KR20190074186A - Condensed cyclic compound, composition including the same and organic light-emitting device including the same - Google Patents

Abstract

The present invention relates to a heterocyclic compound, a composition including the same, and an organic light emitting device including the same. The heterocyclic compound is represented by chemical formula 1, (A)_n-L. In chemical formula 1, n is an integer from 1 to 8, and L is hydrogen, a single bond, or an n-valent linking group. Therefore, the organic light emitting device including the heterocyclic compound can have high current efficiency and long lifetime.

Description

[0001] The present invention relates to a heterocyclic compound, a composition containing the same, and an organic light emitting device including the same.

The present invention relates to a heterocyclic compound, a material for the organic light emitting device including the same, and an organic light emitting device including the same.

The organic light emitting device is a self light emitting type device, which has a wider viewing angle and superior contrast as well as a faster response time, superior luminance, driving voltage and response speed characteristics, .

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 holes and electrons recombine in the light emitting layer region to generate excitons. This exciton changes from the excited state to the ground state and light is generated.

A composition containing the heterocyclic compound, and an organic light emitting device containing the same.

In particular, the organic light emitting device including the heterocyclic compound can provide a high current efficiency and a long life. In addition, the heterocyclic compound may provide properties suitable for use in solution coating methods.

According to one aspect, there is provided a heterocyclic compound represented by the formula:

≪ Formula 1 >

(A) _n- L

Wherein A is a group excluding one hydrogen atom from a compound represented by the following general formula (1-1) or a compound excluding a hydrogen atom from a compound represented by the general formula (1-2)

n is an integer of 1 to 8,

L is hydrogen, a single bond or an n-valent linking group,

when n is 1, L is hydrogen,

≪ Formula 1-1 >

(1-2)

Of the above formulas (1-1) and (1-2)

X ₁ to X ₁₆ independently of one another are N or C,

X ₁ to at least one of X ₈ is - carbon bond and, - _a1 (L ₁₎

In formula (1-1), one of X ₉ to X ₁₂ is a carbon bonded to A _3, and one of X ₁₃ to X ₁₆ is a carbon bonded to A ₄ ,

Of formulas 1-2, X ₉ to X ₁₂ is one of the - (L _{1) a1} - and the carbon bond, and one of X ₁₃ to X ₁₆ is a carbon bond with A _4,

A ₁ and A ₄ independently represent hydrogen, a group represented by * - (L ₂ ) a ₂ -R _ET , a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkene A substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl alkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted hwandoen C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed A polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group,

A ₃ and A ₄ is a group represented by * - (L ₂ ) a ₂ -R _ET ,

A ₁ and A ₂ are optionally linked to each other to form a saturated ring or an unsaturated ring,

L ₁ and L ₂ are each independently selected from a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

a1 and a2 are independently of each other, is selected from an integer from 0 to 3, in the case of a1 is _{0 * - (L 1) a1} - * ' is a single bond, if a2 is _{0 * - (L 2) a2} - * Is a single bond,

R _ET is a substituted or unsubstituted C ₁ -C ₆₀ nitrogenous heterocyclic group,

R ₁ to R ₅ 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, 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, a substituted or unsubstituted C ₂ -C _A substituted or unsubstituted C ₁ -C ₆ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, A substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic Condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q 4) (Q 5), -B (Q 6 ) is selected from _{(Q 7), -P (=} O) (Q 8) (Q 9) , and _{-C (= O) (Q 10} ),

b1 and b2 are independently selected from the integers of 0 to 4, b3 and b4 are each independently selected from integers of 0 to 3,

n1 is selected from integers from 1 to 8,

However, the formula of 1-1, A ₁ and A ₂ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group when R _ET substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl group in , A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group are excluded,

Said substituted C ₁ -C ₆₀ nitrogenous heterocyclic group, substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted A C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted Substituted C ₃ -C ₁₀ cycloalkenyl groups, substituted C ₁ -C ₁₀ heterocycloalkenyl groups, substituted C ₆ -C ₆₀ aryl groups, substituted C ₆ -C ₆₀ aryloxy groups, substituted C ₆ -C ₆₀ At least one of the substituents of the substituted monovalent non-aromatic heterocyclic polycyclic group, the arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, An alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 11) (Q} 12), -Si (Q 13) (Q 14) (Q 15), -B (Q _{16) (Q 17), -P} (= O) (Q 18) (Q 19) and -C (= O) (at least one substituted, C ₁ -C ₆₀ alkyl group of the Q _20), C ₂ -C ₆₀ An alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic _{, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27), -P (= O) (Q 28) (Q _29), and -C (= O) with at least one a, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ substituted one (Q ₃₀₎ A heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic condensed Polycyclic group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35), -B (Q 36) (Q 37), -P (= O) (Q 38) (Q 39 ) And -C (= O) (Q ₄₀ );

≪ / RTI >

Wherein Q ₁ to Q ₁₀ , Q ₁₁ to Q ₂₀ , Q ₂₁ to Q ₃₀ and Q ₃₁ to Q ₄₀ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group substituted by at least one of C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

According to another aspect, a composition comprising the heterocyclic compound is provided.

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 and including a light emitting layer, wherein the organic layer includes at least one kind of the heterocyclic compound.

Since the heterocyclic compound has improved electrical and / or thermal stability, the organic light emitting device employing the heterocyclic compound has improved current efficiency and lifetime characteristics.

1 is a schematic cross-sectional view of an organic light emitting device according to an embodiment.

[Heterocyclic compound]

The heterocyclic compounds represented by the following formula (1) according to one embodiment of the present invention are described below:

≪ Formula 1 >

(A) _n- L

In the above formula (1), A is a group excluding one hydrogen atom from a compound represented by the following general formula (1-1) or a compound excluding a hydrogen atom from a compound represented by the general formula (1-2).

In Formula 1, n may be an integer of 1 to 8.

According to one embodiment, n may be an integer from 1 to 4. For example, n may be 1 or 2.

In Formula 1, L may be hydrogen, a single bond, or an n-linkage group. Provided that when n is 1, L is hydrogen.

According to one embodiment, L is selected from the group consisting of hydrogen, a single bond, a substituted or unsubstituted C ₁ -C ₆₀ alkylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, -O-, -S-, or -N (R < ₁₀₁ >) -.

The R ₁₀₁ may be hydrogen, deuterium, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, or a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group.

According to one embodiment, L may be selected from methylene, ethylene, n-propylene, n-butylene, phenylene, biphenylene, terphenylene and fluorenylene.

≪ Formula 1-1 >

(1-2)

In the above formulas (1-1) and (1-2), X ₁ to X ₁₆ may independently be N or C.

According to one embodiment, at least one of X ₁ to X ₁₆ in Formulas 1-1 and 1-2 may be N.

According to one embodiment, in the above formulas 1-1 and 1-2, X ₄ or X ₅ may be N, or X ₄ and X ₅ may be N.

In Formula 1-1 and Formula 1-2, at least one of X ₁ to X ₈ is a carbon bonded to - (L ₁ ) _a1 -.

In Formula 1-1, one of X ₉ to X ₁₂ is a carbon bonded to A _3, and one of X ₁₃ to X ₁₆ is a carbon bonded to A ₄ .

One of the above formula 1-2, X ₉ to X ₁₂ is - (L _{1) a1} - and the carbon bond, and one of X ₁₃ to X ₁₆ is a carbon bond, and A _4.

In Formulas 1-1 and 1-2, A ₁ and A ₄ independently represent hydrogen, a group represented by * - (L ₂ ) a ₂ -R _ET , a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, A substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo alkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl alkenyl group, a substituted or unsubstituted ring unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group.

Provided that at least one of A ₃ and A ₄ is a group represented by * - (L ₂ ) a ₂ -R _ET .

In one embodiment, in Formula 1-1, the carbon position at which A ₃ is bonded and the carbon position at which A ₄ is bonded may be asymmetric.

In another embodiment, in Formula 1-1, X ₁₂ is carbon bonded with A ₃ , X ₁₄ is carbon bonded with A ₄ , A ₃ is * - (L ₂ ) a ₂ -R _ET And A ₄ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group.

In another embodiment, in Formula 1-1, X ₁₂ is carbon bonded with A ₃ , X ₁₄ is carbon bonded with A ₄ , A ₃ is * - (L ₂ ) a ₂ -R _ET And A ₄ is a phenyl group, a biphenyl group, a terphenyl group, or a quaterphenyl group.

In one embodiment, in Formula 1-2, the carbon position bonded to - (L ₁ ) _a1 - and the carbon position bonded to A ₄ may be asymmetric.

In other embodiments, the above formula 1-2, X ₁₁ is - (L _{1) a1} - a, and a carbon bond, and X ₁₃ and the carbon bond with A _4, wherein A ₄ * - (L _{2) lt; 2} > -R < _ET >.

According to one embodiment, in formulas (1-1) and (1-2), A ₁ to A ₄ are, independently of each other,

_{Hydrogen, * - (L 2) a2} -R group is represented by _ET, a methyl group, an ethyl group, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n Isopropyl group, 1-methylpropyl group, 1-methylpropyl group, 1-ethylbutyl group, Methyl-1-isopropylpropyl group, 1-ethyl-3-methylbutyl group, n-heptyl group, n-heptyl group, Methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, n-nonyl group, Pentadecyl group, n-pentadecyl group, n-pentadecyl group, n-pentadecyl group, n-octadecyl group, N-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group, n-heneicosyl group, N-docosyl group, n -Tricosyl group, n-tetracosyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec- , n-pentoxy group, isopentoxy group, tert-pentoxy group, neopentoxy group, n-hexyloxy group, isohexyloxy group, heptyloxy group, octyloxy group, , Undecyloxy group, dodecyloxy group, tridecyloxy group, tetradecyloxy group, pentadecyloxy group, hexadecyloxy group, heptadecyloxy group, octadecyloxy group, 2-ethylhexyloxy group, 2-thienyloxy group, 2-indolyloxy group, 3-indolyloxy group, 2-naphthyloxy group, 2-thienylthio group, A 2-benzothienyloxy group, an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N-dipropylamino group, N, N-dimethylamino group, N, , N-diisopropylamino group, N, N-dibutylamino group, N, N-diisobutylamino group, N, N-dipentylamino group and N, N-dihexylamino group;

An acenaphthyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a di A phenanthrenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a fluoranthenyl group, a pyrenyl group, a klychenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, , Hexaphenyl group, hexacenyl group, rubicenyl group, trinaphthyl group, heptaphenyl group, pyranthrenyl group, pyridinyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, A benzoquinolinyl group, a phenanthridinyl group, a phenanthrolinyl group, a benzoquinonyl group, a coumarinyl group, a benzoquinolinyl group, a benzoquinolyl group, a benzoquinolyl group, a benzoquinolyl group, Anthraquinone group, fluorenone group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a furyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, Benzoxazolyl group, benzoxazolyl group, dibenzocarbazolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indazolyl group, oxazolyl group, isoxazolyl group, A thiazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzisothiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazophenanthridinyl group, a benzimidazophenanthryl group, An azadibenzofuranyl group, an azacabazolyl group, an azadibenzothienyl group, a diazadibenzofuranyl group, a diazacabazolyl group, a diazadibenzothienyl group, a jazminonyl group, and a thioxanthonyl group; And

A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C ₁ -C ₃₀ alkyl group, a C ₁ -C ₃₀ alkoxy group, a phenyl group , A phenanthrenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, an heptalenyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, A fluorenyl group, a pyrenyl group, a klycenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenyl group, a fluorenyl group, a pyrenyl group, a phenanthryl group, A pyridinyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, A quinoxalinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group, a benzoquinone group, A phenanthrolinyl group, a benzoquinone group, a coumarinyl group, an anthraquinone group, a fluorenone group, a furanyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a dibenzothiophenyl group, a dibenzoyl group, a pyrrolyl group, An oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, , Benzisothiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazophenanthridinyl group, benzimidazophenanthridinyl group, azadibenzofuranyl group, azacarbazolyl group, azadibenzoyl group, Thienyl group, diazodibenzofura Naphthyl group, anthracenyl group, azulenyl group, heptareyl group, thiazolidinyl group, thiazolyl group, thiazolidinyl group, thiazolidinyl group, thiazolidinyl group, thiazolidinyl group, diazacarbazolyl group, diazabazoyl group, diazadibenzothienyl group, A phenanthrenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a fluorenyl group, an acenaphthyl group, a phenanthryl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, An alkenyl group, an alkynyl group, an alkenyl group, an alkynyl group, an alkenyl group, an alkynyl group, an alkenyl group, an alkenyl group, an alkynyl group, A pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group , Benzoquinolinyl group, benzo A thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, a benzoylolyl group, a diethoxycarbonyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A benzofuranyl group, a dibenzothiophenyl group, a dibenzoylsilyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazolyl group, a benzimidazolyl group, A thiazolyl group, a thiazolyl group, a tetrazolyl group, an indazolyl group, an oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, A diazo group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazophenanthridinyl group, a benzimidazophenanthridinyl group, an azadibenzofuranyl group, an azacabazolyl group, an azadibenzothienyl group, Benzofuranyl group, diazacar Sol group, dia jadi benzothienyl group, janton group and thioxanthone group;

≪ / RTI >

In the above formulas (1-1) and (1-2), A ₁ and A ₂ may be optionally connected to each other to form a saturated ring or an unsaturated ring.

According to one embodiment, A ₁ and A _{2 in the} above formulas (1-1) and (1-2) may be connected to form a group represented by the following formula (9)

≪ Formula 9 >

In the formula (9)

X ₉₁ to X ₉₈ independently of one another are N or C,

R ₉₁ to R ₉₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, 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, a substituted or unsubstituted C ₂ -C _A substituted or unsubstituted C ₁ -C ₆ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-direction Condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q 4) (Q 5) and -B (Q ₆ ) is selected from (Q _7),

b91 to b92 are independently selected from integers from 1 to 4,

* Is a binding site with neighboring carbon atoms.

In Formulas 1-1 and 1-2, L ₁ and L ₂ independently represent a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group ≪ / RTI >

According to one embodiment, L ₁ and L ₂ independently of one another are selected from the group consisting of a benzene group, a pentalene group, an indene group, a naphthalene group, an anthracene group, an azulene group, an hethalene group, an acenaphthalene group, Group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, a biphenyl group, a terphenyl group, a triphenylene group, a fluoranthene group, , Pentacene group, pentacene group, pentacene group, pentacene group, tetraphene group, hexaphene group, hexasene group, rubisene group, trinaphthalene group, heptapene group, pyranthrene ) Group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, naphthyridine group, acridine group, A phenanthroline group, a benzoquinone group, a coumarin group, an anthraquinone group, a fluorenone group, a furan group, a thiophene group, a silole group, a benzofuran group, a benzothiophene group, Group, a benzoyl group, a dibenzofuran group, a dibenzothiophene group, a dibenzoylsilyl group, a pyrrole group, an indole group, an isoindole group, a carbazole group, a benzocarbazole group, a dibenzocarbazole group, , Benzimidazole group, pyrazole group, triazole group, tetrazole group, indazole group, oxazole group, isoxazole group, benzoxazole group, benzisoxazole group, thiazole group, isothiazole group, Benzothiazole group, benzisothiazole group, imidazolinone group, benzimidazolinone group, imidazopyridine group, imidazopyrimidine group, imidazophenanthridine group, benzimidazophenanthridine group, Dean A diazabenzothiophene group, a xanthone group, a thioxanthone group, a thioxanthone group, a thioxanthone group, a thioxanthone group, a thioxanthone group, a thioxanthone group, ) group; And

A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C ₁ -C ₃₀ alkyl group, a C ₁ -C ₃₀ alkoxy group, a phenyl group , A phenanthrenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, an heptalenyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, A fluorenyl group, a pyrenyl group, a klycenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenyl group, a fluorenyl group, a pyrenyl group, a phenanthryl group, A pyridinyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, A quinoxalinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group, a benzoquinone group, A phenanthrolinyl group, a benzoquinone group, a coumarinyl group, an anthraquinone group, a fluorenone group, a furanyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a dibenzothiophenyl group, a dibenzoyl group, a pyrrolyl group, An oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, , Benzisothiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazophenanthridinyl group, benzimidazophenanthridinyl group, azadibenzofuranyl group, azacarbazolyl group, azadibenzoyl group, Thienyl group, diazodibenzofura A benzene group, a pentane group, an indene group, a naphthalene group, an anthracene group, an azulene group, a heptarene group, a thiazole group, a thiophene group, Group, an acenaphthalene group, a phenalene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, a biphenyl group, a terphenyl group, A pentacene group, a pentacene group, a tetraphene group, a hexaphene group, a hexacene group, a rubisene group, a pyrenylene group, a pyrenylene group, a pyrenylene group, A triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinone group, a pyrazine group, a pyrazine group, a pyridazine group, a pyrimidine group, A phenanthrene group, a phenanthrene group, a phenanthroline group, a benzoquinone group, a coumarin group, an anthraquinone group, a fluorenone group, an anthraquinone group, a phenanthrene group, A dibenzothiophene group, a dibenzoylsilyl group, a pyrrole group, an indole group, an isoindole group, a carbamoyl group, an isoindole group, an isoindole group, a carbamoyl group, A thiazole group, an indazole group, an oxazole group, an isoxazole group, a benzoxazole group, a benzoxazole group, an imidazole group, a benzimidazole group, a pyrazole group, A benzimidazole group, a benzimidazole group, a benzimidazole group, an imidazopyridine group, an imidazopyrimidine group, an imidazopyrimidine group, an imidazopyrimidine group, Anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, Diazabenzothiophene group, xanthone group and thioxanthone group; ≪ / RTI >

In the above formulas (1-1) and (1-2), a1 and a2 may be independently selected from integers of 0 to 3. If a1 is _{0 * - (L 1) a1} - * ' case is a is a single bond, a2 is _{0 * - (L 2) a2} - *' is a single bond.

The R _ET may be a substituted or unsubstituted C ₁ -C ₆₀ nitrogen heterocyclic group.

However, the formula of 1-1, A ₁ and A ₂ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group when R _ET substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl group in , A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, and a substituted or unsubstituted triazinyl group are excluded.

According to one embodiment, the R _ET is selected from the group consisting of imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, A thiazolyl group, a thiazolyl 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, a benzooxazolyl group, an isobenzothiazolyl group, a benzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, an isoxazolyl group, A thiazolyl group, a tetrazolyl group, an oxadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazoquinolinyl group, an imidazoisoquinolinyl group, an azadibenzofuranyl group, a diazodibenzo A furanyl group, an azadibenzothiophenyl group, Aza-dibenzo thiophenyl group, a fluorenyl group aza, diaza fluorenyl group, a fluorenyl group, and by by-fluorenyl group as a spy-diaza-aza spy;

A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group , A phenanthrenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, an heptalenyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, A phenanthryl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a pyranyl group, a pyranyl group, a phenanthryl group, a phenanthrenyl group, a triphenylenyl group, a fluoranthenyl group, a pyrenyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group, A pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indazolyl group, A phenanthridinyl group, an acridinyl group, a phenanthryl group, a phenanthryl group, an acridinyl group, an acridinyl group, an acridinyl group, an acridinyl group, an acridinyl group, A benzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, An imidazopyrimidinyl group, an imidazoquinolinyl group, an imidazoisoquinolinyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azadibenzothiophenyl group , A diazadibenzothiophenyl group, an azafluorenyl group, a diazafluorenyl group, an azaspirofiburanyl group, and a diazaspirofluoranyl group; And

An acenaphthyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a di A phenanthrenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, A phenyl group substituted with at least one member selected from the group consisting of a pyridyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group, a phentalenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, A phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a pyrenyl group, a cyanecyl group, a phenanthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a fluorenyl group, Group, a phenenyl group, a perylenyl group An imidazolyl group substituted with at least one member selected from the group consisting of a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group, An isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an iso 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, An isothiazolyl group, a benzimidazolyl group, a naphthomidazolyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, Zofiridinyl group, imidachoxifene An imidazoquinolinyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azadibenzothiophenyl group, a diazabenzothiophenyl group, an azafluorenyl group, a diazafluoro group, Aza-spirobifluorenyl group, and a diazaspirofluoranyl group;

≪ / RTI >

According to another embodiment, the R _ET can be selected from the group consisting of the following formulas (2-1) to (2-3):

X ₂₁ to X ₃₃ are independently N or C, at least one of X ₂₁ to X ₂₅ is N, at least one of X ₂₆ to X ₂₉ is N, and X ₃₀ to X ₃₃ may be N.

In the general formulas 2-2 to 2-3, Y ₂₁ and Y ₂₂ may be independently selected from O, S, N (R ₂₅ ), and C (R ₂₅ ) (R ₂₆ ).

According to one embodiment, Y ₂₁ and Y ₂₂ may be independently selected from O, S, and N (R ₂₅ ).

In the above formulas 2-1 to 2-3, Z may be selected from a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₂ -C ₃₀ heterocyclic group.

According to one embodiment, Z may be a substituted or unsubstituted 6-membered carbocyclic group or a substituted or unsubstituted 6-membered heterocyclic group.

In formulas (2-1) to (2-3), R ₂₁ to R ₂₆ 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 alkene 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 ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl alkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted hwandoen C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted Or an unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group,

Two adjacent substituents of R ₂₁ to R ₂₆ may be optionally linked to each other to form a saturated ring or an unsaturated ring.

In addition, R ₂₁ to R ₂₆ which is substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl, substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C _A substituted C ₁ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted C ₆ -C ₆₀ aryl group , A substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent The aromatic heterocyclic polycyclic group may be substituted with at least one of the substituents as described above. In this case, the substituent 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 group, C ₁ -C ₁₀ heteroaryl cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group is a condensed polycyclic connected through a linking group such as alkylene group, an oxy group (-O-), thio (-S-) .

In the general formulas (2-1) to (2-3), b21 to b23 are independently selected from integers of 1 to 4, b24 is selected from integers of 1 to 3,

* Is a binding site with neighboring atoms.

According to one embodiment, the R _ET can be selected from the group consisting of the following formulas (3-1) to (3-18):

Of the above formulas (3-1) to (3-18)

The definitions of R ₂₁ to R ₂₄ , b ₂₁ to b ₂₃ , and Y ₂₂ are the same as those described in the definitions of the above formulas 2-1 to 2-3,

The definitions of R ₂₅ and R ₂₆ refer to the definition of R ₂₁ above,

b25 and b26 are each independently selected from integers from 1 to 4,

"Ph" is a phenyl group, and * is a bonding site with neighboring atoms.

According to one embodiment, the R _ET can be selected from the group represented by the following formulas 3-4 to 3-7.

According to one embodiment, in the general formulas (2-1) to (2-3), R ₂₁ to R ₂₆ independently of one another can be selected from hydrogen, deuterium and R-1 to R-

Among the above-mentioned formulas R-1 to R-28,

* Is a binding site with neighboring atoms.

According to another embodiment, in the general formulas (2-1) to (2-3), R ₂₁ to R ₂₆ independently represent hydrogen, deuterium, -20 to R-28.

In Formulas 1-1 and 1-2, R ₁ to R ₅ 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 alkene 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 ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl alkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted hwandoen C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted addition Unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or non-monovalent unsubstituted aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q 4) (Q ₅ ) and -B (Q ₆ ) (Q ₇ ).

According to one embodiment, R ₁ to R ₅ in the general formulas 1-1 and 1-2 are independently selected from the group consisting of hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, Butyl group, n-pentyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, Dimethylbutyl group, 1-isopropylpropyl group, 1,2-dimethylbutyl group, n-heptyl group, 1,4-dimethylpentyl group, 3-ethylpentyl group, 2-methyl- , 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylhexyl group, 3-methyl-1-isopropylbutyl group, An ethyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-propyl group, an isopropyl group, an n-butyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group, n-pentadecyl group, An n-heptyl group, an n-heneicosyl group, an n-docosyl group, an n-tricosyl group, an n-tetracosyl group, Propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, n-pentoxy group, isopentoxy group, An isohexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, a tridecyloxy group, a tetradecyloxy group, a pentadecyloxy group, 2-naphthyloxy group, 2-azulenyloxy group, 2-naphthyloxy group, 3-ethylhexyloxy group, 2-benzothienyloxy group, N-methylamino group, N-ethylamino group, N-propylamino group, N-ethylamino group, An N-isopropylamino group, an N-isopropylamino group, an N-butylamino group, an N-isobutylamino group, an N-sec-butylamino group, Diethylamino group, N, N-dipropylamino group, N, N-diisopropylamino group, N, N-dibutylamino group, N, N-diisobutylamino group, N-dihexylamino group;

An acenaphthyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a di A phenanthrenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a fluoranthenyl group, a pyrenyl group, a klychenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, , Hexaphenyl group, hexacenyl group, rubicenyl group, trinaphthyl group, heptaphenyl group, pyranthrenyl group, pyridinyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, A benzoquinolinyl group, a phenanthridinyl group, a phenanthrolinyl group, a benzoquinonyl group, a coumarinyl group, a benzoquinolinyl group, a benzoquinolyl group, a benzoquinolyl group, a benzoquinolyl group, Anthraquinone group, fluorenone group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a furyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, Benzoxazolyl group, benzoxazolyl group, dibenzocarbazolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indazolyl group, oxazolyl group, isoxazolyl group, A thiazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzisothiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazophenanthridinyl group, a benzimidazophenanthryl group, An azadibenzofuranyl group, an azacabazolyl group, an azadibenzothienyl group, a diazadibenzofuranyl group, a diazacabazolyl group, a diazadibenzothienyl group, a jazminonyl group, and a thioxanthonyl group; And

A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C ₁ -C ₃₀ alkyl group, a C ₁ -C ₃₀ alkoxy group, a phenyl group , A phenanthrenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, an heptalenyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, A fluorenyl group, a pyrenyl group, a klycenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenyl group, a fluorenyl group, a pyrenyl group, a phenanthryl group, A pyridinyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, A quinoxalinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group, a benzoquinone group, A phenanthrolinyl group, a benzoquinone group, a coumarinyl group, an anthraquinone group, a fluorenone group, a furanyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a dibenzothiophenyl group, a dibenzoyl group, a pyrrolyl group, An oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, , Benzisothiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazophenanthridinyl group, benzimidazophenanthridinyl group, azadibenzofuranyl group, azacarbazolyl group, azadibenzoyl group, Thienyl group, diazodibenzofura Naphthyl group, anthracenyl group, azulenyl group, heptareyl group, thiazolidinyl group, thiazolyl group, thiazolidinyl group, thiazolidinyl group, thiazolidinyl group, thiazolidinyl group, diazacarbazolyl group, diazabazoyl group, diazadibenzothienyl group, A phenanthrenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a fluorenyl group, an acenaphthyl group, a phenanthryl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, An alkenyl group, an alkynyl group, an alkenyl group, an alkynyl group, an alkenyl group, an alkynyl group, an alkenyl group, an alkenyl group, an alkynyl group, A pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group , Benzoquinolinyl group, benzo A thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, a benzoylolyl group, a diethoxycarbonyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A benzofuranyl group, a dibenzothiophenyl group, a dibenzoylsilyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazolyl group, a benzimidazolyl group, A thiazolyl group, a thiazolyl group, a tetrazolyl group, an indazolyl group, an oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, A diazo group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazophenanthridinyl group, a benzimidazophenanthridinyl group, an azadibenzofuranyl group, an azacabazolyl group, an azadibenzothienyl group, Benzofuranyl group, diazacar Sol group, dia jadi benzothienyl group, janton group and thioxanthone group;

≪ / RTI >

In Formulas 1-1 and 1-2, b1 and b2 are independently selected from integers of 0 to 4, and b3 and b4 are independently selected from integers of 0 to 3.

In the formulas (1-1) and (1-2), n1 may be an integer of 1 to 8.

According to one embodiment, the heterocyclic compound may be selected from the following compounds, but is not limited thereto:

The compound represented by Formula 1-1 or 1-2 includes a structure in which the carbazole ring is connected to the fluorene ring, so that the electron transporting ability and the electron injecting ability can be excellent. Accordingly, the heterocyclic compound represented by Formula 1 can be suitably used as a material for an organic light emitting device.

The heterocyclic compound represented by the above formula (1) may exhibit high solubility in a solvent (especially an ester-based organic solvent). Further, since the heterocyclic compound represented by the above formula (1) has a high glass transition temperature (Tg), it is not readily deformed or deformed by heat when the solvent after the film formation by the coating method is removed. Accordingly, the heterocyclic compound represented by Formula 1 can be applied to the solution coating method. In addition, the organic layer formed by the solution coating method using the heterocyclic compound represented by the formula (1) has less unevenness and uniform thickness, and the organic layer can have a smooth surface. Therefore, even when the organic light emitting device using the heterocyclic compound represented by Formula 1 is manufactured by the solution coating method, the application of the driving voltage and the change in the light emission are small, so that the current efficiency and the light emission lifetime can be improved.

The heterocyclic compound represented by the general formula (1) has a relatively high glass transition temperature and excellent thermal stability. Accordingly, the organic light emitting device including the heterocyclic compound represented by Formula 1 is relatively stable against the driving heat. Deterioration and deformation of the organic light emitting device due to driving heat are suppressed. As a result, the organic light emitting device including the heterocyclic compound represented by Formula 1 may exhibit an improved lifetime.

At this time, the heterocyclic compound represented by Formula 1 may have a glass transition temperature of 120 ° C or higher, for example, 125 ° C or higher. As another example, the glass transition temperature of the heterocyclic compound may be at least 140 < 0 > C. The glass transition temperature can be measured, for example, by the method specified in JIS K 7121 or ISO 3146. In the following Examples, glass transition temperature was measured by differential scanning calorimetry.

The molecular weight of the heterocyclic compound represented by Formula 1 may be 850 to 3000, for example, 850 to 2500. When the molecular weight of the heterocyclic compound is 850 or more, the heat resistance of the heterocyclic compound is improved. When the molecular weight of the heterocyclic compound is 3000 or less, solubility in a solvent (for example, an ester organic solvent) .

The solubility of the heterocyclic compound in methylbenzoate at 25 DEG C may be 0.5% by weight or more, for example, 1% by weight or more.

The heterocyclic compound represented by Formula 1 may be included in an organic layer disposed between a pair of electrodes of the organic light emitting device. For example, the heterocyclic compound represented by Formula 1 may be included in the light emitting layer and may be suitable as a host.

The heterocyclic compound represented by the formula (1) can be synthesized by a known organic synthesis method. A specific method for synthesizing the heterocyclic compound represented by the formula (1) can be easily understood by those skilled in the art with reference to the following examples.

[Material for light emitting device]

The material for a light emitting device according to an embodiment of the present invention may include a heterocyclic compound represented by the formula (1). Since the heterocyclic compound represented by the formula (1) has high solubility in solvents and excellent thermal stability as described above, a thin film of good quality can be produced even in the wet coating method. Also, the heterocyclic compound represented by Formula 1 may have high charge transportability. Therefore, the light-emitting device material containing the heterocyclic compound represented by Formula 1 can be used, for example, in the charge transport layer and the light-emitting layer of the organic light emitting device.

Accordingly, the organic light emitting device using the heterocyclic compound represented by Formula 1 can improve the current efficiency and the luminescent lifetime even when it is produced by the wet coating method.

Therefore, the light emitting device material containing the heterocyclic compound represented by the above formula (1) can be used for manufacturing the light emitting device, and in this case, the light emitting device having excellent current efficiency and light emitting life can be manufactured by the coating method.

 [Composition]

Hereinafter, the composition according to one embodiment of the present invention will be described in detail.

The composition is used, for example, to form each layer of the light emitting device by a solution coating method.

The composition may include a heterocyclic compound represented by the general formula (1).

According to one embodiment, the composition may further comprise a light emitting material.

The light emitting material is not particularly limited as long as it has a light emitting function, but may be a fluorescent dopant, a phosphorescent dopant, a quantum dot, or the like.

The fluorescent dopant is a compound capable of emitting light from singlet excitons and includes, for example, perlene and derivatives thereof, rubrene and derivatives thereof, coumarin and derivatives thereof, 4- 4-dicyanomethylene-2- (p-dimethylaminostyryl) -6-methyl-4H-pyran: DCM) and derivatives thereof. However, the present invention is not limited thereto.

The phosphorescent dopant is a compound capable of emitting light from triplet excitons and may be an organic metal compound. For example, the phosphorescent dopant may be bis [2- (4,6-difluorophenyl) pyridinate] picolinate iridium (III) (bis [2- (4,6-difluorophenyl) pyridinate] III): FIrpic), bis (1-phenyl isoquinoline) (acetylacetonate) iridium (III) (bis (1- phenylisoquinoline) (acetylacetonate) iridium (III): Ir (piq) 2 (acac)), tris ( 2-phenylpyridine iridium (III): Ir (ppy) ₃ ), tris (2- (3-p-xylyl) phenyl) pyridine iridium (III) An iridium complex such as 2- (3-p-xylyl) phenyl) pyridine iridium (III)) (dopant), an osmium complex, a platinum complex and the like.

The quantum dot may be a nanoparticle made of a II-VI group semiconductor, a III-V group semiconductor, or an IV-IV group semiconductor. For example, the quantum dots may be CdO, CdS, CdSe, CdTe, ZnO, ZnS, ZnSe, ZnTe, HgS, HgSe, HgTe, MgSe, MgS CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, GaN, GaN, GaP, GaAs, AlN, AlP, AlAs, InN, InP, InAs, InSb, GaNP, GaNAs, GaNSb, GaPb, GaN, GaN, GaN, GaN, GaN, GaN, GaN, SnPbSe, PbSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, SnPbSe, SnPbSe, SnPbSe, SnPbSe, SnPbTe, or the like, but is not limited thereto. The diameter of the quantum dots is not particularly limited, but may be, for example, 1 nm to 20 nm. The quantum dot may be a single core structure or a core-shell structure.

Wherein the composition is selected from the group consisting of a compound represented by the following formula 4-1, a compound represented by the following formula 4-2, a compound represented by the following formula 5, a compound represented by the following formula 6 and a compound represented by the following formula 7 Or more.

<Formula 4-1>

<Formula 4-2>

&Lt; Formula 5 >

&Lt; Formula 5A >

(6)

&Lt; Formula 7 >

Of the above-mentioned formulas 4-1, 4-2, 5, 5A, 6, and 7,

X ₄₁ to X ₄₈ independently of one another are N or C,

At least one of X ₄₁ to X ₄₈ is - (L _{41) a41} -, and the carbon bond and,

X ₅₁ is N (R ₅₁ ), O or S, X ₅₂ is N (R ₅₂ ), O or S,

C ₅₁ to C ₅₄ are carbon atoms (C), and two adjacent ones of C ₅₁ to C ₅₄ are condensed to the group represented by the formula (5) through Y ₅₁ and Y ₅₂ respectively,

L _41, L ₆₁ to L ₆₃ and L ₇₁ are selected from a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

a41, a61 to a63 and a71 are each independently selected from integers of 0 to 3,

A is a group represented by the formula (5A)

R ₄₁ to R ₄₆ , R ₅₁ to R ₅₅ , R ₆₁ to R ₆₆ and R ₇₁ to R ₇₆ 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 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, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ H. Loa group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N ( Q ₄ ) (Q ₅ ) and -B (Q ₆ ) (Q ₇ )

b41 to b43, b46, b53 to b54, b71 to b73 are independently selected from integers of 0 to 4,

b44, b45, b72 and b74 are independently selected from integers of 0 to 3,

b55 is selected from an integer of 0 to 2,

B ₁ and B ₄ are, independently of each other, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, An unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkane Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl groups, substituted or unsubstituted C ₆ -C ₆₀ aryl groups, substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent ring non-fused polycyclic aromatic group and a substituted or unsubstituted monovalent ring non-aromatic heterocyclic group condensed polycyclic &Lt; / RTI &gt;

m is an integer from 1 to 8,

p1 to p3 are independently selected from integers of 0 to 4;

The composition may further comprise a solvent.

The solvent contained in the composition is not particularly limited so long as the heterocyclic compound represented by the formula (1) is dissolved. For example, the solvent may be selected from the group consisting of toluene, xylene, ethylbenzene, diethylbenzene, mesitylene, propylbenzene, cyclohexylbenzene, But are not limited to, dimethoxybenzene, anisole, ethoxytoluene, phenoxytoluene, isopropylbiphenyl, dimethylanisole, phenyl acetate, But are not limited to, phenyl propionic acid, methyl benzoate, ethyl benzoate, and the like.

The concentration of the heterocyclic compound represented by Formula 1 in the composition may be 0.1 wt% to 10 wt%, more specifically, 0.5 wt% to 5 wt%, but is not limited thereto. When the above range is satisfied, the coatability can be improved.

Therefore, the composition can be used as a material for a light emitting device (e.g., an organic light emitting device, a quantum dot light emitting device, and the like). Specifically, the composition can be used for the light emitting layer, the charge injecting layer and / or the charge transporting layer of the light emitting device. More specifically, the composition can be used in the light emitting layer of the light emitting device. In particular, the composition can be used when the light emitting device is manufactured by the solution coating method, and the current efficiency and the light emitting lifetime of the light emitting device can be maintained or improved.

[Organic light emitting element]

Hereinafter, the organic light emitting device according to one embodiment of the present invention will be described in detail with reference to FIG. 1 is a schematic cross-sectional view of an organic light emitting diode according to an embodiment of the present invention.

An organic light emitting diode 100 according to an exemplary embodiment of the present invention includes a substrate 110, a first electrode 120 disposed on the substrate 110, a hole injection layer 130 disposed on the first electrode 120, A hole transporting layer 140 disposed on the hole injecting layer 130, a light emitting layer 150 disposed on the hole transporting layer 140, an electron transporting layer 160 disposed on the light emitting layer 150, an electron transporting layer 160 An electron injection layer 170 disposed on the electron injection layer 170, and a second electrode 180 disposed on the electron injection layer 170.

The heterocyclic compound represented by Formula 1 may include an organic layer (for example, a hole injection layer 130, a hole transport layer 140) interposed between the first electrode 120 and the second electrode 180, The light emitting layer 150, the electron transport layer 160, and the electron injection layer 170). Specifically, the heterocyclic compound represented by Formula 1 may be included in the light emitting layer 150 as a host. Alternatively, the heterocyclic compound represented by Formula 1 may be contained in an organic layer other than the light emitting layer 150. For example, the heterocyclic compound represented by Formula 1 may be included in the hole injecting layer 130 and / or the hole transporting layer 140 as a charge transporting material.

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 compound including a metal.

In the present specification, the phrase "(the organic layer) contains one or more organometallic compounds" means that one kind of heterocyclic compounds belonging to the general formula (1) Quot; may include more than two species of heterocyclic compounds. "

For example, the organic layer may contain only the compound 1 as the heterocyclic 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 the compound 1 and the compound 2 as the heterocyclic 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 exist in the light emitting layer).

The substrate 110 may be a substrate used in general organic light emitting devices. For example, the substrate 110 may be, but is not limited to, a glass substrate, a silicon substrate, a transparent plastic substrate, and the like, which are excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and waterproofness.

A first electrode 120 is formed on a substrate 110. The first electrode 120 is specifically an anode and may be formed of a material having a high work function such as a metal, an alloy, or a conductive compound to facilitate hole injection. The first electrode 120 may be a reflective electrode, a transflective electrode, or a transmissive electrode. The first electrode 120 may have a single layer or a multilayer structure including two or more layers. For example, the first electrode 120 may be a transparent electrode formed of indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) or the like with excellent transparency and conductivity . The first electrode 120 may be formed of at least one selected from the group consisting of Mg, Al, Al-Li, Ca, Mg-In, -Ag) or the like may be laminated to form a reflective electrode. Alternatively, the first electrode 120 may have a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

A hole transporting region may be formed on the first electrode 120.

The hole transporting region may include at least one of a hole injection layer 130, a hole transporting layer 140, an electron blocking layer (not shown), and a buffer layer (not shown).

The hole transporting region may include only the hole injecting layer 130, or may include only the hole transporting layer 140. 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 sequentially stacked from the first electrode 120.

The hole injecting layer 130 may be formed of, for example, poly (ether ketone) -containing triphenylamine (TPAPEK) containing triphenylamine, 4-isopropyl-4'-methyldiphenyl iodonium tetrakis (4-isopropyl-4'-methyldiphenyliodonium tetrakis (pentafluorophenyl) borate: PPBI), N, N'-diphenyl-N, N'- - phenyl] -biphenyl-4,4'-diamine (N, N'-diphenyl-N, N'- -diamine: DNTPD), copper phthalocyanine, 4,4 ', 4 "-tris (3-methylphenylphenylamino) triphenylamine: m -MTDATA), N, N'-di (1-naphthyl) -N, N'-diphenylbenzidine: NPB) 4 ', 4 "-tris (diphenylamino) triphenylamine (TDATA), 4,4' (4,4 ', 4 "-tris (N, N-2-naphthylphen styrene sulfonate (poly (3, 4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (vinylidene fluoride) Polyaniline / 10-camphorsulfonic acid (PANI / CSA) and polyaniline / poly (4-styrenesulfonate): PEDOT / PSS, Poly (4-styrenesulfonate): PANI / PSS).

The hole injection layer 130 may be formed to a thickness of about 10 nm to about 1000 nm, more specifically, about 10 nm to about 100 nm.

The hole transporting layer 140 may be formed of, for example, 1,1-bis [(di-4-tolylamino) phenyl] cyclohexane: TAPC) Carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, carbazole derivatives such as N, N'-bis (3-methylphenyl) -N, N'- Phenyl] -4,4'-diamine (TPD), N, N'-bis (3-methylphenyl) N, N'-di (1-naphthyl) -N, N ', N'-tetramethyldicyclohexylcarbodiimide, N'-diphenylbenzidine (NPB), poly (9,9-dioctyl-fluorene-co-N- (4-butylphenyl) (4-butylphenyl) -diphenylamine (TFB) and an amine-based polymer.

The hole transporting layer 140 may be formed to a thickness of about 10 nm to about 1000 nm, more specifically, about 10 nm to about 150 nm.

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 HT-D2, but are not limited thereto.

When the hole transporting region includes a buffer layer, the buffer layer material may be selected from a material that can be used in the hole transporting region as described above and a host material described below, but is not limited thereto.

In addition, when the hole transporting region includes an electron blocking layer, the electron blocking layer material may be selected from a material that can be used in the hole transporting region as described above and a host material described below, but is not limited thereto . For example, when the hole transporting region includes an electron blocking layer, mCP can be used as the electron blocking layer material.

And a light emitting layer 150 is formed on the hole transporting region. The light emitting layer 150 is a layer that emits light by fluorescence or phosphorescence. The light emitting layer 150 may include a host and / or a dopant, and the host may include a heterocyclic compound represented by the above formula (1). As the host and the dopant used for the light emitting layer 150, known materials can be used.

For example, the host is tris (8-quinolinato) aluminum (tris (8-quinolinato) aluminium : Alq 3), 4,4'- bis (carbazol-9-yl) biphenyl (4, 4 ' poly (n-vinylcarbazole): PVK), 9,10-di (naphthalene-2-yl) anthracene (9,10 4,4 ', 4 "-tris (N-carbazolyl) anthracene (ADTA), 4,4' 3-tert-butyl-9,10-di-tert-butylbenzene (N-phenylbenzimidazol- Di (naphth-2-yl) anthracene (TBADN), distyrylarylene (DSA), 4,4'- Bis (9-carbazole) -2,2'-dimethyl-bipheny: dmCBP) and the following compounds and the like. However, the present invention is not limited thereto.

According to one embodiment, the light emitting layer includes the heterocyclic compound represented by Formula 1, and the light emitting layer includes the compound represented by Formula 4-1, the compound represented by Formula 4-2, The compound represented by Formula (6), and the compound represented by Formula (7).

For example, the dopant may be selected from the group consisting of perlene and derivatives thereof, rubrene and derivatives thereof, coumarin and derivatives thereof, 4-dicyanomethylene-2- (p-dimethylaminostyryl) 4-pyran: DCM) and derivatives thereof, bis [2- (4,6-difluorophenyl) pyridyl) Bis (1-phenylisoquinoline) (acetylacetonate) iridium (III) (III) (bis [2- (4,6-difluorophenyl) pyridinate] picolinate iridium Ir (ppy) ₂ (acac)), tris (2-phenylpyridine) iridium (III), bis (1-phenylisoquinoline) acetylacetonate iridium ) _3), tris (2- (3-p- xylyl) phenyl) pyridine iridium (III) (tris (2- ( 3-p-xylyl) phenyl) pyridine iridium (III)) ( dopant) such as the iridium complex , An osmium complex, a platinum complex, and the like, but is not limited thereto.

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 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

The light emitting layer 150 may be formed to a thickness of about 10 nm to about 60 nm.

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.

An electron transporting region may be formed on the light emitting layer 150.

The electron transporting region may include at least one of a hole blocking layer (not shown), an electron transporting layer 160, and an electron injection layer 170.

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.

For example, the organic light emitting device 100 may include a hole blocking layer between the electron transporting layer 160 and the light emitting layer 150 to prevent excitons or holes from diffusing into the electron transporting layer 160. The hole blocking layer may include, but is not limited to, at least one of oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, Bphen, and Balq.

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.

Electron-transporting layer 160 of tris (8-quinolinato) aluminum (tris (8-quinolinato) aluminium : Alq 3), Balq; A pyridine ring such as 1,3,5-tri [(3-pyridyl) -phen-3-yl] benzene (1,3,5-tri [(3-pyridyl) -phen- ; 2,4,6-tris (3 '- (pyridin-3-yl) biphenyl- -yl) biphenyl-3-yl) -1,3,5-triazine); 2- (4- (N-phenylbenzimidazol-1-yl-phenyl) -9,10-dinaphthylanthracene (2- (4- (N-phenylbenzimidazolyl- -dinaphthylanthracene, compounds containing an imidazole ring such as TAZ and NTAZ, 1,3,5-tris (N-phenylbenzimidazol-2-yl) benzene , 5-tris (N-phenyl-benzimidazol-2-yl) benzene: TPBi), BCP, Bphen and the like.

Alternatively, the electron transport layer 160 may include commercially available products such as KLET-01, KLET-02, KLET-03, KLET-10 and KLET-M1 (available from Chemipro Kasei).

The electron transporting layer 160 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 transporting layer 160 may be formed to a thickness of, for example, about 15 nm to about 50 nm.

An electron injection layer 170 is formed on the electron transport layer 160.

The electron injection layer 170 may be formed of a lithium compound such as (8-hydroxyquinolinato) lithium (Liq) and lithium fluoride (LiF), sodium chloride (NaCl), cesium fluoride CsF), lithium oxide (Li ₂ O), barium oxide (BaO), or the like.

The electron injection layer 170 may be formed to a thickness of about 0.3 nm to about 9 nm.

A second electrode 180 is formed on the electron injection layer 170. The second electrode 180 is a negative electrode, and may be formed of a material having a small work function among metals, alloys, electrically conductive compounds, and combinations thereof. For example, the second electrode 180 may be formed of a metal such as lithium (Li), magnesium (Mg), aluminum (Al), calcium (Ca), or aluminum- ), Magnesium-silver (Mg-Ag), or the like. Alternatively, the second electrode 180 is a transparent conductive film made of the metal or alloy thin film, an indium tin oxide having a thickness of less than _{20nm (In 2 O 3 -SnO 2} ) and indium zinc oxide (In ₂ O ₃ -ZnO) And may be formed as a transparent electrode.

In addition, the stacking structure of the organic light emitting diode 100 according to an embodiment of the present invention is not limited to the above-described example. The organic light emitting diode 100 according to an exemplary embodiment of the present invention may be formed in any other known laminated structure. For example, in the organic light emitting diode 100, one or more layers of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, and the electron injection layer 170 may be omitted, As shown in FIG. In addition, each layer of the organic light emitting diode 100 may be formed as a single layer or may be formed as multiple layers.

The method for manufacturing each layer of the organic light emitting device 100 according to an embodiment of the present invention is not particularly limited and may be manufactured by various methods such as vacuum deposition, solution coating, LB method, and the like.

The solution coating method may be applied by a spin coating method, a casting method, a micro gravure coat method, a gravure coat method, a bar coat method, a roll coat A wire bar coat method, a dip coat method, a spry coat method, a screen printing method, a flexographic method, an offset printing method, , An ink jet printing method, and the like.

The solvent used in the solution coating method is selected from the group consisting of toluene, xylene, diethyl ether, chloroform, ethyl acetate, dichloromethane, tetrahydrofuran, acetone, acetonitrile, N, N-dimethylformamide, dimethylsulfoxide, Methylenephosphoric triamide, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene, o-dichlorobenzene, dioxane, cyclohexane, n-pentane, n- But are not limited to, ethylene, propylene, butylene, octane, n-nonane, n-decane, methyl ethyl ketone, cyclohexanone, butyl acetate, ethyl cellosolve acetate, ethylene glycol, ethylene glycol monobutyl ether, ethylene glycol monomethyl ether, , Propylene glycol, diethoxymethane, triethylene glycol monoethyl ether, glycerin, 1,2-hexanediol, methanol, ethanol, propanol, isopropanol, cyclohexanol, And the like, but it is not limited as long as it can dissolve the material used for forming each layer.

The concentration of the composition used in the solution coating method may be specifically from 0.1% by weight or more to 10% by weight or less, more specifically from 0.5% by weight or more to 5% by weight or less in consideration of coating property and the like, but is not limited thereto .

The vacuum deposition method may be carried out at a deposition temperature of about 100 to about 500 DEG C, a vacuum degree of about 10 ^-8 to about ^10-3 torr, a deposition rate of about 0.01 To about 100 A / sec.

In one embodiment, the first electrode 120 may be an anode and the second electrode 180 may be a cathode.

For example, the first electrode 120 is an anode, the second electrode 180 is a cathode, and an organic layer including a light emitting layer 150 interposed between the first electrode 120 and the second electrode 180 Wherein the organic layer further includes a hole transporting region interposed between the first electrode and the light emitting layer and an electron transporting region interposed between the light emitting layer and the second electrode, The hole transporting region includes at least one selected from a hole injection layer 130, a hole transporting layer 140, a buffer layer, and an electron blocking layer. The electron transporting region includes a hole blocking layer, an electron transporting layer 160, 170). &Lt; / RTI &gt;

In another embodiment, the first electrode 120 may be a cathode and the second electrode 180 may be an anode.

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

[Description of Substituent]

In the present specification, "X and Y independently of each other" means that X and Y may be mutually the same or different from each other.

In the present specification, "substituted" means that the hydrogen atom of a substituent such as R ₁ can be further substituted with another substituent.

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 a methyl group, ethyl group, n-propyl group, isopropyl group, n An n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, Butyl group, 1-methylbutyl group, 1-methylbutyl group, 1-methylbutyl group, 1-methylbutyl group, Methylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylhexyl group, 3- an n-decyl group, an n-decyl group, a 1-methyldecyl group, a n-dodecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-octadecyl group, an n- N-eicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, n-octadecyl group, n-tetracosyl 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 C ₁ -C ₂₄ alkyl group), and specific examples thereof include methoxy group, ethoxy group , Propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, n-pentoxy group, isopentoxy group, tert- A heptyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxyl group, a dodecyloxyl group, a tridecyloxyl group, a tetradecyloxyl group, a pentadecyloxyl group, Heptadecyloxy group, octadecyloxy group, 2-ethylhexyloxy group, 3-ethylpentyloxy group and the like.

In the present specification, a C ₁ -C ₆₀ alkylthio group means a monovalent group having the formula: -SA ₁₀₂ (wherein A ₁₀₂ is the above C ₁ -C ₆₀ alkyl 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 which participates in the ring formation, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group , A cyclohexyl group, a cycloheptyl 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.

As used herein, the term &quot; C ₆ -C ₆₀ aryl &quot; means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms participating in the ring formation (that is, when substituted by a substituent, the atom contained in the ring formed is not included in the number of carbon), and C ₆ -C ₆₀ arylene group refers to a divalent (divalent) group having a carbon number of 6 to 60 carbocyclic 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 cryanecyl group and the like. The C ₆ -C ₆₀ aryl groups and C ₆ -C ₆₀ arylene If the group contains two or more rings, the 2 or more rings may be fused to each other.

The specification of the C ₆ -C ₆₀ aryloxy group -OA ₁₀₃ refers to (wherein, A ₁₀₃ is the C ₆ -C ₆₀ aryl group). Specific examples thereof include 1-naphthyloxy group, 2-naphthyloxy group, 2-azulenyloxy group and the like.

In the specification C ₆ -C ₆₀ arylthio group -SA ₁₀₄ refers to (wherein, A ₁₀₄ is the C ₆ -C ₆₀ aryl group).

As used herein, a C ₁ -C ₆₀ heteroaryl group includes at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, and includes a heterocyclic group having 1 to 60 carbon atoms Aromatic group, wherein the C ₁ -C ₆₀ heteroarylene group comprises at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom, Means a divalent group having from 1 to 60 carbon atoms in the heterocyclic aromatic system. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, two or more rings may be condensed with each other.

In the present specification, a C ₁ -C ₆₀ heteroaryloxy group refers to -OA ₁₀₅ (wherein A ₁₀₅ is the above C ₁ -C ₆₀ heteroaryl group). Specific examples thereof include 2-furanyloxy group, 2-thienyloxy group, 2-indolyloxy group, 3-indolyloxy group, 2-benzopyryloxy group, 2-benzothienyloxy group and the like.

In the present specification, a C ₁ -C ₆₀ heteroarylthio group refers to -SA ₁₀₆ (wherein A ₁₀₆ is the above C ₁ -C ₆₀ heteroaryl group).

In the present specification, the C ₇ -C ₃₀ arylalkyl group refers to a monovalent group having 7 to 30 carbon atoms in the alkyl group and the aryl group constituting the aryl group as an alkyl group. Specific examples of the C ₇ -C ₃₀ arylalkyl group include a benzyl group, a phenylethyl group, a phenylpropyl group, and a naphthylmethyl group.

In the present specification, the C ₆ -C ₃₀ arylalkyloxy group indicates -OA ₁₀₅ (wherein A ₁₀₅ is the above C ₇ -C ₃₀ arylalkyl group).

In the specification C ₆ -C ₃₀ aryl alkylthio group -SA ₁₀₆ (wherein, A ₁₀₆ is being the C ₇ -C ₃₀ arylalkyl group) refers to.

In the present specification, the C ₈ -C ₃₀ arylalkenyl group refers to a monovalent group having 8 to 30 carbon atoms in the alkenyl group and the aryl group constituting the aryl group in the alkenyl group.

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

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group is a condensed heteropolycyclic group in which two or more rings are condensed with each other and a hetero atom selected from N, O, P, Si and S Quot; refers to a monovalent group (e.g., having from 1 to 60 carbon atoms) having a non-aromacity throughout the molecule. 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, a C ₅ -C ₃₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as a ring forming atom. The C ₅ -C ₃₀ carbocyclic group may be a monocyclic group or a polycyclic group, and may be a monovalent, divalent, trivalent, tetravalent, pentavalent or hexavalent group, depending on the chemical structure.

In the present specification, a C ₁ -C ₃₀ heterocyclic group refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si and S in addition to 1 to 30 carbons as a ring forming atom. The C ₁ -C ₃₀ heterocyclic group may be a monocyclic group or a polycyclic group, and may be monovalent, divalent, trivalent, tetralic, pentavalent or hexavalent, depending on the structure of the formula.

In the present specification, the substituted C ₅ -C ₃₀ carbocyclic group, the substituted C ₁ -C ₃₀ heterocyclic group, the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted a C ₁ -C ₁₀ heteroaryl cycloalkenyl 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 ₁ -C ₆₀ At least one of a substituted aryl group, a heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic heterocyclic polycyclic group,

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, An alkynyl group and a C ₁ -C ₆₀ alkoxy group;

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 11) (Q} 12), -Si (Q 13) (Q 14) (Q 15), -B (Q _{16) (Q 17), -P} (= O) (Q 18) (Q 19) and -C (= O) (at least one substituted, C ₁ -C ₆₀ alkyl group of the Q _20), C ₂ -C ₆₀ An alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

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

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic _{, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27), -P (= O) (Q 28) (Q _29), and -C (= O) with at least one a, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ substituted one (Q ₃₀₎ A heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic condensed Polycyclic group; And

_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35), -B (Q 36) (Q 37), -P (= O) (Q 38) (Q 39 ) And -C (= O) (Q ₄₀ );

&Lt; / RTI &gt;

Wherein Q ₁ to Q ₁₀ , Q ₁₁ to Q ₂₀ , Q ₂₁ to Q ₃₀ and Q ₃₁ to Q ₄₀ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group substituted by at least one of C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

[Other]

In the present specification, "A to B" means a range from A to B including A and B.

While the present invention has been described in connection with what is presently considered to be the most practical and preferred embodiment, it is to be understood that the invention is not limited to the disclosed embodiments. It will be understood by those skilled in the art that various changes and modifications may be made without departing from the scope of the invention as defined in the appended claims. It is understood that various changes and modifications are within the technical scope of the present invention.

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, referring to Examples and Comparative Examples, a heterocyclic compound represented by Formula 1 and an organic light emitting device including the same will be described in detail. The embodiments described below are only illustrative, and the heterocyclic compound and the organic light emitting diode according to one embodiment of the present invention are not limited by the following embodiments.

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.

In addition, "%" is by weight unless otherwise specified.

[Example]

Hereinafter, a light emitting device material and an organic light emitting device according to the present embodiment will be described in detail with reference to examples and comparative examples. The following embodiments are merely examples, and the light emitting device material and the organic light emitting device according to the present embodiment are not limited to the following embodiments.

Synthesis Example 1: Synthesis of Compound 1

(1) Synthesis of intermediate 1

Phenyl] -6 (5'-phenyl [1,1 ': 3'1''-terphenyl] -3-yl) -1,3,5-triazine (4.00 g, 7.67 mmol), 3-phenyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaboran- , Sodium carbonate (2.03 g, 19.18 mmol), dioxane (77 ml) and water (38 ml) were added and mixed. Next, the mixture was stirred at 85 캜 for 4 hours, and after completion of the reaction, the reaction mixture was cooled to room temperature, and the impurities were separated by filtration using Celite (registered trademark). Next, the solvent was distilled, purified by column chromatography, and then dispersed and washed with methanol to obtain Intermediate 1 (2.92 g).

(2) Synthesis of Compound 1

(2.30 g, 2.95 mmol), 2-bromo-9,9'-spirobifluorene (1.28 g, 3.25 mmol), tris (dibenzylideneacetone) dipalladium 0) (0.135 g, 0.15 mmol), (tBu) ₃ P / BF ₄ (0.09 g, 0.30 mmol), sodium tert-butoxide (0.85 g, 8.86 mmol) and xylene (46 ml) were added and mixed. Next, after the reaction was completed by stirring the mixture at 120 DEG C for 6 hours, the reaction mixture was cooled to room temperature, and the impurities were separated by filtration using Celite (registered trademark). Then, the solvent was distilled off and purified by column chromatography to obtain Compound 1 (6 g).

Synthesis Example 2: Synthesis of Compound 2

(1) Synthesis of intermediate 2

(5.00 g, 12.55 mmol), 3- (4,4,5,5, -tetramethyl-l, 3,2-di (3.31g, 11.30mmol), bis (triphenylphosphine) palladium (II) dichloride (0.18g, 0.25mmol), sodium carbonate (3.33g, 31.38mmol), dioxane (126 ml) and water (63 ml) were added and mixed. Next, after the mixture was stirred at 85 캜 for 4 hours to terminate the reaction, the reaction mixture was cooled to room temperature and the impurities were separated by filtration using Celite (registered trademark). The next solvent was distilled and purified by column chromatography to give precipitated intermediate 2 (6.5 g).

(2) Synthesis of Compound 2

(3.00 g, 6.19 mmol), 4-bromo-9,9'-spirobifluorene (2.20 g, 5.57 mmol), tris (dibenzylideneacetone) dipalladium (0) (0.113 g, 0.12 mmol), (tBu) ₃ P / BF ₄ (0.14 g, 0.50 mmol), sodium tert-butoxide (0.89 g, 9.29 mmol) and xylene (26 ml). Next, after the reaction was completed by stirring the mixture at 120 DEG C for 6 hours, the reaction mixture was cooled to room temperature, and the impurities were separated by filtration using Celite (registered trademark). Then, the solvent was distilled off and then purified by column chromatography to obtain Compound 2 (2 g).

Examples 1 to 6 and Comparative Examples 1 to 3

First, PEDOT-PSS (manufactured by Sigma-Aldrich) was applied by spin coating onto an ITO glass substrate on which a stripe-shaped indium tin oxide (ITO) film having a thickness of 150 nm was deposited with a first electrode A hole injection layer having a film thickness of 15 nm was formed.

Next, P-1 and FA-14 were dissolved in anisole to prepare a coating liquid for a hole transport layer. Here, FA-14 was formulated so as to be 20% by weight based on the total weight of the hole transporting layer. On the hole injection layer, a coating liquid for a hole transport layer was applied by spin coating to form a hole transport layer having a thickness of 125 nm. Here, the chemical formulas of P-1 and FA-14 are as follows. P-1 was also synthesized according to the synthesis method described in International Publication No. 2011/159872.

Then, a tris (2- (3-p-xylyl) phenyl) pyridine iridium (III) (tris (2- (3-p-xylyl) phenyl) pyridine iridium (III) ) (TEG)) was dissolved in methylbenzoate to prepare a coating solution for a light emitting layer. Here, the doping amount of the dopant material was 10 wt% based on the total weight of the light emitting layer. Next, a coating liquid for a light-emitting layer was coated on the hole-transporting layer by a spin coating method to form a light-emitting layer having a thickness of 55 nm.

Lithium quinolate (Liq) and KLET-03 (chemiluminescent agent) were uniformly adhered on the light emitting layer by vacuum deposition to a mass ratio of 1: 1 to form an electron transporting layer having a thickness of 20 nm.

Lithium quinolate (Liq) was vapor-deposited on the electron transport layer by a vacuum deposition method to form an electron injection layer with a thickness of 3.5 nm.

Aluminum (Al) was deposited on the electron injecting layer by a vacuum deposition method to form a second electrode (cathode) having a thickness of 100 nm to manufacture an organic light emitting device.

Here, the chemical formulas of the compounds 3 to 7 used as the host material are as follows. Further, the compounds 3 to 5 were synthesized according to the synthetic methods described in International Patent Publication Nos. WO08 / 078795, International Publication No. 2016/033167 and International Publication No. 2016/033167. Compounds 6 and 7 were also synthesized according to the synthetic method described in U.S. Patent Application Publication No. 2017-174705.

&Lt; Current efficiency and lifetime of organic light emitting device >

The current efficiency and device lifetime of the organic luminescent devices of Examples 1 to 6 and Comparative Examples 1 to 3 were evaluated by the following methods.

A predetermined voltage was applied to each organic light emitting element using a DC constant voltage power source meter (KEYENCE) to emit the organic light emitting element. At this time, the luminance of the organic light emitting element that emits light was measured using the luminance measuring device SR-3 (manufactured by Topcom). Then, the current density was gradually increased to 6000 cd / m &lt; ² &gt; by increasing the current, and the current was kept constant. The current efficiency was calculated at the obtained current density.

Further, a value obtained by measuring the time (LT95) until the luminance value of the organic light emitting element that emits light reaches 95% of the initial measured value was defined as the element lifetime.

Table 1 shows the evaluation results of current efficiency and device lifetime of the organic light emitting device. In Table 1, the ratio of the host material means the mass ratio, and the current efficiency and device lifetime are relative values when the measured value of the organic light emitting device of Comparative Example 1 is 100.

The light- Current efficiency
(Optional unit) Device life
(Optional unit) Example 1 Compound 1 123 150 Example 2 Compound 1: Compound 2 (5: 5) 121 400 Example 3 Compound 1: Compound 3 (5: 5) 126 250 Example 4 Compound 1: Compound 4 (5: 5) 120 300 Example 5 Compound 1: Compound 5 (7: 3) 125 300 Example 6 Compound 1: Compound 5 (3: 7) 121 500 Example 7 Compound 1: Compound 5 (2: 8) 122 700 Comparative Example 1 Compound 6: Compound 7 (5: 5) 100 100 Comparative Example 2 Compound 6 28 10

In Table 1, the organic luminescent device of Example 1 using the compound 1 alone had higher current efficiency and longer device life than the organic luminescent device of Comparative Example 2 using only the compound 6 and the compound 7 and Comparative Example 2 using only the compound 6 It can be seen that it is excellent.

It is also understood that the lifetime of the device is further improved in the organic light emitting devices of Examples 2 to 6 using the compound 1 and the compounds 2 to 5 together.

&Lt; Glass transition temperature of compound and solubility in methyl benzoate >

The glass transition temperature (Tg) of compounds 1, 2, 6, 7 and compound A and their solubility in methyl benzoate were measured.

Here, the glass transition temperature (Tg) of the compound was measured in accordance with JIS K 7121 using SII DSC6220 (manufactured by Seiko Instruments Inc.).

Further, the solubility of the compound in methylbenzoate was determined by thoroughly mixing the compound and methylbenzoate so that the concentration of the compound became a predetermined value in an environment of 25 캜, and then visually determining the mixture. More specifically, it was determined that the compound was dissolved when the mixture was transparent, and when the mixture was opaque, it was determined that the compound was not dissolved.

Table 2 shows the results of the evaluation of the solubility of the compounds 1, 2, 6, 7 and Compound A to Tg and methylbenzoate.

Tg (占 폚) Solubility in methyl benzoate (% by mass) Compound 1 178 > 4 Compound 2 194 > 4 Compound 6 146 > 4 Compound 7 157 > 4 Compound A 120 Does not melt

<Compound A>

From Table 2, it can be seen that Compounds 1 and 2 are superior in heat resistance and solubility to Compounds 6 and 7 and Compound A, and are suitable as materials for organic light emitting devices for solution coating methods.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, is intended to cover various modifications and equivalent arrangements included within the scope of the appended claims.

100: Organic light emitting device
110: substrate
120: first electrode
130: Hole injection layer
140: hole transport layer
150: light emitting layer
160: electron transport layer
170: electron injection layer
180: second electrode

Claims (20)

A heterocyclic compound represented by the following formula (1):
&Lt; Formula 1 >
(A) _n- L
Wherein A is a group excluding one hydrogen atom from a compound represented by the following general formula (1-1) or a compound excluding a hydrogen atom from a compound represented by the general formula (1-2)
n is an integer of 1 to 8,
L is hydrogen, a single bond or an n-valent linking group,
when n is 1, L is hydrogen,
&Lt; Formula 1-1 >

(1-2)

Of the above formulas (1-1) and (1-2)
X ₁ to X ₁₆ independently of one another are N or C,
X ₁ to at least one of X ₈ is - carbon bond and, - _a1 (L ₁₎
In formula (1-1), one of X ₉ to X ₁₂ is a carbon bonded to A _3, and one of X ₁₃ to X ₁₆ is a carbon bonded to A ₄ ,
Of formulas 1-2, X ₉ to X ₁₂ is one of the - (L _{1) a1} - and the carbon bond, and one of X ₁₃ to X ₁₆ is a carbon bond with A _4,
A ₁ and A ₄ independently represent hydrogen, a group represented by * - (L ₂ ) a ₂ -R _ET , a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkene A substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl alkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted hwandoen C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed A polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group,
A ₃ and A ₄ is a group represented by * - (L ₂ ) a ₂ -R _ET ,
A ₁ and A ₂ are optionally linked to each other to form a saturated ring or an unsaturated ring,
L ₁ and L ₂ are each independently selected from a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
a1 and a2 are independently of each other, is selected from an integer from 0 to 3, in the case of a1 is _{0 * - (L 1) a1} - * ' is a single bond, if a2 is _{0 * - (L 2) a2} - * Is a single bond,
R _ET is a substituted or unsubstituted C ₁ -C ₆₀ nitrogenous heterocyclic group,
R ₁ to R ₅ 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, 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, a substituted or unsubstituted C ₂ -C _A substituted or unsubstituted C ₁ -C ₆ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, A substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic Condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q 4) (Q 5), -B (Q 6 ) is selected from _{(Q 7), -P (=} O) (Q 8) (Q 9) , and _{-C (= O) (Q 10} ),
b1 and b2 are independently selected from the integers of 0 to 4, b3 and b4 are each independently selected from integers of 0 to 3,
n1 is selected from integers from 1 to 8,
However, the formula of 1-1, A ₁ and A ₂ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group when R _ET substituted or unsubstituted pyridinyl, substituted or unsubstituted pyrimidinyl group in , A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group are excluded,
Said substituted C ₁ -C ₆₀ nitrogenous heterocyclic group, substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -C ₃₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted A C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted Substituted C ₃ -C ₁₀ cycloalkenyl groups, substituted C ₁ -C ₁₀ heterocycloalkenyl groups, substituted C ₆ -C ₆₀ aryl groups, substituted C ₆ -C ₆₀ aryloxy groups, substituted C ₆ -C ₆₀ At least one of the substituents of the substituted monovalent non-aromatic heterocyclic polycyclic group, the arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, An alkynyl group and a C ₁ -C ₆₀ alkoxy group;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, 1 is a non-condensed polycyclic aromatic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -N (Q 11) (Q} 12), -Si (Q 13) (Q 14) (Q 15), -B (Q _{16) (Q 17), -P} (= O) (Q 18) (Q 19) and -C (= O) (at least one substituted, C ₁ -C ₆₀ alkyl group of the Q _20), C ₂ -C ₆₀ An alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl, C ₁ -C ₁₀ heterocycloalkyl, C ₃ -C ₁₀ cycloalkenyl, C ₁ -C ₁₀ heterocycloalkenyl, C ₆ -C ₆₀ aryl, C ₆ -C ₆₀ aryl A C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group;
Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic _{, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27), -P (= O) (Q 28) (Q _29), and -C (= O) with at least one a, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ substituted one (Q ₃₀₎ A heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic condensed Polycyclic group; And
_{-N (Q 31) (Q 32} ), -Si (Q 33) (Q 34) (Q 35), -B (Q 36) (Q 37), -P (= O) (Q 38) (Q 39 ) And -C (= O) (Q ₄₀ );
&Lt; / RTI &gt;
Wherein Q ₁ to Q ₁₀ , Q ₁₁ to Q ₂₀ , Q ₂₁ to Q ₃₀ and Q ₃₁ to Q ₄₀ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group substituted by at least one of C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group. The method according to claim 1,
R _ET is an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, A quinolinyl group, a quinolizinyl group, a phenanthridinyl group, an acridinyl group, a phenanthridinyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, a pyrazolyl group, A phenanthrolinyl group, a benzophenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a naphthomidazolyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, An imidazopyrimidinyl group, an imidazoquinolinyl group, an imidazoisoquinolinyl group, an azadibenzofuranyl group, a diazodibenzofuranyl group, a azadibenzothiocarbamoyl group, A phenyl group, a diazadibenzothiophenyl group, Here fluorenyl group, diaza fluorenyl group, a fluorenyl group, and by by-fluorenyl group as a spy-diaza-aza spy;
A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group , A phenanthrenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, an heptalenyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, A phenanthryl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a pyranyl group, a pyranyl group, a phenanthryl group, a phenanthrenyl group, a triphenylenyl group, a fluoranthenyl group, a pyrenyl group, A thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group, A pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indazolyl group, A phenanthridinyl group, an acridinyl group, a phenanthryl group, a phenanthryl group, an acridinyl group, an acridinyl group, an acridinyl group, an acridinyl group, an acridinyl group, A benzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, a tetrazolyl group, An imidazopyrimidinyl group, an imidazoquinolinyl group, an imidazoisoquinolinyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azadibenzothiophenyl group , A diazadibenzothiophenyl group, an azafluorenyl group, a diazafluorenyl group, an azaspirofiburanyl group, and a diazaspirofluoranyl group; And
An acenaphthyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a di A phenanthrenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, A phenyl group substituted with at least one member selected from the group consisting of a pyridyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group, a phentalenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, A phenanthrenyl group, a triphenylenyl group, a fluorenyl group, a pyrenyl group, a cyanecyl group, a phenanthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a fluorenyl group, Group, a phenenyl group, a perylenyl group An imidazolyl group substituted with at least one member selected from the group consisting of a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group, An isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an iso 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, An isothiazolyl group, a benzimidazolyl group, a naphthomidazolyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, Zofiridinyl group, imidachoxifene An imidazoquinolinyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azadibenzothiophenyl group, a diazabenzothiophenyl group, an azafluorenyl group, a diazafluoro group, Aza-spirobifluorenyl group, and a diazaspirofluoranyl group;
&Lt; / RTI &gt; The method according to claim 1,
R _ET is a heterocyclic compound selected from the group consisting of the following formulas (2-1) to (2-3):

Of the above-mentioned formulas (2-1) to (2-3)
X ₂₁ to X ₃₃ are independently of each other N or C,
At least one of X ₂₁ to X ₂₅ is N, at least one of X ₂₆ to X ₂₉ is N, at least one of X ₃₀ to X ₃₃ is N,
Y ₂₁ and Y ₂₂ are independently selected from O, S, N (R ₂₅ ) and C (R ₂₅ ) (R ₂₆ )
Z is selected from a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₂ -C ₃₀ heterocyclic group,
R ₂₁ to R ₂₆ 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, 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, a substituted or unsubstituted C ₂ -C _A substituted or unsubstituted C ₁ -C ₆ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-direction The condensed polycyclic groups, and substituted or unsubstituted 1, a non-aromatic heterocyclic is selected from a condensed polycyclic group,
Two adjacent substituents of R ₂₁ to R ₂₆ may be optionally linked to each other to form a saturated ring or an unsaturated ring,
b21 to b23 are each independently selected from an integer of 1 to 4, b24 is selected from an integer of 1 to 3,
* Is a binding site with neighboring atoms. The method according to claim 1,
R _ET is a heterocyclic compound selected from the group consisting of the following formulas (3-1) to (3-18)

Of the above formulas (3-1) to (3-18)
The definitions of R ₂₁ to R ₂₄ , b ₂₁ to b ₂₃ , and Y ₂₂ are the same as those described in the definitions of the above formulas 2-1 to 2-3,
The definitions of R ₂₅ and R ₂₆ refer to the definition of R ₂₁ above,
b25 and b26 are each independently selected from integers from 1 to 4,
"Ph" is a phenyl group, and * is a bonding site with neighboring atoms. The method of claim 3,
R ₂₁ to R ₂₆ are, independently from each other, hydrogen, deuterium, a heterocyclic compound selected from the following formulas R-1 to R-28:

Among the above-mentioned formulas R-1 to R-28,
* Is a binding site with neighboring atoms. 6. The method of claim 5,
R ₂₁ to R ₂₆ are each independently of the other hydrogen, deuterium, a heterocyclic compound selected from the above-mentioned R-1, R-9, R-12 to R-15 and R-20 to R-28. The method according to claim 1,
A ₁ to A ₄ are, independently of each other,
_{Hydrogen, * - (L 2) a2} -R group is represented by _ET, a methyl group, an ethyl group, n- propyl group, isopropyl group, n- butyl group, isobutyl group, sec- butyl group, tert- butyl group, n Isopropyl group, 1-methylpropyl group, 1-methylpropyl group, 1-ethylbutyl group, Methyl-1-isopropylpropyl group, 1-ethyl-3-methylbutyl group, n-heptyl group, n-heptyl group, Methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, n-nonyl group, Pentadecyl group, n-pentadecyl group, n-pentadecyl group, n-pentadecyl group, n-octadecyl group, N-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group, n-heneicosyl group, N-docosyl group, n -Tricosyl group, n-tetracosyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec- , n-pentoxy group, isopentoxy group, tert-pentoxy group, neopentoxy group, n-hexyloxy group, isohexyloxy group, heptyloxy group, octyloxy group, , Undecyloxy group, dodecyloxy group, tridecyloxy group, tetradecyloxy group, pentadecyloxy group, hexadecyloxy group, heptadecyloxy group, octadecyloxy group, 2-ethylhexyloxy group, 2-thienyloxy group, 2-indolyloxy group, 3-indolyloxy group, 2-naphthyloxy group, 2-thienylthio group, A 2-benzothienyloxy group, an N-methylamino group, an N-ethylamino group, an N-propylamino group, an N-isopropylamino group, an N-butylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N-dipropylamino group, N, N-dimethylamino group, N, , N-diisopropylamino group, N, N-dibutylamino group, N, N-diisobutylamino group, N, N-dipentylamino group and N, N-dihexylamino group;
An acenaphthyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a di A phenanthrenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a fluoranthenyl group, a pyrenyl group, a klychenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, , Hexaphenyl group, hexacenyl group, rubicenyl group, trinaphthyl group, heptaphenyl group, pyranthrenyl group, pyridinyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, A benzoquinolinyl group, a phenanthridinyl group, a phenanthrolinyl group, a benzoquinonyl group, a coumarinyl group, a benzoquinolinyl group, a benzoquinolyl group, a benzoquinolyl group, a benzoquinolyl group, Anthraquinone group, fluorenone group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a furyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, Benzoxazolyl group, benzoxazolyl group, dibenzocarbazolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indazolyl group, oxazolyl group, isoxazolyl group, A thiazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzisothiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazophenanthridinyl group, a benzimidazophenanthryl group, An azadibenzofuranyl group, an azacabazolyl group, an azadibenzothienyl group, a diazadibenzofuranyl group, a diazacabazolyl group, a diazadibenzothienyl group, a jazminonyl group, and a thioxanthonyl group; And
A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C ₁ -C ₃₀ alkyl group, a C ₁ -C ₃₀ alkoxy group, a phenyl group , A phenanthrenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, an heptalenyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, A fluorenyl group, a pyrenyl group, a klycenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenyl group, a fluorenyl group, a pyrenyl group, a phenanthryl group, A pyridinyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, A quinoxalinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group, a benzoquinone group, A phenanthrolinyl group, a benzoquinone group, a coumarinyl group, an anthraquinone group, a fluorenone group, a furanyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a dibenzothiophenyl group, a dibenzoyl group, a pyrrolyl group, An oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, , Benzisothiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazophenanthridinyl group, benzimidazophenanthridinyl group, azadibenzofuranyl group, azacarbazolyl group, azadibenzoyl group, Thienyl group, diazodibenzofura Naphthyl group, anthracenyl group, azulenyl group, heptareyl group, thiazolidinyl group, thiazolyl group, thiazolidinyl group, thiazolidinyl group, thiazolidinyl group, thiazolidinyl group, diazacarbazolyl group, diazabazoyl group, diazadibenzothienyl group, A phenanthrenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a fluorenyl group, an acenaphthyl group, a phenanthryl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, An alkenyl group, an alkynyl group, an alkenyl group, an alkynyl group, an alkenyl group, an alkynyl group, an alkenyl group, an alkenyl group, an alkynyl group, A pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group , Benzoquinolinyl group, benzo A thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, a benzoylolyl group, a diethoxycarbonyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A benzofuranyl group, a dibenzothiophenyl group, a dibenzoylsilyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazolyl group, a benzimidazolyl group, A thiazolyl group, a thiazolyl group, a tetrazolyl group, an indazolyl group, an oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, A diazo group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazophenanthridinyl group, a benzimidazophenanthridinyl group, an azadibenzofuranyl group, an azacabazolyl group, an azadibenzothienyl group, Benzofuranyl group, diazacar Sol group, dia jadi benzothienyl group, janton group and thioxanthone group;
&Lt; / RTI &gt; The method according to claim 1,
A ₁ and A ₂ are linked together to form a heterocyclic compound represented by the following formula (9):
&Lt; Formula 9 >

In the formula (9)
X ₉₁ to X ₉₈ independently of one another are N or C,
R ₉₁ to R ₉₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, 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, a substituted or unsubstituted C ₂ -C _A substituted or unsubstituted C ₁ -C ₆ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C _A substituted or unsubstituted C ₁ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-direction Condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N (Q 4) (Q 5) and -B (Q ₆ ) is selected from (Q _7),
b91 to b92 are independently selected from integers from 1 to 4,
* Is a binding site with neighboring carbon atoms. The method according to claim 1,
L ₁ and L ₂ each independently represent a group selected from the group consisting of a benzene group, a phenalene group, an indene group, a naphthalene group, an anthracene group, an azulene group, an hethalene group, an acenaphthalene group, a phenalene group, A phenylene group, a phenanthrene group, a biphenyl group, a terphenyl group, a triphenylene group, a fluoranthene group, a pyrenylene group, a chrysene group, a picene group, a perylene group Group, a pentaphene group, a pentacene group, a tetraphene group, a hexaphene group, a hexasene group, a rubisene group, a trinaphthalene group, a heptapene group, a pyranthrene group, A pyrazine group, a pyridazine group, a pyrimidine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a naphthyridine group, an acridine group, a phenazine group, a benzoquinoline group, A quinoline group, a phenanthridine group, a phenanthroline group, a benzoquinone group, a coumarin group, an anthraquinone group, a fluorenone group, a furan group, a thiophene group, a silole group, a benzofuran group, a benzothiophene group, , Dibenzofuran group, dibenzothiophene group, dibenzosilyl group, pyrrole group, indole group, isoindole group, carbazole group, benzocarbazole group, dibenzocarbazole group, imidazole group, benzimidazole group , A pyrazole group, a triazole group, a tetrazole group, an indazole group, an oxazole group, an isoxazole group, a benzoxazole group, a benzisoxazole group, a thiazole group, an isothiazole group, A benzimidazolinone group, an imidazopyrimidine group, an imidazopyrimidine group, an imidazophenanthridine group, a benzimidazophenanthridine group, an azadiene group, Benzofuran Group, azacavazole group, azadibenzothiophene group, diazadibenzofurane group, diazacavazole group, diazadibenzothiophene group, xanthone group, and thioxanthone group; And
A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C ₁ -C ₃₀ alkyl group, a C ₁ -C ₃₀ alkoxy group, a phenyl group , A phenanthrenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, an heptalenyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, A fluorenyl group, a pyrenyl group, a klycenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenyl group, a fluorenyl group, a pyrenyl group, a phenanthryl group, A pyridinyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, A quinoxalinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group, a benzoquinone group, A phenanthrolinyl group, a benzoquinone group, a coumarinyl group, an anthraquinone group, a fluorenone group, a furanyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a dibenzothiophenyl group, a dibenzoyl group, a pyrrolyl group, An oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, , Benzisothiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazophenanthridinyl group, benzimidazophenanthridinyl group, azadibenzofuranyl group, azacarbazolyl group, azadibenzoyl group, Thienyl group, diazodibenzofura A benzene group, a pentane group, an indene group, a naphthalene group, an anthracene group, an azulene group, a heptarene group, a thiazole group, a thiophene group, Group, an acenaphthalene group, a phenalene group, a fluorene group, a spirobifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, a biphenyl group, a terphenyl group, A pentacene group, a pentacene group, a tetraphene group, a hexaphene group, a hexacene group, a rubisene group, a pyrenylene group, a pyrenylene group, a pyrenylene group, A triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinone group, a pyrazine group, a pyrazine group, a pyridazine group, a pyrimidine group, A phenanthrene group, a phenanthrene group, a phenanthroline group, a benzoquinone group, a coumarin group, an anthraquinone group, a fluorenone group, an anthraquinone group, a phenanthrene group, A dibenzothiophene group, a dibenzoylsilyl group, a pyrrole group, an indole group, an isoindole group, a carbamoyl group, an isoindole group, an isoindole group, a carbamoyl group, A thiazole group, an indazole group, an oxazole group, an isoxazole group, a benzoxazole group, a benzoxazole group, an imidazole group, a benzimidazole group, a pyrazole group, A benzimidazole group, a benzimidazole group, a benzimidazole group, an imidazopyridine group, an imidazopyrimidine group, an imidazopyrimidine group, an imidazopyrimidine group, Anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, anthraquinone group, Diazabenzothiophene group, xanthone group and thioxanthone group; &Lt; / RTI &gt; The method according to claim 1,
R ₁ to R ₅ independently represent hydrogen, deuterium, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, Isopropyl group, 1,2-dimethylpropyl group, isopentyl group, isopentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, Propyl group, a 1-ethyl-3-methylbutyl group, an n-octyl group, a 2-methylbutyl group, a 2-methylbutyl group, a 2-methylbutyl group, Methyl-1-isopropyl group, 1-tert-butyl-2-methylpropyl group, n-nonyl group, 3,5,5-trimethyl N-pentadecyl, n-hexadecyl, n-hexadecyl, n-hexadecyl, n-hexadecyl, N-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, n-eicosyl group, n-heneicosyl group, -docosy n-tricosyl group, n-tetracosyl group, methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, isobutoxy group , sec-butoxy group, tert-butoxy group, n-pentoxy group, isopentoxy group, tert-pentoxy group, neopentoxy group, n-hexyloxy group, isohexyloxy group, heptyloxy group, octyloxy group, A heptadecyloxy group, an octadecyloxy group, an octadecyloxy group, a 2-ethylhexyloxy group, a heptadecyloxy group, a heptadecyloxy group, a heptadecyloxy group, , 3-ethylpentyloxy group, phenoxy group, 1-naphthyloxy group, 2-naphthyloxy group, 2-azulenyloxy group, 2-furanyloxy group, 2-thienyloxy group, 2- N-propylamino group, N-isopropylamino group, N-butylamino group, N-isoamyl group, N-isopropylamino group, N-isopropylamino group, Butylamino group, N-pentylamino group, N-hexylamino group, N, N-dimethylamino group, N, N-diethylamino group, N, N-dipropylamino group, N, N-diisopropylamino group, N, N-dibutylamino group, N, N-diisobutylamino group, N, N-dipentylamino group and N, N-dihexylamino group;
An acenaphthyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a di A phenanthrenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a fluoranthenyl group, a pyrenyl group, a klychenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, , Hexaphenyl group, hexacenyl group, rubicenyl group, trinaphthyl group, heptaphenyl group, pyranthrenyl group, pyridinyl group, pyrazinyl group, pyridazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, A benzoquinolinyl group, a phenanthridinyl group, a phenanthrolinyl group, a benzoquinonyl group, a coumarinyl group, a benzoquinolinyl group, a benzoquinolyl group, a benzoquinolyl group, a benzoquinolyl group, Anthraquinone group, fluorenone group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a furyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, Benzoxazolyl group, benzoxazolyl group, dibenzocarbazolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indazolyl group, oxazolyl group, isoxazolyl group, A thiazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a benzisothiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazophenanthridinyl group, a benzimidazophenanthryl group, An azadibenzofuranyl group, an azacabazolyl group, an azadibenzothienyl group, a diazadibenzofuranyl group, a diazacabazolyl group, a diazadibenzothienyl group, a jazminonyl group, and a thioxanthonyl group; And
A halogen atom, a hydroxyl group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C ₁ -C ₃₀ alkyl group, a C ₁ -C ₃₀ alkoxy group, a phenyl group , A phenanthrenyl group, an indenyl group, a naphthyl group, an anthracenyl group, an azulenyl group, an heptalenyl group, an acenaphthyl group, a phenalenyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, A fluorenyl group, a pyrenyl group, a klycenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a pentacenyl group, a tetraphenyl group, a fluorenyl group, a pyrenyl group, a phenanthryl group, A pyridinyl group, a pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, A quinoxalinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group, a benzoquinone group, A phenanthrolinyl group, a benzoquinone group, a coumarinyl group, an anthraquinone group, a fluorenone group, a furanyl group, a thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, A benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a benzoyl group, a dibenzothiophenyl group, a dibenzoyl group, a pyrrolyl group, An oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, , Benzisothiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, imidazophenanthridinyl group, benzimidazophenanthridinyl group, azadibenzofuranyl group, azacarbazolyl group, azadibenzoyl group, Thienyl group, diazodibenzofura Naphthyl group, anthracenyl group, azulenyl group, heptareyl group, thiazolidinyl group, thiazolyl group, thiazolidinyl group, thiazolidinyl group, thiazolidinyl group, thiazolidinyl group, diazacarbazolyl group, diazabazoyl group, diazadibenzothienyl group, A phenanthrenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, a fluorenyl group, an acenaphthyl group, a phenanthryl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, An alkenyl group, an alkynyl group, an alkenyl group, an alkynyl group, an alkenyl group, an alkynyl group, an alkenyl group, an alkenyl group, an alkynyl group, A pyridinyl group, a pyridazinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a naphthyridinyl group, an acridinyl group, a phenazinyl group , Benzoquinolinyl group, benzo A thienyl group, a silyl group, a benzofuranyl group, a benzothienyl group, a benzoylolyl group, a diethoxycarbonyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzothiazolyl group, A benzofuranyl group, a dibenzothiophenyl group, a dibenzoylsilyl group, a pyrrolyl group, an indolyl group, an isoindolyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazolyl group, a benzimidazolyl group, A thiazolyl group, a thiazolyl group, a tetrazolyl group, an indazolyl group, an oxazolyl group, an isoxazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, A diazo group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazophenanthridinyl group, a benzimidazophenanthridinyl group, an azadibenzofuranyl group, an azacabazolyl group, an azadibenzothienyl group, Benzofuranyl group, diazacar Sol group, dia jadi benzothienyl group, janton group and thioxanthone group;
&Lt; / RTI &gt; The method according to claim 1,
In Formula 1-1, the carbon position at which A ₃ is bonded and the carbon position at which A ₄ are bonded are asymmetric,
In the formula (1-2), the carbon position at which the - (L ₁ ) _a1 - is bonded to the carbon position at which the A ₄ is bonded is asymmetric with respect to each other. The method according to claim 1,
In Formula 1-1, X ₁₂ is carbon bonded with A ₃ , X ₁₄ is carbon bonded with A ₄ , A ₃ is a group represented by * - (L ₂ ) a ₂ -R _ET , A ₄ is a substituted or unsubstituted C ₆ -C ₆₀ aryl group,
In the formula 1-2, X ₁₁ is - (L _{1) a1} - shown in (L _{2) a2} -R _ET - with a combined carbon, and ₁₃ X is a carbon bond, and A _4, A is the ₄ * Lt; RTI ID = 0.0 &gt; heterocyclic &lt; / RTI &gt; The method according to claim 1,
The heterocyclic compound has a molecular weight of 850 to 3,000. 14. A composition comprising a heterocyclic compound of any one of claims 1 to 13. 15. The method of claim 14,
At least one compound selected from the group consisting of a compound represented by the following formula (4-1), a compound represented by the following formula (4-2), a compound represented by the following formula (5), a compound represented by the following formula (6) Composition comprising:
<Formula 4-1>

<Formula 4-2>

&Lt; Formula 5 >

&Lt; Formula 5A >

(6)

&Lt; Formula 7 >

Of the above-mentioned formulas 4-1, 4-2, 5, 5A, 6, and 7,
X ₄₁ to X ₄₈ independently of one another are N or C,
At least one of X ₄₁ to X ₄₈ is - (L _{41) a41} -, and the carbon bond and,
X ₅₁ is N (R ₅₁ ), O or S, X ₅₂ is N (R ₅₂ ), O or S,
C ₅₁ to C ₅₄ are carbon atoms (C), and two adjacent ones of C ₅₁ to C ₅₄ are condensed to the group represented by the formula (5) through Y ₅₁ and Y ₅₂ respectively,
L _41, L ₆₁ to L ₆₃ and L ₇₁ are selected from a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
a41, a61 to a63 and a71 are each independently selected from integers of 0 to 3,
A is a group represented by the formula (5A)
R ₄₁ to R ₄₆ , R ₅₁ to R ₅₅ , R ₆₁ to R ₆₆ and R ₇₁ to R ₇₆ 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 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, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ H. Loa group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 1) (Q} 2) (Q 3), -N ( Q ₄ ) (Q ₅ ) and -B (Q ₆ ) (Q ₇ )
b41 to b43, b46, b53 to b54, b71 to b73 are independently selected from integers of 0 to 4,
b44, b45, b72 and b74 are independently selected from integers of 0 to 3,
b55 is selected from an integer of 0 to 2,
B ₁ and B ₄ are, independently of each other, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, An unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkane Substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl groups, substituted or unsubstituted C ₆ -C ₆₀ aryl groups, substituted or unsubstituted C ₆ -C ₆₀ aryloxy groups, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent ring non-fused polycyclic aromatic group and a substituted or unsubstituted monovalent ring non-aromatic heterocyclic group condensed polycyclic &Lt; / RTI >
m is an integer from 1 to 8,
p1 to p3 are independently selected from integers of 0 to 4; A first electrode;
A second electrode; And
And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer,
Wherein the organic layer contains at least one heterocyclic compound of any one of claims 1 to 13. 17. The method of claim 16,
The first electrode is an anode,
The second electrode is a cathode,
Wherein the organic layer further comprises a hole transporting region interposed between the first electrode and the light emitting layer and an electron transporting region interposed between the light emitting layer and the second electrode,
Wherein the hole transporting region includes at least one selected from a hole injecting layer, a hole transporting layer, a buffer layer, and an electron blocking layer,
Wherein the electron transporting region includes at least one selected from a hole blocking layer, an electron transporting layer, and an electron injection layer. 17. The method of claim 16,
Wherein the light emitting layer comprises the heterocyclic compound. 19. The method of claim 18,
Wherein the light emitting layer further comprises a light emitting material capable of emitting light from triplet excitons. 18. The method of claim 17,
Wherein the hole transporting region comprises an amine-based polymer.

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