KR20150134248A - Carbazole-based compound and organic light emitting device including the same - Google Patents

Abstract

The present invention relates to a carbazole-based compound and an organic light emitting device comprising the carbazole-based compound. The organic light emitting device comprises: an anode; a cathode; and an organic layer which is interposed between the anode and the cathode, and comprises a light emitting layer. According to one embodiment of the present invention, provided is a carbazole-based compound represented by chemical formula 1.

Description

[0001] The present invention relates to a carbazole-based compound and an organic light-

Carbazole-based compounds and organic light emitting devices containing the same are presented.

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.

According to an example, the organic light emitting element may include an anode, a cathode, and an organic layer interposed between the anode and the cathode and including a light emitting layer. A hole transporting region may be provided between the anode and the light emitting layer, and an electron transporting region may be provided between the light emitting layer and the cathode. The holes injected from the anode move to the light emitting layer via the hole transporting region, and electrons injected from the cathode move to the light emitting layer via the electron transporting region. The carriers such as holes and electrons recombine in the light emitting layer to generate excitons. This exciton changes from the excited state to the ground state and light is generated.

A novel carbazole-based compound and an organic light-emitting device employing the same.

According to one aspect, there is provided a carbazole-based compound represented by the following formula (1): < EMI ID =

≪ Formula 1 >

In Formula 1,

X ₁ is O or S;

L ₁ to L ₅ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkylene group, a substituted or unsubstituted C ₂ -C ₆₀ alkenylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group , A substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, hwandoen C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group), and Substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group (substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group);

a1 to a5 are independently selected from the integers of 0 to 5;

R ₁ to R ₄ , R ₁₁ and R ₁₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, , A hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, hwandoen 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 ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ hetero 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 ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1 Non-condensed polycyclic aromatic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) and -B It is selected from _{(Q 6) (Q 7)} ;

At least one of R ₂ to R ₄ is, independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ hetero cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted Aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;

b1 to b4, b11, b12 and c1 are each independently selected from integers from 1 to 4;

The substituted C ₁ -C ₆₀ alkylene group, a substituted C ₂ -C ₆₀ alkenylene group, substituted C ₃ -C ₁₀ cycloalkylene group, a substituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted C ₃ - C ₁₀ cycloalkenyl group, a substituted C ₂ -C ₁₀ heterocycloalkyl alkenylene group, substituted C ₆ -C ₆₀ aryl group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic Group, a substituted divalent non-aromatic heterocyclic polycyclic 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 A substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₂ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic group, And substituted monovalent non-aromatic The at least one substituent of the parent hetero-

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 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;

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 ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic 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 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 ₂ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) A C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₂ -C ₁₀ heterocycloalkyl group substituted with at least one of -B (Q ₂₆ ) (Q ₂₇ ) alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -C ₆₀ H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;

Wherein Q ₁ to Q _7, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are independently of each other, hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic heterocyclic is selected from a condensed polycyclic group, aromatic condensed polycyclic group, and 1 is non.

According to another aspect, there is provided a liquid crystal display comprising: a first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode, the organic layer including a light emitting layer and containing at least one carbazole-based compound represented by the formula (1).

Since the carbazole compound has excellent electrical properties and thermal stability, the organic light emitting device employing the carbazole compound can have excellent power consumption, efficiency, brightness, and lifetime characteristics.

1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.
Fig. 2 is a diagram showing the emission spectrum and the UV absorption spectrum of Compound 2. Fig.
Fig. 3 is a diagram showing the emission spectrum and UV absorption spectrum of Compound 3. Fig.

The carbazole-based compound is represented by the following Formula 1:

≪ Formula 1 >

In the above formula (1), X ₁ is O or S.

Wherein L ₁ to L ₅ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkylene group, a substituted or unsubstituted C ₂ -C ₆₀ alkenylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl alkenylene , A substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group (substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group).

For example, L ₁ to L ₅ in the above formula (1)

A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, And examples thereof include acenaphthylene, fluorenylene, spiro-fluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluorantrenylene, a perylene group, a perylene group, a fluorenyl group, a fluorenyl group, a fluorenthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, Examples thereof include pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidine, Pyrimidinylene, And examples thereof include pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, isoindolylene, A benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, , Carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzooxazolylene, benzoimidene, and the like. Benzothiophenylene, thiazolylene, isothiazolylene, isothiazolyl, isothiazolyl, isothiazolyl, isothiazolyl, isothiazolyl, isothiazolyl, isothiazolyl, The present invention also relates to a process for preparing a compound represented by the formula (I): wherein R 1, R 2 and e are the same as or different from each other, benzothiazolylene, isoxazolylene, oxazolylene, triazolylene, tetrazolylene, oxadiazolylene, Dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, imidazopyrimidinylene group and imidazopyridinylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group, a phenyl group-substituted phenyl group, a C ₂ -C ₂₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group 1 is a non-aromatic heterocyclic group and the condensed polycyclic _{-Si (Q 33) (Q 34} ) (Q 35) of the at least one substituted phenyl group, pental alkylenyl group, an indenyl group, a naphthyl group, an azulenyl group , A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, , A pyrenylene group, a chryshenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, A thiophenylene group, a thienylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolene group, an indolylene group, , An isoquinolinylene group, a benzoquinolinylene group, a phthalazylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinyl A thiophenylene group, a thiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, A thiazolyl group, a thiazolyl group, a thiazolyl group, an isoxazolyl group, an isoxazolyl group, an oxazolylene group, a triazoylene group, a tetrazolylene group, an oxadiazoloylene group, a triazienylene group, a dibenzofuranylene group, a dibenzothiophenylene group, Jolil Kengi Imida Joppy Limi A dienylene group and an imidazopyridinylene group; ≪ / RTI >

Q ₃₃ to Q ₃₅ independently represent hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, A pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group phthalazinyl group, a quinoxalinyl group , A cyano group, and a quinazolinyl group.

According to one embodiment, L ₁ to L ₅ in the above formula (1) may independently be any one of the formulas (2-1) to (2-37)

Among the above-mentioned formulas (2-1) to (2-37)

Y ₁ is O, S, S (= O), S (= O) ₂ , C (Z ₃ ) (Z ₄ ), N (Z ₅ ) or Si (Z ₆ ) (Z ₇ );

Z ₁ to Z ₇ 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, An anthracenyl group or a salt thereof, an acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, , A pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, Quinolinyl group, quinazolinyl group, quinoxalinyl group, and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₄₅ );

Q ₃₃ to Q ₄₅ independently represent hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, A pyrimidinyl group, a pyridinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group phthalazinyl group, a quinoxaline group, a quinoxaline group, A cyano group, a cyano group, a cyano group, and a quinazolinyl group;

d1 is selected from integers from 1 to 4;

d2 is selected from integers from 1 to 3;

d3 is selected from integers from 1 to 6;

d4 is selected from integers from 1 to 8;

d5 is 1 or 2;

d6 is selected from integers from 1 to 5;

* Is the binding site with neighboring atoms.

According to another embodiment, L ₁ to L ₅ in the general formula (1)

A phenylene group, a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a carbazolylene group, a pyridinylene group, a pyrimidinylene group, a triazienylene group, a quinazolinylene group, Norbornylene group, naphthyridinylene group and oxadiazolene 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, A phenylene group substituted with at least one of a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group and a phenanthrenyl group, , Naphthylene group, phenanthrenylene group, anthracenylene group, triphenylenylene group, carbazolylene group, pyridinylene group, pyrimidinylene group, triazylene group, quinazolinylene group, quinolinylene group, isoquinolinyl Naphthyridinylene group and oxadiazolene ring group; , But is not limited thereto.

According to another embodiment, L ₁ to L ₅ in the above formula (1) may independently be, but not limited to, one of formulas (3-1) to (3-33)

In the above formulas (3-1) to (3-33), * and * are independently bonding sites with neighboring atoms.

In formula (1), a1 represents the number of L ₁ , and may be 0, 1, 2, 3, 4 or 5, for example, 0, 1 or 2, or 0 or 1. When a1 is 0, L ₁ becomes a single bond. When a1 is 2 or more, 2 or more L < ₁ > may be the same or different from each other. The description of a2 to a5 can be understood with reference to a1 and the structure of the formula (1).

According to one embodiment, a1 to a5 in the above formula (1) may be independently 0, 1 or 2, for example, 0 or 1, but is not limited thereto.

In Formula 1, R ₁ to R ₄ , R ₁₁ and R ₁₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, 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 alkenyl 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 ₂ -C ₁₀ A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted aryl group, a C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted A substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group, -N (Q ₁ ) (Q ₂ ), -Si (Q ₃ ) (Q ₄ ) ( Q ₅ ) and -B (Q ₆ ) (Q ₇ );

At least one of R ₂ to R ₄ is, independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ hetero cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted Aromatic monocyclic non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

For example, R ₁ to R ₄ , R ₁₁ and R ₁₂ in Formula 1 are independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, amino group, amidino group, a hydrazine group, a hydrazone jongi, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or salts thereof, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ - C ₂₀ alkoxy group, a substituted or unsubstituted C ₆ -C ₂₀ aryl group, a substituted or unsubstituted C ₂ -C ₂₀ heteroaryl group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic group and a substituted or unsubstituted Aromatic monovalent heterocyclic polycyclic group;

At least one of R ₂ to R ₄ independently represents a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non- Aromatic condensed polycyclic groups and substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic groups.

According to one embodiment, R ₁ to R ₄ , R ₁₁ and R ₁₂ in Formula 1 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 sulfonic acid or a salt thereof and a phosphoric acid or a sulfonic acid or a salt thereof, or a salt thereof, or a salt thereof, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of the salts thereof;

A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptenyl 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, Examples of the substituent include fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaerythritol, A substituted or unsubstituted heteroaromatic group such as pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, ), Furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, thiazolyl, isoxazolyl, isoxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, isoxazolyl, isoxazolyl, isoxazolyl, isoxazolyl, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, a phthalazinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group a benzoimidazolyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoimidazolyl group, Benzooxazolyl, isobenzooxazolyl, isobenzoxazolyl, Triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, A dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a naphthalenyl group, A pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, A pyridinyl 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 benzoquinolyl group, A phenanthridinyl group, a phenanthridinyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A furanyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzothiophenyl group , benzo carbazole group, a dibenzo carbazole group, imidazolidin jopi piperidinyl group, an already substituted by at least one of the imidazo pyrimidinyl group and a _{-Si (Q 33) (Q 34} ) (Q 35), a phenyl group, a pen Frontale group, An indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a pyrenyl group, a phenanthryl group, A naphthacenyl group, a phenanthryl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrroyl group, a thiophenyl group, a furanyl group, An imidazolyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, A carbazolyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, Phenanthrolinyl, phenanthryl, benzoimidazolyl, benzo A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, , A benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, and a pyrimido A benzothiophenyl group; And

_{-Si (Q 3) (Q 4} ) (Q 5); ;

Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ each independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, A heterocyclic group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, an isoquinolyl group, Naphthyl, quinazolinyl, quinazolinyl and quinoxalinyl groups.

According to another embodiment, at least one of R ₂ to R ₄ in the formula (1)

A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, A thiazolyl 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 quinoxalinyl group, A benzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a oxazolyl group, an oxazolyl group, an oxazolyl group, A thiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, and a pyrimido A benzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ at least one substituted one, triphenyl LES group, a carbazole group, a pyrrole group, an imidazole group, a pyrazole group, a thiazole group, isothiazole group, oxazole group, isoxazole group , A pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, A phenanthrolinyl group, a phenanthryl group, a benzoimidazolyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, An imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, and a pyrimidobenzothiophenyl group; ≪ / RTI >

According to another embodiment, at least one of R ₂ to R ₄ in the formula (1)

A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a benzothiazolyl group, an isobenzothiazolyl group, An imidazopyrimidinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, a pyridobenzothiophenyl group, and a pyridylbenzothiophenyl group. A midbenzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, pyridinyl, group possess is, pyrimidinyl group, pyridyl group pyrazinyl, quinolinyl group, an isoquinolinium group, a naphthyridin piperidinyl group, a quinoxalinyl group, a quinazolinyl A benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a tri Group, imidazolidin jopi piperidinyl group, a pyrimidinyl group imidazo, pyrido benzo furanoid group, pyrimido benzo furanoid group, a thiophenyl group and the benzo-pyrido-pyrimido benzo thiophenyl group; , But is not limited thereto.

According to another embodiment, at least one of R ₂ to R ₄ in the formula (1)

A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group, each of which is substituted with at least one of Q ₃₄ and Q ₃₅ ; ≪ / RTI >

According to another embodiment, at least one of R ₂ to R ₄ in the formula (1)

A phenyl group, a phenanthrenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spioro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, A chenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted phenyl group, a pen Frontale group, an indenyl group, a naphthyl group, an azulenyl group, a heptyl Frontale group, indazol hexenyl group, an acetoxy-naphthyl group, a fluorenyl group, a spy-fluorene A perfluorenyl group, a perfluorenyl group, a perfluorenyl group, a perfluorenyl group, a perfluorenyl group, a perfluorenyl group, a perfluorenyl group, , Triphenylmethyl group les, Pie LES group, Cry hexenyl group, a hexenyl group naphtha, blood hexenyl group, a perylenyl group, pentamethylene group, hexamethylene group enyl, penta-hexenyl group, a hexenyl group ruby, nose Ro group and Ovalle group; ≪ / RTI >

According to another embodiment, at least one of R ₂ to R ₄ in the formula (1)

A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A phenanthryl group, a pentalenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, thiophenyl group, furanoid group, a carbazole group, acridinyl, dibenzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a phenyl group , A phenalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A phenylene group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl group; , But is not limited thereto.

For example, R ₁ to R ₄ , R ₁₁ and R ₁₂ in the formula (1)

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 sulfonic acid or a salt thereof and a phosphoric acid or a sulfonic acid or a salt thereof, or a salt thereof, or a salt thereof, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of the salts thereof;

4-1 to 4-48, 5-1 to 5-6 and 6-1 to 6-5 shown below; And

_{-Si (Q 3) (Q 4} ) (Q 5); ;

Q ₃ to Q ₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group And a quinoxalinyl group,

At least one of R ₂ to R ₄ may be independently selected from the following formulas 4-1 to 4-48, 5-1 to 5-6, and 6-1 to 6-5, but is not limited thereto :

Of the above-mentioned formulas 4-1 to 4-48, 5-1 to 5-6 and 6-1 to 6-5,

Y ₃₁ is O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ) or 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, acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, C ₁ -C ₂₀ alkyl-substituted phenyl group, a phenyl-substituted phenyl group, A benzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dicyclopentadienyl group, A quinolinyl group, a quinazolinyl group, a quinoxalinyl group, and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ );

Q ₃₃ to Q ₃₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group And a quinoxalinyl group;

e2 is 1 or 2;

e3 is selected from integers from 1 to 3;

e4 is selected from integers from 1 to 4;

e5 is selected from integers from 1 to 5;

e6 is selected from integers from 1 to 6;

e7 is selected from integers from 1 to 7;

* Is the binding site with neighboring atoms.

In the formula 1, b1 are illustrated as a number of R _1, for 1, 2, 3 or 4, for example, may be a day or two, the other examples. When b1 is 2 or more, two or more R < ₁ > may be the same or different from each other. The description of b2 to b4 can be understood with reference to the description of b1 and the structure of the formula (1).

According to one embodiment, b1 to b4 in the above formula (1) may independently be 1 or 2, for example, 1, but are not limited thereto.

C1 in the formula ( ₁ ) represents the number of - [(L ₁ ) _a1 - (R ₁ ) _b1 ], which may be 1, 2, 3 or 4, for example 1 or 2; When c1 is 2 or more, two or more _{- [(L 1) a1 -} (R 1) b1] may be the same or different from each other.

According to one embodiment, and c1 are 1 In the formula 1, wherein a1 is 0, R ₁ may be hydrogen.

According to another embodiment, R < ₁₁ > and R < ₁₂ > in formula (1) may all be hydrogen.

According to another embodiment, a1 in the formula 1 is 0, c1, b11 and b12 are 1, and R ₁ , R ₁₁ and R ₁₂ independently of one another are 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 hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C ₂₀ alkyl group, A C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group, but is not limited thereto.

According to another embodiment, a2 and a3 in the above formula (1) may be 0, and R ₂ and R ₃ may be hydrogen.

According to another embodiment the of the above formula 1 a3 and a4 is 0, R ₃ and R ₄ may be hydrogen.

According to another embodiment, a2 and a4 in the formula (1) may be 0, and R ₂ and R ₄ may be hydrogen.

According to another embodiment, the carbazole-based compound may be represented by the following formula (1A) or (1B):

≪

≪ Formula 1B >

(1A) of the _{X 1, L 3, L 5} , a description of a3, a5, b2, b3, R _11, R _12, b11 and b12 are the same as those described in claim 1, and

R ₂ and R ₃ are selected from the group consisting of a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, Substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl groups, substituted or unsubstituted C ₆ -C ₆₀ aryl groups, substituted or unsubstituted C ₂ -C ₆₀ heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensation A polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

For example, in the above formulas (1A) and (1B)

L ₃ and L ₅ are, independently of each other,

A phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group and a carbazolylene 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, A phenylene group substituted with at least one of a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group and a phenanthrenyl group, , A naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylrenylene group and a carbazolylene group;

a3 and a5 are independently of each other 0, 1 or 2;

R ₁₁ and R ₁₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, 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 naphthyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group;

Wherein R ₂ and R ₃ are independently selected from the above-mentioned formulas (4-1) to (4-48), (5-1) to (5-6)

b11 and b12 may be 1, but are not limited thereto.

According to another embodiment, R < ₁₁ > and R < ₁₂ > in Formulas 1A and 1B may all be hydrogen, but are not limited thereto.

The carbazole-based compound represented by Formula 1 may be one of the following compounds 1 to 131, but is not limited thereto:

The carbazole-based compound represented by the above-mentioned formula (1) is 1) the "carbazole ring" is bonded to the "carbon number 3" of the "A ring", optionally with - (L ₅ ) _a5 - 1), 2) at least one of R ₂ to R ₄ is, independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ Aromatic heterocyclic polycyclic group (i.e., at least one of R ₂ to R ₄ in Formula 1 is selected from the group consisting of a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non- Quot; cyclic group "). Therefore, the electron density of the "A ring" of the formula (1) can be effectively controlled and the charge transport ability of the carbazole compound represented by the formula (1) can be easily controlled by controlling the substituents of R ₂ to R ₄ .

≪ Formula (1) >

For example, the results of simulations using Gaussian for HOMO, LUMO, T ₁ energy levels and S ₁ energy levels for some of the compounds 1 to 131 and the following compounds A and B are shown in the following Table 1:

HOMO (eV) LUMO (eV) T ₁ (eV) S ₁ (eV) Compound 1 -5.299 -1.649 2.857 3.231 Compound 2 -5.369 -1.845 2.957 3.101 Compound 3 -5.294 -1.694 2.936 3.23 Compound 4 -5.501 -1.598 2.965 3.217 Compound 7 -5.32 -1.800 2.860 2.95 Compound 9 -5.297 -1.222 2.840 3.387 Compound 10 -5.287 -1.904 2.53 3.018 Compound 11 -5.504 -1.803 2.561 3.205 Compound 12 -5.218 -1.748 2.806 2.941 Compound 13 -5.185 -1.967 2.556 2.666 Compound 16 -5.309 -1.878 2.812 2.913 Compound 17 -5.224 -1.187 3.031 3.290 Compound 18 -5.283 -1.224 2.988 3.255 Compound 19 -5.336 -1.357 2.988 3.255 Compound 22 -5.328 -1.924 3.004 3.089 Compound 25 -5.31 -1.722 2.644 3.075 Compound 27 -5.299 -1.709 2.747 3.052 Compound 28 -5.377 -1.893 2.791 3.023 Compound 29 -5.393 -1.916 2.82 3.079 Compound 37 -5.353 -1.777 2.674 3.157 Compound 38 -5.326 -1.686 2.699 3.156 Compound 39 -5.255 -1.818 2.787 3.048 Compound 40 -5.322 -1.730 2.808 3.122 Compound 41 -5.377 -1,290 2.789 3.365 Compound 124 -5.317 -1.730 2.911 3.007 Compound 125 -5.241 -1.789 2.853 2.916

The method for synthesizing the carbazole-based compound represented by the above formula (1) can be easily recognized by those skilled in the art with reference to the following synthesis examples.

Accordingly, the carbazole-based compound represented by Formula 1 may be suitable for use as an organic layer of an organic light emitting device, for example, as a host of a light emitting layer in the organic layer. A second electrode; And an organic layer interposed between the first electrode and the second electrode, the organic layer including a light emitting layer and containing at least one carbazole-based compound represented by the formula (1).

The organic light emitting device has an organic layer containing a carbazole compound represented by the general formula (1) as described above, so that it can have excellent power consumption, efficiency, brightness, and lifetime characteristics.

The carbazole compound represented by Formula 1 may be used between a pair of electrodes of an organic light emitting device. For example, the carbazole compound may include at least one of a luminescent layer, a hole transport region between the first electrode and the luminescent layer (for example, at least one of a hole injection layer, a hole transport layer and an electron blocking layer) (For example, at least one of a hole blocking layer, an electron transporting layer, and an electron injection layer) of the electron transporting layer. For example, the carbazole compound represented by Formula 1 may be included in the light emitting layer. At this time, the light emitting layer may further include a dopant, and the carbazole compound contained in the light emitting layer may serve as a host. The light emitting layer may be a green light emitting layer or a red light emitting layer emitting green light or red light, and the dopant may be a phosphorescent dopant.

In the present specification, the phrase "(organic layer) contains at least one carbazole-based compound" means that one or more carbazole-based compounds (organic layer) belonging to the above- Based carbazole-based compound. "

For example, the organic layer may contain only the compound 1 as the carbazole compound. At this time, the compound 1 may exist in the light emitting layer of the organic light emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the carbazole compound. At this time, the compound 1 and the compound 2 are present in the same layer (for example, both the compound 1 and the compound 2 may be present in the light emitting layer), or they may be present in different layers.

The first electrode is a cathode which is a hole injection electrode and the second electrode is a cathode which is an electron injection electrode. The first electrode is a cathode which is an electron injection electrode and the second electrode is a cathode which is a hole injection electrode.

For example, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may include i) at least one of a hole injecting layer, a hole transporting layer, and an electron blocking layer interposed between the first electrode and the light emitting layer A hole transport region including one; And ii) an electron transporting region interposed between the light emitting layer and the second electrode, the electron transporting region including at least one of a hole blocking layer, an electron transporting layer, and an electron injection layer.

In the present specification, the term "organic layer" refers to a single layer and / or a plurality of layers interposed between the first and second electrodes of the organic light emitting device. The "organic layer" may include not only an organic compound but also an organic metal complex including a metal.

1 schematically shows a cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG. The organic light emitting diode 10 has a structure in which the first electrode 11, the organic layer 15, and the second electrode 19 are sequentially stacked.

A substrate may further be disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a conventional organic light emitting device can be used. A glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.

The first electrode 11 can be formed, for example, by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. The first electrode 11 may be an anode. The first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 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 can be used. Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- .

The first electrode 11 may have a single layer or a multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the present invention is not limited thereto.

An organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region; An emission layer; And an electron transport region.

The hole transporting region may be disposed between the first electrode 11 and the light emitting layer.

The hole transporting region may include at least one of a hole injecting layer, a hole transporting layer, an electron blocking layer, and a buffer layer.

The hole transporting region may include only a hole injecting layer, or may include only a hole transporting layer. Alternatively, the hole transporting region may have a structure of a hole injecting layer / a hole transporting layer or a hole injecting layer / a hole transporting layer / an electron blocking layer which are sequentially stacked from the first electrode 11.

When the hole transporting region includes a hole injecting layer, the hole injecting layer (HIL) may be formed on the first electrode 11 by various methods such as a vacuum deposition method, a spin coating method, a casting method, an LB method, have.

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

When the hole injection layer is formed by the spin coating method, the coating conditions vary depending on the structure and thermal properties of the compound used as the hole injection layer material, the desired hole injection layer, and the coating speed of about 2000 rpm to about 5000 rpm, The heat treatment temperature for removing the solvent after coating may be selected from the range of about 80 캜 to 200 캜, but is not limited thereto.

The conditions for forming the hole transporting layer and the electron blocking layer refer to conditions for forming the hole injection layer.

TPO, Spiro-NPB,? -NPB, TAPC, HMTPD, TCTA (4,4 ', 4,4'-tetramethylpiperidine) , 4 "-tris (N-carbazolyl) triphenylamine), Pani / DBSA (polyaniline / dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrene sulfonate), Pani / CSA (Polyaniline / Camphor sulfonicacid (Polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)), the compound represented by Chemical Formula 201 and the compound represented by Chemical Formula 202 And may include at least one:

≪ Formula 201 >

≪ EMI ID =

In the above formula (201), Ar ₁₀₁ and Ar ₁₀₂ , independently of each other,

A phenanthrenyl group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, an acenaphthylene group, A phenylene group, a phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene 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, 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 ₃ -C ₁₀ cycloalkene group, C ₂ -C ₁₀ heterocycloalkyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - C ₆₀ heteroaryl group, a monovalent non-inde aromatic hydrocarbon ring condensed with at least one substituted one polycyclic group, phenylene group, penta alkylenyl group, a carbonyl group, a naphthyl group, an azulenyl group, an aromatic condensed polycyclic group, and 1 is non- A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a phenanthrenylene group, a phenanthrenylene group, Lai enyl alkylenyl group, a hexenyl group naphtha, blood hexenyl group, a perylenyl group and a carbonyl penta hexenyl groups; ≪ / RTI >

In Formula 201, xa and xb may be independently an integer of 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but is not limited thereto.

In Formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R _119, and R ₁₂₁ to R ₁₂₄ are, independently of each other,

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 , phosphoric acid group or a salt thereof, C ₁ -C ₁₀ alkyl group (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.) and C ₁ -C ₁₀ alkoxy group (e.g., methoxy group, Ethoxy group, propoxy group, butoxy group, pentoxy group, etc.);

Wherein the substituent is selected from the group consisting of 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 hydrazone group, a carboxylic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl 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, A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group which are substituted with at least one of a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group; , But is not limited thereto.

In the above formula (201), R < ₁₀₉ &

A phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl 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, a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group substituted with at least one of a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group; ≪ / RTI >

According to one embodiment, the compound represented by Formula 201 may be represented by Formula 201A below, but is not limited thereto:

≪ Formula 201A >

In the above formula (201A), R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ are described in detail above.

For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include, but are not limited to, the following compounds HT1 to HT20:

The thickness of the hole transporting region may be from about 100 A to about 10,000 A, for example, from about 100 A to about 1000 A. When the hole transporting region includes both the hole injecting layer and the hole transporting layer, the thickness of the hole injecting layer is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transporting layer is about 50 Å For example, from about 100 A to about 1500 A, for example. When the thicknesses of the hole transporting region, the hole injecting layer, and the hole transporting layer satisfy the above-described ranges, satisfactory hole transporting characteristics can be obtained without substantially increasing the driving voltage.

In addition to the materials described above, the hole transporting region 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-tetracano-1,4-benzoquinone di Quinone derivatives such as phosphorus (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as the following compounds HT-D1 and the like, but are not limited thereto.

<Compound HT-D1> <F4-TCNQ>

The hole transporting region may further include a buffer layer.

The buffer layer may serve to increase the efficiency by compensating the optical resonance distance according to the wavelength of the light emitted from the light emitting layer.

A light emitting layer (EML) may be formed on the hole transporting region by a method such as a vacuum evaporation method, a spin coating method, a casting method, or an LB method. In the case of forming the light emitting layer by the vacuum deposition method and the spin coating method, the deposition conditions and the coating conditions vary depending on the compound used, but generally, the conditions can be selected from substantially the same range as the formation of the hole injection layer.

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned as a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked to emit white light.

The light emitting layer may include a carbazole compound represented by the general formula (1). The light emitting layer may further include a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant.

The light emitting layer may include a host and a dopant, and the host may include at least one of the carbazole-based compounds represented by Formula 1.

According to an embodiment, the light emitting layer comprises a first host and a second host,

Wherein the first host and the second host are different from each other,

The carbazole compound represented by Formula 1 is included in the light emitting layer,

I) at least one of R ₂ to R ₄ in Formula 1 is independently selected from the group consisting of hydrogen,

A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a benzothiazolyl group, an isobenzothiazolyl group, An imidazopyrimidinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, a pyridobenzothiophenyl group, and a pyridylbenzothiophenyl group. A midbenzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, pyridinyl, group possess is, pyrimidinyl group, pyridyl group pyrazinyl, quinolinyl group, an isoquinolinium group, a naphthyridin piperidinyl group, a quinoxalinyl group, a quinazolinyl A benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a tri Group, imidazolidin jopi piperidinyl group, a pyrimidinyl group imidazo, pyrido benzo furanoid group, pyrimido benzo furanoid group, a thiophenyl group and the benzo-pyrido-pyrimido benzo thiophenyl group; A carbazole-based compound,

Wherein the second host comprises i) at least one of R ₂ to R ₄ in Formula 1 is represented by Formula 1,

A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A phenanthryl group, a pentalenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, thiophenyl group, furanoid group, a carbazole group, acridinyl, dibenzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a phenyl group , A phenalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A phenylene group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl group; A carbazole-based compound selected from the group consisting of

Q ₃₃ to Q ₃₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group And quinoxalinyl groups.

For example, the light emitting layer includes a first host and a second host,

Wherein the first host and the second host are different from each other,

The carbazole compound represented by Formula 1 is included in the light emitting layer,

I) at least one of R ₂ to R ₄ in the formula (1) is independently selected from the group consisting of a carbazole-based group represented by one of formulas (4-1) to (4-48) &Lt; / RTI &gt;

(Ii) at least one of R ₂ to R ₄ in the formula (1) is independently selected from the group consisting of the formulas (5-1) to (5-6) and (6-1) to -5 &lt; / RTI &gt;

By including the first host and the second host as described above, a balance of hole and electron transport into the light emitting layer can be effectively achieved, and the efficiency, brightness and lifetime of the organic light emitting device can be improved.

On the other hand, according to another embodiment, the light emitting layer includes a host 1 and a host 2,

The host 1 and the host 2 are different from each other,

The carbazole compound represented by Formula 1 is included in the light emitting layer,

The host 1 comprises the carbazole-based compound represented by Formula 1;

The host 2 may include at least one of a first compound represented by the following chemical formula 41 and a second compound represented by the following chemical formula 61:

&Lt; EMI ID =

&Lt; Formula 61 >

<Formula 61A> &Lt; Formula 61B >

Among the above formulas

X ₄₁ is _{N - [(L 42) a42} - (R 42) b42], S, O, S (= O), S (= O) 2, C (= O), C (R 43) (R 44 ), Si (R ₄₃ ) (R ₄₄ ), P (R ₄₃ ), P (= O) (R ₄₃ ) or C = N (R ₄₃ );

Ring A ₆₁ in the above formula (61) is represented by the above formula (61A);

Ring A ₆₂ in the above formula (61) is represented by the above formula (61B);

X ₆₁ is _{N - [(L 62) a62} - (R 62) b62], S, O, S (= O), S (= O) 2, C (= O), C (R 63) (R 64 ), Si ( _R63 ) ( _R64 ), P ( _R63 ), P (= O) ( _R63 ) or C = N ( _R63 );

And X ₇₁ are C (R ₇₁₎ or N, X ₇₂ is C (R ₇₂₎ or N, X ₇₃ is C, and (R ₇₃₎ or N, X ₇₄ is a C (R ₇₄₎ or N, X ₇₅ is C (R ₇₅₎ or N, X ₇₆ is a C (R ₇₆₎ or N, X ₇₇ is a C (R ₇₇₎ or N, X ₇₈ is C (R ₇₈₎ or N;

Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ - C ₆₀ heteroaryl group, an unsubstituted 2-substituted or unsubstituted non-aromatic condensed polycyclic group, and a substituted or unsubstituted 2 non-aromatic heterocyclic is selected from the condensed polycyclic group;

n1 and n2 are each independently selected from integers from 0 to 3;

a41, a42, a61 and a62 are each independently selected from integers from 0 to 3;

R ₄₁ to R ₄₄ , R ₅₁ to R ₅₄ , R ₆₁ to R ₆₄ and R ₇₁ to R ₇₉ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, , a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone 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 thereof, a substituted or unsubstituted 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, hwandoen C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ hetero cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ unsubstituted 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 ₂ -C ₆₀ hetero O Group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q ₄ ) (Q ₅ ) and -B (Q ₆ ) (Q ₇ );

b41, b42, b51 to b54, b61, b62 and b79 are independently selected from integers from 1 to 3;

The substituted C ₁ -C ₆₀ alkylene group, a substituted C ₂ -C ₆₀ alkenylene group, substituted C ₃ -C ₁₀ cycloalkylene group, a substituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted C ₃ - C ₁₀ cycloalkenyl group, a substituted C ₂ -C ₁₀ heterocycloalkyl alkenylene group, substituted C ₆ -C ₆₀ aryl group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic Group, a substituted divalent non-aromatic heterocyclic polycyclic 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 A substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₂ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic group, And substituted monovalent non-aromatic The at least one substituent of the parent hetero-

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 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;

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 ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic 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 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 ₂ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) A C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₂ -C ₁₀ heterocycloalkyl group substituted with at least one of -B (Q ₂₆ ) (Q ₂₇ ) alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -C ₆₀ H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;

Wherein Q ₁ to Q _7, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are independently of each other, hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic heterocyclic is selected from a condensed polycyclic group, aromatic condensed polycyclic group, and 1 is non.

According to one embodiment, R ₄₁ to R ₄₄ , R ₅₁ to R ₅₄ , R ₆₁ to R _64, and R ₇₁ to R ₇₉ 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 sulfonic acid or a salt thereof and a phosphoric acid or a sulfonic acid or a salt thereof, or a salt thereof, or a salt thereof, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of the salts thereof;

A phenyl group, a phenyl group-substituted phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spioro-fluorenyl group, A phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, A thiophene group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isothiazolyl group, a thiazolyl group, , An isoxazolyl group, a pyridinyl group, a pyrazinyl 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 phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl A benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, a benzoxazolyl group, a benzoxazolyl group, a benzoxazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzothiazolyl group, A thiazolyl 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 imidazo group A phenanthryl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenenyl group, a perylenyl group , A pentaphenyl group, a hexacenyl group, a penta A thiazolyl group, an isothiazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridyl group, a pyridyl 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 naphthyl group, A phenanthrolinyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isothiophenyl group, a benzothiophenyl group, a benzothiophenyl group, an isothiazolyl group, Benzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranoyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzoyl group A carbazolyl group, an imidazopyridinyl group, and an imidazo group Lee Media 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 ₂₀ alkyl, C ₁ -C ₂₀ alkoxy _{group, -Si (Q 33) (Q} 34) (Q 35), a phenyl group, a phenyl-substituted phenyl group, a pen Frontale group, an indenyl group, a naphthyl group , An azulenyl group, an heptalenyl 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, , A fluorenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, An imidazolyl group, an imidazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, A pyridinyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, Benzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, dibenzothiophenyl group, A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an imidazolyl group, an imidazolyl group, an imidazopyrimidinyl group, an imidazopyrimidinyl group, An acenaphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, a thienyl group, A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isothiazolyl group, an isothiazolyl group, an isoxazolyl group, an isoxazolyl group, A phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, A benzoimidazolyl group, a benzofuranyl group, a benzothiophene group, An isothiazolyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranoyl group, a dibenzothiophenyl group, , Dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl group; And

_{-Si (Q 3) (Q 4} ) (Q 5); ;

Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ each independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, A heterocyclic group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, an isoquinolyl group, Naphthyl, quinazolinyl, quinazolinyl and quinoxalinyl groups, but is not limited thereto.

For example, the first compound may be represented by one of the following formulas (41-1) to (41-12), and the second compound may be represented by one of the following formulas (61-1) to

In the formula, 41-1 to 41-12 and 61-1 to _{61-6 X 41, X 61, L} 41, L 42, a41, a42, L 61, L 62, a61, a62, R 41 to R _44, Description of the b41, b42, R ₆₁ to _{R 64, b61, b62, R} 71 to R ₇₉ and b79, see bar described herein.

For example, at least one of R &lt; ₂ &gt; to R &lt; ₄ &gt; in the carbazole-based compound represented by the formula (1)

A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a benzothiazolyl group, an isobenzothiazolyl group, An imidazopyrimidinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, a pyridobenzothiophenyl group, and a pyridylbenzothiophenyl group. A midbenzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, pyridinyl, group possess is, pyrimidinyl group, pyridyl group pyrazinyl, quinolinyl group, an isoquinolinium group, a naphthyridin piperidinyl group, a quinoxalinyl group, a quinazolinyl A benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a tri Group, imidazolidin jopi piperidinyl group, a pyrimidinyl group imidazo, pyrido benzo furanoid group, pyrimido benzo furanoid group, a thiophenyl group and the benzo-pyrido-pyrimido benzo thiophenyl group; &Lt; / RTI &gt;

When the first compound represented by Formula 41 is included in the host 2 and at least one of R ₄₁ , R _42, and R ₅₂ of the first compound and the second compound represented by Formula 61 is contained in the host 2, At least one of R ₆₁ and R ₆₂ of the second compound is, independently of each other,

A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A phenanthryl group, a pentalenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, thiophenyl group, furanoid group, a carbazole group, acridinyl, dibenzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a phenyl group , A phenalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A phenylene group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl group; , &Lt; / RTI &gt;

Q ₃₃ to Q ₃₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group Or a quinoxalinyl group.

As another example, at least one of R ₂ to R ₄ in the carbazole-based compound represented by Formula 1 contained in Host 1 may be,

A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A phenanthryl group, a pentalenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, thiophenyl group, furanoid group, a carbazole group, acridinyl, dibenzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a phenyl group , A phenalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A phenylene group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl group; , &Lt; / RTI &gt;

When the first compound represented by Formula 41 is included in the host 2 and at least one of R ₄₁ , R _42, and R ₅₂ of the first compound and the second compound represented by Formula 61 is contained in the host 2, At least one of R ₆₁ and R ₆₂ of the second compound is, independently of each other,

An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indole group A phenanthrolinyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazolidinyl group, 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ group of at least one substituted, a pyrrolyl group, an imidazole group, a pyrazole group, a thiazole group, isothiazole group, oxazole group, isoxazole group, a pyridinyl group, pyrazinyl, 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 benzyl group, A benzothiazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; &Lt; / RTI &gt;

Q ₃₃ to Q ₃₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group And quinoxalinyl groups.

As another example, at least one of R ₂ to R ₄ in the carbazole-based compound represented by Formula 1 contained in Host 1 is independently selected from the group consisting of those represented by one of Formulas 4-1 to 4-48,

When the first compound represented by Formula 41 is included in the host 2 and at least one of R ₄₁ , R _42, and R ₅₂ of the first compound and the second compound represented by Formula 61 is contained in the host 2, At least one of R ₆₁ and R ₆₂ of the second compound may be independently represented by any one of the above-mentioned formulas (5-1) to (5-6) and (6-1) to (6-5).

As another example, at least one of R &lt; ₂ &gt; to R &lt; ₄ &gt; in the carbazole-based compound represented by the above formula (1) -5, &lt; / RTI &gt;

When the first compound represented by Formula 41 is included in the host 2 and at least one of R ₄₁ , R _42, and R ₅₂ of the first compound and the second compound represented by Formula 61 is contained in the host 2, At least one of R ₆₁ and R ₆₂ of the second compound may be independently represented by any one of the above-mentioned formulas (4-1) to (4-48).

According to one embodiment, the first compound represented by Formula 41 includes one of the following compounds A1 to A83, and the second compound represented by Formula 61 may include one of the following Compounds B1 to B20, But are not limited to:

For example, the light emitting layer may include one of the compounds 1 to 131 as the host 1, and the host 2 may include one of the above-described compounds A1 to A83 and B1 to B20, but is not limited thereto.

When both the host 1 and the host 2 are included in the light emitting layer, the balance of holes and electrons injected into the light emitting layer can be effectively controlled, thereby realizing an organic light emitting device having improved light emitting efficiency and life.

The weight ratio between the first host and the second host in the light emitting layer and the weight ratio between the host 1 and the host 2 in the light emitting layer are independently from 1:99 to 99: 1, for example, from 10:90 to 90:10 Can be selected within the range. When the weight ratio range of the first host and the second host and the weight ratio range of the host 1 and the host 2 satisfy the above-described conditions, the hole and electron injection balance into the light emitting layer can be effectively controlled.

The dopant in the light emitting layer may include a phosphorescent dopant that emits light in accordance with a fluorescence emission mechanism or a phosphorescent dopant that emits light in accordance with a phosphorescent emission mechanism.

According to one embodiment, the dopant in the light emitting layer may be a phosphorescent dopant, and the phosphorescent dopant may include an organometallic compound represented by the following general formula (81)

<Formula 81>

In the above formula (81)

M is iridium, platinum, osmium, titanium, zirconium, hafnium, europium, terbium or thorium;

Y ₁ to Y ₄ independently of one another are carbon (C) or nitrogen (N);

Y ₁ and Y ₂ are connected through a single bond or a double bond, Y ₃ and Y ₄ are connected through a single bond or a double bond;

CY ₁ and CY ₂ are each independently selected from the group consisting of benzene, naphthalene, fluorene, spiro-fluorene, indene, pyrrole, thiophene, furan, imidazole, pyrazole, thiazole, isothiazole, Isooxazole, pyridine, pyrazine, pyrimidine, pyridazine, quinoline, isoquinoline, benzoquinoline, quinoxaline, quinazoline, carbazole, benzoimidazole, benzofuran, benzothiophene, isobenzo CY ₁ and CY ₂ are optionally substituted with _one or more substituents selected from the group consisting of halogen, cyano, nitro, cyano, nitro, cyano, thiophene, benzooxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, dibenzofuran or dibenzothiophene, Bonded to each other through a single bond or an organic linking group;

R ₈₁ and R ₈₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, acid or its salt, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, -SF _5, 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 Substituted or unsubstituted C ₂ -C ₁₀ 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 ₂ -C ₁₀ heterocycloalkyl group, hwandoen C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ hetero cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl oxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic Sum polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) or -B (Q ₆ (Q &lt; ₇ &gt;);

a81 and a82 are each independently selected from integers from 1 to 5;

n81 is selected from integers from 0 to 4;

n82 is 1, 2 or 3;

L ₈₁ is a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand.

The descriptions of R ₈₁ and R ₈₂ refer to the description of R ₄₁ in the present specification.

The phosphorescent dopant may include, but is not limited to, at least one of the following compounds PD1 to PD78:

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.

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 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.

Next, an electron transporting region is disposed above the light emitting layer.

The electron transporting region may include at least one of a hole blocking layer, an electron transporting layer, and an electron injection layer.

For example, the electron transporting region may have a structure of a hole blocking layer / electron transporting layer / electron injecting layer or electron transporting layer / electron injecting layer, but is not limited thereto. The electron transporting layer may have a single layer or a multi-layer structure including two or more different materials.

The forming conditions of the hole blocking layer, the electron transporting layer and the electron injecting layer in the electron transporting region refer to the forming conditions of the hole injecting layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of the following BCP and Bphen, but is not limited thereto.

The thickness of the hole blocking layer may be about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics can be obtained without increasing the driving voltage substantially.

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

Alternatively, the electron transporting layer may include at least one of the following compounds ET1 and ET2, but is not limited thereto.

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 also include an electron injection layer (EIL) that facilitates the injection of electrons from the second electrode 19.

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

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.

A second electrode 19 is formed on the organic layer 15. The second electrode 19 may be a cathode. As the material for the second electrode 19, a metal, an alloy, an electrically conductive compound having a relatively low work function, or a combination thereof may be used. Specific examples thereof include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- And may be used as a material for forming the second electrode 19. Alternatively, the transmissive second electrode 19 can be formed using ITO or IZO to obtain a front light emitting element.

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

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, and 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.

In the present specification, the C ₁ -C ₆₀ alkoxy group 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 a methoxy group, Isopropyloxy group and the like.

In the present specification, the C ₂ -C ₆₀ alkenyl group has a structure containing 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, and a butenyl group do. 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, the C ₂ -C ₆₀ alkynyl group has a structure containing one or more carbon triple bonds 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, Tyl 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 ₂ -C ₁₀ heterocycloalkyl group means a monovalent monocyclic group having 2 to 10 carbon atoms including at least one hetero atom selected from N, O, P and S as a ring-forming atom, Examples include tetrahydrofuranyl, tetrahydrothiophenyl, and the like. In the present specification, a C ₂ -C ₁₀ heterocycloalkylene group means a divalent group having the same structure as the C ₂ -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.

The C ₂ -C ₁₀ heterocycloalkenyl group in the present specification is a monovalent monocyclic group having 2 to 10 carbon atoms including at least one hetero atom selected from N, O, P and S as a ring-forming atom, It has one double bond. Specific examples of the C ₂ -C ₁₀ heterocycloalkenyl group include a 2,3-hyrofuranyl group, a 2,3-hydrothiophenyl group and the like. In the present specification, the C ₂ -C ₁₀ heterocycloalkenylene group means a divalent group having the same structure as the C ₂ -C ₁₀ heterocycloalkenyl group.

In the present specification, the 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 aryl If the alkylene group contains two or more rings, the two or more rings may be fused to each other.

As used herein, a C ₂ -C ₆₀ heteroaryl group means a monovalent 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 from 2 to 60 carbon atoms And the C ₂ -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 2 to 60 carbon atoms do. Specific examples of the C ₂ -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 ₂ -C ₆₀ heteroaryl group and the C ₂ -C ₆₀ heteroarylene group include two or more rings, two or more rings may be fused with each other.

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 include only carbon as a ring-forming atom (for example, the number of carbon atoms may be from 8 to 60) , And a monovalent group in which the entire molecule has non-aromacity. Examples of the 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 group in which two or more rings are condensed with each other, and in addition to carbon (for example, the number of carbon atoms may be from 2 to 60) as a ring-forming atom Means a monovalent group containing a heteroatom selected from N, O, P and S, and the whole molecule having non-aromacity. 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 ₁ -C ₆₀ alkylene group, the substituted C ₂ -C ₆₀ alkenylene group, the substituted C ₂ -C ₆₀ alkynylene group, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C _A substituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted C ₃ -C ₁₀ cycloalkenylene group, a substituted C ₂ -C ₁₀ heterocycloalkenylene group, a substituted C ₆ -C ₆₀ arylene group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic group, a substituted bivalent non-condensed polycyclic aromatic heterocyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C C ₂ -C ₁₀ alkynyl group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₂ -C ₁₀ heterocycloalkenyl group , substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted monovalent non- Aromatic condensed polycyclic groups and groups 1 is a non-at least one substituent of the aromatic heterocyclic group is a condensed polycyclic,

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 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;

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 ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic 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 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, a C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) A C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₂ -C ₁₀ heterocycloalkyl group substituted with at least one of -B (Q ₂₆ ) (Q ₂₇ ) alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ A heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); &Lt; / RTI &gt;

In addition, the specification of the Q ₁ to Q _7, Q ₁₁ to Q ₁₇ and Q ₃₁ to Q ₃₇ are, each independently, hydrogen, C ₁ -C ₆₀ alkyl groups to each other, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl C ₁ -C ₆ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₂ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₁₀ heterocycloalkyl group, _A C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

In the present specification, "phenyl group-substituted phenyl group" means "phenyl group substituted with at least one phenyl group".

In the present specification, the "C ₁ -C ₂₀ alkyl group-substituted phenyl group" means "a phenyl group substituted with at least one C ₁ -C ₂₀ alkyl group".

Hereinafter, compounds and organic light emitting devices according to one embodiment of the present invention will be described in more detail with reference to the following Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples. In the following Synthesis Examples, the amounts of 'B' and 'A' used in the expression "B" was used in place of "A" were the same on the molar equivalent basis.

[Example]

Synthesis Example 1: Synthesis of Compound 2

Synthesis of intermediate A

To a 1 L round bottom flask was dissolved 3-amino-2-methoxydibenzofuran (11.1 g, 52 mmol) in Et ₂ O (130 mL) and BF ₃ O Et ₂ O (26.4 mL, 208 mmol) Lt; / RTI &gt; To the resulting mixture was slowly added a mixture of tert- Butyl nitrile (21.7 mL, 64 mL) in Et ₂ O (64 mL) for 30 min, stirred for 30 min and Et ₂ O (300 mL) And the mixture was stirred at 0 ° C for 10 minutes. The resulting reaction mixture was concentrated, and then a solution prepared by dissolving NaI (9.4 g, 62.4 mmol) and I ₂ (1.2 g, 4.7 mmol) in dry CH ₃ CN (340 mL) was slowly added dropwise at room temperature and stirred for 1 hour After adding 20% aqueous Na ₂ S ₂ O ₃ (20 mL) and stirring, chloroform (300 mL × 3) was added. The obtained organic layer was dried over MgSO ₄ and the solvent was evaporated. The obtained residue was purified by silica gel The crude product was purified by column chromatography to obtain Intermediate A (12.1 g, yield 72%). The resulting compound was confirmed by LC-MS.

LC-MS ( m / z ) = C ₁₃ H ₁₁ NO ₂ (M ⁺ ) 213.

Synthesis of intermediate B

Intermediate A (8.92 g, 27.5 mmol), carbazole (5.06 g, 30.3 mmol), CuI (0.52 g, 2.75 mmol), K ₃ PO ₄ (8.76 g, 41.3 mmol) cyclohexanediamine (74 μL , 0.07 mmol) was mixed with 1,4-dioxane (140 mL), and the mixture was heated to 110 ° C. under nitrogen and refluxed for 48 hours. The mixture was cooled to room temperature, methylene chloride (200 mL). The resulting organic layer was dried over MgSO ₄ and the solvent was evaporated. The resulting residue was purified by silica gel column chromatography to obtain Intermediate B (3.5 g, 35%). The resulting compound was confirmed by LC-MS.

LC-MS (m / z) = C 25 H 17 NO 2 (M +) 363.

Synthesis of intermediate C

Boron tribromide (15.0 mL, 15.0 mmol; 1.0 M in dichloromethane) was slowly added dropwise over 10 minutes to a mixture of intermediate B (3.64 g, 10.0 mmol) in methylene chloride (100 mL) 0.0 &gt; 0 C &lt; / RTI &gt; for 10 hours. Subsequently, 30 mL of water was added to the mixture at 0 ° C., and the mixture was stirred. Then, methylene chloride (60 mL × 3) was added thereto, and the obtained organic layer was dried over MgSO ₄ and the solvent was evaporated to obtain intermediate C.

Synthesis of intermediate D

Trifluoromethanesulfonic anhydride (5.14 mL, 30.5 mmol) was slowly added dropwise to the mixture at 0 ° C under nitrogen atmosphere and the mixture was stirred for 7 hours at 0 ° C Lt; / RTI &gt; Next, 15 mL of 1.0 M aqueous HCl was added to the mixture at 0 ° C., and the mixture was stirred. Then, methylene chloride (60 mL × 3) was added to the organic layer, and the obtained organic layer was dried over MgSO ₄ and the solvent was evaporated. The crude product was purified by column chromatography to obtain Intermediate D (3.2 g, 65%). The resulting compound was confirmed by LC-MS.

LC-MS (m / z) = C 25 H 14 F 3 NO 4 S (M +) 481.

Synthesis of Compound 2

Intermediate D (7.0 g, 14.5 mmol), 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- , 5-triazine (6.31 g, 14.5 mmol), Pd (Pph ₃ ) ₄ (0.84 g, 0.725 mmol) and K ₂ CO ₃ (5.01 g, 36.3 mmol) were mixed with 50 mL of THF and 25 mL of distilled water The mixture was heated to 80 DEG C and stirred for 18 hours while refluxing. The resultant mixture was cooled to room temperature, and the resulting solid was filtered. The resulting solid was dissolved in toluene, dried over MgSO ₄ , and the solvent was removed. The resulting residue was recrystallized from toluene: MeO to obtain Compound 2 g, 67%). The resulting compound was confirmed by LC-MS.

LC-MS ( m / z ) = C ₄₅ H ₂₈ N ₄ O (M ⁺ ) 640.

Synthesis Example 2: Synthesis of Compound 3

Instead of 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- pyrimidine (6.17 g, 14.5 mmol) was used instead of diphenyl-2- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan- Compound 3 (8.5 g, 91%) was obtained in the same manner as in the synthesis of Compound 2 of Synthesis Example 1 above. The resulting compound was confirmed by LC-MS.

LC-MS ( m / z ) = C ₄₅ H ₂₈ N ₄ O (M ⁺ ) 639.

Synthesis Example 3: Synthesis of Compound 27

Intermediate D (7.88 g, 16.4 mmol), 9- (quinolin-5-yl) -3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -9H-carbazole A mixture of Pd (Pph ₃ ) ₄ (0.94 g, 0.82 mmol) and K ₂ CO ₃ (5.66 g, 40.9 mmol) in 100 mL of THF and 50 mL of distilled water was heated to 80 ° C. And stirred for 18 hours while refluxing. The resulting mixture was cooled to room temperature, and 100 mL of distilled water was added to the mixture. After stirring, methylene chloride (150 mL X 3) was added to the mixture, and the obtained organic layer was dried over MgSO ₄ and the solvent was removed. The residue was purified by silica gel column chromatography to obtain Compound 27 (7.57 g, 74%). The resulting compound was confirmed by LC-MS.

LC-MS ( m / z ) = C ₄₅ H ₂₈ N ₄ O (M ⁺ ) 625.

Evaluation Example 1: Evaluation of HOMO, LUMO and triplet (T1) energy levels

The HOMO, LUMO and T1 energy levels of compounds 2, 3 and 27 were evaluated according to the method of Table 2 and the results are shown in Table 3.

HOMO energy level evaluation method Cyclic voltammetry (CV) (electrolyte: 0.1 M Bu ₄ NClO ₄ / solvent: CH ₂ Cl ₂ / electrode: three electrode system (working electrode: GC, reference electrode: Ag / AgCl, After obtaining a graph of the potential (V) -current (A) of each compound, the HOMO energy level of each compound was calculated from the reduction onset of the graph LUMO energy level evaluation method Each compound was diluted with CHCl ₃ to a concentration of 1 x 10 ^-5 M and the UV absorption spectrum was measured at room temperature using a Shimadzu UV-350 Spectrometer. The edge of the absorption spectrum LUMO energy level is calculated using the optical band gap (Eg) T1 energy level evaluation method A mixture of toluene and each compound (1 mg of each compound dissolved in 3 ml of toluene) was placed in a quartz cell, and the mixture was placed in liquid nitrogen (77 K). The photoluminescence spectrum was measured using a photoluminescence measuring instrument, Calculate the T1 energy level by analyzing only peaks observed at low temperatures compared to the luminescence spectrum

Compound No. HOMO (eV)
(Measured value) LUMO (eV)
(Measured value) T1 energy level (eV) 2 -5.72 -2.15 2.70 3 -5.69 -2.15 2.65 27 -5.56 -2.21 2.54

It can be seen from Table 3 that the compounds have electrical characteristics suitable for use as a material for an organic light emitting device.

Evaluation example  2: Evaluation of thermal properties

Thermal analysis (N ₂ atmosphere, temperature range: room temperature to 800 ° C (10 ° C / min) - TGA) was performed using TGA (Thermo Gravimetric Analysis) and DSC (Differential Scanning Calorimetry) Disposable Al Pan (TGA), Disposable Al pan (DSC)) were performed in the same manner as in Example 1, and the results are summarized in Table 4. According to Table 4, it can be confirmed that the compounds have excellent thermal stability.

Compound No. Tg (占 폚) Tm (占 폚) Tc (占 폚) Td (1% / 5%, 占 폚) 2 144.4 309.8 n / a 389/418 3 139.8 289.6 n / a 387/419 27 155.3 N / A N / A 379/414

Evaluation example  3: Evaluation of luminescence spectrum

The UV absorption spectrum and PL (photoluminescence) spectrum of Compound 2 were evaluated to evaluate the luminescence properties of each polymer. First, Compound 2 was diluted with toluene to a concentration of 0.2 mM, and the UV absorption spectrum was measured using a Shimadzu UV-350 Spectrometer. This was repeated for compounds 3 and 27.

Meanwhile, Compound 2 was diluted in toluene to a concentration of 10 mM, and PL (Photoluminecscence) spectrum (@ 298K) was measured using an ISC PC1 Spectrofluorometer equipped with a Xenon lamp. This was repeated for compounds 3 and 27.

The PL spectrum and the UV absorption spectrum of the compound 2 are shown in FIG. 2, and the PL spectrum and the UV absorption spectrum of the compound 3 are shown in FIG. 3. The maximum wavelength of each spectrum and the half width ratio (FWHM) Respectively.

UV absorption spectrum PL spectrum Compound No. lambda max lambda max FWHM 2 323 nm 425 nm 67 nm 3 322 nm 383 nm 70 nm 27 328 nm 413 nm 54 nm

2 and 3 and Table 5, it can be confirmed that the compounds 3, 2 and 27 have excellent luminescence properties.

Example  One

A glass substrate on which an ITO (Indium Tin Oxide) electrode (first electrode, anode) having a thickness of 1500 Å was formed was washed with distilled water ultrasonic waves. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried and transferred to a plasma cleaner, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transferred to a vacuum deposition machine.

Compound NPB was vacuum deposited on the ITO electrode of the glass substrate to form a hole transporting layer having a thickness of 1000 A to form a hole transporting region.

The compound 2 (host) and Ir (ppy) ₃ (dopant (compound PD1 in this specification), 10 wt%) were co-deposited on the hole transporting region to form a 300Å thick light emitting layer.

BAlq was vacuum-deposited on the light-emitting layer to form a first electron transporting layer having a thickness of 50 A, and Alq ₃ was vacuum-deposited on the first electron transporting layer to form a second electron transporting layer having a thickness of 250 A, To form an electron injection layer having a thickness of 5 A and an Al second electrode (cathode) having a thickness of 1000 A on the electron injection layer. Thus, an organic light emitting device was fabricated.

Example 2

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 3 was used instead of Compound 2 as a host in forming the light emitting layer.

Example 3

An organic light emitting device was fabricated in the same manner as in Example 1, except that Compound 27 was used instead of Compound 2 as a host in forming the light emitting layer.

Example 4

Except that the thickness of the hole transport layer was changed to 1350 ANGSTROM and Compound 27 and PtOEP were used in place of Compound 2 and Ir (ppy) _{3 in} forming the light emitting layer, respectively. Respectively.

Comparative Example 1

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound A was used instead of Compound 2 as a host in forming the light emitting layer.

<Compound A>

Comparative Example 2

An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound B was used instead of Compound 2 as a host in forming the light emitting layer.

<Compound B>

Comparative Example 3

Except that Compound A and PtOEP were used instead of Compound 2 and Ir (ppy) _{3 in} forming the light emitting layer while changing the thickness of the hole transport layer to 1350 ANGSTROM, Respectively.

Comparative Example 4

Except that Compound B and PtOEP were respectively used instead of Compound 2 and Ir (ppy) _{3 in} forming the light emitting layer while changing the thickness of the hole transport layer to 1350 ANGSTROM, Respectively.

Comparative Example 5

An organic light emitting device was fabricated in the same manner as in Example 1, except that CBP was used instead of Compound 2 in forming the light emitting layer.

Comparative Example 6

Except that CBP and PtOEP were used instead of the compound 2 and Ir (ppy) _{3 in the} formation of the light emitting layer while changing the thickness of the hole transport layer to 1350 ANGSTROM. Respectively.

Evaluation Example 4: Characteristic evaluation of organic light emitting device

The power consumption, luminance, efficiency, luminescent color and lifetime of each of the organic light emitting devices manufactured in Examples 1 to 4 and Comparative Examples 1 to 6 were evaluated using Kethley SMU 236 and luminance meter PR650, Respectively. The lifetime LT ₉₇ is a measurement of the time (hr) required for the luminance after driving to become 9% when the initial luminance is 100%. The lifetime of green OLED (LT ₉₇ ) was evaluated under 6000 nit conditions, and the lifetime of red OLED (LT ₉₇ ) was evaluated under 1500 nit conditions.

EML Power Consumption
(lm / W) Luminance
(cd / m 2) efficiency
(cd / A) Luminous color LT ₉₇ (hr) Host Dopant Example 1 Compound 2 Ir (ppy) ₃ 28.2 4755 48.5 green 90 Example 2 Compound 3 Ir (ppy) ₃ 28.3 4865 49.6 green 88 Example 3 Compound 27 Ir (ppy) ₃ 25.3 4715 47.5 green 84 Example 4 Compound 27 PtOEP 10.9 2435 24.0 Red 95 Comparative Example 1 Compound A Ir (ppy) ₃ 23.9 4815 48.0 green 72 Comparative Example 2 Compound B Ir (ppy) ₃ 22.6 4690 47.5 green 74 Comparative Example 3 Compound A PtOEP 10.3 2365 23.0 Red 85 Comparative Example 4 Compound B PtOEP 9.95 2270 22.5 Red 88 Comparative Example 5 CBP Ir (ppy) ₃ 22.0 4,766 47.7 green 61 Comparative Example 6 CBP PtOEP 22.1 2.212 22.1 Red 89

From the above Table 6, it can be seen that the organic light emitting devices of Examples 1 to 3 have superior power consumption, brightness, efficiency and lifetime characteristics as compared with the organic light emitting devices of Comparative Examples 1, 2 and 5, It can be confirmed that the organic electroluminescent devices of Comparative Examples 3, 4 and 6 have excellent power consumption, brightness, efficiency and lifetime characteristics.

10: Organic light emitting device
11: first electrode
15: Organic layer
19: Second electrode

Claims (20)

A carbazole-based compound represented by the following formula
&Lt; Formula 1 >

In Formula 1,
X ₁ is O or S;
L ₁ to L ₅ independently represent a substituted or unsubstituted C ₁ -C ₆₀ alkylene group, a substituted or unsubstituted C ₂ -C ₆₀ alkenylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group , A substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, hwandoen C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group), and Substituted or unsubstituted divalent non-aromatic heterocyclic polycyclic group (substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group);
a1 to a5 are independently selected from the integers of 0 to 5;
R ₁ to R ₄ , R ₁₁ and R ₁₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, , A hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, hwandoen 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 ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ hetero 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 ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted 1 Non-condensed polycyclic aromatic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) and -B It is selected from _{(Q 6) (Q 7)} ;
At least one of R ₂ to R ₄ is, independently of each other, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ hetero cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted Aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group;
b1 to b4, b11, b12 and c1 are each independently selected from integers from 1 to 4;
The substituted C ₁ -C ₆₀ alkylene group, a substituted C ₂ -C ₆₀ alkenylene group, substituted C ₃ -C ₁₀ cycloalkylene group, a substituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted C ₃ - C ₁₀ cycloalkenyl group, a substituted C ₂ -C ₁₀ heterocycloalkyl alkenylene group, substituted C ₆ -C ₆₀ aryl group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic Group, a substituted divalent non-aromatic heterocyclic polycyclic 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 A substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₂ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic group, And substituted monovalent non-aromatic The at least one substituent of the parent hetero-
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 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;
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 ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic 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 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 ₂ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) A C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₂ -C ₁₀ heterocycloalkyl group substituted with at least one of -B (Q ₂₆ ) (Q ₂₇ ) alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -C ₆₀ H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; And
_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;
Wherein Q ₁ to Q _7, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are independently of each other, hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic heterocyclic is selected from a condensed polycyclic group, aromatic condensed polycyclic group, and 1 is non. The method according to claim 1,
L ₁ to L ₅ 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, And examples thereof include acenaphthylene, fluorenylene, spiro-fluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluorantrenylene, a perylene group, a perylene group, a fluorenyl group, a fluorenyl group, a fluorenthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, Examples thereof include pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidine, Pyrimidinylene, And examples thereof include pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, isoindolylene, A benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, , Carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzooxazolylene, benzoimidene, and the like. Benzothiophenylene, thiazolylene, isothiazolylene, isothiazolyl, isothiazolyl, isothiazolyl, isothiazolyl, isothiazolyl, isothiazolyl, isothiazolyl, The present invention also relates to a process for preparing a compound represented by the formula (I): wherein R 1, R 2 and e are the same as or different from each other, benzothiazolylene, isoxazolylene, oxazolylene, triazolylene, tetrazolylene, oxadiazolylene, Dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, imidazopyrimidinylene group and imidazopyridinylene 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, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group, a phenyl group-substituted phenyl group, a C ₂ -C ₂₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group 1 is a non-aromatic heterocyclic group and the condensed polycyclic _{-Si (Q 33) (Q 34} ) (Q 35) of the at least one substituted phenyl group, pental alkylenyl group, an indenyl group, a naphthyl group, an azulenyl group , A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, , A pyrenylene group, a chryshenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, A thiophenylene group, a thienylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolene group, an indolylene group, , An isoquinolinylene group, a benzoquinolinylene group, a phthalazylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinyl A thiophenylene group, a thiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, a benzothiophenylene group, A thiazolyl group, a thiazolyl group, a thiazolyl group, an isoxazolyl group, an isoxazolyl group, an oxazolylene group, a triazoylene group, a tetrazolylene group, an oxadiazoloylene group, a triazienylene group, a dibenzofuranylene group, a dibenzothiophenylene group, Jolil Kengi Imida Joppy Limi A dienylene group and an imidazopyridinylene group; &Lt; / RTI &gt;
Q ₃₃ to Q ₃₅ independently represent hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, A pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group phthalazinyl group, a quinoxalinyl group , A cyinolinyl group, and a quinazolinyl group. The method according to claim 1,
And L &_lt; ₁ &gt; to L &_lt; ₅ &gt; independently of each other represent one of the following formulas 2-1 to 2-37:

Among the above-mentioned formulas (2-1) to (2-37)
Y ₁ is O, S, S (= O), S (= O) ₂ , C (Z ₃ ) (Z ₄ ), N (Z ₅ ) or Si (Z ₆ ) (Z ₇ );
Z ₁ to Z ₇ 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, An anthracenyl group or a salt thereof, an acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, , A pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, Quinolinyl group, quinazolinyl group, quinoxalinyl group, and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₄₅ );
Q ₃₃ to Q ₄₅ independently represent hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, A pyrimidinyl group, a pyridinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group phthalazinyl group, a quinoxaline group, a quinoxaline group, A cyano group, a cyano group, a cyano group, and a quinazolinyl group;
d1 is selected from integers from 1 to 4;
d2 is selected from integers from 1 to 3;
d3 is selected from integers from 1 to 6;
d4 is selected from integers from 1 to 8;
d5 is 1 or 2;
d6 is selected from integers from 1 to 5;
* Is the binding site with neighboring atoms. The method according to claim 1,
L ₁ to L ₅ are, independently of each other,
A phenylene group, a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a carbazolylene group, a pyridinylene group, a pyrimidinylene group, a triazienylene group, a quinazolinylene group, Norbornylene group, naphthyridinylene group and oxadiazolene 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, A phenylene group substituted with at least one of a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group and a phenanthrenyl group, , Naphthylene group, phenanthrenylene group, anthracenylene group, triphenylenylene group, carbazolylene group, pyridinylene group, pyrimidinylene group, triazylene group, quinazolinylene group, quinolinylene group, isoquinolinyl Naphthyridinylene group and oxadiazolene ring group; &Lt; / RTI &gt; The method according to claim 1,
A1 to a5 are, independently of each other, 0, 1 or 2; The method according to claim 1,
R ₁ to R ₄ , R ₁₁ and R ₁₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, A substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, Unsubstituted C ₆ -C ₂₀ aryl groups, substituted or unsubstituted C ₂ -C ₂₀ heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, and substituted and unsubstituted monovalent non-aromatic hetero A condensed polycyclic group;
At least one of R ₂ to R ₄ independently represents a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non- An aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group. The method according to claim 1,
R ₁ to R ₄ , R ₁₁ and R ₁₂ 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 sulfonic acid or a salt thereof and a phosphoric acid or a sulfonic acid or a salt thereof, or a salt thereof, or a salt thereof, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of the salts thereof;
A phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptenyl 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, Examples of the substituent include fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaerythritol, A substituted or unsubstituted heteroaromatic group such as pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrolyl, thiophenyl, ), Furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, thiazolyl, isoxazolyl, isoxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, isoxazolyl, isoxazolyl, isoxazolyl, isoxazolyl, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, a phthalazinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group a benzoimidazolyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoimidazolyl group, Benzooxazolyl, isobenzooxazolyl, isobenzoxazolyl, Triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, A dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group and a pyrimidobenzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a naphthalenyl group, A pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, A pyridinyl 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 benzoquinolyl group, A phenanthridinyl group, a phenanthridinyl group, a benzoimidazolyl group, a benzoimidazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A furanyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzothiophenyl group , benzo carbazole group, a dibenzo carbazole group, imidazolidin jopi piperidinyl group, an already substituted by at least one of the imidazo pyrimidinyl group and a _{-Si (Q 33) (Q 34} ) (Q 35), a phenyl group, a pen Frontale group, An indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, A phenanthrenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a pyrenyl group, a phenanthryl group, A naphthacenyl group, a phenanthryl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrroyl group, a thiophenyl group, a furanyl group, An imidazolyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, A carbazolyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a phenanthridinyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, Phenanthrolinyl, phenanthryl, benzoimidazolyl, benzo A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, , A benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, and a pyrimidobenzothiophenyl group; And
_{-Si (Q 3) (Q 4} ) (Q 5); ;
Q ₃ to Q ₅ and Q ₃₃ to Q ₃₅ each independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, A heterocyclic group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, an isoquinolyl group, A pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, The method according to claim 1,
At least one of R &lt; ₂ &gt; to R &lt; ₄ &gt;
A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, A thiazolyl 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 quinoxalinyl group, A benzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a oxazolyl group, an oxazolyl group, an oxazolyl group, A thiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, and a pyrimido A benzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ at least one substituted one, triphenyl LES group, a carbazole group, a pyrrole group, an imidazole group, a pyrazole group, a thiazole group, isothiazole group, oxazole group, isoxazole group , A pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, A phenanthrolinyl group, a phenanthryl group, a benzoimidazolyl group, a benzoquinolinyl group, a benzoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, an imidazolyl group, An imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, and a pyrimidobenzothiophenyl group; &Lt; / RTI &gt; The method according to claim 1,
At least one of R &lt; ₂ &gt; to R &lt; ₄ &gt;
A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a benzothiazolyl group, an isobenzothiazolyl group, An imidazopyrimidinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, a pyridobenzothiophenyl group, and a pyridylbenzothiophenyl group. A midbenzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, pyridinyl, group possess is, pyrimidinyl group, pyridyl group pyrazinyl, quinolinyl group, an isoquinolinium group, a naphthyridin piperidinyl group, a quinoxalinyl group, a quinazolinyl A benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a tri Group, imidazolidin jopi piperidinyl group, a pyrimidinyl group imidazo, pyrido benzo furanoid group, pyrimido benzo furanoid group, a thiophenyl group and the benzo-pyrido-pyrimido benzo thiophenyl group; &Lt; / RTI &gt; The method according to claim 1,
At least one of R &lt; ₂ &gt; to R &lt; ₄ &gt;
A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A phenanthryl group, a pentalenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, thiophenyl group, furanoid group, a carbazole group, acridinyl, dibenzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a phenyl group , A phenalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A phenylene group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl group; &Lt; / RTI &gt; The method according to claim 1,
R ₁ to R ₄ , R ₁₁ and R ₁₂ 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 sulfonic acid or a salt thereof and a phosphoric acid or a sulfonic acid or a salt thereof, or a salt thereof, or a salt thereof, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of the salts thereof;
4-1 to 4-48, 5-1 to 5-6 and 6-1 to 6-5 shown below; And
_{-Si (Q 3) (Q 4} ) (Q 5); ;
Q ₃ to Q ₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group And a quinoxalinyl group,
At least one of R ₂ to R ₄ is independently selected from the group consisting of carbazole-based compounds represented by the following formulas 4-1 to 4-48, 5-1 to 5-6, and 6-1 to 6-5:

Of the above-mentioned formulas 4-1 to 4-48, 5-1 to 5-6 and 6-1 to 6-5,
Y ₃₁ is O, S, C (Z ₃₃ ) (Z ₃₄ ), N (Z ₃₅ ) or 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, acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, C ₁ -C ₂₀ alkyl-substituted phenyl group, a phenyl-substituted phenyl group, A benzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dicyclopentadienyl group, A quinolinyl group, a quinazolinyl group, a quinoxalinyl group, and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ );
Q ₃₃ to Q ₃₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group And a quinoxalinyl group;
e2 is 1 or 2;
e3 is selected from integers from 1 to 3;
e4 is selected from integers from 1 to 4;
e5 is selected from integers from 1 to 5;
e6 is selected from integers from 1 to 6;
e7 is selected from integers from 1 to 7;
* Is the binding site with neighboring atoms. The method according to claim 1,
A carbazole-based compound represented by the following general formula (1A) or (1B)
&Lt;

&Lt; Formula 1B &gt;

(1A) of the _{X 1, L 3, L 5} , a description of a3, a5, b2, b3, R _11, R _12, b11 and b12 are the same as those described in claim 1, and
R ₂ and R ₃ are selected from the group consisting of a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, Substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkenyl groups, substituted or unsubstituted C ₆ -C ₆₀ aryl groups, substituted or unsubstituted C ₂ -C ₆₀ heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensation A polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group. The method according to claim 1,
A carbazole-based compound, which is one of the following compounds 1 to 131:

A first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode and including at least one carbazole-based compound represented by Formula 1 of any one of Claims 1 to 13, Organic light emitting device. 15. The method of claim 14,
Wherein the first electrode is an anode,
The second electrode is a cathode,
The organic layer may include: i) a hole transporting region interposed between the first electrode and the light emitting layer, the hole transporting region including at least one of a hole injecting layer, a hole transporting layer, and an electron blocking layer; And ii) an electron transporting region interposed between the light emitting layer and the second electrode, the electron transporting region including at least one of a hole blocking layer, an electron transporting layer, and an electron injection layer. 15. The method of claim 14,
Wherein the carbazole compound represented by Formula 1 is contained in the light emitting layer. 15. The method of claim 14,
Wherein the light emitting layer includes a first host and a second host,
Wherein the first host and the second host are different from each other,
The carbazole compound represented by Formula 1 is included in the light emitting layer,
I) at least one of R ₂ to R ₄ in Formula 1 is independently selected from the group consisting of hydrogen,
A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a benzothiazolyl group, an isobenzothiazolyl group, An imidazopyrimidinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, a pyridobenzothiophenyl group, and a pyridylbenzothiophenyl group. A midbenzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, pyridinyl, group possess is, pyrimidinyl group, pyridyl group pyrazinyl, quinolinyl group, an isoquinolinium group, a naphthyridin piperidinyl group, a quinoxalinyl group, a quinazolinyl A benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a tri Group, imidazolidin jopi piperidinyl group, a pyrimidinyl group imidazo, pyrido benzo furanoid group, pyrimido benzo furanoid group, a thiophenyl group and the benzo-pyrido-pyrimido benzo thiophenyl group; A carbazole-based compound,
Wherein the second host comprises i) at least one of R ₂ to R ₄ in Formula 1 is represented by Formula 1,
A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A phenanthryl group, a pentalenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, thiophenyl group, furanoid group, a carbazole group, acridinyl, dibenzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a phenyl group , A phenalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A phenylene group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl group; . A carbazole-based compound,
Q ₃₃ to Q ₃₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group And a quinoxalinyl group. 15. The method of claim 14,
The light-emitting layer includes a host 1 and a host 2,
The host 1 and the host 2 are different from each other,
The carbazole compound represented by Formula 1 is included in the light emitting layer,
The host 1 comprises the carbazole-based compound represented by Formula 1;
Wherein the host 2 comprises at least one of a first compound represented by the following Chemical Formula 41 and a second compound represented by the following Chemical Formula 61:
&Lt; EMI ID =

&Lt; Formula 61 &gt;

&Lt; Formula 61A &gt;&lt; EMI ID =

Among the above formulas
X ₄₁ is _{N - [(L 42) a42} - (R 42) b42], S, O, S (= O), S (= O) 2, C (= O), C (R 43) (R 44 ), Si (R ₄₃ ) (R ₄₄ ), P (R ₄₃ ), P (= O) (R ₄₃ ) or C = N (R ₄₃ );
Ring A ₆₁ in the above formula (61) is represented by the above formula (61A);
Ring A ₆₂ in the above formula (61) is represented by the above formula (61B);
X ₆₁ is _{N - [(L 62) a62} - (R 62) b62], S, O, S (= O), S (= O) 2, C (= O), C (R 63) (R 64 ), Si ( _R63 ) ( _R64 ), P ( _R63 ), P (= O) ( _R63 ) or C = N ( _R63 );
And X ₇₁ are C (R ₇₁₎ or N, X ₇₂ is C (R ₇₂₎ or N, X ₇₃ is C, and (R ₇₃₎ or N, X ₇₄ is a C (R ₇₄₎ or N, X ₇₅ is C (R ₇₅₎ or N, X ₇₆ is a C (R ₇₆₎ or N, X ₇₇ is a C (R ₇₇₎ or N, X ₇₈ is C (R ₇₈₎ or N;
Ar ₄₁ , L ₄₁ , L ₄₂ , L ₆₁ and L ₆₂ independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₂ - C ₆₀ heteroaryl group, an unsubstituted 2-substituted or unsubstituted non-aromatic condensed polycyclic group, and a substituted or unsubstituted 2 non-aromatic heterocyclic is selected from the condensed polycyclic group;
n1 and n2 are each independently selected from integers from 0 to 3;
a41, a42, a61 and a62 are each independently selected from integers from 0 to 3;
R ₄₁ to R ₄₄ , R ₅₁ to R ₅₄ , R ₆₁ to R ₆₄ and R ₇₁ to R ₇₉ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, , a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone 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 thereof, a substituted or unsubstituted 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, hwandoen C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₂ -C ₁₀ hetero cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ unsubstituted 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 ₂ -C ₆₀ hetero O Group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q ₄ ) (Q ₅ ) and -B (Q ₆ ) (Q ₇ );
b41, b42, b51 to b54, b61, b62 and b79 are independently selected from integers from 1 to 3;
The substituted C ₁ -C ₆₀ alkylene group, a substituted C ₂ -C ₆₀ alkenylene group, substituted C ₃ -C ₁₀ cycloalkylene group, a substituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted C ₃ - C ₁₀ cycloalkenyl group, a substituted C ₂ -C ₁₀ heterocycloalkyl alkenylene group, substituted C ₆ -C ₆₀ aryl group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted divalent non-aromatic condensed polycyclic Group, a substituted divalent non-aromatic heterocyclic polycyclic 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 A substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₂ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₂ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic group, And substituted monovalent non-aromatic The at least one substituent of the parent hetero-
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 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;
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 ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N (Q _{11) (Q 12), -Si (Q} 13) (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) of the at least one substituted, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl , A C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic 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 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 ₂ -C ₁₀ heterocyclo alkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ - C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25) A C ₃ -C ₁₀ cycloalkyl group, a C ₂ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₂ -C ₁₀ heterocycloalkyl group substituted with at least one of -B (Q ₂₆ ) (Q ₂₇ ) alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come tea, C ₂ -C ₆₀ H. Heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocyclic polycyclic group; or
_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ); ;
Wherein Q ₁ to Q _7, Q ₁₁ to Q _17, Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are independently of each other, hydrogen, C ₁ -C ₆₀ alkyl, C ₂ -C ₆₀ alkenyl, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl, C ₂ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₂ -C ₆₀ heteroaryl group, a monovalent non-aromatic heterocyclic is selected from a condensed polycyclic group, aromatic condensed polycyclic group, and 1 is non. 19. The method of claim 18,
At least one of R ₂ to R ₄ in Formula 1 is, independently of each other,
A pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a benzothiazolyl group, an isobenzothiazolyl group, An imidazopyrimidinyl group, an imidazopyrimidinyl group, a pyridobenzofuranyl group, a pyrimidobenzofuranyl group, a pyridobenzothiophenyl group, a pyridobenzothiophenyl group, and a pyridylbenzothiophenyl group. A midbenzothiophenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, pyridinyl, group possess is, pyrimidinyl group, pyridyl group pyrazinyl, quinolinyl group, an isoquinolinium group, a naphthyridin piperidinyl group, a quinoxalinyl group, a quinazolinyl A benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a tri Group, imidazolidin jopi piperidinyl group, a pyrimidinyl group imidazo, pyrido benzo furanoid group, pyrimido benzo furanoid group, a thiophenyl group and the benzo-pyrido-pyrimido benzo thiophenyl group; &Lt; / RTI &gt;
At least one of R ₄₁ , R ₄₂ and R ₅₂ in the formula (41) and at least one of R ₆₁ and R ₆₂ in the formula (61)
A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A phenanthryl group, a pentalenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, thiophenyl group, furanoid group, a carbazole group, acridinyl, dibenzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a phenyl group , A phenalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A phenylene group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl group; &Lt; / RTI &gt;
Q ₃₃ to Q ₃₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group And a quinoxalinyl group. 19. The method of claim 18,
At least one of R ₂ to R ₄ in Formula 1 is, independently of each other,
A thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, , Anthracenyl group, anthracenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, A phenanthryl group, a pentalenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ of the at least one substituted, thiophenyl group, furanoid group, a carbazole group, acridinyl, dibenzo furanoid group, a dibenzo thiophenyl group, benzo carbazole group, a dibenzo carbazole group, a phenyl group , A phenalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, A phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a phenanthryl group, a phenanthryl group, A phenylene group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group and an obarenyl group; &Lt; / RTI &gt;
At least one of R ₄₁ , R ₄₂ and R ₅₂ in the formula (41) and at least one of R ₆₁ and R ₆₂ in the formula (61)
An isothiazolyl group, an isoxazolyl group, an isoxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indole group A phenanthrolinyl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, a phenanthryl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazopyridinyl group, an imidazolidinyl group, 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 C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a C ₁ -C ₂₀ alkyl group-substituted phenyl group, a phenyl group-substituted phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, A pyrazinyl group, a pyridinyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group and a -Si (Q ₃₃ ) group, (Q ₃₄₎ (Q ₃₅₎ group of at least one substituted, a pyrrolyl group, an imidazole group, a pyrazole group, a thiazole group, isothiazole group, oxazole group, isoxazole group, a pyridinyl group, pyrazinyl, 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 benzyl group, A benzothiazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A thiazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group; &Lt; / RTI &gt;
Q ₃₃ to Q ₃₅ independently represent a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, , A carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group And a quinoxalinyl group.

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