KR102400484B1 - Amine-based compound and organic light-emitting device comprising the same - Google Patents

Abstract

An amine-based compound and an organic light emitting device including the same are disclosed.

Description

An amine-based compound and an organic light-emitting device including the same

It relates to an amine-based compound and an organic light-emitting device including the same.

An organic light emitting device is a self-luminous device, and compared to a conventional device, a viewing angle is wide and the contrast is excellent, and the response time is fast, and the luminance, driving voltage and response speed characteristics are excellent, and it is multicolored. It is possible.

In the organic light emitting device, a first electrode is disposed on a substrate, and a hole transport region, a light emitting layer, an electron transport region, and a second electrode are sequentially formed on the first electrode. can have a structure with Holes injected from the first electrode move to the emission layer via the hole transport region, and electrons injected from the second electrode move to the emission layer via the electron transport region. Carriers such as holes and electrons recombine in the emission layer region to generate excitons. Light is generated as this exciton changes from an excited state to a ground state.

An amine-based compound and an organic light emitting device including the same are provided.

According to one aspect, there is provided an amine-based compound represented by the following Chemical Formula 1A or 1B:

<Formula 1A>

<Formula 1B>

In Formulas 1A and 1B,

A ₁ to A ₅ are each independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group;

X ₁ is O, S, N-(L ₁ ) _a1- (R ₁ ) _b1 or C(R ₉ )(R ₁₀ ),

X ₂ is O, S or C(R ₁₁ )(R ₁₂ ),

L ₁ to L ₃ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

a1 to a3 are each independently selected from an integer of 1 to 5;

R ₁ to R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, A substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group , substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ - C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or Unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -B(Q ₁ )(Q ₂ ) and -C(=O)(Q ₁ ),

R ₉ and R ₁₀ and/or R ₁₁ and R ₁₂ are optionally linked to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group can be formed,

b1 to b3 and b5 to b8 are each independently selected from an integer of 1 to 10;

b4 is selected from an integer of 1 to 3,

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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ an alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )( Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ) substituted with at least one selected from a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -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, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group and a terphenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ Heterocycloalkenyl group, C 6 -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, _monovalent non-aromatic condensed polycyclic group, 1 Condensed non-aromatic heteropolycyclic group, biphenyl group, terphenyl group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O)(Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), C ₃ -C substituted with at least one selected from ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );

is selected from

The Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl group is selected from a C ₆ -C ₆₀ aryl group substituted with a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group and a terphenyl group.

According to another aspect, the first electrode; a second electrode opposite to the first electrode; and an organic layer disposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer includes at least one kind of the amine-based compound.

The organic light-emitting device including the amine-based compound may have a low driving voltage, high efficiency, long lifespan, and high maximum quantum efficiency.

1 to 4 are views each schematically showing a structure of an organic light emitting diode according to an exemplary embodiment.

Since the present invention can apply various transformations and can have various implementations, specific implementations are illustrated in the drawings and described in detail in the detailed description. Effects and features of the present invention, and a method of achieving them, will become apparent with reference to the embodiments described below in detail in conjunction with the drawings. However, the present invention is not limited to the embodiments disclosed below and may be implemented in various forms.

Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings, and when described with reference to the drawings, the same or corresponding components are given the same reference numerals, and the overlapping description thereof will be omitted. .

In the following embodiments, the singular expression includes the plural expression unless the context clearly dictates otherwise.

In the following embodiments, the terms include or have means that the features or components described in the specification are present, and the possibility that one or more other features or components will be added is not excluded in advance.

In the following embodiments, when a part such as a film, region, or component is on or on another part, not only when it is directly on the other part, but also another film, region, component, etc. is interposed therebetween. Including cases where there is

In the drawings, the size of the components may be exaggerated or reduced for convenience of description. For example, since the size and thickness of each component shown in the drawings are arbitrarily indicated for convenience of description, the present invention is not necessarily limited to the illustrated bar.

The amine-based compound is represented by the following Formula 1A or 1B:

<Formula 1A>

<Formula 1B>

In Formulas 1A and 1B, A ₁ to A ₅ may be each independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group.

In one embodiment, in Formulas 1A and 1B, A ₁ to A ₅ may each independently represent a benzene group, an indene group, a naphthalene group, an anthracene group, a fluorene group, a phenanthrene group, a triphenylene group, and a pyrene group group, chrysene group, naphthacene group, pyrrole group, imidazole group, pyrazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, indole group, isoindole group, indazole group, quinoline group, iso Quinoline group, benzoquinoline group, naphthyridine group, quinoxaline group, quinazoline group, cinoline group, carbazole group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group , furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, isoxazole group, oxazole group, triazole group, oxadiazole group, tri It may be selected from an azine group, a benzoxazole group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group and a dibenzocarbazole group.

For example, in Formulas 1A and 1B, A ₁ to A ₅ may each independently represent a benzene group, an indene group, a naphthalene group, an anthracene group, a fluorene group, a phenanthrene group, a pyridine group, a pyrimidine group, and a pyrazine group , but may be selected from a pyridazine group and a carbazole group, but is not limited thereto.

As another example, in Formulas 1A and 1B, A ₁ to A ₅ may be each independently selected from a benzene group and a naphthalene group, but are not limited thereto.

As another example, in Formulas 1A and 1B, A ₁ to A ₅ may each independently represent a benzene group, but is not limited thereto.

In Formulas 1A and 1B, X ₁ is O, S, N-(L ₁ ) _a1- (R ₁ ) _b1 or C(R ₉ )(R ₁₀ ), and X ₂ is O, S, or C(R ₁₁ ) ) (R ₁₂ ).

In one embodiment, in Formulas 1A and 1B, X ₁ is N-(L ₁ ) _a1- (R ₁ ) _b1 , and X ₂ is O, S, or C(R ₁₁ )(R ₁₂ ); Alternatively, X ₁ may be O, and X ₂ may be C(R ₁₁ )(R ₁₂ ), but is not limited thereto.

In Formulas 1A and 1B, L ₁ to L ₃ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group can be selected.

In one embodiment, in Formulas 1A and 1B, L ₁ to L ₃ are each independently a single bond, a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, and an indacene group , acenaphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group , naphthacene group, picene group, perylene group, pentaphenylene group, hexacene group, pyrrole group, imidazole group, pyrazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, isoindole group, Indole group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinoline group, carbazole group, phenanthridine group , acridine group, phenanthroline group, phenazine group, benzimidazole group, furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, Isoxazole group, oxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, benzooxazole group, dibenzofuran group, dibenzothiophene group, benzocarbazole group and dibenzocarba sol group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ A benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, substituted with at least one selected from an alkoxy group, a C ₆ -C ₂₀ aryl group, and a C ₁ -C ₂₀ heteroaryl group , acenaphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthrene group, triphenylene group, pyrene group, chrysene group , naphthacene group, picene group, perylene group, pentaphenylene group, hexacene group, pyrrole group, imidazole group, pyrazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, isoindole group, Indole group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinoline group, carbazole group, phenanthridine group , acridine group, phenanthroline group, phenazine group, benzimidazole group, furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, Isoxazole group, oxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, benzooxazole group, dibenzofuran group, dibenzothiophene group, benzocarbazole group and dibenzocarba sol group; may be selected from, but is not limited thereto.

In another embodiment, in Formulas 1A and 1B, L ₁ to L ₃ may be each independently selected from a single bond and a group represented by Formulas 3-1 to 3-46:

In Formulas 3-1 to 3-46,

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

Z ₁ To Z ₇ are each independently, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, spiro-bi Fluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group Nyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and - Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ),

d2 is selected from an integer of 0 to 2, and when d2 is 2 or more, Z ₁ of 2 or more are the same as or different from each other,

d3 is selected from an integer of 0 to 3, and when d3 is 2 or more, Z ₁ and Z ₂ of 2 or more are the same as or different from each other,

d4 is selected from an integer of 0 to 4, and when d4 is 2 or more, Z ₁ and Z ₂ of 2 or more are the same as or different from each other,

**d5 is selected from an integer of 0 to 5, and when d5 is 2 or more, Z ₁ and Z ₂ of 2 or more are the same as or different from each other,

d6 is selected from an integer of 0 to 6, and when d6 is 2 or more, Z ₁ and Z ₂ of 2 or more are the same as or different from each other,

d8 is selected from an integer of 0 to 8, and when d8 is 2 or more, Z ₁ of 2 or more are the same as or different from each other,

*** and *' are binding sites with neighboring atoms.

For example, L ₁ to L ₃ may be each independently selected from the group represented by a single bond, Formulas 3-1 to 3-7, 3-31 to 3-34, 3-42, and 3-43 there is.

As another example, L ₁ to L ₃ may be each independently selected from a single bond and a group represented by Formulas 3-1, 3-2, and 3-34.

In one embodiment, in Formulas 3-1 to 3-46, Z ₁ to Z ₇ are each independently hydrogen, deuterium, -F, cyano group, methyl group, ethyl group, n-propyl group, tert-butyl group , may be selected from a phenyl group and a naphthyl group, but is not limited thereto.

In another embodiment, in Formulas 1A and 1B, L ₁ to L ₃ may be each independently selected from a single bond and a benzene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ a benzene group substituted with at least one selected from an alkoxy group, a C ₆ -C ₂₀ aryl group, and a C ₁ -C ₂₀ heteroaryl group; may be selected from, but is not limited thereto.

In Formulas 1A and 1B, a1 to a3 may be each independently selected from an integer of 1 to 5. a1 indicates the number of L ₁ , and when a1 is 2 or more, two or more L ₁ may be the same or different from each other. Descriptions of a2 and a3 may be understood with reference to the description of a1.

In one embodiment, in Formulas 1A and 1B, a1 to a3 may be each independently selected from an integer of 1 to 3.

For example, a1 to a3 may be 1, but is not limited thereto.

In Formulas 1A and 1B, R ₁ to R ₁₂ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydra Zino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl 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 ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or an unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si (Q ₁ )(Q ₂ )(Q ₃ ), -B(Q ₁ )(Q ₂ ) and -C(=O)(Q ₁ ),

R ₉ and R ₁₀ and/or R ₁₁ and R ₁₂ are optionally linked to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic groups can be formed.

In one embodiment, in Formulas 1A and 1B, R ₁ and R ₂ are each independently a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and 1 is a non-aromatic condensed heteropolycyclic group; and

Deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non- C ₆ -C ₆₀ substituted with at least one of a condensed aromatic polycyclic group, a condensed monovalent non-aromatic heterocondensed polycyclic group, -N(Q ₃₁ )(Q ₃₂ ) and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) an aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group; can be selected from

In another embodiment, in Formulas 1A and 1B, R ₁ and R ₂ are each independently a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group (azulenyl), heptalenyl group, indacenyl group (indacenyl), acenaphthyl group, fluorenyl group (fluorenyl), spiro-fluorenyl group, spiro-bifluorenyl group, benzofluorene Nyl group, phenalenyl group (phenalenyl), phenanthrenyl group (phenanthrenyl), anthracenyl group (anthracenyl), fluoranthenyl group (fluoranthenyl), triphenylenyl group (triphenylenyl), pyrenyl group (pyrenyl), chrysenyl group ( chrysenyl), naphthacenyl, picenyl, perylenyl, pentaphenyl, hexacenyl, pyrrolyl, imidazolyl, Pyrazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, ind Zolyl group (indazolyl), purinyl group (purinyl), quinolinyl group (quinolinyl), isoquinolinyl group (isoquinolinyl), benzoquinolinyl group (benzoquinolinyl), phthalazinyl group (phthalazinyl), naphthyridinyl group (naphthyridinyl), quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, benzooxazolyl, ben Zimidazolyl, furanyl, benzofuranyl, thiophenyl, benzothiophenyl, thiazolyl, isothiazolyl, benzo Thiazolyl group (benzothiazolyl), isoxazolyl group (isoxazolyl), oxazolyl group (oxazolyl), triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, benzooxazolyl group ), a dibenzofuranyl group (dibenzofuranyl), a dibenzothiophenyl group (dibenzothiophenyl), a benzocarbazolyl group and a dibenzocarbazolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ A phenyl group, _{a pentarenyl} group, an indenyl group, a naphthyl group, an azulenyl group, a _heptarenyl group, an _indacenyl group, Acenaphthyl group, fluorenyl group, spiro-fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, Sinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzooxazolyl group, benzimidazolyl group, furanyl group, benzofuranyl group, thiophenyl group, benzothiophenyl group, thia Zolylene group, isothiazolyl group, benzothiazolyl group, isoxazolyl group, oxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, benzoxazolyl group, dibenzofuranyl group, dibenzo a thiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group; may be selected from, but is not limited thereto.

For example, in Formulas 1A and 1B, R ₁ and R ₂ may be each independently selected from the group represented by Formulas 5-1 to 5-79, but are not limited thereto:

In Formulas 5-1 to 5-79,

Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ), or Si(Z ₃₆ )(Z ₃₇ ),

Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, spiro-bi Fluorenyl group, spiro-fluorene-benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenane selected from a trollinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ );

Z ₃₃ and Z ₃₄ may be optionally linked to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

e2 is selected from an integer of 0 to 2, and when e2 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,

e3 is selected from an integer of 0 to 3, and when e3 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,

e4 is selected from an integer of 0 to 4, and when e4 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,

e5 is selected from an integer of 0 to 5, and when e5 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,

e6 is selected from an integer of 0 to 6, and when e6 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,

e7 is selected from an integer of 0 to 7, and when e7 is 2 or more, Z ₃₁ of 2 or more are the same as or different from each other,

e9 is selected from an integer of 0 to 9, and when e9 is 2 or more, Z ₃₁ of 2 or more are the same as or different from each other,

* is a binding site with a neighboring atom.

For example, in Formulas 1A and 1B, R ₁ and R ₂ may be each independently selected from the group represented by Formulas 5-1 to 5-20, but are not limited thereto.

As another example, in Formulas 1A and 1B, R ₁ and R ₂ may be each independently selected from the group represented by Formulas 5-1 to 5-3, 5-13 to 5-16 and 5-20. However, the present invention is not limited thereto.

In one embodiment, in Formulas 5-1 to 5-79, Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, -F, cyano group, methyl group, ethyl group, n-propyl group, tert-butyl group , may be selected from a phenyl group and a naphthyl group, but is not limited thereto.

In another embodiment, in Formulas 1A and 1B, R ₁ and R ₂ may be each independently selected from Formulas 6-1 to 6-42, but are not limited thereto:

In Formulas 6-1 to 6-42,

"Ph" represents a phenyl group,

* is a binding site with a neighboring atom.

In Formulas 1A and 1B, R ₃ to R ₁₂ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ) and -N(Q ₁ )(Q ₂ );

deuterium, -F, -Cl, -Br, -I, a C ₁ -C ₆₀ alkyl group and a C ₁ -C ₆₀ alkoxy group substituted with at least one of a cyano group and a nitro group; and

Deuterium, -F, -Cl, -Br, -I, a cyano group, a nitro group, a methyl group, a methoxy group, a phenyl group, a naphthyl group and at least one substituted with a biphenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed polycyclic group; may be selected from, but is not limited thereto.

In another embodiment, R ₃ to R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group group, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, may be selected from a phenyl group and a biphenyl group, but is not limited thereto.

In Formulas 1A and 1B, b1 to b3 and b5 to b8 may be each independently selected from an integer of 1 to 10, and b4 may be selected from an integer of 1 to 3.

b1 represents the number of R ₁ , and when b1 is 2 or more, two or more R ₁ may be the same or different from each other. Descriptions of b2 to b8 may be understood with reference to the description of b1.

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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ an alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )( Q ₁₂ ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ) substituted with at least one selected from a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -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, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group and a terphenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ Alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ Heterocycloalkenyl group, C 6 -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, _monovalent non-aromatic condensed polycyclic group, 1 Condensed non-aromatic heteropolycyclic group, biphenyl group, terphenyl group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ) ), -C(=O)(Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), C ₃ -C substituted with at least one selected from ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, biphenyl group and terphenyl group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );

is selected from

The Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl group may be selected from a C ₆ -C ₆₀ aryl group substituted with a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero polycyclic group, a biphenyl group and a terphenyl group.

** In one embodiment, the amine-based compound represented by Formula 1A or 1B may be represented by Formula 1C or 1D, but is not limited thereto:

<Formula 1C>

<Formula 1D>

In Formulas 1C and 1D,

The definitions for X ₁ , X ₂ , L ₁ to L ₃ , a1 to a3 , R ₁ to R ₁₂ and b1 and b2 are the same as those described in the description for Formulas 1A and 1B above,

b4, b6 and b8 are each independently selected from an integer of 1 to 3,

b3, b5 and b7 are each independently selected from an integer of 1 to 4.

In another embodiment, the amine compound represented by Formula 1A or 1B may be represented by any one selected from Formulas 1A-1 to 1A-4 and 1B-1 to 1B-16, but is not limited thereto:

<Formula 1A-1>

<Formula 1A-2>

<Formula 1A-3>

<Formula 1A-4>

<Formula 1B-1>

<Formula 1B-2>

<Formula 1B-3>

<Formula 1B-4>

<Formula 1B-5>

<Formula 1B-6>

<Formula 1B-7>

<Formula 1B-8>

<Formula 1B-9>

<Formula 1B-10>

<Formula 1B-11>

<Formula 1B-12>

*

<Formula 1B-13>

<Formula 1B-14>

<Formula 1B-15>

<Formula 1B-16>

In Formulas 1A-1 to 1A-4 and 1B-1 to 1B-16,

The definitions for X ₁ , X ₂ , L ₁ to L ₃ , a1 to a3 and R ₁ to R ₁₂ and b1 and b2 are the same as those described in the description for Formulas 1A and 1B above,

b4, b6 and b8 are each independently selected from an integer of 1 to 3,

b3, b5 and b7 are each independently selected from an integer of 1 to 4.

In one embodiment, in Formulas 1A-1 to 1A-4 and 1B-1 to 1B-16, X ₁ is N-(L ₁ ) _a1- (R ₁ ) _b1 , and X ₂ is O, S or C(R ₁₁ )(R ₁₂ );

X ₁ is O and X ₂ is C(R ₁₁ )(R ₁₂ ); or

X ₁ may be C(R ₉ )(R ₁₀ ), and X ₂ may be C(R ₁₁ )(R ₁₂ ), but is not limited thereto.

In another embodiment, in Formulas 1A-1 to 1A-4 and 1B-1 to 1B-16, L ₁ to L ₃ may be each independently selected from a single bond and a benzene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ a benzene group substituted with at least one selected from an alkoxy group, a C ₆ -C ₂₀ aryl group, and a C ₁ -C ₂₀ heteroaryl group; may be selected from, but is not limited thereto.

In another embodiment, in Formulas 1A-1 to 1A-4 and 1B-1 to 1B-16, R ₁ and R ₂ may be each independently selected from Formulas 6-1 to 6-42, , but is not limited thereto.

In one embodiment, in Formulas 1A and 1B, R ₉ and R ₁₀ and/or R ₁₁ and R ₁₂ may be bonded to each other to be represented by any one of Formulas 7-1 to 7-3 below:

In Formulas 7-1 to 7-3,

Z ₅₁ and Z ₅₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, spiro-bi Fluorenyl group, spiro-fluorene-benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenane selected from a trollinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ );

n1 is selected from an integer of 1 to 8,

n2 is selected from an integer of 1 to 10,

n3 and n4 are each independently selected from an integer of 1 to 4,

* is a carbon atom to which R ₉ and R ₁₀ or R ₁₁ and R ₁₂ are bonded.

In one embodiment, the amine compound represented by Formula 1A or 1B may be selected from the following compounds 1 to 284, but is not limited thereto:

The amine-based compound represented by Formula 1A or 1B has a molecular structure with large steric hindrance by satisfying a structure in which a substituent represented by Formula 1A' is connected to nitrogen at a specific position. Accordingly, the amine-based compound may maintain an optimal intermolecular density. In addition, it is possible to have excellent hole mobility through an increase in interaction by a lone pair of oxygen atoms that are less sterically covered.

<Formula 1A'>

In addition, since the amine-based compound includes one amine group in the molecule, it has an appropriate energy level compared to a compound including two or more amine groups. Accordingly, hole mobility may be improved by reducing hole injection and hole injection barriers.

Accordingly, an electronic device including the amine compound, for example, an organic light emitting device, may have a low driving voltage, high efficiency, and long lifespan.

A method of synthesizing the amine-based compound represented by Formula 1A or 1B may be recognized by those skilled in the art with reference to Examples to be described later.

At least one of the amine-based compounds represented by Formula 1A or 1B may be used between a pair of electrodes of the organic light emitting diode. For example, the amine-based compound may be included in at least one of a hole transport region, an electron transport region, and a light emitting layer. Alternatively, the amine-based compound represented by Formula 1A or 1B may be used as a material for a capping layer positioned outside a pair of electrodes of the organic light-emitting device.

Accordingly, the first electrode; a second electrode opposite to the first electrode; and an organic layer disposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer includes at least one amine compound represented by Formula 1A or 1B.

In the present specification, "(organic layer) includes one or more amine compounds" means "(organic layer) is one type of amine compound belonging to the scope of Chemical Formula 1A or 1B, or belonging to the scope of Chemical Formula 1A or 1B. may include two or more different amine-based compounds.”

* For example, the organic layer may include only Compound 1 as the amine-based compound. In this case, the compound 1 may be present in the emission layer of the organic light emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the amine-based compound. In this case, the compound 1 and the compound 2 are present in the same layer (for example, both the compound 1 and the compound 2 may be present in the light emitting layer) or exist in different layers (eg, the compound 1 is the light emitting layer) and the compound 2 may be present in the electron transport layer).

According to one embodiment, the first electrode is an anode, the second electrode is a cathode, the organic layer is disposed between the hole transport region and the light emitting layer and the second electrode disposed between the first electrode and the light emitting layer and an electron transport region, wherein the hole transport region comprises a hole injection layer, a hole transport layer, a light emitting auxiliary layer, an electron blocking layer, or any combination thereof, wherein the electron transport region is a hole blocking layer, It may include an electron injection layer or any combination thereof.

In one embodiment, the hole transport region may include the amine-based compound.

In another embodiment, the hole transport region may include a hole injection layer and a hole transport layer, and at least one of the hole injection layer and the hole transport layer may include the amine compound.

In another embodiment, the hole transport region may include a hole transport layer, and the hole transport layer may include the amine compound.

In an embodiment, the hole transport region may include a p-dopant, and the LUMO energy level of the p-dopant may be -3.5 eV or less.

For example, the p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound.

For example, the hole transport region may include a hole injection layer, and the hole injection layer may include the p-dopant.

In one embodiment, the light emitting layer may include at least one of a styryl-based compound, an anthracene-based compound, a pyrene-based compound, and a spiro-bifluorene-based compound.

In the present specification, the term “organic layer” refers to a single and/or a plurality of all layers interposed between the first electrode and the second electrode of the organic light emitting device. The material included in the layer of the "organic layer" is not limited to an organic material.

[Description of Fig. 1]

1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The organic light emitting device 10 includes a first electrode 110 , an organic layer 150 , and a second electrode 190 .

Hereinafter, the structure and manufacturing method of the organic light emitting device 10 according to an embodiment of the present invention will be described with reference to FIG. 1 .

[First electrode 110]

A substrate may be additionally disposed on a lower portion of the first electrode 110 or an upper portion of the second electrode 190 of FIG. 1 . As the substrate, a glass substrate or a plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, handling easiness and water resistance may be used.

The first electrode 110 may be formed, for example, by providing a material for the first electrode on the upper portion of the substrate using a deposition method or a sputtering method. When the first electrode 110 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 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In order to form the first electrode 110 which is a transmissive electrode, the material for the first electrode is indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and any thereof. It may be selected from a combination of, but is not limited thereto. Alternatively, in order to form the first electrode 110 that is a transflective electrode or a reflective electrode, the material for the first electrode is magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li). ), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combination thereof, but is not limited thereto.

The first electrode 110 may have a single-layer structure that is a single layer or a multi-layer structure having a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto.

[Organic layer 150]

An organic layer 150 is disposed on the first electrode 110 . The organic layer 150 includes a light emitting layer.

The organic layer 150 includes a hole transport region interposed between the first electrode 110 and the light emitting layer and an electron transport region interposed between the light emitting layer and the second electrode 190 . region) may be further included.

[Hole transport region in organic layer 150]

The hole transport region may include i) a single layer structure made of a single layer made of a single material, ii) a single layer structure made of a single layer made of a plurality of different materials, or iii) a multilayer having a plurality of layers made of a plurality of different materials can have a structure.

The hole transport region may include at least one layer selected from a hole injection layer (HIL), a hole transport layer (HTL), an emission auxiliary layer, and an electron blocking layer (EBL).

For example, the hole transport region may have a single-layer structure including a single layer made of a plurality of different materials, or a hole injection layer/hole transport layer and a hole injection layer/hole transport layer sequentially stacked from the first electrode 110 . It may have a multilayer structure of /emission auxiliary layer, hole injection layer / light emission auxiliary layer, hole transport layer / light emission auxiliary layer, or hole injection layer / hole transport layer / electron blocking layer, but is not limited thereto.

The hole transport region may include an amine-based compound represented by Formula 1A or 1B.

In addition, the hole transport region is m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated- NPB, TAPC, HMTPD, TCTA (4,4',4"-tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N-carbazolyl)triphenylamine)), Pani/DBSA (Polyaniline /Dodecylbenzenesulfonic acid (polyaniline/dodecylbenzenesulfonic acid), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate) (poly(3,4-ethylenedioxythiophene)/poly(4-styrene) Sulfonate))), Pani/CSA (Polyaniline/Camphor sulfonic acid (polyaniline/camphorsulfonic acid)), PANI/PSS (Polyaniline/Poly(4-styrenesulfonate) (polyaniline/poly(4-styrenesulfonate)), It may include at least one selected from a compound represented by 201 and a compound represented by the following formula 202:

<Formula 201>

<Formula 202>

In Formulas 201 and 202,

L ₂₀₁ to L ₂₀₄ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted It is selected from a cyclic divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

L ₂₀₅ is, *-O-*', *-S-*', *-N(Q ₂₀₁ )-*', a substituted or unsubstituted C ₁ -C ₂₀ alkylene group, a substituted or unsubstituted C ₂ - C ₂₀ alkenylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted or unsubstituted C ₆ -C ₆₀ arylene group, a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, a substituted or unsubstituted divalent It is selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xa1 to xa4 are each independently selected from an integer of 0 to 3,

xa5 is selected from an integer of 1 to 10,

R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ Cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted a C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic hetero condensed group It may be selected from a polycyclic group.

For example, in Formula 202, R ₂₀₁ and R ₂₀₂ may be optionally connected to each other through a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R ₂₀₃ and R ₂₀₄ are optionally, They may be linked to each other through a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

According to one embodiment, in Formulas 201 and 202,

L ₂₀₁ to L ₂₀₅ are each independently,

Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorene Nylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, phenyl Relenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubycenylene group, coronenylene group, ovalenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group , benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group and pyridinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C ₁ -C ₁₀ phenyl group substituted with an alkyl group, -F substituted phenyl group, pentale Nyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group , phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, Rubycenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole phenyl, substituted with at least one selected from a diyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) and -N(Q ₃₁ )(Q ₃₂ ) Rene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenyl group Ren group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylene group Nylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubycenylene group, coronenylene group, ovalenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group;

is selected from

The Q ₃₁ to Q ₃₃ may be each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

According to another embodiment, xa1 to xa4 may each independently be 0, 1, or 2.

According to another embodiment, xa5 may be 1, 2, 3 or 4.

According to another embodiment, R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ are each independently selected from a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, Acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, phi Renyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubysenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazole group diary, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C ₁ -C ₁₀ phenyl group substituted with an alkyl group, -F substituted phenyl group, pentale Nyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group , phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, Rubycenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole A phenyl group substituted with at least one selected from a diyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) and -N(Q ₃₁ )(Q ₃₂ ) , biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, Dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group , hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group , a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group and a pyridinyl group;

can be selected from

For the description of Q ₃₁ to Q ₃₃ , refer to the bar described herein.

According to another embodiment, at least one of R ₂₀₁ to R ₂₀₃ in Formula 201 is each independently selected from the group consisting of:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C ₁ -C ₁₀ phenyl group substituted with an alkyl group, -F substituted phenyl group, naphthyl group , fluorenyl group, spiro-bifluorenyl group, carbazolyl group, dibenzofuranyl group and at least one substituted with dibenzothiophenyl group substituted, fluorenyl group, spiro-bifluorenyl group, carbazolyl group, di a benzofuranyl group and a dibenzothiophenyl group;

may be selected from, but is not limited thereto.

According to another embodiment, in Formula 202, i) R ₂₀₁ and R ₂₀₂ may be connected to each other through a single bond, and/or ii) R ₂₀₃ and R ₂₀₄ may be connected to each other through a single bond.

According to another embodiment, at least one of R ₂₀₁ to R ₂₀₄ in Formula 202 is,

carbazolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C ₁ -C ₁₀ phenyl group substituted with an alkyl group, -F substituted phenyl group, naphthyl group , a carbazolyl group substituted with at least one selected from a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

may be selected from, but is not limited thereto.

The compound represented by Chemical Formula 201 may be represented by the following Chemical Formula 201A:

<Formula 201A>

For example, the compound represented by Chemical Formula 201 may be represented by the following Chemical Formula 201A(1), but is not limited thereto:

<Formula 201A(1)>

As another example, the compound represented by Formula 201 may be represented by Formula 201A-1 below, but is not limited thereto:

<Formula 201A-1>

Meanwhile, the compound represented by Chemical Formula 202 may be represented by the following Chemical Formula 202A:

<Formula 202A>

According to another embodiment, the compound represented by Chemical Formula 202 may be represented by the following Chemical Formula 202A-1:

<Formula 202A-1>

In Formulas 201A, 201A(1), 201A-1, 202A and 202A-1,

For the description of L ₂₀₁ to L ₂₀₃ , xa1 to xa3, xa5 and R ₂₀₂ to R ₂₀₄ refer to the description in the present specification,

For the description of R ₂₁₁ and R ₂₁₂ , refer to the description of R ₂₀₃ in the present specification,

R ₂₁₃ to R ₂₁₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C ₁ -C ₁₀ alkyl group substituted phenyl group, -F substituted phenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzoflu Orenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group , pentaphenyl group, hexacenyl group, pentacenyl group, rubycenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, di It may be selected from a benzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.

The hole transport region may include at least one compound selected from the following compounds HT1 to HT39, but is not limited thereto:

The hole transport region may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 Å to about 9000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is about 50 Å to about 2000 Angstroms, for example from about 100 Angstroms to about 1500 Angstroms. When the thickness of the hole transport region, the hole injection layer, and the hole transport layer satisfies the above-described ranges, a satisfactory level of hole transport characteristics may be obtained without a substantial increase in driving voltage.

The light emitting auxiliary layer serves to increase light emission efficiency by compensating for an optical resonance distance according to a wavelength of light emitted from the light emitting layer, and the electron blocking layer serves to prevent electron injection from the electron transport region. am. The light emitting auxiliary layer and the electron blocking layer may include the materials described above.

[p-dopant]

The hole transport region may further include a charge-generating material to improve conductivity in addition to the above-described material. The charge-generating material may be uniformly or non-uniformly dispersed in the hole transport region.

The charge-generating material may be, for example, a p-dopant.

According to one embodiment, the LUMO of the p-dopant may be -3.5 eV or less.

The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto.

For example, the p-dopant is

quinone derivatives such as TCNQ (Tetracyanoquinodimethane) and F4-TCNQ (2,3,5,6-Tetrafluoro-7,7,8,8-tetracyanoquinodimethane);

metal oxides such as tungsten oxide and molybdenum oxide;

HAT-CN (1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile); and

A compound represented by the following Chemical Formula 221;

It may include at least one selected from, but is not limited thereto:

<HAT-CN> <F4-TCNQ>

<Formula 221>

In Formula 221,

R ₂₂₁ to R ₂₂₃ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group , substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent It is selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, wherein at least one of R ₂₂₁ to R ₂₂₃ is a cyano group, -F, -Cl, -Br, -I, At least selected from a C ₁ -C ₂₀ alkyl group substituted with -F, a C ₁ -C ₂₀ alkyl group substituted with -Cl, a C ₁ -C ₂₀ alkyl group substituted with -Br and a C ₁ -C ₂₀ alkyl group substituted with -I It has one substituent.

[The light emitting layer of the organic layer 150]

When the organic light emitting device 10 is a full color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer for each sub-pixel. Alternatively, the light-emitting layer has a structure in which two or more layers selected from a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer are stacked in contact or spaced apart, or two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material are layered It has a mixed structure without it, and can emit white light.

The emission layer may include a host and a dopant. The dopant may include at least one of a phosphorescent dopant and a fluorescent dopant.

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

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

[Host in the light-emitting layer]

The host may include a compound represented by the following Chemical Formula 301.

**<Formula 301>

[Ar ₃₀₁ ] _xb11 -[(L ₃₀₁ ) _xb1 -R ₃₀₁ ] _xb21

In Formula 301,

**Ar ₃₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

xb11 is 1, 2 or 3,

L ₃₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent non- It is selected from a condensed aromatic polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xb1 is selected from an integer of 0 to 5,

R ₃₀₁ is deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ Alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl 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 ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted A substituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl Group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₃₀₁ )(Q ₃₀₂ )(Q ₃₀₃ ), -N(Q ₃₀₁ )(Q ₃₀₂ ), -B(Q ₃₀₁ )(Q ₃₀₂ ), -C(=O)(Q ₃₀₁ ), -S(=O) ₂ (Q ₃₀₁ ) and -P(=O)(Q ₃₀₁ ) ) (Q ₃₀₂ ),

xb21 is selected from an integer of 1 to 5,

Q ₃₀₁ to Q ₃₀₃ may be each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but is not limited thereto.

According to one embodiment, Ar ₃₀₁ in Formula 301 is,

Naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group , chrysene group, naphthacene group, picene group, perylene group, pentaphen group, indenoanthracene group, dibenzofuran group and dibenzothiophene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), - C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ ) substituted with at least one selected from a naphthalene group, a fluorene group, Spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphen group, indenoanthracene group, dibenzofuran group and dibenzothiophene group;

is selected from

Q ₃₁ to Q ₃₃ may be each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but is not limited thereto.

In Formula 301, when xb11 is two or more, two or more Ar ₃₀₁ may be connected to each other through a single bond.

According to another embodiment, the compound represented by Chemical Formula 301 may be represented by the following Chemical Formula 301-1 or 301-2:

<Formula 301-1>

<Formula 301-2>

In Formulas 301-1 to 301-2,

A ₃₀₁ to A ₃₀₄ are each independently, benzene, naphthalene, phenanthrene, fluoranthene, triphenylene, pyrene, chrysen, pyridine, pyrimidine, indene, fluorene, spiro-bifluorene, benzoflu Orene, dibenzofluorene, indole, carbazole, benzocarbazole, dibenzocarbazole, furan, benzofuran, dibenzofuran, naphthofuran, benzonaphthofuran, dinaphthofuran, thiophene, benzothiophene, selected from dibenzothiophene, naphthothiophene, benzonaphthothiophene and dinaphthothiophene;

X ₃₀₁ is O, S or N-[(L ₃₀₄ ) _xb4 -R ₃₀₄ ],

R ₃₁₁ to R ₃₁₄ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), - B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ ); ,

xb22 and xb23 are each independently 0, 1 or 2,

Description of L ₃₀₁ , xb1, R ₃₀₁ and Q ₃₁ to Q ₃₃ refer to the bar described in the present specification,

For descriptions of L ₃₀₂ to L ₃₀₄ , refer to the description of L ₃₀₁ , independently of each other,

For descriptions of Xb2 to xb4, independently of each other, refer to the description of xb1,

For the description of R ₃₀₂ to R ₃₀₄ independently of each other, refer to the description of R ₃₀₁ .

For example, in Formulas 301, 301-1 and 301-2, L ₃₀₁ to L ₃₀₄ are each independently

Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl Renylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzo furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group , thiazolylene group, isothiazolylene group, oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl Ren group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, phenanthridinylene group, acridinylene group, phenane Trollinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazollylene group, imidazopyridinylene group, imidazopyrimidi a nylene group and an azacarbazolylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N( Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), and -P(=O)(Q ₃₁ ) (Q ₃₂ ) substituted with at least one selected from a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenyl group Ren group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carba Zolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, Dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group, oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadia Zolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxali Nylene group, quinazolinylene group, cinolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, iso a benzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group;

is selected from

For the description of Q ₃₁ to Q ₃₃ , reference may be made to the bar described in the present specification.

As another example, in Formulas 301, 301-1, and 301-2, R ₃₀₁ to R ₃₀₄ are each independently

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group , isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group , naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N( Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ), and -P(=O)(Q ₃₁ ) (Q ₃₂ ) substituted with at least one selected from a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group , anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group , isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosyl group rollyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, arc Lidinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyridinyl group midinyl group and azacarbazolyl group;

is selected from

For the description of Q ₃₁ to Q ₃₃ , reference may be made to the bar described in the present specification.

As another example, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (eg, compound H55 below), an Mg complex, and a Zn complex.

The host is ADN (9,10-Di(2-naphthyl)anthracene), MADN (2-Methyl-9,10-bis(naphthalen-2-yl)anthracene), TBADN (9,10-di-(2- naphthyl)-2-t-butyl-anthracene), CBP (4,4′-bis(N-carbazolyl)-1,1′-biphenyl), mCP (1,3-di-9-carbazolylbenzene), TCP (1 ,3,5-tri(carbazol-9-yl)benzene) and at least one selected from the following compounds H1 to H55, but is not limited thereto:

[Phosphorescent dopant included in the emission layer of the organic layer 150]

The phosphorescent dopant may include an organometallic complex represented by the following Chemical Formula 401:

<Formula 401>

M(L ₄₀₁ ) _xc1 (L ₄₀₂ ) _xc2

<Formula 402>

In Formulas 401 and 402,

M is iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh) ) and thulium (Tm),

L ₄₀₁ is selected from the ligands represented by Formula 402, xc1 is 1, 2, or 3, and when xc1 is 2 or more, two or more L ₄₀₁ are the same as or different from each other,

L ₄₀₂ is an organic ligand, xc2 is selected from an integer of 0 to 4, and when xc2 is 2 or more, two or more L ₄₀₂ are the same as or different from each other,

X ₄₀₁ to X ₄₀₄ are each independently nitrogen or carbon,

X ₄₀₁ and X ₄₀₃ are connected through a single bond or a double bond, X ₄₀₂ and X ₄₀₄ are connected through a single bond or a double bond,

A ₄₀₁ and A ₄₀₂ are each independently a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group,

X ₄₀₅ is a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q ₄₁₁ )-*', *-C(Q ₄₁₁ )( Q ₄₁₂ )-*', *-C(Q ₄₁₁ )=C(Q ₄₁₂ )-*', *-C(Q ₄₁₁ )=*' or *=C=*', wherein Q ₄₁₁ and Q ₄₁₂ are , hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group or naphthyl group,

X ₄₀₆ is a single bond, O or S,

R ₄₀₁ and R ₄₀₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ - C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₄₀₁ )(Q ₄₀₂ )(Q ₄₀₃ ), -N(Q ₄₀₁ )(Q ₄₀₂ ), -B(Q ₄₀₁ )(Q ₄₀₂ ), -C(=O)(Q ₄₀₁ ), -S(=O) ₂ (Q ₄₀₁ ) and -P(=O)(Q ₄₀₁ )(Q ₄₀₂ ), wherein Q ₄₀₁ to Q ₄₀₃ are independent of each other , selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a C ₆ -C ₂₀ aryl group and a C ₁ -C ₂₀ heteroaryl group,

xc11 and xc12 are each independently selected from an integer of 0 to 10;

In Formula 402, * and *' represent a binding site with M in Formula 401.

According to one embodiment, in Formula 402, A ₄₀₁ and A ₄₀₂ are each independently a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, furan ( furan) group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, quinoline group, iso Quinoline group, benzoquinoline group, quinoxaline group, quinazoline group, carbazole group, benzoimidazole group, benzofuran group, benzothiophene group, isobenzothiophene group, benzoxazole group, isobenzoxa It may be selected from a sol group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group and a dibenzothiophene group.

According to another embodiment, in Formula 402, i) X ₄₀₁ may be nitrogen, X ₄₀₂ may be carbon, or ii) both X ₄₀₁ and X ₄₀₂ may be nitrogen.

According to another embodiment, in Formula 402, R ₄₀₁ and R ₄₀₂ are each independently

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, phenyl group, naphthyl group, cyclopentyl group, cyclohexyl group, ada a C ₁ -C ₂₀ alkyl group and a C ₁ -C ₂₀ alkoxy group substituted with at least one selected from a mantanyl group, a norbornanyl group and a norbornenyl group;

Cyclopentyl group, cyclohexyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group group, triazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, dibenzofuranyl group and dibenzothiophenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyrida substituted with at least one selected from a zinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, a cyclopentyl group, a cyclohexyl group Sil group, adamantanyl group, norbornanyl group, norbornenyl group phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, qui a nolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; and

-Si(Q ₄₀₁ )(Q ₄₀₂ )(Q ₄₀₃ ), -N(Q ₄₀₁ )(Q ₄₀₂ ), -B(Q ₄₀₁ )(Q ₄₀₂ ), -C(=O)(Q ₄₀₁ ), -S (=O) ₂ (Q ₄₀₁ ) and -P(=O)(Q ₄₀₁ )(Q ₄₀₂ );

is selected from

The Q ₄₀₁ to Q ₄₀₃ may be each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but is not limited thereto.

According to another embodiment, when xc1 in Formula 401 is 2 or more, two A ₄₀₁ of two or more L ₄₀₁ are optionally connected to each other through a linking group X ₄₀₇ , or two A ₄₀₂ are optionally , may be linked to each other through a linking group, X ₄₀₈ (see compounds PD1 to PD4 and PD7 below). The X ₄₀₇ and X ₄₀₈ are each independently a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q ₄₁₃ )-*', *-C(Q ₄₁₃ )(Q ₄₁₄ )-*' or *-C(Q ₄₁₃ )=C(Q ₄₁₄ )-*', wherein Q ₄₁₃ and Q ₄₁₄ are independently of each other hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group or naphthyl group), but is not limited thereto.

In Formula 401, L ₄₀₂ may be any monovalent, divalent, or trivalent organic ligand. For example, L ₄₀₂ is halogen, diketone (eg, acetylacetonate), carboxylic acid (eg, picolinate), -C(=O), isonitrile, -CN and phosphorus (For example, phosphine, phosphite) may be selected from, but is not limited thereto.

Alternatively, the phosphorescent dopant may be, for example, selected from the following compounds PD1 to PD25, but is not limited thereto:

[Fluorescent dopant in the light emitting layer]

The fluorescent dopant may include an arylamine compound or a styrylamine compound.

The fluorescent dopant may include a compound represented by the following Chemical Formula 501:

<Formula 501>

In Formula 501,

Ar ₅₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

L ₅₀₁ to L ₅₀₃ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cyclo Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted It is selected from a cyclic divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xd1 to xd3 are each independently selected from an integer of 0 to 3,

R ₅₀₁ and R ₅₀₂ are each independently, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group , substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group selected,

xd4 may be selected from an integer of 1 to 6.

According to one embodiment, Ar ₅₀₁ in Formula 501 is,

Naphthalene group, heptalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group , pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphen group, indenoanthracene group and indenophenanthrene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, and naphthyl group substituted with at least one selected from, naphthalene group, heptalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group and indenophenane Tren group;

can be selected from

According to another embodiment, in Formula 501, L ₅₀₁ to L ₅₀₃ are each independently

Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl Renylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzo furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group , a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenylene group, a naphthylene group, a fluorenylene group, substituted with at least one selected from a dibenzosilolyl group and a pyridinyl group Rho-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, perylene group Nylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranyl Ren group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group;

can be selected from

According to another embodiment, in Formula 501, R ₅₀₁ and R ₅₀₂ are each independently

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group and a pyridinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group , a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) Substituted with at least one selected from phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, tri Phenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothio a phenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group and a pyridinyl group;

is selected from

Q ₃₁ to Q ₃₃ may be selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

According to another embodiment, xd4 in Formula 501 may be 2, but is not limited thereto.

For example, the fluorescent dopant may be selected from the following compounds FD1 to FD22:

Alternatively, the fluorescent dopant may be selected from the following compounds, but is not limited thereto.

[electron transport region in organic layer 150]

The electron transport region may have i) a single layer structure comprising a single layer made of a single material, ii) a single layer structure comprising a single layer made of a plurality of different materials, or iii) a multilayer structure having a plurality of layers made of a plurality of different materials can have

The electron transport region may include at least one layer selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer (ETL), and an electron injection layer, but is not limited thereto.

For example, the electron transport region may include an electron transport layer/electron injection layer, a hole blocking layer/electron transport layer/electron injection layer, an electron control layer/electron transport layer/electron injection layer, or a buffer layer/electron transport layer/ It may have a structure such as an electron injection layer, but is not limited thereto.

The electron transport region (eg, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing ring. .

The "π electron deficient nitrogen-containing ring" refers to a C ₁ -C ₆₀ heterocyclic group having at least one *-N=*′ moiety as a ring-forming moiety.

For example, the "π electron deficient nitrogen-containing ring" is i) a 5-7 membered heteromonocyclic group having at least one *-N=*' moiety, or ii) at least one *- two or more of the 5- to 7-membered heteromonocyclic groups having an N=*' moiety are heteropolycyclic groups condensed with each other, or iii) a 5-membered 5-membered group having at least one *-N=*' moiety It may be a heteropolycyclic group in which at least one of the to 7 membered heteromonocyclic group and at least one C ₅ -C ₆₀ carbocyclic group are condensed with each other.

Specific examples of the π electron deficient nitrogen-containing ring include imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, indazole, purine. , quinoline, isoquinoline, benzoquinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinoline, phenanthridine, acridine, phenanthroline, phenazine, benzoimidazole, isobenzothiazole, benzo oxazole, isobenzoxazole, triazole, tetrazole, oxadiazole, triazine, thiadiazole, imidazopyridine, imidazopyrimidine, azacarbazole, and the like, but are not limited thereto.

For example, the electron transport region may include a compound represented by the following Chemical Formula 601.

<Formula 601>

[Ar ₆₀₁ ] _xe11 -[(L ₆₀₁ ) _xe1 -R ₆₀₁ ] _xe21

In Formula 601,

Ar ₆₀₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

xe11 is 1, 2 or 3,

L ₆₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, a substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent non- It is selected from a condensed aromatic polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xe1 is selected from an integer of 0 to 5,

R ₆₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group , A substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, -Si(Q ₆₀₁ ) (Q ₆₀₂ )(Q ₆₀₃ ), -C(=O)(Q ₆₀₁ ), -S(=O) ₂ (Q ₆₀₁ ) and -P(=O)(Q ₆₀₁ )(Q ₆₀₂ ); ,

wherein Q ₆₀₁ to Q ₆₀₃ are each independently a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group or a naphthyl group,

xe21 is selected from an integer of 1 to 5;

According to one embodiment, at least one of xe11 Ar ₆₀₁ and xe21 R ₆₀₁ may include a π-electron deficient nitrogen-containing ring as described above.

According to one embodiment, the ring Ar ₆₀₁ in Formula 601 is,

Benzene group, naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphen group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carbazole group, imidazole group, pyrazole group , thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, Phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, isobenzothiazole group , benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group and azacarbazole group ; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )( Q ₃₂ ) substituted with at least one selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, Fluorantene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carba azole group, imidazole group, pyrazole group, thiazole group, isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, Benzoimidazole group, isobenzothiazole group, benzooxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imida group dazopyrimidine group and azacarbazole group;

can be selected from

The Q ₃₁ to Q ₃₃ may be each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In Formula 601, when xe11 is two or more, two or more Ar ₆₀₁ may be connected to each other through a single bond.

According to another embodiment, Ar ₆₀₁ in Formula 601 may be an anthracene group.

According to another embodiment, the compound represented by 601 may be represented by the following Chemical Formula 601-1:

<Formula 601-1>

In Formula 601-1,

X ₆₁₄ is N or C(R ₆₁₄ ), X ₆₁₅ is N or C(R ₆₁₅ ), X ₆₁₆ is N or C(R ₆₁₆ ), and at least one of X ₆₁₄ to X ₆₁₆ is N,

L ₆₁₁ to L ₆₁₃ are each independently, refer to the description of L ₆₀₁ ,

xe611 to xe613 refer to the description of xe1 above, independently of each other,

R ₆₁₁ to R ₆₁₃ are each independently refer to the description of R ₆₀₁ ,

R ₆₁₄ to R ₆₁₆ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C ₁ It may be selected from a -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

According to one embodiment, L ₆₀₁ and L ₆₁₁ to L ₆₁₃ in Formulas 601 and 601-1 are each independently

Phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl Renylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzo furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group , thiazolylene group, isothiazolylene group, oxazolylene group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl Ren group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, phenanthridinylene group, acridinylene group, phenane Trollinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazollylene group, imidazopyridinylene group, imidazopyrimidi a nylene group and an azacarbazolylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and at least one substituted with an azacarbazolyl group, a phenylene group, a naphthylene group, a fluorenylene group, Spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, phenyl Relenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofu Ranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylene group, isothiazolylene group, oxazolyl Ren group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, Pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group , phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolylene group, benzoxazolylene group, isobenzoxazolylene group, triazolylene group, tetrazolylene group , an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group;

may be selected from, but is not limited thereto.

According to another embodiment, in Formulas 601 and 601-1, xe1 and xe611 to xe613 may each independently be 0, 1, or 2.

According to another embodiment, in Formulas 601 and 601-1, R ₆₀₁ and R ₆₁₁ to R ₆₁₃ are each independently

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group , isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group , naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary, isoxazolyl group, thiadiazolyl group, oxadiazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , phenyl group, biphenyl group, terphenyl group, naphthyl group, flu Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylene group Nyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarba Zolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, thiadiazolyl group, oxadia Zolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoqui Nolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group , isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group; and

-S(=O) ₂ (Q ₆₀₁ ) and -P(=O)(Q ₆₀₁ )(Q ₆₀₂ );

is selected from

For the description of Q ₆₀₁ and Q ₆₀₂ , refer to the description herein.

The electron transport region may include at least one compound selected from the following compounds ET1 to ET36, but is not limited thereto:

Alternatively, the electron transport region is BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-Diphenyl-1,10-phenanthroline), Alq ₃ , BAlq, TAZ ( It may include at least one compound selected from 3-(Biphenyl-4-yl)-5-(4- tert -butylphenyl)-4-phenyl-4H-1,2,4-triazole) and NTAZ .

The thickness of the buffer layer, the hole blocking layer, or the electron control layer may be, independently of each other, about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the buffer layer, the hole blocking layer, or the electron control layer satisfies the above-described ranges, excellent hole blocking characteristics or electron control characteristics can be obtained without a substantial increase in driving voltage.

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 range, a satisfactory electron transport characteristic may be obtained without a substantial increase in driving voltage.

The electron transport region (eg, an electron transport layer in the electron transport region) may further include a metal-containing material in addition to the above-described material.

The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. Metal ions of the alkali metal complex may be selected from Li ions, Na ions, K ions, Rb ions and Cs ions, and the metal ions of the alkaline earth metal complex include Be ions, Mg ions, Ca ions, Sr ions, and Ba ions. ions may be selected. The ligand coordinated to the metal ion of the alkali metal complex and the alkaline earth metal complex is, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl Oxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclo It may be selected from pentadiene, but is not limited thereto.

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

The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190 . The electron injection layer may directly contact the second electrode 190 .

The electron injection layer has i) a single layer structure including a single layer made of a single material, ii) a single layer structure comprising a single layer made of a plurality of different materials, or iii) a multilayer structure having a plurality of layers made of a plurality of different materials can have

The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

The alkali metal may be selected from Li, Na, K, Rb and Cs. According to one embodiment, the alkali metal may be Li, Na, or Cs. According to another embodiment, the alkali metal may be Li or Cs, but is not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth metal compound and the rare earth metal compound may be selected from oxides and halides (eg, fluoride, chloride, bromide, iodide, etc.) of the alkali metal, the alkaline earth metal and the rare earth metal. there is.

The alkali metal compound may be selected from alkali metal oxides such as Li ₂ O, Cs ₂ O, K ₂ O, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, and the like. According to an embodiment, the alkali metal compound may be selected from LiF, Li ₂ O, NaF, LiI, NaI, CsI, and KI, but is not limited thereto.

The alkaline earth metal compound may be selected from alkaline earth metal compounds such as BaO, SrO, CaO, Ba _x Sr _1-x O (0<x<1), Ba _x Ca _1-x O (0<x<1), and the like. there is. According to an embodiment, the alkaline earth metal compound may be selected from BaO, SrO, and CaO, but is not limited thereto.

The rare earth metal compound may be selected from YbF ₃ , ScF ₃ , ScO ₃ , Y ₂ O ₃ , Ce ₂ O ₃ , GdF ₃ , and TbF ₃ . According to one embodiment, the rare earth metal compound may be selected from YbF ₃ , ScF ₃ , TbF ₃ , YbI ₃ , ScI ₃ , and TbI ₃ , but is not limited thereto.

The alkali metal complex, the alkaline earth metal complex and the rare earth metal complex include ions of an alkali metal, an alkaline earth metal and a rare earth metal as described above, and are coordinated to a metal ion of the alkali metal complex, the alkaline earth metal complex and the rare earth metal complex. The ligands are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadia sol, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but is not limited thereto. .

The electron injection layer consists of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof as described above, or , the organic material may be further included. When the electron injection layer further includes an organic material, the alkali metal, alkaline earth metal, rare earth metal, alkali metal compound, alkaline earth metal compound, rare earth metal compound, alkali metal complex, alkaline earth metal complex, rare earth metal complex, or any of these The combination may be uniformly or non-uniformly dispersed in the matrix made of the organic material.

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

[Second electrode 190]

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode that is an electron injection electrode. In this case, as a material for the second electrode 190 , a metal, an alloy, an electrically conductive compound, and a combination thereof having a low work function. (combination) can be used.

The second electrode 190 includes lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), and magnesium-indium (Mg-In). ), magnesium-silver (Mg-Ag), may include at least one selected from ITO and IZO, but is not limited thereto. The second electrode 190 may be a transmissive electrode, a transflective electrode, or a reflective electrode.

The second electrode 190 may have a single-layer structure that is a single layer or a multi-layer structure having a plurality of layers.

[Description of FIGS. 2 to 4]

Meanwhile, the organic light emitting device 20 of FIG. 2 has a structure in which a first capping layer 210 , a first electrode 110 , an organic layer 150 , and a second electrode 190 are sequentially stacked, and the organic light emitting diode 20 of FIG. The light emitting device 30 has a structure in which a first electrode 110 , an organic layer 150 , a second electrode 190 and a second capping layer 220 are sequentially stacked, and the organic light emitting device 40 of FIG. 4 is The first capping layer 210 , the first electrode 110 , the organic layer 150 , the second electrode 190 , and the second capping layer 220 have a structure in which they are sequentially stacked.

For a description of the first electrode 110 , the organic layer 150 , and the second electrode 190 in FIGS. 2 to 4 , refer to the description of FIG. 1 .

The light generated in the light emitting layer among the organic layers 150 of the organic light emitting devices 20 and 40 may be extracted to the outside through the first electrode 110 and the first capping layer 210 that are transflective or transmissive electrodes, The light generated in the light emitting layer among the organic layers 150 of the organic light emitting devices 30 and 40 may pass through the second electrode 190 and the second capping layer 220 that are transflective or transmissive electrodes and may be extracted to the outside.

The first capping layer 210 and the second capping layer 220 may serve to improve external luminous efficiency according to the principle of constructive interference.

The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer made of an organic material, an inorganic capping layer made of an inorganic material, or a composite capping layer including an organic material and an inorganic material.

At least one of the first capping layer 210 and the second capping layer 220 is, independently of each other, a carbocyclic compound, a heterocyclic compound, an amine compound, a porphine derivative, a phthalocyanine derivative ( phthalocyanine derivatives), naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes may include at least one material selected from the group consisting of. The carbocyclic compound, the heterocyclic compound, and the amine compound may be optionally substituted with a substituent including at least one element selected from O, N, S, Se, Si, F, Cl, Br and I. . According to one embodiment, at least one of the first capping layer 210 and the second capping layer 220, independently of each other, may include an amine-based compound.

According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may include, independently of each other, the compound represented by Formula 201 or the compound represented by Formula 202. there is.

According to another embodiment, at least one of the first capping layer 210 and the second capping layer 220 may include, independently of each other, a compound selected from the compounds HT28 to HT33 and the following compounds CP1 to CP5. However, the present invention is not limited thereto.

In the above, the organic light emitting device has been described with reference to FIGS. 1 to 4 , but the present invention is not limited thereto.

Each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are respectively vacuum deposition, spin coating, casting, LB (Langmuir-Blodgett), inkjet printing, laser printing, laser It may be formed in a predetermined area using various methods such as laser induced thermal imaging (LITI).

When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region is respectively formed by the vacuum deposition method, the deposition conditions are, for example, a deposition temperature of about 100 to about 500° C., about 10 Within the vacuum degree of ^-8 to about 10 ^-3 torr and the deposition rate of about 0.01 to about 100 Å/sec, it may be selected in consideration of the material to be included in the layer to be formed and the structure of the layer to be formed.

When each layer included in the hole transport region, the light emitting layer, and each layer included in the electron transport region are respectively formed by spin coating, the coating conditions are, for example, a coating speed of about 2000 rpm to about 5000 rpm and about 80 Within the heat treatment temperature range of ℃ to 200 ℃, it may be selected in consideration of the material to be included in the layer to be formed and the structure of the layer to be formed.

[General definition of a substituent]

In the present specification, the C ₁ -C ₆₀ alkyl group refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include a methyl group, an ethyl group, a propyl group, an isobutyl group, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, and the like. In the present specification, the C ₁ -C ₆₀ alkylene group refers to a divalent group having the same structure as the C ₁ -C ₆₀ alkyl group.

In the present specification, the C ₂ -C ₆₀ alkenyl group refers to a hydrocarbon group including one or more carbon double bonds in the middle or at the terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, a butenyl group. etc. are included. In the present specification, the C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

** In the present specification, the C ₂ -C ₆₀ alkynyl group refers to a hydrocarbon group including at least one carbon triple bond in the middle or at the terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, etc. are included. In the present specification, the C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

In the present specification, the C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the formula of -OA ₁₀₁ (here, A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group , an isopropyloxy group, and the like.

In the present specification, the C ₃ -C ₁₀ cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclo a heptyl group and the like. In the present specification, the C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

In the present specification, the C ₁ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, and , and specific examples thereof include a 1,2,3,4-oxatriazolidinyl group (1,2,3,4-oxatriazolidinyl), a tetrahydrofuranyl group (tetrahydrofuranyl), a tetrahydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

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

In the present specification, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom. has at least one double bond in it. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl group, 2,3-dihydrofuranyl group, 2,3-dihydro A thiophenyl group and the like are included. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

In the present specification, the C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group is a carbocyclic aromatic system having 6 to 60 carbon atoms. It means a divalent group having Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a chrysenyl group, and the like. When the C ₆ -C ₆₀ aryl group and the C ₆ -C ₆₀ arylene group include two or more rings, the two or more rings may be condensed with each other.

In the present specification, the C ₁ -C ₆₀ heteroaryl group includes at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom and is a monovalent group having a heterocyclic aromatic system having 1 to 60 carbon atoms. means, and the C ₁ -C ₆₀ heteroarylene group contains at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom and has a heterocyclic aromatic system having 1 to 60 carbon atoms. means group. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. When the C ₁ -C ₆₀ heteroaryl group and the C ₁ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be condensed with each other.

In the present specification, the C ₆ -C ₆₀ aryloxy group refers to -OA ₁₀₂ (here, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group is -SA ₁₀₃ (here , A ₁₀₃ is the above C ₆ -C ₆₀ aryl group).

In the present specification, a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring-forming atom, and the entire molecule is non-aromatic. means a monovalent group having (eg, having 8 to 60 carbon atoms). Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group and the like. In the present specification, the divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

In the present specification, the monovalent non-aromatic condensed heteropolycyclic group includes two or more rings condensed with each other, and at least one selected from N, O, Si, P and S in addition to carbon as a ring forming atom. It includes a hetero atom and refers to a monovalent group (eg, having 1 to 60 carbon atoms) in which the entire molecule is non-aromatic. Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group and the like. In the present specification, the condensed divalent non-aromatic heteropolycyclic group refers to a divalent group having the same structure as the condensed monovalent non-aromatic heteropolycyclic group.

In the present specification, the C ₅ -C ₆₀ carbocyclic group refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms including only carbon as a ring-forming atom. The C ₅ -C ₆₀ carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C ₅ -C ₆₀ carbocyclic group may be a ring such as benzene, a monovalent group such as a phenyl group, or a divalent group such as a phenylene group. Alternatively, depending on the number of substituents connected to the C ₅ -C ₆₀ carbocyclic group, the C ₅ -C ₆₀ carbocyclic group may be a trivalent group or a tetravalent group, and various modifications are possible.

In the present specification, the C ₁ -C ₆₀ heterocyclic group has the same structure as the C ₅ -C ₆₀ carbocyclic group, but as a ring-forming atom, carbon (the number of carbon atoms may be 1 to 60) other than carbon (which may be 1 to 60), N , means a group including at least one hetero atom selected from O, Si, P and S.

In the present specification, the substituted C ₅ -C ₆₀ carbocyclic group, substituted C ₁ -C ₆₀ heterocyclic group, substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkyl Ren group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted Condensed divalent non-aromatic polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, Substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ hetero Cycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted 1 At least one of the substituents of the non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed polycyclic group is,

Deuterium (-D), -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, 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, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero Cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₁ )(Q ₁₂ ) ), -B(Q ₁₁ )(Q ₁₂ ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ), and -P(=O)(Q ₁₁ )(Q ₁₂ ) 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 selected from the group consisting of;

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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo Alkenyl group, C _{6 -C 60 aryl group, C 6 -C 60} aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, _monovalent non-aromatic condensed polycyclic group, monovalent ratio -Aromatic condensed heteropolycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₁ )(Q ₂₂ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O) (Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C substituted with at least one selected from ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ );

is selected from

The Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group dino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic group It may be selected from a condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl group and a terphenyl group.

In the present specification, "Ph" means a phenyl group, "Me" means a methyl group, "Et" means an ethyl group, "ter-Bu" or "But ^t " means a tert-butyl group, "OMe"" means a methoxy group.

In the present specification, "biphenyl group" means "a phenyl group substituted with a phenyl group". The "biphenyl group" belongs to a "substituted phenyl group" in which the substituent is a "C ₆ -C ₆₀ aryl group".

In the present specification, "terphenyl group" means "a phenyl group substituted with a biphenyl group". The "terphenyl group" belongs to a "substituted phenyl group" in which the substituent is a "C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group".

In the present specification, * and *', unless otherwise defined, refer to binding sites with neighboring atoms in the corresponding chemical formula.

Hereinafter, a compound and an organic light emitting device according to an embodiment of the present invention will be described in more detail with reference to Synthesis Examples and Examples. In the following synthesis examples, in the expression "B was used instead of A", the molar equivalent of A and the molar equivalent of B are the same.

[Synthesis Example]

Synthesis Example 1: Synthesis of compound 1

(1) Synthesis of Intermediate 1-1

1-bromodibenzo[ b,d ]furan (a) (5g), 9,9-dimethyl-9 H -fluoren-2-amine (b) (6.4g), K _t OBu (Potassium tert-butoxide) (6.4 g), P(tBu) ₃ (0.3 g), and Pd ₂ (dba) ₃ (0.4 g) were diluted in toluene and stirred under reflux. After 20 hours, the temperature was lowered to room temperature and the reaction was terminated with water. After extraction three times with ethyl acetate, the resultant was dried over anhydrous magnesium sulfate, and then filtered under reduced pressure. The residue thus obtained was separated and purified using column chromatography to obtain Intermediate 1-1 6.5 (86%). The resulting compound was confirmed through LC-MS. C27H21NO : calc'd : M+ 375.16 foun'd : 375.26

(2) Synthesis of compound 1

Intermediate 1-1 (3.8 g) was used instead of Intermediate (b), and 3-iodo-9-phenyl-9H-carbazole (c) (3.7 g) was used instead of 1-bromodibenzo[ b , d ]furan (a). Compound 1 was obtained in the same manner as in Intermediate 1-1, except that

C45H32N2O : calc'd : M+ 616.25 foun'd : 616.35

Synthesis Example 2: Synthesis of compound 2

(1) Synthesis of Intermediate 2-1

Intermediate 2-1 (8.2 g, 82%) was obtained in the same manner as Intermediate 1-1 except that Intermediate (d) (8 g) was used instead of Intermediate (b). C37H25NO: calc'd : M+ 499.19 foun'd : 499.29

(2) Synthesis of compound 2

Compound 2 was obtained in the same manner as in Compound 1, except that Intermediate 2-1 (5g) was used instead of Intermediate 1-1. C55H36N2O : calc'd : M+ 740.28 foun'd : 740.38

Synthesis Example 3: Synthesis of compound 3

(1) Synthesis of Intermediate 3-1

Intermediate 3-1 (5.2 g, 52%) was obtained in the same manner as Intermediate 1-1 except that Intermediate (e) (8 g) was used instead of Intermediate (b). C37H25NO: calc'd : M+ 497.18 foun'd : 497.28

(2) Synthesis of compound 3

Compound 3 (7.4 g, 75%) was obtained in the same manner as in Compound 1, except that Intermediate 3-1 (5 g) was used instead of Intermediate 1-1. C55H36N2O : calc'd : M+ 740.28 foun'd : 740.38

Synthesis Example 4: Synthesis of compound 4

(1) Synthesis of Intermediate 4-1

Use 1-bromodibenzo[b,d]furan (4.9g) and spiro[cyclopentane-1,9'-fluoren]-2'-amine (7.1g) instead of intermediate (a) (5g) and intermediate (b), respectively Intermediate 4-1 (5.1 g, 64%) was obtained in the same manner as Intermediate 1-1 except that.

C29H23NO : calc'd : M+ 401.18 foun'd : 401.20

(2) Synthesis of compound 4

Same method as Intermediate 1-1 except that Intermediate 4-1 (4g) and 3-iodo-9-phenyl-9H-carbazole (3.7g) were used instead of Intermediate (a) (5g) and Intermediate (b), respectively. to obtain compound 4 (4.6 g, 72%).

C47H34N2O : calc'd : M+ 647.27 foun'd : 647.28

¹ H NMR (500 MHz, CDCl ₃ ) δ = 8.22 (m, 1H), 7.79 (dd, 2H), 7.72 (dd, 1H), 7.67 (d, 1H), 7.54-7.14 (m, 17H), 6.95 (d, 1H), 6.90 (dd, 1H), 6.66 (dd, 1H),. 6.54 (dd, 1H), 2.19-2.08 (m, 2H), 1.95-1.72 (m, 6H)

Synthesis Example 5: Synthesis of compound 5

Intermediate 1- except that Intermediate 1-1 (3.8g) is used instead of Intermediate (b) and 3-bromo-9-(4-fluorophenyl)-9H-carbazole (3.4g) is used instead of Intermediate (a) Compound 5 (4.7 g, 74%) was obtained in the same manner as in 1. C45H31FN2O : calc'd : M+ 634.24 foun'd : 634.34

Synthesis Example 6: Synthesis of compound 6

Intermediate 1-1 except that Intermediate 2-1 (5g) is used instead of Intermediate (b) and 3-bromo-9-(4-fluorophenyl)-9H-carbazole (3.4g) is used instead of Intermediate (a) Compound 6 (5.2 g, 68%) was obtained in the same manner as described above. C55H35FN2O : calc'd : M+ 758.27 foun'd : 758.37

Synthesis Example 7: Synthesis of compound 8

Compound 8 (5g, 76%) was obtained in the same manner as in Compound 4 except for using Intermediate 4-1 (4g) and 9-(4-fluorophenyl)-3-iodo-9H-carbazole (3.9g).

C47H33FN2O : calc'd : M+ 660.26 foun'd : 660.27

¹ H NMR (500 MHz, CDCl ₃ ) δ=8.22(m, 1H), 7.79(dd, 2H), 7.72(dd, 1H), 7.67(d, 1H), 7.48-7.23(m, 13H), 7.18 -7.14 (m, 1H), 7.09-7.04 (m, 2H), 6.95 (d, 1H), 6.90 (dd, 1H), 6.66 (dd, 1H),. 6.54 (dd, 1H), 2.19-2.08 (m, 2H), 1.95-1.72 (m, 6H)

Synthesis Example 8: Synthesis of compound 16

Compound 16 (compound 16 ( 4.7 g, 66%) was obtained.

C53H38N2O : calc'd : M+ 718.30 foun'd : 718.33

¹ H NMR (500 MHz, CDCl ₃ ) δ=8.22(m, 1H), 7.79(dd, 2H), 7.72(dd, 1H), 7.67(d, 1H), 7.63-7.59(m, 2H), 7.57 -7.23(m, 18H), 7.18(dt, 1H), 6.95(d, 1H), 6.90(dd, 1H), 6.66(dd, 1H), 6.59(dd, 1H), 2.19-2.08(m, 2H) ), 1.95-1.72 (m, 6H)

Synthesis Example 9: Synthesis of compound 21

Compound 1-1 in the same manner as in Intermediate 1-1, except that Intermediate 1-1 (3.8 g) was used instead of Intermediate (b), and 2-bromodibenzo[b,d]furan (2.5 g) was used instead of Intermediate (a). 21 (4.3 g, 80%) was obtained. C45H31FN2O: calc'd : M+ 541.20 foun'd : 541.30

Synthesis Example 10: Synthesis of compound 37

In the same manner as in Intermediate 1-1, compound 37 (3.8 g, 76%) was obtained.

C36H24N2O M+ calc'd : 500.19 foun'd : 500.29

Synthesis Example 11: Synthesis of compound 93

Compound 93 (5.1g, 74) in the same manner as in Intermediate 1-1, except that Intermediate 1-1 (3.8g) was used instead of Intermediate (b), and Intermediate 93-1 (4g) was used instead of Intermediate (a). %) was obtained.

C51H36N2O M+ calc'd : 692.28 foun'd : 692.38

Synthesis Example 12: Synthesis of compound 94

Compound 94 (6.3 g, 77% ) was obtained.

C61H40N2O M+ calc'd : 816.31 foun'd : 816.41

Synthesis Example 13: Synthesis of compound 95

Compound 95 (6.1 g, 75%) in the same manner as in Intermediate 1-1, except that Intermediate 3-1 (5g) was used instead of Intermediate (b), and Intermediate 93-1 (4g) was used instead of Intermediate (a). ) was obtained.

C61H38N2O M+ calc'd : 814.30 foun'd : 814.40

Synthesis Example 14: Synthesis of compound 101

Compound 101 (7.1 g, 7.1 g, 75%) was obtained.

C51H35FN2O M+ calc'd : 710.27 foun'd : 710.37

Synthesis Example 15: Synthesis of compound 187

In the same manner as in Intermediate 1-1, except that Intermediate 2-1 (2.5g) and 2-bromo-9,9-diphenyl-9H-fluorene (2g) were used instead of Intermediate (a) and Intermediate (b), respectively. Compound 187 (3.1 g, 77%) was obtained.

C62H39NO : calc'd : M+ 813.30 foun'd : 813.34

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.92-7.84(m, 4H), 7.79(m, 1H), 7.72(dd, 1H), 7.61(d, 1H), 7.58(d, 1H), 7.48 -7.41(m, 5H), 7.36-7.28(m, 3H), 7.21-7.06(m, 14H), 6.92(dd, 1H), 6.81-6.72(m, 5H), 6.66(dd, 1H), 6.57 (d, 1H), 6.43 (d, 1H)

Synthesis Example 16: Synthesis of compound 188

In the same manner as in Intermediate 1-1, except that Intermediate 3-1 (2.5g) and 2-bromo-9,9'-spirobi[fluorene] (2g) were used instead of Intermediate (a) and Intermediate (b), respectively. Compound 188 (3.3 g, 81%) was obtained.

C62H37NO : calc'd : M+ 811.29 foun'd : 811.31

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.92 (dd, 4H), 7.89 (dd, 2H), 7.79 (td, 1H), 7.72 (dd, 1H), 7.61 (d, 2H), 7.48-7.41 (m, 7H), 7.36-7.26 (m, 3H), 7.21-7.15 (m, 6H), 6.92 (dd, 2H), 6.77-6.73 (m, 6H), 6.68 (dd, 1H), 6.43 (d) , 2H)

Synthesis Example 17: Synthesis of compound 204

Compound 1-1 in the same manner as in Intermediate 1-1, except that Intermediate 2-1 (5g) was used instead of Intermediate (b) and 2-bromo-1,1'-biphenyl (2.3g) was used instead of Intermediate (a). 204 (3.8 g, 58%) was obtained.

C49H33NO : M+ calc'd : 651.26 foun'd : 651.36

Synthesis Example 18: Synthesis of compound 210

(1) Synthesis of intermediate 210-1

Except for using [1,1'-biphenyl]-2-amine (2.5g) and 1-bromodibenzo[b,d]furan (2.5g) instead of intermediate (b) and intermediate (a) (5g), respectively Intermediate 210-1 (3 g, 91%) was obtained in the same manner as in Intermediate 1-1.

C24H17NO: calc'd : M+ 335.13 foun'd : 335.14

(2) Synthesis of compound 210

In the same manner as in Intermediate 1-1, except that Intermediate 210-1 (3g) and 2-bromo-9,9'-spirobi[fluorene] (3.7g) were used instead of Intermediate (b) and Intermediate (a), respectively. Compound 210 (5.1 g, 86%) was obtained.

C49H31NO: calc'd: M+649.24 foun'd: 649.25

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.92 (dd, 2H), 7.89 (dd, 1H), 7.80 (d, 1H), 7.72 (d, 1H), 7.59-7.51 (m, 5H), 7.49 -7.41(m, 5H), 7.32-7.27(m, 3H), 7.21-7.14(m, 5H), 7.01(t, 1H), 6.77-6.73(m, 4H), 6.66(dd, 1H), 6.61 (dd, 1H), 5.47 (d, 1H)

Synthesis Example 19: Synthesis of compound 213

(1) Synthesis of Intermediate 213-2

Dilute 2,7-dibromo-9,9'-spirobi[fluorene] (4.7 g) and phenyl boronic acid (3.4 g) in tetrahydrofuran (60 ml) and water (20 ml). K ₂ CO ₃ (4.1g) and Pd(PPh ₃ ) ₄ (580 mg) were added dropwise and stirred under reflux at 65°C. When the reaction was completed, the temperature was slowly lowered to room temperature, extracted three times with ethyl artesate, and filtered under reduced pressure. Then, the residue obtained by distillation under reduced pressure was separated and purified by column chromatography to obtain Intermediate 213-2 (4.4 g, 93%).

C31H19Br : calc'd : M+ 470.07 foun'd : 470.08

(2) Synthesis of Intermediate 213-1

Except for using [1,1'-biphenyl]-4-amine (2.5 g) and 1-bromodibenzo[b,d]furan (2.5 g) in the place of intermediate (b) and intermediate (a) (5 g), respectively Intermediate 213-1 (3 g, 91%) was obtained in the same manner as Intermediate 1-1.

C24H17NO: calc'd : M+ 335.13 foun'd : 335.14

(3) Synthesis of compound 213

Compound 213 (5.1g, 79%) in the same manner as in Intermediate 1-1, except that Intermediate 213-2 (4.4g) and Intermediate 213-1 (3g) were used instead of Intermediate (a) and Intermediate (b), respectively. got

C55H35NO: calc'd : M+ 725.27 foun'd : 725.30

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.93 (dd, 2H), 7.79-7.78 (m, 2H), 7.72-7.59 (m, 6H), 7.54-7.28 (m, 15H), 7.20 (t, 2H), 6.89 (m, 2H), 6.75 (dd, 2H), 6.68 (dd, 1H), 6.56-6.54 (m, 2H), 5.68 (d, 1H)

Synthesis Example 20: Synthesis of compound 219

Compound 219 (3.1g, 81)% in the same manner as in Intermediate 1-1, except that Intermediate 213-(2.4g) and Intermediate 1-1 (1.9g) were respectively used instead of Intermediate (a) and Intermediate (b). got

C58H39NO : calc'd : M+ 765.30 foun'd : 765.34

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.93 (dd, 2H), 7.79-7.67 (m, 6H), 7.62 (d, 1H), 7.53-7.28 (m, 11H), 7.18 (dt, 2H) , 7.11 (dd, 2H), 6.89-6.82 (m, 3H), 6.75 (dd, 2H), 6.68 (dd, 1H), 6.50 (d, 1H). 6.10 (d, 1H), 1.61 (s, 6H)

Synthesis Example 21: Synthesis of compound 240

In the same manner as in Intermediate 1-1 except for using 6-bromo-2,9-diphenyl-9H-carbazole (2g) and Intermediate 213-1 (1.7g) instead of Intermediate (a) and Intermediate (b), respectively. Compound 240 (2.5 g, 78%) was obtained.

C48H32N2O: calc'd : M+ 625.25 foun'd : 625.29

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.86(dd, 1H), 7.79-7.76(m, 2H), 7.73-7.70(m, 3H), 7.65-7.61(m, 2H), 7.55-7.28( m, 18H), 7.24-7.21 (m, 2H), 6.70-6.65 (m, 3H), 6.59 (dd, 1H)

Synthesis Example 22: Synthesis of compound 251

(1) Synthesis of Intermediate 251-1

Except for using 9,9-dimethyl-9H-fluoren-1-amine (2.1g) and 1-bromodibenzo[b,d]furan (2.5g) in place of intermediate (b) and intermediate (a) (5g), respectively and Intermediate 251-1 (3.1 g, 83%) was obtained in the same manner as Intermediate 1-1.

C27H21NO: calc'd: M+ 375.16 foun'd: 375.19

(2) Synthesis of compound 251

Compounds in the same manner as in Intermediate 1-1 except that Intermediate 251-1 (3.1g) and 3-iodo-9-phenyl-9H-carbazole (3.1g) were used instead of Intermediate (b) and Intermediate (a), respectively. 251 (4 g, 78%) was obtained.

C45H32N2O: calc'd : M+ 616.25 foun'd : 616.29

¹ H NMR (500 MHz, CDCl ₃ ) δ = 8.22 (d, 1H), 7.82 (d, 1 H), 7.77 (td, 1H), 7.70 (dd, 1H), 7.54-7.44 (m, 7H), 7.39-7.22 (m, 10H), 7.11 (dd, 1H), 6.96 (dd, 1H), 6.57-6.47 (m, 3H), 1.68 (s, 6H)

Synthesis Example 23: Synthesis of compound 253

(1) Synthesis of Intermediate 253-1

Except for using 9,9-dimethyl-9H-fluoren-4-amine (2.1g) and 1-bromodibenzo[b,d]furan (2.5g) in place of intermediate (b) and intermediate (a) (5g), respectively and Intermediate 253-1 (3.5 g, 92%) was obtained in the same manner as Intermediate 1-1.

C27H21NO: calc'd: M+ 375.16 foun'd: 375.19

(2) Synthesis of compound 253

In the same manner as in Intermediate 1-1, except that Intermediate 253-1 (3.5 g) and 3-iodo-9-phenyl-9H-carbazole (3.6 g) were used instead of Intermediate (b) and Intermediate (a), respectively. 253 (4.6 g, 81%) was obtained.

C45H32N2O: calc'd : M+ 616.25 foun'd : 616.29

¹ H NMR (500 MHz, CDCl ₃ ) δ = 8.22 (d, 1H), 7.82 (d, 1 H), 7.72 (d, 1H), 7.63 (dd, 1 H), 7.51-7.21 (m, 16H) , 7.14-7.07 (m, 2H), 6.86 (dd, 1H), 6.61-6.59 (m, 1H), 6.53 (dd, 1H), 6.24 (td, 1H), 1.61 (s, 6H)

Synthesis Example 24: Synthesis of compound 256

Intermediate 1-1 and Intermediate 1-1, except that Intermediate 253-1 (3.5 g) and 3-bromo-9-(4-fluorophenyl)-9H-carbazole (3.2 g) were used instead of Intermediate (b) and Intermediate (a), respectively. Compound 256 (5.0 g, 84%) was obtained in the same manner.

C45H31FN2O: calc'd : M+ 634.24 foun'd : 634.25

¹ H NMR (500 MHz, CDCl ₃ ) δ = 8.23 (d, 1H), 7.82 (d, 1H), 7.72 (td, 1 H), 7.62 (dd, 1H), 7.58-7.35 (m, 3H), 7.34-7.21 (m, 10H), 7.14-7.03 (m, 4H), 6.86 (dd, 1H), 6.61 (m, 1H), 6.53 (dd, 1 H), 6.24 (dd, 1H, 1.61 (s, 6H)

Synthesis Example 25: Synthesis of compound 268

(1) Synthesis of intermediate 268-1

Except for using 9,9-dimethyl-9H-fluoren-2-amine (2.1g) and 1-bromodibenzo[b,d]furan (2.5g) in place of intermediate (b) and intermediate (a) (5g), respectively and Intermediate 268-1 (3.2 g, 85%) was obtained in the same manner as Intermediate 1-1.

C27H21NO: calc'd: M+ 375.16 foun'd: 375.18

(2) Synthesis of compound 268

Compound 268 (5.7 g, 88%) in the same manner as in Intermediate 1-1, except that Intermediate 268-1 (3.2 g) and Intermediate 213-2 (4.0 g) were used instead of Intermediate (b) and Intermediate (a), respectively. ) was obtained.

C58H39NO: calc'd : M+ 765.30 foun'd : 765.32

¹ H NMR (500 MHz, CDCl ₃ ) δ=7.93 (dd, 2H), 7.79-7.66 (m, 6H). 7.62(d, 1H), 7.53-7.29(m, 11H), 7.20(dt,2H), 7.11-7.04(m, 4H), 6.89(d,1H), 6.87(t, 1H), 6.75( t, 1H), 6.74 (d, 1H), 6.66 (dd, 1H), 6.42 (dd, 1 H), 5.68 (d, 1 H), 1.52 (s, 6H)

Synthesis Example 26: Synthesis of compound 269

Compound 269 (4.8 g, 74%) in the same manner as in Intermediate 1-1 except that Intermediate 253-1 (3.2 g) and 213-2 (4.0 g) were used instead of Intermediate (b) and Intermediate (a), respectively. got

C58H39NO: calc'd : M+ 765.30 foun'd : 765.32

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.93(d, 2H), 7.82(d, 1H), 7.80(d, 1H), 7.72-7.58(m, 5H), 7.53-7.36(m, 7H) , 7.33-7.05 (m, 9H), 6.87-6.84 (m, 2H), 6.79 (dd, 1 H), 6.75 (dd, 2 H), 6.61 (m, 1H), 6.23 (d, 1H), 5.49 (d, 1H), 1.61 (s, 6H)

Synthesis Example 27: Synthesis of compound 278

Same method as Intermediate 1-1, except that Intermediate 253-1 (3.2 g) and 2-bromo-9,9'-spirobi[fluorene] (3.8 g) were used instead of Intermediate (b) and Intermediate (a), respectively. to give compound 278 (4.3 g, 86%).

C52H35NO: calc'd : M+ 689.27 foun'd : 689.28

¹ H NMR (500 MHz, CDCl ₃ ) δ=7.92(d, 2H), 7.89(d, 1H), 7.82(d,1H), 7.72(d, 1H), 7.62(dd, 1H), 7.59( d,1 H), 7.48-7.41 (m, 4H), 7.32-7.06 (m, 10H), 6.87 (d, 1H), 6.81 (dd,1 H), 6.77-6.73 (m, 3H), 6.61 ( m,1 H), 6.23 (d, 1H), 5.72 (dd, 1H), 1.61 (s, 6H)

Synthesis Example 28: Synthesis of compound 281

(1) Synthesis of intermediate 281-1

Except for the use of 9,9-diphenyl-9H-fluoren-4-amine (3.3g) and 1-bromodibenzo[b,d]furan (2.5g) instead of intermediate (b) and intermediate (a) (5g), respectively and Intermediate 281-1 (3.8 g, 77%) was obtained in the same manner as Intermediate 1-1.

C37H25NO: calc'd : M+ 499.19 foun'd : 499.23

(2) Synthesis of compound 281

Same method as Intermediate 1-1 except that Intermediate 281-1 (3.8 g) and 2-bromo-9,9'-spirobi[fluorene] (3.2 g) were used instead of Intermediate (b) and Intermediate (a), respectively. to give compound 281 (4.9 g, 79%).

C62H39NO: calc'd : M+ 813.30 foun'd : 813.33

¹ H NMR (500 MHz, CDCl ₃ ) δ = 7.92 (d, 2H), 7.89 (d, 1 H), 7.82 (d, 1 H), 7.72 (d, 1 H), 7.59 (dd, 2H), 7.49-7.40 (m, 4H), 7.33-7.26 (m, 4H), 7.21-7.05 (m, 14H), 6.81-6.71 (m, 6H), 6.62 (m, 1H), 6.56 (dd, 1H), 5.72 (d, 1H), 5.68 (t, 1H)

¹ H NMR of the compounds synthesized in Synthesis Examples 1 to 28 are shown in Tables 1 and 2 below. Compounds other than those shown in Tables 1 and 2 can also be easily recognized by those skilled in the art by referring to the above synthetic routes and raw materials.

compound 1H NMR (400Mhz) One 8.25(d, 1H), 7.85(d, 2H), 7.80-7.75(m,2H), 7.73-7.70(m, 1H), 7.56(d, 1H), 7.53-7.21(m, 14H), 7.15 7.09 (m, 2H), 7.00 (dd, 3H), 6.85 (dd, 1H), 6.65 (dd, 1H), 6.55 (dd, 1H), 1.61 (s, 6H) 2 8.22-8.20(m, 1H), 7.86(td, 1H), 7.79-7.77(m, 1H), 7.72(m,1H), 7.58(d, 1H), 7.51-7.23(m, 15H), 7.21- 7.05 (m, 11H), 6.81 (td, 1H), 6.73 (dd, 1H), 6.65 (dd, 1H), 6.53-6.48 (m, 2H) 3 8.22-8.20 (m, 1H), 7.90 (dd, 2H), 7.87 (dd, 1H), 7.79 (m, 1H), 7.72 (m, 1H), 7.61 (d, 1H), 7.54-7.12 (m, 20H), 6.92 (dd, 1H), 6.77-6.73 (m, 3H), 6.66 (dd, 1H), 6.51 (dd, 1H), 5.97 (q, 1H) 5 8.22-8.20 (m, 1H), 7.85 (m, 1H), 7.79-7.76 (m, 2H), 7.71 (m, 1H), 7.57 (m, 1H), 7.46 (dd, 1H), 7.40-7.21 ( m, 10H), 7.14-7.03 (m, 4H), 7.01 (dd, 1H), 6.85 (dd, 1H), 6.66 (dd, 1H), 6.54 (dd, 1H), 1.61 (s, 6H) 6 8.22-8.20 (m, 1H), 7.86 (td, 1H), 7.79-7.77 (m, 1H), 7.72-7.70 (m, 1H), 7.58 (d, 1H). 7.48-7.23 (m, 12H), 7.20-7.03 (m, 13H), 6.81 (dd, 1H), 6.73 (dd, 1H), 6.66 (dd, 1H), 6.53 (q, 1H), 6.51 (dd, 1H) 21 7.84-7.82(m, 1H), 7.79-7.75(m, 2H), 7.73-7.70(m, 2H), 7.68-7.65(m, 1H), 7.57-7.40(m, 5H), 7.34-7.25(m) , 4H), 7.14-7.09 (m, 2H), 7.03 (dd, 1H), 6.85 (m, 1H), 6.66 (dd, 1H), 6.54 (dd, 1H), 1.61 (s, 6H) 37 8.22-8.20 (m, 1H), 7.79 (m, 1H), 7.72 (m, 1H), 7.54-7.21 (m, 14H), 7.08-7.02 (m, 2H), 6.67-6.53 (m, 3H), 6.34-6.31(m, 2H) 93 8.24-8.22(m, 1H), 8.15(m, 1H), 7.79-7.70(m, 4H), 7.67(d, 1H), 7.58-7.42(m, 8H), 7.39-7.25(m, 7H), 7.21-7.19(m, 1H), 7.14-7.09(m, 2H), 6.84(dd, 1H), 6.68(dd, 1H), 6.63-6.59(m, 2H), 6.49(m, 1H), 1.61( s, 6H) 94 8.24-8.22(m, 1H), 8.15(m, 1H), 7.86(td, 1H), 7.79-7.70(m, 3H), 7.67(d, 1H), 7.60-7.53(m, 3H),7.50- 7.25 (m, 12H), 7.21-7.03 (m, 12H), 6.81 (td, 1H), 6.75 (dd, 1H), 6.68 (dd, 1H), 6.63-6.57 (m, 3H), 6.44 (d, 1H) 95 8.24-8.22(m, 1H), 8.15(m, 1H), 8.02-7.87(m, 3H), 7.79-7.70(m, 3H), 7.67(d, 1H), 7.60-7.53(m, 3H), 7.50-7.25 (m, 14H), 7.23-7.15 (m, 4H), 6.92 (dd, 1H), 6.77-6.71 (m, 3H), 6.68 (dd, 1H), 6.63-6.57 (m, 3H), 5.95 (d, 1H) 101 8.24-8.22(m, 1H), 8.15(m, 1H), 7.79-7.70(m, 4H), 7.67(d, 1H), 7.58-7.52(m, 3H), 7.48-7.44(m, 1H), 7.39-7.25 (m, 8H), 7.21-7.19 (m, 1H), 7.14-7.03 (m, 4H), 6.84 (dd, 1H), 6.68 (dd, 1H), 6.63-6.59 (m, 2H), 6.49 (m, 1H), 1.61 (s, 6H) 204 7.92-7.87(m, 3H), 7.79(m, 1H), 7.72(m,1H), 7.63-7.58(m, 3H), 7.52-7.24(m,12H), 7.21-7.15(m, 3H), 6.92 (dd, 1H), 6.77-6.71 (m, 3H), 6.68-6.66 (dd, 1H), 6.58-6.54 (m, 2H), 5.95 (dd, 1H)

compound 1H NMR (500Mhz) 4 8.22 (m, 1H), 7.79 (dd, 2H), 7.72 (dd, 1H), 7.67 (d, 1H), 7.54-7.14 (m, 17H), 6.95 (d, 1H), 6.90 (dd, 1H) , 6.66 (dd, 1H),. 6.54 (dd, 1H), 2.19-2.08 (m, 2H), 1.95-1.72 (m, 6H) 8 8.22(m, 1H), 7.79(dd, 2H), 7.72(dd, 1H), 7.67(d, 1H), 7.48-7.23(m, 13H), 7.18-7.14(m, 1H), 7.09-7.04( m, 2H), 6.95 (d, 1H), 6.90 (dd, 1H), 6.66 (dd, 1H),. 6.54 (dd, 1H), 2.19-2.08 (m, 2H), 1.95-1.72 (m, 6H) 16 8.22(m, 1H), 7.79(dd, 2H), 7.72(dd, 1H), 7.67(d, 1H), 7.63-7.59(m, 2H), 7.57-7.23(m, 18H), 7.18(dt, 1H), 6.95 (d, 1H), 6.90 (dd, 1H), 6.66 (dd, 1H), 6.59 (dd, 1H), 2.19-2.08 (m, 2H), 1.95-1.72 (m, 6H) 187 7.92-7.84(m, 4H), 7.79(m, 1H), 7.72(dd, 1H), 7.61(d, 1H), 7.58(d, 1H), 7.48-7.41(m, 5H), 7.36-7.28( m, 3H), 7.21-7.06 (m, 14H), 6.92 (dd, 1H), 6.81-6.72 (m, 5H), 6.66 (dd, 1H), 6.57 (d, 1H), 6.43 (d, 1H) 188 7.92 (dd, 4H), 7.89 (dd, 2H), 7.79 (td, 1H), 7.72 (dd, 1H), 7.61 (d, 2H), 7.48-7.41 (m, 7H), 7.36-7.26 (m, 3H), 7.21-7.15 (m, 6H), 6.92 (dd, 2H), 6.77-6.73 (m, 6H), 6.68 (dd, 1H), 6.43 (d, 2H) 210 7.92(dd, 2H), 7.89(dd, 1H), 7.80(d, 1H), 7.72(d, 1H), 7.59-7.51(m, 5H), 7.49-7.41(m, 5H), 7.32-7.27( m, 3H), 7.21-7.14 (m, 5H), 7.01 (t, 1H), 6.77-6.73 (m, 4H), 6.66 (dd, 1H), 6.61 (dd, 1H), 5.47 (d, 1H) 213 7.93(dd, 2H), 7.79-7.78(m, 2H), 7.72-7.59(m, 6H), 7.54-7.28(m, 15H), 7.20(t, 2H), 6.89(m, 2H), 6.75( dd, 2H), 6.68 (dd, 1H), 6.56-6.54 (m, 2H), 5.68 (d, 1H) 219 7.93 (dd, 2H), 7.79-7.67 (m, 6H), 7.62 (d, 1H), 7.53-7.28 (m, 11H), 7.18 (dt, 2H), 7.11 (dd, 2H), 6.89-6.82 ( m, 3H), 6.75 (dd, 2H), 6.68 (dd, 1H), 6.50 (d, 1H). 6.10 (d, 1H), 1.61 (s, 6H) 240 7.86(dd, 1H), 7.79-7.76(m, 2H), 7.73-7.70(m, 3H), 7.65-7.61(m, 2H), 7.55-7.28(m, 18H), 7.24-7.21(m, 2H) ), 6.70-6.65 (m, 3H), 6.59 (dd, 1H) 251 8.22(d, 1H), 7.82(d,1H), 7.77(td, 1H), 7.70(dd, 1H), 7.54-7.44(m, 7H), 7.39-7.22(m, 10H), 7.11(dd , 1H), 6.96 (dd, 1H), 6.57-6.47 (m, 3H), 1.68 (s, 6H) 253 8.22(d, 1H), 7.82(d,1 H), 7.72(d, 1H), 7.63(dd,1H), 7.51-7.21(m, 16H), 7.14-7.07(m, 2H), 6.86( dd, 1H), 6.61-6.59 (m, 1H), 6.53 (dd, 1H), 6.24 (td, 1H), 1.61 (s, 6H) 256 8.23(d, 1H), 7.82(d, 1H), 7.72(td,1H), 7.62(dd, 1H), 7.58-7.35(m, 3H), 7.34-7.21(m, 10H), 7.14-7.03 (m, 4H), 6.86 (dd, 1H), 6.61 (m, 1H), 6.53 (dd, 1 H), 6.24 (dd, 1H, 1.61 (s, 6H) 268 7.93 (dd, 2H), 7.79-7.66 (m, 6H). 7.62(d, 1H), 7.53-7.29(m, 11H), 7.20(dt,2H), 7.11-7.04(m, 4H), 6.89(d,1H), 6.87(t, 1H), 6.75( t, 1H), 6.74 (d, 1H), 6.66 (dd, 1H), 6.42 (dd, 1 H), 5.68 (d, 1 H), 1.52 (s, 6H) 269 7.93(d, 2H), 7.82(d, 1H), 7.80(d, 1H), 7.72-7.58(m, 5H), 7.53-7.36(m, 7H), 7.33-7.05(m, 9H), 6.87- 6.84(m, 2H), 6.79(dd,1 H), 6.75(dd,2H), 6.61(m, 1H), 6.23(d, 1H), 5.49(d, 1H), 1.61(s, 6H) 278 7.92(d, 2H), 7.89(d, 1H), 7.82(d,1H), 7.72(d, 1H), 7.62(dd, 1H), 7.59(d,1H), 7.48-7.41(m, 4H), 7.32-7.06 (m, 10H), 6.87 (d, 1H), 6.81 (dd, 1 H), 6.77-6.73 (m, 3H), 6.61 (m, 1 H), 6.23 (d, 1H) , 5.72 (dd, 1H), 1.61 (s, 6H) 281 7.92(d, 2H), 7.89(d,1 H), 7.82(d,1 H), 7.72(d,1 H), 7.59(dd, 2H), 7.49-7.40(m, 4H), 7.33-7.26 (m, 4H), 7.21-7.05 (m, 14H), 6.81-6.71 (m, 6H), 6.62 (m, 1H), 6.56 (dd, 1H), 5.72 (d, 1H), 5.68 (t, 1H) )

[Example] Comparative Example 1

For the anode, a Corning 15Ω/cm ² (1200Å) ITO glass substrate was cut into a size of 50mm x 50mm x 0.7mm, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, and then irradiated with ultraviolet rays for 30 minutes, It was cleaned by exposure to ozone, and this glass substrate was installed in a vacuum deposition apparatus.

First, 2-TNATA, a known material as a hole injection layer, was vacuum-deposited on the upper portion of the substrate to form a thickness of 600 Å, and then 4,4'-bis[N-(1-naphthyl), a hole transporting material as a hole transporting compound )-N-phenylamino]biphenyl (hereinafter, NPB) was vacuum-deposited to a thickness of 300 Å to form a hole transport layer.

9,10-di(naphthalen-2-yl)anthracene (hereinafter, DNA) as a known blue fluorescent host on the hole transport layer and 4,4'-bis[2-(4-), a known compound as a blue fluorescent dopant (N,N-diphenylamino)phenyl)vinyl]biphenyl (hereinafter, DPAVBi) was simultaneously deposited at a weight ratio of 98:2 to form a light emitting layer to a thickness of 300 Å.

Subsequently, Alq ₃ as an electron transport layer was deposited on the light emitting layer to a thickness of 300 Å, and then LiF, an alkali metal halide, was deposited on the electron transport layer to a thickness of 10 Å as an electron injection layer, and Al was deposited to a thickness of 3000 Å (cathode electrode). An organic light-emitting device was manufactured by vacuum deposition with a LiF/Al electrode to form a LiF/Al electrode.

Examples 1-28

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the compound shown in Table 3 was used instead of the NPB when the hole transport layer was formed.

Comparative Example 2

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the following compound A was used instead of the NPB when the hole transport layer was formed.

<Compound A>

Comparative Example 3

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the following compound B was used instead of the NPB when the hole transport layer was formed.

<Compound B>

Comparative Example 4

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the following compound C was used instead of the NPB when the hole transport layer was formed.

<Compound C>

Comparative Example 5

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the following compound D was used instead of the NPB when the hole transport layer was formed.

<Compound D>

Comparative Example 6

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the following compound E was used instead of the NPB when the hole transport layer was formed.

<Compound E>

Comparative Example 7

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the following compound F was used instead of the NPB when the hole transport layer was formed.

<Compound F>

Comparative Example 8

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the following compound G was used instead of the NPB when the hole transport layer was formed.

<Compound G>

Comparative Example 9

An organic light emitting diode was manufactured in the same manner as in Comparative Example 1, except that the following compound H was used instead of the NPB when the hole transport layer was formed.

<Compound H>

Device performance (driving voltage, luminance, efficiency and color coordinates) and current density of 100 mA/cm when driving at a current density of 50 mA/cm ² for the organic light emitting devices manufactured in Examples 1 to 28 and Comparative Examples 1 to 9 ² , the time (half-life) until the initial luminance decreases by 50% was measured and shown in Table 3 below.

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

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

hole transport material drive voltage
(V) current density
(mA/cm ² ) luminance
(cd/m ² ) efficiency
(cd/A) luminous color Half life (hr @100 mA/cm ² ) Example 1 compound 1 4.32 50 3670 7.34 blue 362 Example 2 compound 2 4.21 50 3715 7.43 blue 353 Example 3 compound 3 4.22 50 3665 7.33 blue 372 Example 4 compound 4 4.85 50 3876 7.75 blue 374 Example 5 compound 5 4.26 50 3730 7.46 blue 374 Example 6 compound 6 4.26 50 3730 7.46 blue 374 Example 7 compound 8 4.67 50 3985 7.97 blue 356 Example 8 compound 16 4.72 50 3451 6.90 blue 382 Example 9 compound 21 4.25 50 3630 7.26 blue 384 Example 10 compound 37 4.41 50 3725 7.45 blue 343 Example 11 compound 93 4.26 50 3630 7.26 blue 366 Example 12 compound 94 4.32 50 3670 7.34 blue 378 Example 13 compound 95 4.45 50 3440 6.88 blue 325 Example 14 compound 101 4.60 50 3490 6.98 blue 330 Example 15 compound 187 4.55 50 3655 7.31 blue 375 Example 16 compound 188 4.69 50 3492 6.98 blue 356 Example 17 compound 204 4.82 50 3540 7.08 blue 381 Example 18 compound 210 4.96 50 3987 7.97 blue 351 Example 19 compound 213 4.74 50 3859 7.72 blue 348 Example 20 compound 219 4.73 50 3565 7.13 blue 316 Example 21 compound 240 4.89 50 3529 7.06 blue 355 Example 22 compound 251 4.82 50 3983 7.97 blue 327 Example 23 compound 253 4.76 50 3852 7.70 blue 331 Example 24 compound 256 4.96 50 3874 7.75 blue 326 Example 25 compound 268 4.81 50 3721 7.44 blue 312 Example 27 compound 269 4.53 50 3652 7.30 blue 332 Example 27 compound 278 4.56 50 3552 7.10 blue 351 Example 28 compound 281 4.66 50 3512 7.02 blue 366 Comparative Example 1 NPB 7.01 50 2645 5.29 blue 258 Comparative Example 2 compound A 6.50 50 2805 5.61 blue 220 Comparative Example 3 compound B 5.81 50 3105 6.21 blue 180 Comparative Example 4 compound C 6.02 50 3205 6.41 blue 210 Comparative Example 5 compound D 8.21 50 1851 3.70 blue 127 Comparative Example 6 compound E 6.01 50 2353 5.98 blue 231 Comparative Example 7 compound F 7.32 50 2553 5.90 blue 221 Comparative Example 8 compound G 5.88 50 2678 5.34 blue 231 Comparative Example 9 compound H 5.68 50 2635 5.27 blue 235

As shown in Table 3, when the compound according to an embodiment of the present invention is used in an organic light emitting device as a hole transport material, all examples using the compound of the present invention are organic of Comparative Example 1 using NPB, a known material. Compared to the light emitting device, it exhibited excellent I-V-L characteristics with improved driving voltage and improved efficiency. Also, compared with Comparative Examples 2 to 9 using compounds A to H, it can be seen that the driving voltage is improved and the luminance, luminous efficiency and half-life are excellent. Although described, this is merely exemplary, and those of ordinary skill in the art to which the present invention pertains will understand that various modifications and equivalent other embodiments are possible therefrom. Therefore, the true technical protection scope of the present invention should be determined by the technical spirit of the appended claims.

10, 20, 30, 40: organic light emitting device
110: first electrode
150: organic layer
190: second electrode
210: first capping layer
220: second capping layer

Claims (13)

An amine-based compound represented by the following formula 1A or 1B:
<Formula 1A>

<Formula 1B>

In Formulas 1A and 1B,
A ₁ to A ₅ are each independently selected from a C ₅ -C ₃₀ carbocyclic group and a C ₁ -C ₃₀ heterocyclic group;
X ₁ is O, S, N-(L ₁ ) _a1- (R ₁ ) _b1 or C(R ₉ )(R ₁₀ ),
X ₂ is O, S or C(R ₁₁ )(R ₁₂ ),
L ₁ to L ₃ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,
a1 to a3 are each independently selected from an integer of 1 to 5;
R ₁ to R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl 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 ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ Heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted a C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁ )(Q ₂ )( Q ₃ ), -B(Q ₁ )(Q ₂ ) and -C(=O)(Q ₁ );
R ₉ and R ₁₀ and/or R ₁₁ and R ₁₂ are optionally linked to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group can be formed,
b1 to b3 and b5 to b8 are each independently selected from an integer of 1 to 10;
b4 is selected from an integer of 1 to 3,
However, in Formulas 1A and 1B, when A ₂ and A ₃ are a benzene group and X ₁ is C(R ₉ )(R ₁₀ ), R ₉ and R ₁₀ are bonded to each other and represented by Formula 7-3 excluded,

In Formula 7-3,
Z ₅₁ and Z ₅₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, spiro-bi Fluorenyl group, spiro-fluorene-benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenane selected from a trollinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ );
n3 and n4 are each independently selected from an integer of 1 to 4,
* is a carbon atom to which R ₉ and R ₁₀ are bonded,
Said substituted C ₅ -C ₆₀ carbocyclic group, substituted C ₁ -C ₆₀ heterocyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group , At least one of the substituents of the substituted C ₁ -C ₆₀ heteroaryloxy group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed polycyclic group is,
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, 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, amidino group, hydrazino group, hydrazono group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ hetero Cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed hetero polycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -B(Q ₁₁ )(Q ₁₂ ) ), -C(=O)(Q ₁₁ ), -S(=O) ₂ (Q ₁₁ ) and -P(=O)(Q ₁₁ )(Q ₁₂ ), C ₁ -C substituted with at least one selected from ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group and a terphenyl group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo Alkenyl group, C _{6 -C 60 aryl group, C 6 -C 60} aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, _monovalent non-aromatic condensed polycyclic group, monovalent ratio -Aromatic condensed heterocyclic polycyclic group, biphenyl group, terphenyl group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -B(Q ₂₁ )(Q ₂₂ ), -C(=O)(Q ₂₁ ), -S(=O) ₂ (Q ₂₁ ) and -P(=O)(Q ₂₁ )(Q ₂₂ ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, substituted with at least one selected from among; C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group and a terphenyl group; and
-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and - P(=O)(Q ₃₁ )(Q ₃₂ );
is selected from
The Q ₁ to Q ₃ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl group substituted selected from a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group and a terphenyl group. According to claim 1,
A ₁ to A ₅ are each independently, a benzene group, an indene group, a naphthalene group, an anthracene group, a fluorene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a pyrrole group, Imidazole group, pyrazole group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, indole group, isoindole group, indazole group, quinoline group, isoquinoline group, benzoquinoline group, naphthyridine group, quinoxaline group, quinazoline group, cinoline group, carbazole group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzimidazole group, furan group, benzofuran group, thiophene group, benzo Thiophene group, thiazole group, isothiazole group, benzothiazole group, isoxazole group, oxazole group, triazole group, oxadiazole group, triazine group, benzoxazole group, dibenzofuran group, An amine compound selected from a dibenzothiophene group, a benzocarbazole group and a dibenzocarbazole group. According to claim 1,
A ₁ to A ₅ are each independently selected from a benzene group and a naphthalene group, an amine-based compound. According to claim 1,
X ₁ is N-(L ₁ ) _a1- (R ₁ ) _b1 and X ₂ is O, S or C(R ₁₁ )(R ₁₂ );
X ₁ is O and X ₂ is C(R ₁₁ )(R ₁₂ ); or
X ₁ is C(R ₉ )(R ₁₀ ), and X ₂ is C(R ₁₁ )(R ₁₂ ), an amine-based compound. According to claim 1,
L ₁ to L ₃ are each independently, a single bond, a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthalene group, a fluorene group, spiro-by Fluorene group, benzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, penta phenylene group, hexacene group, pyrrole group, imidazole group, pyrazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, isoindole group, indole group, indazole group, purine group, quinoline group, Isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, cinoline group, carbazole group, phenanthridine group, acridine group, phenanthroline group, phenazine group group, benzimidazole group, furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, isoxazole group, oxazole group, triazole group, a tetrazole group, an oxadiazole group, a triazine group, a benzooxazole group, a dibenzofuran group, a dibenzothiophene group, a benzocarbazole group and a dibenzocarbazole group; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , C ₆ -C ₂₀ aryl group and C ₁ -C ₂₀ heteroaryl group substituted with at least one selected from a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, ace Naphthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthrene group, triphenylene group, pyrene group, chrysene group, naphtha sen group, picene group, perylene group, pentaphenylene group, hexacene group, pyrrole group, imidazole group, pyrazole group, pyridine group, pyrazine group, pyrimidine group, pyridazine group, isoindole group, indole group , indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, quinazoline group, synoline group, carbazole group, phenanthridine group, a Creidine group, phenanthroline group, phenazine group, benzimidazole group, furan group, benzofuran group, thiophene group, benzothiophene group, thiazole group, isothiazole group, benzothiazole group, isoxa Zole group, oxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, benzooxazole group, dibenzofuran group, dibenzothiophene group, benzocarbazole group and dibenzocarbazole group ;
selected from among, amine-based compounds. According to claim 1,
L ₁ to L ₃ are each independently,
single bonds and benzene groups; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , a benzene group substituted with at least one selected from a C ₆ -C ₂₀ aryl group and a C ₁ -C ₂₀ heteroaryl group;
selected from among, amine-based compounds. According to claim 1,
R ₁ and R ₂ are each independently selected from a C ₆ -C ₆₀ aryl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and
Deuterium, -F, -Cl, -Br, -I, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non- C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, substituted with at least one of an aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) , a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group;
selected from among, amine-based compounds. According to claim 1,
R ₁ and R ₂ are each independently selected from the group represented by the following Chemical Formulas 5-1 to 5-79, an amine compound:

In Formulas 5-1 to 5-79,
Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ), or Si(Z ₃₆ )(Z ₃₇ ),
Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, spiro-bi Fluorenyl group, spiro-fluorene-benzofluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyridi Nyl group, pyrazinyl group, pyrimidinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenane selected from a trollinyl group, a phenazinyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ );
Z ₃₃ and Z ₃₄ may be optionally linked to each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
e2 is selected from an integer of 0 to 2, and when e2 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,
e3 is selected from an integer of 0 to 3, and when e3 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,
e4 is selected from an integer of 0 to 4, and when e4 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,
e5 is selected from an integer of 0 to 5, and when e5 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,
e6 is selected from an integer of 0 to 6, and when e6 is 2 or more, Z ₃₁ and Z ₃₂ of 2 or more are the same as or different from each other,
e7 is selected from an integer of 0 to 7, and when e7 is 2 or more, Z ₃₁ of 2 or more are the same as or different from each other,
e9 is selected from an integer of 0 to 9, and when e9 is 2 or more, Z ₃₁ of 2 or more are the same as or different from each other,
* is a binding site with a neighboring atom. According to claim 1,
R ₁ and R ₂ are each independently selected from the following formulas 6-1 to 6-10 and 6-12 to 6-42, an amine-based compound:

In Formulas 6-1 to 6-10 and 6-12 to 6-42,
"Ph" represents a phenyl group,
* is a binding site with a neighboring atom. According to claim 1,
R ₃ to R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group , ter-butyl group, pentyl group, iso-amyl group, hexyl group, selected from a phenyl group and a biphenyl group, an amine compound. According to claim 1,
An amine compound represented by any one selected from the following formulas 1A-1 to 1A-4 and 1B-1 to 1B-16:
<Formula 1A-1>

<Formula 1A-2>

<Formula 1A-3>

<Formula 1A-4>

<Formula 1B-1>

<Formula 1B-2>

<Formula 1B-3>

<Formula 1B-4>

<Formula 1B-5>

<Formula 1B-6>

<Formula 1B-7>

<Formula 1B-8>

<Formula 1B-9>

<Formula 1B-10>

<Formula 1B-11>

<Formula 1B-12>

<Formula 1B-13>

<Formula 1B-14>

<Formula 1B-15>

<Formula 1B-16>

In Formulas 1A-1 to 1A-4 and 1B-1 to 1B-16,
The definitions for X ₁ , X ₂ , L ₁ to L ₃ , a1 to a3 and R ₁ to R ₁₂ and b1 and b2 are the same as in the description in claim 1 ,
b4, b6 and b8 are each independently selected from an integer of 1 to 3,
b3, b5 and b7 are each independently selected from an integer of 1 to 4. 12. The method of claim 11,
The L ₁ to L ₃ are independently of each other,
single bonds and benzene groups; and
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , a benzene group substituted with at least one selected from a C ₆ -C ₂₀ aryl group and a C ₁ -C ₂₀ heteroaryl group;
selected from among, amine-based compounds. According to claim 1,
An amine compound selected from the following compounds 1 to 284, 208A and 226A:

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