KR102235594B1 - Heterocyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

A heterocyclic compound and an organic light-emitting device including the same are disclosed.

Description

Heterocyclic compound and organic light emitting device comprising the same

It relates to a heterocyclic compound and an organic light emitting device including the same.

An organic light-emitting device is a self-luminous device that has a wide viewing angle, excellent contrast, a fast response time, excellent luminance, driving voltage, and response speed characteristics, and has the advantage of enabling multicolorization.

A typical organic light-emitting device may have a structure in which an anode is formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode. Here, the hole transport layer, the light emitting layer, and the electron transport layer are organic thin films made of an organic compound.

The driving principle of the organic light-emitting device having the above-described structure is as follows.

When a voltage is applied between the anode and the cathode, holes injected from the anode move to the emission layer via the hole transport layer, and electrons injected from the cathode move to the emission layer via the electron transport layer. Carriers such as holes and electrons recombine in the emission layer region to generate excitons. Light is produced as the excitons change from an excited state to a ground state.

It is to provide a novel heterocyclic compound and an organic light emitting device including the same.

A heterocyclic compound represented by the following formula (1) is provided:

<Formula 1>

In Formula 1,

A is a substituted or unsubstituted C ₆ -C ₃₀ aromatic ring;

Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ A cycloalkenylene group, a C ₂ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group;

The R ₁ to R ₄ , R ₁₁ and R ₁₂ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine Group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted A substituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, Substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group , -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein, Q ₁ and Q ₂ are independently of each other, substituted or unsubstituted C ₃ -C ₁₀ Cycloalkyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, and selected from a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group; The Q ₃ to Q ₅ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydr A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, A substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ Cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, and selected from a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group);

n and m are each independently selected from an integer of 0 to 5;

a is selected from an integer of 1 to 4,

However, when n is 0, R ₁₁ is not hydrogen.

In addition, the first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one heterocyclic compound.

The organic light-emitting device including the heterocyclic compound may have a low driving voltage, high efficiency, high luminance, high color purity, and long life.

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

The heterocyclic compound is represented by the following formula (1):

<Formula 1>

In Formula 1, ring A is a substituted or unsubstituted C ₆ -C ₃₀ aromatic ring. For example, the A ring may be a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted substituted or unsubstituted anthracene ring, or a substituted or unsubstituted phenanthrene ring. It is not limited. When the ring A is a substituted ring, the substituent of the substituted ring A refers to the description of R ₅ in the present specification.

According to one embodiment, the A ring may be a substituted or unsubstituted benzene ring. Thus, the heterocyclic compound may be represented by the following formula 1A:

<Formula 1A>

In Formula 1A, Ar ₁ , Ar ₂ , R ₁ to R ₄ , R ₁₁ , R ₁₂ , n, m and a are described in reference to those described herein. For the description of R ₅ in Formula 1A, refer to the description _{of R 1 in the present specification.} In Formula 1A, b is selected from an integer of 1 to 4.

In the above chemistry 1, Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted Selected from C _{3 -C 10} cycloalkenylene group, C ₂ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group and substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group Can be.

For example, in Formula 1, Ar ₁ and Ar ₂ are independently of each other,

Phenylene group (phenylene), pentalenylene group (pentalenylene), indenylene group (indenylene), naphthylene group (naphtylene), azulenylene group (azulenylene), heptalenylene group (heptalenylene), indacenylene group (indacenylene), Acenaphthylene group (acenaphtylene), fluorenylene group (fluorenylene), spiro-fluorenylene group, phenalenylene group (phenalenylene), phenanthrenylene group (phenanthrenylene), anthrylene group (anthrylene), fluoranthenylene group (fluoranthenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl Pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene, and quinolinylene , Benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinolinylene, Carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene group (ph enanthrolinylene), phenazinylene, benzooxazolylene, benzoimidazolylene, furanylene, benzofuranylene, thiophenylene, benzo Thiophenylene group (benzothiophenylene), thiazolylene group (thiazolylene), isothiazolylene group (isothiazolylene), benzothiazolylene group (benzothiazolylene), isoxazolylene group (isoxazolylene), oxazolylene group (oxazolylene), triazolylene group, tetra Zolylene group, oxadiazolylene, triazinylene, benzooxazolylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene and di Benzosilolylene group (dibenzosilolylene); And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts; C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group; And deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylflu At least one of orenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group A substituted, C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heteroaryl group; Phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptarenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spy substituted with at least one substituent selected from among Ro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthrylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylene group , Pentaphenylene group, hexaenylene group, pyrroleylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, inda Zolylene group, furinylene group, quinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, sinolinylene group, carbazolylene group, phenanthridinyl Ethylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, iso Thiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, benzoxazolylene group, dibenzofuranylene group, dibenzothiophenyl A ren group, a benzocarbazolylene group, and a dibenzosilolylene group; Can be selected from.

According to an embodiment, in Formula 1, Ar ₁ is

Phenylene group, naphthalene group, and carbazolyl group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group and an isoquinolinyl group substituted with at least one of a phenylene group, a naphthalene group, and a carbazolyl group; Can be selected from.

According to another embodiment, Ar ₁ in Formula 1 is

Carbazolyl group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A carbazolyl group substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group; It may be selected from among, but is not limited thereto.

In Formula 1, n represents _{the number of Ar 1} , and may be selected from an integer of 0 to 5. When n is 0, R ₁₁ is directly connected to the heterocyclic core of Formula 1. When n is 2 or more, 2 or more R ₁₁ may be the same as or different from each other. For example, n can be 0, 1 or 2.

Meanwhile, in Formula 1, Ar ₂ is

A phenylene group and a naphthalene group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenylene group and a naphthalene group substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group and an isoquinolinyl group; Can be selected from.

In Formula 1, m represents _{the number of Ar 2} , and may be selected from an integer of 0 to 5. When m is 0, R ₁₂ is directly connected to N of the heterocyclic core of Formula 1. When m is 2 or more, 2 or more R ₁₂ may be the same as or different from each other.

According to another embodiment, Ar ₁ and Ar ₂ may be each independently represented by one of the following Formulas 2-1 to 2-29, but are not limited thereto:

In Formulas 2-1 to 2-29,

Y ₁ is O, S, C(Z ₃ )(Z ₄ ) or N(Z ₅ );

Z ₁ to Z ₅ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;

C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluore At least one of a nil group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group A substituted, C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heteroaryl group; And

-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group Or a C ₂ -C ₂₀ heteroaryl group); Is selected from;

d1 is an integer of 1 to 4, d2 is an integer of 1 to 3, d3 is an integer of 1 to 6, d4 is an integer of 1 to 8, d5 is 1 or 2, * is a heterocycle in Formula 1 A binding site with a core, a binding site with a neighboring Ar ₁ or a binding site with a neighboring Ar ₂ , *'is _{a binding site with a neighboring Ar 1} in Formula 1, a binding site with a neighboring Ar ₂ , R ₁₁ It is a binding site with or a binding site with _{R 12.}

For example, in Formulas 2-1 to 2-29, Z ₁ to Z ₅ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;

Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, Carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; And

-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group Group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group , Or isoquinolinyl group); It may be selected from among, but is not limited thereto.

For example, Ar ₁ in Formula 1 may be one of Formulas 2-26 to 2-29, and Ar ₂ may be Formula 2-1 or 2-2, but is not limited thereto.

According to another embodiment, Ar ₁ and Ar ₂ may be each independently represented by one of the following Formulas 3-1 to 3-23:

In Formulas 3-1 to 3-23, * is a bonding site with a heterocyclic core in Formula 1, a bonding site with an adjacent Ar ₁ , or a bonding site with an _{adjacent Ar 2; *'is a binding site with a neighboring Ar 1} in Formula 1, a binding site with a neighboring Ar ₂ , a binding site with R ₁₁ or a binding site with _{R 12.}

For example, in Formula 1, Ar ₁ may be represented by one of Formulas 3-20 to 3-23, and Ar ₂ may be represented by Formula 3-1, but is not limited thereto.

In Formula 1, R ₁ to R ₄ , R ₁₁ and R ₁₂ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, Amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alke Nyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C _2- C ₆₀ heteroaryl group, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein, Q ₁ and Q ₂ are independently of each other, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted Is selected from a C ₆ -C ₆₀ aryl group, and a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group; The Q ₃ to Q ₅ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br , -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, substituted or It may be selected from an unsubstituted C ₆ -C ₆₀ aryl group, and a substituted or unsubstituted C ₂ -C _{60 heteroaryl group).}

For example, in Formula 1, R ₁₁ and R ₁₂ are independently of each other,

Phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaphtyl ), fluorenyl group (fluorenyl), spiro-fluorenyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group (anthracenyl), fluoranthenyl group (fluoranthenyl), triphenylenyl group ( triphenylenyl), pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl , Pyrroleyl group (pyrrolyl), imidazolyl group (imidazolyl), pyrazolyl group (pyrazolyl), pyridinyl group (pyridinyl), pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group (pyridazinyl), Isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, benzoquinolinyl, phthalazinyl, naphthyl Naphthyridinyl, quinoxalinyl, quinazolinyl, cinolinyl, carbazolyl, phenanthridinyl, acridinyl, phenane Trolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothio Phenyl group (benzothiopheny l), thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxa Diazolyl, triazolyl, benzooxazolyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl and dibenzosilolyl ;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts; C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group; And deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylflu At least one of orenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group A substituted, C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heteroaryl group; Phenyl group, pentarenyl group, indenyl group, naphthyl group, azulenyl group, heptarenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, p Nalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, hexasenyl group, pyrroleyl group , Imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, benzoquinolinyl group, p Thalasinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group , Furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group , Triazinyl group, benzoxazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzosilolyl group; And

-N(Q ₁ )(Q ₂ ) (here, Q ₁ and Q ₂ are each independently a phenyl group, pentarenyl group, indenyl group, naphthyl group, azulenyl group, heptarenyl group, indacenyl group, acenaphthyl group , Fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, Perylenyl group, pentaphenyl group, hexaenyl group, pyrroleyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, Purinyl group, quinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, Phenazinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group , Triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, benzooxazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzosilolyl group); Can be selected from.

For example, in Formula 1, R ₁₁ and R ₁₂ are independently of each other,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, iso Quinolinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group and triazinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , Substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, iso Quinolinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group and triazinyl group; And

-N(Q ₁ )(Q ₂ ) (wherein, Q ₁ and Q ₂ are each independently selected from a phenyl group, a naphthyl group, and an anthracenyl group); Can be selected from.

For example, in Formula 1, R ₁₁ and R ₁₂ may be each independently represented by one of the following Formulas 4-1 to 4-18:

In Formulas 4-1 to 4-18,

Y ₁₁ is O, S, N(Z ₁₃ ) or C(Z ₁₄ )(Z ₁₅ );

The Z ₁₁ to Z ₁₅ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;

C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluore At least one of a nil group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group A substituted, C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heteroaryl group; And

-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group Or a C ₂ -C ₂₀ heteroaryl group); Is selected from;

Q ₁ and Q ₂ are each independently a phenyl group, pentarenyl group, indenyl group, naphthyl group, azulenyl group, heptarenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, p. Nalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, hexasenyl group, pyrroleyl group , Imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, benzoquinolinyl group, p Thalasinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group , Furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group , Triazinyl group, benzooxazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzosilolyl group;

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

In Formulas 4-1 to 4-18, Z ₁₁ to Z ₁₅ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;

Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, Carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; And

-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group Group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group , Or isoquinolinyl group); It may be selected from among, but is not limited thereto.

In Formula 1, R ₁ to R ₄ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;

Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, Carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; And

-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group Group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group , Or isoquinolinyl group); Can be selected from.

For example, in Formula 1, R ₁ to R ₄ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group , Hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorine Phenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoqui It may be selected from the nolinyl group, but is not limited thereto.

In Formula 1, when n is 0, R ₁₁ is not hydrogen. That is, "?? (Ar ₁ ) _n -R ₁₁ "in Formula 1 is not hydrogen.

The heterocyclic compound may be represented by the following Formula 1A(1), 1A(2), or 1A(3), but is not limited thereto:

<Formula 1A(1)> <Formula 1A(2)>

<Formula 1A(3)>

In Formulas 1A(1), 1A(2), and 1A(3), _{descriptions of R 1} to R ₅ , a, b, Ar ₂ , m, R ₁₁ and R ₁₂ refer to those described herein.

For example, in Formulas 1A(1), 1A(2), and 1A(3),

Ar ₂ is

A phenylene group and a naphthalene group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenylene group and a naphthalene group substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group and an isoquinolinyl group; Is selected from;

m is 0, 1 or 2;

R ₁₁ and R ₁₂ are independently of each other,

Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, iso Quinolinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group and triazinyl group; And

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , Substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. Phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, iso Quinolinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group and triazinyl group; Is selected from;

R ₁ to R ₅ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;

Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, Carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; And

-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group Group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group , Or isoquinolinyl group); Is selected from;

a and b may be independently selected from an integer of 1 to 4, but are not limited thereto.

In Formulas 1A(1), 1A(2), and 1A(3), R ₁ to R ₅ may be hydrogen.

The heterocyclic compound may be one of the following compounds 1 to 52, but is not limited thereto:

The substituted C ₆ -C ₆₀ cyclic moiety, the substituted C ₂ -C ₆₀ heterocyclic moiety, the substituted C ₃ -C ₁₀ cycloalkylene group, the substituted C ₃ -C ₁₀ heterocycloalkyl Ene group, the substituted C ₃ -C ₁₀ cycloalkenylene group, the substituted C ₃ -C ₁₀ heterocycloalkenylene group, the substituted C ₆ -C ₆₀ arylene group, the substituted C ₂ -C ₆₀ heteroaryl Ene group, the substituted C ₃ -C ₁₀ cycloalkyl group, the substituted C ₃ -C ₁₀ heterocycloalkyl group, the substituted C ₃ -C ₁₀ cycloalkenyl group, the substituted C ₃ -C ₁₀ heterocycloalkenyl group, The substituted C ₆ -C ₆₀ aryl group, the substituted C ₂ -C ₆₀ heteroaryl group, the substituted C ₁ -C ₆₀ alkyl group, the substituted C ₂ -C ₆₀ alkenyl group, the substituted C _2- At least _{one substituent of the C 60} alkynyl group, the substituted C 1 -C ₆₀ alkoxy group, the substituted C ₆ -C ₆₀ aryloxy group and the substituted C ₆ -C ₆₀ arylthio group,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group substituted with at least one of its salts;

C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl An oxy group, a C ₆ -C ₆₀ arylthio group and a C ₂ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluore At least one of a nil group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group Substituted, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C _6- C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₂ -C ₆₀ heteroaryl group; And

-N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) (wherein, Q ₁₁ and Q ₁₂ are independently of each other, C ₆ -C ₆₀ aryl group, or C ₂ -C ₆₀ heteroaryl group, Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ aryl group, or a C ₂ -C ₆₀ heteroaryl group ); It may be selected from among, but is not limited thereto.

The organic light-emitting device employing the heterocyclic compound represented by Formula 1 may have high driving voltage, high efficiency, high luminance, high color purity, and long life.

The heterocyclic compound having Formula 1 may be synthesized using a known organic synthesis method. The method for synthesizing the heterocyclic compound can be easily recognized by those skilled in the art with reference to Examples to be described later.

The heterocyclic compound of Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the heterocyclic compound may be used in at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function and/or a light emitting layer at the same time.

Accordingly, a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer is a heterogeneous layer represented by Chemical Formula 1 as described above. An organic light-emitting device comprising at least one cyclic compound is provided.

The organic layer is i) a functional layer having a hole injection layer, a hole transport layer, a hole injection function and a hole transport function between the first electrode and the emission layer (hereinafter referred to as "H-functional layer" H), at least one of a buffer layer and an electron blocking layer, and ii) at least one of a hole blocking layer, an electron transport layer, and an electron injection layer between the emission layer and the second electrode.

In the present specification, “(organic layer) includes one or more heterocyclic compounds” means “(organic layer) one heterocyclic compound belonging to the category of Formula 1 or two different types belonging to the category of Formula 1 above. It may be interpreted as "may include the above heterocyclic compound."

For example, the organic layer may include only Compound 8 as the heterocyclic compound. In this case, the compound 8 may be present in the emission layer of the organic light emitting device. Alternatively, the organic layer may include Compound 8 and Compound 35 as the heterocyclic compound. At this time, the compound 8 and the compound 35 are present in the same layer (for example, the compound 8 and the compound 35 may be present in the light emitting layer) or in different layers (for example, the compound 8 is in the light emitting layer) And the compound 35 may be present in the hole transport layer).

In the present specification, the term "organic layer" refers to a single layer and/or a plurality of layers interposed between the first electrode and the second electrode of the organic light emitting device.

The heterocyclic compound may be present in the emission layer included in the organic layer among the organic light emitting devices. For a description of the heterocyclic compound, refer to the description described herein. For example, the heterocyclic compound included in the emission layer may serve as a host, and the emission layer may further include a dopant. The dopant included in the emission layer may include an organometallic compound including at least one of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.

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 method of manufacturing an organic light-emitting device according to an embodiment of the present invention will be described with reference to FIG. 1.

As the substrate 11, a substrate used in a typical organic light emitting device may be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and waterproofness may be used.

The first electrode 13 may be formed by providing a material for a first electrode on the substrate by using a vapor deposition method or a sputtering method. When the first electrode 13 is an anode, the material for the first electrode may be selected from materials having a high work function to facilitate hole injection. The first electrode 13 may be a reflective electrode or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like, which are transparent and have excellent conductivity, may be used. Alternatively, using magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. One electrode 13 may be formed as a reflective electrode.

The first electrode 13 may have a single layer or a multilayer structure of two or more. For example, the first electrode 13 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto.

An organic layer 15 is provided on the first electrode 13.

The organic layer 15 may include a hole injection layer, a hole transport layer, a buffer layer, an emission layer, an electron transport layer, and an electron injection layer.

The hole injection layer HIL may be formed on the first electrode 13 by various methods such as a vacuum deposition method, a spin coating method, a cast method, and an LB method.

In the case of forming the hole injection layer by vacuum evaporation, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the target hole injection layer, etc., but for example, the deposition temperature is about 100 to It may be selected from a range of about 500°C, a vacuum degree of about 10 ^-8 to about 10 ^-3 torr, and a deposition rate of about 0.01 to about 100 Å/sec, but is not limited thereto.

In the case of forming the hole injection layer by spin coating, the coating conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, but coating at about 2000 rpm to about 5000 rpm. The speed and the heat treatment temperature for removing the solvent after coating may be selected in a temperature range of about 80° C. to 200° C., but are not limited thereto.

As the hole injection material, a known hole injection material may be used. As a known hole injection material, for example, N,N′-diphenyl-N,N′-bis-[4-(phenyl-m- Tolyl-amino)-phenyl]-biphenyl-4,4'-diamine (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl- 4,4′-diamine: DNTPD), phthalocyanine compounds such as copper phthalocyanine, m-MTDATA [4,4',4''-tris (3-methylphenylphenylamino) triphenylamine], NPB(N,N'-di(1- Naphthyl)-N,N'-diphenylbenzidine (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)), TDATA, 2-TNATA, Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid: Polyaniline /Dodecylbenzenesulfonic acid), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate):poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)), Pani /CSA (Polyaniline/Camphor sulfonic acid: polyaniline/camphor sulfonic acid) or PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate): polyaniline)/poly(4-styrenesulfonate)), etc., may be used, but are limited thereto. no:

Alternatively, the hole injection layer may include the heterocyclic compound represented by Formula 1, but is not limited thereto.

The hole injection layer may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. When the thickness of the hole injection layer satisfies the above-described range, satisfactory hole injection characteristics may be obtained without a substantial increase in driving voltage.

Next, a hole transport layer (HTL) may be formed on the hole injection layer by using various methods such as a vacuum deposition method, a spin coating method, a cast method, and an LB method. In the case of forming the hole transport layer by vacuum evaporation and spinning, the deposition conditions and coating conditions vary depending on the compound to be used, but may generally be selected from a range of conditions substantially the same as those of the hole injection layer.

Known hole transport materials include, for example, carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, and N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1 ,1-biphenyl]-4,4'-diamine (TPD), TCTA (4,4',4"-tris (N-carbazolyl) triphenylamine (4,4',4"-tris (N- carbazolyl)triphenylamine)), NPB(N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)) And the like, but are not limited thereto.

Alternatively, the hole transport layer may include the heterocyclic compound represented by Formula 1, but is not limited thereto. For example, the hole transport layer may include a heterocyclic compound represented by Formula 1A-HTL1 or 1B-HTL2.

The hole transport layer may have a thickness of about 50 Å to about 2000 Å, for example, about 100 Å to about 1500 Å. When the thickness of the hole transport layer satisfies the above-described range, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

The H-functional layer (functional layer having a hole transport function at the same time) may include one or more of the above-described hole injection layer material and hole transport layer material, and the thickness of the H-functional layer is about 500 Å to about 10000 Å. , For example, it may be about 100 Å to about 1000 Å. When the thickness of the H-functional layer satisfies the above-described range, satisfactory hole injection and aqueous characteristics may be obtained without a substantial increase in driving voltage.

Meanwhile, the H-functional layer may include the heterocyclic compound represented by Formula 1, but is not limited thereto. For example, the H-functional layer may include a heterocyclic compound represented by Formula 1A-HTL1 or 1B-HTL2.

At least one of the hole injection layer, the hole transport layer, and the H-functional layer, in addition to the known hole injection material, the known hole transport material and/or a material having a hole injection function and a hole transport function as described above, the conductivity of the film In order to improve the like, a charge-generating material may be further included.

The charge-generating 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 tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane Quinone derivatives such as phosphorus (F4-CTNQ) and the like; Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as the following Compound 200, etc., but are not limited thereto.

<Compound 200> <F4-TCNQ>

When the hole injection layer, the hole transport layer, or the H-functional layer further includes the charge-generating material, the charge-generating material is homogeneous among the hole injection layer, the hole transport layer, or the H-functional layer. ) Various modifications are possible, such as being dispersed or non-uniformly distributed.

A buffer layer may be interposed between at least one of the hole injection layer, the hole transport layer, and the H-functional layer and the emission layer. The buffer layer may serve to increase efficiency by compensating for an optical resonance distance according to a wavelength of light emitted from the emission layer. The buffer layer may include a known hole injection material or a hole transport material. Alternatively, the buffer layer may include the same material as one of materials included in the hole injection layer, the hole transport layer, and the H-functional layer formed under the buffer layer.

Subsequently, the light emitting layer EML may be formed on the hole transport layer, the H-functional layer, or the buffer layer by using a method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method. In the case of forming the light emitting layer by vacuum deposition or spin coating, the deposition conditions vary depending on the compound to be used, but may generally be selected from a range of conditions substantially the same as for forming the hole injection layer.

The emission layer may include a host and a dopant. The dopant may include a fluorescent dopant and/or a phosphorescent dopant. The phosphorescent dopant may be an organometallic compound including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, or Tm. The host may include a heterocyclic compound represented by Formula 1.

When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. Alternatively, the emission layer may have a structure in which two or more of a red emission layer, a green emission layer, and/or a blue emission layer are stacked to emit white light, but is not limited thereto.

Meanwhile, at least one of the red emission layer, the green emission layer, and the blue emission layer may include the following dopant (ppy = phenylpyridine).

For example, the following compounds may be used as the blue dopant, but the present invention is not limited thereto.

DPAVBi

TBPe

For example, the following compounds may be used as the red dopant, but the present invention is not limited thereto. Alternatively, as the red dopant, DCM or DCJTB described later may be used.

For example, the following compounds may be used as the green dopant, but the present invention is not limited thereto. Alternatively, as a green dopant, the following C545T may be used.

Meanwhile, the dopant that may be included in the emission layer may be a complex as described below, but is not limited thereto:

In addition, the dopant that may be included in the emission layer may be an Os-complex as described below, but is not limited thereto:

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

The thickness of the emission layer may be about 100 Å to about 1000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer satisfies the above-described range, excellent emission characteristics may be exhibited without a substantial increase in driving voltage.

Next, an electron transport layer (ETL) is formed on the light emitting layer by various methods such as vacuum deposition, spin coating, and casting. In the case of forming the electron transport layer by vacuum evaporation and spin coating, the conditions vary depending on the compound to be used, but in general, it may be selected from a range of conditions substantially the same as for the formation of the hole injection layer. As the material for the electron transport layer, a known electron transport material may be used as it has a function of stably transporting electrons injected from an electron injection electrode (Cathode). Examples of known electron transport materials include quinoline derivatives, in particular tris (8-quinolinorate) aluminum (Alq3), TAZ, Balq, beryllium bis (benzoquinolin-10-noate) (beryllium bis (benzoquinolin-10- olate: Bebq ₂ ), ADN, compound 201, compound 202, and the like may be used, but is not limited thereto.

<Compound 201> <Compound 202>

BCP

The electron transport layer may have a thickness of about 100 Å to about 1000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the above-described range, satisfactory electron transport characteristics can be obtained without a substantial increase in driving voltage.

Alternatively, the electron transport layer may further include a metal-containing material in addition to a known electron transport organic compound.

The metal-containing compound may include a Li complex as the metal-containing material. Non-limiting examples of the Li complex include lithium quinolate (LiQ) or the following compound 203:

<Compound 203> <LiQ>

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the material is not particularly limited.

In addition, an electron injection layer (EIL), which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the material is not particularly limited.

As the material for forming the electron injection layer, any material known as the material for forming the electron injection layer such as _{LiF, NaCl, CsF, Li 2 O, and BaO may be used.} The deposition conditions of the electron injection layer vary depending on the compound to be used, but may generally be selected from a range of conditions substantially the same as the formation of the hole injection layer.

The electron injection layer may have a thickness of about 1 Å to about 100 Å, and about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above-described range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

A second electrode 17 is provided on the organic layer 15. The second electrode may be a cathode, which is an electron injection electrode. In this case, a metal having a low work function, an alloy, an electroconductive compound, and a mixture thereof may be used as the metal for forming the second electrode. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). By forming a thin film, a transmissive electrode can be obtained. On the other hand, in order to obtain a top light emitting device, various modifications are possible, such as being able to form a transmissive electrode using ITO or IZO.

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

In addition, in the case of using a phosphorescent dopant in the light emitting layer, in order to prevent diffusion of triplet excitons or holes into the electron transport layer, vacuum deposition method, spin coating method, between the hole transport layer and the light emitting layer or between the H-functional layer and the light emitting layer, The hole blocking layer (HBL) may be formed using a method such as a cast method or an LB method. In the case of forming the hole blocking layer by vacuum deposition or spin coating, the conditions vary depending on the compound to be used, but may generally be within the same range of conditions as the formation of the hole injection layer. A known hole blocking material can also be used, and examples thereof include oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, and the like. For example, the following BCP can be used as the hole blocking layer material.

The hole blocking layer may have a thickness of 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 may be obtained without a substantial increase in driving voltage.

In the present specification, _{specific examples of an unsubstituted C 1} -C ₆₀ alkyl group (or C ₁ -C ₆₀ alkyl group) include 1 carbon number such as methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc. To 60 linear or branched alkyl groups, and at least one substituent of the substituted _{C 1} -C _{60 alkyl group,}

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group substituted with at least one of its salts;

C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl An oxy group, a C ₆ -C ₆₀ arylthio group and a C ₂ -C ₆₀ heteroaryl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluore At least one of a nil group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group Substituted, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₃ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C _6- C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group and C ₂ -C ₆₀ heteroaryl group; And

-N(Q ₁₁ )(Q ₁₂ ) and -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ) (wherein, Q ₁₁ and Q ₁₂ are independently of each other, C ₆ -C ₆₀ aryl group, or C ₂ -C ₆₀ heteroaryl group, Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group, a C ₆ -C ₆₀ aryl group, or a C ₂ -C ₆₀ heteroaryl group ); It may be selected from among, but is not limited thereto.

In the present specification, an unsubstituted C ₁ -C ₆₀ alkoxy group (or C ₁ -C ₆₀ alkoxy group) has a formula of -OA (wherein A is an unsubstituted C ₁ -C _{60 alkyl group as described above)} , As specific examples thereof, there are methoxy, ethoxy, isopropyloxy, and the like, and at least one hydrogen atom among these alkoxy groups may be substituted with the same substituent as in the case of the substituted _{C 1} -C _{60 alkyl group described above.} .

In the present specification, the unsubstituted C ₂ -C ₆₀ alkenyl group (or C ₂ -C ₆₀ alkenyl group) contains one or more carbon double bonds in the middle or end of the _{unsubstituted C 2} -C _{60 alkyl group.} it means. Examples include ethenyl, propenyl, butenyl and the like. At least one hydrogen atom among these unsubstituted C ₂ -C ₆₀ alkenyl groups may be substituted with the same substituent as in the case of the above-described substituted C ₁ -C _{60 alkyl group.}

In the present specification, the unsubstituted C ₂ -C ₆₀ alkynyl group (or C ₂ -C ₆₀ alkynyl group) contains one or more carbon triple bonds in the middle or end of the _{C 2} -C _{60 alkyl group as defined above.} Means that. Examples include ethynyl, propynyl, and the like. At least one hydrogen atom among these alkynyl groups may be substituted with the same substituent as in the case _{of the above-described substituted C 1} -C _{60 alkyl group.}

In the present specification, an unsubstituted C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms including one or more aromatic rings, and an unsubstituted C _6- C ₆₀ arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms including one or more aromatic rings. When the aryl group and the arylene group include two or more rings, the two or more rings may be fused to each other. At least one hydrogen atom of the aryl group and the arylene group may be substituted with the same substituent as in the case _{of the above-described substituted C 1} -C _{60 alkyl group.}

Examples of the substituted or unsubstituted C ₆ -C ₆₀ aryl group include a phenyl group, a C ₁ -C ₁₀ alkylphenyl group (eg, ethylphenyl group), a C ₁ -C ₁₀ alkylbiphenyl group (eg, ethylbiphenyl group). ), halophenyl group (e.g., o-, m- and p-fluorophenyl group, dichlorophenyl group), dicyanophenyl group, trifluoromethoxyphenyl group, o-, m-, and p-tolyl group, o-, m- and p-cumenyl group, mesityl group, phenoxyphenyl group, (α,α-dimethylbenzene) phenyl group, (N,N'-dimethyl) aminophenyl group, (N,N'-diphenyl) aminophenyl group, pentare Nyl group, indenyl group, naphthyl group, halonaphthyl group (e.g., fluoronaphthyl group), C ₁ -C ₁₀ alkylnaphthyl group (e.g. methylnaphthyl group), C ₁ -C ₁₀ alkoxynaphthyl group (e.g. For example, methoxynaphthyl group), anthracenyl group, azrenyl group, heptarenyl group, acenaphthylenyl group, phenalenyl group, fluorenyl group, anthraquinolyl group, methylanthracenyl group, phenanthryl group, triphenyle Nyl group, pyrenyl group, chrysenyl group, ethyl-chrycenyl group, pisenyl group, perylenyl group, chloroperylenyl group, pentaphenyl group, pentacenyl group, tetraphenylenyl group, hexaphenyl group, hexaenyl group, rubisenyl group , A coroneryl group, a trinaphthylenyl group, a heptaphenyl group, a heptacenyl group, a pyrantrenyl group, an ovarenyl group, and the like, _{and examples of the substituted C 6} -C ₆₀ aryl group are unsubstituted C as described above. It can be easily recognized by referring to _{the example of the 6} -C ₆₀ aryl group and the substituent of the substituted C ₁ -C _{60 alkyl group.} Examples of the substituted or unsubstituted C ₆ -C ₆₀ arylene group may be easily recognized with reference to the examples of the substituted or unsubstituted C ₆ -C ₆₀ aryl group.

In the present specification, an unsubstituted C ₂ -C ₆₀ heteroaryl group refers to a monovalent group having a system consisting of at least one aromatic ring in which one or more heteroatoms are selected from N, O, P, or S, and the remaining ring atoms are C. And, the unsubstituted C ₂ -C ₆₀ heteroarylene group refers to a divalent group having a system consisting of one or more aromatic rings including one or more heteroatoms selected from N, O, P, or S, and the remaining ring atoms being C do. Here, when the heteroaryl group and the heteroarylene group include two or more rings, the two or more rings may be fused to each other. At least one hydrogen atom among the heteroaryl group and the heteroarylene group may be substituted with the same substituent as in the case of _{the C 1} -C _{60 alkyl group described above.}

Examples of the unsubstituted C ₂ -C ₆₀ heteroaryl group include pyrazolyl group, imidazolyl group, oxazolyl group, thiazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, pyridinyl group, and pyri Dazinyl group, pyrimidinyl group, triazinyl group, carbazolyl group, indolyl group, quinolinyl group, isoquinolinyl group, benzoimidazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and the like. Examples of the unsubstituted C ₂ -C ₆₀ hetero arylene groups may be easily recognized with reference to the examples of the substituted or unsubstituted C ₂ -C ₆₀ arylene group.

The substituted or unsubstituted C ₆ -C ₆₀ aryloxy group _{refers to -OA 2} (wherein, A ₂ is the substituted or unsubstituted C ₆ -C ₆₀ aryl group), and the substituted or unsubstituted C ₅ -C ₆₀ arylthio group refers to -SA ₃ (wherein, A ₃ is the above substituted or unsubstituted C ₆ -C ₆₀ aryl group).

Hereinafter, the organic light emitting device according to an embodiment of the present invention will be described in more detail by way of Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples. In the following synthesis example, in the expression "B was used instead of A", the amounts of A and B are the same on a molar equivalent basis.

[Example]

Example 1

A glass substrate on which ITO/Ag/ITO (70Å/1000Å/70Å) was formed as an anode was cut into a size of 50mm x 50mm x 0.5mm and ultrasonically cleaned for about 5 minutes using isopropyl alcohol and pure water, and then UV rays were applied for 30 minutes. It was irradiated, washed by exposure to ozone, and mounted in a vacuum evaporation apparatus. 2-TNATA was deposited on the anode to form a hole injection layer having a thickness of 60 nm, and NPB was deposited on the hole injection layer to form a hole transport layer having a thickness of 100 nm. Compound 19 (host) and Ir (ppy) ₃ (dopant) were co-deposited on the hole transport layer at a weight ratio of 91:9 to form a 25 nm-thick emission layer, and then BCP was deposited on the emission layer to form 5 nm-thick holes. A blocking layer was formed. _{Alq 3} is deposited on the hole blocking layer to form an electron transport layer having a thickness of 35 nm, and then LiF is deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm, and then Mg and Al are formed on the electron injection layer. Was co-deposited at a weight ratio of 9:1 to form a 12 nm-thick cathode, thereby fabricating an organic light-emitting device (emission of green light).

Alq ₃

Example 2

An organic light-emitting device (green light emission) was manufactured using the same method as in Example 1, except that Compound 20 was used instead of Compound 19 as a host when forming the emission layer.

Example 3

An organic light-emitting device (green light emission) was manufactured using the same method as in Example 1, except that Compound 23 was used instead of Compound 19 as a host when forming the emission layer.

Example 4

Except that the thickness of the hole transport layer was changed to 135 nm, the thickness of the emission layer was changed to 40 nm, and when forming the emission layer, compound 18 was used instead of compound 19 as a host, and PtOEP was used instead _{of Ir(ppy) 3 as a dopant.} , Using the same method as in Example 1, an organic light emitting device (red light emission) was manufactured.

Example 5

An organic light-emitting device (red light emission) was manufactured using the same method as in Example 4, except that Compound 22 was used instead of Compound 18 as a host when forming the emission layer.

Example 6

An organic light-emitting device (red light emission) was manufactured using the same method as in Example 4, except that Compound 25 was used instead of Compound 18 as a host when forming the emission layer.

Comparative Example 1

An organic light-emitting device was manufactured using the same method as in Example 1, except that CBP was used instead of Compound 19 as a host when forming the emission layer.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Example 4, except that CBP was used instead of Compound 18 as a host when forming the emission layer.

Evaluation Example 1

The driving voltage, current density, luminance, efficiency, color purity, and lifetime (LT ₉₇ ) of the organic light emitting devices fabricated in Examples 1 to 6 and Comparative Examples 1 and 2 were measured using the following method, and the results are shown in Table 1 and It is shown in 2:

-Color coordinates: Power was supplied from a current-voltmeter (Kethley SMU 236) and measured using a luminance meter PR650.

-Luminance: Power was supplied from a current-voltmeter (Kethley SMU 236) and measured using a luminance meter PR650.

-Efficiency: Power was supplied from a current-voltmeter (Kethley SMU 236) and measured using a luminance meter PR650.

Meanwhile, the lifetime LT97 represents the time (hr) it takes for the luminance to become 97% when the initial luminance (at 10mA/cm ^{2) is 100%.}

Host Dopant Driving voltage
(V) Current density
(mA/cm ² ) Luminance
(cd/m ² ) efficiency
(cd/A) Example 1 Compound 19 Ir(ppy) ₃ 5.7 10 5,950 59.5 Example 2 Compound 20 Ir(ppy) ₃ 5.8 10 6,455 64.5 Example 3 Compound 23 Ir(ppy) ₃ 5.9 10 6,601 66.0 Example 4 Compound 18 PtOEP 6.3 10 3,250 32.5 Example 5 Compound 22 PtOEP 6.6 10 2,974 29.7 Example 6 Compound 25 PtOEP 6.5 10 3,174 31.7 Comparative Example 1 CBP Ir(ppy) ₃ 6.8 10 4,766 47.7 Comparative Example 2 CBP PtOEP 7.3 10 2,212 22.1

Host material Dopant Luminous color Color coordinates LT97
(hr/@10mA/cm ² ) Example 1 Compound 19 Ir(ppy) ₃ green 0.25, 0.73 80 Example 2 Compound 20 Ir(ppy) ₃ green 0.26, 0.72 72 Example 3 Compound 23 Ir(ppy) ₃ green 0.25, 0.71 81 Example 4 Compound 18 PtOEP Red 0.65, 0.34 118 Example 5 Compound 22 PtOEP Red 0.68, 0.30 95 Example 6 Compound 25 PtOEP Red 0.64, 0.30 98 Comparative Example 1 CBP Ir(ppy) ₃ green 0.25, 0.70 61 Comparative Example 2 CBP PtOEP Red 0.67, 0.32 89

From Tables 1 and 2 above, the driving voltage, efficiency, luminance, color purity, and lifetime of the organic light-emitting devices of Examples 1 to 6 are determined by Compared to that, it can be confirmed that it is excellent.

11: substrate
13: first electrode
15: organic layer
17: second electrode

Claims (18)

Heterocyclic compounds represented by the following formulas 1A(1), 1A(2), or 1A(3):
<Formula 1A(1)><Formula1A(2)>

<Formula 1A(3)>

In the above formula,
Ar ₁ and Ar ₂ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ A cycloalkenylene group, a C ₂ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, and a substituted or unsubstituted C ₂ -C ₆₀ heteroarylene group;
Y ₁₁ is O, S, N(Z ₁₃ ) or C(Z ₁₄ )(Z ₁₅ );
The R ₁ to R ₅ , R ₁₂ , Z ₁ , Z ₂ , Z ₁₁ and Z ₁₃ to Z ₁₅ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyanide No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted A C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or Unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted Or an unsubstituted C ₂ -C ₆₀ heteroaryl group, -N(Q ₁ )(Q ₂ ) and -Si(Q ₃ )(Q ₄ )(Q ₅ ) (wherein, Q ₁ and Q ₂ are independent of each other As, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ heterocyclo An alkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, and a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group; The Q ₃ to Q ₅ are independently of each other, hydrogen, deuterium,- F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₂ -C ₁₀ heterocyclo Alkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, C ₂ -C ₁₀ hetero Selected from a cycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, and a substituted or unsubstituted C ₂ -C ₆₀ heteroaryl group);
n and m are each independently selected from an integer of 0 to 5;
d1 is selected from an integer of 1 to 3;
d2 is selected from an integer of 1 to 4;
e3 is selected from an integer of 1 to 3;
e4 is selected from an integer of 1 to 4;
a and b are each independently selected from an integer of 1 to 4. delete The method of claim 1,
The Ar ₁ and Ar ₂ are independently of each other,
Phenylene group (phenylene), pentalenylene group (pentalenylene), indenylene group (indenylene), naphthylene group (naphtylene), azulenylene group (azulenylene), heptalenylene group (heptalenylene), indacenylene group (indacenylene), Acenaphthylene group (acenaphtylene), fluorenylene group (fluorenylene), spiro-fluorenylene group, phenalenylene group (phenalenylene), phenanthrenylene group (phenanthrenylene), anthrylene group (anthrylene), fluoranthenylene group (fluoranthenylene), triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenyl Pentaphenylene, hexacenylene, pyrrolylene, imidazolylene, pyrazolylene, pyridinylene, pyrazinylene, pyrimidi Nylene group (pyrimidinylene), pyridazinylene group (pyridazinylene), isoindolylene group (isoindolylene), indolylene group (indolylene), indazolylene group (indazolylene), purinylene group (purinylene), quinolinylene group (quinolinylene) , Benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinolinylene, Carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene group (ph enanthrolinylene), phenazinylene, benzooxazolylene, benzoimidazolylene, furanylene, benzofuranylene, thiophenylene, benzo Thiophenylene, thiazolylene, isothiazolylene, benzothiazolylene, isoxazolylene, oxazolylene, triazolylene, tetra Zolylene, oxadiazolylene, triazinylene, benzooxazolylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene and di Benzosilolylene group (dibenzosilolylene); And
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts; C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group; And deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylflu At least one of orenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group A substituted, C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heteroaryl group; Phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptarenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spy substituted with at least one substituent selected from among Ro-fluorenylene group, phenalenylene group, phenanthrenylene group, anthrylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylene group , Pentaphenylene group, hexaenylene group, pyrroleylene group, imidazolylene group, pyrazolylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, inda Zolylene group, furinylene group, quinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, sinolinylene group, carbazolylene group, phenanthridinyl Ethylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzooxazolylene group, benzoimidazolylene group, furanylene group, benzofuranylene group, thiophenylene group, benzothiophenylene group, thiazolylene group, iso Thiazolylene group, benzothiazolylene group, isoxazolylene group, oxazolylene group, triazolylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, benzoxazolylene group, dibenzofuranylene group, dibenzothiophenyl A ren group, a benzocarbazolylene group, and a dibenzosilolylene group; A heterocyclic compound selected from The method of claim 1,
Ar ₁ and Ar ₂ are each independently a heterocyclic compound represented by one of the following Formulas 2-1 to 2-29:

In Formulas 2-1 to 2-29,
Y ₁ is O, S, C(Z ₃ )(Z ₄ ) or N(Z ₅ );
Z ₁ to Z ₅ are independently of each other,
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;
C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluore At least one of a nil group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group A substituted, C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heteroaryl group; And
-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group Or a C ₂ -C ₂₀ heteroaryl group); Is selected from;
d1 is an integer of 1 to 4, d2 is an integer of 1 to 3, d3 is an integer of 1 to 6, d4 is an integer of 1 to 8, d5 is 1 or 2, * is a heterocycle in Formula 1 A binding site with a core, a binding site with a neighboring Ar ₁ or a binding site with a neighboring Ar ₂ , *'is _{a binding site with a neighboring Ar 1} in Formula 1, a binding site with a neighboring Ar ₂ , R ₁₁ It is a binding site with or a binding site with _{R 12.} The method of claim 4,
Z ₁ to Z ₅ are independently of each other,
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;
Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, Carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; And
-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group Group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group , Or isoquinolinyl group); A heterocyclic compound selected from among. The method of claim 1,
Ar ₁ and Ar ₂ are each independently a heterocyclic compound represented by one of the following Formulas 3-1 to 3-23:

* Is a bonding site with a heterocyclic core in Formula 1, a bonding site with an adjacent Ar ₁ , or a bonding site with an _{adjacent Ar 2;
*'is a binding site with a neighboring Ar 1} in Formula 1, a binding site with a neighboring Ar ₂ , a binding site with R ₁₁ or a binding site with _{R 12.} The method of claim 1,
R ₁₂ is phenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, indacenyl, acenaph Acenaphtyl, fluorenyl, spiro-fluorenyl, phenalenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenyl Renyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group (chrysenyl), naphthacenyl group (naphthacenyl), pisenyl group (picenyl), perylenyl group (perylenyl), pentaphenyl group (pentaphenyl), hexasenyl group (hexacenyl), pyrroleyl group (pyrrolyl), imidazolyl group (imidazolyl), pyrazolyl group (pyrazolyl), pyridinyl group (pyridinyl), pyrazinyl group (pyrazinyl), pyrimidinyl group (pyrimidinyl), pyridazinyl group ( pyridazinyl), isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, benzoquinolinyl, phthalazinyl ), naphthyridinyl, quinoxalinyl, quinazolinyl, cinolinyl, carbazolyl, phenanthridinyl, acridinyl ), phenanthrolinyl, phenazinyl, benzooxazolyl, benzoimidazolyl, furanyl, benzofuranyl, thiophenyl , Benzothiophenyl group (benzoth iophenyl), thiazolyl, isothiazolyl, benzothiazolyl, isoxazolyl, oxazolyl, triazolyl, tetrazolyl, oxa Diazolyl group (oxadiazolyl), triazolyl group (triazinyl), benzooxazolyl group (benzooxazolyl), dibenzofuranyl group (dibenzofuranyl), dibenzothiophenyl group (dibenzothiophenyl), benzocarbazolyl group and dibenzosilolyl group (dibenzosilolyl) ;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group; Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts; C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group; And deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylflu At least one of orenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group A substituted, C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heteroaryl group; Phenyl group, pentarenyl group, indenyl group, naphthyl group, azulenyl group, heptarenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, p Nalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, hexasenyl group, pyrroleyl group , Imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, benzoquinolinyl group, p Thalasinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group , Furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group , Triazinyl group, benzoxazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzosilolyl group; And
-N(Q ₁ )(Q ₂ ) (here, Q ₁ and Q ₂ are each independently a phenyl group, pentarenyl group, indenyl group, naphthyl group, azulenyl group, heptarenyl group, indacenyl group, acenaphthyl group , Fluorenyl group, spiro-fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, Perylenyl group, pentaphenyl group, hexaenyl group, pyrroleyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, Purinyl group, quinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, Phenazinyl group, benzoxazolyl group, benzoimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group , Triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, benzooxazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzosilolyl group);
Selected from among, heterocyclic compounds. The method of claim 1,
R ₁₂ is a heterocyclic compound represented by one of the following formulas 4-1 to 4-18:

In Formulas 4-1 to 4-18,
Y ₁₁ is O, S, N(Z ₁₃ ) or C(Z ₁₄ )(Z ₁₅ );
The Z ₁₁ to Z ₁₅ are independently of each other,
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;
C ₆ -C ₂₀ aryl group and C ₂ -C ₂₀ heteroaryl group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluore At least one of a nil group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group A substituted, C ₆ -C ₂₀ aryl group and a C ₂ -C ₂₀ heteroaryl group; And
-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a C ₆ -C ₂₀ aryl group Or a C ₂ -C ₂₀ heteroaryl group); Is selected from;
Q ₁ and Q ₂ are each independently a phenyl group, pentarenyl group, indenyl group, naphthyl group, azulenyl group, heptarenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl group, p. Nalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, pisenyl group, perylenyl group, pentaphenyl group, hexasenyl group, pyrroleyl group , Imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, benzoquinolinyl group, p Thalasinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzoimidazolyl group , Furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group , Triazinyl group, benzooxazolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group and dibenzosilolyl group;
e1 is selected from an integer of 1 to 5, e2 is selected from an integer of 1 to 7, e3 is selected from an integer of 1 to 3, e4 is selected from an integer of 1 to 4, and e5 is 1 or 2 , e6 is selected from an integer of 1 to 6, and * is a bonding site with neighboring atoms. The method of claim 8,
The Z ₁₁ to Z ₁₅ are independently of each other,
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;
Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, Carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; And
-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group Group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group , Or isoquinolinyl group); A heterocyclic compound selected from among. The method of claim 1,
R ₁ to R ₅ are independently of each other,
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;
Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, Carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; And
-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group Group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group , Or isoquinolinyl group); Selected from among, heterocyclic compounds. The method of claim 1,
Ar ₂ is
A phenylene group and a naphthalene group; And
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenylene group and a naphthalene group substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group and an isoquinolinyl group; Is selected from;
m is 0, 1 or 2;
R ₁₂ is a phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinoli Nil group, isoquinolinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group and triazinyl group; And
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , Pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group and isoquinolinyl group substituted with at least one of, phenyl group, naphthyl group, fluorenyl group, spiro-fluore Nyl group, phenanthrenyl group, anthracenyl group, pyrenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinazolinyl group, carbazolyl group, phenanthri Denyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group and triazinyl group; Is selected from;
R ₁ to R ₅ are independently of each other,
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or a salt thereof, a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or _{A C 1} -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one of its salts;
Phenyl group, naphthyl group, anthracenyl group, fluorenyl group, carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or Salts thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group , A phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, substituted with at least one of a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group, Carbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, and isoquinolinyl group; And
-Si (Q ₁₃ ) (Q ₁₄ ) (Q ₁₅ ) (wherein, the Q ₁₃ to Q ₁₅ are each independently a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group Group, fluorenyl group, dimethylfluorenyl group, diphenylfluorenyl group, carbazolyl group, phenylcarbazolyl group, pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group , Or isoquinolinyl group); Is selected from;
a and b are each independently selected from an integer of 1 to 4, a heterocyclic compound. The method of claim 1,
In Formulas 1A(1), 1A(2) and 1A(3), R ₁ to R ₅ are hydrogen, a heterocyclic compound. The method of claim 1,
A heterocyclic compound, which is one of the following compounds 2,5,6,9,10,13,14,18 to 20, 22 to 31 and 34 to 52:

A first electrode; A second electrode facing the first electrode; And an organic layer interposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer contains at least one heterocyclic compound of any one of claims 1 and 3 to 13, Organic light emitting device. The method of claim 14,
The organic layer includes: i) at least one of a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function simultaneously, a buffer layer, and an electron blocking layer between the first electrode and the emission layer, ii ) An organic light-emitting device comprising at least one of a hole blocking layer, an electron transport layer, and an electron injection layer between the emission layer and the second electrode. The method of claim 14,
The organic light-emitting device, wherein the heterocyclic compound is present in the emission layer. The method of claim 16,
The heterocyclic compound included in the emission layer serves as a host, and the emission layer further includes a dopant. The method of claim 17,
The organic light-emitting device, wherein the dopant included in the emission layer includes an organometallic compound including at least one of Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, and Tm.

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