KR102611207B1 - 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 2A>

<Formula 2B>

<Formula 2C>

<Formula 10>

In formulas 1, 2A to 2C and 10,

A ₁ is selected from the group represented by Formulas 2A to 2C, n1 is selected from the integer of 1 to 3,

_{and _ _ _ _ _ _}

The B ₂ ring, B ₃ ring and B ₄ ring are condensed with each other,

B ₁ ring and B ₄ ring are independently selected from C ₆ -C ₆₀ aromatic ring and C ₁ -C ₆₀ heteroaromatic ring,

B ₂ ring is selected from C ₇ -C ₆₀ aromatic ring and C ₁ -C ₆₀ heteroaromatic ring,

_The B ₃ ring _is represented _{by the} above formula ( ₁₀ ) _{, where}

L ₁ , L ₂ , L ₁₁ and L ₁₂ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C _{1 -C 10 heterocycloalkylene group, or a substituted or unsubstituted C 1} -C ₁₀ heterocycloalkylene group. 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 hetero Arylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group) aromatic condensed heteropolycyclic group),

a1, a2, a11 and a12 are independently selected from integers from 0 to 3,

Ar ₁ , Ar ₁₁ and Ar ₁₂ 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 ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted selected from monovalent non-aromatic condensed polycyclic groups and substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic groups,

b1, b11 and b12 are independently selected from integers from 1 to 5,

R ₁ to R ₈ and R ₁₄ to R ₁₇ are each independently selected from hydrogen, 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 C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ aryl group Group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁ )(Q ₂ )(Q ₃ ), -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 ),

R ₁₁ to R ₁₃ 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 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 aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted Substituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -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 ). is selected from,

c11 to c13 are independently selected from integers from 0 to 4,

* is the binding site with the neighboring atom,

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 selected from the group consisting of _{a 6} -C ₆₀ arylthio group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituent of a 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 substituted with alkyl group C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl group substituted with C ₆ -C ₆₀ aryl group, terphenyl group, C ₁ -C ₆₀ heteroaryl group, C ₁ - substituted with C ₁ -C ₆₀ alkyl group. It is selected from a C ₆₀ heteroaryl group, a C ₁ -C ₆₀ heteroaryl group substituted with a C ₆ -C ₆₀ aryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

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 one or more types of condensed ring compounds as described above.

Organic light-emitting devices containing the condensed cyclic compound can have high efficiency and long lifespan.

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

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

<Formula 1>

<Formula 2A>

<Formula 2B>

<Formula 2C>

<Formula 10>

_{In Formula 1 , _ _ _} Here, descriptions of L ₁₁ , a11, Ar ₁₁ , b11, R ₁₄ and R ₁₅ refer to what is described herein. For example, X ₁ may be selected from O, S and C(R ₁₄ )(R ₁₅ ). According to one embodiment, X ₁ may be O or S.

In Formula 1, A ₁ is selected from the group represented by Formulas 2A to 2C, and n1 is selected from an integer of 1 to 3. n1 represents the number of A _1s , and when n1 is 2 or more, 2 or more A _1s are the same or different from each other. According to one embodiment, n1 is 1 or 2, or may be 1, but is not limited thereto.

In Formulas 2A to 2C, the B ₂ ring, B ₃ ring, and B ₄ ring are condensed with each other.

In Formulas 2A to 2C, the B ₁ ring and the B ₄ ring are independently selected from a C ₆ -C ₆₀ aromatic ring and a C ₁ -C ₆₀ heteroaromatic ring.

For example, the B ₁ ring and the B ₄ ring may be independently selected from benzene, naphthalene, pyridine, pyrimidine, pyrazine, quinoline, isoquinoline, quinoxaline, quinazoline, and cynoline. . For example, the A ₁ ring and the A ₂ ring may be independently selected from benzene and naphthalene. According to one embodiment, the B ₁ ring and the B ₄ ring may be benzene, but are not limited thereto.

In Formulas 2A to 2C, the B ₂ ring is selected from a C ₇ -C ₆₀ aromatic ring and a C ₁ -C ₆₀ heteroaromatic ring.

For example, the B ₂ ring is naphthalene, heptalene, phenalene, phenanthrene, anthracene, triphenylene, pyrene, chrysene, naphthacene, picene, perylene, pentaphene, quinoline, isoquinoline, quinoxaline, quinazoline, cinnoline, naphthyridine, acridine and It may be selected from phenanthroline. For example, the B ₂ ring may be naphthalene, but is not limited thereto.

In _{Formulas 2A} to 2C, _the B ₃ ring _is represented by Formula _{10 , and} is selected. Here, descriptions of L ₁₂ , a12, Ar ₁₂ , b12, R ₁₆ and R ₁₇ refer to those described herein. According to one embodiment, X ₂ may be O or S.

L ₁ , L ₂ , L ₁₁ and L ₁₂ are each independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkylene group, a substituted or unsubstituted C _{1 -C 10 heterocycloalkylene group, or a substituted or unsubstituted C 1} -C ₁₀ heterocycloalkylene group. 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 hetero Arylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic group and substituted or unsubstituted divalent non-aromatic heterocondensed polycyclic group (substituted or unsubstituted divalent non-aromatic condensed polycyclic group) aromatic condensed heteropolycyclic group).

For example, L ₁ , L ₂ , L ₁₁ and L ₁₂ are independently of each other,

Phenylene, pentalenylene, indenylene, naphthylene, azulenylene, heptalenylene, indacenylene, acetate Acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene, phenanthrenylene , anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenylene, picenylene. ), perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, coronenylene, ovalenylgylene ovalenylene, pyrrolylene, thiophenylene, furanylene, imidazolylene, pyrazolylene, thiazolylene, isothia isothiazolylene, oxazolylene, isoxazolylene, pyridinylene, pyrazinylene, pyrimidinylene, pyridazinylene , isoindolylene, indolylene, indazolylene, purinylene, quinolinylene, isoquinolinylene, benzoquinoli Benzoquinolinylene, phthalazinylene, naphthyridinylene, quinoxalinylene, quinazolinylene, cinnolinylene, carbazolinylene ( carbazolylene, phenanthridinylene, acridinylene, phenanthrolinylene, phenazinylene, benzoimidazolylene, benzofuranylene , benzothiophenylene, isobenzothiazolylene, benzoxazolylene, isobenzooxazolylene, triazolylene, tetrazolylene, oxa Oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group, benzocarbazolylene group, dibenzocarbazolylene group, thiadiazolylene group, imida Zopyridinylene 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, perylgyrenyl 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, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) Substituted with at least one selected from phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, hepthalenylene group, indacenylene group, acetate Naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl Lenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexasenylene group, pentacenylene group, rubycenylene group, coronenylene group, ovalenylene group, Pyrroylene group, thiophenylene group, furanylene group, imidazolylene group, pyrazoylene group, thiazonylene group, isothiazolylene group, oxazonylene group, isoxazonylene group, pyridinylene group, pyrazinylene group, pyrimidinyl Len group, pyridazinylene group, isoindolylene group, indolylene group, indazolylene group, purinylene group, quinolinylene group, isoquinolinylene group, benzoquinollinylene group, phthalazinylene group, naphthyridinylene group , quinoxalinylene group, quinazolinylene group, cinolinylene group, carbazonylene group, phenanthridinylene group, acridinylene group, phenanthrolinylene group, phenazynylene group, benzoimidazolylene group, benzofuranylene group, Benzothiophenylene group, isobenzothiazonylene group, benzooxazonylene group, isobenzooxazonylene group, triazonylene group, tetrazolylene group, oxadiazolylene group, triazinylene group, dibenzofuranylene group, dibenzothiophenylene group , benzocarbazolylene group, dibenzocarbazolylene group, thiadiazolylene group, imidazopyridinylene group and imidazopyrimidinylene 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.

As another example, L ₁ , L ₂ , L ₁₁ and L ₁₂ may be independently selected from the group represented by Formulas 3-1 to 3-41 below:

In Formulas 3-1 to 3-41,

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

Z ₁ to Z ₇ are 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, fluorenyl group, spiro-bifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group , anthracenyl group, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group , dibenzofuranyl group, dibenzothiophenyl group, triazinyl group, benzoimidazolyl group, phenanthrolinyl 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,

d2 is 1 or 2,

d3 is selected from an integer of 1 to 3,

d4 is selected from an integer of 1 to 4,

d5 is selected from an integer of 1 to 5,

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 one embodiment, L ₁ , L ₂ , L ₁₁ and L ₁₂ may be independently selected from the group represented by the following Formulas 4-1 to 4-35:

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

In Formulas 1 and 10, a1, a2, a11, and a12 are independently selected from integers of 0 to 3. a1 represents the number of L ₁ , and when a1 is 2 or more, 2 or more L ₁ are the same or different from each other. The description of a2, a11 and a12 can be understood by referring to the description of a1 and the structures of Formulas 1 and 10.

According to one embodiment, a1, a2, a11, and a12 in Formula 1 may be independently 0, 1, or 1, but are not limited thereto.

In Formulas 1 and 10, Ar ₁ , Ar ₁₁ and Ar ₁₂ 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 ₁ -C 10 heterocycloalkyl group. 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 heteropolycyclic group.

For example, Ar ₁ , Ar ₁₁ and Ar ₁₂ are independently of each other,

Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, Indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl ( phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl , perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl, ovalenyl, pyrrole pyrrolyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl ( oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl ), indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, phthalazinyl, naphthyridinyl ( naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthridinyl, acridinyl, phenanthrolinyl ( phenanthrolinyl, phenazinyl, benzoimidazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, isobenzothiazolyl, benz Benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, benzocarbazolyl ( benzocarbazolyl), dibenzocarbazolyl, thiadiazolyl, imidazopyridinyl and imidazopyrimidinyl; 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, perylgyrenyl 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, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) Substituted with at least one selected from phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group , acenaphthyl group, fluorenyl group, spiro-fluorenyl 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, 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, cynolinyl group, carbazolyl group, phenanthridinyl group , acridinyl group, phenanthrolinyl group, phenazinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzothiazolyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazole diyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, benzocarbazolyl group, dibenzocarbazolyl group, thiadiazolyl group, imidazopyridinyl group and imidazopyrimidinyl 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.

As another example, Ar ₁ , Ar ₁₁ and Ar ₁₂ may be independently selected from the group represented by Formulas 5-1 to 5-79 below:

In formulas 5-1 to 5-79,

Y ₃₁ and Y ₃₂ are, independently of each other, 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, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group , dibenzofuranyl group, dibenzothiophenyl group, benzoimidazolyl group, phenanthrolinyl group, 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,

e2 is 1 or 2,

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,

e8 is selected from integers from 1 to 8,

* is a bonding site with a neighboring atom.

According to one embodiment, Ar ₁ , Ar ₁₁ and Ar ₁₂ may be independently selected from the group represented by Formulas 6-1 to 6-44 below:

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

In Formulas 1 and 10, b1, b11, and b12 may be independently selected from integers of 1 to 5. b1 represents the number of Ar _1s , and when b1 is 2 or more, 2 or more Ar _1s are the same or different from each other. The description of b11 and b12 can be understood by referring to the description of b1 and the structures of Formulas 1 and 10.

According to one embodiment, b1, b11, and b12 may be independently 1 or 2, or may be 1, but are not limited thereto.

In the above formulas, R ₁ to R ₈ and R ₁₄ to R ₁₇ are each independently selected from hydrogen, 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 C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ - C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, - Si(Q ₁ )(Q ₂ )(Q ₃ ), -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 ),

R ₁₁ to R ₁₃ 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 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 aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted Substituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -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 ). can be selected from among.

For example, in the above formulas, R ₁ to R ₈ and R ₁₄ to R ₁₇ are each independently selected from 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 ₆ -C ₂₀ aryl group, A substituted or unsubstituted C ₁ -C ₂₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and -Si(Q ₁ ) (Q ₂ ) is selected from (Q ₃ ),

R ₁₁ to R ₁₃ 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 monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group. group, and -Si(Q ₁ )(Q ₂ )(Q ₃ ).

As another example, R ₁ to R ₈ and R ₁₄ to R ₁₇ 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;

C ₁ -C ₂₀ alkyl group and C ₁ substituted with at least one of deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group and hydrazono group -C ₂₀ alkoxy group;

Phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl 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, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrole Diary 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, imidazopyrimidinyl group and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) Substituted with at least one of: phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenyl Renyl 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, pyrazolyl group Zinyl 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 ); is selected from,

R ₁₁ to R ₁₃ 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;

C ₁ -C ₂₀ alkyl group and C ₁ substituted with at least one of deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group and hydrazono group -C ₂₀ alkoxy group;

fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl 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 ₁₀ alkyl group, C ₁ -C ₁₀ alkoxy group , phenyl group, naphthyl group, fluorenyl group, spiro-fluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthrenyl group, anthracenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrole Diary 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, imidazopyrimidinyl group and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) substituted with at least one of a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

-Si(Q ₁ )(Q ₂ )(Q ₃ ); is selected from,

Q ₁ to Q ₃ and 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 one embodiment, R ₁ to R ₈ and R ₁₄ to R ₁₇ 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 ₁₀ alkyl group and C ₁ -C ₁₀ Alkoxy group;

C ₁ -C ₁₀ alkyl group and C ₁ substituted with at least one of deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group and hydrazono group -C ₁₀ alkoxy group;

phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridinyl group, pyrimidinyl group and triazinyl 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, pyridinyl group, pyrimidinyl group and triazinyl group, substituted with at least one of phenyl group, naphthyl group, pyridinyl group, pyrimidinyl group and triazinyl group,

R ₁₁ to R ₁₃ 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 ₁₀ alkyl group and C ₁ -C ₁₀ Alkoxy group; can be selected from among.

According to another embodiment, R ₁ to R ₈ and R ₁₁ to R ₁₃ may be hydrogen, and R ₁₄ to R ₁₇ may independently be hydrogen or a methyl group.

In Formulas 2A to 2C, c11 to c13 are independently selected from integers of 0 to 4. c11 represents the number of R ₁₁ , and when c1 is 2 or more, 2 or more R ₁₁ are the same or different from each other. The description of c12 and c13 can be understood by referring to the description of c11 and the structures of Formulas 2A to 2C.

According to one embodiment, c11 to c13 may be independently 0 or 1.

According to one embodiment, the condensed ring compound may be represented by one of the following formulas 1-1 to 1-42:

<Formula 1-1>

<Formula 1-2>

<Formula 1-3>

<Formula 1-4>

<Formula 1-5>

<Formula 1-6>

<Formula 1-7>

<Formula 1-8>

<Formula 1-9>

<Formula 1-10>

<Formula 1-11>

<Formula 1-12>

<Formula 1-13>

<Formula 1-14>

<Formula 1-15>

<Formula 1-16>

<Formula 1-17>

<Formula 1-18>

<Formula 1-19>

<Formula 1-20>

<Formula 1-21>

<Formula 1-22>

<Formula 1-23>

<Formula 1-24>

<Formula 1-25>

<Formula 1-26>

<Formula 1-27>

<Formula 1-28>

<Formula 1-29>

<Formula 1-30>

<Formula 1-31>

<Formula 1-32>

<Formula 1-33>

<Formula 1-34>

<Formula 1-35>

<Formula 1-36>

<Formula 1-37>

<Formula 1-38>

<Formula 1-39>

<Formula 1-40>

<Formula 1-41>

<Formula 1-42>

In _{Formulas 1-1 to 1-42 , description of X 1} , Refer to what is described herein.

According to another embodiment, the condensed ring compound may be represented by one of the following formulas 1-1(1) to 1-42(1):

<Formula 1-1(1)>

<Formula 1-2(1)>

<Formula 1-3(1)>

<Formula 1-4(1)>

<Formula 1-5(1)>

<Formula 1-6(1)>

<Formula 1-7(1)>

<Formula 1-8(1)>

<Formula 1-9(1)>

<Formula 1-10(1)>

<Formula 1-11(1)>

<Formula 1-12(1)>

<Formula 1-13(1)>

<Formula 1-14(1)>

<Formula 1-15(1)>

<Formula 1-16(1)>

<Formula 1-17(1)>

<Formula 1-18(1)>

<Formula 1-18(1)>

<Formula 1-19(1)>

<Formula 1-20(1)>

<Formula 1-21(1)>

<Formula 1-22(1)>

<Formula 1-23(1)>

<Formula 1-24(1)>

<Formula 1-25(1)>

<Formula 1-26(1)>

<Formula 1-27(1)>

<Formula 1-28(1)>

<Formula 1-29(1)>

<Formula 1-30(1)>

<Formula 1-31(1)>

<Formula 1-32(1)>

<Formula 1-33(1)>

<Formula 1-34(1)>

<Formula 1-35(1)>

<Formula 1-36(1)>

<Formula 1-37(1)>

<Formula 1-38(1)>

<Formula 1-39(1)>

<Formula 1-40(1)>

<Formula 1-41(1)>

<Formula 1-42(1)>

_{For descriptions of X 1} ,

For example, X ₁ is selected from O, S and C(R ₁₄ )(R ₁₅ );

X ₂ is selected from O and S,

L ₁ and L ₂ are independently selected from the group represented by Formulas 4-1 to 4-35,

a1 and a2 are independently 0 or 1,

Ar ₁ is selected from the group represented by Formulas 6-1 to 6-44,

b1 can be 1 or 2.

The condensed ring compound may be one of the following compounds:

Among the condensed ring compounds represented by Formula 1, the B ₂ ring is selected from a C ₇ -C ₆₀ aromatic ring and a C ₁ -C ₆₀ heteroaromatic ring, so the size of the entire molecular structure increases to form heteroatoms (for example, O Alternatively, electrons on S) become easily dispersed, and thus the entire molecular structure can be stabilized. Therefore, an organic light emitting device containing the condensed ring compound can achieve high efficiency and long lifespan.

In addition, the condensed ring compound is suitable for use as a host of a light-emitting layer because one of the groups represented by formulas 2A to 2C is bonded to a specific position, as represented by the following formula 1-1', and accordingly, the Organic light-emitting devices containing condensed cyclic compounds can achieve high efficiency and long lifespan.

<Formula 1-1'>

The condensed ring compound represented by Formula 1 can be synthesized using known organic synthesis methods. The method for synthesizing the condensed ring compound can be recognized by those skilled in the art by referring to the examples described below.

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 at least one condensed ring compound represented by Formula 1.

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 light-emitting 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, Compound 1 and Compound 2 may both exist in the light-emitting layer) or in different layers (for example, Compound 1 may exist in a hole present in the transport layer and Compound 2 may be present in the light-emitting 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 buffer layer, and an electron blocking layer, and ii) the light-emitting layer and the second electrode (cathode), and may include an electron transport region including at least one of a hole blocking 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 at least one of the hole transport region and the light emitting layer. For example, the light emitting layer of the organic light emitting device may include at least one of the condensed ring compounds represented by Formula 1 above. The condensed cyclic compound represented by Formula 1 included in the light-emitting layer may serve as a host, and in this case, the light-emitting layer may further include a dopant. The dopant may be a phosphorescent dopant or a fluorescent dopant. According to one embodiment, the dopant may be a fluorescent dopant.

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, 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 sulfonicacid:Polyaniline/ Camphorsulfonic acid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), at least one of the compound represented by Formula 201 below and the compound represented by Formula 202 below More may include:

<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 condensed ring compound as described above.

According to one embodiment, the host may be composed of the first compound as described above.

[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>

Among the 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 (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. .

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, Gd, and Tb.

The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may be selected from oxides and halides (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, etc. 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 mixtures thereof having a low work function. 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 is, independently of each other, a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphine derivative, a phthalocyanine derivative ( It may include at least one material 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 to about 500° C., about 10 A vacuum degree of ^-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 compound 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 compound 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-hydrofuranyl group, and 2,3-hydrothiophenyl 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

Synthesis Example 1: Synthesis of Compound H1

Synthesis of Intermediate A

Intermediate A was synthesized according to Scheme 1-1 below:

<Scheme 1-1>

(1) Synthesis of intermediate A-1

Under argon atmosphere, 22.0 g of (2,3-dimethoxynaphthalen-1-yl) boronic acid, 17.5 g of 1-bromo-2-fluorobenzene, 2.32 g of tetrakistriphenylphosphine palladium (0), 300 mL of 1,2-dimethoxyethane, and 150 mL of 2M sodium carbonate solution. was added to the flask, heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the water layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 23.9 g of Intermediate A-1 (yield: 84.8 %).

(2) Synthesis of intermediate A-2

Under an argon atmosphere, 23.9 g of Intermediate A-1 and 5 mL of anhydrous THF were added to the flask, 60 mL of a 1.6 M n-butyllithium hexane solution was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78°C, and 30 mL of a solution of 28.1 g of trimethyl borate in THF was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted using ether, the water layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was washed with hexane to obtain 18.0 g of Intermediate A-2 (yield: 64.9%).

(3) Synthesis of intermediate A-3

Under argon atmosphere, 18.0g of intermediate A-2, 16.6g of 4-bromo-1-fluoro-2-iodobenzene, 1.28g of Tetrakis(triphenylphosphine) palladium(0), 180mL of toluene, and 90mL of 2M sodium carbonate solution were added to the flask and incubated for 8 hours. It was refluxed and stirred while heating. After cooling to room temperature, the reaction solution was extracted using toluene, the water layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 20.0 g of Intermediate A-3 (yield: 79.8%).

(4) Synthesis of intermediate A-4

20.0 g of Intermediate A-3 and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. 27.5 g of BBr ₃ was added to the flask and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and carefully inactivated in methanol and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , then impurities of origin were removed through a silica gel short column, the solution was concentrated, and the obtained sample was vacuum dried to obtain 18.6 g of intermediate A-4 (yield 99.6%).

(5) Synthesis of intermediate A

18.6 g of intermediate A-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated), and 24.5 g of K ₂ CO ₃ were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of Toluene was added to the solution, and the solution was transferred to a separatory funnel and washed with water. After drying this solution with MgSO ₄ , origin impurities were removed through a silica gel short column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 11.6 g of intermediate A (yield 68.5%).

Synthesis of Compound H1

Compound H1 was synthesized according to Scheme 1-2 below:

<Scheme 1-2>

Under argon atmosphere, 4.3g of intermediate A, 3.8g of (10-(naphthalen-2-yl)-anthracen-9-yl) boronic acid, 0.232g of Tetrakis (triphenylphosphine) palladium (0) 1 2-dimethoxyethane 40mL, 2M sodium carbonate 20mL of solution was added and stirred under reflux for 8 hours. After cooling to room temperature, the precipitated solid was separated by filtration. The obtained solid was washed with a mixture of water and methanol and then recrystallized with toluene to obtain 4.4 g of compound H1 (yield: 66.2%). The produced compound was confirmed through MS/FAB.

Calculated value: 610.71 Measured value: 610.19

Synthesis Example 2: Synthesis of Compound H2

Compound H2 was synthesized according to Scheme 2 below:

<Scheme 2>

(1) Synthesis of intermediate H2-1

38.7 g of Intermediate A and 500 mL of tetrahydrofuran (dehydrated) were added to the flask and cooled to -78°C. 66mL of n-BuLi (1.6M in hexane) was added thereto and stirred for 2 hours while raising the temperature to 0°C. Then, it was cooled again to -78°C, 327.5 g of B(OMe) ₃ was added, and the mixture was stirred at -78°C for 10 minutes and then stirred at room temperature for 5 hours. After completion of the reaction, 1N HCl aq. 200 mL was added and stirred at room temperature for 1 hour. Afterwards, it was transferred to a separatory funnel and extracted with ethyl acetate. This solution was dried over MgSO ₄ , concentrated, and washed with n-hexane to obtain 22.8 g of intermediate H2-1 (yield: 65.3%).

(2) Synthesis of intermediate H2-2

Under argon atmosphere, 22.8g of intermediate H2-1, 8.4g of 1-bromo-4-iodobenzene, 1.52g of Tetrakis (triphenylphosphine) palladium(0), 200mL of toluene, and 100mL of 2M sodium carbonate solution were added to the flask and heated for 8 hours. It was refluxed and stirred. After cooling to room temperature, the reaction solution was extracted with toluene. The water layer was removed, and the organic layer was dried with MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 23.7 g of intermediate H2-2 (yield: 71.7%).

(3) Synthesis of compound H2

20.5 g of compound H2 (yield: 64.3%) was obtained using the same method as the synthesis of compound H1, except that intermediate H2-2 was used instead of intermediate A. The produced compound was confirmed through MS/FAB.

Calculated value: 686.81 Measured value: 686.22

Synthesis Example 3: Synthesis of Compound H3

Synthesis of Intermediate B

Intermediate B was synthesized according to Scheme 3-1 below:

<Scheme 3-1>

(1) Synthesis of intermediate B-1

Under argon atmosphere, (2,3-bis (methylthio) naphthalen-1-yl) boronic acid 25.0g, 1-bromo-2-fluorobenzene 17.5g, tetrakistriphenylphosphine palladium (0) 2.32g, 1,2-dimethoxyethane 300mL, 2M 150 mL of sodium carbonate solution was added to the flask and stirred under reflux while heating for 8 hours. After cooling to room temperature, the water layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO4, concentrated, and the residue was purified by silica gel column chromatography to obtain 24.5g of Intermediate B-1 (yield: 82.1%).

(2) Synthesis of intermediate B-2

Under an argon atmosphere, 24.5 g of Intermediate B-1 and 500 mL of anhydrous THF were added to the flask, 55 mL of a 1.6 M n-butyllithium hexane solution was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78°C, and 30 mL of a solution of 28.1 g of trimethyl borate in THF was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over Mg ₂ So ₄ and concentrated, and the residue was washed with hexane to obtain 17.7 g of intermediate B-2 (yield: 63.4%).

(3) Synthesis of intermediate B-3

Under argon atmosphere, (4- (2-fluorophenyl) -2,3-bis (methylthio) naphthalen-1-yl) boronic acid 17.7g, Tetrakis (triphenylphosphine) palladium (0) 1.28g, toluene 180mL, 2M sodium carbonate solution 90mL was added to the flask and stirred under reflux while heating for 8 hours. After cooling to room temperature, the reaction solution was extracted using toluene, the aqueous solution layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 18.3 g of intermediate B-3 (yield: 76.2%).

(4) Synthesis of intermediate B-4

18.3 g of Intermediate B-3 and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. 27.5 g of BBr ₃ was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and carefully inactivated in methanol and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , then impurities of origin were removed through a silica gel short column, the solution was concentrated, and the obtained sample was vacuum dried to obtain 17.2 g of intermediate B-4 (yield: 99.5%). .

(5) Synthesis of intermediate B

17.2 g of Intermediate B-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated), and 24.2 g of K2CO3 were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of Toluene was transferred to an additional separatory funnel, and the solution was washed with water. After drying this solution with MgSO4, origin impurities were removed through a silica gel short column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 10.1 g of intermediate B (yield: 64.3%).

Synthesis of compound H3

Compound H3 was synthesized according to Scheme 3-2 below:

<Scheme 3-2>

(1) Synthesis of intermediate H3-1

10.1 g of Intermediate B and 500 mL of tetrahydrofuran (dehydrated) were added to the flask and cooled to -78°C. 66mL of n-BuLi (1.6M in hexane) was added thereto and stirred for 2 hours while raising the temperature to 0°C. Then, it was cooled again to -78°C, 327.5 g of B(OMe) ₃ was added, and the mixture was stirred at -78°C for 10 minutes and then stirred at room temperature for 5 hours. After completion of the reaction, 1N HCl aq. 200 mL was added and stirred at room temperature for 1 hour. Afterwards, it was transferred to a separatory funnel and extracted with ethyl acetate. This solution was dried over MgSO ₄ , concentrated, and washed with n-hexane to obtain 5.9 g of intermediate H3-1 (yield: 64.1%).

(2) Synthesis of intermediate H3-2

Under argon atmosphere, 5.9g of intermediate H3-1, 4.2g of 1-bromo-4-iodobenzene, 0.8g of Tetrakis (triphenylphosphine) palladium(0), 200mL of toluene, and 100mL of 2M sodium carbonate solution were added to the flask and heated for 8 hours. It was refluxed and stirred. After cooling to room temperature, the reaction solution was extracted with toluene. The water layer was removed, and the organic layer was dried with MgSO ₄ and concentrated. The residue was purified by silica gel column chromatography to obtain 6.0 g of intermediate H3-2 (yield: 71.6%).

(3) Synthesis of compound H3

5.1 g of compound H3 (yield: 63.8%) was obtained using the same method as the synthesis of compound H1, except that intermediate H3-2 was used instead of intermediate A. The produced compound was confirmed through MS/FAB.

Calculated value: 718.93 Measured value: 718.18

Synthesis Example 4: Synthesis of Compound H4

Compound H4 was synthesized according to Scheme 4 below:

<Scheme 4>

(1) Synthesis of intermediate H4-2

23.5g of intermediate H4-2 (yield: 70.6 %) was obtained.

(2) Synthesis of compound H4

Except that intermediate H4-2 was used instead of intermediate A, and (10-phenylanthracen-9-yl) boronic acid was used instead of 10-(naphthalen-2-yl) anthracen-9-yl) boronic acid. , 18.9g of compound H4 (yield: 64.3%) was obtained using the same method as the synthesis of compound H1. The produced compound was confirmed through MS/FAB.

Calculated value: 636.21, Measured value: 636.75

Synthesis Example 5: Synthesis of Compound H5

Synthesis of Intermediate C

Intermediate C was synthesized according to Scheme 5-1 below:

(1) Synthesis of intermediate C-1

Under argon atmosphere, 10.3 g of 5-iodonaphtho [2,1-b] benzofuran (5-bromo-2- (ethoxycarbonyl) phenyl) boronic acid 8.2 g, Tetrakis (triphenylphosphine) palladium (0) 0.4 g, 30 mL of 2M sodium carbonate aqueous solution and toluene. 60 mL of the mixture was heated to reflux for 8 hours. The resulting mixture was cooled to room temperature, extracted with toluene, and the organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 8.8 g of intermediate C-1 (yield: 66.2%).

(2) Synthesis of intermediate C-2

Under an argon atmosphere, 30 mL of 1 M methyl magnesium bromide tetrahydrofuran solution was added to 90 mL of tetrahydrofuran solution of 8.8 g of intermediate C-1 under ice cooling, and then stirred at room temperature for 5 hours. Water was added to the reaction solution under ice cooling, extracted with toluene, and the organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 6.3g of intermediate C-2 (yield: 74.1%).

(3) Synthesis of intermediate C

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

Synthesis of compound H5

Compound H5 was synthesized according to Scheme 5-2 below:

<Scheme 5-2>

Except that intermediate C was used instead of intermediate A, and (10-phenylanthracen-9-yl) boronic acid was used instead of 10-(naphthalen-2-yl) anthracen-9-yl) boronic acid. 2.2g of compound H5 (yield: 62.4%) was obtained using the same method as the synthesis of compound H1. The produced compound was confirmed through MS/FAB.

Calculated value: 712.89, Measured value: 712.28

Synthesis Example 6: Synthesis of Compound H6

Synthesis of Intermediate D

Intermediate B was synthesized according to Scheme 6-1 below:

<Scheme 2-1>

(1) Synthesis of intermediate D-1

Under argon atmosphere, (1,6-dimethoxynaphthalen-2-yl) boronic acid 32.4g, 1-bromo-2-fluorobenzene 17.6g, tetrakistriphenylphosphine palladium (0) 2.34g, 1,2-dimethoxyethane 300mL and 2M sodium carbonate solution 150mL was added to the flask, heated for 8 hours, and stirred under reflux. After cooling to room temperature, the aqueous solution layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 53.9 g of intermediate D-1 (yield: 84.8 %).

(2) Synthesis of intermediate D-2

Under an argon atmosphere, 53.9 g of intermediate D-1 and 500 mL of anhydrous THF were added to the flask, 55 mL of a 1.6 M n-butyllithium hexane solution was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78°C, and 30 mL of THF solution containing 28.1 g of trimethyl borate was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over Mg ₂ SO ₄ and concentrated, and the residue was washed with hexane to obtain 25.1 g of intermediate D-2 (yield: 64.9%).

(3) Synthesis of intermediate D-3

Under an argon atmosphere, 25.1 g of intermediate D-2, 16.5 g of 4-bromo-1-fluoro-2-iodobenzene, 1.28 g of Tetrakis (triphenylphosphine) palladium (0), 180 mL of toluene, and 95 mL of 2M sodium carbonate solution were added to the flask and incubated for 8 hours. It was heated and stirred under reflux. After cooling to room temperature, the reaction solution was extracted using toluene, the aqueous solution layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 16.5 g of intermediate D-3 (yield: 79.8%).

(4) Synthesis of intermediate D-4

16.5 g of intermediate D-3 and 480 mL of N, N-dimethylformamide were added to the flask, and 20 mL of N, N-dimethylformamide solution containing 6.4 g of N-bromosuccinimide was added. Stirring of the reaction solution was continued at 40°C for 5 hours. An additional 2.2 g of N-bromosuccinimide was added, and stirring was continued at 50°C for 8 hours. After cooling to room temperature and adding 300 mL of water, the reaction solution was extracted using toluene to remove the aqueous solution layer, and then sequentially washed with saturated saline solution (sodium thiosulfate). The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 19.5 g of intermediate D-4 (yield: 97.9%).

(5) Synthesis of intermediate D-5

Under an argon atmosphere, 19.5 g of intermediate D-4 and 300 mL of dichloromethane (dehydrated) were added to the flask, cooled to -78°C while stirring, and 90 mL of a 1M boron tribromide (BBr ₃ ) dichloromethane solution was added. Stirring was continued for 3 hours while heating the reaction solution to room temperature. The reaction solution was ice-cooled and 150 mL of water was added. After removing the aqueous solution layer, the organic layer was dried with MgSO ₄ . After concentrating the organic layer, the residue was purified using a silica gel short column to obtain 17.2g of intermediate D-5 (yield: 94.0%).

(6) Synthesis of intermediate D

17.2 g of intermediate D-5, 300 mL of N-methyl-2-pyrrolidinone (dehydrated), and 24.2 g of K2CO3 were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of toluene was added, and the solution was transferred to a separatory funnel and washed with water. After drying this solution with MgSO ₄ , origin impurities were removed through a silica gel short column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 1.7 g of intermediate D (yield: 10.8%).

Synthesis of compound H6

Compound H6 was synthesized according to Scheme 6-2 below:

<Scheme 6-2>

Use intermediate D instead of intermediate A, and (10-(4-(dibenzo [b, d] furan-2-yl)naphthalen-1 instead of 10-(naphthalen-2-yl)anthracen-9-yl)boronic acid. Compound H6 2.2g (yield: 61.7%) was obtained using the same method as the synthesis of compound H1, except that -yl) anthracen-9-yl) boronic acid was used. The produced compound was confirmed through MS/FAB.

Calculated value: 718.93, Measured value: 718.18

Synthesis Example 7: Synthesis of Compound H7

Synthesis of intermediate E

Intermediate E was synthesized according to Scheme 7-1 below:

(1) Synthesis of intermediate E-1

Under argon atmosphere, (3,5-dimethoxynaphthalen-2-yl) boronic acid 22.0g, 1-bromo-2-fluorobenzene 17.5g, tetrakistriphenylphosphine palladium (0) 2.32g, 1,2-dimethoxyethane 300mL, 2M sodium carbonate solution 150mL was added to the flask and heated, refluxed, and stirred for 8 hours. After cooling to room temperature, the aqueous solution layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 22.4 g of intermediate E-1 (yield 83.6%).

(2) Synthesis of intermediate E-2

Under an argon atmosphere, 22.4 g of intermediate E-1 and 500 mL of anhydrous THF were added to the flask, 55 mL of a 1.6 M n-butyllithium hexane solution was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78°C, and 30 mL of THF solution containing 28.2 g of trimethyl borate was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCL was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted using ether, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over Mg ₂ SO ₄ and concentrated, and the residue was washed with hexane to obtain 16.9 g of intermediate E-2 (yield: 65.2 %).

(3) Synthesis of intermediate E-3

Under argon atmosphere, 16.9g of intermediate E-2, 16.8g of 4-bromo-1-fluoro-2-iodobenzene, 1.28g of Tetrakis (triphenylphosphine) palladium (0), 180mL of toluene, and 90mL of 2M sodium carbonate solution were added to the flask and added to the flask. It was refluxed and stirred while heating for an hour. After cooling to room temperature, the reaction solution was extracted using toluene, the water layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 18.4 g of intermediate E-3 (yield: 78.3 %).

(4) Synthesis of intermediate E-4

18.4 g of intermediate E-3 and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. 27.8 g of BBr3 was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and carefully inactivated in methanol and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , then impurities of origin were removed through a silica gel short column, and the sample obtained by concentrating the solution was vacuum dried to obtain 17.2 g of intermediate E-4 (yield 99.8%).

(5) Synthesis of intermediate E

17.2 g of intermediate E-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated), and 24.5 g of K2CO3 were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of Toluene was transferred to an additional separatory funnel, and the solution was washed with water. After drying this solution with MgSO ₄ , origin impurities were removed through a silica gel short column, the solution was concentrated, and recrystallized in a toluene / methanol mixed solvent to obtain 10.1 g of intermediate E (yield: 65.1%).

Synthesis of compound H7

Compound H7 was synthesized according to Scheme 7-2 below:

<Scheme 7-2>

(1) Synthesis of intermediate H7-1

6.0 g (yield: 65.6%) of Intermediate H7-1 was obtained using the same method as the synthesis of Intermediate H2-1, except that Intermediate E was used instead of Intermediate A.

(2) Synthesis of intermediate H7-2

6.1 g (yield: 69.9%) of Intermediate H7-2 was obtained using the same method as the synthesis of Intermediate H7-2, except that Intermediate H7-1 was used instead of Intermediate H2-1.

(3) Synthesis of compound H7

Except that intermediate H7-2 was used instead of intermediate A, and (10-phenylanthracen-9-yl) boronic acid was used instead of (10- (naphthalen-2-yl) anthracen-9-yl) boronic acid. , 4.9g of compound H7 (yield: 64.1%) was obtained using the same method as the synthesis of compound H1. The produced compound was confirmed through MS/FAB.

Calculated value: 636.75, Measured value: 636.21

Synthesis Example 8: Synthesis of Compound H8

Synthesis of Intermediate F

Intermediate F was synthesized according to Scheme 8-1 below:

<Scheme 8-1>

(1) Synthesis of intermediate F-1

Under argon atmosphere, (3,5-bis (methylthio) naphthalen-2-yl) boronic acid 25.0g, 1-bromo-2-fluorobenzene 17.5g, tetrakistriphenylphosphine palladium (0) 2.32g, 1,2-dimethoxyethane 300mL, 2M 150 mL of sodium carbonate solution was added to the flask and stirred under reflux while heating for 8 hours. After cooling to room temperature, the aqueous solution layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 24.8 g of intermediate F-1 (83.3% yield).

(2) Synthesis of intermediate F-2

Under an argon atmosphere, 24.8 g of intermediate F-1 and 500 mL of anhydrous THF were added to the flask, 55 mL of a 1.6 M n-butyllithium hexane solution was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78°C, and 30 mL of THF solution containing 27.9 g of trimethyl borate was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over Mg ₂ SO ₄ and concentrated, and the residue was washed with hexane to obtain 18.2 g of intermediate F-2 (yield 64.2%).

(3) Synthesis of intermediate F-3

Under argon atmosphere, 18.2g of intermediate F-2, 16.5g of 4-bromo-1-fluoro-2-iodobenzene, 1.28g of Tetrakis (triphenylphosphine) palladium (0), 180mL of toluene, and 90mL of 2M sodium carbonate solution were added to the flask and incubated for 8 hours. It was refluxed and stirred while heating. After cooling to room temperature, the reaction solution was extracted using toluene, the aqueous solution layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 19.0 g of intermediate F-3 (yield 76.8%).

(4) Synthesis of intermediate F-4

19.0 g of intermediate F-3 and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. 27.5 g of BBr3 was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and carefully inactivated in methanol and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , then impurities of origin were removed through a silica gel short column, and the sample obtained by concentrating the solution was vacuum dried to obtain 17.9 g of intermediate F-4 (yield: 99.8%). .

(5) Synthesis of intermediate F

10.8 g of intermediate F-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated), and 24.2 g of K2CO3 were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of toluene was added, and the solution was transferred to a separatory funnel and washed with water. After drying this solution with MgSO ₄ , origin impurities were removed through a silica gel short column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 10.8 g of intermediate F (yield: 66.1%).

Synthesis of compound H8

Compound H8 was synthesized according to Scheme 8-2 below:

<Scheme 8-2>

(1) Synthesis of intermediate H8-1

6.4g of Intermediate H8-1 (yield: 64.3%) was obtained using the same method as the synthesis of Intermediate H2-1, except that Intermediate F was used instead of Intermediate A.

(2) Synthesis of intermediate H8-2

Intermediate H7-1 was used instead of Intermediate H2-1, and 1-bromo-4-iodonaphthalene was used instead of 1-bromo-4-iodobenzene, using the same method as the synthesis of Intermediate H7-2. 7.1g of H8-2 (yield: 71.2%) was obtained.

(3) Synthesis of compound H8

Except that intermediate H8-2 was used instead of intermediate A, and (10-phenylanthracen-9-yl) boronic acid was used instead of (10- (naphthalen-2-yl) anthracen-9-yl) boronic acid. , 5.4g of compound H7 (yield: 63.6%) was obtained using the same method as the synthesis of compound H1. The produced compound was confirmed through MS/FAB.

Calculated value: 718.93, Measured value: 718.18

Synthesis Example 9: Synthesis of Compound H9

Synthesis of Intermediate G

Intermediate G was synthesized according to Scheme 9-1 below:

<Scheme 9-1>

(1) Synthesis of intermediate G-1

Under argon atmosphere, (1,6-bis (methylthio) naphthalen-2-yl) boronic acid 25.0g, 1-bromo-2-fluorobenzene 17.5g, tetrakistriphenylphosphine palladium (0) 2.32g, 1,2-dimethoxyethane 300mL, 2M 150 mL of sodium carbonate solution was added to the flask and stirred under reflux while heating for 8 hours. After cooling to room temperature, the aqueous solution layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO4, concentrated, and the residue was purified by silica gel column chromatography to obtain 25.4g of intermediate G-1 (yield: 85.2%).

(2) Synthesis of intermediate G-2

Under an argon atmosphere, 25.4 g of intermediate G-1 and 500 mL of anhydrous THF were added to the flask, 55 mL of a 1.6 M n-butyllithium hexane solution was added, and the reaction solution was stirred at room temperature for 4 hours. It was cooled to -78°C, and 30 mL of a solution of 28.2 g of trimethyl borate in THF was added dropwise. The reaction solution was stirred for 8 hours while raising the temperature to room temperature. 200 mL of 10% HCl was added to the reaction solution and stirred for 2 hours. The reaction solution was extracted with ether, the aqueous layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over Mg2SO4, concentrated, and the residue was washed with hexane to obtain 18.8g of intermediate G-2 (yield: 64.8%).

(3) Synthesis of intermediate G-3

Under argon atmosphere, 18.8g of intermediate G-2, 16.5g of 4-bromo-1-fluoro-2-iodobenzene, 1.28g of Tetrakis (triphenylphosphine) palladium (0), 180mL of toluene, and 90mL of 2M sodium carbonate solution were added to the flask and incubated for 8 hours. It was refluxed and stirred while heating. After cooling to room temperature, the reaction solution was extracted using toluene, the aqueous solution layer was removed, and the organic layer was washed with saturated saline solution. The organic layer was dried over MgSO ₄ and concentrated, and the residue was purified by silica gel column chromatography to obtain 19.4 g of intermediate G-3 (yield: 76.2 %).

(4) Synthesis of intermediate G-4

19.4 g of intermediate G-3 and 250 mL of dichloromethane (dehydrated) were added to the flask and cooled to 0°C. 27.5 g of BBr3 was added and stirred at room temperature for 24 hours. After completion of the reaction, the solution was cooled to -78 °C and carefully inactivated in methanol and inactivated with a sufficient amount of water. The solution was transferred to a separatory funnel, extracted with dichloromethane, dried with MgSO ₄ , then impurities of origin were removed through a silica gel short column, and the sample obtained by concentrating the solution was vacuum dried to obtain 18.2 g of intermediate G-4 (yield: 99.5%). .

(5) Synthesis of intermediate G

18.2 g of intermediate G-4, 300 mL of N-methyl-2-pyrrolidinone (dehydrated), and 24.2 g of K2CO3 were added to the flask and stirred at 200°C for 2 hours. After completion of the reaction, the solution was cooled to room temperature, 2L of toluene was added, and the solution was transferred to a separatory funnel and washed with water. After drying this solution with MgSO4, origin impurities were removed through a silica gel short column, the solution was concentrated, and recrystallized in a toluene/methanol mixed solvent to obtain 11.2g of intermediate G (yield: 67.3%).

Synthesis of compound H9

Compound H9 was synthesized according to Scheme 8-2 below:

<Scheme 8-2>

Use intermediate G instead of intermediate A, and (10-(9-dimethyl-9H-fluoren-3-yl)anthracen-9-yl instead of 10-(naphthalen-2-yl)anthracen-9-yl)boronic acid. ) 12.0g of compound H9 (yield: 62.6%) was obtained using the same method as the synthesis of compound H1, except that boronic acid was used. The produced compound was confirmed through MS/FAB.

Calculated value: 708.94, Measured value: 708.19

Example 1

As a substrate and anode, a corning 15Ω/cm ² (1200Å) ITO glass substrate was cut into 50mm After irradiation and cleaning by exposure to ozone, this glass substrate was installed in a vacuum deposition apparatus.

HT13 was vacuum deposited on top of the ITO anode to form a hole injection layer with a thickness of 500 Å, and HT3 was vacuum deposited on top of the hole injection layer to form a hole transport layer with a thickness of 450 Å.

Compound H1 (host) and FD1 (dopant) were co-deposited on the top of the hole transport layer at a weight ratio of 95:5 to form a 30 nm thick light emitting layer.

Compound ET1 was deposited on top of the light emitting layer to form a 250Å thick electron transport layer, LiF was deposited on top of the electron transport layer to form a 5Å thick electron injection layer, and Al was vacuum deposited on top of the electron injection layer to form a 1500Å thick electron injection layer. An organic light-emitting device was manufactured by forming a cathode.

Examples 2 to 9 and Comparative Examples 1 to 5

An organic light-emitting device was manufactured using the same method as Example 1, except that the compounds listed in Table 2 were used as the host instead of compound H1 when forming the light-emitting layer.

Evaluation example 1

(Measurement of driving voltage)

The efficiency of the organic light emitting devices manufactured in Examples 1 to 9 and Comparative Examples 1 to 5 was measured using Kethley SMU 236 at a current density of 10 mA/cm ² , and the results are shown in Table 2.

(Measurement of half-life)

The half lifespan of the organic light emitting devices manufactured in Examples 1 to 9 and Comparative Examples 1 to 5 was measured using a luminance meter PR650 at a current density of 50 mA/cm ² , and the results are shown in Table 2. The half life is a measure of the time it takes for the luminance to reach 80% of the initial luminance after driving the organic light emitting device.

host efficiency
(cd/A) Half life (T80)
(hr) Example 1 Compound H1 5.1 90 Example 2 Compound H2 5.1 110 Example 3 Compound H3 5.0 100 Example 4 Compound H4 5.1 100 Example 5 Compound H5 5.2 90 Example 6 Compound H6 5.0 100 Example 7 Compound H7 5.2 100 Example 8 Compound H8 5.0 110 Example 9 Compound H9 5.1 90 Comparative Example 1 Compound A 4.5 50 Comparative Example 2 Compound B 4.7 80 Comparative Example 3 Compound C 4.9 70 Comparative Example 4 Compound D 4.6 70 Comparative Example 5 Compound E 4.6 60

From Table 2, it can be seen that the efficiency and half-life of the organic light-emitting devices of Examples 1 to 9 are superior to those of the organic light-emitting devices of Comparative Examples 1 to 5.

10: Organic light emitting device
110: first electrode
150: Organic layer
190: second electrode

Claims (20)

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

<Formula 2A>

<Formula 2B>

<Formula 2C>

<Formula 10>

In formulas 1, 2A to 2C and 10,
A ₁ is selected from the group represented by Formulas 2A to 2C, n1 is selected from the integer of 1 to 3,
X ₁ is selected from O, S and C(R ₁₄ )(R ₁₅ ),
The B ₂ ring, B ₃ ring and B ₄ ring are condensed with each other,
B ₁ ring and B ₄ ring are independently selected from C ₆ -C ₆₀ aromatic ring and C ₁ -C ₆₀ heteroaromatic ring,
B ₂ ring is selected from C ₇ -C ₆₀ aromatic ring and C ₁ -C ₆₀ heteroaromatic ring,
The B ₃ ring is represented by Formula 10 above, where X ₂ is selected from O, S and C(R ₁₆ )(R ₁₇ ),
L ₁ and L ₂ are independently of each other, phenylene, pentalenylene, indenylene, naphthylene, azulenylene, and heptalenylene. ), indacenylene, acenaphthylene, fluorenylene, spiro-fluorenylene, benzofluorenylene, dibenzofluorenylene, phenalenylene ( phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, triphenylenylene, pyrenylene, chrysenylene, naphthacenyl naphthacenylene, picenylene, perylenylene, pentaphenylene, hexacenylene, pentacenylene, rubicenylene, corone coronenylene and ovalenylene; 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, perylgyrenyl 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, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) Substituted with at least one selected from phenylene group, pentalenylene group, indenylene group, naphthylene group, azulenylene group, hepthalenylene group, indacenylene group, acetate Naphthylene group, fluorenylene group, spiro-fluorenylene group, benzofluorenylene group, dibenzofluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl lenylene group, pyrenylene group, chrysenylene group, naphthacenylene group, picenylene group, perylenylene group, pentaphenylene group, hexasenylene group, pentacenylene group, rubycenylene group, coronenylene group and ovalenylene group; is selected from,
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,
a1 and a2 are independently selected from integers from 0 to 3,
Ar ₁ is selected from a substituted or unsubstituted C ₆ -C ₆₀ aryl group and a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group,
b1 is selected from an integer of 1 to 5,
R ₁ to R ₈ , R ₁₁ to R ₁₃ are independently selected from hydrogen and deuterium,
R ₁₄ to R ₁₇ are independently selected from substituted or unsubstituted C ₁ -C ₆₀ alkyl groups,
c11 to c13 are independently selected from integers from 0 to 4,
* is a binding site with a neighboring atom,
At least one selected from the group consisting of a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₆ -C ₆₀ aryl group, and a substituted monovalent non-aromatic condensed polycyclic 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 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 ₆ -C ₆₀ substituted with a C ₁ -C ₆₀ alkyl group Aryl group, C ₆ -C ₆₀ aryl group substituted with C ₆ -C ₆₀ aryl group, terphenyl group, C ₁ -C ₆₀ heteroaryl group, C ₁ -C ₆₀ heteroaryl group substituted with C ₁ -C ₆₀ alkyl group, It is selected from a C ₁ -C ₆₀ heteroaryl group substituted with a C ₆ -C ₆₀ aryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. According to paragraph 1,
X ₂ is O or S, a condensed ring compound. According to paragraph 1,
B ₁ ring and B ₄ ring are benzene,
B ₂ ring is naphthalene, condensed ring compound. delete According to paragraph 1,
Wherein L ₁ and L ₂ are each independently selected from the group represented by the following formulas 3-1 to 3-9, 3-25, 3-33 to 3-41:

In formulas 3-1 to 3-9, 3-25, 3-33 to 3-41,
Y ₁ is C(Z ₃ )(Z ₄ );
Z ₃ to Z ₄ 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, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group , dibenzofuranyl group, dibenzothiophenyl group, triazinyl group, benzoimidazolyl group, phenanthrolinyl 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,
d2 is 1 or 2,
d3 is selected from an integer of 1 to 3,
d4 is selected from an integer of 1 to 4,
d5 is selected from an integer of 1 to 5,
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,
The L ₁ and L ₂ are independently selected from the group represented by the following formulas 4-1, 4-3, 4-5, 4-7 to 4-13, 4-17, 4-24 to 4-35. Condensed ring compounds, which are:

In the above formulas 4-1, 4-3, 4-5, 4-7 to 4-13, 4-17, 4-24 to 4-35, * and *' are bonding sites with neighboring atoms. According to paragraph 1,
wherein a1 and a2 are independently 0 or 1, a condensed ring compound. According to paragraph 1,
The Ar ₁ is
Phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, Indacenyl, acenaphthyl, fluorenyl, spiro-fluorenyl, benzofluorenyl, dibenzofluorenyl, phenalenyl, phenanthrenyl ( phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl , perylenyl, pentaphenyl, hexacenyl, pentacenyl, rubicenyl, coronenyl and ovalenyl; 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, perylgyrenyl 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, thiadiazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, and -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ) Substituted with at least one selected from phenyl group, biphenyl group, terphenyl group, pentalenyl group, indenyl group, naphthyl group, azulenyl group, hepthalenyl group, indacenyl group , acenaphthyl group, fluorenyl group, spiro-fluorenyl 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 and ovalenyl group; is selected from,
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, and a naphthyl group. According to paragraph 1,
Ar ₁ is a condensed ring compound selected from the group represented by the following formulas 5-1 to 5-19 and 5-21 to 5-24:

In formulas 5-1 to 5-19 and 5-21 to 5-24,
Y ₃₁ and Y ₃₂ are independently C(Z ₃₃ )(Z ₃₄ );
Z ₃₃ to Z ₃₄ 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, pyrenyl group, chrysenyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, quinolinyl group, isoquinolinyl group, quinoxalinyl group, quinazolinyl group, carbazolyl group , dibenzofuranyl group, dibenzothiophenyl group, benzoimidazolyl group, phenanthrolinyl group, triazinyl group, -N (Q ₃₁ ) (Q ₃₂ ) and -Si (Q ₃₁ ) (Q ₃₂ ) (Q ₃₃ ). selected,
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,
e2 is 1 or 2,
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,
e8 is selected from integers from 1 to 8,
* is a bonding site with a neighboring atom. According to paragraph 1,
Ar ₁ is represented by the following formulas 6-1 to 6-4, 6-8 to 6-10, 6-13, 6-15, 6-16 to 6-18, 6-21 to 6-23, 6-28, Condensed ring compounds selected from the group represented by 6-29, 6-32 to 6-41:




The formulas 6-1 to 6-4, 6-8 to 6-10, 6-13, 6-15, 6-16 to 6-18, 6-21 to 6-23, 6-28, 6-29, In 6-32 to 6-41, * is a bonding site with a neighboring atom. According to paragraph 1,
R ₁₄ to R ₁₇ are each independently selected from a substituted or unsubstituted C ₁ -C ₂₀ alkyl group. According to paragraph 1,
R ₁₄ to R ₁₇ are independently of each other,
C ₁ -C ₂₀ alkyl group; and
C ₁ -C ₂₀ alkyl group substituted with at least one of deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amidino group, hydrazino group and hydrazono group;
A condensed ring compound selected from among. delete According to paragraph 1,
A condensed ring compound represented by one of the following formulas 1-1 to 1-42:
<Formula 1-1>

<Formula 1-2>

<Formula 1-3>

<Formula 1-4>

<Formula 1-5>

<Formula 1-6>

<Formula 1-7>

<Formula 1-8>

<Formula 1-9>

<Formula 1-10>

<Formula 1-11>

<Formula 1-12>

<Formula 1-13>

<Formula 1-14>

<Formula 1-15>

<Formula 1-16>

<Formula 1-17>

<Formula 1-18>

<Formula 1-19>

<Formula 1-20>

<Formula 1-21>

<Formula 1-22>

<Formula 1-23>

<Formula 1-24>

<Formula 1-25>

<Formula 1-26>

<Formula 1-27>

<Formula 1-28>

<Formula 1-29>

<Formula 1-30>

<Formula 1-31>

<Formula 1-32>

<Formula 1-33>

<Formula 1-34>

<Formula 1-35>

<Formula 1-36>

<Formula 1-37>

<Formula 1-38>

<Formula 1-39>

<Formula 1-40>

<Formula 1-41>

<Formula 1-42>

In _{Formulas 1-1 to 1-42 , description of X 1} , is the same as described in paragraph 1. According to paragraph 1,
A condensed ring compound represented by one of the following formulas 1-1(1) to 1-42(1):
<Formula 1-1(1)>

<Formula 1-2(1)>

<Formula 1-3(1)>

<Formula 1-4(1)>

<Formula 1-5(1)>

<Formula 1-6(1)>

<Formula 1-7(1)>

<Formula 1-8(1)>

<Formula 1-9(1)>

<Formula 1-10(1)>

<Formula 1-11(1)>

<Formula 1-12(1)>

<Formula 1-13(1)>

<Formula 1-14(1)>

<Formula 1-15(1)>

<Formula 1-16(1)>

<Formula 1-17(1)>

<Formula 1-18(1)>

<Formula 1-18(1)>

<Formula 1-19(1)>

<Formula 1-20(1)>

<Formula 1-21(1)>

<Formula 1-22(1)>

<Formula 1-23(1)>

<Formula 1-24(1)>

<Formula 1-25(1)>

<Formula 1-26(1)>

<Formula 1-27(1)>

<Formula 1-28(1)>

<Formula 1-29(1)>

<Formula 1-30(1)>

<Formula 1-31(1)>

<Formula 1-32(1)>

<Formula 1-33(1)>

<Formula 1-34(1)>

<Formula 1-35(1)>

<Formula 1-36(1)>

<Formula 1-37(1)>

<Formula 1-38(1)>

<Formula 1-39(1)>

<Formula 1-40(1)>

<Formula 1-41(1)>

<Formula 1-42(1)>

_The descriptions _{of X 1 ,} According to clause 15,
X ₂ is selected from O and S,
L ₁ and L ₂ are independently selected from the group represented by the following formulas 4-1 to 4-3, 4-5, 4-7 to 4-13, 4-17, 4-24 to 4-35, and ,
a1 and a2 are independently 0 or 1,
Ar ₁ is represented by the following formulas 6-1 to 6-4, 6-8 to 6-10, 6-13, 6-15, 6-16 to 6-18, 6-21 to 6-23, 6-28, selected from the group represented by 6-29, 6-32 to 6-41,
b1 is 1 or 2, a condensed ring compound:







The formulas 4-1 to 4-3, 4-5, 4-7 to 4-13, 4-17, 4-24 to 4-35 and 6-1 to 6-4, 6-8 to 6-10, Among 6-13, 6-15, 6-16 to 6-18, 6-21 to 6-23, 6-28, 6-29, 6-32 to 6-41, * and *' refer to neighboring atoms. It is a binding site. 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 i) a hole transport region interposed between the first electrode and the light-emitting layer and including at least one of a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer, and ii) between the light-emitting layer and the second electrode. An organic light-emitting device comprising an electron transport region including at least one of a hole blocking layer, an electron transport layer, and an electron injection layer. According to clause 17,
An organic light-emitting device wherein the light-emitting layer contains the condensed cyclic compound. According to clause 17,
An organic light-emitting device wherein the light-emitting layer further includes a fluorescent dopant.