KR20190079495A - Heterocyclic compound, composition including the same and organic light-emitting device including the same - Google Patents

Abstract

Disclosed are a heterocyclic compound, a composition comprising the same, and an organic light emitting device comprising the same. Since the heterocyclic compound has improved electrical properties and/or thermal stability, the organic light emitting device including the heterocyclic compound has improved current efficiency and lifespan properties.

Description

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

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

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

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

In particular, by including the heterocyclic compound, it is possible to provide an organic light emitting device having excellent current efficiency and luminescent lifetime. In addition, the heterocyclic compound may provide properties suitable for use in solution coating methods.

According to one aspect, heterocyclic compounds represented by the following formula (1) are disclosed:

≪ Formula 1 >

In Formula 1,

X ₁ to X ₂₄ independently of one another are C or N,

And at least one of X ₁ and X ₄ is C, - be combined with the (L _{2) b2} -A _1,

L ₁ is a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

L ₂ and L ₃ are, independently of each other, a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₆₀ A carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

b1 is an integer of 1 to 5,

b2 and b3 are independently of each other an integer of 0 to 5,

A ₁ and A ₂ independently represent 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 C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted Aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group and a substituted or unsubstituted C ₅ -C ₆₀ heteroaryl group, provided that at least one of A ₁ and A ₂ is a C ₅ -C ₆₀ heteroaryl group,

R ₁ to R ₆ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH _2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C _A C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ hetero 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 groups, C ₁ -C ₆₀ heteroaryl An aryloxy group, a C ₁ -C ₆₀ heteroarylthio group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group,

a1, a4 and a5 are each independently an integer of 0 to 3,

a2, a3 and a6 are each independently an integer of 0 to 4;

According to another aspect, there is provided a composition comprising at least one heterocyclic compound represented by Formula 1 above.

According to another aspect, there is provided a liquid crystal display comprising: a first electrode; A second electrode; And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic light emitting device includes at least one kind of the heterocyclic compound.

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

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

One embodiment of the present invention will be described in detail with reference to the accompanying drawings. In the present specification and drawings, constituent elements having substantially the same function and / or configuration are denoted by the same reference numerals, and redundant description is omitted.

The condensed ring compound is represented by the following formula (1): < EMI ID =

≪ Formula 1 >

In Formula 1, X ₁ to X ₂₄ are independently C or N with each other, and at least one of X ₁ and X ₄ is C, - be combined with the (L _{2) b2} -A _1.

For example, wherein X ₁ is C, - be combined with (L _{2) b2} -A _1. For another example, wherein X ₄ is C, - be combined with (L _{2) b2} -A _1.

According to one embodiment, at least one of X ₁ to X ₈ may be N.

According to one embodiment, X ₉ to X ₂₄ are each C.

According to another embodiment, X ₁ to X ₂₄ are each C, respectively.

Wherein L ₁ is a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group, Substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group.

According to one embodiment, L ₁ is selected from the group consisting of a phenylene group, a biphenylene group, a terphenylene group, a tetraphenylene group, an indenylene group, a naphthylene group, an acenaphthylene group, a fluorenylene group, A phenanthrenylene group, a phenanthrenylene group, a phenanthrenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, A thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a pyridazinyl group, a pyrimidinyl group, a pyridazinyl group, A thiadiazolyl group, an isothiadiazolyl group, a pyranyl group, an imidazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoyl group, A quinolinylene group, a phthalazylene group, A phenanthrolinylene group, a phenanthrolinylene group, a phenazylene group, a benzoxazienylene group, a benzothiazolylene group, a benzimidazolylene group, a benzimidazolyl group, a benzothiazolyl group, a benzothiazolyl group, A dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, a dibenzothiophenylene group, An imidazopyrimidinylene group, an imidazopyridinylene group, a methylene group, an ethylene group, an ethylene group, an ethylene group, a propylene group, , A propylene group, an isopropylene group, a butylene group, a pentylene group, a hexylene group, a cyclobutylene group, a cyclopentylene group and a cyclohexylene group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, alkynyl group and a C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic condensed polycyclic group, A biphenylene group, a terphenylene group, a tetraphenylene group, an indenylene group, a naphthylene group, an acenaphthylene group, a fluorenylene group, spearorbiorenylene (hereinafter referred to as " spiro-bifluorenylene group, A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, A thiazolyl group, an isothiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, A thiadiazolyl group, an isothiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, , Naphthyridinylene group, quinazolinylene group, cyano group, phenanthridinyl group, acanthienylene group, phenanthrolylene group, phenanthrene group, benzoxazienylene group, benzothiazolene group, benzimidazolylene group , Isoindolinylene group, phosphorus A benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, An imidazopyrimidinylene group, an imidazopyridinylene group, a methylene group, an ethylene group, a propylene group, an isopropylene group, an isobutylene group, an isobutylene group, , A butylene group, a pentylene group, a hexylene group, a cyclobutylene group, a cyclopentylene group and a cyclohexylene group;

≪ / RTI >

For example, the L < ₁ > may be any of a phenylene group, a fluorenylene group, a 9,9-diarylfluorenylene group, a 9,9-dialkylfluorenylene group, a spirobifluorenylene group and a triphenylenylene group Can be selected. According to one embodiment, when L ₁ is a phenylene group, L ₁ is an m-phenylene group or a p-phenylene group.

As another example, the heterocyclic group may be a substituted or unsubstituted heterocyclic group having 5 to 60 ring-forming atoms. When L < ₁ > is a substituted or unsubstituted heterocyclic group having 5 to 60 ring-forming atoms, L < ₁ > is a substituted or unsubstituted three or more ring condensed ring group containing O or S as a hetero atom , For example, a substituted or unsubstituted dibenzofuranylene group or a substituted or unsubstituted dibenzothiophenylene group.

Wherein L ₂ and L ₃ independently represent a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₆₀ when carbonyl is selected from the cyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group upon.

According to one embodiment, L ₂ and L ₃ are, independently of each other, a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, A substituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group.

According to one embodiment, L ₂ and L ₃ independently of one another are a single bond, a phenylene group, a biphenylene group, a terphenylene group, a tetraphenylene group, an indenylene group, a naphthylene group, an acenaphthyl 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, a phenanthrene group, , An imidazolylene group, a pyrazolylene group, a triazolylene group, a pyridinylene group, a pyridazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazienylene group, a furanylene group, a thienylene group, An isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isoxazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, Naphthylene group, naphthylene group, naphthylene group, A phenanthrolinylene group, a phenanthrolinylene group, a phenoxylene group, a benzoxylene group, a benzothiazole group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, a phenanthrene group, A benzofuranyl group, a benzofuranyl group, a benzothiophenylene group, a carbazolylene group, an azacabazolylene group, a dibenzofuranylene group, a azadibenzofuranylene group, a benzimidazolyl group, , Dibenzothiophenylene group, azadibenzothiophenylene group, benzocarbazolylene group, naphthobenzocarbazolylene group, naphthobenzopureanylene group, naphthobenzothiophenylene group, imidazopyrimidinylene group, imidazopyridine group, A methylene group, an ethylene group, a propylene group, an isopropylene group, a butylene group, a pentylene group, a hexylene group, a cyclobutylene group, a cyclopentylene group and a cyclohexylene group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, alkynyl group and a C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group condensed polycyclic A biphenylene group, a terphenylene group, a tetraphenylene group, an indenylene group, a naphthylene group, an acenaphthylene group, a fluorenylene group, spearorbiorenylene (hereinafter referred to as " spiro-bifluorenylene group, A substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heteroaryl group, A thiazolyl group, an isothiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, an oxadiazolyl group, A thiadiazolyl group, an isothiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, a thiadiazolyl group, , Naphthyridinylene group, quinazolinylene group, cyano group, phenanthridinyl group, acanthienylene group, phenanthrolylene group, phenanthrene group, benzoxazienylene group, benzothiazolene group, benzimidazolylene group , Isoindolinylene group, phosphorus A benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, a benzophenylene group, An imidazopyrimidinylene group, an imidazopyridinylene group, a methylene group, an ethylene group, a propylene group, an isopropylene group, an isobutylene group, an isobutylene group, , A butylene group, a pentylene group, a hexylene group, a cyclobutylene group, a cyclopentylene group and a cyclohexylene group;

≪ / RTI >

For example, L ₂ and L ₃ are, independently of each other, a phenylene group, And a triphenylenylene group. According to one embodiment, when L ₂ or L ₃ is a phenylene group, L ₂ or L ₃ may be an m-phenylene group or a p-phenylene group.

As another example, the heterocyclic group may be a substituted or unsubstituted heterocyclic group having 5 to 60 ring-forming atoms. When L ₂ or L ₃ is a substituted or unsubstituted heterocyclic group having 5 to 60 ring-forming atoms, L ₂ or L ₃ is a substituted or unsubstituted A condensed ring group having three or more rings, for example, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

According to one embodiment, L ₁ to L ₃ , independently of each other, can be selected from among the following structures:

.

.

remind Represents the position to be combined with neighboring atoms.

According to one embodiment, at least one of L ₁ through L ₃ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group, a hetero A cyclic group and a substituted or unsubstituted C ₃ -C ₆₀ cycloalkylene group.

In the above formula (1), b1 is an integer of 1 to 5.

According to one embodiment, b1 may be an integer from 1 to 3.

In the above formula (1), b2 and b3 are each independently an integer of 0 to 5.

According to one embodiment, b2 and b3 are independently of one another an integer from 0 to 2.

In Formula 1, A ₁ and A ₂ are, each independently, 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 ring with each other - C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl, tea, A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group and a substituted or unsubstituted C ₅ -C ₆₀ heteroaryl group, provided that A ₁ and A at least one of a _divalent C ₅ -C ₆₀ heteroaryl group.

According to one embodiment, A ₁ and A ₂ are each independently selected from the group consisting of phenyl, biphenyl, terphenyl, tetraphenyl, indenyl, naphthyl, acenaphthyl, A thiazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyrazinyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, a pyrrolidinyl group, A thiazolyl group, a thiadiazolyl group, an isothiadiazolyl group, an isothiadiazolyl group, a pyrazolyl group, a thiadiazolyl group, a thiadiazolyl group, an isothiadiazolyl group, a pyrazolyl group, A quinolinyl group, a quinolinyl group, a phenanthryl group, a phenanthryl group, an imidazolyl group, a quinolinyl group, an imidazolyl group, a quinolinyl group, a quinolinyl group, A decyl group, an acridinyl group, a phenanthrolinyl group, A benzofuranyl group, a dibenzofuranoyl group, a dibenzothiophenyl group, an azadibenzofuranyl group, a benzodioxolyl group, a benzodioxolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzimidazolyl group, an isoindolyl group, an indolyl group, a benzofuranyl group, a benzothiophenyl group, , A diazabenzofuranyl group, an azadibenzothiophenyl group, a diazabenzothiophenyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, an imidazopyrimidinyl group and an imidazopyridinyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, alkynyl group and a C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group condensed polycyclic A phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, an indenyl group, a naphthyl group, an acenaphthyl group, a fluorenyl group, a spirobifluorenyl group, a phenanthrene group, a fluoranthenyl group, a triphenyl Rengi, A pyrazolyl group, a triazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridinyl group, a triazinyl group, a furanyl group, a thienyl group, an oxazolyl group, an imidazolyl group, A thiadiazolyl group, an isothiadiazolyl group, a pyranyl group, an indazolyl group, a purinyl group, an isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isoxazolyl group, A phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, a phenanthrolinyl group, A benzofuranyl group, a dibenzofuranoyl group, a dibenzothiophenyl group, an azadibenzofuranyl group, a benzodioxolyl group, a benzodioxolyl group, a benzothiazolyl group, a benzothiazolyl group, a benzimidazolyl group, an isoindolyl group, an indolyl group, a benzofuranyl group, a benzothiophenyl group, , Diazabenzofuranyl group, azadibenzothiophene A thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, a thiazolyl group, , ≪ / RTI >

At least one of A ₁ and A ₂ is a pyrrole group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridinyl group, a triazinyl group, a furanyl group, An isothiazolyl group, an isothiazolyl group, an isothiazolyl group, an isoxazolyl group, an isothiazolyl group, an isothiazolyl group, an isothiadiazolyl group, a pyranyl group, an indazolyl group, a purinyl A quinolinyl group, a quinolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a quinolinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, , A phenanthryl group, a benzothiazolyl group, a benzothiazolyl group, a benzimidazolyl group, an isoindolyl group, an indolyl group, a benzofuranyl group, a benzothiophenyl group, a carbazolyl group, a dibenzothiophenyl group, A benzofuranyl group, a diazabenzofuranyl group, azadibenzo O group, diaza-benzo thiophenyl group, benzo carbazole group, a naphthoquinone benzo furanoid group, naphthoquinone benzo thiophenyl group, imidazo pyrimidinyl group and already jopi piperidinyl group; And

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, alkynyl group and a C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl groups, C ₁ -C ₆₀ heteroaryloxy group, C ₁ -C ₆₀ heteroaryl T An imidazolyl group, a pyrazolyl group, a triazolyl group, a pyridinyl group, a pyrazinyl group, a pyridazinyl group, a pyridazinyl group, a pyridazinyl group, a pyrazinyl group, a pyrazinyl group, a pyrazinyl group, A pyrimidinyl group, a pyridinyl group, An isothiazolyl group, an isothiazolyl group, an isoxazolyl group, an isothiazolyl group, a thiadiazolyl group, an isothiadiazolyl group, a pyranyl group, a pyranyl group, a thiazolyl group, A quinolinyl group, a quinolinyl group, a quinolinyl group, a quinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, A benzothiazolyl group, a benzimidazolyl group, an isoindolyl group, an indolyl group, a benzofuranyl group, a benzothiophenyl group, a carbazolyl group, a dibenzofuranyl group, a benzothiopyranyl group, A thiophenyl group, a dibenzothiophenyl group, an azadibenzofuranyl group, a diazabenzofuranyl group, an azabibenzothiophenyl group, a diazabenzothiophenyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, An imidazopyridinyl group; ≪ / RTI >

According to one embodiment, at least one of A < ₁ > and A < ₂ > may be selected from the following formulas (5-1) to

.

.

는 이웃한 원자와 결합되는 위치를 나타낸다.remind

Represents the position to be combined with neighboring atoms.

According to one embodiment, A ₁ and A ₂ may be independently selected from the above formulas (5-1) to (5-25).

According to one embodiment, A ₁ may be selected from among the formulas (5-1) to (5-11).

According to one embodiment, A ₂ may be selected from among the formulas 5-12 to 5-25.

In Formula 1, R ₁ to R ₆ independently represent hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH _2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ - C ₁₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a 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, C _A C ₁ -C ₆₀ heteroaryloxy group, a C ₁ -C ₆₀ heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

According to one embodiment, R ₁ to R ₆ independently of one another are hydrogen, -F, -Cl, -Br, -I, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ A substituted or unsubstituted C ₃ -C ₆₀ cycloalkyl group, a substituted or unsubstituted C ₃ -C ₆₀ heterocycloalkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group And monovalent non-aromatic heterocyclic polycyclic groups.

For example, R ₁ to R ₆ independently represent hydrogen, -F, -Cl, -Br, -I, methyl, ethyl, n-propyl, isopropyl, n-butyl or isobutyl butyl group, n-pentyl group, isopentyl group, tert-pentyl group, neopentyl group, 1,2-dimethylpropyl group, n-hexyl group, isohexyl group, A cyclohexyl group, a cycloheptyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chlorenyl group, a cyclopentyl group, A thienyl group, a thienyl group, a quinolinyl group, a quinolinyl group, an isoquinolinyl group, a carbamoyl group, A dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, and a terphenyl group.

According to another embodiment, R ₁ to R ₆ independently of one another are hydrogen, -F, -Cl, -Br, -I, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C _A C ₁ -C ₂₀ alkyl group and a substituted or unsubstituted C ₃ -C ₆₀ heterocycloalkyl group.

In formula (1), a1, a4 and a5 are independently an integer of 0 to 3.

According to one embodiment, a1, a4 and a5 may be integers of 1 to 3, independently of one another.

A2, a3 and a6 are independently an integer of 0 to 4;

According to one embodiment, a2 and a3 may be integers of from 1 to 4, independently of each other. According to one embodiment, a6 may be an integer from 1 to 4.

According to one embodiment, the heterocyclic compound represented by Formula 1 may be represented by Formula 1A or 1B:

≪

≪ Formula 1B >

Among the above general formulas (1A) and (1B)

Y ₁ to Y ₂₄ independently of one another are N or C,

The descriptions of L ₁ to L ₃ , A ₁ , A ₂ , b ₁ to b ₃ , R ₁ to R _6, and a ₁ to a ₆ can be referred to those described in this specification.

According to one embodiment, at least one of Y ₁ to Y ₈ in the above formulas (1A) and (1B) may be N.

According to one embodiment, Y ₉ to Y ₂₄ in the above formulas (1A) and (1B) are each C, respectively.

According to another embodiment, in the above formulas (1A) and (1B), Y ₁ to Y ₂₄ are each C.

According to one embodiment, the heterocyclic compound represented by Formula 1 may be represented by Formula 10:

≪ Formula 10 >

In the formula (10)

The descriptions of L ₁ to L ₃ , A ₁ , A ₂ and b ₁ to b ₃ are given in this specification,

The description of R ₁₁ to R ₁₃ refers to the description of R ₁ ,

For a description of R ₂₁ to R ₂₄ refer to the description of R ₂ ,

For a description of R ₃₁ to R ₃₄ refer to the description of R ₃ ,

For a description of R ₄₁ to R ₄₃ , refer to the description of R ₄ ,

For a description of R ₅₁ to R ₅₃ , refer to the description of R ₅ ,

For a description of R ₆₁ to R ₆₄ , see the description of R ₆ .

According to one embodiment, R ₁₁ to R ₁₃ , R ₂₁ , R ₂₂ , R ₂₄ , R ₃₁ , R ₃₂ , R ₃₄ , R ₄₁ to R ₄₃ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₄ are each Hydrogen,

R ₂₃ represents a hydrogen atom, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group, a triphenylenyl group, a fluorenyl group, A carbamoyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, A biphenyl group and a terphenyl group,

R ₃₃ represents a group selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group, a triphenylenyl group, a fluorenyl group, A pyridazinyl group, a triazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a biphenyl group And a terphenyl group.

According to one embodiment, the heterocyclic compound represented by Formula 1 may be any one of the following compounds 1 to 36, but is not limited thereto:

The organic light emitting device includes an organic layer including a light emitting layer, and the organic layer may have a laminated structure of, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer. The organic layer is mainly produced by a vapor deposition method and a coating method. Of these, the coating method (also referred to as a solution coating method or a wet film forming method) is a method which can produce a large-area element at low cost and can expect high productivity. However, in the case of using the coating method, the material forming the organic layer is required to have solubility in a solvent and durability to a step of drying the coating liquid.

In addition, a device in which a light emitting layer is formed using a coating method tends to have a low current efficiency and a short emission life as compared with a device manufactured using a vapor deposition method. This is thought to be due to the fact that the material of the layer produced by the coating method is easy to move through the interface with the adjacent layer, thereby degrading the function of each layer.

The heterocyclic compound according to an embodiment of the present invention has a structure in which at least one carbazole or azacarbazole is N-substituted in a structure in which two carbazoles are directly linked to each other, At least one heterocyclic group is further substituted. Accordingly, the heterocyclic compound can be suitably used for manufacturing an organic light emitting device by a coating method, and can provide a high current efficiency and a long life, that is, a high performance device.

Although it is not intended to limit the present invention by a specific theory, it is considered that the heterocyclic compound has a high molecular weight due to the structure represented by the above formula (1), and therefore can inhibit the migration of substances at the adjacent interlayer interface.

For example, when the heterocyclic compound is used for forming the light emitting layer in the organic layer of the organic light emitting device, the movement of the light emitting layer material at the interface with the hole transporting layer can be suppressed. In another example, the movement of the substance at the interface with the light emitting layer and / or the hole injection layer which is adjacent to the organic layer other than the light emitting layer, for example, in the case of using the heterocyclic compound in the formation of the hole transporting layer, can be suppressed. In this way, when each layer is formed using the heterocyclic compound, the movement of the substance at the interface with the adjacent layer is suppressed, the function of each layer is stably maintained, and the organic light emitting element having high efficiency and long life is obtained You can do it.

According to one embodiment, the molecular weight of the heterocyclic compound represented by Formula (1) may be 1000 to 3000. Alternatively, the molecular weight of the heterocyclic compound represented by Formula 1 may be 1000 or more and less than 3000. For example, the molecular weight of the heterocyclic compound represented by Formula 1 may be 1000 or more and less than 2,500. In another example, the molecular weight of the heterocyclic compound represented by Formula 1 may be 1000 or more and less than 2000. As another example, the molecular weight of the heterocyclic compound represented by Formula 1 may be 1200 or more and less than 1,800.

When the heterocyclic compound has a molecular weight in the above range, the molecular weight of the compound is high and the molecular size is large, so that the migration of molecules at the interface with the adjacent layer can be suppressed, And the function of the layer adjacent thereto can be stably maintained. Particularly, when the above heterocyclic compound is used as a host material for the light emitting layer, it is possible to prevent the migration of the substance at the interface with the hole transporting layer, and to provide an organic light emitting device excellent in current efficiency and light emission life.

[Organic light emitting element]

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

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

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

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

In the present specification, the phrase "(the organic layer) contains one or more organometallic compounds" means that one or more kinds of condensed ring compounds belonging to the above formula (1) Or more of the condensed ring compound. "

For example, the organic layer may contain only the compound 1 as the condensed ring compound. At this time, the compound 1 may exist in the light emitting layer of the organic light emitting device. Alternatively, the organic layer may include the compound 1 and the compound 2 as the condensed ring compound. At this time, the compound 1 and the compound 2 are present in the same layer (for example, both the compound 1 and the compound 2 may exist in the light emitting layer).

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

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

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

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

The hole transporting region may include only the hole injecting layer 130, or may include only the hole transporting layer 140. Alternatively, the hole transporting region may have a structure of a hole injecting layer / a hole transporting layer or a hole injecting layer / a hole transporting layer / an electron blocking layer sequentially stacked from the first electrode 120.

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

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

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

For example, the hole transport layer 140 may include at least one selected from the following compound P-1, an amine-based polymer similar thereto, and a compound FA-14:

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

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

The charge-producing material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracano-1,4-benzoquinone di Quinone derivatives such as phosphorus (F4-TCNQ); Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as the following compounds HT-D1 and HT-D2, but are not limited thereto.

When the hole transporting region includes a buffer layer, the electron blocking layer material may be selected from a material that can be used for the hole transporting region as described above and a host material described below. However, no.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The electron transporting layer 160 may further include a metal-containing material in addition to the above-described materials.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[Description of Substituent]

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

"Substituted" in the present specification means that the hydrogen atom of a substituent such as R < ₁₁ > can be further substituted with another substituent.

In the present specification, the C ₁ -C ₆₀ alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, ethyl group, n-propyl group, isopropyl group, n An n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a tert-pentyl group, a neopentyl group, Butyl group, 1-methylbutyl group, 1-methylbutyl group, 1-methylbutyl group, 1-methylbutyl group, Methylpropyl group, 1-ethyl-3-methylbutyl group, n-octyl group, 2-ethylhexyl group, 3- an n-decyl group, an n-decyl group, a 1-methyldecyl group, a n-dodecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-octadecyl group, an n- N-eicosyl group, n-heneicosyl group, n-docosyl group, n-tricosyl group, n-octadecyl group, n-tetracosyl group and the like.

In the present specification, a C ₁ -C ₆₀ alkylene group means a divalent group having the same structure as the above C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₁ -C ₆₀ alkoxy group means a monovalent group having the formula: -OA ₁₀₁ (wherein A ₁₀₁ is the C ₁ -C ₂₄ alkyl group), and specific examples thereof include methoxy group, ethoxy group , Propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, n-pentoxy group, isopentoxy group, tert- A heptyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, an undecyloxyl group, a dodecyloxyl group, a tridecyloxyl group, a tetradecyloxyl group, a pentadecyloxyl group, Heptadecyloxy group, octadecyloxy group, 2-ethylhexyloxy group, 3-ethylpentyloxy group and the like.

In the present specification, a C ₁ -C ₆₀ alkylthio group means a monovalent group having the formula: -SA ₁₀₂ (wherein A ₁₀₂ is the above C ₁ -C ₂₄ alkyl group).

In the present specification, the C ₃ -C ₆₀ cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 60 carbon atoms participating in the ring-forming, examples of which include cyclopropyl group, cyclobutyl group, cyclopentyl group A t-butyl group, a cyclohexyl group, a cycloheptyl group, and the like. The C ₃ -C ₆₀ cycloalkylene group of the specification and the second having the same structure as the above C ₃ -C ₆₀ cycloalkyl group means a group.

The C ₆ -C ₆₀ aryl group in the present specification means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms participating in the ring-forming (that is, when substituted by a substituent, The atoms contained in the substituent are not included in the number of ring-forming carbon atoms), and the C ₆ -C ₆₀ arylene group means a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a cryanecyl group and the like. The C ₆ -C ₃₀ aryl groups and C ₆ -C ₃₀ aryl If the alkylene group contains two or more rings, the 2 or more rings may be fused to each other.

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

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

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

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

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

In the present specification, the C ₇ -C ₃₀ arylalkyl group refers to a monovalent group in which the alkyl group is substituted with an aryl group and the sum of the carbon number of the alkyl group and the aryl group constituting the alkyl group is 7 to 30. Specific examples of the C ₇ -C ₃₀ arylalkyl group include a benzyl group, a phenylethyl group, a phenylpropyl group, and a naphthylmethyl group.

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

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

In the present specification, the C ₈ -C ₃₀ arylalkenyl group means a monovalent group in which the alkenyl group is substituted with an aryl group and the sum of the carbon number of the alkenyl group and the aryl group constituting the alkenyl group is 8 to 30.

In the present specification, the C ₈ -C ₃₀ arylalkynyl group refers to a monovalent group in which the alkynyl group is substituted with an aryl group, and the sum of the carbon numbers of the alkynyl group and the aryl group constituting the alkynyl group is 8 to 30.

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

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

The specification of the C ₅ -C ₆₀ carbocyclic group, when the ring-refers to a saturated or unsaturated cyclic group having only 5 to 60 carbon atoms as formed. The C ₅ -C ₆₀ carbocyclic group may be a monocyclic group or a polycyclic group, and may be monovalent, divalent, trivalent, tetralic, pentavalent or hexavalent, depending on the structure of the formula.

As used herein, a C ₁ -C ₆₀ heterocyclic group refers to a saturated or unsaturated cyclic group having at least one heteroatom selected from N, O, P, Si and S, in addition to 1 to 60 carbons as ring-forming atoms . The C ₁ -C ₆₀ heterocyclic group may be a monocyclic group or a polycyclic group, and may be monovalent, divalent, trivalent, tetralic, pentavalent or hexavalent, depending on the structure of the formula.

In the present specification, the substituted C ₅ -C ₆₀ carbocyclic group, the substituted C ₁ -C ₆₀ heterocyclic group, the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C ₂ -C ₆₀ alkynyl group, a substituted C ₁ -C ₆₀ alkoxy group, a substituted C ₃ -C ₁₀ cycloalkyl group, a substituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted C ₃ -C ₁₀ cycloalkenyl group, a substituted a C ₁ -C ₁₀ heteroaryl cycloalkenyl group, a substituted C ₆ -C ₆₀ aryl, substituted C ₆ -C ₆₀ aryloxy group, a substituted C ₆ -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ At least one of a substituted aryl group, a heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic heterocyclic polycyclic group,

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

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

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

Heavy hydrogen, -F, -Cl, -Br, -I , -CD 3, -CD 2 H, -CDH 2, -CF 3, -CF 2 H, -CFH 2, a hydroxyl group, a cyano group, a nitro group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkenyl group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid group or salt thereof, alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic group condensed polycyclic _{, -N (Q 21) (Q} 22), -Si (Q 23) (Q 24) (Q 25), -B (Q 26) (Q 27) and _{-P (= O) (Q 28} ) (Q ₂₉₎ of at least one substituted, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl , C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic heterocyclic group, fused polycyclic; And

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

≪ / RTI >

Wherein Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, A nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its salt, a sulfonic acid group or its salt, a phosphoric acid group or its salt, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group substituted by at least one of C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic heterocyclic polycyclic group.

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

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

Hereinafter, the heterocyclic compound represented by Formula 1 and the organic light emitting device including the same will be described in detail with reference to Examples and Comparative Examples. The embodiments described below are only illustrative, and the heterocyclic compound and the organic light emitting diode according to one embodiment of the present invention are not limited by the following embodiments.

In the following Synthesis Examples, the amounts of 'B' and 'A' used in the expression "B" was used in place of "A" were the same on the molar equivalent basis.

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

[Example]

Synthesis Example 1: Synthesis of Compound 1

(1) Compound 1 was synthesized according to Reaction Scheme 1 below. Intermediate E was synthesized according to Reaction Scheme 2 below.

<Reaction Scheme 1>

<Reaction Scheme 2>

(1) Synthesis of intermediate A

Phenyl-9H-carbazole (15.00 g, 46.55 mmol), 3-phenyl-6- (4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.61 g, 1.40 mmol), toluene (137 ml), ethanol (51 ml) and a 2 M aqueous sodium carbonate solution (137 ml) were added to a solution of 4- , And the mixture was stirred in a nitrogen atmosphere at 90 DEG C for 3 hours. After completion of the reaction, the reaction mixture was extracted with toluene / water, and the solvent of the organic layer was distilled and purified by column chromatography to obtain an intermediate A.

(2) Synthesis of intermediate B

Intermediate A (10.00 g, 20.64 mmol), 3-bromo-3'-chlorophenyl (6.07 g, 46.55 mmol), palladium (II) acetate (0.37 g, 1.65 mmol), tri-tert-butylphosphonium tetrafluoro (0.96 g, 3.30 mmol), sodium tert-butoxide (2.98 g, 30.95 mmol) and toluene (100 ml) were added and the mixture was stirred at 120 ° C for 4 hours in a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with toluene / water, and the solvent of the organic layer was distilled and purified by column chromatography to obtain an intermediate B.

(3) Synthesis of intermediate C

A mixture of intermediate B (8.00 g, 11.92 mmol), bis (pinacolato) diboron (4.54 g, 17.88 mmol), tris (dibenzylideneacetone) dipalladium (0) (0.55 g, 0.6 mmol), Xphos , 1.19 mmol), potassium acetate (5.26 g, 53.63 mmol) and 120 ml of 1,4-dioxane, and the mixture was stirred at 100 ° C for 4 hours in a nitrogen atmosphere. After completion of the reaction, the solvent was distilled off to obtain intermediate C.

(4) Synthesis of intermediate D

In a nitrogen atmosphere, a solution of 5-bromo-3-phenyl-9H-carbazole (18.30 g, 56.8 mmol), 2,4-diphenyl-6- (3- (4,4,5,5- Dioxaborolan-2-yl) phenyl) -1,3,5-triazine (24.52 g, 54.1 mmol), dichlorobis (triphenylphosphine ) dipalladium (0.949 g, 1.35 mmol), 154 ml of dioxane, 77 ml of toluene and 148 ml of 1M sodium carbonate aqueous solution were added and the mixture was stirred at 85 ° C for 6 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, extracted with toluene / water, and then washed with chloroform / hexane to obtain Intermediate D.

(5) Synthesis of intermediate E

Bromo-3-iodobenzene (14.51 g, 51.3 mmol), copper iodide (I) (1.86 g, 9.77 mmol), trans-1, 2-Cyclohexanediamine (3.35 g, 29.3 mmol), sodium tert-butoxide (9.39 g, 97.7 mmol) and dioxane (242 ml) were added and the mixture was stirred at 100 ° C for 7 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and the impurities were separated by filtration using Celite (registered trademark). The solvent was distilled off and purified by column chromatography to obtain intermediate E.

(6) Synthesis of compound 1

Intermediate C (8.00 g, 10.49 mmol), Intermediate E (7.40 g, 10.49 mmol), tris (dibenzylideneacetone) dipalladium (0) (0.49 g, 0.52 mmol), Xphos (0.50 g, 1.05 mmol) 127 ml of toluene, 32 ml of ethanol and 13 ml of 2M sodium carbonate aqueous solution were added, and the mixture was stirred at 90 캜 for 4 hours under a nitrogen atmosphere. After completion of the reaction, the reaction mixture was extracted with toluene / water, and the solvent of the organic layer was distilled and purified by column chromatography to obtain Compound 1. The molecular weight of Compound 1 was 1261.54.

Synthesis Example 2: Synthesis of hole transport layer material

Polymer P-1 corresponding to Compound T was synthesized according to the method described in International Publication No. 2011-159872. The structural formula of P-1 is as follows. The molecular weight of P-1 was Mn = 141,000 and Mw = 511,000.

FA-14 according to U.S. Patent Publication No. 2016/0315259 was synthesized. The structural formula of FA-14 is as follows.

Example 1

PEDOT-PSS (Sigma-Aldrich product) was coated on a glass substrate having a stripe shape of ITO (anode) of 150 nm by spin coating so as to have a dry film thickness of 15 nm, .

(FA-14: 20% by weight based on the total weight of the hole transport layer) was coated on the hole injection layer by spin coating to form a coating solution for forming a hole transport layer in which P-1 and FA-14 were dissolved in anisole Lt; 0 &gt; C for 1 hour to form a hole transporting layer having a dry film thickness of 125 nm.

Further, on the hole transporting layer, Compound 1 as a host material and tris (2- (3-p-xylyl) phenyl) pyridine iridium (III) (tris 4 wt% of a coating liquid for a light emitting layer in which iridium (III) was dissolved in methyl benzoate was applied to the hole transport layer by spin coating to form a light emitting layer having a dry film thickness of 55 nm (the doping amount of the dopant material was the total weight 10% by weight based on &lt; / RTI &gt;

Lithium quinolate (hereinafter referred to as Liq) and KLET-03 (manufactured by KEMIPRO Chemicals) were co-deposited on the light emitting layer at a ratio of 1: 1 in a vacuum vapor deposition apparatus to form an electron transport layer having a thickness of 20 nm. Lithium fluoride (hereinafter referred to as LiF) was deposited on the electron transport layer using a vacuum deposition equipment to form an electron injection layer with a thickness of 3.5 nm. Further, aluminum was vapor-deposited on the electron injecting layer using a vacuum vapor deposition equipment to form a second electrode (cathode) having a thickness of 100 nm, thereby manufacturing an organic light emitting device.

Examples 2 to 4, Comparative Examples 1 and 2

An organic light emitting device was fabricated in the same manner as in Example 1, except that the composition of the host material was changed to the composition shown in Table 1 below.

However, the host material of Comparative Example 1 was not completely dissolved in the solvent, so that the light emitting layer could not be formed, and the organic light emitting device could not be manufactured.

Evaluation example 1

The current efficiency and the luminescent lifetime of the organic luminescent devices of Examples 1 to 4 and Comparative Examples 1 and 2 were evaluated according to the following methods.

A predetermined voltage was applied to each organic light emitting element by using a DC constant voltage power source (for example, source meter: KEYENCE) to emit the organic light emitting element. Light-emitting luminance measurement of the organic light emitting diode device: as measured using a (e.g., SR-3 Topcom Co.) while gradually increasing the current applied to the organic light emitting element, a constant current when the luminance is the 6000cd / m ² And left.

Here, as to calculate the per unit current value (current density) of the organic light-emitting device, dividing the luminance (cd / m ²⁾ with the current density (A / m ^2), calculate the "current efficiency (cd / A)" Respectively.

Further, the time until the luminance value measured by the luminance measuring device gradually decreased to 95% of the initial luminance was defined as "light emission lifetime (LT ₉₅ , time) &quot;.

The evaluation results are shown in Table 1 below. The current efficiency and the luminescence lifetime of Examples 1 to 4 and Comparative Examples 1 and 2 are expressed as relative values when the measured value of Comparative Example 1 is taken as 100. [

Host material Current efficiency (relative value) Luminescent lifetime (relative value) Example 1 Compound 1 125 450 Example 2 Compound 1: Compound 41 (1: 1 weight ratio) 137 636 Example 3 Compound 1: Compound 41 (2: 3 weight ratio) 135 830 Example 4 Compound 1: Compound 44 145 363 Comparative Example 1 Compound 42: Compound 43
(1: 1 weight ratio) No tabernacle No tabernacle Comparative Example 2 Compound 44: Compound 45
(1: 1 weight ratio) 100 100

Referring to Table 1, it was confirmed that the organic light emitting devices of Examples 1 to 4 can be manufactured by a coating method, and that the current efficiency and the light emission lifetime are excellent.

Further, with reference to Example 2, it was confirmed that when a known material and the above heterocyclic compound were used together, the current efficiency and the luminescence lifetime were excellent, and with reference to Example 3, the mixing ratio with a known material was controlled Whereby an organic light emitting device having a longer life can be obtained.

In addition, referring to Example 4, when the electron transporting host and the heterocyclic compound were used together, an organic light emitting device having excellent current efficiency and emission lifetime and in particular, higher efficiency was obtained.

In addition, in Comparative Example 1, the host material was not completely dissolved in the solvent, and the light emitting layer could not be formed. Therefore, the organic light emitting device can not be manufactured by the first comparative example, and the current efficiency and the light emission lifetime can not be measured.

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

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

Claims (20)

A heterocyclic compound represented by the following formula (1):
&Lt; Formula 1 >

In Formula 1,
X ₁ to X ₂₄ independently of one another are C or N,
And at least one of X ₁ and X ₄ is C, - be combined with the (L _{2) b2} -A _1,
L ₁ is a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,
L ₂ and L ₃ are, independently of each other, a single bond, a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₃ -C ₂₀ cycloalkylene group, a substituted or unsubstituted C ₅ -C ₆₀ A carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,
b1 is an integer of 1 to 5,
b2 and b3 are independently of each other an integer of 0 to 5,
A ₁ and A ₂ independently represent 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 C ₁ -C ₆₀ heteroaryloxy group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylthio group, a substituted or unsubstituted Aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic heterocyclic polycyclic group and a substituted or unsubstituted C ₅ -C ₆₀ heteroaryl group, provided that at least one of A ₁ and A ₂ is a C ₅ -C ₆₀ heteroaryl group,
R ₁ to R ₆ independently of one another are hydrogen, deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH _2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone jongi, carboxylic acid or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl, C _A C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a C ₃ -C ₁₀ cycloalkenyl group, a C ₁ -C ₁₀ hetero 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 groups, C ₁ -C ₆₀ heteroaryl An aryloxy group, a C ₁ -C ₆₀ heteroarylthio group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic heterocyclic polycyclic group,
a1, a4 and a5 are each independently an integer of 0 to 3,
a2, a3 and a6 are each independently an integer of 0 to 4; The method according to claim 1,
The heterocyclic compound has a molecular weight of 1000 to 3000. The method according to claim 1,
At least one of L ₁ to L ₃ is a substituted or unsubstituted C ₆ -C ₆₀ carbocyclic group, a heterocyclic group having 5 to 60 ring-forming atoms including O or S as a heteroatom, Or an unsubstituted C ₃ -C ₆₀ cycloalkylene group. The method according to claim 1,
Wherein L ₁ to L ₃ are, independently of each other, a heterocyclic compound selected from the following structures:

. The method according to claim 1,
Wherein at least one of A ₁ and A ₂ is a substituted or unsubstituted C ₁ -C ₆₀ nitrogen heterocyclic group. The method according to claim 1,
At least one of A ₁ and A ₂ is a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyridazinyl group, a substituted or unsubstituted pyrazinyl group, A substituted or unsubstituted azabicyclohexyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted azadibenzofuranyl group, a substituted or unsubstituted diazabenzofuranyl group, a substituted or unsubstituted azadibenzothiophenyl group and a substituted or unsubstituted diazabenzothiophenyl group &Lt; / RTI &gt; The method according to claim 1,
Wherein at least one of A &lt; _{1 &gt;} and A &lt; ₂ &gt; is a heterocyclic compound selected from the following formulas (5-1) to

. 8. The method of claim 7,
A ₁ is a group selected from the above formulas (5-1) to (5-11). The method according to claim 1,
R ₁ to R ₆ independently represent hydrogen, -F, -Cl, -Br, -I, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₃ -C ₆₀ cycloalkyl group, A substituted or unsubstituted C ₃ -C ₆₀ heterocycloalkyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic Heterocyclic &lt; / RTI &gt; polycyclic groups. The method according to claim 1,
The heterocyclic compound represented by Formula 1 is a heterocyclic compound represented by Formula 10:
&Lt; Formula 10 >

In the formula (10)
L ₁ to L ₃ , A ₁ , A ₂ and b ₁ to b ₃ refer to the first paragraph,
R ₁₁ to R ₁₃ refer to the description of R ₁ in the first paragraph,
The description of R ₂₁ to R ₂₄ refers to the description of R ₂ in the first paragraph,
The description of R ₃₁ to R _{34 is based} on the description of R ₃ in the first paragraph,
The description of R ₄₁ to R ₄₃ refers to the description of R ₄ in the first paragraph,
R ₅₁ to R ₅₃ refer to the description of R ₅ in the first paragraph,
For a description of R ₆₁ to R ₆₄ , see the description of R ₆ in the first paragraph. 11. The method of claim 10,
Wherein R ₁₁ to R ₁₃ , R ₂₁ , R ₂₂ , R ₂₄ , R ₃₁ , R ₃₂ , R ₃₄ , R ₄₁ to R ₄₃ , R ₅₁ to R ₅₃ and R ₆₁ to R ₆₄ are each hydrogen,
R ₂₃ represents a hydrogen atom, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group, a triphenylenyl group, a fluorenyl group, A carbamoyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, A biphenyl group and a terphenyl group,
R ₃₃ represents a group selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group, a triphenylenyl group, a fluorenyl group, A pyridazinyl group, a triazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzothiophenyl group, a dibenzothiophenyl group, a biphenyl group And a terphenyl group. The method according to claim 1,
The heterocyclic compound represented by Formula 1 is an asymmetric structure. The method according to claim 1,
Wherein the heterocyclic compound represented by Formula 1 is any one selected from the following compounds 1 to 36:

. A composition for an organic light emitting device, comprising at least one heterocyclic compound according to any one of claims 1 to 13. 15. The method of claim 14,
Wherein the composition for organic light emitting devices further comprises a solvent,
Wherein the content of the heterocyclic compound in the composition for organic light emitting devices is 0.01 mass% or more. A first electrode;
A second electrode; And
And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer,
Wherein the organic layer comprises at least one heterocyclic compound of any one of claims 1 to 13. 17. The method of claim 16,
The first electrode is an anode,
The second electrode is a cathode,
Wherein the organic layer further comprises a hole transporting region interposed between the first electrode and the light emitting layer and an electron transporting region interposed between the light emitting layer and the second electrode,
Wherein the hole transporting region comprises at least one selected from the group consisting of a hole injection layer, a hole transporting layer, a buffer layer, a light emission assisting layer and an electron blocking layer,
Wherein the heterocyclic compound is included in the light emitting layer. 18. The method of claim 17,
Wherein the heterocyclic compound emits light from the triplet exciton. 18. The method of claim 17,
Wherein the hole transporting region comprises an amine-based polymer. 20. The method of claim 19,
Wherein the hole transporting region includes a hole transporting layer directly contacting the light emitting layer, and the amine-based polymer is contained in the hole transporting layer.

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