KR102644563B1 - Condensed-cyclic compound and organic light emitting device comprising the same - Google Patents

Abstract

Condensed cyclic compounds and organic light-emitting devices containing the same are disclosed.

Description

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

It relates to condensed cyclic compounds and organic light-emitting devices containing them.

Organic light emitting devices (organic light emitting devices) are self-emitting devices that not only have a wide viewing angle and excellent contrast, but also have the advantages of fast response time, excellent brightness, driving voltage, and response speed characteristics, and the ability to be multicolored.

The organic light-emitting device has a first electrode disposed on an upper part of 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. It can have a structure. 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. Light is generated as this exciton changes from the excited state to the ground state.

The aim is to provide novel condensed cyclic compounds and organic light-emitting devices containing them.

According to one aspect, a condensed ring compound represented by the following formula (1) is provided:

<Formula 1>

<Formula 2-1> <Formula 2-2> <Formula 2-3>

<Formula 2-4> <Formula 2-5>

In Formulas 1 and 2-1 to 2-5,

A ring is selected from C ₅ -C ₃₀ carbocyclic ring and C ₂ -C ₃₀ heterocyclic ring,

X ₁ is C(R ₁ ) or N, and X ₂ is C(R ₂ ) or N, where at least one of X ₁ and X ₂ is N,

L ₁ to L ₁₁ 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 cyclo Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted Among the substituted or unsubstituted divalent non-aromatic condensed polycyclic group and the substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group selected,

a1 to a11 are independently of each other 0, 1, 2, 3, 4 or 5,

Ar ₁ to Ar ₇ are 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, or a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic selected from a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group,

b1 to b4 are each independently 1, 2, or 3,

R ₁ to R ₁₁ are each independently a group represented by Formulas 2-1 to 2-5, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, hydra Zino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic hetero Condensed polycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -B(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S(=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ),

c3 is 0, 1, 2, 3, 4, 5 or 6,

The 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 C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ Alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ 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 condensed heteropolycyclic group,

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

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

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 Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo Alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent 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 ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C substituted with at least one selected from ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

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

is selected from,

Q ₁ to Q ₃ , 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, hydroxyl group, cyano group, 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 bonding site with a neighboring atom.

According to another aspect, a first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer includes at least one condensed ring compound represented by Formula 1.

Organic light-emitting devices containing the condensed cyclic compound may have low driving voltage, high brightness, high efficiency, and long lifespan.

1 to 4 schematically show cross-sectional views of an organic light-emitting device according to an embodiment of the present invention.

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

<Formula 1>

In Formula 1, ring A may be selected from a C ₅ -C ₃₀ carbocyclic ring and a C ₂ -C ₃₀ heterocyclic ring. For example, the A ring is benzene, pyridine, pyridazine, pyrimidine, pyrazine, naphthalene, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, anthracene, phenanthrene, benzoquinoline, and phenanthridine. , acridine, phenanthroline and phenazine. According to one aspect, the A ring may be selected from benzene, pyridine, naphthalene, quinoline, and isoquinoline, but is not limited thereto.

In Formula 1, X ₁ is C(R ₁ ) or N, and X ₂ is C(R ₂ ) or N, but at least one of X ₁ and X ₂ may be N.

In Formula 1, at least one of R ₁ to R ₁₁ may be selected from the group represented by the following Formulas 2-1 to 2-5:

<Formula 2-1> <Formula 2-2> <Formula 2-3>

<Formula 2-4> <Formula 2-5>

In Formulas 2-1 to 2-5, * represents a bonding site with a neighboring atom.

In Formulas 2-1 to 2-5, L ₁ to L ₁₁ each independently represent a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, 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 non-aromatic condensed polycyclic group, and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group. or unsubstituted divalent non-aromatic condensed heteropolycyclic group). For example, L ₁ to L ₁₁ are independently of each other,

Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetate Acenaphthylene, fluorenylene, spiro-bifluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene ), anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene ( picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovale ovalenylene, pyrrolylene, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, iso Isothiazolylene, oxazolylene, isoxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene ), isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquine Benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinnolinylene group, carbazolinylene group (carbazolylene), phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene ), benzothiophenylene, isobenzothiazolylene, benzoxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, Oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, Thiadiazolylene group, imidazopyridinylene group and imidazopyrimidinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group. 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, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, Furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indole Diary group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenanthri Dinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetra Zolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyridinyl group Polyzopyrimidinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ ( Q ₃₁ ) and -P (=O) (Q ₃₁ ) (Q ₃₂ ), substituted with at least one of phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, hepthalenylene group, indacenyl Len group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenyl Len group, triphenyleneylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubisenylene group, coronenylene group, O Valenylene group, pyrrolylene group, thiophenylene group, furanylene group, imidazolylene group, pyrazonylene group, thiazonylene group, isothiazolylene group, oxazonylene group, isoxazonylene group, pyridinylene group, pyrazinylene group , pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, Naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cynolinylene group, carbazoylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazynylene group, benzoimidazolylene group, benzo Furanylene group, benzothiophenylene group, isobenzothiazonylene group, benzooxazolylene group, isobenzooxazolylene group, triazonylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, di Benzothiophenylene group, benzocarbazolylene group, dibenzosylrollylene group, dibenzocarbazolylene group, thiadiazolylene group, imidazopyridinylene group and imidazopyrimidinylene group;

is selected from,

Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, and a benzoyl group. It may be selected from a fluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, and carbazolyl group.

According to one embodiment, L ₁ to L ₁₁ may be independently selected from the group represented by the following formulas 3-1 to 3-25:

In formulas 3-1 to 3-25,

Y ₁ is O, S, C(Z ₅ )(Z ₆ ), N(Z ₇ ) or Si(Z ₈ )(Z ₉ ),

Z ₁ to Z ₉ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, 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, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, is selected from triazinyl group and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ),

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

d3 is selected from an integer of 1 to 3,

d4 is selected from an integer of 1 to 4,

d6 is selected from integers from 1 to 6,

d8 is selected from integers from 1 to 8,

* and *' are binding sites with neighboring atoms. For example, L ₁ to L ₁₁ may be independently selected from groups represented by the following formulas 4-1 to 4-19, but are not limited thereto:

In Formulas 4-1 to 4-19, * and *' are bonding sites with neighboring atoms.

In Formulas 2-1 to 2-5, a1 to a11 may each independently be 0, 1, 2, 3, 4, or 5. a1 represents the number of L ₁ . When a1 is 0, *-(L ₁ ) _a1 -*' becomes a single bond, and when a1 is 2 or more, 2 or more L ₁ may be the same or different from each other. The description of a2 to a11 can be understood by referring to the description of a1 and the structures of Formulas 2-1 to 2-5. For example, a1 to a10 may be independently 0, 1, 2, or 3, but are not limited thereto.

In Formulas 2-1 to 2-5, Ar ₁ to Ar ₇ are a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, or a substituted or unsubstituted C ₂ - C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group , a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group (substituted or unsubstituted monovalent non-aromatic non-aromatic hetero) -condensed polycyclic group). For example, Ar ₁ to Ar ₇ are independently of each other,

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, 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 Phenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group , phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofura Nyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, Benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzonaphthofuranyl group, dinaphthofuranyl group, benzonaphthothiophenyl group, dinaphthothiophenyl group, benzonaphthosilolyl group and dinaphthosilolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group. 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, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, Furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indole Diary group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, carbazolyl group, phenanthri Dinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetra Zolyl group, oxadiazolyl group, triazinyl group, dibenzosilolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyridinyl group, imidazolyl group Polyzopyrimidinyl group, benzonaphthofuranyl group, dinaphthofuranyl group, benzonaphthothiophenyl group, dinaphthothiophenyl group, benzonaphthosilolyl group, dinaphthosilolyl group, -Si(Q ₃₁ )( ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ ) Substituted with at least one of: phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl group, fluorenyl group, spiro-biflu Orenyl group, benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, Isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinol group Nolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, Benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofura Nyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzonaphthofuranyl group, dinaphthofuranyl group , benzonaphthothiophenyl group, dinaphthothiophenyl group, benzonaphthosilolyl group and dinaphthosilolyl group;

is selected from,

Q ₃₁ to Q ₃₃ are each independently selected from a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, and a benzoyl group. It may be selected from a fluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, and carbazolyl group.

According to one embodiment, Ar ₁ to Ar ₇ may be independently selected from the group represented by the following formulas 5-1 to 5-25:

In formulas 5-1 to 5-25,

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

Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, 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, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, is selected from triazinyl group and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ),

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

e3 is selected from an integer of 1 to 3,

e4 is selected from integers 1 to 4,

e5 is selected from integers 1 to 5,

e6 is selected from integers from 1 to 6,

e7 is selected from integers from 1 to 7,

e9 is selected from integers from 1 to 9,

* is a bonding site with a neighboring atom. For example, Ar ₁ to Ar ₇ may be independently selected from groups represented by the following formulas 6-1 to 6-18, but are not limited thereto:

In Formulas 6-1 to 6-18, * represents a bonding site with a neighboring atom.

In Formulas 2-1 to 2-4, b1 to b4 may be independently 1, 2, or 3. For example, b1 to b4 may be 1, but are not limited thereto.

In Formula 1, R ₁ to R ₁₁ are each independently selected from a group represented by Formulas 2-1 to 2-5, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, No group, nitro group, hydrazino group, hydrazono group, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group , substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ Cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group (aryloxy), 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 heterocondensed polycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -B(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S( =O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ),

Q ₁ to Q ₃ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group group, biphenyl group, and terphenyl group. For example, R ₁ to R ₁₁ are independently of each other,

Groups represented by Formulas 2-1 to 2-5, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazo No 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, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group. , pyridazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group. , benzoxazolyl group, isobenzooxazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, imidazopyridinyl group and imidazopyrimidinyl group;

Deuterium, -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, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrethyl group. Nyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidi Nyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazole Diary group, benzoxazolyl group, isobenzooxazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, imidazopyridinyl group, imidazopyrimidinyl group, -Si (Q ₃₁ ) (Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)( Q ₃₁ ) (Q ₃₂ ) Substituted with at least one of 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, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazole Diary group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, benzoimidazolyl group, Benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, imidazopyridinyl group, and imidazopyrimidinyl group; and

-Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -B(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S (=O) ₂ (Q ₁ ) and -P(=O)(Q ₁ )(Q ₂ ),

Q ₁ to Q ₃ and 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 biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro- It may be selected from a bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, and carbazolyl group.

According to one embodiment, R ₁ to R ₁₁ are independently of each other,

Groups represented by Formulas 2-1 to 2-5, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazo No 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, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -N(Q ₁ )(Q ₂ ), -C(=O)(Q ₁ ), -S(=O) ₂ (Q ₁ ), and -P(=O)(Q ₁ )(Q ₂ ). is selected from,

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

In Formula 1, c3 may be 0, 1, 2, 3, 4, 5, or 6. c3 represents the number of R ₃ , and when c3 is 2 or more, 2 or more R ₃ are the same or different from each other. For example, c3 may be 0, 1, 2, or 3, but is not limited thereto.

According to one aspect, in Formula 1, X ₁ is N, X ₂ is C(R ₂ ), and R ₂ is selected from the group represented by Formulas 2-1 to 2-5, R ₃ to R ₁₁ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, 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, carbazolyl group, benzocarbazolyl group, and dibenzocarbazolyl group.

According to another aspect, in Formula 1, X ₁ is C(R ₁ ), X ₂ is N, and R ₁ is selected from the group represented by Formulas 2-1 to 2-5, R ₃ to R ₁₁ are each independently selected from hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, 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, carbazolyl group, benzocarbazolyl group, and dibenzocarbazolyl group.

According to another aspect, in Formula 1, R ₃ is selected from the group represented by Formulas 2-1 to 2-5, and R ₁ , R ₂ and R ₄ to R ₁₁ are independently of each other, Group represented by Formula 2-5, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ - C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, It may be selected from anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group and dibenzocarbazolyl group.

According to one embodiment, Formula 1 may be represented by one of the following Formulas 1A to 1S:

In formulas 1A to 1S,

The description of R ₃₁ to R ₃₆ is the same as the description of R ₃ ,

For a description of X ₁ , X ₂ , R ₃ to R ₁₁ , refer to what is described herein.

In one aspect, in Formulas 1A to 1S, X ₁ is N, X ₂ is C(R ₂ ), and R ₂ may be selected from the group represented by Formulas 2-1 to 2-5. there is. For example, in Formulas 1A to 1S, X ₁ is N, X ₂ is C(R ₂ ), R ₂ is selected from the group represented by Formulas 2-1 to 2-5, and R ₃₁ to R ₃₆ and R ₄ to R ₁₁ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydra Zono 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, dibenzofluore It may be selected from a nyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, and dibenzocarbazolyl group.

In another aspect, in Formulas 1A to 1S, X ₁ is C(R ₁ ), X ₂ is N, and R ₁ may be selected from the group represented by Formulas 2-1 to 2-5. there is. For example, in Formulas 1A to 1S, X ₁ is C(R ₁ ), X ₂ is N, R ₁ is selected from the group represented by Formulas 2-1 to 2-5, and R ₃₁ to R ₃₆ and R ₄ to R ₁₁ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydra Zono 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, dibenzofluore It may be selected from a nyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carbazolyl group, benzocarbazolyl group, and dibenzocarbazolyl group.

In another aspect, in Formulas 1A, 1B, 1D to 1G, 1I to 1N, and 1P to 1S, X ₁ is N, X ₂ is C(R ₂ ), and R ₃₂ is represented by Formula 2 It may be selected from the group indicated by -1 to 2-5. For example, in Formulas 1A, 1B, 1D to 1G, 1I to 1N, and 1P to 1S, X ₁ is N, X ₂ is C(R ₂ ), and R ₃₂ is represented by Formula 2-1 to 2-5, wherein R ₂ , R ₃₁ , R ₃₃ to R ₃₆ and R ₄ to R ₁₁ are independently selected from a group represented by Formula 2-5, hydrogen, deuterium, - F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, 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, cry It may be selected from cenyl group, carbazolyl group, benzocarbazolyl group and dibenzocarbazolyl group.

In another aspect, in Formulas 1A, 1B, 1D to 1G, 1I to 1N, and 1P to 1S, X ₁ is C(R ₁ ), X ₂ is N, and R ₃₂ is represented by Formula 2 It may be selected from the group indicated by -1 to 2-5. For example, in Formulas 1A, 1B, 1D to 1G, 1I to 1N, and 1P to 1S, X ₁ is C(R ₁ ), X ₂ is N, and R ₃₂ is represented by Formula 2-1 to 2-5, and R ₁ , R ₃₁ , R ₃₃ to R ₃₆ and R ₄ to R ₁₁ are independently selected from the group represented by Formula 2-5, hydrogen, deuterium, -F , -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, ratio Phenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group group, carbazolyl group, benzocarbazolyl group, and dibenzocarbazolyl group.

The condensed ring compound represented by Formula 1 may be one of the following compounds 1 to 192, but is not limited thereto:

The condensed cyclic compound represented by Formula 1 has excellent charge transport ability and thermal stability, and an organic light-emitting device employing the condensed cyclic compound represented by Formula 1 can have low driving voltage, high efficiency, high brightness, and long lifespan. .

A method for synthesizing the condensed ring compound represented by Formula 1 can be recognized by those skilled in the art by referring to the examples described below.

At least one of the condensed ring compounds represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the condensed ring compound may be included in the electron transport region.

Therefore, the first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer includes one or more condensed cyclic compounds represented by Formula 1. An organic light-emitting device may be provided.

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

For example, the organic layer may include only Compound 1 as the condensed ring compound. At this time, Compound 1 may be present in the electron transport layer of the organic light-emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the condensed ring compound. At this time, Compound 1 and Compound 2 may exist in the same layer (for example, both Compound 1 and Compound 2 may exist in the electron transport layer) or in different layers (for example, Compound 1 may exist in the electron transport layer). may be present in the electron transport layer, and Compound 2 may be present in the electron injection layer.

The organic layer includes: i) a hole transport region interposed between the first electrode (anode) and the light emitting layer and including at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, and an electron blocking layer; ii) It is interposed between the light emitting layer and the second electrode (cathode) and may include an electron transport region including at least one of a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer. At least one of the condensed ring compounds represented by Formula 1 may be included in the electron transport region. For example, the electron transport region of the organic light emitting device may include an electron transport layer, and the electron transport layer may include at least one of the condensed ring compounds represented by Formula 1 above. Alternatively, the electron transport region of the organic light emitting device may include an electron injection layer, and the electron injection layer may include at least one of the compounds represented by Formula 1 above.

The organic light-emitting device includes a first capping layer disposed on a path through which light generated in the light-emitting layer passes through the first electrode and is taken out to the outside, and a first capping layer disposed on a path through which light generated by the light-emitting layer passes through the second electrode and is taken out to the outside. It may further include at least one of the disposed second capping layers, and at least one of the first capping layer and the second capping layer may include one or more types of condensed ring compounds represented by Formula 1.

For example, the organic light emitting device has i) a structure in which a first electrode, an organic layer, a second electrode, and a second capping layer are sequentially stacked, ii) a first capping layer, a first electrode, an organic layer, and a second electrode. A sequentially stacked structure or iii) a structure in which a first capping layer, a first electrode, an organic layer, a second electrode, and a second capping layer are sequentially stacked, and at least one of the first capping layer and the second capping layer The condensed ring compound may be included.

In this specification, “organic layer” is a term referring to all single and/or multiple layers interposed between the first electrode and the second electrode of the organic light emitting device. Materials included in the “organic layer” layer are not limited to organic materials.

[Description of Figure 1]

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

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

[First electrode (110)]

A substrate may be additionally disposed below the first electrode 110 or above the second electrode 190 in FIG. 1 . As the substrate, a glass substrate or a plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness can be used.

The first electrode 110 may be formed, for example, by providing a first electrode material on the upper part of the substrate using a deposition method or sputtering method. When the first electrode 110 is an anode, the material for the first electrode may be selected from materials with a high work function to facilitate hole injection.

The first electrode 110 may be a reflective electrode, a transflective electrode, or a transmissive electrode. In order to form the first electrode 110, which is a transmissive electrode, the first electrode material is indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and any of them. It may be selected from a combination of, but is not limited to this. Alternatively, to form the first electrode 110, which is a transflective electrode or a reflective electrode, the first electrode material is magnesium (Mg), silver (Ag), aluminum (Al), or 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 or a multi-layer structure having a plurality of layers. For example, the first electrode 110 may have a three-layer structure of ITO/Ag/ITO, but is not limited to this.

[Organic layer (150)]

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

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

[Hole transport area in organic layer 150]

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

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

For example, the hole transport region has a single-layer structure consisting of a single layer made of a plurality of different materials, or a hole injection layer/hole transport layer or a hole injection layer/hole transport layer sequentially stacked from the first electrode 110. /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/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)), a compound represented by Formula 201 below, and a compound represented by Formula 202 below It may include at least one compound selected from:

<Formula 201>

<Formula 202>

In formulas 201 and 202,

L ₂₀₁ to L ₂₀₄ 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 cyclo Alkenylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted selected from a substituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group,

L ₂₀₅ is, *-O-*', *-S-*', *-N(Q ₂₀₁ )-*', substituted or unsubstituted C ₁ -C ₂₀ alkylene group, substituted or unsubstituted C ₂ - C ₂₀ alkenylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkylene group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenylene group, 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 selected from non-aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic condensed polycyclic groups,

xa1 to xa4 are independently selected from integers from 0 to 3,

xa5 is selected from an integer from 1 to 10,

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

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

According to one embodiment, among Formulas 201 and 202,

L ₂₀₁ to L ₂₀₅ are independently of each other,

Phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, hepthalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluore Nylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, pe Relenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubcenylene group, coronenylene group, ovalenylene group, thiophenylene group, furanylene group, carbazonylene group, indolylene group, isoindolylene group , benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group and pyridinylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, pentale Nyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl 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, Rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole phenyl substituted with at least one selected from the group consisting of dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) and -N(Q ₃₁ )(Q ₃₂ ) Len group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, hepthalenylene group, indacenylene group, acenaphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenyl Len group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perile Nylene group, pentaphenylene group, hexacenylene group, pentacenylene group, rubisenylene group, coronenylene group, ovalenylene group, thiophenylene group, furanylene group, carbazonylene group, indolelylene group, isoindolylene group, Benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group and pyridinylene group;

is selected from,

Q ₃₁ to Q ₃₃ may be 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 independently 0, 1, or 2.

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

According to another embodiment, R ₂₀₁ to R ₂₀₄ and Q ₂₀₁ are each independently selected from a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a hepthalenyl 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, rubisenyl 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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, pentale Nyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl 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, Rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole A phenyl group substituted with at least one selected from the group consisting of 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, hepthalenyl 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, rubisenyl group, coronenyl group, ovalenyl 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 and pyridinyl group;

can be selected from,

For a description of Q ₃₁ to Q ₃₃ , refer to what is described in the present specification.

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

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

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

It may be selected from among, but is not limited to.

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

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

Carbazole diary; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, phenyl group substituted with C ₁ -C ₁₀ alkyl group, phenyl group substituted with -F, 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 among, but is not limited to.

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

<Formula 201A>

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

<Formula 201A(1)>

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

<Formula 201A-1>

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

<Formula 202A>

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

<Formula 202A-1>

Among the formulas 201A, 201A(1), 201A-1, 202A and 202A-1,

For descriptions of L ₂₀₁ to L ₂₀₃ , xa1 to xa3, xa5 and R ₂₀₂ to R ₂₀₄ , refer to what is described herein,

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

R ₂₁₃ to R ₂₁₇ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, phenyl group, biphenyl group, terphenyl group, C ₁ -C ₁₀ substituted with alkyl group. phenyl group, phenyl group substituted with -F, 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, rubisenyl group, coronenyl group, ovalenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, di It may be selected from benzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, and 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 thickness of the hole transport region may be about 100Å to about 10000Å, for example, about 100Å to about 1000Å. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 Å to about 9000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is about 50 Å. It may be from about 2000 Å, for example from about 100 Å to about 1500 Å. When the thickness of the hole transport region, hole injection layer, and hole transport layer satisfies the above-mentioned ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

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

[p-dopant]

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

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

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

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

For example, the p-dopant is,

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

metal oxides such as tungsten oxide and molybdenum oxide;

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

A compound represented by the following formula 221;

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

<HAT-CN> <F4-TCNQ>

<Formula 221>

In Formula 221,

R ₂₂₁ to R ₂₂₃ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, or a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group. , substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent selected from a non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed 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 It has one substituent.

[Emitting layer of 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 may have a structure in which two or more layers selected from a red light-emitting layer, a green light-emitting layer, and a blue light-emitting layer are stacked in contact or spaced apart, or two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material may be layered. It has a mixed structure 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 content of the dopant in the light-emitting layer can typically be selected in the range of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host, but is not limited thereto.

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

[Host in the emitting layer]

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

<Formula 301>

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

In the above formula 301,

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

xb11 is 1, 2 or 3,

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

xb1 is selected from integers from 0 to 5,

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

xb21 is selected from integers from 1 to 5,

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

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

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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), - C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )(Q ₃₂ ), substituted with at least one selected from 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 and dibenzothiophene group;

is selected from,

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

In Formula 301, when xb11 is 2 or more, 2 or more Ar ₃₀₁ may be connected to each other through a single bond.

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

<Formula 301-1>

<Formula 301-2>

Of the above formulas 301-1 to 301-2

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

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

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

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

For descriptions of L ₃₀₁ , xb1, R ₃₀₁ and Q ₃₁ to Q ₃₃ , refer to what is described herein,

For the description of L ₃₀₂ to L ₃₀₄ , refer independently to the description of L ₃₀₁ above,

The description of Xb2 to xb4 independently refers to the description of xb1 above,

The description of R ₃₀₂ to R ₃₀₄ independently refers to the description of R ₃₀₁ above.

For example, in the formulas 301, 301-1 and 301-2, L ₃₀₁ to L ₃₀₄ 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 Lenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazonylene group, indolylene group, isoindolylene group, benzoyl group Furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, pyridinylene group, imidazolylene group, pyrazonylene group , thiazonylene group, isothiazolylene group, oxazonylene group, isoxazonylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl Len group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinilene group, quinazolinylene group, cynolinylene group, phenanthridinylene group, acridinylene group, phenane Trolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazonylene group, benzoxazonylene group, isobenzooxazolylene group, triazonylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidi nylene group and azacarbazolylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl 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 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 , isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N( Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ ) (Q ₃₂ ) Substituted with at least one selected from phenylene group, naphthylene group, fluorenylene group, spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenyl Len group, anthracenylene group, fluoranthenylene group, triphenylene group, pyrenylene group, chrycenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carboxymethylene group Zolylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group , pyridinylene group, imidazolylene group, pyrazonylene group, thiazonylene group, isothiazolylene group, oxazoylene group, isoxazonylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group. , pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinylene group, quinazolinylene group, cinolinyl Len group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazynylene group, benzoimidazolylene group, isobenzothiazonylene group, benzoxazonylene group, isobenzooxazonylene group, triazonylene group, tetrazolyl Len group, imidazopyridinylene group, imidazopyrimidinylene group and azacarbazolylene group;

is selected from,

For a description of Q ₃₁ to Q ₃₃ , refer to what is described in the present specification.

As another example, in Formulas 301, 301-1 and 301-2, R ₃₀₁ to R ₃₀₄ 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, triphenyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl 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, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl 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 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 , isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N( Q ₃₁ )(Q ₃₂ ), -B(Q ₃₁ )(Q ₃₂ ), -C(=O)(Q ₃₁ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ ) (Q ₃₂ ) Substituted with at least one selected from phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group , anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group. , isoindoleyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, 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, iso Quinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cynolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazole diary group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group;

is selected from,

For a description of Q ₃₁ to Q ₃₃ , refer to what is described in the present specification.

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

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

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

The phosphorescent dopant may include an organometallic complex represented by the following chemical formula 401:

<Formula 401>

M(L ₄₀₁ ) _xc1 (L ₄₀₂ ) _xc2

<Formula 402>

In formulas 401 and 402,

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

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

L ₄₀₂ is an organic ligand, xc2 is selected from an integer of 0 to 4, and when xc2 is 2 or more, 2 or more L ₄₀₂ are the same 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 double bond, X ₄₀₂ and X ₄₀₄ are connected through a single bond or double bond,

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

X ₄₀₅ is a single binding, *-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, deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, biphenyl group, terphenyl group, or naphthyl group,

X ₄₀₆ is a single bond, O or S,

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

xc11 and xc12 are independently selected from integers from 0 to 10,

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

According to one embodiment, in Formula 402, A ₄₀₁ and A ₄₀₂ are each independently selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, and 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, benzoxazole group, isobenzooxa It may be selected from the sol group, triazole group, tetrazole group, oxadiazole group, triazine group, dibenzofuran group and dibenzothiophene group.

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

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

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

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

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

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

is selected from,

Q ₄₀₁ to Q ₄₀₃ may be 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 _{401 out of two or more L 401 are} optionally connected to each other through X ₄₀₇ , which is a linking group, or two A ₄₀₂ are optionally connected to each other. , can be connected to each other through the linking group X ₄₀₈ (see compounds PD1 to PD4 and PD7 below). Wherein _{X 407 and} *-C(Q ₄₁₃ )(Q ₄₁₄ )-*' or *-C(Q ₄₁₃ )=C(Q ₄₁₄ )-*' (where 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 (e.g., acetylacetonate), carboxylic acid (e.g., picolinate), -C(=O), isonitrile, -CN, and phosphorus. (For example, phosphine, 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 emitting layer]

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

The fluorescent dopant may include a compound represented by the following 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 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 cycloalkylene 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 selected from a substituted divalent non-aromatic condensed polycyclic group and a substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group,

xd1 to xd3 are independently selected from integers from 0 to 3,

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

Xd4 may be selected from an integer of 1 to 6.

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

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

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , naphthalene group, hepthalene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene, substituted with at least one selected from phenyl group, biphenyl group, terphenyl group and 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 indenophenan. Tren Group;

can be selected from among.

According to another embodiment, in Formula 501, L ₅₀₁ to L ₅₀₃ 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 Lenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazonylene group, indolylene group, isoindolylene group, benzoyl group furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, pyridinylene group; and

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

can be selected from among.

According to another embodiment, in Formula 501, R ₅₀₁ and R ₅₀₂ 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, triphenyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl group, benzofuranyl group, benzothiophenyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , 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, isoindolyl group, benzofuranyl group, benzothiophenyl group. , dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, pyridinyl group and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ). 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, isoindolyl group, benzofuranyl group, benzothio phenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group and pyridinyl group;

is selected from,

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

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

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

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

[Electron transport area in organic layer 150]

The electron transport region has i) a single-layer structure consisting of a single layer made of a single material, ii) a single-layer structure consisting 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. You can have

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

For example, the electron transport region may be 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 (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a condensed ring compound represented by Formula 1.

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

The "π electron-deficient nitrogen 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 ring" is i) a 5-7 membered heteromonocyclic group with 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 group having at least one *-N=*' moiety. It may be a heteropolycyclic group in which at least one of the to 7-membered heteromonocyclic group and at least one C ₅ -C ₆₀ carbocyclic group are condensed with each other.

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

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

<Formula 601>

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

In the above 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, substituted or Unsubstituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted or unsubstituted C ₆ -C ₆₀ arylene group, substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group, substituted or unsubstituted divalent non- selected from aromatic condensed polycyclic groups and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic groups,

xe1 is selected from integers from 0 to 5,

R ₆₀₁ is a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group , substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 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 from 1 to 5.

According to one embodiment, at least one of the xe11 Ar _601s and the xe21 R _601s may include a 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 , benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group and azacarbazole group. ; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -S(=O) ₂ (Q ₃₁ ) and -P(=O)(Q ₃₁ )( Q ₃₂ ) substituted with at least one selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, 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, cinoline 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, imidazopyridine group, polyzopyrimidine group and azacarbazole group;

can be selected from,

Q ₃₁ to Q ₃₃ may be 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 2 or more, 2 or more Ar ₆₀₁ may be connected to each other through a single bond.

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

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

<Formula 601-1>

In the above formula 601-1,

X ₆₁₄ is N _or C(R ₆₁₄ ), X ₆₁₅ is N or C(R _{615 )} , X ₆₁₆ is N or C(R ₆₁₆ ), and at least one of

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

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

According to one embodiment, in Formulas 601 and 601-1, L ₆₀₁ and L ₆₁₁ to L ₆₁₃ 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 Lenylene group, pyrenylene group, chrysenylene group, perylenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazonylene group, indolylene group, isoindolylene group, benzoyl group Furanylene group, benzothiophenylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, pyridinylene group, imidazolylene group, pyrazonylene group , thiazonylene group, isothiazolylene group, oxazonylene group, isoxazonylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinyl Len group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinilene group, quinazolinylene group, cynolinylene group, phenanthridinylene group, acridinylene group, phenane Trolinylene group, phenazinylene group, benzoimidazolylene group, isobenzothiazonylene group, benzoxazonylene group, isobenzooxazolylene group, triazonylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidi nylene group and azacarbazolylene group; and

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl 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 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 , isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group, substituted with at least one selected from phenylene group, naphthylene group, fluorenylene group, Spiro-bifluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, pe Relenylene group, pentaphenylene group, hexacenylene group, pentacenylene group, thiophenylene group, furanylene group, carbazoylene group, indolylene group, isoindolylene group, benzofuranylene group, benzothiophenylene group, dibenzofu Lanylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, pyridinylene group, imidazolylene group, pyrazoylene group, thiazonylene group, isothiazolylene group, oxazolyl Len group, isoxazolylene group, thiadiazolylene group, oxadiazolylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, triazinylene group, quinolinylene group, isoquinolinylene group, benzoquinolinyl Len group, phthalazinylene group, naphthyridinylene group, quinoxalinilene group, quinazolinylene group, cinolinylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazynylene group, benzoimidazolyl Len group, isobenzothiazonylene group, benzoxazonylene group, isobenzooxazonylene group, triazonylene group, tetrazolylene group, imidazopyridinylene group, imidazopyrimidinylene group and azacarbazolylene group;

It may be selected from among, but is not limited to.

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

According to another embodiment, in Formulas 601 and 601-1, R ₆₀₁ and R ₆₁₁ to R ₆₁₃ 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, triphenyl group Nyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl 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, isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group , phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenyl Renyl group, pyrenyl group, chrysenyl group, perylenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl 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 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 , isobenzooxazolyl group, triazolyl group, tetrazolyl group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group, substituted with at least one selected from phenyl group, biphenyl group, terphenyl group, naphthyl group, flu Orenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, perile Nyl group, pentaphenyl group, hexacenyl group, pentacenyl group, thiophenyl group, furanyl group, carbazolyl group, indolyl group, isoindolyl 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, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazole diary group, imidazopyridinyl group, imidazopyrimidinyl group and azacarbazolyl group; and

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

is selected from,

For descriptions of Q ₆₀₁ and Q ₆₀₂ , refer 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 may be BCP (2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-Diphenyl-1,10-phenanthroline), Alq ₃ , BAlq, TAZ ( It may include at least one compound selected from 3-(Biphenyl-4-yl)-5-(4- tert -butylphenyl)-4-phenyl- 4H -1,2,4-triazole) and NTAZ.

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

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

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

The metal-containing material may include at least one selected from an alkali metal complex and an alkaline earth metal complex. The metal ion of the alkaline metal complex may be selected from Li ions, Na ions, K ions, Rb ions, and Cs ions, and the metal ions of the alkaline earth metal complex may be Be ions, Mg ions, Ca ions, Sr ions, and Ba ions may 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, and 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 consisting of a single layer made of a single material, ii) a single-layer structure consisting 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. You can have

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

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

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

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

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

The alkali metal compound may be selected from alkali metal oxides such as Li ₂ O, Cs ₂ O, K ₂ O, and alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, KI, RbI, etc. there is. 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), etc. 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, alkaline earth metal complex, and 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, alkaline earth metal complex, and rare earth metal complex. The ligands are, independently of each other, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, and hydroxydiphenyloxa. It may be selected from diazole, hydroxydiphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline and cyclopentadiene, but is limited thereto. That is not the case.

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

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

[Second electrode (190)]

The second electrode 190 is disposed on the organic layer 150 as described above. The second electrode 190 may be a cathode, which is an electron injection electrode. In this case, materials for the second electrode 190 include metals, alloys, electrically conductive compounds, and combinations thereof having a low work function. (combination) can be used.

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

The second electrode 190 may have a single-layer structure or a multi-layer structure having 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, and the organic light emitting device 20 of FIG. 3 The light emitting device 30 has a structure in which a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 are sequentially stacked, and the organic light emitting device 40 of FIG. 4 is It has a structure in which the first capping layer 210, the first electrode 110, the organic layer 150, the second electrode 190, and the second capping layer 220 are sequentially stacked.

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

The light generated in the light-emitting layer of the organic layer 150 of the organic light-emitting device 20 and 40 may pass through the first electrode 110 and the first capping layer 210, which are semi-transmissive electrodes or transmissive electrodes, and 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 be extracted to the outside through the second electrode 190 and the second capping layer 220, which are semi-transmissive or transmissive electrodes.

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

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

At least one of the first capping layer 210 and the second capping layer 220 may include a condensed ring compound represented by Formula 1.

Alternatively, at least one of the first capping layer 210 and the second capping layer 220 may independently contain a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphine derivative, or a phthalocyanine. It may include at least one substance selected from phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth metal complexes. The carbocyclic compounds, heterocyclic compounds and amine compounds 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.

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

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

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, respectively, vacuum deposition method, spin coating method, cast method, LB method (Langmuir-Blodgett), inkjet printing method, laser printing method, and laser method. It can be formed in a predetermined area using various methods such as thermal transfer (Laser Induced Thermal Imaging, LITI).

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

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

[General definition of substituent]

As used herein, 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 group, ethyl group, propyl group, isobutyl group, and sec-butyl group. group, ter-butyl group, pentyl group, iso-amyl group, hexyl group, etc. As used herein, the C ₁ -C ₆₀ alkylene group refers to a divalent group having the same structure as the C ₁ -C ₆₀ alkyl group.

As used herein, the C ₂ -C ₆₀ alkenyl group refers to a hydrocarbon group containing at least one carbon double bond at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethenyl group, propenyl group, and butenyl group. etc. are included. As used herein, the C ₂ -C ₆₀ alkenylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkenyl group.

As used herein, the C ₂ -C ₆₀ alkynyl group refers to a hydrocarbon group containing one or more carbon triple bonds at the middle or end of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include ethynyl group, propynyl group, etc. Included. As used herein, the C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

As used herein, C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the formula -OA ₁₀₁ (where A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include methoxy group and ethoxy group. , isopropyloxy group, etc.

As used herein, 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 cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and cyclo Heptyl group, etc. are included. As used herein, the C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

As used herein, C ₁ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 1 to 10 carbon atoms containing at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom. , Specific examples thereof include 1,2,3,4-oxatriazolidinyl, tetrahydrofuranyl, tetrahydrothiophenyl, etc. As used herein, the C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

As used herein, C ₃ -C ₁₀ cycloalkenyl group refers to 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, and its specific details Examples include cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, etc. As used herein, the C ₃ -C ₁₀ cycloalkenylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

As used herein, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms containing at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom, forming a ring. It has at least one double bond within it. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include 4,5-dihydro-1,2,3,4-oxatriazolyl group, 2,3-dihydrofuranyl group, 2,3-dihydro Thiophenyl group, etc. are included. As used herein, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

As used herein, the C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the C ₆ -C ₆₀ arylene group refers to a carbocyclic aromatic system having 6 to 60 carbon atoms. It means a divalent group with . Specific examples of the C ₆ -C ₆₀ aryl group include phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, chrysenyl group, etc. 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.

As used herein, the C ₁ -C ₆₀ heteroaryl group is a monovalent group containing at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom and having a heterocyclic aromatic system having 1 to 60 carbon atoms. means, and the C ₁ -C ₆₀ heteroarylene group is 2 which contains at least one hetero atom selected from N, O, Si, P and S as a ring-forming atom and has a heterocyclic aromatic system having 1 to 60 carbon atoms. means group. Specific examples of the C ₁ -C ₆₀ heteroaryl group include pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, etc. 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.

As used herein, 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 (where A 102 is the C 6 -C ₆₀ aryl group). , A ₁₀₃ refers to the C ₆ -C ₆₀ aryl group).

As used herein, a monovalent non-aromatic condensed polycyclic group has two or more rings condensed with each other, contains only carbon as a ring forming atom, and the entire molecule is non-aromatic. 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. As used herein, a divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

As used herein, a monovalent non-aromatic condensed heteropolycyclic group (non-aromatic condensed heteropolycyclic group) has 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 refers to a monovalent group (for example, having 1 to 60 carbon atoms) that contains a heteroatom and the entire molecule is non-aromatic. Specific examples of the monovalent non-aromatic condensed heteropolycyclic group include carbazolyl group and the like. As used herein, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

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

As used herein, the C ₁ -C ₆₀ heterocyclic group has the same structure as the C ₅ -C ₆₀ carbocyclic group, but as ring-forming atoms, in addition to carbon (carbon number may be 1 to 60), N , refers to a group containing at least one hetero atom selected from O, Si, P and S.

As used herein, 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 Len group, substituted C ₃ -C ₁₀ cycloalkenylene group, substituted C ₁ -C ₁₀ heterocycloalkenylene group, substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted Divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed heteropolycyclic group, substituted C ₁ -C ₆₀ alkyl group, substituted C 2 -C ₆₀ alkenyl group, substituted C _{2 -C 60} alkynyl group, Substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ hetero Cycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted 1 At least one of the substituents of the divalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group is,

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

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

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 Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group , C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocyclo Alkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent 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 ), C ₃ -C ₁₀ cycloalkyl group, C ₁ -C substituted with at least one selected from ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group; and

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

is selected from,

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, hydroxyl group, cyano group, nitro group, amine Dino group, hydrazino group, hydrazono group, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C 2 -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C _{3 -C 10} cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic It may be selected from a condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, a biphenyl group, and a terphenyl group.

In this specification, “Ph” refers to a phenyl group, “Me” refers to a methyl group, “Et” refers to an ethyl group, “ter-Bu” or “Bu ^t ” refers to a tert-butyl group, and “OMe " means a methoxy group.

As used herein, “biphenyl group” means “a phenyl group substituted with a phenyl group.” The “biphenyl group” belongs to the “substituted phenyl group” in which the substituent is a “C ₆ -C ₆₀ aryl group”.

As used herein, “terphenyl group” means “a phenyl group substituted with a biphenyl group.” The “terphenyl group” belongs to the “substituted phenyl group” in which the substituent is a “C ₆ -C ₆₀ aryl group substituted with a C ₆ -C ₆₀ aryl group.”

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

Hereinafter, a compound and an organic light-emitting device according to an embodiment of the present invention will be described in more detail through synthesis examples and examples. 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 5]

<Scheme 1>

Synthesis of Intermediate A-1

phenylboronic acid (2.44 g, 20.0 mmol), 9-bromo-10-nitrophenanthrene (6.04 g, 20.0 mmol), Pd(PPh ₃ ) ₄ (1.16 g, 1.00 mmol), TBAB (Tetrabutylammonium bromide) (0.322 g, 1.00 mmol) ) and Na ₂ CO ₃ (6.28 g, 60.0 mmol) were dissolved in 80 mL of toluene/ethanol/H ₂ O (3/3/1) mixed solution and stirred at 80°C for 16 hours. After the reaction solution was cooled to room temperature, it was extracted three times with 60 mL of water and 60 mL of diethyl ether. The organic layer obtained therefrom was dried with MgSO ₄ , the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain 4.91 g of Intermediate A-1 (yield 82%). The produced compound was confirmed by LC-MS. C ₂₀ H ₁₃ NO ₂ : M+1 299.1

Synthesis of Intermediate A-2

Intermediate A-1 (4.91 g, 16.4 mmol), Tin (5.84 g, 49.2 mmol), and 8.2 mL (82 mmol, conc. 36.5%) of HCl were dissolved in 60 mL of ethanol and stirred at 100°C for 8 hours. After the reaction solution was cooled to room temperature, 5 g of sodium hydroxide dissolved in 10 mL of water was added to the filtrate obtained through a reduced-pressure filter, and then extracted three times with 60 mL of water and 60 mL of dichloromethane. The organic layer obtained therefrom was dried with MgSO ₄ , the solvent was evaporated, and the resulting residue was separated and purified by silica gel column chromatography to obtain 3.98 g of Intermediate A-2 (yield 90%). The produced compound was confirmed by LC-MS. C ₂₀ H ₁₅ N: M+1 269.1

Synthesis of Intermediate A-3

Intermediate A-2 (3.98 g, 14.7 mmol) and 3-bromobenzaldehyde (5.38 g, 29.4 mmol) were dissolved in 30 mL of trifluoroacetic acid and stirred in a sealed tube at 130°C for 3 days. The reaction solution was cooled to room temperature, quenched with NaHCO ₃ , and extracted three times with 60 mL of water and 60 mL of dichloromethane. The organic layer obtained therefrom was dried over MgSO ₄ , the solvent was evaporated, and the resulting residue was separated and purified by silica gel column chromatography to obtain 3.83 g of Intermediate A-3 (yield 60%). The produced compound was confirmed by LC-MS. C ₂₇ H ₁₆ BrN: M+1 433.1

Synthesis of compound 5

Intermediate A-3 (3.83 g, 8.82 mmol), 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2- Carbonitrile (3.05 g, 10 mmol), Pd(PPh ₃ ) ₄ (0.51 g, 0.44 mmol) and K ₂ CO ₃ (3.66 g, 2.65 mmol) were mixed in 60 mL of THF/H ₂ O (2/1 volume ratio). After dissolving in , it was stirred at 80°C for 16 hours. After the reaction solution was cooled to room temperature, 40 mL of water was added and extracted three times with 50 mL of ethylether. The collected organic layer was dried with MgSO ₄ , the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain 3.63 g of Compound 5 (yield 72%). The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₃ H ₂₈ N ₂ cal. 572.23, found 572.22

[Synthesis Example 2: Synthesis of Compound 7]

In the synthesis of compound 5, 9-phenyl was used instead of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile. The compound was prepared in the same manner as in Synthesis Example 1, except that -6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-2-carbonitrile was used. 7 3.83 g (yield 70%) was obtained. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₆ H ₂₇ N ₃ O cal. 621.22, found 621.23

[Synthesis Example 3: Synthesis of Compound 12]

<Scheme 2>

Synthesis of Intermediate B-1

6.05 g (80% yield) of Intermediate B-1 was obtained in the same manner as the synthesis of Intermediate A-1, except that 4-bromophenylboronic acid was used instead of phenylboronic acid. The produced compound was confirmed by LC-MS. C ₂₀ H ₁₂ NBrO ₂ : M+1 377.0

Synthesis of Intermediate B-2

5.01 g (yield 90%) of Intermediate B-2 was obtained in the same manner as the synthesis of Intermediate A-2, except that Intermediate B-1 was used instead of Intermediate A-1. The produced compound was confirmed by LC-MS. C ₂₀ H ₁₄ BrN: M+1 347.0

Synthesis of Intermediate B-3

4.38 g (yield 70%) of Intermediate B-3 was obtained in the same manner as the synthesis of Intermediate A-3, except that Intermediate B-2 was used instead of Intermediate A-2. The produced compound was confirmed by LC-MS. C ₂₇ H ₁₆ BrN: M+1 433.1

Synthesis of compound 12

In the synthesis of compound 5, 2-( Except for using 3-(dinaphtho[2,1-b:1',2'-d]furan-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. obtained 4.57 g of compound 12 (yield 65%) in the same manner as the synthesis of compound 5. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₅₃ H ₃₁ NO cal. 697.24, found 697.23

[Synthesis Example 4: Synthesis of Compound 19]

In the synthesis of compound 12, 2-(3-(dinaphtho[2,1-b:1',2'-d]furan-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3, The above synthesis, except that 4,4,5,5-tetramethyl-2-(10-(naphthalen-1-yl)anthracen-9-yl)-1,3,2-dioxaborolane was used instead of 2-dioxaborolane. 3.98 g (yield 60%) of Compound 19 was obtained in the same manner as Example 3. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₅₁ H ₃₁ N cal. 657.25, found 657.26

[Synthesis Example 5: Synthesis of Compound 30]

In the synthesis of intermediate B-1, (4-bromonaphthalen-1-yl)boronic acid was used instead of 4-bromophenylboronic acid, and in the synthesis of compound 12, 2-(3-(dinaphtho[2,1-b:1 ',2'-d]furan-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane instead of 9,9-dimethyl-7-(4,4,5, 4.27 g (yield 68%) of Compound 30 was obtained in the same manner as in Synthesis Example 3, except that 5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile was used. . The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₇ H ₃₀ N ₂ cal. 622.24, found 622.25

[Synthesis Example 6: Synthesis of Compound 47]

In the synthesis of intermediate A-1, 2-naphthaleneboronic acid was used instead of phenylboronic acid, and in the synthesis of compound 5, 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2 9-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole instead of -dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile 4.23 g of compound 47 (yield 63%) was obtained in the same manner as in Synthesis Example 1, except that -2-carbonitrile was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₅₀ H ₂₉ N ₃ cal. 671.24, found 671.23

[Synthesis Example 7: Synthesis of Compound 56]

In the synthesis of intermediate A-1, 2-pyridineboronic acid was used instead of phenylboronic acid, and in the synthesis of compound 5, 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2 2-(dinaphtho[2,1-b:1',2'-d]furan-6-yl)-4,4,5,5 instead of -dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile 4.36 g of Compound 56 (yield 70%) was obtained in the same manner as in Synthesis Example 1, except that -tetramethyl-1,3,2-dioxaborolane was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₆ H ₂₆ N ₂ O cal. 622.20, found 622.19

[Synthesis Example 8: Synthesis of Compound 67]

In the synthesis of intermediate A-1, 4-pyridineboronic acid is used instead of phenylboronic acid, in the synthesis of intermediate A-3, 4-bromobenzaldehyde is used instead of 3-bromobenzaldehyde, and in the synthesis of compound 5, 9,9- 3,3'-(5-(4,4, 3.52 g of Compound 67 (yield 60%) in the same manner as in Synthesis Example 1, except that 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)dipyridine was used. got it The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₂ H ₂₆ N ₄ cal. 586.22, found 586.21

[Synthesis Example 9: Synthesis of Compound 79]

In the synthesis of intermediate A-1, 8-quinolineboronic acid was used instead of phenylboronic acid, and in the synthesis of compound 5, 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2 9-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole instead of -dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile 4.51 g of compound 79 (yield 67%) was obtained in the same manner as in Synthesis Example 1, except that -2-carbonitrile was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₉ H ₂₈ N ₄ cal. 672.23, found 672.22

[Synthesis Example 10: Synthesis of Compound 88]

In the synthesis of intermediate A-1, 3-isoquinolineboronic acid was used instead of phenylboronic acid, and in the synthesis of compound 5, 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2 2-(dinaphtho[2,1-b:1',2'-d]furan-6-yl)-4,4,5,5 instead of -dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile 4.64 g of Compound 88 (yield 69%) was obtained in the same manner as in Synthesis Example 1, except that -tetramethyl-1,3,2-dioxaborolane was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₅₀ H ₂₈ N ₂ O cal. 672.22, found 672.20

[Synthesis Example 11: Synthesis of Compound 89]

Intermediate B-3 (3.91 g, 9.00 mmol) prepared in Synthesis Example 3 was dissolved in 30 mL of THF, and then n -butyllithium (3.6 mL, 2.5 M in Hexane) was added at -80°C. One hour later, chlorodiphenylphosphine (1.99 g, 9 mmol) was added at the same temperature. After stirring at room temperature for 3 hours, water was added and washed three times with diethylether (30 mL). The washed diethylether layer was dried with MgSO ₄ and then dried under reduced pressure to obtain a product. Then, 30 mL of H ₂ O ₂ was added and stirred for 1 hour. After stirring, water was added and washed three times with diethylether (30 mL). The washed diethylether layer was dried over MgSO ₄ and then dried under reduced pressure to obtain a product, which was then separated and purified using silica gel column chromatography to obtain 3.00 g (yield 60%) of Compound 89 as a white solid. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₃₉ H ₂₆ NOP cal. 555.18, found 555.19

[Synthesis Example 12: Synthesis of Compound 91]

Intermediate B-3 (4.35 g, 10.0 mmol) prepared in Synthesis Example 3, diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide ( 4.04 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.58 g, 0.50 mmol) and K ₂ CO ₃ (4.15 g, 30.0 mmol) were dissolved in 60 mL of THF/H ₂ O (2/1 volume ratio) mixed solution. , and stirred at 80°C for 16 hours. After cooling the reaction solution to room temperature, 40 mL of water was added and extracted three times with 50 mL of diethylether. The collected organic layer was dried with MgSO ₄ , the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain 4.29 g of compound 91 (yield 68%). The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₅ H ₃₀ NOP cal. 631.21, found 631.22

[Synthesis Example 13: Synthesis of Compound 103]

In the synthesis of Intermediate B-1, 3.45 g (yield 67%) of Compound 103 was produced in the same manner as in Synthesis Example 11, except that (4-bromonaphthalen-1-yl)boronic acid was used instead of 4-bromophenylboronic acid. got it The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₃ H ₂₈ NOP cal. 605.19, found 605.18

[Synthesis Example 14: Synthesis of Compound 119]

In the synthesis of compound 91, 4,4,5,5-tetramethyl-2 was used instead of diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide. 4.29 g of Compound 119 (yield 68%) was obtained in the same manner as in Synthesis Example 12, except that -(10-(phenylsulfonyl)anthracen-9-yl)-1,3,2-dioxaborolane was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₇ H ₂₉ NO ₂ S cal. 671.19, found 671.18

[Synthesis Example 15: Synthesis of Compound 129]

<Scheme 3>

Synthesis of Intermediate C-1

9-bromophenanthrene (2.57 g, 10.0 mmol) was dissolved in 30 mL of THF, and n -butyllithium (4.0 mL, 2.5 M in Hexane) was added at -80°C. One hour later, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.24 mL, 11 mmol) was added at the same temperature. After stirring at room temperature for 3 hours, water was added and washed three times with diethylether (30 mL). The washed diethylether layer was dried over MgSO ₄ and then dried under reduced pressure to obtain a product, which was then separated and purified using silica gel column chromatography to obtain 1.88 g (yield 62%) of Intermediate C-1. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₂₀ H ₃₁ BO ₂ : M+1 378.0

Synthesis of Intermediate C-2

Intermediate C-2 (3.04 g, 10.0 mmol), 1,4-dibromo-2-nitrobenzene (2.81 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.58 g, 0.50 mmol), TBAB (Tetrabutylammonium bromide) (0.161 g, 0.50 mmol) and Na ₂ CO ₃ (3.14 g, 30.0 mmol) were dissolved in 40 mL of a toluene/ethanol/H ₂ O (3/3/1) mixed solution and stirred at 80°C for 16 hours. After the reaction solution was cooled to room temperature, it was extracted three times with 60 mL of water and 60 mL of diethyl ether. The organic layer obtained from this was dried over MgSO ₄ and the solvent was evaporated. The resulting residue was separated and purified by silica gel column chromatography to obtain 3.06 g of intermediate C-2 (yield 81%). The produced compound was confirmed by LC-MS. C ₂₀ H ₁₂ NBrO ₂ : M+1 378.0

Synthesis of intermediate C-3

Intermediate C-1 (3.78 g, 10.0 mmol), Tin (3.56 g, 30.0 mmol), and 5.0 mL (50 mmol, conc. 36.5%) of HCl were dissolved in 40 mL of ethanol and stirred at 100°C for 8 hours. The reaction solution was cooled to room temperature, and then 5 g of sodium hydroxide dissolved in 10 mL of water was added to the filtrate obtained by vacuum filtering, and then extracted three times with 60 mL of water and 60 mL of dichloromethane. The organic layer obtained therefrom was dried over MgSO ₄ and the solvent was evaporated. The resulting residue was separated and purified using silica gel column chromatography to obtain 2.99 g of intermediate C-3 (yield 86%). The produced compound was confirmed by LC-MS. C ₂₀ H ₁₄ BrN: M+1 348.0

Synthesis of intermediate C-4

Intermediate C-3 (3.48 g, 10.0 mmol) and 3-bromobenzaldehyde (3.70 g, 20.0 mmol) were dissolved in 20 mL of trifluoroacetic acid and stirred in a sealed tube at 130°C for 3 days. The reaction solution was cooled to room temperature, quenched with NaHCO ₃ , and extracted three times with 40 mL of water and 60 mL of dichloromethane. The organic layer obtained therefrom was dried over MgSO ₄ , the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain 2.99 g of intermediate C-4 (yield 69%). The produced compound was confirmed by LC-MS. C ₂₇ H ₁₆ BrN: M+1 434.1

Synthesis of compound 129

Intermediate C-4 (4.34 g, 10.00 mmol) was dissolved in 30 mL of THF, and then n -butyllithium (4.0 mL, 2.5 M in Hexane) was added at -80°C. One hour later, chlorodiphenylphosphine (2.20 g, 10 mmol) was added at the same temperature. After stirring at room temperature for 3 hours, water was added and washed three times with diethylether (30 mL). The washed diethylether layer was dried with MgSO ₄ and then dried under reduced pressure to obtain a product. Then, 30 mL of H ₂ O ₂ was added and stirred for 1 hour. After stirring, water was added and washed three times with diethylether (30 mL). The washed diethylether layer was dried over MgSO ₄ and then dried under reduced pressure to obtain a product, which was then separated and purified using silica gel column chromatography to obtain 3.27 g of compound 129 (yield 59%). The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₃₉ H ₂₆ NOP cal. 555.18, found 555.19

[Synthesis Example 16: Synthesis of Compound 134]

Intermediate C-4 (4.34 g, 10.0 mmol) prepared in Synthesis Example 15, diphenyl(10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9- yl)phosphine oxide (5.04 g, 10.0 mmol), Pd(PPh ₃ ) ₄ (0.58 g, 0.50 mmol) and K ₂ CO ₃ (4.15 g, 30.0 mmol) were mixed in THF/H ₂ O (2/1 volume ratio) After dissolving in 60 mL of solution, it was stirred at 80°C for 16 hours. After cooling the reaction solution to room temperature, 40 mL of water was added and extracted three times with 50 mL of diethylether. The collected organic layer was dried over MgSO ₄ , the solvent was evaporated, and the resulting residue was purified by separation using silica gel column chromatography to obtain 4.29 g of compound 134 (yield 68%). The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₅₃ H ₃₄ NOP cal. 731.24, found 731.23

[Synthesis Example 17: Synthesis of Compound 138]

In the synthesis of intermediate C-2, 3,6-dibromo-2-nitropyridine was used instead of 1,4-dibromo-2-nitrobenzene, and in the synthesis of compound 134, diphenyl (3-(4,4,5,5 Instead of -tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide, use diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen- 4.37 g of compound 138 (yield 64%) was obtained in the same manner as in Synthesis Example 16, except that 1-yl)phosphine oxide was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C48H31N2OP cal. 682.22, found 682.21

[Synthesis Example 18: Synthesis of Compound 143]

In the synthesis of intermediate C-2, 3.88 g of compound 143 (yield 64 %) was obtained. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₃ H ₂₈ NOP cal. 605.19, found 605.18

[Synthesis Example 19: Synthesis of Compound 146]

In the synthesis of intermediate C-2, 1,4-dibromo-2-nitronaphthalene was used instead of 1,4-dibromo-2-nitrobenzene, and in the synthesis of compound 134, diphenyl (3-(4,4,5,5 Instead of -tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide, use diphenyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin- 4.43 g of Compound 146 (yield 65%) was obtained in the same manner as in Synthesis Example 16, except that 3-yl)phosphine oxide was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₈ H ₃₁ N ₂ OP cal. 682.22, found 682.21

[Synthesis Example 20: Synthesis of Compound 153]

In the synthesis of intermediate C-2, 5,8-dibromo-6-nitroquinoline was used instead of 1,4-dibromo-2-nitrobenzene, and in the synthesis of compound 134, diphenyl (10-(4,4,5,5 Instead of -tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9-yl)phosphine oxide, use diphenyl(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2- 4.17 g (yield 61%) of Compound 153 was obtained in the same manner as in Synthesis Example 16, except that yl)pyridin-2-yl)phosphine oxide was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₇ H ₃₀ N ₃ OP cal. 685.22, found 685.23

[Synthesis Example 21: Synthesis of Compound 154]

In the synthesis of intermediate C-2, 5,8-dibromo-7-nitroquinoline was used instead of 1,4-dibromo-2-nitrobenzene, and in the synthesis of compound 134, diphenyl (10-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9-yl)phosphine oxide instead of diphenyl(3-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl) 4.43 g of compound 154 (yield 65%) was obtained in the same manner as in Synthesis Example 16, except that phenyl)phosphine oxide was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₈ H ₃₁ N ₂ OP cal. 682.22, found 682.21

[Synthesis Example 22: Synthesis of Compound 168]

In the synthesis of intermediate C-2, 5,8-dibromo-6-nitroquinoline was used instead of 1,4-dibromo-2-nitrobenzene, and in the synthesis of compound 134, diphenyl (10-(4,4,5,5 -tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9-yl)phosphine oxide instead of 2-(phenylsulfonyl)-6-(4,4,5,5-tetramethyl-1,3,2- 4.12 g (yield 66%) of Compound 168 was obtained in the same manner as in Synthesis Example 16, except that dioxaborolan-2-yl)pyridine was used. The produced compound was confirmed through MS/FAB and ¹ H NMR. C ₄₁ H ₂₅ N ₃ O ₂ S cal. 623.17, found 623.18

Additional compounds were synthesized using the same synthetic method as the above synthetic route and appropriate intermediate materials, and ¹ H NMR and MS/FAB of the synthesized compounds are shown in Table 1 below.

Those skilled in the art can easily recognize the synthetic methods for compounds other than those shown in Table 1 by referring to the synthetic routes and raw materials.

compound
¹ H NMR (CDCl ₃ , 400 MHz) δ MS/FAB found calc. 5 δ = 9.23 (d, 1H), 8.87 (d, 1H), 8.69-8.65 (m, 2H), 8.36-8.34 (m, 1H), 8.22 (d, 1H), 7.92-7.76 (m, 7H), 7.70-7.64 (m, 3H), 7.60-7.45 (m, 4H), 7.36 (t, 1H), 7.12-7.08 (m, 1H), 1.65 (s, 6H) 572.22 572.23 7 δ = 9.22 (d, 1H), 8.86 (d, 1H), 8.69-8.66 (m, 2H), 8.57-8.55 (m, 1H), 8.23-8.21 (m, 2H), 8.08 (d, 1H), 8.03 (d, 1H), 7.92-7.76 (m, 7H), 7.70-7.48 (m, 8H), 7.41 (t, 1H), 7.32-7.28 (m, 1H), 7.13-7.09 (m, 1H) 621.23 621.22 12 δ = 9.23-9.19 (m, 1H), 8.83 (t, 2H), 8.69-8.63 (m, 4H), 8.33 (s, 1H), 8.06-7.90 (m, 7H), 7.86-7.48 (m, 15H) ), 7.09 (t, 1H) 697.23 697.24 19 δ = 9.22-9.20 (m, 1H), 8.82, 8.73-8.65 (m, 4H), 8.18 (d, 1H), 7.98-7.96 (m, 2H), 7.86-7.79 (m, 6H), 7.72-7.44 (m, 10H), 7.40-7.27 (m, 5H), 7.09 (t, 1H), 6.96 (t, 1H) 657.26 657.25 30 δ = 9.27 (d, 1H), 8.86 (d, 1H), 8.70 (d, 1H), 8.67 (d, 1H), 8.28 (s, 1H), 8.20-8.18 (m, 2H), 8.06-8.02 ( m, 2H), 7.95-7.79 (m, 5H), 7.74-7.45 (m, 8H), 7.23 (t, 1H), 7.07 (t, 1H), 1.66 (s, 6H) 622.25 622.24 47 δ = 9.29-9.26 (m, 1H), 8.82-8.76 (m, 2H), 8.70-8.64 (m, 3H), 8.23, 8.16-8.03 (m, 5H), 7.94 (d, 1H), 7.89-7.79 (m, 6H), 7.70-7.45 (m, 8H), 7.42 (t, 1H), 7.32-7.28 (m, 1H), 7.13 (t, 1H) 671.23 671.24 56 δ = 9.31-9.28 (m, 1H), 9.01 (d, 1H), 8.89-8.76 (m, 5H), 8.60-8.56 (m, 2H), 8.39 (s, 1H), 7.96-7.87 (m, 6H) ), 7.83-7.78 (m, 3H), 7.72-7.48 (m, 6H), 7.37 (t, 1H) 622.19 622.20 66 δ = 9.52-9.50 (m, 1H), 9.23-9.21 (m, 1H), 8.94 (d, 2H), 8.81 (d, 1H), 8.69-8.65 (m, 4H), 8.46 (d, 1H), 8.38-8.35 (m, 2H), 8.06-8.00 (m, 3H), 7.95-7.79 (m, 8H), 7.54-7.46 (m, 3H) 586.21 586.22 78 δ = 9.53-9.51 (m, 1H), 9.18 (d, 1H), 8.80-8.70 (m, 3H), 8.46 (d, 1H), 8.27 (d, 1H), 8.23 (d, 1H), 8.08 ( d, 1H), 8.04-7.94 (m, 3H), 7.86-7.76 (m, 5H), 7.70-7.48 (m, 8H), 7.41 (t, 1H), 7.31-7.28 (m, 1H), 7.16 ( t, 1H) 672.22 672.23 87 δ = 9.55 (d, 1H), 9.37-8.34 (m, 1H), 8.92 (d, 1H), 8.85-8.76 (m, 3H), 8.67-8.63 (m, 2H), 8.39 (d, 1H), 8.29 (dd, 1H), 8.19 (d, 1H), 8.01-7.76 (m, 11H), 7.72-7.48 (m, 6H) 672.20 672.22 89 δ = 9.23-9.16(m, 2H), 8.74-8.66(m, 3H), 7.95-7.93(m, 1H), 7.85-7.81(m, 5H), 7.69-7.61(m, 7H), 7.55-7.47 (m, 3H), 7.45-7.39(m, 4H), 7.12-7.07(m, 1H) 555.19 555.18 91 δ = 9.23-9.21(m, 1H), 8.71-8.65(m, 2H), 8.52-8.50(m, 1H), 8.37-8.36(m, 1H), 8.13-8.11(m, 1H), 7.98-7.97 (m, 2H), 7.87-7.81(m, 4H), 7.68-7.61(m, 8H), 7.57-7.48(m, 5H), 7.44-7.41(m, 4H), 7.12-7.08(m, 1H) 631.22 631.21 103 δ = 9.29-9.24(m, 2H), 8.96-8.94(m, 1H), 8.78-8.71(m, 2H), 8.67-8.66(m, 1H), 8.01-8.00(m, 2H), 7.85-7.81 (m, 2H), 7.74-7.72(m, 4H), 7.68-7.66(m, 2H), 7.63-7.53(m, 5H), 7.51-7.49(m, 1H), 7.41-7.39(m, 4H) , 7.08-7.06(m, 1H) 605.18 605.19
119 δ = 9.76-9.74(m, 1H), 9.26-9.22(m, 2H), 8.85-8.68(m, 4H), 8.06-8.01(m, 2H), 7.96-7.93(m, 3H), 7.80-7.63 (m, 12H), 7.54-7.52(m, 2H), 7.44-7.42(m, 4H) 671.18 671.19 129 δ = 8.84-8.83(m, 2H), 8.71-8.61(m, 4H), 8.00-7.99(m, 2H), 7.84-7.74(m, 3H), 7.70-7.68(m, 5H), 7.64-7.62 (m, 4H), 7.49-7.42(m, 5H) 555.19 555.18 134 δ = 8.84-8.83(m, 2H), 8.71-8.62(m, 3H), 8.20-8.18(m, 2H), 8.04-8.00(m, 3H), 7.83-7.68(m, 4H), 7.64-7.62 (m, 8H), 7.54-7.45(m, 6H), 7.39-7.37(m, 4H), 7.19-7.16(m, 2H) 731.23 731.24 138 δ = 8.93-8.85(m, 4H), 8.73-8.71(m, 1H), 8.59-8.55(m, 2H), 8.01-7.92(m, 4H), 7.79-7.72(m, 10H), 7.64-7.63 (m, 2H), 7.53-7.51(m, 3H), 7.45-7.39(m, 5H) 682.21 682.22 143 δ = 8.92-8.90(m, 2H), 8.85-8.69(m, 5H), 8.02-8.00(m, 2H), 7.80-7.69(m, 8H), 7.65-7.63(m, 4H), 7.55-7.53 (m, 3H), 7.40-7.38(m, 4H) 605.18 605.19 146 δ = 8.93-8.85(m, 4H), 8.79-8.77(m, 2H), 8.66-8.59(m, 2H), 8.40-8.39(m, 1H), 8.02-7.97(m, 3H), 7.83-7.80 (m, 6H), 7.74-7.69(m, 2H), 7.64-7.63(m, 4H), 7.50-7.48(m, 3H), 7.41-7.39(m, 4H) 682.21 682.22 153 δ = 9.76-9.74(m, 1H), 9.26-9.22(m, 2H), 8.85-8.68(m, 4H), 8.06-8.01(m, 2H), 7.96-7.93(m, 3H), 7.80-7.63 (m, 12H), 7.54-7.52(m, 2H), 7.44-7.42(m, 4H) 685.23 685.22 154 δ = 9.06-9.02(m, 2H), 8.94-8.79(m, 3H), 8.65-8.63(m, 1H), 8.39-8.38(m, 1H), 8.22-8.21(m, 1H), 8.02-7.93 (m, 3H), 7.80-7.74(m, 3H), 7.65-7.63(m, 9H), 7.57-7.56(m, 1H), 7.50-7.48(m, 3H), 7.44-7.41(m, 4H) 682.21 682.22 168 δ = 9.76-9.74(m, 2H), 9.26-9.25(m, 1H), 8.85-8.77(m, 3H), 8.70-8.69(m, 1H), 8.40-8.38(m, 1H), 8.15-8.14 (m, 1H), 8.05-8.02(m, 4H), 7.89-7.80(m, 3H), 7.74-7.69(m, 2H), 7.65-7.55(m, 7H) 623.18 623.17

Example 1

Corning as substrate and anode 15Ω/cm ² (1200Å) ITO glass substrate was cut into 50mm The glass substrate was installed.

2-TNATA was vacuum deposited on the ITO anode formed on the glass substrate to form a hole injection layer with a thickness of 600 Å, and then 4,4'-bis[N-(1-naphthyl)- was placed on the hole injection layer. N-phenylamino]biphenyl (hereinafter referred to as NPB) was vacuum deposited to a thickness of 300 Å to form a hole transport layer.

Host on top of the hole transport layer9,10-di-naphthalene-2-yl-anthracene (hereinafter referred to as ADN) and the dopant 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (hereinafter referred to as DPAVBi) was simultaneously deposited at a weight ratio of 98:2 to form a light emitting layer with a thickness of 300 Å.

After depositing Compound 5 to a thickness of 300 Å on the top of the light emitting layer to form an electron transport layer, LiF was deposited on the top of the electron transport layer to a thickness of 10 Å to form an electron injection layer, and Al was deposited on the top of the electron injection layer to a thickness of 3000 Å ( An organic light-emitting device was manufactured by forming a LiF/Al electrode by vacuum deposition to the thickness of the cathode electrode.

Example 2 to 22 and Comparative example 1 and 2

An organic light-emitting device was manufactured using the same method as Example 1, except that the compounds listed in Table 2 were used instead of Compound 1 when forming the electron transport layer.

Evaluation example One

The driving voltage, current density, luminance, efficiency, emission color, and half-life of the organic light-emitting devices manufactured in Examples 1 to 22 and Comparative Examples 1 and 2 were measured using Keithley SMU 236 and luminance meter PR650, and the results were measured. It is shown in Table 2.

ingredient Driving
Voltage
(V) current density
(㎃/㎠) Luminance
(cd/㎡) efficiency
(cd/A) Luminous color half life
(hr @100㎃
/㎠) Example 1 Compound 5 3.60 50 3,425 7.20 blue 618 Example 2 Compound 7 3.42 50 3,755 8.12 blue 625 Example 3 Compound 12 3.54 50 3,500 7.53 blue 656 Example 4 Compound 19 3.38 50 3,615 8.07 blue 602 Example 5 Compound 30 3.47 50 3,830 8.27 blue 635 Example 6 Compound 47 3.33 50 3,550 7.75 blue 620 Example 7 Compound 56 3.46 50 3,745 8.03 blue 635 Example 8 Compound 66 3.50 50 3,570 7.55 blue 662 Example 9 Compound 78 3.47 50 3,600 8.10 blue 627 Example 10 Compound 87 3.52 50 3,815 8.16 blue 640 Example 11 Compound 89 3.60 50 3,425 6.85 blue 618 Example 12 Compound 91 3.42 50 3,755 7.51 blue 625 Example 13 Compound 103 3.54 50 3,500 7.00 blue 656 Example 14 Compound 119 3.38 50 3,615 7.23 blue 602 Example 15 Compound 129 3.47 50 3,830 7.66 blue 635 Example 16 Compound 134 3.34 50 3,727 7.45 blue 627 Example 17 Compound 138 3.41 50 3,750 7.50 blue 637 Example 18 Compound 143 3.37 50 3,627 7.25 blue 608 Example 19 Compound 146 3.52 50 3,635 7.27 blue 650 Example 20 Compound 153 3.59 50 3,487 6.97 blue 591 Example 21 Compound 154 3.42 50 3,562 7.12 blue 613 Example 22 Compound 168 3.48 50 3,612 7.22 blue 647 Comparative Example 1 Compound A 5.06 50 3,010 6.52 blue 325 Comparative Example 2 Compound B 4.88 50 2,948 5.89 blue 411

From Table 2, it can be seen that the driving voltage, brightness, efficiency, and half-life of the organic light-emitting devices of Examples 1 to 22 are superior to the driving voltage, brightness, efficiency, and half-life of the organic light-emitting devices of Comparative Examples 1 and 2. .

Claims (20)

Condensed ring compound represented by the following formula (1):
<Formula 1>

<Formula 2-1><Formula2-2><Formula2-3>

<Formula 2-4><Formula2-5>

In Formulas 1 and 2-1 to 2-5,
A ring is selected from pyridine, naphthalene, quinoline and isoquinoline,
X ₁ is C(R ₁ ) or N, and X ₂ is C(R ₂ ) or N, where at least one of X ₁ and X ₂ is N,
One of R ₁ , R ₂ and R ₃ is Formula 2-1, Formula 2-2, Formula 2-3, Formula 2-4 or Formula 2-5, and the other is substituted or unsubstituted C ₆ -C ₆₀ aryl It's awesome,
R ₄ to R ₁₁ are independently hydrogen or deuterium,
L ₁ to L ₁₁ are independently selected from a substituted or unsubstituted C ₆ -C ₆₀ arylene group and a substituted or unsubstituted C ₁ -C ₆₀ heteroarylene group,
a1, a4, a7, a9, and a11 are independently 0, 1, or 2,
a2, a3, a5, a6, a8 and a10 are 0,
Ar ₁ to Ar ₇ are a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group (substituted or unsubstituted). monovalent non-aromatic condensed polycyclic group),
b1 to b4 are each independently 1, 2, or 3,
c3 is 0, 1, 2, 3, 4, 5 or 6,
The substituted C ₆ -C ₆₀ arylene group, substituted C ₁ -C ₆₀ heteroarylene group, substituted C ₆ -C ₆₀ aryl group, substituted C ₁ -C ₆₀ heteroaryl group and substituted monovalent non-aromatic At least one of the substituents of the condensed polycyclic group is,
selected from deuterium (-D), cyano group, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group,
* is a bonding site with a neighboring atom. delete According to paragraph 1,
The L ₁ to L ₁₁ are independently of each other,
Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetate Naphthylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group ), chrysenylene, naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene ), rubicenylene, coronenylene, ovalenylene, pyrrolylene, thiophenylene, furanylene, imidazolyl Imidazolylene, pyrazolylene, thiazolylene, isothiazolylene, oxazolylene, isoxazolylene, pyridinylene, pyra pyrazinylene, pyrimidinylene, pyridazinylene, isoindolylene, indolylene, indazolylene, purinylene , quinolinylene, isoquinolinylene, benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene. , quinazolinylene, cinnolinylene, carbazolilene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinyl. phenazinylene, benzoimidazolylene, benzofuranylene, benzothiophenylene, isobenzothiazolylene, benzoxazolylene, isobenzooxa Isobenzooxazolylene, triazolylene, tetrazolylene, oxadiazolylene, triazinylene, dibenzofuranylene, dibenzothiophenylene ( dibenzothiophenylene), benzocarbazolylene group, dibenzocarbazolylene group, dibenzosylrollylene group, thiadiazolylene group, imidazopyridinylene group and imidazopyrimidinylene group; and
Deuterium, cyano group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl 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, rubisenyl group, coronenyl group, Ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, Cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, iso Benzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, thiadia Substituted with at least one of a zolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, hepthalenylene group, indacenylene group, acenaph Thylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group , hexacenylene group, pentacenylene group, rubisenylene group, coronenylene group, ovalenylene group, pyrrolylene group, thiophenylene group, furanylene group, imidazolylene group, pyrazonylene group, thiazonylene group, isothia Zolylene group, oxazonylene group, isoxazonylene group, pyridinylene group, pyrazinylene group, pyrimidinylene group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinyl Len group, isoquinolinylene group, benzoquinolinylene group, phthalazinylene group, naphthyridinylene group, quinoxalinilene group, quinazolinylene group, cynolinylene group, carbazoylene group, phenanthridinylene group, acridi Nylene group, phenanthrolinylene group, phenazynylene group, benzoimidazolylene group, benzofuranylene group, benzothiophenylene group, isobenzothiazonylene group, benzoxazonylene group, isobenzooxazonylene group, triazonylene group, tetra Zolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzosylrollylene group, dibenzocarbazolylene group, thiadiazolylene group, imidazopyridi Nylene group and imidazopyrimidinylene group;
Condensed ring compounds selected from among. According to paragraph 1,
Wherein L ₁ to L ₁₁ are each independently selected from the group represented by the following formulas 3-1 to 3-16 and 3-19 to 3-25:

In the above formula,
Y ₁ is O, S or N(Z ₇ ),
Z ₁ , Z ₂ and Z ₇ are each independently hydrogen, deuterium, cyano group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group , carbazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group,
d3 is selected from an integer of 1 to 3,
d4 is selected from an integer of 1 to 4,
d6 is selected from integers from 1 to 6,
d8 is selected from integers from 1 to 8,
* and *' are binding sites with neighboring atoms. According to paragraph 1,
Wherein L ₁ to L ₁₁ are independently selected from the group represented by the following formulas 4-1 to 4-16:

In the above formula, * and *' are bonding sites with neighboring atoms. According to paragraph 1,
Ar ₁ to Ar ₇ are independently of each other,
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, 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 Phenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazole Diary group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group , phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofura Nyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, Benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzonaphthofuranyl group, dinaphthofuranyl group, benzonaphthothiophenyl group, dinaphthothiophenyl group, benzonaphthosilolyl group and dinaphthosilolyl group; and
Deuterium, cyano group, phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, heptalenyl group, indacenyl group, acenaphthyl 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, rubisenyl group, coronenyl group, Ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, Pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, Cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, iso Benzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzosilolyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadia At least one of zolyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzonaphthofuranyl group, dinaphthofuranyl group, benzonaphthothiophenyl group, dinaphthothiophenyl group, benzonaphthosilolyl group and dinaphthosilolyl group. Substituted by one, 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, Benzofluorenyl group, dibenzofluorenyl group, phenalenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, naphthacenyl group, picenyl group, pe Relenyl group, pentaphenyl group, hexacenyl group, pentacenyl group, rubisenyl group, coronenyl group, ovalenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazole Diary group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, Benzoquinolinyl group, phthalazinyl group, naphthyridinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, benzimidazole diary group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, di Benzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, dibenzosilolyl group, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, benzonaphthofuranyl group, dinaphthofuranyl group, benzonaph tothiophenyl group, dinaphthothiophenyl group, benzonaphthosilolyl group and dinaphthosilolyl group;
Condensed ring compounds selected from among. According to paragraph 1,
Ar ₁ to Ar ₇ are independently selected from the group represented by the following formulas 5-1 to 5-25:

In formulas 5-1 to 5-25,
Y ₃₁ is O, S, C(Z ₃₃ )(Z ₃₄ ), N(Z ₃₅ ) or Si(Z ₃₆ )(Z ₃₇ ),
Z ₃₁ to Z ₃₇ are each independently hydrogen, deuterium, cyano group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, carboxymethyl group selected from zolyl group, benzocarbazolyl group, dibenzocarbazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group,
e3 is selected from an integer of 1 to 3,
e4 is selected from integers 1 to 4,
e5 is selected from integers 1 to 5,
e6 is selected from integers from 1 to 6,
e7 is selected from integers from 1 to 7,
e9 is selected from integers from 1 to 9,
* is a bonding site with a neighboring atom. According to paragraph 1,
Ar ₁ to Ar ₇ are independently selected from the group represented by the following formulas 6-1 to 6-18:

In Formulas 6-1 to 6-18, * represents a bonding site with a neighboring atom. According to paragraph 1,
R ₁ to R ₃ are independently of each other,
Groups represented by Formulas 2-1 to 2-5;
Phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group; and
Deuterium, cyano group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, Pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, benzoquinoli Nyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, oxadiazolyl group, tria Substituted with at least one of a zinyl group, dibenzofuranyl group, dibenzothiophenyl group, imidazopyridinyl group and imidazopyrimidinyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrenyl group, anthracenyl group, tri phenylenyl group, pyrenyl group and chrysenyl group; Condensed ring compounds selected from among. According to paragraph 1,
R ₁ to R ₃ are independently of each other,
A condensed ring selected from the groups represented by Formulas 2-1 to 2-5, phenyl group, biphenyl group, terphenyl group, naphthyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, and chrysenyl group compound. According to paragraph 1,
A condensed ring compound represented by one of the formulas 1B to 1S:

In the above formula,
The description of R ₃₁ to R ₃₆ is the same as the description of R ₃ ,
The description of X ₁ , X ₂ , R ₃ to R ₁₁ is the same as that described in paragraph 1. According to clause 11,
In formulas 1B to 1S,
X ₁ is N, X ₂ is C(R ₂ ),
The R ₂ is a condensed ring compound selected from the group represented by Formulas 2-1 to 2-5. According to clause 11,
In formulas 1B to 1S,
The X ₁ is C(R ₁ ), the X ₂ is N,
The R ₁ is a condensed ring compound selected from the group represented by Formulas 2-1 to 2-5. According to clause 11,
Among the formulas 1B, 1D to 1G, 1I to 1N, and 1P to 1S,
X ₁ is N, X ₂ is C(R ₂ ),
The R ₃₂ is a condensed ring compound selected from the group represented by Formulas 2-1 to 2-5. According to clause 11,
Among the formulas 1B, 1D to 1G, 1I to 1N, and 1P to 1S,
The X ₁ is C(R ₁ ), the X ₂ is N,
The R ₃₂ is a condensed ring compound selected from the group represented by Formulas 2-1 to 2-5. According to paragraph 1,
The condensed ring compound is one of the following compounds:

. first electrode; a second electrode opposite the first electrode; and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer includes one or more of the condensed ring compounds of claim 1. According to clause 17,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer includes a hole transport region between the first electrode and the light-emitting layer and an electron transport region between the light-emitting layer and the second electrode,
The hole transport region includes at least one selected from a hole injection layer, a hole transport layer, a light emission auxiliary layer, and an electron blocking layer,
The electron transport region is an organic light emitting device comprising at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer. According to clause 18,
An organic light-emitting device wherein the electron transport region includes an electron transport layer, and the electron transport layer includes the condensed ring compound. According to clause 18,
An organic light-emitting device wherein the electron transport region includes an electron injection layer, and the electron injection layer includes the condensed ring compound.