KR20160129710A - Organic light emitting device - Google Patents

Abstract

Disclosed is an organic light-emitting device including: a first electrode; a second electrode; a light-emitting layer between the first electrode and the second electrode; and a hole transfer region between the first electrode and the light-emitting layer. According to the present invention, the organic light-emitting device exhibits low driving voltage, high efficiency, and long lifespan, and improves low voltage efficiency.

Description

[0001] The present invention relates to an organic light emitting device,

And an organic light emitting device.

The organic light emitting device 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 hole transport region, an emission layer, an electron transport region, and a second electrode are sequentially formed on the first electrode in the organic light emitting device. Lt; / RTI > structure. The holes injected from the first electrode migrate to the light emitting layer via the hole transporting region and electrons injected from the second electrode migrate to the light emitting layer via the electron transporting region. The carriers such as holes and electrons recombine in the light emitting layer region to generate excitons. This exciton changes from the excited state to the ground state and light is generated.

To provide an organic light emitting device having a low driving voltage, a high efficiency and a long life, and an improved low voltage efficiency.

According to one aspect,

A first electrode;

A second electrode;

An emission layer between the first electrode and the second electrode; And

And a hole transporting region between the first electrode and the light emitting layer,

Wherein the hole transporting region comprises a first compound represented by the following Formula 1 and a second compound represented by the following Formula 2:

≪ Formula 1 >

(2)

≪ Formula 2A > (2B)

Among the above formulas,

X ₁ and X ₂ are independently selected from N, B and P;

L ₁ to L ₆ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ aryl A substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group ;

a1 to a6 are each independently selected from integers from 0 to 3;

Ar ₁ is, independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group;

X ₁₁ to X ₁₃ are independently selected from the group represented by the above formulas (2A) and (2B);

c1 to c3 are independently selected from integers of 0 to 3, and the sum of c1, c2 and c3 is 1 or more;

The rings A ₁ to A ₄ are, independently of each other, benzene or naphthalene;

R ₁ to R ₁₁ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, the acid or its salt, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ A substituted or unsubstituted C ₁ -C ₁₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed A ring group, a substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from a condensed polycyclic group, and _{-Si (Q 1) (Q 2} ) (Q 3);

One of R ₈ and one of R ₉ of Formula 2A is optionally connected to form a saturated or unsaturated ring and one of R ₁₀ and R ₁₁ of Formula 2B is optionally linked to form a saturated or unsaturated ring, Or form an unsaturated ring;

b1 and b4 are each independently selected from integers from 1 to 4;

b2, b3 and b9 to b11 are each independently selected from integers from 1 to 3;

b5 to b7 are independently selected from integers from 1 to 5;

b8 is 1 or 2;

R ₁₂ to R ₁₅ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted Or an unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;

The substituted C ₃ -C ₁₀ cycloalkylene group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₆ -C ₆₀ arylene group, a substituted 2 non-condensed polycyclic aromatic group, a substituted C ₁ - C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted a C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic hydrocarbon ring, at least one of the substituents of the fused polycyclic group,

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group (aryloxy), C ₆ -C ₆₀ arylthio group (arylthio), C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group, a condensed polycyclic, non- at least one of the substituted phenyl group, a terphenyl group and a _{-Si (Q 11) (Q 12} ) (Q 13), C 1 -C 60 alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ A -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group and a terphenyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ hetero aryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, a biphenyl group, a terphenyl group and a _{-Si (Q 21) (Q 22} ) (Q 23) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl An oxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, Monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocyclic polycyclic group, biphenyl group and terphenyl group; And

_{-Si (Q 31) (Q 32} ) (Q 33); ;

Wherein Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, C ₂ -C ₁₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group , A C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group and a terphenyl group, It is a bonding site with atoms.

The organic light emitting device has a low driving voltage, a high efficiency and a long life, and the low voltage efficiency is improved.

1 is a schematic view showing the structure of an organic light emitting device according to an embodiment.

1 schematically shows a cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110, a hole transporting region 130, a light emitting layer 150, an electron transporting region 170, and a second electrode 190. Here, the first electrode 110 may be an anode, and the second electrode 190 may be a cathode.

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.

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

The first electrode 110 may be formed, for example, by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. When the first electrode 110 is an anode, the first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), or the like is used as the first electrode material for forming the first electrode 110 which is a translucent electrode or a reflective electrode. ), Magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag).

The first electrode 110 may have a single layer or a multilayer structure having a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

A hole transporting region 130, a light emitting layer 150, and an electron transporting region 170 are sequentially stacked on the first electrode 110.

The hole transporting region 130 includes the first compound represented by Formula 1 and the second compound represented by Formula 2.

≪ Formula 1 >

(2)

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

X ₁ and X ₂ may be independently selected from N, B, and P, respectively.

For example, X ₁ and X ₂ may be the same or different from each other.

In the general formulas (1) and (2), L ₁ to L ₆ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, A substituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group.

For example, in the general formulas (1) and (2), L ₁ to L ₆ are independently of each other.

A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, A phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, , Anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, and the like. ), Perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, and ovalenyl (hereinafter referred to as "Ovalenylene; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, An acenaphthyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, A thienyl group, a thienyl group, a thienyl group, an anthracenyl group, a fluoranthenyl group, a triphenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a picenyl group, a perylrionyl group, a pentaphenyl group, A phenylene group substituted with at least one of a fluorine, chlorine, bromine, iodine, A thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thienylene group, a thienylene group, a thienylene group, A phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, A phenylene group, a hexacenylene group, a pentacenylene group, a rubicecylene group, a coronenylene group and an ovalenylene group; ≪ / RTI >

According to another embodiment, in the general formulas (1) and (2), L ₁ to L ₆ independently represent a phenylene group, a naphthylene group, a fluorenylene group, a spioro-fluorenylene group, a phenanthrenylene group, A cyanylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group and a chrysenylene group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoran Te in group, a triphenylmethyl group les, pie LES group, a hexenyl group and the Cry _{-Si (Q 31) (Q 32} ) (Q 33) at least one substituted phenyl group, a naphthyl group, a fluorenyl group, a spy of A fluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group and a chrysenylene group; ≪ / RTI >

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

According to another embodiment, L ₁ to L ₆ in the general formulas (1) and (2) may be independently selected from the groups represented by the following formulas (3-1) to (3-11)

Among the above-mentioned formulas (3-1) to (3-11)

Y ₁ is C (Z ₃ ) (Z ₄ );

Z ₁ to Z ₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, Wherein R _{1 is} selected from the group consisting of an acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a klycenyl group,

d1 is selected from an integer of 1 to 4, d2 is selected from an integer of 1 to 3, d3 is selected from an integer of 1 to 6, d4 is selected from an integer of 1 to 8, Is selected from integers, and * and * are binding sites with neighboring atoms.

According to another embodiment, L ₁ to L ₆ , independently of each other, may be selected from the group of the following formulas (4-1) to (4-13):

In the above formulas (4-1) to (4-13), * and * are binding sites with neighboring atoms.

In the general formulas (1) and (2), a1 to a6 may be independently selected from integers of 0 to 3.

a1 represents the number of L < ₁ > and may be an integer selected from 0 to 3; For example, when a1 in the formula 1 is 0, * - (L ₁ ) _a1 - * 'is a single bond, and when a1 is 2 or more, 2 or more L _{1 s} may be the same or different.

The description of a2 to a6 can be understood with reference to the description of a1 and the structures of the formulas (1) and (2).

For example, in Formula 1,

a1 = 1, a2 = 0, a3 = 0,

a1 = 0, a2 = 1, a3 = 0, or

a1 = 0, a2 = 0, and a3 = 1.

For example, a1 = 0, a2 = 1, a3 = 0 in the above formula (1).

According to another embodiment, in Formula 2,

a4 = a5 = a6 = 1,

a4 = 1, a5 = 0, a6 = 0,

a4 = 0, a5 = 1, a6 = 0,

a4 = 0, a5 = 0, a6 = 1,

a4 = 1, a5 = 1, a6 = 0,

a4 = 0, a5 = 1, a6 = 1, or

a4 = 1, a5 = 0, and a6 = 1.

In the above formula (1), Ar ₁ independently represents a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo alkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted ring unsubstituted 1 is selected from a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group (substituted or unsubstituted monovalent non-aromatic condensed polycyclic group) .

For example, in Formula 1, Ar ₁ represents a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, A thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, A benzothiophene group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazopyrimidinyl group, A pyrimidinyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl group A pyranyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, a thiophenol group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoyl group, a benzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an isoxazolyl group, a isoxazolyl group, a isoxazolyl group, a pyrimidinyl group, a pyridazinyl group, Imidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazine Group, iso-benzoxazole group, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole jopi piperidinyl group, a media group, and -Si (Q ₃₁₎ -imidazo flutes (Q ₃₂₎ ( Q ₃₃ ), phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, A thiazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, an imidazolyl group, an imidazolyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, A thiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzyl group Oxazolyl, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole group and a piperidinyl jopi imidazo pyrimidinyl group; ≪ / RTI >

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, and a naphthyl group.

According to another embodiment, in Formula 1, Ar ₁ represents a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, A benzofuranyl group and a dibenzothiophenyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, possess group, a dibenzo furanoid group, a dibenzo thiophenyl group and _{-Si (Q 31) (Q 32} ) (Q 33) of the at least one substituted phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a fluorenyl A phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; ≪ / RTI >

Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, and a naphthyl group.

In the formula (2), X ₁₁ to X ₁₃ may be independently selected from the group represented by the following formulas (2A) and (2B).

≪ Formula 2A > (2B)

In the above formulas (2A) and (2B), the A ₁ to A ₄ rings may be, independently of one another, benzene or naphthalene.

For example, the A ₁ to A ₄ rings in the above formulas (2A) and (2B) may be benzene.

One of R ₈ and one of R ₉ of Formula 2A is optionally connected to form a saturated or unsaturated ring and one of R ₁₀ and R ₁₁ of Formula 2B is optionally linked to form a saturated or unsaturated ring, Or an unsaturated ring. The description of R ₈ to R ₁₁ in the above formulas (2A) and (2B) will be described later.

For example, in the above formula (2), X ₁₁ to X ₁₃ may independently be selected from the group represented by the following formulas (2A) to (2A) and (B)

&Lt; Formula 2A (1) > < Formula (2A) >

&Lt; Formula 2A (3) > < Formula 2A (4) >

&Lt; Formula 2B (1) >

Wherein R _8a refers to R ₈ as defined herein, R _9a refers to R ₉ as defined herein, and R _10a represents the same as defined in the specification, refer to a R ₁₀ as defined herein and, R _11a is selected from the integer of the reference to R _11, and, b8a 1 to 3 defined herein, b9a to b11a are independently of each other, from an integer from 1 to 4 And one of R _8a and R _9a in the above formulas (2A) to (2A) is optionally connected to form a saturated or unsaturated ring, and R _10a (1) And R &lt; _11a & gt _; are optionally linked together to form a saturated or unsaturated ring, and * is a binding site with neighboring atoms.

According to another embodiment, X ₁₁ to X ₁₃ in Formula 2 may be independently selected from the group represented by the following Formulas (2A) (5) to (7) and (2B)

&Lt; Formula 2A (5) > < Formula 2A (6)

&Lt; Chemical Formula 2A (7) > < Chemical Formula 2B (2)

In the above formulas 2A (5) to 2A (7) and 2B (2), R _8b refers to R ₈ as defined herein, R _9b refers to R ₉ as defined herein, and R _10b represents refer to the R ₁₀ defined herein, R _11b is selected from and with reference to the R ₁₁ as defined herein, and b8b is 1 or 2, b9b to b11b are each independently an integer of 1 to 3, and * Is a bonding site with neighboring atoms.

According to another embodiment, it may be selected from the group represented by the following formula (2B) (1) 1 to 2B (1) 5:

&Lt; Formula 2B (1) 1 >   &Lt; Formula 2B (1) 2 > &Lt; Formula 2B (1) 3 >

&Lt; Formula 2B (1) 4 >     &Lt; Formula 2B (1) 5 >

In the above formulas 2B (1) 1 to 2B (1) 5, R _10a refers to R ₁₀ as defined herein, R _11a refers to R ₁₁ as defined herein, and * refers to Binding sites.

In the general formula (2), c1 to c3 are independently selected from integers of 0 to 3, and the sum of c1, c2 and c3 may be one or more.

As the above formula (2) of c1 is shown the number of X _11, may be the same or different from one another if more than 2 X _11, X ₁₁ 2 or more. The description of c2 and c3 in the formula (2) can be understood with reference to the description of the c1 and the structure of the formula (2).

For example, the sum of c1, c2 and c3 in the above formula (2) may be 1 or 2.

R ₁ to R ₁₁ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, Hydra jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ A substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1 Aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, and -Si (Q ₁ ) (Q ₂ ) (Q ₃ ). Q ₁ to Q ₃ refer to those described in this specification.

Among the above formulas,

b1 and b4 are each independently selected from integers from 1 to 4;

b2, b3 and b9 to b11 are each independently selected from integers from 1 to 3;

b5 to b7 are independently selected from integers from 1 to 5;

b8 may be 1 or 2;

In the above formulas, b1 represents the number of R ₁ , and when b1 is 2 or more, b1 of 2 or more may be the same or different from each other. The description of b2 to b11 can be understood by referring to the description of b1 and the structure of the above formulas, respectively.

In the above formulas, R ₁₂ to R ₁₅ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ A substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, Substituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

For example, in the above formulas, R ₁ to R ₁₁ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, A benzothiophenyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, A benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group and an imidazopyrimidinyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl group A pyranyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, a thiophenol group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoyl group, a benzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an isoxazolyl group, a isoxazolyl group, a isoxazolyl group, a pyrimidinyl group, a pyridazinyl group, Imidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazine Group, iso-benzoxazole group, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole jopi piperidinyl group, a media group, and -Si (Q ₃₁₎ -imidazo flutes (Q ₃₂₎ ( Q ₃₃ ), phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, A thiazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, an imidazolyl group, an imidazolyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, A thiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzyl group Oxazolyl, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole group and a piperidinyl jopi imidazo pyrimidinyl group; And

_{-Si (Q 1) (Q 2} ) (Q 3); ;

R ₁₂ to R ₁₅ , independently of each other,

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

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, A benzothiophenyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, A benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group and an imidazopyrimidinyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl group A pyranyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, a thiophenol group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoyl group, a benzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an isoxazolyl group, a isoxazolyl group, a isoxazolyl group, a pyrimidinyl group, a pyridazinyl group, Imidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazine Group, iso-benzoxazole group, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole jopi piperidinyl group, a media group, and -Si (Q ₃₁₎ -imidazo flutes (Q ₃₂₎ ( Q ₃₃ ), phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, A thiazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, an imidazolyl group, an imidazolyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, A thiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzyl group Oxazolyl, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole group and a piperidinyl jopi imidazo pyrimidinyl group; And

_{-Si (Q 1) (Q 2} ) (Q 3); &Lt; / RTI &gt;

The Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group and a naphthyl group.

According to another embodiment, in the above formulas, R ₁ to R ₁₁ are, independently of each other,

A halogen atom, a hydroxyl group, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A cresyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and the _{-Si (Q 31) (Q 32} ) a phenyl group substituted with at least one of (Q ₃₃₎ A biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, A cyanyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; And

_{-Si (Q 1) (Q 2} ) (Q 3); ;

R ₁₂ to R ₁₅ are, independently of each other,

A C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A cresyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and the _{-Si (Q 31) (Q 32} ) a phenyl group substituted with at least one of (Q ₃₃₎ A biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, A cyanyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; And

_{-Si (Q 1) (Q 2} ) (Q 3); ;

Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ may be independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

According to another embodiment, in the above formulas, Ar ₁ is selected from the group consisting of the following formulas (5-1) to (5-19)

R ₁ to R ₁₁ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, A salt thereof, an acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group and a group represented by the following general formulas (5-1) to (5-11)

R ₁₂ to R ₁₅ independently of each other may be selected from the group consisting of a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group and groups represented by the following formulas (5-1) to (5-11)

In the above formulas 5-1 to 5-19

Y ₃₁ is selected from O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ) and Si (Z ₃₆ ) (Z ₃₇ );

Z ₃₁ to Z ₃₇ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, Wherein R _{1 is} selected from the group consisting of an acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group;

e1 is an integer of 1 to 5, e2 is an integer of 1 to 7, e3 is an integer of 1 to 3, e4 is an integer of 1 to 4, e5 is 1 or 2, e6 is an integer of 1 to 6 E7 is an integer of 1 to 9, and * is a binding site with neighboring atoms.

According to another embodiment, Ar ₁ is selected from the group consisting of the following formulas (6-1) to (6-26)

R ₁ to R ₁₁ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, Wherein the acid generator is selected from the group consisting of an acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group and the following formulas (6-1 to 6-23)

R ₁₂ to R ₁₅ independently of each other may be selected from the group consisting of a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group and groups represented by the following formulas (6-1) to (6-23)

In the formulas (6-1) to (6-26), * denotes a bonding site with neighboring atoms.

According to one embodiment, the first compound may be represented by one of the following formulas 1-1 to 1-4:

&Lt; Formula 1-1 >

(1-2)

<Formula 1-3>

<Formula 1-4>

In the above formulas 1-1 to 1-4, X ₁ , L ₁ to L ₃ , a ₁ to a ₃ , Ar ₁ , R ₁₂ to R ₁₄ , R ₁ to R ₄ and b ₁ to b ₄ are as described in the specification .

For example, in Formulas 1-1 through 1-4, a1 through a3 may be independently 0 or 1.

According to one embodiment, a1 and a3 in Formulas 1-1 through 1-4 may be 0, and a2 may be 1.

According to another embodiment, the first compound may be represented by one of the following formulas (1-1) and (1-1):

&Lt; Formula 1-1 (1) >

&Lt; Formula 1-1 (2)

X ₁ , L ₁ , L ₃ , a ₁ , a ₃ , Ar ₁ , R ₁ to R ₄ , b ₁ to b ₄ and R ₁₅ in the above formulas 1-1 (1) and 1-1 (2) the same can be seen and, R ₃₁ to R ₃₃ is the reference to the description of the R ₁ defined herein, b31 are selected from selected from an integer of 1 to 4 and, b32 and b33 are independently an integer of 1 to 5 with each other do.

According to one embodiment, the second compound may be represented by one of the following Formulas 2-1 and 2-2:

&Lt; Formula (2-1)

&Lt; Formula (2-2)

X ₂ , X ₁₁ to X ₁₃ , c 1 to c 3, R ₅ to R ₇ and b ₅ to b _{7 in} the general formulas (2-1) and (2-2) are the same as defined in this specification,

R ₁₆ to R ₁₈ refer to the description of R ₁ defined in the present specification, and b ₁₆ to b ₁₈ are independently selected from an integer of 1 to 4.

For example, in formulas (2-1) and (2-2), R ₁₆ to R ₁₈ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a sulfonyl group or a salt thereof, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, A cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an hendalenyl group, an indacenyl group, an acenaphthyl group , A fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylgrenyl group, A naphthacenyl group, a picenyl group, a peryl-guanyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, Rubicenyl group, coronenyl group and ovalenyl group.

The first compound represented by Formula 1 may be one of the following compounds 101 to 109, and the second compound represented by Formula 2 may be one of the following compounds 1 to 22, but is not limited thereto:

When the hole transporting region includes the first compound represented by Formula 1 and the second compound represented by Formula 2, an optimal recombination balance of holes and electrons can be achieved, The efficiency can be improved and the lifetime can be improved.

The hole transport region may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a hole assist layer, a buffer layer, and an electron blocking layer (EBL).

According to one embodiment, the hole transporting region 130 includes a hole transporting layer and a hole assisting layer, and the hole transporting layer includes a first compound represented by Formula 1, And a second compound to be displayed.

In another embodiment, the hole transport layer comprises a first compound represented by one of Formulas 1-1 and 1-4, and the hole-assist layer includes a second compound represented by one of Formulas 2-1 and 2-2. .

In another embodiment, the hole transport layer comprises a first compound represented by one of the formulas 1-1 (1) and 1-1 (2), and the hole-assist layer includes the compounds represented by Formulas 2-1 and 2-2 Lt; RTI ID = 0.0 &gt; 1 &lt; / RTI &gt;

In yet another embodiment, the hole transport layer comprises one of the compounds 101 to 109, and the hole assisting layer may comprise one of the compounds 1 to 22.

In one embodiment, the hole-assist layer is disposed between the light-emitting layer 150 and the first electrode 110, the hole-transport layer is disposed between the hole-assist layer and the first electrode, May include a first compound represented by Formula 1, and the hole-assist layer may include a second compound represented by Formula 2. [

The hole-assist layer may directly contact the light-emitting layer.

For example, the hole transporting region 130 may include a hole injection layer / a hole transporting layer / a hole transporting layer, a hole transporting layer / a hole transporting layer / a buffer layer / a hole transporting layer, a hole transporting layer / Auxiliary layer and hole transporting layer / buffer layer / hole supporting layer, but the present invention is not limited thereto.

When the hole transporting region includes a hole injection layer, a vacuum evaporation method, a spin coating method, a casting method, an LB method (Langmuir-Blodgett), an inkjet printing method, a laser printing method, a laser induced thermal imaging (LITI) The hole injection layer may be formed on the first electrode 110 by using various methods.

When a hole injection layer is formed by a vacuum deposition method, the deposition conditions are, for example, a deposition temperature of about 100 to about 500 DEG C, a vacuum degree of about 10 ^-8 to about ^10-3 torr, and a deposition rate of about 0.01 to about 100 &lt; sec in the deposition rate range, considering the compound for the hole injection layer to be deposited and the hole injection layer structure to be formed.

When the hole injection layer is formed by the spin coating method, the coating conditions include a compound for a hole injection layer to be deposited and a hole for formation to be formed within a range of a coating speed of about 2000 rpm to about 5000 rpm and a heat treatment temperature range of about 80 [ Can be selected in consideration of the injection layer structure.

The hole transport layer, the hole assisting layer, the buffer layer, and the electron blocking layer may be formed by a method of forming a hole injection layer.

The thickness of the hole transport region 130 may range from about 100 angstroms to about 10,000 angstroms, for example, from about 100 angstroms to about 1000 angstroms. When the hole transporting region 130 includes both the hole transporting layer and the hole supporting layer, the thickness of the hole transporting layer is about 50 Å to about 2000 Å, for example, about 100 Å to about 1500 Å, To about 2,000 angstroms. When the thickness of the hole transporting region 130, the hole transporting layer, and the hole transporting layer satisfy the above-described ranges, satisfactory hole transporting characteristics can be obtained without substantial increase in driving voltage .

The hole transporting region may contain at least one of m-MTDATA, TDATA, 2-TNATA, NPB, beta-NPB, TPD, Spiro-TPD, Spiro- NPB, alpha-NPB, TAPC, HMTPD , TCTA (4,4 ', 4 "-tris (N-carbazolyl) triphenylamine), Pani / DBSA (Polyaniline / Dodecylbenzenesulfonic acid: / Dodecylbenzenesulfonic acid), PEDOT / PSS (poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) (Polyaniline / camphor sulfonic acid) and PANI / PSS (polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)

In addition to the materials described above, the hole transporting region 130 may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly or non-uniformly dispersed within the hole transport region.

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

<Compound HT-D1> <F4-TCNQ>

The hole transporting region may further include at least one of a buffer layer and an electron blocking layer in addition to the hole transporting layer and the hole blocking layer as described above. The buffer layer may compensate the optical resonance distance according to the wavelength of the light emitted from the light emitting layer to increase the light emission efficiency. As the material contained in the buffer layer, a material that can be included in the hole transporting region may be used. The electron blocking layer is a layer that prevents the injection of electrons from the electron transporting region.

Various methods such as vacuum deposition, spin coating, casting, LB method, inkjet printing, laser printing, laser induced thermal imaging (LITI) The light emitting layer 150 is formed. When the light emitting layer 150 is formed by the vacuum deposition method and the spin coating method, the deposition conditions and coating conditions of the first layer 150 refer to deposition conditions and coating conditions of the hole injection layer.

The light emitting layer 150 may include a host and a dopant.

The host may comprise at least one of the following TPBi, TBADN, ADN (also referred to as "DNA "), CBP, CDBP and TCP:

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

&Lt; Formula 301 >

Ar ₃₀₁ - [(L ₃₀₁ ) _{xb 1} -R ₃₀₁ ] _{xb 2}

In Formula 301,

Ar _&lt;

And examples thereof include naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, But are not limited to, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, Indenoanthracene;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl giok group, C ₆ -C ₆₀ aryl giti import, C ₁ -C ₆₀ hetero aryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, a biphenyl group, a terphenyl group and a _{-Si (Q 301) (Q 302} ) (Q 303) ( Q ₃₀₁ to the Q ₃₀₃ is independently selected from hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₆ -C ₆₀ aryl group, and a C ₁ -C ₆₀ heteroaryl group, naphthalene , Heptalene, fluorene, And examples thereof include pyro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, klysene, naphthacene, picene, perylene, anthracene; ;

L ₃₀₁ represents a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene groups, substituted or unsubstituted C ₆ -C ₆₀ arylene groups, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene groups, substituted or unsubstituted divalent non-aromatic A substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;

R ₃₀₁ is

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, Substituted with at least one member selected from the group consisting of a halogen atom, a cyano group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, , A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group and a triazinyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, A naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group which is substituted with at least one member selected from the group consisting of a halogen atom, , A pyrenyl group, a crycenyl group, a pyridinyl group, Group, pyrimidinyl group, pyridazinyl group, a quinolinyl group, an isoquinolinium group, a quinoxaline group salicylate group, a quinazolinyl group, a carbazole group, and triazinyl; ;

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

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

For example, in Formula 301,

L ₃₀₁ ,

A phenylene group, a phenanthrene group, an anthracenylene group, a pyrenylene group and a chrysene ring group; a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl A phenylene group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a klycenyl group, which are substituted with at least one selected from the group consisting of a phenylene group, a naphthylene group, a fluorenylene group, a spioro fluorenylene group, a benzofluorenylene group, A dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, and a chrysenylene group; ;

R ₃₀₁ is

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one selected from a C ₁ -C ₂₀ alkenyl group;

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group and a klycenyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group substituted with at least one member selected from the group consisting of a phenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group and a klycenyl group , A dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a klycenyl group; , But is not limited thereto.

For example, the host may comprise a compound represented by the formula &lt; RTI ID = 0.0 &gt; 301A &

&Lt; Formula 301A >

For a description of the substituents in the above formula (301A), reference is made to what is described herein.

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

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

The dopant in the light emitting layer may include at least one of a fluorescent dopant and a phosphorescent dopant.

The phosphorescent dopant may include an organometallic complex represented by the following formula (401): &lt; EMI ID =

&Lt; Formula 401 >

In the above formula (401)

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

X ₄₀₁ to X ₄₀₄ independently of one another are nitrogen or carbon;

The A ₄₀₁ and A ₄₀₂ rings may be, independently of one another, substituted or unsubstituted benzene, substituted or unsubstituted naphthalene, substituted or unsubstituted fluorene, substituted or unsubstituted spirofluorene, substituted or unsubstituted indene Substituted or unsubstituted thiophenes, substituted or unsubstituted thiophenes, substituted or unsubstituted furan, substituted or unsubstituted imidazoles, substituted or unsubstituted pyrazoles, substituted or unsubstituted thiols, substituted or unsubstituted thiophenes, Substituted or unsubstituted thiazoles, substituted or unsubstituted isothiazoles, substituted or unsubstituted oxazoles, substituted or unsubstituted isoxazoles, substituted or unsubstituted pyridines, substituted or unsubstituted pyrazines, substituted or unsubstituted pyrimidines, Substituted or unsubstituted quinoxaline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, substituted or unsubstituted quinazoline, Substituted or unsubstituted benzoimidazoles, substituted or unsubstituted benzofuran, substituted or unsubstituted benzothiophenes, substituted or unsubstituted isobenzothiophenes, substituted or unsubstituted benzothiophenes, substituted or unsubstituted benzothiophenes, Substituted or unsubstituted benzoxazole, substituted or unsubstituted benzoxazole, substituted or unsubstituted isobenzoxazole, substituted or unsubstituted triazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted triazine, substituted or unsubstituted dibenzofuran, And substituted or unsubstituted dibenzothiophene;

The substituted benzene, substituted naphthalene, substituted fluorene, substituted spiro-fluorene, substituted indene, substituted pyrrole, substituted thiophene, substituted furan, substituted imidazole, substituted pyrazole, Substituted thiazoles, substituted thiazoles, substituted isothiazoles, substituted oxazoles, substituted isoxazoles, substituted pyridines, substituted pyrazines, substituted pyrimidines, substituted pyridazines, substituted quinolines, substituted isoquinolines, Substituted quinoxaline, substituted quinazoline, substituted carbazole, substituted benzoimidazole, substituted benzofuran, substituted benzothiophene, substituted isobenzothiophene, substituted benzoxazole, substituted iso At least one substituent of the benzooxazole, the substituted triazole, the substituted oxadiazole, the substituted triazine, the substituted dibenzofuran and the substituted dibenzothiophene,

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non- of aromatic heterocyclic condensed polycyclic group, a biphenyl group, a terphenyl _{group, -N (Q 401) (Q} 402), -Si (Q 403) (Q 404) (Q 405) and _{-B (Q 406) (Q 407} ) - A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group substituted with at least one group;

C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group and a terphenyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl giok group, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ hetero aryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, a biphenyl group, a terphenyl _{group, -N (Q 411) (Q} 412), -Si (Q 413) (Q 414 ) (Q ₄₁₅₎ and _{-B (Q 416) (Q 417} ) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ Rilti import, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, a biphenyl group and a terphenyl group; And

Q ₄₂₁ , Q ₄₂₂ , Q ₄₂₃ , Q ₄₂₄ , Q ₄₂₅ , and -B Q ₄₂₆ , Q ₄₂₇ ; ;

L ₄₀₁ is an organic ligand;

xc1 is 1, 2 or 3;

xc2 is 0, 1, 2 or 3;

The L ₄₀₁ may be any monovalent, divalent or trivalent organic ligand. For example, L ₄₀₁ may be a halogen ligand (e.g. Cl, F), a diketone ligand (e.g., acetylacetonate, 1,3-diphenyl-l, 3- propanedionate, 6,6-tetramethyl-3,5-heptanedionate, hexafluoroacetonate), carboxylic acid ligands (e.g., picolinate, dimethyl-3-pyrazolecarboxylate, benzoate), carbon But are not limited to, monooxide ligands, isonitrile ligands, cyano ligands, and phosphorus ligands (e.g., phosphine, phosphite).

The Q ₄₀₁ to Q _407, Q ₄₁₁ to Q _417, and Q ₄₂₁ to Q ₄₂₇ are independently, hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₆ -C ₆₀ aryl groups and C ₁ - C ₆₀ heteroaryl is selected from an aryl group.

If the formula of A 401 ₄₀₁ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₁ can form a saturated or unsaturated ring.

If the formula of A 401 ₄₀₂ is to have two or more substituents, bonded to each other at least two substituents of A ₄₀₂ can form a saturated or unsaturated ring.

는 서로 동일하거나 상이할 수 있다. 상기 화학식 401 중 xc1이 2 이상일 경우, A₄₀₁ 및 A₄₀₂는 각각 이웃하는 다른 리간드의 A₄₀₁ 및 A₄₀₂와 각각 직접(directly) 또는 연결기(예를 들면, C₁-C₅알킬렌기, -N(R')-(여기서, R'은 C₁-C₁₀알킬기 또는 C₆-C₂₀아릴기임) 또는 -C(=O)-)를 사이에 두고 연결될 수 있다.When xc1 in Formula 401 is 2 or more, a plurality of ligands of Formula 401

May be the same or different from each other. If the formula xc1 401 is 2 or more of, A ₄₀₁ and A ₄₀₂ are each of the other ligands neighboring A and ₄₀₁ respectively direct and A ₄₀₂ (directly) or linking group (e.g., C ₁ -C ₅ alkylene group, -N (R ') - (wherein, R' - may be connected across a) is C ₁ -C ₁₀ alkyl or C ₆ -C ₂₀ aryl group), or -C (= O).

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

Alternatively, the phosphorescent dopant may comprise the following PtOEP:

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

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

<Formula 501>

In the above formula (501)

Ar ₅₀₁

And examples thereof include naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, But are not limited to, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, Indenoanthracene; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ hetero aryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, a biphenyl group, a terphenyl group and a _{-Si (Q 501) (Q 502} ) (Q 503) ( Q ₅₀₁ to the Q ₅₀₃ independently from each other are selected from hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₆ -C ₆₀ aryl group and a C ₁ -C ₆₀ heteroaryl group), naphthalene , Heptalene, fluorene, spy There is provided a process for the production of a compound of the formula I wherein R 1 is selected from the group consisting of hydrogen, fluorine, fluorine, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, fluoranthene, triphenylene, ; &Lt; / RTI &gt;

The descriptions of L ₅₀₁ to L ₅₀₃ refer to the description of L ₃₀₁ in the present specification, respectively;

R ₅₀₁ and R ₅₀₂ , independently of each other,

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl group A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorene group substituted with at least one member selected from a carbazolyl group, a triazinyl group, a dibenzofuranyl group and a dibenzothiophenyl group A dibenzofluorenyl group, a phenanthrenyl group, anthracenyl group, A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a pyrazinyl group, a pyrazinyl group, a pyridinyl group, A dibenzofuranyl group, and a dibenzothiophenyl group; ;

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

xd4 is selected from 1, 2, 3 and 4.

The fluorescent dopant may comprise at least one of the following compounds FD1 to FD9:

<Compound FD9>

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

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

When the organic light emitting device 10 is a full color organic light emitting device, the light emitting layer 150 may be patterned as a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each individual sub-pixel. Alternatively, the light emitting layer 150 may have a structure in which a red light emitting layer, a green light emitting layer, and a blue light emitting layer are laminated, or a structure in which a red light emitting material, a green light emitting material, .

Next, an electron transporting region 170 may be disposed above the light emitting layer 150.

The electron transport region 170 may include at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. The method of forming the hole blocking layer, the electron transporting layer and the electron injecting layer refers to the hole injecting layer forming method.

For example, the electron transporting region may have a structure of an electron transporting layer / electron injecting layer or a hole blocking layer / electron transporting layer / electron injecting layer stacked sequentially from the light emitting layer, but the present invention is not limited thereto.

The electron transporting layer may include at least one of a compound represented by the following formula (601) and a compound represented by the following formula (602).

<Formula 601>

Ar ₆₀₁ - [(L ₆₀₁ ) _{xe 1} -E ₆₀₁ ] _{xe 2}

In the above formula (601)

Ar ₆₀₁

And examples thereof include naphthalene, heptalene, fluorenene, spiro-fluorene, benzofluorene, dibenzofluorene, phenalene, phenanthrene, anthracene, But are not limited to, fluoranthene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, Indenoanthracene; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ hetero aryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, a biphenyl group, a terphenyl group and a _{-Si (Q 301) (Q 302} ) (Q 303) ( Q ₃₀₁ to the Q ₃₀₃ are independently of each other hydrogen, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₆ -C ₆₀ aryl group or a C ₁ -C ₆₀ heteroaryl group, naphthalene, Talen, fluorene, spiro-fluoro , Benzo fluorene, dibenzo fluorene, page nalren, phenanthrene, anthracene, fluoranthene, triphenylene, pyrene, Cry Sen, naphthacene, pisen, perylene, penta pen and indeno anthracene; ;

For a description of L ₆₀₁ , reference is made to the discussion of L ₃₀₁ herein;

E ₆₀₁ ,

A pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, isoxazolyl, isoxazolyl, pyridinyl, pyrimidinyl, pyridazinyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group (ben and examples thereof include benzofuranyl, benzofuranyl, benzofuranyl, benzofuranyl, zofuranyl, benzothiophenyl, isobenzothiazolyl, benzooxazolyl, isobenzooxazolyl, triazolyl, tetrazolyl, An oxadiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, A pyrimidinyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, An alkenyl group having _{1 to 20} carbon atoms, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a thienyl group, a phenanthryl group, a phenanthryl group, A thiophenyl group, a furanyl group, an imidazole group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, A diazo group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, A pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridyl group, A phenanthrolinyl group, a phenanthryl group, a benzoimidazolyl group, a benzothiophenyl group, a benzothiophenyl group, an isobenzyl group, a benzothiophenyl group, an isothiazolyl group, A thiazolyl group, a thiazolyl group, a dibenzofuranoyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbamoyl group, a benzoxazolyl group, A thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, An isoxazolyl group, a pyridinyl group, A pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinolyl group, A substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted thienyl group, , A benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, An imidazopyridinyl group and an imidazolopyrimidinyl group; ;

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

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

<Formula 602>

In the above formula (602)

₆₁₁ X is N or _{C- (L 611) xe611 -R 611} , X 612 is N or _{C- (L 612) xe612 -R 612} , X 613 is N or C- (L _{613) xe613} -R _613, and , At least one of X ₆₁₁ to X ₆₁₃ is N;

For a description of L ₆₁₁ to L ₆₁₆ , refer to the description of L ₃₀₁ in this specification;

R ₆₁₁ to R ₆₁₆ , independently of each other,

A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, A pyridinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group; And

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an azulenyl group, a fluorenyl group, a spy-fluorenyl group, benzo fluorenyl group, di Anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group substituted with at least one of a quinazolinyl group, a carbazolyl group and a triazinyl group , A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, Di group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, quinolinyl group, an isoquinolinium group, a quinoxaline group salicylate group, a quinazolinyl group, a carbazolyl and possess triazole; ;

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

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

Alternatively, the electron transport layer may include at least one of the BCP, Bphen and to Alq _3, Balq, TAZ and NTAZ.

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

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

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

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

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

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

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

The second electrode 190 is disposed above the electron transporting region 170 as described above. The second electrode 190 may be a cathode, which is an electron injection electrode. At this time, the material for the second electrode 190 may be a metal, an alloy, an electrically conductive compound having a low work function, Can be used. Specific examples of the material for the second electrode 190 include Li, Mg, Al, Al-Li, Ca, Mg-In, , Magnesium-silver (Mg-Ag), and the like. Alternatively, ITO or IZO may be used as the material for the second electrode 190. The second electrode 190 may be a transflective electrode or a transmissive electrode.

In the present specification, the C ₁ -C ₆₀ alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Specific examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl A tert-butyl group, a pentyl group, an iso-amyl group, a hexyl group, and the like. In the present specification, a C ₁ -C ₆₀ alkylene group means a divalent group having the same structure as the above C ₁ -C ₆₀ alkyl group.

The C ₁ -C ₆₀ alkoxy group in the present specification means a monovalent group having the formula: -OA ₁₀₁ (wherein A ₁₀₁ is the above C ₁ -C ₆₀ alkyl group), and specific examples thereof include methoxy group, ethoxy group , Isopropyloxy group, and the like.

In the present specification, the C ₂ -C ₆₀ alkenyl group means a hydrocarbon group having at least one carbon double bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group And the like. In the present specification, the C ₂ -C ₆₀ alkenylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

In the present specification, a C ₂ -C ₆₀ alkynyl group means a hydrocarbon group containing at least one carbon-carbon triple bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl, propynyl, and the like. In the present specification, the C ₂ -C ₆₀ alkynylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclo Heptyl group and the like. The C ₃ -C ₁₀ cycloalkylene group of the specification and the second having the same structure as the above C ₃ -C ₁₀ cycloalkyl group means a group.

In the present specification, the C ₁ -C ₁₀ heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms including at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom , And specific examples thereof include tetrahydrofuranyl, tetrahydrothiophenyl, and the like. In the present specification, a C ₁ -C ₁₀ heterocycloalkylene group means a divalent group having the same structure as the above-mentioned C ₁ -C ₁₀ heterocycloalkyl group.

In the present specification, the C ₃ -C ₁₀ cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one double bond in the ring, but does not have aromatics, Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group and the like. In the present specification, the C ₃ -C ₁₀ cycloalkenylene group means a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

In the present specification, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, Lt; RTI ID = 0.0 &gt; a &lt; / RTI &gt; Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-hyrofuranyl group, a 2,3-hydrothiophenyl group and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

In the present specification, a C ₆ -C ₆₀ aryl group means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C ₆ -C ₆₀ arylene group means a carbamoyl group having 6 to 60 carbon atoms Quot; means a divalent group having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group and the like. The C ₆ -C ₆₀ aryl groups and C ₆ -C ₆₀ arylene If the group contains two or more rings, the 2 or more rings may be fused to each other.

As used herein, a C ₁ -C ₆₀ heteroaryl group is a monovalent group having at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and having a carbocyclic aromatic system having from 1 to 60 carbon atoms C ₁ -C ₆₀ heteroarylene group means a divalent group having at least one heteroatom selected from N, O, P and S as a ring-forming atom and having a carbocyclic aromatic system having 1 to 60 carbon atoms . Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, two or more rings may be fused together.

In the present specification, the C ₆ -C ₆₀ aryloxy group indicates -OA ₁₀₂ (wherein A ₁₀₂ is the C ₆ -C ₆₀ aryl group), the C ₆ -C ₆₀ arylthio is -SA ₁₀₃ , And A ₁₀₃ is the above-mentioned C ₆ -C ₆₀ aryl device).

In the present specification, a monovalent non-aromatic condensed polycyclic group is a condensed polycyclic group in which two or more rings are condensed with each other and contain only carbon as a ring-forming atom, and the whole molecule is a non- (E. G., Having from 8 to 60 carbon atoms). Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. In the present specification, the divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group is a condensed heteropolycyclic group in which two or more rings are condensed with each other and a heteroatom selected from N, O, Si, P and S in addition to carbon as a ring- (For example, having from 1 to 60 carbon atoms) having a non-aromatic group as a whole. The monovalent non-aromatic heterocyclic polycyclic group includes a carbazolyl group and the like. In the present specification, the divalent non-aromatic heterocyclic polycyclic group means a divalent group having the same structure as the monovalent non-aromatic heterocyclic polycyclic group.

In the present specification, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₁ -C ₁₀ heterocycloalkylene group A substituted divalent non-aromatic heterocyclic polycyclic group, a substituted C ₆ -C ₆₀ arylene group, a substituted C ₁ -C ₆₀ heteroarylene group, a substituted divalent non-aromatic condensed polycyclic group, a substituted divalent non-aromatic heterocyclic polycyclic group, a substituted C ₁ -C ₆₀ alkyl, substituted C ₂ -C ₆₀ alkenyl, substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl groups, substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group of aromatic heterocyclic substituents of the fused polycyclic group -, substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non- Least one,

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group (aryloxy), C ₆ -C ₆₀ arylthio group (arylthio), C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group, a condensed polycyclic, non- at least one of the substituted phenyl group, a terphenyl group and a _{-Si (Q 11) (Q 12} ) (Q 13), C 1 -C 60 alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ A -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group and a terphenyl group;

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ hetero aryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, a biphenyl group, a terphenyl group and a _{-Si (Q 21) (Q 22} ) (Q 23) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl An oxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, Monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocyclic polycyclic group, biphenyl group and terphenyl group; And

_{-Si (Q 31) (Q 32} ) (Q 33); &Lt; / RTI &gt;

Wherein Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, C ₂ -C ₁₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group , A C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group and a terphenyl group.

In the present specification, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, and "ter-Bu" or "Bu ^t " means a tert-butyl group.

In the present specification, "biphenyl group" means a monovalent group in which two benzenes are connected to each other through a single bond, and "terphenyl group" means a monovalent group in which three benzenes are connected to each other through a single bond.

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]

Example 1

An ITO glass substrate (manufactured by Corning) having an ITO layer of 15 Ω / cm ² (1,200 Å) formed was cut into a size of 50 mm × 50 mm × 0.7 mm and ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes Thereafter, the substrate was irradiated with ultraviolet rays for 30 minutes, exposed to ozone and cleaned, and the ITO glass substrate (anode) was installed in a vacuum deposition apparatus.

 2-TNATA was vacuum deposited on the ITO anode substrate to form a hole injection layer having a thickness of 600 A, and a hole transport layer was formed by vacuum evaporation of the compound 105 to a thickness of 300 A on the hole injection layer to form a hole transport region Respectively.

 Compound 1 was vacuum deposited on the hole transporting layer to a thickness of 60 Å to form a hole-assist layer.

CBP (host) and PD2 (dopant) were co-deposited on the hole-assist layer in a weight ratio of 95: 5 to form a light-emitting layer with a thickness of 20 nm.

Subsequently, an electron transport layer having a thickness of 300 Å was formed by depositing the following compound ET1 on the light emitting layer, and LiF was deposited on the electron transport layer to form an electron transport layer having a thickness of 10 Å.

Thereafter, Al was deposited on the electron transport region to form a cathode having a thickness of 3,000 Å, thereby preparing an organic light emitting device.

Example 2

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 4 was used instead of Compound 1 in forming the hole auxiliary layer.

Example 3

An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound 7 was used instead of the compound 1 in forming the hole auxiliary layer.

Example 4

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 9 was used instead of Compound 1 in forming the hole auxiliary layer.

Comparative Example 1

An organic light emitting device was fabricated in the same manner as in Example 1 except that TPD was used instead of Compound 105 in forming the hole transport layer.

Comparative Example 2

An organic light emitting device was fabricated in the same manner as in Example 1 except that NPB was used instead of Compound 1 in the formation of the hole assist layer.

Comparative Example 3

An organic light emitting device was fabricated in the same manner as in Example 1, except that TPD was used instead of Compound 105 in the formation of the hole transport layer, and Compound 8 was used instead of Compound 1 in forming the hole assist layer.

Comparative Example 4

TPD was used instead of Compound 105 in the formation of the hole transport layer, and organic light emitting devices were fabricated in the same manner as in Example 1, except that NPB was used instead of Compound 1 in forming the hole assist layer.

Comparative Example 5

An organic light emitting device was fabricated in the same manner as in Example 1, except that the hole-assist layer was not formed, and Compound A was used instead of Compound 105 in forming the hole transport layer.

<Compound A>

Comparative Example 6

An organic light emitting device was fabricated in the same manner as in Example 1, except that the hole-assist layer was not formed and that Compound B was used instead of Compound 105 in forming the hole transport layer.

<Compound B>

Evaluation example 1

The driving voltage, the current density, the efficiency, the luminance, the luminescent color, and the half-life at 1000 nits of the organic light-emitting devices fabricated in Examples 1 to 4 and Comparative Examples 1 to 6 were measured using Kethley SMU 236 and luminance meter PR650 , And the results are shown in Table 1. The half life time is the time taken for the luminance to become 50% of the initial luminance after driving the organic light emitting element.

Hole transport layer material Hole-assisted layer material Driving voltage
(V) electric current
density
(mA / cm ² ) efficiency
(cd / A) Luminance
(cd / m ² ) Luminous color Half-life
(hr) Example 1 compound
105 compound
One 4.1 11.5 6.8 545 blue 215 Example 2 compound
105 compound
4 4.0 10.9 5.3 550 blue 130 Example 3 compound
105 compound
7 4.1 11.3 5.1 560 blue 185 Example 4 compound
105 compound
9 3.8 16.0 3.7 324 blue 235 Comparative Example 1 TPD compound
One 5.2 12.3 4.2 450 blue 40 Comparative Example 2 compound
105 NPB 4.9 12.0 3.6 393 blue 72 Comparative Example 3 TPD compound
8 5.9 9.9 2.7 299 blue 91 Comparative Example 4 TPD NPB 6.5 9.7 3.4 345 blue 77 Comparative Example 5 compound
A - 4.3 10.1 5.1 565 blue 120 Comparative Example 6 compound
B - 5.0 13.0 2.4 254 blue 129

From Table 1, it can be confirmed that the driving voltage, the efficiency, the luminance, and the half life time of the organic light emitting devices of Examples 1 to 4 are superior to the driving voltage, efficiency, luminance, and half life of the organic light emitting devices of Comparative Examples 1 to 6 .

10: Organic light emitting device
110: first electrode
130: hole transport region
150: light emitting layer
170: electron transport region
190: second electrode

Claims (20)

A first electrode;
A second electrode;
An emission layer between the first electrode and the second electrode; And
And a hole transporting region between the first electrode and the light emitting layer,
Wherein the hole transporting region comprises a first compound represented by the following Formula 1 and a second compound represented by the following Formula 2:
&Lt; Formula 1 >

(2)

&Lt; Formula 2A >< EMI ID =

Among the above formulas,
X ₁ and X ₂ are independently selected from N, B and P;
L ₁ to L ₆ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ aryl A substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group;
a1 to a6 are each independently selected from integers from 0 to 3;
Ar ₁ is, independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;
X ₁₁ to X ₁₃ are independently selected from the group represented by the above formulas (2A) and (2B);
c1 to c3 are independently selected from integers of 0 to 3, and the sum of c1, c2 and c3 is 1 or more;
The rings A ₁ to A ₄ are, independently of each other, benzene or naphthalene;
R ₁ to R ₁₁ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, the acid or its salt, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ A substituted or unsubstituted C ₁ -C ₁₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed A ring group, a substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from a condensed polycyclic group, and _{-Si (Q 1) (Q 2} ) (Q 3);
One of R ₈ and one of R ₉ of Formula 2A is optionally connected to form a saturated or unsaturated ring and one of R ₁₀ and R ₁₁ of Formula 2B is optionally linked to form a saturated or unsaturated ring, Or form an unsaturated ring;
b1 and b4 are each independently selected from integers from 1 to 4;
b2, b3 and b9 to b11 are each independently selected from integers from 1 to 3;
b5 to b7 are independently selected from integers from 1 to 5;
b8 is 1 or 2;
R ₁₂ to R ₁₅ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted Or an unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;
The substituted C ₃ -C ₁₀ cycloalkylene group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₆ -C ₆₀ arylene group, a substituted 2 non-condensed polycyclic aromatic group, a substituted C ₁ - C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted a C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic hydrocarbon ring, at least one of the substituents of the fused polycyclic group,
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ - C ₆₀ aryloxy group (aryloxy), C ₆ -C ₆₀ arylthio group (arylthio), C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group, a condensed polycyclic, non- at least one of the substituted phenyl group, a terphenyl group and a _{-Si (Q 11) (Q 12} ) (Q 13), C 1 -C 60 alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl groups and C ₁ A -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group and a terphenyl group;
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group , C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ hetero aryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, a biphenyl group, a terphenyl group and a _{-Si (Q 21) (Q 22} ) (Q 23) of the at least one substituted, C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl An oxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, Monovalent non-aromatic condensed polycyclic groups and monovalent non-aromatic heterocyclic polycyclic groups; And
_{-Si (Q 31) (Q 32} ) (Q 33); ;
Wherein Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, C ₁ -C ₆ alkenyl group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, C ₂ -C ₁₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group , A C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic polycyclic group, a biphenyl group and a terphenyl group, It is a bonding site with atoms. The method according to claim 1,
And L &_lt; ₁ &gt; to L &_lt; ₆ &gt;
A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, A phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, , Anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, and the like. ), Perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, and ovalenyl (hereinafter referred to as &quot;Ovalenylene; And
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, A C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, An acenaphthyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, A thienyl group, a thienyl group, a thienyl group, an anthracenyl group, a fluoranthenyl group, a triphenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a picenyl group, a perylrionyl group, a pentaphenyl group, A phenylene group substituted with at least one of a fluorine, chlorine, bromine, iodine, A thiophenylene group, a thiophenylene group, a thiophenylene group, a thiophenylene group, a thienylene group, a thienylene group, a thienylene group, A phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, A phenylene group, a hexacenylene group, a pentacenylene group, a rubicecylene group, a coronenylene group and an ovalenylene group; &Lt; / RTI &gt; The method according to claim 1,
Wherein L ₁ to L ₆ are independently selected from the group consisting of the following formulas (3-1) to (3-11):

Among the above-mentioned formulas (3-1) to (3-11)
Y ₁ is C (Z ₃ ) (Z ₄ );
Z ₁ to Z ₄ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, Wherein R _{1 is} selected from the group consisting of an acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a klycenyl group,
d1 is selected from an integer of 1 to 4, d2 is selected from an integer of 1 to 3, d3 is selected from an integer of 1 to 6, d4 is selected from an integer of 1 to 8, Is selected from integers, and * and * are binding sites with neighboring atoms. The method according to claim 1,
In Formula 1,
a1 = 1, a2 = 0, a3 = 0,
a1 = 0, a2 = 1, a3 = 0, or
a1 = 0, a2 = 0, and a3 = 1. The method according to claim 1,
In Formula 2,
a4 = a5 = a6 = 1,
a4 = 1, a5 = 0, a6 = 0,
a4 = 0, a5 = 1, a6 = 0,
a4 = 0, a5 = 0, a6 = 1,
a4 = 1, a5 = 1, a6 = 0,
a4 = 0, a5 = 1, a6 = 1, or
a4 = 1, a5 = 0, and a6 = 1. The method according to claim 1,
Ar ₁ represents a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, An isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazolyl group, a pyrazolyl group, a thiazolyl group, A benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, an imidazolyl group, A thiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; And
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl group A pyranyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, a thiophenol group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoyl group, a benzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an isoxazolyl group, a isoxazolyl group, a isoxazolyl group, a pyrimidinyl group, a pyridazinyl group, Imidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazine Group, iso-benzoxazole group, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole jopi piperidinyl group, a media group, and -Si (Q ₃₁₎ -imidazo flutes (Q ₃₂₎ ( Q ₃₃ ), phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, A thiazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, an imidazolyl group, an imidazolyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, A thiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzyl group Oxazolyl, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole group and a piperidinyl jopi imidazo pyrimidinyl group; &Lt; / RTI &gt;
Wherein Q ₃₁ to Q ₃₃ are independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, and a naphthyl group. The method according to claim 1,
X ₁₁ to X ₁₃ in Formula 2 are independently selected from the group consisting of the following Formulas 2A (1) to 2A (4) and 2B (1)
&Lt; Formula 2A (1) >< Formula (2A) >

&Lt; Formula 2A (3) >< Formula 2A (4) >

&Lt; Formula 2B (1) >

Wherein R _8a refers to R ₈ as defined in claim 1, R _9a refers to R ₉ as defined in claim 1, and R (1) to R _10a refers to the R ₁₀ defined in claim 1 and, R _11a is a reference to the R ₁₁ defined in claim 1 and, b8a is selected from an integer of 1 to 3, b9a to b11a are each independently 1 to And one of R &lt; _8a &gt; and R &lt; _9a &gt; in the above formulas 2A (1) to 2A (4) are optionally linked to each other to form a saturated or unsaturated ring, ), One of R _{&lt; 10a} & gt _; and one of R &lt; _11a & gt _; are optionally linked together to form a saturated or unsaturated ring, and * is a binding site with neighboring atoms. The method according to claim 1,
X ₁₁ to X ₁₃ in the general formula (2) are, independently of each other, selected from the group consisting of the following general formulas (2A) to (7A) and (2B)
&Lt; Formula 2A (5) >< Formula 2A (6)

&Lt; Chemical Formula 2A (7) &gt;&lt; Chemical Formula 2B (2)

Wherein R _8b refers to R ₈ as defined in claim 1, R _9b refers to R ₉ as defined in claim 1, and R _10b refers to the R ₁₀ defined in claim 1 and, R _11b is a reference to the R ₁₁ defined in claim 1 and, b8b is 1 or 2, b9b to b11b are independently of each other, from an integer from 1 to 3 And * is a binding site with neighboring atoms. The method according to claim 1,
(2B) is selected from the group consisting of the following chemical formulas (2B) (1) 1 to 2B (1) 5:
&Lt; Formula 2B (1) 1 >< Formula 2B (1) 2 &

&Lt; Formula 2B (1) 4 >< Formula 2B (1) 5 &

Wherein R _10a refers to R ₁₀ defined in claim 1, R _11a refers to R ₁₁ defined in claim 1, and * refers to an atom adjacent to the atom (1) &Lt; / RTI > The method according to claim 1,
R ₁ to R ₁₁ are, independently of each other,
A halogen atom, a hydroxyl group, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, A benzothiophenyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, A benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group and an imidazopyrimidinyl group;
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl group A pyranyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, a thiophenol group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoyl group, a benzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an isoxazolyl group, a isoxazolyl group, a isoxazolyl group, a pyrimidinyl group, a pyridazinyl group, Imidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazine Group, iso-benzoxazole group, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole jopi piperidinyl group, a media group, and -Si (Q ₃₁₎ -imidazo flutes (Q ₃₂₎ ( Q ₃₃ ), phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, A thiazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, an imidazolyl group, an imidazolyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, A thiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzyl group Oxazolyl, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole group and a piperidinyl jopi imidazo pyrimidinyl group; And
_{-Si (Q 1) (Q 2} ) (Q 3); ;
R ₁₂ to R ₁₅ are, independently of each other,
A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrimidinyl group, A benzothiophenyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an isobenzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, A benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group and an imidazopyrimidinyl group;
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spy-fluorenyl group, a fluorenyl group benzo, dibenzo fluorenyl group A pyranyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, a thiophenol group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoyl group, a benzothiazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an isoxazolyl group, a isoxazolyl group, a isoxazolyl group, a pyrimidinyl group, a pyridazinyl group, Imidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazine Group, iso-benzoxazole group, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole jopi piperidinyl group, a media group, and -Si (Q ₃₁₎ -imidazo flutes (Q ₃₂₎ ( Q ₃₃ ), phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, A thiazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, an imidazolyl group, an imidazolyl group, , A pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, A thiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzyl group Oxazolyl, oxadiazole group, a triazinyl group, a dibenzo furanoid group, a dibenzo thiophenyl group, imidazole group and a piperidinyl jopi imidazo pyrimidinyl group; And
_{-Si (Q 1) (Q 2} ) (Q 3); &Lt; / RTI &gt;
Wherein Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group. The method according to claim 1,
R ₁ to R ₁₁ are, independently of each other,
A halogen atom, a hydroxyl group, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;
A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A cresyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and the _{-Si (Q 31) (Q 32} ) a phenyl group substituted with at least one of (Q ₃₃₎ A biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, A cyanyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; And
_{-Si (Q 1) (Q 2} ) (Q 3); ;
R ₁₂ to R ₁₅ are, independently of each other,
A C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;
A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, A cresyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;
Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or its salt, a salt thereof, C ₁ -C ₁₀ alkyl, C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and the _{-Si (Q 31) (Q 32} ) a phenyl group substituted with at least one of (Q ₃₃₎ A biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, A cyanyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; And
_{-Si (Q 1) (Q 2} ) (Q 3); ;
Wherein Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group. The method according to claim 1,
Ar ₁ is selected from the group consisting of the following formulas (5-1) to (5-19)
R ₁ to R ₁₁ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, A salt thereof, an acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group and a group represented by the following general formulas (5-1) to (5-11)
R ₁₂ to R ₁₅ are each independently selected from the group consisting of C ₁ -C ₁₀ alkyl groups, C ₁ -C ₁₀ alkoxy groups and groups represented by the following formulas (5-1) to (5-11):

In the above formulas 5-1 to 5-19
Y ₃₁ is selected from O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ) and Si (Z ₃₆ ) (Z ₃₇ );
Z ₃₁ to Z ₃₇ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, Wherein R _{1 is} selected from the group consisting of an acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a pyrenyl group, a klychenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, An isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group and a triazinyl group;
e1 is an integer of 1 to 5, e2 is an integer of 1 to 7, e3 is an integer of 1 to 3, e4 is an integer of 1 to 4, e5 is 1 or 2, e6 is an integer of 1 to 6 E7 is an integer of 1 to 9, and * is a binding site with neighboring atoms. The method according to claim 1,
Ar ₁ is selected from the group of the following formulas (6-1) to (6-26)
R ₁ to R ₁₁ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, Wherein the acid generator is selected from the group consisting of an acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group and the following formulas (6-1 to 6-23)
R ₁₂ to R ₁₅ are each independently selected from the group consisting of a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group and groups represented by the following Formulas 6-1 to 6-23:

In the formulas (6-1) to (6-26), * denotes a bonding site with neighboring atoms. The method according to claim 1,
Wherein the first compound is represented by one of the following formulas (1-1) to (1-4):
&Lt; Formula 1-1 >

(1-2)

<Formula 1-3>

<Formula 1-4>

Wherein X ₁ , L ₁ to L ₃ , a ₁ to a ₃ , Ar ₁ , R ₁₂ to R ₁₄ , R ₁ to R ₄ and b ₁ to b _{4 in the} above formulas 1-1 to 1-4 are as defined in claim 1 same. The method according to claim 1,
Wherein the first compound is represented by one of the following formulas (1-1) and (1-1):
&Lt; Formula 1-1 (1) >

&Lt; Formula 1-1 (2)

Wherein X ₁ , L ₁ , L ₃ , a ₁ , a ₃ , Ar ₁ , R ₁ to R ₄ , b ₁ to b ₄ and R ₁₄ in the formulas 1-1 (1) R ₃₁ to R ₃₃ refer to the description of R ₁ in the first paragraph, b ₃₁ is selected from integers from 1 to 4, and b 32 and b 33 are independently selected from integers from 1 to 5 . The method according to claim 1,
Wherein the second compound is represented by one of the following formulas (2-1) and (2-2):
&Lt; Formula (2-1)

&Lt; Formula (2-2)

Wherein X ₂ , X ₁₁ to X ₁₃ , c 1 to c 3, R ₅ to R _7, and b ₅ to b ₇ are the same as defined in claim 1,
R ₁₆ to R ₁₈ refer to R ₁ defined in claim ₁ , and b ₁₆ to b ₁₈ are each independently selected from integers from 1 to 4. The method according to claim 1,
Wherein the first compound is one of the following compounds 101 to 109, and the second compound is one of the following compounds 1 to 22:

The method according to claim 1,
Wherein the hole transporting region includes a hole transporting layer and a hole transporting layer,
Wherein the hole transport layer comprises the first compound and the hole assisting layer comprises the second compound. 19. The method of claim 18,
Wherein the hole-assist layer is disposed between the light-emitting layer and the first electrode, and the hole-transport layer is disposed between the hole-assist layer and the first electrode. 19. The method of claim 18,
Wherein the hole-assist layer directly contacts the light-emitting layer.

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