the above equations (1), (2), and (3) and the third color light is blue light, the first electrode of the third subpixel and the hole transporting- And the sum of the distance and the hole transporting-third emitting layer thickness D ₃ may be 900 ANGSTROM to 1800 ANGSTROM, for example, 1000 ANGSTROM to 1600 ANGSTROM.

If D ₁ , D _2, and D ₃ satisfy the ranges as described above, optimal constructive interference may occur at the resonance of each color. In addition, in the first sub-pixel and the second sub-pixel, the light emission is caused in the first light emitting layer and the second light emitting layer other than the hole transporting-third light emitting layer, so that the first and second sub- Color mixing can be prevented. In addition, the organic light emitting device emits light while radiating an exciton, which can be regarded as electric dipole radiation. A weak microcavity phenomenon is a phenomenon in which the dipole radiation is located at a distance less than the wavelength of the light to be emitted to the stronger reflector, the damping of the dipole due to the image dipole induced by the reflector rate) is changed, and thus a phenomenon that the force is changed to be emitted in accordance with, if satisfied with the range of D _1, D ₂ and D _3, as described above, the first color light by the weak microcavity development, second-color and third The luminous efficiency of the color light can be improved.

D ₁ , D ₂ and D ₃ may have the relationship of D ₁ > D ₂ = D ₃ as shown in FIG. That is, by forming the first auxiliary layer 114 between the hole transporting-third light emitting layer 110 and the red light emitting layer 113-1, D ₁ > D ₂ can be obtained.

Since the organic light emitting device 100 of FIG. 1 emits the third color light by the hole transporting-third light emitting layer 110, which is a common layer, the light emitting layer for emitting the third color light is separately patterned into the third sub pixel region no need. Therefore, there is no risk of misalignment of the light emitting layer for the third color light emission. The organic light emitting device 100 has a simple manufacturing process and low manufacturing cost.

2 is a schematic cross-sectional view of an organic light emitting diode 200 according to another embodiment. The substrate 201 of the organic light emitting diode 200 includes a first sub-pixel, a second sub-pixel, and a third sub-pixel. The plurality of first electrodes 203 are patterned for each of the first sub-pixel, the second sub-pixel and the third sub-pixel. On the first electrode 203, a hole injection layer 207 and a hole transporting-third light emitting layer 210 are formed as a common layer. The hole transporting property of the first sub-pixel-The first auxiliary layer 214-1 and the first light emitting layer 213-1 for emitting the first color light are sequentially disposed on the third light emitting layer 210, Hole transporting property - On the third light emitting layer 110, a second auxiliary layer 2140-2 and a second light emitting layer 213-2 for emitting a second color light are provided. And an electron transport layer 215, an electron injection layer 217, and a second electrode 219 are sequentially provided as a common layer thereon.

The first electrode 203, the hole injection layer 207, the hole transporting-third light emitting layer 210, the first auxiliary layer 214-1, and the first light emitting layer (not shown) of the organic light emitting diode 200 L ₁ , L ₂ , L ₃ , D ₁ , D _2, and D _{3 are} formed on the first electrode 213 - ₁ , the second light emitting layer 213 - 2, the electron transport layer 215, the electron injection layer 217, ₃ , please refer to the description of FIG.

The second auxiliary layer 214-2 of the organic light emitting diode 200 maximizes the resonance of the second color light. The second auxiliary layer 214-2 material refers to the material of the first auxiliary layer 214-1. The second auxiliary layer 214-2 material and the first auxiliary layer 214-1 material may be the same or different from each other. The thickness of the second auxiliary layer 214-2 can be selected within a range satisfying L ₂ and D ₂ as described above.

D ₁ , D _2, and D ₃ in the organic light emitting device 200 have the relationship of D ₁ > D ₂ > D ₃ . For example, by the organic light-emitting device 200, the first auxiliary layer (214-1) and the second auxiliary layer (214-2) of, and may be _{D 1> D 2> D 3} .

Although the organic light emitting device has been described with reference to FIGS. 1 and 2, the organic light emitting device of the present invention is not limited thereto. For example, the first electrodes 103 and 203 may be formed as translucent electrodes, and the second electrodes 119 and 219 may be formed as reflective electrodes. In addition, instead of the hole injection layers 107 and 207, a functional layer having both a hole injection function and a hole transport function can be provided, and various modifications are possible.

The organic light emitting diode may be included in a flat panel display device including a thin film transistor. The thin film transistor may include a gate electrode, a source and a drain electrode, a gate insulating film, and an active layer, and one of the source and drain electrodes may be in electrical contact with the first electrode of the organic light emitting device.

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

Example  One

Aluminum (Al) and ITO (manufactured by SDI) substrates having a thickness of 1300 Å were cut into a size of 50 mm × 50 mm × 0.7 mm as a first electrode (reflective electrode), and ultrasonically cleaned in isopropyl alcohol and pure water for 5 minutes each , UV and ozone cleaning for 30 minutes. 2-TNATA was deposited on the first electrode to form a 200 Å thick hole injection layer. Then, Compound 1 and DPAVBi were co-deposited on the hole injection layer at a weight ratio of 98: 2 to form a 200 Å thick hole transporting- After forming a blue light emitting layer, Balq was deposited on the hole transporting-blue light emitting layer to form a hole blocking layer having a thickness of 50 Å. Alq ₃ was deposited on the hole blocking layer to form an electron transporting layer having a thickness of 200 A, and LiF was deposited thereon to form an electron injection layer having a thickness of 5 ANGSTROM. An organic light emitting device (blue light emission) was fabricated by depositing Mg (Ag) on the electron injection layer to form a second electrode (translucent electrode) 180 Å thick.

The device exhibited a high luminance at a driving voltage of 4.1 V at a current density of 26.0 mA / cm 2 and a luminance of 1029 cd / m 2, a color coordinate of (0.113, 0.120) and a luminous efficiency of 3.96 cd / A.

Example  2

Hole transporting - blue Except that CBP and Ir (ppy) ₃ were co-deposited on the light emitting layer at a weight ratio of 90:10 to form a green light emitting layer having a thickness of 200 Å, and then a hole blocking layer was formed. An organic light emitting device (green light emission) was produced.

The device exhibited a high luminance at a driving voltage of 4.5 V at a current density of 9.8 mA / cm 2 and an emission luminance of 2530 cd / m 2, a color coordinate of (0.244, 0.68) and a luminous efficiency of 26.8 cd / A.

Example  3

Hole transporting property - NPB was deposited on the blue light emitting layer to form a first auxiliary layer having a thickness of 250 Å, and CBP and BPTIr were co-deposited on the first auxiliary layer at a weight ratio of 90:10 to form a 400 Å thick red light emitting layer (Red light emission) was prepared in the same manner as in Example 1, except that a hole blocking layer was formed on the red light emitting layer.

The device exhibited a high luminance at a driving voltage of 4.2 V with a current density of 13.8 A / cm 2 and a luminance of 1934 cd / m 2, a color coordinate of (0.687, 0.310) and a luminous efficiency of 14.0 cd / A.

Example  4

A substrate provided with a thin film transistor was prepared, and then a 1000 Å thick first electrode (reflective electrode) made of Al was formed in a stripe shape. At this time, the first electrode is formed to be electrically connected to the source electrode or the drain electrode of the thin film transistor provided under the substrate.

A pixel defining layer for defining red, green, and blue light-emitting layers is formed on the first electrode using silicon oxide. Then, 2-TNATA is red, green, and deposited to form a 200 Å thick hole injection layer A common layer) was formed.

Compound 1 and DPAVBi were co-deposited on the hole injection layer at a weight ratio of 98: 2 to form a hole transporting-blue light emitting layer (common layer) having a thickness of 200 ANGSTROM.

Subsequently, NPB is deposited on the hole transporting blue light emitting layer of the red sub-pixel to form a first auxiliary layer having a thickness of 250 A on the red sub-pixel, CBP and BTPIr are mixed in a weight ratio of 90 on the first auxiliary layer, : (10) to form a 400 Å thick red light emitting layer. Subsequently, CBP and Ir (ppy) ₃ were co-deposited on the hole transporting blue light emitting layer of the green sub-pixel at a weight ratio (90) :( 10) to form a green light emitting layer having a thickness of 200 Å in the green sub-pixel.

Thereafter, Balq was deposited to form a hole blocking layer (common layer) having a thickness of 50 ANGSTROM and Alq ₃ was deposited on the hole blocking layer to form an electron transport layer (common layer) having a thickness of 200 ANGSTROM, To form a 5 Å thick electron injecting layer (common layer), and then a Mg (Ag) layer was deposited on the electron injecting layer to form a 180 Å thick second electrode (translucent electrode, common layer) An organic light emitting device that emits both green light and blue light was manufactured.

The efficiency and color coordinates of the organic light emitting device of Example 4 were evaluated using an IVL measuring device (PhotoResearch PR650, Keithley 238), and the results are shown in Table 1 below.

Efficiency (cd / A) x color coordinates y color coordinate Red light 14.3 0.68 0.32 Green light 28.9 0.22 0.69 Blue light 2.7 0.13 0.07

According to Table 1, the organic light emitting device of Example 4 has excellent efficiency and color purity for each light emitting color.

On the other hand, the organic light-emitting device of Example 4 exhibited a luminous efficiency of 13.1 cd / A at a light emission luminance of ²⁰⁰ cd / m ² and a 40% device on state as white light blended with red light, green light and blue light, One power consumption was 165mW. The power consumption was calculated by calculating efficiency and color purity using an IVL measuring device (PhotoResearch PR650, Keithley 238).

Example  5

As the first electrode (reflective electrode), aluminum and ITO (manufactured by SDI) having a thickness of 1300 Å were cut into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically cleaned in isopropyl alcohol and pure water for 5 minutes each, UV and ozone cleaning. 2-TNATA was deposited on the first electrode to form a hole injection layer having a thickness of 1200 A, and compound 21 and DPAVBi were co-deposited on the hole injection layer at a weight ratio of 98: 2 to form a hole transporting- And Balq was deposited on the hole transporting-blue light emitting layer to form a hole blocking layer having a thickness of 50 ANGSTROM. Alq ₃ was deposited on the hole blocking layer to form an electron transport layer having a thickness of 250 Å. LiF was deposited to form an electron injection layer having a thickness of 10 Å. Then, Mg: Ag was deposited on the electron injection layer to form a 180 Å thick (Semi-transparent electrode) of the organic light-emitting device (blue light emission).

The organic light-emitting device exhibited a high luminance at a driving voltage of 5.5 V at a current density of 26.0 mA / cm 2 and an emission luminance of 1103 cd / m 2, a color coordinate of (0.133, 0.110) and a luminous efficiency of 4.24 cd / A.

<Compound 21>

Example  6

Hole transportability-CBP and Ir (ppy) ₃ were co-deposited on the blue light emitting layer at a weight ratio of 90:10 to form a green light emitting layer with a thickness of 400 Å, and then a hole blocking layer was formed. (Green light emission) was prepared in the same manner as in Example 1.

The device exhibited a high luminance at a driving voltage of 6.5 V at a current density of 8.3 mA / cm 2 and an emission luminance of 2152 cd / m 2, a color coordinate of (0.238, 0.691) and a luminous efficiency of 25.9 cd / A.

Example  7

Hole transporting property - NPB was deposited on the blue light emitting layer to form a first auxiliary layer having a thickness of 400 Å, and CBP and BPTIr were co-deposited on the first auxiliary layer at a weight ratio of 90:10 to form a 300 Å thick red light emitting layer (Red light emission) was prepared in the same manner as in Example 5, except that a hole blocking layer was formed on the red light emitting layer.

The organic light-emitting device exhibited a high luminance at a driving voltage of 6.2 V, a current density of 12.1 A / cm 2 and an emission luminance of 1,643 cd / m 2, a color coordinate of (0.678, 0.320) and a luminous efficiency of 13.58 cd / A.

Example  8

A substrate provided with a thin film transistor was prepared, and then a 1000 Å thick first electrode made of Al was formed in a stripe shape. At this time, the first electrode is formed to be electrically connected to the source electrode or the drain electrode of the thin film transistor provided under the substrate.

A pixel defining layer for defining red, green, and blue sub-pixels is formed on the first electrode using silicon oxide, and 2-TNATA is co-deposited along the pixel defining layer to form a 1200 Å thick hole injection layer ).

Compound 21 and DPAVBi were co-deposited on the hole injection layer at a weight ratio of 98: 2 to form a hole transporting-blue light emitting layer (common layer) 300 Å thick.

Subsequently, NPB was deposited on the hole transporting blue light-emitting layer of the red sub-pixel to form a first auxiliary layer having a thickness of 300 A, and then CBP and BTPIr were mixed in a weight ratio (90) :( 10) on the first auxiliary layer Followed by co-deposition to form a 300 Å thick red light emitting layer. Subsequently, CBP and Ir (ppy) ₃ were co-deposited on the hole transporting blue light emitting layer of the green sub-pixel at a weight ratio (90): (10) to form a green light emitting layer 300 Å thick.

Thereafter, Balq was deposited to form a hole blocking layer (common layer) having a thickness of 50 A, and Alq ₃ was deposited on the hole blocking layer to form an electron transporting layer (common layer) having a thickness of 250 ANGSTROM, LiF was deposited to form a 10 Å thick hole injection layer (common layer), and then Mg: Ag was deposited on the electron injection layer to form a 180 Å thick second electrode (translucent electrode, common layer) (Emitting red light, green light and blue light).

The efficiency and color coordinates of the organic luminescent device of Example 8 were evaluated using an IVL measuring device (PhotoResearch PR650, Keithley 238), and the results are shown in Table 2 below.

Efficiency (cd / A) x color coordinates y color coordinate Red light 13.6 0.68 0.32 Green light 26.5 0.22 0.71 Blue light 2.7 0.14 0.06

According to Table 2, the organic light emitting device obtained from Example 8 has excellent efficiency and color purity for each light emitting color. On the other hand, the organic luminescent device of Example 8 exhibited a luminous efficiency of 13.3 cd / A at an emission luminance of ²⁰⁰ cd / m ² and a 40% device on state as the luminous efficiency of white light obtained by mixing red light, green light and blue light, One power consumption was 187.3mW. Power consumption was calculated by calculating efficiency and color purity using an IVL measuring device (PhotoResearch PR650, Keithley 238).

Example  9

Compound 27 and DPAVBi were co-deposited on the hole injection layer above Compound 1 and DPAVBi in a weight ratio of 98: 2 to form a hole transporting-blue light emitting layer (common layer) 300 Å thick. The device was fabricated.

<Compound 27>

The efficiency and color coordinates of the organic luminescent device of Example 9 were evaluated using an IVL measuring device (PhotoResearch PR650, Keithley 238), and the results are shown in Table 3 below.

Efficiency (cd / A) x color coordinates y color coordinate Red light 15.4 0.67 0.34 Green light 28.1 0.23 0.69 Blue light 3.8 0.14 0.08

Comparative Example  One

A substrate having a thin film transistor was prepared, and then a 1000 Å thick first electrode (reflective electrode) made of aluminum was formed in a stripe shape. At this time, the first electrode is formed to be electrically connected to the source electrode or the drain electrode of the thin film transistor provided under the substrate.

A pixel defining layer is formed on the first electrode to define red, green, and blue light emitting layers using silicon oxide, and then 2-TNATA is deposited along the pixel defining layer to form a 1000 A thick hole injection layer Then, NPB was deposited to a thickness of 400 Å on the hole injection layer. After that, a 400 Å thick NPB was further deposited on the green subpixel and a 800 Å thick NPB was deposited on the red subpixel using a photomask. The hole transport layer thickness of the red subpixel was 1200 Å, the hole transport layer thickness of the green subpixel And the thickness of the hole transport layer of the blue sub-pixel is 400 ANGSTROM.

Then, the red portion and a hole transport layer formed on the CBP BTPIr the weight ratio (90) :( 10) to co-deposited to form a red light-emitting layer of 300Å thickness, a hole transport layer formed on the green sub-CBP and Ir (ppy) ₃ weight ratio of the pixels of the pixel (90) :( 10) to form a 300 Å thick green luminescent layer, and ADN and DPAVBi were co-deposited on the hole transport layer of the blue sub-pixel at a weight ratio of 90: (10) to form a 150 Å thick blue luminescent layer Respectively.

Thereafter, Balq was deposited to form a hole blocking layer (common layer) having a thickness of 50 A, and Alq ₃ was deposited on the hole blocking layer to form an electron transporting layer (common layer) having a thickness of 250 ANGSTROM, LiF was deposited to form a 5 Å thick electron injection layer (common layer), and then Mg: Ag was deposited on the electron injection layer to form a 180 Å thick second electrode (translucent electrode, common layer) Devices (red light, green light and blue light emission).

The efficiency and color coordinates of the organic light emitting device were evaluated using an IVL measuring device (PhotoResearch PR650, Keithley 238), and the results are shown in Table 4 below.

Efficiency (cd / A) x color coordinates y color coordinate Red light 5.39 0.67 0.32 Green light 24.45 0.21 0.72 Blue light 1.4 0.14 0.06

According to Tables 1 to 4, the efficiency and color purity of the red light, green light and blue light of the organic light emitting devices of Examples 4 and 9 were superior to those of the red light, the green light and the blue light of the organic light emitting device of Comparative Example 1 have.

101, 201: substrate
103: 203: first electrode
107, 207: Hole injection layer
110: 210: hole transporting property - third light emitting layer
113-1 and 223-1: a first light emitting layer
113-2 and 223-2: a second light emitting layer
114, 214-1: a first auxiliary layer
214-2: second auxiliary layer
115, 215: electron transport layer
117, 217: electron injection layer
119, 219: second electrode

Claims (20)

A substrate including a first sub-pixel, a second sub-pixel, and a third sub-pixel;
A plurality of first electrodes formed for each of the first sub-pixel, the second sub-pixel and the third sub-pixel of the substrate;
A second electrode facing the first electrode;
A first light emitting layer formed between the first electrode and the second electrode of the first sub-pixel and emitting a first color light;
A second light emitting layer formed between the first electrode and the second electrode of the second sub-pixel and emitting a second color light; And
A hole transporting third light emitting layer formed on the first sub-pixel, the second sub-pixel and the third sub-pixel and being a common layer emitting a third color light;
Wherein the first electrode is a reflective electrode and the second electrode is a translucent electrode, or ii) the plurality of first electrodes are translucent electrodes and the second electrode is a reflective electrode,
Wherein the first color light is red light, the second color light is green light, the third color light is blue light,
The organic electroluminescent device satisfying the following expressions (1), (2) and (3):
(1) &quot; (2) &quot;

&Quot; (3) &quot;

Among the above-mentioned expressions 1 to 3,
L ₁ is the distance between the first electrode and the second electrode of the first sub-pixel;
L ₂ is a distance between the first electrode and the second electrode of the second sub-pixel;
L ₃ is a distance between the first electrode and the second electrode of the third sub-pixel;
The wavelengths of the first color light, the second color light, and the third color light are respectively lambda ₁ , lambda ₂ and lambda ₃ ;
N ₁ is the refractive index of the layers located between the first electrode and the second electrode of the first sub-pixel;
And n ₂ is a refractive index of a layer positioned between the first electrode and the second electrode of the second sub-pixel;
And n ₃ is the refractive index of the layers positioned between the first electrode and the second electrode of the third sub-pixel;
M ₁ , m ₂ and m ₃ are independently a natural number. The method according to claim 1,
Wherein the hole transporting-third light emitting layer comprises at least one of a compound represented by the following Formula 1 and a compound represented by the following Formula 2:
&Lt; Formula 1 >< EMI ID =

Among the above general formulas (1) and (2)
R ₁ to R ₈ and R ₂₀ to R ₃₅ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, A substituted or unsubstituted C ₂ -C ₅₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₅₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₅₀ aryl group, a substituted or unsubstituted C ₅ -C ₅₀ aryloxy group, a substituted or unsubstituted C ₅ -C ₅₀ aryl Im come, a substituted or unsubstituted C ₂ -C ₅₀ A heteroaryl group, - (X ₂ ) _a -N (R ₄₀ ) (R ₄₁ ) and (X ₃ ) _b -Si (R ₄₂ ) (R ₄₃ ) (R ₄₄ );
X ₁ to X ₃ are each a substituted or unsubstituted C ₅ -C ₅₀ aryl group and a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group;
Ar ₁ and Ar ₂ are independently of each other a substituted or unsubstituted C ₅ -C ₅₀ aryl group and a substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group;
R ₄₀ to R ₄₄ independently represent hydrogen, deuterium, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a carboxyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkyl group, a substituted or unsubstituted C ₂ -C ₅₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₅₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₅₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₅₀ cycloalkyl group, a substituted or unsubstituted C ₅ -C ₅₀ aryl group, a substituted or unsubstituted C ₅ -C ₅₀ aryloxy group, a substituted or unsubstituted C ₅ -C ₅₀ aryl Im import and substituted or unsubstituted C ₂ -C ₅₀ heteroaryl group, and one of the ;
a and b are independently of each other an integer of 0 to 5; The method according to claim 1,
Wherein the hole transporting-third light emitting layer comprises at least one compound represented by the following formula (1a) or (1b):
&Lt; Formula 1a >< EMI ID =

Among the above general formulas (1a) and (1b)
R ₁ is a phenyl group; Carbazolyl group; A fluorenyl group; Naphthyl group; Anthryl group; A pyridinyl group; A quinolinyl group; A benzimidazolyl group; Imidazopyridinyl group; An imidazopyrimidinyl group; A phenyl group substituted by at least one of deuterium, a halogen atom, a hydroxyl group cyano group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a C ₆ -C ₁₄ aryl group and a C ₂ -C ₁₄ heteroaryl group, A carbazolyl group, a fluorenyl group, a naphthyl group, an anthryl group, a pyridinyl group, a quinolinyl group, a benzoimidazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; / RTI >
Z ₁₁ , Z ₁₂ , Z ₂₁ and Z ₂₂ independently represent hydrogen, deuterium, a halogen atom, a methyl group, an ethyl group, a propyl group, a butyl group, a methoxy group, an ethoxy group, a propoxy group, Group;
Ar ₂ represents a phenyl group, a halogenated phenyl group, a C ₁ -C ₁₀ alkylphenyl group, a di (C ₁ -C ₁₀ alkyl) phenyl group, a (C ₆ -C ₁₄ aryl) phenyl group, a di (C ₆ -C ₁₄ aryl) a phenyl group substituted with an amino group, a carbazole group (carbazolyl), halogenated carbazole group, a C ₁ -C ₁₀ alkyl carbazole group, a di (C ₁ -C ₁₀ alkyl) carbazole group, a C ₆ -C ₁₄ aryl group carbazol , di (C ₆ -C ₁₄ aryl) carbazole group, a phenyl group substituted with dia reel group, a fluorenyl group (fluorenyl), halogenated fluorenyl group, C ₁ -C ₁₀ alkyl fluorenyl group, a di (C ₁ -C ₁₀ alkyl) fluorenyl group, a (C ₆ -C ₁₄ aryl) fluorenyl group, a di (C ₆ -C ₁₄ aryl) fluorenyl group, a fluorenyl group substituted by Dia reel group, a naphthyl group (naphthyl) group, a halogenated a naphthyl group, a C ₁ -C ₁₀ alkyl naphthyl group, a di (C ₁ -C ₁₀ alkyl) naphthyl group _{(naphthylene), (C 6 -C} 14 aryl) naphthyl group, a di (C ₆ -C ₁₄ aryl) naphthyl group, A naphthyl group substituted with a diarylamino group, an anthryl group, a halogenated An anthryl group, a C ₁ -C ₁₀ alkyl anthryl group, a di (C ₁ -C ₁₀ alkyl) anthryl group, a (C ₆ -C ₁₄ aryl) anthryl group, a di (C ₆ -C ₁₄ aryl) anthryl Or an anthryl group substituted with a diarylamino group, and the aryl group of the diarylamino group is a phenyl group, a naphthyl group or an anthryl group. The method according to claim 1,
Wherein the hole transporting-third light emitting layer comprises at least one compound represented by the following formula (2a):
&Lt; EMI ID =

In the formula (2a)
R ₄₀ and R ₄₁ independently from each other are a phenyl group; Carbazolyl group; A fluorenyl group; Naphthyl group; Anthryl group; A pyridinyl group; A quinolinyl group; A benzimidazolyl group; Imidazopyridinyl group; An imidazopyrimidinyl group; A phenyl group substituted with at least one of deuterium, a halogen atom, a hydroxyl group cyano group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a C ₆ -C ₁₄ aryl group and a C ₃ -C ₁₄ heteroaryl group, A carbazolyl group, a fluorenyl group, a naphthyl group, an anthryl group, a pyridinyl group, a quinolinyl group, a benzoimidazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; / RTI >
X ₂ is a phenylene group, a C ₁ -C ₁₀ alkylphenylene group, a di (C ₁ -C ₁₀ alkyl) phenylene group, a (C ₆ -C ₁₄ aryl) phenylene group or a di (C ₆ -C ₁₄ aryl)
a is 1 or 2; The method according to claim 1,
And the hole transporting-third light emitting layer further comprises at least one of a phosphorescent dopant and a fluorescent dopant. delete The method according to claim 1,
The hole transporting-third light emitting layer includes a first region located in the first sub-pixel, a second region located in the second sub-pixel, and a third region located in the third sub-pixel, Wherein the first region transports holes from the first electrode to the first light emitting layer, the second region transports holes from the first electrode to the second light emitting layer, and the third region emits the third color light. . delete The method according to claim 1,
Wherein m ₁ , m ₂ and m ₃ in the above formulas (1), ( ₂₎ and ( ₃₎ are 1. 10. The method of claim 9,
A distance between the first electrode of the first sub-pixel and the first light-emitting layer is D ₁ , and D ₁ is 400 ANGSTROM to 1000 ANGSTROM. 10. The method of claim 9,
A distance between the first electrode of the second sub-pixel and the second light-emitting layer is D ₂ , and D ₂ is 300 ANGSTROM to 900 ANGSTROM. 10. The method of claim 9,
A sum of a distance between the first electrode of the third sub-pixel and the hole transporting-third light emitting layer, and a thickness of the hole transporting-third light emitting layer is D ₃ , and D ₃ is 200 ANGSTROM to 800 ANGSTROM. The method according to claim 1,
Wherein m ₁ , m ₂ and m ₃ in the above-mentioned formulas (1), ( ₂₎ and ( ₃₎ are 2. 14. The method of claim 13,
Wherein a distance between the first electrode of the first sub-pixel and the first light-emitting layer is D ₁ , and D ₁ is from 1600 A to 2300 A. 14. The method of claim 13,
A distance between the first electrode of the second sub-pixel and the second light-emitting layer is D ₂ , and D ₂ is 1300 Å to 2000 Å. 14. The method of claim 13,
A sum of a distance between the first electrode of the third sub-pixel and the hole transporting-third light emitting layer, and a thickness of the hole transporting-third light emitting layer is D ₃ , and D ₃ is 900 ANGSTROM to 1800 ANGSTROM. The method according to claim 1,
The distance between the first electrode of the first sub-pixel and the first light emitting layer is D ₁ , the distance between the first electrode of the second sub-pixel and the second light emitting layer is D ₂ , The sum of the distance between the first electrode and the hole transporting-third light emitting layer, and the thickness of the hole transporting-emitting layer is D ₃ , and D ₁ > D ₂ = D ₃ . The method according to claim 1,
The distance between the first electrode of the first sub-pixel and the first light emitting layer is D ₁ , the distance between the first electrode of the second sub-pixel and the second light emitting layer is D ₂ , A sum of a distance between the first electrode and the hole transporting-third light emitting layer and a thickness of the hole transporting-third emitting layer is D ₃ , and D ₁ > D ₂ > D ₃ . The method according to claim 1,
And a first auxiliary layer interposed between the hole transporting-emitting layer and the first emitting layer. The method according to claim 1,
A hole injecting layer or a functional layer simultaneously having a hole injecting function and a hole transporting function is interposed between the hole transporting-third light emitting layer and the first electrode, and the hole injecting layer or the functional layer is disposed between the hole transporting- Wherein the organic layer is in contact with the light emitting layer.

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