KR20190123238A - Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same - Google Patents

Abstract

Provided are: an organometallic compound represented by chemical formula 1, an organic light emitting device comprising the same, and a composition for diagnosis comprising the same. The description of the chemical formula 1 refers to the present invention as stated above. The organometallic compound has excellent electrical properties and thermal stability.

Description

Organometallic compound, organic light emitting device including the same and a composition for diagnosing including the same}

An organometallic compound, an organic light emitting device including the same, and a diagnostic composition including the same are provided.

An organic light emitting device is a self-luminous device, and is excellent in viewing angle, response time, brightness, driving voltage and response speed, and may be multicolored.

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

On the other hand, a light emitting compound, for example, a phosphorescent light emitting compound may be used for monitoring, sensing, and detection of biological material such as various cells, proteins and the like.

It is to provide a novel organometallic compound and an organic light emitting device and diagnostic composition employing the same.

According to one aspect, an organometallic compound represented by Formula 1 is provided:

<Formula 1>

R ₁ to R ₁₂ and R ₁₉ in Formula 1 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amino Dino 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 alke Nyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted hwandoen C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, Chi Or unsubstituted monovalent non-ring - is an aromatic condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{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 ) and -P (Q ₈ ), Q ₉ ,

At least one of the R ₁ to R ₆ are independently selected from each other, selected from the group represented by the following formula (2),

<Formula 2>

The number of carbons contained in Formula 2 is 4 or more,

R ₁₃ in Formula 2 is hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group or deuterium-containing C ₃ -C ₁₀ cycloalkyl group,

R ₁₄ and R ₁₅ in Formula 2 are each independently a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group or a deuterium-containing C ₃ -C ₁₀ cycloalkyl group ,

Provided that R ₁₃ , R ₁₄ and R ₁₅ are not methyl at the same time,

* Is a binding site with a neighboring atom,

Two or more of R ₁ to R ₉ and R ₁₉ in Formula 1 may be optionally bonded to each other, and substituted or substituted with at least one R _1a to a C ₅ -C ₃₀ carbocyclic group or at least one R _1a . May form a substituted or unsubstituted C ₂ -C ₃₀ heterocyclic group,

For the description of R _1a refer to the description of R 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 condensed 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 alkoxy A silyl group and 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 polycyclic 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 ) and -P (Q ₁₈ ) (Q ₁₉ ) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic 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 ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkoxy 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 (= 0) (Q ₂₈ ) (Q ₂₉ ) and -P (Q ₂₈ ) (Q ₂₉ ), a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl The condensed polycyclic aromatic group and a 1-claw alkenyl, 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- Non-aromatic heterocondensed polycyclic groups; And

-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 (= 0) (Q ₃₈ ) (Q ₃₉ ) and -P (Q ₃₈ ) (Q ₃₉ );

Is selected from,

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, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cya No 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 alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group, at least one substituted C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group of, C ₆ -C ₆₀ An arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group.

According to another aspect, a first electrode, a second electrode, and disposed between the first electrode and the second electrode, and comprises an organic layer including a light emitting layer, the organic layer comprises at least one organic metal compound, organic A light emitting element is provided.

The organometallic compound may be included in the emission layer of the organic layer, and the organometallic compound included in the emission layer may serve as a dopant.

The organometallic compound has excellent electrical characteristics and thermal stability, and the organic light emitting device employing the organometallic compound has excellent driving voltage, current density, external quantum luminous efficiency, roll-off ratio, and lifetime characteristics.

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

The organometallic compound is represented by the following Chemical Formula 1:

<Formula 1>

R ₁ to R ₁₂ and R ₁₉ in Formula 1 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amino Dino 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 alke Nyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted hwandoen C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, Chi Or unsubstituted monovalent non-ring - is an aromatic condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{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 ) and -P (Q ₈ Q ₉ may be selected. For the description of Formulas 2 and 3 and Q ₁ to Q ₉ refer to what is described herein.

For example, R ₁ to R ₁₂ and R ₁₉ 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 , Phosphoric acid groups or salts thereof, -SF ₅ , C ₁ -C ₂₀ alkyl groups and C ₁ -C ₂₀ alkoxy groups;

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 ₁₀ alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclo Octyl group, adamantanyl group (adamantanyl), norbornanyl group (norbornanyl), norbornenyl group (norbornenyl), cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1.1] pentyl group (bicyclo [1.1 .1] pentyl), bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2 ] C ₁ -C ₂₀ alkyl group and C ₁ -C ₂₀ alkoxy group substituted with at least one of octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridinyl group and pyrimidinyl group;

Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, adamantanyl group, norbornanyl group, norbornenyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl group 2.2.1] heptyl), bicyclo [2.2.2] octyl, phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, triphenylenyl, Pyrenyl, chrysenyl, pyrroyl, thiophenyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, Pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxal Nyl group, quinazolinyl group, sinolinyl group, carbazolyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazole Diary, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group and imidazopyrimidinyl 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, C ₁ -C ₂₀ alkoxy group, cyclopentyl group, cyclo Hexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, adamantanyl group, norbornanyl group, norbornenyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo [1.1. 1] bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl ), Bicyclo [2.2.2] octyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, cry Senyl group, pyrroleyl group, thiophenyl group, pu Nyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group , Indazolyl, furinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenanthrolinyl, benzoimidazolyl, benzofuranyl , Benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzo A cyclopentyl group, a cyclohexyl group, substituted with at least one selected from a carbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and -Si (Q ₃₃ ) (Q ₃₄ ) (Q ₃₅ ) , Cycloheptyl group, cyclooctyl group, adamantanyl group (adamanta nyl), norbornanyl, norbornenyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [1.1.1] pentyl, non Cyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, non Phenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrroylyl group, thiophenyl group, furanyl group, imidazolyl group , Pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, Furinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cynolinyl, carbazolyl, phenanthrolinyl, benzoimidazole Group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, di Benzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, and imidazopyrimidinyl group; And

-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 (= 0) (Q ₈ ) (Q ₉ ) and -P (Q ₈ ) (Q ₉ );

Is selected from,

Q ₁ to Q ₉ and Q ₃₃ to Q ₃₅ are each independently,

-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 and -CD ₂ CDH ₂ ;

n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph Til group; And

N-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, substituted with at least one selected from deuterium, C ₁ -C ₁₀ alkyl group and phenyl group, Isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;

Can be selected from.

According to one embodiment, R ₁ to R ₉ and R ₁₉ are independently of each other hydrogen, deuterium, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group or- Si (Q ₃ ) (Q ₄ ) (Q ₅ ). For the description of the above Q ₃ to Q ₅ refer to what is described herein, respectively.

According to another embodiment, R ₁ to R ₁₂ and R ₁₉ are each independently,

Hydrogen, deuterium, 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, tert -decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group ( adamantanyl), norbornanyl, norbornenyl, cyclopentenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [1.1.1] pentyl, non Bicyclo [2.1.1] hexyl , Bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, carba Zolyl group, fluorenyl group, dibenzosilolyl group, dibenzofuranyl group, dibenzothiophenyl group, or -Si (Q ₃ ) (Q ₄ ) (Q ₅ );

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, substituted with at least one deuterium, 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 Tilyl group, 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; or

Methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group substituted with at least one of deuterium and C ₁ -C ₁₀ alkyl group ( adamantanyl), norbornanyl, norbornenyl, cyclopentenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [1.1.1] pentyl, non Cyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, non Phenyl group, terphenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, carbazolyl group, fluorenyl group, dibenzosilolyl group, dibenzofuranyl group or dibenzothiophenyl group;

Can be. For the description of the above Q ₃ to Q ₅ refer to what is described herein, respectively.

According to another embodiment, R ₁ to R ₁₂ and R ₁₉ are each independently of the other hydrogen, deuterium, -F, cyano group, nitro group, -SF ₅ , -CH ₃ , -CD ₃ , -CD ₂ H , -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , at least one hydrogen of the group represented by the following formulas 9-1 to 9-66, substituted with deuterium A group, a group represented by the following formulas 10-1 to 10-249, a group in which at least one hydrogen of the following formulas 10-1 to 10-249 is substituted with deuterium, or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) (However, the description of the above Q ₃ to Q ₅ refer to each bar described herein), but is not limited thereto.

In Formulas 9-1 to 9-66 and 10-1 to 10-249, * is a binding site with a neighboring atom, Ph is a phenyl group, and TMS is a trimethylsilyl group.

The group in which at least one hydrogen of Formulas 9-1 to 9-66 is substituted with deuterium may be, for example, a group represented by one of Formulas 9-501 to 9-552:

The "group in which at least one hydrogen of Formula 10-1 to 10-249 is substituted with deuterium" may be, for example, a group represented by one of Formulas 10-501 to 10-510:

At least one of R ₁ to R ₆ of Formula 1 may be independently selected from a group represented by Formula 2 below:

<Formula 2>

The number of carbons included in Formula 2 is 4 or more (eg, 4 to 20, 4 to 15, or 4 to 10),

R ₁₃ in Formula 2 is hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group or deuterium-containing C ₃ -C ₁₀ cycloalkyl group,

R ₁₄ and R ₁₅ in Formula 2 are each independently a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group or a deuterium-containing C ₃ -C ₁₀ cycloalkyl group ,

* May be a binding site with a neighboring atom.

As used herein, the terms “deuterium-containing C ₁ -C ₂₀ alkyl group” and “deuterium-containing C ₃ -C ₁₀ cycloalkyl group” refer to a C ₁ -C ₂₀ alkyl group and C ₃ -C ₁₀ cyclo substituted with at least one deuterium. It means an alkyl group. For example, deuterium-containing methyl group refers to -CDH ₂ , -CD ₂ H and -CD ₃ .

Examples of the "C ₁ -C ₂₀ alkyl group" in the present specification are methyl group, ethyl group, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -pen Tyl group, tert -pentyl group, neopentyl group, isopentyl group, sec -pentyl group, 3-pentyl group, sec -isopentyl group, n -hexyl group, isohexyl group, sec -hexyl group, tert -hexyl group, n - heptyl, iso-heptyl, sec - heptyl group, tert - heptyl, n - octyl, yisook group, sec - octyl, tert - octyl, n - nonyl, iso-nonyl, sec - nonyl , tert -nonyl group, n -decyl group, isodecyl group, sec -decyl group, tert -decyl group and the like, but is not limited thereto.

Examples of the "C ₃ -C ₁₀ cycloalkyl group" in the present specification include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, adamantanyl group, norbornanyl group, norbornanyl group and bicyclo [1.1 .1] bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl groups (bicyclo [2.2.1] heptyl), a bicyclo [2.2.2] octyl group, and the like, but is not limited thereto.

According to one embodiment, one of R ₂ to R ₅ of Formula 1 may be a group represented by Formula 2.

According to another embodiment, one of R ₂ to R ₅ of Formula 1 is a group represented by Formula 2, and the remaining R ₁ to R ₆ other than the group represented by Formula 2 may be hydrogen.

According to another embodiment, in Formula 1,

1) R ₂ is a group represented by Formula 2, R ₁ and R ₃ to R ₆ are hydrogen,

2) R ₃ is a group represented by Formula 2, R ₁ , R ₂ and R ₄ to R ₆ are hydrogen,

3) R ₄ is a group represented by Formula 2, R ₁ to R ₃ , R ₅ and R ₆ are hydrogen,

4) R ₅ is a group represented by Formula 2, R ₁ to R ₄ and R ₆ is hydrogen,

5) R ₄ is a group represented by Formula 2, and R ₅ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₂ , R ₃ and R ₆ are hydrogen, or

6) R ₅ is a group represented by Formula 2, R ₃ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₂ , R ₄ and R ₆ are hydrogen, or

7) R ₂ is a group represented by Formula 2, R ₅ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₃ , R ₄ and R ₆ are hydrogen, or

8) R ₄ is a group represented by Formula 2, R ₆ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₂ , R ₃ and R ₅ are hydrogen, or

9) R ₃ is a group represented by Formula 2, R ₅ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₂ , R ₄ and R ₆ are hydrogen, or

10) R ₂ is a group represented by Formula 2, R ₄ and R ₅ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, Or a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ), and R ₁ , R ₃ and R ₆ may be hydrogen, but are not limited thereto.

According to another embodiment, at least one of R ₇ to R ₉ of Formula 1 may not be hydrogen.

According to another embodiment, at least one of R ₇ to R ₉ of Chemical Formula 1 is independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted group Or an unsubstituted C ₆ -C ₆₀ aryl group.

According to another embodiment, at least one of R ₇ to R ₉ of Chemical Formula 1 may be independently a substituted or unsubstituted C ₂ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, or a substituted group Or an unsubstituted C ₆ -C ₆₀ aryl group.

According to another embodiment,

1) R ₇ and R ₉ of Formula 1 are not hydrogen, R ₈ and R ₁₉ is hydrogen,

2) R ₇ and R ₈ of Chemical Formula 1 are not hydrogen, and R ₉ and R ₁₉ are hydrogen;

3) R ₇ to R ₉ of Chemical Formula 1 are not hydrogen, R ₁₉ is hydrogen, or

4) R ₇ of Formula 1 is not hydrogen, R ₈ , R ₉ and R ₁₉ may be hydrogen, but is not limited thereto.

According to another embodiment, R ₁₉ of Formula 1 may be hydrogen.

According to another embodiment, R ₇ and R ₉ of Chemical Formula 1 are not hydrogen, and R ₇ and R ₉ may be identical to each other.

According to another embodiment, R ₇ and R ₉ in Chemical Formula 1 are not hydrogen, and R ₇ and R ₉ may be different from each other.

According to another embodiment, R ₇ and R ₉ of Formula 1 are not hydrogen, R ₇ and R ₉ are different from each other, and the number of carbons included in R ₇ is greater than the number of carbons included in R ₉ . Can be.

According to another embodiment, R ₁₃ in Formula 2 may be hydrogen or deuterium.

According to another embodiment, R ₁₃ in Formula 2 is a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group or a deuterium-containing C ₃ -C ₁₀ cycloalkyl group Can be.

According to another embodiment, R ₁₄ and R ₁₅ in Formula 2 may be different from each other.

According to another embodiment, in Formula 2,

R ₁₃ is hydrogen, deuterium, -CH ₃ , -CDH ₂ , -CD ₂ H or -CD ₃ ,

R ₁₄ and R ₁₅ are independently of each other,

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, tert -decyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1. 1] hexyl group (bicyclo [2.1.1] hexyl), bicyclo [2.2.1] heptyl group or bicyclo [2.2.2] octyl group; or

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, substituted with at least one deuterium, 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 Tilyl group, 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, iso-decyl, sec-decyl, tert-decyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, bicyclo [1.1.1] pentyl group (bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl or bicyclo [2.2.2] octyl ;

Can be.

According to another embodiment, in Formula 2, R ₁₄ and R ₁₅ are independently of each other, -CH ₃ , -CDH ₂ , -CD ₂ H, -CD ₃ , represented by Formulas 9-1 to 9-33 Hydrogen in a group, at least one hydrogen of Formulas 9-1 to 9-33 is substituted with deuterium, a group represented by Formulas 10-1 to 10-10 and at least one hydrogen of Formulas 10-1 to 10-10 May be selected from the group substituted with deuterium, but is not limited thereto.

According to another embodiment, the case where R ₁₃ to R ₁₅ in Formula 2 are all the same may be excluded.

According to another embodiment, R ₁₃ to R ₁₅ in Formula 2 may be different from each other.

When R ₁₃ to R ₁₅ in Formula 2 are all methyl groups, they may be excluded.

Meanwhile, at least one of R ₁₀ and R ₁₂ of Formula 1 may be a group represented by the following Formula 3, independently of each other:

<Formula 3>

R ₁₆ to R ₁₈ in Formula 3 may be each independently

Hydrogen, deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₆ -C ₆₀ aryl group and a C ₁ -C ₆₀ heteroaryl group; And

Heavy hydrogen and C ₁ -C ₂₀ substituted by at least one of the alkyl groups, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group;

Is selected from,

* May be a binding site with a neighboring atom.

For example, in Formula 3, R ₁₆ to R ₁₈ may be each independently hydrogen or deuterium.

As another example, at least one of R ₁₆ to R ₁₈ in Formula 3 may not be hydrogen and deuterium. That is, Formula 3 may have two or less benzylic protons.

As another example, two or more of R ₁₆ to R ₁₈ in Formula 3 may not be hydrogen and deuterium. That is, Formula 3 may have one or less benzylic protons.

As another example, all of R ₁₆ to R _{18 in} Formula 3 may not be hydrogen and deuterium.

According to one embodiment, in Formula 3,

R ₁₆ to R ₁₈ are each independently hydrogen or deuterium;

R ₁₆ to R ₁₈ are each independently a methyl group or a deuterium-containing methyl group,

R ₁₆ and R ₁₇ are, independently from each other, hydrogen or deuterium, and R ₁₈ is a methyl group or a deuterium-containing methyl group, or

R ₁₆ and R ₁₇ are, independently from each other, hydrogen or deuterium, and R ₁₈ is a C ₂ -C ₂₀ alkyl group or a deuterium-containing C ₂ -C ₂₀ alkyl group,

R ₁₆ is hydrogen or deuterium and R ₁₇ and R ₁₈ are, independently from each other, a methyl group or a deuterium-containing methyl group, or

R ₁₆ is hydrogen or deuterium, and R ₁₇ and R ₁₈ are, independently from each other, a C ₂ -C ₂₀ alkyl group or a deuterium-containing C ₂ -C ₂₀ alkyl group,

R ₁₆ is a methyl group or a deuterium-containing methyl group, R ₁₇ and R ₁₈ are, independently from each other, a C ₂ -C ₂₀ alkyl group or a deuterium-containing C ₂ -C ₂₀ alkyl group, or

R ₁₆ and R ₁₇ are, independently from each other, a methyl group or a deuterium-containing methyl group, and R ₁₈ may be a C ₂ -C ₂₀ alkyl group or a deuterium-containing C ₂ -C ₂₀ alkyl group.

Examples of the "C ₂ -C ₂₀ alkyl group or deuterium-containing C ₂ -C ₂₀ alkyl 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 Tyl 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 and tert -decyl groups; And

Ethyl group, n -propyl group, isopropyl group, n -butyl group, sec -butyl group, isobutyl group, tert -butyl group, n -pentyl group, tert -pentyl group, neophene substituted with at least one deuterium 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, n - octyl, yisook group, sec - octyl, tert - octyl group, n - nonyl, iso-nonyl, sec - nonyl, tert - nonyl group, n - having Real, isodecyl, sec -decyl and tert -decyl groups;

It may include, but is not limited thereto.

According to another embodiment, R ₁₀ and R ₁₂ in Formula 1 may be identical to each other.

According to another embodiment, R ₁₀ and R ₁₂ in Formula 1 may be different from each other.

For example, R ₁₀ of Formula 1 may be an ethyl group, and R ₁₂ may be a methyl group, n-propyl group, or iso-propyl group, but is not limited thereto.

According to another embodiment, at least one of R ₁₀ , R _12, and R ₁₄ of Formulas 1 and 2 may independently be a C ₃ -C ₁₀ cycloalkyl group or a deuterium-containing C ₃ -C ₁₀ cycloalkyl group, It is not limited to this.

Two or more of R ₁ to R ₉ and R ₁₉ in Formula 1 may be optionally bonded to each other, and substituted or substituted with at least one R _1a to a C ₅ -C ₃₀ carbocyclic group or at least one R _1a . It may form a substituted or unsubstituted C ₂ -C ₃₀ heterocyclic group.

For example, at least two of R ₁ to R ₉ and R ₁₉ of Formula 1 are optionally bonded to each other, substituted or unsubstituted with at least one R _1a , a cyclopentadiene group, a cyclohexane group, a cycloheptane group , Adamantane group, bicyclo-heptanes group, bicyclo-octane group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, naphthalene group, anthracene group, tetracene group, Phenanthrene group, dihydronaphthalene group, phenylene group, benzofuran group, benzothiophene group, benzoselenophene group, indole group, indene group, benzosilol group, azabenzofuran group, azabenzothiophene group, azabenzo A selenophene group, an azaindole group, an azaindene group and an azabenzosilol group may be formed, but are not limited thereto.

For the description of R _1a refer to the description of R ₇ in the present specification.

According to one embodiment, the organometallic compound represented by Formula 1 may satisfy at least one of the following <Condition 1> to <Condition 6>:

<Condition 1>

At least one of R ₁ to R ₃ , R _5, and R ₆ of Formula 1 is not hydrogen

<Condition 2>

At least one of R ₇ to R ₉ of Formula 1 is independently of each other, a group having two or more carbons

<Condition 3>

At least one of R ₇ to R ₉ of Chemical 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 _6- C ₆₀ aryl group

<Condition 4>

At least one of R ₁₀ and R ₁₂ of Formula 1 is independently of each other, a group represented by Formula 3, and R ₁₆ to R ₁₈ in Formula 3 are not all hydrogen

<Condition 5>

At least one of R ₁₀ and R ₁₂ of Formula 1 is independently of each other, a group represented by Formula 3, at least one of R ₁₆ to R ₁₈ of Formula 3 is independently of each other, C ₂ -C ₂₀ Alkyl group, C ₃ -C ₁₀ cycloalkyl group or C ₆ -C ₆₀ aryl group; Or a C ₂ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group or a C ₆ -C ₆₀ aryl group, substituted with at least one of deuterium and a C ₁ -C ₂₀ alkyl group;

<Condition 6>

At least one of R ₁₀ and R ₁₂ in Formula 1 is independently a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group

According to another embodiment, the organometallic compound may be one of Compounds 1 to 20, but is not limited thereto:

TMS in the compounds 1 to 20 is a trimethylsilyl group.

Formula 1 has a structure as described herein, at least one of R ₁ to R ₆ is independently selected from the group represented by the following formula (2):

<Formula 2>

The number of carbons contained in Formula 2 is 4 or more, R ₁₃ is hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group or deuterium-containing C _{A 3} -C ₁₀ cycloalkyl group, R ₁₄ and R ₁₅ are, independently from each other, a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group or a deuterium-containing C ₃ -C _{Is a 10} cycloalkyl group, and * is a bonding site with a neighboring atom.

That is, the group represented by Formula 2 is an alkyl group or derivative thereof having one or less benzylic protons.

While not wishing to be bound by any theory, benzylic protons are more chemically reactive than non-benzylic protons and may cause side reactions caused by the production of various forms of intermediates. However, at least one of R ₁ to R ₆ of Formula 1 is a group represented by Formula 2, which is an alkyl group having a benzylic proton number of 1 or less, or a derivative thereof, so that the organometallic compound represented by Formula 1 is before synthesis Interaction between the organometallic compound molecules can be minimized during the operation of an electronic device (eg, an organic light emitting device) employing the same, while having a stable chemical structure with minimal post-reaction. As a result, the driving voltage, current density, external quantum luminous efficiency, roll-off ratio, and lifetime characteristics of the electronic device employing the organometallic compound represented by Formula 1, for example, the organic light emitting device, may be improved.

In addition, in Formula 2, R ₁₃ , R _14, and R ₁₅ are not methyl groups at the same time. That is, Formula 2 is not a t-butyl group. While not wishing to be bound by any theory, when driving a device, the t-butyl group may be separated from the quinoline ring of Formula 1 and become a t-butyl radical (or t-butyl cation), which may cause device lifetime degradation. have. However, since Chemical Formula 2 is not a t-butyl group, the lifespan of an electronic device employing the organometallic compound represented by Chemical Formula 1, for example, an organic light emitting device, may not be substantially reduced.

The synthesis method of the organometallic compound represented by Chemical Formula 1 may be recognized by those skilled in the art with reference to the synthesis examples described later.

Accordingly, the organometallic compound represented by Formula 1 may be suitable for use as an organic layer of an organic light emitting device, for example, as a dopant of a light emitting layer in the organic layer. According to another aspect, a first electrode; Second electrode; And an organic layer disposed between the first electrode and the second electrode and including a light emitting layer, the organic layer including at least one or more organometallic compounds represented by Chemical Formula 1.

The organic light emitting diode may include an organic layer including an organometallic compound represented by Chemical Formula 1 as described above, and thus may have improved driving voltage, current density, external quantum luminous efficiency, roll-off ratio, and lifespan.

The organometallic compound represented by Formula 1 may be used between a pair of electrodes of the organic light emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. In this case, the organometallic compound may serve as a dopant, and the emission layer may further include a host (that is, the content of the organometallic compound represented by Formula 1 in the emission layer is smaller than that of the host). .

According to one embodiment, the light emitting layer may emit red light.

In the present specification, "(organic layer) contains at least one organometallic compound" means "(organic layer) one organometallic compound belonging to the category of Formula 1 or two different kinds belonging to the category of Formula 1. It may include the above organometallic compound ".

For example, the organic layer may include only Compound 1 as the organometallic compound. In this case, the compound 1 may be present in the light emitting layer of the organic light emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the organometallic compound. In this case, Compound 1 and Compound 2 may be present in the same layer (for example, both Compound 1 and Compound 2 may be present in the light emitting layer).

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

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

As used herein, the term "organic layer" refers to a single 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 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. Hereinafter, a structure and a manufacturing method of an organic light emitting diode according to an embodiment of the present invention will be described with reference to FIG. 1. The organic light emitting diode 10 has a structure in which the first electrode 11, the organic layer 15, and the second electrode 19 are sequentially stacked.

A substrate may be additionally disposed below the first electrode 11 or the second electrode 19. As the substrate, a substrate used in a conventional 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 by, for example, providing a first electrode material on the substrate by using a 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. Indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), or the like may be used as the material for the first electrode. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like 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.

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

The organic layer 15 may include 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 light emitting 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, which are sequentially stacked from the first electrode 11.

When the hole transport region includes the hole injection layer, the hole injection layer HIL may be formed on the first electrode 11 using various methods such as vacuum deposition, spin coating, cast, LB, and the like. 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 characteristics of the hole injection layer, and the like, 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 vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the desired hole injection layer, but a coating speed of about 2000 rpm to about 5000 rpm, The heat treatment temperature for solvent removal after coating may be selected from a temperature range of about 80 ° C. to 200 ° C., but is not limited thereto.

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

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 sulfonicacid : Polyaniline / camphorsulfonic acid), PANI / PSS (Polyaniline) / Poly (4-styrenesulfonate): polyaniline) / poly (4-styrenesulfonate)), a compound represented by the following formula 201 and a compound represented by the following formula 202 At least one may include:

<Formula 201>

<Formula 202>

In Formula 201, Ar ₁₀₁ and Ar ₁₀₂ may be each independently

Phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptalylene group, acenaphthylene group, fluorenylene group, phenenalenylene group, phenanthrenylene group, anthracenylene group, fluoranthhenyl Ethylene group, triphenylenylene group, pyrenylene group, chrysenenylene group, naphthacenylene group, pisenylene group, peryleneylene group and pentaxenylene group; And

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 Salts thereof, C ₁ -C ₆₀ alkyl groups, C ₂ -C ₆₀ alkenyl groups, C ₂ -C ₆₀ alkynyl groups, C ₁ -C ₆₀ alkoxy groups, C ₃ -C ₁₀ cycloalkyl groups, C ₃ -C ₁₀ cycloalkenyl groups , C ₁ -C ₁₀ heterocycloalkyl 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 _A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptal substituted with at least one of a ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed polycyclic group Renylene group, acenaphthylene group, fluorenylene group, phenenylene group, phenanthrenylene group, anthracenylene group, fluoranthrenylene group, triphenylenylene group, pyrenylene group, cry Carbonyl alkylenyl group, a hexenyl group naphtha, blood hexenyl group, a perylenyl group and a carbonyl penta hexenyl groups;

Can be selected from.

In Formula 201, xa and xb may be each independently an integer of 0 to 5, or 0, 1 or 2. For example, xa may be 1 and xb may be 0, but 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 salts thereof, C ₁ -C ₁₀ alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl groups, etc.) and C ₁ -C ₁₀ alkoxy groups (e.g., methoxy, ethoxy Time period, 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 C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group substituted with one or more of its salts;

Phenyl group, naphthyl group, anthracenyl group, fluorenyl group and pyrenyl group; And

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 Phenyl, naphthyl, anthracenyl, fluorenyl and pyrenyl groups substituted with one or more of salts thereof, C ₁ -C ₁₀ alkyl groups and C ₁ -C ₁₀ alkoxy groups;

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

In Formula 201, R ₁₀₉ is

Phenyl group, naphthyl group, anthracenyl group and pyridinyl group; And

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 Phenyl, naphthyl, anthracenyl and pyridinyl groups substituted with one or more of salts thereof, C ₁ -C ₂₀ alkyl groups, C ₁ -C ₂₀ alkoxy groups, phenyl groups, naphthyl groups, anthracenyl groups and pyridinyl groups;

Can be selected from.

According to one embodiment, the compound represented by Formula 201 may be represented by the following Formula 201A, but is not limited thereto.

<Formula 201A>

In Formula 201A, R ₁₀₁ , R ₁₁₁ , R _112, and R ₁₀₉ may be referred to for the detailed description.

For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include Compounds HT1 to HT20, but are not limited thereto.

The hole transport region may have a thickness of about 100 kPa to about 10000 kPa, for example, about 100 kPa to about 1000 kPa. If the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 kPa to about 10000 kPa, for example, about 100 kPa to about 1000 kPa, and the thickness of the hole transport layer is about 50 kPa. To about 2000 kPa, for example, about 100 kPa to about 1500 kPa. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in driving voltage.

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

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. For example, non-limiting examples of the p-dopant include tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethe. Quinone derivatives such as phosphorus (F4-TCNQ) and the like; Metal oxides such as tungsten oxide and molybdenum oxide; And cyano group-containing compounds such as the compound HT-D1, and the like, but are not limited thereto.

The hole transport region may further include a buffer layer.

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

The emission layer EML may be formed on the hole transport region by using a method such as vacuum deposition, spin coating, casting, and LB. When the light emitting layer is formed by a vacuum deposition method and a spin coating method, the deposition conditions and coating conditions vary depending on the compound to be used, and in general, may be selected from a range of conditions substantially the same as the formation of the hole injection layer.

Meanwhile, when the hole transport region includes an electron blocking layer, the electron blocking layer material may be selected from materials that can be used in the hole transport region as described above and host materials described below, but is not limited thereto. . For example, when the hole transport region includes an electron blocking layer, mCP described later can be used as the electron blocking layer material.

The emission layer may include a host and a dopant, and the dopant includes an organometallic compound represented by Chemical Formula 1.

The host may comprise at least one of the following TPBi, TBADN, ADN (also called "DNA"), CBP, CDBP, TCP, Mcp, Compound H50 and Compound H51:

Alternatively, the host may further include a compound represented by Formula 301:

<Formula 301>

In Formula 301, Ar ₁₁₁ and Ar ₁₁₂ are independently of each other,

Phenylene group, naphthylene group, phenanthrenylene group and pyrenylene group; And

Phenylene group, naphthylene group, phenanthrenylene group and pyrenylene group substituted with at least one of phenyl group, naphthyl group and anthracenyl group;

Can be selected from.

Ar ₁₁₃ to Ar ₁₁₆ in Formula 301 may be each independently

C ₁ -C ₁₀ alkyl group, phenyl group, naphthyl group, phenanthrenyl group and pyrenyl group; And

Phenyl group, naphthyl group, phenanthrenyl group and pyrenyl group substituted with at least one of phenyl group, naphthyl group and anthracenyl group;

Can be selected from.

In Formula 301 g, h, i and j may be an integer of 0 to 4 independently from each other, for example, 0, 1 or 2.

In Formula 301, Ar ₁₁₃ to Ar ₁₁₆ may be each independently,

C ₁ -C ₁₀ alkyl group substituted with one or more of phenyl group, naphthyl group and anthracenyl group;

Phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group, and fluorenyl group;

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 Salts thereof, C ₁ -C ₆₀ alkyl groups, C ₂ -C ₆₀ alkenyl groups, C ₂ -C ₆₀ alkynyl groups, C ₁ -C ₆₀ alkoxy groups, phenyl groups, naphthyl groups, anthracenyl groups, pyrenyl groups, phenanthrenyl groups And a phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group and fluorenyl group substituted with at least one of fluorenyl group; And

;

;

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

Alternatively, the host may include a compound represented by Formula 302:

<Formula 302>

Ar _{122 in} Formula 302 For details about Ar ₁₂₅ , refer to the description of Ar ₁₁₃ of Chemical Formula 301.

Ar ₁₂₆ and Ar ₁₂₇ in Formula 302 may be each independently a C ₁ -C ₁₀ alkyl group (eg, a methyl group, an ethyl group, or a propyl group).

In Formula 302 k and l may be an integer of 0 to 4 independently of each other. For example, k and l may be 0, 1 or 2.

When the organic light emitting device is a full color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer. Alternatively, the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked to emit white light.

When the light emitting 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 light emitting layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 200 kPa to about 600 kPa. When the thickness of the light emitting layer satisfies the aforementioned range, the light emitting layer may exhibit excellent light emission characteristics 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.

The formation conditions of the hole blocking layer, the electron transport layer, and the electron injection layer of the electron transport region may be referred to the formation conditions of the hole injection layer.

When the electron transport region includes the hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and Balq, but is not limited thereto.

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

The electron transport layer may include at least one of BCP, Bphen and Alq ₃ , Balq, TAZ, and NTAZ.

Alternatively, the electron transport layer may include at least one of the following compounds ET1 to ET25, but is not limited thereto.

The electron transport layer may have a thickness of about 100 kPa to about 1000 kPa, for example, about 150 kPa to about 500 kPa. When the thickness of the electron transporting layer satisfies the aforementioned range, a satisfactory electron transporting characteristic can be obtained without a substantial increase in driving voltage.

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

The metal-containing material may comprise a Li complex. The Li complex may include, for example, the following compound ET-D1 (LiQ) 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 at least one selected from LiF, NaCl, CsF, Li ₂ O, and BaO.

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

The 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 having a relatively low work function, or a combination thereof may be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. It may be used as a material for forming the second electrode 19. Alternatively, various modifications are possible, such as forming the transmissive second electrode 19 by using ITO or IZO to obtain a top light emitting device.

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

According to another aspect, a diagnostic composition including at least one organometallic compound represented by Formula 1 is provided.

Since the organometallic compound represented by Formula 1 may provide a high luminous efficiency, the diagnostic composition including the organometallic compound may have a high diagnostic efficiency.

The diagnostic composition may be variously applied to various diagnostic kits, diagnostic reagents, biosensors, biomarkers, and the like.

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

In the present specification, a C ₁ -C ₆₀ alkoxy group refers to a monovalent group having a chemical formula of —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 at least one carbon-carbon double bond in the middle or the terminal of the C ₂ -C ₆₀ alkyl group, and specific examples thereof include an ethenyl group, propenyl group, butenyl group, and the like. This includes. As used herein, a 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 at least one carbon-carbon triple bond 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), and the like. As used herein, a C ₂ -C ₆₀ alkynylene group refers to a divalent group having the same structure as the C ₂ -C ₆₀ alkynyl group.

As used herein, a C ₃ -C ₁₀ cycloalkyl group means a monovalent saturated hydrocarbon monocyclic or polycyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group And a cycloheptyl group. As used herein, a C ₃ -C ₁₀ cycloalkylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkyl group.

As used herein, a C ₁ -C ₁₀ heterocycloalkyl group means 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 tetrahydrofuranyl group, tetrahydrothiophenyl group and the like. As used herein, a C ₁ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₁ -C ₁₀ heterocycloalkyl group.

As used herein, a 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 having no aromaticity. Specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, and the like. As used herein, a C ₃ -C ₁₀ cycloalkenylene group refers to a divalent group having the same structure as the C ₃ -C ₁₀ cycloalkenyl group.

As used herein, a C ₁ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms that includes at least one hetero atom selected from N, O, P, Si, and S as a ring-forming atom, Have at least one double bond in it. Specific examples of the C ₁ -C ₁₀ heterocycloalkenyl group include 2,3-dihydrofuranyl group, 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.

As used herein, a C ₆ -C ₆₀ aryl group refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C ₆ -C ₆₀ arylene group refers to a carbo having 6 to 60 carbon atoms By divalent group having a cyclic aromatic system. Specific examples of the C ₆ -C ₆₀ aryl group include a phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, 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, two or more rings may be fused to each other.

As used herein, a C ₁ -C ₆₀ heteroaryl group means a monovalent group containing at least one hetero atom selected from N, O, P, Si, and S as a ring-forming atom and having a heteroaromatic system having 1 to 60 carbon atoms. And a C ₁ -C ₆₀ heteroarylene group means a divalent group containing at least one hetero atom selected from N, O, P, Si, and S as a ring-forming atom and having a heteroaromatic system having 1 to 60 carbon atoms. do. Specific examples of the C ₁ -C ₆₀ heteroaryl group include a pyridinyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolinyl group, 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, 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 is the C ₆ -C ₆₀ aryl group.

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

In the present specification, a monovalent non-aromatic condensed heteropolycyclic group includes two or more rings 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. And monovalent groups (eg, having from 1 to 60 carbon atoms) in which the entire molecule has non-aromaticity. The monovalent non-aromatic heterocondensed polycyclic group includes a carbazolyl group and the like. As used herein, the divalent non-aromatic heterocondensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

As used herein, a C ₅ -C ₃₀ carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbons as ring forming atoms. The C ₅ -C ₃₀ carbocyclic group may be a monocyclic group or a polycyclic group.

C ₁ -C ₃₀ heterocyclic group as used herein 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 30 carbons as ring forming atoms. The C ₁ -C ₃₀ heterocyclic group may be a monocyclic group or a polycyclic group.

The substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₂ -C ₃₀ 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, , A substituent of a substituted monovalent non-aromatic condensed polycyclic group and a substituted monovalent non-aromatic condensed polycyclic 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 ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkoxy A silyl group and 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 polycyclic 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 ) and -P (Q ₁₈ ) (Q ₁₉ ) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic 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 ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkoxy 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 (= 0) (Q ₂₈ ) (Q ₂₉ ) and -P (Q ₂₈ ) (Q ₂₉ ), a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl The condensed polycyclic aromatic group and a 1-claw alkenyl, 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- Non-aromatic heterocondensed polycyclic groups; And

-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 (= 0) (Q ₃₈ ) (Q ₃₉ ) and -P (Q ₃₈ ) (Q ₃₉ );

Can be selected from.

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, hydrogen, deuterium, -F, -Cl, -Br, -I, and hydroxy. Practical 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 alke Nyl 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 hetero cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group, at least one substituted C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group of, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, and monovalent non-aromatic condensed polycyclic group.

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

 EXAMPLE

Synthesis Example  1 (compound 2)

Synthesis of Intermediate 2-B

4 g (17.48 mmol) of starting material 2-A were mixed with 72 mL of THF, cooled to 0 ° C., and 29 mL of 1M LiAlH ₄ in THF solution was added dropwise. Thereafter, the temperature of the reaction was raised to room temperature and refluxed overnight. 1 mL of water was added to the reaction product, 2 mL of 50% NaOH (aq) was added thereto, and EA (ethyl acetate) was added thereto to separate the organic layer. After drying the obtained organic layer was subjected to column chromatography to give 3.0g of intermediate 2-B (82% yield).

Synthesis of Intermediate 2-E

3 g (19.04 mmol) of Intermediate 2-B, 4.23 g (28.55 mmol) of Intermediate 2-C, 0.18 g (0.190 mmol) of RuCl ₂ (PPh ₃ ) ₃ and 1.92 g (34.26 mmol) of KOH were mixed with 53 mL of toluene And refluxed at 120 ° C. overnight. The resulting product was cooled to room temperature, washed with water, and subjected to column chromatography to obtain 4.4 g of intermediate 2-E (yield 48%). The obtained compound was confirmed by LC-MS analysis.

LC-MS m / z = 268.14 (M + H) &lt; + &gt;

Synthesis of Intermediate 2-G

4.4 g (16.43 mmol) of Intermediate 2-E, 1.81 g (18.08 mmol) of Intermediate 2-F, 0.37 g (1.64 mmol) of Pd (OAc) ₂ , 6.81 g (49.30 mmol) of K ₂ CO ₃ and 2.70 g (3.29 Sphos) mmol) was mixed with 154 mL of Dioxane and 38 mL of H ₂ O and refluxed at 90 ° C. overnight. The resulting product was cooled to room temperature, washed with water and Methylene chloride, and subjected to column chromatography to obtain 3.8 g of intermediate 2-G (80% yield). The obtained compound was confirmed by LC-MS analysis.

LC-MS m / z = 288.28 (M + H) &lt; + &gt;

Synthesis of Intermediate 2-H

1.8 g (6.26 mmol) of intermediate 2-G were mixed with methanol, and 0.36 g of Pd on carbon was added thereto. Hydrogen gas was bubbling for 6 hours or more with respect to the reaction product obtained therefrom. After the reaction was completed, MeOH was removed, washed with H ₂ O and methylene chloride, and column chromatography was performed to obtain 0.8 g of intermediate 2-H (yield 44%). The obtained compound was confirmed by LC-MS analysis.

LC-MS m / z = 290.20 (M + H) &lt; + &gt;

Synthesis of Intermediate 2-I

0.40 g (1.13 mmol) of IrCl ₃ -4H ₂ O, 14 mL of 2-ethoxyethanol and 4.5 mL of H ₂ O were added to 0.74 g (2.55 mmol) of Intermediate 2-H and refluxed at 120 ° C. overnight. The resulting product was cooled to room temperature, filtered, washed with methanol and dried to yield 0.65 g of intermediate 2-I.

Synthesis of Compound 2

0.65 g (0.40 mmol) of intermediate 2-I, 0.74 g (4.04 mmol) of 2,2,6,6-tetramethylheptane-3,5-dione, and 0.56 g (4.04 mmol) of K ₂ CO ₃ were mixed with 22 mL of 2-ethoxyethanol And stirred overnight at room temperature. The resultant was washed with Ethylene acetate and H ₂ O, and then subjected to column chromatography to obtain 0.43 g (57% yield) of Compound 2. The obtained compound was confirmed by LC-MS analysis.

m / z = 953.27 (M + H) &lt; + &gt;

Synthesis Example  2 (compound 1)

Synthesis of Intermediate 1-C

3.70 g (18.67 mmol) of starting material 1-A, 2.94 g (19.61 mmol) of starting material 1-B, 1.08 g (0.93 mmol) of Pd (PPh ₃ ) ₄ and 6.45 g (46.68 mmol) of K ₂ CO ₃ were added to THF 60 mL. And 30 mL of H ₂ O and refluxed at 90 ° C. overnight. The resulting product was cooled to room temperature, washed with water and Methylene chloride, and subjected to column chromatography to obtain 4.00 g of Intermediate 1-C (yield 80%). The obtained compound was confirmed by LC-MS analysis.

LC-MS m / z = 268.12 (M + H) &lt; + &gt;

Synthesis of Intermediate 1-E

Intermediate 1-C 4.00 g (14.96 mmol), Intermediate 1-D 1.79 g (18.95 mmol), Pd (OAc) ₂ 0.17 g (0.75 mmol), K ₂ CO ₃ 5.17 g (37.40 mmol) and Sphos 0.61 g (1.50 mmol) was mixed with 50 mL of THF and 25 mL of H ₂ O and refluxed at 90 ° C. overnight. The resulting product was cooled to room temperature, washed with water and Methylene chloride, and subjected to column chromatography to obtain 2.20 g (51%) of intermediate 1-E. The obtained compound was confirmed by LC-MS analysis.

LC-MS m / z = 288.22 (M + H) &lt; + &gt;

Synthesis of Intermediate 1-F

2.20g (7.60mmol) of intermediate 1-E was mixed with methanol, and 0.24g of Pd on carbon was added thereto. Hydrogen gas was bubbling for more than 6 hr to the reaction product obtained therefrom. After the reaction was completed, MeOH was removed, washed with H ₂ O and methylene chloride, and subjected to column chromatography to obtain 1.55 g (70% yield) of intermediate 1-F. The obtained compound was confirmed by LC-MS analysis.

LC-MS m / z = 290.22 (M + H) &lt; + &gt;

Synthesis of Intermediate 1-G

To 1.58 g (5.47 mmol) of Intermediate 1-F, 0.96 g (2.73 mmol) of IrCl ₃ -4H ₂ O, 10 mL of 2-ethoxyethanol and 3.5 mL of H ₂ O were added and refluxed at 120 ° C. overnight. The resulting product was cooled to room temperature, filtered, washed with methanol and dried to yield 1.35 g of intermediate 1-G.

Synthesis of Compound 1

1.35 g (0.86 mmol) of intermediate 1-G, 0.89 g (8.64 mmol) of pentane-2,4-dione, and 0.91 g (8.64 mmol) of Na ₂ CO ₃ were mixed with 17 mL of 2-ethoxyethanol and refluxed overnight. The resultant was washed with Ethylene acetate and H ₂ O, and then subjected to column chromatography to obtain 0.50 g (yield 33%) of Compound 1. The obtained compound was confirmed by LC-MS analysis.

m / z = 869.36 (M + H) &lt; + &gt;

Synthesis Example  3 (compound 5)

Synthesis of Intermediate 5-B

Intermediate 5-B, using the same method as for the synthesis of Intermediate 2-B of Synthesis Example 1, except that 4.00 g (18.52 mmol) of the starting material 5-A was used instead of the starting material 2-A. 3.33 g (89% yield) were obtained.

Synthesis of Intermediate 5-E

Intermediate 2 of Synthesis Example 1, except that 3.33 g (16.48 mmol) of Intermediate 5-B was used instead of Intermediate 2-B and 3.66 g (24.72 mmol) of Intermediate 5-C was used instead of Intermediate 2-C. Intermediate 5-E, using the same method as for the synthesis of -E 3.09 g (60% yield) were obtained.

Synthesis of Intermediate 5-G

Intermediate of Synthesis Example 1, except that 3.00 g (9.61 mmol) of Intermediate 5-E was used instead of Intermediate 2-E, and 1.06 g (10.57 mmol) of Intermediate 5-F was used instead of Intermediate 2-F. Intermediate 5-G, using the same method as for the synthesis of 2-G 2.26 g (yield 82%) were obtained. The obtained compound was confirmed by LC-MS analysis. LC-MS m / z = 288.28 (M + H) &lt; + &gt;

Synthesis of Intermediate 5-H

Intermediate 5-H, using the same method as the synthesis method of Intermediate 2-H of Synthesis Example 1, except that 2.2 g (7.65 mmol) of Intermediate 5-G was used instead of Intermediate 2-G. 1.22 g (yield 55%) were obtained. The obtained compound was confirmed by LC-MS analysis.

LC-MS m / z = 290.20 (M + H) &lt; + &gt;

Synthesis of Intermediate 5-I

Intermediate 5-I, using the same method as the synthesis of Intermediate 2-I of Synthesis Example 1, except that 1.22 g (4.22 mmol) of Intermediate 5-H was used instead of Intermediate 2-H. 1.00 g were obtained.

Synthesis of Compound 5

1.00 g (0.97 mmol) of Intermediate 5-I was used in place of Intermediate 2-I and pentane-2,4-dione was used in place of 2,2,6,6-tetramethylheptane-3,5-dione Obtained compound 5 0.72g (yield 55%) using the method similar to the synthesis method of the said synthesis example 1. The obtained compound was confirmed by LC-MS analysis.

m / z = 869.40 (M + H) &lt; + &gt;

Synthesis Example  4 (compound 12)

Compound 2 of Synthesis Example 1, except that 3,7-diethyl-3,7-dimethylnonane-4,6-dione was used instead of 2,2,6,6-tetramethylheptane-3,5-dione Compound 12 (1.10 g, yield 65%) was synthesized using the same method as the synthesis method of.

m / z = 1008.61 (M + H) &lt; + &gt;

Example  One

ITO / Ag / ITO as an anode was cut into glass substrates with a thickness of 70/1000 / 70Å to 50mm x 50mm x 0.5mm, ultrasonically cleaned with isopropyl alcohol and pure water for 5 minutes, and then UV light for 30 minutes. Was irradiated, exposed to ozone, washed and installed in a vacuum deposition 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 was formed on the hole injection layer. (Hereinafter referred to as NPB) was vacuum deposited to form a hole transport layer having a thickness of 1350 kPa.

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

Thereafter, BCP is vacuum deposited on the light emitting layer to form a hole blocking layer having a thickness of 50 kV, and Alq _{3 is} then vacuum deposited on the hole blocking layer to form an electron transporting layer having a thickness of 350 kV. LiF was vacuum-deposited to form an electron injection layer having a thickness of 10 μs, and an organic light emitting device (red light emission) was formed by co-depositing Mg and Ag on a weight ratio of 90:10 on the electron injection layer to form a cathode having a thickness of 120 μs. Produced.

Example  2 to 4 and Comparative example  A to F

An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1, instead of compound 2, was used as a dopant in forming the emission layer.

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

Driving voltage, current density, maximum external quantum luminous efficiency (Max EQE), roll-off ratio, and half-width of the emission peak in the EL spectrum of each of the organic light emitting devices manufactured in Examples 1 to 4 and Comparative Examples A to F. And the maximum emission wavelength and lifetime (LT ₉₇ ) were evaluated and the results are shown in Table 1. As an evaluation device, a current-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used, and the life time (LT ₉₇ ) (at 3500 nit) was evaluated for the time taken for the luminance of 97% to 100% of the initial luminance. The roll-off ratio was calculated according to the following equation 20.

(Eq. 20)

Roll-off ratio = {1- (Efficiency (at 3500nit) / Max Luminous Efficiency)} X 100%

Dopant in emitting layer Driving
Voltage
(V) electric current
density
(㎃ / ㎠) Max EQE
(%) Roll-Off ratio
(%) Half width
(nm) Emission wavelength
(nm) LT ₉₇
(hr) Example 1 Compound 2 5.35 17.4 25.8 10 62.47 617 250 Example 2 Compound 1 5.02 17.3 26.8 11 58.64 608 226 Example 3 Compound 5 5.06 17.3 26.0 13 61.98 614 207 Example 4 Compound 12 5.10 16.7 27.8 10 62.75 619 280 Comparative Example A Compound A 5.49 12.2 20.4 28 82.39 623 50 Comparative Example B Compound B 9.82 670.2 13.7 89 23.6 652 One Comparative Example C Compound C 5.81 20.1 21.2 25 78.21 602 22 Comparative Example D Compound d 5.65 19.4 21.8 17 68.17 615 80 Comparative Example E Compound E 5.65 19.4 22.8 16 63.57 614 23 Comparative Example F Compound F 5.80 20.0 25.9 13 59.41 616 150

N-Hex in the said compound A means n-hexyl group.

From Table 1, it can be seen that the organic light emitting diodes of Examples 1 to 4 have improved driving voltage, current density, external quantum luminous efficiency, roll-off ratio, and lifespan characteristics as compared to the organic light emitting diodes of Comparative Examples A to F. Can be.

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

Claims (20)

An organometallic compound represented by Formula 1 below:
<Formula 1>

R ₁ to R ₁₂ and R ₁₉ in Formula 1 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , hydroxyl group, cyano group, nitro group, amino group, amino Dino 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 alke Nyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted hwandoen C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, Chi Or unsubstituted monovalent non-ring - is an aromatic condensed polycyclic group, a substituted or unsubstituted 1, a non-aromatic heterocyclic condensed polycyclic _{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 ) and -P (Q ₈ ), Q ₉ ,
At least one of the R ₁ to R ₆ are independently selected from each other, selected from the group represented by the following formula (2),
<Formula 2>

The number of carbons contained in Formula 2 is 4 or more,
R ₁₃ in Formula 2 is hydrogen, deuterium, C ₁ -C ₂₀ alkyl group, deuterium-containing C ₁ -C ₂₀ alkyl group, C ₃ -C ₁₀ cycloalkyl group or deuterium-containing C ₃ -C ₁₀ cycloalkyl group,
R ₁₄ and R ₁₅ in Formula 2 are each independently a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group or a deuterium-containing C ₃ -C ₁₀ cycloalkyl group ,
Provided that R ₁₃ , R ₁₄ and R ₁₅ are not methyl at the same time,
* Is a binding site with a neighboring atom,
Two or more of R ₁ to R ₉ and R ₁₉ in Formula 1 may be optionally bonded to each other, and substituted or substituted with at least one R _1a to a C ₅ -C ₃₀ carbocyclic group or at least one R _1a . May form a substituted or unsubstituted C ₂ -C ₃₀ heterocyclic group,
For the description of R _1a refer to the description of R 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 condensed polycyclic group At least one of the substituents,
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 alkoxy A silyl group and 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 polycyclic 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 ) and -P (Q ₁₈ ) (Q ₁₉ ) A C ₁ -C ₆₀ alkyl group, a C ₂ -C ₆₀ alkenyl group, a C ₂ -C ₆₀ alkynyl group and a C ₁ -C ₆₀ alkoxy group;
C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl Oxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed polycyclic 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 ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkoxy 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 (= 0) (Q ₂₈ ) (Q ₂₉ ) and -P (Q ₂₈ ) (Q ₂₉ ), a C ₃ -C ₁₀ cycloalkyl group, a C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl The condensed polycyclic aromatic group and a 1-claw alkenyl, 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- Non-aromatic heterocondensed polycyclic groups; And
-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 (= 0) (Q ₃₈ ) (Q ₃₉ ) and -P (Q ₃₈ ) (Q ₃₉ );
Is selected from,
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, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cya No 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 alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group , C ₆ -C ₆₀ aryl group, C ₁ -C ₆₀ alkyl and C ₆ -C ₆₀ aryl group, at least one substituted C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group of, C ₆ -C ₆₀ An arylthio group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group. The method of claim 1,
R ₁ to R ₁₂ and R ₁₉ are each independently,
Hydrogen, deuterium, 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, tert -decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group ( adamantanyl), norbornanyl, norbornenyl, cyclopentenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [1.1.1] pentyl, non Bicyclo [2.1.1] hexyl , Bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, carba Zolyl group, fluorenyl group, dibenzosilolyl group, dibenzofuranyl group, dibenzothiophenyl group, or -Si (Q ₃ ) (Q ₄ ) (Q ₅ );
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, substituted with at least one deuterium, 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 Tilyl group, 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; or
Methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group substituted with at least one of deuterium and C ₁ -C ₁₀ alkyl group ( adamantanyl), norbornanyl, norbornenyl, cyclopentenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo [1.1.1] pentyl, bicyclo [1.1.1] pentyl, non Cyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl, phenyl, non Phenyl group, terphenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, carbazolyl group, fluorenyl group, dibenzosilolyl group, dibenzofuranyl group or dibenzothiophenyl group;
Is selected from,
Q ₃ to Q ₅ 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 and -CD ₂ CDH ₂ ;
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naph Til group; And
N-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n-pentyl group, substituted with at least one selected from deuterium, C ₁ -C ₁₀ alkyl group and phenyl group, Isopentyl group, sec-pentyl group, tert-pentyl group, phenyl group and naphthyl group;
Selected from among the organometallic compounds. The method of claim 1,
An organometallic compound of Formula 1, wherein one of R ₂ to R ₅ is a group represented by Formula 2. The method of claim 1,
1) R ₂ is a group represented by Formula 2, R ₁ and R ₃ to R ₆ are hydrogen,
2) R ₃ is a group represented by Formula 2, R ₁ , R ₂ and R ₄ to R ₆ are hydrogen,
3) R ₄ is a group represented by Formula 2, R ₁ to R ₃ , R ₅ and R ₆ are hydrogen,
4) R ₅ is a group represented by Formula 2, R ₁ to R ₄ and R ₆ is hydrogen,
5) R ₄ is a group represented by Formula 2, and R ₅ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₂ , R ₃ and R ₆ are hydrogen, or
6) R ₅ is a group represented by Formula 2, R ₃ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₂ , R ₄ and R ₆ are hydrogen, or
7) R ₂ is a group represented by Formula 2, R ₅ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₃ , R ₄ and R ₆ are hydrogen, or
8) R ₄ is a group represented by Formula 2, R ₆ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₂ , R ₃ and R ₅ are hydrogen, or
9) R ₃ is a group represented by Formula 2, R ₅ is a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) and R ₁ , R ₂ , R ₄ and R ₆ are hydrogen, or
10) R ₂ is a group represented by Formula 2, R ₄ and R ₅ are each independently a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, a phenyl group, An organometallic compound, wherein a biphenyl group or -Si (Q ₃ ) (Q ₄ ) (Q ₅ ) is R ₁ , R ₃ and R ₆ are hydrogen. The method of claim 1,
At least one of R ₇ to R ₉ is independently of each other, 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 ₆ -C ₆₀ aryl Organic metal compounds. The method of claim 1,
R ₁₃ in Formula 2 is hydrogen or deuterium, an organometallic compound. The method of claim 1,
R ₁₃ in Formula 2 is a C ₁ -C ₂₀ alkyl group, a deuterium-containing C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group or a deuterium-containing C ₃ -C ₁₀ cycloalkyl group, an organometallic compound. The method of claim 1,
An organometallic compound wherein R ₁₄ and R ₁₅ in Formula 2 are different from each other. The method of claim 1,
In Formula 2,
R ₁₃ is hydrogen, deuterium, -CH ₃ , -CDH ₂ , -CD ₂ H or -CD ₃ ,
R ₁₄ and R ₁₅ are independently of each other,
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, tert -decyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, bicyclo [1.1.1] pentyl group, bicyclo [2.1. 1] hexyl group (bicyclo [2.1.1] hexyl), bicyclo [2.2.1] heptyl group or bicyclo [2.2.2] octyl group; or
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, substituted with at least one deuterium, 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 Tilyl group, 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, iso-decyl, sec-decyl, tert-decyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, bicyclo [1.1.1] pentyl group (bicyclo [1.1.1] pentyl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1] heptyl or bicyclo [2.2.2] octyl ;
Phosphorus, organometallic compounds. The method of claim 1,
At least one of R ₁₀ and R ₁₂ of Formula 1 is independently of each other, an organometallic compound of the group represented by the following formula (3):
<Formula 3>

In Formula 3,
R ₁₆ to R ₁₈ are independently of each other,
Hydrogen, deuterium, a C ₁ -C ₂₀ alkyl group, a C ₃ -C ₁₀ cycloalkyl group, a C ₆ -C ₆₀ aryl group and a C ₁ -C ₆₀ heteroaryl group; And
Heavy hydrogen and C ₁ -C ₂₀ substituted by at least one of the alkyl groups, C ₁ -C ₂₀ alkyl, C ₃ -C ₁₀ cycloalkyl, C ₆ -C ₆₀ aryl group and C ₁ -C ₆₀ heteroaryl group;
Is selected from,
* Is a bonding site with a neighboring atom. The method of claim 1,
An organometallic compound wherein R ₁₀ and R ₁₂ of Formula 1 are the same as each other. The method of claim 1,
An organometallic compound wherein R ₁₀ and R ₁₂ in Formula 1 are different from each other. The method of claim 1,
At least one of R ₁₀ , R _12, and R ₁₄ of Formulas 1 and 2, independently of each other, is a C ₃ -C ₁₀ cycloalkyl group or a deuterium-containing C ₃ -C ₁₀ cycloalkyl group, an organometallic compound. The method of claim 1,
An organometallic compound, which is one of the following compounds 1 to 20:

A first electrode;
Second electrode; And
An organic layer disposed between the first electrode and the second electrode and including a light emitting layer;
Including,
The organic light emitting device of claim 1, wherein the organic layer comprises at least one organometallic compound according to any one of claims 1 to 14. The method of claim 15,
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 light emitting layer, and an electron transport region disposed between the light emitting layer and the second electrode,
The hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer or any combination thereof,
And the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. The method of claim 15,
An organic light emitting device, wherein the organometallic compound is included in the light emitting layer. The method of claim 17,
The organic light emitting device, wherein the light emitting layer emits red light. The method of claim 17,
The light emitting layer further comprises a host, wherein the content of the host in the light emitting layer is larger than the content of the organometallic compound in the light emitting layer. A diagnostic composition comprising at least one organometallic compound according to any one of claims 1 to 14.

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