KR102547684B1 - Condensed-cyclic compound and organic light-emitting device comprising the same - Google Patents

Abstract

A condensed cyclic compound and an organic light emitting device including the same are disclosed.

Description

Condensed-cyclic compound and organic light-emitting device comprising the same

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

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

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 light emitting layer via the hole transport region, and electrons injected from the second electrode move to the light emitting layer via the electron transport region. Carriers such as holes and electrons recombine in the light emitting layer region to generate excitons. As these excitons change from the excited state to the ground state, light is generated.

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

According to one aspect,

A condensed cyclic compound represented by Formula 1-1 or 1-2 is provided:

<Formula 1-1> <Formula 1-2>

In Chemical Formulas 1-1 and 1-2,

ring A ₁ is benzene;

A ₂ ring is a C ₆ -C ₆₀ aromatic ring or a C ₁ -C ₆₀ heteroaromatic ring;

A ₃ ring is a C ₇ -C ₆₀ aromatic ring or a C ₁ -C ₆₀ heteroaromatic ring;

X ₁ is selected from C(R ₁₁ )(R ₁₂ ), O and S;

X ₂ is selected from C(R ₁₃ )(R ₁₄ ), O and S;

R ₁ to R ₃ and R ₁₁ to R ₁₄ are each independently selected from hydrogen, deuterium (-D), -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, 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 ₂ -C ₆₀ alkynyl group a C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ - C ₆₀ arylthio group, 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 polycyclic group, - Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=0)(Q ₁ ), -S( =O) is selected from ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ );

b1 is selected from an integer of 0 to 2, b2 and b3 are each independently selected from an integer of 0 to 10,

T ₁ is a group represented by Formula 2 below;

<Formula 2>

In Formula 2,

L ₁ and L ₂ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group. 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 Among substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic groups being selected,

a1 is selected from 0, 1, 2 and 3, a2 is selected from 1, 2 and 3;

Ar ₁ is hydrogen, deuterium (-D), -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 substituted 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 heterocycloalke Nyl 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 polycyclic group, -Si(Q ₄ )(Q ₅ )(Q ₆ ) , -N(Q ₄ )(Q ₅ ), -B(Q ₄ )(Q ₅ ), -C(=O)(Q ₄ ), -S(=O) ₂ (Q ₄ ) and -P(= O) (Q ₄ ) (Q ₅ ) selected from,

c1 is selected from an integer of 1 to 9;

f1 is selected from integers from 1 to 3;

The above substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic heterocondensed polycyclic 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 hetero Cycloalkyl 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 At least one of the substituents of _{the 6} -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heteropolycyclic group,

Heavy hydrogen (-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;

Heavy hydrogen, -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 heterocondensed polycyclic 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;

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 hetero condensed polycyclic group;

Heavy hydrogen, -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 non-aromatic group -Aromatic heterocondensed polycyclic 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 ) substituted with at least one selected from, 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, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=0) ₂ (Q ₃₁ ) and -P(=0)(Q ₃₁ )(Q ₃₂ );

is selected from

Wherein Q ₁ to Q ₆ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, and cyanide. 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 heteroaryl group , a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl group, and a terphenyl group,

* is a binding site with a neighboring atom.

An organic light emitting device including the condensed cyclic compound may have high efficiency and long lifespan.

1 to 4 are diagrams each schematically showing a structure of an organic light emitting device according to an embodiment.

The condensed cyclic compound is represented by Formula 1-1 or 1-2:

<Formula 1-1> <Formula 1-2>

In Chemical Formulas 1-1 and 1-2,

The A ₁ ring may be benzene.

In Formulas 1-1 and 1-2, ring A ₂ is a C ₆ -C ₆₀ aromatic ring or C ₁ -C ₆₀ heteroaromatic ring, and ring A ₃ is a C ₇ -C ₆₀ aromatic ring or C ₁ -C ₆₀ It may be a heteroaromatic ring.

For example, in Chemical Formulas 1-1 and 1-2, ring A ₂ is selected from benzene, naphthalene, anthracene, phenanthrene, and triphenylene;

The A ₃ ring may be selected from naphthalene, anthracene, phenanthrene and triphenylene.

According to another embodiment, ring A ₂ in Chemical Formulas 1-1 and 1-2 may be benzene, and ring A ₃ may be naphthalene.

In Formulas 1-1 and 1-2, X ₁ is selected from C(R ₁₁ )(R ₁₂ ), O and S, and X ₂ is selected from C(R ₁₃ )(R ₁₄ ), O and S. can The R ₁₁ to R ₁₄ will be described later.

For example, in Chemical Formulas 1-1 and 1-2,

X ₁ and X ₂ are S;

X ₁ is C(R ₁₁ )(R ₁₂ ) and X ₂ is S;

X ₁ is S and X ₂ is C(R ₁₃ )(R ₁₄ );

X ₁ is O and X ₂ is S;

X ₁ and X ₂ are O;

X ₁ is C(R ₁₁ )(R ₁₂ ) and X ₂ is O;

X ₁ is O and X ₂ is C(R ₁₃ )(R ₁₄ ); or

X ₁ may be S, and X ₂ may be O;

In Chemical Formulas 1-1 and 1-2,

R ₁ to R ₃ and R ₁₁ to R ₁₄ are each independently selected from hydrogen, deuterium (-D), -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, 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 ₂ -C ₆₀ alkynyl group a C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ - C ₆₀ arylthio group, 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 polycyclic group, - Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=0)(Q ₁ ), -S( =O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ). The Q ₁ to Q ₃ will be described later.

For example, in Formulas 1-1 and 1-2, R ₁ to R ₃ and R ₁₁ to R ₁₄ are each independently

Hydrogen, heavy hydrogen (-D), -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;

A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, Indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group (phenanthrenyl), anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl Picenyl, perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl ( ovalenyl), thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group ), a benzocarbazolyl group, a dibenzocarbazolyl group and a dibenzosilolyl group; and

Heavy hydrogen, -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, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorene Nyl 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, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group , A benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, substituted with at least one selected from Nyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthre Nyl 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, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group and dibenzo silole diary; is selected from

Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, and 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, phenanthre It may be selected from a yl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, and a carbazolyl group.

According to another embodiment, in Chemical Formulas 1-1 and 1-2,

R ₁ to R ₃ and R ₁₁ to R ₁₄ are independently of each other,

Hydrogen, heavy hydrogen, -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;

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group, carbazolyl group , A benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group; and

Heavy hydrogen, -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, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group, carbazole a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), a phenyl group, a biphenyl group, substituted with at least one selected from A phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl 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, in Chemical Formulas 1-1 and 1-2,

R ₁ to R ₃ and R ₁₁ to R ₁₄ are each independently selected from hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, It may be selected from a hydrazono group, a C ₁ -C ₂₀ alkyl group, and a C ₁ -C ₂₀ alkoxy group.

In Chemical Formulas 1-1 and 1-2, b1 may be selected from an integer of 0 to 2, and b2 and b3 may be each independently selected from an integer of 0 to 10.

In Formulas 1-1 and 1-2, b1 indicates the number of R ₁ s, and when b1 is 2 or more, two or more R _1s are the same as or different from each other. Descriptions of b2 and b3 may be understood with reference to the description of b1 and the structures of Chemical Formulas 1-1 and 1-2 above.

For example, in Chemical Formulas 1-1 and 1-2, b1 may be selected from an integer of 0 to 2, b2 may be selected from an integer of 0 to 4, and b3 may be selected from an integer of 0 to 5. It is not limited to this.

In Formulas 1-1 and 1-2, T ₁ may be a group represented by Formula 2 below:

<Formula 2>

In Formula 2,

L ₁ and L ₂ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group. 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 Among substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic groups can be chosen

For example, in Formula 2,

L ₁ and L ₂ are each independently a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group ( heptalenylene), indacenylene, acenaphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenyl phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, Coronenylene group, ovalenylene group, pyrrolylene group, thiophenylene group, furanylene group, carbazolylene group, benzofuranylene group (benzofuranylene), benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene and dibenzocarbazolylene groups; and

Heavy hydrogen, -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, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, flu Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group, pyrenyl group, chrysenyl group group, naphthacenyl group, picenyl group, peryl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group , A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, and an azulenylene group, substituted with at least one of a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group , Heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, Anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubycenylene group , coronenylene group, ovalenylene group, pyrrolene group, thiophenylene group, furanylene group, carbazolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzo a carbazolylene group and a dibenzocarbazolylene group; can be selected from.

According to another embodiment, L ₁ and L ₂ in Formula 2 may be each independently selected from the group represented by Formula 3-1 to Formula 3-22, but are not limited thereto:

In Chemical Formulas 3-1 to 3-22,

Y ₁ is selected from O, S, C(Z ₃ )(Z ₄ ), N(Z ₅ ) and Si(Z ₆ )(Z ₇ );

Z ₁ to Z ₇ are each independently selected from hydrogen, heavy hydrogen, -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, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, It is selected from an anthracenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ),

Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a biphenyl group, and a terphenyl group;

d1 is selected from an integer from 1 to 4, d2 is selected from an integer from 1 to 3, d3 is selected from an integer from 1 to 6, d4 is selected from an integer from 1 to 8, and d5 is selected from an integer from 1 to 5 It is selected from integers, and * and *' are binding sites with neighboring atoms.

According to another embodiment, L ₁ and L ₂ in Formula 2 may be each independently selected from the groups represented by Formulas 4-1 to 4-35:

In Formulas 4-1 and 4-35, * and *' are binding sites with neighboring atoms.

In Formula 2, a1 indicates the number of L ₁ , and is selected from 0, 1, 2, and 3. For example, a1 in Formula 2 may be 0 or 1, but is not limited thereto. When a1 is 0, *-(L ₁ ) _a1 -*' is a single bond. When a1 is 2 or more, 2 or more L ₁ 's are the same as or different from each other.

In Formula 2, a2 indicates the number of L ₂ , and is selected from 1, 2, and 3. For example, a2 in Chemical Formula 1 may be 1 or 2. When a2 is 2 or more, 2 or more L ₂ are the same as or different from each other.

For example, in Formula 2, a1 may be 0 or 1, and a2 may be 1, but is not limited thereto.

In Formula 2, Ar ₁ is 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 group, substituted 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 ₁ -C ₆₀ alkoxy group Cyclic 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 heterocycloalkyl group Alkenyl 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 polycyclic group, -Si(Q ₄ )(Q ₅ )(Q ₆ ), -N(Q ₄ )(Q ₅ ), -B(Q ₄ )(Q ₅ ), -C(=O)(Q ₄ ), -S(=O) ₂ (Q ₄ ) and -P( =0) (Q ₄ ) (Q ₅ ).

For example, Ar ₁ in Formula 2 is

Hydrogen, heavy hydrogen, -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;

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, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a 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, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzo a carbazolyl group, a dibenzocarbazolyl group and a dibenzosilolyl group; and

Heavy hydrogen, -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, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl 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, penta A phenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, which is substituted with at least one selected from a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) Nyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl 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, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group and dibenzosilol diary; 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 naphthyl group, a biphenyl group, and a terphenyl group.

According to another embodiment, Ar ₁ in Formula 2 is

Hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group; and

It may be selected from groups represented by Chemical Formulas 5-1 to 5-16, but is not limited thereto:

In Chemical Formulas 5-1 to 5-16,

Y ₃₁ is selected from O, S, C(Z ₃₃ ) (Z ₃₄ ), N(Z ₃₅ ) and Si(Z ₃₆ ) (Z ₃₇ );

Z ₃₁ to Z ₃₇ are each independently hydrogen, heavy hydrogen, -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 and 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, triphenylenyl group, pyrenyl group , chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group; and

Heavy hydrogen, -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, triphenylenyl group, pyrene A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, substituted with at least one selected from a phenyl group, a chrysenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group , Fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group , a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; is selected from

e3 is selected from an integer from 1 to 3, e4 is selected from an integer from 1 to 4, e5 is selected from an integer from 1 to 5, e6 is selected from an integer from 1 to 6, and e7 is selected from an integer from 1 to 7 It is selected from integers, and e9 is selected from integers from 1 to 9.

According to another embodiment, Ar ₁ in Formula 2 is

Hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group; and

It may be selected from Chemical Formulas 6-1 to 6-44, but is not limited thereto:

In Formulas 6-1 to 6-44, * is a binding site with a neighboring atom.

According to another embodiment, in Formula 2,

Ar ₁ is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzo group. Thiophenyl group; and

Heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazole, substituted with at least one selected from a phenyl group and a naphthyl group diyl groups, dibenzofuranyl groups and dibenzothiophenyl groups; can be selected from.

In Formula 2, c1 may be selected from an integer of 1 to 9.

In Formula 2, c1 represents the number of -[(L ₁ ) _a1 -Ar ₁ ], and when c1 is 2 or more, two or more -[(L ₁ ) _a1 -Ar ₁ ] are the same as or different from each other. For example, c1 may be selected from an integer of 1 to 4. As another example, c1 in Chemical Formula 2 may be 1 or 2.

In Chemical Formulas 1-1 and 1-2, f1 represents the number of T ₁ , and f1 may be an integer selected from 1 to 3. When f1 is 2 or more, two or more T ₁ are the same as or different from each other. For example, f1 may be 1.

According to one embodiment, in Chemical Formulas 1-1 and 1-2, T ₁ may be represented by the following Chemical Formula 2A:

<Formula 2A>

In Formula 2A, L ₁ , L ₂ , a1 and a2 are the same as those described herein, Ar _1a to Ar _1i refer to Ar ₁ described herein, and * is a binding site with a neighboring atom.

For example, in Formula 2A, Ar _1a to Ar _1i are each independently

Hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group; and

It may be selected from the groups represented by Chemical Formulas 6-1 to 6-44.

According to another embodiment, in Chemical Formulas 1-1 and 1-2, T ₁ may be represented by Chemical Formula 2A(1):

<Formula 2A (1)>

In Formula 2A(1), L ₁ , L ₂ , a1 and a2 are the same as those described herein, Ar _1e refers to Ar ₁ described herein, and * is a binding site with a neighboring atom.

For example, in Chemical Formula 2A(1), Ar _1e may be selected from the groups represented by Chemical Formulas 6-1 to 6-44.

As another example, in Formula 2A(1), Ar _1e is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, or a chrysenyl group. group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group; and

Heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group , Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazole, substituted with at least one selected from a phenyl group and a naphthyl group diyl groups, dibenzofuranyl groups and dibenzothiophenyl groups; can be selected from.

According to one embodiment, the condensed cyclic compound may be represented by one of Formulas 1(1) to 1(18) below.

In Chemical Formulas 1(1) to 1(18), X ₁ , X ₂ , R ₁ to R ₃ , b1 and T ₁ are referred to as described herein, b2 is an integer selected from 0 to 4, and b3 is selected from an integer of 0 to 5, and f1 is 1 or 2.

For example, in Chemical Formulas 1(1) to 1(18), T ₁ may be a group represented by Chemical Formula 2A, and f1 may be 1.

As another example, in Chemical Formulas 1(1) to 1(18), T ₁ may be a group represented by Chemical Formula 2A(1), and f1 may be 1.

According to another embodiment, the condensed cyclic compound may be represented by one of the following Chemical Formulas 1(1)-1 to 1(18)-1, but is not limited thereto:

In Chemical Formulas 1(1)-1 to 1(18)-1, X ₁ , X ₂ and T ₁ refer to those described herein.

For example, in Chemical Formulas 1(1)-1 to 1(18)-1, T ₁ may be a group represented by Chemical Formula 2A.

As another example, in Chemical Formulas 1(1)-1 to 1(18)-1, T ₁ may be a group represented by Chemical Formula 2A(1).

As another example, in Formulas 1(1)-1 to 1(18)-1,

X ₁ and X ₂ are S;

X ₁ is C(R ₁₁ )(R ₁₂ ) and X ₂ is S;

X ₁ is S and X ₂ is C(R ₁₃ )(R ₁₄ );

X ₁ is O and X ₂ is S;

X ₁ and X ₂ are O;

X ₁ is C(R ₁₁ )(R ₁₂ ) and X ₂ is O;

X ₁ is O and X ₂ is C(R ₁₃ )(R ₁₄ ); or

X ₁ may be S and X ₂ may be O; but is not limited thereto.

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

Alternatively, the condensed cyclic compound may be one of the following compounds H1 to H9, but is not limited thereto:

In Formulas 1-1 and 1-2, ring A ₃ is a C ₇ -C ₆₀ aromatic ring or a C ₁ -C ₆₀ heteroaromatic ring. That is, the C ₆ aromatic ring (ie, benzene) is excluded from the list of A ₃ rings. When ring A ₃ in Formulas 1-1 and 1-2 is benzene, the size of the molecular structure is, but is not limited to, the size of the structure of the condensed cyclic compound represented by Formula 1-1 or 1-2. Since it is smaller, the degree of dispersion of electrons is small and does not contribute to stabilizing the molecular structure.

In Formula 1-1 or 1-2, T ₁ is a group represented by Formula 2, and the condensed cyclic compound and the group represented by Formula 2 are connected to each other by L ₂ . When the group represented by Chemical Formula 2 is linked to the condensed cyclic compound by L ₂ , the degree of electron dispersion is greater than that when the group is directly linked without L ₂ , and may contribute to stabilization of the entire molecular structure. In addition, since the entire molecular structure is three-dimensional, it is excellent in non-crystallization, and film properties can be improved.

The condensed cyclic compound represented by Chemical Formula 1-1 or 1-2 may be synthesized using a known organic synthesis method. A method of synthesizing the condensed cyclic compound can be recognized by those skilled in the art by referring to Examples to be described later.

[Description of Figure 1]

1 is a schematic cross-sectional view of an organic light emitting diode 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 below the first electrode 110 or above the second electrode 190 in FIG. 1 . As the substrate, a glass substrate or a plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance may be used.

The first electrode 110 may be formed, for example, by providing a material for the first electrode on a substrate using a deposition method or a sputtering method. When the first electrode 110 is an anode, a material for the first electrode may be selected from materials having a high work function so as 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 of these It may be selected from a combination of, but is not limited thereto. Alternatively, in order to form the first electrode 110, which 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 of a single layer or a multi-layer structure of 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 may include a condensed cyclic compound represented by Chemical Formula 1-1 or 1-2.

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 have i) a single layer structure composed of a single layer made of a single material, ii) a single layer structure composed of a single layer composed 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 a structure.

The hole transport region may include the condensed cyclic compound represented by Chemical Formula 1-1 or 1-2.

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 has a single layer structure made of a plurality of single layers made of different materials, or a hole injection layer/hole transport layer sequentially stacked from the first electrode 110, or a hole injection layer/hole transport layer. / It may have a multi-layer structure of a light emitting auxiliary layer, a hole injection layer/light emitting auxiliary layer, a hole transport layer/a light emitting auxiliary layer, or a hole injection layer/hole transport layer/electron blocking layer, but is not limited thereto.

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) , PEDOT/PSS (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate) (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate)), Pani/CSA (Polyaniline/ Camphor sulfonic acid (polyaniline/camphorsulfonic acid)), PANI/PSS (Polyaniline/Poly(4-styrenesulfonate) (polyaniline/poly(4-styrenesulfonate)), a compound represented by Formula 201 and Formula 202 below It may include at least one selected from compounds:

<Formula 201>

<Formula 202>

In Chemical 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, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group. 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 hetero condensed polycyclic 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 - A C ₂₀ alkenylene group, 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, 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 It is selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group,

xa1 to xa4 are each independently selected from integers of 0 to 3;

xa5 is an integer selected from 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 heterocondensed group. It can be selected from polycyclic groups.

For example, R ₂₀₁ and R ₂₀₂ in Formula 202 may optionally be linked 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 Chemical Formulas 201 and 202,

L ₂₀₁ to L ₂₀₅ are independently of each other;

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 Ryllenylene 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; and

Heavy hydrogen, -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 Alkyl group substituted phenyl 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, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, substituted with at least one selected from -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) and -N(Q ₃₁ )(Q ₃₂ ) Ren group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenyl Ren group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, peryle 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 be 0, 1 or 2 independently of each other.

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, pi Renyl group, chrysenyl group, naphthacenyl group, picenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazole diyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group; and

Heavy hydrogen, -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 Alkyl group substituted phenyl 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 diyl group, dibenzocarbazolyl group, dibenzosilolyl group, 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, rubicenyl 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

The description of the above Q ₃₁ to Q ₃₃ refers to what is described herein.

According to another embodiment, at least one of R ₂₀₁ to R ₂₀₃ in Formula 201 is independently of each other,

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

Heavy hydrogen, -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 Alkyl group substituted phenyl group, -F substituted phenyl group, naphthyl group , A fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group substituted with at least one selected from a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a di A benzofuranyl group and a dibenzothiophenyl group;

It 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,

Carbazolyl group; and

Heavy hydrogen, -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 Alkyl group substituted phenyl 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;

It may be selected from, but is not limited thereto.

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

<Formula 201A>

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

<Formula 201A (1)>

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

<Formula 201A-1>

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

<Formula 202A>

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

<Formula 202A-1>

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

Descriptions of L ₂₀₁ to L ₂₀₃ , xa1 to xa3, xa5 and R ₂₀₂ to R ₂₀₄ refer to those described herein,

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

R ₂₁₃ to R ₂₁₇ are each independently selected from hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, C ₁ Substituted with -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, rubicenyl 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 hole injection layer has a thickness of about 100 Å to about 9000 Å, for example, about 100 Å to about 1000 Å, and the hole transport layer has a thickness of about 50 Å. to about 2000 Å, for example about 100 Å to about 1500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the aforementioned ranges, satisfactory hole transport characteristics may be obtained without a substantial increase in driving voltage.

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

[p-dopant]

The hole transport region may further include a charge-generating material to improve conductivity in addition to the material described above. 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 -3.5eV or less.

The p-dopant may include at least one selected from quinone derivatives, metal oxides, and cyano group-containing compounds, but is not limited thereto.

For example, the p-dopant,

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 (1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile); and

a compound represented by Formula 221;

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

<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. , 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 ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent group, It is selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, wherein at least one of R ₂₂₁ to R ₂₂₃ is a cyano group, -F, -Cl, -Br, -I, At least one 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 has one substituent.

[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 subpixel. 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 contacted or separated from each other and stacked, 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 any light, and can emit white light.

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

The light emitting layer may include a condensed cyclic compound represented by Chemical Formula 1-1 or 1-2.

The host may include a condensed cyclic compound represented by Formula 1-1 or 1-2.

The emission layer may further include a fluorescent dopant in addition to the condensed cyclic compound represented by Formula 1-1 or 1-2.

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

The 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 aforementioned range, excellent light emitting characteristics may be exhibited without a substantial increase in driving voltage.

[Phosphorescent dopant included in the light emitting layer of the organic layer 150]

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

<Formula 401>

M(L ₄₀₁ ) _xc1 (L ₄₀₂ ) _xc2

<Formula 402>

Among Chemical 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 ligands represented by Formula 402, xc1 is 1, 2, or 3, and when xc1 is 2 or more, two or more L _401s are the same as or different from each other;

L ₄₀₂ is an organic ligand, xc2 is an integer selected from 0 to 4, and when xc2 is 2 or more, two or more L _402s 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(Q ₄₁₁ )=*', and the Q ₄₁₁ and Q ₄₁₂ is hydrogen, heavy hydrogen, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group;

X ₄₀₆ is a single bond, O or S;

R ₄₀₁ and R ₄₀₂ are each independently selected from 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 An unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or unsubstituted C ₁ -C ₂₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, A substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ - A C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or Unsubstituted monovalent non-aromatic heterocondensed polycyclic group -Si(Q ₄₀₁ )(Q ₄₀₂ )(Q ₄₀₃ ), -N(Q ₄₀₁ )(Q ₄₀₂ ), -B(Q ₄₀₁ )(Q ₄₀₂ ), - selected from C(=O)(Q ₄₀₁ ), -S(=O) ₂ (Q ₄₀₁ ) and -P(=O)(Q ₄₀₁ )(Q ₄₀₂ ), and the Q ₄₀₁ to Q ₄₀₃ are independently from each other , C ₁ -C ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group, C ₆ -C ₂₀ aryl group and C ₁ -C ₂₀ selected from heteroaryl group,

xc11 and xc12 are each independently selected from integers from 0 to 10;

In Formula 402, * and *' are binding sites with M in Formula 401.

According to one embodiment, A ₄₀₁ and A ₄₀₂ in Formula 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, a 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, benzooxazole 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.

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

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

Hydrogen, heavy hydrogen, -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;

Heavy hydrogen, -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 groups, triazinyl groups, quinolinyl groups, isoquinolinyl groups, quinoxalinyl groups, quinazolinyl groups, carbazolyl groups, dibenzofuranyl groups and dibenzothiophenyl groups;

Heavy hydrogen, -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 A cyclopentyl group, a cyclohexyl group, substituted with at least one selected from a ginyl 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 Pyl 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, que 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 (=0) ₂ (Q ₄₀₁ ) and -P(=0)(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 are not limited thereto.

According to another embodiment, when xc1 in Formula 401 is 2 or more, two A _401s among two or more L _401s are optionally linked to each other through a linking group X ₄₀₇ , or two A _402s are optionally , and may be linked to each other through a linking group X ₄₀₈ (see compounds PD1 to PD4 and PD7 below). X ₄₀₇ and X ₄₀₈ are independently of each other, a single bond, *-O-*', *-S-*', *-C(=0)-*', *-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, the L ₄₀₂ is halogen, diketone (eg acetylacetonate), carboxylic acid (eg picolinate), -C(=0), isonitrile, -CN and phosphorus (For example, it may be selected from phosphine and phosphite), but is not limited thereto.

Alternatively, the phosphorescent dopant may be selected from, for example, 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 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, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group. 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 hetero condensed polycyclic group,

xd1 to xd3 are each independently selected from integers from 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. , A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, 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 heteropolycyclic group being 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 , a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, and an indenophenanthrene group; and

Heavy hydrogen, -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 phenyl group, a biphenyl group, a naphthalene group, a heptalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, phenalene, substituted with at least one selected from a terphenyl group and a naphthyl group group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group and indenopenan Tren group;

can be selected from.

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

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, perylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzo A furanylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group; and

Heavy hydrogen, -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, spy, 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, peryle Nylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranyl a rene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group;

can be selected from.

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

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyle 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

Heavy hydrogen, -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 among 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 has 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 multi-layer structure having a plurality of layers made of a plurality of different materials can have

The electron transport region may include a condensed cyclic compound represented by Formula 1-1 or 1-2.

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 among the electron transport regions) may include a metal-free compound including at least one π electron deficient nitrogen 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- to 7-membered heteromonocyclic group having at least one *-N=*' moiety, or ii) at least one *- A heteropolycyclic group in which two or more of the 5- to 7-membered heteromonocyclic groups having an N=*' moiety are condensed with each other, or iii) a 5-membered heterocyclic group having at least one *-N=*' moiety to 7-membered heteromonocyclic group, and at least one C ₅ -C ₆₀ carbocyclic group may be a heteropolycyclic group 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 Formula 601 below.

<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 ₃ -C ₁₀ cycloalkenylene group, An 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 bi- It is selected from an aromatic condensed 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, or a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group. 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 ), and ,

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 the π electron deficient nitrogen-containing ring as described above.

According to one embodiment, 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, pentaphene 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, benzoimidazole group, isobenzothiazole group , Benzooxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group and azacarbazole group ; and

Heavy hydrogen, -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 phenyl group, a biphenyl group, a terphenyl group, a 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, Fluoranthene group, triphenylene group, pyrene group, chrysene group, naphthacene group, picene group, perylene group, pentaphene group, indenoanthracene group, dibenzofuran group, dibenzothiophene group, carba sol 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, sinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, Benzoimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, a dazopyrimidine group and an 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 _601s 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 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 ), at least one of X ₆₁₄ to X ₆₁₆ is N,

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

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

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

R ₆₁₄ to R ₆₁₆ are each independently selected from hydrogen, heavy hydrogen, -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 independently of each other,

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, perylene 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 , Thiazolyne group, isothiazolylene group, oxazolylene group, isoxazolylene group, thiadiazolyne 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, phenan Trollinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazolyne group, benzoxazolylene group, isobenzooxazolylene group, triazolylene group, tetrazolylenic group, imidazopyridinylene group, imidazopyrimidi a nylene group and an azacarbazolylene group; and

Heavy hydrogen, -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, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group , An isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group substituted with at least one selected from 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, dibenzofuran Ranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosilolylene group, pyridinylene group, imidazolylene group, pyrazolylene group, thiazolylenic group, isothiazolylenic group, oxazolyl Ren group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinyl Ren group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazinylene group, benzoimidazolyl a rene group, an isobenzothiazolylene group, a benzooxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group;

It may be selected from, but is not limited thereto.

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

According to another embodiment, R 601 and R ₆₁₁ to R ₆₁₃ in Formulas 601 and _601-1 are independently of each other,

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyle 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, cynolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group;

Heavy hydrogen, -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, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl 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 at least one selected from azacarbazolyl group, substituted with a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, flu Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, peryle 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, 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, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazole diyl, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group; and

-S(=0) ₂ (Q ₆₀₁ ) and -P(=0)(Q ₆₀₁ ) (Q ₆₀₂ );

is selected from

The description of the above Q ₆₀₁ and Q ₆₀₂ refers to what is described 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(3-(Biphenyl-4-yl)-5-(4- tert -butylphenyl)-4-phenyl- 4H -1 ,2,4-triazole) and at least one compound selected from NTAZ.

The buffer layer, the hole blocking layer, or the electron control layer may each independently have a thickness of about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the buffer layer, the hole blocking layer, or the electron control layer satisfies the aforementioned range, excellent hole blocking characteristics or electron control characteristics may 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 aforementioned range, satisfactory electron transport characteristics may be obtained without a substantial increase in driving voltage.

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

The metal-containing material may include at least one selected from alkali metal complexes and alkaline earth metal complexes. The metal ion of the alkali metal complex may be selected from Li ion, Na ion, K ion, Rb ion and Cs ion, and the metal ion of the alkaline earth metal complex is Be ion, Mg ion, Ca ion, Sr ion and Ba ion. ions can be selected. The ligands coordinated to the metal ions of the alkali metal complex and the alkaline earth metal complex are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyl Oxazole, hydroxyphenylthiazole, hydroxydiphenyloxadiazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, 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 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 multi-layer 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 among Sc, Y, Ce, Tb, Yb, Gd and Tb.

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, and K ₂ O, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and KI. According to one 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 one 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 the alkali metal, alkaline earth metal, and rare earth metal as described above, and are coordinated to the metal ions of the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex. Ligands are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiphenyloxa diazoles, hydroxydiphenylthiadiazoles, hydroxyphenylpyridines, hydroxyphenylbenzoimidazoles, hydroxyphenylbenzothiazoles, bipyridines, phenanthrolines, and cyclopentadienes, but are limited thereto. It is not.

The electron injection layer is composed of only 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 , It may further include the organic material. 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 a matrix composed 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 aforementioned range, satisfactory electron injection characteristics may be obtained without a substantial increase in driving voltage.

[Second electrode 190]

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

The second electrode 190 includes lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In) ), magnesium-silver (Mg-Ag), it 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 of a single layer or a multi-layer structure of a plurality of layers.

[Description of Figures 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. The light emitting element 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 element 40 of FIG. 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 sequentially stacked structure.

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 .

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

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

The first capping layer 210 and the second capping layer 220 may be independently of each other 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-based compound, a porphine derivative, or a phthalocyanine derivative ( phthalocyanine derivatives), naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compound, heterocyclic compound and amine-based compound may be optionally substituted with a substituent containing 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 may independently include an amine-based compound.

For example, at least one of the first capping layer 210 and the second capping layer 220 may include the condensed cyclic compound represented by Chemical Formula 1-1 or 1-2.

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

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

In the above, the organic light emitting device has been described with reference to FIGS. 1 to 4, but 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 each vacuum deposition method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, 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 are formed by a vacuum deposition method, the deposition conditions are, for example, a deposition temperature of about 100 to about 500 ° C., about 10 Within the range of ^-8 to about 10 ^-3 torr vacuum degree and about 0.01 to about 100 Å/sec deposition rate, it may be selected in consideration of the compound 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 formed by the spin coating method, 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 °C to 200 °C, it may be selected in consideration of the compound to be included in the layer to be formed and the structure of the layer to be formed.

[General definition of substituents]

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 methyl, ethyl, propyl, isobutyl, sec-butyl group, ter-butyl group, pentyl group, iso-amyl group, hexyl group and the like. In the present specification, a C ₁ -C ₆₀ alkylene group means a divalent group having the same structure as the 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 end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, a propenyl group, and a butenyl group. etc. are included. In the present specification, a C ₂ -C ₆₀ alkenylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

In the present specification, the C ₂ -C ₆₀ alkynyl group refers to a hydrocarbon group including one or more carbon triple bonds in the middle or at the end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group, a propynyl group, and the like included In the present specification, a C ₂ -C ₆₀ alkynylene group means a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

In the present specification, the C ₁ -C ₆₀ alkoxy group refers to a monovalent group having a chemical formula of -OA ₁₀₁ (where A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group and an ethoxy group. , isopropyloxy groups, 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 cycloalkyl group. Heptyl groups and the like are included. In the present specification, a 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 , Specific examples thereof include a 1,2,3,4-oxatriazolidinyl group (1,2,3,4-oxatriazolidinyl), a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. In the present specification, a 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, a C ₃ -C ₁₀ cycloalkenyl group is a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one double bond in the ring but does not have aromaticity. Examples include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group and the like. In the present specification, a 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, and has at least one double bond in it. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-hydrofuranyl group, and a 2,3-hydrothiophenyl group. etc. 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, a C ₆ -C ₆₀ aryl group means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C ₆ -C ₆₀ arylene group refers to 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 has a heterocyclic aromatic system having 1 to 60 carbon atoms. , and the C ₁ -C ₆₀ heteroarylene group includes at least one heteroatom selected from N, O, Si, P and S as a ring-forming atom and has a heterocyclic aromatic system having 1 to 60 carbon atoms. means a 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 (where A ₁₀₂ is the C ₆ -C ₆₀ aryl group), and the C ₆ -C ₆₀ arylthio group refers to -SA ₁₀₃ (wherein , A ₁₀₃ is the C ₆ -C ₆₀ aryl group).

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

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group 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 means a monovalent group (for example, having 1 to 60 carbon atoms) containing a hetero atom and having non-aromaticity in the entire molecule. Specific examples of the monovalent non-aromatic heterocondensed polycyclic group include a carbazolyl group and the like. A divalent non-aromatic condensed heteropolycyclic group in the present specification means a divalent group having the same structure as the monovalent non-aromatic condensed 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 atoms as ring-forming atoms. 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, various modifications such as the C ₅ -C ₆₀ carbocyclic group may be a trivalent group or a tetravalent group are possible depending on the number of substituents connected to the C ₅ -C ₆₀ carbocyclic group.

In the present specification, a C ₁ -C ₆₀ heterocyclic group has the same structure as the C ₅ -C ₆₀ carbocyclic group, but as a ring-forming atom, in addition to carbon (which may have 1 to 60 carbon atoms), N , It means a group containing at least one heteroatom 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 A rene group, a substituted C ₃ -C ₁₀ cycloalkenylene group, a substituted C ₁ -C ₁₀ heterocycloalkenylene group, a substituted C ₆ -C ₆₀ arylene group, a substituted C ₁ -C ₆₀ heteroarylene group, a substituted A divalent non-aromatic condensed polycyclic group, a substituted divalent non-aromatic heterocondensed polycyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a 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 heteropolycyclic group,

Heavy hydrogen (-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;

Heavy hydrogen, -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 heterocondensed polycyclic 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;

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 hetero condensed polycyclic group;

Heavy hydrogen, -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 non-aromatic group -Aromatic heterocondensed polycyclic 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 ) substituted with at least one selected from, 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, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=0) ₂ (Q ₃₁ ) and -P(=0)(Q ₃₁ )(Q ₃₂ );

is selected from

Wherein Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, A dino group, a hydrazino group, a hydrazono group, a C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group, a C ₁ -C ₆₀ alkoxy group, a C ₃ -C ₁₀ cycloalkyl group, 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 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 "Bu ^t " means a tert-butyl group, and "OMe " means a methoxy group.

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

In the present specification, * and *' mean a binding site with a neighboring atom in the corresponding formula, unless otherwise defined.

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

[Example]

Synthesis Example 1: Synthesis of Compound H1

Synthesis of Intermediate (A-1)

Under an argon atmosphere, 22.0 g of 2,3-dimethoxyphenyl boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane and 150 mL of 2M sodium carbonate aqueous solution were put into the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and then concentrated, and the residue was purified by silica gel column chromatography to obtain 19.8 g of intermediate (A-1) (yield: 85.2%).

Synthesis of Intermediate (A-2)

Under an argon atmosphere, 19.8 g of intermediate (A-1) and 500 mL of anhydrous THF were added to a flask, 60 mL of a hexane solution of 1.6M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78 °C and a 30 mL THF solution of 28.1 g of trimethyl borate (B(OMe) ₃ ) was added. The reaction solution was stirred for 8 hours while warming to room temperature. 200mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ , concentrated, and the residue was washed with hexane to obtain 15.3 g of an intermediate (A-2) (yield: 64.9%).

Synthesis of Intermediate (A-3)

Under an argon atmosphere, 18.0 g of intermediate (A-2), 19.2 g of 3-bromo-2-fluoro-1-iodobenzene, 1.28 g of tetrakis(triphenylphosphine) palladium (0), 180 mL of toluene and 2M 90 mL of sodium carbonate aqueous solution was put into the flask and heated, refluxed and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and then concentrated, and the residue was purified by silica gel column chromatography to obtain 19.1 g (yield: 76.6%) of an intermediate (A-3).

Synthesis of intermediate (A-4)

19.2 g of Intermediate (A-3) and 250 mL of dichloromethane (dehydrated) were placed in a flask and cooled to 0°C. After adding 27.5 g of boron tribromide (BBr ₃ ), the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and quenched with methanol and water. The solution was transferred to a separating funnel, extracted with dichloromethane, dried with MgSO ₄ , impurities were removed through a short silica gel column, and the sample obtained by concentrating the solution was vacuum-dried to obtain 17.8 g of intermediate (A-4). (Yield: 99.4%) was obtained.

Synthesis of Intermediate (A)

After adding 17.8 g of intermediate (A-4), 300 mL of N-methyl-2-pyrrolidone (dehydrated) and 24.5 g of K ₂ CO ₃ to a flask, the mixture was stirred at 200° C. for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2 L of toluene was added, and the mixed solution was transferred to a separatory funnel and washed with water. After drying the mixed solution with MgSO ₄ , impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 10.7 g of intermediate (A) (yield: 66.4%).

Synthesis of intermediate (H1-1)

10.7 g of the intermediate (A) and 500 mL of tetrahydrofuran (dehydrated) were placed in a flask and cooled to -78°C. Here, 66mL of n-BuLi (1.6M in hexane) was added and stirred for 2 hours while raising the temperature to 0℃. Then, it was cooled to -78 °C again, 27.5 g of B(OMe) ₃ was added, stirred at -78 °C for 10 minutes, and then stirred at room temperature for 5 hours. After completion of the reaction, 200 mL of 1N HCl aqueous solution was added and the mixture was stirred at room temperature for 1 hour. Then, it was transferred to a separatory funnel and extracted with ethyl acetate. The solution was dried with MgSO ₄ and then washed with concentrated n-hexane to obtain 22.9 g of an intermediate (H1-1) (yield: 65.1%).

Synthesis of intermediate (H1-2)

Under an argon atmosphere, 22.9 g of intermediate (H1-1), 19.8 g of 1-bromo-4-iodobenzene, 1.52 g of tetrakis (triphenylphosphine) palladium (0), 200 mL of toluene, and 100 mL of 2M sodium carbonate aqueous solution were prepared. It was placed in a flask and heated, refluxed and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. The aqueous layer was removed and the organic layer was dried over MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 23.9 g of an intermediate (H1-2) (yield: 71.9%).

Synthesis of Compound H1

Under an argon atmosphere, 23.9 g of intermediate (H1-2), 16.4 g of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid, 0.232 g of tetrakis(triphenylphosphine)palladium(0), 40mL of 1,2-dimethoxyethane and 20mL of 2M sodium carbonate aqueous solution were put into a flask and stirred under reflux for 8 hours. After cooling to room temperature, the precipitated solid was separated by filtration. The obtained solid was washed with water and methanol and then recrystallized with toluene to obtain 21.0 g of compound H1 (yield: 65.4%). Molecular Weight = 686.81, m/e = 686.22

Synthesis Example 2: Synthesis of Compound H2

Synthesis of Intermediate (B-1)

Under an argon atmosphere, 20.3 g of 2,3-bis(methylthio)phenyl boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.34 g of tetrakistriphenylphosphine palladium (0), 1,2-dimethine 300 mL of toxyethane and 150 mL of 2M sodium carbonate aqueous solution were put into a flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and then concentrated, and the residue was purified by silica gel column chromatography to obtain 30.9 g of intermediate (B-1) (yield: 84.9%).

Synthesis of Intermediate (B-2)

Under an argon atmosphere, 30.9 g of the intermediate (B-1) and 500 mL of anhydrous THF were placed in a flask, 55 mL of a hexane solution of 1.6M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. The reaction solution was cooled to -78[deg.] C., and a solution of 28.1 g of trimethyl borate in 30 mL of THF was added thereto. The reaction solution was stirred for 8 hours while warming to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. After the reaction solution was extracted with ether to remove the aqueous layer, the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ , concentrated, and the residue was washed with hexane to obtain 16.8 g of an intermediate (B-2) (yield: 64.1%).

Synthesis of intermediate (B-3)

Under an argon atmosphere, 16.8 g of intermediate (B-2), 16.5 g of 3-bromo-2-fluoro-1-iodobenzene, 1.28 g of tetrakis(triphenylphosphine) palladium (0), 180 mL of toluene and 2M 95 mL of aqueous sodium carbonate solution was put into the flask and heated, refluxed and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene to remove the aqueous layer, and then the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and then concentrated, and the residue was purified by silica gel column chromatography to obtain 20.1 g of an intermediate (B-3) (yield: 75.3%).

Synthesis of intermediate (B-4)

20.1 g of the intermediate (B-3) and 250 mL of dichloromethane (dehydrated) were placed in a flask and cooled to 0°C. After adding 27.5 g of BBr ₃ thereto, the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and quenched with methanol and water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , impurities were removed through a short silica gel column, and the sample obtained by concentrating the solution was vacuum dried to obtain 18.9 g of intermediate (B-4) (yield: 99.5%). got

Synthesis of intermediate (B)

After adding 18.9 g of intermediate (B-4), 300 mL of N-methyl-2-pyrrolidone, and 24.2 g of K ₂ CO ₃ to a flask, the mixture was stirred at 200° C. for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2 L of toluene was added, transferred to a separatory funnel, and washed with water. After drying the mixed solution with MgSO ₄ , impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 11.2 g of intermediate (B) (yield: 65.2%).

Synthesis of intermediate (H2-1)

24.4 g (yield: 63.6%) of intermediate (H2-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (B) was used instead of intermediate (A). .

Synthesis of intermediate (H2-2)

Intermediate (H2-2) 24.9 g (yield: 72.1 %) was obtained.

Synthesis of Compound H2

20.9 g (yield: 63.3%) of compound H2 was obtained using the same method as the synthesis method of compound H1, except that intermediate (H2-2) was used instead of intermediate (H1-2). Molecular Weight = 718.93, m/e = 718.18

Synthesis Example 3: Synthesis of Compound H3

Synthesis of Intermediate (C-1)

Under an argon atmosphere, 12.7 g of 5-bromo-9-iodonaphtho [2,1-b] benzofuran, 5.8 g of 2- (ethoxycarbonyl) phenylboronic acid, tetrakis (triphenylphosphite) palladium ( 0) A mixture of 0.4 g, 30 mL of 2M aqueous sodium carbonate solution and 60 mL of toluene was heated and refluxed for 8 hours. The obtained mixture was cooled to room temperature, extracted with toluene, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 8.7 g of intermediate (C-1) (yield: 65.4%).

Synthesis of intermediate (C-2)

Under an argon atmosphere, 30 mL of a tetrahydrofuran solution of 1M methyl magnesium bromide was added to a 90 mL solution of 8.7 g of intermediate (C-1) in tetrahydrofuran under ice-cooling, and the mixture was stirred at room temperature for 5 hours. Ice water was added to the reaction solution, extraction was performed with toluene, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6.4 g of intermediate (C-2) (yield: 76.1%).

Synthesis of Intermediate (C)

0.7 mL of sulfuric acid was added to a 70 mL solution of 6.4 g of intermediate (C-2) in acetic acid, and the mixture was stirred at 50°C for 8 hours. The resulting mixture was cooled to room temperature, and toluene and water were added to separate the layers, and the toluene layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by chromatography to obtain 2.1 g of intermediate (C) (yield: 34.8%).

Synthesis of intermediate (H3-1)

1.2 g (yield: 63.4%) of intermediate (H3-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (C) was used instead of intermediate (A). .

Synthesis of intermediate (H3-2)

1.2 g of intermediate (H3-2) (yield: 71.8%) using the same method as the synthesis method of intermediate (H1-2), except that intermediate (H3-1) was used instead of intermediate (H1-1) ) was obtained.

Synthesis of Compound H3

Intermediate (H3-2) was used instead of intermediate (H1-2), and 9-(naphthalen-1-yl)anthracen-10- instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. 1.0 g (yield: 62.9%) of compound H3 was obtained using the same method as the synthesis method of compound H1, except that yl-10-boronic acid was used. Molecular Weight = 712.89, m/e = 712.28

Synthesis Example 4: Synthesis of Compound H4

Synthesis of Intermediate (D-1)

Under an argon atmosphere, 12.7 g of 5-bromo-9-iodonaphtho [1,2-b] benzofuran, 5.8 g of 2- (ethoxycarbonyl) phenylboronic acid, tetrakis (triphenylphosphite) palladium ( 0) A mixture of 0.4 g, 30 mL of 2M aqueous sodium carbonate solution and 60 mL of toluene was heated and refluxed for 8 hours. The obtained mixture was cooled to room temperature, extracted with toluene, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 8.8 g of intermediate (D-1) (yield: 66.2%).

Synthesis of Intermediate (D-2)

Under an argon atmosphere, 30 mL of a tetrahydrofuran solution of 1M methyl magnesium bromide was added to a 90 mL solution of 8.8 g of intermediate (D-1) in tetrahydrofuran under ice-cooling, and the mixture was stirred at room temperature for 5 hours. Ice water was added to the reaction solution, extraction was performed with toluene, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6.4 g of intermediate (D-2) (yield: 75.1%).

Synthesis of Intermediate (D)

0.7 mL of sulfuric acid was added to a 70 mL solution of 6.4 g of intermediate (D-2) in acetic acid, and the mixture was stirred at 50°C for 8 hours. The obtained mixture was cooled to room temperature, and toluene and water were added to separate the layers, and the toluene layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography to obtain 2.2 g of intermediate (D) (yield: 35.3%).

Synthesis of intermediate (H4-1)

1.3 g (yield: 64.5%) of intermediate (H4-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (D) was used instead of intermediate (A). .

Synthesis of intermediate (H4-2)

Intermediate (H4-1) was used instead of intermediate (H1-1), and 1-bromo-3-iodobenzene was used instead of 1-bromo-4-iodobenzene. -2) 1.3 g (yield: 72.1%) of the intermediate (H4-2) was obtained using the same method as the synthesis method.

Synthesis of Compound H4

Intermediate (H4-2) was used instead of intermediate (H1-2), and 9-phenylanthracen-10-yl-10-boronic acid was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. 1.0 g (yield: 61.7%) of compound H4 was obtained using the same method as the synthesis method of compound H1, except that was used. Molecular Weight = 662.83, m/e = 662.26

Synthesis Example 5: Synthesis of Compound H5

Synthesis of Intermediate (E-1)

Under an argon atmosphere, 5-bromo-9-iodobenzo [b] naphtho [2,1-b] benzothiophene 13.2 g, 2- (ethoxycarbonyl) phenylboronic acid 5.8 g, tetrakis (tri A mixture of 0.4 g of phenylphosphite) palladium (0), 30 mL of 2M aqueous sodium carbonate solution and 60 mL of toluene was heated and refluxed for 8 hours. The obtained mixture was cooled to room temperature, extracted with toluene, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 9.0 g of intermediate (E-1) (yield: 65.3%).

Synthesis of Intermediate (E-2)

Under an argon atmosphere, 30 mL of a tetrahydrofuran solution of 1 M methyl magnesium bromide was added to a 90 mL solution of 9.0 g of intermediate (E-1) in tetrahydrofuran under ice-cooling, and the mixture was stirred at room temperature for 5 hours. Ice water was added to the reaction solution, extraction was performed with toluene, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6.5 g of intermediate (E-2) (yield: 74.5%).

Synthesis of Intermediate (E)

0.7 mL of sulfuric acid was added to a 70 mL solution of 6.5 g of intermediate (E-2) in acetic acid, and the mixture was stirred at 50°C for 8 hours. The obtained mixture was cooled to room temperature, and toluene and water were added to separate the layers, and the toluene layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography to obtain 2.2 g (yield: 34.6%) of intermediate (E).

Synthesis of intermediate (H5-1)

1.3 g (yield: 63.8%) of intermediate (H5-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (E) was used instead of intermediate (A). .

Synthesis of intermediate (H5-2)

Intermediate (H5-1) was used instead of intermediate (H1-1), and 1-bromo-3-iodobenzene was used instead of 1-bromo-4-iodobenzene. -2) 1.3 g (yield: 72.8%) of intermediate (H5-2) was obtained using the same method as the synthesis method.

Synthesis of Compound H5

1.1 g (yield: 62.6%) of compound H5 was obtained using the same method as the synthesis method of compound H1, except that intermediate (H5-2) was used instead of intermediate (H1-2). Molecular Weight = 728.95, m/e = 728.25

Synthesis Example 6: Synthesis of Compound H6

Synthesis of Intermediate (F-1)

Under an argon atmosphere, 17.3 g of 2,3-dimethoxyphenyl boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.34 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane and 150 mL of 2M sodium carbonate aqueous solution were put into the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and then concentrated, and the residue was purified by silica gel column chromatography to obtain 18.9 g of an intermediate (F-1) (yield: 85.8%).

Synthesis of Intermediate (F-2)

Under an argon atmosphere, 18.9 g of intermediate (F-1) and 500 mL of anhydrous THF were added to a flask, 55 mL of a hexane solution of 1.6M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78°C and a solution of 28.1 g of trimethyl borate in 30 mL of THF was added. The reaction solution was stirred for 8 hours while warming to room temperature. 200mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ , concentrated, and the residue was washed with hexane to obtain 14.3 g of an intermediate (F-2) (yield: 63.9%).

Synthesis of Intermediate (F-3)

Under an argon atmosphere, 14.3 g of intermediate (F-2), 19.2 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of tetrakis(triphenylphosphine) palladium (0), 180 mL of toluene and 2M 95 mL of aqueous sodium carbonate solution was put into the flask and heated, refluxed and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 17.9 g (yield: 75.6%) of an intermediate (F-3).

Synthesis of Intermediate (F-4)

Under an argon atmosphere, 17.9 g of intermediate (F-3) and 300 mL of dichloromethane (dehydrated) were placed in a flask and cooled to -78 °C. 90 mL of a dichloromethane solution of 1 M boron tribromide (BBr ₃ ) was added. Stirring was continued for 3 hours while warming the reaction solution to room temperature. 150 mL of ice water was added to the reaction mixture, and the aqueous layer was removed, and the organic layer was dried over MgSO ₄ . After concentrating the organic layer, the residue was purified with a short silica gel column to obtain 16.7 g (yield: 99.5%) of an intermediate (F-4).

Synthesis of Intermediate (F)

After adding 16.7 g of the intermediate (F-4), 300 mL of N-methyl-2-pyrrolidone (dehydrated) and 24.2 g of K ₂ CO ₃ to the flask, the mixture was stirred at 200° C. for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2 L of toluene was added, and the mixed solution was transferred to a separatory funnel and washed with water. After drying the mixed solution with MgSO ₄ , impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 10.1 g of intermediate (F) (yield: 66.8%).

Synthesis of intermediate (H6-1)

5.9 g (yield: 64.9%) of intermediate (H6-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (F) was used instead of intermediate (A). .

Synthesis of intermediate (H6-2)

6.0 g of intermediate (H6-2) (yield: 69.6%) using the same method as the synthesis method of intermediate (H1-2), except that intermediate (H6-1) was used instead of intermediate (H1-1) got

Synthesis of Compound H6

Intermediate (H6-2) was used instead of intermediate (H1-2) and 9-(3-(naphthalen-1-yl)phenyl was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. ) 5.8 g (yield: 64.3%) of compound H6 was obtained using the same method as the synthesis method of compound H1, except that anthracen-10-yl-10-boronic acid was used. Molecular Weight = 762.91, m/e = 762.26

Synthesis Example 7: Synthesis of Compound H7

Synthesis of intermediate (G-1)

Under an argon atmosphere, 17.3 g of 2,3-dimethoxyphenyl boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.34 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane and 150 mL of 2M sodium carbonate aqueous solution were put into the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and then concentrated, and the residue was purified by silica gel column chromatography to obtain 18.8 g of an intermediate (G-1) (yield: 85.6%).

Synthesis of intermediate (G-2)

Under an argon atmosphere, 18.8 g of intermediate (G-1) and 500 mL of anhydrous THF were added to a flask, 55 mL of a hexane solution of 1.6M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78°C and a solution of 28.1 g of trimethyl borate in 30 mL of THF was added. The reaction solution was stirred for 8 hours while warming to room temperature. 200mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ , concentrated, and the residue was washed with hexane to obtain 14.4 g of an intermediate (G-2) (yield: 64.1%).

Synthesis of intermediate (G-3)

Under an argon atmosphere, 14.4 g of intermediate (G-2), 19.2 g of 6-bromo-2-fluoro-3-iodonaphthalene, 1.28 g of tetrakis(triphenylphosphine) palladium (0), 180 mL of toluene and 2M 95 mL of aqueous sodium carbonate solution was put into the flask and heated, refluxed and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and then concentrated, and the residue was purified by silica gel column chromatography to obtain 17.9 g of an intermediate (G-3) (yield: 75.6%).

Synthesis of intermediate (G-4)

Under an argon atmosphere, 17.9 g of intermediate (G-3) and 300 mL of dichloromethane (dehydrated) were placed in a flask and cooled to -78 °C. 90 mL of a dichloromethane solution of 1 M boron tribromide (BBr ₃ ) was added. Stirring was continued for 3 hours while warming the reaction solution to room temperature. 150 mL of ice water was added to the reaction mixture, and the aqueous layer was removed, and the organic layer was dried over MgSO ₄ . After concentrating the organic layer, the residue was purified with a short silica gel column to obtain 16.7 g (yield: 99.6%) of an intermediate (G-4).

Synthesis of Intermediate (G)

After adding 16.7 g of the intermediate (G-4), 300 mL of N-methyl-2-pyrrolidone (dehydrated) and 24.2 g of K ₂ CO ₃ to the flask, the mixture was stirred at 200° C. for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2 L of toluene was added, and the mixed solution was transferred to a separatory funnel and washed with water. After drying the mixed solution with MgSO ₄ , impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 9.9 g of intermediate (G) (yield: 65.6%).

Synthesis of intermediate (H7-1)

6.0 g (yield: 65.4%) of intermediate (H7-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (G) was used instead of intermediate (A). .

Synthesis of intermediate (H7-2)

Intermediate (H1-1) was used instead of intermediate (H7-1), except that 1-bromo-4-iodonaphthalene was used instead of 1-bromo-4-iodobenzene, intermediate (H1 -2) 6.7 g (yield: 70.4%) of intermediate (H7-2) was obtained using the same method as the synthesis method.

Synthesis of Compound H7

Intermediate (H7-2) was used instead of intermediate (H1-2) and 9-(3-(naphthalen-2-yl)phenyl was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. ) 6.2 g (yield: 63.9%) of compound H7 was obtained using the same method as the synthesis method of compound H1, except that anthracen-10-yl-10-boronic acid was used. Molecular Weight = 812.97, m/e = 812.27

Synthesis Example 8: Synthesis of Compound H8

Synthesis of Intermediate (H-1)

Under an argon atmosphere, 17.3 g of 2,4-dimethoxyphenyl boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.34 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane and 150 mL of 2M sodium carbonate aqueous solution were put into the flask, and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 18.7 g of intermediate (H-1) (yield: 84.9%).

Synthesis of Intermediate (H-2)

Under an argon atmosphere, 18.7 g of intermediate (H-1) and 500 mL of anhydrous THF were added to a flask, 55 mL of a hexane solution of 1.6M n-butyllithium was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78°C and a solution of 28.1 g of trimethyl borate in 30 mL of THF was added. The reaction solution was stirred for 8 hours while warming to room temperature. 200mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ , concentrated, and the residue was washed with hexane to obtain 14.3 g of an intermediate (H-2) (yield: 64.3%).

Synthesis of Intermediate (H-3)

Under an argon atmosphere, 14.3 g of intermediate (H-2), 19.2 g of 4-bromo-2-fluoro-1-iodonaphthalene, 1.28 g of tetrakis(triphenylphosphine) palladium (0), 180 mL of toluene and 2M 95 mL of aqueous sodium carbonate solution was put into the flask and heated, refluxed and stirred for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene, the aqueous layer was removed, and the organic layer was washed with saturated brine. The organic layer was dried over MgSO ₄ , concentrated, and the residue was purified by silica gel column chromatography to obtain 17.8 g of an intermediate (H-3) (yield: 75.4%).

Synthesis of intermediate (H-4)

Under an argon atmosphere, 17.9 g of intermediate (H-3) and 300 mL of dichloromethane (dehydrated) were placed in a flask and cooled to -78 °C. 90 mL of a dichloromethane solution of 1 M boron tribromide (BBr ₃ ) was added. Stirring was continued for 3 hours while warming the reaction solution to room temperature. 150 mL of ice water was added to the reaction mixture, and the aqueous layer was removed, and the organic layer was dried over MgSO ₄ . After concentrating the organic layer, the residue was purified with a short silica gel column to obtain 16.7 g (yield: 99.6%) of an intermediate (H-4).

Synthesis of Intermediate (H)

After adding 16.7 g of the intermediate (H-4), 300 mL of N-methyl-2-pyrrolidone (dehydrated) and 24.2 g of K ₂ CO ₃ to the flask, the mixture was stirred at 200 °C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2 L of toluene was added, and the mixed solution was transferred to a separatory funnel and washed with water. After drying the mixed solution with MgSO ₄ , impurities were removed through a short silica gel column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 9.7 g of intermediate (H) (yield: 64.3%).

Synthesis of intermediate (H8-1)

5.7 g (yield: 64.5%) of intermediate (H8-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (H) was used instead of intermediate (A). .

Synthesis of intermediate (H8-2)

Intermediate (H1-1) was used instead of intermediate (H8-1), except that 1-bromo-4-iodonaphthalene was used instead of 1-bromo-4-iodobenzene, intermediate (H1 -2) 5.8 g (yield: 64.6%) of intermediate (H8-2) was obtained using the same method as the synthesis method.

Synthesis of Compound H8

Intermediate (H8-2) was used instead of intermediate (H1-2), and 9-phenylanthracen-10-yl-10-boronic acid was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. 4.5 g (yield: 63.2%) of compound H8 was obtained using the same method as the synthesis method of compound H1, except that was used. Molecular Weight = 686.81, m/e = 686.22

Synthesis Example 9: Synthesis of Compound H9

Synthesis of Intermediate (I-1)

Under an argon atmosphere, 12.7 g of 5-bromo-10-iodonaphtho [2,1-b] benzofuran, 5.8 g of 2- (ethoxycarbonyl) phenylboronic acid, tetrakis (triphenylphosphite) palladium ( 0) A mixture of 0.4 g, 30 mL of 2M aqueous sodium carbonate solution and 60 mL of toluene was heated and refluxed for 8 hours. The obtained mixture was cooled to room temperature, extracted with toluene, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 8.6 g of intermediate (I-1) (yield: 64.6%).

Synthesis of Intermediate (I-2)

Under an argon atmosphere, 30 mL of a tetrahydrofuran solution of 1M methyl magnesium bromide was added to a 90 mL solution of 8.6 g of intermediate (I-1) in tetrahydrofuran under ice-cooling, and the mixture was stirred at room temperature for 5 hours. Ice water was added to the reaction solution, extraction was performed with toluene, and the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 6.3 g of intermediate (I-2) (yield: 74.9%).

Synthesis of Intermediate (I)

0.7 mL of sulfuric acid was added to a 70 mL solution of 6.3 g of intermediate (I-2) in acetic acid, and the mixture was stirred at 50°C for 8 hours. The obtained mixture was cooled to room temperature, and toluene and water were added to separate the layers, and the toluene layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by chromatography to obtain 2.1 g of intermediate (I) (yield: 34.6%).

Synthesis of intermediate (H9-1)

1.2 g (yield: 64.9%) of intermediate (H9-1) was obtained using the same method as the synthesis method of intermediate (H1-1), except that intermediate (I) was used instead of intermediate (A). .

Synthesis of intermediate (H9-2)

Intermediate (H1-1) was used instead of intermediate (H9-1), except that 2-bromo-6-iodonaphthalene was used instead of 1-bromo-4-iodobenzene, intermediate (H1 -2) 1.3 g (yield: 67.2%) of intermediate (H9-2) was obtained using the same method as the synthesis method.

Synthesis of Compound H9

Intermediate (H9-2) was used instead of intermediate (H1-2), and 9-(9H-dibenzofuran-2-yl) was used instead of 9-(naphthalen-3-yl)anthracen-10-yl-10-boronic acid. 1.1 g (yield: 64.7%) of compound H9 was obtained using the same method as the synthesis method of compound H1, except that anthracene-10-yl-10-boronic acid was used. Molecular Weight = 802.97, m/e = 802.29

Example 1

As a substrate and anode, a Corning 15Ω/cm2 (1200Å) ITO glass substrate was cut into 50mm x 50mm x 0.7mm size, ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, and then irradiated with ultraviolet rays for 30 minutes. After cleaning by exposure to ozone, the glass substrate was installed in a vacuum deposition apparatus.

Compound HT13 was vacuum deposited on the ITO anode to form a 500 Å thick hole injection layer, and compound HT3 was vacuum deposited on the hole injection layer to form a 450 Å thick hole transport layer.

Compound H1 (host) and FD1 (dopant) were co-deposited at a weight ratio of 95:5 on the hole transport layer to form a light emitting layer having a thickness of 300 Å.

Compound ET1 was deposited on the light emitting layer to form an electron transport layer with a thickness of 250 Å, LiF was deposited on the electron transport layer to form an electron injection layer with a thickness of 50 Å, and Al was vacuum deposited on the electron injection layer to form an electron transport layer with a thickness of 1500 Å. A cathode was formed to manufacture an organic light emitting device.

Examples 2 to 9 and Comparative Examples 1 to 4

An organic light emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Table 1 were used in forming the light emitting layer.

Evaluation Example 1

Efficiency and lifetime (T ₈₀ ) data of the organic light emitting diodes prepared in Examples 1 to 9 and Comparative Examples 1 to 4 were measured using a Kethley SMU 236 and a luminance meter PR650, and the results are shown in Table 1. The lifetime (T ₈₀ ) is a measure of the time taken for the luminance to reach 80% of the initial luminance (100%) after driving the device at a current density of 50 mA/cm ² .

host material efficiency
(cd/A) life span
(hr@50mA/cm ² ) Example 1 H1 5.2 110 Example 2 H2 5.1 100 Example 3 H3 5.3 90 Example 4 H4 5.2 100 Example 5 H5 5.1 90 Example 6 H6 5.1 100 Example 7 H7 5.1 90 Example 8 H8 5.0 110 Example 9 H9 5.2 100 Comparative Example 1 compound A 4.5 50 Comparative Example 2 compound B 4.7 80 Comparative Example 3 compound C 4.9 70 Comparative Example 4 compound D 5.0 90

From Table 1, it can be confirmed that the efficiency and lifespan of the organic light emitting devices of Examples 1 to 9 are superior to those of the organic light emitting devices of Comparative Examples 1 to 4.

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

Claims (20)

A condensed cyclic compound represented by one of the following formulas 1(1)-1 to 1(18)-1:

Among Formulas 1(1)-1 to 1(18)-1,
X ₁ is selected from O and S;
X ₂ is selected from O and S;
T ₁ is a group represented by the following formula 2A(1);
<Formula 2A (1)>

In Formula 2A (1),
L ₁ and L ₂ are each independently selected from a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group. 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 Among substituted or unsubstituted divalent non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic groups being selected,
a1 is selected from 0, 1, 2 and 3, a2 is selected from 1, 2 and 3;
Ar _1e is hydrogen, deuterium (-D), -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 substituted 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 heterocycloalke Nyl 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 polycyclic group, -Si(Q ₄ )(Q ₅ )(Q ₆ ) , -N(Q ₄ )(Q ₅ ), -B(Q ₄ )(Q ₅ ), -C(=O)(Q ₄ ), -S(=O) ₂ (Q ₄ ) and -P(= O) (Q ₄ ) (Q ₅ ) selected from,
The above substituted C ₃ -C ₁₀ cycloalkylene group, substituted C ₁ -C ₁₀ heterocycloalkylene group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic heterocondensed polycyclic 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 hetero Cycloalkyl 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 At least one of the substituents of _{the 6} -C ₆₀ arylthio group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic heteropolycyclic group,
Heavy hydrogen (-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;
Heavy hydrogen, -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 heterocondensed polycyclic 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;
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 hetero condensed polycyclic group;
Heavy hydrogen, -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 non-aromatic group -Aromatic heterocondensed polycyclic 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 ) substituted with at least one selected from, 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, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group; and
-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S (=0) ₂ (Q ₃₁ ) and -P(=0)(Q ₃₁ )(Q ₃₂ );
is selected from
Wherein Q ₄ to Q ₆ , Q ₁₁ to Q ₁₃ , Q ₂₁ to Q ₂₃ and Q ₃₁ to Q ₃₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cyano 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 heteroaryl group , a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl group, and a terphenyl group,
* is a binding site with a neighboring atom. delete According to claim 1,
Among Formulas 1(1)-1 and 1(18)-1,
X ₁ and X ₂ are S;
X ₁ is O and X ₂ is S;
X ₁ and X ₂ are O;
or
A condensed cyclic compound wherein X ₁ is S and X ₂ is O; delete According to claim 1,
In Formula 2A (1),
L ₁ and L ₂ are each independently a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group ( heptalenylene), indacenylene, acenaphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenyl phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, Coronenylene group, ovalenylene group, pyrrolylene group, thiophenylene group, furanylene group, carbazolylene group, benzofuranylene group (benzofuranylene), benzothiophenylene, dibenzofuranylene, dibenzothiophenylene, benzocarbazolylene and dibenzocarbazolylene groups; and
Heavy hydrogen, -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, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, flu Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl group, pyrenyl group, chrysenyl group group, naphthacenyl group, picenyl group, peryl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group , A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, and an azulenyl group substituted with at least one selected from a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group. A rene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group , anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubycenyl A rene group, a coronenylene group, an ovalenylene group, a pyrrolene group, a thiophenylene group, a furanylene group, a carbazolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, A benzocarbazolylene group and a dibenzocarbazolylene group; A condensed cyclic compound selected from among. According to claim 1,
In Formula 2A(1), L ₁ and L ₂ are each independently selected from the group represented by the following Formulas 3-1 to 3-22, a condensed cyclic compound:

In Chemical Formulas 3-1 to 3-22,
Y ₁ is selected from O, S, C(Z ₃ )(Z ₄ ), N(Z ₅ ) and Si(Z ₆ )(Z ₇ );
Z ₁ to Z ₇ are each independently selected from hydrogen, heavy hydrogen, -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, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, It is selected from an anthracenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ),
Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a biphenyl group, and a terphenyl group;
d1 is selected from an integer from 1 to 4, d2 is selected from an integer from 1 to 3, d3 is selected from an integer from 1 to 6, d4 is selected from an integer from 1 to 8, and d5 is selected from an integer from 1 to 5 It is selected from integers, and * and *' are binding sites with neighboring atoms. According to claim 1,
In Formula 2A(1), L ₁ and L ₂ are each independently selected from the group represented by the following Formulas 4-1 to 4-35, a condensed cyclic compound:

In Formulas 4-1 and 4-35, * and *' are binding sites with neighboring atoms. According to claim 1,
In Formula 2A(1), a1 is 0 or 1, and a2 is 1 or 2, a condensed cyclic compound. According to claim 1,
Ar _1e in Formula 2A (1) is
Hydrogen, heavy hydrogen, -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;
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, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a 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, rubicenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzo a carbazolyl group, a dibenzocarbazolyl group and a dibenzosilolyl group; and
Heavy hydrogen, -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, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl 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, penta A phenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, A phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, which is substituted with at least one selected from a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) Nyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-fluorenyl 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, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group and dibenzosilol diary; is selected from
Wherein Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, a phenyl group, a naphthyl group, a biphenyl group, and a terphenyl group. According to claim 1,
Ar _1e in Formula 2A (1) is
Hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group; and
A condensed cyclic compound selected from the group represented by Formulas 5-1 to 5-16:

In Chemical Formulas 5-1 to 5-16,
Y ₃₁ is selected from O, S, C(Z ₃₃ ) (Z ₃₄ ), N(Z ₃₅ ) and Si(Z ₃₆ ) (Z ₃₇ );
Z ₃₁ to Z ₃₇ are each independently hydrogen, heavy hydrogen, -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 and 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, triphenylenyl group, pyrenyl group , chrysenyl group, thiophenyl group, furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group and dibenzothiophenyl group; and
Heavy hydrogen, -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, triphenylenyl group, pyrene A phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, substituted with at least one selected from a phenyl group, a chrysenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group , Fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, thiophenyl group, furanyl group , a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; is selected from
e3 is selected from an integer from 1 to 3, e4 is selected from an integer from 1 to 4, e5 is selected from an integer from 1 to 5, e6 is selected from an integer from 1 to 6, and e7 is selected from an integer from 1 to 7 It is selected from integers, and e9 is selected from integers from 1 to 9. According to claim 1,
Ar _1e in Formula 2A (1) is
Hydrogen, heavy hydrogen, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₁₀ alkyl group and C ₁ -C ₁₀ alkoxy group; and
A condensed cyclic compound selected from the group represented by Formulas 6-1 to 6-44:

In Formulas 6-1 to 6-44, * is a binding site with a neighboring atom. delete delete delete delete delete delete a first electrode; a second electrode facing the first electrode; and an organic layer interposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one condensed cyclic compound of claim 1 . According to claim 18,
The light emitting layer includes the condensed cyclic compound, an organic light emitting device. According to claim 19,
The light emitting layer further comprises a fluorescent dopant, an organic light emitting device.

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