KR20210113037A - Organic light emitting device - Google Patents

Abstract

Disclosed is an organic light emitting element which comprises: a first electrode; a second electrode; and an organic layer including a light emitting layer disposed between the first electrode and the second electrode. The light emitting layer comprises a polycyclic compound having a predetermined chemical formula and a host. A content of the polycyclic compound is smaller than a content of the host.

Description

Organic light emitting device

An organic light emitting device is provided.

An organic light emitting device is a self-luminous device that has a wide viewing angle and excellent contrast, has a fast response time, has excellent luminance, drive voltage and response speed characteristics, and can be multicolored compared to conventional devices. .

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

An object of the present invention is to provide an organic light emitting device having high efficiency and high color purity.

According to one aspect, the first electrode; a second electrode; and an organic layer including a light emitting layer disposed between the first electrode and the second electrode.

The organic layer includes a polycyclic compound represented by the following formula (1) and a host,

An organic light emitting device is provided, wherein the content of the polycyclic compound is smaller than the content of the host:

<Formula 1>

<Formula 1A>

In Formulas 1 and 1A,

Ar ₁ is a group represented by Formula 1A,

rings CY ₁ and CY ₂ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,

Y ₁ is B, N, P, P(=O), P(=S), Al, Ga, As, Si(R ₅ ) or Ge(R ₅ ),

X ₁ and X ₂ are each independently O, S, Se, N(R ₆ ), C(R ₆ )(R ₇ ), Si(R ₆ )(R ₇ ), Ge(R ₆ )(R _{7 )} ), P(=O)(R ₆ ),

L ₁ and L ₁₁ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,

a1 and a11 are each independently an integer selected from 1 to 3,

When a1 is 2 or more, two or more L ₁ are the same or different from each other, and when a11 is 2 or more, two or more L ₁₁ are the same or different from each other,

R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₁₁ and R ₁₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group , substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted 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 a C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₆ -C ₆₀ arylalkyl group, A substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ ) ( Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=O)(Q ₈ )(Q ₉ ),

The R ₁ and R ₂ may be optionally combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, and ,

b1 and b2 are each independently an integer selected from 0 to 10,

When b1 is 2 or more, two or more R ₁ are the same as or different from each other, and when b2 is 2 or more, two or more R ₂ are the same or different from each other,

b11 is an integer selected from 1 to 5;

When b11 is 2 or more, two or more R ₁₁ are the same as or different from each other,

b12 is an integer selected from 1 to 8;

When b12 is 2 or more, 2 or more R ₁₂ are the same as or different from each other,

c11 is an integer selected from 1 to 8;

When c11 is 2 or more, two or more -(L ₁₁ ) _a11 -(R ₁₁ ) _b11 are the same as or different from each other,

The sum of b12 and c11 is 9,

said substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -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 ₆ -C ₆₀ arylalkyl group, At least one of the substituents of the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed polycyclic group is,

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, 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 ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ an alkynyl 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 group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₆ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₄ )( Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), and -P(=O)(Q ₁₈ )(Q _{19 ), C 1} -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group substituted with at least one selected from , C ₂ -C ₆₀ alkynyl group and 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 an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₆ -C ₆₀ arylalkyl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, 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 ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₆ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, 1 A non-aromatic condensed heteropolycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₄ )(Q ₂₅ ) -B(Q ₂₆ )(Q ₂₇ ) and -P(=O) )(Q ₂₈ )(Q _{29 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalke, substituted with at least one selected from (Q 28 )(Q 29 ) group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₆ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocondensed polycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) and -P(=O)(Q ₃₈ )(Q _{39 )} );

is selected from;

The Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted substituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or an unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ - C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₆ -C ₆₀ arylalkyl group, a substituted or unsubstituted selected from a C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

The organic light emitting device may have high efficiency and high color purity.

1 is a cross-sectional view schematically illustrating an organic light emitting diode according to an exemplary embodiment.
2A to 2C are diagrams schematically illustrating energy transfer in a light emitting layer of an organic light emitting device according to an exemplary embodiment.

The organic light emitting device includes a first electrode; a second electrode; and an organic layer including a light emitting layer disposed between the first electrode and the second electrode, wherein the organic layer includes a polycyclic compound represented by Formula 1 and a host, wherein the content of the polycyclic compound is the content of the host may be smaller than

The polycyclic compound may include a compound represented by the following formula (1):

<Formula 1>

<Formula 1A>

In Formulas 1 and 1A,

Ar ₁ is a group represented by Formula 1A. In Formula 1A, * is a binding site with Formula 1.

In Formula 1, rings CY ₁ and CY ₂ may each independently represent a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group.

According to one embodiment, the CY ₁ and CY ₂ are each independently formed by a condensed ring formed by condensing two or more groups selected from the following group A, group B, and group A, and at least two groups selected from group B below are condensed It may be selected from a condensed ring, and a condensed ring formed by condensing at least one A group and at least one B group:

Group A is cyclopenta-1,3-diene, indene group, azulene group, benzene group, naphthalene group, anthracene group, phenanthrene group, tetracene group, tetrapene group, pyrene group, chrysene group, triphenyl is a lene group or a fluorene group,

Group B is a furan group, a thiophene group, a pyrrole group, a borol group, a silol group, a pyrrolidine group, an imidazole group, a thiazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, isothia. Zole group, pyridine group, pyrimidine group, pyridazine group, triazine group, indole group, isoindole group, indolizine group, quinoline group, isoquinoline group, quinoxaline group, isoquinoxaline group, carbazole group, di benzofuran, dibenzothiophene, dibenzosilol group, or dibenzoborol group.

According to another embodiment, the A group may be a benzene group, a naphthalene group, or an anthracene group, and the B group may be a carbazole group, dibenzofuran, dibenzothiophene, dibenzosilol group, or dibenzoborol group. have.

For example, CY ₁ and CY ₂ may be each independently selected from a benzene group, a naphthalene group, an anthracene group, and a fluorene group, but is not limited thereto.

In Formula 1, Y ₁ may be B, N, P, P(=O), P(=S), Al, Ga, As, Si(R ₅ ), or Ge(R ₅ ). For example, Y ₁ may be B, N, P, P(=O), P(=S), Al, or Ga.

In Formula 1, X ₁ and X ₂ are each independently O, S, Se, N(R ₆ ), C(R ₆ )(R ₇ ), Si(R ₆ )(R ₇ ), Ge(R ₆ )(R ₇ ) and P(=O)(R ₆ ) may be selected.

According to one embodiment, X ₁ and X ₂ may be the same as each other. For example, X ₁ and X ₂ may each be O, S, N(R ₆ ), C(R ₆ )(R ₇ ), or Si(R ₆ )(R ₇ ), but are not limited thereto. .

According to another embodiment, X ₁ and X ₂ may be different from each other. For example, X ₁ is O and X ₂ is S; X ₁ is O and X ₂ is N(R ₆ ); X ₁ is O and X ₂ is C(R ₆ )(R ₇ ); X ₁ is O and X ₂ is Si(R ₆ )(R ₇ ); X ₁ is S and X ₂ is N(R ₆ ); X ₁ is S and X ₂ is C(R ₆ )(R ₇ ); X ₁ is S and X ₂ is Si(R ₆ )(R ₇ ); X ₁ is N(R ₆ ) and X ₂ is C(R ₆ )(R ₇ ); X ₁ is N(R ₆ ) and X ₂ is Si(R ₆ )(R ₇ ); Alternatively, X ₁ may be C(R ₆ )(R ₇ ) and X ₂ may be Si(R ₆ )(R ₇ ). In another example, X ₂ is O and X ₁ is S; X ₂ is O and X ₁ is N(R ₆ ); X ₂ is O and X ₁ is C(R ₆ )(R ₇ ); X ₂ is O and X ₁ is Si(R ₆ )(R ₇ ); X ₂ is S and X ₁ is N(R ₆ ); X ₂ is S and X ₁ is C(R ₆ )(R ₇ ); X ₂ is S and X ₁ is Si(R ₆ )(R ₇ ); X ₂ is N(R ₆ ) and X ₁ is C(R ₆ )(R ₇ ); X ₂ is N(R ₆ ) and X ₁ is Si(R ₆ )(R ₇ ); Alternatively, X ₂ may be C(R ₆ )(R ₇ ) and X ₁ may be Si(R ₆ )(R ₇ ).

According to one embodiment, Y ₁ is B, X ₁ and X ₂ are, independently of each other, O, S, Se, N(R ₆ ), C(R ₆ )(R ₇ ) and Si(R ₆ )( R ₇ ) may be selected from, but is not limited thereto.

In Formulas 1 and 1A, L ₁ and L ₁₁ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group can be selected.

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

single bond;

Phenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl a renylene group, a pyrenylene group, and a chrysenylene group; and

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalke group, 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 ₆ - C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group substituted with at least one selected from a phenylene group, an indenylene group, a naphthylene group, Azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, and chrysenylenyl group Rengi; and

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalke group, 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 ₆ - C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group substituted with at least one selected from a phenyl group, indenyl group, naphthyl group, azulenyl group , heptalenyl group, acenaphthyl group, fluorenyl group, phenarenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, and at least one selected from chrysenylenyl group is substituted Phenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl a renylene group, a pyrenylene group, and a chrysenylene group;

may be selected from, but is not limited thereto.

For example, L ₁ and L ₁₁ may be a single bond and may be selected from Formulas 3-1 to 3-32, but is not limited thereto:

In Formulas 3-1 to 3-32,

Z ₃₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group Or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthi group, C ₆ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl 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 ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₆ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, 1 A non-aromatic condensed heteropolycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₄ )(Q ₂₅ ) -B(Q ₂₆ )(Q ₂₇ ) and -P(=O) _{) (Q 28) (Q 29} ) from the at least one selected substituted, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl group, 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 arylthio, C ₆ -C ₆₀ arylalkyl group, and C ₁ -C ₆₀ heteroaryl group;

e4 is an integer selected from 1 to 4,

e6 is an integer selected from 1 to 6,

e8 is an integer selected from 1 to 8,

* and *' are binding sites with neighboring atoms.

In Formulas 1 and 1A, a1 and a11 are each independently an integer selected from 1 to 3, when a1 is 2 or more, two or more L ₁ are the same as or different from each other, and when a11 is 2 or more, two or more L ₁₁ are each other may be the same or different.

In Formulas 1 and 1A, R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₁₁ and R ₁₂ are each independently hydrogen, deuterium, -F, -Cl, -Br , -I, -SF ₅ , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, substituted or unsubstituted substituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted A substituted C ₃ -C ₁₀ cycloalkyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocyclo alkenyl group, a substituted or unsubstituted C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₆ -C ₆₀ arylalkyl group, substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=O)(Q ₈ )(Q _{9 )} ), wherein in Formula 1, R ₁ and R ₂ are optionally bonded to each other, and a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group.

According to one embodiment, in Formula 1, R ₁ and R ₂ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group , a triphenylenyl group, a pyrenyl group, a C ₁ -C ₆₀ alkyl group substituted with at least one of a chrysenyl group, a C ₁ -C ₆₀ alkoxy group;

cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, Triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group , pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, Sinolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, C ₁ -C ₆₀ alkyl group, C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ arylalkyl group, cyclo Pentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, tri phenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, Pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cy Nolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, tria Zinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )( Q ₃₇ ) and -P(=O)(Q ₃₈ )(Q ₃₉ ) substituted with at least one of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, Biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyra Zolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group , quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, Benzooxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group , a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group and a carbazolyl group; and

-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=O)(Q ₈ )(Q _{9 )} );

may be selected from, but is not limited thereto.

For example, R ₁ and R ₂ are independently of each other,

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group , iso-hexyl group, sec-hexyl group and tert-hexyl group;

Deuterium, -F, -Cl, -Br, -I, a methyl group substituted with at least one of a hydroxyl group, a cyano group, a nitro group, and a phenyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso -Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group;

can be selected from

According to one embodiment _{, at least one of R 1} and R ₂ may be selected from the group represented by the following Chemical Formulas 5-1 and 5-2, but is not limited thereto:

In Formulas 5-1 and 5-2,

R ₅₁ to R ₅₅ are each independently,

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec- Butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso -hexyl group, sec-hexyl group and tert-hexyl group, phenyl group, biphenyl group and terphenyl group; and

Deuterium, -F, -Cl, -Br, -I, a methyl group substituted with at least one of a hydroxyl group, a cyano group, a nitro group, and a phenyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso -Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group;

is selected from

The R ₅₄ and R ₅₅ may be optionally combined with each other to form a heterocycle,

b54 and b55 are each independently an integer selected from 0 to 4.

For example, in Formula 5-1, one of R ₅₁ to R ₅₃ is a phenyl group, and the remainder is a methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec- Butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso It may be selected from a -hexyl group, a sec-hexyl group, and a tert-hexyl group.

For example, in Formula 5-2, R ₅₄ and R ₅₅ may combine with each other to form a pentagonal ring together with a ring member N.

According to one embodiment, in Formula 1, R ₃ and R ₄ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group , iso-hexyl group, sec-hexyl group and tert-hexyl group;

Deuterium, -F, -Cl, -Br, -I, a methyl group substituted with at least one of a hydroxyl group, a cyano group, a nitro group, and a phenyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso -Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group;

may be selected from, but is not limited thereto.

For example, R ₃ and R ₄ may each be hydrogen.

According to one embodiment, in Formula 1, R ₅ , R ₆ and R ₇ are each independently

hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group , iso-hexyl group, sec-hexyl group and tert-hexyl group;

Deuterium, -F, -Cl, -Br, -I, a methyl group substituted with at least one of a hydroxyl group, a cyano group, a nitro group, and a phenyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group , n-hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group;

a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

A phenyl group substituted with at least one of a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

may be selected from, but is not limited thereto.

According to one embodiment, in Formula 1A, R ₁₁ is selected from Formulas 4-1 to 4-42,

R ₁₂ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso- Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n -hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group;

Deuterium, -F, -Cl, -Br, -I, a methyl group substituted with at least one of a hydroxyl group, a cyano group, a nitro group, and a phenyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso -Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group; may be selected from, but not limited to:

In Formulas 4-1 to 4-42,

Y ₃₁ is O, S, C(Z ₄₅ )(Z ₄₆ ), N(Z ₄₇ ), or Si(Z ₄₈ )(Z ₄₉ ),

Z ₄₁ to Z ₄₉ are each independently,

Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof , phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₆₀ arylalkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, Phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group , pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, Purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazole diary, benzoxazolyl group, benzoisooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, and carbazolyl group;

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, a cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group substituted with at least one of a _{C 1} -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, and a C ₆ -C _{60 arylalkyl group} group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imine Dazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazole group Diary, furinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoiso a thiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group; may be selected from, but not limited to,

f3 is selected from an integer of 1 to 3,

f4 is selected from an integer of 1 to 4,

f5 is selected from an integer of 1 to 5,

f6 is selected from an integer of 1 to 6,

f7 is selected from an integer of 1 to 7,

f9 is selected from an integer of 1 to 9,

* is a binding site with a neighboring atom.

In Formula 1, b1 and b2 are each independently an integer selected from 0 to 10, when b1 is 2 or more, two or more R ₁ are the same as or different from each other, and when b2 is 2 or more, two or more R ₂ are the same or different from each other can do.

In Formula 1A, b11 is an integer selected from 1 to 5, and when b11 is 2 or more, two or more R ₁₁ may be the same as or different from each other.

In Formula 1A, b12 is an integer selected from 1 to 8, and when b12 is 2 or more, two or more R ₁₂ may be the same as or different from each other.

In Formula 1A, c11 is an integer selected from 1 to 8, and when c11 is 2 or more, two or more -(L ₁₁ ) _a11 -(R ₁₁ ) _b11 may be the same as or different from each other.

In Formula 1A, the sum of b12 and c11 may be 9. For example, b12 may be 8, and c11 may be 1.

According to one embodiment, Formula 1A may be selected from the following Formulas 1A-1 to 1A-5:

In Formulas 1A-1 to 1A-5,

For the description of L ₁₁ , a ₁₁ , R ₁₁ and b ₁₁ , refer to the above bar, respectively,

For a description of R ₂₁ to R ₂₉ , refer to the description of _{R 12 described above, respectively,}

* is a binding site with a neighboring atom.

According to one embodiment, the polycyclic compound may include a compound represented by the following Chemical Formulas 2-1 to 2-8:

In Formulas 2-1 to 2-8,

Y ₁ , X ₁ , X ₂ , R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , L ₁ , a _{1 ,} and Ar ₁ refer to the above description.

According to one embodiment, the polycyclic compound may be selected from the following compounds 1 to 468:

.

.

_{The cyclic compound exhibits high color purity because the element Y 1} containing core has a planar structure of multiple resonance as shown in Chemical Formula 1, and has a robust skeleton condensed while sharing a benzene ring. At the same time, the fluorescence emitter represented by Chemical Formula 1 includes an anthracenyl group having the lowest excitation triplet (T1*) similar to the lowest excitation triplet (T1) of the core structure, and spin orbit due to resonance between T1-T1* The inverse interterm transition speed is amplified by the coupling (SOC) mechanism, and the efficiency is remarkably improved.

On the other hand, the conventional compound having a multi-resonance structure achieved the improvement of color purity, but the efficiency was not improved due to the minimization of spatial overlap between the highest occupied molecular orbital (HOMO) and the lowest occupied molecular orbital (LUMO). Conversely, a donor-acceptor structure in which HOMO and LUMO are spatially completely separated was proposed to lower ΔEst to improve efficiency. phenomenon occurred. Color purity and efficiency had a trade-off relationship with each other.

However, since the organic light emitting device of the present invention includes the polycyclic compound represented by Formula 1, color purity and efficiency are improved at the same time by a triple resonance mechanism that simultaneously utilizes a multiple resonance mechanism and a resonance mechanism between triplets.

According to one embodiment, the polycyclic compound represented by Formula 1 may be a fluorescent emitter.

According to one embodiment, the light emitting layer may further include a sensor satisfying Equation 1 below, and the content of the host may be greater than the sum of the contents of the sensitizer and the polycyclic compound:

[Equation 1]

ΔE _ST ≤ 0.3 eV

Here, ΔE _ST denotes the energy difference between the lowest excitation singlet (S ₁ ) and the lowest excitation triplet (T _{1 ).}

The triplet energy level and the singlet energy level may be evaluated using a DFT method of a Gaussian program that is structurally optimized at the B3LYP/6-31G(d,p) level.

The sensitizer and the polycyclic compound may satisfy the following conditions 1 and 2:

<Condition 1>

T _decay (PC)<T _decay (S)

<Condition 2>

T _decay (PC)<1.5 μs

Among conditions 1 and 2 above,

T _decay (PC) is the decay time of the polycyclic compound;

T _decay (S) is the decay time of the sensitizer.

The decay time of the polycyclic compound was obtained by vacuum co-depositing the host and the polycyclic compound included in the light emitting layer on a quartz substrate in a weight ratio of 90:10 ^{at a vacuum degree of 10 -7} torr (hereinafter referred to as a 40 nm thick film) It is a value calculated from a Time-Resolved Photoluminescence (TRPL) spectrum at room temperature for "film (CD)").

The attenuation time of the sensor is determined by vacuum co-depositing the host and the sensor included in the light emitting layer on a quartz substrate at a weight ratio of 90: 10 ^{at a vacuum degree of 10 −7} torr to a 40 nm thick film (hereinafter It is a value calculated from a TRPL (Time-Resolved Photoluminescence) spectrum at room temperature for "film (S)").

In general, triplet excitons are known to affect the reduction of the lifetime of the organic light emitting device because the residence time in the excited state is long. However, in the present invention, since the polycyclic compound is used, the lifetime of the organic light emitting device including the same can be improved by reducing the retention time of the triplet exciton of the sensor.

Specifically, as the number of triplet excitons of the sensor increases, extra energy is accumulated in the sensor, so that more hot excitons are generated. That is, the amount of triplet excitons of the sensory and the amount of high-temperature excitons are proportional to each other. The high-temperature exciton breaks various chemical bonds of the compound included in the light emitting layer and/or the compound present at the interface of the light emitting layer, thereby decomposing the compound. Accordingly, the lifespan of the organic light emitting diode may be reduced. However, in the present invention, by using the polycyclic compound, the triplet exciton of the sensor can be rapidly converted into the singlet exciton of the polycyclic compound, so ultimately the amount of high-temperature exciton can be reduced, and the organic The lifetime of the light emitting device can be improved.

Here, "high-temperature exciton" refers to exciton-exciton annihilation due to an increase in the density of excitons in the light emitting layer, exciton-charge annihilation due to charge imbalance in the light emitting layer, and/or host-polycyclic It can be generated and increased due to radical ion pairing according to electron transfer between the liver.

In order to rapidly convert the triplet exciton of the sensor into the singlet exciton of the polycyclic compound, the above-mentioned condition 1 must be satisfied.

In addition, since the polycyclic compound emits fluorescence, an organic light emitting device of high color purity can be provided. Accordingly, it is possible to prevent the accumulation of singlet excitons in the excited state of the cooling dopant, and to improve the lifespan of the organic light emitting diode.

More specifically, when the following condition 3 is further satisfied, the conversion from the triplet exciton of the sensorizer to the singlet exciton of the polycyclic compound may occur more smoothly, so that the lifespan improvement effect of the organic light emitting device is further improved It can be large:

<Condition 3>

T _decay (PC) / T _decay (S) < 0.5

Among the above conditions 3,

T _decay (PC) is the decay time of the polycyclic compound;

T _decay (S) is the decay time of the sensor.

In another embodiment, the organic light emitting device may further satisfy the following condition 4:

<Condition 4>

BDE(S) - T ₁ (S) < 3.0 eV

Among the above conditions 4,

BDE(S) is the binding dissociation energy level of the sensor;

T ₁ (S) is the lowest excitation triplet energy level of the sensor.

Ultimately, the organic light emitting device may have a desired level of lifespan by satisfying the following condition 5:

<Condition 5>

R(Hex)/e ¹⁰ < 15

Among the above conditions 5,

R(Hex) is the high-temperature exciton production rate.

Here, R(Hex) was calculated through the Gaussian 09 program according to Equation C below after performing photochemical stability analysis of the organic light emitting diode.

<Formula C>

R(Hex) = ax T _decay (S) xe ^{-(BDE(S) - T} ₁ ^(S))

In the above formula C,

a is any constant,

T _decay (S) is the decay time of the sensor;

BDE(S) is the binding dissociation energy level of the sensor;

T ₁ (S) is the lowest excitation triplet energy level of the sensor.

The high-temperature exciton generation rate is ^{estimated to be proportional to (decaying time) X e -(BDE-T1) , and (high-temperature exciton generation rate)/e 10} must be less than 15 in order to obtain a desired level of lifetime of the organic light emitting diode.

Here, the degradation analysis (PCS) of the organic light emitting device is calculated according to the following Equation P:

<Formula P>

PCS (%) = I ₂ /I ₁ x 100

In the above formula P,

For _{the film formed by depositing the compound for which I 1} is to measure PCS, KIMMON-KOHA's He-Cd laser (excitation wavelength = 325 nanometers, laser power density = 100 mW/cm ² ) is used. Thus, the maximum light intensity obtained from the PL spectrum after evaluating the PL spectrum at room temperature in an Ar atmosphere in which the outside air is blocked immediately after film formation,

I ₂ is with respect to the film formed by depositing the compound to be measured the PCS, under the outdoor air is cut off Ar atmosphere, I ₁ rating when using a pumping laser of KIMMON-KOHA's He-Cd laser (excitation wavelength = 325 nanometers, After exposure to light of laser power density = 100 mW/cm ² ) for 3 hours, the PL spectrum was evaluated at room temperature using a He-Cd laser (excitation wavelength = 325 nanometers) manufactured by KIMMON-KOHA, and the This is the maximum light intensity obtained in the PL spectrum. In the sensor, Reverse Inter System Crossing (RISC) and/or intersystem crossing (ISC) actively occur, thereby allowing excitons generated in the host to be transferred to the polycyclic compound.

Specifically, a general energy transfer of an organic light emitting device (type I) according to an exemplary embodiment will be described with reference to FIG. 2A as follows.

Singlet and triplet excitons are formed in the host in the light emitting layer, and the singlet and triplet excitons formed in the host are transferred to a sensor, and then transferred to a polycyclic compound through Fㆆrster energy transfer (FRET). . In this case, in order to secure high efficiency and long lifespan of the organic light emitting diode, it is necessary to control high-temperature excitons generated in the light emitting layer, and for this, optimization of energy transfer is required.

More specifically, a general energy transfer of an organic light emitting diode according to an embodiment will be described with reference to FIG. 2B as follows. This case corresponds to the case where the sensor is a thermally activated delayed fluorescence (TADF) emitter with _{ΔE ST ≤ 0.3 eV.}

25% of the singlet excitons formed in the host are transferred to the sensor through Fㆆrster energy transfer, and the energy of 75% of the triplet excitons formed in the host is transferred to singlets and triplets of the sensor, Among them, the energy transferred to the triplet is crossed inversely to the singlet, and then the singlet energy of the sensorizer is transferred to the polycyclic compound through Fㆆrster energy transfer.

More specifically, a general energy transfer of an organic light emitting diode (type II) according to another embodiment will be described with reference to FIG. 2C as follows. This case corresponds to a case in which the sensortizer is an organometallic compound including one or more metals selected from a 1-period transition metal, a 2-period transition metal, and a 3-period transition metal.

75% of triplet excitons formed in the host are transferred to the sensor through Dexter energy transfer, and 25% of the energy of singlet excitons formed in the host is transferred to singlets and triplets of the sensor, among which The energy transferred to the singlet is crossed over to the triplet, and then the triplet energy of the sensor is transferred to the polycyclic compound through Fㆆrster energy transfer.

Accordingly, by transferring both singlet excitons and triplet excitons generated in the emission layer to polycyclics, an organic light emitting diode with improved efficiency can be obtained. In addition, since an organic light emitting diode having significantly reduced energy loss can be obtained, lifespan characteristics of the organic light emitting diode can be improved.

The content of the sensor in the light emitting layer may be selected within the range of 5 wt% to 50 wt%. When the above-described range is satisfied, effective energy transfer in the light emitting layer can be achieved, and thus an organic light emitting device with high efficiency and long life can be realized.

In an embodiment, the host, the polycyclic compound, and the sensitizer may further satisfy the following condition 6:

<Condition 6>

T ₁ (H) ≥ T ₁ (S) ≥ S ₁ (PC)

Among the above conditions 6,

T ₁ (H) is the lowest excitation triplet energy level of the host;

S ₁ (PC) is the lowest singlet excitation energy level of the polycyclic compound;

T ₁ (S) is the lowest excitation triplet energy level of the sensor.

When the host, the polycyclic compound, and the sensor further satisfy Equation 3, an organic light emitting device with improved efficiency may be obtained by effectively transferring triplet excitons to the polycyclic compound in the emission layer.

The light emitting layer may consist of the host, the polycyclic compound, and the sensor. That is, the light emitting layer does not further include a material other than the host, the polycyclic compound, and the sensor.

According to another embodiment, the light emitting layer may further include a light emitting dopant, and in this case, the content of the host may be greater than the sum of the contents of the light emitting dopant and the polycyclic compound represented by Formula 1. The light emitting dopant may include a light emitting dopant having _{S 1} and T ₁ energy levels suitable for receiving energy from _{the excitation S 1} energy level of the polycyclic compound. In this case, the polycyclic compound may serve as a sensor that transmits energy, and in this case, the polycyclic compound and the light emitting dopant may equally satisfy the above-described relation between the sensor and the polycyclic compound.

A method for synthesizing the polycyclic compound represented by Chemical Formula 1 may be recognized by those skilled in the art with reference to Synthesis Examples to be described later.

According to one embodiment, among the organic light emitting device,

The first electrode is an anode, the second electrode is a cathode,

The organic layer 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 includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof,

The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof, but is not limited thereto.

The light emitting layer may emit blue light. For example, the blue light means a wavelength range of 440 nm to 490 nm.

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

A substrate may be additionally disposed below the first electrode 11 or above the second electrode 19 . As the substrate, a substrate used in a 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, handling easiness and waterproofness may be used.

The first electrode 11 may be formed, for example, by providing a material for the first electrode on a substrate 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. As a material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO ₂ ), zinc oxide (ZnO), or the like may be used. Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used. .

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

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

The organic layer 15 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 emission layer.

The hole transport region may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

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

When the hole transport region includes the hole injection layer, the hole injection layer (HIL) may be formed on the first electrode 11 by using various methods such as vacuum deposition, spin coating, casting, LB, and the like. have.

In the case of forming the hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure and thermal characteristics of the target hole injection layer, etc., but for example, the deposition temperature of about 100 to about 500° C., a vacuum degree of about 10 ⁻⁸ to about 10 ⁻³ torr, and a deposition rate of about 0.01 to about 100 Å/sec may be selected from the range, but is not limited thereto.

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

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

The hole transport region is, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, TCTA (4,4' ,4"-tris(N-carbazolyl)triphenylamine (4,4',4"-tris(N-carbazolyl)triphenylamine)), Pani/DBSA (Polyaniline/Dodecylbenzenesulfonic acid: polyaniline/dodecylbenzenesulfonic acid), PEDOT/PSS (Poly(3,4-ethylenedioxythiophene)/Poly(4-styrenesulfonate):poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate)), Pani/CSA (Polyaniline/Camphor sulfonicacid) : polyaniline/camphorsulfonic acid), PANI/PSS (Polyaniline)/Poly(4-styrenesulfonate):polyaniline)/poly(4-styrenesulfonate)), a compound represented by the following Chemical Formula 201 and a compound represented by the following Chemical Formula 202 It may include at least one:

<Formula 201>

<Formula 202>

In Formula 201, Ar ₁₀₁ and Ar ₁₀₂ are each independently

Phenylene group, pentarenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenyl a lene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group; and

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalke group, 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 - A phenylene group, a pentarenylene group, an indenylene group, a naphthylene group, an azulenylene group, substituted with at least one selected from a _{C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed polycyclic group.} , heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenylenylene group, naphthacenylene group , picenylene group, perylenylene group and pentacenylene group;

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 each independently

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

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof, substituted with one or more of a C ₁ -C ₁₀ alkyl group and a C ₁ -C ₁₀ alkoxy group;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group; and

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group substituted with one or more of a _{C 1} -C ₁₀ alkyl group and a C ₁ -C _{10 alkoxy group;}

may be selected from, but is not limited thereto.

In Formula 201, R ₁₀₉ is,

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; and

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group substituted with at least one of a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group ;

can be selected from

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

<Formula 201A>

_{For a detailed description of R 101} , R ₁₁₁ , R ₁₁₂ and R ₁₀₉ in Formula 201A, refer to the above description.

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

The hole transport region may have a thickness of about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å. If the hole transport region includes both a hole injection layer and a hole transport layer, the thickness of the hole injection layer is about 100 Å to about 10000 Å, for example, about 100 Å to about 1000 Å, and the thickness of the hole transport layer is about 50 Å to about 2000 Angstroms, for example about 100 Angstroms to about 1500 Angstroms. When the thickness of the hole transport region, the hole injection layer, and the hole transport layer satisfies the above-described ranges, satisfactory hole transport characteristics may be obtained without a substantial increase in driving voltage.

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

The charge-generating material may be, for example, a p-dopant. The p-dopant may be 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-benzoquinonedimethane 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 following compounds HT-D1 and HT-D2, 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 for an optical resonance distance according to a wavelength of light emitted from the light emitting layer.

The hole transport region may further include an electron blocking layer. The electron blocking layer may include a known material, for example, mCP, but is not limited thereto.

The emission layer EML may be formed on the hole transport region by using a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. In the case of forming the light emitting layer by vacuum deposition or spin coating, the deposition conditions and coating conditions vary depending on the compound used, but in general, they may be selected from within the same range of conditions as those for forming the hole injection layer.

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 has a structure in which a red light emitting layer, a green light emitting layer, and/or a blue light emitting layer are stacked, so that various modifications are possible, such as emitting white light.

The light emitting layer includes a host and a dopant, the dopant includes the polycyclic compound represented by Chemical Formula 1, and the description of the polycyclic compound refers to the bar described in the present specification.

The host may comprise at least one of the following TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, compound H50 to compound H52:

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

<Formula 301>

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

a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group; and

a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group, each substituted with one or more of a phenyl group, a naphthyl group, and an anthracenyl group;

can be selected from

In Formula 301, Ar ₁₁₃ to Ar ₁₁₆ are each independently

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

a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group substituted with one or more of a phenyl group, a naphthyl group, and an anthracenyl group;

can be selected from

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

In Formula 301, Ar ₁₁₃ to Ar ₁₁₆ are each independently

_{a C 1} -C ₁₀ alkyl group substituted with at least one of a phenyl group, a naphthyl group, and an anthracenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group and a fluorenyl group;

Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or Salts 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, phenyl group, naphthyl group, anthracenyl group, pyrenyl group, phenanthrenyl group and a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, each substituted with one or more of a fluorenyl group; and

;

;

may be selected from, but is not limited thereto.

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

<Formula 302>

For a detailed description of Ar ₁₂₂ to Ar ₁₂₅ in Formula 302, refer to the description _{of Ar 113 in Formula 301.}

_{Ar 126} and Ar ₁₂₇ in Formula 302 may each independently represent 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 each independently an integer of 0 to 4. For example, k and l may be 0, 1, or 2.

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

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

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

The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

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.

For the formation conditions of the hole blocking layer, the electron transport layer, and the electron injection layer in the electron transport region, refer to the formation conditions of the hole injection layer.

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

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

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

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

The metal-containing material may include a Li complex. The Li complex may include, for example, the following compound ET-D1 (lithium quinolate, LiQ) or ET-D2.

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

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

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

In the present specification, the C ₅ -C ₃₀ carbocyclic group refers to an aromatic or non-aromatic mono or polycyclic group having 1 to 30 carbon atoms. C ₁ -C ₃₀ heterocyclic group means an aromatic or non-aromatic mono or polycyclic group having 1 to 30 carbon atoms including at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom do.

In the present specification, the C ₁ -C ₆₀ alkyl group means a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, and a sec-butyl group. , ter-butyl group, pentyl group, iso-amyl group, hexyl group, and the like are included. 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, the C ₁ -C ₆₀ alkoxy group refers to a _{monovalent group having the formula of -OA 101} (here, A _{101 is the C 1} -C ₆₀ alkyl group), and specific examples thereof include a methoxy group, an ethoxy group, isopropyloxy group and the like.

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

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

In the present specification, the C ₃ -C ₁₀ cycloalkyl group refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclohep group. til groups, and the like. The C ₃ -C ₁₀ cycloalkylene group of the specification and the second having the same structure as the above C ₃ -C ₁₀ cycloalkyl group means a group.

In the present specification, the C ₂ -C ₁₀ heterocycloalkyl group refers to a monovalent monocyclic group having 2 to 10 carbon atoms including at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom, Specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. In the present specification, the C ₂ -C ₁₀ heterocycloalkylene group refers to a divalent group having the same structure as the C ₂ -C _{10 heterocycloalkyl group.}

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

In the present specification, the C ₂ -C ₁₀ heterocycloalkenyl group is a monovalent monocyclic group having 2 to 10 carbon atoms including at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom, has at least one double bond in it. Specific examples of the C ₂ -C ₁₀ heterocycloalkenyl group include a 2,3-hydrofuranyl group, a 2,3-hydrothiophenyl group, and the like. In the present specification, the C ₂ -C ₁₀ heterocycloalkenylene group refers to a divalent group having the same structure as the C ₂ -C _{10 heterocycloalkenyl group.}

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

In the present specification, the C ₂ -C ₆₀ heteroaryl group includes at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom and a monovalent group having a carbocyclic aromatic system having 2 to 60 carbon atoms. means, and the C ₂ -C ₆₀ heteroarylene group contains at least one hetero atom selected from N, O, P, Si and S as a ring-forming atom and has 2 to 60 carbon atoms in a carbocyclic aromatic system. means group. Specific examples of the C ₂ -C ₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like. When the C ₂ -C ₆₀ heteroaryl group and the C ₂ -C ₆₀ heteroarylene group include two or more rings, the two or more rings may be fused to each other.

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

In the present specification, the C ₆ -C ₆₀ arylalkyl group refers to -A ₁₀₄ A ₁₀₅ (where A104 is a C ₁ -C ₅₄ alkyl group, and A ₁₀₅ is a C ₆ -C ₅₉ aryl group ₎ , for example, a cumyl group ( cumyl group) and the like.

In the present specification, the monovalent non-aromatic condensed polycyclic group includes two or more rings condensed with each other and contains only carbon as a ring-forming atom (eg, carbon number may be 8 to 60). and a monovalent group in which the entire molecule has non-aromaticity. Specific examples of the non-aromatic condensed polycyclic group include a fluorenyl group and the like. In the present specification, 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, in the monovalent non-aromatic condensed heteropolycyclic group, two or more rings are condensed with each other, and carbon as a ring forming atom (eg, carbon number may be 2 to 60) in addition to It includes a hetero atom selected from N, O, P, Si and S, and refers to a monovalent group having non-aromaticity in the entire molecule. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group and the like. In the present specification, the condensed divalent non-aromatic heteropolycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

In the present specification, the substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -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 heteroaryl 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 ₆ -C _{At least one of the substituents of the 60} arylalkyl group, the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed polycyclic group is,

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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;

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthio group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ ) substituted with at least one of (Q ₁₂ )(Q ₁₃ ), -N(Q ₁₄ )(Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), and -P(=O)(Q ₁₈ )(Q _{19 )} , C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group and C ₁ -C ₆₀ alkoxy group;

C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryl an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₆ -C ₆₀ arylalkyl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group;

Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a 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 heterocyclo alkyl 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 ₆ - C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N _{C 3} -C ₁₀ cycloalkyl group, C ₁ substituted with at least one of (Q ₂₄ )(Q ₂₅ ), -B(Q ₂₆ )(Q ₂₇ ), and -P(=O)(Q ₂₈ )(Q _{29 )} -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthi a group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group; and

-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) and -P(=O)(Q ₃₈ )(Q _{39 )} );

is selected from

The Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group, a substituted or unsubstituted C ₂ - ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, substituted or unsubstituted C ₆ -C ₆₀ aryl group, substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₆ -C ₆₀ arylalkyl group, a substituted or unsubstituted C ₁ -C _{60 may be selected from a} heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In this specification, "room temperature" refers to a temperature of about 25 ℃.

In the present specification, "biphenyl group and terphenyl group" refers to a monovalent group in which two or three benzene groups are bonded to each other by a single bond.

Hereinafter, a compound and an organic light emitting device according to an 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. In the following Synthesis Example, in the expression "'B' was used instead of 'A'", the amount of 'B' and the amount of 'A' used are the same on the basis of molar equivalent.

[Example]

Synthesis Example 1: Synthesis of compound 158

Synthesis of Intermediate 158(a)

Phenylboronic acid (2.09 g, 17.11 mmol), 9,10-dibromoanthracene (9,10-dibromoanthracene) (5.0 g, 14.88 mmol), Palladium tetrakis (triphenylphosphine) ), Pd(PPh ₃ ) ₄ ) (1.72 g, 1.49 mmol), potassium carbonate (K ₂ CO ₃ ) (4.11 g, 29.76 mmol), S-phos (1.22 g, 2.98 mmol) ) was put into 50 ml of tetrahydrofuran and 50 ml of distilled water and heated to reflux. After completion of the reaction, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the obtained organic layer was dried over anhydrous sodium sulfate (Na ₂ SO ₄ ), concentrated, and separated by silica gel column chromatography (dichloromethane/hexane). did. The resulting solid was recrystallized from hexane to obtain an intermediate 158(a) as a white solid (4.23 g, 14.88 mmol, yield 85%).

LC-Mass (Calculated: 333.02 g/mol, Measured: 333.12 g/mol (M+1))

Synthesis of Intermediate 158(b)

Intermediate 158(a) (4.2g, 12.60mmol), Bis(pinacolato)diboron) (4.8g, 18.91mmol), Potassium acetate (AcOK) (3.09g, 31.51mmol) ), [1,1'-bis (diphenylphosphino) ferrocene] palladium (II), [1,1'-bis (diphenylphosphino) ferrocene] palladium (II) dichloride, Pd (dppf) Cl _2), and (0.46g , 0.63 mmol), was placed in a reaction vessel, dissolved in 30 mL of dioxane, and stirred at 100°C. After completion of the reaction, the organic layer was cooled to room temperature, extracted with ethyl acetate and water, and the obtained organic layer was filtered through silica gel and concentrated. The obtained solid compound, Intermediate 158(b), was directly used in the next reaction without further purification. (4.1 g, yield 86%)

LC-Mass (Calculated: 380.19 g/mol, Measured: 380.3 g/mol (M+1))

Synthesis of compound 158

Intermediate 158(b) (5.99 g, 15.76 mmol), 7-chloro-5,9-dioxa-13b-borannaphtho [3,2,1-de] anthracene (7-chloro-5,9-dioxa- 13b-boranaphtho[3,2,1-de]anthracene) (4.0 g, 13.13 mmol), bis(dibenzylideneacetone)palladium(0) (bis(dibenzylideneacetone)palladium(0)), Pd(dba) ₂ ) (0.38 g, 0.66 mmol), potassium phosphate tribasic, K ₃ PO ₄ (5.58 g, 26.27 mmol), S-phos (1.08 g, 2.63 mmol) in toluene 40 ml and 40 ml of distilled water and heated to reflux. After completion of the reaction, the reaction was cooled to room temperature, the organic layer was extracted with ethyl acetate, and the obtained organic layer was dried over anhydrous sodium sulfate (Na ₂ SO ₄ ), concentrated, and separated by silica gel column chromatography (dichloromethane/hexane). did. The resulting solid was recrystallized from hexane to give compound 158 as a yellow solid (3.6 g, 13.13 mmol, yield 52%).

LC-Mass (Calculated: 522.41 g/mol, Measured: 522.51 g/mol (M+1))

Synthesis Example 2: Synthesis of compound 160

Synthesis of compound 160

7-chloro-5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene (7-chloro-5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene ) instead of 2,12-di-tert-butyl-7-chloro-5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene (2,12-di-tert-butyl-7 -chloro-5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene) was used, and using the same method as the synthesis method of compound 158 of Synthesis Example 1, compound 160 (4.2 g, yield) 69%) was synthesized.

LC-Mass (calculated: 634.3 g/mol, measured: 634.4 g/mol (M+1))

Synthesis Example 3: Synthesis of compound 170

Synthesis of compound 170

7-chloro-5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene (7-chloro-5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene ) instead of 3,11-di-tert-butyl-7-chloro-5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene (3,11-di-tert-butyl-7 -chloro-5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene) was used, and compound 170 (4.2 g, yield) was used in the same method as that of compound 158 of Synthesis Example 1 69%) was synthesized.

LC-Mass (calculated: 634.3 g/mol, measured: 634.4 g/mol (M+1))

Synthesis Example 4: Synthesis of compound 165

Synthesis of Intermediate 165(a)

Using 3-bromophenylboronic acid ((3-bromophenyl)boronic acid) instead of phenylboronic acid, and using the same method as the synthesis method of compound 158(a) of Synthesis Example 1, intermediate 165 ( a) (5.24 g, yield 86%) was synthesized.

LC-Mass (calculated: 408.05 g/mol, measured: 408.15 g/mol (M+1))

Synthesis of Intermediate 165(b)

Intermediate 165(a) was used instead of Intermediate 158(a), and Intermediate 165(b) (5.8 g, yield 99%) was synthesized using the same method as the synthesis method of compound 158(b) of Synthesis Example 1. .

LC-Mass (Calculated: 456.23 g/mol, Measured: 456.33 g/mol (M+1))

Synthesis of compound 165

Intermediate 165(b) was used instead of Intermediate 158(b), and compound 165 (2.6 g, yield 43%) was synthesized using the same method as the synthesis method of compound 158 of Synthesis Example 1.

LC-Mass (Calculated: 598.21 g/mol, Measured: 598.31 g/mol (M+1))

Synthesis Example 5: Synthesis of compound 167

Synthesis of compound 167

Intermediate 165(b) was used instead of Intermediate 158(b), and compound 167 (3.8 g, yield 55%) was synthesized using the same method as the synthesis method of compound 160 of Synthesis Example 2.

LC-Mass (Calculated: 710.34 g/mol, Measured: 710.44 g/mol (M+1))

Evaluation Example 1: Material property evaluation

Some of the polycyclic compounds represented by Formula 1, for example, the optical bandgap Eg, S ₁ energy level, PL spectrum, and half width of some compounds of compounds 158, 160 and 170 were measured according to the method described in Table 1 below, The results are shown in Table 2 below.

Optical Bandgap Eg Evaluation Method ^{Each compound was diluted to a concentration of 1x10 -5} M in Toluene, and the UV absorption spectrum was measured at room temperature using a Shimadzu UV-350 Spectrometer, and the edge of the absorption spectrum Calculate the LUMO energy level using the optical bandgap (Eg) and HOMO energy level from S ₁ Energy Level Assessment Method The on set S1 energy level was calculated by measuring the photoluminescence spectrum of a mixture of toluene and each compound ( ^{diluted to a concentration of 1x10 -4} M) at room temperature using a photoluminescence measuring instrument and analyzing the observed peak. PL (photoluminescence) spectrum measurement method Each compound was diluted in toluene to a ^{concentration of 10 -4} M, and the PL (Photoluminecscence) spectrum was measured (@ 298K) using a Hitachi F7000 Spectrofluorometer equipped with a Xenon lamp, and from this, the half width of each compound was obtained. Calculate the height ratio (FWHM)

Compound No. Eg S _1,max
(eV) S _{1, onset}
(nm) PL
(nm) FWHM
(nm) 158 2.98 2.84 408 436 48 160 2.98 2.86 415 433 49 170 3.0 2.88 401 430 52

From Table 2, it can be seen that the polycyclic compound represented by Chemical Formula 1 is suitable for use as a dopant for an electronic device, for example, an organic light emitting device, and has excellent light emitting properties and electrical properties.

Evaluation Example 2: Evaluation of luminescence efficiency (PLQY) and decay time

(1) Thin film preparation

After preparing a quartz substrate washed with chloroform and pure water, each of the compounds shown in Table 2 (PMMA: 0.5 wt % compound) was dissolved in dichloromethane to prepare a thin film with a thickness of 30 nm or more by spin coating.

(2) Evaluation of luminous quantum efficiency

A xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere are installed to measure the quantum luminescence efficiency of the thin film. PLQY for each of the compounds listed in Table 2 was evaluated by measuring the thin film prepared previously using the Hamamatsu Photonics absolute PL quantum yield measurement system, employing PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan). did.

(3) Estimation of decay time

For the thin film, the PL spectrum was evaluated at room temperature using FluoTime 300, PicoQuant's TRPL measurement system, and PicoQuant's pumping source, PLS340 (excitation wavelength = 340 nanometers, spectral width = 20 nanometers). The wavelength of the main peak is determined, and the number of photons emitted at the wavelength of the main peak from the thin film by a photon pulse (pulse width = 500 picoseconds) applied by the PLS340 to the thin film is time- Measurements were repeated over time based on Time-Correlated Single Photon Counting (TCSPC) to obtain a TRPL curve capable of sufficiently fitting. _{T decay} (Ex) (decay time) of the thin film was obtained by fitting two or more exponential decay functions to the result obtained therefrom. Function used in the fitting is to the same as the <Equation 1>, by taking the largest value of T obtained from the respective _decay exponential decay function used to _decay fitting T (Ex) are shown in Table 3 below. The remaining T _decay values can be used to determine the decay lifetime of normal fluorescence. At this time, the same measurement is repeated once more in the dark state (the state in which the pumping signal incident to the predetermined film is blocked) for the same measurement time as the measurement time for obtaining the TRPL curve to obtain a baseline or A background signal curve was obtained and used as a baseline for fitting.

<Formula 1>

Compound No. PLQY T _decay (Ex) (ns)
(attenuation time) 158 0.957 91 160 0.934 19 170 0.954 109

From Table 3, it can be seen that the polycyclic compounds represented by Formula 1, for example, compounds 158, 160 and 170, are suitable for use as a dopant and have excellent PLQY (in film) and decay time characteristics.

Example 1

The glass substrate on which the ITO electrode was disposed was cut into a size of 50 mm x 50 mm x 0.5 mm and ultrasonically cleaned in acetone isopropyl alcohol and pure water for 15 minutes each, followed by UV ozone cleaning for 30 minutes.

Then, HAT-CN is deposited on the ITO electrode (anode) on the glass substrate to form a hole injection layer with a thickness of 100 Å, and NPB is deposited on the hole injection layer to form a first transport and transport layer with a thickness of 500 Å, TCTA was deposited on the first hole transport layer to form a second forward transport layer with a thickness of 50 Å, and mCP was deposited on the second hole transport layer to form an electron blocking layer with a thickness of 50 Å.

On the electron blocking layer, the host, the sensor, and the emitter described in Table 4 were co-deposited at a predetermined weight ratio to form a light emitting layer having a thickness of 400 Å.

DBFPO was deposited on the light emitting layer to form a hole blocking layer with a thickness of 100 Å, then DBFPO and Liq were co-deposited in a weight ratio of 5:5 to form an electron transport layer with a thickness of 300 Å, and then Liq was deposited on the electron transport layer. to form an electron injection layer with a thickness of 10 Å, and by depositing Al with a thickness of 1000 Å on the electron injection layer to form a cathode, an organic light emitting device was manufactured.

Examples 2 to 5, and Comparative Examples 1 to 3

An organic light emitting diode was manufactured in the same manner as in Example 4, except that the compounds shown in Table 1 were used when the emission layer was formed.

host
(mixed weight ratio) sensor
(content) emitter
(content) Example 1 H1, H2
(50:50) S-1
(13% by weight) compound 158
(3% by weight) Example 2 H1, H2
(50:50) S-1
(13% by weight) compound 160
(3% by weight) Example 3 H1, H2
(50:50) S-1
(13% by weight) compound 170
(3% by weight) Example 4 H1, H2
(50:50) S-1
(13% by weight) compound 165
(3% by weight) Example 5 H1, H2
(50:50) S-1
(13% by weight) compound 167
(3% by weight) Comparative Example 1 H1, H2
(50:50) S-1
(13% by weight) compound A
(3% by weight) Comparative Example 2 H1, H2
(50:50) S-1
(13% by weight) compound B
(3% by weight) Comparative Example 3 compound C
(97% by weight) - compound A
(3% by weight)

Evaluation Example 3: Characterization of an organic light emitting device

For each of the organic light emitting devices manufactured in Examples 1 to 5 and Comparative Examples 1 to 3, the T95 lifetime characteristics and quantum efficiency, which is the time it takes for the driving voltage and initial luminance to decrease by 95%, were measured, and Comparative Example 3 It is shown in Table 5 below as relative values for .

Driving voltage (V) maximum emission wavelength
(nm) Relative quantum efficiency (%) Relative lifespan
(%) Example 1 4.24 423 102 101 Example 2 4.27 422 102 126 Example 3 4.11 456 113 88 Example 4 3.53 461 104 348.3 Example 5 3.23 459 68 127.2 Comparative Example 1 No luminescence characteristics (not driven) Comparative Example 2 No luminescence characteristics (not driven) Comparative Example 3 3.7 463 100 100

As shown in Table 5, it was confirmed that Examples 1 to 5 had high efficiency and/or longer lifespan characteristics compared to Comparative Example 3, and Comparative Examples 1 and 2 did not perform energy transfer to the dopant, so that the light emitting characteristics were not confirmed. didn't

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

Claims (20)

a first electrode;
a second electrode; and
an organic layer including a light emitting layer disposed between the first electrode and the second electrode; and
The light emitting layer comprises a polycyclic compound represented by the following formula (1) and a host,
An organic light emitting device, wherein the content of the polycyclic compound is smaller than the content of the host:
<Formula 1>

<Formula 1A>

In Formulas 1 and 1A,
Ar ₁ is a group represented by Formula 1A,
rings CY ₁ and CY ₂ are each independently a C ₅ -C ₃₀ carbocyclic group or a C ₁ -C ₃₀ heterocyclic group,
Y ₁ is B, N, P, P(=O), P(=S), Al, Ga, As, Si(R ₅ ) or Ge(R ₅ ),
X ₁ and X ₂ are each independently O, S, Se, N(R ₆ ), C(R ₆ )(R ₇ ), Si(R ₆ )(R ₇ ), Ge(R ₆ )(R _{7 )} ), P(=O)(R ₆ ),
L ₁ and L ₁₁ are each independently selected from a single bond, a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group and a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group,
a1 and a11 are each independently an integer selected from 1 to 3,
When a1 is 2 or more, two or more L ₁ are the same or different from each other, and when a11 is 2 or more, two or more L ₁₁ are the same or different from each other,
R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₁₁ and R ₁₂ are independently of each other hydrogen, deuterium, -F, -Cl, -Br, -I, -SF ₅ , a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C ₁ -C ₆₀ alkyl group , substituted or unsubstituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted 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 a C ₆ -C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₆ -C ₆₀ arylalkyl group, A substituted or unsubstituted C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q ₁ ) ( Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=O)(Q ₈ )(Q ₉ ),
The R ₁ and R ₂ may be optionally combined with each other to form a substituted or unsubstituted C ₅ -C ₃₀ carbocyclic group or a substituted or unsubstituted C ₁ -C ₃₀ heterocyclic group, and ,
b1 and b2 are each independently an integer selected from 0 to 10,
When b1 is 2 or more, two or more R ₁ are the same as or different from each other, and when b2 is 2 or more, two or more R ₂ are the same or different from each other,
b11 is an integer selected from 1 to 5;
When b11 is 2 or more, two or more R ₁₁ are the same as or different from each other,
b12 is an integer selected from 1 to 8;
When b12 is 2 or more, 2 or more R ₁₂ are the same as or different from each other,
c11 is an integer selected from 1 to 8;
When c11 is 2 or more, two or more -(L ₁₁ ) _a11 -(R ₁₁ ) _b11 are the same as or different from each other,
The sum of b12 and c11 is 9,
said substituted C ₅ -C ₃₀ carbocyclic group, substituted C ₁ -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 ₆ -C ₆₀ arylalkyl group, At least one of the substituents of the substituted C ₁ -C ₆₀ heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed polycyclic group is,
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, 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 ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ an alkynyl 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 group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ - C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ aryl come T, C ₆ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q ₁₁ )(Q ₁₂ )(Q ₁₃ ), -N(Q ₁₄ )( Q ₁₅ ), -B(Q ₁₆ )(Q ₁₇ ), and -P(=O)(Q ₁₈ )(Q _{19 ), C 1} -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group substituted with at least one selected from , C ₂ -C ₆₀ alkynyl group and 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 an oxy group, a C ₆ -C ₆₀ arylthio group, a C ₆ -C ₆₀ arylalkyl group, a C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group;
Deuterium, -F, -Cl, -Br, -I, -CD ₃ , -CD ₂ H, -CDH ₂ , -CF ₃ , -CF ₂ H, -CFH ₂ , hydroxyl group, cyano group, nitro group, 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 ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₆ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, 1 A non-aromatic condensed heteropolycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₄ )(Q ₂₅ ) -B(Q ₂₆ )(Q ₂₇ ) and -P(=O) )(Q ₂₈ )(Q _{29 ), C 3} -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalke, substituted with at least one selected from (Q 28 )(Q 29 ) group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₆ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic heterocondensed polycyclic group; and
-Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )(Q ₃₇ ) and -P(=O)(Q ₃₈ )(Q _{39 )} );
is selected from;
The Q ₁ to Q ₉ , Q ₁₁ to Q ₁₉ , Q ₂₁ to Q ₂₉ and Q ₃₁ to Q ₃₉ are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, cya No group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, substituted or unsubstituted C ₁ -C ₆₀ alkyl group, substituted or unsubstituted substituted C ₂ -C ₆₀ alkenyl group, substituted or unsubstituted C ₂ -C ₆₀ alkynyl group, substituted or unsubstituted C ₁ -C ₆₀ alkoxy group, substituted or unsubstituted C ₃ -C ₁₀ cycloalkyl group, substituted or an unsubstituted C ₁ -C ₁₀ heterocycloalkyl group, a substituted or unsubstituted C ₃ -C ₁₀ cycloalkenyl group, a substituted or unsubstituted C ₁ -C ₁₀ heterocycloalkenyl group, a substituted or unsubstituted C ₆ - C ₆₀ aryl group, a substituted or unsubstituted C ₆ -C ₆₀ aryloxy group, a substituted or unsubstituted C ₆ -C ₆₀ arylthio group, a substituted or unsubstituted C ₆ -C ₆₀ arylalkyl group, a substituted or unsubstituted selected from a C ₁ -C ₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. According to claim 1,
Y ₁ is B,
X ₁ and X ₂ are each independently selected from O, S, Se, N(R ₆ ), C(R ₆ )(R ₇ ) and Si(R ₆ )(R ₇ ), an organic light-emitting device. According to claim 1,
Wherein CY ₁ and CY ₂ are each independently, a condensed ring formed by condensing two or more groups selected from the following group A, group B, and group A, a condensed ring formed by condensing two or more groups selected from the following group B, and at least one An organic light emitting device selected from a condensed ring formed by condensing the A group of at least one B group with each other:
Group A is cyclopenta-1,3-diene, indene group, azulene group, benzene group, naphthalene group, anthracene group, phenanthrene group, tetracene group, tetrapene group, pyrene group, chrysene group, triphenyl is a lene group or a fluorene group,
Group B is a furan group, a thiophene group, a pyrrole group, a borol group, a silol group, a pyrrolidine group, an imidazole group, a thiazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, isothia. Zole group, pyridine group, pyrimidine group, pyridazine group, triazine group, indole group, isoindole group, indolizine group, quinoline group, isoquinoline group, quinoxaline group, isoquinoxaline group, carbazole group, di benzofuran, dibenzothiophene, dibenzosilol group, or dibenzoborol group. According to claim 1,
CY ₁ and CY ₂ are each independently selected from a benzene group, a naphthalene group, an anthracene group, and a fluorene group, an organic light emitting device. According to claim 1,
L ₁ and L ₁₁ are independently of each other,
single bond;
Phenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl a renylene group, a pyrenylene group, and a chrysenylene group; and
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalke group, 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 ₆ - C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group substituted with at least one selected from a phenylene group, an indenylene group, a naphthylene group, Azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, and chrysenylenyl group Rengi; and
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group Or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalke group, 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 ₆ - C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, monovalent non-aromatic condensed polycyclic group and monovalent non-aromatic condensed heteropolycyclic group substituted with at least one selected from a phenyl group, indenyl group, naphthyl group, azulenyl group , heptalenyl group, acenaphthyl group, fluorenyl group, phenarenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, and at least one selected from chrysenylenyl group is substituted Phenylene group, indenylene group, naphthylene group, azulenylene group, heptalenylene group, acenaphthylene group, fluorenylene group, phenarenylene group, phenanthrenylene group, anthracenylene group, fluoranthenylene group, triphenyl a renylene group, a pyrenylene group, and a chrysenylene group;
selected from among, an organic light emitting device. According to claim 1,
L ₁ and L ₁₁ are a single bond, and an organic light emitting device selected from the following Chemical Formulas 3-1 to 3-32:

In Formulas 3-1 to 3-32,
Z ₃₁ is hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group Or a salt thereof, a phosphoric acid group or a salt thereof, C ₁ -C ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ -C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy group, C ₆ -C ₆₀ arylthi a group, a C ₆ -C ₆₀ arylalkyl group, and a C ₁ -C ₆₀ heteroaryl 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 ₆₀ alkyl group, C ₂ -C ₆₀ alkenyl group, C ₂ -C ₆₀ alkynyl group, C ₁ -C ₆₀ alkoxy group, C ₃ -C ₁₀ cycloalkyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkenyl group, C ₆ - C ₆₀ aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₆ -C ₆₀ arylalkyl group, C ₁ -C ₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, 1 A non-aromatic condensed heteropolycyclic group, -Si(Q ₂₁ )(Q ₂₂ )(Q ₂₃ ), -N(Q ₂₄ )(Q ₂₅ ) -B(Q ₂₆ )(Q ₂₇ ) and -P(=O) _{) (Q 28) (Q 29} ) from the at least one selected substituted, C ₃ -C ₁₀ cycloalkyl, C ₃ -C ₁₀ cycloalkenyl group, C ₁ -C ₁₀ heterocycloalkyl group, C ₁ -C ₁₀ heteroaryl cycloalkenyl group, C ₆ -C ₆₀ is selected from an aryl group, C ₆ -C ₆₀ aryloxy, C ₆ -C ₆₀ arylthio, C ₆ -C ₆₀ arylalkyl group, and C ₁ -C ₆₀ heteroaryl group,
e4 is an integer selected from 1 to 4,
e6 is an integer selected from 1 to 6,
e8 is an integer selected from 1 to 8,
* and *' are binding sites with neighboring atoms. According to claim 1,
R ₁ and R ₂ are independently of each other,
hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, a C ₁ -C ₆₀ alkyl group, a C ₁ -C ₆₀ alkoxy group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group , a triphenylenyl group, a pyrenyl group, a C ₁ -C ₆₀ alkyl group substituted with at least one of a chrysenyl group, a C ₁ -C ₆₀ alkoxy group;
cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, Triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group , pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, Sinolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group;
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, C ₁ -C ₆₀ alkyl group and C ₁ -C ₆₀ alkoxy group, C ₆ -C ₆₀ arylalkyl group, cyclo Pentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, tri phenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, Pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cy Nolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, benzoxazolyl group, benzoisoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, tria Zinyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, -Si(Q ₃₁ )(Q ₃₂ )(Q ₃₃ ), -N(Q ₃₄ )(Q ₃₅ ), -B(Q ₃₆ )( Q ₃₇ ) and -P(=O)(Q ₃₈ )(Q ₃₉ ) substituted with at least one of a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, Biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyra Zolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group , quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, Benzoxazolyl group, benzoisooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group and carbazolyl group; and
-N(Q ₁ )(Q ₂ ), -Si(Q ₃ )(Q ₄ )(Q ₅ ), -B(Q ₆ )(Q ₇ ) and -P(=O)(Q ₈ )(Q _{9 )} );
An organic light emitting device selected from According to claim 1,
At least one of R ₁ and R ₂ is selected from the group represented by the following Chemical Formulas 5-1 and 5-2, an organic light emitting device:

In Formulas 5-1 and 5-2,
R ₅₁ to R ₅₅ are each independently,
Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec- Butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso -hexyl group, sec-hexyl group and tert-hexyl group, phenyl group, biphenyl group and terphenyl group; and
Deuterium, -F, -Cl, -Br, -I, a methyl group substituted with at least one of a hydroxyl group, a cyano group, a nitro group, and a phenyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso -Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group;
is selected from
The R ₅₄ and R ₅₅ may be optionally combined with each other to form a heterocycle,
b54 and b55 are each independently an integer selected from 0 to 4. According to claim 1,
R ₃ and R ₄ are independently of each other,
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group , iso-hexyl group, sec-hexyl group and tert-hexyl group;
Deuterium, -F, -Cl, -Br, -I, a methyl group substituted with at least one of a hydroxyl group, a cyano group, a nitro group, and a phenyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso -Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group;
selected from, an organic light emitting device. According to claim 1,
R ₃ and R ₄ are each hydrogen, an organic light emitting device. According to claim 1,
R ₅ , R ₆ and R ₇ are independently of each other,
hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group , iso-hexyl group, sec-hexyl group and tert-hexyl group;
Deuterium, -F, -Cl, -Br, -I, a methyl group substituted with at least one of a hydroxyl group, a cyano group, a nitro group, and a phenyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso -Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group;
a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;
A phenyl group substituted with at least one of a phenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, a biphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;
selected from, an organic light emitting device. According to claim 1,
R ₁₁ is selected from Formulas 4-1 to 4-42,
R ₁₂ is hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso- Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n -hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group;
Deuterium, -F, -Cl, -Br, -I, a methyl group substituted with at least one of a hydroxyl group, a cyano group, a nitro group, and a phenyl group, an ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso -Butyl group, sec-butyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group, iso-pentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, iso-hexyl group, sec-hexyl group and tert-hexyl group; An organic light emitting device selected from:

In Formulas 4-1 to 4-42,
Y ₃₁ is O, S, C(Z ₄₅ )(Z ₄₆ ), N(Z ₄₇ ), or Si(Z ₄₈ )(Z ₄₉ ),
Z ₄₁ to Z ₄₉ are each independently,
Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof , phosphoric acid group or a salt thereof, C ₁ -C ₂₀ alkyl group, C ₁ -C ₂₀ alkoxy group, C ₆ -C ₆₀ arylalkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclopentenyl group, cyclohexenyl group, Phenyl group, biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group , pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, Purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazole diary, benzoxazolyl group, benzoisooxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, and carbazolyl group;
Deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C ₁ -C ₂₀ alkyl group, a C ₁ -C ₂₀ alkoxy group, and a cyclopentyl group substituted with at least one of a cumyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, Biphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyra Zolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindoleyl group, indolyl group, indazolyl group, purinyl group , quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinolinyl group, phenanthrolinyl group, benzoimidazolyl group, benzofuranyl group, benzothiophenyl group, benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group;
f3 is selected from an integer of 1 to 3,
f4 is selected from an integer of 1 to 4,
f5 is selected from an integer of 1 to 5,
f6 is selected from an integer of 1 to 6,
f7 is selected from an integer of 1 to 7,
f9 is selected from an integer of 1 to 9,
* is a binding site with a neighboring atom. According to claim 1,
Formula 1A is an organic light emitting device selected from the following Formulas 1A-1 to 1A-5:

In Formulas 1A-1 to 1A-5,
For descriptions of L ₁₁ , a ₁₁ , R ₁₁ and b ₁₁ , refer to paragraph 1, respectively,
For a description of R ₂₁ to R ₂₉ , refer to the description of _{R 12 of claim 1, respectively,}
* is a binding site with a neighboring atom. According to claim 1,
The polycyclic compound is an organic light emitting device comprising a compound represented by any one of the following Chemical Formulas 2-1 to 2-8.

In Formulas 2-1 to 2-8,
For the description of Y ₁ , X ₁ , X ₂ , R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , L ₁ , a _{1 ,} and Ar ₁ , see the description of claim 1 . According to claim 1,
The polycyclic compound is an organic light emitting device selected from the following compounds 1 to 468:

. According to claim 1,
The polycyclic compound is a fluorescent emitter, an organic light emitting device. 17. The method of claim 16,
An organic light emitting device, wherein the light emitting layer further comprises a sensor that satisfies the following formula 1:
[Equation 1]
ΔE _ST ≤ 0.3 eV
Here, ΔE _ST denotes the energy difference between the lowest excitation singlet (S ₁ ) and the lowest excitation triplet (T _{1 ).} 18. The method of claim 17,
The sensor and the polycyclic compound satisfy the following conditions 1 and 2, an organic light emitting device:
<Condition 1>
T _decay (PC)<T _decay (S)
<Condition 2>
T _decay (PC)<1.5 μs
Among conditions 1 and 2 above,
T _decay (PC) is the decay time of the polycyclic compound;
T _decay (S) is the decay time of the sensitizer. According to claim 1,
The light emitting layer further comprises a light emitting dopant,
The content of the host is greater than the total content of the polycyclic compound and the light emitting dopant, an organic light emitting device. According to claim 1,
The first electrode is an anode,
The second electrode is a cathode,
The organic layer further includes a hole transport region interposed between the first electrode and the light emitting layer and an electron transport region interposed between the light emitting layer and the second electrode,
The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof,
The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

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