KR20190022316A - Organic light-emitting device - Google Patents

Abstract

The present invention relates to an organic light emitting device having excellent electrical properties and thermal stability, which comprises: a first electrode; a second electrode; and an organic layer disposed between the first and second electrodes, and including an emission layer.

Description

Organic light-emitting device

An organic light emitting device is presented.

An organic light-emitting device is a self-light-emitting device having a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, and being able to have multiple colors .

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

Embodiments of the present invention provide an organic light emitting device.

One embodiment of the present invention is a liquid crystal display comprising: a first electrode; A second electrode; And

And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer,

Wherein the light emitting layer comprises at least one condensed ring compound represented by the following formula (1)

Wherein a ratio of a thermally activated delayed fluorescence (TADF) light emission component emitted from the condensed cyclic compound among the total light emission components emitted from the light emitting layer is 80% or more.

≪ Formula 1 >

Ar ₁ - (L ₁ ) _{n 1} -Ar ₂

(2) (3)

≪ Formula 4 > ≪ Formula 5 >  (6)

Among the above formulas (1) to (6)

Ar ₁ is a group represented by the general formula (2)

Ar ₂ is a group represented by the formula (3) or a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group,

L ₁ is selected from the group represented by the formula (4), the group represented by the formula (5) and the group represented by the formula (6)

n1 is an integer selected from 0 to 5,

CY ₁ to CY ₃ are, independently of each other, a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,

CY ₄ to CY ₆ are each independently selected from C ₅ -C ₃₀ carbocyclic groups,

Z ₁ is N or C (R ₁ ), Z ₂ is N or C (R ₂ ), Z ₃ is N or C (R ₃ )

Y ₁ is a single bond, C (R ₅ ) (R ₆ ), N (R ₅ ), O or S,

Y ₂ is a single bond, C (R ₇ ) (R ₈ ), N (R ₇ ), O or S,

R ₁ to R ₃ , R ₅ to R ₈ , R ₁₀ , R ₂₀ and R ₃₀ independently of each other represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, , A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkyl group, a substituted or unsubstituted C ₂ -C ₃₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₃₀ 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 heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group , 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, Chi 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 )

R ₄₀ , R ₅₀ and R ₆₀ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, nitro, amino, amidino, hydrazine, 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-aromatic condensed A ring 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₎ (Q < ₇ >),

a1 to a6 are, independently of each other, an integer selected from 1 to 10,

at least one of a1 R < ₁₀ > is a substituted or unsubstituted carbazolyl group,

* And * are bonding sites with neighboring atoms,

The substituted C ₅ -C ₃₀ carbocyclic 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, the substituted C ₃ -C ₁₀ cyclo alkyl, substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic heterocyclic fused polycyclic At least one of the substituents of the group is,

_{Deuterium, -CD 3, -CD 2 H,} -CDH 2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic A carboxylic acid or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

_{Deuterium, -CD 3, -CD 2 H,} -CDH 2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic A C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkene group, a C ₁ -C ₁₀ aralkyl group, 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, a monovalent non- at least one substitution selected from the group consisting of condensed polycyclic aromatic heterocyclic _{group, -Si (Q 11) (Q} 12) (Q 13), -N (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

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;

_{Deuterium, -CD 3, -CD 2 H,} -CDH 2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C 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 heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 21) (Q} 22) (Q 23 A C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group substituted with at least one group selected from the group consisting of -N (Q ₂₄ ) (Q ₂₅ ) and -B (Q ₂₆ ) (Q ₂₇ ) A C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₆₀ An aryloxy group, 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; And

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

≪ / RTI >

Wherein Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted A substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, 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 hete An aryl group, a substituted or unsubstituted non-1 is selected from the group consisting of condensed polycyclic aromatic heterocyclic group, aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent ratio.

The organic light emitting device has excellent electrical characteristics and thermal stability, can emit retarded fluorescence by employing a condensed cyclic compound that is easily controlled in energy level, and can have high efficiency, long life and high color purity.

1 is a cross-sectional view schematically showing an organic light emitting device according to an embodiment of the present invention.
2 shows an emission spectrum of an organic light emitting device according to an embodiment of the present invention.

In one embodiment, the first electrode;

A second electrode; And

And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer,

Wherein the light emitting layer comprises at least one condensed ring compound represented by the following formula (1)

Wherein a ratio of a thermally activated delayed fluorescence (TADF) light emission component emitted from the condensed cyclic compound is at least 80% of the total light emission components emitted from the light emitting layer.

≪ Formula 1 >

Ar ₁ - (L ₁ ) _{n 1} -Ar ₂

(2) (3)

≪ Formula 4 > ≪ Formula 5 >  (6)

In the above formula (1), Ar ₁ is a group represented by the formula (2), and Ar ₂ is a group represented by the formula (3) or a C ₅ -C ₃₀ carbocyclic group.

In Formula 1, L ₁ is selected from the group represented by Formula 4, the group represented by Formula 5, and the group represented by Formula 6.

In the general formula (1), n1 is an integer selected from 0 to 5.

According to one implementation, of the formula, or the group wherein n1 is 1 or 2 Ar ₂ is represented by Formula 3,

Wherein n1 is 0 or 1, Ar ₂ may be a C ₅ -C ₃₀ carbocyclic group.

In the general formulas (2) and (3), CY ₁ to CY ₃ are, independently of each other, a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group.

According to one embodiment, the CY ₁ to CY ₃ may be independently selected from a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group.

For example, the CY ₁ may be a benzene group, but is not limited thereto.

According to another embodiment, the CY < ₂ > is a benzene group,

The CY ₃ may be selected from a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group.

For example, the CY ₂ and CY ₃ may each be a benzene group.

In the above formulas (4) and (5), CY ₄ to CY ₆ are independently selected from C ₅ -C ₃₀ carbocyclic groups.

According to one embodiment, the CY ₄ to CY ₆ may be independently selected from a benzene group, a naphthalene group and a fluorene group.

Wherein Z ₁ is N or C (R ₁ ), Z ₂ is N or C (R ₂ ), and Z ₃ is N or C (R ₃ ).

According to one embodiment, Z ₁ to Z ₃ may each be C, or any of Z ₁ to Z ₃ may be N.

According to another embodiment, Z ₁ is N and Z ₂ and Z ₃ can each be C.

Wherein Y ₁ is a single bond, C (R ₅ ) (R ₆ ), N (R ₅ ), O or S, Y ₂ is a single bond, C (R ₇ ) (R ₈ ) N (R < ₇ >), O or S.

According to one embodiment, Y ₁ may be a single bond.

According to another embodiment, the Y < ₂ > may be a single bond.

According to one embodiment, Ar ₁ is selected from the group consisting of any one of the following formulas (2-1) to (2-7).

R ₁ to R ₃ , R ₅ to R ₈ , R ₁₀ , R ₂₀ , R ₄₀ , R ₅₀ and R ₆₀ in the general formulas 1 to 6 are independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br A sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C < RTI ID = 0.0 > ₁ -C ₆₀ alkyl group, a substituted or unsubstituted ring 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 ring ring 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 , 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), is selected from the group consisting of _{-N (Q 4) (Q 5} ) and _{-B (Q 6) (Q 7} ),

a1 to a6 are, independently of each other, an integer selected from 1 to 10,

and at least one of a1 R < ₁₀ > is a substituted or unsubstituted carbazolyl group. That is, at least one of a1 R < ₁₀ > includes a carbazole group.

According to one embodiment, R ₁ to R ₃ may be hydrogen.

According to one _{embodiment, R 10, R 20, R} 30, R 40, R 50 and R ₆₀ are independently from each other,

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

A cyclopentenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, A heterocyclic group such as azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, phenalenyl, phenanthryl, Phenanthrenyl, anthracenyl, fluoranthrenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, naphthacenyl, phenanthrenyl, phenanthrenyl, A substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, iso And examples thereof include isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthaloyl group, A phenanthridinyl group such as phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, And examples thereof include acridinyl, phenanthrolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiophene, thiophene, A thiophenyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, Triazolyl group, tetrazolyl group, oxadiazolyl group, A triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, A pyridobenzooxazinyl group and a pyridobenzothiazinyl group;

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, a C ₂ -C ₂₀ alkynyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, A pyridinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, a pyridazinyl group, a pyrazinyl group, a pyranyl group, a pyrazinyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, group and isoquinolinium group, a phthalazine group possess, salicylate quinoxaline group, when fun group, a quinazolinyl _{group, -Si (Q 31) (Q} 32) (Q 33), -N (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ) at least one substituted selected from the group consisting of cyclopentyl, cyclohexyl, cyclopentenyl group, cyclohexenyl group, heptenyl cycloalkyl group, a phenyl group, a biphenyl An acenaphthyl group, an acenaphthyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, a phenanthrenyl group, An anthracenyl group, a fluoranthrenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, A pyrimidinyl group, a pyrimidinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, A phenanthridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a quinazolinyl group, a quinazolinyl group, a quinazolinyl group, a quinazolinyl group, A thiophenyl group, a benzothiophenyl group, a thiophenyl group, A thiazolyl group, a thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a benzo thiophenyl group, a benzothiophene group, a benzothiophene group, A carbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzopyropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzopyrimidinyl group , A benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzoxazinyl group, and a pyridobenzothiazinyl group; And

_{-Si (Q 1) (Q 2} ) (Q 3), -N (Q 4) (Q 5) and _{-B (Q 6) (Q 7} );

≪ / RTI >

At least one of R < ₁₀ > is a carbazolyl group; And a metal salt of a metal selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, A phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, a C ₂ -C ₂₀ alkynyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, , A pyranyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, fun group, isoquinolinium group, a salicylate group possess phthalazine, quinoxaline group, when fun group, a quinazolinyl _{group, -Si (Q 31) (Q} 32) (Q 33), -N (Q 34) (Q 35) And -B (Q ₃₆ ) (Q ₃₇ );

≪ / RTI >

Q ₁ to Q ₇ and Q ₃₁ to Q ₃₇ are independently selected from the group consisting of hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, A sulfonyl group, a dibenzofuranyl group, and a dibenzothiophenyl group.

According to one embodiment, Ar ₁ may be selected from the group consisting of any one selected from the following formulas (2-1) to (2-7):

Of the above-mentioned formulas (2-1) to (2-7)

X ₁ is C (R ₁₇ ) (R ₁₈ ), N (R ₁₉ ), O or S,

Y ₁ , Z ₁ , Z ₂ and Z ₃ are each as defined herein,

R ₁ to R ₃ , R ₅ to R ₈ and R ₁₁ to R ₁₉ independently of one another,

Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of hydrogen, deuterium, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranoyl group and a dibenzothiophenyl group;

(Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) from the group consisting of hydrogen, deuterium, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, biphenyl, terphenyl, naphthyl, carbazolyl and -Si A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group which is substituted with at least one selected from a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, And dibenzothiophenyl groups; And

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

≪ / RTI >

At least one of R ₁₁ to R ₁₄ is a carbazolyl group; And deuterium, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, the group consisting of a carbazole group and a _{-Si (Q 31) (Q 32} ) (Q 33) A carbazolyl group substituted with at least one selected from a carbazolyl group; ≪ / RTI >

Wherein Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are independently selected from the group consisting of hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group ,

* Is the binding site with neighboring atoms.

According to one embodiment, Ar ₂ may be a group represented by any one of the following formulas (3-1) to (3-7) and (4-1) to (4-19)

Among the above-mentioned formulas (3-1) to (3-7) and (4-1) to (4-19)

X ₂ is C (R ₂₇ ) (R ₂₈ ), N (R ₂₉ ), O or S,

Y < ₂ > is as defined herein,

Z ₅ is N or C (R ₃₁₎ and, Z ₆ is N or C (R ₃₂₎ and, Z ₇ is N or C (R ₃₃₎ and, Z ₈ is N or C (R _34),

R ₂₁ to R ₂₉ and R ₃₁ to R ₃₄ , independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of hydrogen, deuterium, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranoyl group and a dibenzothiophenyl group;

(Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) from the group consisting of hydrogen, deuterium, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, biphenyl, terphenyl, naphthyl, carbazolyl and -Si A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group which is substituted with at least one selected from a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, And dibenzothiophenyl groups; And

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

Wherein Q ₁ to Q ₃ independently represent hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, Lt; / RTI > is selected from the group consisting of < RTI ID = 0.0 >

Y ₇₁ is O, S, C (R ₇₅ ) (R ₇₆ ) or Si (R ₇₅ ) (R ₇₆ );

R ₇₁ and R ₇₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ - C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group and a phenanthrenyl group and any one selected from,

e2 is an integer of 0 to 2,

e3 is an integer of 0 to 3,

e4 is an integer of 0 to 4,

e5 is an integer of 0 to 5,

e6 is an integer of 0 to 6,

e7 is an integer of 0 to 7,

e9 is an integer of 0 to 9,

* Is the binding site with neighboring atoms.

According to one embodiment, R ₁ to R ₈ , R ₁₁ to R ₁₉ , R ₂₁ to R ₂₉ and R ₃₁ to R ₃₄ in the general formulas (2-1) to (2-7) to,

Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, phenyl, biphenyl, terphenyl and naphthyl group;

A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranoyl group and a dibenzothiophenyl group;

(Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ), which is selected from the group consisting of hydrogen, deuterium, cyano, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, biphenyl, terphenyl, naphthyl and -Si A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzofuranyl group which are substituted with at least one group selected from the group consisting of a cyclopentyl group, A dibenzothiophenyl group; And

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

≪ / RTI >

Wherein Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are each independently selected from the group consisting of hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group .

According to one embodiment, X _{1 in the} above formulas (2-1) to (2-7) and (3-1) to (3-14) may be O or S.

According to one embodiment, the Ar ₁ may be represented by the formula (2-7), Ar ₂ may be represented by the formula (3-7), but the present invention is not limited thereto.

According to one embodiment, the condensed ring compound represented by Formula 1 may be represented by one of the following Formulas 1-1 to 1-9:

Among the above formulas 1-1 to 1-9,

The description of Ar < _{1 >} and Ar < ₂ >

The description for R ₄₁ to R ₄₈ independently of each other, see the description of R ₄₀ ,

The descriptions for R ₅₁ to R ₅₈ independently of each other refer to the description of R ₅₀ ,

The description of R ₆₁ to R ₆₈ is independent of each other, see the description of R ₆₀ .

According to one embodiment, R ₄₁ to R ₄₈ , R ₅₁ to R _58, and R ₆₁ to R ₆₈ in the general formulas 1-1 to 1-9 are, independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;

A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of hydrogen, deuterium, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranoyl group and a dibenzothiophenyl group;

(Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group and -Si A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofurano group and a dibenzothiophene group A phenyl group; And

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

≪ / RTI >

Wherein Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are each independently selected from the group consisting of hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group .

According to an embodiment, in the above formulas 1-1 to 1-9, Ar ₁ is selected from the group represented by any one of formulas 2-1 to 2-7,

And Ar ₂ may be a group represented by any one of formulas (3-1) to (3-7) and (4-1) to (4-19).

According to one embodiment, the number of carbazole groups contained in the condensed ring compound represented by Formula 1 may be 1, 2, 3, or 4.

According to one embodiment, the number of carbazole groups contained in R ₁₀ of Formula 1 may be 1 or 2.

According to one embodiment, the condensed ring compound represented by Formula 1 may be selected from the following Compounds 1 to 168, but is not limited thereto:

.

.

Since the condensed ring compound represented by the above formula (1) includes Ar ₁ as an electron acceptor moiety, R ₁₀ and Ar ₂ as substituents of Ar ₁ as a first electron donating moiety and a second electron donating moiety, respectively, The movement of electrons occurs easily. Also, a dipole is formed from the electron donor moiety in the condensed ring compound represented by Formula 1 to the electron acceptor moiety, and the dipole moment inside the molecule is increased. Therefore, the organic light emitting device including the condensed cyclic compound has excellent luminous efficiency.

The condensed ring compound represented by the above formula (1) is a compound capable of emitting delayed fluorescence, and not only singlet state excitons but also triplet excitons can be used for luminescence. Therefore, the condensed ring compounds are employed An organic light emitting device is excellent in luminous efficiency.

For example, the HOMO, LUMO, T ₁ , S ₁ energy levels, NPA (natural population analysis) charge and dipole moments of the above Compounds 1 to 168 and the following compounds A to E were measured by the DFT method of the Gaussian program (B3LYP, The structure is optimized at the level of 6-31G (d, p). The evaluation results are shown in Table 1 below.

Compound No. HOMO
(eV) LUMO
(eV) S1
(eV) T1
(eV) ΔE _ST
(eV) NPA charge Dipole moment One -5.165 -1,288 3.436 3.132 0.303 0.464 3.156 2 -5.227 -1.307 3.514 3.153 0.361 0.464 0.96 3 -5.253 -1.321 3.524 3.063 0.461 0.463 1.21 4 -5.225 -1.315 3.486 3.031 0.455 0.464 2.437 5 -5.118 -1.304 3.438 3.14 0.298 0.468 2.833 6 -5.263 -1.307 3.563 3.151 0.413 0.468 2.242 7 -5.22 -1,239 3.595 3.162 0.433 0.466 2.262 8 -5.224 -1.263 3.532 3.022 0.51 0.465 4.493 9 -5.267 -1.309 3.553 3.033 0.52 0.464 2.471 10 -5.303 -1,271 3.554 3.026 0.528 0.465 3.608 11 -5.29 -1.337 3.57 3.021 0.549 0.464 2.445 12 -5.161 -1,283 3.484 2.98 0.503 0.469 3.737 13 -5.301 -1.28 3.623 3.019 0.604 0.468 2.336 14 -5.267 -1,195 3.672 3.034 0.638 0.467 3.2 15 -5.386 -1.2 3.654 3.179 0.476 0.462 3.275 16 -5.428 -1.229 3.661 3.18 0.481 0.462 1.923 17 -5.395 -1.221 3.668 3.078 0.59 0.463 2.462 18 -5.388 -1.246 3.625 3.051 0.574 0.463 1.41 19 -5.459 -1.22 3.734 3.176 0.557 0.468 2.348 20 -5.448 -1.208 3.753 3.178 0.576 0.468 1.641 21 -5.474 -1.114 3.75 3.182 0.568 0.466 2.45 22 -5.16 -1.348 3.467 3.029 0.438 0.466 3.986 23 -5.141 -1.46 3.382 3.055 0.327 0.465 3.756 24 -5.235 -1.374 3.469 2.964 0.505 0.466 3.003 25 -5.175 -1.478 3.391 2.98 0.411 0.466 2.433 26 -5.197 -1.355 3.46 3.044 0.416 0.469 1.835 27 -5.175 -1.355 3.442 3.037 0.406 0.469 2.374 28 -5.168 -1,286 3.496 3.053 0.443 0.469 3.056 29 -5.235 -1.329 3.535 3.04 0.495 0.467 2.743 30 -5.196 -1.397 3.434 3.024 0.41 0.466 3.571 31 -5.242 -1.392 3.54 3.008 0.532 0.467 3.566 32 -5.255 -1.455 3.429 2.98 0.449 0.467 2.122 33 -5.258 -1.311 3.549 3.026 0.523 0.47 1.758 34 -5.306 -1.282 3.622 3.033 0.589 0.47 2.046 35 -5.225 -1.251 3.576 3.021 0.555 0.47 2.939 36 -5.364 -1,288 3.617 3.02 0.597 0.465 2.172 37 -5.362 -1.427 3.534 3.033 0.5 0.465 2.855 38 -5.342 -1.379 3.558 3.025 0.533 0.465 2.899 39 -5.373 -1.441 3.52 2.975 0.545 0.465 2.037 40 -5.382 -1.234 3.613 3.023 0.59 0.471 2.709 41 -5.396 -1.245 3.611 3.028 0.584 0.47 1.976 42 -5.338 -1.164 3.637 3.04 0.597 0.469 3.313 43 -5.1 -1.457 3.404 3.152 0.252 0.465 7.164 44 -5.111 -1,497 3.38 3.122 0.258 0.465 6.551 45 -5.105 -1.474 3.395 3.028 0.366 0.465 7.148 46 -5.119 -1.519 3.362 2.971 0.391 0.465 5.375 47 -5.101 -1.34 3.38 3.149 0.231 0.469 6.809 48 -5.113 -1.349 3.382 3.151 0.231 0.468 6.157 49 -5.108 -1,275 3.45 3.154 0.295 0.468 6.388 50 -5.192 -1.44 3.487 3.03 0.457 0.466 4.912 51 -5.178 -1.476 3.454 3.029 0.425 0.466 5.108 52 -5.168 -1.446 3.463 3.03 0.433 0.465 5.825 53 -5.175 -1.487 3.447 2.974 0.473 0.466 5.12 54 -5.178 -1,297 3.482 3.026 0.456 0.47 5.777 55 -5.184 -1.306 3.479 3.027 0.452 0.469 4.974 56 -5.208 -1,235 3.591 3.038 0.553 0.469 4.62 57 -5.266 -1.414 3.51 3.154 0.356 0.464 5.629 58 -5.277 -1.458 3.475 3.088 0.387 0.464 4.626 59 -5.286 -1.438 3.509 3.017 0.492 0.464 4.556 60 -5.284 -1.471 3.453 2.966 0.488 0.464 3.804 61 -5.284 -1.231 3.495 3.167 0.329 0.469 4.322 62 -5.302 -1.247 3.498 3.164 0.335 0.469 3.717 63 -5.253 -1.159 3.535 3.173 0.361 0.469 5.145 64 -5.09 -1.443 3.385 3.156 0.229 0.466 7.216 65 -5.079 -1.481 3.366 3.126 0.24 0.466 7.687 66 -5.08 -1.475 3.365 3.004 0.361 0.466 7.754 67 -5.082 -1,497 3.354 2.994 0.36 0.466 6.885 68 -5.084 -1.312 3.352 3.148 0.204 0.47 7.532 69 -5.095 -1.319 3.353 3.148 0.206 0.47 6.714 70 -5.068 -1.245 3.397 3.156 0.241 0.47 7.965 71 -5.172 -1.361 3.498 3.031 0.467 0.467 6.444 72 -5.149 -1.441 3.437 3.026 0.411 0.467 4.853 73 -5.135 -1.419 3.429 3.013 0.416 0.467 5.945 74 -5.146 -1.465 3.415 2.981 0.435 0.467 4.981 75 -5.144 -1.262 3.438 3.019 0.419 0.472 5.253 76 -5.159 -1.279 3.438 3.025 0.413 0.471 4.81 77 -5.161 -1.203 3.539 3.033 0.506 0.471 5.975 78 -5.356 -1.387 3.562 3.152 0.41 0.466 4.853 79 -5.351 -1.434 3.551 3.099 0.452 0.465 5.124 80 -5.356 -1.413 3.544 3.036 0.508 0.466 4.933 81 -5.359 -1.457 3.519 2.976 0.543 0.466 4.497 82 -5.368 -1.18 3.546 3.146 0.4 0.47 5.122 83 -5.378 -1.188 3.544 3.153 0.392 0.471 4.382 84 -5.326 -1.106 3.576 3.155 0.421 0.471 5.665 85 -5.257 -1.616 3.287 3.149 0.139 0.471 2.301 86 -5.215 -1.599 3.259 3.149 0.11 0.471 2.221 87 -5.255 -1.629 3.275 3.107 0.168 0.471 2.759 88 -5.229 -1.626 3.252 3.05 0.203 0.471 3.391 89 -5.12 -1.649 3.128 3.08 0.048 0.477 3.41 90 -5.179 -1.665 3.177 3.106 0.071 0.476 3.391 91 -5.21 -1.577 3.278 3.132 0.146 0.477 2.175 92 -5.221 -1.591 3.253 3.031 0.221 0.472 4.687 93 -5.301 -1.588 3.345 3.029 0.316 0.472 1.489 94 -5.261 -1.582 3.363 3.025 0.338 0.472 3.864 95 -5.307 -1.599 3.34 3.02 0.32 0.472 2.775 96 -5.188 -1.619 3.208 3.02 0.188 0.477 3.135 97 -5.319 -1.641 3.311 3.016 0.295 0.477 2.873 98 -5.258 -1.528 3.341 3.03 0.311 0.479 3.316 99 -5.373 -1.486 3.463 3.178 0.285 0.473 2.144 100 -5.373 -1.51 3.456 3.147 0.309 0.472 2.382 101 -5.312 -1.525 3.5 3.127 0.373 0.472 3.358 102 -5.327 -1.543 3.474 3.06 0.414 0.472 2.817 103 -5.355 -1.546 3.402 3.155 0.247 0.479 2.3 104 -5.348 -1.57 3.427 3.143 0.284 0.479 2.957 105 -5.494 -1.466 3.473 3.143 0.33 0.481 2.051 106 -5.203 -1.662 3.203 2.923 0.281 0.473 2.019 107 -5.176 -1.671 3.166 2.937 0.229 0.473 2.744 108 -5.253 -1.669 3.237 2.969 0.267 0.474 2.795 109 -5.213 -1.669 3.2 2.927 0.273 0.473 2.283 110 -5.189 -1.684 3.165 2.907 0.258 0.478 1.45 111 -5.218 -1.697 3.173 2.9 0.274 0.478 2.234 112 -5.205 -1.626 3.233 2.945 0.288 0.48 1.754 113 -5.193 -1.601 3.236 2.998 0.238 0.474 4.528 114 -5.254 -1.59 3.295 2.957 0.338 0.475 2.211 115 -5.332 -1.631 3.325 2.973 0.352 0.474 2.647 116 -5.271 -1.647 3.257 2.99 0.267 0.474 2.116 117 -5.302 -1.629 3.295 2.971 0.324 0.479 3.6 118 -5.322 -1.641 3.306 2.982 0.324 0.479 2.838 119 -5.237 -1.591 3.27 2.986 0.285 0.482 2.277 120 -5.405 -1.529 3.446 2.918 0.528 0.475 0.47 121 -5.428 -1.566 3.403 2.935 0.468 0.475 1.88 122 -5.383 -1.593 3.417 2.957 0.46 0.475 1.257 123 -5.389 -1.574 3.407 2.931 0.476 0.475 1.276 124 -5.466 -1.613 3.353 2.957 0.396 0.481 1.239 125 -5.461 -1.606 3.397 2.92 0.477 0.481 1.349 126 -5.429 -1.514 3.424 2.94 0.483 0.485 1.686 127 -5.151 -1.651 3.149 3.054 0.095 0.472 4.111 128 -5.169 -1.679 3.136 3.054 0.082 0.473 4.051 129 -5.167 -1.676 3.143 3.051 0.092 0.472 3.292 130 -5.168 -1.685 3.126 2.989 0.137 0.473 3.825 131 -5.173 -1.727 3.092 3.015 0.077 0.478 3.986 132 -5.183 -1.724 3.114 3.03 0.084 0.477 2.705 133 -5.153 -1.636 3.167 3.066 0.101 0.479 4.064 134 -5.245 -1.632 3.23 3.023 0.207 0.473 2.881 135 -5.231 -1.632 3.216 3.019 0.197 0.473 4.555 136 -5.243 -1.637 3.245 3.018 0.227 0.473 3.003 137 -5.245 -1.636 3.221 2.993 0.228 0.474 3.445 138 -5.235 -1.667 3.182 3.025 0.156 0.479 3.96 139 -5.26 -1.674 3.198 3.025 0.173 0.478 3.432 140 -5.221 -1.586 3.246 3.026 0.22 0.48 4.514 141 -5.38 -1.564 3.284 3.067 0.217 0.473 3.735 142 -5.385 -1.578 3.275 3.065 0.211 0.474 2.74 143 -5.389 -1.579 3.277 3.041 0.235 0.473 2.394 144 -5.378 -1.583 3.272 2.989 0.284 0.474 1.839 145 -5.408 -1.646 3.238 3.035 0.202 0.481 2.692 146 -5.396 -1.623 3.249 3.042 0.207 0.48 1.77 147 -5.356 -1.525 3.296 3.075 0.221 0.484 3.16 148 -5.147 -1.599 3.139 3.044 0.095 0.474 6.996 149 -5.182 -1.613 3.176 3.035 0.141 0.474 4.675 150 -5.162 -1.617 3.132 3.043 0.09 0.474 4.977 151 -5.162 -1.627 3.122 2.992 0.13 0.474 5.129 152 -5.178 -1.665 3.103 3.026 0.077 0.479 4.593 153 -5.171 -1.668 3.092 3.011 0.081 0.478 5.044 154 -5.143 -1.573 3.158 3.04 0.118 0.481 6.253 155 -5.258 -1.588 3.256 3.005 0.25 0.475 4.689 156 -5.209 -1.571 3.193 3.002 0.192 0.475 4.882 157 -5.217 -1.565 3.206 3.004 0.202 0.475 4.232 158 -5.222 -1.576 3.202 3.005 0.197 0.475 3.912 159 -5.235 -1.62 3.169 3.003 0.166 0.48 2.977 160 -5.262 -1.633 3.226 3.009 0.217 0.48 3.033 161 -5.197 -1.523 3.23 3.013 0.217 0.482 4.702 162 -5.474 -1.489 3.381 3.071 0.31 0.476 2.682 163 -5.441 -1,492 3.378 3.065 0.313 0.475 3.717 164 -5.438 -1,498 3.369 3.057 0.312 0.475 3.173 165 -5.407 -1,498 3.377 2.994 0.383 0.476 3.087 166 -5.441 -1.56 3.345 3.054 0.291 0.483 3.947 167 -5.471 -1.541 3.359 3.056 0.303 0.482 2.993 168 -5.457 -1.441 3.396 3.077 0.319 0.486 4.105

From the above Table 1, it can be confirmed that the condensed ring compound represented by the formula (1) has an excellent electrical property, for example, a high S ₁ , T ₁ energy level and a high NPA charge. It is confirmed that the cyclic compound is advantageous in terms of the stability of the material itself and the stability of the device when applied to the device, and is suitable for use as an electronic device, for example, as a light emitting layer material of an organic light emitting device.

The method of synthesizing the condensed ring compound represented by the above formula (1) can be easily recognized by those skilled in the art with reference to the following synthesis examples.

The organic light emitting device according to one embodiment is an organic light emitting device using delayed fluorescence emitted from the condensed cyclic compound, and can have high efficiency and long life.

According to one embodiment, the light emitting layer included in the organic light emitting device may emit blue light having a maximum emission wavelength of 380 nm to 475 nm.

The organic light emitting device has a light emitting layer containing the condensed cyclic compound represented by Formula 1, thereby achieving high efficiency and long life.

According to one embodiment, the condensed ring compound contained in the light emitting layer of the organic light emitting device may be a delayed fluorescent emitter.

According to one embodiment, the light emitting layer may consist of only the condensed ring compound.

According to another embodiment, the light emitting layer may further include a host, and the content of the host may be larger than the content of the condensed ring compound.

According to one embodiment, the light emitting layer includes a host and a dopant (the content of the host is larger than the content of the dopant), and the dopant may include the condensed ring compound represented by the general formula (1). The condensed ring compound serving as a dopant may emit retarded fluorescence by a delayed fluorescence emission mechanism. The host may be selected from any known dopants.

According to one embodiment, the light emitting layer may contain the condensed ring compound. At this time, the ratio of the fluorescent light emitting component among the total light emitting components emitted from the light emitting layer may be 90% or more, for example, 95% or more (as another example, 98% or more). The light emitting layer includes the condensed cyclic compound represented by Formula 1, but may not include a phosphorescent emitting compound (for example, an organic metal compound including a heavy metal). Therefore, the light-emitting layer can be clearly distinguished from the phosphorescent light-emitting layer including the phosphorescent dopant so that the proportion of the phosphorescent light-emitting component in the total light-emitting component is, for example, 80% or more.

According to an embodiment wherein the condensed ring compound contained in the light emitting layer is used as a fluorescent emitter, the ratio of the light emitting component emitted from the condensed ring compound among the total light emitting components emitted from the light emitting layer is 80% or more, for example, , 90% or more. For example, the ratio of the light emission component emitted from the condensed cyclic compound among the total light emission components emitted from the light emitting layer may be 95% or more. Here, the light emission component of the condensed cyclic compound is the sum of the immediate emission component of the condensed cyclic compound and the delayed fluorescence component due to the reverse intersystem crossing of the condensed cyclic compound .

According to one embodiment, the light emitting layer is composed of only the condensed ring compound; or

The light emitting layer may further include a host (wherein the host is not the same as the condensed ring compound).

When the light emitting layer further contains a host in addition to the condensed cyclic compound, the content of the condensed cyclic compound may be 50 parts by weight or less, for example, 30 parts by weight or less per 100 parts by weight of the light emitting layer, The content of the host may be 50 parts by weight or more, for example, 70 parts by weight or more per 100 parts by weight of the light emitting layer, but is not limited thereto.

According to another embodiment in which the condensed ring compound contained in the light emitting layer is used as a fluorescent host, the light emitting layer includes a host and a fluorescent dopant, wherein the host contains the condensed ring compound, The proportion of the light emitting component of the fluorescent dopant may be 80% or more, for example, 90% or more (as another example, 95% or more) among the total light emission components.

In this case, the content of the fluorescent dopant in the light emitting layer may be 50 parts by weight or less, for example, 30 parts by weight or less per 100 parts by weight of the light emitting layer, and the content of the host in the light emitting layer may be 50 weight Or more, for example, 70 parts by weight or more, but is not limited thereto.

When the condensed cyclic compound contained in the light emitting layer is used as a fluorescent host, the fluorescent host may be composed of only the condensed cyclic compound or may further include other known hosts.

According to one embodiment, the light emitting layer includes a host, an auxiliary dopant and a fluorescent dopant, the auxiliary dopant includes the condensed cyclic compound, and the light emitting layer may satisfy the following formulas 3 and 4:

&Quot; (3) "

E _{T1 (HOST)} - E _{T1 (AD)} > 0.05 eV

≪ Equation 4 &

E _{S1 ( FD )} - E _{S1 (AD)} <0 eV

_Wherein E _{T1 (HOST)} is the triplet energy (eV ₎ of the host, E _{T1 (AD)} is the triplet energy (eV) of the auxiliary dopant,

_Wherein E _{S1 ( FD )} is the singlet energy (eV ₎ of the fluorescent dopant, E _{S1 (AD)} is the singlet energy (eV) of the auxiliary dopant,

The E _{T1 (HOST)} , E _{T1 (AD),} and E _{S1 ( FD )} were evaluated using the DFT method of the Gaussian program structurally optimized at the B3LYP / 6-31G (d, p) level.

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

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

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

The first electrode 11 can be formed, for example, by providing a first electrode material on the substrate using a deposition method, a sputtering method, or the like. The first electrode 11 may be an anode. The first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO) and the like can be used. Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium- .

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

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

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

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

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

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

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

When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the desired hole injection layer, and the like. For example, 500 ℃, the degree of vacuum of about 10 ^-8 to about ¹⁰ can be selected in the range of ³ torr, a deposition rate of about 0.01 to about 100Å / sec, but is not limited to such.

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

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

NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4 ', 2'- , 4 "-tris (N-carbazolyl) triphenylamine), Pani / DBSA (polyaniline / dodecylbenzenesulfonic acid: polyaniline / dodecylbenzenesulfonic acid) Poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) / poly (4-styrene sulfonate), Pani / CSA (Polyaniline / Camphor sulfonicacid (Polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline) / poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)), the compound represented by Chemical Formula 201 and the compound represented by Chemical Formula 202 And may include at least one:

&Lt; Formula 201 >

&Lt; EMI ID =

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

A phenanthrenyl group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, an acenaphthylene group, A phenylene group, a phenylene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₃ -C ₁₀ cycloalkene group, C ₁ -C ₁₀ heterocycloalkyl 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 non-inde at least one substitution selected from the group consisting of aromatic heterocyclic condensed polycyclic group, a phenylene group, penta alkylenyl group, a carbonyl group, a naphthyl group, an azulenyl group , A phenanthrenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a triphenylenylene group, a pyrenylene group, a phenanthrenylene group, A perylene group, a perylene group, a perylene group, a perylene group, a perylene group, a perylene group, a perylene group and a perylene group;

&Lt; / RTI &gt;

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

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

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof , phosphoric acid group or a salt thereof, C ₁ -C ₁₀ alkyl group (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.) and C ₁ -C ₁₀ alkoxy group (e.g., methoxy group, Ethoxy group, propoxy group, butoxy group, pentoxy group, etc.);

Wherein the substituent is selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group which are substituted with at least one of a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

, But is not limited thereto.

In the above formula (201), R &lt; ₁₀₉ &

A phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; And

A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, A naphthyl group, an anthracenyl group and a pyridinyl group substituted with at least one of a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, ;

&Lt; / RTI &gt;

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

&Lt; Formula 201A >

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

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

Alternatively, the hole transport layer may include the condensed ring compound represented by Formula 1. [

The thickness of the hole transporting region may be from about 100 A to about 10,000 A, for example, from about 100 A to about 1000 A. When the hole transporting region includes at least one of a hole injection layer and a hole transporting layer, the thickness of the hole injection layer is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transporting layer is about 50 Å To about 2000 Angstroms, for example from about 100 Angstroms to about 1500 Angstroms. When the thicknesses of the hole transporting region, the hole injecting layer, and the hole transporting layer satisfy the above-described ranges, satisfactory hole transporting characteristics can be obtained without substantially increasing the driving voltage.

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

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

<Compound HT-D1> <F4-TCNQ>

<HP-1>

The hole transporting region may further include a buffer layer.

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

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

The hole transporting region may further include an electron blocking layer. The electron blocking layer may comprise a known material, for example, mCP, but is not limited thereto.

Alternatively, the hole transporting region may include an electron blocking layer, and the electron blocking layer may include a condensed ring compound represented by Formula 1. [

The thickness of the electron blocking layer may be from about 50 A to about 1000 A, for example, from about 70 A to about 500 A. [ When the thickness of the electron blocking layer satisfies the above-described range, a satisfactory degree of electron blocking characteristics can be obtained without a substantial increase in driving voltage.

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

The light emitting layer may include a condensed ring compound represented by the general formula (1). For example, the light emitting layer may include only the condensed ring compound represented by Formula 1. Alternatively, the light emitting layer may include a host and a dopant, and the host may include a condensed ring compound represented by the general formula (1). According to another example, the light emitting layer may include a host and a dopant, and the dopant may include a condensed ring compound represented by the formula (1).

According to one embodiment, the light emitting layer may further include a phosphorescent dopant, and the phosphorescent dopant may include an organometallic compound represented by the following formula:

<Formula 81>

In the above formula (81)

M is at least one element selected from the group consisting of Ir, Pt, Os, Ti, Zr, Hf, Eu, ) And rhodium (Rh)

Y ₈₁ to Y ₈₄ are independently of each other carbon (C) or nitrogen (N)

Y ₈₁ and Y ₈₂ are connected through a single bond or a double bond, Y ₈₃ and Y ₈₄ are connected through a single bond or a double bond,

CY ₈₁ and CY ₈₂ are each independently selected from the group consisting of benzene group, naphthalene group, fluorene group, spiro-bifluorene group, indene group, pyrrole group, thiophene group, furan group, imidazole group, Group, a thiazole group, an isothiazole group, an oxazole group, an isooxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, , A quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group , an oxadiazole group, a triazine group, dibenzofuran (dibenzofuran) group or di-benzothiophene and thiophene group, CY ₈₁ and CY ₈₂ is determined together with optionally (optionally), added via an organic linking group (organic linking group) And,

R ₈₁ and R ₈₂ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl, a cyano, a nitro, an amino, an amidino, a hydrazine, a hydrazone, acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, -SF _5, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted ring ring C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ 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- Hyangjok condensed polycyclic group, a non-substituted or unsubstituted 1-hetero-condensed polycyclic aromatic _{group, -N (Q 1) (Q} 2), -Si (Q 3) (Q 4) (Q 5) and -B (Q is selected from ₆₎ (Q _7),

a81 and a82 are each independently selected from an integer of 1 to 5,

n81 is selected from an integer of 0 to 4,

n82 is 1, 2 or 3,

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

For the description of Q ₁ to Q ₇ , refer to the description of Q ₁ to Q ₃ of -Si (Q ₁ ) (Q ₂ ) (Q ₃ ) in the formula ( ₁ ).

The descriptions of R ₈₁ and R ₈₂ refer to the description of R ₁₁ in the present specification.

The phosphorescent dopant, but it may include at least one of the following compounds PD1 to PD78 and FIr _6, but not limited to:

Alternatively, the phosphorescent dopant may comprise the following PtOEP:

When the light emitting layer includes a host and a dopant, the dopant may be selected from the range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

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

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

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

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

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

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

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

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

Alternatively, the electron transport layer may include at least one of the following compounds ET1, ET2, and ET3, but is not limited thereto.

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

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

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

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

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

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

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

According to one embodiment, the organic layer 15 of the organic light emitting device 10 includes a hole transporting region and a light emitting layer, and the hole transporting region and the light emitting layer include the condensed ring compound represented by Formula 1, The condensed ring compound represented by the formula (1) and the condensed ring compound represented by the formula (1) contained in the light emitting layer contained in the transport region may be the same.

According to another embodiment, the organic layer 15 of the organic light emitting device 10 includes a hole transporting region and a light emitting layer, and the hole transporting region and the light emitting layer include the condensed ring compound represented by Formula 1, The condensed ring compound represented by Formula 1 and the condensed ring compound represented by Formula 1 contained in the light emitting layer contained in the transport region may be different from each other.

Here, the hole transporting region may include at least one of a hole transporting layer and an electron blocking layer, and the condensed cyclic compound represented by the formula (1) may include: i) a hole transporting layer, ii) an electron blocking layer, or iii) May be included in both the electron blocking layer. The electron blocking layer may be in direct contact with the light emitting layer.

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

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

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

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

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

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

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

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

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

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

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

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

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

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group is a condensed heteropolycyclic group in which two or more rings are condensed with each other, and in addition to carbon (for example, the number of carbon atoms may be 1 to 60) Means a monovalent group comprising a heteroatom selected from N, O, P, Si and S, wherein the entire molecule has a non-aromaticity. 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 substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C _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 arylox group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic hydrocarbon ring at least one substituent of the condensed polycyclic group The one is,

_{Deuterium, -CD 3, -CD 2 H,} -CDH 2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

_{Deuterium, -CD 3, -CD 2 H,} -CDH 2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C 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 condensed polycyclic group, -Si (Q _{11) (Q 12) (Q 13)} , -N (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) at least one substitution selected from the group consisting of, C ₁ -C ₆₀ alkyl, C ₂ - A C ₆₀ 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;

_{Deuterium, -CD 3, -CD 2 H,} -CDH 2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid Or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocyclo alkyl 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, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 21) (Q} 22) (Q 23), -N (Q 24) (Q 25) and _{-B (Q 26) (Q 27} ) at least one substitution selected from the group consisting of, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ - C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, 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; And

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

&Lt; / RTI &gt;

Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently selected from the group consisting of hydrogen, deuterium, hydroxyl, cyano, nitro, amino, Substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted alkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted aryl group, hwandoen C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ ring - 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.

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

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

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

[ Example ]

Synthetic example  1: Synthesis of Compound 43

(1) Synthesis of intermediate 43-2

(i) 9- (3- Iodophenyl ) -9H- Carbazole  synthesis

1,3-Diiodobenzene (7.10 g, 21.5 mmol), copper powder (0.060 g, 0.900 mmol) was added to a stirred solution of 9H-carbazole (3.00 g, 17.9 mmol) in N, N- dimethylacetamide mmol) and potassium carbonate (4.95 g, 35.9 mmol). The resulting solution was heated at 170 &lt; 0 &gt; C for 12 hours under a stream of nitrogen. The reaction solution was cooled to room temperature, filtered through a pad of celite, and washed with ethyl acetate (EtOAc). The combined filtrates were washed repeatedly with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting oily substance was purified by silica gel column chromatography (Hexane: EtOAc = 9: 1) to obtain 9- (3-iodophenyl) -9H-carbazole (2.78 g, yield 42% .

White solid, yield 42%; R _f 0.5 (Hexane / EtOAc: 9/1); ^{1 H NMR (400 MHz, CDCl} 3) δ 8.20 - 8.15 (m, 2H), 7.98 (t, J = 1.9 Hz, 1H), 7.82 (ddt, J = 7.9, 1.5, 0.7 Hz, 1H), 7.60 - 7.55 (m, 1H), 7.48-7.42 (m, 4H), 7.38-7.31 (m, 3H).

(ii) Synthesis of 9- (3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) phenyl) -9H-carbazole

(2.70 g, 11.0 mmol), PdCl ₂ (dppf) ₂ -CH ₂ CI ₂ (dppf) ₂ (2.75 g, 7.6 mmol), and the sealed tube equipped with a magnetic stir bar 0.600 g, 0.730 mmol) and KOAc (1.08 g, 11.0 mmol) in DMF (60 mL). The resulting mixture was stirred at 130 &lt; 0 &gt; C for 24 hours. The reaction mixture was cooled to ambient temperature. The mixture was filtered through a pad of celite and washed with CH ₂ Cl ₂ . The filtrate was concentrated in vacuo and the residue was subjected to column chromatography (Hexane: Toluene = 1: 2) to give the resulting boronate product. (1.94 g, 72% yield).

White solid, yield 72%; R _f 0.5 (Hexane / Toluene: 1/2); ^{1 H NMR (400 MHz, CDCl} 3) δ 8.14 (dt, J = 7.8, 1.0 Hz, 2H), 7.99 (dt, J = 1.9, 0.8 Hz, 1H), 7.91 (ddd, J = 6.8, 1.8, 1.1 Hz, 1H), 7.67-7.58 (m, 2H), 7.43-7.55 (m, 4H), 7.28 (ddd, J = 8.0, 6.6, 1.6 Hz, 2H), 1.35 (s, 12H); ^{13 C NMR (101 MHz, CDCl} 3) δ 141.01, 137.19, 133.78, 133.47, 130.07, 129.25, 128.18, 125.79, 123.23, 120.18, 119.71, 109.78, 84.06, 77.30, 76.98, 76.66, 24.86.

(iii) Synthesis of Intermediate 43-2

(2.00 g, 5.40 mmol), 3-bromoiodobenzene (1.38 mL, 10.8 mmol) , Tetrakis (triphenylphosphine) palladium (0) (0.630 g, 0.540 mmol) , Ag ₂ CO ₃ mmol) and 90 mL tetrahydrofuran were placed in a 150 mL heavy-walled pressure vessel. The mixture was heated and stirred at 100 &lt; 0 &gt; C for 12 hours. The reaction solution was cooled to room temperature and filtered through celite. The filtrate was concentrated in vacuo and the residue was subjected to column chromatography (Hexane: Toluene = 4: 1) to obtain the intermediate 43-2 (9- (3'-bromo- [1,1'-biphenyl] -9H-carbazole) (1.61 g, 75% yield).

White solid, yield 75%; R _f 0.5 (Hexane / Toluene: 4/1); ^{1 H NMR (400 MHz, CDCl} 3) δ 8.18 (dt, J = 7.8, 1.0 Hz, 2H), 7.83 - 7.76 (m, 2H), 7.71 - 7.64 (m, 2H), 7.61 - 7.54 (m, 2H ), 7.54-7.41 (m, 5H), 7.33 (ddt, J = 7.9, 6.5, 1.7 Hz, 3H); ¹³ C NMR (101 MHz, CDCl ₃ ) δ 142.17, 141.59, 140.76, 138.33, 130.77, 130.46, 130.44, 130.20, 129.03,128.22,126.43,126.07,122.03,125.78,125.67,125.30, 123.41, , 109.70.

(2) Synthesis of intermediate 43-1

(i) 4- (2'- Bromoanilino ) Synthesis of pyridine

To a sealed tube equipped with a magnetic stir bar was added 4- aminopyridine (944 mg, 10.0 mmol), t-BuONa (1.14 g, 11.9 mmol), tris (dibenzylideneacetone) -dipalladium (137 mg, 0.150 mmol) 10-bis (diphenylphosphino) ferrocene (200 mg, 0.361 mmol). The resulting mixture was stirred at 120 &lt; 0 &gt; C for 18 hours. The reaction mixture was cooled to ambient temperature. The mixture was filtered through a pad of celite and washed with CH ₂ Cl ₂ . The filtrate was concentrated in vacuo and the residue was purified by column chromatography (CH ₂ Cl ₂ of the 3% MeOH, then 10% MeOH in CH ₂ Cl ₂₎ and was synthesized 4- (2'-Bromoanilino) pyridine ( 2.48 g , 99% yield).

(ii) 5H- pyrido [4,3-b] indole  synthesis

In a sealed tube equipped with a magnetic stir bar, 4- (2'-bromo-anilino) pyridine (2.48 g, 9.96 mmol), Pd (OAc) 2 (112 mg, 4.98 mmol) and Na ₂ CO ₃ (1.48 g , 13.9 mmol). The mixture was purged with nitrogen and DMF (20 mL) was added. The resulting mixture was stirred at 160 &lt; 0 &gt; C for 20 hours. The reaction mixture was cooled to ambient temperature. The mixture was filtered through Celite pad and washed with CH ₂ Cl ₂ . The filtrate was concentrated in vacuo and the residue was diluted with H ₂ O (12 mL), worked up with EtOAc (20 mL x 6), dried over MgSO ₄ and concentrated in vacuo. The residue was purified by flash column chromatography (CH ₂ Cl ₂ 5% of MeOH, then 15% MeOH in CH ₂ Cl ₂₎ to give the 5H-pyrido [4,3-b] indole (1.26 g, 75% yield)

(iii) 8- bromo -5H- pyrido [4,3-b] indole  synthesis

NBS (1.60 g, 8.99 mmol) was added portionwise to a solution of SM (1.26 g, 7.49 mmol) in DMF (20 mL) at room temperature. The reaction mixture was stirred at room temperature for 12 h and then diluted with H ₂ O (20 mL). The aqueous layer was extracted with EtOAc (30 mL x 4) and evaporated in vacuo. The residue was purified by column chromatography (5% MeOH in CH ₂ Cl ₂ ) to give the bromide (1.53 g, 83%).

(iv) 8- bromo -5- tosyl -5H- pyrido [4,3-b] indole  synthesis

Et ₃ N (1.3 mL, 9.29 mmol), TsCl (1.42 g, 7.43 mmol) and DMAP (76 mg, 0.62 mmol) were added to a solution of SM (1.53 g, 6.19 mmol) in CH ₂ Cl ₂ . The reaction mixture was stirred at room temperature for 2 hours and quenched with saturated aqueous NaHCO ₃ (30 mL). Extract the combined organic layer was washed with EtOAc (30 mL x 3), dried with MgSO _4, and concentrated in vacuo. The residue was treated with flash column chromatography (Hexane: EtOAc = 1: 1 then 1: 3) to give 8-bromo-5-tosyl-5H-pyrido [4,3- %).

(v) 9- (5- tosyl -5H- pyrido [4,3-b] indole -8- yl ) -9H-3,9'- bicarbazole  synthesis

To a sealed tube equipped with a magnetic stir bar was added 8-bromo-5-tosyl-5H-pyrido [4,3-b] indole A (1.5 g, 3.74 mmol), 9H-3,9'-bicarbazole (1.37 g, 4.11 mmol), CuI (214 mg, 1.12 mmol) and _{K 3 PO 4 (2.38 g,} 11.2 mmol) was charged. The mixture was purged with nitrogen and dry toluene (19 mL) was added followed by (±) -trans-1,2-Diaminocyclohexane (128 mg, 11.2 mmol). The resulting mixture was stirred at 150 &lt; 0 &gt; C for 16 hours. The reaction mixture was cooled to ambient temperature. The mixture was filtered through a pad of celite and washed with CH ₂ Cl ₂ . The filtrate was concentrated in vacuo and the residue was subjected to column chromatography (acetone: CH ₂ Cl ₂ = 1:30) to give 9- (5-tosyl-5H-pyrido [4,3- b] indol- -9H-3,9'-bicarbazole (2.18 g, 89% yield).

(vi) Synthesis of Intermediate 43-1

To a solution of SM (2.18 g, 3.34 mmol) in EtOH (60 mL) was added 2N KOH (16 mL). The reaction mixture was stirred at 90 &lt; 0 &gt; C for 2 hours, then cooled to 0 &lt; 0 &gt; C and diluted with 2N HCl (12 mL). The remaining EtOH was removed by evaporation and the aqueous layer was extracted with CH ₂ Cl ₂ (30 mL x 3), dried over MgSO ₄ and concentrated in vacuo. The residue was purified by flash column chromatography (acetone: CH ₂ Cl ₂ = 1: 20 then 5% MeOH in CH ₂ Cl ₂ ) to give Intermediate 43-1 (1.40 g, 84%).

(3) Synthesis of Compound 43

Magnetic mounting bar in a sealed tube and intermediate 43-1 (850 mg, 1.70 mmol) , intermediate 43-2 (747 mg, 1.88 mmol) , CuI (97 mg, 0.51 mmol) and _{K 3 PO 4 (1.09 g,} 5.11 mmol). The reaction mixture was purged with nitrogen and dry toluene (8.5 mL) and then (±) -trans-1,2-Diaminocyclohexane (58 mg, 0.51 mmol) was added. The resulting mixture was stirred at 150 占 폚 for 40 hours. The reaction mixture was cooled to room temperature. The mixture was filtered through a pad of celite and washed with CH ₂ Cl ₂ . The filtrate was concentrated in vacuo and the residue was subjected to column chromatography (acetone: CH ₂ Cl ₂ = 1: 15) to obtain Compound 43 (924 mg, 66% yield).

LC-Mass (calculated: 815.98 g / mol, measured: 816.08 g / mol (M + 1))

Synthetic example  2: Synthesis of Compound 64

(1) Synthesis of intermediate 64-1

3-iodopyridin-4-amine (4.0 g, 18.18 mmol) and (2-bromophenyl) boronic acid (4.38 g, 21.82 mmol ), Palladium tetrakis (triphenylphosphine), Pd (PPh ₃ ) ₄ (1.05 g, 0.91 mmol) and potassium carbonate (K ₂ CO ₃ ) (4.67 g, 36.36 mmol) Dioxane (36 mL), and the mixture was heated to reflux. After completion of the reaction, the reaction mixture was cooled to room temperature, extracted with dichloromethane and water, and filtered through a silica gel. The resulting organic layer was concentrated, and then methanol was poured out to precipitate an intermediate 64-1 (3.78 g, yield 83%) as a white solid.

GC-Mass (calculated 249.11 g / mol, measured: 249.1 g / mol (M + 0)).

(2) Synthesis of intermediate 64-2

Pyridin-4-amine (3.5 g, 14.05 mmol) and sodium nitrite (NaNO ₂ ) (1.94 g, 28.10 mmol) were added to a solution of 3- (2-bromophenyl) pyridin- ), And the mixture is stirred at room temperature. An aqueous hydrochloric acid solution (200 mL) was added to the resulting mixture and stirred for another 1 hour. After completion of the reaction, sodium azide (NaN ₃ ) (1.83 g, 28.10 mmol)

To prepare an aqueous solution, and the mixture is further stirred at room temperature for an additional 4 hours. After completion of the reaction, only the organic layer is extracted using an organic solvent, and then the solvent is concentrated. This was obtained without purification intermediate 64-2 (2.35 g, 61%).

GC-Mass (calculated: 275.11 g / mol, measured: 275.1 g / mol (M + 0))

(3) Synthesis of intermediate 64-3

50 mL of o-dichlorobenzene was added to a solution of 4-azido-3- (2-bromophenyl) pyridine (2.35 g, 8.54 mmol) , And the mixture is stirred at 210 占 폚 for 12 hours. After the completion of the reaction, methanol was added, and the mixture was filtered through a silica gel. The obtained organic layer was concentrated, dissolved again in toluene, filtered through silica gel, and concentrated. Recrystallization from toluene afforded Intermediate 64-3 (0.74 g, yield 35%) as a yellow solid.

GC-Mass (calculated 247.1 g / mol, measured: 247.1 g / mol (M + 0)).

(4) Synthesis of intermediate 64-4

Synthesis of Intermediate 43-1 was repeated except that the intermediate 9-bromo-5H-pyrido [4,3-b] indole was used instead of the intermediate 8-bromo-5H-pyrido [4,3- Intermediate 64-4 (900 mg, yield 75%) was synthesized by using the same method as in Example (iv).

LC-Mass (calculated: 401.28 g / mol, measured: 401.38 g / mol (M + 1))

(5) Synthesis of intermediate 64-5

Except that the intermediate 9-bromo-5-tosyl-5H-pyrido [4,3-b] indole was used instead of the intermediate 8-bromo-5-tosyl-5H- , Intermediate 5 (2.3 g, yield 88%) was synthesized in the same manner as in the synthesis example (v) of Intermediate 43-1.

LC-Mass (calculated: 498.59 g / mol, measured: 498.69 g / mol (M + 1))

(6) Synthesis of Compound 64

Compound 64 (2.2 g, yield 58%) was synthesized in the same manner as in the synthesis of the compound 43 of Synthesis Example 1, except that Intermediate 64-5 was used instead of Intermediate 43-1.

LC-Mass (calculated: 815.98 g / mol, measured: 816.08 g / mol (M + 1))

Example  One

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

The compound HT3 was vacuum deposited on the ITO electrode of the glass substrate to form a hole injection layer having a thickness of 100 A and then a compound HT13 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1300 A, .

The compound 43 (host) and the compound DPEPO (dopant, 15% by weight) were deposited on the hole transporting region to form a 300 Å thick light emitting layer.

Et3 and Liq were vacuum deposited on the light emitting layer to form an electron transporting layer having a thickness of 250 A and then Liq was deposited on the electron transporting layer to form an electron injection layer having a thickness of 5 A, (Cathode) was formed, whereby an organic light emitting device was fabricated.

Example  2 and Comparative Example  1 to Comparative Example  5

An organic light emitting device was fabricated using the same method as in Example 1 except that the compound described in Table 2 was used in place of Compound 43 as a host in forming the light emitting layer

Evaluation example  1: Evaluation of characteristics of organic light emitting device

For each of the organic light emitting devices manufactured in Examples 1 and 2 and Comparative Examples 1 to 5, the current density change, the luminance change, and the luminous efficiency were measured according to the voltage. Specific measurement methods are as follows, and the results are summarized in Table 2. The emission spectrum of the organic luminescent device of Example 1 is shown in Fig.

(1) Measurement of change in current density with voltage change

For the organic light emitting device manufactured, the current value flowing through the unit device was measured using a current-voltage meter (Keithley 2400) while raising the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

(2) Measurement of luminance change according to voltage change

For the organic light emitting device manufactured, the luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the result was obtained.

(3) Measurement of luminous efficiency

The current efficiency (cd / A) at the same current density (10 mA / cm ² ) was calculated using the luminance, current density and voltage measured from the above (1) and (2).

(4) Durability measurement

The time required for the luminance to become 95% based on the initial luminance of 100% was evaluated.

Compound No. The driving voltage (V) Emission wavelength (nm) Quantum efficiency (%) life span(%) Example 1 43 7.75 432 100 100 Example 2 64 7.72 431 97.8 114.7 Comparative Example 1 A 8.25 479 83.34 29.4 Comparative Example 2 B 12.23 525 94.5 94.1 Comparative Example 3 C 6.33 399 1.11 2.95 Comparative Example 4 D 6.23 418 2.22 2.95 Comparative Example 5 E 9.25 489 1.11 2.95

Referring to Table 2, it was confirmed that the organic luminescent devices of Examples 1 and 2 had better quantum efficiency and lifetime characteristics than the organic luminescent devices of Comparative Examples 1 to 5. In particular, the organic luminescent devices of Examples 1 and 2 had lower driving voltage than the organic luminescent devices of Comparative Examples 1, 2 and 5, and emitted deep blue light even in the light emission scene. In addition, it was confirmed that the organic light emitting devices of Comparative Examples 3 and 4 did not emit retarded fluorescence, and their quantum efficiency and lifetime were significantly lower than those of the organic light emitting devices of Examples 1 and 2. [

Also, referring to FIG. 2, it was confirmed that the organic light emitting device of Example 1 emits deep blue light having a maximum emission wavelength of 380 nm to 475 nm.

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

Claims (20)

A first electrode;
A second electrode; And
And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer,
Wherein the light emitting layer comprises at least one condensed ring compound represented by the following formula (1)
Wherein a ratio of a thermally activated delayed fluorescence (TADF) light emission component emitted from the condensed ring compound is 80% or more among the total light emission components emitted from the light emitting layer,
&Lt; Formula 1 >
Ar ₁ - (L ₁ ) _{n 1} -Ar ₂
&Lt; Formula 2 >< EMI ID =

&Lt; Formula 4 &gt;&lt; EMI ID =

Among the above formulas (1) to (6)
Ar ₁ is a group represented by the general formula (2)
Ar ₂ is a group represented by the formula (3) or a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group,
L ₁ is selected from the group represented by the formula (4), the group represented by the formula (5) and the group represented by the formula (6)
n1 is an integer selected from 0 to 5,
CY ₁ to CY ₃ are, independently of each other, a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,
CY ₄ to CY ₆ are each independently selected from C ₅ -C ₃₀ carbocyclic groups,
Z ₁ is N or C (R ₁ ), Z ₂ is N or C (R ₂ ), Z ₃ is N or C (R ₃ )
Y ₁ is a single bond, C (R ₅ ) (R ₆ ), N (R ₅ ), O or S,
Y ₂ is a single bond, C (R ₇ ) (R ₈ ), N (R ₇ ), O or S,
R ₁ to R ₃ , R ₅ to R ₈ , R ₁₀ , R ₂₀ , R ₄₀ , R ₅₀ and R ₆₀ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, , A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₁ -C alkyl group, a substituted or unsubstituted C ₁ -C alkyl group, a substituted or unsubstituted C ₁ -C alkyl group, a substituted or unsubstituted aryl group, Or an 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 heteroaryl Group, a substituted or unsubstituted 1, a non-condensed polycyclic aromatic 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 )
a1 to a6 are, independently of each other, an integer selected from 1 to 10,
at least one of a1 R < ₁₀ > is a substituted or unsubstituted carbazolyl group,
* And * are bonding sites with neighboring atoms,
The substituted C ₅ -C ₃₀ carbocyclic 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, the substituted C ₃ -C ₁₀ cyclo alkyl, substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted a non-aromatic condensed polycyclic groups, and substituted monovalent non-aromatic heterocyclic fused polycyclic At least one of the substituents of the group is,
_{Deuterium, -CD 3, -CD 2 H,} -CDH 2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic A carboxylic acid or a salt thereof, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
_{Deuterium, -CD 3, -CD 2 H,} -CDH 2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic A C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkene group, a C ₁ -C ₁₀ aralkyl group, 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, a monovalent non- at least one substitution selected from the group consisting of condensed polycyclic aromatic heterocyclic _{group, -Si (Q 11) (Q} 12) (Q 13), -N (Q 14) (Q 15) and _{-B (Q 16) (Q 17} ) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;
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;
_{Deuterium, -CD 3, -CD 2 H,} -CDH 2, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, C ₁ -C 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 heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic _{group, -Si (Q 21) (Q} 22) (Q 23 A C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group substituted with at least one group selected from the group consisting of -N (Q ₂₄ ) (Q ₂₅ ) and -B (Q ₂₆ ) (Q ₂₇ ) A C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ heterocycloalkenyl group, a C ₆ -C ₆₀ aryl group, a C ₆ -C ₆₀ An aryloxy group, 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; And
_{-Si (Q 31) (Q 32} ) (Q 33), -N (Q 34) (Q 35) and _{-B (Q 36) (Q 37} );
&Lt; / RTI >
Wherein Q ₁ to Q ₇ , Q ₁₁ to Q ₁₇ , Q ₂₁ to Q ₂₇ and Q ₃₁ to Q ₃₇ are each independently selected from the group consisting of hydrogen, deuterium, -F, -Cl, -Br, -I, group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted A substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, 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 hete An aryl group, a substituted or unsubstituted non-1 is selected from the group consisting of condensed polycyclic aromatic heterocyclic group, aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent ratio. The method according to claim 1,
Or the group wherein n1 is 1 or 2 Ar ₂ is represented by Formula 3,
Wherein n1 is 0 or 1, Ar ₂ is a C ₅ -C ₃₀ carbocyclic group, a condensed ring compound. The method according to claim 1,
Wherein the CY ₁ to CY ₃ are independently selected from a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group. The method according to claim 1,
Wherein the CY ₄ to CY ₆ are independently selected from a benzene group, a naphthalene group and a fluorene group. The method according to claim 1,
Z ₁ to Z ₃ are each C,
Wherein _{one of} Z ₁ to Z ₃ is N. The method according to claim 1,
Y ₁ and Y ₂ are each a single bond. The method according to claim 1,
R ₁ to R ₃ are hydrogen,
R ₁₀ , R ₂₀ , R ₃₀ , R ₄₀ , R ₅₀ and R ₆₀ , independently of each other,
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof , A phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;
A cyclopentenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, A heterocyclic group such as azulenyl, heptalenyl, indacenyl, acenaphthyl, fluorenyl, spiro-bifluorenyl, phenalenyl, phenanthryl, Phenanthrenyl, anthracenyl, fluoranthrenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, naphthacenyl, phenanthrenyl, phenanthrenyl, A substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, iso And examples thereof include isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthaloyl group, A phenanthridinyl group such as phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, And examples thereof include acridinyl, phenanthrolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiophene, thiophene, A thiophenyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, Triazolyl group, tetrazolyl group, oxadiazolyl group, A triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, A pyridobenzooxazinyl group and a pyridobenzothiazinyl group;
A halogen atom, a hydroxyl group, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, a C ₂ -C ₂₀ alkynyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, A pyridinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, a pyridazinyl group, a pyrazinyl group, a pyranyl group, a pyrazinyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, group and isoquinolinium group, a phthalazine group possess, salicylate quinoxaline group, when fun group, a quinazolinyl _{group, -Si (Q 31) (Q} 32) (Q 33), -N (Q 34) (Q 35) and _{-B (Q 36) (Q 37} ) at least one substituted selected from the group consisting of cyclopentyl, cyclohexyl, cyclopentenyl group, cyclohexenyl group, heptenyl cycloalkyl group, a phenyl group, a biphenyl An acenaphthyl group, an acenaphthyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, a phenanthrenyl group, An anthracenyl group, a fluoranthrenyl group, a triphenylenyl group, a pyrenyl group, a klychenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, A pyrimidinyl group, a pyrimidinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a pyridyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, A phenanthridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, a benzoimidazolyl group, a quinazolinyl group, a quinazolinyl group, a quinazolinyl group, a quinazolinyl group, A thiophenyl group, a benzothiophenyl group, a thiophenyl group, A thiazolyl group, a thiazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a benzo thiophenyl group, a benzothiophene group, a benzothiophene group, A carbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzopyropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzopyrimidinyl group , A benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzoxazinyl group, and a pyridobenzothiazinyl group; And
_{-Si (Q 1) (Q 2} ) (Q 3), -N (Q 4) (Q 5) and _{-B (Q 6) (Q 7} );
&Lt; / RTI &gt;
At least one of R &lt; ₁₀ &gt; is a carbazolyl group; And a metal salt of a metal selected from the group consisting of deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, A phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₂ -C ₂₀ alkenyl group, a C ₂ -C ₂₀ alkynyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, , A pyranyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, fun group, isoquinolinium group, a salicylate group possess phthalazine, quinoxaline group, when fun group, a quinazolinyl _{group, -Si (Q 31) (Q} 32) (Q 33), -N (Q 34) (Q 35) And -B (Q ₃₆ ) (Q ₃₇ );
&Lt; / RTI &gt;
Q ₁ to Q ₇ and Q ₃₁ to Q ₃₇ are independently selected from the group consisting of hydrogen, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, A divalent group, a divalent group, a divalent group, a divalent group, a divalent group, a divalent group, and a dibenzothiophenyl group. The method according to claim 1,
Wherein Ar ₁ is selected from the group consisting of the following formulas (2-1) to (2-7):

Of the above-mentioned formulas (2-1) to (2-7)
X ₁ is C (R ₁₇ ) (R ₁₈ ), N (R ₁₉ ), O or S,
Y ₁ , Z ₁ , Z ₂ and Z ₃ are each as defined in claim 1,
R ₁ to R ₃ , R ₅ to R ₈ and R ₁₁ to R ₁₉ independently of one another,
Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;
A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of hydrogen, deuterium, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;
A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranoyl group and a dibenzothiophenyl group;
(Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) from the group consisting of hydrogen, deuterium, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, biphenyl, terphenyl, naphthyl, carbazolyl and -Si A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group which is substituted with at least one selected from a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, And dibenzothiophenyl groups; And
_{-Si (Q 1) (Q 2} ) (Q 3);
&Lt; / RTI &gt;
At least one of R ₁₁ to R ₁₄ is a carbazolyl group; And deuterium, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, the group consisting of a carbazole group and a _{-Si (Q 31) (Q 32} ) (Q 33) A carbazolyl group substituted with at least one selected from a carbazolyl group; &Lt; / RTI &gt;
Wherein Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are independently selected from the group consisting of hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group ,
* Is the binding site with neighboring atoms. The method according to claim 1,
Wherein Ar ₂ is a group represented by any one of the following formulas (3-1) to (3-7) and (4-1) to (4-19)

Among the above-mentioned formulas (3-1) to (3-7) and (4-1) to (4-19)
X ₂ is C (R ₂₇ ) (R ₂₈ ), N (R ₂₉ ), O or S,
Y &lt; ₂ &gt; is as defined in claim 1,
Z ₅ is N or C (R ₃₁₎ and, Z ₆ is N or C (R ₃₂₎ and, Z ₇ is N or C (R ₃₃₎ and, Z ₈ is N or C (R _34),
R ₂₁ to R ₂₉ and R ₃₁ to R ₃₄ , independently of each other,
Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;
A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of hydrogen, deuterium, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;
A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranoyl group and a dibenzothiophenyl group;
(Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) from the group consisting of hydrogen, deuterium, C ₁ -C ₂₀ alkyl, C ₁ -C ₂₀ alkoxy, phenyl, biphenyl, terphenyl, naphthyl, carbazolyl and -Si A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group which is substituted with at least one selected from a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, And dibenzothiophenyl groups; And
_{-Si (Q 1) (Q 2} ) (Q 3);
Wherein Q ₁ to Q ₃ independently represent hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, Lt; / RTI &gt; is selected from the group consisting of &lt; RTI ID = 0.0 &gt;
Y ₇₁ is O, S, C (R ₇₅ ) (R ₇₆ ) or Si (R ₇₅ ) (R ₇₆ );
R ₇₁ and R ₇₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazine tank group, a C ₁ - C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group and a phenanthrenyl group and any one selected from,
e2 is an integer of 0 to 2,
e3 is an integer of 0 to 3,
e4 is an integer of 0 to 4,
e5 is an integer of 0 to 5,
e6 is an integer of 0 to 6,
e7 is an integer of 0 to 7,
e9 is an integer of 0 to 9,
* Is the binding site with neighboring atoms. The method according to claim 1,
The condensed cyclic compound represented by the formula (1) is a condensed cyclic compound represented by one of the following formulas (1-1) to (1-9)

Among the above formulas 1-1 to 1-9,
And Ar _{&lt; 2 &gt;} are as defined in claim 1,
R ₄₁ to R ₄₈ independently of one another refer to the description of R ₄₀ described in claim 1,
The descriptions for R ₅₁ to R ₅₈ independently of each other refer to the description of R _{50 set} forth in claim 1,
The description of R ₆₁ to R ₆₈ , independently of each other, refers to the description of R ₆₀ as defined in claim 1. 11. The method of claim 10,
R ₄₁ to R ₄₈ , R ₅₁ to R ₅₈ and R ₆₁ to R ₆₈ independently of one another,
Hydrogen, deuterium, -F, -Cl, -Br, -I, cyano, C ₁ -C ₂₀ alkyl and C ₁ -C ₂₀ alkoxy;
A C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one member selected from the group consisting of hydrogen, deuterium, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;
A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranoyl group and a dibenzothiophenyl group;
(Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ) substituted with at least one substituent selected from the group consisting of hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group and -Si A cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofurano group and a dibenzothiophene group A phenyl group; And
_{-Si (Q 1) (Q 2} ) (Q 3);
&Lt; / RTI &gt;
Wherein Q ₁ to Q ₃ and Q ₃₁ to Q ₃₃ are independently selected from the group consisting of hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, Condensed ring compound. The method according to claim 1,
Wherein the number of carbazole groups contained in the condensed cyclic compound represented by the formula (1) is 1, 2, 3 or 4; The method according to claim 1,
Wherein the number of carbazole groups contained in R &lt; ₁₀ &gt; in the formula (1) is 1 or 2. The method according to claim 1,
Wherein the condensed ring compound represented by the formula (1) is any one selected from the following compounds 1 to 168, a condensed ring compound:

. The method according to claim 1,
The first electrode is an anode, the second electrode is a cathode,
The organic layer includes a hole transporting region disposed between the first electrode and the light emitting layer and an electron transporting region disposed 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, 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 injecting layer. The method according to claim 1,
Wherein the light emitting layer emits blue light having a maximum emission wavelength of 380 nm to 475 nm. The method according to claim 1,
Wherein the condensed ring compound contained in the light emitting layer is a retardation fluorescent emitter. The method according to claim 1,
Wherein the light emitting layer comprises only the condensed ring compound. The method according to claim 1,
Wherein the light emitting layer further comprises a host, and the content of the host is larger than the content of the condensed ring compound. The method according to claim 1,
Wherein the light emitting layer does not contain an organic metal compound.

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