KR20200115011A - Composition and organic light emitting device including the same - Google Patents

Abstract

Disclosed are a composition including a first compound and a second compound, wherein the first compound includes a compound represented by chemical formula 1, and the second compound includes a compound represented by chemical formula 2; and an organic light emitting device including the composition. The descriptions of chemical formula 1 and chemical formula 2 refer to those described in the present application, respectively. According to the present invention, the organic light emitting device may have improved external quantum efficiency and improved life properties.

Description

Composition and organic light emitting device including the same

A composition and an organic light emitting device including the same are provided.

An organic light emitting device is a self-luminous device, has excellent viewing angle, response time, luminance, driving voltage, and response speed, and can be multicolored.

According to an example, the organic light emitting device may include an anode, a cathode, and an organic layer disposed between the anode and the cathode and including an emission layer. A hole transport region may be provided between the anode and the emission layer, and an electron transport region may be provided between the emission layer and the cathode. Holes injected from the anode move to the emission layer via the hole transport region, and electrons injected from the cathode move to the emission layer via the electron transport region. The holes and electrons recombine in the emission layer region to generate excitons. Light is generated as the excitons change from an excited state to a ground state.

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

According to one aspect,

Including the first compound and the second compound,

The first compound includes a compound represented by Formula 1 below,

The second compound is provided with a composition comprising a compound represented by Formula 2:

<Formula 1>

<Formula 2>

Y ₂ in Formula 1 is C,

Ring CY ₁₂ in Formula 1 is a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group,

Formula 2 of Ar ₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or optionally substituted with at least one R ₆₁ or unsubstituted C ₁ -C ₆₀ heterocyclic group with at least one R _61,

Ar ₂ in Formula 2 is a π electron deficient nitrogen-containing C ₁ -C ₆₀ cyclic group unsubstituted or substituted with at least one R ₆₂ ,

Formula 2 of the Ar ₅ is a single bond or, when substituted or unsubstituted C ₅ -C ₆₀ carbonyl to at least one of R ₆₅ or optionally substituted cyclic group with at least one R ₆₅ or unsubstituted C ₁ -C ₆₀ heterocyclic Is a click group or does not exist,

In Formula 2, n is 1, 2 or 3, and when n is 1, Ar ₅ does not exist,

In Formula 2, a1 and a2 are each independently an integer of 0 to 5, but the sum of a1 and a2 is 1 or more,

In Formula 2, ring CY ₂ and ring CY ₃ are each independently a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group, and ring CY ₂ and ring CY ₃ are optionally, at least one Of R ₆₆ substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or at least one R ₆₆ substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group may be bonded to each other through the interposed,

In Formulas 1 and 2, R ₁ to R ₈ , A ₂₀ , A ₁ to A ₇ , R ₂₀ , R ₃₀ , R ₆₁ , R ₆₂ , R ₆₅ and R ₆₆ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or A salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group , A substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ ) (Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(= O)(Q ₈ )(Q ₉ ) or -P(Q ₈ )(Q ₉ ),

In Formula 2, b2 and b3 are each independently an integer of 0 to 20, when b2 is 2 or more, two or more R ₂₀ are the same as or different from each other, and when b3 is 2 or more, two or more R ₃₀ are the same or different from each other, ,

In Formula 1, d2 is an integer of 0 to 10, and when d2 is 2 or more, 2 or more A ₂₀ are the same as or different from each other,

At least one of R ₁ to R ₈ and A ₂₀ in Formula 1 includes at least one fluoro group (-F),

Two or more of R ₁ to R ₈ and A ₂₀ in Formula 1 are optionally combined with each other, and substituted or unsubstituted with at least one R _1a C ₅ -C ₆₀ carbocyclic group or at least one R _1a may form a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

Two or more of A ₁ to A ₇ in Formula 1 are optionally bonded to each other to be substituted or unsubstituted with at least one R _1a C ₅ -C ₆₀ carbocyclic group or at least one R _1a May form a cyclic C ₁ -C ₆₀ heterocyclic group,

Two or more of the ring CY ₂ , the ring CY ₃ , R ₂₀ and R ₃₀ of Formula 2 are optionally bonded to each other and substituted or unsubstituted with at least one R _1a C ₅ -C ₆₀ carbocyclic group or at least One R _1a may form a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,

For a description of R _1a , refer to the description of A ₇ ,

The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic heterocondensed polycyclic group The substituent is,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alky A nil group or a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, Monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or any thereof A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group or a C ₁ -C ₆₀ alkoxy group substituted by a combination of;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alky Nyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ) or any combination thereof substituted or unsubstituted with at least one, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ aryl A thi group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ) or -P(Q ₃₈ )(Q ₃₉ ); or

Any combination thereof;

ego,

The Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; Hydroxyl group; Cyano group; Nitro group; Amidino group; Hydrazine; Hydrazone group; A carboxylic acid group or a salt thereof; Sulfonic acid groups or salts thereof; Phosphoric acid groups or salts thereof; Deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or substituted by any combination thereof or unsubstituted 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; Deuterium, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or a C ₆ -C ₆₀ aryl group unsubstituted or substituted with any combination thereof; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; Monovalent non-aromatic condensed polycyclic group; Or a monovalent non-aromatic condensed heteropolycyclic group;

According to another aspect, the first electrode; A second electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer, wherein the organic layer includes a composition including the first compound and the second compound.

The composition may be included in the emission layer among organic layers, and the first compound included in the emission layer may serve as a dopant.

The composition has excellent electrical properties and stability, and an electronic device employing the composition, for example, an organic light-emitting device, may have improved external quantum efficiency and improved lifespan characteristics.

1 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment.

The composition includes a first compound and a second compound, the first compound includes a compound represented by Formula 1 below, and the second compound may include a compound represented by Formula 2 below:

<Formula 1>

<Formula 2>

The first compound may include only one compound belonging to the compound represented by Chemical Formula 1, or may include two or more different compounds belonging to the compound represented by Chemical Formula 1.

The second compound may include only one compound belonging to the compound represented by Formula 2, or may include two or more different compounds belonging to the compound represented by Formula 2.

Chemical formula Description of 1

In Formula 1, Y ₂ may be C.

Ring CY ₁₂ in Formula 1 may be a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group.

For example, in Formula 1, the ring CY ₁₂ is i) a third ring, ii) a fourth ring, iii) a condensed ring in which two or more third rings are condensed with each other, iv) a condensation in which two or more fourth rings are condensed with each other Ring or v) a condensed ring in which at least one third ring and at least one fourth ring are condensed with each other,

The third ring is a cyclopentane group, cyclopentadiene group, furan group, thiophene group, pyrrole group, silol group, indene group, benzofuran group, benzothiophene group, indole group, benzosilol group, oxazole group, Isoxazole group, oxadiazole group, isoxadiazole group, oxatriazole group, isoxatriazole group, thiazole group, isothiazole group, thiadiazole group, isothiadiazole group, thiatriazole group, Isothiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, azasilol group, diazasilol group or triazasilol group,

The fourth ring is an adamantane group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, and a bicyclo[2.2.1]heptane group (norbornene It may be a norbornane group), a bicyclo[2.2.2]octane group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

According to an embodiment, the ring CY ₁₂ in Formula 1 is a cyclopentane group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, and Sen group, 1,2,3,4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, thiophene group, furan group, pyrrole group, cyclopentadiene group, silol group, borol group, phosphol Group, selenophene group, low molar group, benzothiophene group, benzofuran group, indole group, indene group, benzosilol group, benzoborole group, benzophosphole group, benzoselenophene group, benzojermol group, dibenzothiophene Group, dibenzofuran group, carbazole group, fluorene group, dibenzosilol group, dibenzoborole group, dibenzophosphole group, dibenzoselenophene group, dibenzozermole group, dibenzothiophene 5-oxide group , 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilol group, azabenzoborole Group, azabenzophosphole group, azabenzoselenophene group, azabenzozermol group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, azadibenzosilol group, azadi Benzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzozermole group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothi Offene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazole group, Imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzoimidazole group, benzoxazole group , Benzothiazole group, benzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahyde Leisoquinoline (5,6,7,8-tetrahydroisoquinoline) group, 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group, admantane group, norbor It may be a norbornane group or a norbornene group.

According to another embodiment, the ring CY ₁₂ is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, a thiophene group, a furan group, a pyrrole Group, cyclopentadiene group, silol group, benzothiophene group, benzofuran group, indole group, indene group, benzosilol group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, or di It may be a benzosilol group.

In Formula 1, R ₁ to R ₈ , A ₂₀ and A ₁ to A ₇ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, Nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ Aryl group, 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, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ) or -P(Q ₈ )(Q ₉ ) Can be. For the descriptions of Q ₁ to Q ₉ , each of the descriptions of the present specification is referred to.

According to an embodiment, A ₂₀ in Formula 1 may not include a fluoro group (-F) and a cyano group. For example, A ₂₀ may be any group including a fluoro group (-F) and a cyano group.

For example, in Formula 1, R ₁ to R ₈ , A ₂₀ and A ₁ to A ₇ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof , A phosphoric acid group or a salt thereof, -SF ₅ , a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl group, fluorinated C ₁ -C ₂₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]phen Tyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group (norbonanyl group), bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclopentyl group, ( C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C _1- C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1]heptyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, silolanyl group, phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2, C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group substituted with 3,4-tetrahydronaphthyl group, pyridinyl group, pyrimidinyl group, or any combination thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl group, fluorinated C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclophene Tyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbonenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, ( C ₁ -C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1] Heptyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2, 3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, imidazole Diary, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group , Furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazolyl group, phenane Trolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, Or substituted or unsubstituted by any combination thereof, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bi Cyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pi Renyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyri Midinyl group, pyridazinyl group, isoindole group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazole Diary, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, tria Genyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group or azadibenzo Thiophenyl group; or

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ) or -P(Q ₈ )(Q ₉ );

ego,

Q ₁ to Q ₉ are independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H , -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -CD ₂ CDH ₂ ; or

Substituted or unsubstituted with deuterium, C ₁ -C ₂₀ alkyl group, phenyl group, or any combination thereof, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group , n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, phenyl group, biphenyl group or naphthyl group;

Can be Here, A ₂₀ may not include a fluoro group and a cyano group.

According to an embodiment, in Formula 1, R ₁ to R ₈ , A ₂₀ and A ₁ to A ₇ are independently of each other, hydrogen, deuterium, -F, a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, a substituted or Unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted phenyl group, -Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge It may be (Q ₃ )(Q ₄ )(Q ₅ ). Here, A ₂₀ may not include a fluoro group and a cyano group.

According to another embodiment, in Formula 1, R ₁ to R ₈ and A ₁ to A ₇ are independently of each other,

Hydrogen, deuterium, or -F;

Deuterium, -F, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, a phenyl group, or a C ₁ -C ₂₀ alkyl group unsubstituted or substituted with any combination thereof, A C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or a phenyl group; or

-Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );

Can be

According to another embodiment, A ₂₀ in Formula 1 is,

Hydrogen, or deuterium;

Deuterium, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, phenyl group, or any combination thereof substituted or unsubstituted, C ₁ -C ₂₀ alkyl group, C _3- A C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or a phenyl group; or

-Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );

Can be

In Formula 1, d2 represents the number of A ₂₀ , and may be an integer of 0 to 10. When d2 is 2 or more, 2 or more A ₂₀ may be the same or different from each other. For example, d2 may be an integer of 0 to 6.

At least one of R ₁ to R ₈ and A ₂₀ in Formula 1 may include at least one fluoro group (-F).

For example, at least one of R ₁ to R ₈ in Formula 1 (eg, at least one of R ₂ to R ₈ , or at least one of R ₃ to R ₆ ) is at least one fluoro group (- F) may be included.

As another example, at least one of R ₁ to R ₈ of Formula 1 (eg, at least one of R ₂ to R ₈ , or at least one of R ₃ to R ₆ ) is independently of each other, at least one fluorine It may be any group including logi (-F).

According to an embodiment, at least one of R ₁ to R ₈ in Formula 1 is independently of each other,

Fluoro group (-F); or

A fluorinated C ₁ -C ₂₀ alkyl group substituted or unsubstituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a phenyl group, or any combination thereof , A fluorinated C ₃ -C ₁₀ cycloalkyl group, a fluorinated C ₁ -C ₁₀ heterocycloalkyl group, or a fluorinated phenyl group;

Can be

Meanwhile, according to an embodiment, at least one of A ₁ to A ₆ in Formula 1 is independently of each other, a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, A substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ hetero Cycloalkyl 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 Or it may be a substituted or unsubstituted monovalent non-aromatic condensed heterocyclic polycyclic group.

According to another embodiment, at least one of A ₁ to A ₆ in Formula 1 is independently of each other, a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted Or it may be an unsubstituted C ₁ -C ₁₀ heterocycloalkyl group.

According to another embodiment, at least one of A ₁ to A ₃ of Formula 1 and at least one of A ₄ to A ₆ are independently of each other, a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted It may be a C ₃ -C ₁₀ cycloalkyl group, or a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group.

According to another embodiment, at least one of A ₁ to A ₆ is independently of each other, deuterium, -F, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, Or it may be a substituted or unsubstituted, C ₂ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, or C ₁ -C ₁₀ heterocycloalkyl group by any combination thereof.

According to another embodiment, A ₁ to A ₆ in Formula 1 are independently of each other, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted Substituted 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 an unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or substituted or It may be an unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

According to another embodiment, A ₁ to A ₆ in Formula 1 are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted or non-substituted It may be a cyclic C ₁ -C ₁₀ heterocycloalkyl group.

According to another embodiment, A ₁ to A ₆ in Formula 1 are independently of each other, deuterium, -F, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, Or a substituted or unsubstituted C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, or C ₁ -C ₁₀ heterocycloalkyl group by any combination thereof.

According to another embodiment, A ₇ in Formula 1 may be hydrogen or deuterium.

According to another embodiment, A ₇ in Formula 1 may not be hydrogen.

According to another embodiment, in Formula 1, A ₇ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted or unsubstituted C ₁ -C ₁₀ It may be a heterocycloalkyl group.

According to another embodiment, A ₇ in Formula 1 is substituted with deuterium, -F, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof Or it may be an unsubstituted, C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C ₁ -C ₁₀ heterocycloalkyl group.

For example, in Formula 1, R ₁ to R ₈ , A ₂₀ and A ₁ to A ₇ are independently of each other, hydrogen, deuterium, -F, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , a group represented by one of the following formulas 9-1 to 9-39, wherein at least one hydrogen of one of the following formulas 9-1 to 9-39 is substituted with deuterium A group, a group in which at least one hydrogen of one of the following formulas 9-1 to 9-39 is substituted with -F, a group represented by one of the following formulas 9-201 to 9-233, in the following formulas 9-201 to 9-233 A group in which at least one hydrogen is substituted with deuterium, a group in which at least one hydrogen in one of the following formulas 9-201 to 9-233 is substituted with -F, a group represented by one of the following formulas 10-1 to 10-126 , A group in which at least one hydrogen of one of the following formulas 10-1 to 10-126 is substituted with deuterium, a group in which at least one hydrogen of one of the following formulas 10-1 to 10-126 is substituted with -F, the following formula A group represented by one of 10-201 to 10-343, a group in which at least one hydrogen of one of the following formulas 10-201 to 10-343 is substituted with deuterium, at least one of one of the following formulas 10-201 to 10-343 A group in which hydrogen is substituted with -F, -Si(Q ₃ )(Q ₄ )(Q ₅ ) or -Ge(Q ₃ )(Q ₄ )(Q ₅ ) (However, the description of Q ₃ to Q ₅ is Each refer to the bar described herein), but at least one of R ₁ to R ₈ (eg, at least one of R ₂ to R ₈ , or at least one of R ₃ to R ₆ ) is -F, -CF ₃ , -CF ₂ H, -CFH ₂ , a group in which at least one hydrogen of one of the following formulas 9-1 to 9-39 is substituted with -F, at least one of one of the following formulas 9-201 to 9-233 A group in which hydrogen is substituted with -F, At least one hydrogen of Formulas 10-1 to 10-126 may be a group substituted with -F, or a group in which at least one hydrogen of Formulas 10-201 to 10-343 is substituted with -F .

As another example, in Formula 1, A ₂₀ is hydrogen, deuterium, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , a group represented by one of the following formulas 9-1 to 9-39, the following formula A group in which at least one hydrogen of one of 9-1 to 9-39 is substituted with deuterium, a group represented by one of the following formulas 9-201 to 9-233, at least one of one of the following formulas 9-201 to 9-233 A group in which hydrogen is substituted with deuterium, a group represented by one of the following formulas 10-1 to 10-126, a group in which at least one hydrogen of one of the following formulas 10-1 to 10-126 is substituted with deuterium, the following formula 10-201 The group represented by one of to 10-343, a group in which at least one hydrogen of one of the following Formulas 10-201 to 10-343 is substituted with deuterium, -Si(Q ₃ )(Q ₄ )(Q ₅ ) or -Ge( It may be Q ₃ ) (Q ₄ ) (Q ₅ ) (however, for descriptions of Q ₃ to Q ₅ , each of the descriptions described herein is referred to).

As another example, at least one of A ₁ to A ₆ in Formula 1 is independently of each other, at least one of a group represented by one of the following Formulas 9-1 to 9-39, and at least one of the following Formulas 9-1 to 9-39 A group in which hydrogen of is substituted with deuterium, a group in which at least one hydrogen of one of the following formulas 9-1 to 9-39 is substituted with -F, a group represented by one of the following formulas 9-201 to 9-233, the following formula A group in which at least one hydrogen of one of -201 to 9-233 is substituted with deuterium, a group in which at least one hydrogen of one of the following formulas 9-201 to 9-233 is substituted with -F, the following formulas 10-1 to A group represented by one of 10-126, a group in which at least one hydrogen of one of the following formulas 10-1 to 10-126 is substituted with deuterium, and at least one hydrogen of one of the following formulas 10-1 to 10-126 is -F A group substituted with, a group represented by one of the following formulas 10-201 to 10-343, a group in which at least one hydrogen of one of the following formulas 10-201 to 10-343 is substituted with deuterium, or the following formulas 10-201 to 10 At least one hydrogen of one of -343 may be a group substituted with -F.

As another example, in Formula 1, A ₁ to A ₆ are independently of each other, -CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , the following A group represented by one of Formulas 9-1 to 9-39, a group in which at least one hydrogen of one of the following Formulas 9-1 to 9-39 is substituted with deuterium, at least one of one of the following Formulas 9-1 to 9-39 A group in which hydrogen of is substituted with -F, a group represented by one of the following formulas 9-201 to 9-233, a group in which at least one hydrogen of one of the following formulas 9-201 to 9-233 is substituted with deuterium, the following formula 9 A group in which at least one hydrogen of one of -201 to 9-233 is substituted with -F, a group represented by one of the following formulas 10-1 to 10-126, at least one of one of the following formulas 10-1 to 10-126 A group in which hydrogen is substituted with deuterium, a group in which at least one hydrogen of the following formulas 10-1 to 10-126 is substituted with -F, a group represented by one of the following formulas 10-201 to 10-343, the following formula 10- At least one hydrogen of 201 to 10-343 may be a group substituted with deuterium, or a group in which at least one hydrogen of one of the following Formulas 10-201 to 10-343 is substituted with -F:

In Formulas 9-1 to 9-39, 9-201 to 9-233, 10-1 to 10-126, and 10-201 to 10-343, * is a bonding site with a neighboring atom, Ph is a phenyl group, TMS is a trimethylsilyl group, and TMG is a trimethylgermyl group.

The "group in which at least one hydrogen of formulas 9-1 to 9-39 is substituted with deuterium" and "a group in which at least one hydrogen of formulas 9-201 to 9-233 is substituted with deuterium" is, for example, It may be a group represented by Formulas 9-501 to 9-514 and 9-601 to 9-635:

The "group in which at least one hydrogen of formulas 9-1 to 9-39 is substituted with -F" and "a group in which at least one hydrogen of formulas 9-201 to 9-233 is substituted with -F" is, for example , It may be a group represented by the following Chemical Formulas 9-701 to 9-710:

The "group in which at least one hydrogen in Formulas 10-1 to 10-126 is substituted with deuterium" and "A group in which at least one hydrogen in Formulas 10-201 to 10-343 is substituted with deuterium" is, for example, It may be a group represented by Chemical Formulas 10-501 to 10-553:

The "group in which at least one hydrogen in Formulas 10-1 to 10-126 is substituted with -F" and "a group in which at least one hydrogen in Formulas 10-201 to 10-343 is substituted with -F" is, for example , It may be a group represented by the following Chemical Formulas 10-601 to 10-617:

According to an embodiment, in Formula 1,

1) R ₂ contains at least one fluoro group (-F);

2) R ₃ contains at least one fluoro group (-F);

3) R ₄ contains at least one fluoro group (-F);

4) R ₅ contains at least one fluoro group (-F);

5) R ₆ contains at least one fluoro group (-F);

6) R ₇ contains at least one fluoro group (-F);

7) R ₈ contains at least one fluoro group (-F);

8) each of R ₄ and R ₅ contains at least one fluoro group (-F);

9) each of R ₄ and R ₆ contains at least one fluoro group (-F);

10) each of R ₅ and R ₆ contains at least one fluoro group (-F);

11) each of R ₃ and R ₄ contains at least one fluoro group (-F); or

12) Each of R ₃ and R ₆ may contain at least one fluoro group (-F).

According to another embodiment, in Formula 1,

One or two of R ₁ to R ₈ independently of each other include at least one fluoro group (-F),

At least one of R ₁ to R ₈ may be i) not including a fluoro group (-F), and ii) not hydrogen.

According to another embodiment, A ₂₀ in Formula 1 is substituted or provided with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof. It may be a cyclic, C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, or a C ₁ -C ₁₀ heterocycloalkyl group.

According to another embodiment, A ₂₀ in Formula 1 may be a C ₁ -C ₂₀ alkyl group substituted or unsubstituted with deuterium, a C ₁ -C ₂₀ alkyl group, or any combination thereof.

According to another embodiment, d2 in Formula 1 may be 2.

And According to another embodiment, the formula of A is _20, deuterium, C ₁ -C ₂₀ alkyl group, or substituted by any combination thereof or unsubstituted C ₁ -C ₂₀ alkyl group, d2 may be 2 days.

According to another embodiment, the organometallic compound represented by Formula 1 may contain at least one deuterium.

According to another embodiment, at least one of R ₁ to R ₈ in Formula 1 may include at least one deuterium.

According to another embodiment, at least one of d2 R ₂₀ in Formula 1 may contain deuterium.

According to another embodiment, at least one of d2 R ₂₀ in Formula 1 is a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or any combination thereof. It may be a substituted or unsubstituted, deuterium-containing C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₃ -C ₁₀ cycloalkyl group, or a deuterium-containing C ₁ -C ₁₀ heterocycloalkyl group.

로 표시된 그룹은 하기 화학식 CY1 내지 CY108 중 하나로 표시된 그룹일 수 있다:According to an embodiment, in Formula 1

The group represented by may be a group represented by one of the following formulas CY1 to CY108:

In the above formulas CY1 to CY108

T ₂ to T ₈ are independently of each other,

Fluoro group (-F); or

A fluorinated C ₁ -C ₂₀ alkyl group substituted or unsubstituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a phenyl group or any combination thereof, A fluorinated C ₃ -C ₁₀ cycloalkyl group, a fluorinated C ₁ -C ₁₀ heterocycloalkyl group, or a fluorinated phenyl group;

ego,

For the description of R ₂ to R ₈ and R _1a , refer to the bar described in claim 1, respectively, but R ₂ to R ₈ are not hydrogen,

* Is a binding site with Ir in Formula 1,

*" is a bonding site with neighboring atoms in Formula 1.

For example, in Formulas CY1 to CY108, R ₂ to R ₈ are independently of each other,

heavy hydrogen; or

Deuterium, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₂₀ alkyl group, C ₃ -C unsubstituted or substituted with a phenyl group or any combination thereof ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, or phenyl group;

Can be

로 표시된 그룹은 하기 화학식 A(1) 내지 A(7) 중 하나로 표시된 그룹일 수 있다:According to another embodiment, in Formula 1

The group represented by may be a group represented by one of the following formulas A(1) to A(7):

In Formulas A(1) to A(7),

Y ₂ is C,

X ₂₁ is O, S, N(R ₂₅ ), C(R ₂₅ )(R ₂₆ ) or Si(R ₂₅ )(R ₂₆ ),

For the description of R ₉ to R ₁₂ and R ₂₁ to R ₂₆ , each refer to the description of A ₂₀ in the present specification,

*'is a binding site with Ir in Formula 1,

*" is a bonding site with neighboring atoms in Formula 1.

For example, in Formula A(1), R ₉ and R ₁₁ are independently of each other, deuterium, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, phenyl group or its It may be a substituted or unsubstituted, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, or phenyl group in any combination.

As yet another example, the formula A R ₉ and R ₁₁ of (1) are independently of one another, deuterium, C ₁ -C ₂₀ alkyl group, or substituted by any combination thereof or unsubstituted ring may be a C ₁ -C ₂₀ alkyl group have.

As another example, in Formula A(1), R ₁₀ and R ₁₂ may be each independently hydrogen or deuterium.

As another example, in Formula A(1), R ₉ and R ₁₁ may be the same as each other.

As another example, in Formula A(1), R ₉ and R ₁₁ may be different from each other.

As another example, in Formula A(1), R ₉ and R ₁₁ may be different from each other, and the number of carbons included in R ₁₁ may be greater than the number of carbons included in R ₉ .

As another example, i) at least one of R ₉ to R ₁₂ of Formula A(1), ii) one of R ₁₁ , R ₁₂ , R ₂₁ to R ₂₆ of Formulas A(2) and A(3) , Or any combination thereof, iii) one of R ₉ , R ₁₂ , R ₂₁ to R ₂₆ of Formulas A (4) and A (5), or any combination thereof, and iv) Formula A (6) and One of R ₉ , R ₁₀ , R ₂₁ to R ₂₆ of A(7), or any combination thereof, independently of each other, is a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ A heterocycloalkyl group, or a deuterium-containing C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₃ -C ₁₀ cycloalkyl group, or a deuterium-containing C ₁ -C ₁₀ heterocycloalkyl group, unsubstituted or substituted with any combination thereof I can.

As yet another example, at least one of R ₉ and R ₁₁ of the formula A (1) (for example, R ₉ and R ₁₁ of the formula A (1)) is independently of one another, C ₁ -C ₂₀ alkyl, C _{A 3} -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or a deuterium-containing C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₃ -C ₁₀ cycloalkyl group, unsubstituted or substituted with any combination thereof, or It may be a deuterium-containing C ₁ -C ₁₀ heterocycloalkyl group.

로 표시된 그룹은 하기 화학식 A(1) 또는 A(5)로 표시된 그룹일 수 있다.According to another embodiment, in Formula 1

The group represented by may be a group represented by the following formula A(1) or A(5).

Meanwhile, the number of carbon atoms contained in the group represented by *-C(A ₁ )(A ₂ )(A ₃ ) in Formula 1 is 5 or more, and/or *-C(A ₄ )(A _{5 in} Formula 1 ) The number of carbon atoms contained in the group represented by (A ₆ ) may be 5 or more.

According to an embodiment, A ₁ to A ₃ of the group represented by *-C(A ₁ )(A ₂ )(A ₃ ) in Formula 1 are bonded to each other, and are substituted or unsubstituted with at least one R _1a A C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _1a may be formed. That is, the group represented by *-C(A ₁ )(A ₂ )(A ₃ ) in Formula 1 is a C ₅ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R _1a or at least one R _1a a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group, a click (for example, substituted or unsubstituted with at least one of R _1a, adamantane (admantane) group, norbornene group, bicyclo [ 1.1.1] pentane group, bicyclo[2.1.1] hexane group, bicyclo[2.2.1] heptane group (norbornane group), bicyclo[2.2.2] octane group, cyclopentane group, It may be a cyclohexane group, or a cyclohexene group).

According to another embodiment, A ₄ to A ₆ of the group represented by *-C (A ₄ ) (A ₅ ) (A ₆ ) in Formula 1 are bonded to each other, and unsubstituted or substituted with at least one R _1a A C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group unsubstituted or substituted with at least one R _1a may be formed. That is, the group represented by *-C (A ₄ ) (A ₅ ) (A ₆ ) in Formula 1 is a C ₅ -C ₆₀ carbocyclic group substituted or unsubstituted with at least one R _1a or at least one R _1a a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group, a click (for example, substituted or unsubstituted with at least one of R _1a, adamantane (admantane) group, norbornene group, bicyclo [ 1.1.1] pentane group, bicyclo[2.1.1] hexane group, bicyclo[2.2.1] heptane group (norbornane group), bicyclo[2.2.2] octane group, cyclopentane group, It may be a cyclohexane group, or a cyclohexene group).

According to another embodiment, the group represented by *-C(A ₁ ) (A ₂ ) (A ₃ ) and the group represented by *-C (A ₄ ) (A ₅ ) (A ₆ ) in Formula 1 are It can be the same.

According to another embodiment, the group represented by *-C(A ₁ ) (A ₂ ) (A ₃ ) and the group represented by *-C (A ₄ ) (A ₅ ) (A ₆ ) in Formula 1 are It can be different.

For example, the first compound may contain at least one of the following compounds 1 to 53:

The first compound includes an organometallic compound represented by Chemical Formula 1. Of the organometallic compounds represented by Formula 1, 1) ring CY ₁₁ (see Formula 1'below) is a condensed ring in which two benzene groups and one pyridine group are condensed with each other as shown in Formula 1, and 2) Formula At least one of R ₁ to R ₈ and A ₂₀ of 1 includes at least one fluoro group (-F). As a result, the transition dipole moment of the organometallic compound is improved, the length of conjugation of the organometallic compound is relatively increased, and structural rigidity is increased, so that non-luminescence transition may be reduced. Accordingly, an electronic device employing the organometallic compound represented by Formula 1, for example, an organic light-emitting device, may have high external quantum efficiency (EQE), and thus high light emission efficiency.

<Formula 1'>

In addition, according to an embodiment, at least one of A ₁ to A ₆ in Formula 1 is independently of each other, a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted Or an unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocyclo Alkyl 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, Or in the case of a substituted or unsubstituted monovalent non-aromatic hetero-condensed polycyclic group (that is, when at least one of A ₁ to A ₆ in Formula 1 has 2 or more carbons), Ligand 2 in Formula 1 (the formula 1′), the electron donating ability of the formula 1 is improved, and thus the interaction between Ligand 1 and Ligand 2 in Formula 1 may be enhanced. Accordingly, the organometallic compound represented by Formula 1 may have improved light-emitting transition properties, improved photo-alignment properties, and improved structural rigidity. An electronic device including an organometallic compound represented by Formula 1, for example, an organic light-emitting device May have high luminescence efficiency and lifetime.

Further, according to another embodiment, A ₁ to A ₆ in Formula 1 are independently of each other, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted Substituted 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 an unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or substituted or In the case of an unsubstituted monovalent non-aromatic heterocondensed polycyclic group (that is, when A ₁ to A ₆ in Formula 1 has 1 or more carbons), the carbon bonded to A ₁ to A _{6 in} Formula 1 is α -Proton (α-proton) may not be included, and the organometallic compound represented by Formula 1 has a stable chemical structure in which the occurrence of side reactions before/after synthesis is minimized, and at the same time, an electronic device employing it (for example, For example, during driving of the organic light-emitting device), the interaction between the molecules of the organometallic compound may be minimized, and the interaction between Ligand 2 and Ligand 1 may be enhanced, thereby improving the rigidity of the organometallic compound represented by Formula 1. Accordingly, the full width at half maximum (FWHM) of the PL spectrum or the EL spectrum for the organometallic compound represented by Formula 1 can be reduced, and the vibration of the organometallic compound molecule represented by Formula 1 As the vibronic state is reduced, non-radiative decay can be reduced. Accordingly, an electronic device including the organometallic compound represented by Chemical Formula 1, for example, an organic light-emitting device, may have high light emission efficiency and lifetime.

A method for synthesizing the first compound represented by Chemical Formula 1 may be recognized by those skilled in the art by referring to Synthesis Examples described below.

Chemical formula Description of 2

Formula 2 of Ar ₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or optionally substituted with at least one R ₆₁ or unsubstituted C ₁ -C ₆₀ heterocyclic group with at least one R _61,

Ar ₂ in Formula 2 is a π electron deficient nitrogen-containing C ₁ -C ₆₀ cyclic group unsubstituted or substituted with at least one R ₆₂ ,

In Formula 2 Ar ₅ is a single bond, a substituted or unsubstituted with at least one R ₆₅ C ₅ -C ₆₀ carbocyclic group, or a substituted or unsubstituted with at least one of the R ₆₅ C ₁ -C ₆₀ heterocyclic Is a group, does not exist,

In Formula 2, n is 1, 2 or 3, and when n is 1, Ar ₅ does not exist,

In Formula 2, a1 and a2 are each independently an integer of 0 to 5, but the sum of a1 and a2 is 1 or more,

In Formula 2, ring CY ₂ and ring CY ₃ are each independently a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group, and ring CY ₂ and ring CY ₃ are optionally, at least one with the R ₆₆ substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or at least one R ₆₆ substituted or unsubstituted C ₁ -C ₆₀ heteroaryl the cyclic group may be bonded to each other in between.

In the present specification, "π electron deficient nitrogen-containing C ₁ -C ₆₀ cyclic group" refers to a cyclic group having 1 to 60 carbon atoms including at least one *-N=*' as a cyclic moiety, for example , a) a first ring, b) a condensed ring in which two or more first rings are condensed with each other, or c) a condensed ring in which one or more first rings and one or more second rings are condensed with each other. Specific examples of the first ring and the second ring refer to those described herein.

The π electron deficient nitrogen-containing C ₁ -C ₆₀ cyclic group is, for example, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, and a pyrazine Group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, benzoquinoxaline group , Quinazoline group, sinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, Triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, azadibenzofuran group, azadibenzothiophene Group, azadibenzosilol group, benzonaphthofuran group, benzonaphthothiophene group, (indolo) phenanthrene group, (benzofurano) phenanthrene group, (benzothieno) phenanthrene group, or pyridopyrazine It can be a group.

In the present specification, "π electron rich C ₃ -C ₆₀ cyclic group" refers to a cyclic group having 3 to 60 carbon atoms that does not include *-N=*' as a cyclic moiety, for example, a ) A second ring or b) a condensed ring in which two or more second rings are condensed with each other. Specific examples of the second ring refer to those described herein.

The π electron rich C ₃ -C ₆₀ cyclic group is, for example, a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthylene group. , Fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, cryo Sen group, naphthacene group, picene group, perylene group, pentacene group, hexacene group, pentaphene group, rubicene group, coronene group, ovalene group, pyrrole group, furan group, thiophene group, isoindole Group, indole group, indene group, benzofuran group, benzothiophene group, benzosilol group, naphtopyrrole group, naphthofuran group, naphthothiophene group, naphtosilol group, benzocarbazole group, dibenzocarbazole Group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilol group, indenocarbazole group, indolocarbazole group, benzofurocarbazole Group, benzothienocarbazole group, benzosilolocarbazole group, triindolobenzene group, acridine group, dihydroacridine group, pyrrolophenanthrene group, furanophenanthrene group or thienophenanthrene It can be a group.

According to one embodiment,

Formula 2 of Ar ₁ is i) substituted with at least one R ₆₁ substituted or unsubstituted first ring, ii) at least one R ₆₁ substituted or unsubstituted 2 rings, iii) at least one of R ₆₁ switches to switch to or unsubstituted with at least two first ring is a substituted or unsubstituted at least the ring 2 second ring are condensed with each other to at least one of R ₆₁ a condensed ring, iv) condensed with each other a condensed ring, or v) optionally substituted with at least one R ₆₁ Or an unsubstituted, group derived from a condensed ring in which at least one first ring and at least one second ring are condensed with each other,

Formula 2 of the Ar ₂ is i) at least one of R a ₆₂ substituted or unsubstituted first ring, ii) a substituted or unsubstituted at least the ring 2 the first ring is fused to each other by at least one R ₆₂ in the condensed ring, or iii) a group derived from a condensed ring in which at least one first ring and at least one second ring are condensed with each other, unsubstituted or substituted with at least one R ₆₂ ,

Or the general formula (2) of the Ar ₅ is a single bond, i) at least one substituted with R ₆₅ or unsubstituted first ring, ii) at least one at least one R ₆₅ substituted or unsubstituted second ring, iii ring in) A condensed ring in which two or more first rings substituted or unsubstituted with R ₆₅ are condensed with each other, iv) a condensed ring in which two or more second rings substituted or unsubstituted with R ₆₅ are condensed with each other or v) at least one R ₆₅ substituted or unsubstituted, at least one first ring and at least one second ring is a group derived from a condensed ring condensed with each other, or does not exist,

In Formula 2, ring CY ₂ and ring CY ₃ are independently of each other, i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) two or more second rings are A condensed ring condensed with each other or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other,

The first ring is an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, a triazole group, a tetrazole Group, oxadiazole group, triazine group, or thiadiazole group,

The second ring may be a benzene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group, or a silol group.

According to another embodiment, Ar ₁ in Formula 2 is substituted or unsubstituted with at least one R ₆₁ , a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, Acenaphthylene group, fluorene group, spiro-bifluorene group, benzofluorene group, dibenzofluorene group, phenalene group, phenanthrene group, anthracene group, fluoranthene group, triphenylene group, pi Ren group, chrysene group, naphthacene group, picene group, perylene group, pentacene group, hexacene group, pentaphene group, rubicene group, coronene group, ovalene group, pyrrole group, furan group, thiophene Group, isoindole group, indole group, indene group, benzofuran group, benzothiophene group, benzosilol group, naphtopyrrole group, naphthofuran group, naphthothiophene group, naphtosilol group, benzocarbazole group, Dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilol group, indenocarbazole group, indolocarbazole group, benzo Purocarbazole group, benzothienocarbazole group, benzosilolocarbazole group, triindolobenzene group, acridine group, dihydroacridine group, imidazole group, pyrazole group, thiazole group, Isothiazole group, oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, Phthalargine group, naphthyridine group, quinoxaline group, benzoquinoxaline group, quinazoline group, sinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, Isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group , Azacarbazole group, azadibenzofuran group, azadibenzothiophene It may be a loop or an azadibenzosilol group.

According to another embodiment, Ar ₂ in Formula 2 is substituted or unsubstituted with at least one R ₆₂ , an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, Pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, Benzoquinoxaline group, quinazoline group, sinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, isobenzothiazole group, benzoxazole group, isobenzo Oxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, azadibenzofuran group, aza It may be a dibenzothiophene group, an azadibenzosilol group, or a pyridopyrazine group.

According to another embodiment, the ring CY ₂ and the ring CY ₃ are each independently a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthylene 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, pentacene group, hexacene group, pentaphene group, rubicene group, coronene group, ovalene group, pyrrole group, furan group, thiophene group, isoindole group , Indole group, indene group, benzofuran group, benzothiophene group, benzosilol group, naphtopyrrole group, naphthofuran group, naphthothiophene group, naphtosilol group, benzocarbazole group, dibenzocarbazole group , Dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzosilol group, indenocarbazole group, indolocarbazole group, benzofurocarbazole group , Benzothienocarbazole group, benzosilolocarbazole group, triindolobenzene group, acridine group, dihydroacridine group, imidazole group, pyrazole group, thiazole group, isothiazole group, Oxazole group, isoxazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, phthalazine group, Naphthyridine group, quinoxaline group, benzoquinoxaline group, quinazoline group, sinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, isobenzothiazole group , Benzoxazole group, isobenzoxazole group, triazole group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group , Azadibenzofuran group, azadibenzothiophene group or azadibenzo It may be a silol group.

According to another embodiment, when n is 1 in Formula 2, at least one of the rings CY ₂ and CY ₃ may not be a benzene group.

According to another embodiment, in Formula 2, the ring CY ₂ and the ring CY ₃ may be independently of each other, and may be a π electron rich C ₃ -C ₆₀ cyclic group.

According to another embodiment, when n is 1 in Formula 2, at least one of the rings CY ₂ and CY ₃ is a) a condensed ring in which two or more first rings are condensed with each other, b) two or more second rings are It may be a condensed ring condensed with each other or c) a condensed ring in which at least one first ring and at least one second ring are condensed with each other. Here, the description of the first ring and the second ring refer to the bar described in the present specification, respectively.

According to another embodiment, the second compound may include a compound represented by Formula 2 (1) below:

<Formula 2(1)>

In Formula 2 (1),

Ar ₅ is a single bond, substituted with at least one of R ₆₅ or unsubstituted C ₅ -C ₆₀ carbocyclic group or optionally substituted with at least one R ₆₅ or unsubstituted C ₁ -C ₆₀ heterocyclic group,

Ar ₁ , Ar ₂ , Ar ₅ , a1, a2, ring CY ₂ , ring CY ₃ , R ₂₀ , R ₃₀ , b2 and b3, respectively, refer to the bar described herein,

For the description of Ar ₃ and Ar ₄ , respectively, refer to the description of Ar ₁ in the present specification,

Description of a3, a4, ring CY ₄ , ring CY ₅ , R ₄₀ , R ₅₀ , b4 and b5 are in the present specification, respectively, a1, a2, ring CY ₂ , ring CY ₃ , R ₂₀ , R ₃₀ , b2 and b3 See the description of.

For example, in Formula 2(1), Ar ₅ may be a single bond.

로 표시된 그룹 및 상기 화학식 2(1) 중

로 표시된 그룹 및

로 표시된 그룹은 서로 독립적으로, 하기 화학식 2-1 내지 2-93 중 하나로 표시된 그룹일 수 있다:According to another embodiment, in Formula 2

In the group represented by and Formula 2 (1)

Groups marked with and

The groups represented by may be, independently of each other, a group represented by one of the following Formulas 2-1 to 2-93:

In Formulas 2-1 to 2-93,

X ₁ is O, S, N(R ₃₁ ), C(R ₃₁ )(R ₃₂ ) or Si(R ₃₁ )(R ₃₂ ),

X ₂ is O, S, N(R ₃₃ ), C(R ₃₃ )(R ₃₄ ) or Si(R ₃₃ )(R ₃₄ ),

For the description of R ₃₁ to R ₃₄ , each of the descriptions of R ₃₀ in the present specification refers to

* Is a binding site with Ar ₁ or Ar ₂ in Formula 2.

According to another embodiment, Ar ₂ in Formulas 2 and 2 (1) may be a group represented by one of the following Formulas 5-1 to 5-31:

In Formulas 5-1 to 5-31,

For a description of R ₆₂ , see what is described herein,

c2 is an integer from 0 to 2,

c3 is an integer from 0 to 3,

c4 is an integer from 0 to 4,

c5 is an integer from 0 to 5,

c7 is an integer from 0 to 7,

* Is a binding site with Ar ₁ or N in Formulas 2 and 2(1).

In Formulas 2 and 2(1), a1 and a2 represent the number of Ar ₁ and Ar ₂ , respectively, and are independently an integer of 0 to 5, but the sum of a1 and a2 may be 1 or more. When a1 is 2 or more, 2 or more Ar ₁ is the same as or different from each other, and when a2 is 2 or more, 2 or more Ar ₂ is the same or different from each other. When a1 is 0, *-(Ar ₁ ) _a1 -*' in Formula 2 becomes a single bond.

According to an embodiment, in Formulas 2 and 2(1), a2 is not 0.

For example, in Formulas 2 and 2(1), a2 may be 1 or 2.

According to another embodiment, in Formula 2(1), a2 is 1 or 2, Ar ₃ and Ar ₄ are each independently of each other, deuterium, C ₁ -C ₂₀ alkyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, Or a substituted or unsubstituted π electron rich C ₃ -C ₆₀ cyclic group (e.g., benzene group, naphthalene group, phenanthrene group, carbazole group, dibenzofuran group or di Benzothiophene group, etc.).

According to another embodiment, n in Formula 2 may be 1 or 2.

In Formula 2, R ₂₀ , R ₃₀ , R ₆₁ , R ₆₂ , R ₆₅ and R ₆₆ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, Cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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, A substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, 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, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ) or -P(Q ₈ ) May be (Q ₉ ). For the descriptions of Q ₁ to Q ₉ , each of the descriptions of the present specification is referred to.

For example, in Formula 2, R ₂₀ , R ₃₀ , R ₆₁ , R ₆₂ , R ₆₅ and R ₆₆ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof , A phosphoric acid group or a salt thereof, -SF ₅ , a C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl group, fluorinated C ₁ -C ₂₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]phen Tyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group (norbonanyl group), bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclopentyl group, ( C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbornenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, (C _1- C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1]heptyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, silolanyl group, phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2, C ₁ -C ₂₀ alkyl group or C ₁ -C ₂₀ alkoxy group substituted with 3,4-tetrahydronaphthyl group, pyridinyl group, pyrimidinyl group, or any combination thereof;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl group, fluorinated C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, (C ₁ -C ₂₀ alkyl)cyclophene Tyl group, (C ₁ -C ₂₀ alkyl) cyclohexyl group, (C ₁ -C ₂₀ alkyl) cycloheptyl group, (C ₁ -C ₂₀ alkyl) cyclooctyl group, (C ₁ -C ₂₀ alkyl) adamantanyl group, (C ₁ -C ₂₀ alkyl) norbonenyl group, (C ₁ -C ₂₀ alkyl) cyclopentenyl group, (C ₁ -C ₂₀ alkyl) cyclohexenyl group, (C ₁ -C ₂₀ alkyl) cycloheptenyl group, ( C ₁ -C ₂₀ alkyl)bicyclo[1.1.1]pentyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.1.1]hexyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.1] Heptyl group, (C ₁ -C ₂₀ alkyl)bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C ₁ -C ₂₀ alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2, 3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, imidazole Diary, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group , Furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazolyl group, phenane Trolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, Dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, Or substituted or unsubstituted by any combination thereof, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bi Cyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, siloranyl group, phenyl group, (C ₁ -C ₂₀ alkyl) phenyl group, biphenyl group, terphenyl group, naphthyl group, 1,2,3,4-tetrahydronaphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pi Renyl group, chrysenyl group, pyrroleyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyri Midinyl group, pyridazinyl group, isoindole group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, sinolinyl group, carbazole Diary, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, tria Genyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group or azadibenzo Thiophenyl group; or

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(=O)(Q ₈ )(Q ₉ ) or -P(Q ₈ )(Q ₉ );

ego,

Q ₁ to Q ₉ are independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H , -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -CD ₂ CDH ₂ ; or

Substituted or unsubstituted with deuterium, C ₁ -C ₂₀ alkyl group, phenyl group, or any combination thereof, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group , n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, phenyl group, biphenyl group or naphthyl group;

In Formula 2, b2 and b3 represent the number of R ₂₀ and R ₃₀ , respectively, and independently of each other, may be an integer of 0 to 20. For example, b2 and b3 may each independently be an integer of 0 to 10. When b2 is 2 or more, two or more R ₂₀ are the same as or different from each other, and when b3 is 2 or more, two or more R ₃₀ are the same or different from each other.

For example, in Formula 2, R ₂₀ , R ₃₀ , R ₆₁ , R ₆₂ , R ₆₅ and R ₆₆ are independently of each other,

Hydrogen or deuterium;

Deuterium, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, di(C ₁ -C ₁₀ alkyl) fluorenyl group, di(C ₆ -C ₆₀ aryl) fluorenyl group, Dibenzosilolyl group, di(C ₁ -C ₁₀ alkyl)dibenzosilolyl group, di(C ₆ -C ₆₀ aryl)dibenzosilolyl group, carbazolyl group, (C ₁ -C ₁₀ alkyl)carbazolyl group, ( C ₆ -C ₆₀ aryl) carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, terphenyl group, -N (Q ₃₁ ) (Q ₃₂ ), or unsubstituted or substituted with any combination thereof, A C ₁ -C ₂₀ alkyl group or a C ₁ -C ₂₀ alkoxy group;

Deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, di(C ₁ -C ₁₀ alkyl)fluore Nyl group, di(C ₆ -C ₆₀ aryl) fluorenyl group, dibenzosilolyl group, di(C ₁ -C ₁₀ alkyl) dibenzosilolyl group, di(C ₆ -C ₆₀ aryl) dibenzosilolyl group, carbazole Diary, (C ₁ -C ₁₀ alkyl) carbazolyl group, (C ₆ -C ₆₀ aryl) carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, terphenyl group, -N(Q ₃₁ )(Q ₃₂ ), or a π electron-rich C ₃ -C ₆₀ cyclic group unsubstituted or substituted with any combination thereof; or

-N(Q ₁ )(Q ₂ );

Can be Here, the descriptions of Q ₁ , Q ₂ , Q ₃₁ and Q ₃₂ refer to those described in the present specification, respectively.

As another example, in Formula 2, R ₂₀ , R ₃₀ , R ₆₁ , R ₆₂ , R ₆₅ and R ₆₆ are independently of each other,

Hydrogen or deuterium;

Deuterium, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, di(C ₁ -C ₁₀ alkyl) fluorenyl group, di(C ₆ -C ₆₀ aryl) fluorenyl group, Dibenzosilolyl group, di(C ₁ -C ₁₀ alkyl)dibenzosilolyl group, di(C ₆ -C ₆₀ aryl)dibenzosilolyl group, carbazolyl group, (C ₁ -C ₁₀ alkyl)carbazolyl group, ( C ₆ -C ₆₀ aryl) carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, terphenyl group, -N (Q ₃₁ ) (Q ₃₂ ), or C unsubstituted or substituted with any combination thereof ₁ -C ₂₀ alkyl group; or

Deuterium, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, di(C ₁ -C ₁₀ alkyl)fluore Nyl group, di(C ₆ -C ₆₀ aryl) fluorenyl group, dibenzosilolyl group, di(C ₁ -C ₁₀ alkyl) dibenzosilolyl group, di(C ₆ -C ₆₀ aryl) dibenzosilolyl group, carbazole Diary, (C ₁ -C ₁₀ alkyl) carbazolyl group, (C ₆ -C ₆₀ aryl) carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group, biphenyl group, terphenyl group, or any combination thereof substituted or Unsubstituted, phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, triphenylenyl group, fluorenyl group, dibenzosilolyl group, carbazolyl group, dibenzofuranyl group, dibenzothiophenyl group;

Can be Here, the descriptions of Q ₃₁ and Q ₃₂ refer to those described in the present specification, respectively.

For example, the second compound represented by Formula 2 may contain at least one of the following compounds H1 to H90:

An electronic device employing the composition including the second compound as described above, for example, an organic light-emitting device, may have excellent external quantum efficiency and lifespan characteristics.

In Formulas 1 and 2, 2 or more of 1) R ₁ to R ₈ and A ₂₀ are optionally combined with each other, and C ₅ -C ₆₀ carbocyclic substituted or unsubstituted with at least one R _1a A group or at least one R _1a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group may be formed, and 2) two or more of A ₁ to A ₇ are optionally bonded to each other, at least one R _1a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or at least one R _1a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group may be formed, and 3) ring CY ₂ , ring Two or more of CY ₃ , R ₂₀ and R ₃₀ are optionally bonded to each other and substituted or unsubstituted with at least one R _1a C ₅ -C ₆₀ carbocyclic group or at least one R _1a substituted or unsubstituted Formed C ₁ -C ₆₀ heterocyclic groups. Here, for the description of R _1a , refer to the description of A ₇ in the present specification.

In the present specification, a C ₅ -C ₆₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 60 carbons as ring forming atoms. The C ₅ -C ₆₀ carbocyclic group may be a monocyclic group or a polycyclic group. "C ₅ -C ₆₀ carbocyclic group (unsubstituted or substituted with at least one R _1a )" means, for example, adamantane (unsubstituted or substituted with at least one R _1a ) Group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.1]heptane group (norbornane group), bicyclo[2.2 .2] Octane group, cyclopentane group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, 1,2,3, A 4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, a cyclopentadiene group, a silol group, a fluorene group, and the like may be included.

In the present specification, the C ₁ -C ₆₀ heterocyclic group refers to a saturated or unsaturated cyclic group having at least one hetero atom selected from N, O, P, Si, and S in addition to 1 to 60 carbons as ring forming atoms. The C ₁ -C ₃₀ heterocyclic group may be a monocyclic group or a polycyclic group. "(Unsubstituted or substituted with at least one R _1a ) C ₁ -C ₆₀ heterocyclic group" means, for example, a thiophene group, a furan group (unsubstituted or substituted with at least one R _1a ) , Pyrrole group, silol group, borol group, phosphol group, selenophene group, low molar group, benzothiophene group, benzofuran group, indole group, indene group, benzosilol group, benzoborole group, benzophospol group, benzo Selenophene group, benzozermole group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilol group, dibenzoborole group, dibenzophosphole group, dibenzoselenophene group, dibenzozermole group, Dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, Azabenzosilol group, azabenzoborole group, azabenzophospol group, azabenzoselenophene group, azabenzozermole group, azadibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group, Azadibenzosilol group, azadibenzoborole group, azadibenzophospol group, azadibenzoselenophene group, azadibenzozermole group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9 -One group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenane Troline group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzo Imidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline (5,6,7,8-tetrahydroisoquinoline) group , 5,6,7,8-tetrahydroquinoline (5,6,7,8-tetrahydroquinoline) group, and the like.

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

Examples of C ₁ -C ₆₀ alkyl group, C ₁ -C ₂₀ alkyl group and/or C ₁ -C ₁₀ alkyl group in the present specification include methyl group, ethyl group, n -propyl group, isopropyl group, n -butyl group, sec -butyl group , Isobutyl group, tert -butyl group, n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, n -hexyl group, iso Hexyl group, sec -hexyl group, tert -hexyl group, n -heptyl group, isoheptyl group, sec -heptyl group, tert -heptyl group, n -octyl group, isooctyl group, sec -octyl group, tert -octyl group, Substituted or unsubstituted with n -nonyl group, isononyl group, sec -nonyl group, tert -nonyl group, n -decyl group, isodecyl group, sec -decyl group, tert -decyl group, or any combination thereof, Methyl group, ethyl group, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec - pentyl, 3-pentyl group, sec - iso-pentyl group, n - hexyl group, iso-hexyl, sec - hexyl group, a tert - hexyl, n - heptyl, iso-heptyl, sec - heptyl group, tert -Heptyl group, n -octyl group, isooctyl group, sec -octyl group, tert -octyl group, n -nonyl group, isononyl group, sec -nonyl group, tert -nonyl group, n -decyl group, isodecyl group, sec -decyl group or tert -decyl group, etc. may be included. For example, Formula 9-33 is a branched C ₆ alkyl group, which can be seen as a tert-butyl group substituted with two methyl groups.

In the present specification, the C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the formula -OA ₁₀₁ (wherein A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, Isopropyloxy group, etc. are contained.

Examples of the C ₁ -C ₆₀ alkoxy group, C ₁ -C ₂₀ alkoxy group, or C ₁ -C ₁₀ alkoxy group in the present specification may include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and the like.

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

In the present specification, examples of the C ₃ -C ₁₀ cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, and a bicyclo[1.1. 1] pentyl group (bicyclo[1.1.1]pentyl), bicyclo[2.1.1] hexyl group (bicyclo[2.1.1]hexyl), bicyclo[2.2.1]heptyl group (bicyclo[2.2.1]heptyl ) (Norbornanyl), bicyclo[2.2.2]octyl group, etc. may be included.

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

Examples of the C ₁ -C ₁₀ heterocycloalkyl group in the present specification include siloranyl, silinanyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydro-2H-pyranyl. ), tetrahydrothiophenyl group, etc. may be included.

In the present specification, "deuterium-containing C ₁ -C ₆₀ alkyl group (or deuterium-containing C ₁ -C ₂₀ alkyl group, deuterium-containing C ₂ -C ₂₀ alkyl group, etc.)" means C ₁ -substituted with at least one deuterium It means a C ₆₀ alkyl group (or a C ₁ -C ₂₀ alkyl group substituted with at least one deuterium, C ₂ -C ₂₀ alkyl substituted with at least one deuterium, etc.). For example, "deuterium-containing C ₁ alkyl group (ie, deuterium-containing methyl group)" includes -CD ₃ , -CD ₂ H and -CDH ₂ .

In the present specification, "deuterium-containing C ₃ -C ₁₀ cycloalkyl group" refers to a C ₃ -C ₁₀ cycloalkyl group substituted with at least one deuterium. Examples of the "deuterium-containing C ₃ -C ₁₀ cycloalkyl group" may refer to, for example, Formula 10-501.

In the present specification, "fluorinated C ₁ -C ₆₀ alkyl group (or fluorinated C ₁ -C ₂₀ alkyl group, etc.)", "fluorinated C ₃ -C ₁₀ cycloalkyl group", "fluorinated C ₁ -C ₁₀ heterocycloalkyl group" And "fluorinated phenyl group" is each substituted with at least one fluoro group (-F), C ₁ -C ₆₀ alkyl group (or, C ₁ -C ₂₀ alkyl group, etc.), C ₃ -C ₁₀ cycloalkyl group, C _1- It means a C ₁₀ heterocycloalkyl group and a phenyl group. For example, "fluorinated C ₁ alkyl group (ie, fluorinated methyl group)" includes -CF ₃ , -CF ₂ H and -CFH ₂ . The "fluorinated C ₁ -C ₆₀ alkyl group (or fluorinated C ₁ -C ₂₀ alkyl group, etc.)", "fluorinated C ₃ -C ₁₀ cycloalkyl group", or "fluorinated C ₁ -C ₁₀ heterocycloalkyl group" is , i) a fully fluorinated C ₁ -C ₆₀ alkyl group (or fully fluorinated C ₁ -C ₂₀ alkyl group, etc.), in which all hydrogens in each group are substituted with fluoro groups, fully fluorinated C _3- C ₁₀ cycloalkyl group, or fully fluorinated C ₁ -C ₁₀ heterocycloalkyl group, or ii) partially fluorinated C ₁ -C _{60 in} which all hydrogens in each group are not substituted with fluoro groups It may be an alkyl group (or a partially fluorinated C ₁ -C ₂₀ alkyl group, etc.), a partially fluorinated C ₃ -C ₁₀ cycloalkyl group, or a partially fluorinated C ₁ -C ₁₀ heterocycloalkyl group.

In the present specification, the "(C ₁ -C ₂₀ alkyl)'X'group" refers to a'X' group substituted with at least one C ₁ -C ₂₀ alkyl group. For example, in the present specification, "(C ₁ -C ₂₀ alkyl)C ₃ -C ₁₀ cycloalkyl group" refers to a C ₃ -C ₁₀ cycloalkyl group substituted with at least one C ₁ -C ₂₀ alkyl group, and "(C ₁ -C ₂₀ alkyl)phenyl group" refers to a phenyl group substituted with at least one C ₁ -C ₂₀ alkyl group. An example of a (C ₁ alkyl) phenyl group is a toluyl group.

In the present specification, "azaindole group, azabenzoborole group, azabenzophospol group, azaindene group, azabenzosilol group, azabenzozermole group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group , Azacarbazole group, azadibenzoborole group, azadibenzophospol group, azafluorene group, azadibenzosilol group, azadibenzozermole group, azadibenzothiophene group, azadibenzoselenophene group, Azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, respectively, "indole group, benzoborole group , Benzophosphole group, indene group, benzosilol group, benzozermole group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, Dibenzosilol group, dibenzo low mole group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene It has the same backbone as "5,5-dioxide group", but at least one of carbons forming the ring thereof is substituted with nitrogen, meaning a heterocycle.

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

In the present specification, the C ₂ -C ₆₀ alkynyl group has a structure including one or more carbon-carbon triple bonds in the middle or terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group and a propynyl group ( propynyl), etc. In the present specification, the C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

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

In the present specification, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom, and Has at least one double bond within. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

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

The C ₇ -C ₆₀ alkylaryl group herein means a group of the C ₆ -C ₆₀ aryl substituted with at least one C ₁ -C ₆₀ alkyl group.

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

In the present specification, a C ₂ -C ₆₀ alkylheteroaryl group refers to a C ₁ -C ₆₀ heteroaryl group substituted with at least one C ₁ -C ₆₀ alkyl group.

In the specification C ₆ -C ₆₀ aryloxy group -OA, point ₁₀₂ (where, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), a C ₆ -C ₆₀ arylthio group (arylthio) is -SA ₁₀₃ (where , A ₁₀₃ represents the C ₆ -C ₆₀ aryl group).

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

In the present specification, in the monovalent non-aromatic condensed heteropolycyclic group, two or more rings are condensed with each other, and a hetero atom selected from N, O, P, Si, and S in addition to carbon as a ring forming atom Includes, and refers to a monovalent group (eg, having a carbon number of 1 to 60) in which the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group and the like. In the present specification, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

In the present specification, a substituted C ₅ -C ₃₀ carbocyclic group, a substituted C ₂ -C ₃₀ heterocyclic group, a substituted C ₁ -C ₆₀ alkyl group, a substituted C ₂ -C ₆₀ alkenyl group, a substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₇ -C ₆₀ alkylaryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ aryl Thi group, a substituted C ₁ -C ₆₀ heteroaryl group, a substituted C ₂ -C ₆₀ alkylheteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic heterocondensed polycyclic group Is,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group Or a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si (Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )( Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -substituted by any combination thereof C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group , C ₁ -C ₆₀ alkoxy group, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, 1 Is a non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ ) (Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ), or any Substituted or unsubstituted in combination, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent A non-aromatic condensed polycyclic group or a monovalent non-aromatic condensed heteropolycyclic group;

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ), or -P(Q ₃₈ )(Q ₃₉ ); or

Any combination thereof;

Can be

In the present specification, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; Hydroxyl group; Cyano group; Nitro group; Amidino group; Hydrazine; Hydrazone group; A carboxylic acid group or a salt thereof; Sulfonic acid groups or salts thereof; Phosphoric acid groups or salts thereof; Deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or substituted by any combination thereof or unsubstituted 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; Deuterium, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or a C ₆ -C ₆₀ aryl group unsubstituted or substituted with any combination thereof; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; Monovalent non-aromatic condensed polycyclic group; Or a monovalent non-aromatic condensed heteropolycyclic group; may be.

For example, in the present specification, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H , -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -CD ₂ CDH ₂ ; or

Substituted or unsubstituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, or any combination thereof, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group , n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, phenyl group, biphenyl group or naphthyl group;

Can be

The composition including the first compound and the second compound may be suitable for use as an organic layer of an organic light-emitting device, for example, as a material for a light-emitting layer among the organic layers. A second electrode; And an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the composition.

The organic light emitting device may have a low driving voltage, high external quantum efficiency, and a long lifespan by including a composition including the first compound and the second compound as described above.

The composition may be used between a pair of electrodes of an organic light emitting device. For example, the composition may be included in the emission layer of the organic light emitting device. In this case, the first compound may serve as a dopant, and the second compound may serve as a host. For example, the content of the second compound may be greater than the content of the first compound. The emission layer may emit red light, for example, red light having a maximum emission wavelength in the range of 550 nm or more (eg, 550 nm or more and 900 nm or less).

The first electrode is an anode that is a hole injection electrode, the second electrode is a cathode that is an electron injection electrode, or the first electrode is a cathode that is an electron injection electrode, and the second electrode is an anode that is a hole injection electrode.

For example, of the organic light emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer is a hole transport region disposed between the first electrode and the emission layer, and the emission layer and the second electrode Further comprising an electron transport region disposed therebetween, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region is a hole blocking layer, an electron Transport layers, electron injection layers, or any combination thereof.

In the present specification, the term "organic layer" refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of the organic light emitting device. The "organic layer" may include not only an organic compound, but also an organometallic complex including a metal.

1 schematically shows a cross-sectional view of an organic light-emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a method of manufacturing an organic light-emitting device according to an embodiment of the present invention will be described with reference to FIG. 1. The organic light-emitting device 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are sequentially stacked.

A substrate may be additionally disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a typical organic light emitting device may be used, and a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling and waterproofness may be used.

The first electrode 11 may be formed, for example, by providing a material for the first electrode on the substrate by using a vapor deposition method or a sputtering method. The first electrode 11 may be an anode. The material for the first electrode may be selected from materials having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a transflective electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), and the like may be used. Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) may be used. .

The first electrode 11 may have a single layer or a multilayer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO/Ag/ITO, but is not limited thereto.

An organic layer 15 is disposed on the first electrode 11.

The organic layer 15 includes a hole transport region; An emission layer; And an electron transport region.

The hole transport region may be disposed between the first electrode 11 and the emission layer.

The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

The hole transport region may include only a hole injection layer or only a hole transport layer. Alternatively, the hole transport region may have a structure of a hole injection layer/hole transport layer or a hole injection layer/hole transport layer/electron blocking layer sequentially stacked from the first electrode 11.

When the hole transport region includes a hole injection layer, the hole injection layer HIL may be formed on the first electrode 11 by using various methods such as a vacuum deposition method, a spin coating method, a cast method, and an LB method. have.

When the hole injection layer is formed by vacuum evaporation, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal properties of the target hole injection layer, etc., but, for example, the deposition temperature is about 100 to about 500 ℃, the degree of vacuum of about 10 ^-8 to about ¹⁰ can be selected in the range of ³ torr, a deposition rate of about 0.01 to about 100Å / sec, but is not limited to such.

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

Conditions for forming the hole transport layer and the electron blocking layer refer to conditions for forming the hole injection layer.

The hole transport region is, for example, 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: polyaniline/dodecylbenzenesulfonic acid), PEDOT/PSS(Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate):poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)), Pani/CSA (Polyaniline/Camphor sulfonic acid) :Polyaniline/camphorsulfonic acid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), a compound represented by the following Formula 201, a compound represented by the following Formula 202, Or any combination thereof:

<Formula 201>

<Formula 202>

In Formula 201, Ar ₁₀₁ and Ar ₁₀₂ are each independently deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group , Carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl 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, or any combination thereof substituted or unsubstituted , Phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenalenylene group, phenanthrenylene group, anthracenylene group, fluorane It may be a tenylene group, a triphenylenylene group, a pyrenylene group, a cryenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group.

In Formula 201, xa and xb may each independently be an integer of 0 to 5, or 0, 1, or 2. For example, xa may be 1 and xb may be 0, but the present invention is not limited thereto.

In Formulas 201 and 202, R ₁₀₁ to R ₁₀₈ , R ₁₁₁ to R ₁₁₉ and R ₁₂₁ to R ₁₂₄ are independently of each other,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, Phosphoric acid or its salt, C ₁ -C ₁₀ alkyl group (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.) or C ₁ -C ₁₀ alkoxy group (e.g., methoxy group, ethoxy group, etc. Group, propoxy group, butoxy group, pentoxy group, etc.);

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, and phosphoric acid or A salt thereof, or a C ₁ -C ₁₀ alkyl group or a C ₁ -C ₁₀ alkoxy group unsubstituted or substituted by any combination thereof; or

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or A salt thereof, a C ₁ -C ₁₀ alkyl group, a C ₁ -C ₁₀ alkoxy group, or a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group or a pyrenyl group, which is unsubstituted or substituted with any combination thereof;

Can be

In Formula 201, R ₁₀₉ is deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or its Unsubstituted or substituted with a salt, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyridinyl group, or any combination thereof It may be a phenyl group, a naphthyl group, an anthracenyl group or a pyridinyl group.

According to an embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A:

<Formula 201A>

In Formula 201A, for a detailed description of R ₁₀₁ , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ , refer to the above.

For example, the hole transport region may include one of the following compounds HT1 to HT20, or any combination thereof:

The thickness of the hole transport region may be about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. If the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, the thickness of the hole injection layer is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, and the hole The thickness of the transport layer may be about 50 Å to about 2000 Å, for example, about 100 Å to about 1500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above-described ranges, satisfactory hole transport characteristics may be obtained without a substantial increase in driving voltage.

In addition to the above-described materials, 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 in the hole transport region.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof, but is not limited thereto. For example, the p-dopant is tetracyanoquinonedimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ) , Quinone derivatives such as F6-TCNNQ; Metal oxides such as tungsten oxide and molybdenum oxide; Cyano group-containing compounds such as the following compound HT-D1; Or any combination thereof.

The hole transport region may further include a buffer layer.

The buffer layer may serve to increase efficiency by compensating for an optical resonance distance according to a wavelength of light emitted from the emission layer.

Meanwhile, when the hole transport region includes an electron blocking layer, the electron blocking layer material may include a material that can be used for the hole transport region as described above, a host material to be described later, or any combination thereof. . For example, when the hole transport region includes an electron blocking layer, mCP to be described later may be used as the electron blocking layer material.

An emission layer EML may be formed on the hole transport region by using a method such as a vacuum deposition method, a spin coating method, a cast method, or an LB method. In the case of forming the light emitting layer by the vacuum evaporation method and the spin coating method, the evaporation conditions and coating conditions vary depending on the compound to be used, but may generally be selected from a range of conditions substantially the same as the formation of the hole injection layer.

The light emitting layer may include a composition including the first compound and the second compound as described herein.

According to another embodiment, the emission layer may include a host and a dopant, the dopant may include the first compound, and the host may include the second compound.

Meanwhile, the emission layer may further include an arbitrary dopant and/or host in addition to the composition described herein.

When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned as a red emission layer, a green emission layer, and/or a blue emission layer. Alternatively, the emission layer may have a structure in which a red emission layer, a green emission layer, and/or a blue emission layer are stacked, and thus various modifications such as the ability to emit white light are possible.

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

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

Next, an electron transport region is disposed on the emission layer.

The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

For example, the electron transport region may have a structure of a hole blocking layer/electron transport layer/electron injection layer or an electron transport layer/electron injection layer, but is not limited thereto. The electron transport layer may have a single layer or a multilayer structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer in the electron transport region refer to the conditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and Balq below.

Alternatively, the hole blocking layer may include the host, an electron transport layer material, an electron injection layer material, or any combination thereof.

The hole blocking layer may have a thickness of about 20 Å to about 1000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer satisfies the above-described range, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may include the BCP, Bphen, TPBi, Alq ₃ , Balq, TAZ, NTAZ, or any combination thereof:

Alternatively, the electron transport layer may include at least one of the following compounds ET1 to ET25.

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

In addition to the above-described materials, the electron transport layer may further include a metal-containing material.

The metal-containing material may include a Li complex. The Li complex may include, for example, the following compounds ET-D1 or ET-D2.

In addition, the electron transport region may include an electron injection layer EIL that facilitates injection of electrons from the second electrode 19.

The electron injection layer may include LiF, NaCl, CsF, Li ₂ O, BaO, or any combination thereof.

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

A second electrode 19 is provided on the organic layer 15. The second electrode 19 may be a cathode. As the material for the second electrode 19, a metal, an alloy, an electrically conductive compound, and combinations thereof having a relatively low work function may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). It can be used as a material for forming the second electrode 19. Alternatively, in order to obtain a top light emitting device, various modifications are possible, such as being able to form the second transmissive electrode 19 using ITO or IZO.

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

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

In the present specification, the C ₁ -C ₆₀ alkoxy group refers to a monovalent group having the formula -OA ₁₀₁ (wherein A ₁₀₁ is the C ₁ -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, Isopropyloxy group, etc. are contained.

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

In the present specification, the C ₂ -C ₆₀ alkynyl group has a structure including one or more carbon-carbon triple bonds in the middle or terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethynyl group and a propynyl group ( propynyl), etc. In the present specification, the C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

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

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

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

In the present specification, the C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms including at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom, and Has at least one double bond within. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. In the present specification, the C ₁ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkenyl group.

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

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

In the specification C ₆ -C ₆₀ aryloxy group -OA, point ₁₀₂ (where, A ₁₀₂ is the C ₆ -C ₆₀ aryl group), a C ₆ -C ₆₀ arylthio group (arylthio) is -SA ₁₀₃ (where , A ₁₀₃ represents the C ₆ -C ₆₀ aryl group).

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

In the present specification, in the monovalent non-aromatic condensed heteropolycyclic group, two or more rings are condensed with each other, and a hetero atom selected from N, O, P, Si, and S in addition to carbon as a ring forming atom Includes, and refers to a monovalent group (eg, having a carbon number of 1 to 60) in which the entire molecule has non-aromaticity. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group and the like. In the present specification, a divalent non-aromatic condensed heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

In the present specification, a C ₅ -C ₆₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 60 carbons as ring forming atoms. The C ₅ -C ₆₀ carbocyclic group may be a monocyclic group or a polycyclic group.

In the present specification, the C ₁ -C ₆₀ heterocyclic group refers to a saturated or unsaturated cyclic group having at least one hetero atom selected from N, O, P, Si, and S in addition to 1 to 60 carbons as ring forming atoms. The C ₁ -C ₆₀ heterocyclic group may be a monocyclic group or a polycyclic group.

In the present specification, the C ₁ -C ₆₀ cyclic group may include both a C ₅ -C ₆₀ carbocyclic group and a C ₁ -C ₆₀ heterocyclic group as described above.

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

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group Or a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si (Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )( Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group or C ₁ -substituted by any combination thereof C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group , C ₁ -C ₆₀ alkoxy group, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, 1 Is a non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ ) (Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ), or any Substituted or unsubstituted in combination, 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 ₇ -C ₆₀ alkylaryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, C ₂ -C ₆₀ alkylheteroaryl group, monovalent A non-aromatic condensed polycyclic group or a monovalent non-aromatic condensed heteropolycyclic group;

-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ), or -P(Q ₃₈ )(Q ₃₉ ); or

Any combination thereof;

Can be

In the present specification, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; Hydroxyl group; Cyano group; Nitro group; Amidino group; Hydrazine; Hydrazone group; A carboxylic acid group or a salt thereof; Sulfonic acid groups or salts thereof; Phosphoric acid groups or salts thereof; Deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or substituted by any combination thereof or unsubstituted 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; Deuterium, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or a C ₆ -C ₆₀ aryl group unsubstituted or substituted with any combination thereof; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; Monovalent non-aromatic condensed polycyclic group; Or a monovalent non-aromatic condensed heteropolycyclic group; may be.

For example, in the present specification, Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are independently of each other,

-CH ₃ , -CD ₃ , -CD ₂ H, -CDH ₂ , -CH ₂ CH ₃ , -CH ₂ CD ₃ , -CH ₂ CD ₂ H, -CH ₂ CDH ₂ , -CHDCH ₃ , -CHDCD ₂ H , -CHDCDH ₂ , -CHDCD ₃ , -CD ₂ CD ₃ , -CD ₂ CD ₂ H or -CD ₂ CDH ₂ ; or

Substituted or unsubstituted with deuterium, C ₁ -C ₁₀ alkyl group, phenyl group, or any combination thereof, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group , n -pentyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, phenyl group, biphenyl group or naphthyl group;

Can be

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

[Example]

Synthesis example 1 (compound 3)

Synthesis of Intermediate L3-2

2-chloro-4-iodonicotinaldehyde 2.5 g (9.3 mmol) was mixed with tetrahydrofuran 100 ml and water 30 ml, Pd(PPh ₃ ) ₄ 0.53 g (0.46 mmol), 3-Fluorophenylboronic acid 1.3 g (9.3 mmol) And K ₂ CO ₃ 3.2 g (23.0 mmol) was added and heated to reflux at 80° C. for 24 hours. When the reaction was completed, the reaction mixture was concentrated under reduced pressure, and the organic layer obtained by extraction with dichloromethane and water was dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography to obtain 1.1 g of intermediate L3-2 (yield 51 %) was obtained.

LCMS: m/z calcd for C ₁₂ H ₇ ClFNO 235.02; Found 236.06.

Synthesis of Intermediate L3-1

After adding 5.8 g (17.0 mmol) of (methoxymethyl)triphenylphosphonium chloride and 1.6 g (6.8 mmol) of intermediate L3-2 to 50 ml of tetrahydrofuran, 17 ml of 1.0M potassium tert- butoxide solution was slowly added dropwise at room temperature for 24 hours. Stirred. When the reaction was completed, water and ethyl acetate were added thereto for extraction, and the obtained organic layer was dried over magnesium sulfate and distilled under reduced pressure. The resultant obtained therefrom was dried under reduced pressure, mixed with 40 ml of dichloromethane, and 1.5 ml of methanolic acid was slowly added dropwise at room temperature, followed by stirring at room temperature for about 12 hours. When the reaction was completed, the organic layer obtained by extraction with a saturated aqueous sodium hydrogen carbonate solution was dried over magnesium sulfate, distilled under reduced pressure, and then purified by column chromatography to give 1.1 g (yield 72%) of intermediate L3-1.

LCMS: m/z calcd for C ₁₃ H ₇ ClFN 231.03; Found 231.98.

Synthesis of Intermediate L3

Intermediate L3-1 0.7 g (3.0 mmol) was mixed with 30 ml of THF and 10 ml of water, 0.5 g (3.6 mmol) of 3,5-Dimethylphenylboronic acid, 0.24 g (0.2 mmol) of Pd(PPh ₃ ) ₄ and K ₂ CO ₃ After adding 1.0 g (7.5 mmol), it was heated to reflux for one day. When the reaction was completed, ethyl acetate and water were added to the organic layer obtained by extraction, dried over magnesium sulfate, distilled under reduced pressure, and purified by column chromatography to give 0.72 g (yield 80%) of intermediate L3.

LCMS: m/z calcd for C ₂₁ H ₁₆ FN 301.13; Found 302.05.

Synthesis of Intermediate L3 Dimer

Intermediate L3 1.05g (3.4 mmol) and iridium chloride 0.6g (1.6 mmol) were mixed with 40 mL of ethoxyethanol and 15 mL of distilled water, followed by heating to reflux for 24 hours. When the reaction was completed, the temperature was lowered to room temperature, the resulting solid was filtered and washed thoroughly with water/methanol/hexane. The obtained solid was dried in a vacuum oven to obtain 1.0 g of an intermediate L3 dimer.

Synthesis of compound 3

Intermediate L3 Dimer 1.0g (0.63 mmol), 3,7-diethylnonane-4,6-dione 0.96g (4.5 mmol) and Na ₂ CO ₃ 0.48g (4.5 mmol) mixed with ethoxyethanol 40 mL , The reaction was carried out by stirring at 90° C. for 24 hours. When the reaction was completed, the temperature was lowered to room temperature, the resulting solid was filtered and purified by liquid chromatography to obtain 0.8 g (yield 65%) of compound 3.

LCMS: m/z calcd for C ₅₅ H ₅₃ F ₂ IrN ₂ O ₂ , 1004.37; Found 1005.25.

Synthesis example 2 ( Compound 9)

Synthesis of Intermediate L9

Intermediate L9 was synthesized using the same method as the synthesis of intermediate L3 of Synthesis Example 1, except that the intermediate L9-1 was used instead of the intermediate L3-1.

LC-MS m/z = 303 (M+H) ⁺

Synthesis of Intermediate L9 Dimer

The intermediate L9 dimer was synthesized using the same method as the synthesis method of the intermediate L3 dimer of Synthesis Example 1, except that the intermediate L9 was used instead of the intermediate L3.

Synthesis of compound 9

Synthesis Example 1, except that the intermediate L9 Dimer and 3,7-diethyl-3,7-dimethylnonane-4,6-dione were used instead of the intermediate L3 Dimer and 3,7-diethylnonane-4,6-dione. Compound 9 was synthesized using the same method as for the synthesis method of compound 3.

LC-MS m/z = 1035 (M+H) ⁺

Synthesis example 3 ( Compound 10)

Synthesis of Intermediate L10

Intermediate L10 was synthesized using the same method as the synthesis method of intermediate L3 of Synthesis Example 1, except that intermediate L10-1 was used instead of intermediate L3-1.

LCMS: m/z calcd for C ₂₂ H ₁₆ F ₃ N 351.36; Found 352.21.

Synthesis of Intermediate L10 Dimer

The intermediate L10 dimer was synthesized using the same method as the synthesis method of the intermediate L3 dimer of Synthesis Example 1, except that the intermediate L10 was used instead of the intermediate L3.

Of compound 10 synthesis

Compound 10 was synthesized using the same method as the synthesis method of compound 3 of Synthesis Example 1, except that the intermediate L10 dimer was used instead of the intermediate L3 dimer.

LCMS: m/z calcd for C ₅₇ H ₅₃ F ₆ IrN ₂ O ₂ 1104.35; Found 1105.40.

Example One

As an anode, a glass substrate on which ITO/Ag/ITO was deposited to a thickness of 70/1000/70Å was cut into a size of 50mm x 50mm x 0.5mm and ultrasonically cleaned for 5 minutes each using isopropyl alcohol and pure water, followed by UV light for 30 minutes. Was irradiated, washed by exposure to ozone, and installed in a vacuum evaporation apparatus.

2-TNATA was vacuum-deposited on the anode to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl on the hole injection layer (Hereinafter, NPB) was vacuum deposited to form a hole transport layer having a thickness of 1350 Å.

Subsequently, compound H2 (host) and compound 3 (dopant) were co-deposited at a weight ratio of 98:2 on the hole transport layer to form a light emitting layer having a thickness of 400Å.

Thereafter, BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, and then Alq ₃ was vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 350 Å. LiF is vacuum-deposited to form an electron injection layer having a thickness of 10 Å, and Mg and Ag are co-deposited on the electron injection layer at a weight ratio of 90:10 to form a cathode having a thickness of 120 Å, thereby forming an organic light-emitting device (red light emission). Was produced.

Example 2 to 6 and Comparative example 1 to 3

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds shown in Tables 1 and 2 were used instead of Compound H2 and Compound 3 as a host and a dopant when forming the emission layer.

Evaluation example 1: Evaluation of characteristics of organic light emitting devices

For each of the organic light emitting devices manufactured in Examples 1 to 6 and Comparative Examples 1 to 3, the driving voltage, current density, maximum external quantum efficiency (Max EQE), half width of the EL spectrum, luminous color, color coordinates, and lifetime (LT ₉₇ ) was evaluated and the results are shown in Tables 1 and 2, respectively. As an evaluation device, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used, and the lifetime (LT ₉₇ ) (at 3500nit) was evaluated for the time taken to achieve a luminance of 97% compared to 100% of the initial luminance. Life span (LT ₉₇ ) was expressed as a relative value (%).

Host compound
No. Dopant compound
No. Driving
Voltage
(V) electric current
density
(㎃/㎠) Max EQE
(%) Half width
(nm) Luminous color Color coordinates
(CIEx) LT ₉₇
(Relative value, %) Example 1 H2 3 4.45 10.7 31.5 50.9 Red 0.665, 0.332 162 Example 2 H2 9 4.8 12.2 30.8 51.6 Red 0.679, 0.32 145 Example 3 H2 10 5.02 14.5 30.0 54.5 Red 0.673, 0.323 109 Comparative Example 1 H2 A 5.4 16.2 29.1 51.4 Red 0.677, 0.32 100 Comparative Example 2 H2 B 4.8 10.2 27.8 60.0 Red 0.647, 0.650 60

Host compound
No. Dopant compound
No. Driving
Voltage
(V) electric current
density
(㎃/㎠) Max EQE
(%) Half width
(nm) Luminous color Color coordinates
(CIEx) LT ₉₇
(Relative value, %) Example 4 H12 3 3.9 11.3 29.8 50.7 Red 0.667, 0.332 162 Example 5 H12 9 4.2 12.7 29.7 51 Red 0.680, 0.320 144 Example 6 H12 10 4.38 15.0 29 53.5 Red 0.674, 0.323 116 Comparative Example 3 H12 A 4.6 16.9 27.1 55.8 Red 0.678, 0.320 100

From Table 1, it can be seen that the organic light-emitting devices of Examples 1 to 3 have improved or equivalent driving voltage, improved external quantum efficiency, and improved lifetime characteristics compared to the organic light-emitting devices of Comparative Examples 1 and 2. From Table 2, it can be seen that the organic light emitting devices of Examples 4 to 6 have improved driving voltage, improved external quantum efficiency, and improved lifetime characteristics compared to the organic light emitting device of Comparative Example 3.

10: organic light emitting device
11: first electrode
15: organic layer
19: second electrode

Claims (20)

Including the first compound and the second compound,
The first compound includes a compound represented by Formula 1 below,
The second compound is a composition comprising a compound represented by Formula 2 below:
<Formula 1>

<Formula 2>

Y ₂ in Formula 1 is C,
Ring CY ₁₂ in Formula 1 is a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group,
Formula 2 of Ar ₁ is a substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or optionally substituted with at least one R ₆₁ or unsubstituted C ₁ -C ₆₀ heterocyclic group with at least one R _61,
Ar ₂ in Formula 2 is a π electron deficient nitrogen-containing C ₁ -C ₆₀ cyclic group unsubstituted or substituted with at least one R ₆₂ ,
Formula 2 of the Ar ₅ is a single bond or, when substituted or unsubstituted C ₅ -C ₆₀ carbonyl to at least one of R ₆₅ or optionally substituted cyclic group with at least one R ₆₅ or unsubstituted C ₁ -C ₆₀ heterocyclic Is a click group or does not exist,
In Formula 2, n is 1, 2 or 3, and when n is 1, Ar ₅ does not exist,
In Formula 2, a1 and a2 are each independently an integer of 0 to 5, but the sum of a1 and a2 is 1 or more,
In Formula 2, ring CY ₂ and ring CY ₃ are each independently a C ₅ -C ₆₀ carbocyclic group or a C ₁ -C ₆₀ heterocyclic group, and ring CY ₂ and ring CY ₃ are optionally, at least one Of R ₆₆ substituted or unsubstituted C ₅ -C ₆₀ carbocyclic group or at least one R ₆₆ substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group may be bonded to each other through the interposed,
In Formulas 1 and 2, R ₁ to R ₈ , A ₂₀ , A ₁ to A ₇ , R ₂₀ , R ₃₀ , R ₆₁ , R ₆₂ , R ₆₅ and R ₆₆ are independently of each other, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or A salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, a substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, a substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, substituted or unsubstituted C ₆ -C ₆₀ arylthio group , A substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ ) (Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -Ge(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ), -P(= O)(Q ₈ )(Q ₉ ) or -P(Q ₈ )(Q ₉ ),
In Formula 2, b2 and b3 are each independently an integer of 0 to 20, when b2 is 2 or more, two or more R ₂₀ are the same as or different from each other, and when b3 is 2 or more, two or more R ₃₀ are the same or different from each other, ,
In Formula 1, d2 is an integer of 0 to 10, and when d2 is 2 or more, 2 or more A ₂₀ are the same as or different from each other,
At least one of R ₁ to R ₈ and A ₂₀ in Formula 1 includes at least one fluoro group (-F),
Two or more of R ₁ to R ₈ and A ₂₀ in Formula 1 are optionally combined with each other, and substituted or unsubstituted with at least one R _1a C ₅ -C ₆₀ carbocyclic group or at least one R _1a may form a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,
Two or more of A ₁ to A ₇ in Formula 1 are optionally bonded to each other to be substituted or unsubstituted with at least one R _1a C ₅ -C ₆₀ carbocyclic group or at least one R _1a May form a cyclic C ₁ -C ₆₀ heterocyclic group,
Two or more of the ring CY ₂ , the ring CY ₃ , R ₂₀ and R ₃₀ of Formula 2 are optionally bonded to each other and substituted or unsubstituted with at least one R _1a C ₅ -C ₆₀ carbocyclic group or at least One R _1a may form a substituted or unsubstituted C ₁ -C ₆₀ heterocyclic group,
For a description of R _1a , refer to the description of A ₇ ,
The substituted C ₁ -C ₆₀ alkyl group, substituted C ₂ -C ₆₀ alkenyl group, substituted C ₂ -C ₆₀ alkynyl group, substituted C ₁ -C ₆₀ alkoxy group, substituted C ₃ -C ₁₀ cycloalkyl group, Substituted C ₁ -C ₁₀ heterocycloalkyl group, substituted C ₃ -C ₁₀ cycloalkenyl group, substituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted C ₆ -C ₆₀ aryl group, substituted C ₆ -C ₆₀ aryloxy group, substituted C ₆ -C ₆₀ arylthio group, substituted C ₁ -C ₆₀ heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic heterocondensed polycyclic group The substituent is,
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alky A nil group or a C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, Monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁₁ )(Q ₁₂ ), -Si(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -Ge(Q ₁₃ )(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), -P(=O)(Q ₁₈ )(Q ₁₉ ), -P(Q ₁₈ )(Q ₁₉ ), or any thereof A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group or a C ₁ -C ₆₀ alkoxy group substituted by a combination of;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, Amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alky Nyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocyclic condensed polycyclic group, -N(Q ₂₁ )(Q ₂₂ ), -Si(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -Ge(Q ₂₃ )(Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), -P(=O)(Q ₂₈ )(Q ₂₉ ), -P(Q ₂₈ )(Q ₂₉ ) or any combination thereof substituted or unsubstituted with at least one, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ aryl A thi group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;
-N(Q ₃₁ )(Q ₃₂ ), -Si(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -Ge(Q ₃₃ )(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ), -P(=O)(Q ₃₈ )(Q ₃₉ ) or -P(Q ₃₈ )(Q ₃₉ ); or
Any combination thereof;
ego,
The Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen; heavy hydrogen; -F; -Cl; -Br; -I; Hydroxyl group; Cyano group; Nitro group; Amidino group; Hydrazine; Hydrazone group; A carboxylic acid group or a salt thereof; Sulfonic acid groups or salts thereof; Phosphoric acid groups or salts thereof; Deuterium, C ₁ -C ₆₀ alkyl, C ₆ -C ₆₀ aryl group, or substituted by any combination thereof or unsubstituted 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; Deuterium, a C ₁ -C ₆₀ alkyl group, a C ₆ -C ₆₀ aryl group, or a C ₆ -C ₆₀ aryl group unsubstituted or substituted with any combination thereof; C ₆ -C ₆₀ aryloxy group; C ₆ -C ₆₀ arylthio group; C ₁ -C ₆₀ heteroaryl group; Monovalent non-aromatic condensed polycyclic group; Or a monovalent non-aromatic condensed heteropolycyclic group; The method of claim 1,
Ring CY ₁₂ in Formula 1 is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene (1,2,3,4-tetrahydronaphthalene) group, a thiophene group, a furan group, a pyrrole group, and a cyclo Pentadiene group, silol group, benzothiophene group, benzofuran group, indole group, indene group, benzosilol group, dibenzothiophene group, dibenzofuran group, carbazole group, fluorene group, or dibenzosilol group Phosphorus, composition. The method of claim 1,
In Formula 1, R ₁ to R ₈ and A ₁ to A ₇ are independently of each other,
Hydrogen, deuterium, or -F;
Deuterium, -F, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, a phenyl group, or a C ₁ -C ₂₀ alkyl group unsubstituted or substituted with any combination thereof, A C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or a phenyl group; or
-Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );
ego,
A ₂₀ in Formula 1 is,
Hydrogen, or deuterium;
Deuterium, C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, phenyl group, or any combination thereof substituted or unsubstituted, C ₁ -C ₂₀ alkyl group, C _3- A C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, or a phenyl group; or
-Si(Q ₃ )(Q ₄ )(Q ₅ ), or -Ge(Q ₃ )(Q ₄ )(Q ₅ );
Phosphorus, composition. The method of claim 1,
At least one of R ₁ to R ₈ in Formula 1 is independently of each other,
Fluoro group (-F); or
A fluorinated C ₁ -C ₂₀ alkyl group substituted or unsubstituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a phenyl group, or any combination thereof , A fluorinated C ₃ -C ₁₀ cycloalkyl group, a fluorinated C ₁ -C ₁₀ heterocycloalkyl group, or a fluorinated phenyl group;
Phosphorus, composition. The method of claim 1,
At least one of A ₁ to A ₆ in Formula 1 is independently of each other, a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group. The method of claim 1,
In Formula 1, A ₁ to A ₆ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted or unsubstituted C ₁ -C ₁₀ The composition, which is a heterocycloalkyl group. The method of claim 1,
In Formula 1

A composition wherein the group represented by is a group represented by one of the following formulas CY1 to CY108:

In the above formulas CY1 to CY108
T ₂ to T ₈ are independently of each other,
Fluoro group (-F); or
A fluorinated C ₁ -C ₂₀ alkyl group substituted or unsubstituted with deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, a phenyl group, or any combination thereof , A fluorinated C ₃ -C ₁₀ cycloalkyl group, a fluorinated C ₁ -C ₁₀ heterocycloalkyl group, or a fluorinated phenyl group;
ego,
For the description of R ₂ to R ₈ and R _1a , refer to the bar described in claim 1, respectively, but R ₂ to R ₈ are not hydrogen,
* Is a binding site with Ir in Formula 1,
*" is a bonding site with neighboring atoms in Formula 1. The method of claim 1,
In Formula 1

A composition wherein the group represented by is a group represented by one of the following formulas A(1) to A(7):

In Formulas A(1) to A(7),
Y ₂ is C,
X ₂₁ is O, S, N(R ₂₅ ), C(R ₂₅ )(R ₂₆ ) or Si(R ₂₅ )(R ₂₆ ),
For descriptions of R ₉ to R ₁₂ and R ₂₁ to R ₂₆ , refer to the description of A ₂₀ in claim 1, respectively,
*'is a binding site with Ir in Formula 1,
*" is a bonding site with neighboring atoms in Formula 1. The method of claim 1,
The composition, wherein the first compound comprises at least one of the following compounds 1 to 53:

The method of claim 1,
Formula 2 of Ar ₁ is i) substituted with at least one R ₆₁ substituted or unsubstituted first ring, ii) at least one R ₆₁ substituted or unsubstituted 2 rings, iii) at least one of R ₆₁ switches to switch to or unsubstituted with at least two first ring is a substituted or unsubstituted at least the ring 2 second ring are condensed with each other to at least one of R ₆₁ a condensed ring, iv) condensed with each other a condensed ring, or v) optionally substituted with at least one R ₆₁ Or an unsubstituted, group derived from a condensed ring in which at least one first ring and at least one second ring are condensed with each other,
Formula 2 of the Ar ₂ is i) at least one of R a ₆₂ substituted or unsubstituted first ring, ii) a substituted or unsubstituted at least the ring 2 the first ring is fused to each other by at least one R ₆₂ in the condensed ring, or iii) a group derived from a condensed ring in which at least one first ring and at least one second ring are condensed with each other, unsubstituted or substituted with at least one R ₆₂ ,
Or the general formula (2) of the Ar ₅ is a single bond, i) at least one substituted with R ₆₅ or unsubstituted first ring, ii) at least one at least one R ₆₅ substituted or unsubstituted second ring, iii ring in) A condensed ring in which two or more first rings substituted or unsubstituted with R ₆₅ are condensed with each other, iv) a condensed ring in which two or more second rings substituted or unsubstituted with R ₆₅ are condensed with each other or v) at least one R ₆₅ substituted or unsubstituted, at least one first ring and at least one second ring is a group derived from a condensed ring condensed with each other, or does not exist,
In Formula 2, ring CY ₂ and ring CY ₃ are independently of each other, i) a first ring, ii) a second ring, iii) a condensed ring in which two or more first rings are condensed with each other, iv) two or more second rings are A condensed ring condensed with each other or v) a condensed ring in which at least one first ring and at least one second ring are condensed with each other,
The first ring is an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, a triazole group, a tetrazole Group, oxadiazole group, triazine group, or thiadiazole group,
The second ring is a benzene group, a cyclopentadiene group, a pyrrole group, a furan group, a thiophene group or a silol group. The method of claim 1,
Ar ₂ in Formula 2 is an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, which is unsubstituted or substituted with at least one R ₆₂ Pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzoquinoline group, benzoisoquinoline group, phthalazine group, naphthyridine group, quinoxaline group, benzoquinoxaline group, quina Sleepy group, sinoline group, phenanthridine group, acridine group, phenanthroline group, phenazine group, benzoimidazole group, isobenzothiazole group, benzoxazole group, isobenzoxazole group, triazole Group, tetrazole group, oxadiazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, azadibenzofuran group, azadibenzothiophene group, The composition, which is an azadibenzosilol group or a pyridopyrazine group. The method of claim 1,
In Formula 2, a2 is 1 or 2, the composition. The method of claim 1,
A composition wherein the second compound comprises a compound represented by the following formula (2):
<Formula 2(1)>

In Formula 2 (1),
Ar ₅ is a single bond, substituted with at least one of R ₆₅ or unsubstituted C ₅ -C ₆₀ carbocyclic group or optionally substituted with at least one R ₆₅ or unsubstituted C ₁ -C ₆₀ heterocyclic group,
Ar ₁ , Ar ₂ , Ar ₅ , a1, a2, ring CY ₂ , ring CY ₃ , R ₂₀ , R ₃₀ , b2 and b3, respectively, refer to the bar described in paragraph 1,
For the description of Ar ₃ and Ar ₄ , refer to the description of Ar ₁ of claim 1, respectively,
Description of a3, a4, ring CY ₄ , ring CY ₅ , R ₄₀ , R ₅₀ , b4 and b5 is a1, a2, ring CY ₂ , ring CY ₃ , R ₂₀ , R ₃₀ , b2 and See the description of b3. The method of claim 1,
In Formula 2

The composition, wherein the group represented by is a group represented by one of the following formulas 2-1 to 2-93:

In Formulas 2-1 to 2-93,
X ₁ is O, S, N(R ₃₁ ), C(R ₃₁ )(R ₃₂ ) or Si(R ₃₁ )(R ₃₂ ),
X ₂ is O, S, N(R ₃₃ ), C(R ₃₃ )(R ₃₄ ) or Si(R ₃₃ )(R ₃₄ ),
For the description of R ₃₁ to R ₃₄ , refer to the description of R ₃₀ in claim 1, respectively,
* Is a binding site with Ar ₁ or Ar ₂ in Formula 2. The method of claim 1,
Ar ₂ in Formula ₂ is a group represented by one of the following Formulas 5-1 to 5-31, a composition:

In Formulas 5-1 to 5-31,
For the description of R ₆₂ , see what is described in paragraph 1,
c2 is an integer from 0 to 2,
c3 is an integer from 0 to 3,
c4 is an integer from 0 to 4,
c5 is an integer from 0 to 5,
c7 is an integer from 0 to 7,
* Is a binding site with Ar ₁ or N in Formula 2. The method of claim 1,
The composition, wherein the second compound comprises at least one of the following compounds H1 to H90:

A first electrode;
A second electrode; And
An organic layer disposed between the first electrode and the second electrode and including an emission layer;
Including,
The organic layer comprises at least one composition of any one of claims 1 to 16, an organic light-emitting device. The method of claim 17,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer further includes a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode,
The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof,
The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. The method of claim 17,
The organic light-emitting device, wherein the composition is included in the emission layer. The method of claim 17,
The organic light-emitting device, wherein the emission layer emits red light.

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